Sulfonyl derivatives as CCR6 inhibitors

Abstract

The present invention provides novel derivatives having the general formula (I) wherein R1, R2, R3, R4, R5, R6, R7, X1, X2, X3, X4 and X5 are as defined herein; comprising the compound; methods of making the compounds; and methods of using the compounds. # imgabs0 #

Description

Background Art

[0001] Immune surveillance (i.e., the migration of immune cells throughout the body) is a tightly regulated process that is involved in many aspects of health and disease. Chemokines and their corresponding receptors play a key role in these trafficking patterns, responsible for transporting the right cells to the right tissues (Griffith, J.W., Sokol, C.L. & Luster, A.D. (2014). Chemokines and Chemokine Receptors: Positioning Cells for Host Defense and Immunity. Immunology, 32(1), 659–702 and Zlotnik, A. & Yoshie, O. (2012). The Chemokine Superfamily Revisited. Immunity, 36(5), 705–716).

[0002] Chemokines, or chemotactic cytokines, are a family of approximately 50 small signaling proteins secreted by a variety of cell populations (David, B. A. & Kubes, P. (2019). Exploring the complex role of chemokines and chemoattractants in vivo on leukocyte dynamics. Immunological Reviews, 289(1), 9–30 and Griffith, J. W., Sokol, C. L. & Luster, A. D. (2014). Chemokines and Chemokine Receptors: Positioning Cells for Host Defense and Immunity. Immunology, 32(1), 659–702). Based on the position of characteristic cysteine residues in the N-terminal region, chemokines are divided into four main subfamilies, called CC, CXC, CX3C, and C. Chemokine secretion and diffusion generate concentration gradients that guide the migration of cells expressing the corresponding receptors. Chemokine receptors are a family of approximately 20 seven-transmembrane proteins that are differentially expressed on the surface of immune cells and can be divided into two main subfamilies, the first called G protein-coupled chemokine receptors, which mediate immune cell trafficking; and the second called atypical chemokine receptors, which appear to be chemokine scavengers that affect chemokine gradients. They are also grouped into four subfamilies according to the subfamily of their main chemokine ligands. In some cases, a single chemokine can signal through multiple receptors, and in many cases, a single receptor can be stimulated by multiple chemokines. These promiscuous interactions make pharmacological intervention in signaling more complex.

[0003] CCR6, also known as CD196, is a chemokine receptor expressed on a variety of adaptive and innate immune cells, including B cells, T cells, dendritic cells, and neutrophils. For example, TH17 cells (which play a key role in the pathogenesis of a variety of autoimmune diseases) express CCR6, and this signaling has been shown to recruit these cells to inflamed peripheral tissues (Esplugues, E., Huber, S., Gagliani, N., Hauser, A. E., Town, T., Wan, Y. Y., O’Connor, W., Rongvaux, A., Rooijen, N. V., Haberman, A. M., Iwakura, Y., Kuchroo, V. K., Kolls, J. K., Bluestone, J. A., Herold, K. C. & Flavell, R. A. (2011). Control of TH17 cells occurs in the Small Intestine. Nature, 475(7357), 514–518 and Singh, S. P., Zhang, H. H., Foley, J. F., Hedrick, M. N. & Farber, J. M. (2008). Human T Cells That Are Able to Produce IL-17 Express the Chemokine Receptor CCR6. The Journal of Immunology, 180(1), 214–221). The ligand for CCR6 is CCL20, also known as macrophage inflammatory protein 3α (MIP-3α) and liver and activation-regulated chemokine (LARC). The CCR6 / CCL20 pair is unique because they have only one binding partner and thus form a pharmacologically selective receptor-ligand pair (Schutyser, E., Struyf, S. & Damme, J. V. (2003). The CC chemokine CCL20 and its receptor CCR6. Cytokine & Growth Factor Reviews, 14(5), 409–426).

[0004] In the presence of inflammatory stimuli, CCL20 expression and secretion are increased. High levels of CCL20 can be found in inflamed tissues associated with a variety of inflammatory autoimmune diseases, including psoriasis, asthma, Crohn's disease, ulcerative colitis, rheumatoid arthritis, systemic lupus erythematosus, and multiple sclerosis (Richmond, J.M., Strassner, J.P., Essien, K.I. & Harris, J.E. (2019). T-cell positioning by chemokines in autoimmune skin diseases. Immunological Reviews, 289(1), 186–204, Lee, A.Y. & H. (2014). CCR6 and CCL20: emerging players in the pathogenesis of rheumatoid arthritis. Immunology and Cell Biology, 92(4), 354–358, Raman, D., Sobolik-Delmaire, T. & Richmond, A. (2011). Chemokines in health and disease. Experimental Cell Research, 317(5), 575–589, Pène, J., Chevalier, S., Preisser, L., Vénéreau, E., Guilleux, M.-H., Ghannam, S., Molès, J.-P., Danger, Y., Ravon, E., Lesaux, S., Yssel, H. & Gascan, H. (2008). Chronically Inflamed Human Tissues Are Infiltrated by Highly Differentiated Th17 Lymphocytes. The Journal of Immunology, 180(11), 7423–7430 and Schutyser, E., Struyf, S. & Damme, J.V. (2003). The CC chemokine CCL20 and its receptor CCR6. Cytokine & Growth Factor Reviews, 14(5), 409–426).

[0005] Genetic linkage, clinical association, and preclinical studies have highlighted the key role of CCR6 in these inflammatory diseases (Hamburg, J.P. van & Tas, S.W. (2018). Molecular mechanisms underpinning T helper17 cell heterogeneity and functions in rheumatoid arthritis. Journal of Autoimmunity, 87, 69–81 and Kurkó, J., Besenyei, T., Laki, J., Glant, T.T., Mikecz, K. & Szekanecz, Z. (2013). Genetics of Rheumatoid Arthritis—A Comprehensive Review. Clinical Reviews in Allergy & Immunology, 45(2), 170–179). For example, among the chemokine receptor family, CCR6 gene variants have the highest risk association with Crohn's disease (CD) (Lee, A.Y.S., Eri, R., Lyons, A.B., Grimm, M.C. & Korner, H. (2013). CC Chemokine Ligand 20 and Its Cognate Receptor CCR6 in Mucosal T Cell Immunology and Inflammatory Bowel Disease: Odd Couple or Axis of Evil? Frontiers in Immunology, 4, 194).

[0006] This high selectivity makes CCR6 an attractive drug target. Selective CCR6 inhibitors will only produce on-target pharmacology. Summary of the Invention

[0007] The first object of the present invention is a compound of formula (I)

[0008]

[0009] wherein

[0010] X 1 is CH or N;

[0011] X 2 is CH or N;

[0012] X 3 is CH or N;

[0013] X 4 is O or NH;

[0014] X 5 is CH or N;

[0015] R 1 is aryl, heterocyclic group or heteroaryl, wherein the aryl, heterocyclic group and heteroaryl are optionally substituted by one or more R 1a substituents;

[0016] R 1a is C 1-6 alkyl, cyano, -NR 1b R 1c -C 1-6 alkyl-NR 1b R 1c -CONR 1b R 1c -PO(Me)2, hydroxy, C 3-6 cycloalkyl, -C 1-6 alkyl-C 1-6 alkoxy, C 3-6 heterocyclic group, halo-C 1-6 alkyl, halo, C 1-6 alkoxy;

[0017] R 1b is hydrogen, C 3-6 cycloalkyl or C 1-6 alkyl;

[0018] R 1c is hydrogen, C 3-6 cycloalkyl or C 1-6 alkyl;

[0019] R 2 is hydrogen or halogen;

[0020] R 3 is hydrogen or halogen;

[0021] R 4 is hydrogen, C 1-6 alkyl or halogen;

[0022] R 5 is hydrogen, halogen or C 1-6 alkyl;

[0023] R 6 is hydrogen or -SF5, wherein R 6 and R 7 must be different;

[0024] R 7 is hydrogen or -SF5, wherein R 6 and R7 Must be different;

[0025] or a pharmaceutically acceptable salt thereof.

[0026] A second object of the present invention is a method for preparing a compound of formula (I) or a pharmaceutically acceptable salt thereof as described above, wherein X 1 is N and X 4 is O, and the method comprises:

[0027] reacting a compound of formula (VI), wherein R 6 , R 7 and X 5 are as defined above,

[0028]

[0029] with a compound of formula (VII), wherein R 5 and R 4 are as defined above,

[0030]

[0031] to form a compound of formula (VIII), wherein R 4 , R 5 , X 5 , R 6 , R 7 are as defined above,

[0032]

[0033] reacting the compound of formula (VIII) with an acid to form a compound of formula (IX), wherein R 4 , R 5 , X 5 , R 6 , R 7 are as defined above,

[0034]

[0035] reacting the compound of formula (XI) with a compound of formula (XI), wherein X 2 , X 3 , R 2 and R 3 are as defined above,

[0036]

[0037] to form a compound of formula (III), wherein R 2 , R 3 , R 4 , R 6 , R7 , R 5 , X 2 , X 5 and X 3 as defined above,

[0038]

[0039] reacting the compound of formula (III) with a compound of formula (X), wherein R 1 is as defined above, and R 9 and R 10 are independently selected from C 1-6 alkyl, or R 9 and R 10 together with the oxygen atom to which they are attached form a 3- to 14-membered heterocyclic group, which heterocyclic group is optionally substituted by one or more C 1-6 alkyl, especially optionally substituted by four C 1-6 alkyl,

[0040]

[0041] to form a compound of formula (I).

[0042] A third object of the present invention is a method for preparing a compound of formula (I) or a pharmaceutically acceptable salt thereof as described above, wherein X 1 is CH and X 4 is O, the method comprising:

[0043] reacting a compound of formula (XII), wherein R 5 and R 4 are as defined above,

[0044]

[0045] with CH3SO2Cl to form a compound of formula (XIII), wherein R 5 and R 4 are as defined above,

[0046]

[0047] reacting the said compound of formula (XIII) with a compound of formula (XIV), wherein R 3 , R 2 , X 2 and X 3 are as defined above,

[0048]

[0049] to form a compound of formula (XV), wherein R 3, R 2 , R 5 , R 4 , X 2 and X 3 as defined above,

[0050]

[0051] react the compound of formula (XV) with an oxidizing agent to form a compound of formula (XVI), wherein R 3 , R 2 , R 5 , R 4 , X 2 and X 3 as defined above,

[0052]

[0053] react the compound of formula (XVI) with an acid to form a compound of formula (XVII), wherein R 3 , R 2 , R 5 , R 4 , X 2 and X 3 as defined above,

[0054]

[0055] react the compound of formula (XVII) with a compound of formula (VI), wherein R 6 , R 7 and X 5 as defined above,

[0056]

[0057] to form a compound of formula (XVIII), wherein R 2 , R 3 , R 4 , R 6 , R 7 , R 5 , X 2 , X 5 and X 3 as defined above,

[0058]

[0059] react the compound of formula (XVIII) with a compound of formula (X), wherein R 1 as defined above, and R 9 and R 10 are independently selected from C 1-6alkyl, or R 9 and R 10 together with the oxygen atom to which they are attached form a 3- to 14-membered heterocyclic group, which heterocyclic group is optionally substituted by one or more C 1-6 alkyl groups, especially optionally substituted by four C 1-6 alkyl groups,

[0060]

[0061] react to form a compound of formula (I).

[0062] A fourth object of the present invention is a method for preparing a compound of formula (I) or a pharmaceutically acceptable salt thereof as described above, wherein X 1 is CH and X 4 is NH, and the method comprises:

[0063] reacting a compound of formula (XV), wherein R 3 、R 2 、R 5 、R 4 、X 2 and X 3 are as defined above,

[0064]

[0065] with an acid to form a compound of formula (XX), wherein R 3 、R 2 、R 5 、R 4 、X 2 and X 3 are as defined above,

[0066]

[0067] reacting the said compound of formula (XX) with a compound of formula (VI), wherein R 6 、R 7 and X 5 are as defined above,

[0068]

[0069] to form a compound of formula (XXI), wherein R 2 、R 3 、R 4 、R 6 、R 7 、R 5 、X 2 、X 5 and X 3 are as defined above,

[0070]

[0071] React the compound of formula (XXI) with ammonium carbamate and (diacetoxyiodo)benzene to form a compound of formula (XXII), wherein R 2 、R 3 、R 4 、R 6 、R 7 、R 5 、X 2 、X 5 and X 3 are as defined above,

[0072]

[0073] React the compound of formula (XXII) with a compound of formula (X), wherein R 1 is as defined above, and R 9 and R 10 are independently selected from C 1-6 alkyl, or R 9 and R 10 together with the oxygen atom to which they are attached form a 3- to 14-membered heterocyclic group, which heterocyclic group is optionally substituted by one or more C 1-6 alkyl, especially optionally substituted by four C 1-6 alkyl,

[0074]

[0075] to form a compound of formula (I).

[0076] The fifth object of the present invention is a method for preparing the compound of formula (I) or a pharmaceutically acceptable salt thereof as described above, wherein X 1 is N and X 4 is NH, and the method comprises:

[0077] React a compound of formula (IX), wherein R 4 、R 5 、X 5 、R 6 、R 7 are as defined above,

[0078]

[0079] with a compound of formula (XIV), wherein R 2 and R 3 are as defined above,

[0080]

[0081] A reaction is carried out to form a compound of formula (XXIV), wherein R 2 、R 3 、R 4 、R 6 、R 7 、R 5 、X 2 、X 5 and X 3 are as defined above,

[0082]

[0083] The compound of formula (XXIV) is reacted with ammonium carbamate and (diacetoxyiodo)benzene to form a compound of formula (XXV), wherein R 2 、R 3 、R 4 、R 6 、R 7 、R 5 、X 2 、X 5 and X 3 are as defined above,

[0084]

[0085] The compound of formula (XXV) is reacted with di-tert-butyl dicarbonate and NaH to form a compound of formula (XXVI), wherein R 2 、R 3 、R 4 、R 6 、R 7 、R 5 、X 2 、X 5 and X 3 are as defined above,

[0086]

[0087] The compound of formula (XXVI) is reacted with a compound of formula (X), wherein R 1 is as defined above, and R 9 and R 10 are independently selected from C 1-6 alkyl, or R 9 and R 10 together with the oxygen atom to which they are attached form a 3- to 14-membered heterocyclic group, which heterocyclic group is optionally substituted by one or more C 1-6 alkyl, especially optionally substituted by four C 1-6 alkyl,

[0088]

[0089] A reaction is carried out to form a compound of formula (XXVII), wherein R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 5 , X 2 , X 5 and X 3 are as defined above,

[0090]

[0091] The compound of formula (XXVII) is reacted with an acid to form a compound of formula (I).

[0092] A sixth object of the present invention is a pharmaceutical composition comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof as described above, and a pharmaceutically acceptable excipient.

[0093] A seventh object of the present invention is a compound of formula (I) or a pharmaceutically acceptable salt thereof as described above, which is used for use in the treatment, prevention and / or delay of inflammatory autoimmune diseases.

[0094] An eighth object of the present invention is a method for treating, preventing and / or delaying the progression of inflammatory autoimmune diseases, the method comprising administering a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof.

[0095] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, suitable methods and materials are described below.

[0096] All publications, patent applications, patents and other references mentioned herein are incorporated herein by reference in their entirety.

[0097] Unless otherwise indicated, the nomenclature used in this application is based on the IUPAC system of nomenclature.

[0098] Definitions

[0099] “-SF5” means pentafluorothio.

[0100] "Acid" refers to a compound capable of the following operations: donating a proton as defined by Brønsted, dissociating into a proton and a counterion in water at 25 °C, and giving a solution with a neutral or lower pH. Specific examples of acids are phosphoric acid (orthophosphoric acid), sulfuric acid, nitric acid, hypophosphorous acid, phosphonic acid, diphosphonic acid, hydrochloric acid, pyrophosphoric acid, metaphosphoric acid, nitrous acid, etc. These acids can be used in the form of metal salts, ammonium salts, etc. In particular, the acid means hydrochloric acid.

[0101] "Alkoxy" refers to a C alkyl group as previously defined attached to the parent molecular moiety via an oxygen atom. 1-6 Unless otherwise specified, the alkoxy group contains 1 to 12 carbon atoms ("C-alkoxy"), preferably 1 to 10 carbon atoms ("C-alkoxy"), more preferably 1 to 6 carbon atoms ("C-alkoxy"). 1-12 -alkoxy"), more preferably 1 to 6 carbon atoms ("C 1-10 -alkoxy"). In some specific embodiments, the alkoxy group contains 1 to 4 carbon atoms. In other embodiments, the alkoxy group contains 1 to 3 carbon atoms. Some non-limiting examples of alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, and tert-butoxy. 1-6 -alkoxy"). In some specific embodiments, the alkoxy group contains 1 to 4 carbon atoms. In other embodiments, the alkoxy group contains 1 to 3 carbon atoms. Some non-limiting examples of alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, and tert-butoxy.

[0102] "C 1-6 alkyl" refers to a saturated straight-chain (i.e., non-branched) or branched monovalent hydrocarbon chain or a combination thereof having the specified number of carbon atoms (i.e., C means one to six carbon atoms). Specific C alkyl groups are those having 1 to 6 carbon atoms, having 2 to 6 carbon atoms ("C 1-6 alkyl") or having 1 to 4 carbon atoms ("C 1-6 alkyl"). Examples of C alkyl groups include, but are not limited to, groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, and homologs and isomers such as n-pentyl, n-hexyl, etc. 2-6 alkyl") or having 1 to 4 carbon atoms ("C 1-4 alkyl"). Examples of C alkyl groups include, but are not limited to, groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, and homologs and isomers such as n-pentyl, n-hexyl, etc. 1-6 alkyl" refers to a saturated straight-chain (i.e., non-branched) or branched monovalent hydrocarbon chain or a combination thereof having the specified number of carbon atoms (i.e., C means one to six carbon atoms). Specific C alkyl groups are those having 1 to 6 carbon atoms, having 2 to 6 carbon atoms ("C

[0103] "Amino", used alone or in combination with other groups, refers to NH2.

[0104] "Aromatic" refers to the conventional concept of aromatic as defined in the literature, particularly in the IUPAC - Compendium of Chemical Terminology, 2nd edition, A.D. McNaught & A. Wilkinson (eds.). Blackwell Scientific Publications, Oxford (1997).

[0105] "Aryl" means a cyclic aromatic hydrocarbon moiety of a monocyclic, bicyclic or tricyclic aromatic ring having 5 to 14 carbon ring atoms ("C 5-14 -aryl"). Bicyclic aryl ring systems include fused bicyclics having two fused five-membered aryl rings (represented as 5-5), fused bicyclics having one five-membered aryl ring and one fused six-membered aryl ring (represented as 5-6 and 6-5), and fused bicyclics having two fused six-membered aryl rings (represented as 6-6). The aryl group can be optionally substituted as described above. Examples of aryl moieties include, but are not limited to, phenyl, naphthyl, phenanthryl, fluorenyl, indenyl, cyclopentadienyl, azulenyl, etc. In particular, aryl means phenyl.

[0106] "Autoimmune disease" or "inflammatory autoimmune disease" means a disease that results from an immune response (including both autoantibody responses and cell-mediated responses) directed against self-tissues or tissue components. As used herein, the term autoimmune disease or inflammatory autoimmune disease encompasses organ-specific autoimmune diseases. Examples of autoimmune diseases are psoriasis, asthma, inflammatory bowel disease (IBD), Crohn's disease, obstructive lung disease, ulcerative colitis, rheumatoid arthritis, systemic lupus erythematosus, and multiple sclerosis.

[0107] "Cyano", used alone or in combination with other groups, means CN (i.e., nitrile).

[0108] "Cycloalkyl" means a saturated or partially unsaturated carbocyclic moiety having a monocyclic, bicyclic (including bridged bicyclic and cycloalkyl spiro moieties) or tricyclic ring and 3 to 10 carbon atoms within the ring (i.e., (C3-C 10 ) cycloalkyl). The cycloalkyl moiety can be optionally substituted with one or more substituents. In certain aspects, cycloalkyl contains 3 to 8 carbon atoms (i.e., (C3-C8) cycloalkyl). In other certain aspects, cycloalkyl contains 3 to 6 carbon atoms (i.e., (C3-C6) cycloalkyl). Examples of cycloalkyl moieties include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and their partially unsaturated (cycloalkenyl) derivatives (e.g., cyclopentenyl, cyclohexenyl, and cycloheptenyl), bicyclo[3.1.0]hexyl, bicyclo[3.1.0]hexenyl, bicyclo[3.1.1]heptyl, bicyclo[3.1.1]heptenyl, and bicyclo[1.1.1]pentane. The cycloalkyl moiety can be attached in a "spiro-cycloalkyl" or "cycloalkyl spiro" fashion, such as "spirocyclopropyl".

[0109] "Halo" or "halogen" means fluorine, chlorine, bromine, or iodine, particularly chlorine or fluorine.

[0110] "Halo-C 1-6 C 1-6"Alkyl" refers to a C group as defined above substituted by one or more halogen atoms, in particular by one to three halogen atoms. 1-6 C 1-6 More particularly, halo-C 1-6 C 1-6 Alkyl is chloro- and fluoro-C 1-6 C 1-6 In a particular embodiment, the halo-C 1-6 C 1-6 Alkyl refers to a perhalogenated C 1-3 C 1-6 More particularly, halo-C 1-6 C 1-6 Alkyl is trifluoromethyl, difluoromethyl or fluoromethyl. Most particularly, halo-C 1-6 C 1-6 The alkyl group is trifluoromethyl (-CF3).

[0111] "Haloalkoxy" refers to an alkoxy group in which at least one halogen replaces the C 1-6 An alkoxy group for each H in the hydrocarbon of the alkyl portion. Examples of haloalkoxy groups are difluoromethoxy (-OCHF2), trifluoromethoxy (-OCF3).

[0112] "Heteroaryl" refers to a monocyclic, bicyclic or tricyclic ring system of an aromatic heterocycle having 5 to 14 ring atoms, preferably 5 to 10 ring atoms, more preferably 5 to 6 ring atoms, which contains 1, 2, 3 or 4 heteroatoms selected from N, O and S, and the remaining ring atoms are carbon. In some aspects, the monocyclic heteroaryl ring can be 5- to 6-membered. The bicyclic heteroaryl ring systems include fused bicyclics having two fused five-membered heteroaryl rings (designated as 5-5), fused bicyclics having one five-membered heteroaryl ring and one fused six-membered heteroaryl ring (designated as 5-6 and 6-5), and fused bicyclics having two fused six-membered heteroaryl rings (designated as 6-6). The heteroaryl group can be optionally substituted as described above. Examples of heteroaryl moieties include indazolyl, indolyl, triazolopyridyl, imidazopyridyl, imidazopyrazinyl, pyridyl, triazolopyridazinyl, pyridazinyl, triazolopyrazinyl, pyrrolotriazinyl, spirocyclopropanedihydroindolyl, pyrrolyl, furyl, thienyl, imidazolyl, oxazolyl, thiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrazolyl, pyridazinyl, pyrimidinyl, triazinyl, isoxazolyl, benzofuryl, isothiazolyl, benzothienyl, benzophenylthio, indolyl, azaindolyl, isoindolyl, isobenzofuryl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzotriazolyl, pyrrolopyridyl, furanopyridyl, thiophenopyridyl, pyridopyrazinyl, pyrrolopyrimidinyl, pyrrolopyrazinyl, thiophenopyridazinyl, thiophenopyrimidinyl, thiophenopyrazinyl, furanopyridazinyl, furanopyrimidinyl and furanopyrazinyl. More particularly, heteroaryl is pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl.

[0113] "Heterocyclic" or "heterocyclic group" refers to a 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-membered monocyclic, 7-, 8-, 9- and 10-membered bicyclic (including bridged bicyclic and cycloalkyl spiro moieties) or 10-, 11-, 12-, 13-, 14- and 15-membered bicyclic heterocyclic moiety, which is saturated or partially unsaturated and has one or more (e.g., 1, 2, 3 or 4) heteroatoms selected from oxygen, nitrogen and sulfur located in the ring, and the remaining ring atoms are carbon. In some aspects, the heterocycle is a heterocycloalkyl. In certain aspects, heterocyclic or heterocyclic group refers to a 4-, 5-, 6- or 7-membered heterocycle. When used to refer to the ring atoms of a heterocycle, nitrogen or sulfur can also be in an oxidized form, and nitrogen can be substituted by one or more (C1-C6)C 1-6 alkyl or groups. The heterocycle can be attached to its side group at any heteroatom or carbon atom, resulting in a stable structure. Any ring atom of the heterocycle can be optionally substituted by one or more substituents described herein. Examples of such saturated or partially unsaturated heterocycles include, but are not limited to, tetrahydrofuryl, tetrahydrothienyl, pyrrole

[0114] alkyl, pyrrolidinyl, piperidinyl, pyrrolinyl, isoindolinyl, quinolinyl, isoquinolinyl, tetrahydroquinolinyl, dihydroindolyl, tetrahydroisoquinolinyl, decahydroquinolinyl, oxazolidinyl, piperazinyl, dioxolanyl, dioxolyl, diaza yl, oxaza yl, thiaza yl, morpholinyl, pyrrolidine 1-oxide, N-hydroxypiperidine, 1-methylpyrrolidine N-oxide, bisaziridinyl, and quinuclidinyl. The term heterocycle also includes groups in which the heterocycle is fused to one or more aryl, heteroaryl, or cycloalkyl rings, such as indolinyl, 3H-indolyl, chromanyl, azabicyclo[2.2.1]heptanyl, azabicyclo[3.1.0]hexanyl, azabicyclo[3.1.1]heptanyl, octahydroindolyl, or tetrahydroquinolinyl.

[0115] "Hydroxy", used alone or in combination with other groups, means -OH.

[0116] "Hydroxyalkyl" means a C 1-6 alkyl group in which one or more of the hydrogen atoms of the C 1-6 alkyl group have been replaced by a hydroxy moiety. Examples include alcohols and diols.

[0117] The term "inflammatory bowel disease" or "IBD" means several diseases associated with inflammation of the small intestine, large intestine (colon), rectum, or anus (anal sphincter), and may specifically include ulcerative colitis and Crohn's disease (including proctitis in both cases). As used in this context, the term "IBD" also includes gastrointestinal (GI) tract cancer, which may be a result of GI tract inflammation. As used in this specification, the term "gastrointestinal tract" or "GI tract" means the small intestine, large intestine (colon), rectum, or anus (anal sphincter).

[0118] "Moiety" and "substituent" mean an atom or a group of atoms bonded together, which is attached to another atom or molecule by one or more chemical bonds to form part of a molecule.

[0119] When indicating the number of substituents, the term "one or more" means a range from one substituent to the highest possible number of substituents, i.e., replacing one hydrogen with a substituent up to replacing all hydrogens, particularly where "one or more" means one, two, or three, and most particularly "one or more" means one or two.

[0120] "Obstructive lung disease" refers to any disease that causes the airways in the lungs to narrow or become blocked, preventing the patient from exhaling completely. Due to damage to the lungs or narrowing of the airways within the lungs, the air exhaled comes out more slowly than normal. At the end of a complete exhalation, an abnormally large amount of air may still remain in the lungs. Examples of obstructive lung diseases are asthma, bronchiectasis, bronchitis, and chronic obstructive pulmonary disease (COPD).

[0121] "Optional" or "optionally" means that the subsequent described event or circumstance may but does not necessarily occur, and the description includes the case where the event or circumstance occurs and the case where the event or circumstance does not occur. For example, "optionally substituted by a C 1-6 alkyl group aryl group" means that the C 1-6 alkyl may or may not be present, and the description includes the case where the aryl group is substituted by a C 1-6 alkyl group and the case where the aryl group is not substituted by a C 1-6 alkyl group.

[0122] "Optionally substituted" means unsubstituted or substituted. Generally, these substituents may be the same or different.

[0123] "Oxidizing agent" refers to one or more suitable electron acceptors or electron sharers and can be an element, a combination of elements, a compound, or a combination of compounds (which includes reducible compounds), and is a vapor, solid, or liquid under process conditions. An example of an oxidizing agent is mCPBA (3-chloroperoxybenzoic acid).

[0124] "Oxo", used alone or in combination with other groups, refers to =O.

[0125] "Pharmaceutically acceptable salt" refers to those salts that retain the biological effects and properties of the free base or free acid and are not undesirable biologically or otherwise. These salts are formed with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid (especially hydrochloric acid) and organic acids such as acetic acid, propionic acid, glycolic acid, pyruvic acid, oxalic acid, maleic acid, malonic acid, succinic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid, salicylic acid, N-acetylcysteine.

[0126] More particularly, the pharmaceutically acceptable salts of the compounds of formula (I) are salts of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, and methanesulfonic acid.

[0127] As used herein, "prevent" includes: preventing or delaying the appearance of clinical symptoms of a relevant condition, disease, or disorder in a mammal and especially in a human who may be suffering from or be predisposed to a condition, disease, or disorder but has not yet developed or manifested clinical or subclinical symptoms of the condition, disease, or disorder.

[0128] "Protecting group" means a group that selectively blocks a reactive site in a multifunctional compound to allow a chemical reaction to occur selectively at another unprotected reactive site typically associated with it in synthetic chemistry. The protecting group can be removed at an appropriate point. Exemplary protecting groups are amino protecting groups, carboxyl protecting groups, or hydroxyl protecting groups. Specific protecting groups are tert-butoxycarbonyl (Boc), benzyloxycarbonyl (Cbz), fluorenylmethoxycarbonyl (Fmoc), and benzyl (Bn). Further specific protecting groups are tert-butoxycarbonyl (Boc) and fluorenylmethoxycarbonyl (Fmoc). Even more specific protecting group is tert-butoxycarbonyl (Boc). Exemplary protecting groups and their applications in organic synthesis are described in, for example: Protective Groups in Organic Chemistry by T.W. Greene and P.G.M. Wuts, 5th Edition, 2014, John Wiley & Sons, N.Y.

[0129] "Substituted" means that at least one hydrogen atom of a compound or moiety is replaced by another substituent or moiety. Examples of such substituents include, but are not limited to, halogen, -OH, -CN, oxo, alkoxy, C 1-6 alkyl, alkylene, aryl, heteroaryl, haloalkyl, haloalkoxy, cycloalkyl, and heterocycle. For example, the term "haloalkyl" refers to the fact that one or more hydrogen atoms of C 1-6 alkyl (as defined below) are replaced by one or more halogen atoms (e.g., trifluoromethyl, difluoromethyl, fluoromethyl, chloromethyl, etc.). In one aspect, substitution as used herein can mean that at least one hydrogen atom of a compound or moiety described herein is replaced by a halogen or C

[0130] alkyl. 1-6

[0131] "Therapeutically effective amount" means an amount of a compound or molecule of the present invention that, when administered to a subject, (i) treats or prevents a specific disease, disorder, or affliction, (ii) attenuates, ameliorates, or eliminates one or more symptoms of a specific disease, disorder, or affliction, or (iii) prevents or delays the onset of one or more symptoms of a specific disease, disorder, or affliction described herein. The therapeutically effective amount depends on the compound, the disease state being treated, the severity of the disease being treated, the age and relative health of the subject, the route and form of administration, the judgment of the attending medical or veterinary practitioner, and other factors.

[0132] "Therapeutically inert carrier" means any non-therapeutically active and non-toxic ingredient used in formulating a pharmaceutical product, such as a disintegrant, binder, filler, solvent, buffer, tonicity agent, stabilizer, antioxidant, surfactant, or lubricant. Detailed Description ​

[0133] In one embodiment, the present invention relates to a compound of formula (I),

[0134]

[0135] wherein

[0136] X 1 is CH or N;

[0137] X 2 is CH or N;

[0138] X 3 is CH or N;

[0139] X 4 is O or NH;

[0140] X 5 is CH or N;

[0141] R 1 is aryl, heterocyclic group or heteroaryl, wherein the aryl, heterocyclic group and heteroaryl are optionally substituted by one or more R 1a substituents;

[0142] R 1a is C 1-6 alkyl, cyano, -NR 1b R 1c -C 1-6 alkylNR 1b R 1c oxo, -CONR 1b R 1c -PO(Me)2, hydroxy, C 3-6 cycloalkyl, -C 1-6 alkylC 1-6 alkoxy, C 3-6 heterocyclic group, haloC 1-6 alkyl, halo, C 1-6 alkoxy;

[0143] R 1b is hydrogen, C 3-6 cycloalkyl or C 1-6 alkyl;

[0144] R 1c is hydrogen, C 3-6 cycloalkyl or C 1-6 alkyl;

[0145] R 2 is hydrogen or halogen;

[0146] R 3 is hydrogen or halogen;

[0147] R4 is hydrogen, C 1-6 alkyl or halogen;

[0148] R 6 is hydrogen or -SF5, where R 6 and R 7 must be different;

[0149] R 7 is hydrogen or -SF5, where R 6 and R 7 must be different;

[0150] R 5 is hydrogen, halogen or C 1-6 alkyl;

[0151] or a pharmaceutically acceptable salt thereof.

[0152] A particular embodiment of the invention relates to a compound of formula (I) as described herein, wherein

[0153] R 1a is C 1-6 alkyl, cyano, oxo, -CONR 1b R 1c 、-PO(Me)2, hydroxy, C 3-6 cycloalkyl, -C 1-6 alkyl C 1-6 alkoxy, halo C 1-6 alkyl, halo, C 1-6 alkoxy;

[0154] R 1b is hydrogen or C 1-6 alkyl;

[0155] R 1c is hydrogen or C 1-6 alkyl;

[0156] X 5 is CH;

[0157] R 5 is hydrogen;

[0158] or a pharmaceutically acceptable salt thereof.

[0159] A particular embodiment of the invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein X 1 is CH.

