Novel compound used as CBP / p300 inhibitor, and pharmaceutical composition for preventing or treating cancer, inflammatory disorders, or autoimmune diseases comprising same as active ingredient

Abstract

The present invention provides a novel compound used as a CBP / p300 inhibitor, an isomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof, and a solvate thereof, and provides a pharmaceutical composition for preventing or treating cancer, an inflammatory disorder, or an autoimmune disease, the pharmaceutical composition comprising at least one of the compound, isomer, salt, hydrate or solvate as an active ingredient.

Description

Novel compounds used as CBP / P300 inhibitors, and pharmaceutical compositions containing the same as active ingredients for preventing or treating cancer, inflammatory disorders, or autoimmune diseases

[0001] This application claims the benefit of priority to Republic of Korea Patent Application No. 2024-0007542, filed January 17, 2024, the entire disclosure of which is incorporated herein by reference. The present invention relates to a novel compound used as a CBP / p300 inhibitor, and a pharmaceutical composition comprising the same as an active ingredient for the prevention or treatment of cancer, inflammatory disorders, or autoimmune diseases.

[0002] CBP (CREB (cyclic-AMP response element-binding protein) binding protein) and its paralog p300 are transcription coactivators composed of multiple functional domains, including a histone acetyl-transferase (HAT) domain and a bromodomain (BRD). They recognize and induce histone lysine acetylation at specific loci, such as enhancers and promoters, on chromatin, and are major epigenetic modulators that regulate the expression of various genes.

[0003] Given their high structural similarity and functional redundancy, overexpression or mutations of CBP and p300, often referred to as CBP / p300, have been associated with several diseases, particularly malignancies. For example, CBP and p300 bind to chromatin via BRD and HAT and acetylate histones at enhancer sites of oncogenes. This relaxes chromatin structure and allows transcriptional proteins, including RNA polymerase II, to recruit. Consequently, they increase the expression of oncogenes such as MYC and IRF4 in tumor cells, leading to tumor formation and growth. Inhibition of the HAT domain results in an overall decrease in acetylation, which is crucial for transcription, affecting not only tumor cells but also normal cells, particularly stem cells. It has been reported that this makes it difficult to secure a therapeutic window and may cause toxicity, so it is expected that these concerns can be overcome through a bromodomain inhibitor strategy.

[0004] Accordingly, various studies have been conducted to develop inhibitors that selectively inhibit the bromodomain of CBP / p300 and thereby reduce the transcription of activated oncogenes in tumor cells. For example, CCS1477, a CBP / p300 bromodomain inhibitor developed by CellCentric, is in phase 1b / 2a clinical trials for the treatment of hematological malignancies and advanced drug-resistant prostate cancer, and various CBP / p300 activity modulators are also disclosed in patent documents 1 to 3 below.

[0005] However, developing effective and selective therapeutics targeting CBP / p300 remains a challenging task. Therefore, the development of more chemotypes of CBP / p300 inhibitors is necessary.

[0006] [Patent Document 1] WO2018073587

[0007] [Patent Document 2] WO2019191667

[0008] [Patent Document 3] WO2017205538

[0009] One object of the present invention is to provide a novel compound used as a CBP / p300 inhibitor.

[0010] Another object of the present invention is to provide an isomer of the compound, a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof.

[0011] Another object of the present invention is to provide a pharmaceutical composition for preventing or treating cancer, inflammatory disorders or autoimmune diseases, comprising at least one of the compound, an isomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof as an active ingredient.

[0012] In order to solve the above problem, according to one aspect of the present invention, a compound represented by the following chemical formula I is provided:

[0013] <Chemical Formula I>

[0014]

[0015] During the meal,

[0016] W, X or Y are each independently C or N,

[0017] n is an integer from 0 to 3, and when n is an integer greater than or equal to 2, each R is equal to or different from each other, and each R is independently NR a R b , SO2NHR c , CONHR d , SO2R e , CO2R f , halogen, C 1-4 Alkyl, C 1-4 Haloalkyl, or 3- to 9-membered heteroaryl, R aInland R f are each independently hydrogen, C 1-6 Alkyl, hydroxy, C 1-5 Selected from the group consisting of alkoxy, or 3- to 10-membered heterocycloalkyl,

[0018] m is an integer from 0 to 3, and when m is an integer greater than or equal to 2, each A is the same or different, and each A is independently amide, hydroxy, C 1-5 alkoxy, 3- to 10-membered heterocycloalkyl, 3- to 9-membered heteroaryl, or halogen, or two As are fused to each other to form a 3- to 10-membered heterocycloalkyl, or a 3- to 9-membered heteroaryl together with the atoms bonded thereto,

[0019] Z is hydrogen, amide, hydroxy, C 1-5 Alkoxy, C 1-4 Alkyl, C 6-14 aryl, 3- to 10-membered heterocycloalkyl or 3- to 14-membered heteroaryl,

[0020] At this time, the above R, R a Inland R f , A and Z are each substituted or unsubstituted with substituent group I.

[0021] Another aspect of the present invention relates to an isomer of the compound, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof.

[0022] Another aspect of the present invention relates to a pharmaceutical composition for preventing or treating cancer, inflammatory disorders or autoimmune diseases, comprising at least one of the compound, an isomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof as an active ingredient.

[0023] According to the present invention, it has been found that the compound represented by Chemical Formula I has excellent CBP / p300 inhibitory activity. Therefore, the compound represented by Chemical Formula I of the present invention; an isomer of the compound, a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof; and a pharmaceutical composition comprising at least one of these as an active ingredient can be usefully used for the prevention or treatment of cancer, inflammatory disorders, or autoimmune diseases, etc.

[0024] The effects of the present invention are not limited to the above-described effects, and should be understood to include all effects that can be inferred from the composition of the invention described in the description or claims of the present invention.

[0025] Below, the present invention will be described in more detail to facilitate understanding. The terms and words used in this specification and claims should not be interpreted based on their conventional or dictionary meanings. Based on the principle that the inventor can appropriately define the concepts of terms to best explain his or her invention, they should be interpreted in a way that aligns with the technical spirit of the present invention.

[0026] The present invention provides a compound represented by the following chemical formula I:

[0027] <Chemical Formula I>

[0028]

[0029] During the meal,

[0030] W, X or Y are each independently C or N,

[0031] n is an integer from 0 to 3, and when n is an integer greater than or equal to 2, each R is equal to or different from each other, and each R is independently NR a R b , SO2NHR c , CONHR d , SO2R e , CO2Rf , halogen, C 1-4 Alkyl, C 1-4 Haloalkyl, or 3- to 9-membered heteroaryl, R a Inland R f are each independently hydrogen, C 1-6 Alkyl, hydroxy, C 1-5 Selected from the group consisting of alkoxy, or 3- to 10-membered heterocycloalkyl,

[0032] m is an integer from 0 to 3, and when m is an integer greater than or equal to 2, each A is the same or different, and each A is independently amide, hydroxy, C 1-5 alkoxy, 3- to 10-membered heterocycloalkyl, 3- to 9-membered heteroaryl, or halogen, or two As are fused to each other to form a 3- to 10-membered heterocycloalkyl, or a 3- to 9-membered heteroaryl together with the atoms bonded thereto,

[0033] Z is hydrogen, amide, hydroxy, C 1-5 Alkoxy, C 1-4 Alkyl, C 6-14 aryl, 3- to 10-membered heterocycloalkyl or 3- to 14-membered heteroaryl,

[0034] At this time, the above R, R a Inland R f , A and Z may each be substituted or unsubstituted with substituent group I:

[0035] Substituent group I: substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 2-10 Alkenyl, substituted or unsubstituted C 3-20 Carbocycle, substituted or unsubstituted C 3-20 Cycloalkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted 3- to 30-membered heterocycle, substituted or unsubstituted C 1-10 Alkoxy, substituted or unsubstituted C2-10 Alkenyloxy, substituted or unsubstituted C 3-10 Cycloalkyloxy, substituted or unsubstituted C 6-30 Aryloxy, substituted or unsubstituted 3- to 30-membered heterocycloxy, substituted or unsubstituted C 1-10 Alkyl ketone, substituted or unsubstituted C 2-10 Alkenyl ketone, substituted or unsubstituted C 3-10 Cycloalkyl ketone, substituted or unsubstituted C 6-30 Aryl ketone, substituted or unsubstituted 3- to 30-membered heterocyclic ketone, substituted or unsubstituted C 1-10 Alkylthio, substituted or unsubstituted C 2-10 Alkenylthio, substituted or unsubstituted C 3-10 Cycloalkylthio, substituted or unsubstituted C 6-30 Arylthio, substituted or unsubstituted 3 to 30 membered heterocyclicthio, aldehyde, carboxy, halogen, substituted or unsubstituted C 1-10 Consisting of haloalkyl, hydroxy, substituted or unsubstituted amino, substituted or unsubstituted imine, cyano, substituted or unsubstituted nitro, substituted or unsubstituted amide, thiol, sulfone and phosphoric acid,

[0036] Here, C 1-10 Alkyl moieties are -O-, -S-, -SO-, -SO2-, -NR g -(R g is hydrogen or substituted or unsubstituted C 1-10 alkyl), -N=, =N-, -POR g - and -PO4R g - is interrupted by a heteroatom group selected from, and the heterocycle moiety may include at least one of S, N, P and O as a ring member atom.

[0037] In this specification, the matters regarding R are R 112 , R 313 , R 114 , R 314, R 215 , R 315 , R 116 , R 216 , R 316 . R 322 , R 223 , R 323 , R 132 , R 333 , R 134 , R 334 , R 142 , R 243 , R 344 , R 145 , R 345 , R 146 , R 246 , R 346 , R 352 , R 153 and R 353 The same can be applied to .

[0038] In defining the compound represented by Chemical Formula I throughout this specification, the following defined concepts are used. The following definitions apply to terms used individually or as part of a larger group throughout this specification, unless otherwise specified. Terms and abbreviations used herein have their original meanings unless otherwise defined.

[0039] As used herein, the term "substituted" may mean that a hydrogen atom bonded to a compound or each substituent listed in the substituent group is replaced and bonded with an arbitrary substituent. At this time, the position to be substituted is not limited to the position where the hydrogen atom bonded to each substituent listed in the compound or the substituent group exists, i.e., as long as the hydrogen atom is replaceable by a substituent. If two or more are substituted, the two or more substituents may be the same or different. Conversely, "unsubstituted" may mean that no hydrogen atom bonded to a carbon atom is replaced by an arbitrary substituent.

[0040] Any substituent applicable to the above “substitution” may be appropriately selected from the substituents listed in the substituent group described herein, but the category of substituents possible for substitution is not limited to this substituent group.

[0041] If a substituent is not separately described or mentioned in the chemical formula described herein, it may be considered that hydrogen is bonded, and in some cases, a substituent may be absent depending on the ring constituents forming the heterocycle.

[0042] As used herein, the term “halogen” includes, but is not limited to, fluoro, chloro, bromo, or iodo.

[0043] As used herein, the term “alkyl” by itself or as part of another substituent, unless otherwise stated, refers to a group having the indicated number of carbon atoms (i.e., C 1-10 It means a straight or branched chain monovalent hydrocarbon having 1 to 10 carbons.

[0044] Examples of the above alkyl include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but these are non-limiting examples and the scope of the present invention is not limited thereto.

[0045] As used herein, the term “aryl” refers to a ring containing multiple unsaturated, typically aromatic hydrocarbon rings, wherein the aryl may be monocyclic or polycyclic. In the case of polycyclic rings, it includes a form in which only aromatic hydrocarbon rings are fused and a form in which an aliphatic hydrocarbon ring is fused with an aromatic hydrocarbon ring. Examples of such aryls include monocyclic aryls such as phenyl, biphenyl, terphenyl, and quaternyl, and polycyclic aryls such as naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and benzopyrenyl.

[0046] As used herein, the term “heterocycle” means a ring comprising, as ring constituents, carbon atoms and 1 to 5 heteroatoms selected from non-carbon atoms, i.e., O, N, P and S. Here, the heterocycle may be aromatic, aliphatic, monocyclic or polycyclic and includes, but is not limited to, a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridinyl group, a bipyridinyl group, a pyrimidinyl group, a triazinyl group, a triazolyl group, a pyridazinyl group, a pyrazinyl group, a pyridopyrimidyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoxazolyl group, a thiadiazolyl group, and the like, but the scope of the present invention is not limited thereto.

[0047] As used herein, the term “heterocycloalkyl” means a partially or fully saturated hydrocarbon group containing one or more heteroatoms selected from O, N, P and S as a reducing group and forming a single or fused ring. Preferably, the heteroatoms may be 1, 1 to 2 or 1 to 3. Examples thereof include, but are not limited to, piperazinyl, piperazinedioneyl, piperidinyl, pyrrolidinyl, morpholinyl, imidazolidinyl, imidazolidinonyl, lactamyl, tetrahydropyranyl, tetrahydrofuranyl, diazabicyclooctanyl or diazaspiroctanyl.

[0048] As used herein, the term “heterocycloalkenyl” refers to an unsaturated hydrocarbon group containing one or more heteroatoms selected from O, N, P, and S as a reducing group and forming a single or fused ring. Preferably, the number of heteroatoms may be 1, 1 to 2, or 1 to 3. Examples include, but are not limited to, tetrahydropyridinyl.

[0049] As used herein, the term “heteroaryl” refers to an aromatic heterocycle, which may be monocyclic or polycyclic. Polycyclic includes not only a form in which multiple aromatic rings are fused, but also a form in which an aromatic ring and an aliphatic ring are fused. Examples of heteroaryl include pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, tetrazolyl, isothiazolyl, furyl, thienyl, pyridinyl, pyridyl N-oxide, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, benzothiazolyl, benzoxazolyl, benzothienyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, isoquinolinyl, thiophenyl, acridyl, indazolyl, carbazolyl, benzimidazolyl, benzocarbazolyl, benzofuranyl, benzothiophenyl, dibenzothiophenyl, pyrazolopyrimidinyl, indazolyl, pyrrolopyridinyl, pyrazolopyridinyl, or azaindoleyl, but are not limited thereto. The scope of the present invention is not limited.

[0050] As used herein, the term “amide” refers to a substituent that can be represented, for example, by RC(=O)-NR'R'', wherein R, R' and R'' are each, but not limited to, hydrogen, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 3-10 Carbocycle, substituted or unsubstituted C 3-10 Cycloalkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted 3- to 30-membered heterocycle or substituted or unsubstituted C 1-10 It may be haloalkyl, but is not limited to these.

[0051] As used herein, the term “alkenyl” may be straight-chain or branched-chain. Alkenyl is, for example, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-Dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-Ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl, 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, 1-nonenyl,These include, but are not limited to, 2-nonenyl, 3-nonenyl, 4-nonenyl, 1-decenyl, 2-decenyl, 3-decenyl, 4-decenyl, and 5-decenyl.

[0052] As used herein, the terms "carbocycle" and "carbocyclic" refer to a ring whose ring members are composed of carbon. A carbocycle can be aliphatic or aromatic, saturated or unsaturated, and monocyclic or polycyclic. Polycyclic rings can be fused, bridged, or spiro polycyclic rings. A monocyclic carbocycle can have 3 to 17 carbon atoms, specifically 3 to 14 carbon atoms, more specifically 3 to 10 carbon atoms, and particularly specifically 3 to 7 carbon atoms.

[0053] As used herein, the term “cycloalkyl” refers to a monovalent aliphatic carbocycle in which a hydrogen atom is missing from any of the carbon atoms constituting the ring. Examples of cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexylene, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

[0054] As used herein, the term “alkoxy” refers to a substituent having oxygen bonded to alkyl, which may be straight-chain, branched-chain or cyclic. Specific examples of alkoxy include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy or monohalogenated and polyhalogenated variants thereof.

[0055] In this specification, the term “oxy” means “-OR oxy As a substituent that can be represented as ", where R oxy are, but are not limited to, substituted or unsubstituted C respectively 1-10 Alkyl, substituted or unsubstituted C 2-10 Alkenyl, substituted or unsubstituted C 3-10 Carbocycle, substituted or unsubstituted C 3-10 Cycloalkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted 3- to 30-membered heterocycle, substituted or unsubstituted C 1-10 It may be haloalkyl, but is not limited to these.

[0056] As used herein, the term “carbonyl” means “-C(=O)R car As a substituent that can be represented as ", where R car are, but are not limited to, substituted or unsubstituted C respectively 1-10 Alkyl, substituted or unsubstituted C 2-10 Alkenyl, substituted or unsubstituted C 3-10 Carbocycle, substituted or unsubstituted C 3-10 Cycloalkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted 3- to 30-membered heterocycle, substituted or unsubstituted C 1-10It can be haloalkyl, and the definitions of each of these are as explained above. “Carbonyl” can be referred to as “ketone”, and depending on its substituent and bonding site, it can be referred to as “alkylketone”.

[0057] In this specification, the term “thior” means “-SR thio As a substituent that can be represented as ", where R thio are, but are not limited to, substituted or unsubstituted C respectively 1-10 Alkyl, substituted or unsubstituted C 2-10 Alkenyl, substituted or unsubstituted C 3-10 Carbocycle, substituted or unsubstituted C 3-10 Cycloalkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted 3- to 30-membered heterocycle, substituted or unsubstituted C 1-10 It may be haloalkyl, but is not limited to these.

[0058] As used herein, the term “haloalkyl” is synonymous with “halogenated alkyl” and “halogen-substituted alkyl,” and may refer to alkyl in which any hydrogen atom in the alkyl is replaced with any halogen atom. For example, -CF3, -CF2H, -CH2Cl, -CH2CF3, -C(Cl2)CF3, etc. are haloalkyl, but the scope of the present invention is not limited thereto.

[0059] In this specification, the term “amino” is intended to encompass monovalent primary amines, monovalent secondary amines, and monovalent tertiary amines. That is, amino refers to both monovalent groups having two hydrogen atoms bonded to a nitrogen atom and monovalent groups having at least one hydrogen atom replaced by another substituent. In the above, a group having two hydrogen atoms bonded to a nitrogen atom may be an unsubstituted amino, and a group having at least one hydrogen atom replaced by another substituent may be a substituted amino. Meanwhile, for dialkylamino, the alkyl moieties may be the same or different.

[0060] As used herein, the term “imine or imino” refers to a primary ketimine (-C(=NH)R i-1 ), secondary ketamine (-C(N=R i-2 )R i-1 ), primary aldimine (-C(=NH)H), secondary aldimine (-C(=NR i-1 )H) is intended to encompass. At this time, R i-1 and R i-2 is, without limitation, Independently, C 1-10 Alkyl, C 2-10 Alkenyl, C 3-10 Carbocycle, C 3-10 Cycloalkyl, C 6-30 Aryl, 3- to 30-membered heterocycle, C 1-10 It may be haloalkyl, each of which may be substituted or unsubstituted, but is not limited thereto.

[0061] As used herein, the term “sulfonyl” means “-S(=O)2R s1 As a substituent that can be represented as ", where R s1 Silver, but not limited to, each substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 2-10 Alkenyl, substituted or unsubstituted C 3-10 Carbocycle, substituted or unsubstituted C 3-10 Cycloalkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted 3- to 30-membered heterocycle, substituted or unsubstituted C 1-10 It may be haloalkyl, but is not limited to these.

[0062] In this specification, the term “thioamide” means “-C(=S)NR ta 2”, “-C(=S)NHR ta ” and “-C(=S)NH2” as substituents, R ta are independently and non-limitingly, each substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C2-10 Alkenyl, substituted or unsubstituted C 3-10 Carbocycle, substituted or unsubstituted C 3-10 Cycloalkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted 3- to 30-membered heterocycle, substituted or unsubstituted C 1-10 It may be haloalkyl, but is not limited to these.

[0063] In this specification, the term “sulfinyl” means “-S(=O)R s2 As a substituent that can be represented as ", where R s2 are, but are not limited to, substituted or unsubstituted C respectively 1-10 Alkyl, substituted or unsubstituted C 2-10 Alkenyl, substituted or unsubstituted C 3-10 Carbocycle, substituted or unsubstituted C 3-10 Cycloalkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted 3- to 30-membered heterocycle, substituted or unsubstituted C 1-10 Haloalkyl may be used, each of which is defined as described above. Sulfinyl may also be used interchangeably with "thiocarbonyl", and in a narrower sense R s2 When it is alkyl, it may also be referred to as alkylthiocarbonyl.

[0064] In this specification, the term “phosphoric acid” means “-OP(=O)(OH)2” or “-OP(=O)(OH)(OR P )” as a substituent, where R P are, but are not limited to, substituted or unsubstituted C respectively 1-10 Alkyl, substituted or unsubstituted C 2-10 Alkenyl, substituted or unsubstituted C 3-10 Carbocycle, substituted or unsubstituted C 3-10 Cycloalkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted 3- to 30-membered heterocycle, substituted or unsubstituted C 1-10It may be haloalkyl, but is not limited to these.

[0065] In this specification, the term “ester” means “-OC(=O)R ester As a substituent that can be represented as ", where R ester is non-limitingly substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 3-10 Carbocycle, substituted or unsubstituted C 3-10 Cycloalkyl, C 6-30 Aryl, substituted or unsubstituted 3- to 30-membered heterocycle, substituted or unsubstituted C 1-10 It may be haloalkyl, but is not limited to these.

[0066] In one embodiment, the R, R a Inland R f , A and Z may each be substituted or unsubstituted with substituent group I-1:

[0067] Substituent group I-1: substituted or unsubstituted C 1-5 Alkyl, substituted or unsubstituted C 3-5 Cycloalkyl, substituted or unsubstituted amino, substituted or unsubstituted C 6-8 Aryl, substituted or unsubstituted 3- to 9-membered heterocycloalkyl, substituted or unsubstituted 3- to 11-membered heteroaryl, substituted or unsubstituted C 1-3 Haloalkyl, substituted or unsubstituted C 1-3 Alkoxy, hydroxy, halogen, aldehyde, cyano, substituted or unsubstituted amide.

[0068] In one embodiment, the compound of formula I may be represented by any one of the following formulae I-1 to I-5:

[0069] <Chemical Formula I-1>

[0070]

[0071] <Chemical Formula I-2>

[0072]

[0073] <Chemical Formula I-3>

[0074]

[0075] <Chemical Formula I-4>

[0076]

[0077] <Chemical Formula I-5>

[0078]

[0079] In the above formula,

[0080] R, A, Z, n and m may each be as defined above.

[0081] In one embodiment, the chemical formula I-1 may be represented by any one of the following chemical formulas I-1-1 to I-1-6:

[0082] <Chemical Formula I-1-1>

[0083]

[0084] <Chemical Formula I-1-2>

[0085]

[0086] <Chemical Formula I-1-3>

[0087]

[0088] <Chemical Formula I-1-4>

[0089]

[0090] <Chemical Formula I-1-5>

[0091]

[0092] <Chemical Formula I-1-6>

[0093]

[0094] In the above formula,

[0095] R 112 , R 313 ,R 114 , R 314 , R 215 , R 315 , R 116 , R 216 and R 316 are the same or different, and each independently SO2NHR c , CONHR d , SO2R e , CO2R f , C 1-4 haloalkyl, or 3 to 9 membered heteroaryl, each of which is unsubstituted or substituted with substituent group I,

[0096] R c , R d , R e , R f , A, Z and m may each be as defined above.

[0097] In one embodiment, the chemical formula I-2 may be represented by any one of the following chemical formulas I-2-1 to I-2-3:

[0098] <Chemical Formula I-2-1>

[0099]

[0100] <Chemical Formula I-2-2>

[0101]

[0102] <Chemical Formula I-2-3>

[0103]

[0104] In the above formula,

[0105] R 322 , R 223 and R 323 may be the same or different and are each independently NR a R b , SO2NHR c , CONHR d , C 1-4 alkyl, or 3- to 9-membered heteroaryl, each of which is optionally substituted with substituent group I,

[0106] R a , R b , R c , R d , A, Z and m may each be as defined above.

[0107] In one embodiment, the chemical formula I-3 may be represented by any one of the following chemical formulas I-3-1 to I-3-4:

[0108] <Chemical Formula I-3-1>

[0109]

[0110] <Chemical Formula I-3-2>

[0111]

[0112] <Chemical Formula I-3-3>

[0113]

[0114] <Chemical Formula I-3-4>

[0115]

[0116] In the above formula,

[0117] R 132 , R 333 , R 134 and R 334 may be the same or different and each is independently NR a R b or may be halogen, each of which is substituted or unsubstituted with substituent group I,

[0118] R a ,R b , A, Z and m may each be as defined above.

[0119] In one embodiment, the chemical formula I-4 may be represented by any one of the following chemical formulas I-4-1 to I-4-6:

[0120] <Chemical Formula I-4-1>

[0121]

[0122] <Chemical Formula I-4-2>

[0123]

[0124] <Chemical Formula I-4-3>

[0125]

[0126] <Chemical Formula I-4-4>

[0127]

[0128] <Chemical Formula I-4-5>

[0129]

[0130] <Chemical Formula I-4-6>

[0131]

[0132] In the above formula,

[0133] R 142 , R 243 , R 344 , R 145 , R 345 , R 146 , R 246 and R 346 may be the same or different and are each independently NR a R b or CONHR d may be substituted or unsubstituted with substituent group I, respectively,

[0134] R a , R b , R d, A, Z and m may each be as defined above.

[0135] In one embodiment, the chemical formula I-5 may be represented by any one of the following chemical formulas I-5-1 to I-5-3:

[0136] <Chemical Formula I-5-1>

[0137]

[0138] <Chemical Formula I-5-2>

[0139]

[0140] <Chemical Formula I-5-3>

[0141]

[0142] In the above formula,

[0143] R 352 , R 153 and R 353 may be the same or different and are each independently NR a R b or may be halogen, each of which is substituted or unsubstituted with substituent group I,

[0144] R a , R b , A, Z and m may each be as defined above.

[0145] In one embodiment, each of the R's is independently NR a R b , SO2NHR c , CONHR d , SO2R e , CO2R f , chloro, C 1-2 haloalkyl, or pyrazolyl, wherein R a Inland R f are each independently hydrogen, methyl, ethyl, propyl, pyrrolidinyl, or morpholinyl, and R a Inland R fEach of which may be substituted or unsubstituted with substituent group I-1-1, and wherein R may be substituted or unsubstituted with substituent group I-1-2:

[0146] Substituent group I-1-1: substituted or unsubstituted C 1-3 Alkyl, substituted or unsubstituted C 3-5 Cycloalkyl, substituted or unsubstituted amino, substituted or unsubstituted C 6-8 Aryl, substituted or unsubstituted 3- to 9-membered heterocycloalkyl, substituted or unsubstituted 3- to 11-membered heteroaryl;

[0147] Substituent group I-1-2: substituted or unsubstituted C 1-3 Alkyl.

[0148] In one embodiment, A may be acetamide, carbamide, hydroxy, isoxazolyl, hydropyranyl or tetrahydropyranyl, or two As may be fused together to form imidazolidinonyl, lactamyl, piperazine dioyl or pyrrolyl together with the atoms bonded thereto, and A may be unsubstituted or substituted with substituent group I-1-3:

[0149] Substituent group I-1-3: substituted or unsubstituted C 1-4 Alkyl, substituted or unsubstituted C 3-5 Cycloalkyl, substituted or unsubstituted amide.

[0150] In one embodiment, Z may be hydrogen, methyl, hydroxy, amide, phenyl, naphthalenyl, tetrahydrofuranyl, lactamyl, tetrahydropyranyl, pyrrolyl, thiazolyl, imidazolyl, thiophenyl, isoxazolyl, pyrazolyl, pyridinyl, benzimidazolyl, indolyl, azaindolyl, indazolyl, benzofuranyl, benzothiophenyl, pyrazolopyridinyl, pyrazolopyrimidinyl, pyrrolopyridinyl, quinolinyl or isoquinolinyl, and Z may be unsubstituted or substituted with substituent group I-1-4:

[0151] Substituent group I-1-4: substituted or unsubstituted C 1-5 Alkyl, substituted or unsubstituted C 3-5 Cycloalkyl, C 1-3 Haloalkyl, substituted or unsubstituted C 6-8 Aryl, substituted or unsubstituted 3- to 8-membered heteroaryl, substituted or unsubstituted 4- to 8-membered heterocycloalkyl, substituted or unsubstituted 3- to 8-membered heterocycloalkenyl, substituted or unsubstituted C 1-3 Alkoxy, hydroxy, halogen, aldehyde, cyano, substituted or unsubstituted amide.

[0152] In one embodiment, the compound represented by the above chemical formula I may be any one selected from Table 2 below.

[0153] In one embodiment, the compound represented by the above formula I may be used as a CBP / p300 inhibitor. In the present specification, CBP / p300 may refer to CBP and / or p300. The CBP refers to CREB (cyclic-AMP response element binding protein) binding protein, and the p300 refers to a paralog of CBP.

[0154] The above CBP / p300 induces histone H3 lysine 27 acetylation (H3K27ac) at target gene promoters, enhancers, and super enhancers, and simultaneously recognizes acetylated histones through BRD to activate gene transcription. As the above CBP / p300 is overexpressed in cancer cells and drug-resistant cancer cells, it activates oncogene transcription and induces cancer cell proliferation, survival, tumor formation, metastasis, immune evasion, or drug resistance. Therefore, there is a need to inhibit the overexpression of CBP / p300 in cancer cells, etc. The use of the compound represented by the chemical formula I herein as a CBP / p300 inhibitor may mean that it has the above-described activity of inhibiting the overexpression of CBP / p300. The compound represented by the formula (I) of the present invention can, for example, reduce the H3K27ac and downregulate oncogene transcription, thereby inhibiting cancer cell growth and inducing apoptosis, activating the immune response, overcoming drug resistance, and inhibiting tumor progression in vivo. The compound represented by the formula (I) of the present invention can also, for example, enhance the anticancer efficacy of chemotherapy, radiotherapy, and epigenetic anticancer agents by inhibiting BRD.

[0155] The present invention also provides an isomer of the compound represented by the above chemical formula I, a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof.

[0156] As used herein, the term “isomer” may include enantiomers, diastereomers thereof, tautomers thereof, and geometric isomers thereof. As used herein, enantiomers refer to two stereoisomers of a compound that are non-superimposable mirror images of each other.

[0157] As used herein, diastereomers refer to stereoisomers that have two or more chiral centers and whose molecules are not mirror images of each other. Diastereoisomers have different physical properties, such as melting points, boiling points, spectral characteristics, and reactivities. Mixtures of diastereomers can be separated using high-resolution analytical procedures such as electrophoresis and chromatography.

[0158] In this specification, geometric isomers refer to cis type, in which the same type of atoms or atomic groups are on the same side of a double bond, and trans type, in which the same type of atoms or atomic groups are on the opposite side of a double bond.

[0159] As used herein, the term "tautomer" or "tautomeric form" refers to structural isomers of different energies that are compatible with each other through a low energy barrier. For example, proton tautomers (also known as protic tautomers) interconvert via the transfer of a proton, such as keto-enol and imine-enamine isomerization. Valence tautomers interconvert via the retransfer of some bonding electrons.

[0160] In the present specification, any atom present in the compounds of the present invention may exist in the form of its available naturally occurring isotopes. For example, isotopes of hydrogen, carbon, nitrogen, oxygen, phosphorus, sulfur, fluorine, chlorine, and iodine, 2 H(“D”), 3 H, 11 C, 12 C, 13 C, 14 C, 13 N, 15 N, 15 O, 17 O, 18 O, 32 P, 33 P, 35 S, 18 F, 36 Cl, 123 I and 125I may be present. The term "acceptable salt" as used herein refers to a salt of the active compound prepared with an acid or base, which depends on the specific substituents based on the compound described herein. When a compound according to the present invention contains a relatively acidic functional group, a base addition salt can be obtained by contacting such a neutral compound with a sufficient amount of the desired base in the absence of solvent or in a suitable inert solvent.