[0160] A particular embodiment of the invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein X 1 is N.

[0161] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein X 2 is CH.

[0162] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein X 2 is N.

[0163] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein X 3 is CH.

[0164] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein X 3 is N.

[0165] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein X 4 is O.

[0166] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein X 4 is NH.

[0167] A particular embodiment of the present invention relates to a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein X 5 is N.

[0168] A particular embodiment of the present invention relates to a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein X 5 is CH.

[0169] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein X 1 is N, X 2 is CH, X 3 is CH, X 4 is O and X 5 is CH.

[0170] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein X 1 is CH, X 2 is CH, X 3 is CH, X 4 is O and X 5 is CH.

[0171] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein, or a pharmaceutically acceptable salt thereof, wherein X 1 is N, X 2 is N, X 3 is CH, X 4 is O and X 5 is CH.

[0172] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein, or a pharmaceutically acceptable salt thereof, wherein X 1 is N, X 2 is CH, X 3 is N, X 4 is O and X 5 is CH.

[0173] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein, or a pharmaceutically acceptable salt thereof, wherein X 1 is CH, X 2 is CH, X 3 is CH, X 4 is NH and X 5 is CH.

[0174] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein, or a pharmaceutically acceptable salt thereof, wherein X 1 is N, X 2 is CH, X 3 is CH, X 4 is NH and X 5 is CH.

[0175] A particular embodiment of the present invention relates to a compound of formula (I), formula (I') or formula (I") as described herein, or a pharmaceutically acceptable salt thereof, wherein R 1 is azaspiro[nonane], triazaspiro[decane], diazaspiro[decane], oxadiazaspiro[decane], oxazaspiro[nonane], oxazabicyclo[octane], pyrazolopyridinyl, pyrrolopyrimidinyl, pyrrolopyridinyl, thienyl, thienopyridinyl, pyrrolopyrazinyl, pyrrolo[1,2 - a]diazinyl, furyl, indazolyl, indolyl, isoindolinyl, triazolopyridinyl, imidazopyridinyl, imidazopyrazinyl, dihydroindolyl, phenyl, pyridinyl, triazolopyridazinyl, isoquinolinyl, pyridazinyl, triazolopyrazinyl, pyrrolotriazinyl or spiro[cyclopropane - 1,3 - dihydroindole], wherein azaspiro[nonane], triazaspiro[decane], diazaspiro[decane], oxadiazaspiro[decane], oxazaspiro[nonane], oxazabicyclo[octane], pyrazolopyridinyl, pyrrolopyrimidinyl, pyrrolopyridinyl, thienyl, thienopyridinyl, pyrrolopyrazinyl, pyrrolo[1,2 - a]diazinyl group, furyl, indazolyl, indolyl, isoindolinyl, triazolopyridinyl, imidazopyridinyl, imidazopyrazinyl, dihydroindolyl, phenyl, pyridinyl, triazolopyridazinyl, isoquinolinyl, pyridazinyl, triazolopyrazinyl, pyrrolotriazinyl or spiro[cyclopropane - 1,3 - dihydroindole], A base, furyl, indazolyl, indolyl, isoindolinyl, triazolopyridinyl, imidazopyridinyl, imidazopyrazinyl, indolinyl, phenyl, pyridyl, triazolopyridazinyl, isoquinolinyl, pyridazinyl, triazolopyrazinyl, pyrrolotriazinyl and spirocyclopropane indolinyl are optionally substituted with one or more R 1a substituted.

[0176] A particular embodiment of the present invention relates to a compound of formula (I), formula (I') or formula (I") as described herein or a pharmaceutically acceptable salt thereof, wherein R 1 is indazolyl, indolyl, isoindolinyl, triazolopyridinyl, imidazopyridinyl, imidazopyrazinyl, indolinyl, phenyl, pyridyl, triazolopyridazinyl, isoquinolinyl, pyridazinyl, triazolopyrazinyl, pyrrolotriazinyl or spirocyclopropane indolinyl, wherein indazolyl, indolyl, isoindolinyl, triazolopyridinyl, imidazopyridinyl, imidazopyrazinyl, indolinyl, phenyl, pyridyl, triazolopyridazinyl, isoquinolinyl, pyridazinyl, triazolopyrazinyl, pyrrolotriazinyl and spirocyclopropane indolinyl are optionally substituted with one or more R 1a substituted.

[0177] A particular embodiment of the present invention relates to a compound of formula (I), formula (I') or formula (I") as described herein or a pharmaceutically acceptable salt thereof, wherein R 1 is indazolyl, indolyl, pyridyl, triazolopyridinyl, phenyl or imidazopyridinyl, wherein indazolyl, indolyl, pyridyl, triazolopyridinyl, phenyl and imidazopyridinyl are optionally substituted with one or more R 1a substituted.

[0178] A particular embodiment of the present invention relates to a compound of formula (I), formula (I') or formula (I") as described herein or a pharmaceutically acceptable salt thereof, wherein R 1be methyl indazolyl, cyano-indolyl, cyano-indazolyl, oxo-isoindolinyl, carbamoylpyridyl, methyl-triazolopyridyl, imidazopyridyl, cyano-imidazopyridyl, imidazopyrazinyl, methylimidazopyridyl, carbamoyl-imidazopyridyl, isopropyl-triazolopyridyl, triazolopyridyl, carbamoylindazolyl, oxo-indolinyl, carbamoyl-triazolopyridyl, cyano-triazolopyridyl, (dimethylcarbamoyl)phenyl, methylimidazopyrazinyl, (dimethylcarbamoyl)pyridyl, (methylcarbamoyl)phenyl, (methylcarbamoyl)pyridyl, oxo-triazolopyridyl, carbamoylphenyl, isopropyl-triazolopyridazinyl, oxo-dihydroisoquinolinyl, carbamoylpyridazinyl, dimethylphosphorylphenyl, isopropyl-triazolopyrazinyl, oxo-pyridyl, oxo-pyrrolotriazinyl, hydroxypyridyl, (dimethylcarbamoyl)pyridyl, oxo-spiropropaneindolinyl, methoxyazaspiro[4.5]decanyl, oxo-triazaspiro[5.5]undecanyl, oxo-diazaspiro[5.5]undecanyl, oxo-oxadiazaspiro[5.5]undecanyl, oxaazaspiro[4.5]decanyl, oxaazabicyclo[3.3.0]octanyl, carbamoylfluorophenyl, propyltriazolopyrazinyl, isopropylcarbamoylphenyl, methylpyrazolopyridyl, N,N-dimethylamineimidazopyridyl, cyclopropylcarbamoylphenyl, pyrrolopyrimidinyl, pyrrolopyridyl, pyrazolopyridyl, carbamoylthienyl, methylimidazopyridyl, (trifluoromethyl)imidazopyridyl, fluoroimidazopyridyl, oxo-thienopyridyl, oxo-pyrrolopyrazinyl, oxo-pyrrolo[2,3-d]pyrimidinyl, carbamoyl-imidazopyridyl, furancarboxamide, cyano-imidazopyridyl, pyrrolidinyl-triazolopyridyl, propyltriazolopyrazinyl or azetidinyl-triazolopyridyl. group, be furancarboxamide, cyano-imidazopyridyl, pyrrolidinyl-triazolopyridyl, propyltriazolopyrazinyl or azetidinyl-triazolopyridyl.

[0179] A particular embodiment of the invention relates to a compound of formula (I), formula (I') or formula (I") as described herein or a pharmaceutically acceptable salt thereof, wherein R 1be methyl indazolyl, cyanoindolyl, cyanoindazolyl, oxoisoindolinyl, carbamoylpyridyl, methyl-triazolopyridyl, imidazopyridyl, cyanoimidazopyridyl, imidazopyrazinyl, methylimidazopyridyl, carbamoyl imidazopyridyl, isopropyl-triazolopyridyl, triazolopyridyl, carbamoyl indazolyl, oxindolyl, carbamoyl-triazolopyridyl, methyl-triazolopyridyl, methyl-triazolopyridyl, cyano-triazolopyridyl, (dimethylcarbamoyl)phenyl, methylimidazopyrazinyl, (dimethylcarbamoyl)pyridyl, (methylcarbamoyl)phenyl, (methylcarbamoyl)pyridyl, oxo-triazolopyridyl, carbamoylphenyl, carbamoylpyridyl, isopropyl-triazolopyridazinyl, oxo-dihydroisoquinolinyl, carbamoylpyridazinyl, dimethylphosphorylphenyl, oxoisoindolinyl, oxindolyl, oxo-dihydroisoquinolinyl, isopropyl-triazolopyrazinyl, oxo-pyridyl, oxo-dihydroisoquinolinyl, oxo-pyrrolotriazinyl, hydroxypyridyl, methyl-triazolopyridyl, imidazopyridyl, triazolopyridyl, carbamoylphenyl, carbamoylpyridyl, (dimethylcarbamoyl)pyridyl, oxospiropropane indolinyl.

[0180] A particular embodiment of the present invention relates to a compound of formula (I), formula (I') or formula (I") as described herein or a pharmaceutically acceptable salt thereof, wherein R 1 be methyl-indazolyl, cyano-indolyl, carbamoyl-pyridyl, methyl-imidazopyridyl, methyl-triazolopyridyl, isopropyl-triazolopyridyl, cyano-indazolyl, (methylcarbamoyl)phenyl, imidazopyridyl, cyanoimidazopyridyl.

[0181] A particular embodiment of the present invention relates to a compound of formula (I), formula (I') or formula (I") as described herein or a pharmaceutically acceptable salt thereof, wherein R 1a be methoxy, fluoro, -CONH[(CH(CH3)2], -CONH(cyclopropyl), dimethylamino, -CF3, pyrrolidinyl, azetidinyl, methyl, cyano, oxo, -CONH2, isopropyl, -CON(Me)2, -CH2-O-CH3, -CONH(Me), -PO(Me)2, -OH.

[0182] A particular embodiment of the present invention relates to a compound of formula (I), formula (I') or formula (I") as described herein or a pharmaceutically acceptable salt thereof, wherein R 1a be methyl, cyano, oxo, -CONH2, isopropyl, -CON(Me)2, -CH2-O-CH3, -CONH(Me), -PO(Me)2, -OH.

[0183] A particular embodiment of the present invention relates to a compound of formula (I), formula (I') or formula (I") as described herein or a pharmaceutically acceptable salt thereof, wherein R 1a is methyl, cyano, -CONH2, isopropyl, -CONH(Me).

[0184] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein R 2 is hydrogen, fluorine or -CF3.

[0185] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein R 2 is hydrogen.

[0186] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein R 3 is hydrogen, fluorine, chlorine or -CF3.

[0187] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein R 3 is hydrogen. A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein R 4 is hydrogen or fluorine.

[0188] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein R 4 is hydrogen.

[0189] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein R 6 is -SF5.

[0190] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein R 7 is hydrogen.

[0191] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein R 5 is hydrogen.

[0192] A particular embodiment of the present invention relates to a compound of formula (I) as described herein or a pharmaceutically acceptable salt thereof, wherein the compound is a compound of formula (I')

[0193]

[0194] or a pharmaceutically acceptable salt thereof, wherein R 1, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X 1 , X 2 , X 3 , X 4 and X 5 as defined above.

[0195] A particular embodiment of the invention relates to a compound of formula (I) or a pharmaceutically acceptable salt thereof as described herein, wherein the compound is a compound of formula (I")

[0196]

[0197] or a pharmaceutically acceptable salt thereof, wherein R 1 , X 1 and X 4 as defined above.

[0198] A particular embodiment of the invention relates to a compound of formula (I) or formula (I') or a pharmaceutically acceptable salt thereof as described herein, wherein

[0199] X 1 is CH or N,

[0200] X 2 is CH,

[0201] X 3 is CH,

[0202] X 4 is O or NH,

[0203] X 5 is CH,

[0204] R 1 is indazolyl, indolyl, pyridyl, triazolopyridyl, phenyl or imidazopyridyl, wherein indazolyl, indolyl, pyridyl, triazolopyridyl, phenyl and imidazopyridyl are optionally substituted by one or more R 1a substituents,

[0205] R 1a is methyl, cyano, -CONH2, isopropyl, -CONH(Me),

[0206] R 2 is hydrogen,

[0207] R 3 is hydrogen,

[0208] R 4 is hydrogen,

[0209] R 5 is hydrogen,

[0210] R 6 is -SF5,

[0211] R 7 is hydrogen.

[0212] A particular embodiment of the present invention relates to a compound of formula (I) or formula (I') as described herein or a pharmaceutically acceptable salt thereof, wherein

[0213] X 1 is CH or N,

[0214] X 2 is CH,

[0215] X 3 is CH,

[0216] X 4 is O or NH,

[0217] X 5 is CH,

[0218] R 1 is methyl - indazolyl, cyano - indolyl, carbamoyl - pyridyl, methyl - imidazopyridyl, methyl - triazolopyridyl, isopropyl - triazolopyridyl, cyano - indazolyl, (methylcarbamoyl)phenyl, imidazopyridyl, cyanoimidazopyridyl,

[0219] R 2 is hydrogen,

[0220] R 3 is hydrogen,

[0221] R 4 is hydrogen,

[0222] R 5 is hydrogen,

[0223] R 6 is -SF5,

[0224] R 7 is hydrogen.

[0225] In addition, it should be understood that with respect to the specific X 1 、X 2 、X 3 、X 4 、R 1 、R 1a 、R 1b 、R 1c 、R 2 、R 3 、R4 , R 5 , R 6 and R 7 Each embodiment of and R can be combined with another X as disclosed herein 1 , X 2 , X 3 , X 4 , R 1 , R 1a , R 1b , R 1c , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 and any other embodiment of R.

[0226] A particular embodiment of the present invention relates to a compound of formula (I) or a pharmaceutically acceptable salt thereof as described herein, the compound being selected from:

[0227] 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0228] 1-[4-(3-Methyl-2H-indazol-5-yl)benzenesulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0229] 5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indole-3-carbonitrile

[0230] 5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indazole-3-carbonitrile

[0231] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[cis-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline

[0232] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile

[0233] 5-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile

[0234] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one

[0235] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0236] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0237] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0238] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0239] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one

[0240] N,N-dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide

[0241] N-methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide

[0242] 6-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[0243] 4-(pentafluoro-λ 6-Thiol)-N-[cis-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0244] N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[0245] N,N-Dimethyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0246] N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[0247] N-Methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0248] 4'-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[0249] 1-(4-{imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -Thiol)phenyl]piperidin-4-amine

[0250] 6-{4-[(4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0251] 6-{4-[(4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide

[0252] 1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -Thiol)phenyl]piperidin-4-amine

[0253] N-[4-(pentafluoro-λ 6-thiol)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[0254] N-[4-(pentafluoro-λ 6 -thiol)phenyl]-1-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[0255] 1-{4-[3-(methoxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -thiol)phenyl]piperidin-4-amine

[0256] 1-(4-{3-cyclopentyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -thiol)phenyl]piperidin-4-amine

[0257] 6-{4-[(4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[0258] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[0259] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide

[0260] 4-(pentafluoro-λ 6 -thiol)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0261] 4-(pentafluoro-λ 6 -thiol)-N-[trans-4-(4-{[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0262] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carboxamide

[0263] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carbonitrile

[0264] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide

[0265] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0266] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl}benzenesulfonyl)cyclohexyl]aniline

[0267] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carbonitrile

[0268] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methylimidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0269] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0270] N,N-dimethyl-6-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[0271] N,N-dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[0272] N-methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[0273] N-Methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0274] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[0275] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0276] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0277] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2-dihydropyridin-2-one

[0278] 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one

[0279] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one

[0280] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-3H,4H-pyrrolo[2,1-f][1,2,4]triazin-4-one

[0281] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridin-2-ol

[0282] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{[4'-(dimethylphosphoryl)-[1,1'-biphenyl]-4-yl]sulfonyl}cyclohexyl]aniline

[0283] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one

[0284] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one

[0285] 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[0286] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[0287] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridazine-3-carboxamide

[0288] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0289] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[8-methyl-3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0290] 5'-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2'-one

[0291] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[0292] 1-(2-fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl]benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0293] 1-(3-Fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0294] 1-[(6-{3-methylimidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0295] 1-[(5-{3-methylimidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0296] 6-{2-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0297] 1-(3-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0298] 6-{3-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0299] 1-(2-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0300] 1-[(5-{imidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0301] 6-{5-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-2-yl}imidazo[1,2-a]pyridine-3-carbonitrile

[0302] 1-[(6-{imidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0303] 6-{6-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-3-yl}imidazo[1,2-a]pyridine-3-carbonitrile

[0304] 1-(2-Chloro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0305] 6-{3-Chloro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0306] 6-{4-[(4-{[3-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0307] 1-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[3-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0308] 4-(4-{[(3S,4S)-3-Fluoro-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl]sulfonyl}phenyl)pyridine-2-carboxamide

[0309] N-[3-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[0310] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1H-indole-3-carbonitrile

[0311] [4-(3-Methyl-1H-indazol-5-yl)phenyl][trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0312] (4-{imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6-Sulfone

[0313] (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[cis-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0314] (4-{3-Methylimidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0315] 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[0316] 4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide

[0317] N,N-Dimethyl-4'-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}-[1,1'-biphenyl]-4-carboxamide

[0318] (4-{Imidazo[1,2-a]pyridin-7-yl}phenyl)[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0319] [trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](4-{[1,2,4]triazolo[1,5-a]pyridin-7-yl}phenyl)(imino)-λ 6 -sulfone

[0320] N-Methyl-4'-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}-[1,1'-biphenyl]-4-carboxamide

[0321] 4'-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}-[1,1'-biphenyl]-4-carboxamide

[0322] N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide

[0323] N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide

[0324] 4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide

[0325] N,N-Dimethyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[0326] N-Methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[0327] {4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0328] (4-{2-Methylimidazo[1,2-a]pyrazin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0329] (4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0330] (4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0331] N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-3-carboxamide

[0332] N-Methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-3-carboxamide

[0333] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide

[0334] N,N-Dimethyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide

[0335] N-Methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide

[0336] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-3-carboxamide

[0337] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-2,3-dihydro-1H-isoindol-1-one

[0338] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[0339] 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[0340] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-2,3-dihydro-1H-isoindol-1-one

[0341] 5-(4-{[trans-4-{[4-(pentafluoro-λ6 {4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ

[0342] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-2,3-dihydro-1H-indol-2-one

[0343] {4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0344] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[0345] 5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinyl]phenyl}-1H-indole-3-carbonitrile

[0346] N-methyl-5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinyl]phenyl}pyridine-2-carboxamide

[0347] 4'-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinyl]-[1,1'-biphenyl]-4-carbonitrile

[0348] 5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinyl]phenyl}-2,3-dihydro-1H-indol-2-one

[0349] (4-{imidazo[1,2-a]pyridin-6-yl}phenyl)(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)(imino)-λ 6 -sulfone

[0350] 4-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinyl]phenyl}pyridine-2-carboxamide

[0351] (+)-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1H-indole-3-carbonitrile

[0352] (-)-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1H-indole-3-carbonitrile

[0353] (+)-(4-{imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0354] (-)-(4-{imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0355] (+)-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[0356] (-)-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[0357] 1-(4-{2-methoxy-7-azaspiro[3.5]nonan-7-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine,

[0358] 8-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1,3,8-triazaspiro[4.5]decane-2,4-dione,

[0359] 8-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2,8-diazaspiro[4.5]decan-1-one,

[0360] 8-{4-[(4-{[4-(pentafluoro-λ 6-Thiol)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-3-oxa-1,8-diazaspiro[4.5]decan-2-one,

[0361] 1-(4-{2-Oxa-7-azaspiro[3.5]nonan-7-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -Thiol)phenyl]piperidin-4-amine,

[0362] 1-(4-{8-Oxa-3-azabicyclo[3.2.1]octan-3-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -Thiol)phenyl]piperidin-4-amine,

[0363] 4-Fluoro-N-methyl-4'-[(4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}piperidin-1-yl)sulfonyl]-[1,1'-biphenyl]-3-carboxamide,

[0364] 3-Fluoro-N-methyl-4'-[(4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}piperidin-1-yl)sulfonyl]-[1,1'-biphenyl]-4-carboxamide,

[0365] N-[4-(pentafluoro-λ 6 -Thiol)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}piperidin-4-amine,

[0366] N-(propan-2-yl)-4'-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide,

[0367] 4-(pentafluoro-λ 6 -Thiol)-N-[trans-4-(4-{3-methyl-1H-pyrazolo[3,4-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline,

[0368] N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridin-3-amine,

[0369] N-Cyclopropyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide,

[0370] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{5H-pyrrolo[3,2-d]pyrimidin-2-yl}benzenesulfonyl)cyclohexyl]aniline,

[0371] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{1H-pyrrolo[2,3-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline,

[0372] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{1H-pyrazolo[3,4-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline,

[0373] 4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)thiophene-2-carboxamide,

[0374] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{8-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline,

[0375] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline,

[0376] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[8-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline,

[0377] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{8-fluoroimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline,

[0378] 2-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-4H,5H,6H,7H-thieno[3,2-c]pyridin-4-one,

[0379] 7-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H-pyrrolo[1,2-a]pyrazin-1-one,

[0380] 8-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H,3H,4H,5H-pyrrolo[1,2-a][1,4]diazepin -1-one,

[0381] 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one,

[0382] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-8-carboxamide,

[0383] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)furan-2-carboxamide,

[0384] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{8-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline,

[0385] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-8-carbonitrile,

[0386] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-[(2R)-pyrrolidin-2-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline,

[0387] {4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone,

[0388] (+)-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone,

[0389] (-)-{4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone,

[0390] N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-(4-{3-[(3R)-Pyrrolidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-amine,

[0391] N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-(4-{3-[(3S)-Pyrrolidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-amine,

[0392] 1-{4-[3-(Azetidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine,

[0393] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(Azetidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline;

[0394] {4-[3-(Difluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone;

[0395] (4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyrazin-6-yl}phenyl)[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone;

[0396] {4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[5-(Pentafluoro-λ 6 -sulfanyl)pyridin-2-yl]amino}cyclohexyl](imino)-λ 6 -sulfone;

[0397] 5-(pentafluoro-λ 6 -sulfanyl)-N-(1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-yl)pyridin-2-amine;

[0398] N-[1-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-yl]-5-(pentafluoro-λ 6 -sulfanyl)pyridin-2-amine;

[0399] N-[1-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-yl]-5-(pentafluoro-λ 6 -sulfanyl)pyridin-2-amine;

[0400] 4-{4-[(4-{[5-(pentafluoro-λ 6 -sulfanyl)pyridin-2-yl]amino}piperidin-1-yl)sulfonyl]phenyl}pyridine-2-carboxamide;

[0401] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(difluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline;

[0402] 4-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}pyridine-2-carboxamide;

[0403] 5-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]pyridin-2-amine;

[0404] 5-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]pyridin-2-amine;

[0405] 5-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]pyridin-2-amine;

[0406] or

[0407] 5-(pentafluoro-λ 6-Thiol)-N-[trans-4-{4-[8-Methyl-3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]pyridin-2-amine.

[0408] A particular embodiment of the invention relates to a compound of formula (I) as described herein or a pharmaceutically acceptable salt thereof, the compound being selected from:

[0409] 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -Thiol)phenyl]piperidin-4-amine

[0410] 1-[4-(3-Methyl-2H-indazol-5-yl)benzenesulfonyl]-N-[4-(pentafluoro-λ 6 -Thiol)phenyl]piperidin-4-amine

[0411] 5-{4-[(4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indole-3-carbonitrile

[0412] 5-{4-[(4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indazole-3-carbonitrile

[0413] 4-(pentafluoro-λ 6 -Thiol)-N-[cis-4-[4-(3-Methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline 4-(pentafluoro-λ 6 -Thiol)-N-[trans-4-[4-(3-Methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline

[0414] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile

[0415] 5-(4-{[cis-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile

[0416] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one

[0417] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6-thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0418] 4-(Pentafluoro-λ 6 -thio)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0419] 4-(Pentafluoro-λ 6 -thio)-N-[trans-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0420] 4-(Pentafluoro-λ 6 -thio)-N-[trans-4-(4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0421] 5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one

[0422] N,N-dimethyl-4'-{[trans-4-{[4-(Pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide

[0423] N-methyl-4'-{[trans-4-{[4-(Pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide

[0424] 6-(4-{[cis-4-{[4-(Pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[0425] 4-(Pentafluoro-λ 6 -thio)-N-[cis-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0426] N,N-dimethyl-4'-{[trans-4-{[4-(Pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[0427] N,N-dimethyl-5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0428] N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[0429] N-Methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0430] 4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[0431] 1-(4-{imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0432] 6-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0433] 6-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide

[0434] 1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0435] N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[0436] N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[0437] 1-{4-[3-(methoxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0438] 1-(4-{3-Cyclopentyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0439] 6-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[0440] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[0441] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide

[0442] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0443] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0444] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carboxamide

[0445] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carbonitrile

[0446] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide

[0447] 4-(pentafluoro-λ 6-Thiol)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0448] 4-(Pentafluoro-λ 6 -Thiol)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl}benzenesulfonyl)cyclohexyl]aniline

[0449] 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carbonitrile

[0450] 4-(Pentafluoro-λ 6 -Thiol)-N-[trans-4-(4-{2-methylimidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0451] 4-(Pentafluoro-λ 6 -Thiol)-N-[trans-4-(4-{imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0452] N,N-Dimethyl-6-(4-{[cis-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[0453] N,N-Dimethyl-6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[0454] N-Methyl-6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[0455] N-Methyl-4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0456] 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[0457] 4-(Pentafluoro-λ 6-Thiol)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0458] 4-(Pentafluoro-λ 6 -Thiol)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0459] 4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2-dihydropyridin-2-one

[0460] 7-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one

[0461] 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one

[0462] 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-3H,4H-pyrrolo[2,1-f][1,2,4]triazin-4-one

[0463] 5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridin-2-ol

[0464] 4-(Pentafluoro-λ 6 -Thiol)-N-[trans-4-{[4'-(dimethylphosphoryl)-[1,1'-biphenyl]-4-yl]sulfonyl}cyclohexyl]aniline

[0465] 5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one

[0466] 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one

[0467] 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[0468] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[0469] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridazine-3-carboxamide

[0470] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0471] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[8-methyl-3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0472] 5'-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1',2'-dihydrospiro[cyclopropane-1,3'-indol]-2'-one

[0473] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[0474] 1-(2-fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0475] 1-(3-fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0476] 1-[(6-{3-methylimidazo[1,2-a]pyridin-6-yl]pyridin-3-yl]sulfonyl}-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0477] 1-[(5-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0478] 6-{2-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0479] 1-(3-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0480] 6-{3-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0481] 1-(2-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0482] 1-[(5-{imidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0483] 6-{5-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-2-yl}imidazo[1,2-a]pyridine-3-carbonitrile

[0484] 1-[(6-{imidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0485] 6-{6-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-3-yl}imidazo[1,2-a]pyridine-3-carbonitrile

[0486] 1-(2-Chloro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0487] 6-{3-chloro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0488] 6-{4-[(4-{[3-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0489] 1-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[3-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0490] 4-(4-{[(3S,4S)-3-fluoro-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl]sulfonyl}phenyl)pyridine-2-carboxamide

[0491] N-[3-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[0492] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-1H-indole-3-carbonitrile

[0493] [4-(3-methyl-1H-indazol-5-yl)phenyl][trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0494] (4-{imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0495] (4-{imidazo[1,2-a]pyridin-6-yl}phenyl)[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0496] (4-{3-methylimidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ6 -thiol)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0497] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[0498] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[0499] N,N-dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide

[0500] (4-{imidazo[1,2-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0501] [trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl](4-{[1,2,4]triazolo[1,5-a]pyridin-7-yl}phenyl)(imino)-λ 6 -sulfone

[0502] N-methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide

[0503] 4'-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide

[0504] N,N-dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide

[0505] N-methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide

[0506] 4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}-[1,1'-biphenyl]-3-carboxamide

[0507] N,N-dimethyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)pyridine-2-carboxamide

[0508] N-methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)pyridine-2-carboxamide

[0509] {4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0510] (4-{2-methylimidazo[1,2-a]pyrazin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0511] (4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0512] (4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0513] N,N-dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)pyridine-3-carboxamide

[0514] N-methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)pyridine-3-carboxamide

[0515] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide

[0516] N,N-dimethyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide

[0517] N-methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide

[0518] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-3-carboxamide

[0519] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-2,3-dihydro-1H-isoindol-1-one

[0520] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[0521] 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[0522] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-2,3-dihydro-1H-isoindol-1-one

[0523] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-2,3-dihydro-1H-indole-2-one

[0524] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-2,3-dihydro-1H-indole-2-one

[0525] {4-[3-(Propan-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0526] 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[0527] 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylamino]phenyl}-1H-indole-3-carbonitrile

[0528] N-Methyl-5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylamino]phenyl}pyridine-2-carboxamide

[0529] 4'-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylamino]-[1,1'-biphenyl]-4-carbonitrile

[0530] 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylamino]phenyl}-2,3-dihydro-1H-indol-2-one

[0531] (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)(imino)-λ 6 -sulfone

[0532] 4-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylamino]phenyl}pyridine-2-carboxamide

[0533] (+)-5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-1H-indole-3-carbonitrile

[0534] (-)-5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-1H-indole-3-carbonitrile

[0535] (+)-(4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0536] (-)-(4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0537] (+)-4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide

[0538] (-)-4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide

[0539] 1-(4-{2-Methoxy-7-azaspiro[3.5]nonan-7-yl}benzenesulfonyl)-N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine,

[0540] 8-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1,3,8-triazaspiro[4.5]decane-2,4-dione,

[0541] 8-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2,8-diazaspiro[4.5]decane-1-one,

[0542] 8-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-3-oxa-1,8-diazaspiro[4.5]decane-2-one,

[0543] 1-(4-{2-Oxa-7-azaspiro[3.5]nonan-7-yl}benzenesulfonyl)-N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine,

[0544] 1-(4-{8-Oxa-3-azabicyclo[3.2.1]octan-3-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine,

[0545] 4-Fluoro-N-methyl-4'-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]-[1,1'-biphenyl]-3-carboxamide,

[0546] 3-Fluoro-N-methyl-4'-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]-[1,1'-biphenyl]-4-carboxamide,

[0547] N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}piperidin-4-amine,

[0548] N-(propan-2-yl)-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide,

[0549] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-1H-pyrazolo[3,4-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline,

[0550] N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridin-3-amine,

[0551] N-Cyclopropyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide,

[0552] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{5H-pyrrolo[3,2-d]pyrimidin-2-yl}benzenesulfonyl)cyclohexyl]aniline,

[0553] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{1H-pyrrolo[2,3-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline,

[0554] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{1H-pyrazolo[3,4-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline,

[0555] 4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)thiophene-2-carboxamide,

[0556] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{8-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline,

[0557] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline,

[0558] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[8-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline,

[0559] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{8-fluoroimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline,

[0560] 2-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-4H,5H,6H,7H-thieno[3,2-c]pyridin-4-one,

[0561] 7-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H-pyrrolo[1,2-a]pyrazin-1-one,

[0562] 8-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H,3H,4H,5H-pyrrolo[1,2-a][1,4]diazepin -1-one,

[0563] 7-(4-{[trans-4-{[4-(Pentafluoro-λ 6-thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one,

[0564] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-8-carboxamide,

[0565] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)furan-2-carboxamide,

[0566] 4-(pentafluoro-λ 6 -thio)-N-[trans-4-(4-{8-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline,

[0567] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-8-carbonitrile,

[0568] 4-(pentafluoro-λ 6 -thio)-N-[trans-4-(4-{3-[(2R)-pyrrolidin-2-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline,

[0569] {4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone,

[0570] (+)-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone,

[0571] (-)-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone,

[0572] N-[4-(pentafluoro-λ6 -sulfanyl)phenyl]-1-(4-{3-[(3R)-pyrrolidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-amine,

[0573] N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-(4-{3-[(3S)-pyrrolidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-amine,

[0574] 1-{4-[3-(azetidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine, or

[0575] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(azetidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline.

[0576] A particular embodiment of the present invention relates to a compound of formula (I) as described herein or a pharmaceutically acceptable salt thereof, which compound is selected from:

[0577] 1-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0578] 1-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0579] 5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indole-3-carbonitrile

[0580] 5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indazole-3-carbonitrile

[0581] 4-(pentafluoro-λ 6 -sulfanyl)-N-[cis-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline

[0582] 4-(pentafluoro-λ 6-Thiol)-N-[trans-4-[4-(3-Methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline

[0583] 5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile

[0584] 5-(4-{[cis-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile

[0585] 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one

[0586] 4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0587] 4-(Pentafluoro-λ 6 -Thiol)-N-[trans-4-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0588] 4-(Pentafluoro-λ 6 -Thiol)-N-[trans-4-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0589] 4-(Pentafluoro-λ 6 -Thiol)-N-[trans-4-(4-{3-Methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0590] 5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one

[0591] N,N-Dimethyl-4'-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide

[0592] N-Methyl-4'-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide

[0593] 6-(4-{[Cis-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[0594] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[cis-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0595] N,N-Dimethyl-4'-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[0596] N,N-Dimethyl-5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0597] N-Methyl-4'-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[0598] N-Methyl-5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0599] 4'-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[0600] 1-(4-{imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)-N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0601] 6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0602] 6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide

[0603] 1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0604] N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[0605] N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[0606] 1-{4-[3-(methoxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0607] 1-(4-{3-Cyclopentyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0608] 6-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[0609] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[0610] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide

[0611] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0612] 4-(pentafluoro-λ 6-Thiol)-N-[trans-4-(4-{[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0613] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carboxamide

[0614] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carbonitrile

[0615] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide

[0616] 4-(pentafluoro-λ 6 -Thiol)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0617] 4-(pentafluoro-λ 6 -Thiol)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl}benzenesulfonyl)cyclohexyl]aniline

[0618] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carbonitrile

[0619] 4-(pentafluoro-λ 6 -Thiol)-N-[trans-4-(4-{2-methylimidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0620] 4-(pentafluoro-λ 6 -Thiol)-N-[trans-4-(4-{imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0621] N,N-Dimethyl-6-(4-{[cis-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[0622] N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[0623] N-Methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[0624] N-Methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0625] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[0626] 4-(pentafluoro-λ 6 -thio)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0627] 4-(pentafluoro-λ 6 -thio)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0628] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2-dihydropyridin-2-one

[0629] 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one

[0630] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one

[0631] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-3H,4H-pyrrolo[2,1-f][1,2,4]triazin-4-one

[0632] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6-thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridin-2-ol

[0633] 4-(Pentafluoro-λ 6 -thio)-N-[trans-4-{[4'-(dimethylphosphoryl)-[1,1'-biphenyl]-4-yl]sulfonyl}cyclohexyl]aniline

[0634] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one

[0635] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one

[0636] 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[0637] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[0638] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridazine-3-carboxamide

[0639] 4-(Pentafluoro-λ 6 -thio)-N-[trans-4-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0640] 4-(Pentafluoro-λ 6 -thio)-N-[trans-4-{4-[8-methyl-3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0641] 5'-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2'-one

[0642] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6-thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[0643] 1-(2-Fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine

[0644] 1-(3-Fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine

[0645] 1-[(6-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine

[0646] 1-[(5-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine

[0647] 6-{2-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0648] 1-(3-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine

[0649] 6-{3-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0650] 1-(2-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine

[0651] 1-[(5-{imidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine

[0652] 6-{5-[(4-{[4-(pentafluoro-λ 6-thio)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-2-yl}imidazo[1,2-a]pyridine-3-carbonitrile

[0653] 1-[(6-{Imidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine

[0654] 6-{6-[(4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-3-yl}imidazo[1,2-a]pyridine-3-carbonitrile

[0655] 1-(2-chloro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine

[0656] 6-{3-chloro-4-[(4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0657] 6-{4-[(4-{[3-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0658] 1-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[3-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine

[0659] 4-(4-{[(3S,4S)-3-fluoro-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl]sulfonyl}phenyl)pyridine-2-carboxamide

[0660] N-[3-(pentafluoro-λ 6 -thio)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[0661] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1H-indole-3-carbonitrile

[0662] [4-(3-methyl-1H-indazol-5-yl)phenyl][trans-4-{[4-(pentafluoro-λ6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0663] (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0664] (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0665] (4-{3-Methylimidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0666] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[0667] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)pyridine-2-carboxamide

[0668] N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}-[1,1'-biphenyl]-4-carboxamide

[0669] (4-{Imidazo[1,2-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0670] [trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](4-{[1,2,4]triazolo[1,5-a]pyridin-7-yl}phenyl)(imino)-λ 6 -sulfone

[0671] N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6-thio)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide

[0672] 4'-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide

[0673] N,N-dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide

[0674] N-methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide

[0675] 4'-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide

[0676] N,N-dimethyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[0677] N-methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[0678] {4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0679] (4-{2-methylimidazo[1,2-a]pyrazin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0680] (4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0681] (4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0682] N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)pyridine-3-carboxamide

[0683] N-Methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)pyridine-3-carboxamide

[0684] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)pyridine-2-carboxamide

[0685] N,N-Dimethyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)pyridine-2-carboxamide

[0686] N-Methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)pyridine-2-carboxamide

[0687] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)pyridine-3-carboxamide

[0688] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one

[0689] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[0690] 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[0691] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-2,3-dihydro-1H-isoindol-1-one

[0692] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-2,3-dihydro-1H-indol-2-one

[0693] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-2,3-dihydro-1H-indol-2-one

[0694] {4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0695] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[0696] 5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylamino]phenyl}-1H-indole-3-carbonitrile

[0697] N-methyl-5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylamino]phenyl}pyridine-2-carboxamide

[0698] 4'-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinyl]-[1,1'-biphenyl]-4-carbonitrile

[0699] 5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylamino]phenyl}-2,3-dihydro-1H-indol-2-one

[0700] (4-{imidazo[1,2-a]pyridin-6-yl}phenyl)(4-{[4-(pentafluoro-λ 6}-thio)phenyl]amino}piperidin-1-yl)(imino)-λ 6 -sulfone

[0701] 4-{4-[(4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)sulfinyl]phenyl}pyridine-2-carboxamide

[0702] (+)-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1H-indole-3-carbonitrile

[0703] (-)-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1H-indole-3-carbonitrile

[0704] (+)-(4-{imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0705] (-)-(4-{imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0706] (+)-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[0707] (-)-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide.

[0708] A more specific embodiment of the present invention relates to a compound of formula (I) as described herein or a pharmaceutically acceptable salt thereof, which compound is selected from:

[0709] 1-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine

[0710] {4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0711] N-Methyl-4'-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide

[0712] 4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[0713] 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[0714] 5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carbonitrile

[0715] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0716] (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0717] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0718] 4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0719] 5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile

[0720] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline

[0721] 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indazole-3-carbonitrile

[0722] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0723] (4-{3-Methylimidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0724] 6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0725] 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[0726] A more specific embodiment of the invention relates to a compound of formula (I) as described herein or a pharmaceutically acceptable salt thereof, the compound being selected from:

[0727] 1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0728] {4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0729] N-Methyl-4'-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide

[0730] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[0731] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[0732] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carbonitrile

[0733] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0734] (4-{imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0735] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0736] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0737] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile

[0738] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline

[0739] 5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indazole-3-carbonitrile

[0740] 4-(pentafluoro-λ 6-Thiol)-N-[trans-4-(4-{3-Methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0741] (4-{3-Methylimidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl](imino)-λ 6 -Sulfone

[0742] 6-{4-[(4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[0743] 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -Thiol)phenyl]piperidin-4-amine;

[0744] 5-(Pentafluoro-λ 6 -Thiol)-N-(1-{4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-yl)pyridin-2-amine;

[0745] N-[1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-yl]-5-(pentafluoro-λ 6 -Thiol)pyridin-2-amine;

[0746] Or

[0747] N-[1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-yl]-5-(pentafluoro-λ 6 -Thiol)pyridin-2-amine.

[0748] A more specific embodiment of the invention relates to a compound of formula (I) as described herein or a pharmaceutically acceptable salt thereof, the compound being selected from:

[0749] 4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[0750] 4-(Pentafluoro-λ 6 -Thiol)-N-[trans-4-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[0751] 6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide

[0752] 1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[0753] 6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[0754] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0755] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[0756] (+)-4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[0757] (+)-{4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[0758] (-)-{4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[0759] Another object of the present invention is all forms of optically pure enantiomers, racemates or mixtures of diastereomers of the compounds of formula (I) or formula (I').

[0760] Manufacturing method

[0761] A method for manufacturing a compound of formula (I) or a pharmaceutically acceptable salt thereof as described herein is also an object of the present invention.

[0762] The present invention provides a method for preparing a compound or a pharmaceutically acceptable salt thereof as described herein, wherein X 1 is N and X 4 is O, and the method comprises:

[0763] reacting a compound of formula (VI), wherein R 6 , R 7 and X 5 are as defined above,

[0764]

[0765] with a compound of formula (VII), wherein R 5 and R 4 are as defined above,

[0766]

[0767] to form a compound of formula (VIII), wherein R 4 , R 5 , X 5 , R 6 , R 7 are as defined above,

[0768]

[0769] reacting the compound of formula (VIII) with an acid to form a compound of formula (IX), wherein R 4 , R 5 , X 5 , R 6 , R 7 are as defined above,

[0770]

[0771] reacting the compound of formula (IX) with a compound of formula (XI), wherein X 2 , X 3 , R 2 and R 3 are as defined above,

[0772]

[0773] to form a compound of formula (III), wherein R 2 , R 3 , R 4 , R 6, R 7 , R 5 , X 2 , X 5 and X 3 as defined above,

[0774]

[0775] reacting the compound of formula (III) with a compound of formula (X), wherein R 1 as defined above, and R 9 and R 10 are independently selected from C 1-6 alkyl, or R 9 and R 10 together with the oxygen atom to which they are attached form a 3- to 14-membered heterocyclic group, which heterocyclic group is optionally substituted by one or more C 1-6 alkyl, especially optionally substituted by four C 1-6 alkyl,

[0776]

[0777] to form a compound of formula (I).

[0778] The present invention provides a method for preparing a compound as described herein or a pharmaceutically acceptable salt thereof, wherein X 1 is CH and X 4 is O, the method comprising:

[0779] reacting a compound of formula (XII), wherein R 5 and R 4 are as defined above,

[0780]

[0781] with CH3SO2Cl to form a compound of formula (XIII), wherein R 5 and R 4 are as defined above,

[0782]

[0783] reacting the said compound of formula (XIII) with a compound of formula (XIV), wherein R 3 , R 2 , X 2 and X 3 are as defined above,

[0784]

[0785] to form a compound of formula (XV), wherein R 3 , R2 , R 5 , R 4 , X 2 and X 3 as defined above,

[0786]

[0787] react the compound of formula (XV) with an oxidizing agent to form a compound of formula (XVI), wherein R 3 , R 2 , R 5 , R 4 , X 2 and X 3 as defined above,

[0788]

[0789] react the compound of formula (XVI) with an acid to form a compound of formula (XVII), wherein R 3 , R 2 , R 5 , R 4 , X 2 and X 3 as defined above,

[0790]

[0791] react the compound of formula (XVII) with a compound of formula (VI), wherein R 6 , R 7 and X 5 as defined above,

[0792]

[0793] to form a compound of formula (XVIII), wherein R 2 , R 3 , R 4 , R 6 , R 7 , R 5 , X 2 , X 5 and X 3 as defined above,

[0794]

[0795] react the compound of formula (XVIII) with a compound of formula (X), wherein R 1 as defined above, and R 9 and R 10 are independently selected from C 1-6alkyl, or R 9 and R 10 together with the oxygen atom to which they are attached form a 3- to 14-membered heterocyclic group, which heterocyclic group is optionally substituted by one or more C 1-6 alkyl groups, particularly optionally substituted by four C 1-6 alkyl groups,

[0796]

[0797] react to form a compound of formula (I).

[0798] The present invention provides a method for preparing a compound or a pharmaceutically acceptable salt thereof as described herein, wherein X 1 is CH and X 4 is NH, the method comprising:

[0799] reacting a compound of formula (XV), wherein R 3 、R 2 、R 5 、R 4 、X 2 and X 3 are as defined above,

[0800]

[0801] with an acid to form a compound of formula (XX), wherein R 3 、R 2 、R 5 、R 4 、X 2 and X 3 are as defined above,

[0802]

[0803] reacting said compound of formula (XX) with a compound of formula (VI), wherein R 6 、R 7 and X 5 are as defined above,

[0804]

[0805] to form a compound of formula (XXI), wherein R 2 、R 3 、R 4 、R 6 、R 7 、R 5 、X 2 、X 5 and X 3 are as defined above,

[0806]

[0807] React the compound of formula (XXI) with ammonium carbamate and (diacetoxyiodo)benzene to form a compound of formula (XXII), wherein R 2 、R 3 、R 4 、R 6 、R 7 、R 5 、X 2 、X 5 and X 3 are as defined above,

[0808]

[0809] React the compound of formula (XXII) with a compound of formula (X), wherein R 1 is as defined above, and R 9 and R 10 are independently selected from C 1-6 alkyl, or R 9 and R 10 together with the oxygen atom to which they are attached form a 3- to 14-membered heterocyclic group, which heterocyclic group is optionally substituted by one or more C 1-6 alkyl, especially optionally substituted by four C 1-6 alkyl,

[0810]

[0811] to form a compound of formula (I).

[0812] The present invention provides a method for preparing a compound as described herein or a pharmaceutically acceptable salt thereof, wherein X 1 is N and X 4 is NH, the method comprising:

[0813] React a compound of formula (IX), wherein R 4 、R 5 、X 5 、R 6 、R 7 are as defined above,

[0814]

[0815] with a compound of formula (XIV), wherein R 2 and R 3 are as defined above,

[0816]

[0817] to form a compound of formula (XXIV), wherein R2 , R 3 , R 4 , R 6 , R 7 , R 5 , X 2 , X 5 and X 3 as defined above,

[0818]

[0819] React the compound of formula (XXIV) with ammonium carbamate and (diacetoxyiodo)benzene to form the compound of formula (XXV), wherein R 2 , R 3 , R 4 , R 6 , R 7 , R 5 , X 2 , X 5 and X 3 as defined above,

[0820]

[0821] React the compound of formula (XXV) with di-tert-butyl dicarbonate and NaH to form the compound of formula (XXVI), wherein R 2 , R 3 , R 4 , R 6 , R 7 , R 5 , X 2 , X 5 and X 3 as defined above,

[0822]

[0823] React the compound of formula (XXVI) with the compound of formula (X), wherein R 1 as defined above, and R 9 and R 10 are independently selected from C 1-6 alkyl, or R 9 and R 10 together with the oxygen atom to which they are attached form a 3- to 14-membered heterocyclic group, which heterocyclic group is optionally substituted by one or more C 1-6 alkyl, especially optionally substituted by four C 1-6 alkyl,

[0824]

[0825] A reaction is carried out to form a compound of formula (XXVII), wherein R 1 、R 2 、R 3 、R 4 、R 6 、R 7 、R 5 、X 2 、X 5 and X 3 are as defined above,

[0826]

[0827] The compound of formula (XXVII) is reacted with an acid to form a compound of formula (I).

[0828] General preparation method

[0829] The compounds described herein (including the compounds of general formula (I)) can be readily prepared using readily available starting materials, reagents and conventional synthetic procedures according to the following reaction schemes and examples or modifications thereof. Many of the reactions in this reaction can also be carried out under microwave conditions or using conventional heating or by other techniques (such as solid-phase reagents / scavengers or flow chemistry). In these reactions, variants known to those skilled in the art but not mentioned in more detail per se can also be utilized. For example, when specific acids, bases, reagents, coupling agents, solvents, etc. are mentioned, it should be understood that other suitable acids, bases, reagents, coupling agents, solvents, etc. can also be used and these are all included within the scope of the present invention. In addition, in view of the following reaction schemes and examples, other methods for preparing the compounds of the present invention will be apparent to those of ordinary skill in the art. In cases where the synthetic intermediates and final products contain potentially reactive functional groups (such as amino, hydroxyl, thiol and carboxylic acid groups, which may interfere with the desired reactions), it may be advantageous to use protected forms of the intermediates. Methods for selecting, introducing and subsequently removing protecting groups are well known to those skilled in the art. The compounds obtained by using the general reaction sequence may not be of sufficient purity. The compounds are purified by using any of the methods for purifying organic compounds, such as crystallization or silica gel, alumina or C18 column chromatography, which use different solvents in appropriate ratios. All possible stereoisomers are contemplated within the scope of the present invention. In the following discussion, unless otherwise indicated, the variables have the meanings indicated above. All final compounds have been characterized using, for example, LC-MS, NMR and / or specific rotation.

[0830] The abbreviations used in these experimental details are listed below, and additional abbreviations should be considered known to those skilled in the art of synthetic chemistry.

[0831] The abbreviations used in this text are as follows: r.t.: room temperature; DMF: dimethylformamide; DiPEA: diisopropylethylamine; DMAP: 4-(dimethylamino)pyridine; TFA: trifluoroacetic acid; THF: tetrahydrofuran; DMSO: dimethyl sulfoxide; EtOH: ethanol; TLC: thin layer chromatography; mCPBA: 3-chloroperoxybenzoic acid; MeOH: methanol; HOAc: acetic acid; NMP: N-methylpyrrolidone, KOAc: potassium acetate; N: normal; Josiphos SL J009-1: cyclopentane; di-tert-butyl-[(1R)-1-(2-dicyclohexylphosphanylcyclopentyl)ethyl]phosphine; iron.

[0832] If both a chemical structure and a chemical name are used to refer to a compound and there is an ambiguity between the structure and the name, the structure shall prevail. General process

[0833] Scheme 1:

[0834]

[0835] Conditions: i) aminophenylsulfur pentafluoride (VI) , 2-methylpyridine borane complex, MeOH, HOAc, 0 °C; ii) bis(pinacolato)diboron, KOAc, Pd(dppf)Cl2, DMF, 75 °C iii) R 1 -halide (V) , 2N K2CO3, toluene / ethanol, Pd(PPh3)4, 90 °C; iv) R 1 -boronic acid / boronate (X) , Pd(PPh3)4, 2N K2CO3, toluene / ethanol, 90 °C; v) aminophenylsulfur pentafluoride (VI) , 2-methylpyridine borane complex, MeOH, HOAc, 0 °C; vi) 5N HCl in 2-propanol, CH2Cl2, room temperature; vii) 4-bromobenzenesulfonyl chloride (XI) , Et3N, CH2Cl2, room temperature.

[0836] As depicted in Scheme 1, the derivatives of the present invention having formula (I) (when X1 = N and X4 = O) can be prepared by methods known in the art of organic chemistry. The compounds of the present invention can be obtained, for example, by coupling a commercially available ketone derivative of formula (II) (wherein X2, X3, R2, R3, R4 and R5 have the meanings as previously described) and an aniline derivative of formula (VI) (wherein X5, R6 and R7 have the meanings as previously described) under reductive amination conditions to give the corresponding N-phenylpiperidin-4-amine derivative of formula (III) .

[0837] Alternatively, the N-phenylpiperidin-4-amine derivatives of formula (III) can be prepared starting from N-protected piperidin-4-one derivatives of formula (VII) (wherein R4 and R5 have the meanings as described previously) and aniline derivatives of formula (VI) (wherein X5, R6 and R7 have the meanings as described previously). Under reductive amination conditions, the compounds of formula (VI) and formula (VII) can be converted into the corresponding piperidine derivatives of formula (VIII) which, after deprotection under acidic conditions (using, for example, HCl or TFA as the acid), gives the piperidin-4-amine derivatives of formula (IX) . These piperidine derivatives of formula (IX) can be converted into derivatives of formula (XI) by reaction with 4-bromobenzene-1-sulfonyl chloride derivatives of formula (III) (wherein X2, X3, R2 and R3 have the meanings as described previously).

[0838] The derivatives of formula (I) can be prepared by any of the following methods: coupling the derivatives of formula (III) directly with a commercially available boric acid or borate ester of formula (X) (wherein R1, R 9 and R 10 are as defined previously) under Suzuki conditions, using, for example, Pd(PPh3)4 and NaHCO3 in a dioxane / water mixture; or first converting the piperidine derivatives of formula (III) into the corresponding boric acid or borate ester of formula (IV) which is then reacted with an R1-halide of formula (V) (wherein R1 has the meaning as described previously) under Suzuki conditions.

[0839] Scheme 2:

[0840]

[0841] Conditions: i) CH3SO2Cl, Et3N, CH2Cl2, room temperature; ii) 4-bromobenzenethiol (XIV) , Cs2CO3, acetone, 60 °C; iii) mCPBA, ethyl acetate, room temperature; iv) 2N HCl, THF, room temperature; v) 4-aminophenylsulfur pentafluoride, 2-methylpyridine borane complex, CH3OH, HOAc, room temperature; vi) bis(pinacolato)diboron, KOAc, Pd(dppf)Cl2, DMF, 75 °C; vii) R 1 -Br (V) , 2N K2CO3, toluene / ethanol, Pd(PPh3)4, 90 °C; viii) R1 - Boric acid / borate ester (X) , Pd(PPh3)4, 2N K2CO3, toluene / ethanol, 90 °C.

[0842] Scheme 2 describes the route for synthesizing the derivatives of the present invention having formula (I) (when X1 = C and X4 = O).

[0843] These compounds can be obtained, for example, by starting from the readily available ketone - protected 4 - hydroxycyclohexan - 1 - one of formula (XII) (wherein R4 and R5 have the meanings as described previously), where the hydroxyl group is converted into a suitable leaving group, such as a mesyl or tosyl group, to give a derivative of formula (XIII) , which can react with a 4 - bromobenzenethiol derivative of formula (XIV) to form a phenylthio derivative of formula (XV) . After oxidation of sulfur using, for example, mCPBA, the resulting sulfonyl derivative of formula (XVI) can be deprotected under acidic conditions to give a sulfonylcyclohexanone derivative of formula (XVII) . These sulfonylcyclohexanone derivatives of formula (XVII) can be coupled with an aniline of formula (VI) (wherein X5, R6 and R7 have the meanings as described previously) under reductive amination conditions to give the corresponding N - phenylpiperidin - 4 - amine derivative of formula (XVIII) .

[0844] The derivatives of formula (I) can be prepared by either of the following methods: coupling a derivative of formula (XVIII) directly with a commercially available boric acid or borate ester of formula (X) (wherein R1, R 9 and R 10 are as defined previously) under Suzuki conditions, which uses, for example, Pd(PPh3)4 and NaHCO3 in a dioxane / water mixture; or first converting the piperidine derivative of formula (XVIII) into the corresponding boric acid or borate ester of formula (XIX) , which then reacts with an R1 - halide of formula (V) (wherein R1 has the meaning as described previously) under Suzuki conditions.

[0845] Scheme 3:

[0846]

[0847] Conditions: i) 2N HCl, THF, room temperature; ii) 4-aminophenylsulfur pentafluoride, 2-methylpyridine borane complex, CH3OH, HOAc, room temperature; iii) ammonium carbamate, (diacetoxyiodo)benzene, CH3OH, CH3CN, room temperature; iv) bis(pinacolato)diboron, KOAc, Pd(dppf)Cl2, DMF, 75 °C; v) R 1 -halide (V) 、2N K2CO3, toluene / ethanol, Pd(PPh3)4, 90 °C; vi) R 1 -boronic acid / boronate (X) 、Pd(PPh3)4, 2N K2CO3, toluene / ethanol, 90 °C.

[0848] Scheme 3 describes the route for synthesizing the derivatives of the present invention having formula (I) (when X1 = C and X4 = N).

[0849] Formula (XV) of the ketone-protected sulfanyl derivative can be deprotected under acidic conditions (using, for example, HCl or TFA) to give the 4-(phenylthio)cyclohexan-1-one derivative of formula (XX) . Under reductive amination conditions, the derivative of formula (XX) can be coupled with a suitable aniline derivative of formula (VI) (wherein X5, R6 and R7 have the meanings as described previously) to give the corresponding N-[4-(phenylthio)cyclohexyl]aniline derivative of formula (XXI) . The derivative of formula (XXII) can be prepared by first converting the derivative of formula (XXI) to the corresponding sulfoximine derivative (by using ammonium carbamate, (diacetoxyiodo)benzene and CH3CN in CH3OH). Finally, the derivative of formula (XXII) can be converted to the derivative of the compound of formula (I) by any of the following methods: reacting with a suitable boronic acid or boronate of formula (X) (wherein R1, R 9 and R 10 are as defined previously) under Suzuki conditions, using, for example, Pd(PPh3)4 as a catalyst; or first converting the derivative of formula (XXII) to its corresponding boronic acid / boronate of formula (XXIII) , which can be further reacted with a suitable (V) bromoaryl derivative under Suzuki conditions, as described previously.

[0850] Scheme 4:

[0851]

[0852] Conditions: i) 4-Bromobenzenethiol (XIV) , Cs2CO3, acetone, 60 °C; ii) ammonium carbamate, (diacetoxyiodo)benzene, CH3OH, CH3CN, room temperature; iii) NaH, di-tert-butyl dicarbonate, THF, room temperature; iv) R 1 -boronic acid / boronic ester (X) , Pd(PPh3)4, 2N K2CO3, toluene / ethanol, 90 °C; v) 5N HCl, 2-propanol, room temperature.

[0853] Scheme 4 describes the route for synthesizing the derivatives of the present invention having formula (I) (when X1 and X4 are N).

[0854] Formula (IX) of N-phenylpiperidin-4-amine derivatives (where X5, R4, R5, R6 and R7 have the meanings as described previously) can be converted to the formula (XXIV) of N-phenyl-1-(phenylthio)piperidin-4-amine derivatives: by reacting with a 4-bromobenzene-1-thiol derivative of the formula (XIV) (where X2, X3, R2 and R3 have the meanings as described previously), using, for example, Cs2CO3 as a base. The derivative of the formula (XXIV) can be converted to the corresponding sulfoniminamide derivative of the formula (XXV) by using ammonium carbamate, (diacetoxyiodo)benzene and CH3CN in CH3OH. After protecting the sulfonimide amide nitrogen with, for example, a Boc group, the derivative of the formula (XXVI) can be reacted with a suitable boronic acid or boronic ester of the formula (X) under Suzuki conditions, as described previously, to give the derivative of formula (XXVII). In the last step, the Boc group can be removed under acidic conditions to give the corresponding derivative of formula (I), where X1 and X4 are N, and X2, X3, X5, R1, R2, R3, R4, R5, R6 and R7 have the meanings as described previously.

[0855] Scheme 5:

[0856]

[0857] Conditions: i) 4-Fluorobenzenesulfonyl chloride (XXVIII) , triethylamine, CH2Cl2, room temperature; ii) heterocycle (XXX), K2CO3, NMP, 120 °C.

[0858] Scheme 5 describes the route for synthesizing the derivatives of the present invention having formula (I) (when R1 is an N-linked heterocyclic group).

[0859] Formula (IX) The N-phenylpiperidin-4-amine derivative (wherein X5, R4, R5, R6 and R7 have the meanings as described previously) can be converted into the 1-(4-fluorobenzenesulfonyl)-N-phenylpiperidin-4-amine derivative of formula (XXIX) by reacting with a 4-fluorobenzene-1-sulfonyl chloride derivative of formula (XXVIII) (wherein X2, X3, R2 and R3 have the meanings as described previously), using, for example, triethylamine as the base. In the last step, the NH-heterocyclic group (XXX) can be coupled under basic conditions to give the corresponding derivative of formula (I), wherein X1 is N, X4 is O, and X2, X3, X5, R1, R2, R3, R4, R5, R6 and R7 have the meanings as described previously.

[0860] Scheme 6:

[0861]

[0862] Conditions: i) methanesulfonyl chloride, TEA, 0 °C to room temperature; ii) 4-bromobenzenethiol (XIV), Cs2CO3, acetone, 60 °C; iii) mCPBA, ethyl acetate, room temperature; iv) TFA, CH2Cl2, room temperature; v) Pd(OAc)2, pyridyl chloride (XXXVI), NaOtBu, Josiphos SL J009-1; vi) R 1 -boronic acid / boronate (X), Pd(PPh3)4, 2N K2CO3, toluene / ethanol, 90 °C; vii: bis(pinacolato)diboron, KOAc, Pd(dppf)Cl2, DMF, 75 °C; viii) R 1 -halide (V) , 2N K2CO3, toluene / ethanol, Pd(PPh3)4, 90 °C;

[0863] Scheme 6 describes the route for synthesizing the derivative of the present invention having formula (I) (when X1 is O, X4 is O, and X2, X3, X5, R1, R2, R3, R4, R5, R6 and R7 have the meanings as described previously).

[0864] As depicted in Scheme 5, the derivative of the present invention having formula (I) can be obtained by subjecting an N-Boc protected cis-4-aminocyclohexan-1-ol derivative of formula (XXXI) (wherein R 4 and R 5(having the meaning as described previously) (which can be easily prepared by those skilled in the art of organic chemistry) and methanesulfonyl chloride are coupled under basic conditions to give the corresponding N-Boc protected cis-4-aminocyclohexyl methanesulfonate derivatives of formula (XXXII). These sulfonate derivatives of formula (XXXII) can be converted to the N-Boc protected 4-[(4-bromophenyl)thio]cyclohexan-1-amine derivatives of formula (XXXIII) via a nucleophilic substitution reaction with the 4-bromobenzene-1-thiol derivatives of formula (XIV) using a suitable base (such as Cs2CO3), which can be oxidized to the corresponding N-Boc _ protected sulfonyl derivatives using, for example, mCPBA as an oxidant. After removal of the Boc group of the derivatives of formula (XXXIV) under acidic conditions (using, for example, TFA), the obtained derivatives of formula (XXXV) can be, for example, under Buchwald conditions, using a suitable pyridyl halide (XXXVI) (where R 6 and R 7 having the meaning as described previously) using, for example, Josiphos SL J009-1, Pd(OAc)2 and a suitable base (such as NaOtBu) to be converted to the derivatives of formula (XXXVII), where X 2 、X 3 、X 5 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 and R 7 having the meaning as described previously. Finally, the derivatives of formula (XXXVII) can be converted to the derivatives of the compound of formula (I) in any of the following ways: reacting with a suitable boronic acid or boronate of formula (X) (where R1, R 9 and R 10 are as defined previously) under Suzuki conditions, using, for example, Pd(PPh3)4 as a catalyst; or first converting the derivatives of formula (XXXVII) to their corresponding boronic acid / boronate of formula (XXXVIII) , which can be further reacted with a suitable (V) bromoaryl derivative under Suzuki conditions, as described previously.

[0865] Scheme 7:

[0866]

[0867] Conditions: i) Pd(OAc)2, aryl halide (XXXVI), NaOtBu, Josiphos SL J009-1; ii) TFA, CH2Cl2, room temperature.

[0868] Scheme 7 describes different ways for synthesizing derivatives of formula (IX) (when X5 is N).

[0869] The tert-butyl 4-aminopiperidine-1-carboxylate derivative of formula (XXXIX) can be converted, for example, under Buchwald conditions using a suitable pyridyl chloride (XXXVI) (where R 6 and R 7 have the meanings as described previously) using, for example, Josiphos SL J009-1, Pd(OAc)2 and a suitable base (such as NaOtBu) to give a derivative of formula (XL), which, after removal of the Boc group under acidic conditions (using, for example, TFA), gives the corresponding pyridyl derivative of formula (XI) (where R 4 、R 5 、R 6 and R 7 have the meanings as described previously).

[0870] Another embodiment of the invention is a compound of formula (I) as described herein, which is manufactured according to the method described herein.

[0871] Pharmaceutical composition and administration

[0872] Another object of the invention is to provide a pharmaceutical composition, which comprises a compound of formula (I) as described herein or a pharmaceutically acceptable salt thereof, and a pharmaceutical excipient.

[0873] Another embodiment of the invention is a pharmaceutical composition, which comprises a compound as described herein or a pharmaceutically acceptable salt thereof, and a pharmaceutical excipient.

[0874] Another embodiment of the invention is a pharmaceutical composition as described herein, which further comprises an additional therapeutic agent.

[0875] Indications

[0876] The compounds of formula (I), formula (I') or formula (I") as described herein can be used in an effective amount to treat a subject, particularly a human, affected by an inflammatory autoimmune disease.

[0877] In one embodiment of the invention is a compound as described herein or a pharmaceutically acceptable salt thereof, which is used as a therapeutic active substance.

[0878] In one embodiment of the present invention, it is a compound as described herein or a pharmaceutically acceptable salt thereof, which is used for treatment, prevention, and / or delaying of inflammatory autoimmune diseases.

[0879] In one embodiment of the present invention, it is a compound as described herein or a pharmaceutically acceptable salt thereof, which is used for treatment, prevention, and / or delaying the progression of psoriasis, asthma, inflammatory bowel disease (IBD), Crohn's disease, obstructive pulmonary disease, ulcerative colitis, rheumatoid arthritis, systemic lupus erythematosus, and multiple sclerosis.

[0880] In one embodiment of the present invention, it is a compound as described herein or a pharmaceutically acceptable salt thereof, which is used for treatment, prevention, and / or delaying the progression of psoriasis, asthma, Crohn's disease, ulcerative colitis, rheumatoid arthritis, systemic lupus erythematosus, and multiple sclerosis.

[0881] In one embodiment of the present invention, it is a compound as described herein or a pharmaceutically acceptable salt thereof, which is used for preparing a medicament for treating, preventing, and / or delaying the progression of psoriasis, asthma, Crohn's disease, ulcerative colitis, rheumatoid arthritis, systemic lupus erythematosus, and multiple sclerosis.

[0882] In one embodiment of the present invention, it is a compound as described herein or a pharmaceutically acceptable salt thereof, which is used for preparing a medicament for treating, preventing, and / or delaying inflammatory autoimmune diseases.

[0883] In a further embodiment, the present invention provides a method for treating, preventing, and / or delaying the progression of inflammatory autoimmune diseases, the method comprising administering a therapeutically effective amount of a compound as described herein or a pharmaceutically acceptable salt thereof.

[0884] In a further embodiment, the present invention provides a method for treating, preventing, and / or delaying the progression of psoriasis, asthma, inflammatory bowel disease (IBD), Crohn's disease, obstructive pulmonary disease, ulcerative colitis, rheumatoid arthritis, systemic lupus erythematosus, or multiple sclerosis, the method comprising administering a therapeutically effective amount of a compound as described herein or a pharmaceutically acceptable salt thereof.