[0161] Acceptable salts include, for example, alkali metal salts, for example, sodium or potassium salts; alkaline earth metal salts, for example, calcium or magnesium salts; ammonium salts; aliphatic amine salts, for example, trimethylamine, triethylamine, dicyclohexylamine, ethanolamine, diethanolamine, triethanolamine or procaine salts; aralkyl amine salts, for example, N,N-dibenzylethylenediamine salts; heterocyclic aromatic amine salts, for example, pyridine salts, picolino salts, quinoline salts or isoquinoline salts; quaternary ammonium salts, for example, tetramethylammonium salts, tetraethylammonium salts, benzyltrimethylammonium salts, benzyltriethylammonium salts, benzyltributylammonium salts, methyltrioctylammonium salts or tetrabutylammonium salts; and basic amino acid salts, for example, arginine salts or lysine salts. The acid salts may be, for example, inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate, carbonate, hydrogencarbonate or perchlorate; organic acid salts such as acetate, propionate, lactate, malate, fumarate, tartrate, malate, fumarate, citrate, ascorbate, formic acid; sulfonates such as methanesulfonate, isothionate, benzenesulfonate or p-toluenesulfonate; and acidic amino acid salts such as aspartate or glutamate.

[0162] As used herein, the term “hydrate” means a compound in which water (H2O) is bound to another compound.

[0163] As used herein, the term "solvate" refers to an aggregate or complex of one or more solvent molecules and a compound of the present invention. Examples of solvents that form solvates include, but are not limited to, water, isopropanol, ethanol, methanol, dimethyl sulfoxide, ethyl acetate, acetic acid, and ethanolamine.

[0164] The present invention also provides a pharmaceutical composition for preventing or treating cancer, inflammatory disorders or autoimmune diseases, comprising at least one of a compound represented by the above chemical formula I, an isomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof as an active ingredient.

[0165] In one embodiment, the cancer may be a cancer dependent on the oncogene MYC, a tumor harboring a loss of function mutation of CBP or p300, or a cancer with activation of CBP and / or p300 function.

[0166] In one embodiment, the cancer disease may be at least one selected from the group consisting of blood cancer, prostate cancer, breast cancer, lung cancer, pancreatic cancer, colorectal cancer, and melanoma.

[0167] In one embodiment, the cancer disease is acoustic neuroma, acute leukemia, acute lymphoblastic leukemia, acute myeloid leukemia, acute T-cell leukemia, basal cell carcinoma, cholangiocarcinoma, bladder cancer, brain cancer, breast cancer, bronchial carcinoma, cervical cancer, chondrosarcoma, chordoma, choriocarcinoma, chronic leukemia, chronic lymphocytic leukemia, chronic myeloid leukemia, chronic myeloid leukemia, colon cancer, colorectal cancer, craniopharyngioma, cystadenocarcinoma, diffuse large B-cell lymphoma, dysproliferative changes, embryonal carcinoma, endometrial cancer, endotheliosarcoma, ependymoma, epithelioid carcinoma, erythroleukemia, esophageal cancer, estrogen receptor-positive breast cancer, essential thrombocythemia, Ewing's tumor, fibrosarcoma, follicular lymphoma, germ cell testicular cancer, glioma, glioblastoma, glioma, heavy chain disease head and neck cancer, hemangioblastoma, Hepatoma, hepatocellular carcinoma, hormone-insensitive prostate cancer, leiomyosarcoma, leukemia, liposarcoma, lung cancer, lymphoendothelioma, lymphangiosarcoma, lymphocytic leukemia, lymphoma, lymphoid malignancy of T-cell or B-cell origin, medullary carcinoma, medulloblastoma, melanoma, meningioma, mesothelioma, multiple myeloma, myeloid leukemia, myeloma, myxosarcoma, neuroblastoma, NUT midline carcinoma (NMC), non-small cell lung cancer, oligodendroglioma, oral cancer, osteosarcoma, ovarian cancer, pancreatic cancer, papillary adenocarcinoma, papillary carcinoma, pinealoma, polycythemia vera, prostate cancer, rectal cancer, renal cell carcinoma, retinoblastoma, rhabdomyosarcoma, sarcoma, sebaceous carcinoma, seminoma, skin cancer, small cell lung carcinoma, solid tumors (carcinoma and sarcoma), small cell lung cancer, gastric cancer, squamous cell It may be at least one selected from the group consisting of carcinoma, synovial tumor, sweat gland carcinoma, thyroid cancer, Waldenstrom macroglobulinemia, testicular tumor, uterine cancer, and Wilms tumor.

[0168] In one embodiment, the inflammatory disorder or autoimmune disease is Addison's disease, acute gout, ankylosing spondylitis, asthma, atherosclerosis, Behcet's disease, bullous skin disease, chronic obstructive pulmonary disease, Crohn's disease, dermatitis, eczema, giant cell arteritis, fibrosis, glomerulonephritis, hepatic vascular occlusion, hepatitis, hypophysitis, immunodeficiency syndrome, inflammatory bowel disease, Kawasaki disease, lupus nephritis, multiple sclerosis, myocarditis, myositis, nephritis, organ transplant rejection, osteoarthritis, pancreatitis, pericarditis, polyarteritis nodosa pneumonia, primary biliary cirrhosis, psoriasis, psoriatic arthritis, rheumatoid arthritis, scleritis, sclerosing cholangitis, sepsis, systemic lupus erythematosus, Takayasu's arteritis, toxic shock, thyroiditis, type 1 diabetes, ulcerative colitis, uveitis, vitiligo, vasculitis, and Wegener's It may be one or more selected from the group consisting of granulomatous diseases.

[0169] In one embodiment, the pharmaceutical composition may further comprise a pharmaceutically acceptable diluent or carrier. Specifically, the pharmaceutical composition of the present invention may comprise a pharmaceutically acceptable carrier, and may be formulated into oral dosage forms such as powders, granules, tablets, capsules, suspensions, emulsions, syrups, aerosols, topical preparations, suppositories, and sterile injectable solutions, each according to a conventional method. The pharmaceutically acceptable carrier may include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia gum, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methylcellulose, microcrystalline cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, and mineral oil. In addition, the pharmaceutically acceptable carrier may include diluents or excipients such as fillers, bulking agents, binders, wetting agents, disintegrating agents, and surfactants. Oral solid preparations may include tablets, pills, powders, granules, capsules, etc., and these solid preparations may include at least one excipient, such as starch, calcium carbonate, sucrose or lactose, gelatin, etc., and lubricants, such as magnesium stearate, talc, etc. Oral liquid preparations may include suspensions, oral solutions, emulsions, syrups, etc., and may include diluents, such as water or liquid paraffin, wetting agents, sweeteners, flavoring agents, preservatives, etc. Parenteral preparations may include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilized preparations, suppositories, and non-aqueous solvents and suspending agents may include propylene glycol, polyethylene glycol, vegetable oils, such as olive oil, and injectable esters, such as ethyl oleate.Suppository bases that can be used include witepsol, macrogol, tween 61, cocoa butter, laurin butter, and glycerogelatin.

[0170] In one embodiment, the dosage of the compound represented by Chemical Formula 1, its isomer, its pharmaceutically acceptable salt, its hydrate or its solvate contained in the pharmaceutical composition of the present invention varies depending on the patient's condition and weight, the degree of the disease, the drug form, the route and period of administration, and may be appropriately selected by a person skilled in the art. For example, the pyrazole derivative compound represented by Chemical Formula 1, or its pharmaceutically acceptable salt, may be administered at a dosage of 0.0001 to 1000 mg / kg per day, preferably 0.01 to 1000 mg / kg, and the administration may be administered once a day or divided into several times. In addition, the pharmaceutical composition of the present invention may contain the pyrazole derivative compound represented by Chemical Formula 1, or its pharmaceutically acceptable salt, in a weight percentage of 0.001 to 90% based on the total weight of the composition.

[0171] In one embodiment, the pharmaceutical composition of the present invention can be administered to mammals such as rats, mice, livestock, and humans by various routes, for example, orally, intraperitoneally, rectally, or by intravenous, intramuscular, subcutaneous, intrauterine, or intracerebroventricular injection.

[0172] Hereinafter, the present invention will be described in more detail through manufacturing examples, working examples, and experimental examples. However, the following working examples and experimental examples are intended to illustrate the present invention and are not intended to limit the scope of the present invention.

[0173] A compound having the structure of the above chemical formula I can be synthesized by the following method.

[0174] <General scheme I>

[0175]

[0176] <General scheme II>

[0177]

[0178] The analyses of the compounds prepared in the following manufacturing examples and examples were performed as follows: Nuclear magnetic resonance (NMR) spectral analysis was performed on a Bruker 500 MHz or Jeol 400 MHz spectrometer. Mass spectrometry was performed using LC / MS (Agilent 1260 infinity II / Agilent infinity lab LC / MSD, API-ES mode, UV detection at 220 nm / 254 nm). (Column: ZORBAX RRHT StableBond C18, 2.1 x 50 mm, 1.8 μm, 80Å, Mobile phase: water / acetonitrile / formic acid (30 / 70 / 0.1%), isocratic elution for 3 min.)

[0179] In addition, MPLC (Medium pressure liquid chromatography, CombiFlash Nextgen 300+) or prepHPLC (Thermo Ultimate 3000 equipped with a diode array detector, UV detection: 215 nm, 254 nm, 280 nm) was used for the purification of the compound. The prepHPLC conditions were as follows. (Column: Agilent Prep-C18, 250 x 21.2 mm, 10 μm, Mobile phase A: water / 0.1% formic acid, Mobile phase B: acetonitrile / 0.1% formic acid, gradient elution for 30 min, A:B = 90:10 - 30:70)

[0180] Each starting material was a known compound, synthesized according to the literature, or purchased commercially.

[0181] Intermediate synthesis method

[0182] Intermediate I-1 (Synthetic Method IA): 5-Amino-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0183] Step 1) Preparation of 5-nitro-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0184] 4-Nitrobenzene-1,2-diamine (10 g, 65.3 mmol) was dissolved in tetrahydrofuran (365 mL), cooled to 0 °C, and 1,1-carboimidazole (21 g, 130.6 mmol) was added. The reaction solution was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and the resulting solid was washed with diethyl ether, 1 N hydrochloric acid, and water. The solid was dried under vacuum to obtain the title compound. (9.59 g, 53.5 mmol, 82% yield)

[0185] 1 H NMR (500 MHz, DMSO-d6) δ 11.43 (s, 1H), 11.20 (s, 1H), 7.94 (dd, J = 8.6, 2.3 Hz, 1H), 7.71 (d, J = 2.2 Hz, 1H), 7.10 (d, J = 8.6 Hz, 1H).

[0186] Step 2) Preparation of 1,3-dimethyl-5-nitro-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0187] 5-Nitro-1,3-dihydro-2H-benzo[d]imidazol-2-one (4.9 g, 27.5 mmol) was dissolved in dimethylformamide (70 mL) and cooled to 0°C. Sodium hydride (60% dispersion in mineral oil, 4.4 g, 110 mmol) was added little by little, and methyl iodide (11.7 g, 5.13 mL, 83.0 mmol) was added. The reaction solution was stirred at 60°C for 2 hours, and then water was added to quench the reaction. The reaction solution was diluted with ethyl acetate and washed with 0.1 N hydrochloric acid and brine. The oil layer was concentrated under reduced pressure, and the obtained solid was washed with hexane and dried in vacuo to obtain the title compound. (4.95 g, 23.4 mmol, 87% yield)

[0188] 1 H NMR (500 MHz, Chloroform-d) δ 8.12 (dd, J = 8.6, 2.2 Hz, 1H), 7.89 (d, J = 2.1 Hz, 1H), 7.02 (d, J = 8.6 Hz, 1H), 3.50 (s, 3H), 3.49 (s, 3H).

[0189] Step 3) Preparation of 5-amino-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0190] 1,3-Dimethyl-5-nitro-1,3-dihydro-2H-benzo[d]imidazol-2-one (3.5 g, 16.9 mmol) was dissolved in ethyl acetate / methanol (50 ml / 50 mL), and palladium / carbon (10 wt%, 0.7 g) was added. The reaction system was replaced with hydrogen using a hydrogen balloon, and the reaction solution was stirred under hydrogen conditions for 3 hours. After the reaction was completed, the reaction solution was filtered through a celite pad to remove the catalyst. The filtrate was concentrated under reduced pressure to obtain the title compound, which was used in the next reaction without further purification (2.79 g, 15.7 mmol, 93% yield).

[0191] 1H NMR (500 MHz, DMSO-d6) δ 6.78 (d, J = 8.2 Hz, 1H), 6.35 (d, J = 2.0 Hz, 1H), 6.31 (dd, J = 8.2, 2.1 Hz, 1H), 4.77 (s, 2H), 3.22 (s, 3H), 3.21 (s, 3H).

[0192] Intermediate I-2 (Synthetic Method IB): Preparation of 3-fluoro-N-methyl-4-nitrobenzenesulfonamide

[0193] Step 1) Preparation of 3-fluoro-N-methyl-4-nitrobenzenesulfonamide

[0194] A solution of 3-fluoro-4-nitrobenzenesulfonyl chloride (10 g, 41.7 mmol) in dichloromethane (100 mL) was cooled to 0°C, and then a methanamine solution (2 M in tetrahydrofuran, 52.2 mL, 104 mmol) was slowly added dropwise. The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the methylamine salt was filtered and washed with dichloromethane. The filtrate was concentrated under reduced pressure and used in the next reaction without further purification (11.4 g, 48.6 mmol).

[0195] 1 H-NMR (400 MHz, Chloroform-d) δ 8.26-8.14 (m, 2H), 7.80 (t, J = 9.3 Hz, 2H), 4.56 (s, 1H), 2.83-2.74 (3H).

[0196] Intermediate I-3: Preparation of 4-amino-3-((1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)-N-methylbenzenesulfonamide

[0197] Step 1) Preparation of 3-((1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)-N-methyl-4-nitrobenzenesulfonamide

[0198] 3-Fluoro-N-methyl-4-nitrobenzenesulfonamide (intermediate I-2, 0.5 g, 2.156 mmol) was added to 1,4-dioxane (5 mL), and 5-amino-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (intermediate I-1, 420 mg, 2.37 mmol) and N,N-diisopropylethylamine (1.13 mL, 6.47 mmol) were added. The solution was heated to 100 °C under reflux conditions and stirred for 18 h. The reaction solution was cooled to 0 °C and stirred for 1 h, and the precipitated solid was filtered and the orange filter cake was washed with ethyl acetate (797 mg, 2.04 mmol, 94% yield).

[0199] 1 H-NMR (400 MHz, Chloroform-d) δ 9.58 (s, 1H), 8.34 (d, J = 9.1 Hz, 1H), 7.52 (t, J = 2.1 Hz, 1H), 7.11 (dd, J = 8.7, 1.8 Hz, 1H), 7.02 (d, J = 1.4 Hz, 2H), 6.89 (s, 1H), 4.31 (d, J = 5.0 Hz, 1H), 3.46 (s, 3H), 3.44-3.35 (m, 3H), 2.73-2.60 (m, 3H)

[0200] Step 2) Preparation of 4-amino-3-((1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)-N-methylbenzenesulfonamide

[0201] 3-((1,3-Dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)-N-methyl-4-nitrobenzenesulfonamide (1.03 g, 2.64 mmol) was dissolved in ethanol (26 mL) and tin(II) chloride dihydrate (SnCl 2ㆍ2H2O)(0.89 g, 3.96 mmol) was added. The solution was heated to 80°C and stirred for 4 h under reflux conditions. The reaction solution was cooled to 0°C, diethyl ether (5 mL) was added, and stirred for 30 min. The resulting solid was filtered and the filter cake was washed with diethyl ether. The red solid was dried under nitrogen (840 mg, 2.32 mmol, 88% yield).

[0202] 1 H-NMR (400MHz, DMSO-d6) δ 7.31 (s, 1H), 7.12 (d, J = 8.2 Hz, 1H), 7.05 (s, 1H), 7.02 (d, J = 8.2 Hz, 1H), 6.94 (q, J = 5.1 Hz, 1H), 6.77 (d, J = 8.2 Hz, 1H), 6.69 (s, 1H), 6.64 (d, J = 7.3 Hz, 1H), 5.55 (s, 2H), 3.30 (s, 3H), 3.24 (s, 3H), 2.34 (d, J = 4.9 Hz, 3H)

[0203] Intermediate I-4: Preparation of 5-((6-chloro-5-nitropyrimidin-4-yl)amino)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0204] 4,6-Dichloro-5-nitropyrimidine (137.03 mg, 0.773 mmol) was added to a solution of 5-amino-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (Intermediate I-1, 150 mg, 0.77 mmol) in tetrahydrofuran (10 mL). A solution of sodium bicarbonate (129.8 mg, 1.55 mmol) in water (2 mL) was added at 0 °C. The reaction solution was stirred at low temperature for 1 h. Water and ethyl acetate were added to the reaction solution, and the oil layer was extracted. The collected oil layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The title compound was obtained by separation using prepHPLC (200.00 mg, 0.60 mmol, 77.73% yield).

[0205] Intermediate I-5 (Synthetic Method IC): Preparation of 3-fluoro-N-methyl-4-nitrobenzamide

[0206] 3-Fluoro-4-nitrobenzoic acid (1 g, 5.4 mmol) and N-ethylcarbodiimide hydrochloride (1.3 g, 7.02 mmol) were dissolved in dichloromethane (15 mL), and methylamine (2 M in tetrahydrofuran, 2.7 mL, 5.4 mmol) was slowly added dropwise at 0 °C. The mixture was warmed to room temperature and stirred for 2 hours. After cooling to 0 °C, water and 1 N hydrochloric acid were added, and the mixture was extracted with dichloromethane. The oil layer was washed with 1 N sodium hydroxide, concentrated under reduced pressure, and used in the next reaction without further purification.

[0207] Intermediate I-6: Preparation of 4-(difluoromethyl)-2-fluoro-1-nitrobenzene

[0208] 3-Fluoro-4-nitrobenzaldehyde (1 g, 5.91 mmol) was dissolved in dichloromethane (60 mL), cooled to 0 °C, and diethylaminosulfur trifluoride (3.34 g, 20.70 mmol) was slowly added. The reaction solution was stirred at room temperature for 12 hours. Saturated sodium bicarbonate solution was added to the reaction solution, and it was extracted with dichloromethane. Sodium sulfate was added to the combined oil layer to remove water, and then filtered. The filtrate was concentrated under reduced pressure and purified by MPLC to obtain the title compound (540 mg, 5.91 mmol, 47.8% yield).

[0209] Intermediate I-7: Preparation of 3-(3,5-dimethylisoxazol-4-yl)aniline

[0210] 3-Bromoaniline (4.8 g, 27.9 mmol) was dissolved in 1,4-dioxane (100 mL). (3,5-dimethylisoxazol-4-yl)boronic acid (5.90 g, 41.9 mmol) and sodium carbonate (2 M in water) (27.9 mL, 55.8 mmol) were added under nitrogen, and nitrogen was bubbled for 5 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.967 g, 0.837 mmol) was added to the reaction mixture, and the mixture was stirred at 90 °C for 24 h. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The oil layer was washed with brine, concentrated under reduced pressure, and then purified by MPLC to obtain the desired material (5.05 g, 26.8 mmol, 96% yield).

[0211] 1 H-NMR (500 MHz, Chloroform-d) δ 7.21 (t, J = 7.8 Hz, 1H), 6.68 (dd, J = 7.9, 2.1 Hz, 1H), 6.63 (d, J = 7.6 Hz, 1H), 6.55 (d, J = 1.5 Hz, 1H), 3.73 (s, 2H), 2.40 (s, 3H), 2.26 (s, 3H)

[0212] Intermediate I-8: Preparation of 1-(3-aminophenyl)-1,3,3-trimethylurea

[0213] Step 1) Preparation of 1-methyl-3-(3-nitrophenyl)urea

[0214] 3-Nitroaniline (300 mg, 2.172 mmol) and N-methyl-1H-imidazole-1-carboxamide (1359 mg, 10.86 mmol) were dissolved in dimethylformamide (7.2 mL), and N,N-diisopropylethylamine (759 μL, 4.34 mmol) was added. The reaction solution was stirred at 90 °C for 18 h. After the reaction was complete, water was added, and the oil layer was extracted using dichloromethane. The oil layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by MPLC to obtain the title compound (193 mg, 0.989 mmol, 45.5% yield).

[0215] 1 H-NMR (500 MHz, DMSO-d6) δ 9.08 (d, J = 1.8 Hz, 1H), 8.19 (s, 1H), 8.12 (m, 1H), 8.06-8.03 (m, 1H), 7.62 (d, J = 9.2 Hz, 1H), 2.80 (d, J = 4.3 Hz, 3H)

[0216] Step 2) Preparation of 1,1,3-trimethyl-3-(3-nitrophenyl)urea

[0217] 1-Methyl-3-(3-nitrophenyl)urea (193.3 mg, 0.990 mmol) was dissolved in dimethylformamide (10 mL), and sodium hydride (60% dispersion in mineral oil, 158 mg, 3.96 mmol) was slowly added at 0 °C, stirred for 30 minutes, and then iodomethane (0.247 mL, 3.96 mmol) was added. The reaction solution was stirred for 6 hours. After the reaction was completed, water was added at 0 °C to terminate the reaction. The reaction solution was filtered, and the filtrate was extracted with dichloromethane. The oil layer was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain the title compound, which was used directly in the next step without further purification (146 mg, 0.654 mmol, 66.0% yield).

[0218] Step 3) Preparation of 1-(3-aminophenyl)-1,3,3-trimethylurea

[0219] 1,1,3-Trimethyl-3-(3-nitrophenyl)urea (146.9 mg, 0.658 mmol) was dissolved in methanol (6.6 mL), palladium / carbon (210 mg, 0.197 mmol) was added, and the mixture was stirred at room temperature for 18 h under a hydrogen balloon. After the reaction was completed, the mixture was passed through a celite filter, and the filtrate was concentrated. After MPLC purification, the title compound was obtained (140 mg, 0.724 mmol, 110% yield).

[0220] 1 H-NMR (500 MHz, DMSO-d6) δ 6.99 (t, J = 7.9 Hz, 1H), 6.36-6.33 (m, 1H), 6.30 (s, 1H), 6.24 (d, J = 7.9 Hz, 1H), 2.98 (s, 3H), 2.63 (s, 6H)

[0221] Intermediate I-9: Preparation of 5-amino-N-methyl-1H-indole-3-carboxamide

[0222] Step 1) Preparation of N-methyl-5-nitro-1H-indole-3-carboxamide

[0223] 5-Nitro-1H-indole-3-carboxylic acid (310 mg, 1.504 mmol), N,N-diisopropylethylamine (0.524 mL, 3.00 mmol), 1-(bis(dimethylamino)methylene)-1H-benzo[d][1,2,3]triazol-1-ium 3-oxide tetrafluoroborate (963 mg, 3.00 mmol) were dissolved in dimethylformamide (1.5 mL), and then methaneamine (2 M in tetrahydrofuran, 1.5 mL, 3.00 mmol) was added. The reaction solution was stirred at room temperature for 18 hours. After the reaction was complete, water was added, the reaction solution was basified with 1 N aqueous sodium hydroxide solution, and the resulting solid was filtered. The filter cake was washed with water, dried under nitrogen conditions, and used directly in the next step without further purification (264 mg, 1.204 mmol, 40.1% yield).

[0224] 1 H-NMR (500 MHz, DMSO-d6) δ 9.08 (d, J = 1.8 Hz, 1H), 8.19 (s, 1H), 8.12-8.13 (m, 1H), 8.06-8.03 (m, 1H), 7.62 (d, J = 9.2 Hz, 1H), 2.80 (d, J = 4.3 Hz, 3H)

[0225] Step 2) Preparation of 5-amino-N-methyl-1H-indole-3-carboxamide

[0226] N-Methyl-5-nitro-1H-indole-3-carboxamide (310 mg, 1.414 mmol) was dissolved in methanol (7.1 mL) and tetrahydrofuran (7.1 mL), palladium / carbon (452 ​​mg, 0.424 mmol) was added, and the mixture was stirred at room temperature under a hydrogen balloon for 18 h. After the reaction was completed, the mixture was passed through a celite filter, and the filtrate was concentrated to obtain the title compound (264 mg, 1.395 mmol, 99% yield).

[0227] 1H-NMR (400 MHz, DMSO-d6) δ 11.02 (s, 1H), 7.72 (d, J = 3.2 Hz, 1H), 7.59-7.58 (m, 1H), 7.31 (d, J = 2.3 Hz, 1H), 7.07 (d, J = 8.2 Hz, 1H), 6.51 (dd, J = 8.7, 2.3 Hz, 1H), 2.73 (d, J = 4.6 Hz, 3H)

[0228] Intermediate I-10: Preparation of 5-amino-1,4-dimethyl-1,4-dihydroquinoxaline-2,3-dione

[0229] Step 1) Preparation of 5-nitro-1,4-dihydroquinoxaline-2,3-dione

[0230] 3-Nitrobenzene-1,2-diamine (500 mg, 3.26 mmol) and oxalic acid (588 mg, 6.53 mmol) were dissolved in 4N aqueous hydrochloric acid solution (0.816 mL, 3.26 mmol) and stirred at 120 °C for 6 hours. After the reaction was completed, the resulting solid was filtered to obtain the title compound as a light green solid (483 mg, 2.332 mmol, 71.4% yield).

[0231] Step 2) Preparation of 1,4-dimethyl-5-nitro-1,4-dihydroquinoxaline-2,3-dione

[0232] 5-Nitro-1,4-dihydroquinoxaline-2,3-dione (200 mg, 0.966 mmol) was dissolved in dimethylformamide (10 mL), and sodium hydride (60% dispersed in mineral oil, 116 mg, 2.90 mmol) was slowly added at 0 °C. The mixture was stirred for 30 minutes, and then iodomethane (0.247 mL, 3.96 mmol) was added. The reaction mixture was stirred for 2 hours. After the reaction was completed, water was added at 0 °C to terminate the reaction. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure and purified by MPLC to obtain the title compound as a yellow solid (71 mg, 0.302 mmol, 31.3% yield).

[0233] 1 H-NMR (500 MHz, DMSO-d6) δ 7.76 (d, J = 2.7 Hz, 1H), 7.74 (d, J = 3.7 Hz, 1H), 7.59 (t, J = 8.2 Hz, 1H), 3.93 (s, 3H), 3.64 (s, 3H)

[0234] Step 3) Preparation of 5-amino-1,4-dimethyl-1,4-dihydroquinoxaline-2,3-dione

[0235] 1,4-Dimethyl-5-nitro-1,4-dihydroquinoxaline-2,3-dione (71.3 mg, 0.303 mmol) was dissolved in methanol (3 mL) and 1,4-dioxane (3 mL), palladium / carbon (32.3 mg, 0.030 mmol) was added, and the mixture was stirred at room temperature under a hydrogen balloon for 18 h. After the reaction was completed, the mixture was passed through a celite filter, and the filtrate was concentrated to obtain the title compound (50 mg, 0.244 mmol, 80% yield).

[0236] 1 H-NMR (400 MHz, DMSO-d6) δ 7.12 (t, J = 8.0 Hz, 1H), 6.59-6.54 (m, 2H), 5.64 (s, 2H), 3.96 (s, 3H), 3.54 (s, 3H), LC / MS 206 (M+H)

[0237] Intermediate I-11: Preparation of N-(3-amino-5-(tetrahydro-2H-pyran-4-yl)phenyl)acetamide

[0238] Step 1) Preparation of N-(3-bromo-5-nitrophenyl)acetamide

[0239] 3-Bromo-5-nitroaniline (300 mg, 1.382 mmol) was dissolved in dichloromethane (10 mL), and acetyl chloride (0.104 mL, 1.451 mmol) and pyridine (0.223 mL, 2.76 mmol) were added. The mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was concentrated under reduced pressure and separated by MPLC to obtain the title compound (385.6 mg, 1.488 mmol, 108% yield).

[0240] 1 H-NMR (500 MHz, Chloroform-d) δ 8.25 (s, 1H), 8.23 ​​(s, 1H), 8.09 (s, 1H), 2.24 (s, 3H)

[0241] Step 2) Preparation of N-(3-(3,6-dihydro-2H-pyran-4-yl)-5-nitrophenyl)acetamide

[0242] N-(3-Bromo-5-nitrophenyl)acetamide (240 mg, 0.926 mmol) was added to 1,4-dioxane (5.8 mL) / water (1.4 mL), and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (214 mg, 1.019 mmol) and sodium carbonate (0.463 mL, 0.926 mmol) (2 M in water) were added. 1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(Pd(dppf)Cl2)·dichloromethane (151 mg, 0.185 mmol) was added and bubbled with nitrogen for 5 minutes. The reaction mixture was stirred at 90 °C for 18 h. After the reaction was completed, water was added and extracted with ethyl acetate. The oil layer was washed with brine, concentrated under reduced pressure, and separated by MPLC to obtain the title compound (163 mg, 0.62 mmol, 67.1%).

[0243] 1H-NMR (500 MHz, Chloroform-d) δ 8.16 (s, 1H), 8.04 (s, 1H), 7.98 (s, 1H), 7.37 (s, 1H), 6.30 (s, 1H), 4.35 (q, J = 2.7 Hz, 2H), 3.95 (t, J = 5.5 Hz, 2H), 2.53 (m, 2H), 2.23 (s, 3H)

[0244] Step 3) Preparation of N-(3-amino-5-(tetrahydro-2H-pyran-4-yl)phenyl)acetamide

[0245] N-(3-(3,6-dihydro-2H-pyran-4-yl)-5-nitrophenyl)acetamide (161.7 mg, 0.617 mmol) was added to methanol (6 mL), and palladium / carbon (10 wt%, 52.5 mg, 0.049 mmol) was added. The reaction solution was stirred at room temperature under a hydrogen balloon for 2 h. The reaction solution was filtered through a pad of Celite and washed with methanol. The filtrate was concentrated under reduced pressure and used in the next reaction without further purification. (158.4 mg, 110%)

[0246] 1 H-NMR (400 MHz, Chloroform-d) δ 7.60 (s, 1H), 7.00 (1H), 6.59 (1H), 6.30 (s, 1H), 4.38-3.95 (m, 2H), 3.72 (s, 2H), 3.48 (s, 3H), 2.75-2.46 (m, 1H), 2.13 (s, 3H), 1.73 (s, 4H)

[0247] Intermediate I-12: Preparation of 3-amino-5-(tetrahydro-2H-pyran-4-yl)phenol

[0248] Step 1) Preparation of 3-(3,6-dihydro-2H-pyran-4-yl)-5-nitrophenol

[0249] 3-Bromo-5-nitrophenol (60 mg, 0.275 mmol) was dissolved in 1,4-dioxane (1.5 mL), and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (69.4 mg, 0.330 mmol) and sodium carbonate (2 M in water) (0.275 mL, 0.550 mmol) were added. The reaction solution was stirred for 5 minutes while bubbling with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (9.54 mg, 8.26 μmol) was added to the reaction solution, and the mixture was stirred under reflux conditions (120 °C) for 18 hours. Water was added to the reaction solution, the mixture was extracted with dichloromethane, and the oil layer was concentrated under reduced pressure. The title compound was obtained by separation using MPLC (58 mg, 0.262 mmol, 95% yield).

[0250] Step 2) Preparation of 3-amino-5-(tetrahydro-2H-pyran-4-yl)phenol

[0251] 3-(3,6-Dihydro-2H-pyran-4-yl)-5-nitrophenol (950 mg, 4.29 mmol) was added to methanol (40 mL), and palladium / carbon (137 mg, 1.288 mmol) was added. The reaction solution was stirred under a hydrogen balloon for 3 h. The reaction solution was filtered through a pad of Celite and washed with methanol. The filtrate was concentrated under reduced pressure and purified by MPLC to obtain the title compound (530 mg, 2.74 mmol, 63.9% yield).

[0252] 1 H-NMR (500 MHz, Chloroform-d) δ 6.19 (s, 1H), 6.13 (s, 1H), 6.05 (s, 1H), 4.68 (s, 1H), 4.06 (d, J = 11.0 Hz, 2H), 3.68 (s, 2H), 3.50 (t, J = 11.3 Hz, 2H), 2.59 (s, 1H), 1.81-1.68 (m, 4H)

[0253] In addition, intermediates synthesized in a similar manner as above and their synthesis methods are shown in Table 1.

[0254] No. Name 1 H NMR synthesis method I-135-amino-1,3-diethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one 1 H NMR (500 MHz, DMSO-d6) δ 6.83 (d, J = 8.2 Hz, 1H), 6.40 (d, J = 2.0 Hz, 1H), 6.30 (dd, J = 8.2, 2.0 Hz, 1H), 4.75 (s, 2H), 3.74 (qd, J = 7.2, 5.0 Hz, 4H), 1.16 (q, J = 7.1 Hz, 6H).I-AI-145-amino-1,3-dicyclopropyl-1,3-dihydro-2H-benzo[d]imidazol-2-one 1 H NMR (500 MHz, DMSO-d6) δ 6.92 (d, J = 8.2 Hz, 1H), 6.64 (s, 1H), 6.47 (d, J = 8.2 Hz, 1H), 6.35 (s, 2H), 2.75 (tq, J = 6.8, 3.5 Hz, 2H), 1.01 - 0.90 (m, 4H), 0.83 - 0.75 (m, 4H).I-AI-153-Fluoro-N-(2-morpholinoethyl)-4-nitrobenzenesulfonamide N / DI-BI-163-Fluoro-4-nitro-N-(2-(pyrrolidin-1-yl)ethyl)benzenesulfonamide N / DI-BI-17N-(cyclopropylmethyl)-3-fluoro-4-nitrobenzenesulfonamide N / DI-BI-184-((3-fluoro-4-nitrophenyl)sulfonyl)morpholine N / DI-BI-193-Fluoro-4-nitrobenzenesulfonamide N / DI-BI-20N-Ethyl-3-fluoro-4-nitrobenzenesulfonamide N / DI-BI-21N-Benzyl-3-fluoro-4-nitrobenzenesulfonamide N / DI-BI-223-Fluoro-N-isobutyl-4-nitrobenzenesulfonamide N / DI-BI-236-Chloro-N-methyl-5-nitropicolinamide N / DI-C

[0255] The synthesis method commonly used in each example is as follows.

[0256] Example 1 (Synthetic Method A): Preparation of N,1',3'-trimethyl-2-(1-methyl-1H-pyrazol-4-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide

[0257]

[0258] To a solution of 4-amino-3-((1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)-N-methylbenzenesulfonamide (intermediate I-3, 30.00 mg, 83.01 μmol) and 1-methyl-1H-pyrazole-4-carbaldehyde (9.14 mg, 83.01 μmol) in acetic acid (3 mL) was added copper acetate (3.02 mg, 16.60 μmol). The solution was heated at 110 °C for 1 h and then cooled to room temperature. Water was added, and the oil layer was extracted with ethyl acetate. Sodium sulfate was added to the collected oil layer to remove water, then filtered. The filtrate was concentrated under reduced pressure and separated by MPLC to obtain the title compound (20.00 mg, 44.30 μmol, 53.37% yield).

[0259] 1 H-NMR (400 MHz, Methanol-d4) δ 7.86 (d, J =8.5 Hz, 1H), 7.82 (dd, J =8.5, 1.7 Hz, 1H), 7.61 (s, 1H), 7.56 (d, J =1.6 Hz, 1H), 7.53 (s, 1H), 7.44 (d, J =8.2 Hz, 1H), 7.39 (d, J =2.0 Hz, 1H), 7.27 (dd, J =8.2, 2.0 Hz, 1H), 3.84 (s, 3H), 3.55 (s, 3H), 3.44 (s, 3H), 2.48 (s, 3H). LC / MS: 452 (M+H)

[0260]

[0261] Example 20 (Synthetic Method B): Preparation of 2-(isoquinolin-8-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide

[0262]

[0263] 4-Amino-3-((1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)-N-methylbenzenesulfonamide (Intermediate I-3, 50 mg, 0.138 mmol) and isoquinoline-8-carboxylic acid (23.9 mg, 0.138 mmol) were dissolved in dichloromethane (1.4 mL). Propanephosphonic anhydride (50 wt% in ethyl acetate, 0.086 mL, 0.14 mmol), N-N-diisopropylethylamine (0.025 mL, 0.144 mmol), and acetic acid (2–5 drops, catalytic amount) were added. The reaction solution was heated to 80 °C and stirred for one day. The reaction solution was cooled to room temperature, water was added, and the oil layer was extracted with ethyl acetate. The oil layer obtained by removing water with magnesium sulfate and filtering was concentrated under reduced pressure and separated by MPLC and PTLC to obtain the title compound.

[0264] 1 H-NMR (500 MHz, Methanol-d4) δ 9.49-9.37 (m, 1H), 8.57-8.44 (1H), 8.15 (s, 1H), 8.07 (t, J = 8.7 Hz, 2H), 7.92 (dd, J = 8.5, 1.5 Hz, 1H), 7.90 (d, J = 5.8 Hz, 1H), 7.88 (s, 1H), 7.85 (d, J = 7.0 Hz, 1H), 7.78 (t, J = 7.6 Hz, 1H), 7.33 (d, J = 12.2 Hz, 1H), 7.17-7.08 (m, 2H), 3.39 (s, 3H), 3.31 (s, 3H), 2.54 (d, J = 12.8 Hz, 3H)

[0265]

[0266] Example 21 (Synthetic Method C): Preparation of 5-(6-((3-(azepan-1-yl)propyl)(methyl)amino)-8-(1H-pyrrolo[2,3-b]pyridin-2-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0267] Step 1) Preparation of 5-((6-((3-(azepan-1-yl)propyl)(methyl)amino)-5-nitropyrimidin-4-yl)amino)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0268]

[0269] 5-((6-chloro-5-nitropyrimidin-4-yl)amino)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (intermediate I-4, 200 mg, 601 μmol) and 3-(azepan-1-yl)-N-methylpropan-1-amine (102 mg, 0.60 mmol) were added to dichloromethane (10 mL), and N,N-diisopropylethylamine (155 mg, 1.2 mmol, 209 uL) was added. The reaction solution was heated to 100 °C and stirred for 5 hours. The reaction product was concentrated under reduced pressure and separated by MPLC to obtain the title compound (200 mg, 0.42 mmol, 71.3% yield).

[0270] Step 2) Preparation of 5-((5-amino-6-((3-(azepan-1-yl)propyl)(methyl)amino)pyrimidin-4-yl)amino)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0271]

[0272] 5-((6-((3-(azepan-1-yl)propyl)(methyl)amino)-5-nitropyrimidin-4-yl)amino)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (200 mg, 0.43 mmol) was added to methanol (10 mL) and Raney nickel (100 mg, 0.43 mmol) was added. The reaction solution was stirred at room temperature for 2 h under hydrogen conditions. The reaction solution was filtered through a pad of Celite to remove the catalyst, and the filter filtrate was concentrated under reduced pressure and used in the next reaction without further purification.

[0273] Step 3) Preparation of 5-(6-((3-(azepan-1-yl)propyl)(methyl)amino)-8-(1H-pyrrolo[2,3-b]pyridin-2-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0274]

[0275] 5-((5-amino-6-((3-(azepan-1-yl)propyl)(methyl)amino)pyrimidin-4-yl)amino)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (30 mg, 0.068 mmol) and 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (10.0 mg, 0.068 mmol) were added to ethanol (8 mL), and acetic acid (0.5 mL) was added. The reaction solution was stirred at 60 °C for 1 h. The reaction solution was concentrated under reduced pressure and separated by MPLC to obtain the title compound. (11.40 mg, 0.020 mmol, 29.3% yield)

[0276] 1H-NMR (400 MHz, Methanol-d4) δ 8.27-8.36 (m, 2 H), 8.10 (d, J = 8.0 Hz, 1 H), 7.42 (q, J = 6.4 Hz, 2 H), 7.24-7.28 (m, 2 H), 5.99 (s, 1 H), 4.41-4.53 (m, 2 H), 3.44-3.53 (m, 6 H), 3.41 (s, 5 H), 3.22 (t, J = 12.0 Hz, 2 H), 2.31 (t, J = 8.0 Hz, 2 H), 1.67-1.88 (m, 8 H)

[0277]

[0278] Example 34 (Synthetic Method D): Preparation of 5-(8-(1H-indol-5-yl)-6-(methyl(2-(m-tolyloxy)ethyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0279] Step 1) Preparation of 6-chloro-N-methyl-5-nitro-N-(2-(m-tolyloxy)ethyl)pyrimidin-4-amine

[0280]

[0281] To a solution of 4,6-dichloro-5-nitropyrimidine (387.95 mg, 2.00 mmol) in acetonitrile (10 mL) were added N,N-diisopropylethylamine (258.00 mg, 2.00 mmol) and N-methyl-2-(m-tolyloxy)ethan-1-amine (330.46 mg, 2.00 mmol) at 0 °C. The mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure and used in the next reaction without further purification.

[0282] Step 2) Preparation of 1,3-dimethyl-5-((6-(methyl(2-(m-tolyloxy)ethyl)amino)-5-nitropyrimidin-4-yl)amino)-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0283]

[0284] To a solution of 6-chloro-N-methyl-5-nitro-N-(2-(m-tolyloxy)ethyl)pyrimidin-4-amine (appx. 2.00 mmol) and 5-amino-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (intermediate I-1, 354.41 mg, 2.00 mmol) in dimethylformamide (30 mL) was added N,N-diisopropylethylamine (516.96 mg, 4.00 mmol, 0.696 mL), and the mixture was stirred at 60 °C for 2 h. The reaction mixture was concentrated under reduced pressure and used in the next reaction without further purification.

[0285] Step 3) Preparation of 5-((5-amino-6-(methyl(2-(m-tolyloxy)ethyl)amino)pyrimidin-4-yl)amino)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0286]

[0287] The above material (appx. 2.00 mmol) was dissolved in acetic acid (25 mL), and zinc (780.00 mg, 12.00 mmol) was added. The reaction solution was stirred at room temperature for 30 minutes. The reaction solution was filtered through Celite, the filtrate was concentrated under reduced pressure, and the desired material was obtained by MPLC separation (485.00 mg, 55.94% yield over 3 steps, crude).

[0288] Step 4) Preparation of 5-(8-(1H-indol-5-yl)-6-(methyl(2-(m-tolyloxy)ethyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0289]

[0290] 5-((5-amino-6-(methyl(2-(m-tolyloxy)ethyl)amino)pyrimidin-4-yl)amino)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (385.00 mg, 0.88 mmol) and 1H-indole-5-carbaldehyde (154.70 mg, 1.07 mmol) were added to ethanol (30 mL), and acetic acid (53.29 mg, 0.88 mmol) was added. The reaction solution was stirred at 60 °C for 24 h. The reaction solution was concentrated under reduced pressure and separated by MPLC to obtain the title compound (23.60 mg, 0.041 mmol, 4.71% yield).

[0291] 1 H-NMR (400 MHz, DMSO-d6) δ 11.25 (s, 1H), 8.18 (s, 1H), 7.78 (s, 1H), 7.35 (d, J = 6.0 Hz, 3H), 7.28 (t, J = 8.4 Hz, 2H), 7.18 (t, J = 8.4) Hz, 1 H), 6.98 (d, J = 8.0 Hz, 1 H), 6.72-6.80 (m, 3 H), 6.38 (s, 1H), 4.34-4.67 (m, 4 H), 3.37 (s, 3H), 3.30 (s, 3H), 3.29 (s, 3H), 2.24 (s, 3H), LC / MS: 559 (M+H)

[0292]

[0293] Example 44 (Synthetic Method E): Preparation of (S)-2-(1-(3,4-difluorophenyl)-6-oxopiperidin-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide

[0294]

[0295] 3-(1,3-Dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(6-oxo-2-piperidyl)benzimidazole-5-sulfonamide (Example 43, 10 mg, 0.021 mmol) was dissolved in dichloromethane (1 mL), and copper acetate (5.04 mg, 0.028 mmol), pyridine (17 uL, 0.213 mmol), and (3,4-difluorophenyl)boronic acid (11.8 mg, 0.075 mmol) were added. The solution was stirred at room temperature for 4 h. Water was added to the reaction mixture, extracted with dichloromethane, and the oil layer was washed with brine. The oil layer was concentrated under reduced pressure and separated by prepHPLC to obtain the title compound (8 mg, 0.021 mmol, 64.6% yield).

[0296] 1 H-NMR (500 MHz, Chloroform-d) δ 7.95 (d, J = 8.5 Hz, 1H), 7.77 (d, J = 8.2 Hz, 1H), 7.51 (s, 1H), 7.17-7.08 (m, 1H), 7.08-6.93 (m, 3H), 6.93-6.85 (m, 1H), 6.83 (s, 1H), 5.03-4.91 (m, 1H), 4.47-4.34 (m, 1H), 3.62-3.47 (m, 3H), 3.45 (d, J = 6.7 Hz, 1H), 3.32 (s, 2H), 2.86 (dt, J = 17.7, 5.5 Hz, 1H), 2.67-2.59 (m, 3H), 2.50 (m, 1H), 2.29-2.18 (m, 2H), 1.90 (m, 1H), 1.76-1.54 (m, 1H)

[0297]

[0298] Example 48 (Synthetic Method F): Preparation of 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-[6-(1-methylpyrazol-4-yl)-1H-indol-3-yl]benzimidazole-5-sulfonamide

[0299]

[0300] 2-(6-Bromo-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide (Example 42, 35 mg, 0.062 mmol) was dissolved in 1,4-dioxane (1.5 mL), and 2 M aqueous sodium carbonate solution (42.0 mg, 0.396 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (25.8 mg, 0.124 mmol), and tetrakis(triphenylphosphine)palladium(0) (2.86 mg, 2.476 μmol) were added, and the mixture was stirred at 100 °C for 18 h under nitrogen conditions. The mixture was stirred. After completion of the reaction, ethyl acetate (10 mL) and water (10 mL) were added, and the oil layer was extracted. The oil layer was washed with water and brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by MPLC and PTLC to obtain the title compound. (7 mg, 0.012 mmol, 19.96% yield)

[0301] 1 H-NMR (500 MHz, Chloroform-d) δ 8.75-8.69 (m, 1H), 8.63-8.57 (m, 1H), 7.92 (d, J = 8.5 Hz, 1H), 7.74-7.71 (m, 2H), 7.60 (d, J = 7.6 Hz, 2H), 7.48-7.38 (m, 2H), 7.18-7.13 (m, 2H), 6.99 (m, 1H), 6.59 (d, J = 7.9 Hz, 1H), 4.49 (s, 1H), 3.93 (s, 3H), 3.53 (s, 3H), 3.38(s, 3H), 2.63 (s, 3H)

[0302]

[0303] Example 49 (Synthetic Method G): Preparation of tert-butyl 4-(3-(1',3'-dimethyl-6-(N-methylsulfamoyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazol]-2-yl)-1H-indol-6-yl)piperidine-1-carboxylate

[0304]

[0305] Tert-Butyl-4-[3-[1-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-6-(methylsulfamoyl)benzimidazol-2-yl]-1H-indol-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylate (Example 47, 30 mg, 0.045 mmol) was added to ethanol (1.5 mL), palladium / carbon (9.56 mg, 8.98 μmol) was added, and the mixture was stirred at room temperature for 18 h under a hydrogen balloon. After the reaction was completed, the residue was passed through a celite filter, and the filtrate was concentrated and separated by PTLC to obtain the title compound (15 mg, 0.022 mmol, 49.8% yield).

[0306] LC / MS: 670 (M+H)

[0307]

[0308] Example 50 (Synthetic Method H): Preparation of N,1',3'-trimethyl-2'-oxo-2-(6-(piperidin-4-yl)-1H-indol-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide

[0309]

[0310] Tert-Butyl-4-[3-[1-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-6-(methylsulfamoyl)benzimidazol-2-yl]-1H-indol-6-yl]piperidine-1-carboxylate (Example 49, 30 mg, 0.045 mmol) was dissolved in dichloromethane (1 mL), and then trifluoroacetic acid (0.3 mL, 3.89 mmol) was added. The reaction solution was stirred at room temperature for 2 hours. After the reaction was completed, 1 N sodium hydroxide was added, and the oil layer was extracted with dichloromethane, which was then washed with water and brine. The oil layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by MPLC to obtain the title compound (13 mg, 0.023 mmol, 50.9% yield).

[0311] 1H-NMR (500 MHz, DMSO-d6) δ 11.40 (s, 1H), 8.57 (d, J = 8.2 Hz, 1H), 7.90 (d, J = 8.5 Hz, 1H), 7.65 (dd, J = 8.5, 1.5 Hz, 1H), 7.51 (d, J = 1.8 Hz, 1H), 7.47 (d, J = 8.2 Hz, 1H), 7.36 (d, J = 1.5 Hz, 1H), 7.33 (d, J = 5.2 Hz, 1H), 7.29 (dd, J = 8.2, 1.8 Hz, 1H), 7.26 (s, 1H), 7.13 (d, J = 8.5 Hz, 1H), 6.59 (d, J = 3.1 Hz, 1H), 3.47 (s, 3H), 3.38-3.36 (m, 2H), 3.34 (s, 3H), 3.17 (d, J = 5.2 Hz, 1H), 3.03-2.94 (m, 3H), 2.36 (d, J = 5.2 Hz, 3H), 1.98-1.95 (m, 2H), 1.91-1.86 (m, 2H), LC / MS: 570 (M+H)

[0312]

[0313] Example 52 (Synthetic Method I): Preparation of N,1',3'-trimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-carboxamide

[0314] Step 1) Preparation of 4-amino-3-((1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)-N-methylbenzamide

[0315]

[0316] The title compound was synthesized using 5-amino-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (intermediate I-1) and 3-fluoro-N-methyl-4-nitrobenzamide (intermediate I-5) in the same manner as in the synthesis of intermediate I-3.

[0317] 1H-NMR (500 MHz, DMSO-d6) δ 7.98-7.90 (m, 1H), 7.52 (s, 1H), 7.32 (d, J = 8.2 Hz, 1H), 6.96 (d, J = 8.2 Hz, 1H), 6.70 (d, J = 7.9 Hz, 1H), 6.61-6.55 (m, 1H), 6.54 (d, J = 3.7 Hz, 1H), 3.28 (s, 3H), 3.25-3.20 (3H), 2.69 (d, J = 4.6 Hz, 3H)

[0318] Step 2) Preparation of N,1',3'-trimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-carboxamide

[0319]

[0320] The title compound was synthesized (8 mg, 0.017 mmol, 11.21% yield) using the same method as in Synthetic Method A using 4-amino-3-((1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)-N-methylbenzamide (50 mg, 0.154 mmol).

[0321] 1 H-NMR (400 MHz, Chloroform-d) δ 8.59 (d, J = 8.7 Hz, 1H), 8.08 (s, 1H), 7.88 (d, J = 8.7 Hz, 1H), 7.59 (dd, J = 8.2, 1.4 Hz, 1H), 7.51 (s, 1H), 7.23 (s, 1H), 7.18-7.12 (2H), 7.02-6.99 (1H), 6.56 (d, J = 3.0 Hz, 1H), 6.15 (d, J = 4.6 Hz, 1H), 3.49 (d, J = 12.3 Hz, 3H), 3.40-3.33 (3H), 3.03-2.95 (3H), 2.49-2.44 (3H), LC / MS: 465 (M+H)

[0322]

[0323] Examples 55 and 56 (Synthetic Method J): Preparation of 5-(4-chloro-2-(6-methyl-1H-indol-3-yl)-1H-imidazo[4,5-c]pyridin-1-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one and 5-[4-(dimethylamino)-2-(6-methyl-1H-indol-3-yl)imidazo[4,5-c]pyridin-1-yl]-1,3-dimethyl-benzimidazol-2-one

[0324] Step 1) Preparation of 5-((2-chloro-3-nitropyridin-4-yl)amino)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0325]

[0326] 5-Amino-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (Intermediate I-1, 2 g, 10.36 mmol) was dissolved in 1,4-dioxane (50 mL), and 2,4-dichloro-3-nitropyridine (1.84 g, 10.36 mmol) and N,N-diisopropylethylamine (2 g, 15.55 mmol, 2.72 mL) were added. The reaction mixture was heated to 80 °C and stirred for 5 hours. The reaction mixture was concentrated under reduced pressure and purified by MPLC to obtain the title compound (1.8 g, 5.39 mmol, 52.0% yield).

[0327] Step 2) Preparation of 5-((3-amino-2-chloropyridin-4-yl)amino)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0328]

[0329] Compound 5-((2-chloro-3-nitropyridin-4-yl)amino)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (1.8 g, 5.39 mmol) obtained in Step 1 was dissolved in methanol / water (20 ml / 10 mL), and then iron powder (904 mg, 16.18 mmol) and ammonium chloride (1.44 g, 27.0 mmol) were added. The reaction solution was heated to 100 °C and stirred for 2 hours. The reaction solution was filtered to remove the solid, and the filtrate was concentrated under reduced pressure and purified by MPLC to obtain the title compound (1.2 g, 3.95 mmol, 73.2% yield).

[0330] LC / MS: 304 (M+H)

[0331] Step 3) Preparation of 5-(4-chloro-2-(6-methyl-1H-indol-3-yl)-1H-imidazo[4,5-c]pyridin-1-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0332]

[0333] Step 2 Compound 5-((3-amino-2-chloropyridin-4-yl)amino)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (300 mg, 0.99 mmol) obtained in Step 2 was dissolved in acetic acid (7 mL). 6-Methyl-1H-indole-3-carbaldehyde (157 mg, 0.99 mmol) and copper acetate (179 mg, 0.99 mmol) were added. The solution was heated at 110 °C for 1 h and then cooled to room temperature. Water was added, and the oil layer was extracted with ethyl acetate. The combined oil layer was added with sodium sulfate to remove water, filtered, and the filtrate was concentrated under reduced pressure and purified by MPLC to obtain the title compound (200 mg, 0.45 mmol, 45.7% yield).

[0334] 1H-NMR (400 MHz, DMSO-d6) δ 11.30 (s, 1H), 8.53 (d, 1H), 8.07 (s, 1H), 7.54 (d, 1H), 7.36 (m, 1H), 7.29 (m, 2H), 7.09 (m, 2H), 6.54 (brs, 1H), 3.46 (s, 3H), 3.35 (s, 3H), 2.43 (s, 3H), LC / MS: 443(M+H)

[0335] As a by-product of the reaction, 5-(4-chloro-1H-imidazo[4,5-c]pyridin-1-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one was obtained (30 mg, 96.0 μmol, 9.7% yield).

[0336]

[0337] 1 H-NMR (400 MHz, DMSO-d6) δ 11.30 (s, 1H), 8.53 (d, 1H), 8.07 (s, 1H), 7.54 (d, 1H), 7.36 (m, 1H), 7.29 (m, 2H), 7.09 (m, 2H), 6.54 (brs, 1H), 3.46 (s, 3H), 3.35 (s, 3H), 2.43 (s, 3H), LC / MS: 314 (M+H)

[0338] Step 4) Preparation of 5-[4-(dimethylamino)-2-(6-methyl-1H-indol-3-yl)imidazo[4,5-c]pyridin-1-yl]-1,3-dimethyl-benzimidazol-2-one

[0339]

[0340] 5-(4-Chloro-2-(6-methyl-1H-indol-3-yl)-1H-imidazo[4,5-c]pyridin-1-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (Example 55, 50 mg, 113 μmol) was added to 2M dimethylamine in methanol (2.8 mL, 5.64 mmol). The reaction solution was heated to 150 °C in a microwave reactor and stirred for 2 hours. The reaction product was concentrated under reduced pressure and purified by MPLC to obtain the title compound (24 mg, 53 μmol, 47.1% yield).

[0341] 1 H-NMR (400 MHz, DMSO-d6) δ 11.06 (s, 1H), 8.42 (d, 1H), 7.78 (d, 1H), 7.37 (m, 2H), 7.19 (m, 1H), 7.13 (m, 1H), 7.03 (d, 1H), 6.41 (m, 2H), 3.50 (s, 6H), 3.45 (s, 3H), 3.33 (s, 3H), 2.41 (s, 3H), LC / MS: 452 (M + H)

[0342]

[0343] Example 58 (Synthetic Method K): Preparation of 1,3-dimethyl-5-[2-(6-methyl-1H-indol-3-yl)-6-(1-methylpyrazol-4-yl)benzimidazol-1-yl]benzimidazol-2-one

[0344] Step 1) Preparation of 6-bromo-1',3'-dimethyl-2-(6-methyl-1H-indol-3-yl)-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one

[0345]

[0346] The title compound was synthesized from 5-amino-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (intermediate I-1, 2 g, 10.36 mmol) and 4-bromo-2-fluoro-1-nitrobenzene (1.84 g, 10.36 mmol) in a similar manner to Synthetic Method I (29.4% yield over 3 steps).

[0347] LC / MS: 486, 488 (M+H)

[0348] Step 2) Preparation of 1',3'-dimethyl-2-(6-methyl-1H-indol-3-yl)-6-(1-methyl-1H-pyrazol-4-yl)-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazole]-2'-one

[0349]

[0350] 6-Bromo-1',3'-dimethyl-2-(6-methyl-1H-indol-3-yl)-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one (50 mg, 103 μmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (22 mg, 0.103 mmol), potassium carbonate (22 mg, 0.154 mmol) in 1,4-dioxane (2 mL) and water (0.5 mL) was added 1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)(Pd(dppf)Cl2)ㆍdichloromethane (8.4 mg, 10.3 μmol). After addition, the mixture was stirred at 110°C for 3 hours. After cooling the reaction solution to room temperature, the oil layer was extracted with ethyl acetate. The obtained oil layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The title compound was obtained by purification using MPLC (27 mg, 0.055 mmol, 53.9% yield).

[0351] 1H-NMR (400 MHz, DMSO-d6) δ 11.10 (s, 1H), 8.51 (d, 1H), 8.06 (d, 1H), 7.78 (s, 1H), 7.70 (d, 1H), 7.47 (m, 3H), 7.23 (m, 2H), 7.09 (s, 1H), 7.02 (d, 1H), 6.46 (d, 1H), 3.81 (s, 3H), 3.47 (s, 3H), 3.36 (s, 3H), 2.42 (s, 3H), LC / MS: 488 (M+H)

[0352]

[0353] Example 74 (Synthetic Method L): Preparation of N,1',3'-trimethyl-2,2'-dioxo-2,2',3,3'-tetrahydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide

[0354]

[0355] To a solution of 4-amino-3-((1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)-N-methylbenzenesulfonamide (intermediate I-3, 41.0 mg, 113.0 μmol) and triphosgene (11.0 mg, 39.00 μmol) in tetrahydrofuran (1 mL) was added triethylamine (23.0 mg, 227.0 μmol). The solution was stirred at room temperature for 1 h. Water and ethyl acetate were added to extract the oil layer. The combined oil layer was added with magnesium sulfate to remove water, filtered, and the filtrate was concentrated under reduced pressure and separated by MPLC to obtain the title compound (17.0 mg, 44.0 μmol, 39% yield).

[0356] 1H NMR (500 MHz, DMSO-d6) δ 8.74 (s, 1H), 7.98 (d, 1H), 7.89 (d, 1H), 7.72 (d, 2H), 7.58 (d, 1H), 7.72 (m, 2H), 7.38 (d, 1H), 3.43 (s, 3H), 3.39 (s, 3H), 2.38 (d, 3H), LC / MS: 388 (M+H)

[0357]

[0358] Example 77 (Synthetic Method M): Preparation of 2-(6-bromo-1H-pyrrolo[3,2-c]pyridin-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide

[0359] Step 1) Preparation of sodium (6-bromo-1H-pyrrolo[3,2-c]pyridin-3-yl)(hydroxy)methanesulfonate

[0360]

[0361] Sodium metabisulfite (169 mg, 0.889 mmol) was dissolved in water (0.8 mL), and then a solution of 6-bromo-1H-pyrrolo[3,2-c]pyridine-3-carbaldehyde (200 mg, 0.889 mmol) in ethanol (0.8 mL) was slowly added at 0 °C. The reaction solution was stirred at 50 °C for 18 hours. The resulting white solid was filtered to obtain the title compound (130 mg, 0.547 mmol, 95% yield).

[0362] Step 2) Preparation of 2-(6-bromo-1H-pyrrolo[3,2-c]pyridin-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide

[0363]

[0364] 4-Amino-3-((1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)-N-methylbenzenesulfonamide (Intermediate I-3, 89 mg, 0.246 mmol) and sodium (6-bromo-1H-pyrrolo[3,2-c]pyridin-3-yl)(hydroxy)methanesulfonate (89 mg, 0.270 mmol) were added to dimethylformamide (1.2 mL) and stirred at 80 ℃ for 18 h. After the reaction was completed, water (10 mL) was added, the resulting solid was filtered, and the filtrate was concentrated under reduced pressure. The title compound was obtained by purification by PTLC. (80 mg, 0.246 mmol, 57.4% yield)

[0365] 1 H-NMR (500 MHz, DMSO-d6) δ 9.48 (s, 1H), 7.94 (d, J = 6.1 Hz, 1H), 7.67-7.63 (m, 2H), 7.54 (s, 1H), 7.47 (d, J = 7.6 Hz, 1H), 7.37-7.30 (m, 3H), 6.74 (s, 1H), 3.46 (s, 3H), 3.34 (s, 3H), 2.36 (d, J = 4.0 Hz, 3H), LC / MS: 566, 568 (M+H)

[0366]

[0367] Example 80 (Synthetic Method N): Preparation of 1,3-dimethyl-5-[2-(6-methyl-1H-indol-3-yl)imidazo[4,5-c]pyridin-3-yl]benzimidazol-2-one

[0368] Step 1) Preparation of 3-((1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)-4-nitropyridine-1-oxide

[0369]

[0370] 5-Amino-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (intermediate I-1, 1 g, 5.64 mmol) and 3-fluoro-4-nitropyridine 1-oxide (0.98 g, 6.21 mmol) were dissolved in 1,4-dioxane (12 mL), and N,N-diisopropylethylamine (1.97 mL, 11.3 mmol) was added. The solution was stirred at 110 °C under reflux conditions for 24 h. The reaction mixture was cooled to 0 °C, and the resulting solid was filtered. The filter cake was washed with ethyl acetate and dried. The obtained solid was used in the next reaction without further purification. (2.2 g, 124% yield)

[0371] 1 H-NMR (400 MHz, DMSO-d6) δ 9.61 (s, 1H), 8.13-8.06 (m, 1H), 7.63-7.53 (m, 2H), 7.27-7.23 (m, 3H), 7.14-7.06 (m, 1H), 3.36 (s, 6H)

[0372] Step 2) Preparation of 5-((4-aminopyridin-3-yl)amino)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0373]

[0374] 3-((1,3-Dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)-4-nitropyridine 1-oxide (2.2 g, 6.85 mmol) was added to a solution of ethanol (20 mL) and water (3.5 mL), and iron (1.9 g, 34.3 mmol) and acetic acid (10 mL, 175 mmol) were added. The reaction solution was stirred at 60 °C for 5 h. The reaction solution was filtered through a pad of Celite and washed with ethanol. The filtrate was concentrated under reduced pressure to remove ethanol, and the residue was diluted with ethyl acetate and washed with water and 1 N sodium hydroxide. The oil layer was concentrated under reduced pressure and separated by MPLC to obtain the title compound. (1.3 g, 4.8 mmol, 71% yield)

[0375] LC / MS: 270 (M+H)

[0376] Step 3) Preparation of 1,3-dimethyl-5-(2-(6-methyl-1H-indol-3-yl)-3H-imidazo[4,5-c]pyridin-3-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one

[0377]

[0378] 5-((4-Aminopyridin-3-yl)amino)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one (300 mg, 1.11 mmol) and 6-methyl-1H-indole-3-carbaldehyde (177 mg, 1.11 mmol) were added to ethanol (6 mL), and copper acetate (101 mg, 0.58 mmol) and acetic acid (0.6 mL) were added. The reaction solution was stirred at 120 °C for 4 h. Water was added to the reaction solution, and the oil layer was extracted with dichloromethane. The combined oil layers were concentrated under reduced pressure and separated by prepHPLC to obtain the title compound (72 mg, 0.18 mmol, 15.8% yield).