[0885] As used herein, the term "treatment / treating" and its grammatical variants mean a therapeutic treatment. With respect to a particular disorder, treatment means: (1) ameliorating one or more of the biological manifestations of the disorder or the biological manifestations of the disorder, (2) interfering with one or more points in the biological cascade that causes or contributes to the disorder or (b) one or more of the biological manifestations of the disorder, (3) alleviating one or more of the symptoms, effects, or side effects associated with the disorder or its treatment, or (4) slowing the progression of the disorder or one or more of the biological manifestations of the disorder. Prophylactic treatment using the methods and / or compositions of the invention is also contemplated. Those skilled in the art will recognize that "prevention" is not an absolute term. In medicine, "prevention" is understood to refer to the prophylactic administration of a drug to significantly reduce the likelihood or severity of a disorder or its biological manifestations, or to delay the onset of such a disorder or its biological manifestations. For example, when a subject is considered to be at high risk of developing psoriasis, asthma, inflammatory bowel disease (IBD), Crohn's disease, obstructive lung disease, ulcerative colitis, rheumatoid arthritis, systemic lupus erythematosus, or multiple sclerosis, such as when the subject has a strong family history of psoriasis, asthma, inflammatory bowel disease (IBD), Crohn's disease, obstructive lung disease, ulcerative colitis, rheumatoid arthritis, systemic lupus erythematosus, or multiple sclerosis, prophylactic therapy is appropriate.

[0886] Experimental section

[0887] As depicted in the examples below, in certain exemplary embodiments, the compounds are prepared according to the following general procedure. It should be understood that although the general method describes the synthesis of certain compounds of the invention, the following general method and other methods known to those skilled in the art can be applied to all compounds described herein and to subclasses and species of each of these compounds.

[0888] Example 1: 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[0889]

[0890] i) At 0 °C, to 1-(4-bromobenzenesulfonyl)piperidin-4-one (500 mg) and 4-(pentafluoro-λ 6A suspension of (1.38 g) of aniline in a mixture of 10% HOAc in CH3OH (16.5 mL) was added to 2-methylpyridine borane complex (168 mg). After removal of the ice bath, the reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and 2N aqueous HCl solution (10 mL) was added. After stirring for 1 h at room temperature, 5N aqueous NaOH solution (20 mL) was added, and the product was extracted into CH2Cl2. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified on SiO2 using 30% ethyl acetate in heptane as the eluent to give 1-(4-Bromobenzenesulfonyl)-N-[4-(penta fluoro-λ 6 -thiol)phenyl]piperidin-4-amine (1.75 g), which is a white solid.

[0891] ii) To a solution of the product (200 mg) obtained in the previous step, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine (112 mg) and NaHCO3 (193 mg) in a mixture of dioxane / water (4 / 1) (5 mL) (purged with N2 gas) was added Pd(PPh3)4 (22 mg). The reaction mixture was heated in a microwave at 110 °C for 2 h. After cooling to room temperature, the product was extracted into ethyl acetate, and the organic layer was washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified on C18 using 10% to 100% CH3CN in water as the eluent to give the title compound 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfur yl)phenyl]piperidin-4-amine (59 mg), which is a white solid. MS (ES + ) m / z 559.2 (M+H) + .

[0892] 1 1H NMR (400 MHz, DMSO) δ 9.10 (dd, J = 1.9, 1.0 Hz, 1H), 8.06–7.98 (m, 3H), 7.91–7.84 (m, 2H), 7.72 (dt, J = 9.4, 0.9, 0.9 Hz, 1H), 7.67 (dd, J = 9.1, 1.6 Hz, 2H), 7.52–7.43 (m, 2H), 6.61 (d, J = 9.0 Hz, 2H), 6.47 (d, J = 7.9 Hz, 1H), 3.62 (d, J = 11.9 Hz, 2H), 3.44–3.34 (m, 1H), 2.63–2.52 (m, 2H), 1.97 (d, J = 12.8 Hz, 2H), 1.52–1.38 (m, 2H).

[0893] Following a procedure similar to that described for Example 1, Examples 2 to 4 have been prepared using an appropriate borate or boric acid in step ii.

[0894] Examples 2 to 4

[0895] Example 2: 1-[4-(3-methyl-2H-indazol-5-yl)phenylsulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[0896]

[0897] MS(ES + ) m / z 573.3 (M+H) +

[0898] Structural unit: Step ii: (3-methyl-1H-indazol-5-yl)boronic acid.

[0899] Example 3: 5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indole-3-carbonitrile.

[0900]

[0901] MS(ES + ) m / z 583.2 (M+H) +

[0902] Structural unit: Step ii: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-carbonitrile.

[0903] Example 4: 5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indazol-3-carbonitrile.

[0904]

[0905] MS(ES + ) m / z 584.3 (M+H) +

[0906] Structural unit: Step ii: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-3-carbonitrile.

[0907] Example 5: 4-(pentafluoro-λ 6-Thiol)-N-[cis-4-[4-(3-Methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline.

[0908]

[0909] i) At 0 °C, a solution of methanesulfonyl chloride (1.3 mL) in CH2Cl2 (10 mL) was added dropwise to a solution of 4-hydroxycyclohexanone monoethylene ketal (2.0 g) and triethylamine (2.3 mL) in CH2Cl2 (15 mL). The reaction mixture was stirred overnight at room temperature. After completion, the reaction mixture was quenched by pouring it into a saturated aqueous NaHCO3 solution. The layers were separated, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The yellow oil obtained was dissolved in heptane, the precipitated solid was filtered off, and the filtrate was concentrated under reduced pressure to give 1,4-Dioxaspiro[4.5]decane-8-yl methanesulfonate (3.3 g), which was an oil that slowly solidified. The product was used in the next step without further purification.

[0910] ii) 4-Bromobenzenethiol (2.64 g) was added to a suspension of the product (3.3 g) obtained in the previous step and cesium carbonate (5.46 g) in acetone (50 mL). The reaction mixture was stirred overnight at 60 °C. After cooling to room temperature, the reaction mixture was filtered, and the solid was washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and the oil obtained was purified on SiO2 using 0% to 60% ethyl acetate in heptane as the eluent to give 8-[(4-Bromoben yl)thio]-1,4-dioxaspiro[4.5]decane (3.68 g), which was a white solid.

[0911] iii) 3-Chloroperoxybenzoic acid (9.64 g) was added to a solution of the product (3.68 g) obtained in the previous step in ethyl acetate (50 mL), and the reaction mixture was stirred overnight at room temperature. The reaction mixture was washed with a saturated NaHCO3 solution, and the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified on SiO2 using 0% to 100% ethyl acetate in heptane as the eluent to give 8-(4-Bromo benzenesulfonyl)-1,4-dioxaspiro[4.5]decane (3.68 g), which was a white solid.

[0912] iv) At room temperature, 2N aqueous HCl solution (39 mL) was added to a solution of the product (3.5 g) obtained in the previous step in THF (50 mL), and the reaction mixture was stirred overnight at room temperature. After completion, the reaction mixture was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give 4- (4-Bromobenzenesulfonyl)cyclohexan-1-one (3.0 g), which was a white solid and was used in the next step without further purification.

[0913] v) At 0 °C, 2-methylpyridine borane complex (219 mg) was added to a suspension of the product (500 mg) obtained in the previous step and 4-(pentafluoro-λ 6 -sulfanyl)aniline (0.35 ml g) in a mixture of 10% HOAc in CH3OH (11 mL). After removing the ice bath, the reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and 2N aqueous HCl solution (5 mL) was added at 0 °C. After stirring for 1 h at 0 °C, 5N aqueous NaOH solution (12 mL) was added, and the product was extracted into CH2Cl2. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified on SiO2 using 0% to 40% ethyl acetate in heptane as the eluent to give N-[4-(4-Bromoben acyl)cyclohexyl]-4-(pentafluoro-λ 6 -thio)aniline (0.5 g), which was a white solid.

[0914] vi) Under a nitrogen atmosphere, Pd(PPh3)4 (28 mg) was added to a solution of the product (250 mg) obtained in the previous step, 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indazole (148 mg) and NaHCO3 (242 mg) in a mixture of 1,4-dioxane (8 mL) and water (2 mL). In a microwave, the reaction mixture was stirred at 110 °C for 2 hours. After cooling to room temperature, the reaction mixture was poured into water, and the product was extracted into ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained brown oil was purified on C18 using 10% to 90% CH3CN in water as the eluent to give the title compound 4-(Pentafluoro-λ 6 -sulfur zenesulfonyl)-N-[cis-4-[4-(3-Methylindazol-5-yl)benzenesulfonyl]cyclohexyl]aniline (92 mg), which was a white solid. MS(ES + ) m / z 572.2 (M + H) + .

[0915] 11H NMR (400 MHz, DMSO) δ 12.78 (s, 1H), 8.15 (dd, J = 1.8, 0.8 Hz, 1H), 8.08–8.00 (m, 2H), 7.95–7.88 (m, 2H), 7.75 (dd, J = 8.8, 1.7 Hz, 1H), 7.59 (d, J = 8.7 Hz, 1H), 7.54–7.49 (m, 2H), 6.67 (d, J = 8.9 Hz, 2H), 6.58 (d, J = 6.4 Hz, 1H), 3.59 (s, 1H), 3.41–3.34 (m, 1H), 2.56 (s, 3H), 1.94–1.56 (m, 8H).

[0916] Following a procedure similar to that described for Example 5 and using an appropriate borate or boric acid in step vi, Examples 6 to 23 have been prepared.

[0917] Examples 6 to 23

[0918] Example 6: 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline.

[0919]

[0920] MS (ES + ) m / z 572.2 (M+H) +

[0921] Structural unit: Step vi: 3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indazole.

[0922] Example 7: 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile.

[0923]

[0924] MS (ES + ) m / z 582.2 (M+H) +

[0925] Structural unit: Step vi: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-carbonitrile.

[0926] Example 8: 5-(4-{[cis-4-{[4-(pentafluoro-λ 6{[trans-4-({4-(pentafluoro-λ6-sulfanyl)phenyl}amino)cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile

[0927]

[0928] MS(ES + ) m / z 582.2 (M+H) +

[0929] Structural unit: Step vi: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-carbonitrile

[0930] Example 9: 6-(4-{[trans-4-{[4-(pentafluoro-λ6-sulfanyl)phenyl}amino)cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one 6

[0931]

[0932] MS(ES + ) m / z 573.4 (M+H) +

[0933] Structural unit: Step vi: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-isoindol-1-one

[0934] Example 10: 4-(4-{[trans-4-{[4-(pentafluoro-λ6-sulfanyl)phenyl}amino)cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide 6

[0935]

[0936] MS(ES + ) m / z 562.3 (M+H) +

[0937] Structural unit: Step vi: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide

[0938] Example 11: 4-(pentafluoro-λ6-sulfanyl)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 6

[0939]

[0940] MS(ES​​​+ ) m / z 573.3 (M+H) +

[0941] Structural unit: Step vi: {3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}boronic acid.

[0942] Example 12: 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline.

[0943]

[0944] MS(ES + ) m / z 558.2 (M+H) +

[0945] Structural unit: Step vi: {Imidazo[1,2-a]pyridin-6-yl}boronic acid.

[0946] Example 13: 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-Methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline.

[0947]

[0948] MS(ES + ) m / z 572 (M+H) +

[0949] Structural unit: Step vi: 3-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[0950] Example 14: 5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one.

[0951]

[0952] MS(ES + ) m / z 573.2 (M+H) +

[0953] Structural unit: Step vi: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indol-2-one.

[0954] Example 15: N,N-dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide.

[0955]

[0956] MS(ES + ) m / z 589.3 (M+H) +

[0957] Structural unit: Step vi: N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide.

[0958] Example 16: N-methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide.

[0959]

[0960] MS(ES + ) m / z 575.3 (M+H) +

[0961] Structural unit: Step vi: N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide.

[0962] Example 17: 6-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile.

[0963]

[0964] MS(ES + ) m / z 583.3 (M+H) +

[0965] Structural unit: Step vi: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-3-carbonitrile.

[0966] Example 18: 4-(pentafluoro-λ 6 -sulfanyl)-N-[cis-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline.

[0967]

[0968] MS(ES + )m / z 558.3(M+H) +

[0969] Structural unit: Step vi: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[0970] Example 19: N,N-dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide.

[0971]

[0972] MS(ES + )m / z 587.3(M-H) +

[0973] Structural unit: Step vi: N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide.

[0974] Example 20: N,N-dimethyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide.

[0975]

[0976] MS(ES + )m / z 590.3(M+H) +

[0977] Structural unit: Step vi: N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide.

[0978] Example 21: N-methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide.

[0979]

[0980] MS(ES + )m / z 575(M+H) +

[0981] Structural unit: Step vi: [3-(methylcarbamoyl)phenyl]boronic acid.

[0982] Example 22: N-Methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide.

[0983]

[0984] MS(ES + ) m / z 576.3 (M+H) +

[0985] Structural unit: Step vi: N-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide.

[0986] Example 23: 4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide.

[0987]

[0988] MS(ES + ) m / z 561.3 (M+H) +

[0989] Structural unit: Step vi: (3-carbamoylphenyl)boronic acid.

[0990] Example 24: 1-(4-{Imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[0991]

[0992] i) To a suspension of 1-(4-bromobenzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine (Example 1, Step i, 500 mg), bis(pinacolato)diboron (365 mg) and potassium acetate (235 mg) in cyclopentyl methyl ether (5 mL) (purged with N2 gas) was added PdCl2(dppf).CH2Cl2 (39 mg). The reaction mixture was heated in a microwave at 100 °C for 1 h. After cooling to room temperature, the reaction mixture was poured into water and the product was extracted into ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure to give N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-[4-(4,4,5, 5-Tetramethyl-1,3,2-dioxaborolane-2-yl)benzenesulfonyl]piperidin-4-amine, which is a brown oil (558 mg), and is used in the next step without further purification.

[0993] ii) According to the procedure described in step ii of Example 1, the product (150 mg) obtained in the previous step and 6-bromoimidazo[1,2-a]pyridazine (63 mg) were converted into the title compound 1-(4-{Imidazo[1,2-a]pyrazin-6-yl}benzenesulf (base)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine (48 mg), which is a white solid. MS (ES + ) m / z 560.3 (M + H) + .

[0994] 1 H NMR (400 MHz, DMSO) δ 9.43 (d, J = 1.5 Hz, 1H), 9.25–9.20 (m, 1H), 8.36–8.28 (m, 2H), 8.20 (t, J = 0.9, 0.9 Hz, 1H), 7.94–7.85 (m, 3H), 7.51–7.42 (m, 2H), 6.60 (d, J = 8.9 Hz, 2H), 6.46 (d, J = 7.9 Hz, 1H), 3.61 (d, J = 12.0 Hz, 2H), 3.43–3.34 (m, 1H), 2.59 (td, J = 11.7, 11.6, 2.7 Hz, 2H), 2.01–1.93 (m, 2H), 1.52–1.38 (m, 2H).

[0995] Following a procedure similar to that described for Example 24, appropriate aryl halides were used in step ii, and Examples 25 to 31 were prepared.

[0996] Examples 25 to 31

[0997] Example 25: 6-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile.

[0998]

[0999] MS (ES + ) m / z 584.3 (M + H) +

[1000] Structural unit: Step ii: 6-bromoimidazo[1,2-a]pyridine-3-carbonitrile.

[1001] Example 26: 6-{4-[(4-{[4-(pentafluoro-λ 6-{[1,2,4]Triazolo[4,3-a]pyridine-3-carboxamido}phenyl}-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide.

[1002]

[1003] MS(ES + ) m / z 603.3 (M+H) +

[1004] Structural unit: Step ii: 6-Bromo-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide.

[1005] Example 27: 1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1006]

[1007] MS(ES + ) m / z 574.3 (M+H) +

[1008] Structural unit: Step ii: 6-Bromo-3-methyl-[1,2,4]triazolo[4,3-a]pyridine.

[1009] Example 28: N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine.

[1010]

[1011] MS(ES + ) m / z 602.3 (M+H) +

[1012] Structural unit: Step ii: 6-Bromo-3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridine.

[1013] Example 29: N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine.

[1014]

[1015] MS(ES +)m / z 601.4(M+H) +

[1016] Structural unit: Step ii: 6-bromo-3-(propan-2-yl)imidazo[1,2-a]pyridine.

[1017] Example 30: 1-{4-[3-(methoxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1018]

[1019] MS(ES + )m / z 604.4(M+H) +

[1020] Structural unit: Step ii: 6-bromo-3-(methoxymethyl)-[1,2,4]triazolo[4,3-a]pyridine.

[1021] Example 31: 1-(4-{3-cyclopentyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1022]

[1023] MS(ES + )m / z 628.4(M+H) +

[1024] Structural unit: Step ii: 6-bromo-3-cyclopentyl-[1,2,4]triazolo[4,3-a]pyridine.

[1025] Example 32: 6-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one.

[1026]

[1027] i) Following a procedure similar to that described for Example 24, 6-bromo-2-[(4-methoxyphenyl)methyl]-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one (97 mg) was used in Step ii, and 2-[(4-Methoxyphenyl)meth Base]-6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2H,3H-[1,2,4] yl]-1,2,4-triazolo[4,3-a]pyridin-3-one (48 mg) was prepared, which is a white solid.

[1028] ii) The solution of the product (48 mg) obtained in the previous step and L-cysteine (17 mg) in trifluoroacetic acid (604 μL) was stirred at 70 °C for 4 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure, and the residue was purified on C18 using 10% to 60% acetonitrile in water as the eluent, giving the title compound 6-{4- [(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2H,3H-[1,2,4]triazolo[4, 3-a]pyridin-3-one (6 mg), which is a white solid. MS (ES + ) m / z 576.3 (M+H) + .

[1029] 1 1H NMR (400 MHz, DMSO) δ 12.61 (s, 1H), 8.23 (t, J = 1.4, 1.4 Hz, 1H), 8.07–8.00 (m, 2H), 7.86–7.78 (m, 2H), 7.66 (dd, J = 9.8, 1.8 Hz, 1H), 7.51–7.44 (m, 2H), 7.40 (dd, J = 9.8, 1.1 Hz, 1H), 6.60 (d, J = 9.0 Hz, 2H), 6.46 (d, J = 7.8 Hz, 1H), 3.60 (d, J = 11.9 Hz, 2H), 3.42–3.34 (m, 1H), 2.61–2.53 (m, 2H), 2.02–1.93 (m, 2H), 1.51–1.37 (m, 2H).

[1030] Example 33: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile.

[1031]

[1032] i) According to the procedure described in Example 24, step i, N-[4-(4-Bromobenzenesulfonyl)cyclohexyl]-4-(penta Fluoro-λ 6 -thiol)aniline (Example 5, step v, 500 mg) was converted to 4-(Pentafluoro-λ 6 -sulfanyl)-N-{4-[4-(4,4,5,5-tetrameth yl-1,3,2-dioxaborolane-2-yl)benzenesulfonyl]cyclohexyl}aniline (916 mg), which is a brown oil and was used in the next step without further purification.

[1033] ii) According to the procedure described in Example 1, step ii, the product (126 mg) obtained in the previous step and 6-bromoimidazo[1,2-a]pyridine-3-carbonitrile (60 mg) were converted to the title compound 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfur yl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile (10 mg), which is a white solid. MS (ES+ ) m / z 583.3 (M+H) + 。

[1034] 1 H NMR (400 MHz, DMSO) δ 9.00 (t, J = 1.4, 1.4 Hz, 1H), 8.54 (s, 1H), 8.19–8.12 (m, 2H), 8.07–7.96 (m, 4H), 7.52–7.45 (m, 2H), 6.62 (d, J = 8.9 Hz, 2H), 6.43 (d, J = 7.8 Hz, 1H), 3.45–3.35 (m, 1H), 3.29–3.20 (m, 1H), 2.02 (t, J = 15.8, 15.8 Hz, 4H), 1.56 (q, J = 12.2, 12.1, 12.1 Hz, 2H), 1.21 (q, J = 11.9, 11.6, 11.6 Hz, 2H).

[1035] Following a procedure similar to that described for Example 33, using the appropriate aryl halide in step ii, Examples 34 to 65 have been prepared.

[1036] Examples 34 to 65

[1037] Example 34: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide.

[1038]

[1039] MS (ES + ) m / z 601.3 (M+H) +

[1040] Structural unit: Step ii: 6-bromoimidazo[1,2-a]pyridine-3-carboxamide.

[1041] Example 35: 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline.

[1042]

[1043] MS (ES + ) m / z 601.4 (M+H) +

[1044] Structural unit: Step ii: 6-bromo-3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridine.

[1045] Example 36: 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline.

[1046]

[1047] MS(ES + ) m / z 559.3 (M+H) +

[1048] Structural unit: Step ii: 6-bromo-[1,2,4]triazolo[4,3-a]pyridine.

[1049] Example 37: 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carboxamide.

[1050]

[1051] MS(ES + ) m / z 601.3 (M+H) +

[1052] Structural unit: Step ii: 5-bromo-1H-indazole-3-carboxamide.

[1053] Example 38: 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carbonitrile.

[1054]

[1055] MS(ES + ) m / z 583.3 (M+H) +

[1056] Structural unit: Step ii: 5-bromo-1H-indazole-3-carbonitrile.

[1057] Example 39: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide.

[1058]

[1059] MS(ES + )m / z 602.3(M+H) +

[1060] Structural unit: Step ii: 6-bromo-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide.

[1061] Example 40: 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline.

[1062]

[1063] MS(ES + )m / z 573.3(M+H) +

[1064] Structural unit: Step ii: 6-bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine.

[1065] Example 41: 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl}benzenesulfonyl)cyclohexyl]aniline.

[1066]

[1067] MS(ES + )m / z 573.3(M+H) +

[1068] Structural unit: Step ii: 7-bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine.

[1069] Example 42: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carbonitrile.

[1070]

[1071] MS(ES + )m / z 584.3(M+H) +

[1072] Structural unit: Step ii: 6-bromo-[1,2,4]triazolo[4,3-a]pyridine-3-carbonitrile.

[1073] Example 43: 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methylimidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline.

[1074]

[1075] MS(ES + ) m / z 573.3 (M+H) +

[1076] Structural unit: Step ii: 6-bromo-2-methylimidazo[1,2-a]pyrazine.

[1077] Example 44: 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline.

[1078]

[1079] MS(ES + ) m / z 559.3 (M+H) +

[1080] Structural unit: Step ii: 6-bromoimidazo[1,2-a]pyrazine.

[1081] Example 45: N,N-dimethyl-6-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide.

[1082]

[1083] MS(ES + ) m / z 590.3 (M+H) +

[1084] Structural unit: Step ii: 6-chloro-N,N-dimethylpyridine-3-carboxamide.

[1085] Example 46: N,N-dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide.

[1086]

[1087] MS(ES + ) m / z 590.3 (M+H)+

[1088] Structural unit: Step ii: 6-chloro-N,N-dimethylpyridine-3-carboxamide.

[1089] Example 47: N-methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide.

[1090]

[1091] MS(ES + ) m / z 576.3 (M+H) +

[1092] Structural unit: Step ii: 6-chloro-N-methylpyridine-3-carboxamide.

[1093] Example 48: N-methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide.

[1094]

[1095] MS(ES + ) m / z 576.3 (M+H) +

[1096] Structural unit: Step ii: 4-chloro-N-methylpyridine-2-carboxamide.

[1097] Example 49: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide.

[1098]

[1099] MS(ES + ) m / z 562.3 (M+H) +

[1100] Structural unit: Step ii: 6-chloropyridine-3-carboxamide.

[1101] Example 50: 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]benzenesulfonyl}cyclohexyl]aniline.

[1102]

[1103] MS(ES + ) m / z 602.3 (M+H) +

[1104] Structural unit: Step ii: 6-chloro-3-(propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazine.

[1105] Example 51: 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}cyclohexyl]aniline.

[1106]

[1107] MS(ES + ) m / z 602.4 (M+H) +

[1108] Structural unit: Step ii: 6-bromo-3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazine.

[1109] Example 52: 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2-dihydropyridin-2-one.

[1110]

[1111] MS(ES + ) m / z 533.2 (M-H) +

[1112] Structural unit: Step ii: 4-bromo-1,2-dihydropyridin-2-one.

[1113] Example 53: 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one.

[1114]

[1115] MS(ES + ) m / z 587.4 (M+H) +

[1116] Structural unit: Step ii: 7-bromo-1,2,3,4-tetrahydroisoquinolin-3-one.

[1117] Example 54: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one.

[1118]

[1119] MS(ES + ) m / z 587.4 (M+H) +

[1120] Structural unit: Step ii: 6-bromo-1,2,3,4-tetrahydroisoquinolin-3-one.

[1121] Example 55: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-3H,4H-pyrrolo[2,1-f][1,2,4]triazin-4-one.

[1122]

[1123] MS(ES + ) m / z 575.3 (M+H) +

[1124] Structural unit: Step ii: 6-bromo-3H,4H-pyrrolo[2,1-f][1,2,4]triazin-4-one.

[1125] Example 56: 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridin-2-ol.

[1126]

[1127] MS(ES + ) m / z 535.2 (M+H) +

[1128] Structural unit: Step ii: 5-bromopyridin-2-ol.

[1129] Example 57: 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{[4'-(dimethylphosphoryl)-[1,1'-biphenyl]-4-yl]sulfonyl}cyclohexyl]aniline.

[1130]

[1131] MS(ES +)m / z 594.3(M+H) +

[1132] Structural unit: Step ii: 1-bromo-4-(dimethylphosphoryl)benzene.

[1133] Example 58: 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one.

[1134]

[1135] MS(ES + )m / z 573.3(M+H) +

[1136] Structural unit: Step ii: 5-bromo-2,3-dihydro-1H-isoindol-1-one.

[1137] Example 59: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one.

[1138]

[1139] MS(ES + )m / z 573.3(M+H) +

[1140] Structural unit: Step ii: 6-bromo-2,3-dihydro-1H-indol-2-one.

[1141] Example 60: 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one.

[1142]

[1143] MS(ES + )m / z 585.3(M-H) +

[1144] Structural unit: Step ii: 7-bromo-1,2,3,4-tetrahydroisoquinolin-1-one.

[1145] Example 61: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6-thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one.

[1146]

[1147] MS(ES + ) m / z 587.4 (M+H) +

[1148] Structural unit: Step ii: 6-bromo-1,2,3,4-tetrahydroisoquinolin-1-one.

[1149] Example 62: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridazine-3-carboxamide.

[1150]

[1151] MS(ES + ) m / z 563.3 (M+H) +

[1152] Structural unit: Step ii: 6-chloropyridazine-3-carboxamide.

[1153] Example 63: 4-(pentafluoro-λ 6 -thio)-N-[trans-4-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline.

[1154]

[1155] MS(ES + ) m / z 563.3 (M+H) +

[1156] Structural unit: Step ii: 6-bromo-3-(propan-2-yl)imidazo[1,2-a]pyridine.

[1157] Example 64: 4-(pentafluoro-λ 6 -thio)-N-[trans-4-{4-[8-methyl-3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline.

[1158]

[1159] MS(ES + ) m / z 614.4 (M+H) +

[1160] Structural unit: Step ii: 6-Bromo-8-methyl-3-(propan-2-yl)imidazo[1,2-a]pyridine.

[1161] Example 65: 5'-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1',2'-dihydrospiro[cyclopropane-1,3'-indol]-2'-one.

[1162]

[1163] MS(ES + ) m / z 599.3 (M+H) +

[1164] Structural unit: Step vi: 5'-Bromo-1',2'-dihydrospiro[cyclopropane-1,3'-indol]-2'-one.

[1165] Example 66: 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one.

[1166]

[1167] i) Following a procedure similar to that described for Example 32, 6-bromo-2-[(4-methoxyphenyl)methyl]-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one (447 mg) was used in Step ii to prepare 2-[(4-Methoxyphenyl)meth Base]-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2H,3H-[1,2, yl]-1,2,4-triazolo[4,3-a]pyridin-3-one (400 mg), which was a white solid.

[1168] ii) A solution of the product obtained in the previous step (400 mg) and L-cysteine (104 mg) in trifluoroacetic acid (3.7 mL) was stirred at 70 °C for 6 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and the residue was purified on C18 using 30% to 50% acetonitrile in water as the eluent to give the title compound 6- (4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2H,3H-[1,2,4]triazole 1,2,4-Triazolo[4,3-a]pyridin-3-one (170 mg), which was a white solid. MS(ES + ) m / z 575.3 (M+H) + .

[1169] 11H NMR (400 MHz, DMSO) δ 12.62 (s, 1H), 8.24 (t, J = 1.5, 1.5 Hz, 1H), 8.10–8.00 (m, 2H), 7.95–7.87 (m, 2H), 7.66 (dd, J = 9.9, 1.8 Hz, 1H), 7.52–7.43 (m, 2H), 7.39 (dd, J = 9.8, 1.1 Hz, 1H), 6.62 (d, J = 8.9 Hz, 2H), 6.42 (d, J = 7.8 Hz, 1H), 3.40–3.31 (m, 1H), 3.30–3.19 (m, 1H), 2.10–1.95 (m, 4H), 1.61–1.47 (m, 2H), 1.20 (q, J = 12.0, 11.4, 11.4 Hz, 2H).

[1170] Example 67: 1-(2-Fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1171]

[1172] i) Following a procedure similar to that described for Example 1, Step i, tert-butyl 4-oxopiperidine-1-carboxylate (6 g) and 4-(pentafluoro-λ 6 -sulfanyl)aniline (7.9) were converted to 4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidine-1-carboxylic acid tert-butyl ester (15 g), which was obtained as a white solid and used in the next step without further purification.

[1173] ii) To a solution of the product obtained in the previous step (15 g) in CH2Cl2 (50 mL) was added a 5 N HCl solution in 2-propanol (75 mL). After stirring overnight at room temperature, the reaction mixture was concentrated in vacuo to give N-[4- (Pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine hydrochloride (14.2 g), which was a white solid and used in the next step without further purification.

[1174] iii) To a solution of the product obtained in the previous step (1 g) and Et3N (2.1 mL) in CH2Cl2 (20 mL) was added 4-bromo-2-fluorobenzene-1-sulfonyl chloride (0.89 g). The reaction mixture was stirred overnight at room temperature. The reaction mixture was quenched by pouring it into water. The product was extracted into CH2Cl2, and the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give 1-(4-Bromo-2-fluorobenzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine (1.6 g), which was an off-white solid and used in the next step without further purification.

[1175] iv) According to the procedure described in step ii for Example 1, convert the product (100 mg) obtained in the previous step and 3-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine (57 mg) into the title compound 1-(2-Fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 - (thio)phenyl]piperidin-4-amine (57 mg), which is a white solid. MS(ES + ) m / z 591.3 (M+H) + .

[1176] 1 H NMR (400 MHz, DMSO) δ 8.75 (t, J = 1.4, 1.4 Hz, 1H), 8.07 (dd, J = 12.1, 1.6 Hz, 1H), 7.95–7.84 (m, 2H), 7.68 (d, J = 1.3 Hz, 2H), 7.52–7.47 (m, 2H), 7.45 (t, J = 0.9, 0.9 Hz, 1H), 6.62 (d, J = 8.9 Hz, 2H), 6.50 (d, J = 7.9 Hz, 1H), 3.67 (d, J = 12.3 Hz, 2H), 3.51–3.41 (m, 1H), 2.83 (t, J = 11.4, 11.4 Hz, 2H), 2.57 (d, J = 1.0 Hz, 3H), 2.03–1.95 (m, 2H), 1.52–1.38 (m, 2H).

[1177] Compounds 68 to 80 have been prepared according to a procedure similar to that described for Example 67, using an appropriate sulfonyl chloride in step iii and an appropriate boronic ester or boronic acid in step iv.

[1178] Examples 68 to 80

[1179] Example 68: 1-(3-Fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1180]

[1181] MS(ES + ) m / z 591.3 (M+H) +

[1182] Structural unit: Step iii: 4-Bromo-3-fluorobenzene-1-sulfonyl chloride; Step iv: 3-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1183] Example 69: 1-[(6-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1184]

[1185] MS(ES + ) m / z 574.3 (M+H) +

[1186] Structural unit: Step iii: 6-Bromopyridine-3-sulfonyl chloride; Step iv: 3-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1187] Example 70: 1-[(5-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1188]

[1189] MS(ES + ) m / z 574.3 (M+H) +

[1190] Structural unit: Step iii: 5-Bromopyridine-2-sulfonyl chloride; Step iv: 3-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1191] Example 71: 6-{2-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile.

[1192]

[1193] MS(ES + ) m / z 602.3 (M+H) +

[1194] Structural unit: Step iii: 4-Bromo-3-fluorobenzene-1-sulfonyl chloride; Step iv: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-3-carbonitrile.

[1195] Example 72: 1-(3-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1196]

[1197] MS(ES + ) m / z 577.3 (M+H) +

[1198] Structural unit: Step iii: 4-Bromo-3-fluorobenzene-1-sulfonyl chloride; Step iv: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1199] Example 73: 6-{3-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile.

[1200]

[1201] MS(ES + ) m / z 602 (M+H) +

[1202] Structural unit: Step iii: 4-Bromo-2-fluorobenzene-1-sulfonyl chloride; Step iv: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-3-carbonitrile.

[1203] Example 74: 1-(2-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1204]

[1205] MS(ES + ) m / z 577.3 (M+H) +

[1206] Structural unit: Step iii: 4-Bromo-2-fluorobenzene-1-sulfonyl chloride; Step iv: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1207] Example 75: 1-[(5-{Imidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1208]

[1209] MS(ES + ) m / z 560.3 (M+H) +

[1210] Structural unit: Step iii: 5-Bromopyridine-2-sulfonyl chloride; Step iv: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1211] Example 76: 6-{5-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-2-yl}imidazo[1,2-a]pyridine-3-carbonitrile.

[1212]

[1213] MS(ES + ) m / z 585.3 (M+H) +

[1214] Structural unit: Step iii: 6-Bromopyridine-3-sulfonyl chloride; Step iv: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-3-carbonitrile.