[0379] LC / MS: 409 (M+H)

[0380]

[0381] Example 81 (Synthetic Method O): Preparation of 2-(4-(difluoromethyl)naphthalen-1-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide

[0382]

[0383] 3-(1,3-Dimethyl-2-oxo-benzimidazol-5-yl)-2-(4-formyl-1-naphthyl)-N-methyl-benzimidazole-5-sulfonamide (Example 79, 55 mg, 0.105 mmol) was dissolved in dichloroethane (0.55 mL), and diethylaminosulfur trifluoride (0.048 mL, 0.366 mmol) was slowly added at room temperature. The reaction solution was stirred at 80 °C for 18 hours. The reaction solution was cooled to 0 °C, saturated aqueous sodium bicarbonate solution was added to terminate the reaction, and dichloromethane was added to extract the oil layer. After washing the oil layer with water and brine, drying with anhydrous magnesium sulfate, and concentrating under reduced pressure, the residue was purified by MPLC and PTLC to obtain the title compound (5 mg, 9.13 μmol, 8.73% yield).

[0384] 1 H-NMR (500 MHz, Chloroform-d) δ 8.17 (d, J = 8.2 Hz, 2H), 8.05 (d, J = 8.2 Hz, 1H), 7.91 (s, 1H), 7.87 (d, J = 8.5 Hz, 1H), 7.65-7.57 (m, 3H), 7.49 (d, J = 7.3 Hz, 1H), 7.09 (t, J = 55.5 Hz, 1H), 6.94-6.87 (m, 2H), 6.78 (s, 1H), 4.48-4.46 (m, 1H), 3.39 (s, 3H), 3.24 (s, 3H), 2.68 (d, J = 5.2 Hz, 3H), LC / MS: 548 (M+H)

[0385]

[0386] Example 83 (Synthetic Method P): Preparation of 1',3'-dimethyl-6-(N-methylsulfamoyl)-2'-oxo-N-(pyridin-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-2-carboxamide

[0387] Step 1) Preparation of ethyl 1',3'-dimethyl-6-(N-methylsulfamoyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-2-carboxylate

[0388]

[0389] 4-Amino-3-((1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)-N-methylbenzenesulfonamide (intermediate I-3, 200 mg, 0.553 mmol) and ethyl 2-oxoacetate (0.113 ml, 0.553 mmol) were used in a similar manner to Synthesis A.

[0390] 1 H-NMR (500 MHz, Chloroform-d) δ 7.23 (s, 1H), 7.13 (d, J = 8.2 Hz, 1H), 6.69 (s, 1H), 6.62 (d, J = 8.2 Hz, 1H), 6.60 (s, 1H), 5.70 (s, 1H), 4.43-4.42 (m, 1H), 4.24-4.20 (m, 2H), 3.37 (s, 3H), 3.36 (s, 3H), 2.63 (d, J = 5.2 Hz, 3H), 1.18 (t, J = 7.0 Hz, 3H)

[0391] Step 2) Preparation of 1',3'-dimethyl-6-(N-methylsulfamoyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-2-carboxylic acid

[0392]

[0393] Ethyl 1',3'-dimethyl-6-(N-methylsulfamoyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-2-carboxylate (161 mg, 0.363 mmol) was dissolved in ethanol (0.9 mL), tetrahydrofuran (0.45 mL), and water (0.45 mL), and then lithium hydroxide (38.1 mg, 0.908 mmol) was added. The mixture was stirred at room temperature for 18 h. After the reaction was completed, the reaction solvent was removed by concentration under reduced pressure, and the mixture was diluted with water. The pH was adjusted to 3-4 with 1 N hydrochloric acid, and the resulting solid was filtered and washed with methanol. The filtrate was concentrated under reduced pressure and used directly in the next step without further purification.

[0394] Step 3) Preparation of 1',3'-dimethyl-6-(N-methylsulfamoyl)-2'-oxo-N-(pyridin-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-2-carboxamide

[0395]

[0396] 1',3'-Dimethyl-6-(N-methylsulfamoyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-2-carboxylic acid (130 mg, 0.313 mmol) was dissolved in dimethylformamide (3.1 mL), and hydroxybenzotriazole (HOBt) (62.3 mg, 0.407 mmol), pyridin-3-amine (29.5 mg, 0.313 mmol), and HATU (155 mg, 0.407 mmol) were added. The reaction solution was stirred at room temperature for 18 hours. After the reaction was complete, water was added to the reaction solution, and the oil layer was extracted with ethyl acetate. After washing the oil layer with water and brine, drying with anhydrous magnesium sulfate, and concentrating under reduced pressure, the residue was purified by MPLC and PTLC to obtain the title compound (3 mg, 6.10 μmol, 1.950% yield).

[0397] LC / MS: 492 (M+H)

[0398]

[0399] Example 90 (Synthetic Method Q): Preparation of 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-carboxylic acid

[0400]

[0401] Methyl 1',3'-dimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-carboxylate (Example 89, 30 mg, 0.064 mmol) was added to methanol (0.5 mL) / water (0.5 mL), and lithium hydroxide (4.63 mg, 0.193 mmol) was added. The reaction solution was stirred at 60 °C for 18 hours. Water and 1 N hydrochloric acid were added to the reaction solution to adjust the pH to about 2-4, and the oil layer was extracted with ethyl acetate. The oil layer was concentrated under reduced pressure and purified by prep HPLC to obtain the title compound.

[0402] 1 H-NMR (500MHz, DMSO-d6) δ 11.22 (s, 1H), 8.51 (d, J = 7.9 Hz, 1H), 7.87 (d, J = 7.9 Hz, 1H), 7.77 (d, J = 8.2 Hz, 1H), 7.53 (s, 1H), 7.49 (s, 1H), 7.45 (d, J = 8.2 Hz, 1H), 7.26 (d, J = 8.2 Hz, 1H), 7.22 (s, 1H), 7.05 (d, J = 8.2 Hz, 1H), 6.54 (d, J = 2.7 Hz, 1H), 3.46 (s, 3H), 3.34 (s, 3H), 2.42 (s, 3H) LC / MS: 452 (M+H)

[0403]

[0404] Example 101 (Synthetic Method R): Preparation of 1-(3-(3,5-dimethylisoxazol-4-yl)-5-(tetrahydro-2H-pyran-4-yl)phenyl)-N-methyl-2-(6-methyl-1H-indol-3-yl)-1H-benzo[d]imidazole-6-sulfonamide

[0405] Step 1) Preparation of 3-(2-(6-methyl-1H-indol-3-yl)-6-(N-methylsulfamoyl)-1H-benzo[d]imidazol-1-yl)-5-(tetrahydro-2H-pyran-4-yl)phenyl trifluoromethanesulfonate

[0406]

[0407] 1-(3-Hydroxy-5-(tetrahydro-2H-pyran-4-yl)phenyl)-N-methyl-2-(6-methyl-1H-indol-3-yl)-1H-benzo[d]imidazole-6-sulfonamide (Example 100, 66.2 mg, 0.128 mmol) was added to tetrahydrofuran (1.5 mL), and 4-dimethylaminopyridine (47 mg, 0.384 mmol) and trifluoromethanesulfonic anhydride (0.022 mL, 0.128 mmol) were added at 0 ℃. The reaction solution was stirred for 24 h. Water was added to the reaction solution, and the oil layer was extracted with ethyl acetate. The oil layer was concentrated under reduced pressure and separated by MPLC to obtain the title compound (9.2 mg, 0.014 mmol, 11.07% yield).

[0408] 1 H-NMR (400 MHz, Chloroform-d) δ 8.43 (s, 1H), 8.09 (d, J = 8.2 Hz, 1H), 7.96 (d, J = 8.2 Hz, 1H), 7.80 (dd, J = 8.3, 1.7 Hz, 1H), 7.73-7.67 (1H), 7.35-7.31 (2H), 7.30 (d, J = 1.4 Hz, 1H), 7.17 (s, 1H), 7.06 (d, J = 8.2 Hz, 1H), 6.79 (d, J = 3.2 Hz, 1H), 4.46-4.33 (m, 1H), 4.04 (dd, J = 11.2, 3.4 Hz, 2H), 3.48 (td, J = 11.5, 2.6 Hz, 2H), 3.44-3.35 (m, 2H), 2.93-2.78 (m, 1H), 2.75-2.58 (3H), 2.52-2.42 (3H), 1.83-1.65 (4H)

[0409] Step 2) Preparation of 1-(3-(3,5-dimethylisoxazol-4-yl)-5-(tetrahydro-2H-pyran-4-yl)phenyl)-N-methyl-2-(6-methyl-1H-indol-3-yl)-1H-benzo[d]imidazole-6-sulfonamide

[0410]

[0411] 3-(2-(6-Methyl-1H-indol-3-yl)-6-(N-methylsulfamoyl)-1H-benzo[d]imidazol-1-yl)-5-(tetrahydro-2H-pyran-4-yl)phenyltrifluoromethanesulfonate (9.2 mg, 0.014 mmol) was added to 1,4-dioxane (0.5 mL), and (3,5-dimethylisoxazol-4-yl)boronic acid (3.00 mg, 0.021 mmol) and 2 M sodium carbonate in water (0.014 mL, 0.028 mmol) were added. Tetrakis(triphenylphosphine)palladium(0) (0.819 mg, 0.709 μmol) was added to the reaction mixture, and nitrogen was bubbled for 5 min. The reaction mixture was reacted at 90 °C for 24 h. Water was added to the reaction mixture, the oil layer was extracted with ethyl acetate, and washed with brine. The oil layer was concentrated under reduced pressure and separated by MPLC to obtain the title compound. (3 mg, 5.04 μmol, 35.5% yield)

[0412] LC / MS: 596 (M+H)

[0413]

[0414] Example 104 (Synthetic Method S): Preparation of N-methyl-2-(3-methylimidazol-4-yl)-3-(2-oxo-1,3-dihydrobenzimidazol-5-yl)benzimidazole-5-sulfonamide

[0415] Step 1) Preparation of N-methyl-4-nitro-3-((2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)benzenesulfonamide

[0416]

[0417] 3-Fluoro-N-methyl-4-nitrobenzenesulfonamide (intermediate I-2, 79 mg, 0.335 mmol) and 5-amino-1,3-dihydro-2H-benzo[d]imidazol-2-one (50 mg, 0.335 mmol) were added to 1,4-dioxane (1.5 mL), and N,N-diisopropylethylamine (0.117 mL, 0.670 mmol) was added. The reaction solution was stirred at 110 °C for 18 h. After the reaction was completed, the reaction solution was cooled to room temperature, and the resulting solid was filtered. The filter cake was washed with ethyl acetate, dried under nitrogen, and used in the next reaction without further purification. (56.2 mg, 0.155 mmol, 46.1% yield)

[0418] 1 H-NMR (500 MHz, DMSO-d6) δ 10.76 (d, J = 11.9 Hz, 2H), 9.54 (s, 1H), 8.29 (d, J = 8.8 Hz, 1H), 7.71 (s, 1H), 7.31 (s, 1H), 7.05 (d, J = 9.2 Hz, 1H), 7.00 (d, J = 8.5 Hz, 1H), 6.92 (s, 2H), 2.39 (s, 3H)

[0419] Step 2) Preparation of N-methyl-2-(1-methyl-1H-imidazol-5-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide

[0420]

[0421] N-Methyl-4-nitro-3-((2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)amino)benzenesulfonamide (56 mg, 0.154 mmol) was dissolved in dimethyl sulfoxide (1 mL), and 1-methyl-1H-imidazole-5-carbaldehyde (25.5 mg, 0.231 mmol) and sodium hydrosulfite (95 mg, 0.462 mmol) were added. The reaction solution was stirred at 90 °C for 3 hours. The reaction solution was cooled to 0 °C, diluted with water and ethyl acetate, adjusted to pH 9-11 by adding 25% ammonium hydroxide, and extracted with ethyl acetate. The oil layer was concentrated under reduced pressure and separated by PTLC to obtain the title compound. (20 mg, 0.047 mmol, 30.6% yield)

[0422] 1 H-NMR (500MHz, Methanol-d4) δ 7.93 (d, J = 8.5 Hz, 1H), 7.88 (s, 1H), 7.83-7.78 (1H), 7.63 (s, 1H), 7.28 (d, J = 7.9 Hz, 1H), 7.15 (d, J = 7.9 Hz, 2H), 6.62-6.55 (1H), 4.10 (s, 3H), 2.50-2.45 (3H)

[0423]

[0424] Example 113 (Synthetic Method T): Preparation of 2-(1,6-dimethyl-1H-indol-3-yl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one

[0425]

[0426] 1',3'-Dimethyl-2-(6-methyl-1H-indol-3-yl)-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one (Example 111, 21.3 mg, 0.05 mmol) was dissolved in N,N-dimethylformamide (1 mL), potassium carbonate (21.7 mg, 0.16 mmol) and methyl iodide (0.004 mL, 0.06 mmol) were added, heated to 80 ℃, and stirred for 2 hours. Water and dichloromethane were added to the reaction solution, and the oil layer was extracted, washed with brine, and dried using magnesium sulfate. The oil layer was concentrated under reduced pressure and separated by MPLC to obtain the title compound (15 mg, 0.04 mmol, 68% yield).

[0427] 1 H NMR (500 MHz, Chloroform-d) δ 8.43 (d, J = 8.2 Hz, 1H), 7.88 (d, J = 8.0 Hz, 1H), 7.31 - 7.27 (m, 1H), 7.21 - 7.16 (m, 2H), 7.10 (dd, J = 15.5, 7.7 Hz, 3H), 7.04 (d, J = 7.9 Hz, 1H), 7.00 (d, J = 1.8 Hz, 1H), 6.44 (s, 1H), 3.59 (s, 3H), 3.52 (s, 3H), 3.38 (s, 3H), 2.50 (s, 3H).

[0428]

[0429] Examples 2-19, 22-33, 35-43, 45-47, 51, 53, 54, 57, 59-73, 75-76, 78-79, 82, 84-89, 91-100, 102, 103, 105-112, and 114-165

[0430] It was manufactured similarly using the same synthetic method as the representative examples above.

[0431] Specifically, Examples 2~19, 28~29, 38, 40~42, 51, 60~64, 67~71, 76, 79, 88, 94, 115~116, 118, 123~124, 128~135, 153~165 are Synthesis Method A, Examples 43, 45~46, 75 are Synthesis Method B, Examples 22~27, 30~33, 39, 136~140 are Synthesis Method C, Examples 35~37 are Synthesis Method D, Examples 47, 72~73 are Synthesis Method F, Examples 53~54, 65~66, 82, 85~87, 89, 91~93, 95~100, 102, 106~112, 114, 141~152 were similarly prepared according to Synthesis Method I, Examples 57, 59, 119~122 were similarly prepared according to Synthesis Method J, Example 78 was similarly prepared according to Synthesis Method M, Example 84 was similarly prepared according to Synthesis Method P, Example 103 was similarly prepared according to Synthesis Method Q, Example 105 was similarly prepared according to Synthesis Method S, and Examples 117, 125~127 were similarly prepared according to Synthesis Method T.

[0432]

[0433] The compound structures, names, and NMR / MS synthesized from each of the above examples are listed in Table 2 below.