[1215] Example 77: 1-[(6-{Imidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1216]

[1217] MS(ES + ) m / z 560.3 (M+H) +

[1218] Structural unit: Step iii: 6-Bromopyridine-3-sulfonyl chloride; Step iv: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1219] Example 78: 6-{6-[(4-{[4-(pentafluoro-λ 6{piperidin-1-yl)sulfonyl]pyridin-3-yl}imidazo[1,2-a]pyridine-3-carbonitrile.

[1220]

[1221] MS(ES + ) m / z 585.3 (M+H) +

[1222] Structural unit: Step iii: 5-bromopyridine-2-sulfonyl chloride; Step iv: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-3-carbonitrile.

[1223] Example 79: 1-(2-chloro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1224]

[1225] MS(ES + ) m / z 593.3 (M+H) +

[1226] Structural unit: Step iii: 4-bromo-2-chlorobenzene-1-sulfonyl chloride; Step iv: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1227] Example 80: 6-{3-chloro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile.

[1228]

[1229] MS(ES + ) m / z 618.3 (M+H) +

[1230] Structural unit: Step iii: 4-bromo-2-chlorobenzene-1-sulfonyl chloride; Step iv: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-3-carbonitrile.

[1231] Compounds 81 to 83 have been prepared according to a procedure similar to that described for Example 67, using appropriate SF5-aniline and tert-butyl 4-oxopiperidine-1-carboxylate in step i, appropriate sulfonyl chloride in step iii, and appropriate boronic ester or boronic acid in step iv.

[1232] Examples 81 to 83

[1233] Example 81: 6-{4-[(4-{[3-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile.

[1234]

[1235] MS(ES + ) m / z 584.3 (M+H) +

[1236] Structural units: Step i: 3-(pentafluoro-λ 6 -sulfanyl)aniline; Step iii: 4-bromobenzene-1-sulfonyl chloride; Step iv: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-3-carbonitrile.

[1237] Example 82: 1-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[3-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1238]

[1239] MS(ES + ) m / z 584.3 (M+H) +

[1240] Structural units: Step i: 3-(pentafluoro-λ 6 -sulfanyl)aniline; Step iii: 4-bromobenzene-1-sulfonyl chloride; Step iv: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1241] Example 83: 4-(4-{[(3S,4S)-3-fluoro-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl]sulfonyl}phenyl)pyridine-2-carboxamide.

[1242]

[1243] MS(ES+ ) m / z 579.3 (M+H) +

[1244] Structural unit: Step i: 4-(pentafluoro-λ 6 -sulfanyl)aniline and tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate; Step iii: 4-bromobenzenesulfonyl chloride; Step iv: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide.

[1245] Example 84: N-[3-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine.

[1246]

[1247] MS (ES + ) m / z 584.3 (M+H) +

[1248] i) Following a procedure similar to that described for Example 67, Steps i to iii, using the appropriate SF5-aniline in Step i and the appropriate sulfonyl chloride in Step iii, synthesize 1-(4-bromobenzenesulfonyl)-N-[3-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1249] ii) To a suspension (purged with N2 gas) of the product obtained in the previous step (200 mg), bis(pinacolato)diboron (107 mg), and potassium acetate (94 mg) in cyclopentyl methyl ether (1.5 mL), add PdCl2(dppf).CH2Cl2 (19 mg). Heat the reaction mixture in a microwave at 100 °C for 2 h. After cooling to room temperature, pour the reaction mixture into water and extract the product into ethyl acetate. Wash the organic layer with brine, dry over MgSO4, and concentrate under reduced pressure to give N-[3-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane yl)benzenesulfonyl]piperidin-4-amine , which is a brown oil (290 mg) and is used in the next step without further purification.

[1250] iii) Following the procedure described for Example 1, Step ii, convert the product obtained in the previous step (290 mg) and 6-bromo-3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridine (135 mg) to the title compound N-[3-(Pentafluoro- λ 6 -thiol)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piper yl)piperidin-4-amine (159 mg), which is a white solid. MS (ES+ ) m / z 602.3 (M+H) + 。

[1251] 1 H NMR (400 MHz, DMSO) δ 8.84 (d, J = 1.7 Hz, 1H), 8.14–8.06 (m, 2H), 7.92–7.84 (m, 3H), 7.77 (dd, J = 9.6, 1.7 Hz, 1H), 7.23 (t, J = 8.2, 8.2 Hz, 1H), 7.00 (t, J = 2.3, 2.3 Hz, 1H), 6.91 (dd, J = 8.0, 2.2 Hz, 1H), 6.78 (dd, J = 8.2, 2.2 Hz, 1H), 6.15 (d, J = 8.1 Hz, 1H), 3.74 (p, J = 6.9, 6.9, 6.8, 6.8 Hz, 1H), 3.60 (dd, J = 10.1, 6.2 Hz, 2H), 3.40 (s, 1H), 2.64–2.52 (m, 2H), 1.97 (dd, J = 13.4, 3.7 Hz, 2H), 1.43 (d, J = 6.9 Hz, 8H).

[1252] Example 85: 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-1H-indole-3-carbonitrile

[1253]

[1254] i) A solution of methanesulfonyl chloride (16 mL) in CH2Cl2 (20 mL) was added dropwise to a cold solution of 4-hydroxycyclohexanone monoethylene ketal (25 g) and Et3N (29 mL) in CH2Cl2 (55 mL) at 0 °C. The reaction mixture was stirred overnight at room temperature. After completion, the reaction mixture was poured into saturated aqueous NaHCO3 and the product was extracted into CH2Cl2. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give 1,4-Dioxaspiro[4.5]decane-8-yl Methanesulfonate , which was a yellow oil (40 g) and was used in the next step without further purification.

[1255] ii) At room temperature, 4-bromobenzenethiol (44.8 g) was added to a suspension of the product (37.3 g) obtained in the previous step and Cs2CO3 (128.7 g) in acetone (400 mL). The reaction mixture was stirred overnight at 60 °C. After concentrating the reaction mixture under reduced pressure, water and ethyl acetate were added. The product was extracted into ethyl acetate, and the combined organic layers were washed with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The brown oil (59 g) obtained was purified on SiO2 using 0% to 100% EtOAc in heptane as the eluent, giving 8-[(4-Bromophenyl)th io]-1,4-dioxaspiro[4.5]decane , which was a clear oil (49 g) that slowly solidified.

[1256] iii) 2N aqueous HCl solution (160 mL) was added to a solution of the product (13.2 g) obtained in the previous step in THF (200 mL), and the reaction mixture was stirred overnight at room temperature. After completion, the organic solvent was removed under reduced pressure, and the remaining aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give 4-[(4-Bromophenyl)thio]cyclohexan-1-one , which was a pale yellow oil (11 g) that was used in the next step without further purification.

[1257] iv) At room temperature, 2-methylpyridine borane complex (1.46 g) was added to a solution of the product (3 g) obtained in the previous step, 4-(pentafluoro-λ 6 -sulfanyl)aniline (2.3 mL), and HOAc (1 mL) in methanol (20 mL). The reaction mixture was stirred overnight at room temperature. After completion, the reaction mixture was concentrated under reduced pressure, and 2N aqueous HCl solution (5 mL) was added after cooling to 0 °C. After stirring for 1 hour at 0 °C, 5N aqueous NaOH solution was added. The product was extracted into EtOAc, and the combined organic layers were washed with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give N-{4-[(4-Bromophenyl)th {[Cyclohexyl]}-4-(pentafluoro-λ 6 -sulfanyl)aniline , which was a white solid (3.2 g) that was used in the next step without further purification.

[1258] v) At room temperature, add (diacetoxyiodo)benzene (1.39 g) to a suspension of the product (1.0 g mg) obtained in the previous step and ammonium carbamate (240 mg) in a mixture of methanol (20 mL) and acetonitrile (20 mL). In an open flask to the atmosphere, stir the reaction mixture at room temperature for 30 minutes. After completion, concentrate the reaction mixture under reduced pressure. At this stage, the cis / trans mixture can be separated on C18, using 10% to 100% acetonitrile in water, to give (4-Bromo (phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfonone (0.47 g) and (4-Bromo (phenyl)[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfonone (0.58 g).

[1259] vi) Under a nitrogen atmosphere, add Pd(PPh3)4 (11 mg) to (4-Bromophenyl)[trans-4-{[4-(pentafluoro-λ 6 - {cyclohexyl[(phenylamino)(thio)]imino}-λ 6 -sulfone (100 mg), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-carbonitrile (62 mg) and NaHCO3 (97 mg) in a suspension in a mixture of 1,4-dioxane (4 mL) and water (1 mL). In a microwave, stir the reaction mixture at 110 °C for 1 h. After cooling to room temperature, extract the product into EtOAc, and dry the organic layer over MgSO4, filter and concentrate under reduced pressure. Purify the obtained brown solid on C18, using 10% to 90% acetonitrile in water as the eluent, to give the title compound 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1H-indole-3-carbonitrile, which is a white solid (27 mg). MS (ES + ) m / z 581.3 (M+H) +

[1260] 1 1H NMR (400 MHz, DMSO) δ 12.29 (s, 1H), 8.34 (s, 1H), 8.04–7.97 (m, 3H), 7.96–7.90 (m, 2H), 7.69 (d, J = 1.3 Hz, 2H), 7.52–7.43 (m, 2H), 6.60 (d, J = 8.9 Hz, 2H), 6.40 (d, J = 7.8 Hz, 1H), 4.22 (s, 1H), 3.25–3.15 (m, H), 3.14–3.04 (m, 1H), 2.12–1.99 (m, 4H), 1.59–1.42 (m, 2H), 1.19 (q, J = 12.4, 12.4, 12.4 Hz, 2H).

[1261] Following a procedure similar to that described for Example 85, Examples 86 to 101 have been prepared using an appropriate borate or boric acid in step vi.

[1262] Examples 86 to 101

[1263] Example 86: [4-(3-Methyl-1H-indazol-5-yl)phenyl][trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1264]

[1265] MS(ES + ) m / z 571.3 (M+H) +

[1266] Structural unit: Step vi: (3-Methyl-1H-indazol-5-yl)boronic acid.

[1267] Example 87: (4-{Imidazo[1,2-a]pyridin-6-yl)phenyl][trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1268]

[1269] MS(ES + ) m / z 557.3 (M+H) +

[1270] Structural unit: Step vi: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1271] Example 88: (4-{Imidazo[1,2-a]pyridin-6-yl)phenyl][cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1272]

[1273] MS(ES + ) m / z 557.3 (M+H) +

[1274] Structural unit: Step vi: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1275] Example 89: (4-{3-Methylimidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1276]

[1277] MS(ES + ) m / z 571.3 (M+H) +

[1278] Structural unit: Step vi: 3-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1279] Example 90: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile.

[1280]

[1281] MS(ES + ) m / z 582.3 (M+H) +

[1282] Structural unit: Step vi: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-3-carbonitrile.

[1283] Example 91: 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide.

[1284]

[1285] MS(ES + ) m / z 561.3 (M+H) +

[1286] Structural unit: Step vi: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide.

[1287] Example 92: N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6-thio)phenyl]amino}cyclohexyl]iminosulfinyl}-[1,1'-biphenyl]-4-carboxamide.

[1288]

[1289] MS(ES + ) m / z 588.3 (M+H) +

[1290] Structural unit: N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide.

[1291] Example 93: (4-{Imidazo[1,2-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1292]

[1293] MS(ES + ) m / z 557.3 (M+H) +

[1294] Structural unit: Step vi: 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1295] Example 94: [trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](4-{[1,2,4]triazolo[1,5-a]pyridin-7-yl}phenyl)(imino)-λ 6 -sulfone.

[1296]

[1297] MS(ES + ) m / z 558.3 (M+H) +

[1298] Structural unit: Step vi: 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,2,4]triazolo[1,5-a]pyridine.

[1299] Example 95: N-methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]iminosulfinyl}-[1,1'-biphenyl]-4-carboxamide.

[1300]

[1301] MS(ES + )m / z 574.3(M+H) +

[1302] Structural unit: Step vi: [4-(methylcarbamoyl)phenyl]boronic acid.

[1303] Example 96: 4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide.

[1304]

[1305] MS(ES + )m / z 560.3(M+H) +

[1306] Structural unit: Step vi: (4-carbamoylphenyl)boronic acid.

[1307] Example 97: N,N-dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide

[1308]

[1309] MS(ES + )m / z 588.3(M+H) +

[1310] Structural unit: Step vi: [3-(dimethylcarbamoyl)phenyl]boronic acid.

[1311] Example 98: N-methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide.

[1312]

[1313] MS(ES + )m / z 574.3(M+H) +

[1314] Structural unit: Step vi: [3-(methylcarbamoyl)phenyl]boronic acid.

[1315] Example 99: 4'-{[trans-4-{[4-(pentafluoro-λ6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide.

[1316]

[1317] MS(ES + ) m / z 560.3 (M+H) +

[1318] Structural unit: Step vi: (3-carbamoylphenyl)boronic acid.

[1319] Example 100: N,N-dimethyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide.

[1320]

[1321] MS(ES + ) m / z 589.3 (M+H) +

[1322] Structural unit: N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyridine-2-carboxamide.

[1323] Example 101: N-methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide.

[1324]

[1325] MS(ES + ) m / z 575.3 (M+H) +

[1326] Structural unit: Step vi: N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyridine-2-carboxamide.

[1327] Example 102: {4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1328]

[1329] i) Following a procedure similar to that described for Example 24, step i, (4-bromophenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (Example 85, step v, 411 mg) was converted to [trans-4- {[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl][4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- 6 -sulfone​ (800 mg), which was a brown oil and was used in the next step without further purification.

[1330] ii) Following a procedure similar to that described for Example 1, step ii, the product obtained in the previous step (125 mg) and 6-bromo-3-(propan-2-yl)[1,2,4]triazolo[4,3-a]pyridine (64 mg) were converted to the title compound {4- [3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]phenyl}[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl) {phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (15 mg), which was a white solid. MS (ES + ) m / z 600.4 (M+H) + .

[1331] 1 H NMR (400 MHz, DMSO) δ 8.84 (t, J = 1.4, 1.4 Hz, 1H), 8.10–8.02 (m, 2H), 8.01–7.94 (m, 2H), 7.87 (dd, J = 9.6, 1.1 Hz, 1H), 7.77 (dd, J = 9.6, 1.6 Hz, 1H), 7.52–7.43 (m, 2H), 6.60 (d, J = 8.9 Hz, 2H), 6.40 (d, J = 7.8 Hz, 1H), 4.30 (s, 1H), 3.74 (hept, J = 6.7, 6.7, 6.5, 6.5, 6.5, 6.5 Hz, 1H), 3.26–3.15 (m, 1H), 3.15–3.07 (m, 1H), 2.03 (q, J = 14.8, 14.1, 14.1 Hz, 4H), 1.52 (t, J = 14.9, 14.9 Hz, 2H), 1.43 (d, J = 6.8 Hz, 6H), 1.20 (t, J = 13.2, 13.2 Hz, 2H).

[1332] Following a procedure similar to that described for Example 102, Examples 103 to 118 have been prepared using appropriate aryl halides.

[1333] Examples 103 to 118

[1334] Example 103: (4-{2-Methylimidazo[1,2-a]pyrazin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1335]

[1336] MS(ES + ) m / z 572.3 (M+H) +

[1337] Structural unit: Step ii: 6-bromo-2-methylimidazo[1,2-a]pyrazine.

[1338] Example 104: (4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1339]

[1340] MS(ES + ) m / z 572.3 (M+H) +

[1341] Structural unit: Step ii: 7-bromo-3-methyl-[1,2,4]triazolo[4,3-a]pyridine.

[1342] Example 105: (4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1343]

[1344] MS(ES + ) m / z 572.4 (M+H) +

[1345] Structural unit: Step vi: 6-bromo-3-methyl-[1,2,4]triazolo[4,3-a]pyridine.

[1346] Example 106: N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-3-carboxamide.

[1347]

[1348] MS(ES + )m / z 589.4(M+H) +

[1349] Structural unit: Step vi: 6-chloro-N,N-dimethylpyridine-3-carboxamide.

[1350] Example 107: N-methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-3-carboxamide.

[1351]

[1352] MS(ES + )m / z 575.3(M+H) +

[1353] Structural unit: Step vi: 6-chloro-N-methylpyridine-3-carboxamide.

[1354] Example 108: 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide.

[1355]

[1356] MS(ES + )m / z 561.3(M+H) +

[1357] Structural unit: Step vi: 5-bromopyridine-2-carboxamide.

[1358] Example 109: N,N-dimethyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide.

[1359]

[1360] MS(ES + )m / z 589.3(M+H) +

[1361] Structural unit: Step vi: 4-chloro-N,N-dimethylpyridine-2-carboxamide.

[1362] Example 110: N-methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6{[4-(Pentafluoro-λ6-sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[1363]

[1364] MS(ES + )m / z 575.3(M+H) +

[1365] Structural unit: Step vi: 4-chloro-N-methylpyridine-2-carboxamide.

[1366] Example 111: 6-(4-{[trans-4-{[4-(Pentafluoro-λ6-sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-3-carboxamide 6 {[4-(Pentafluoro-λ6-sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-3-carboxamide

[1367]

[1368] MS(ES + )m / z 561.4(M+H) +

[1369] Structural unit: Step vi: 6-chloropyridine-3-carboxamide.

[1370] Example 112: 5-(4-{[trans-4-{[4-(Pentafluoro-λ6-sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-2,3-dihydro-1H-isoindol-1-one. 6 {[4-(Pentafluoro-λ6-sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-2,3-dihydro-1H-isoindol-1-one.

[1371]

[1372] MS(ES + )m / z 572.3(M+H) +

[1373] Structural unit: Step vi: 5-bromo-2,3-dihydro-1H-isoindol-1-one.

[1374] Example 113: 6-(4-{[trans-4-{[4-(Pentafluoro-λ6-sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one. 6 {[4-(Pentafluoro-λ6-sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one.

[1375]

[1376] MS(ES + )m / z 586.3(M+H) +

[1377] Structural unit: Step vi: 6-bromo-1,2,3,4-tetrahydroisoquinolin-1-one.

[1378] Example 114: 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfamoyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one.

[1379]

[1380] MS(ES + ) m / z 586.3 (M+H) +

[1381] Structural unit: Step vi: 7-bromo-1,2,3,4-tetrahydroisoquinolin-1-one.

[1382] Example 115: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfamoyl}phenyl)-2,3-dihydro-1H-isoindol-1-one.

[1383]

[1384] MS(ES + ) m / z 572.3 (M+H) +

[1385] Structural unit: Step vi: 6-bromo-2,3-dihydro-1H-isoindol-1-one.

[1386] Example 116: 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfamoyl}phenyl)-2,3-dihydro-1H-indol-2-one.

[1387]

[1388] MS(ES + ) m / z 572.3 (M+H) +

[1389] Structural unit: Step vi: 5-bromo-2,3-dihydro-1H-indol-2-one.

[1390] Example 117: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfamoyl}phenyl)-2,3-dihydro-1H-indol-2-one.

[1391]

[1392] MS(ES + ) m / z 572.3 (M+H) +

[1393] Structural unit: Step vi: 6-bromo-2,3-dihydro-1H-isoindol-1-one.

[1394] Example 118: {4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[1395]

[1396] MS(ES + ) m / z 599.3 (M+H) +

[1397] Structural unit: Step vi: 6-bromo-3-(propan-2-yl)imidazo[1,2-a]pyridine.

[1398] Example 119: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfamoyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one.

[1399]

[1400] i) Following a procedure similar to that described for Example 67, in Step i, [trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl][4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl](imino)-λ 6 -sulfone (Example 102, Step i, 300 mg) was used to prepare the title compound 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfamoyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one (75 mg), which is a white solid. MS(ES + ) m / z 574 (M+H) +

[1401] 11H NMR (400 MHz, DMSO) δ 12.61 (s, 1H), 8.23 (t, J = 1.4, 1.4 Hz, 1H), 8.07–8.00 (m, 2H), 7.86–7.78 (m, 2H), 7.66 (dd, J = 9.8, 1.8 Hz, 1H), 7.51–7.44 (m, 2H), 7.40 (dd, J = 9.8, 1.1 Hz, 1H), 6.60 (d, J = 9.0 Hz, 2H), 6.46 (d, J = 7.8 Hz, 1H), 3.60 (d, J = 11.9 Hz, 2H), 3.42–3.34 (m, 1H), 2.61–2.53 (m, 2H), 2.02–1.93 (m, 2H), 1.51–1.37 (m, 2H).

[1402] Example 120: 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)iminosulfonyl]phenyl}-1H-indole-3-carbonitrile.

[1403]

[1404] i) A suspension of N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine hydrochloride (Example 67, step ii) (5 g) in a mixture of 2N aqueous NaOH (400 mL) and ethyl acetate (100 mL) was stirred at room temperature for 1 hour. The product was extracted into ethyl acetate, and the combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure to give N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine (4.2 g), which was a white solid.

[1405] ii) At room temperature, the product obtained in the previous step (3.55 g) and 4-bromobenzenethiol (2.0 g) were added to a mixture of Cu(I)Br (118 mg) and 2,2'-bipyridine (83 mg) in DMSO (10 mL). The reaction mixture was stirred at 60 °C. After 20 hours, more Cu(I)Br (118 mg) and 2,2'-bipyridine (83 mg) were added, and the reaction mixture was stirred at 60 °C for another 20 hours. After cooling to room temperature, the reaction mixture was poured into water, and the product was extracted into ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The brown oil obtained (6.4 g) was purified on SiO2 using 0% to 25% EtOAc in heptane as the eluent to give 1-[(4-Bromophenyl)thio]-N-[4-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine (3.9 g), which was an off-white solid.

[1406] iii) Following a procedure similar to that described in step v of Example 85, the product (1.8 g) obtained in the previous step was converted to (4-Bromophenyl)(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)(imino)-λ 6 -sulfon one (1.18 g), which was a light brown oil.

[1407] iv) At 0 °C, NaH (152 mg) was added to a solution of the product (1.0 g) obtained in the previous step in THF (10 mL). The reaction mixture was stirred until room temperature was reached, then di-tert-butyl dicarbonate (830 mg) was added. The reaction mixture was stirred at room temperature and, after 20 h, another portion of NaH (152 mg) was added. The reaction was stirred at room temperature for a further 20 h. Upon completion, the reaction mixture was quenched by the addition of saturated aqueous NH4Cl. THF was removed under reduced pressure and the product was extracted into ethyl acetate. The combined organic layers were washed with water, brine, dried over MgSO4, filtered and concentrated under reduced pressure. The yellow oil (4.2 g) obtained was purified on SiO2 using 0% to 5% CH3OH in CH2Cl2 as the eluent, giving N-[(4-Bromophenyl)(oxo)(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino} (Piperidin-1-yl)-λ 6 -sulfanylidene]carbamic acid tert-butyl ester (1.08 g), which was an off-white gum.

[1408] v) Following a procedure similar to that described in step vi of Example 85, the product (205 mg) obtained in the previous step and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-carbonitrile (86 mg) were converted to N-{[4-(3-Cyano-1H-indol-5-yl)phenyl](oxo)(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piper (pyridin-1-yl)-λ 6 -sulfanylidene}carbamic acid tert-butyl ester (175 mg), which was a yellow solid.

[1409] vi) 5N HCl solution in 2-propanol (5 mL) was added to a solution of the product (175 mg) obtained in the previous step in ethyl acetate (10 mL) and the reaction mixture was stirred at room temperature overnight. Upon completion, the reaction mixture was concentrated under reduced pressure. The pale yellow oil (100 mg) obtained was purified on C18 using 30% to 70% acetonitrile in water (containing 0.1% TFA) as the eluent. The white solid obtained was dissolved in saturated aqueous NaHCO3 and the product was extracted into ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue obtained was dissolved in an acetonitrile / water mixture and lyophilized to give the title compound 5-{4- [(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)iminosulfonyl]phenyl}-1H-indole-3-carbonitrile (81 mg), which was a white solid. MS (ES + ) m / z 582.4 (M+H) +

[1410] 1 1H NMR (400 MHz, DMSO) δ 12.35 (s, 1H), 8.34 (s, 1H), 8.02–7.95 (m, 3H), 7.90–7.84 (m, 2H), 7.69 (d, J = 1.2 Hz, 2H), 7.50–7.44 (m, 2H), 6.59 (d, J = 9.0 Hz, 2H), 6.44 (d, J = 7.8 Hz, 1H), 4.45 (s, 1H), 3.73–3.61 (m, 2H), 3.31–3.24 (m, 1H), 2.41 (t, J = 11.3, 11.3 Hz, 2H), 1.95 (d, J = 12.5 Hz, 2H), 1.50–1.37 (m, 2H).

[1411] Following a procedure similar to that described for Example 120, Examples 121 to 125 have been prepared using an appropriate boronic ester or boronic acid in step v.

[1412] Examples 121 to 125

[1413] Example 121: N-Methyl-5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylideneamino]phenyl}pyridine-2-carboxamide.

[1414]

[1415] MS (ES + ) m / z 576.3 (M+H) +

[1416] Structural unit: Step v: N-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide.

[1417] Example 122: 4'-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylideneamino]-[1,1'-biphenyl]-4-carbonitrile.

[1418]

[1419] MS (ES + ) m / z 543.3 (M+H) +

[1420] Structural unit: Step v: (4-Cyanophenyl)boronic acid.

[1421] Example 123: 5-{4-[(4-{[4-(pentafluoro-λ 6{[4-(Pentafluoro-λ6-sulfanyl)phenyl]amino}piperidin-1-yl)(imino)-λ6-sulfonyl]phenyl}-2,3-dihydro-1H-indol-2-one.

[1422]

[1423] MS(ES + ) m / z 573.3 (M+H) +

[1424] Structural unit: Step v: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indol-2-one.

[1425] Example 124: (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)(4-{[4-(pentafluoro-λ6- 6 -sulfanyl)phenyl]amino}piperidin-1-yl)(imino)-λ6- 6 -sulfone.

[1426]

[1427] MS(ES + ) m / z 558.3 (M+H) +

[1428] Structural unit: Step v: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1429] Example 125: 4-{4-[(4-{[4-(pentafluoro-λ6- 6 -sulfanyl)phenyl]amino}piperidin-1-yl)imidosulfonyl]phenyl}pyridine-2-carboxamide.

[1430]

[1431] MS(ES + ) m / z 562.3 (M+H) +

[1432] Structural unit: Step v: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide.

[1433] Example 126: (+)-5-(4-{[trans-4-{[4-(pentafluoro-λ6- 6 -sulfanyl)phenyl]amino}cyclohexyl]imidosulfonyl}phenyl)-1H-indole-3-carbonitrile.

[1434]

[1435] [α] D 20 ° = +7.2°; MS(ES + ) m / z 581.3 (M+H) + 。

[1436] Example 127: (-)-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1H-indole-3-carbonitrile.

[1437]

[1438] [α] D 20 ° = -6.6°; MS(ES + ) m / z 581.3 (M+H) + 。

[1439] The single enantiomer Examples 126 and 127 of the racemic mixture Example 85 can be obtained by chiral separation. 60 mg of the racemic Example 85 was dissolved in ethanol (4 mg / mL). The solution was injected onto a chiral semi-preparative HPLC using a semi-preparative Chiralpak AD-H column (available from Daicel) and an isocratic gradient of 20% EtOH, 15% 2-propanol in heptane as the eluent to obtain: 33 mg of the (+)-enantiomer (Example 126): [α] D 20 ° = +7.2°, and 34 mg of the (-)-enantiomer (Example 127): [α] D 20 ° = -6.6°.

[1440] The absolute configurations of Examples 126 and 127 are not yet known. These compounds are characterized by their optical rotations, which were measured using a Jasco P-2000 polarimeter with the following configuration: tungsten halogen (WI) light source; Glan-Taylor prism polarizer; quartz Faraday cell; and a monitoring wavelength of 589 nm.

[1441] Examples 128 to 131 have been prepared according to a procedure similar to that described for Examples 126 and 127, using appropriate starting materials and a suitable Chiralpak column.

[1442] Examples 128 to 131

[1443] Example 128: (+)-(4-{imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6-thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1444]

[1445] Chiral column: Chiralpak IA. [α] D 20 ° = +4.7°; MS(ES + ) m / z 557.3 (M+H) + .

[1446] Example 129: (-)-(4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1447]

[1448] Chiral column: Chiralpak IA. [α] D 20 ° = -5.4°; MS(ES + ) m / z 557.3 (M+H) + .

[1449] Example 130: (+)-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide.

[1450]

[1451] Chiral column: Chiralpak AD-H. [α] D 20 ° = +2.6°; MS(ES + ) m / z 561.3 (M+H) + .

[1452] Example 131: (-)-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide.

[1453]

[1454] Chiral column: Chiralpak AD-H. [α] D 20 ° = -4.5°; MS(ES+ ) m / z 561.3 (M+H) + 。Biological paper

[1455] Example 132: 1-(4-{2-Methoxy-7-azaspiro[3.5]nonan-7-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1456]

[1457] i) To a solution of N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine hydrochloride (Example 67, Step ii) (1.07 g) and Et3N (1.5 mL) in CH2Cl2 (40 mL) was added 4-fluorobenzene-1-sulfonyl chloride (0.70 g). The reaction mixture was stirred overnight at room temperature. The reaction mixture was quenched by pouring it into water. The product was extracted into CH2Cl2, and the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give 1-(4-Fluorobenzenesulfonyl)-N-[4-(pentafluoro- λ 6 -thiol)phenyl]piperidin-4-amine (1.36 g), which was an off-white solid and was used in the next step without further purification.

[1458] ii) In a capped microwave vial, a mixture of the product obtained in the previous step (100 mg), 2-methoxy-7-azaspiro[3.5]nonane hydrochloride (77 mg) and K2CO in NMP (2 mL) was stirred overnight at 120 °C. After cooling to room temperature, the reaction mixture was poured into water, and the product was extracted into ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo, and the oil obtained was purified on C18 using 20% to 60% acetonitrile in water as the eluent to give the title compound 1-(4-{2-Methoxy-7-azaspiro[3.5]nonan-7-yl}benzenesulf -yl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 9 (24 mg), which was a white solid. MS (ES + ) m / z 596.4 (M+H) +

[1459] 11H NMR (400 MHz, DMSO) δ 7.52–7.44 (t, J = 9.1 Hz, 4H), 7.10–7.03 (d, J = 9.1 Hz, 2H), 6.64–6.56 (d, J = 8.9 Hz, 2H), 6.48–6.41 (d, J = 7.9 Hz, 1H), 3.93–3.85 (p, J = 6.9 Hz, 1H), 3.53–3.45 (d, J = 11.6 Hz, 2H), 3.32–3.29 (m, 3H), 3.29–3.23 (m, 2H), 3.14–3.11 (s, 3H), 2.45–2.36 (t, 2H), 2.20–2.13 (m, 2H), 1.98–1.89 (d, 2H), 1.68–1.55 (m, 6H), 1.47–1.33 (m, 2H).

[1460] Following a procedure similar to that described for Example 132 and using an appropriate heterocycle in step ii, Examples 133 to 137 have been prepared.

[1461] Examples 133 to 137

[1462] Example 133: 8-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1,3,8-triazaspiro[4.5]decane-2,4-dione.

[1463]

[1464] MS (ES + ) m / z 610.4 (M + H) +

[1465] Structural unit: Step ii: 1,3,8-triazaspiro[4.5]decane-2,4-dione.

[1466] Example 134: 8-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2,8-diazaspiro[4.5]decan-1-one.

[1467]

[1468] MS (ES + ) m / z 595.3 (M + H) +

[1469] Structural unit: Step ii: 2,8-diazaspiro[4.5]decan-1-one.

[1470] Example 135: 8-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-3-oxa-1,8-diazaspiro[4.5]decan-2-one.

[1471]

[1472] MS(ES + ) m / z 597.3 (M+H) +

[1473] Structural unit: Step ii: 3-oxa-1,8-diazaspiro[4.5]decan-2-one.

[1474] Example 136: 1-(4-{2-Oxa-7-azaspiro[3.5]nonan-7-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1475]

[1476] MS(ES + ) m / z 568.3 (M+H) +

[1477] Structural unit: Step ii: 2-oxa-7-azaspiro[3.5]nonane.

[1478] Example 137: 1-(4-{8-Oxa-3-azabicyclo[3.2.1]octan-3-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

[1479]

[1480] MS(ES + ) m / z 554.3 (M+H) +

[1481] Structural unit: Step ii: 8-oxa-3-azabicyclo[3.2.1]octane.

[1482] Examples 138 to 140 have been prepared following a procedure similar to that described for Example 24, using the appropriate aryl halide in Step ii.

[1483] Examples 138 to 140

[1484] Example 138: 4-Fluoro-N-methyl-4'-[(4-{[4-(pentafluoro-λ 6-thio)phenyl]amino}piperidin-1-yl)sulfonyl]-[1,1'-biphenyl]-3-carboxamide.

[1485]

[1486] MS(ES + ) m / z 594.4 (M+H) +

[1487] Structural unit: Step ii: 5-bromo-2-fluoro-N-methylbenzamide.

[1488] Example 139: 3-fluoro-N-methyl-4'-[(4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)sulfonyl]-[1,1'-biphenyl]-4-carboxamide.

[1489]

[1490] MS(ES + ) m / z 594.4 (M+H) +

[1491] Structural unit: Step ii: 4-bromo-2-fluoro-N-methylbenzamide.

[1492] Example 140: N-[4-(pentafluoro-λ 6 -thio)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}piperidin-4-amine.