[0434] Example Compound Structure Compound Name NMR / MS1 N,1',3'-trimethyl-2-(1-methyl-1H-pyrazol-4-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (400 MHz, Methanol-d4) δ 7.86 (d, J =8.5 Hz, 1H), 7.82 (dd, J =8.5, 1.7 Hz, 1H), 7.61 (s, 1H), 7.56 (d, J =1.6 Hz, 1H), 7.53 (s, 1H), 7.44 (d, J =8.2 Hz, 1H), 7.39 (d, J =2.0 Hz, 1H), 7.27 (dd, J =8.2, 2.0 Hz, 1H), 3.84 (s, 3H), 3.55 (s, 3H), 3.44 (s, 3H), 2.48 (s, 3H); m / z 4522 2-(5-fluoronaphthalen-1-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (400 MHz, DMSO-d6) δ 8.14 (d, J= 8.5 Hz, 1H), 8.07 (d, J= 8.6 Hz, 1H), 7.87 (d, J= 8.6 Hz, 1H), 7.83-7.75 (m, 2H), 7.66 (d, J= 1.7 Hz, 1H), 7.62 (dd, J= 8.5, 7.2 Hz, 1H), 7.56-7.48 (m, 1H), 7.48-7.42 (m, 2H), 7.39 (dd, J= 10.8, 7.7 Hz, 1H), 7.14 (d, J= 8.2 Hz, 1H), 7.09 (dd, J = 8.2, 2.0 Hz, 1H), 3.28 (s, 3H), 3.21 (s, 3H), 2.41 (d, J= 5.0 Hz, 3H); m / z 5163 2-(4-hydroxyphenyl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (400 MHz, DMSO-d6) δ 9.98 (s, 1H), 7.91 (d, J= 8.5 Hz, 1H), 7.67 (dd, J= 8.5, 1.8 Hz, 1H), 7.49-7.46 (m, 2H), 7.45-7.43 (m, 2H), 7.37 (s, 1H), 7.37-7.34 (m, 1H), 7.17 (dd, J= 8.1, 2.0 Hz, 1H), 6.77-6.69 (m, 2H), 3.42 (s, 3H), 3.31 (s, 4H), 2.35 (d, J= 5.1 Hz, 3H); m / z 4644 N,1',3'-trimethyl-2'-oxo-2-(tetrahydrofuran-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (400 MHz, DMSO-d6) δ 7.89 (d, J= 8.5 Hz, 1H), 7.66 (dd, J= 8.4, 1.8 Hz, 1H), 7.50 (s, 1H), 7.46-7.39 (m, 2H), 7.35 (d, J= 5.1 Hz, 1H), 7.32-7.26 (m, 1H), 3.90 (s, 3H), 3.73 (q, J= 7.4 Hz, 1H), 3.57 (q, J= 7.5 Hz, 1H), 3.43 (s, 3H), 3.36 (s, 4H),2.34 (d, J= 4.9 Hz, 4H); m / z 4425 N,1',3'-trimethyl-2'-oxo-2-(quinolin-8-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (400 MHz, DMSO-d6) δ 11.10 (d, J = 2.4 Hz, 1 H), 8.28 (d, J = 8.4 Hz, 1 H), 8.12 (s, 1 H), 7.51 (q, J = 2.8 Hz, 1 H), 7.38 (q, J = 3.6 Hz, 2 H), 7.31 (d, J = 1.6 Hz, 1 H), 7.17 (t, J = 5.6 Hz, 3 H), 6.87 (d, J = 5.2 Hz, 1 H), 6.41 (d, J = 2.8 Hz, 1 H), 3.45 (s, 3 H), 3.34 (s, 6 H), 3.30 (s, 2 H), 3.11 (s, 2 H), 2.39 (s, 3 H); m / z 4996 2-(1H-indazol-4-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (400 MHz, DMSO-d6) δ 13.30 (s, 1H), 8.48 (s, 1H), 8.07 (d, J = 8.5 Hz, 1H), 7.75 (dd, J= 8.5, 1.8 Hz, 1H), 7.62 (d, J= 8.4 Hz, 1H), 7.57 (d, J= 1.7 Hz, 1H), 7.49 (d, J= 2.0 Hz, 1H), 7.46-7.40 (m, 1H), 7.32 (d, J = 8.2 Hz, 1H), 7.29-7.18 (m, 2H), 7.12-7.01 (m, 1H), 3.39 (s, 3H), 3.27 (s, 3H), 2.38 (d, J= 5.0 Hz, 3H); m / z 4887 N,1',3'-trimethyl-2-(2-methyl-3-(trifluoromethyl)phenyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (400 MHz, DMSO-d6) δ 8.02 (d, J =8.5 Hz, 1H), 7.80-7.72 (d, 3H), 7.63 (d, J =1.7 Hz, 1H), 7.49-7.37 (m, 3H), 7.24 (d, J =8.2 Hz, 1H), 7.16 (dd, J =8.2, 2.0 Hz, 1H), 3.34 (s, 3H), 3.26 (s, 3H), 2.39 (d, J =5.1 Hz, 3H), 2.34 (s, J =1.8 Hz, 3H); m / z 5318 2-(2,3-dimethylphenyl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (400 MHz, DMSO-d6) δ 7.98 (d, J= 8.5 Hz, 1H), 7.73 (dd, J= 8.5, 1.8 Hz, 1H), 7.60 (d, J= 1.7 Hz, 1H), 7.45-7.38 (m, 1H), 7.36 (d, J= 2.0 Hz, 1H), 7.26 (d, J= 7.6 Hz, 1H), 7.21 (dd, J= 8.0, 2.4 Hz, 2H), 7.11-7.05 (m, 2H), 3.33 (s, 3H), 3.26 (s, 3H), 2.39 (d, J = 5.1 Hz, 4H), 2.22 (s, 3H), 2.09 (s, 3H); m / z 4769 2-(3-cyclopropyl-1-methyl-1H-pyrazol-4-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (400 MHz, DMSO-d6) δ 7.88 (d, J =8.5 Hz, 1H), 7.65 (dd, J =8.4, 1.8 Hz, 1H), 7.46 (d, J =2.0 Hz, 1H), 7.40 (d, J =8.2 Hz, 1H), 7.38-7.32 (m, 2H), 7.18 (dd, J =8.3, 2.0 Hz, 1H), 6.93 (s, 1H), 3.60 (s, 3H), 3.44 (s, 3H), 3.34 (s, 3H), 2.35 (d, J =5.1 Hz, 3H), 0.91 (dd, J =8.4, 2.8 Hz, 2H), 0.85-0.78 (m, 2H); m / z 49210 2-(4-chloro-1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (400 MHz, DMSO-d6) δ 11.84 (s, 1H), 7.97 (d, J =8.5 Hz, 1H), 7.78 (d, J =2.8 Hz, 1H), 7.72 (dd, J =8.4, 1.8 Hz, 1H), 7.59 (d, J =1.7 Hz, 1H), 7.40 (d, J =7.2 Hz, 2H), 7.35 (d, J =2.0 Hz, 1H), 7.19 (d, J =8.3 Hz, 1H), 7.15-7.07 (m, 2H), 7.04 (d, J =7.4 Hz, 1H), 3.29 (s, 3H), 3.23 (s, 3H), 3.17 (s, 3H), 2.39 (d, J =5.0 Hz, 3H); m / z 52111 N,1',3'-trimethyl-2-(2-methylthiophen-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (400 MHz, DMSO-d6) δ 7.97 (d, J =8.4 Hz, 1H), 7.70 (dd, J =8.5, 1.8 Hz, 1H), 7.54 (d, J =1.7 Hz, 1H), 7.45-7.35 (m, 2H), 7.33 (d, J =8.2 Hz, 1H), 7.21 (d, J =5.4 Hz, 1H), 7.16 (dd, J =8.2, 2.0 Hz, 1H), 6.66 (d, J =5.4 Hz, 1H), 3.40 (s, 3H), 3.30 (s, 3H), 2.66 (s, 3H), 2.36 (d, J =5.0 Hz, 3H); m / z 46812 2-(3-methoxynaphthalen-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (400 MHz, DMSO-d6) δ 8.21 (s, 1H), 8.00 (d, J =8.4 Hz, 1H), 7.96-7.89 (m, 1H), 7.81 (d, J =8.3 Hz, 1H), 7.75 (dd, J =8.5, 1.7 Hz, 1H), 7.65 (d, J =1.7 Hz, 1H), 7.57-7.48 (m, 1H), 7.44-7.38 (m, 2H), 7.36 (d, J =2.0 Hz, 1H), 7.28 (s, 1H), 7.15 (d, J =8.3 Hz, 1H), 6.99 (dd, J =8.2, 2.0 Hz, 1H), 3.58 (s, 3H), 3.30 (s, 3H), 3.26 (s, 3H), 2.40 (d, J =5.1 Hz, 3H); m / z 52813 2-(isoquinolin-1-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (400 MHz, DMSO-d6) δ 8.46 (dd, J= 16.8, 7.1 Hz, 2H), 8.09 (dd, J= 23.8, 8.4 Hz, 2H), 7.92 (d, J= 5.6 Hz, 1H), 7.89-7.77 (m, 2H), 7.78-7.69 (m, 2H), 7.52-7.44 (m, 1H), 7.40 (d, J = 2.0 Hz, 1H), 7.15 (d, J = 8.2 Hz, 1H), 7.03 (dd, J = 8.2, 2.0 Hz, 1H), 3.31 (s, 3H), 3.23 (s, 3H), 2.42 (d, J=5.1 Hz, 3H); m / z 49914 2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (400 MHz, Methanol-d4) δ 7.96-7.84 (m, 2H), 7.63 (s, 1H), 7.45 (d, J =7.9 Hz, 2H), 7.33 (t, J =8.7 Hz, 1H), 3.76 (dd, J =12.3, 4.8 Hz, 1H), 3.66 (t, J =12.0 Hz, 1H), 3.54 (s, 3H), 3.47 (s, 3H), 2.47 (s, 3H), 1.98 (dd, J =18.5, 7.0 Hz, 1H), 1.91-1.83 (m, 3H), 1.23 (d, J =3.7 Hz, 3H), 1.06 (d, J =5.1 Hz, 3H); m / z 48415 N,1',3'-trimethyl-2'-oxo-2-(pyrazolo[1,5-a]pyrimidin-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (400 MHz, Methanol-d4) δ 9.21 (s, 1H), 9.03 (s, 1H), 8.10 (d, J =31.0 Hz, 2H), 7.74 (s, 1H), 7.57-7.44 (m, 18.9 Hz, 5H), 3.58 (s, 3H), 3.44 (s, 3H), 2.51 (s, 3H); m / z 48916 2-(4-hydroxynaphthalen-1-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (400 MHz, DMSO-d6) δ 10.62 (s, 1H), 8.16 (d, J= 7.7 Hz, 1H), 8.07-7.98 (m, 2H), 7.75 (dd, J = 8.6, 1.8 Hz, 1H), 7.61 (d, J= 1.7 Hz, 1H), 7.53-7.36 (m, 5H), 7.14 (d, J= 8.2 Hz, 1H), 7.07-7.00 (m, 1H), 6.79 (d, J= 7.9 Hz, 1H), 3.29 (s, 3H), 3.22 (s, 3H), 2.40 (d, J=5.0 Hz, 3H); m / z 51417 N,1',3'-trimethyl-2-(1-methyl-1H-indazol-7-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (400 MHz, DMSO-d6)δ 8.15 (s, 1H), 8.06 (d, J= 8.6 Hz, 1H), 7.86 (d, J= 8.1 Hz, 1H), 7.78 (dd, J= 8.4, 1.8 Hz, 1H), 7.65 (d, J= 1.7 Hz, 1H), 7.55-7.42 (m, 3H), 7.21 (d, J= 2.4 Hz, 2H), 7.15-7.06 (m, 1H), 3.81 (s, 3H), 3.32 (s, 3H), 3.25 (s, 3H), 2.41 (d, J= 4.9 Hz, 3H); m / z 50218 N,1',3'-trimethyl-2'-oxo-2-(thiazol-5-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (400 MHz, DMSO-d6) δ 9.19 (s, 1H), 7.97 (d, J =8.5 Hz, 1H), 7.80 (s, 1H), 7.72 (d, J =8.7 Hz, 1H), 7.59 (d, J =2.0 Hz, 1H), 7.52-7.39 (m, 3H), 7.39-7.31 (m, 1H), 3.46 (s, 3H), 3.34 (s, 3H), 2.37 (d, J =4.9 Hz, 3H); m / z 45519 2-(4-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide[2-(4-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide] 1H-NMR (400 MHz, DMSO-d6) δ 8.19 (d, J =5.2 Hz, 1H), 7.98 (d, J =8.6 Hz, 1H), 7.90 (d, J =2.8 Hz, 1H), 7.73 (dd, J =8.6, 1.8 Hz, 1H), 7.60 (d, J =1.7 Hz, 1H), 7.46-7.35 (m, 2H), 7.24-7.16 (m, 2H), 7.13 (dd, J =8.3, 1.9 Hz, 1H), 3.31 (s, 3H), 3.25 (s, 3H), 2.39 (d, J =5.0 Hz, 3H); m / z 522, 52320 2-(isoquinolin-8-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500MHz, Methanol-d4) δ 9.49-9.37 (m, 1H), 8.57-8.44 (1H), 8.15 (s, 1H), 8.07 (t, J = 8.7 Hz, 2H), 7.92 (dd, J = 8.5, 1.5 Hz, 1H), 7.90 (d, J = 5.8 Hz, 1H), 7.88 (s, 1H), 7.85 (d, J = 7.0 Hz, 1H), 7.78 (t, J = 7.6 Hz, 1H), 7.33 (d, J = 12.2 Hz, 1H), 7.17-7.08 (m, 2H), 3.39 (s, 3H), 3.31 (s, 3H), 2.54 (d, J = 12.8 Hz, 3H); m / z 49921 5-(6-((3-(azepan-1-yl)propyl)(methyl)amino)-8-(1H-pyrrolo[2,3-b]pyridin-2-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-((3-(azepan-1-yl)propyl)(methyl)amino)-8-(1H-pyrrolo[2,3-b]pyridin-2-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (400 MHz, Methanol-d4) δ 8.27-8.36 (m, 2 H), 8.10 (d, J = 8.0 Hz, 1 H), 7.42 (q, J = 6.4 Hz, 2 H), 7.24-7.28 (m, 2 H), 5.99 (s, 1 H), 4.41-4.53 (m, 2 H), 3.44-3.53 (m, 6 H), 3.41 (s, 5 H), 3.22 (t, J = 12.0 Hz, 2 H), 2.31 (t, J = 8.0 Hz, 2 H), 1.67-1.88 (m, 8 H); m / z 56522 5-(6-((3-(azepan-1-yl)propyl)(methyl)amino)-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-((3-(azepan-1-yl)propyl)(methyl)amino)-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1H-NMR (400 MHz, Methanol-d4) δ 7.36 (d, J = 8.0 Hz, 2 H), 7.22 (q, J = 4.0 Hz, 2 H), 7.09-7.21 (m, 3 H), 6.61 (s, 1 H), 4.45 (s, 2 H), 3.60 (d, J = 12.4 Hz, 2 H), 3.52 (s, 3 H), 3.41 (s, 3 H), 3.35 (t, J = 8.0 Hz, 3 H), 3.08 (t, J = 8.0 Hz, 2 H), 2.46 (s, 3 H), 2.33 (t, J = 8.0 Hz, 2 H), 1.51-1.67 (m, 8 H); m / z 57823 5-(6-((3-(azepan-1-yl)propyl)(methyl)amino)-8-(1H-pyrrolo[3,2-b]pyridin-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one[5-(6-((3-(azepan-1-yl)propyl)(methyl)amino)-8-(1H-pyrrolo[3,2-b]pyridin-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one] 1 H-NMR (400 MHz, Methanol-d4) δ 8.42 (d, J = 8.0 Hz, 1 H), 8.21 (s, 1 H), 7.88 (d, J = 8.0 Hz, 1 H), 7.41 (s, 1 H), 7.32 (d, J = 1.6 Hz, 1 H), 7.27 (q, J = 4.0 Hz, 2 H), 7.19 (d, J = 8.0 Hz, 1 H), 7.10 (q, J = 8.0 Hz, 1 H), 4.31 (s, 2 H), 3.47-3.50 (m, 3 H), 3.44 (s, 3 H), 3.38 (s, 3 H), 3.12-3.13 (m, 2 H), 3.00 (s, 4 H), 2.17 (d, J = 8.0 Hz, 2 H), 1.28-1.51 (m, 8 H); m / z 56524 5-(6-((3-(azepan-1-yl)propyl)(methyl)amino)-8-(1-ethyl-1H-indol-4-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-((3-(azepan-1-yl)propyl)(methyl)amino)-8-(1-ethyl-1H-indol-4-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (400 MHz, Methanol-d4) δ 8.32 (s, 1 H), 7.55 (d, J = 8.0 Hz, 1 H), 7.41 (d, J = 3.2 Hz, 1 H), 7.27 (d, J = 2.0 Hz, 1 H), 7.16 (d, J = 8.0 Hz, 1 H) H), 6.96-7.06 (m, 3 H), 6.78 (d, J = 4.0 Hz, 1 H), 4.24-4.34 (m, 4 H), 3.50 (s, 2 H), 3.27 (s, 3 H), 3.26 (s, 3 H), 3.19 (t, J = 8.0 Hz, 3 H), 3.15 (t, J = 1.2 Hz, 2 H), 2.96 (t, J = 12.0 Hz, 2 H), 2.26-2.29 (m, 2 H), 1.45 (s, 1 H), 1.31 (t, J = 20.0 Hz, 4 H), 1.25 (s, 6 H); m / z 59225 5-(8-(2,5-dimethyl-1-(4-methylpyridin-2-yl)-1H-pyrrol-3-yl)-6-(methyl(2-(methyl(phenyl)amino)ethyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(8-(2,5-dimethyl-1-(4-methylpyridin-2-yl)-1H-pyrrol-3-yl)-6-(methyl(2-(methyl(phenyl)amino)ethyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1H-NMR (400 MHz, Methanol-d4) δ 8.47 (d, J = 5.2 Hz, 1 H), 8.22 (s, 1 H), 7.42 (1 H), 7.35-7.39 (m, 2 H), 7.28 (s, 1 H), 7.23 (q, J = 2.0 Hz, 1 H), 7.14 (t, J = 7.6 Hz, 2 H), 6.87 (d, J = 7.6 Hz, 2 H), 6.73 (d, J = 8.0 Hz, 1 H), 5.39 (s, 1 H), 4.57-4.64 (m, 2 H), 3.90 (t, J = 8.0 Hz, 2 H) H), 3.05 (s, 3 H), 2.51 (s, 3 H), 2.37 (s, 3 H), 1.87 (s, 3 H); m / z 62726 5-(6-((1-Benzylpyrrolidin-3-yl)(methyl)amino)-8-(thiazol-5-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-((1-benzylpyrrolidin-3-yl)(methyl)amino)-8-(thiazol-5-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (400 MHz, DMSO-d6) δ 9.07 (s, 1 H), 8.15 (s, 1 H), 7.64 (s, 1 H), 7.34 (q, J = 20.0 Hz, 3 H), 7.27 (3 H), 7.16 (d, J = 8.4 Hz, 3 H), 3.59 (d, J = 3.6 Hz, 2 H), 3.38 (d, J = 43.2 Hz, 6 H), 2.90 (d, J = 4.0 Hz, 1 H), 2.83 (t, J = 20.0 Hz, 2 H), 2.39-2.52 (m, 3 H), 2.09 (s, 1) H), 1.94-2.06 (m, 2 H), 1.64 - 1.65 (m, 1 H); m / z 55227 1,3-dimethyl-5-(6-(methyl(2-(thiophen-3-yl)ethyl)amino)-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one[1,3-dimethyl-5-(6-(methyl(2-(thiophen-3-yl)ethyl)amino)-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (400 MHz, Methanol-d4) δ 7.86 (d, J =8.5 Hz, 1H), 7.82 (dd, J =8.5, 1.7 Hz, 1H), 7.61 (s, 1H), 7.56 (d, J =1.6 Hz, 1H), 7.53 (s, 1H), 7.44 (d, J =8.2 Hz, 1H), 7.39 (d, J =2.0 Hz, 1H), 7.27 (dd, J =8.2, 2.0 Hz, 1H), 3.84 (s, 3H), 3.55 (s, 3H), 3.44 (s, 3H), 2.48 (s, 3H); m / z 54928 2-(3,5-dimethylisoxazol-4-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (400 MHz, DMSO-d6) δ 8.02 (d, J =8.5 Hz, 1H), 7.74 (dd, J =8.4, 1.8 Hz, 1H), 7.71 (d, J =1.6 Hz, 1H), 7.49-7.40 (m, 2H), 7.34 (d, J =8.2 Hz, 1H), 7.22 (dd, J =8.3, 2.0 Hz, 1H), 3.39 (s, 3H), 3.30 (s, 3H), 2.37 (d, J =5.0 Hz, 3H), 2.18 (s, 3H), 2.08 (s, 3H); m / z 46729 N,1',3'-trimethyl-2'-oxo-2-(1H-pyrazol-4-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (400 MHz, DMSO-d6) δ 13.20 (s, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.65 (dd, J = 8.4, 1.8 Hz, 1H), 7.58-7.48 (m, 3H), 7.44 (d, J = 8.2 Hz, 1H), 7.39 (d, J = 1.8 Hz, 1H), 7.37-7.30 (m, 1H), 7.25 (dd, J = 8.2, 2.0 Hz, 1H), 3.45 (s, 3H), 3.34 (s, 3H), 2.35 (d, J = 4.9 Hz, 3H); m / z 43830 5-(8-(1-isopropyl-1H-pyrrol-3-yl)-6-((2-(6-methoxy-1H-indol-3-yl)ethyl)(methyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(8-(1-isopropyl-1H-pyrrol-3-yl)-6-((2-(6-methoxy-1H-indol-3-yl)ethyl)(methyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (400 MHz, Methanol-d4) δ 8.05 (s, 1 H), 7.50 (d, J = 8.4 Hz, 1 H), 7.36 (d, J = 8.0 Hz, 1 H), 7.23 (d, J = 1.6 Hz, 1 H), 7.14 (q, J = 3.2 Hz, 1 H) H), 7.00 (s, 1 H), 6.81 (q, J = 2.0 Hz, 2 H), 6.71 (t, J = 2.4 Hz, 1 H), 6.51 (q, J = 3.6 Hz, 1 H), 5.98 (q, J = 1.6 Hz, 1 H), 4.78 (t, J = 4.8 Hz, 2H), 3.78-4.76 (m, 1 H), 3.75 (s, 3 H), 3.47-3.74 (m, 9 H), 3.24 (t, J = 6.8 Hz, 2 H), 1.33 (d, J = 6.8 Hz, 6 H); m / z 59031 5-(6-((3-(1H-pyrrol-1-yl)benzyl)(methyl)amino)-8-(1H-benzo[d]imidazol-4-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-((3-(1H-pyrrol-1-yl)benzyl)(methyl)amino)-8-(1H-benzo[d]imidazol-4-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1H-NMR (400 MHz, Methanol-d4) δ 8.32 (s, 1 H), 7.80 (d, J = 8.4 Hz, 1 H), 7.50 (s, 1 H), 7.34-7.42 (m, 4 H), 7.24 (q, J = 8.0 Hz, 3 H), 7.08-7.13 (q, J = 7.6 Hz, 3 H), 6.24 (t, J = 2.4 Hz, 2 H), 3.68-3.85 (m, 2 H), 3.65 (s, 3 H,), 3.48 (s, 3 H), 3.40 (s, 3 H); m / z 58132 5-(6-(((1-cyclohexylpyrrolidin-3-yl)methyl)(methyl)amino)-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-(((1-cyclohexylpyrrolidin-3-yl)methyl)(methyl)amino)-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (400 MHz, Methanol-d4) δ 8.24 (d, J = 8.0 Hz, 2 H), 8.15 (s, 1 H), 7.33 (q, J = 8.4 Hz, 2 H), 7.16-7.22 (m, 2 H), 7.07 (d, J = 8.0 Hz, 1 H), 6.61 (s, 1 H), 3.51 (s, 3 H), 3.47 (s, 2 H), 3.40 (s, 3 H), 3.17 (d, J = 8.0 Hz, 2 H), 3.05 (s, 2 H), 2.55 (s, 1 H), 2.45 (s, 3 H), 2.23 (q, J = 7.2 Hz, 1 H), 1.91 (t, J = 5.6 Hz, 1 H), 1.78 (s, 2 H), 1.59 (s, 2 H), 1.49 (d, J = 12.0 Hz, 1 H), 1.28 (s, 2 H), 0.97-1.10 (m, 4 H); m / z 60433 5-(6-(((1-cyclohexylpyrrolidin-3-yl)methyl)(methyl)amino)-8-(7-ethyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-(((1-cyclohexylpyrrolidin-3-yl)methyl)(methyl)amino)-8-(7-ethyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (400 MHz, Methanol-d4) δ 7.97-8.28 (m, 2 H), 7.34-7.41 (m, 2 H), 7.20-7.25 (m, 2 H), 7.12 (t, J = 7.6 Hz, 1 H), 6.76 (d, J = 104.8 Hz, 1 H), 3.61-3.75 (m, 2 H), 3.53 (s, 3 H), 3.51 (s, 2 H), 3.29 (d, J = 4.0 Hz, 3 H), 3.13-3.20 (m, 2 H), 2.88 (q, J = 11.6 Hz, 2 H), 2.84 (s, 1 H), 2.01-2.46 (m, 2 H), 1.97 (q, J = 9.6 Hz, 2 H), 1.38-1.61 (m, 4 H), 1.27 -1.31 (m, 3 H), 0.95-1.26 (m, 5 H); m / z 61834 5-(8-(1H-indol-5-yl)-6-(methyl(2-(m-tolyloxy)ethyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(8-(1H-indol-5-yl)-6-(methyl(2-(m-tolyloxy)ethyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1H-NMR (400 MHz, DMSO-d6) δ 11.25 (s, 1H), 8.18 (s, 1H), 7.78 (s, 1H), 7.35 (d, J = 6.0 Hz, 3H), 7.28 (t, J = 8.4 Hz, 2H), 7.18 (t, J = 8.4) Hz, 1 H), 6.98 (d, J = 8.0 Hz, 1 H), 6.72-6.80 (m, 3 H), 6.38 (s, 1H), 4.34-4.67 (m, 4 H), 3.37 (s, 3H), 3.30 (s, 3H), 3.29 (s, 3H), 2.24 (s, 3H); m / z 55935 5-(8-(6-chloro-1H-indol-3-yl)-6-(methyl(2-(m-tolyloxy)ethyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(8-(6-chloro-1H-indol-3-yl)-6-(methyl(2-(m-tolyloxy)ethyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (400 MHz, DMSO-d6) δ 11.35 (s, 1 H), 8.43 (d, J = 8.4 Hz, 1 H), 8.17 (s, 1 H), 7.47 (s, 1 H,), 7.37-7.40 (m, 2 H), 7.12-7.24 (m, 2 H), 6.99 (s, 1 H), 6.80-6.84 (m, 2 H), 6.75 (d, J = 7.6 Hz, 1 H), 6.54 (d, J = 2.8 Hz, 1 H), 4.41-4.69 (m, 4 H), 3.86 (s, 3 H), 3.44 (s, 3 H), 3.33 (s, 3 H), 2.26 (s, 3 H); m / z 59336 5-(8-(6-bromo-1H-indol-3-yl)-6-((3-(4-chloro-1H-pyrazol-1-yl)propyl)(methyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one[5-(8-(6-bromo-1H-indol-3-yl)-6-((3-(4-chloro-1H-pyrazol-1-yl)propyl)(methyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one] 1 H-NMR (400 MHz, DMSO-d6) δ 8.42 (d, J = 8.4 Hz, 1 H), 8.11 (s, 1 H), 7.97 (s, 1 H), 7.66 (d, J = 1.6 Hz, 1 H), 7.52 (s, 1 H), 7.33-7.39 (m, 3) H), 7.15 (q, J = 2.4 Hz, 1 H), 6.58 (s, 1 H), 4.25 (t, J = 7.2 Hz, 2 H), 3.78 (s, 5 H), 3.45 (s, 3 H), 3.34 (s, 3 H), 2.31 (s, 2 H); m / z 64737 5-(6-((2-(1-cyclopentylpiperidin-4-yl)ethyl)(methyl)amino)-8-(6-methoxy-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-((2-(1-cyclopentylpiperidin-4-yl)ethyl)(methyl)amino)-8-(6-methoxy-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1H-NMR (400 MHz, DMSO-d6) δ 11.03 (d, J = 2.4 Hz, 1 H), 8.40 (d, J = 8.8 Hz, 1 H), 8.08 (s, 1 H), 7.38 (d, J = 8.0 Hz, 2 H), 7.16 (dd, J = 1.6, 6.4 Hz, 1 H), 6.91 (d, J = 2.4 Hz, 1 H), 6.79 (d, J = 2.0 Hz, 1 H), 6.34 (d, J = 2.8 Hz, 1 H), 3.78 (s, 3 H), 3.44 (s, 3 H), 3.33 (s, 7 H), 3.21 (d, J = 3.6 Hz, 1 H), 2.93 (d, J = 11.2 Hz, 2 H), 2.49 (d, J = 3.6, 2 H), 1.81 (t, J = 12.8 Hz, 2 H), 1.60-1.75 (m, 6 H), 1.46-1.59 (m, 4 H), 1.23-1.34 (m, 4 H) H); m / z 63438 N,1',3'-trimethyl-2-(1-methyl-1H-imidazol-5-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, DMSO-d6) δ 7.96 (d, J = 8.5 Hz, 1H), 7.87 (s, 1H), 7.69 (dd, J = 8.5, 1.8 Hz, 1H), 7.50 (d, J = 1.9 Hz, 1H), 7.41 (d, J = 7.9 Hz, 3H), 7.27 (dd, J = 8.2, 2.0 Hz, 1H), 6.39 (d, J = 1.0 Hz, 1H), 4.07 (s, 3H), 3.44 (s, 6H), 2.35 (s, 3H); m / z ND39 5-(6-(dimethylamino)-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-(dimethylamino)-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (500 MHz, Methanol-d4) δ 8.35 (d, J = 8.2 Hz, 1H), 8.08 (s, 1H), 7.35 (d, J = 8.2 Hz, 1H), 7.31 (d, J = 1.9 Hz, 1H), 7.19 (dd, J = 8.2, 1.9) Hz, 1H), 7.16 (s, 1H), 7.02 (dd, J = 8.3, 1.2 Hz, 1H), 6.47 (s, 1H), 3.68 (s, 6H), 3.52 (s, 3H), 3.41 (s, 3H), 2.44 (s, 3H); m / z ND40 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-sulfonamide 1H-NMR (500 MHz, Methanol-d4) δ 8.20 (d, J = 7.9 Hz, 1H), 8.04 (s, 1H), 7.92 (d, J = 8.5 Hz, 1H), 7.79 (d, J = 8.2 Hz, 1H), 7.57 (s, 1H), 7.43 (d, J = 8.2 Hz, 1H), 7.37 (s, 1H), 7.30 (d, J = 7.9 Hz, 1H), 7.22 (s, 1H), 7.06 (d, J = 7.9 Hz, 1H), 6.81 (s, 1H), 3.55 (s, 3H), 3.41 (s, 3H), 2.51 (s, 3H), 2.46 (s, 3H); m / z 50141 2-[3-(3,4-difluorophenyl)imidazol-4-yl]-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, Chloroform-d) δ 7.81 (d, J = 8.5 Hz, 1H), 7.74-7.72 (m, 1H), 7.69 (d, J = 1.5 Hz, 1H), 7.63 (s, 1H), 7.22 (s, 1H), 7.16-7.10 (m, 1H), 6.97 (d, J = 7.9 Hz, 1H), 6.87-6.81 (m, 2H), 6.76 (dd, J = 8.1, 2.0 Hz, 1H), 6.61 (d, J = 1.8 Hz, 1H), 4.69 (q, J = 5.4 Hz, 1H), 3.48 (s, 3H), 3.34 (s, 3H), 2.59 (d, J = 5.2 Hz, 3H); m / z ND42 2-(6-bromo-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide 1 H-NMR (400 MHz, Chloroform-d) δ 8.61 (d, J = 8.7 Hz, 1H), 8.25 (s, 1H), 7.96 (d, J = 8.2 Hz, 1H), 7.77 (dd, J = 8.5, 1.6 Hz, 1H), 7.60 (d, J = 1.8 Hz, 1H), 7.55-7.52 (m, 1H), 7.43 (dd, J = 8.7, 1.8 Hz, 1H), 7.19-7.18 (m, 2H), 7.00 (s, 1H), 6.60 (d, J = 3.2 Hz, 1H), 4.26 (q, J = 5.2 Hz, 1H), 3.55 (s, 3H), 3.41 (s, 3H), 2.65 (d, J = 5.5 Hz, 3H); m / z 565, 56743 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(6-oxo-2-piperidyl)benzimidazole-5-sulfonamide 1H-NMR (500 MHz, Chloroform-d) δ 8.07-7.98 (1H), 7.89-7.77 (m, 1H), 7.77-7.68 (m, 1H), 7.63 (d, J = 15.3 Hz, 1H), 7.14 (d, J = 8.2 Hz, 1H), 7.11-7.03 (m, 1H), 6.99 (d, J = 25.6 Hz, 1H), 4.77 (s, 1H), 4.24 (td, J = 7.0, 5.2 Hz, 1H), 3.52 (s, 3H), 3.45 (s, 3H), 2.60 (s, 3H), 2.53-2.27 (m, 2H), 2.21 (m, 1H), 2.12-1.95 (1H), 1.99-1.57 (m, 2H); m / z 46944 (S)-2-(1-(3,4-difluorophenyl)-6-oxopiperidin-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500MHz, Chloroform-d) δ 7.95 (d, J = 8.5 Hz, 1H), 7.77 (d, J = 8.2 Hz, 1H), 7.51 (s, 1H), 7.17-7.08 (m, 1H), 7.08-6.93 (m, 3H), 6.93-6.85 (m, 1H), 6.83 (s, 1H), 5.03-4.91 (m, 1H), 4.47-4.34 (m, 1H), 3.62-3.47 (m, 3H), 3.45 (d, J = 6.7 Hz, 1H), 3.32 (s, 2H), 2.86 (dt, J = 17.7, 5.5 Hz, 1H), 2.67-2.59 (m, 3H), 2.50 (m, 1H), 2.29-2.18 (m, 2H), 1.90 (m, 1H), 1.76-1.54 (m, 1H); m / z ND45 2-(5-fluoro-1-phenyl-1H-pyrazol-4-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, Chloroform-d) δ 8.00 (d, J = 8.5 Hz, 1H), 7.82 (d, J = 8.5 Hz, 1H), 7.70 (s, 1H), 7.61 (d, J = 7.9 Hz, 2H), 7.50 (t, J = 7.9 Hz, 2H), 7.41 (t, J = 7.5 Hz, 1H), 7.18 (s, 2H), 7.11 (d, J = 2.1 Hz, 1H), 7.05-6.99 (1H), 4.36 (s, 1H), 3.55 (s, 3H), 3.45 (s, 3H), 2.65 (s, 3H); m / z 53246 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-2-(4-isoquinolyl)-N-methyl-benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, Chloroform-d) δ 9.40 (s, 1H), 8.54 (s, 1H), 8.43 (d, J = 8.5 Hz, 1H), 8.18 (d, J = 8.2 Hz, 1H), 8.16-8.08 (1H), 8.02 (d, J = 15.3 Hz, 1H), 7.96 (t, J = 7.6 Hz, 1H), 7.91 (s, 1H), 7.89 (s, 1H), 7.85-7.79 (1H), 6.95-6.92 (2H), 6.90 (s, 1H), 3.53-3.37 (3H), 3.37-3.24 (3H), 2.69 (s, 3H); m / z 49947 tert-butyl 4-[3-[1-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-6-(methylsulfamoyl)benzimidazol-2-yl]-1H-indol-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylate 1H-NMR (500 MHz, Chloroform-d) δ 8.51 (d, J = 8.2 Hz, 1H), 7.81 (s, 1H), 7.67-7.64 (m, 2H), 7.58 (s, 1H), 7.46-7.44 (m, 1H), 7.12-7.09 (m, 2H), 6.97 (s, 1H), 6.65 (s, 1H), 5.97 (s, 1H), 4.97 (s, 1H), 4.03 (s, 2H), 3.59 (m, 2H), 3.47 (s, 3H), 3.32 (s, 3H), 2.58 (d, J = 4.9 Hz, 3H), 2.45 (s, 2H), 1.22 (s, 9H); m / z 66848 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-[6-(1-methylpyrazol-4-yl)-1H-indol-3-yl]benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, Chloroform-d) δ 8.75-8.69 (m, 1H), 8.63-8.57 (m, 1H), 7.92 (d, J = 8.5 Hz, 1H), 7.74-7.71 (m, 2H), 7.60 (d, J = 7.6 Hz, 2H), 7.48-7.38 (m, 2H), 7.18-7.13 (m, 2H), 6.99-6.99 (m, 1H), 6.59 (d, J = 7.9 Hz, 1H), 4.49 (s, 1H), 3.93 (s, 3H), 3.53 (s, 3H), 3.38(s, 3H), 2.63 (s, 3H); m / z ND49 tert-butyl 4-(3-(1',3'-dimethyl-6-(N-methylsulfamoyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazol]-2-yl)-1H-indol-6-yl)piperidine-1-carboxylate[tert-butyl 4-(3-(1',3'-dimethyl-6-(N-methylsulfamoyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazol]-2-yl)-1H-indol-6-yl)piperidine-1-carboxylate]ND m / z 67050 N,1',3'-trimethyl-2'-oxo-2-(6-(piperidin-4-yl)-1H-indol-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, DMSO-d6) δ 11.40 (s, 1H), 8.57 (d, J = 8.2 Hz, 1H), 7.90 (d, J = 8.5 Hz, 1H), 7.65 (dd, J = 8.5, 1.5 Hz, 1H), 7.51 (d, J = 1.8 Hz, 1H), 7.47 (d, J = 8.2 Hz, 1H), 7.36 (d, J = 1.5 Hz, 1H), 7.33 (d, J = 5.2 Hz, 1H), 7.29 (dd, J = 8.2, 1.8 Hz, 1H), 7.26 (s, 1H), 7.13 (d, J = 8.5 Hz, 1H), 6.59 (d, J = 3.1 Hz, 1H), 3.47 (s, 3H), 3.38-3.36 (m, 2H), 3.34 (s, 3H), 3.17 (d, J = 5.2 Hz, 1H), 3.03-2.94 (m, 3H), 2.36 (d, J = 5.2 Hz, 3H), 1.98-1.95 (m, 2H), 1.91-1.86 (m, 2H); m / z 57051 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-2-(1H-indazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide 1 H-NMR (400 MHz, DMSO-d6) δ 8.07 (s, 1H), 8.03-7.99 (1H), 7.93 (d, J = 8.2 Hz, 1H), 7.67 (dd, J = 8.5, 1.6 Hz, 1H), 7.61 (dd, J = 8.7, 1.4 Hz, 1H), 7.49 (d, J = 8.9 Hz, 1H), 7.47-7.44 (2H), 7.31 (d, J = 8.2 Hz, 1H), 7.17 (dd, J = 8.2, 1.8 Hz, 1H), 3.37 (s, 3H), 3.26 (s, 3H), 2.33 (d, J = 5.0 Hz, 3H); m / z 48852 N,1',3'-trimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-carboxamide 1H-NMR (400 MHz, Chloroform-d) δ 8.59 (d, J = 8.7 Hz, 1H), 8.08 (s, 1H), 7.88 (d, J = 8.7 Hz, 1H), 7.59 (dd, J = 8.2, 1.4 Hz, 1H), 7.51 (s, 1H), 7.23 (s, 1H), 7.18-7.12 (2H), 7.02-6.99 (1H), 6.56 (d, J = 3.0 Hz, 1H), 6.15 (d, J = 4.6 Hz, 1H), 3.49 (d, J = 12.3 Hz, 3H), 3.40-3.33 (3H), 3.03-2.95 (3H), 2.49-2.44 (3H); m / z 46553 3-(1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-2-(3-methoxynaphthalen-2-yl)-N-methyl-3H-imidazo[4,5-b]pyridine-5-carboxamide[3-(1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-2-(3-methoxynaphthalen-2-yl)-N-methyl-3H-imidazo[4,5-b]pyridine-5-carboxamide] 1 H-NMR (400 MHz, DMSO-d6) δ 8.35 (d, J = 8.2 Hz, 1H), 8.25 (s, 1H), 8.23-8.14 (m, 1H), 8.10 (d, J = 8.3 Hz, 1H), 7.94 (d, J = 8.1 Hz, 1H), 7.82 (d, J = 8.1 Hz, 1H), 7.58-7.49 (m, 1H), 7.46-7.35 (m, 2H), 7.28 (s, 1H), 7.07 (d, J = 8.2 Hz, 1H), 6.91 (dd, J = 8.2, 2.0 Hz, 1H), 3.53 (s, 3H),3.29 (s, 6H), 2.81 (d, J = 4.7 Hz, 3H); m / z 49354 5-[6-(difluoromethyl)-2-(6-methyl-1H-indol-3-yl)benzimidazol-1-yl]-1,3-dimethyl-benzimidazol-2-one 1 H-NMR (500 MHz, Chloroform-d) δ 8.50 (d, 1H), 7.93 (d, 1H), 7.72 (d, 1H), 7.12 (m, 3H), 6.82 (m, 3H), 6.67 (m, 1H), 3.54 (s, 3H), 3.39 (s, 3H), 2.15 (s, 3H); m / z 45855 5-(4-chloro-2-(6-methyl-1H-indol-3-yl)-1H-imidazo[4,5-c]pyridin-1-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(4-chloro-2-(6-methyl-1H-indol-3-yl)-1H-imidazo[4,5-c]pyridin-1-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (400 MHz, DMSO-d6) δ 11.30 (s, 1H), 8.53 (d, 1H), 8.07 (s, 1H), 7.54 (d, 1H), 7.36 (m, 1H), 7.29 (m, 2H), 7.09 (m, 2H), 6.54 (brs, 1H), 3.46 (s, 3H), 3.35 (s, 3H), 2.43 (s, 3H); m / z 44356 5-[4-(dimethylamino)-2-(6-methyl-1H-indol-3-yl)imidazo[4,5-c]pyridin-1-yl]-1,3-dimethyl-benzimidazol-2-one] 1H-NMR (400MHz, DMSO-d6) δ 11.06 (s, 1H), 8.42 (d, 1H), 7.78 (d, 1H), 7.37 (m, 2H), 7.19 (m, 1H), 7.13 (m, 1H), 7.03 (d, 1H), 6.41 (m, 2H), 3.50 (s, 6H), 3.45 (s, 3H), 3.33 (s, 3H), 2.41 (s, 3H); m / z 45257 5-[4-(dimethylamino)imidazo[4,5-c]pyridin-1-yl]-1,3-dimethyl-benzimidazol-2-one] 1 H-NMR (500 MHz, Chloroform-d) δ 8.00 (d, 1H), 7.93 (s, 1H), 7.28 (s, 1H), 7.17 (m, 1H), 7.13 (m, 1H), 7.06 (s, 1H), 6.70 (d, 1H), 3.58 (s, 6H), 3.51 (s, 3H), 3.48 (s, 3H); m / z 32358 1,3-dimethyl-5-[2-(6-methyl-1H-indol-3-yl)-6-(1-methylpyrazol-4-yl)benzimidazol-1-yl]benzimidazol-2-one 1 H-NMR (400 MHz, DMSO-d6) δ 11.10 (s, 1H), 8.51 (d, 1H), 8.06 (d, 1H), 7.78 (s, 1H), 7.70 (d, 1H), 7.47 (m, 3H), 7.23 (m, 2H), 7.09 (s, 1H), 7.02 (d, 1H), 6.46 (d, 1H), 3.81 (s, 3H), 3.47 (s, 3H), 3.36 (s, 3H), 2.42 (s, 3H); m / z 48859 5-[7-(dimethylamino)-2-(6-methyl-1H-indol-3-yl)imidazo[4,5-b]pyridin-3-yl]-1,3-dimethyl-benzimidazol-2-one[5-[7-(dimethylamino)-2-(6-methyl-1H-indol-3-yl)imidazo[4,5-b]pyridin-3-yl]-1,3-dimethyl-benzimidazol-2-one] 1 H-NMR (500 MHz, DMSO-d6) δ 11.06 (s, 1H), 8.42 (d, 1H), 7.78 (d, 1H), 7.37 (m, 2H), 7.19 (m, 1H), 7.13 (m, 1H), 7.03 (d, 1H), 6.41 (m, 2H), 3.50 (s, 6H), 3.45 (s, 3H), 3.33 (s, 3H), 2.41 (s, 3H); m / z 45260 2-(7-bromo-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, DMSO-d6) δ 11.64 (s, 1H), 8.66 (d, J = 7.9 Hz, 1H), 7.95 (d, J = 8.2 Hz, 1H), 7.67 (dd, J = 8.4, 1.7 Hz, 1H), 7.55 (d, J = 8.4, 1.7 Hz, 1H) 1.8 Hz, 1H), 7.50 (d, J = 8.2 Hz, 1H), 7.47 (d, J = 7.6 Hz, 1H), 7.40 (d, J = 1.5 Hz, 1H), 7.35-7.33 (m, 2H), 7.21-7.18 (m, 1H), 6.61 (s, 1H), 3.47 (s, 3H), 3.34 (s, 3H), 2.37 (d, J = 4.9 Hz, 3H); m / z ND61 2-(7-chloro-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, DMSO-d6) δ 11.81 (s, 1H), 8.62 (d, J = 7.9 Hz, 1H), 7.95 (d, J = 8.2 Hz, 1H), 7.68-7.66 (m, 1H), 7.55 (d, J = 1.5 Hz, 1H), 7.49 (d, J = 8.2 Hz, 1H), 7.40 (s, 1H), 7.35-7.32 (m, 3H), 7.27-7.24 (m, 1H), 6.62 (s, 1H), 3.47 (s, 3H), 3.34 (s, 3H), 2.37 (d, J = 4.9 Hz, 3H); m / z ND62 2-(5-chloro-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide 1H-NMR (500 MHz, DMSO-d6) δ 11.56 (s, 1H), 8.68-8.68 (m, 1H), 7.97 (d, J = 8.5 Hz, 1H), 7.67-7.65 (m, 1H), 7.54 (d, J = 2.1 Hz, 1H), 7.49 (d, J = 7.0 Hz, 1H), 7.47 (d, J = 6.4 Hz, 1H), 7.37 (d, J = 1.5 Hz, 1H), 7.32-7.30 (m, 2H), 7.24 (dd, J = 8.9, 2.1 Hz, 1H), 6.68 (s, 1H), 3.47 (s, 3H), 3.34 (s, 3H), 2.37-2.36 (m, 3H); m / z ND63 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(5-methyl-1H-indazol-3-yl)benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, Chloroform-d) δ 8.41 (s, 1H), 8.06 (d, J = 8.5 Hz, 1H), 7.82 (d, J = 8.5 Hz, 1H), 7.71 (s, 1H), 7.39-7.37 (m, 2H), 7.32-7.30 (m, 2H), 7.17-7.15 (m, 1H), 7.11-7.09 (m, 1H), 7.02 (s, 1H), 4.29 (q, J = 5.5 Hz, 1H), 3.52 (s, 3H), 3.40 (s, 3H), 2.66 (d, J = 5.2 Hz, 3H), 2.56 (s, 3H); m / z ND64 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(5-methyl-1H-indol-3-yl)benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, Chloroform-d) δ 8.50 (s, 1H), 8.16 (s, 1H), 7.99 (d, J = 8.7 Hz, 1H), 7.77 (d, J = 8.2 Hz, 1H), 7.60 (s, 1H), 7.28 (s, 1H), 7.21-7.13 (m, 3H), 6.99 (s, 1H), 6.60 (d, J = 2.7 Hz, 1H), 4.24 (q, J = 5.3 Hz, 1H), 3.55 (s, 3H), 3.40 (s, 3H), 2.65 (d, J = 5.2 Hz, 3H), 2.55 (s, 3H); m / z ND65 1,3-dimethyl-5-[2-(6-methyl-1H-indol-3-yl)-6-methylsulfonyl-benzimidazol-1-yl]benzimidazol-2-one 1 H-NMR (400 MHz, DMSO-d6) δ 11.28 (s, 1H), 8.53 (d, J = 8.7 Hz, 1H), 7.98-7.93 (1H), 7.78 (d, J = 8.7 Hz, 1H), 7.54-7.50 (1H), 7.48 (d, J = 8.2 Hz, 1H), 7.45-7.42 (1H), 7.29 (d, J = 6.4 Hz, 1H), 7.23 (s, 1H), 7.09-7.04 (1H), 6.54 (d, J = 2.7 Hz, 1H), 3.34 (s, 6H), 3.29 (s, 3H), 2.44-2.41 (3H); m / z ND66 1,3-dimethyl-5-[2-(6-methyl-1H-indol-3-yl)imidazo[4,5-c]pyridin-1-yl]benzimidazol-2-one 1 H-NMR (500 MHz, Chloroform-d) δ 9.06 (s, 1H), 8.83 (s, 1H), 8.51 (d, J = 8.5 Hz, 1H), 8.23 ​​(d, J = 4.9 Hz, 1H), 7.19-7.10 (m, 4H), 7.07 (s, 1H), 6.88 (d, J = 5.2 Hz, 1H), 6.46 (s, 1H), 3.53 (s, 3H), 3.44 (s, 3H), 2.47 (s, 3H); m / z 40967 N-methyl-2-(6-methyl-1H-indol-3-yl)-1-(1,3,3-trimethyl-2-oxoindolin-6-yl)-1H-benzo[d]imidazole-6-sulfonamide 1 H-NMR (500 MHz, DMSO-d6) δ 11.37 (s, 1H), 8.48 (d, 1H), 7.93 (d, 1H), 7.71 (m, 2H), 7.44 (s, 1H), 7.38 (m, 2H), 7.28 (m, 1H), 7.23 (d, 1H), 7.07 (d, 1H), 6.62 (brs, 1H), 3.13 (s, 3H), 2.43 (s, 3H), 2.34 (d, 3H), 1.43 (s, 6H); m / z 51468 2-(5-cyano-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, DMSO-d6) δ 11.85 (s, 1H), 9.07 (s, 1H), 8.01 (d, J = 8.5 Hz, 1H), 7.69-7.65 (m, 2H), 7.61-7.59 (m, 1H), 7.56 (d, J = 2.1 Hz, 1H), 7.48 (d, J = 8.2 Hz, 1H), 7.39 (d, J = 1.2 Hz, 1H), 7.37-7.35 (m, 1H), 7.33 (dd, J = 8.2, 1.8 Hz, 1H), 6.82 (s, 1H), 3.47 (s, 3H), 3.34 (s, 3H), 2.37 (d, J = 4.9 Hz, 3H); m / z ND69 2-(5-bromo-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, DMSO-d6) δ 11.59 (s, 1H), 8.81 (d, J = 1.8 Hz, 1H), 7.98 (d, J = 8.5 Hz, 1H), 7.66 (dd, J = 8.2, 1.5 Hz, 1H), 7.54 (d, J = 1.8 Hz, 1H), 7.48-7.43 (m, 2H), 7.37-7.30 (m, 4H), 6.67 (s, 1H), 3.47 (s, 3H), 3.34 (s, 3H), 2.37 (s, 3H); m / z ND70 2-(4-bromo-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, DMSO-d6) δ 11.83 (s, 1H), 7.96 (d, J = 8.5 Hz, 1H), 7.83 (s, 1H), 7.71 (dd, J = 8.4, 1.7 Hz, 1H), 7.59 (d, J = 1.5 Hz, 1H), 7.44 (d, J = 7.9 Hz, 1H), 7.38 (s, 1H), 7.35 (d, J = 1.5 Hz, 1H), 7.20-7.14 (m, 3H), 7.03 (t, J = 7.9 Hz, 1H), 3.28 (s, 3H), 3.22 (s, 3H), 2.39 (s, 3H); m / z ND71 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-[6-(trifluoromethyl)-1H-indol-3-yl]benzimidazole-5-sulfonamide 1H-NMR (500 MHz, DMSO-d6) δ 11.72 (s, 1H), 8.84 (d, J = 8.5 Hz, 1H), 7.96 (d, J = 8.5 Hz, 1H), 7.84 (s, 1H), 7.67 (dd, J = 8.4, 1.7 Hz, 1H), 7.56-7.54 (m, 2H), 7.49-7.47 (m, 1H), 7.39 (d, J = 1.5 Hz, 1H), 7.36-7.31 (m, 2H), 6.86 (s, 1H), 3.47 (s, 3H), 3.34 (s, 3H), 2.37 (d, J = 4.9 Hz, 3H); m / z N.D72 2-(7-cyclopropyl-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide 1 H-NMR (400 MHz, Chloroform-d) δ 8.54 (d, J = 8.2 Hz, 1H), 8.48 (s, 1H), 7.96 (d, J = 8.7 Hz, 1H), 7.75 (dd, J = 8.5, 1.6 Hz, 1H), 7.59 (d, J = 1.8 Hz, 1H), 7.20 (d, J = 1.8 Hz, 1H), 7.16 (s, 1H), 7.05 (d, J = 7.3 Hz, 1H), 6.99-6.99 (m, 1H), 6.64 (d, J = 2.7 Hz, 1H), 4.24 (q, J = 5.0 Hz, 1H), 3.54 (s, 3H), 3.40 (s, 3H), 2.64 (d, J = 5.5 Hz, 3H), 2.01-1.96 (m, 1H), 0.96-0.92 (m, 2H), 0.76-0.72 (m, 2H); m / z 52773 2-(4-cyclopropyl-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, Chloroform-d) δ 8.32 (s, 1H), 7.95 (d, J = 8.2 Hz, 1H), 7.80-7.79 (m, 2H), 7.21 (d, J = 7.6 Hz, 1H), 7.18-7.15 (m, 1H), 7.10-7.07 (m, 1H), 6.98-6.97 (m, 1H), 6.90 (s, 1H), 6.81 (d, J = 7.0 Hz, 1H), 4.28 (q, J = 5.5 Hz, 1H), 3.43 (s, 3H), 3.27 (s, 3H), 2.68 (d, J = 5.5 Hz, 3H), 2.41-2.38 (m, 1H), 0.89-0.87 (m, 2H), 0.66-0.64 (m, 2H); m / z 52774 N,1',3'-trimethyl-2,2'-dioxo-2,2',3,3'-tetrahydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, DMSO-d6) δ 8.74 (s, 1H), 7.98 (d, 1H), 7.89 (d, 1H), 7.72 (d, 2H), 7.58 (d, 1H), 7.72 (m, 2H), 7.38 (d, 1H), 3.43 (s, 3H), 3.39 (s, 3H), 2.38 (d, 3H); m / z 38875 N-[4-[1-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-6-(methylsulfamoyl)benzimidazol-2-yl]-3-methyl-phenyl]acetamide 1 H-NMR (400 MHz, Chloroform-d) δ 7.99 (d, 1H), 7.84 (m, 2H), 7.48 (s, 1H), 7.34 (m, 1H), 7.23 (m, 2H), 6.99 (m 2H), 6.77 (s, 1H), 3.47 (s, 3H), 3.35 (s, 3H), 2.29 (s, 3H), 2.19 (s, 3H), 1.28 (s, 3H); m / z 51976 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-[5-(trifluoromethyl)-1H-indol-3-yl]benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, DMSO-d6) δ 11.80 (s, 1H), 8.97 (s, 1H), 8.00 (d, J = 8.2 Hz, 1H), 7.68 (s, 1H), 7.66 (s, 1H), 7.56 (s, 1H), 7.53 (d, J = 7.0 Hz, 1H), 7.47 (d, J = 7.9 Hz, 1H), 7.40 (s, 1H), 7.36-7.34 (m, 1H), 7.32 (dd, J = 8.2, 1.8 Hz, 1H), 6.84 (s, 1H), 3.46 (s, 3H), 3.34 (s, 3H), 2.37 (d, J = 4.3 Hz, 3H); m / z ND77 2-(6-bromo-1H-pyrrolo[3,2-c]pyridin-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, DMSO-d6) δ 9.48 (s, 1H), 7.94 (d, J = 6.1 Hz, 1H), 7.67-7.63 (m, 2H), 7.54 (s, 1H), 7.47 (d, J = 7.6 Hz, 1H), 7.37-7.30 (m, 3H), 6.74 (s, 1H), 3.46 (s, 3H), 3.34 (s, 3H), 2.36 (d, J = 4.0 Hz, 3H); m / z 566, 56878 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(1H-pyrrolo[3,2-c]pyridin-3-yl)benzimidazole-5-sulfonamide 1 H-NMR (400 MHz, Methanol-d4) δ 9.53 (s, 1H), 8.26 (d, J = 5.9 Hz, 1H), 7.96 (d, J = 8.7 Hz, 1H), 7.81-7.79 (m, 1H), 7.60 (d, J = 1.4 Hz, 1H), 7.48 (d, J = 5.5 Hz, 1H), 7.44-7.42 (m, 2H), 7.32-7.29 (m, 1H), 7.00 (s, 1H), 3.54 (s, 3H), 3.41 (s, 3H), 2.50 (s, 3H); m / z ND79 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-2-(4-formyl-1-naphthyl)-N-methyl-benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, Chloroform-d) δ 10.41 (s, 1H), 9.26 (d, J = 8.5 Hz, 1H), 8.18 (d, J = 8.5 Hz, 1H), 8.05 (d, J = 8.2 Hz, 1H), 7.93-7.87 (m, 3H), 7.74-7.71 (m, 1H), 7.64-7.61 (m, 2H), 6.92-6.85 (m, 2H), 6.82 (s, 1H), 4.53-4.51 (m, 1H), 3.37 (s, 3H), 3.25 (s, 3H), 2.68 (d, J = 5.2 Hz, 3H); m / z 52680 1,3-dimethyl-5-[2-(6-methyl-1H-indol-3-yl)imidazo[4,5-c]pyridin-3-yl]benzimidazol-2-one]ND m / z 40981 2-(4-(difluoromethyl)naphthalen-1-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Chloroform-d) δ 8.17 (d, J = 8.2 Hz, 2H), 8.05 (d, J = 8.2 Hz, 1H), 7.91 (s, 1H), 7.87 (d, J = 8.5 Hz, 1H), 7.65-7.57 (m, 3H), 7.49 (d, J = 7.3 Hz, 1H), 7.09 (t, J = 55.5 Hz, 1H), 6.94-6.87 (m, 2H), 6.78 (s, 1H), 4.48-4.46 (m, 1H), 3.39 (s, 3H), 3.24 (s, 3H), 2.68 (d, J = 5.2 Hz, 3H); m / z 54882 N-methyl-2-(6-methyl-1H-indol-3-yl)-3-(1,3,3-trimethyl-2-oxo-indolin-5-yl)benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, DMSO-d6) δ 11.33 (s, 1H), 8.47 (d, 1H), 7.92 (d, 1H), 7.67 (m, 2H), 7.55 (d, 1H), 7.40 (m, 3H), 7.24 (m, 1H), 7.06 (d, 1H), 6.60 (d, 1H), 3.27 (s, 3H), 3.43 (s, 3H), 2.39 (d, 3H), 1.32 (s, 6H); m / z 51483 1',3'-dimethyl-6-(N-methylsulfamoyl)-2'-oxo-N-(pyridin-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-2-carboxamide[1',3'-dimethyl-6-(N-methylsulfamoyl)-2'-oxo-N-(pyridin-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-2-carboxamide]ND; m / z 49284 1-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-6-(methylsulfamoyl)-N-(4-pyridyl)benzimidazole-2-carboxamide[1-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-6-(methylsulfamoyl)-N-(4-pyridyl)benzimidazole-2-carboxamide]ND; m / z 49285 3-(1,3-dimethyl-2-oxo-benzimidazol-4-yl)-N-methyl-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-sulfonamide 1 H-NMR (400 MHz, Chloroform-d) δ 8.61 (d, J = 8.2 Hz, 1H), 8.41 (s, 1H), 7.97 (d, J = 8.2 Hz, 1H), 7.78 (dd, J = 8.2, 1.8 Hz, 1H), 7.50 (d, J = 1.4 Hz, 1H), 7.31-7.27 (m, 1H), 7.21-7.11 (m, 4H), 6.51 (d, J = 3.2 Hz, 1H), 4.46 (q, J = 5.3 Hz, 1H), 3.48 (s, 3H), 2.61 (d, J = 5.5 Hz, 3H), 2.60 (s, 3H), 2.46 (s, 3H); m / z ND86 3-(1,3-dimethyl-2-oxo-benzimidazol-4-yl)-N-methyl-2-(3-methylimidazol-4-yl)benzimidazole-5-sulfonamide 1H-NMR (400 MHz, Chloroform-d) δ 7.94 (d, J = 8.2 Hz, 1H), 7.81 (dd, J = 8.2, 1.8 Hz, 1H), 7.56-7.55 (m, 2H), 7.31-7.27 (m, 1H), 7.22 (dd, J = 8.0, 1.1 Hz, 1H), 7.04 (dd, J = 8.0, 1.1 Hz, 1H), 6.48 (s, 1H), 4.38 (q, J = 5.5 Hz, 1H), 4.21 (s, 3H), 3.51 (s, 3H), 2.63 (d, J = 5.5 Hz, 3H), 2.61 (s, 3H); m / z ND87 N-methyl-2-(6-methyl-1H-indol-3-yl)-3-(2-oxo-3,4-dihydro-1H-quinolin-7-yl)benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, Chloroform-d) δ 8.54 (s, 1H), 8.40 (d, J = 8.2 Hz, 1H), 8.28 (s, 1H), 8.01-7.93 (1H), 7.74 (d, J = 8.5 Hz, 1H), 7.56 (s, 1H), 7.29 (d, J = 7.9 Hz, 1H), 7.11 (d, J = 8.2 Hz, 1H), 7.05 (s, 1H), 6.93 (d, J = 7.9 Hz, 1H), 6.67 (s, 1H), 6.48 (s, 1H), 4.59-4.47 (1H), 3.08 (t, J = 7.5 Hz, 2H), 2.74 (t, J = 7.5 Hz, 2H), 2.62 (d, J = 5.5 Hz, 3H), 2.43 (s, 3H); m / z 48688 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-2-(1H-indazol-3-yl)-N-methyl-benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, DMSO-d6) δ 13.53 (s, 1H), 8.57 (d, J = 8.2 Hz, 1H), 8.05 (d, J = 8.7 Hz, 1H), 7.73 (d, J = 8.5 Hz, 1H), 7.57 (d, J = 8.2 Hz, 1H), 7.50-7.44 (m, 3H), 7.42-7.39 (m, 1H), 7.37-7.32 (m, 2H), 7.26 (dd, J = 8.1, 1.7 Hz, 1H), 3.44 (s, 3H), 2.38 (d, J = 4.0 Hz, 3H); m / z ND89 Methyl 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-carboxylate 1 H-NMR (500 MHz, DMSO-d6) δ 11.24 (s, 1H), 8.53 (d, 1H), 7.90 (m, 1H), 7.84 (d, 1H), 7.53 (s, 1H), 7.47 (d, 2H), 7.28 (d, 1H), 7.23 (d, 1H), 7.07 (d, 1H), 6.54 (s, 1H), 3.93 (s, 3H), 3.81 (s, 3H), 3.48 (s, 3H), 2.43 (s, 3H); m / z 46690 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-carboxylic acid 1 H-NMR (500MHz, DMSO-d6) δ 11.22 (s, 1H), 8.51 (d, J = 7.9 Hz, 1H), 7.87 (d, J = 7.9 Hz, 1H), 7.77 (d, J = 8.2 Hz, 1H), 7.53 (s, 1H), 7.49 (s, 1H), 7.45 (d, J = 8.2 Hz, 1H), 7.26 (d, J = 8.2 Hz, 1H), 7.22 (s, 1H), 7.05 (d, J = 8.2 Hz, 1H), 6.54 (d, J = 2.7 Hz, 1H), 3.46 (s, 3H), 3.34 (s, 3H), 2.42 (s, 3H); m / z 45291 3-[3-(3,5-dimethylisoxazol-4-yl)phenyl]-N-methyl-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-sulfonamide 1H-NMR (Chloroform-d) δ 8.73 (s, 1H), 8.01-7.95 (1H), 7.93 (d, J = 8.5 Hz, 1H), 7.78 (s, 1H), 7.77-7.73 (1H), 7.69 (t, J = 7.9 Hz, 1H), 7.53 (d, J = 7.9 Hz, 1H), 7.43 (d, J = 7.9 Hz, 1H), 7.19 (s, 1H), 7.12 (s, 1H), 7.00 (d, J = 8.2 Hz, 1H), 6.92 (d, J = 2.7 Hz, 1H), 4.54 (q, J = 5.4 Hz, 1H), 2.65 (d, J = 5.2 Hz, 3H), 2.42 (s, 3H), 2.23 (s, 3H), 2.05 (s, 3H); m / z 51292 1,1,3-trimethyl-3-[3-[2-(6-methyl-1H-indol-3-yl)-6-(methylsulfamoyl)benzimidazol-1-yl]phenyl]urea 1 H-NMR (500 MHz, Methanol-d4) δ 7.88 (d, J = 8.2 Hz, 1H), 7.81-7.78 (m, 2H), 7.67-7.63 (m, 2H), 7.37 (d, J = 7.9 Hz, 1H), 7.28 (dd, J = 8.2, 1.8 Hz, 1H), 7.21 (s, 1H), 7.12 (s, 1H), 7.03 (t, J = 1.8 Hz, 1H), 6.94 (d, J = 8.2 Hz, 1H), 3.08 (s, 3H), 2.54 (s, 6H), 2.50 (s, 3H), 2.41 (s, 3H); m / z 51793 N-methyl-5-[2-(6-methyl-1H-indol-3-yl)-6-(methylsulfamoyl)benzimidazol-1-yl]-1H-indole-3-carboxamide 1 H-NMR (500 MHz, Methanol-d4) δ 8.29 (d, J = 1.8 Hz, 1H), 8.22 (d, J = 8.2 Hz, 1H), 8.05 (s, 1H), 7.90 (d, J = 8.2 Hz, 1H), 7.77 (dd, J = 8.5, 1.5 Hz, 1H), 7.70 (d, J = 8.5 Hz, 1H), 7.55 (d, J = 1.2 Hz, 1H), 7.24 (dd, J = 8.5, 2.1 Hz, 1H), 7.17 (s, 1H), 7.04 (d, J = 8.2 Hz, 1H), 6.70 (s, 1H), 2.87 (s, 3H), 2.49 (s, 3H), 2.44 (s, 3H); m / z 51394 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(2-pyridyl)benzimidazole-5-sulfonamide 1H-NMR (500 MHz, DMSO-d6) δ 8.38 (d, J = 4.9 Hz, 1H), 8.21 (d, J = 7.9 Hz, 1H), 8.03 (d, J = 8.2 Hz, 1H), 7.96 (td, J = 7.7, 1.6 Hz, 1H), 7.74 (dd, J = 8.5, 1.5 Hz, 1H), 7.55 (d, J = 1.5 Hz, 1H), 7.42-7.39 (m, 3H), 7.29 (d, J = 8.2 Hz, 1H), 7.13 (dd, J = 8.2, 1.8 Hz, 1H), 3.40 (s, 3H), 3.29 (s, 3H), 2.37 (d, J = 2.7 Hz, 3H); m / z 44995 3-(1,4-dimethyl-2,3-dioxo-quinoxalin-5-yl)-N-methyl-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-sulfonamide 1 H-NMR (500 MHz, Methanol-d4) δ 8.11 (d, J = 8.2 Hz, 1H), 7.91 (d, J = 8.2 Hz, 1H), 7.78-7.71 (m, 3H), 7.66 (dd, J = 7.3, 1.5 Hz, 1H), 7.45 (d, J) = 1.5 Hz, 1H), 7.17 (s, 1H), 7.02 (d, J = 8.2 Hz, 1H), 6.81 (s, 1H), 3.77 (s, 3H), 3.40 (s, 3H), 2.46 (s, 3H), 2.43 (s, 3H); m / z ND96 N-[3-[2-(6-methyl-1H-indol-3-yl)-6-(methylsulfamoyl)benzimidazol-1-yl]-5-tetrahydropyran-4-yl-phenyl]acetamide 1 H-NMR (500 MHz, Chloroform-d) δ 8.58 (s, 1H), 8.35 (d, J = 8.2 Hz, 1H), 8.32 (s, 1H), 7.87 (d, J = 8.5 Hz, 1H), 7.77-7.71 (2H), 7.57 (s, 1H), 7.16 (s, 1H), 7.10 (d, J = 8.5 Hz, 1H), 7.07-7.02 (1H), 6.81 (s, 1H), 6.37 (d, J = 2.4 Hz, 1H), 4.63-4.54 (1H), 4.04-3.90 (m, 2H), 3.42 (td, J = 11.4, 2.7 Hz, 2H), 2.77-2.64 (m, 1H), 2.65-2.61 (3H), 2.44 (s, 3H), 2.28 (s, 3H), 1.69-1.61 (m, 4H); m / z 55897 3-[3-(3,5-dimethylisoxazol-4-yl)phenyl]-N-methyl-2-(3-methylimidazol-4-yl)benzimidazole-5-sulfonamide 1H-NMR (500 MHz, Chloroform-d) δ 7.93 (d, J = 8.5 Hz, 1H), 7.80 (dd, J = 8.5, 1.5 Hz, 1H), 7.76-7.71 (m, 2H), 7.60 (s, 1H), 7.53 (d, J = 7.9 Hz, 1H), 7.42 (d, J = 7.9 Hz, 1H), 7.22 (s, 1H), 6.57 (s, 1H) 4.37 (q, J = 5.3 Hz, 1H), 4.20 (d, J = 12.2 Hz, 3H), 2.66 (d, J = 5.5 Hz, 3H), 2.41 (s, 3H), 2.26 (s, 3H); m / z 46398 N-[3-[2-(6-methyl-1H-indol-3-yl)-6-(methylsulfamoyl)benzimidazol-1-yl]phenyl]acetamide 1 H-NMR (500 MHz, Methanol-d4) δ 8.08 (d, J = 8.2 Hz, 1H), 7.89 (d, J = 8.2 Hz, 1H), 7.81-7.77 (m, 3H), 7.62 (s, 1H), 7.59 (t, J = 7.9 Hz, 1H), 7.22-7.21 (m, 2H), 7.02 (d, J = 8.2 Hz, 1H), 6.91 (s, 1H), 2.50 (s, 3H), 2.44 (s, 3H), 2.12 (s, 3H); m / z ND99 N-methyl-5-[2-(6-methyl-1H-indol-3-yl)-6-(methylsulfamoyl)benzimidazol-1-yl]-7-tetrahydropyran-4-yl-1H-indole-3-carboxamide 1H-NMR (500 MHz, Methanol-d4) δ 8.22 (d, J = 1.8 Hz, 1H), 8.13 (d, J = 8.2 Hz, 1H), 8.07 (s, 1H), 7.92 (d, J = 8.5 Hz, 1H), 7.79 (dd, J = 8.5, 1.5 Hz, 1H), 7.63 (d, J = 1.2 Hz, 1H), 7.19 (s, 1H), 7.10 (s, 1H), 7.02 (d, J = 8.2 Hz, 1H), 6.75 (s, 1H), 4.02 (d, J = 10.7 Hz, 2H), 3.65 (td, J = 11.7, 2.2 Hz, 2H), 3.36 (m, 1H), 2.90 (s, 3H), 2.52 (s, 3H), 2.45 (s, 3H), 1.81 (s, 4H); m / z ND100 3-(3-hydroxy-5-tetrahydropyran-4-yl-phenyl)-N-methyl-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-sulfonamide 1 H-NMR (Chloroform-d) δ 8.41 (s, 1H), 8.32 (d, J = 8.2 Hz, 1H), 7.92 (d, J = 8.5 Hz, 1H), 7.74 (d, J = 10.1 Hz, 1H), 7.48 (s, 1H), 7.09 (d, J = 8.2 Hz, 1H), 7.03 (s, 1H), 6.85 (s, 1H), 6.57 (s, 1H), 6.43 (s, 1H), 6.23-6.15 (1H), 4.44 (q, J = 5.3 Hz, 1H), 3.98 (d, J = 10.7 Hz, 2H), 3.42 (td, J = 11.1, 3.3 Hz, 2H), 2.62 (d, J = 5.5 Hz, 4H), 2.39 (s, 3H), 1.69-1.60 (m, 4H); m / z ND101 1-(3-(3,5-dimethylisoxazol-4-yl)-5-(tetrahydro-2H-pyran-4-yl)phenyl)-N-methyl-2-(6-methyl-1H-indol-3-yl)-1H-benzo[d]imidazole-6-sulfonamide[1-(3-(3,5-dimethylisoxazol-4-yl)-5-(tetrahydro-2H-pyran-4-yl)phenyl)-N-methyl-2-(6-methyl-1H-indol-3-yl)-1H-benzo[d]imidazole-6-sulfonamide]ND; m / z 596102 methyl 3-(3-acetamido-5-tetrahydropyran-4-yl-phenyl)-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-carboxylate 1 H-NMR (500 MHz, Chloroform-d) δ 8.96 (s, 1H), 8.88 (s, 1H), 8.23 ​​(d, J = 8.2 Hz, 1H), 7.98 (d, J = 8.2 Hz, 1H), 7.84 (s, 1H), 7.78 (d, J = 8.2 Hz, 1H), 7.63 (s, 1H), 7.01 (d, J = 7.9 Hz, 1H), 6.93 (s, 1H), 6.83 (s, 1H), 6.74 (s, 1H), 6.24 (s, 1H), 3.93 (d, J = 11.3 Hz, 2H), 3.88 (s, 3H), 3.44-3.29 (m, 2H), 2.72-2.58 (m, 1H), 2.37 (s, 3H), 2.30 (s, 3H), 1.62-1.52 (m, 4H); m / z 523103 3-(3-acetamido-5-tetrahydropyran-4-yl-phenyl)-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-carboxylic acid [3-(3-acetamido-5-tetrahydropyran-4-yl-phenyl)-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-carboxylic acid]ND; m / z 509104 N-methyl-2-(3-methylimidazol-4-yl)-3-(2-oxo-1,3-dihydrobenzimidazol-5-yl)benzimidazole-5-sulfonamide 1 H-NMR (500MHz, Methanol-d4) δ 7.93 (d, J = 8.5 Hz, 1H), 7.88 (s, 1H), 7.83-7.78 (1H), 7.63 (s, 1H), 7.28 (d, J = 7.9 Hz, 1H), 7.15 (d, J = 7.9 Hz, 2H), 6.62-6.55 (1H), 4.10 (s, 3H), 2.50-2.45 (3H); m / z ND105 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(1-methylimidazol-4-yl)benzimidazole-5-sulfonamide 1H-NMR (500 MHz, Chloroform-d) δ 7.85 (d, J = 8.2 Hz, 1H), 7.73 (d, J = 8.2 Hz, 1H), 7.63 (s, 1H), 7.43 (s, 1H), 7.17-7.09 (2H), 7.09-6.96 (2H), 4.99 (s, 1H), 3.66 (s, 3H), 3.51 (s, 3H), 3.41 (s, 3H), 2.61 (s, 3H); m / z 452106 1',3'-dimethyl-2-phenyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one 1 H-NMR (500 MHz, Chloroform-d) δ 7.90 (d, J = 8.0 Hz, 1H), 7.61 (d, J = 7.0 Hz, 2H), 7.37 - 7.32 (m, 2H), 7.31 (dd, J = 6.2, 1.4 Hz, 2H), 7.28 (dd, J = 8.3, 1.1 Hz, 1H), 7.20 (d, J = 8.1 Hz, 1H), 7.05 (s, 2H), 6.93 (s, 1H), 3.49 (s, 3H), 3.37 (s, 3H); m / z ND107 2-(3-Bromophenyl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one 1H-NMR (500 MHz, Chloroform-d) δ 7.96 (s, 1H), 7.90 (d, J = 8.0 Hz, 1H), 7.48 (d, J = 8.0 Hz, 1H), 7.37 (d, J = 6.3 Hz, 2H), 7.29 (t, J = 7.6 Hz, 1H), 7.20 (d, J = 8.0 Hz, 1H), 7.12 (t, J = 7.9 Hz, 1H), 7.10 - 7.03 (m, 2H), 6.93 (d, J = 1.4 Hz, 1H), 3.51 (s, 3H), 3.40 (s, 3H); m / z ND108 2-(4-Bromophenyl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one 1 H-NMR (500 MHz, Chloroform-d) δ 7.88 (d, J = 7.9 Hz, 1H), 7.45 (dd, J = 23.3, 8.4 Hz, 4H), 7.34 (t, J = 7.5 Hz, 1H), 7.27 (dd, J = 8.3, 4.0 Hz, 1H), 7.18 (d, J = 8.0 Hz, 1H), 7.04 (dd, J = 18.1, 8.1 Hz, 2H), 6.93 (s, 1H), 3.50 (s, 3H), 3.39 (s, 3H); m / z ND109 2-(1H-Imidazol-5-yl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one[2-(1H-Imidazol-5-yl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one] 1H-NMR (500 MHz, Chloroform-d) δ 7.76 (d, J = 8.0 Hz, 1H), 7.72 (s, 1H), 7.34 (t, J = 7.1 Hz, 1H), 7.28 (d, J = 7.1 Hz, 1H), 7.24 - 7.17 (m, 2H), 7.12 (d, J = 8.0 Hz, 1H), 7.05 (d, J = 1.7 Hz, 1H), 6.54 (s, 1H), 3.55 (s, 3H), 3.44 (s, 3H); m / z ND110 2-(1H-Indol-3-yl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one[2-(1H-Indol-3-yl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one] 1 H-NMR (500 MHz, Chloroform-d) δ 8.62 (s, 1H), 8.56 (s, 1H), 7.90 (d, J = 8.0 Hz, 1H), 7.31 (dd, J = 12.1, 4.2 Hz, 2H), 7.25 - 7.20 (m, 3H), 7.17 (dd, J = 8.1, 1.8 Hz, 1H), 7.12 - 7.06 (m, 2H), 6.98 (d, J = 1.7 Hz, 1H), 6.60 (d, J = 2.4 Hz, 1H), 3.51 (s, 3H), 3.36 (s, 3H); m / z ND111 1',3'-Dimethyl-2-(6-methyl-1H-indol-3-yl)-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one[1',3'-Dimethyl-2-(6-methyl-1H-indol-3-yl)-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one] 1H-NMR (500 MHz, Chloroform-d) δ 8.42 (d, J = 7.8 Hz, 1H), 8.35 (s, 1H), 7.89 (d, J = 8.0 Hz, 1H), 7.30 (t, J = 7.6 Hz, 1H), 7.21 (t, J = 7.5 Hz, 1H), 7.17 (dd, J = 8.1, 1.6 Hz, 1H), 7.08 (dd, J = 12.1, 8.1 Hz, 4H), 6.98 (s, 1H), 6.55 (s, 1H), 3.51 (s, 3H), 3.36 (s, 3H), 2.45 (s, 3H); m / z ND112 2-(1H-Indol-2-yl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one[2-(1H-Indol-2-yl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one] 1 H-NMR (500 MHz, Chloroform-d) δ 10.40 (s, 1H), 7.81 (d, J = 8.0 Hz, 1H), 7.43 (d, J = 8.0 Hz, 1H), 7.38 - 7.30 (m, 2H), 7.28 - 7.24 (m, 2H), 7.23 - 7.16 (m, 2H), 7.12 - 7.07 (m, J = 4.8, 3.0 Hz, 2H), 7.04 (t, J = 7.1 Hz, 1H), 5.89 (d, J = 1.3 Hz, 1H), 3.59 (s, 3H), 3.44 (s, 3H); m / z ND113 2-(1,6-Dimethyl-1H-indol-3-yl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one[2-(1,6-Dimethyl-1H-indol-3-yl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one] 1H-NMR (500 MHz, Chloroform-d) δ 8.43 (d, J = 8.2 Hz, 1H), 7.88 (d, J = 8.0 Hz, 1H), 7.31 - 7.27 (m, 1H), 7.21 - 7.16 (m, 2H), 7.10 (dd, J = 15.5, 7.7 Hz, 3H), 7.04 (d, J = 7.9 Hz, 1H), 7.00 (d, J = 1.8 Hz, 1H), 6.44 (s, 1H), 3.59 (s, 3H), 3.52 (s, 3H), 3.38 (s, 3H), 2.50 (s, 3H); m / z ND114 