[1493]

[1494] MS(ES + ) m / z 603.4 (M+H) +

[1495] Structural unit: Step ii: 6-bromo-3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazine.

[1496] Examples 141 to 161 have been prepared according to a procedure similar to that described for Example 33, using the appropriate aryl halide in Step ii.

[1497] Examples 141 to 161

[1498] Example 141: N-(propan-2-yl)-4'-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide.

[1499]

[1500] MS(ES + )m / z 603.3(M+H) +

[1501] Structural unit: Step ii: 3-bromo-N-(propan-2-yl)benzamide.

[1502] Example 142: 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-1H-pyrazolo[3,4-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline.

[1503]

[1504] MS(ES + )m / z 573.3(M+H) +

[1505] Structural unit: Step ii: 5-bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine.

[1506] Example 143: N,N-dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridin-3-amine.

[1507]

[1508] MS(ES + )m / z 601.4(M+H) +

[1509] Structural unit: Step ii: 6-bromo-N,N-dimethylimidazo[1,2-a]pyridin-3-amine.

[1510] Example 144: N-cyclopropyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide.

[1511]

[1512] MS(ES + )m / z 601.4(M+H) +

[1513] Structural unit: Step ii: 3-bromo-N-cyclopropylbenzamide.

[1514] Example 145: 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{5H-pyrrolo[3,2-d]pyrimidin-2-yl}benzenesulfonyl)cyclohexyl]aniline.

[1515]

[1516] MS(ES + ) m / z 559.4 (M+H) +

[1517] Structural unit: Step ii: 2-chloro-5H-pyrrolo[3,2-d]pyrimidine.

[1518] Example 146: 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{1H-pyrrolo[2,3-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline.

[1519]

[1520] MS(ES + ) m / z 558.4 (M+H) +

[1521] Structural unit: Step ii: 5-chloro-1H-pyrrolo[2,3-c]pyridine.

[1522] Example 147: 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{1H-pyrazolo[3,4-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline.

[1523]

[1524] MS(ES + ) m / z 559.4 (M+H) +

[1525] Structural unit: Step ii: 5-bromo-1H-pyrazolo[3,4-c]pyridine.

[1526] Example 148: 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)thiophene-2-carboxamide.

[1527]

[1528] MS(ES + ) m / z 567.3 (M+H)+

[1529] Structural unit: Step ii: 4-Bromothiophene-2-carboxamide.

[1530] Example 149: 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{8-Methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline.

[1531]

[1532] MS(ES + ) m / z 572.3 (M+H) +

[1533] Structural unit: Step ii: 6-Bromo-8-methylimidazo[1,2-a]pyridine.

[1534] Example 150: 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-Methyl-1H-pyrazolo[3,4-b]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline.

[1535]

[1536] MS(ES + ) m / z 573.3 (M+H) +

[1537] Structural unit: Step ii: 5-Bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine.

[1538] Example 151: 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[8-(Trifluoromethyl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline.

[1539]

[1540] MS(ES + ) m / z 623.4 (M+H) +

[1541] Structural unit: Step ii: 6-Bromo-8-(trifluoromethyl)imidazo[1,2-a]pyridine.

[1542] Example 152: 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{8-Fluoroimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline.

[1543]

[1544] MS(ES + )m / z 576.4(M+H) +

[1545] Structural unit: Step ii: 6-bromo-8-fluoroimidazo[1,2-a]pyridine.

[1546] Example 153(): 2-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-4H,5H,6H,7H-thieno[3,2-c]pyridin-4-one.

[1547]

[1548] MS(ES + )m / z 593.4(M+H) +

[1549] Structural unit: Step ii: 2-bromo-4H,5H,6H,7H-thieno[3,2-c]pyridin-4-one.

[1550] Example 154: 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H-pyrrolo[1,2-a]pyrazin-1-one.

[1551]

[1552] MS(ES + )m / z 574.4(M+H) +

[1553] Structural unit: Step ii: 7-bromo-1H,2H-pyrrolo[1,2-a]pyrazin-1-one.

[1554] Example 155: 8-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H,3H,4H,5H-pyrrolo[1,2-a][1,4]diazepin -1-one.

[1555]

[1556] MS(ES + )m / z 590.3(M+H) +

[1557] Structural unit: Step ii: 8-bromo-1H,2H,3H,4H,5H-pyrrolo[1,2-a][1,4]diazepin -1-one.

[1558] Example 156: 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one.

[1559]

[1560] MS(ES + ) m / z 576.3 (M+H) +

[1561] Structural unit: Step ii: 7-bromo-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one.

[1562] Example 157: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-8-carboxamide.

[1563]

[1564] MS(ES + ) m / z 601.3 (M+H) +

[1565] Structural unit: Step ii: 6-bromoimidazo[1,2-a]pyridine-8-carboxamide.

[1566] Example 158: 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)furan-2-carboxamide.

[1567]

[1568] MS(ES + ) m / z 551.3 (M+H) +

[1569] Structural unit: Step ii: 4-bromofuran-2-carboxamide.

[1570] Example 159: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6-thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridin-8-amine.

[1571]

[1572] MS(ES + ) m / z 573.3 (M+H) +

[1573] Structural unit: Step ii: 6-bromoimidazo[1,2-a]pyridin-8-amine.

[1574] Example 160: 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-8-carbonitrile.

[1575]

[1576] MS(ES + ) m / z 583.3 (M+H) +

[1577] Structural unit: Step ii: 6-bromoimidazo[1,2-a]pyridine-8-carbonitrile.

[1578] Example 161: 4-(pentafluoro-λ 6 -thio)-N-[trans-4-(4-{3-[(2S)-pyrrolidin-2-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline.

[1579]

[1580] MS(ES + ) m / z 628.4 (M+H) +

[1581] Structural unit: Step ii: (9H-fluoren-9-yl)methyl (2S)-2-{6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl}pyrrolidine-1-carboxylate.

[1582] Following a procedure similar to that described for Example 102 and using an appropriate aryl halide in Step ii, Example 162 has been prepared.

[1583] Example 162: {4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ6 -Sulfone.

[1584]

[1585] MS(ES + ) m / z 601.3 (M+H) +

[1586] Structural unit: Step ii: 6-Bromo-3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazine.

[1587] Examples 163 to 164 have been prepared according to a procedure similar to that described for Examples 126 and 127, using appropriate starting materials and a suitable Chiralpak column.

[1588] Examples 163 to 164

[1589] Example 163: (+)-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1590]

[1591] Chiral column: Chiralpak AD-H. [α] D 20 ° = +2.9°; MS(ES + ) m / z 600.4 (M+H) + .

[1592] Example 164: (-)-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1593]

[1594] Chiral column: Chiralpak AD-H. [α] D 20 ° = -3.4°; MS(ES + ) m / z 600.4 (M+H) + .

[1595] Example 165: N-[4-(pentafluoro-λ 6-Thiol)phenyl]-1-(4-{3-[(3R)-Pyrrolidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-amine.

[1596]

[1597] i) Using a procedure similar to that described for Example 24, (3R)-3-{6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl}pyrrolidine-1-carboxylic acid tert-butyl ester was used in Step ii, and (3R)-3-(6-{4-[(4-{[4-(pentafluoro- λ 6 -thiol)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridin-3-yl)pyrrole yl)piperidin-1-yl}benzenesulfonyl)phenyl]piperidin-4-amine (200 mg) was prepared, which is a yellow solid.

[1598] ii) To a solution of the product obtained in the previous step (200 mg) in ethyl acetate (10 mL) was added a 5N HCl solution in 2-propanol (10 mL), and the reaction mixture was stirred overnight at room temperature. After completion, the reaction mixture was concentrated under reduced pressure. The yellow oil (123 mg) was purified on C18 using 10% to 80% CH3CN in water as the eluent, giving the title compound N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-(4-{3-[(3R)-pyrrolidin-3-yl]- [1,2,4]Triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-amine (75 mg), which is a white solid. MS (ES + ) m / z 629.3 (M+H) +

[1599] 1 1H NMR (400 MHz, DMSO) δ 8.92–8.88 (m, 1H), 8.13–8.08 (m, 2H), 7.92–7.86 (m, 3H), 7.81–7.75 (m, 1H), 7.51–7.44 (m, 2H), 6.63–6.57 (d, J = 8.8 Hz, 2H), 6.50–6.44 (d, 1H), 4.01–3.88 (m, 1H), 3.67–3.57 (m, 2H), 3.40–3.34 (m, 3H), 3.16–3.01 (m, 2H), 3.01–2.91 (m, 1H), 2.62–2.54 (m, 2H), 2.35–2.24 (m, 1H), 2.17–2.07 (m, 1H), 2.02–1.92 (m, 2H), 1.52–1.39 (m, 2H).

[1600] Following a procedure similar to that described for Example 165 and using an appropriate aryl halide in Step i, Example 166 was prepared.

[1601] Example 166: N-[4-(Pentafluoro-λ 6-thiol)phenyl]-1-(4-{3-[(3S)-pyrrolidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-amine.

[1602]

[1603] MS(ES + ) m / z 629.4 (M+H) +

[1604] Structural unit: Step i: tert-butyl (3S)-3-{6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl}pyrrolidine-1-carboxylate.

[1605] Example 167: 1-{4-[3-(azetidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -thiol)phenyl]piperidin-4-amine.

[1606]

[1607] i) Following a procedure similar to that described for Example 24, using benzyl 3-{6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl}azetidine-1-carboxylate in Step ii, has prepared 3-(6-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl) {[1,2,4]Triazolo[4,3-a]pyridin-3-yl}azetidin-1-yl]-[4-[[(4-phenyl)phenyl]sulfonyl]piperidin-1-yl]amine Benzyl carbamate (244 mg), which is a yellow solid.

[1608] ii) A solution of the product obtained in the previous step (244 mg) in TFA (1 mL) was stirred at 65 °C for 3 h. After completion, the reaction mixture was concentrated under reduced pressure. The yellow oil (123 mg) was purified on C18 using 10% to 60% CH3CN in water as the eluent, giving the title compound 1-{4-[3-(Azetidin-3-yl)-[1, {2,4]Triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine (22 mg), which is a white solid. MS(ES + ) m / z 615.4 (M+H) +

[1609] 11H NMR (400 MHz, DMSO) δ 9.15–9.11 (s, 1H), 9.01–8.97 (s, 1H), 8.86–8.80 (t, J = 1.4 Hz, 1H), 8.12–8.04 (m, 2H), 7.98–7.93 (dd, J = 9.7, 1.0 Hz, 1H), 7.93–7.88 (m, 2H), 7.88–7.83 (dd, J = 9.6, 1.6 Hz, 1H), 7.52–7.44 (m, 2H), 6.64–6.57 (d, J = 9.0 Hz, 2H), 6.50–6.45 (s, 1H), 4.88–4.75 (p, J = 8.3 Hz, 1H), 4.53–4.40 (m, 4H), 3.65–3.59 (m, 2H), 3.42–3.29 (s, 1H), 2.63–2.54 (m, 2H), 2.01–1.94 (m, 2H), 1.52–1.40 (m, 2H).

[1610] Example 168: 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(azetidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline.

[1611]

[1612] i) Following a procedure similar to that described for Example 33, using benzyl 3-{6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl}azetidine-1-carboxylate in step ii, there was prepared 3-[6-(4-{[trans-4-{[4-(pentafluoro-λ 6 - {4-[[(4-phenyl)phenyl]sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridin-3-yl]azetidin-1-yl]-[4-[[(4-phenyl)phenyl]sulfonyl]piperidin-1-yl]amine Benzyl 1-{4-[3-(azetidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]phenylsulfonyl}piperidine-1-carboxylate (170 mg), which was a yellow solid.

[1613] ii) A solution of the product obtained in the previous step (170 mg) in TFA (1 mL) was stirred at 65 °C for 3 h. After completion, the reaction mixture was concentrated under reduced pressure. The yellow oil (123 mg) was purified on C18 using 10% to 60% CH3CN in water as the eluent, giving the title compound 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4- {4-[[(4-phenyl)phenyl]sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline (30 mg), which was a white solid. MS (ES + ) m / z 614.4 (M+H) +

[1614] 11H NMR (400 MHz, DMSO) δ 9.15–9.11 (s, 1H), 9.01–8.96 (s, 1H), 8.86–8.83 (t, J = 1.4 Hz, 1H), 8.13–8.05 (m, 2H), 8.04–7.98 (m, 2H), 7.97–7.93 (dd, J = 9.6, 1.0 Hz, 1H), 7.90–7.83 (dd, J = 9.7, 1.7 Hz, 1H), 7.52–7.45 (m, 2H), 6.65–6.58 (d, J = 9.0 Hz, 2H), 6.46–6.41 (s, 1H), 4.87–4.74 (p, J = 8.3 Hz, 1H), 4.53–4.42 (m, 4H), 3.45–3.34 (m, 1H), 3.34–3.19 (m, 1H), 2.08–1.92 (m, 4H), 1.63–1.50 (m, 2H), 1.26–1.14 (m, 2H).

[1615] Examples 169 to 170 have been prepared according to a procedure similar to that described for Example 102, using the appropriate aryl halide in step ii.

[1616] Example 169: {4-[3-(Difluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1617]

[1618] MS (ES + ) m / z 608.3 (M + H) +

[1619] Structural unit: Step ii: 6-Bromo-3-(difluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine.

[1620] Example 170: (4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyrazin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1621]

[1622] MS (ES + ) m / z 573.3 (M + H) +

[1623] Structural unit: Step ii: 6-chloro-3-methyl-[1,2,4]triazolo[4,3-a]pyrazine.

[1624] Example 171: {4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[5-(pentafluoro-λ 6 -sulfanyl)pyridin-2-yl]amino}cyclohexyl](imino)-λ 6 -sulfone.

[1625]

[1626] MS(ES + ) m / z 601.3 (M+H) +

[1627] Structural unit: Step ii: 6-bromo-3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridine.

[1628] Example 172: 5-(pentafluoro-λ 6 -sulfanyl)-N-(1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-yl)pyridin-2-amine.

[1629]

[1630] i) Under a nitrogen atmosphere, tert-butyl 4-aminopiperidine-1-carboxylate (217 mg), 2-chloro-5-(pentafluoro-λ 6 -sulfanyl)pyridine (249 mg), and NaOtBu (145 mg) were added to a solution of Pd(OAc)2 (29 mg) and Josiphos SL J009-1 (58 mg) in THF (10 mL). The reaction mixture was stirred at 100 °C for 18 h, and after cooling to room temperature, the reaction mixture was poured into water, and the product was extracted into CH2Cl2. The combined organic layers were dried over a phase separation filter and concentrated under reduced pressure. The obtained orange solid was purified on SiO2 using 0% to 100% ethyl acetate in heptane as the eluent to give 4-{[5-(Pentafluoro-λ 6 -sulfanyl)pyridin-2-yl]amino}piperidine-1-carboxylic acid tert-butyl ester (247 mg), which was a white solid.

[1631] ii) At 0 °C, 6N HCl solution in 2-propanol (2.5 mL) was added to a solution of the product obtained in the previous step (247 mg) in ethyl acetate (5 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure to give 5-(Pentafluoro-λ 6 -sulfanyl)-N-(piperidin-4-yl)pyridin-2-amine hydrochloride(230 mg), which is a white solid and is used in the next step without further purification.

[1632] iii) To a solution of the product obtained in the previous step (131 mg) and Et3N (0.14 mL) in CH2Cl2 (4 mL) was added 4-bromobenzenesulfonyl chloride (87 mg). The reaction mixture was stirred overnight at room temperature. The reaction mixture was quenched by pouring it into water. The product was extracted into CH2Cl2, and the combined organic layers were dried over a phase separation filter and concentrated in vacuo. The yellow solid obtained was purified on SiO2 using 0% to 100% ethyl acetate in heptane as the eluent to give N-[1-(4-Bromobenzenesulfonyl)piperidin-4-yl]-5-(pentafluoro-λ 6 -sulfanyl)pyridin-2-amine (306 mg), which is a white solid.

[1633] iv) According to the procedure described for Example 1, Step ii, the product obtained in the previous step (50 mg) and [3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]boronic acid (100 mg) were converted to the title compound 5-(Pentafluoro- λ 6 -thiol)-N-(1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin- 4-yl)pyridin-2-amine (10 mg), which is a white solid. MS (ES + ) m / z 603.3 (M+H) + .

[1634] 1 1H NMR (400 MHz, DMSO) δ 8.87–8.82 (t, J = 1.3 Hz, 1H), 8.39–8.34 (d, J = 2.8 Hz, 1H), 8.13–8.06 (m, 2H), 7.92–7.84 (m, 3H), 7.81–7.74 (m, 2H), 7.53–7.47 (d, J = 7.3 Hz, 1H), 6.55–6.48 (d, J = 9.4 Hz, 1H), 3.87–3.68 (m, 1H), 3.64–3.56 (m, 3H), 2.64–2.55 (m, 2H), 2.01–1.94 (m, 2H), 1.59–1.47 (m, 2H), 1.46–1.44 (s, 3H), 1.43–1.41 (s, 3H).

[1635] Following a procedure similar to that described for Example 172, Examples 173 to 174 have been prepared using the appropriate boronic ester / boronic acid in Step iv.

[1636] Example 173: N-[1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-yl]-5-(pentafluoro-λ 6 -sulfanyl)pyridin-2-amine.

[1637]

[1638] MS(ES + )m / z 560.4(M+H) +

[1639] Structural unit: Step iv: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine.

[1640] Example 174: N-[1-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-yl]-5-(pentafluoro-λ 6 -sulfanyl)pyridin-2-amine.

[1641]

[1642] MS(ES + )m / z 575.4(M+H) +

[1643] Structural unit: Step iv: {3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}boronic acid.

[1644] Example 175: 4-{4-[(4-{[5-(pentafluoro-λ 6 -sulfanyl)pyridin-2-yl]amino}piperidin-1-yl)sulfonyl]phenyl}pyridine-2-carboxamide.

[1645]

[1646] MS(ES + )m / z 564.4(M+H) +

[1647] Structural unit: Step iv: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide.

[1648] Following a procedure similar to that described for Example 33 and using the appropriate aryl halide in Step ii, Example 176 has been prepared.

[1649] Example 176: 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(difluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline.

[1650]

[1651] MS(ES + ) m / z 609.3 (M+H) +

[1652] Structural unit: Step ii: 3-bromo-N-(propan-2-yl)benzamide.

[1653] Following a procedure similar to that described for Example 1, Example 177 has been prepared using the appropriate boronic acid / boronate in Step ii.

[1654] Example 177: 4-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}pyridine-2-carboxamide.

[1655]

[1656] MS(ES + ) m / z 563.3 (M+H) +

[1657] Structural unit: Step ii: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide.

[1658] Example 178: 5-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]pyridin-2-amine.

[1659]

[1660] i) At 0 °C, a solution of methanesulfonyl chloride (12 mL) in CH2Cl2 (100 mL) was added dropwise to a solution of tert-butyl N-[(1s,4s)-4-hydroxycyclohexyl]carbamate (25 g) and triethylamine (21 mL) in CH2Cl2 (100 mL). The reaction mixture was stirred overnight at room temperature. Upon completion, the reaction mixture was quenched by pouring into saturated aqueous NaHCO3. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give tert-Butyl N-[(1S,4S)-4-(methylsulfonyloxy)cyclohexyl]carbamate (36.3 g), which was a pale gray solid. The product was used in the next step without further purification.

[1661] ii) 4-Bromobenzen-1-thiol (39.5 g) was added to a suspension of the product obtained in the previous step (34.1 g) and cesium carbonate (94.5 g) in acetone (550 mL). The reaction mixture was stirred at 60 °C overnight. After cooling to room temperature, the reaction mixture was filtered and the solid was washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the resulting oil was purified on SiO2 using 0% to 60% ethyl acetate in heptane as the eluent, giving N-[(1r,4r)- tert-Butyl 4-[(4-bromophenyl)sulfanyl]cyclohexyl]carbamate (25.4 g), which is a white solid.

[1662] iii) At 0 °C, 3-Chloroperoxybenzoic acid (56.5 g) was added to a solution of the product obtained in the previous step (25.3 g) in ethyl acetate (250 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was washed with saturated NaHCO3 solution and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure, giving tert-Butyl N-[(1R,4R)-4-(4-bromobenzenesulfonyl)cyclohexyl]carbamate (23 g), which is a white solid and was used in the next step without further purification.

[1663] iv) To a suspension (purged with N2 gas) of the product obtained in the previous step (2 g), bis(pinacolato)diboron (1.7 g) and potassium acetate (1.1 g) in cyclopentyl methyl ether (15 mL) was added PdCl2(dppf).CH2Cl2 (166 mg). The reaction mixture was heated in a microwave at 100 °C for 2 h. After cooling to room temperature, the reaction mixture was poured into water and the product was extracted into ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure, giving 5- (Pentafluoro-λ 6 -sulfanyl)-N-[(1r,4r)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfon {4-[[(4-phenyl)phenyl]sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]pyridin-2-amine , which is a brown oil and was used in the next step without further purification.

[1664] v) Under a nitrogen atmosphere, Pd(PPh3)4 (248 mg) was added to a solution of the product (2 g) obtained in the previous step, 6-bromo-3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridine hydrochloride (1.43 g), and NaHCO3 (1.44 g) in a mixture of 1,4-dioxane (40 mL) and water (10 mL). In a microwave, the reaction mixture was stirred at 110 °C for 2 h. After cooling to room temperature, the reaction mixture was poured into water, and the product was extracted into ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The brown oil obtained was purified on C18 using 10% to 100% CH3CN in water as the eluent to give tert-butyl N-[(1r,4r)-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]carbamate (2.2 g), which is a white solid.

[1665] vi) At 0 °C, a 6N HCl solution in 2-propanol (4.8 mL) was added to a solution of the product (1.2 g) obtained in the previous step in ethyl acetate (10 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure to give (1R,4R)-4-{4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl yl}cyclohexan-1-amine hydrochloride (1.1 g), which is a brown solid and was used in the next step without further purification.

[1666] vii) Under a nitrogen atmosphere, the product (159 mg) obtained in the previous step, 2-chloro-5-(pentafluoro-λ 6 -sulfanyl)pyridine (99 mg), and NaOtBu (55 mg) were added to a solution of Pd(OAc)2 (12 mg) and Josiphos SL J009-1 (24 mg) in THF (20 mL). The reaction mixture was stirred at 100 °C for 18 h, and after cooling to room temperature, the reaction mixture was poured into water, and the product was extracted into CH2Cl2. The combined organic layers were dried over a phase separation filter and concentrated under reduced pressure. The brown oil obtained was purified on SiO2 using 0% to 70% ethyl acetate in heptane as the eluent to give the title compound 5-(Pentafluoro-λ 6 -sulfanyl)-N-[(1R,4R)-4-{4-[3-(propan-2-yl)- [1,2,4]Triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]pyridin-2-amine (11 mg), which is a white solid. MS (ES + ) m / z 602.3 (M + H) + .

[1667] 11H NMR (400 MHz, DMSO) δ 8.92–8.84 (t, J = 1.4 Hz, 1H), 8.45–8.37 (d, J = 2.8 Hz, 1H), 8.17–8.10 (m, 2H), 8.03–7.96 (m, 2H), 7.91–7.85 (m, 1H), 7.82–7.73 (m, 2H), 7.50–7.43 (d, J = 7.4 Hz, 1H), 6.55–6.47 (d, J = 9.3 Hz, 1H), 3.79–3.70 (dt, J = 13.8, 6.9 Hz, 1H), 3.69–3.60 (s, 1H), 3.46–3.35 (m, 1H), 2.11–1.98 (t, J = 12.3 Hz, 4H), 1.54–1.46 (d, J = 14.0 Hz, 2H), 1.45–1.43 (s, 3H), 1.43–1.41 (s, 3H), 1.35–1.20 (m, 2H).

[1668] Example 179 was prepared according to a procedure similar to that described for Example 178, using the appropriate aryl halide in step v.

[1669] Example 179: 5-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]pyridin-2-amine.

[1670]

[1671] MS (ES + ) m / z 574.4 (M+H) +

[1672] Structural unit: Step v: 6-bromo-3-methyl-[1,2,4]triazolo[4,3-a]pyridine.

[1673] Example 180: 5-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]pyridin-2-amine.

[1674]

[1675] i) Under a nitrogen atmosphere, Pd(PPh3)4 (33 mg) was added to tert-Butyl N-[(1R,4R)-4-(4-bromobenzenesulfonyl)cyclohex yl]carbamate(232 mg, Example 178, Step iii), a solution of {imidazo[1,2-a]pyridin-6-yl}boronic acid (88 mg) and NaHCO3 (179 mg) in a mixture of 1,4-dioxane (4 mL) and water (1 mL). In a microwave, the reaction mixture was stirred at 110 °C for 16 h. After cooling to room temperature, the reaction mixture was poured into water and the product was extracted into ethyl acetate. The combined organic layers were washed with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The brown oil obtained was purified on C18 using 10% to 90% CH3CN in water as the eluent to give N-[(1r, tert-Butyl (1R,4R)-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]carbamate (71 mg), which was a beige foam.

[1676] ii) At 0 °C, a solution of 6N HCl in 2-propanol (3.1 mL) was added to a solution of the product obtained in the previous step (71 mg) in ethyl acetate (2 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure to give (1R,4R)-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexan-1-amine (63 mg), which was a white solid and was used in the next step without further purification.

[1677] iii) Under a nitrogen atmosphere, the product obtained in the previous step (63 mg), 2-chloro-5-(pentafluoro-λ 6 -sulfanyl)pyridine (47 mg) and NaOtBu (25 mg) were added to a solution of Pd(OAc)2 (4 mg) and Josiphos SL J009-1 (12 mg) in THF (4 mL). The reaction mixture was stirred at 100 °C for 18 h and after cooling to room temperature, the reaction mixture was poured into water and the product was extracted into CH2Cl2. The combined organic layers were dried over a phase separation filter and concentrated under reduced pressure. The brown oil obtained was purified on SiO2 using 0% to 70% ethyl acetate in heptane as the eluent to give the title compound 5-(Pentafluoro-λ 6 -sulfanyl)-N-[(1R,4R)-4-(4-{Imidazo[1,2-a]pyridin-6- {4-[[(4-phenyl)phenyl]sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]pyridin-2-amine (3 mg), which was a white solid. MS (ES + ) m / z 559.3 (M + H) + .

[1678] 11H NMR (400 MHz, DMSO) δ 9.15–9.09 (t, J = 1.5 Hz, 1H), 8.42–8.37 (d, J = 2.7 Hz, 1H), 8.06–8.02 (m, 2H), 8.02–8.00 (t, J = 0.8 Hz, 1H), 7.99–7.94 (m, 2H), 7.78–7.74 (dd, J = 9.3, 2.9 Hz, 1H), 7.74–7.64 (m, 3H), 7.49–7.42 (d, J = 7.5 Hz, 1H), 6.55–6.45 (d, J = 9.4 Hz, 1H), 3.75–3.61 (s, 1H), 3.40–3.36 (m, 1H), 2.09–1.98 (m, 4H), 1.56–1.40 (m, 2H), 1.33–1.25 (m, 2H).

[1679] Following a procedure similar to that described for Example 180, using the appropriate boronic acid / boronate in Step i, Example 181 has been prepared.

[1680] Example 181: 5-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[8-methyl-3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]pyridin-2-amine.

[1681]

[1682] MS (ES + ) m / z 616.4 (M+H) +

[1683] Structural unit: Step i: [8-Methyl-3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]boronic acid.

[1684] Example 182: Determination of CCR6 activity

[1685] Human CCR6-CRE reporter gene assay

[1686] Transfect 293FT cells with 2 constructs using TransIT-293 (Mirus). The first construct (pGL4.29, Promega) expresses the luciferase reporter gene luc2P in response to cAMP-induced CREB binding to the CRE element in its promoter. The second construct contains the open reading frame of human CCR6 in the pUNO1 backbone under the control of the enhanced CMV promoter (InVivoGen). After 48 h of transfection, harvest the cells and dilute them to 750,000 cells / ml in medium (DMEM, 10% FBS, 1x pen / strep (Gibco 15140)). Serial dilute the compounds 2.5-fold in DMSO. Make further dilutions in assay medium (DMEM, 10% FBS, 1x pen / strep, 6 μM forskolin, 6 nM CCL20). Add 4 μl of the compound solution to a white MW384 plate, then add 20 μl of the cell suspension. The final DMSO concentration in the assay is 0.1%. Place the MW384 plate in an incubator at 37 °C, 5% CO2 for 5 h. Determine luciferase activity by adding 24 μl of 2.5-fold diluted BriteLite luciferase solution (Perkin Elmer), then performing luminescence measurements using a VICTOR microplate reader (Perkin Elmer). To de-select compounds that do not specifically bind to CCR6, the assay was also performed with transfected 293FT cells in which CCR6 was replaced with an empty vector using the same backbone. Use a four-parameter dose-response model with GraphPad Prism 9 to determine the relative-LogIC50.

[1687] CHO-K1 CCR6 chemotaxis assay against CCL20

[1688] Cells overexpressing human CCR6 (DiscoverX, cAMP Hunter) were used in the chemotaxis assay TMCHO-K1 CCR6Gi cell line). The growth medium for these cells consisted of DMEM / F12, non-essential amino acids (1xNEAA, Gibco 11140050), 10% FBS, and 1x pen / strep (Gibco 15140). For the chemotaxis assay, a Corning Transwell plate (Corning 351164) with an 8-μm pore size was used. Trypsin was used to harvest the cells, which were diluted to 4×10^6 cells / ml in chemotaxis medium (DMEM, 0.25% BSA, pen / strep). The compounds were serially diluted four-fold in DMSO. Further dilutions were made in chemotaxis medium. Before starting the assay, the cells were incubated with the test compounds at 37 °C for 30 min (2×10^6 cells / ml). The final DMSO concentration in the assay was 0.2%. The wells of the Transwell plate were filled with 200 μl of chemotaxis medium containing 100 ng / ml CCL20 (R&D systems 360-MP). 50 μl of the cell / compound suspension was added to the inserts of the Transwell plate (100,000 cells / insert). The Transwell plate was placed in an incubator at 37 °C, 5% CO2 for 4 h. After 4 h, CellTiter Glo (Promega) was used to quantify the number of migrated cells. The percentage inhibition values were calculated based on the low and high signals obtained with 0.2% DMSO in chemotaxis medium without and with CCL20, respectively. The relative-LogIC50 was determined using a four-parameter dose-response model with GraphPad Prism 9.

[1689] CD4+ T cell chemotaxis assay against CCL20

[1690] Human CD4+ T cells were isolated from the buffy coat of healthy donors using a CD4+ T cell isolation kit (Miltenyi Biotec 130 - 096 - 533). The isolated T cells were stimulated overnight with anti - CD3 and anti - CD28 antibodies (Biolegend 300314 / 302934) in growth medium (RPMI1640, 10% heat - inactivated FBS, 1x pen / strep (Gibco 15140)). For the chemotaxis assay, a Corning Transwell plate (Corning 3388) with a pore size of 5 μm was used. The T cells were counted and diluted to 6*10^6 cells / ml in chemotaxis medium (RPMI1640, 1% BSA, pen / strep). The compound was serially diluted four - fold in DMSO. Further dilution was performed in chemotaxis medium. Before initiating the assay, the cells were incubated with the test compound at 37 °C for 30 min (3*10^6 cells / ml). The final DMSO concentration in the assay was 0.2%. The wells of the Transwell plate were filled with 200 μl of chemotaxis medium containing 150 ng / ml CCL20 (R&D systems 360 - MP). 50 μl of the cell / compound suspension was added to the insert of the Transwell plate (150,000 cells / insert). The Transwell plate was placed in an incubator at 37 °C, 5% CO2 for 3 h. After 3 h, CellTiter Glo (Promega) was used to quantify the number of migrated cells. The percentage of inhibition values was calculated based on the low signal and high signal obtained with 0.2% DMSO in chemotaxis medium without and with CCL20, respectively. The relative - LogIC50 was determined using a four - parameter dose - response model with GraphPad Prism 9.

[1691] The following table presents the data of the selected compounds:

[1692] Table 1: CCR6 - CRE reporter gene assay

[1693]

[1694]

[1695]

[1696]

[1697] Table 2: CHO - K1 CCR6 chemotaxis assay

[1698]

[1699]

[1700]

[1701]

[1702]

[1703]

[1704] Table 3: CD4+ T Cell Chemotaxis Assay

[1705]

[1706]

[1707]

[1708]

[1709] Aspect:

[1710] Aspect 1. A compound of formula (I),

[1711]

[1712] wherein

[1713] X 1 is CH or N;

[1714] X 2 is CH or N;

[1715] X 3 is CH or N;

[1716] X 4 is O or NH;

[1717] X 5 is CH or N;

[1718] R 1 is aryl, heterocyclic group or heteroaryl, wherein the aryl, heterocyclic group and heteroaryl are optionally substituted by one or more R 1a substituents;

[1719] R 1a is C 1-6 alkyl, cyano, -NR 1b R 1c -C 1-6 alkyl-NR 1b R 1c oxo, -CONR1b R 1c 、 -PO(Me)2, hydroxy, C 3-6 cycloalkyl, -C 1-6 alkyl-C 1-6 alkoxy, C 3-6 heterocyclic group, halo-C 1-6 alkyl, halo, C 1-6 alkoxy;

[1720] R 1b is hydrogen, C 3-6 cycloalkyl or C 1-6 alkyl;

[1721] R 1c is hydrogen, C 3-6 cycloalkyl or C 1-6 alkyl;

[1722] R 2 is hydrogen or halogen;

[1723] R 3 is hydrogen or halogen;

[1724] R 4 is hydrogen, C 1-6 alkyl or halogen;

[1725] R 5 is hydrogen, halogen or C 1-6 alkyl;

[1726] R 6 is hydrogen or -SF5, where R 6 and R 7 must be different;

[1727] R 7 is hydrogen or -SF5, where R 6 and R 7 must be different;

[1728] or a pharmaceutically acceptable salt thereof.

[1729] Aspect 2. The compound according to Aspect 1, wherein

[1730] R 1a is C 1-6 alkyl, cyano, oxo, -CONR 1b R 1c 、 -PO(Me)2, hydroxy, C 3-6 cycloalkyl, -C 1-6 alkyl C 1-6 alkoxy, halo-C 1-6 alkyl, halo, C 1-6 alkoxy;

[1731] R1b is hydrogen or C 1-6 alkyl;

[1732] R 1c is hydrogen or C 1-6 alkyl;

[1733] X 5 is CH;

[1734] R 5 is hydrogen;

[1735] or a pharmaceutically acceptable salt thereof.

[1736] Aspect 3. The compound or a pharmaceutically acceptable salt thereof according to Aspect 1 or 2, wherein X 1 is CH.

[1737] Aspect 4. The compound or a pharmaceutically acceptable salt thereof according to Aspect 1 or 2, wherein X 1 is N.

[1738] Aspect 5. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 4, wherein X 2 is CH.

[1739] Aspect 6. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 4, wherein X 2 is N. Aspect 7. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 6, wherein X 3 is CH.

[1740] Aspect 8. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 6, wherein X 3 is N.

[1741] Aspect 9. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 8, wherein X 4 is O.

[1742] Aspect 10. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 8, wherein X 4 is NH.

[1743] Aspect 11. The compound or a pharmaceutically acceptable salt thereof according to Aspect 1 or any one of Aspects 3 to 10, wherein X 5 is N.

[1744] Aspect 12. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 10, wherein X 5 is CH.

[1745] Aspect 13. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 2, 4 to 5, 7, 9 or 12, wherein X 1 is N, X2 is CH, X 3 is CH, X 4 is O and X 5 is CH.

[1746] Aspect 14. The compound or its pharmaceutically acceptable salt according to any one of Aspects 1 to 3, 5, 7, 9 or 12, wherein X 1 is CH, X 2 is CH, X 3 is CH, X 4 is O and X 5 is CH.

[1747] Aspect 15. The compound or its pharmaceutically acceptable salt according to any one of Aspects 1 to 2, 4, 6 to 7, 9 or 12, wherein X 1 is N, X 2 is N, X 3 is CH, X 4 is O and X 5 is CH.

[1748] Aspect 16. The compound or its pharmaceutically acceptable salt according to any one of Aspects 1 to 2, 4 to 5, 8 to 9 or 12, wherein X 1 is N, X 2 is CH, X 3 is N, X 4 is O and X 5 is CH.

[1749] Aspect 17. The compound or its pharmaceutically acceptable salt according to any one of Aspects 1 to 3, 5, 7, 10 or 12, wherein X 1 is CH, X 2 is CH, X 3 is CH, X 4 is NH and X 5 is CH.

[1750] Aspect 18. The compound or its pharmaceutically acceptable salt according to any one of Aspects 1 to 2, 4 to 5, 7, 10 or 12, wherein X 1 is N, X 2 is CH, X 3 is CH, X 4 is NH and X 5 is CH.

[1751] Aspect 19. The compound or its pharmaceutically acceptable salt according to any one of Aspects 1 to 18, wherein R 1is azaspiro[nonane]yl, triazaspiro[decane]yl, diazaspiro[decane]yl, oxadiazaspiro[decane]yl, oxazaspiro[nonane]yl, oxazaspirobicyclooctyl, pyrazolopyridinyl, pyrrolopyrimidinyl, pyrrolopyridinyl, thienyl, thienopyridinyl, pyrrolopyrazinyl, pyrrolodiazinyl yl, furyl, indazolyl, indolyl, isoindolinyl, triazolopyridinyl, imidazopyridinyl, imidazopyrazinyl, indolinyl, phenyl, pyridinyl, triazolopyridazinyl, isoquinolinyl, pyridazinyl, triazolopyrazinyl, pyrrolotriazinyl or spirocyclopropaneisoindolinyl, wherein azaspiro[nonane]yl, triazaspiro[decane]yl, diazaspiro[decane]yl, oxadiazaspiro[decane]yl, oxazaspiro[nonane]yl, oxazaspirobicyclooctyl, pyrazolopyridinyl, pyrrolopyrimidinyl, pyrrolopyridinyl, thienyl, thienopyridinyl, pyrrolopyrazinyl, pyrrolodiazinyl yl, furyl, indazolyl, indolyl, isoindolinyl, triazolopyridinyl, imidazopyridinyl, imidazopyrazinyl, indolinyl, phenyl, pyridinyl, triazolopyridazinyl, isoquinolinyl, pyridazinyl, triazolopyrazinyl, pyrrolotriazinyl and spirocyclopropaneisoindolinyl are optionally substituted with one or more R 1a substituents.

[1752] Aspect 20. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 19, wherein R 1 is indazolyl, indolyl, isoindolinyl, triazolopyridinyl, imidazopyridinyl, imidazopyrazinyl, indolinyl, phenyl, pyridinyl, triazolopyridazinyl, isoquinolinyl, pyridazinyl, triazolopyrazinyl, pyrrolotriazinyl or spirocyclopropaneisoindolinyl, wherein indazolyl, indolyl, isoindolinyl, triazolopyridinyl, imidazopyridinyl, imidazopyrazinyl, indolinyl, phenyl, pyridinyl, triazolopyridazinyl, isoquinolinyl, pyridazinyl, triazolopyrazinyl, pyrrolotriazinyl and spirocyclopropaneisoindolinyl are optionally substituted with one or more R 1a substituents.

[1753] Aspect 21. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 20, wherein R 1 is indazolyl, indolyl, pyridinyl, triazolopyridinyl, phenyl or imidazopyridinyl, wherein indazolyl, indolyl, pyridinyl, triazolopyridinyl, phenyl and imidazopyridinyl are optionally substituted with one or more R 1a substituents.

[1754] Aspect 22. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 21, wherein R 1is methylindazolyl, cyano - indolyl, cyano - indazolyl, oxo - isoindolinyl, carbamoylpyridyl, methyl - triazolopyridyl, imidazopyridyl, cyano - imidazopyridyl, imidazopyrazinyl, methylimidazopyridyl, carbamoylimidazopyridyl, isopropyl - triazolopyridyl, triazolopyridyl, carbamoylindazolyl, oxo - dihydroindolyl, carbamoyl - triazolopyridyl, cyano - triazolopyridyl, (dimethylcarbamoyl)phenyl, methylimidazopyrazinyl, (dimethylcarbamoyl)pyridyl, (methylcarbamoyl)phenyl, (methylcarbamoyl)pyridyl, oxo - triazolopyridyl, carbamoylphenyl, isopropyl - triazolopyridazinyl, oxo - dihydro - isoquinolinyl, carbamoylpyridazinyl, dimethylphosphorylphenyl, isopropyl - triazolopyrazinyl, oxo - pyridyl, oxo - pyrrolotriazinyl, hydroxypyridyl, (dimethylcarbamoyl)pyridyl, oxo - spiropropane dihydroindolyl, methoxyazaspiro nonanyl, oxo - triazaspiro decanyl, oxo - diazaspiro decanyl, oxo - oxadiazaspiro decanyl, oxaazaspiro nonanyl, oxaazabicyclo octanyl, carbamoylfluorophenyl, propyltriazolopyrazinyl, isopropylcarbamoylphenyl, methylpyrazolopyridyl, N,N - dimethylamineimidazopyridyl, cyclopropylcarbamoylphenyl, pyrrolopyrimidyl, pyrrolopyridyl, pyrazolopyridyl, carbamoylthienyl, methylimidazopyridyl, (trifluoromethyl)imidazopyridyl, fluoroimidazopyridyl, oxo - thiophenopyridyl, oxo - pyrrolopyrazinyl, oxo - pyrrolodiaz yl, carbamoylimidazopyridyl, furan carboxamide, cyano - imidazopyridyl, pyrrolidinyl - triazolopyridyl, propyl - triazolopyrazinyl or azetidinyl - triazolopyridyl.

[1755] Aspect 23. The compound or its pharmaceutically acceptable salt according to any one of Aspects 1 to 22, wherein R 1is methylindazolyl, cyanoindolyl, cyanoindazolyl, oxoisoindolinyl, carbamoylpyridyl, methyl-triazolopyridyl, imidazopyridyl, cyanoimidazopyridyl, imidazopyrazinyl, methylimidazopyridyl, carbamoylimidazopyridyl, isopropyl-triazolopyridyl, triazolopyridyl, carbamoylindazolyl, oxodihydroindolyl, carbamoyl-triazolopyridyl, methyl-triazolopyridyl, methyl-triazolopyridyl, cyano-triazolopyridyl, (dimethylcarbamoyl)phenyl, methylimidazopyrazinyl, (dimethylcarbamoyl)pyridyl, (methylcarbamoyl)phenyl, (methylcarbamoyl)pyridyl, oxo-triazolopyridyl, carbamoylphenyl, carbamoylpyridyl, isopropyl-triazolopyridazinyl, oxo-dihydroisoquinolinyl, carbamoylpyridazinyl, dimethylphosphorylphenyl, oxoisoindolinyl, oxodihydroindolyl, oxo-dihydroisoquinolinyl, isopropyl-triazolopyrazinyl, oxo-pyridyl, oxo-dihydroisoquinolinyl, oxo-pyrrolotriazinyl, hydroxypyridyl, methyl-triazolopyridyl, imidazopyridyl, triazolopyridyl, carbamoylphenyl, carbamoylpyridyl, (dimethylcarbamoyl)pyridyl, oxospiropropanedihydroindolyl.

[1756] Aspect 24. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 23, wherein R 1 is methyl-indazolyl, cyano-indolyl, carbamoyl-pyridyl, methyl-imidazopyridyl, methyl-triazolopyridyl, isopropyl-triazolopyridyl, cyano-indazolyl, (methylcarbamoyl)phenyl, imidazopyridyl, cyanoimidazopyridyl.

[1757] Aspect 25. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 24, wherein R 1a is methoxy, fluoro, -CONH[(CH(CH3)2], -CONH(cyclopropyl), dimethylamino, -CF3, pyrrolidinyl, azetidinyl, methyl, cyano, oxo, -CONH2, isopropyl, -CON(Me)2, -CH2-O-CH3, -CONH(Me), -PO(Me)2, -OH.

[1758] Aspect 26. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 25, wherein R 1a is methyl, cyano, oxo, -CONH2, isopropyl, -CON(Me)2, -CH2-O-CH3, -CONH(Me), -PO(Me)2, -OH.

[1759] Aspect 27. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 26, wherein R 1ais methyl, cyano, -CONH2, isopropyl, -CONH(Me).

[1760] Aspect 28. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 27, wherein R 2 is hydrogen, fluorine or -CF3.

[1761] Aspect 29. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 28, wherein R 2 is hydrogen. Aspect 30. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 29, wherein R 3 is hydrogen, fluorine, chlorine or -CF3.

[1762] Aspect 31. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 30, wherein R 3 is hydrogen. Aspect 32. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 31, wherein R 4 is hydrogen or fluorine. Aspect 33. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 32, wherein R 4 is hydrogen. Aspect 34. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 33, wherein R 6 is -SF5.

[1763] Aspect 35. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 34, wherein R 7 is hydrogen.

[1764] Aspect 36. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 35, wherein R 5 is hydrogen. Aspect 37. The compound according to any one of Aspects 1 to 3, 5 to 12, 14, 17 or 19 to 36, wherein the compound is a compound of formula (I'),

[1765]

[1766] or a pharmaceutically acceptable salt thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X 2 , X 3 , X 4 and X 5 are as defined in any one of Aspects 1 to 3, 5 to 12, 14, 17 or 19 to 36, and X 1 is CH. Aspect 38. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 5, 7, 9 to 10, 12 to 37, wherein

[1767] X 1 is CH or N,

[1768] X 2 is CH,

[1769] X 3 is CH,

[1770] X 4 is O or NH,

[1771] X 5 is CH,

[1772] R 1 is indazolyl, indolyl, pyridyl, triazolopyridyl, phenyl or imidazopyridyl, wherein indazolyl, indolyl, pyridyl, triazolopyridyl, phenyl and imidazopyridyl are optionally substituted by one or more R 1a substituents,

[1773] R 1a is methyl, cyano, -CONH2, isopropyl, -CONH(Me),

[1774] R 2 is hydrogen,

[1775] R 3 is hydrogen,

[1776] R 4 is hydrogen,

[1777] R 5 is hydrogen,

[1778] R 6 is -SF5,

[1779] R 7 is hydrogen.

[1780] Aspect 39. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 5, 7, 9 to 10, 12 to 38, wherein

[1781] X 1 is CH or N,

[1782] X 2 is CH,

[1783] X 3 is CH,

[1784] X 4 is O or NH,

[1785] X 5 is CH,

[1786] R1 be methyl-indazolyl, cyano-indolyl, carbamoyl-pyridyl, methyl-imidazopyridyl, methyl-triazolopyridyl, isopropyl-triazolopyridyl, cyano-indazolyl, (methylcarbamoyl)phenyl, imidazopyridyl, cyanoimidazopyridyl,

[1787] R 2 be hydrogen,

[1788] R 3 be hydrogen,

[1789] R 4 be hydrogen,

[1790] R 5 be hydrogen,

[1791] R 6 be -SF5,

[1792] R 7 be hydrogen.

[1793] Aspect 40. The compound or its pharmaceutically acceptable salt according to any one of Aspects 1 to 39, wherein the compound is selected from:

[1794] 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[1795] 1-[4-(3-Methyl-2H-indazol-5-yl)benzenesulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[1796] 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indole-3-carbonitrile

[1797] 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indazole-3-carbonitrile

[1798] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[cis-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline

[1799] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline

[1800] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile

[1801] 5-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile

[1802] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one

[1803] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[1804] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[1805] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[1806] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[1807] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one

[1808] N,N-dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide

[1809] N-methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide

[1810] 6-(4-{[cis-4-{[4-(pentafluoro-λ 6-thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[1811] 4-(pentafluoro-λ 6 -thio)-N-[cis-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[1812] N,N-dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[1813] N,N-dimethyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[1814] N-methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[1815] N-methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[1816] 4'-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[1817] 1-(4-{imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine

[1818] 6-{4-[(4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[1819] 6-{4-[(4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide

[1820] 1-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6-Thiol)phenyl]piperidin-4-amine

[1821] N-[4-(Pentafluoro-λ 6 -Thiol)phenyl]-1-{4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[1822] N-[4-(Pentafluoro-λ 6 -Thiol)phenyl]-1-{4-[3-(Propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[1823] 1-{4-[3-(Methoxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(Pentafluoro-λ 6 -Thiol)phenyl]piperidin-4-amine

[1824] 1-(4-{3-Cyclopentyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(Pentafluoro-λ 6 -Thiol)phenyl]piperidin-4-amine

[1825] 6-{4-[(4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[1826] 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[1827] 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide

[1828] 4-(Pentafluoro-λ 6 -Thiol)-N-[trans-4-{4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[1829] 4-(Pentafluoro-λ 6 -Thiol)-N-[trans-4-(4-{[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[1830] 5-(4-{[trans-4-{[4-(Pentafluoro-λ6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carboxamide

[1831] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carbonitrile

[1832] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide

[1833] 4-(pentafluoro-λ 6 -thio)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[1834] 4-(pentafluoro-λ 6 -thio)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl}benzenesulfonyl)cyclohexyl]aniline

[1835] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carbonitrile

[1836] 4-(pentafluoro-λ 6 -thio)-N-[trans-4-(4-{2-methylimidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[1837] 4-(pentafluoro-λ 6 -thio)-N-[trans-4-(4-{imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[1838] N,N-dimethyl-6-(4-{[cis-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[1839] N,N-dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[1840] N-methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6-thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[1841] N-methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[1842] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[1843] 4-(pentafluoro-λ 6 -thio)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[1844] 4-(pentafluoro-λ 6 -thio)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[1845] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2-dihydropyridin-2-one

[1846] 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one

[1847] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one

[1848] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-3H,4H-pyrrolo[2,1-f][1,2,4]triazin-4-one

[1849] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridin-2-ol

[1850] 4-(pentafluoro-λ 6-Thiol)-N-[trans-4-{[4'-(dimethylphosphoryl)-[1,1'-biphenyl]-4-yl]sulfonyl}cyclohexyl]aniline

[1851] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one

[1852] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one

[1853] 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[1854] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[1855] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridazine-3-carboxamide

[1856] 4-(pentafluoro-λ 6 -Thiol)-N-[trans-4-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[1857] 4-(pentafluoro-λ 6 -Thiol)-N-[trans-4-{4-[8-methyl-3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[1858] 5'-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2'-one

[1859] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[1860] 1-(2-Fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[1861] 1-(3-Fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[1862] 1-[(6-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[1863] 1-[(5-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[1864] 6-{2-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[1865] 1-(3-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[1866] 6-{3-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[1867] 1-(2-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[1868] 1-[(5-{imidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[1869] 6-{5-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-2-yl}imidazo[1,2-a]pyridine-3-carbonitrile

[1870] 1-[(6-{Imidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[1871] 6-{6-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-3-yl}imidazo[1,2-a]pyridine-3-carbonitrile

[1872] 1-(2-chloro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[1873] 6-{3-chloro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[1874] 6-{4-[(4-{[3-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[1875] 1-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[3-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[1876] 4-(4-{[(3S,4S)-3-fluoro-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl]sulfonyl}phenyl)pyridine-2-carboxamide

[1877] N-[3-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[1878] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-1H-indole-3-carbonitrile

[1879] [4-(3-methyl-1H-indazol-5-yl)phenyl][trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[1880] (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfon

[1881] (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfon

[1882] (4-{3-Methylimidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfon

[1883] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]imidosulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[1884] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]imidosulfonyl}phenyl)pyridine-2-carboxamide

[1885] N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]imidosulfonyl}-[1,1'-biphenyl]-4-carboxamide

[1886] (4-{Imidazo[1,2-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfon

[1887] [trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](4-{[1,2,4]triazolo[1,5-a]pyridin-7-yl}phenyl)(imino)-λ 6 -sulfon

[1888] N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]imidosulfonyl}-[1,1'-biphenyl]-4-carboxamide

[1889] 4'-{[trans-4-{[4-(pentafluoro-λ6 -thio)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide

[1890] N,N-dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide

[1891] N-methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide

[1892] 4'-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide

[1893] N,N-dimethyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[1894] N-methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[1895] {4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[1896] (4-{2-methylimidazo[1,2-a]pyrazin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[1897] (4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[1898] (4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ6 -thiol)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[1899] N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-3-carboxamide

[1900] N-Methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-3-carboxamide

[1901] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[1902] N,N-Dimethyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[1903] N-Methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[1904] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-3-carboxamide

[1905] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-2,3-dihydro-1H-isoindol-1-one

[1906] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[1907] 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thiol)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[1908] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6-thio)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-2,3-dihydro-1H-isoindol-1-one

[1909] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-2,3-dihydro-1H-indol-2-one

[1910] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-2,3-dihydro-1H-indol-2-one

[1911] {4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[1912] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[1913] 5-{4-[(4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)sulfinyl]phenyl}-1H-indole-3-carbonitrile

[1914] N-methyl-5-{4-[(4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)sulfinyl]phenyl}pyridine-2-carboxamide

[1915] 4'-[(4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)sulfinyl]-[1,1'-biphenyl]-4-carbonitrile

[1916] 5-{4-[(4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)sulfinyl]phenyl}-2,3-dihydro-1H-indol-2-one

[1917] (4-{imidazo[1,2-a]pyridin-6-yl}phenyl)(4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)(imino)-λ 6 -sulfone

[1918] 4-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinyl]phenyl}pyridine-2-carboxamide

[1919] (+)-5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1H-indole-3-carbonitrile

[1920] (-)-5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1H-indole-3-carbonitrile

[1921] (+)-(4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[1922] (-)-(4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[1923] (+)-4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[1924] (-)-4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide

[1925] 1-(4-{2-Methoxy-7-azaspiro[3.5]nonan-7-yl}benzenesulfonyl)-N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine,

[1926] 8-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1,3,8-triazaspiro[4.5]decane-2,4-dione,

[1927] 8-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2,8-diazaspiro[4.5]decan-1-one,

[1928] 8-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-3-oxa-1,8-diazaspiro[4.5]decan-2-one,

[1929] 1-(4-{2-oxa-7-azaspiro[3.5]nonan-7-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine,

[1930] 1-(4-{8-oxa-3-azabicyclo[3.2.1]octan-3-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine,

[1931] 4-Fluoro-N-methyl-4'-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]-[1,1'-biphenyl]-3-carboxamide,

[1932] 3-Fluoro-N-methyl-4'-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]-[1,1'-biphenyl]-4-carboxamide,

[1933] N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}piperidin-4-amine,

[1934] N-(Propan-2-yl)-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide,

[1935] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-1H-pyrazolo[3,4-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline,

[1936] N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridin-3-amine,

[1937] N-Cyclopropyl-4'-{[trans-4-{[4-(pentafluoro-λ 6-thio)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide,

[1938] 4-(Pentafluoro-λ 6 -thio)-N-[trans-4-(4-{5H-pyrrolo[3,2-d]pyrimidin-2-yl}benzenesulfonyl)cyclohexyl]aniline,

[1939] 4-(Pentafluoro-λ 6 -thio)-N-[trans-4-(4-{1H-pyrrolo[2,3-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline,

[1940] 4-(Pentafluoro-λ 6 -thio)-N-[trans-4-(4-{1H-pyrazolo[3,4-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline,

[1941] 4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)thiophene-2-carboxamide,

[1942] 4-(Pentafluoro-λ 6 -thio)-N-[trans-4-(4-{8-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline,

[1943] 4-(Pentafluoro-λ 6 -thio)-N-[trans-4-(4-{3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline,

[1944] 4-(Pentafluoro-λ 6 -thio)-N-[trans-4-{4-[8-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline,

[1945] 4-(Pentafluoro-λ 6 -thio)-N-[trans-4-(4-{8-fluoroimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline,

[1946] 2-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-4H,5H,6H,7H-thieno[3,2-c]pyridin-4-one,

[1947] 7-(4-{[trans-4-{[4-(Pentafluoro-λ 6-thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H-pyrrolo[1,2-a]pyrazin-1-one,

[1948] 8-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H,3H,4H,5H-pyrrolo[1,2-a][1,4]diazepin -1-one,

[1949] 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one,

[1950] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-8-carboxamide,

[1951] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)furan-2-carboxamide,

[1952] 4-(pentafluoro-λ 6 -thio)-N-[trans-4-(4-{8-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline,

[1953] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-8-carbonitrile,

[1954] 4-(pentafluoro-λ 6 -thio)-N-[trans-4-(4-{3-[(2R)-pyrrolidin-2-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline,

[1955] {4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone,

[1956] (+)-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone,

[1957] (-)-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone,

[1958] N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-(4-{3-[(3R)-pyrrolidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-amine,

[1959] N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-(4-{3-[(3S)-pyrrolidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-amine,

[1960] 1-{4-[3-(azetidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine,

[1961] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(azetidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline;

[1962] {4-[3-(difluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone;

[1963] (4-{3-methyl-[1,2,4]triazolo[4,3-a]pyrazin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone;

[1964] {4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[5-(Pentafluoro-λ 6 -sulfanyl)pyridin-2-yl]amino}cyclohexyl](imino)-λ 6 -sulfone;

[1965] 5-(Pentafluoro-λ 6 -sulfanyl)-N-(1-{4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-yl)pyridin-2-amine;

[1966] N-[1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-yl]-5-(pentafluoro-λ 6 -sulfanyl)pyridin-2-amine;

[1967] N-[1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-yl]-5-(pentafluoro-λ 6 -sulfanyl)pyridin-2-amine;

[1968] 4-{4-[(4-{[5-(Pentafluoro-λ 6 -sulfanyl)pyridin-2-yl]amino}piperidin-1-yl)sulfonyl]phenyl}pyridine-2-carboxamide;

[1969] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(Difluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline;

[1970] 4-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}pyridine-2-carboxamide;

[1971] 5-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]pyridin-2-amine;

[1972] 5-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]pyridin-2-amine;

[1973] 5-(Pentafluoro-λ 6-Thiol)-N-[trans-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]pyridin-2-amine;

[1974] or

[1975] 5-(Pentafluoro-λ 6 -Thiol)-N-[trans-4-{4-[8-methyl-3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]pyridin-2-amine.

[1976] Aspect 41. The compound or a pharmaceutically acceptable salt thereof according to any one of Aspects 1 to 40, wherein the compound is selected from:

[1977] 1-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -Thiol)phenyl]piperidin-4-amine

[1978] 1-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]-N-[4-(pentafluoro-λ 6 -Thiol)phenyl]piperidin-4-amine

[1979] 5-{4-[(4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indole-3-carbonitrile

[1980] 5-{4-[(4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indazole-3-carbonitrile

[1981] 4-(Pentafluoro-λ 6 -Thiol)-N-[cis-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline 4-(pentafluoro-λ 6 -Thiol)-N-[trans-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline

[1982] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile

[1983] 5-(4-{[cis-4-{[4-(pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile

[1984] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one

[1985] 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[1986] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[1987] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[1988] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[1989] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one

[1990] N,N-dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide

[1991] N-methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide

[1992] 6-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[1993] 4-(pentafluoro-λ 6 -sulfanyl)-N-[cis-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[1994] N,N-dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6-Thiol)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[1995] N,N-Dimethyl-5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[1996] N-Methyl-4'-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[1997] N-Methyl-5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[1998] 4'-{[trans-4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide

[1999] 1-(4-{Imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -Thiol)phenyl]piperidin-4-amine

[2000] 6-{4-[(4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[2001] 6-{4-[(4-{[4-(Pentafluoro-λ 6 -Thiol)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide

[2002] 1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -Thiol)phenyl]piperidin-4-amine

[2003] N-[4-(Pentafluoro-λ 6 -Thiol)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[2004] N-[4-(Pentafluoro-λ 6-thio)phenyl]-1-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[2005] 1-{4-[3-(methoxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine

[2006] 1-(4-{3-cyclopentyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -thio)phenyl]piperidin-4-amine

[2007] 6-{4-[(4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[2008] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile

[2009] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide

[2010] 4-(pentafluoro-λ 6 -thio)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[2011] 4-(pentafluoro-λ 6 -thio)-N-[trans-4-(4-{[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[2012] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carboxamide

[2013] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -thio)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carbonitrile

[2014] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide

[2015] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[2016] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl}benzenesulfonyl)cyclohexyl]aniline

[2017] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carbonitrile

[2018] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methylimidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[2019] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline

[2020] N,N-dimethyl-6-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[2021] N,N-dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[2022] N-methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[2023] N-methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide

[2024] 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide

[2025] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[2026] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[2027] 4-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2-dihydropyridin-2-one

[2028] 7-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one

[2029] 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one

[2030] 6-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-3H,4H-pyrrolo[2,1-f][1,2,4]triazin-4-one

[2031] 5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridin-2-ol

[2032] 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{[4'-(dimethylphosphoryl)-[1,1'-biphenyl]-4-yl]sulfonyl}cyclohexyl]aniline

[2033] 5-(4-{[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one

[2034] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one

[2035] 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[2036] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one

[2037] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridazine-3-carboxamide

[2038] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[2039] 4-(pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[8-methyl-3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline

[2040] 5'-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2'-one

[2041] 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

[2042] 1-(2-fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl]benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[2043] 1-(3-fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl]benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[2044] 1-[(6-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[2045] 1-[(5-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[2046] 6-{2-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[2047] 1-(3-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[2048] 6-{3-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[2049] 1-(2-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[2050] 1-[(5-{imidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[2051] 6-{5-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-2-yl}imidazo[1,2-a]pyridine-3-carbonitrile

[2052] 1-[(6-{imidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[2053] 6-{6-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-3-yl}imidazo[1,2-a]pyridine-3-carbonitrile

[2054] 1-(2-chloro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[2055] 6-{3-chloro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[2056] 6-{4-[(4-{[3-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile

[2057] 1-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[3-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine

[2058] 4-(4-{[(3S,4S)-3-fluoro-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl]sulfonyl}phenyl)pyridine-2-carboxamide

[2059] N-[3-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine

[2060] 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1H-indole-3-carbonitrile

[2061] [4-(3-methyl-1H-indazol-5-yl)phenyl][trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[2062] (4-{imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone

[2063] (4-{imidazo[1,2-a]pyridin-6-yl}phenyl)[cis-4-{[4-(pentafluoro-λ 6((4-{3-Methylimidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfone

[2064] (4-{3-Methylimidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentaf...

Claims

1. A compound of formula (I), wherein X 1 is CH or N; X 2 is CH or N; X 3 is CH or N; X 4 is O or NH; X 5 is CH or N; R 1 is an aryl, heterocyclic group or heteroaryl group, wherein the aryl, heterocyclic group and heteroaryl group are optionally substituted by one or more R 1a substituents; R 1a is C 1-6 alkyl, cyano, -NR 1b R 1c , -C 1-6 alkyl-NR 1b R 1c , oxo, -CONR 1b R 1c , -PO(Me)2, hydroxy, C 3-6 cycloalkyl, -C 1-6 alkyl-C 1-6 alkoxy, C 3-6 heterocyclyl, halo-C 1-6 alkyl, halo, C 1-6 alkoxy; R 1b is hydrogen, C 3-6 cycloalkyl or C 1-6 alkyl; R 1c is hydrogen, C 3-6 cycloalkyl or C 1-6 alkyl; R 2 is hydrogen or a halogen; R 3 is hydrogen or a halogen; R 4 is hydrogen, C 1-6 alkyl or halogen; R 5 is hydrogen, a halogen or C 1-6 alkyl; R 6 is hydrogen or -SF5, where R 6 and R 7 must be different; R 7 is hydrogen or -SF5, where R 6 and R 7 must be different; or a pharmaceutically acceptable salt thereof.

2. The compound according to claim 1, wherein R 1a is C 1-6 alkyl, cyano, oxo, -CONR 1b R 1c , -PO(Me)2, hydroxy, C 3-6 cycloalkyl, -C 1-6 alkyl C 1-6 alkoxy, halo C 1-6 alkyl, halo, C 1-6 alkoxy; R 1b is hydrogen or C 1-6 alkyl; R 1c is hydrogen or C 1-6 alkyl; X 5 is CH; R 5 is hydrogen; or a pharmaceutically acceptable salt thereof.

3. The compound or its pharmaceutically acceptable salt according to claim 1 or 2, wherein X 1 is CH.

4. The compound or its pharmaceutically acceptable salt according to claim 1 or 2, wherein X 1 is N.

5. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 4, wherein X 2 is CH.

6. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 4, wherein X 2 is N.

7. The compound according to any one of claims 1 to 6 or a pharmaceutically acceptable salt thereof, wherein X 3 is CH.

8. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 6, wherein X 3 is N.

9. The compound according to any one of claims 1 to 8 or a pharmaceutically acceptable salt thereof, wherein X 4 is O.

10. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 8, wherein X 4 is NH.

11. The compound or its pharmaceutically acceptable salt according to any one of claims 1 or 3 to 10, wherein X 5 is N.

12. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 10, wherein X 5 is CH.

13. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 2, 4 to 5, 7, 9 or 12, wherein X 1 is N, X 2 is CH, X 3 is CH, X 4 is O and X 5 is CH.

14. A compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 3, 5, 7, 9 or 12, wherein X 1 is CH, X 2 is CH, X 3 is CH, X 4 is O and X 5 is CH.

15. A compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 2, 4, 6 to 7, 9 or 12, wherein X 1 is N, X 2 is N, X 3 is CH, X 4 is O and X 5 is CH.

16. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 2, 4 to 5, 8 to 9 or 12, wherein X 1 is N, X 2 is CH, X 3 is N, X 4 is O and X 5 is CH.

17. A compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 3, 5, 7, 10 or 12, wherein X 1 is CH, X 2 is CH, X 3 is CH, X 4 is NH and X 5 is CH.

18. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 2, 4 to 5, 7, 10 or 12, wherein X 1 is N, X 2 is CH, X 3 is CH, X 4 is NH and X 5 is CH.

19. A compound according to any one of claims 1 to 18 or a pharmaceutically acceptable salt thereof, wherein R 1 is azaspironanyl, triazaspirodecanyl, diazaspirodecanyl, oxadiazaspirodecanyl, oxazaspironanyl, oxazabicyclooctanyl, pyrazolopyridinyl, pyrrolopyrimidinyl, pyrrolopyridinyl, thienyl, thienopyridinyl, pyrrolopyrazinyl, pyrrolodiazepine 1, 2, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 66, 67, 68, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92 phenyl, pyridyl, triazolopyridinyl, isoquinolyl, pyridazinyl, triazolopyrazinyl, pyrrolotriazinyl and spirocyclopropanedihydroindolinyl are optionally substituted with one or more R 1a replace.

20. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 19, wherein R 1 is indazolyl, indolyl, isoindolinyl, triazolopyridinyl, imidazopyridinyl, imidazopyrazinyl, dihydroindolyl, phenyl, pyridinyl, triazolopyridazinyl, isoquinolinyl, pyridazinyl, triazolopyrazinyl, pyrrolotriazinyl or spirocyclopropane dihydroindolyl, wherein the indazolyl, indolyl, isoindolinyl, triazolopyridinyl, imidazopyridinyl, imidazopyrazinyl, dihydroindolyl, phenyl, pyridinyl, triazolopyridazinyl, isoquinolinyl, pyridazinyl, triazolopyrazinyl, pyrrolotriazinyl and spirocyclopropane dihydroindolyl are optionally substituted by one or more R 1a substituents.