1',3'-Dimethyl-2-(1-methyl-1H-imidazol-5-yl)-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one[1',3'-Dimethyl-2-(1-methyl-1H-imidazol-5-yl)-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one] 1 H-NMR (500 MHz, Chloroform-d) δ 7.83 (dt, 1H), 7.51 (s, 1H), 7.33 (ddd, J = 8.1, 7.2, 1.2 Hz, 1H), 7.27 - 7.23 (m, 1H), 7.13 - 7.07 (m, 3H), 6.94 (dd, J = 1.5, 0.6 Hz, 1H), 6.46 (s, 1H), 4.16 (s, 3H), 3.52 (s, 3H), 3.40 (s, 3H); m / z ND115 2-(1H-Imidazol-5-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 7.82 (d, J = 8.5 Hz, 1H), 7.77 (ddd, J = 7.4, 4.1, 0.8 Hz, 1H), 7.73 (dd, J = 8.5, 1.7 Hz, 1H), 7.64 - 7.58 (m, 1H), 7.54 (dd, J = 1.7, 0.6 Hz, 1H), 7.41 - 7.38 (m, 1H), 7.35 (s, 1H), 7.25 (s, 1H), 6.28 (dd, J = 10.1, 5.2 Hz, 1H), 3.51 (s, 3H), 3.41 (s, 3H), 2.52 (d, J = 5.2 Hz, 3H); m / z ND116 2-(1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, Acetone-d6) δ 10.35 (s, 1H), 7.75 (d, J = 8.4 Hz, 1H), 7.68 (dd, J = 8.4, 1.7 Hz, 1H), 7.44 (d, J = 1.6 Hz, 1H), 7.38 (d, J = 8.1 Hz, 1H), 7.32 (d, J = 1.9 Hz, 1H), 7.23 (dd, J = 8.1, 2.0 Hz, 1H), 6.80 (dt, J = 3.1, 1.7 Hz, 1H), 6.77 (dd, J = 4.6, 2.6 Hz, 1H), 6.36 (dd, J = 4.2, 2.7 Hz, 1H), 6.17 (q, J = 5.3 Hz, 1H), 3.51 (s, 3H), 3.42 (s, 3H), 2.51 (d, J = 5.2 Hz, 3H); m / z ND117 2-(1,6-Dimethyl-1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, DMSO-d6) δ 8.53 (d, J = 8.3 Hz, 1H), 7.94 (d, J = 8.1 Hz, 2H), 7.60 (dd, J = 8.4, 1.8 Hz, 1H), 7.51 (d, J = 2.0 Hz, 1H), 7.45 (d, J = 8.2 Hz, 1H), 7.27 (dd, J = 12.8, 4.6 Hz, 2H), 7.22 (s, 1H), 7.11 (d, J = 6.9 Hz, 1H), 6.59 (s, 1H), 3.62 (s, 3H), 3.46 (s, 3H), 2.89 (s, 3H), 2.73 (s, 3H), 2.56 (s, 3H); m / z ND118 2-(1H-indol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 7.96 (d, J = 8.5 Hz, 1H), 7.72 (dd, J = 8.0, 1.7 Hz, 1H), 7.59 (s, 1H), 7.49 (dd, J = 13.3, 8.2 Hz, 2H), 7.43 - 7.39 (m, 3H), 7.37 (dd, J = 8.3, 1.9 Hz, 1H), 7.16 (t, 1H), 6.95 (t, J = 7.4 Hz, 1H), 5.87 (s, 1H), 3.49 (s, 3H), 2.89 (s, 3H), 2.73 (s, 3H); m / z ND119 5-(6-Chloro-8-(1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-Chloro-8-(1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (500 MHz, Acetone-d6) δ 10.93 (s, 1H), 8.84 (dd, J = 7.7, 1.5 Hz, 1H), 8.16 (s, 1H), 7.63 (d, J = 2.9 Hz, 1H), 7.50 (d, J = 23.2 Hz, 2H), 7.27 - 7.24 (m, 2H), 7.21 (s, 1H), 6.93 (s, 1H), 3.38 (s, 3H), 3.33 (s, 3H); m / z ND120 5-(6-Chloro-8-(1H-indol-2-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-Chloro-8-(1H-indol-2-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1H-NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 7.95 (s, 1H), 7.72 (dd, J = 8.0, 1.7 Hz, 1H), 7.59 (d, J = 1.9 Hz, 1H), 7.50 (d, J = 8.1 Hz, 1H), 7.47 (d, J = 8.3 Hz, 1H), 7.37 (dd, J = 7.9, 2.3 Hz, 1H), 7.18 - 7.14 (m, 1H), 6.95 (t, J = 7.0 Hz, 1H), 5.87 (s, 1H), 2.89 (s, 3H), 2.73 (s, 3H); m / z ND121 5-(6-Chloro-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-Chloro-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (500 MHz, Methanol-d4) δ 8.53 (s, 1H), 8.40 (d, J = 8.4 Hz, 1H), 7.41 (dd, J = 5.1, 3.1 Hz, 2H), 7.28 (dd, J = 8.3, 1.9 Hz, 1H), 7.21 (s, 1H), 7.10 (d, J = 8.1 Hz, 1H), 6.71 (s, 1H), 3.54 (s, 3H), 3.42 (s, 3H), 2.46 (s, 3H); m / z ND122 5-(6-Chloro-8-(1H-imidazol-5-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-Chloro-8-(1H-imidazol-5-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1H-NMR (500 MHz, Acetone-d6) δ 8.57 (s, 1H), 7.77 (s, 1H), 7.42 - 7.21 (m, 4H), 3.50 (s, 3H), 3.40 (s, 3H); m / z ND123 N,1',3'-Trimethyl-2-(3-(1-methyl-1H-pyrazol-4-yl)phenyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, Acetone-d6) δ 7.94 (dd, J = 8.5, 0.5 Hz, 1H), 7.91 (t, J = 1.6 Hz, 1H), 7.85 (s, 1H), 7.79 (dd, J = 8.5, 1.7 Hz, 1H), 7.67 (d, J = 1.2 Hz, 1H), 7.62 - 7.58 (m, 2H), 7.49 (ddd, J = 7.8, 1.7, 1.1 Hz, 1H), 7.38 (d, J = 1.9 Hz, 1H), 7.35 (d, J = 8.1 Hz, 1H), 7.32 (t, J = 8.0 Hz, 1H), 7.26 (dd, J = 8.1, 2.0 Hz, 1H), 6.26 (dd, J = 10.4, 5.2 Hz, 1H), 3.88 (s, 3H), 3.49 (s, 3H), 3.38 (s, 3H), 2.54 (d, J = 5.2 Hz, 3H); m / z ND124 N,1',3'-Trimethyl-2-(4-(1-methyl-1H-pyrazol-4-yl)phenyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, Acetone-d6) δ 8.03 (s, 1H), 7.91 (d, J = 8.4 Hz, 1H), 7.83 (s, 1H), 7.77 (dd, J = 8.5, 1.7 Hz, 1H), 7.69 (d, J = 8.5 Hz, 2H), 7.63 (d, J = 1.6 Hz, 1H), 7.55 (d, J = 8.6 Hz, 2H), 7.37 (d, J = 2.1 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.23 (dd, J = 8.2, 2.0 Hz, 1H), 6.27 (s, 1H), 3.90 (s, 3H), 3.49 (s, 3H), 3.38 (s, 3H), 2.53 (d, J = 5.2 Hz, 3H); m / z ND125 2-(1-(Cyclopropylmethyl)-6-methyl-1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 8.69 (d, J = 8.2 Hz, 1H), 7.87 (d, J = 8.4 Hz, 1H), 7.73 (dd, J = 8.4, 1.8 Hz, 1H), 7.51 (d, J = 1.4 Hz, 1H), 7.45 (d, J = 8.1 Hz, 1H), 7.38 (d, J = 1.9 Hz, 1H), 7.33 - 7.29 (m, 2H), 7.12 (d, J = 8.2 Hz, 1H), 6.72 (s, 1H), 6.20 (q, J = 5.2 Hz, 1H), 3.84 (d, J = 7.0 Hz, 2H), 3.53 (s, 3H), 3.42 (s, 3H), 2.53 (d, J = 5.2 Hz, 3H), 2.48 (s, 3H), 1.07 - 1.01 (m, 1H), 0.35 (dd, J = 8.0, 1.3 Hz, 2H), 0.12 (d, J = 5.2 Hz, 2H); m / z ND126 N,1',3'-Trimethyl-2-(6-methyl-1-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 8.69 (d, J = 8.2 Hz, 1H), 7.88 (d, J = 8.4 Hz, 1H), 7.73 (dd, J = 8.4, 1.7 Hz, 1H), 7.48 (s, 1H), 7.42 (d, J = 8.1 Hz, 1H), 7.38 (d, J = 1.8 Hz, 1H), 7.29 (dd, J = 8.1, 2.0 Hz, 1H), 7.25 (s, 1H), 7.10 (d, J = 8.4 Hz, 1H), 6.71 (d, J = 2.7 Hz, 1H), 6.19 (d, J = 5.2 Hz, 1H), 4.03 (s, 3H), 3.52 (s, 3H), 3.41 (s, 3H), 3.30 (s, 6H), 3.09 (q, J = 5.4 Hz, 2H), 2.53 (d, J = 5.3 Hz, 4H), 2.44 (s, 3H); m / z ND127 N,1',3'-Trimethyl-2-(6-methyl-1-(2-morpholinoethyl)-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 8.70 (d, J = 8.2 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.72 (dd, J = 8.4, 1.8 Hz, 1H), 7.48 (d, J = 1.4 Hz, 1H), 7.44 (d, J = 8.1 Hz, 1H), 7.39 (d, J = 1.9 Hz, 1H), 7.34 - 7.27 (m, 2H), 7.11 (dd, J = 8.2, 0.9 Hz, 1H), 6.78 (s, 1H), 6.18 (dd, J = 10.4, 5.2 Hz, 1H), 4.10 (t, J = 6.0 Hz, 2H), 3.51 (s, 3H), 3.43 - 3.38 (m, 7H), 2.59 - 2.51 (m, 5H), 2.47 (s, 3H), 2.29 - 2.21 (m, 4H); m / z ND128 2-(Benzofuran-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 9.00 (d, J = 8.3 Hz, 1H), 8.03 - 7.98 (m, 2H), 7.82 (dd, J = 8.5, 1.7 Hz, 1H), 7.66 (d, J = 1.3 Hz, 1H), 7.55 (ddd, J = 8.3, 7.1, 1.2 Hz, 1H), 7.49 (dd, J = 8.0, 1.2 Hz, 1H), 7.46 (s, 1H), 7.44 (d, J = 1.9 Hz, 1H), 7.33 (d, J = 8.1 Hz, 1H), 7.27 (dd, J = 8.2, 2.0 Hz, 1H), 6.31 (q, J = 5.2 Hz, 1H), 3.47 (s, 3H), 3.37 (s, 3H), 2.55 (d, J = 5.2 Hz, 3H); m / z ND129 2-(Benzo[b]thiophen-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, Acetone-d6) δ 8.71 (dd, J = 6.3, 2.9 Hz, 1H), 8.00 (d, J = 8.5 Hz, 1H), 7.80 (dd, J = 8.5, 1.7 Hz, 1H), 7.60 (d, J = 1.2 Hz, 1H), 7.57 (dd, J = 6.2, 3.0 Hz, 1H), 7.49 - 7.41 (m, 4H), 7.35 (dd, J = 8.1, 2.0 Hz, 1H), 7.21 (s, 1H), 6.28 (d, J = 5.1 Hz, 1H), 3.53 (s, 3H), 3.42 (s, 3H), 2.55 (d, J = 5.2 Hz, 3H); m / z ND130 N,1',3'-Trimethyl-2-(2-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, Methanol-d4) δ 7.89 (dd, J = 8.8, 2.8 Hz, 2H), 7.80 (d, J = 8.5 Hz, 1H), 7.28 (dd, J = 20.0, 6.0 Hz, 2H), 7.18 (s, 1H), 7.11 (d, J = 1.8 Hz, 2H), 7.01 (td, J = 7.8, 2.2 Hz, 1H), 6.87 (td, J = 7.6, 2.4 Hz, 1H), 3.36 (s, 3H), 3.24 (s, 3H), 2.50 (s, 3H), 2.31 (s, 3H); m / z ND131 2-(4-Fluoro-1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 10.88 (s, 1H), 7.88 (d, J = 8.6 Hz, 1H), 7.76 (dd, J = 8.6, 1.7 Hz, 1H), 7.67 (d, J = 1.6 Hz, 1H), 7.41 (d, J = 2.3 Hz, 1H), 7.30 (d, J = 1.5 Hz, 1H), 7.28 (d, J = 8.0 Hz, 1H), 7.21 (d, J = 8.1 Hz, 1H), 7.19 (dd, J = 8.1, 1.7 Hz, 1H), 7.14 (td, J = 7.9, 4.9 Hz, 1H), 6.79 (dd, J = 11.3, 7.8 Hz, 1H), 6.24 (d, J = 5.3 Hz, 1H), 3.41 (s, 3H), 3.32 (s, 3H), 2.54 (d, J = 5.2 Hz, 3H) ; m / z ND132 2-(5-Fluoro-1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 10.62 (s, 1H), 8.56 (dd, J = 10.4, 2.6 Hz, 1H), 7.91 (d, J = 8.4 Hz, 1H), 7.75 (dd, J = 8.4, 1.7 Hz, 1H), 7.50 (d, J = 1.7 Hz, 1H), 7.48 (dd, J = 8.8, 4.6 Hz, 1H), 7.43 (d, J = 8.1 Hz, 1H), 7.42 (d, J = 1.9 Hz, 1H), 7.32 (dd, J = 8.1, 2.0 Hz, 1H), 7.05 (td, J = 9.0, 2.7 Hz, 1H), 6.85 (d, J = 3.0 Hz, 1H), 6.22 (q, J = 4.9 Hz, 1H), 3.52 (s, 3H), 3.42 (s, 3H), 2.53 (d, J = 5.3 Hz, 3H) ; m / z ND133 2-(6-Fluoro-1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 10.57 (s, 1H), 8.83 (dd, J = 8.9, 5.6 Hz, 1H), 7.90 (d, J = 8.4 Hz, 1H), 7.74 (d, J = 8.4 Hz, 1H), 7.49 (s, 1H), 7.43 (d, J = 8.2 Hz, 1H), 7.41 (s, 1H), 7.32 - 7.29 (m, 1H), 7.22 - 7.18 (m, 1H), 7.08 (t, J = 9.1 Hz, 1H), 6.80 (s, 1H), 6.21 (d, J = 4.8 Hz, 1H), 3.52 (s, 3H), 3.41 (s, 3H), 2.53 (d, J = 6.1 Hz, 3H) ; m / z ND134 2-(5,6-Difluoro-1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, Acetone-d6) δ 10.68 (s, 1H), 8.72 (dd, J = 11.8, 8.4 Hz, 1H), 7.92 (d, J = 8.4 Hz, 1H), 7.75 (dd, J = 8.4, 1.7 Hz, 1H), 7.50 (d, J = 1.4 Hz, 1H), 7.42 (td, J = 8.7, 4.3 Hz, 3H), 7.32 (dd, J = 8.1, 1.9 Hz, 1H), 6.84 (d, J = 2.4 Hz, 1H), 6.23 (d, J = 5.1 Hz, 1H), 3.52 (s, 3H), 3.41 (s, 3H), 2.53 (d, J = 5.2 Hz, 3H) ; m / z ND135 N,1',3'-Trimethyl-2'-oxo-2-(4,5,6,7-tetrafluoro-1H-indol-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, Chloroform-d) δ 8.89 (s, 1H), 7.98 (d, J = 8.5 Hz, 1H), 7.81 (dd, J = 8.5, 1.7 Hz, 1H), 7.76 (d, J = 1.6 Hz, 1H), 7.18 (d, J = 2.4 Hz, 1H), 7.08 (dd, J = 8.2, 1.8 Hz, 1H), 7.03 (d, J = 8.2 Hz, 1H), 6.92 (d, J = 1.7 Hz, 1H), 4.34 (q, J = 5.4 Hz, 1H), 3.47 (s, 3H), 3.37 (s, 3H), 2.66 (d, J = 5.4 Hz, 3H) ; m / z ND136 5-(6-(Dimethylamino)-8-(1-methyl-1H-imidazol-5-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-(Dimethylamino)-8-(1-methyl-1H-imidazol-5-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1H-NMR (500 MHz, Methanol-d4) δ 8.14 (s, 1H), 7.75 (s, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.30 (d, J = 1.9 Hz, 1H), 7.15 (dd, J = 8.2, 1.9 Hz, 1H), 6.36 (d, J = 0.9 Hz, 1H), 4.10 (s, 3H), 3.60 (s, 6H), 3.51 (s, 3H), 3.42 (s, 3H) ; m / z ND137 5-(6-(Dimethylamino)-8-(4-fluoro-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-(Dimethylamino)-8-(4-fluoro-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (500 MHz, Chloroform-d) δ 8.51 (s, 1H), 8.34 (s, 1H), 7.14 - 7.11 (m, 2H), 7.07 - 7.05 (m, 1H), 7.05 (d, J = 2.8 Hz, 1H), 7.02 (d, J = 1.7 Hz, 1H), 6.93 (d, J = 8.2 Hz, 1H), 6.81 (ddd, J = 10.9, 6.2, 2.3 Hz, 1H), 3.63 (s, 6H), 3.39 (s, 3H), 3.33 (s, 3H) ; m / z ND138 5-(6-(Dimethylamino)-8-(5-fluoro-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-(Dimethylamino)-8-(5-fluoro-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1H-NMR (500 MHz, Acetone-d6) δ 10.49 (s, 1H), 8.35 (dd, J = 10.4, 2.7 Hz, 1H), 8.12 (s, 1H), 7.45 (dd, J = 8.8, 4.5 Hz, 1H), 7.32 (d, J = 8.1 Hz, 1H), 7.28 (d, J = 1.9 Hz, 1H), 7.18 (dd, J = 8.1, 1.9 Hz, 1H), 7.03 (td, J = 9.1, 2.6 Hz, 1H), 6.74 - 6.73 (m, 1H), 3.65 (dd, J = 69.5, 42.5 Hz, 6H), 3.49 (s, 3H), 3.40 (s, 3H) ; m / z ND139 5-(6-(Dimethylamino)-8-(6-fluoro-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(6-(Dimethylamino)-8-(6-fluoro-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (500 MHz, Methanol-d4) δ 8.50 (dd, J = 8.9, 5.5 Hz, 1H), 8.10 (s, 1H), 7.38 (d, J = 8.2 Hz, 1H), 7.33 (d, J = 1.9 Hz, 1H), 7.20 (dd, J = 8.2, 2.0 Hz, 1H), 7.08 (dd, J = 9.5, 2.3 Hz, 1H), 7.00 - 6.95 (m, 1H), 6.54 (s, 1H), 3.69 (s, 6H), 3.53 (s, 3H), 3.43 (s, 3H) ; m / z ND140 5-(8-(5,6-Difluoro-1H-indol-3-yl)-6-(dimethylamino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one[5-(8-(5,6-Difluoro-1H-indol-3-yl)-6-(dimethylamino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one] 1 H-NMR (500 MHz, Methanol-d4) δ 8.35 (dd, J = 11.6, 8.2 Hz, 1H), 8.11 (s, 1H), 7.39 (d, J = 8.2 Hz, 1H), 7.34 (d, J = 1.8 Hz, 1H), 7.26 (dd, J = 10.7, 6.9 Hz, 1H), 7.21 (dd, J = 8.2, 2.0 Hz, 1H), 6.56 (s, 1H), 3.69 (s, 6H), 3.54 (s, 3H), 3.43 (s, 3H) ; m / z ND141 1',3'-Diethyl-2-(4-fluoro-1H-indol-3-yl)-N-methyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 10.57 (s, 1H), 8.81 (dd, J = 8.9, 5.7 Hz, 1H), 7.89 (dd, J = 8.4, 0.4 Hz, 1H), 7.75 (dd, J = 8.4, 1.8 Hz, 1H), 7.53 (dd, 1H), 7.48 (dd, J = 7.7, 5.0 Hz, 2H), 7.30 (dd, J = 8.1, 2.0 Hz, 1H), 7.21 (dd, J = 9.6, 2.3 Hz, 1H), 7.07 (ddd, J = 9.7, 8.9, 2.4 Hz, 1H), 6.83 (d, J = 2.9 Hz, 1H), 6.20 (q, J = 5.2 Hz, 1H), 4.06 (dd, J = 14.2, 7.1 Hz, 2H), 3.96 (q, J = 7.2 Hz, 2H), 2.54 (d, J = 5.2 Hz, 3H), 1.39 (t, J = 7.2 Hz, 3H), 1.24 (t, J = 7.2 Hz, 3H) ; m / z ND142 1',3'-Dicyclopropyl-2-(4-fluoro-1H-indol-3-yl)-N-methyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 10.57 (s, 1H), 8.81 (dd, J = 8.9, 5.7 Hz, 1H), 7.90 (d, J = 8.4 Hz, 1H), 7.75 (dd, J = 8.4, 1.7 Hz, 1H), 7.53 (d, J = 1.6 Hz, 1H), 7.49 (d, J = 8.1 Hz, 1H), 7.46 (d, J = 2.0 Hz, 1H), 7.30 (dd, J = 8.1, 2.0 Hz, 1H), 7.20 (dd, J = 9.6, 2.4 Hz, 1H), 7.07 (td, 1H), 6.86 (d, J = 2.9 Hz, 1H), 6.21 (q, J = 5.1 Hz, 1H), 2.97 (tt, J = 6.9, 3.6 Hz, 1H), 2.85 (td, J = 6.8, 3.5 Hz, 1H), 2.55 (d, J = 5.2 Hz, 3H), 1.17 - 1.10 (m, 2H), 1.06 - 1.01 (m, 2H), 0.97 (d, J = 6.8 Hz, 2H), 0.91 (d, J = 3.4 Hz, 2H) ; m / z ND143 1',3'-Dimethyl-2-(6-methyl-1H-indol-3-yl)-N-(2-morpholinoethyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 10.39 (s, 1H), 8.69 (d, J = 8.2 Hz, 1H), 7.87 (d, J = 8.4 Hz, 1H), 7.76 (dd, J = 8.4, 1.8 Hz, 1H), 7.52 (d, J = 1.5 Hz, 1H), 7.42 (d, J = 8.1 Hz, 1H), 7.38 (d, J = 1.9 Hz, 1H), 7.29 (dd, J = 8.1, 2.0 Hz, 1H), 7.25 (s, 1H), 7.10 (dd, J = 8.3, 1.1 Hz, 1H), 6.71 (d, J = 2.9 Hz, 1H), 6.12 (s, 1H), 3.52 (s, 3H), 3.50 (t, 4H), 3.42 (s, 3H), 2.98 (dd, J = 11.8, 5.9 Hz, 2H), 2.44 (s, 3H), 2.35 (t, J = 6.1 Hz, 2H), 2.24 (s, 4H) ; m / z ND144 1',3'-Dimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 10.36 (s, 1H), 8.69 (d, J = 8.2 Hz, 1H), 7.84 (dd, J = 8.4, 0.5 Hz, 1H), 7.80 (dd, J = 8.4, 1.7 Hz, 1H), 7.53 (d, J = 1.2 Hz, 1H), 7.42 (d, J = 8.1 Hz, 1H), 7.37 (d, J = 1.9 Hz, 1H), 7.28 (dd, J = 8.1, 2.0 Hz, 1H), 7.25 (s, 1H), 7.10 (d, J = 8.3 Hz, 1H), 6.69 (d, J = 2.9 Hz, 1H), 6.44 (s, 1H), 3.52 (s, 3H), 3.42 (s, 3H), 2.78 (s, 8H), 2.44 (s, 3H) ; m / z ND145 N-(Cyclopropylmethyl)-1',3'-dimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 10.36 (s, 1H), 8.68 (d, J = 8.2 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.75 (dd, J = 8.4, 1.8 Hz, 1H), 7.50 (d, J = 1.4 Hz, 1H), 7.42 (d, J = 8.1 Hz, 1H), 7.38 (d, J = 1.9 Hz, 1H), 7.29 (dd, J = 8.1, 2.0 Hz, 1H), 7.25 (s, 1H), 7.10 (d, J = 8.3 Hz, 1H), 6.71 (d, J = 2.9 Hz, 1H), 6.44 (t, J = 6.0 Hz, 1H), 3.52 (s, 3H), 3.42 (s, 3H), 2.75 (t, J = 6.5 Hz, 2H), 2.44 (s, 3H), 0.91 - 0.81 (m, 1H), 0.37 (ddd, J = 8.0, 5.9, 4.5 Hz, 2H), 0.09 (dt, J = 5.9, 4.5 Hz, 2H) ; m / z ND146 1',3'-Dimethyl-2-(6-methyl-1H-indol-3-yl)-6-(morpholinosulfonyl)-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one 1H-NMR (500 MHz, Acetone-d6) δ 10.40 (s, 1H), 8.69 (d, J = 8.2 Hz, 1H), 7.93 (d, J = 8.4 Hz, 1H), 7.65 (dd, J = 8.4, 1.7 Hz, 1H), 7.43 - 7.39 (m, 3H), 7.33 (dd, J = 8.1, 2.0 Hz, 1H), 7.25 (s, 1H), 7.11 (dd, J = 8.3, 1.2 Hz, 1H), 6.73 - 6.70 (m, 1H), 3.67 - 3.63 (m, 4H), 3.52 (s, J = 0.6 Hz, 3H), 3.41 (s, J = 0.4 Hz, 3H), 2.93 - 2.88 (m, 4H), 2.44 (s, 3H) ; m / z ND147 1',3'-Dimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, Acetone-d6) δ 10.35 (s, 1H), 8.69 (d, J = 7.9 Hz, 1H), 7.85 (d, J = 8.8 Hz, 1H), 7.82 - 7.78 (m, 1H), 7.53 (s, 1H), 7.42 (d, J = 8.2 Hz, 1H), 7.37 (d, J = 1.9 Hz, 1H), 7.28 (dd, J = 8.1, 2.0 Hz, 1H), 7.24 (s, 1H), 7.10 (d, J = 9.1 Hz, 1H), 6.69 (d, J = 2.9 Hz, 1H), 6.44 (s, 2H), 3.52 (s, 3H), 3.42 (s, 3H), 2.44 (s, 3H) ; m / z ND148 N-Ethyl-1',3'-dimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, Acetone-d6) δ 10.37 (s, 1H), 8.69 (d, J = 8.2 Hz, 1H), 7.87 (d, J = 8.4 Hz, 1H), 7.74 (dd, J = 8.4, 1.8 Hz, 1H), 7.49 (d, J = 1.4 Hz, 1H), 7.42 (d, J = 8.1 Hz, 1H), 7.38 (d, J = 1.9 Hz, 1H), 7.29 (dd, J = 8.1, 2.0 Hz, 1H), 7.25 (s, 1H), 7.10 (dd, J = 8.3, 1.1 Hz, 1H), 6.71 - 6.70 (m, 1H), 6.28 (t, J = 6.0 Hz, 1H), 3.52 (s, 3H), 3.47 (dd, J = 19.2, 7.3 Hz, 2H), 3.41 (s, 3H), 2.44 (s, 3H), 1.04 (t, J = 7.2 Hz, 3H) ; m / z ND149 N-Benzyl-1',3'-dimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 10.36 (s, 1H), 8.70 (d, J = 8.2 Hz, 1H), 7.87 (d, J = 8.4 Hz, 1H), 7.79 (dd, J = 8.4, 1.8 Hz, 1H), 7.51 - 7.50 (m, 1H), 7.42 (d, J = 8.1 Hz, 1H), 7.37 (d, J = 1.9 Hz, 1H), 7.28 (dd, J = 8.1, 2.0 Hz, 1H), 7.26 - 7.23 (m, 5H), 7.20 (dq, J = 5.9, 3.8 Hz, 1H), 7.11 (dd, J = 8.2, 1.0 Hz, 1H), 6.80 (t, J = 6.3 Hz, 1H), 6.73 - 6.69 (m, 1H), 4.08 (d, J = 6.6 Hz, 2H), 3.52 (s, 3H), 3.41 (s, 3H), 2.45 (s, 3H) ; m / z ND150 N-Isopropyl-1',3'-dimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 10.37 (s, 1H), 8.68 (d, J = 8.2 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.76 (dd, J = 8.4, 1.8 Hz, 1H), 7.51 (d, J = 1.5 Hz, 1H), 7.42 (d, J = 8.1 Hz, 1H), 7.38 (d, J = 1.9 Hz, 1H), 7.29 (dd, J = 8.1, 2.0 Hz, 1H), 7.25 (s, 1H), 7.10 (dd, J = 8.3, 1.1 Hz, 1H), 6.71 (d, J = 2.9 Hz, 1H), 6.26 (d, J = 7.3 Hz, 1H), 3.52 (s, 3H), 3.41 (s, 3H), 3.39 - 3.32 (m, 1H), 2.44 (s, 3H), 1.02 (d, J = 6.5 Hz, 6H) ; m / z ND151 2-(5-Fluoro-1H-indol-3-yl)-1',3'-dimethyl-N-(2-morpholinoethyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 10.93 (s, 1H), 7.88 (dd, J = 8.5, 0.5 Hz, 1H), 7.80 (dd, J = 8.5, 1.8 Hz, 1H), 7.70 (d, J = 1.6 Hz, 1H), 7.41 (d, J = 2.8 Hz, 1H), 7.29 (dd, J = 6.9, 5.0 Hz, 2H), 7.21 (d, J = 8.2 Hz, 1H), 7.18 (dd, J = 8.2, 1.8 Hz, 1H), 7.13 (td, J = 8.0, 4.9 Hz, 1H), 6.78 (ddd, J = 11.1, 7.8, 0.7 Hz, 1H), 6.20 (s, 1H), 3.51 - 3.46 (m, 4H), 3.41 (s, 3H), 3.32 (s, 3H), 2.99 (dd, J = 11.6, 6.0 Hz, 2H), 2.37 (t, J = 6.3 Hz, 2H), 2.24 (s, 4H) ; m / z ND152 2-(4-Fluoro-1H-indol-3-yl)-1',3'-dimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 10.89 (s, 1H), 7.84 (dd, J = 2.8, 1.1 Hz, 2H), 7.72 (s, 1H), 7.41 (d, J = 2.7 Hz, 1H), 7.28 (dd, J = 5.0, 3.1 Hz, 2H), 7.21 (d, J = 8.2 Hz, 1H), 7.17 (dd, J = 8.2, 1.9 Hz, 1H), 7.13 (td, J = 8.0, 4.8 Hz, 1H), 6.78 (dd, J = 11.1, 7.8 Hz, 1H), 6.48 (s, 2H), 3.41 (s, 3H), 3.32 (s, 3H) ; m / z ND153 N,1',3'-Trimethyl-2'-oxo-2-(1H-pyrrol-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, Acetone-d6) δ 10.35 (s, 1H), 7.75 (d, J = 8.4 Hz, 1H), 7.68 (dd, J = 8.4, 1.7 Hz, 1H), 7.44 (d, J = 1.6 Hz, 1H), 7.38 (d, J = 8.1 Hz, 1H), 7.32 (d, J = 1.9 Hz, 1H), 7.23 (dd, J = 8.1, 2.0 Hz, 1H), 6.80 (dt, J = 3.1, 1.7 Hz, 1H), 6.77 (dd, J = 4.6, 2.6 Hz, 1H), 6.36 (dd, J = 4.2, 2.7 Hz, 1H), 6.17 (q, J = 5.3 Hz, 1H), 3.51 (s, 3H), 3.42 (s, 3H), 2.51 (d, J = 5.2 Hz, 3H) ; m / z ND154 2-(1-Benzyl-1H-pyrrol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, Acetone-d6) δ 7.73 (d, J = 8.6 Hz, 1H), 7.67 (dd, J = 8.4, 1.8 Hz, 1H), 7.43 (d, J = 1.4 Hz, 1H), 7.30 (dd, J = 12.6, 7.1 Hz, 5H), 7.19 (dd, J = 11.2, 1.9 Hz, 2H), 7.16 - 7.14 (m, J = 8.4, 1.8 Hz, 2H), 6.81 - 6.79 (m, 1H), 6.56 (t, J = 2.0 Hz, 1H), 6.35 (dd, J = 2.9, 1.8 Hz, 1H), 5.04 (s, 2H), 3.51 (s, 3H), 3.36 (s, 3H), 2.50 (d, J = 5.2 Hz, 3H) ; m / z ND155 N,1',3'-trimethyl-2'-oxo-2-(1H-pyrrol-2-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 11.35 (s, 1H), 7.81 (d, J = 7.6 Hz, 1H), 7.75 (d, J = 7.9 Hz, 1H), 7.50 (s, 1H), 7.42 (d, J = 8.2 Hz, 1H), 7.39 (d, J = 1.8 Hz, 1H), 7.30 (dd, J = 8.2, 1.9 Hz, 1H), 7.10 (s, 1H), 6.24 (q, J = 4.8 Hz, 1H), 6.05 (s, 1H), 5.68 (s, 1H), 3.53 (s, 3H), 3.43 (s, 3H), 2.53 - 2.51 (m, 3H) ; m / z ND156 2-(1-(Cyclopropylmethyl)-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 7.85 (d, J = 8.4 Hz, 1H), 7.74 (dd, J = 8.5, 1.8 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.33 (d, J = 8.2 Hz, 1H), 7.29 (d, J = 1.9 Hz, 1H), 7.19 (dd, J = 8.2, 2.0 Hz, 1H), 7.09 - 7.06 (m, 1H), 6.25 - 6.20 (m, 1H), 5.93 (dd, J = 3.9, 2.6 Hz, 1H), 5.83 (dd, J = 3.9, 1.7 Hz, 1H), 4.53 (d, J = 7.1 Hz, 2H), 3.49 (s, 3H), 3.40 (s, 3H), 2.53 (d, J = 5.2 Hz, 3H), 1.45 - 1.36 (m, 1H), 0.53 - 0.48 (m, 2H), 0.40 - 0.36 (m, 2H) ; m / z ND157 2-(1-(Cyclopropylmethyl)-1H-pyrrol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 7.74 (d, J = 8.5 Hz, 1H), 7.68 (dd, J = 8.4, 1.8 Hz, 1H), 7.45 (s, 1H), 7.39 (d, J = 8.2 Hz, 1H), 7.32 (d, J = 2.0 Hz, 1H), 7.23 (dd, J = 8.1, 2.0 Hz, 1H), 6.87 (s, 1H), 6.76 - 6.70 (m, 1H), 6.22 - 6.18 (m, 1H), 6.18 - 6.14 (m, 1H), 3.71 (d, J = 7.1 Hz, 2H), 3.51 (s, 3H), 3.42 (s, 3H), 2.51 (d, J = 5.2 Hz, 3H), 1.11 - 1.08 (m, 1H), 0.48 (d, J = 7.8 Hz, 2H), 0.25 (d, J = 4.9 Hz, 2H) ; m / z ND158 N,1',3'-Trimethyl-2-(1-methyl-1H-pyrrol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, Acetone-d6) δ 7.73 (d, J = 8.4 Hz, 1H), 7.67 (d, J = 1.7 Hz, 1H), 7.43 (d, J = 1.7 Hz, 1H), 7.37 (d, J = 8.1 Hz, 1H), 7.31 (d, J = 1.9 Hz, 1H), 7.21 (dd, J = 8.1, 2.0 Hz, 1H), 6.80 (t, J = 1.9 Hz, 1H), 6.62 (t, 1H), 6.19 - 6.14 (m, 2H), 3.59 (s, 3H), 3.51 (s, 3H), 3.42 (s, 3H), 2.51 (d, J = 5.2 Hz, 3H) ; m / z ND159 2-(1-Benzyl-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1 H-NMR (500 MHz, Acetone-d6) δ 7.87 (d, J = 8.0 Hz, 1H), 7.74 (dd, J = 8.5, 1.8 Hz, 1H), 7.50 (d, J = 1.3 Hz, 1H), 7.30 (d, J = 8.1 Hz, 1H), 7.27 (dd, J = 8.0, 6.4 Hz, 2H), 7.23 (d, J = 7.2 Hz, 1H), 7.13 (d, J = 1.7 Hz, 2H), 7.12 (s, 1H), 7.02 (dd, J = 8.1, 2.0 Hz, 1H), 6.97 (d, J = 1.9 Hz, 1H), 6.23 (q, J = 4.6 Hz, 1H), 6.02 (dd, J = 3.9, 2.7 Hz, 1H), 5.96 (s, 2H), 5.91 (dd, J = 3.9, 1.7 Hz, 1H), 3.49 (s, 3H), 3.37 (s, 3H), 2.53 (d, J = 5.2 Hz, 3H) ; m / z ND160 2-(1-(3-Fluorobenzyl)-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 7.84 (dd, 1H), 7.72 (dd, J = 8.5, 1.8 Hz, 1H), 7.48 (d, J = 1.3 Hz, 1H), 7.35 - 7.27 (m, 2H), 7.14 (dd, J = 2.6, 1.7 Hz, 1H), 7.06 (dd, J = 7.0, 1.9 Hz, 2H), 6.99 - 6.94 (m, 2H), 6.85 (dt, 1H), 6.22 (dd, J = 10.3, 5.1 Hz, 1H), 6.03 (dd, J = 3.9, 2.7 Hz, 1H), 6.00 (s, 2H), 5.91 (dd, J = 3.9, 1.7 Hz, 1H), 3.48 (s, 3H), 3.37 (s, 3H), 2.50 (d, J = 5.2 Hz, 3H) ; m / z ND161 2-(1-(4-Fluorobenzyl)-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 7.85 (d, J = 8.5 Hz, 1H), 7.73 (dd, J = 8.5, 1.7 Hz, 1H), 7.49 (d, J = 1.4 Hz, 1H), 7.31 (d, J = 8.1 Hz, 1H), 7.21 (dd, J = 8.7, 5.4 Hz, 2H), 7.12 (dd, J = 2.6, 1.7 Hz, 1H), 7.05 - 7.01 (m, 4H), 6.23 (d, J = 5.4 Hz, 1H), 6.01 (dd, J = 3.9, 2.7 Hz, 1H), 5.94 (s, 2H), 5.89 (dd, J = 3.9, 1.7 Hz, 1H), 3.48 (s, 3H), 3.37 (s, 3H), 2.51 (d, J = 5.2 Hz, 3H) ; m / z ND162 2-(1-(2,4-Difluorobenzyl)-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 7.82 (d, J = 8.5 Hz, 1H), 7.72 (dd, J = 8.5, 1.7 Hz, 1H), 7.49 (d, J = 1.4 Hz, 1H), 7.33 (d, J = 8.1 Hz, 1H), 7.16 (d, J = 1.9 Hz, 1H), 7.09 (dd, J = 8.1, 1.9 Hz, 2H), 7.06 - 6.87 (m, 3H), 6.23 (d, J = 5.2 Hz, 1H), 6.03 (dd, J = 3.9, 2.7 Hz, 1H), 6.01 (s, 2H), 5.90 (dd, J = 4.0, 1.7 Hz, 1H), 3.49 (s, 3H), 3.39 (s, 3H), 2.51 (d, J = 5.2 Hz, 3H) ; m / z ND163 2-(1-(2,6-Difluorobenzyl)-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 7.91 (d, J = 8.5 Hz, 1H), 7.77 (dd, J = 8.5, 1.7 Hz, 1H), 7.58 (d, J = 1.4 Hz, 1H), 7.43 (tt, J = 8.4, 6.5 Hz, 1H), 7.29 (d, J = 8.1 Hz, 1H), 7.15 (d, J = 1.8 Hz, 1H), 7.12 (dd, J = 8.1, 2.0 Hz, 1H), 7.07 - 7.00 (m, 2H), 6.91 (d, J = 0.9 Hz, 1H), 6.26 (q, J = 10.2, 5.0 Hz, 1H), 6.02 (s, 2H), 5.96 (dd, J = 3.9, 2.8 Hz, 1H), 5.89 (dd, J = 3.9, 1.6 Hz, 1H), 3.46 (s, 3H), 3.35 (s, 3H), 2.55 - 2.53 (m, 3H) ; m / z ND164 2-(1-(4-Methoxybenzyl)-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 7.87 (dd, J = 8.5, 0.4 Hz, 1H), 7.74 (dd, J = 8.5, 1.8 Hz, 1H), 7.51 (dd, J = 1.7, 0.4 Hz, 1H), 7.27 (d, J = 8.1 Hz, 1H), 7.11 - 7.04 (m, 3H), 7.02 (dd, J = 8.2, 2.0 Hz, 1H), 6.93 (d, J = 1.9 Hz, 1H), 6.83 - 6.77 (m, 2H), 6.24 (dd, J = 10.5, 5.3 Hz, 1H), 5.97 (dd, J = 3.9, 2.7 Hz, 1H), 5.87 (dd, J = 3.9, 1.7 Hz, 1H), 5.84 (s, 2H), 3.71 (s, 3H), 3.46 (s, 3H), 3.33 (s, 3H), 2.52 (d, J = 5.2 Hz, 3H) ; m / z ND165 2-(1-(2-Bromo-5-methoxybenzyl)-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide 1H-NMR (500 MHz, Acetone-d6) δ 7.78 (dd, J = 8.5, 0.6 Hz, 1H), 7.69 (dd, J = 8.5, 1.8 Hz, 1H), 7.47 (dd, J = 1.7, 0.6 Hz, 1H), 7.46 (d, J = 8.7 Hz, 1H), 7.34 (dd, J = 7.8, 0.8 Hz, 1H), 7.16 - 7.12 (m, 3H), 6.75 (dd, J = 8.7, 3.1 Hz, 1H), 6.21 (dt, J = 10.4, 5.0 Hz, 1H), 6.09 (dd, J = 4.0, 2.7 Hz, 1H), 6.03 (d, J = 3.1 Hz, 1H), 5.99 (d, J = 3.8 Hz, 2H), 5.96 (dd, J = 3.9, 1.7 Hz, 1H), 3.63 (s, 3H), 3.50 (s, 3H), 3.40 (s, 3H), 2.49 (d, J = 5.2 Hz, 3H) ; m / z ND