21. The compound according to any one of claims 1 to 20 or a pharmaceutically acceptable salt thereof, wherein R 1 is indazolyl, indolyl, pyridyl, triazolopyridyl, phenyl or imidazopyridyl, wherein the indazolyl, indolyl, pyridyl, triazolopyridyl, phenyl and imidazopyridyl are optionally substituted by one or more R 1a substituents.

22. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 21, wherein R 1 is methylindazolyl, cyano - indolyl, cyano - indazolyl, oxo - isoindolinyl, carbamoylpyridyl, methyl - triazolopyridyl, imidazopyridyl, cyano - imidazopyridyl, imidazopyrazinyl, methylimidazopyridyl, carbamoyl - imidazopyridyl, isopropyl - triazolopyridyl, triazolopyridyl, carbamoylindazolyl, oxo - dihydroindolyl, carbamoyl - triazolopyridyl, cyano - triazolopyridyl, (dimethylcarbamoyl)phenyl, methylimidazopyrazinyl, (dimethylcarbamoyl)pyridyl, (methylcarbamoyl)phenyl, (methylcarbamoyl)pyridyl, oxo - triazolopyridyl, carbamoylphenyl, isopropyl - triazolopyridazinyl, oxo - dihydro - isoquinolinyl, carbamoylpyridazinyl, dimethylphosphorylphenyl, isopropyl - triazolopyrazinyl, oxo - pyridyl, oxo - pyrrolotriazinyl, hydroxypyridyl, (dimethylcarbamoyl)pyridyl, oxo - spiropropane dihydroindolyl, methoxyazaspiro nonyl, oxo - triazaspiro decyl, oxo - diazaspiro decyl, oxo - oxadiazaspiro decyl, oxaazaspiro nonyl, oxaazabicyclo octyl, carbamoylfluorophenyl, propyltriazolopyrazinyl, isopropylcarbamoylphenyl, methylpyrazolopyridyl, N,N - dimethylamineimidazopyridyl, cyclopropylcarbamoylphenyl, pyrrolopyrimidyl, pyrrolopyridyl, pyrazolopyridyl, carbamoylthienyl, methylimidazopyridyl, (trifluoromethyl)imidazopyridyl, fluorimidazopyridyl, oxo - thiophenopyridyl, oxo - pyrrolopyrazinyl, oxo - pyrrolodiazinyl group, carbamoyl - imidazopyridyl, furan carboxamide, cyano - imidazopyridyl, pyrrolidinyl - triazolopyridyl, propyl - triazolopyrazinyl or azetidinyl - triazolopyridyl.

23. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 22, wherein R 1 is methylindazolyl, cyanoindolyl, cyanoindazolyl, oxoisoindolinyl, carbamoylpyridyl, methyl-triazolopyridyl, imidazopyridyl, cyanoimidazopyridyl, imidazopyrazinyl, methylimidazopyridyl, carbamoyl-imidazopyridyl, isopropyl-triazolopyridyl, triazolopyridyl, carbamoylindazolyl, oxoindolinyl, carbamoyl-triazolopyridyl, methyl-triazolopyridyl, methyl-triazolopyridyl, cyano-triazolopyridyl, (dimethylcarbamoyl)phenyl, methylimidazopyrazinyl, (dimethylcarbamoyl)pyridyl, (methylcarbamoyl)phenyl, (methylcarbamoyl)pyridyl, oxo-triazolopyridyl, carbamoylphenyl, carbamoylpyridyl, isopropyl-triazolopyridazinyl, oxo-dihydroisoquinolinyl, carbamoylpyridazinyl, dimethylphosphorylphenyl, oxoisoindolinyl, oxoindolinyl, oxo-dihydroisoquinolinyl, isopropyl-triazolopyrazinyl, oxo-pyridyl, oxo-dihydroisoquinolinyl, oxo-pyrrolotriazinyl, hydroxypyridyl, methyl-triazolopyridyl, imidazopyridyl, triazolopyridyl, carbamoylphenyl, carbamoylpyridyl, (dimethylcarbamoyl)pyridyl, oxospiropropaneindolinyl.

24. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 23, wherein R 1 is methyl-indazolyl, cyano-indolyl, carbamoyl-pyridyl, methyl-imidazopyridyl, methyl-triazolopyridyl, isopropyl-triazolopyridyl, cyano-indazolyl, (methylcarbamoyl)phenyl, imidazopyridyl, cyanoimidazopyridyl.

25. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 24, wherein R 1a is methoxy, fluoro, -CONH[(CH(CH3)2], -CONH(cyclopropyl), dimethylamino, -CF3, pyrrolidinyl, azetidinyl, methyl, cyano, oxo, -CONH2, isopropyl, -CON(Me)2, -CH2-O-CH3, -CONH(Me), -PO(Me)2, -OH.

26. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 25, wherein R 1a is methyl, cyano, oxo, -CONH2, isopropyl, -CON(Me)2, -CH2-O-CH3, -CONH(Me), -PO(Me)2, -OH.

27. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 26, wherein R 1a is methyl, cyano, -CONH2, isopropyl, -CONH(Me).

28. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 27, wherein R 2 is hydrogen, fluorine or -CF3.

29. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 28, wherein R 2 is hydrogen.

30. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 29, wherein R 3 is hydrogen, fluorine, chlorine or -CF3.

31. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 30, wherein R 3 is hydrogen.

32. The compound according to any one of claims 1 to 31 or a pharmaceutically acceptable salt thereof, wherein R 4 is hydrogen or fluorine.

33. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 32, wherein R 4 is hydrogen.

34. The compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 33, wherein R 6 is -SF5.

35. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 34, wherein R 7 is hydrogen.

36. The compound or its pharmaceutically acceptable salt according to any one of claims 1 to 35, wherein R 5 is hydrogen.

37. The compound according to any one of claims 1 to 3, 5 to 12, 14, 17 or 19 to 36, wherein the compound is a compound of formula (I'), or a pharmaceutically acceptable salt thereof, wherein R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、X 2 、X 3 、X 4 and X 5 are as defined in any one of claims 1 to 3, 5 to 12, 14, 17 or 19 to 36, and X 1 is CH.

38. The compound according to any one of claims 1 to 5, 7, 9 to 10, 12 to 37 or a pharmaceutically acceptable salt thereof, wherein X 1 is CH or N, X 2 is CH X 3 is CH X 4 is O or NH, X 5 is CH R 1 is indazolyl, indolyl, pyridyl, triazolopyridyl, phenyl or imidazopyridyl, wherein the indazolyl, indolyl, pyridyl, triazolopyridyl, phenyl and imidazopyridyl are optionally substituted by one or more R 1a substituents R 1a is methyl, cyano, -CONH2, isopropyl, -CONH(Me), R 2 is hydrogen, R 3 is hydrogen, R 4 is hydrogen, R 5 is hydrogen, R 6 is -SF5, R 7 is hydrogen.

39. The compound according to any one of claims 1 to 5, 7, 9 to 10, 12 to 38 or a pharmaceutically acceptable salt thereof, wherein X 1 is CH or N, X 2 is CH X 3 is CH X 4 is O or NH, X 5 is CH R 1 being methyl-indazolyl, cyano-indolyl, carbamoyl-pyridyl, methyl-imidazopyridyl, methyl-triazolopyridyl, isopropyl-triazolopyridyl, cyano-indazolyl, (methylcarbamoyl)phenyl, imidazopyridyl, cyanoimidazopyridyl, R 2 is hydrogen, R 3 is hydrogen, R 4 is hydrogen, R 5 is hydrogen, R 6 is - SF5, R 7 is hydrogen.

40. The compound according to any one of claims 1 to 39 or a pharmaceutically acceptable salt thereof, the compound being selected from: 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-[4-(3-Methyl-2H-indazol-5-yl)phenylsulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indole-3-carbonitrile 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indazole-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[cis-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile 5-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide 6-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[cis-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide N,N-Dimethyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide N-Methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide 4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide 1-(4-{Imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide 1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine 1-{4-[3-(methoxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-(4-{3-Cyclopentyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carboxamide 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carbonitrile 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl}benzenesulfonyl)cyclohexyl]aniline 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methylimidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline N,N-Dimethyl-6-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide N-Methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide N-Methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]benzenesulfonyl}cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}cyclohexyl]aniline 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2-dihydropyridin-2-one 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-3H,4H-pyrrolo[2,1-f][1,2,4]triazin-4-one 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridin-2-ol 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{[4'-(dimethylphosphoryl)-[1,1'-biphenyl]-4-yl]sulfonyl}cyclohexyl]aniline 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridazine-3-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[8-methyl-3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline 5'-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1',2'-dihydrospiro[cyclopropane-1,3'-indol]-2'-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one 1-(2-Fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-(3-Fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-[(6-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-[(5-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{2-Fluoro-4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 1-(3-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{3-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 1-(2-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-[(5-{Imidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{5-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-2-yl}imidazo[1,2-a]pyridine-3-carbonitrile 1-[(6-{Imidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{6-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-3-yl}imidazo[1,2-a]pyridine-3-carbonitrile 1-(2-Chloro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{3-chloro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 6-{4-[(4-{[3-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[3-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 4-(4-{[(3S,4S)-3-Fluoro-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl]sulfonyl}phenyl)pyridine-2-carboxamide N-[3-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-1H-indole-3-carbonitrile [4-(3-Methyl-1H-indazol-5-yl)phenyl][trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{3-Methylimidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide (4-{Imidazo[1,2-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone [trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](4-{[1,2,4]triazolo[1,5-a]pyridin-7-yl}phenyl)(imino)-λ 6 -sulfone N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide 4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide 4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide N,N-Dimethyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide N-Methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide {4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{2-Methylimidazo[1,2-a]pyrazin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-3-carboxamide N-Methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-3-carboxamide 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide N,N-Dimethyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)pyridine-2-carboxamide N-Methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-3-carboxamide 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-2,3-dihydro-1H-isoindol-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-2,3-dihydro-1H-isoindol-1-one 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-2,3-dihydro-1H-indol-2-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one {4-[3-(Propan-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylideneamino]phenyl}-1H-indole-3-carbonitrile N-Methyl-5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinyl]phenyl}pyridine-2-carboxamide 4'-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylidene]-[1,1'-biphenyl]-4-carbonitrile 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylideneamino]phenyl}-2,3-dihydro-1H-indol-2-one (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)(imino)-λ 6 -sulfone 4-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylideneamino]phenyl}pyridine-2-carboxamide (+)-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-1H-indole-3-carbonitrile (-)-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-1H-indole-3-carbonitrile (+)-(4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (-)-(4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (+)-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide (-)-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide 1-(4-{2-Methoxy-7-azaspiro[3.5]nonan-7-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine, 8-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1,3,8-triazaspiro[4.5]decane-2,4-dione, 8-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2,8-diazaspiro[4.5]decan-1-one, 8-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-3-oxa-1,8-diazaspiro[4.5]decan-2-one, 1-(4-{2-Oxa-7-azaspiro[3.5]nonan-7-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine, 1-(4-{8-Oxa-3-azabicyclo[3.2.1]octan-3-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine, 4-Fluoro-N-methyl-4'-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]-[1,1'-biphenyl]-3-carboxamide, 3-Fluoro-N-methyl-4'-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]-[1,1'-biphenyl]-4-carboxamide, N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}piperidin-4-amine, N-(propan-2-yl)-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-1H-pyrazolo[3,4-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline, N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridin-3-amine, N-Cyclopropyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{5H-pyrrolo[3,2-d]pyrimidin-2-yl}benzenesulfonyl)cyclohexyl]aniline, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{1H-pyrrolo[2,3-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{1H-pyrazolo[3,4-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline, 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)thiophene-2-carboxamide, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{8-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[8-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{8-fluoroimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline, 2-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-4H,5H,6H,7H-thieno[3,2-c]pyridin-4-one, 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H-pyrrolo[1,2-a]pyrazin-1-one, 8-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H,3H,4H,5H-pyrrolo[1,2-a][1,4]diazepin -1-one, 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one, 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-8-carboxamide, 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)furan-2-carboxamide, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{8-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline, 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-8-carbonitrile, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-[(2R)-pyrrolidin-2-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline, {4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]phenyl}[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone, (+)-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfonone, (-)-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone, N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-(4-{3-[(3R)-pyrrolidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-amine, N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-(4-{3-[(3S)-pyrrolidin-3-yl][1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-amine, 1-{4-[3-(azetidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(azetidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline; {4-[3-(Difluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone; (4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyrazin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone; {4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[5-(Pentafluoro-λ 6 -sulfanyl)pyridin-2-yl]amino}cyclohexyl](imino)-λ 6 -sulfone; 5-(Pentafluoro-λ 6 -sulfanyl)-N-(1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-yl)pyridin-2-amine; N-[1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-yl]-5-(pentafluoro-λ 6 -sulfanyl)pyridin-2-amine; N-[1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-yl]-5-(pentafluoro-λ 6 -sulfanyl)pyridin-2-amine; 4-{4-[(4-{[5-(Pentafluoro-λ 6 -sulfanyl)pyridin-2-yl]amino}piperidin-1-yl)sulfonyl]phenyl}pyridine-2-carboxamide; 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(difluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline; 4-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}pyridine-2-carboxamide; 5-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]pyridin-2-amine; 5-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]pyridin-2-amine; 5-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]pyridin-2-amine; or 5-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[8-methyl-3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]pyridin-2-amine.

41. The compound according to any one of claims 1 to 40 or a pharmaceutically acceptable salt thereof, the compound being selected from: 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indole-3-carbonitrile 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indazole-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[cis-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile 5-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide 6-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[cis-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide N,N-Dimethyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide N-Methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide 4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide 1-(4-{Imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 6-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide 1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine 1-{4-[3-(methoxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-(4-{3-Cyclopentyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carboxamide 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carbonitrile 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl}benzenesulfonyl)cyclohexyl]aniline 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methylimidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline N,N-Dimethyl-6-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide N-Methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide N-Methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]benzenesulfonyl}cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}cyclohexyl]aniline 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2-dihydropyridin-2-one 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-3H,4H-pyrrolo[2,1-f][1,2,4]triazin-4-one 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridin-2-ol 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{[4'-(dimethylphosphoryl)-[1,1'-biphenyl]-4-yl]sulfonyl}cyclohexyl]aniline 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridazine-3-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[8-methyl-3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline 5'-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1',2'-dihydrospiro[cyclopropane-1,3'-indol]-2'-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one 1-(2-Fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-(3-Fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-[(6-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-[(5-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{2-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 1-(3-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{3-Fluoro-4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 1-(2-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-[(5-{Imidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{5-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-2-yl}imidazo[1,2-a]pyridine-3-carbonitrile 1-[(6-{Imidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{6-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-3-yl}imidazo[1,2-a]pyridine-3-carbonitrile 1-(2-chloro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{3-chloro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 6-{4-[(4-{[3-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[3-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 4-(4-{[(3S,4S)-3-Fluoro-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl]sulfonyl}phenyl)pyridine-2-carboxamide N-[3-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-1H-indole-3-carbonitrile [4-(3-Methyl-1H-indazol-5-yl)phenyl][trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{3-Methylimidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide (4-{Imidazo[1,2-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone [trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](4-{[1,2,4]triazolo[1,5-a]pyridin-7-yl}phenyl)(imino)-λ 6 -sulfone N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide 4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide 4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide N,N-Dimethyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide N-Methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide {4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{2-Methylimidazo[1,2-a]pyrazin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-3-carboxamide N-Methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-3-carboxamide 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide N,N-Dimethyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide N-Methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-3-carboxamide 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-2,3-dihydro-1H-indol-2-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one {4-[3-(Propan-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylideneamino]phenyl}-1H-indole-3-carbonitrile N-Methyl-5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylideneamino]phenyl}pyridine-2-carboxamide 4'-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylidene]-[1,1'-biphenyl]-4-carbonitrile 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylidene]phenyl}-2,3-dihydro-1H-indol-2-one (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)(imino)-λ 6 -sulfone 4-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylideneamino]phenyl}pyridine-2-carboxamide (+)-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)-1H-indole-3-carbonitrile (-)-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-1H-indole-3-carbonitrile (+)-(4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (-)-(4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (+)-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide (-)-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide 1-(4-{2-Methoxy-7-azaspiro[3.5]nonan-7-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine, 8-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1,3,8-triazaspiro[4.5]decane-2,4-dione, 8-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2,8-diazaspiro[4.5]decan-1-one, 8-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-3-oxa-1,8-diazaspiro[4.5]decan-2-one, 1-(4-{2-Oxa-7-azaspiro[3.5]nonan-7-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine, 1-(4-{8-Oxa-3-azabicyclo[3.2.1]octan-3-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine, 4-Fluoro-N-methyl-4'-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]-[1,1'-biphenyl]-3-carboxamide, 3-Fluoro-N-methyl-4'-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]-[1,1'-biphenyl]-4-carboxamide, N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}piperidin-4-amine, N-(propan-2-yl)-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-1H-pyrazolo[3,4-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline, N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridin-3-amine, N-Cyclopropyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{5H-pyrrolo[3,2-d]pyrimidin-2-yl}benzenesulfonyl)cyclohexyl]aniline, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{1H-pyrrolo[2,3-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{1H-pyrazolo[3,4-c]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline, 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)thiophene-2-carboxamide, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{8-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl}benzenesulfonyl)cyclohexyl]aniline, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[8-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{8-fluoroimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline, 2-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-4H,5H,6H,7H-thieno[3,2-c]pyridin-4-one, 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H-pyrrolo[1,2-a]pyrazin-1-one, 8-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H,3H,4H,5H-pyrrolo[1,2-a][1,4]diazepin -1-one, 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one, 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-8-carboxamide, 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)furan-2-carboxamide, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{8-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline, 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-8-carbonitrile, 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-[(2R)-pyrrolidin-2-yl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline, {4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]phenyl}[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone, (+)-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfonone, (-)-{4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfonone, N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-(4-{3-[(3R)-pyrrolidin-3-yl][1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-amine, N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-(4-{3-[(3S)-pyrrolidin-3-yl][1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-amine, 1-{4-[3-(azetidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine, or 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(azetidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline.

42. The compound according to any one of claims 1 to 41 or a pharmaceutically acceptable salt thereof, the compound being selected from: 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-[4-(3-Methyl-2H-indazol-5-yl)benzenesulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indole-3-carbonitrile 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indazole-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[cis-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile 5-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide 6-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[cis-4-(4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide N,N-Dimethyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide N-Methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide 4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-3-carboxamide 1-(4-{Imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 6-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide 1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine N-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine 1-{4-[3-(Methoxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-(4-{3-Cyclopentyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carboxamide 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carbonitrile 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl}benzenesulfonyl)cyclohexyl]aniline 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-[1,2,4]triazolo[4,3-a]pyridine-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{2-methylimidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{imidazo[1,2-a]pyrazin-6-yl}benzenesulfonyl)cyclohexyl]aniline N,N-Dimethyl-6-(4-{[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide N-Methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide N-Methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-3-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]benzenesulfonyl}cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}cyclohexyl]aniline 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2-dihydropyridin-2-one 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-3-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-3H,4H-pyrrolo[2,1-f][1,2,4]triazin-4-one 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridin-2-ol 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{[4'-(dimethylphosphoryl)-[1,1'-biphenyl]-4-yl]sulfonyl}cyclohexyl]aniline 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridazine-3-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[8-methyl-3-(propan-2-yl)imidazo[1,2-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline 5'-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1',2'-dihydrospiro[cyclopropane-1,3'-indol]-2'-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one 1-(2-Fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-(3-Fluoro-4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-[(6-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-[(5-{3-Methylimidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{2-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 1-(3-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{3-Fluoro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 1-(2-Fluoro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 1-[(5-{Imidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{5-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-2-yl}imidazo[1,2-a]pyridine-3-carbonitrile 1-[(6-{Imidazo[1,2-a]pyridin-6-yl}pyridin-3-yl)sulfonyl]-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{6-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]pyridin-3-yl}imidazo[1,2-a]pyridine-3-carbonitrile 1-(2-chloro-4-{imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{3-chloro-4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 6-{4-[(4-{[3-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[3-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 4-(4-{[(3S,4S)-3-Fluoro-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl]sulfonyl}phenyl)pyridine-2-carboxamide N-[3-(Pentafluoro-λ 6 -sulfanyl)phenyl]-1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-amine 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-1H-indole-3-carbonitrile [4-(3-Methyl-1H-indazol-5-yl)phenyl][trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[cis-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{3-Methylimidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide (4-{Imidazo[1,2-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfonone [trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](4-{[1,2,4]triazolo[1,5-a]pyridin-7-yl}phenyl)(imino)-λ 6 -sulfone N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide 4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-4-carboxamide N,N-Dimethyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide 4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}-[1,1'-biphenyl]-3-carboxamide N,N-Dimethyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-2-carboxamide N-Methyl-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide {4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{2-Methylimidazo[1,2-a]pyrazin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone N,N-Dimethyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-3-carboxamide N-Methyl-6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinyl}phenyl)pyridine-3-carboxamide 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide N,N-Dimethyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)pyridine-2-carboxamide N-Methyl-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-3-carboxamide 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-2,3-dihydro-1H-isoindol-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one 7-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)-1,2,3,4-tetrahydroisoquinolin-1-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)-2,3-dihydro-1H-isoindol-1-one 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-2,3-dihydro-1H-indol-2-one 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)-2,3-dihydro-1H-indol-2-one {4-[3-(Propan-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylidene]phenyl}-1H-indole-3-carbonitrile N-Methyl-5-{4-[(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylideneamino]phenyl}pyridine-2-carboxamide 4'-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylidene]-[1,1'-biphenyl]-4-carbonitrile 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfinylideneamino]phenyl}-2,3-dihydro-1H-indol-2-one (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)(4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)(imino)-λ 6 -sulfone 4-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)iminosulfonyl]phenyl}pyridine-2-carboxamide (+)-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-1H-indole-3-carbonitrile (-)-5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)-1H-indole-3-carbonitrile (+)-(4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (-)-(4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone (+)-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide (-)-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)pyridine-2-carboxamide.

43. The compound according to any one of claims 1 to 42 or a pharmaceutically acceptable salt thereof, the compound being selected from: 1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine {4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)pyridine-2-carboxamide 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]iminosulfonyl}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indazole-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline (4-{3-Methylimidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone 6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine; 5-(Pentafluoro-λ 6 -sulfanyl)-N-(1-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}piperidin-4-yl)pyridin-2-amine; N-[1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-yl]-5-(pentafluoro-λ 6 -sulfanyl)pyridin-2-amine; or N-[1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)piperidin-4-yl]-5-(pentafluoro-λ 6 -sulfanyl)pyridin-2-amine.

44. The compound according to any one of claims 1 to 43 or a pharmaceutically acceptable salt thereof, the compound being selected from: 1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine {4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfonamide N-Methyl-4'-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}-[1,1'-biphenyl]-4-carboxamide 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide 6-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylideneamino}phenyl)imidazo[1,2-a]pyridine-3-carbonitrile 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indazole-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline (4-{Imidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide 5-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)-1H-indole-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-[4-(3-methyl-2H-indazol-5-yl)benzenesulfonyl]cyclohexyl]aniline 5-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-1H-indazole-3-carbonitrile 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methylimidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline (4-{3-Methylimidazo[1,2-a]pyridin-6-yl}phenyl)[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfone 6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}imidazo[1,2-a]pyridine-3-carbonitrile 1-(4-{Imidazo[1,2-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine.

45. The compound according to any one of claims 1 to 44 or a pharmaceutically acceptable salt thereof, the compound being selected from: 4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfonyl}phenyl)pyridine-2-carboxamide 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-(4-{3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)cyclohexyl]aniline 6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide 1-(4-{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl}benzenesulfonyl)-N-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]piperidin-4-amine 6-{4-[(4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}piperidin-1-yl)sulfonyl]phenyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzenesulfonyl}cyclohexyl]aniline 4-(Pentafluoro-λ 6 -sulfanyl)-N-[trans-4-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyrazin-6-yl]benzenesulfonyl}cyclohexyl]aniline (+)-4-(4-{[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl]sulfinylamino}phenyl)pyridine-2-carboxamide (+)-{4-[3-(propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfon] (-)-{4-[3-(Propan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl}[trans-4-{[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]amino}cyclohexyl](imino)-λ 6 -sulfonone.

46. A process for preparing a compound of formula (I) or formula (I') as claimed in any one of claims 1 to 45 or a pharmaceutically acceptable salt thereof, wherein X 1 is N and X 4 is O, the process comprising: To make a compound of formula (VI), wherein R 6 , R 7 and X 5 are as defined in any one of claims 1 to 45, Compound of formula (VII), wherein R 5 and R 4 as defined in any one of claims 1 to 45 A reaction is carried out to form a compound of formula (VIII), wherein R 4 , R 5 , X 5 , R 6 , R 7 are as defined in any one of claims 1 to 45 React the compound of formula (VIII) with an acid to form a compound of formula (IX), wherein R 4 、R 5 、X 5 、R 6 、R 7 is as defined in any one of claims 1 to 45, reacting the compound of formula (IX) with a compound of formula (XI), wherein X 2 and X 3 , R 2 and R 3 are as defined in any one of claims 1 to 45 A reaction is carried out to form a compound of formula (III), wherein R 2 , R 3 , R 4 , R 6 , R 7 , R 5 , X 2 , X 5 and X 3 are as defined in any one of claims 1 to 45, Reacting the compound of formula (III) with a compound of formula (X), wherein R 1 is as defined in any one of claims 1 to 45, and R 9 and R 10 are independently selected from C 1-6 alkyl, or R 9 and R 10 together with the oxygen atom to which they are attached form a 3- to 14-membered heterocyclic group, which heterocyclic group is optionally substituted by one or more C 1-6 alkyl, especially optionally substituted by four C 1-6 alkyl, react to form a compound of formula (I).

47. A process for preparing a compound of formula (I) or formula (I') or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 45, wherein X 1 is CH and X 4 is O, the process comprising: To cause a compound of formula (XII), wherein R 5 and R 4 is as defined in any one of claims 1 to 45, React with CH3SO2Cl to form a compound of formula (XIII), wherein R 5 and R 4 are as defined in any one of claims 1 to 45, React the compound of formula (XIII) with a compound of formula (XIV), wherein R 3 、R 2 、X 2 and X 3 are as defined in any one of claims 1 to 45, A reaction is carried out to form a compound of formula (XV), wherein R 3 、R 2 、R 5 、R 4 、X 2 and X 3 are as defined in any one of claims 1 to 45, React the compound of formula (XV) with an oxidizing agent to form a compound of formula (XVI), wherein R 3 、R 2 、R 5 、R 4 、X 2 and X 3 are as defined in any one of claims 1 to 45, React the compound of formula (XVI) with an acid to form a compound of formula (XVII), wherein R 3 、R 2 、R 5 、R 4 、X 2 and X 3 are as defined in any one of claims 1 to 45, React the compound of formula (XVII) with a compound of formula (VI), wherein R 6 、R 7 and X 5 are as defined in any one of claims 1 to 45, A reaction is carried out to form a compound of formula (XVIII), wherein R 2 , R 3 ,R 4 ,R 6 ,R 7 ,R 5 ,X 2 ,X 5 and X 3 are as defined in any one of claims 1 to 45, React the compound of formula (XVIII) with a compound of formula (X), wherein R 1 is as defined in any one of claims 1 to 45, and R 9 and R 10 are independently selected from C 1-6 alkyl, or R 9 and R 10 together with the oxygen atom to which they are attached form a 3- to 14-membered heterocyclic group, which heterocyclic group is optionally substituted by one or more, especially four, C 1-6 alkyl, react to form a compound of formula (I).

48. A method for preparing a compound of formula (I) or formula (I') or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 45, wherein X 1 is CH and X 4 is NH, the method comprising: To make a compound of formula (XV), wherein R 3 、R 2 、R 5 、R 4 、X 2 and X 3 as defined in any one of claims 1 to 45, React with an acid to form a compound of formula (XX), wherein R 3 、R 2 、R 5 、R 4 、X 2 and X 3 are as defined in any one of claims 1 to 45, React the compound of formula (XX) with a compound of formula (VI), wherein R 6 , R 7 and X 5 are as defined in any one of claims 1 to 45, React to form a compound of formula (XXI), wherein R 2 、R 3 、R 4 、R 6 、R 7 、R 5 、X 2 、X 5 and X 3 are as defined in any one of claims 1 to 45, React the compound of formula (XXI) with ammonium carbamate and (diacetoxyiodo)benzene to form a compound of formula (XXII), wherein R 2 、R 3 、R 4 、R 6 、R 7 、R 5 、X 2 、X 5 and X 3 are as defined in any one of claims 1 to 45, reacting the compound of formula (XXII) with a compound of formula (X), wherein R 1 is as defined in any one of claims 1 to 45, and R 9 and R 10 are independently selected from C 1-6 alkyl, or R 9 and R 10 together with the oxygen atom to which they are attached form a 3- to 14-membered heterocyclic group, which heterocyclic group is optionally substituted by one or more C 1-6 alkyl, especially optionally substituted by four C 1-6 alkyl, react to form a compound of formula (I).

49. A process for preparing a compound of formula (I) or formula (I') or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 45, wherein X 1 is N and X 4 is NH, the process comprising: To make a compound of formula (IX), wherein R 4 、R 5 、X 5 、R 6 、R 7 as defined in any one of claims 1 to 45, Compound of formula (XIV), wherein R 2 and R 3 as defined in any one of claims 1 to 45 A reaction is carried out to form a compound of formula (XXIV), wherein R 2 、R 3 、R 4 、R 6 、R 7 、R 5 、X 2 、X 5 and X 3 are as defined in any one of claims 1 to 45, React the compound of formula (XXIV) with ammonium carbamate and (diacetoxyiodo)benzene to form the compound of formula (XXV), wherein R 2 、R 3 、R 4 、R 6 、R 7 、R 5 、X 2 、X 5 and X 3 are as defined in any one of claims 1 to 45, React the compound of formula (XXV) with di-tert-butyl dicarbonate and NaH to form a compound of formula (XXVI), wherein R 2 、R 3 、R 4 、R 6 、R 7 、R 5 、X 2 、X 5 and X 3 are as defined in any one of claims 1 to 45, reacting the compound of formula (XXVI) with a compound of formula (X), wherein R 1 is as defined in any one of claims 1 to 45, and R 9 and R 10 are independently selected from C 1-6 alkyl, or R 9 and R 10 together with the oxygen atom to which they are attached form a 3- to 14-membered heterocyclic group, which heterocyclic group is optionally substituted by one or more C 1-6 alkyl, especially optionally substituted by four C 1-6 alkyl, A reaction is carried out to form a compound of formula (XXVII), wherein R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 5 , X 2 , X 5 and X 3 are as defined in any one of claims 1 to 45, react the compound of formula (XXVII) with an acid to form a compound of formula (I).

50. The compound according to any one of claims 1 to 45 or a pharmaceutically acceptable salt thereof, which is prepared by the method according to any one of claims 46 to 49.

51. The compound according to any one of claims 1 to 45 or a pharmaceutically acceptable salt thereof, which is used as a therapeutic active substance.

52. A pharmaceutical composition comprising the compound according to any one of claims 1 to 45 or a pharmaceutically acceptable salt thereof, and a pharmaceutical excipient.

53. The pharmaceutical composition according to claim 52, which further comprises an additional therapeutic agent.

54. The compound according to any one of claims 1 to 45 or a pharmaceutically acceptable salt thereof, which is used for treating, preventing and / or delaying the progression of an inflammatory autoimmune disease.

55. The compound according to any one of claims 1 to 45 or a pharmaceutically acceptable salt thereof, which is used for treating, preventing and / or delaying the progression of psoriasis, asthma, inflammatory bowel disease (IBD), Crohn's disease, obstructive lung disease, ulcerative colitis, rheumatoid arthritis, systemic lupus erythematosus and multiple sclerosis.

56. The compound according to any one of claims 1 to 45 or a pharmaceutically acceptable salt thereof, which is used for treating, preventing and / or delaying the progression of psoriasis, asthma, Crohn's disease, ulcerative colitis, rheumatoid arthritis, systemic lupus erythematosus and multiple sclerosis.

57. Use of the compound according to any one of claims 1 to 45 or a pharmaceutically acceptable salt thereof for the preparation of a medicament for treating, preventing and / or delaying an inflammatory autoimmune disease. Use of a compound according to any one of claims 1 to 45 or a pharmaceutically acceptable salt thereof for the preparation of a medicament for the treatment, prevention and / or delay of psoriasis, asthma, Crohn's disease, ulcerative colitis, rheumatoid arthritis, systemic lupus erythematosus and multiple sclerosis.

59. A method for treating, preventing and / or delaying the progression of an inflammatory autoimmune disease, the method comprising administering a therapeutically effective amount of a compound according to any one of claims 1 to 45 or a pharmaceutically acceptable salt thereof.

60. A method for treating, preventing and / or delaying the progression of psoriasis, asthma, inflammatory bowel disease (IBD), Crohn's disease, obstructive lung disease, ulcerative colitis, rheumatoid arthritis, systemic lupus erythematosus or multiple sclerosis, the method comprising administering a therapeutically effective amount of a compound according to any one of claims 1 to 45 or a pharmaceutically acceptable salt thereof.

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