[0435] Experimental Example 1. CBP Inhibitory Activity

[0436] The CBP bromodomain activity was measured using a time-resolved fluorescence resonance energy transfer (TR-FRET) experiment.

[0437] The assay was performed in a final volume of 14 μl and optimized based on the CREBBP Time Resolved Fluorescence Resonance Energy Transfer (TR-FRET) assay kit (BPS Bioscience, cat. 32619) to maximize the assay window and was performed in a total final volume of 14 μl. The TR-FRET fluorescence acceptor and Tb donor were diluted in assay buffer containing 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid (assay buffer, BPS Bioscience, cat. 33012), and 3 μl of each solution was transferred to all wells of a white 384-low-volume well plate (Corning, cat. 4513). Transfer 2 ul of 4X Ac-H4 peptide (final concentration 85 nM) to the high control wells and test wells. The compounds are serially diluted 3-fold from the highest concentration in dimethyl sulfoxide solvent to prepare 10 concentration points. Then, dilute each concentration of compound in assay buffer to prepare a diluted compound solution 4-fold more concentrated than the final concentration. Dispense 2 ul of each compound or dimethyl sulfoxide prepared in this way into the assay plate so that the final test concentration is from 0.5 uM to 10 uM (final dimethyl sulfoxide concentration 1%). Add 6 μL of 1X assay buffer to the low control wells and 2 ul to the high control and test wells. The PPI reaction was then initiated by adding 2 ul of 4X CBP BRD protein (final concentration 7.5 nM, BPS bioscience, cat 31128). The plate was allowed to react at room temperature for 2 hours before measuring the signal. The TR-FRET signal was measured using an EnVision Multilabel plate reader (PerkinElmer; Mirror LNACE / DELFIA Dual / Bias).Data analysis is performed using the TR-FRET ratio ((Signal665nm / Signal615nm) × 20000) to obtain the value for each well. Data analysis is performed using the TR-FRET ratio ((Signal665nm / Signal615nm) × 20000). Data are reported as percent inhibition compared to control wells based on the following equation: % Activity = ((FRETcompound - FRETLow av) / (FRETHigh av - FRETLow av)) × 100. IC50 analysis was determined by standard four-parameter curve fitting according to the algorithm using GraphPad Prism 7.0 (GraphPad Software Inc., La Jolla, CA, USA). All data are expressed as mean ± standard error of the mean (SEM).

[0438] Experimental Example 2. BRD4 Inhibitory Activity

[0439] BRD4 inhibitory activity was measured using time-resolved fluorescence resonance energy transfer (TR-FRET) assay to verify BRD4 bromodomain activity.

[0440] The assay was performed in a final volume of 14 μl and optimized based on the CREBBP Time Resolved Fluorescence Resonance Energy Transfer (TR-FRET) assay kit (BPS Bioscience, cat. 32613) to maximize the assay window and was performed in a total final volume of 14 μl. The TR-FRET fluorescence acceptor and Tb donor were diluted in assay buffer containing 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid (Assay buffer, BPS Bioscience, cat. 33012), and 3 μl of each solution was transferred to all wells of a white 384-low-volume well plate (Corning, cat. 4513). Transfer 2 ul of 4X Ac-H4 peptide (final concentration 15 nM) to the high control wells and test wells. The compounds are serially diluted 3-fold from the highest concentration in dimethyl sulfoxide to prepare 10 concentration points. Then, dilute each concentration of compound in assay buffer to prepare a diluted compound solution 4-fold more concentrated than the final concentration. Dispense 2 ul of each compound or dimethyl sulfoxide prepared in this way into the assay plate so that the final test concentration is from 0.5 uM to 10 uM (final DMSO concentration 1%). Add 6 μL of 1X assay buffer to the low control wells and 2 ul to the high control and test wells. The PPI reaction was then initiated by adding 2 ul of 4X BRD4 (BD1) protein (final concentration 7.5 nM, BPS bioscience, cat 31040). The plate was allowed to react at room temperature for 2 hours before measuring the signal. The TR-FRET signal was measured using an EnVision Multilabel plate reader (PerkinElmer; Mirror LNACE / DELFIA Dual / Bias).Data analysis is performed using the TR-FRET ratio ((Signal665nm / Signal615nm) × 20000) to obtain the value for each well. Data analysis is performed using the TR-FRET ratio ((Signal665nm / Signal615nm) × 20000). Data are reported as percent inhibition compared to control wells based on the following equation: % Activity = ((FRETcompound - FRETLow av) / (FRETHigh av - FRETLow av)) × 100. IC50 analysis was determined by standard four-parameter curve fitting according to the algorithm using GraphPad Prism 7.0 (GraphPad Software Inc., La Jolla, CA, USA). All data are expressed as mean ± standard error of the mean (SEM).

[0441] The results according to Experimental Examples 1 and 2 are shown in Tables 3 and 4 below.

[0442] In Tables 3 and 4 below, if the activity value is 0 or more and 500 nM or less, it is marked as '+++', if it is more than 500 and 5 uM or less, it is marked as '++', and if it is more than 5 uM, it is marked as '+'.

[0443] Example CBP BRD IC 50 Example CBP BRD IC 501++84+2++85+3++86+4+87+5++88++6+89+7++90+8++91+9+92+10+++93+11++94+12+95+13++96+++14+97+15++98+16+++99+17+++100+18++101+19+++102+20++103+21+104+22++105+23+106+2 4+107+25+108+26+109+27+110+28+111+29++112+30+113+31+114+32+++115+33+++116++34+11 7+35+118+36+119+37+++120+38+++121+39++122+40++123++41+124+42++125+43+126++44+127N .D45+128++46+129++47++130N.D48+++131+++49+132++50++133++51++134++52++135N.D53+13 6+54+137++55+138+56++139++57+140+58+141+59+142+60++143++61++144++62+145++63++146 ++64++147+++65++148++66++149++67++150++68++151++69+152+++70++153++71+154+72++155++73++156++74+157++75+158+76+159+77+160+78++161+79+162+80++163+81+164++82+165+83+

[0444] Example BRD4 (BD1) IC 50 Example BRD4 (BD1) IC 50<h2 style=";text-align:left;direction:ltr">1N.D84N.D2++85+3++86+4N.D87+5+88N.D6N.D89+7++90+8++91+9N.D92+10++93+11+94+12N.D95+13N.D96+14N.D97+15N.D98+16++99+17+100+18+101+19++102+20+103+21N.D104+22+105+23N.D106N.D24N.D107N.D25N.D108N .D26N.D109N.D27N.D110N.D28N.D111N.D29+112N.D30N.D113N.D31N.D114N.D32++115N.D33++116N.D34N.D117N .D35N.D118N.D36N.D119N.D37++120N.D38+121N.D39+122N.D40+123N.D41N.D124N.D42N.D125N.D43N.D126N.D4 4N.D127N.D45N.D128N.D46N.D129+47N.D130N.D48++131++49N.D132N.D50N.D133N.D51++134N.D52+135N.D53N. D136N.D54+137N.D55N.D138N.D56N.D139N.D57N.D140N.D58+141N.D59N.D142N.D60N.D143+61N.D144N.D62N.D1 45N.D63N.D146+64+147++65+148N.D66++149N.D67N.D150N.D68N.D151++69N.D152++70++153+71N.D154+72N.D1 55+73+156++74+157+75+158+76N.D159++77N.D160++78+161++79N.D162+80+163+81N.D164++82N.D165++83N.D

Claims

1. A compound represented by the following chemical formula I: <Chemical Formula I> During the meal, W, X or Y are each independently C or N, n is an integer from 0 to 3, and when n is an integer greater than or equal to 2, each R is equal to or different from each other, and each R is independently NR. a R b , SO2NHR c , CONHR d , SO2R e , CO2R f , halogen, C 1-4 Alkyl, C 1-4 haloalkyl, or 3- to 9-membered heteroaryl, R a Inland R f are each independently hydrogen, C 1-6 Alkyl, Hydroxy, C 1-5 selected from the group consisting of alkoxy, or 3- to 10-membered heterocycloalkyl, m is an integer from 0 to 3, and when m is an integer greater than or equal to 2, each A is the same or different, and each A is independently amide, hydroxy, C 1-5 alkoxy, a 3- to 10-membered heterocycloalkyl, a 3- to 9-membered heteroaryl, or a halogen, or two As are fused to each other to form a 3- to 10-membered heterocycloalkyl, or a 3- to 9-membered heteroaryl together with the atoms bonded thereto, Z is hydrogen, amide, hydroxy, C 1-5 Alkoxy, C 1-4 Alkyl, C 6-14 aryl, 3- to 10-membered heterocycloalkyl or 3- to 14-membered heteroaryl, At this time, the above R, R a Inland R f , A and Z are each substituted or unsubstituted with substituent group I: Substituent group I: substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 2-10 Alkenyl, substituted or unsubstituted C 3-20 Carbocycle, substituted or unsubstituted C 3-20 Cycloalkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted 3- to 30-membered heterocycle, substituted or unsubstituted C 1-10 Alkoxy, substituted or unsubstituted C 2-10 Alkenyloxy, substituted or unsubstituted C 3-10 Cycloalkyloxy, substituted or unsubstituted C 6-30 Aryloxy, substituted or unsubstituted 3- to 30-membered heterocycleoxy, substituted or unsubstituted C 1-10 Alkyl ketone, substituted or unsubstituted C 2-10 Alkenyl ketone, substituted or unsubstituted C 3-10 Cycloalkyl ketone, substituted or unsubstituted C 6-30 Aryl ketone, substituted or unsubstituted 3- to 30-membered heterocyclic ketone, substituted or unsubstituted C 1-10 Alkylthio, substituted or unsubstituted C 2-10 Alkenylthio, substituted or unsubstituted C 3-10 Cycloalkylthio, substituted or unsubstituted C 6-30 Arylthio, substituted or unsubstituted 3 to 30 membered heterocyclicthio, aldehyde, carboxy, halogen, substituted or unsubstituted C 1-10 Consisting of haloalkyl, hydroxy, substituted or unsubstituted amino, substituted or unsubstituted imine, cyano, substituted or unsubstituted nitro, substituted or unsubstituted amide, thiol, sulfone and phosphoric acid, Here, C 1-10 Alkyl moieties are -O-, -S-, -SO-, -SO2-, -NR g -(R g is hydrogen or substituted or unsubstituted C 1-10 alkyl), -N=, =N-, -POR g - and -PO4R g - is interrupted by a heteroatom group selected from, and the heterocycle moiety contains at least one of S, N, P and O as a ring member atom.

2. In paragraph 1, R, R a Inland R f , A compound wherein A and Z are each substituted or unsubstituted with substituent group I-1: Substituent group I-1: substituted or unsubstituted C 1-5 Alkyl, substituted or unsubstituted C 3-5 Cycloalkyl, substituted or unsubstituted amino, substituted or unsubstituted C 6-8 Aryl, substituted or unsubstituted 3- to 9-membered heterocycloalkyl, substituted or unsubstituted 3- to 11-membered heteroaryl, substituted or unsubstituted C 1-3 Haloalkyl, substituted or unsubstituted C 1-3 Alkoxy, hydroxy, halogen, aldehyde, cyano, substituted or unsubstituted amide.

3. In paragraph 1, the compound of formula I is a compound represented by any one of the following formulae I-1 to I-5: <Chemical Formula I-1> <Chemical Formula I-2> <Chemical Formula I-3> <Chemical Formula I-4> <Chemical Formula I-5> In the above formula, R, A, Z, n and m are as defined in Article 1, respectively.

4. In paragraph 3, the chemical formula I-1 is a compound represented by any one of the following chemical formulas I-1-1 to I-1-6: <Chemical Formula I-1-1> <Chemical Formula I-1-2> <Chemical Formula I-1-3> <Chemical Formula I-1-4> <Chemical Formula I-1-5> <Chemical Formula I-1-6> In the above formula, R 112 , R 313 , R 114 , R 314 , R 215 , R 315 , R 116 , R 216 and R 316 are equal or different, and each independently SO2NHR c , CONHR d , SO2R e , CO2R f , C 1-4 haloalkyl, or 3 to 9 membered heteroaryl, each of which is unsubstituted or substituted with substituent group I, R c , R d , R e , R f , A, Z and m are as defined in Article 1, respectively.

5. In paragraph 3, chemical formula I-2 is a compound represented by any one of the following chemical formulas I-2-1 to I-2-3: <Chemical Formula I-2-1> <Chemical Formula I-2-2> <Chemical Formula I-2-3> In the above formula, R 322 , R 223 and R 323 are equal or different and are each independently NR a R b , SO2NHR c , CONHR d , C 1-4 alkyl, or a 3- to 9-membered heteroaryl, each of which is optionally substituted with a substituent group I, R a , R b , R c , R d , A, Z and m are as defined in Article 1, respectively.

6. In the third paragraph, the chemical formula I-3 is a compound represented by any one of the following chemical formulas I-3-1 to I-3-4: <Chemical Formula I-3-1> <Chemical Formula I-3-2> <Chemical Formula I-3-3> <Chemical Formula I-3-4> In the above formula, R 132 , R 333 , R 134 and R 334 are equal or different and each is independently NR a R b or halogen, each of which is substituted or unsubstituted with substituent group I, R a , R b , A, Z and m are as defined in Article 1, respectively.

7. In paragraph 3, the chemical formula I-4 is a compound represented by any one of the following chemical formulas I-4-1 to I-4-6: <Chemical Formula I-4-1> <Chemical Formula I-4-2> <Chemical Formula I-4-3> <Chemical Formula I-4-4> <Chemical Formula I-4-5> <Chemical Formula I-4-6> In the above formula, R 142 , R 243 , R 344 , R 145 , R 345 , R 146 , R 246 and R 346 are equal or different and are each independently NR a R b or CONHR d , each of which is substituted or unsubstituted with a substituent group I, R a , R b , R d , A, Z and m are as defined in Article 1, respectively.

8. In paragraph 3, the chemical formula I-5 is a compound represented by any one of the following chemical formulas I-5-1 to I-5-3: <Chemical Formula I-5-1> <Chemical Formula I-5-2> <Chemical Formula I-5-3> In the above formula, R 352 , R 153 and R 353 are equal or different and are each independently NR a R b or halogen, each of which is substituted or unsubstituted with substituent group I, R a , R b , A, Z and m are as defined in Article 1, respectively.

9. In paragraph 1, R is each independently NR a R b , SO2NHR c , CONHR d , SO2R e , CO2R f , chloro, C 1-2 haloalkyl, or pyrazolyl, At this time, the above R a Inland R f are each independently hydrogen, methyl, ethyl, propyl, pyrrolidinyl, or morpholinyl, and R a Inland R f are each substituted or unsubstituted with substituent group I-1-1. A compound wherein R is substituted or unsubstituted with a substituent group I-1-2: Substituent group I-1-1: substituted or unsubstituted C 1-3 Alkyl, substituted or unsubstituted C 3-5 Cycloalkyl, substituted or unsubstituted amino, substituted or unsubstituted C 6-8 aryl, substituted or unsubstituted 3- to 9-membered heterocycloalkyl, substituted or unsubstituted 3- to 11-membered heteroaryl; Substituent group I-1-2: substituted or unsubstituted C 1-3 Alkyl.

10. In paragraph 1, A is acetamide, carbamide, hydroxy, isoxazolyl, hydropyranyl or tetrahydropyranyl, or imidazolidinonyl, lactamyl, piperazine dionyl or pyrrolyl formed by two As being fused to each other and together with the atoms bonded thereto, The compound wherein A is substituted or unsubstituted with a substituent group I-1-3: Substituent group I-1-3: substituted or unsubstituted C 1-4 Alkyl, substituted or unsubstituted C 3-5 Cycloalkyl, substituted or unsubstituted amide.

11. In paragraph 1, Z is hydrogen, methyl, hydroxy, amide, phenyl, naphthalenyl, tetrahydrofuranyl, lactamyl, tetrahydropyranyl, pyrrolyl, thiazolyl, imidazolyl, thiophenyl, isoxazolyl, pyrazolyl, pyridinyl, benzimidazolyl, indolyl, azaindolyl, indazolyl, benzofuranyl, benzothiophenyl, pyrazolopyridinyl, pyrazolopyrimidinyl, pyrrolopyridinyl, quinolinyl or isoquinolinyl, A compound wherein the above Z is substituted or unsubstituted with a substituent group I-1-4: Substituent group I-1-4: substituted or unsubstituted C 1-5 Alkyl, substituted or unsubstituted C 3-5 Cycloalkyl, C 1-3 Haloalkyl, substituted or unsubstituted C 6-8 Aryl, substituted or unsubstituted 3- to 8-membered heteroaryl, substituted or unsubstituted 4- to 8-membered heterocycloalkyl, substituted or unsubstituted 3- to 8-membered heterocycloalkenyl, substituted or unsubstituted C 1-3 Alkoxy, hydroxy, halogen, aldehyde, cyano, substituted or unsubstituted amide.

12. In paragraph 1, a compound selected from the following group: N,1',3'-Trimethyl-2-(1-methyl-1H-pyrazol-4-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(5-Fluoronaphthalen-1-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(4-hydroxyphenyl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2'-oxo-2-(tetrahydrofuran-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2'-oxo-2-(quinolin-8-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1H-indazol-4-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2-(2-methyl-3-(trifluoromethyl)phenyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(2,3-dimethylphenyl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(3-Cyclopropyl-1-methyl-1H-pyrazol-4-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(4-chloro-1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2-(2-methylthiophen-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(3-methoxynaphthalen-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(Isoquinolin-1-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2'-oxo-2-(pyrazolo[1,5-a]pyrimidin-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide], 2-(4-hydroxynaphthalen-1-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2-(1-methyl-1H-indazol-7-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2'-oxo-2-(thiazol-5-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(4-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(Isoquinolin-8-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 5-(6-((3-(azepan-1-yl)propyl)(methyl)amino)-8-(1H-pyrrolo[2,3-b]pyridin-2-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(6-((3-(azepan-1-yl)propyl)(methyl)amino)-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(6-((3-(azepan-1-yl)propyl)(methyl)amino)-8-(1H-pyrrolo[3,2-b]pyridin-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one, 5-(6-((3-(azepan-1-yl)propyl)(methyl)amino)-8-(1-ethyl-1H-indol-4-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(8-(2,5-dimethyl-1-(4-methylpyridin-2-yl)-1H-pyrrol-3-yl)-6-(methyl(2-(methyl(phenyl)amino)ethyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(6-((1-Benzylpyrrolidin-3-yl)(methyl)amino)-8-(thiazol-5-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 1,3-Dimethyl-5-(6-(methyl(2-(thiophen-3-yl)ethyl)amino)-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one, 2-(3,5-dimethylisoxazol-4-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2'-oxo-2-(1H-pyrazol-4-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 5-(8-(1-isopropyl-1H-pyrrol-3-yl)-6-((2-(6-methoxy-1H-indol-3-yl)ethyl)(methyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(6-((3-(1H-pyrrol-1-yl)benzyl)(methyl)amino)-8-(1H-benzo[d]imidazol-4-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(6-(((1-cyclohexylpyrrolidin-3-yl)methyl)(methyl)amino)-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(6-(((1-cyclohexylpyrrolidin-3-yl)methyl)(methyl)amino)-8-(7-ethyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(8-(1H-Indol-5-yl)-6-(methyl(2-(m-tolyloxy)ethyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(8-(6-chloro-1H-indol-3-yl)-6-(methyl(2-(m-tolyloxy)ethyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(8-(6-bromo-1H-indole-3-yl)-6-((3-(4-chloro-1H-pyrazol-1-yl)propyl)(methyl)amino)-9H-purin-9-yl)-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one, 5-(6-((2-(1-cyclopentylpiperidin-4-yl)ethyl)(methyl)amino)-8-(6-methoxy-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, N,1',3'-Trimethyl-2-(1-methyl-1H-imidazol-5-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 5-(6-(dimethylamino)-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-sulfonamide, 2-[3-(3,4-difluorophenyl)imidazol-4-yl]-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide, 2-(6-bromo-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide, 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(6-oxo-2-piperidyl)benzimidazole-5-sulfonamide, (S)-2-(1-(3,4-difluorophenyl)-6-oxo-piperidin-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(5-Fluoro-1-phenyl-1H-pyrazol-4-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-2-(4-isoquinolyl)-N-methyl-benzimidazole-5-sulfonamide, tert-Butyl 4-[3-[1-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-6-(methylsulfamoyl)benzimidazol-2-yl]-1H-indol-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylate, 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-[6-(1-methylpyrazol-4-yl)-1H-indol-3-yl]benzimidazole-5-sulfonamide, tert-Butyl 4-(3-(1',3'-dimethyl-6-(N-methylsulfamoyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazol]-2-yl)-1H-indol-6-yl)piperidine-1-carboxylate, N,1',3'-Trimethyl-2'-oxo-2-(6-(piperidin-4-yl)-1H-indol-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 3-(1,3-Dimethyl-2-oxo-benzimidazol-5-yl)-2-(1H-indazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide, N,1',3'-Trimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-carboxamide, 3-(1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-2-(3-methoxynaphthalen-2-yl)-N-methyl-3H-imidazo[4,5-b]pyridine-5-carboxamide, 5-[6-(difluoromethyl)-2-(6-methyl-1H-indol-3-yl)benzimidazol-1-yl]-1,3-dimethyl-benzimidazol-2-one, 5-(4-chloro-2-(6-methyl-1H-indol-3-yl)-1H-imidazo[4,5-c]pyridin-1-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-[4-(dimethylamino)-2-(6-methyl-1H-indol-3-yl)imidazo[4,5-c]pyridin-1-yl]-1,3-dimethyl-benzimidazol-2-one, 5-[4-(dimethylamino)imidazo[4,5-c]pyridin-1-yl]-1,3-dimethyl-benzimidazol-2-one, 1,3-Dimethyl-5-[2-(6-methyl-1H-indol-3-yl)-6-(1-methylpyrazol-4-yl)benzimidazol-1-yl]benzimidazol-2-one, 5-[7-(dimethylamino)-2-(6-methyl-1H-indol-3-yl)imidazo[4,5-b]pyridin-3-yl]-1,3-dimethyl-benzimidazol-2-one, 2-(7-bromo-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide, 2-(7-chloro-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide, 2-(5-chloro-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide, 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(5-methyl-1H-indazol-3-yl)benzimidazole-5-sulfonamide, 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(5-methyl-1H-indol-3-yl)benzimidazole-5-sulfonamide, 1,3-Dimethyl-5-[2-(6-methyl-1H-indol-3-yl)-6-methylsulfonyl-benzimidazol-1-yl]benzimidazol-2-one, 1,3-Dimethyl-5-[2-(6-methyl-1H-indol-3-yl)imidazo[4,5-c]pyridin-1-yl]benzimidazol-2-one, N-Methyl-2-(6-methyl-1H-indol-3-yl)-1-(1,3,3-trimethyl-2-oxoindolein-6-yl)-1H-benzo[d]imidazole-6-sulfonamide, 2-(5-cyano-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide, 2-(5-bromo-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide, 2-(4-bromo-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide, 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-[6-(trifluoromethyl)-1H-indol-3-yl]benzimidazole-5-sulfonamide, 2-(7-Cyclopropyl-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide, 2-(4-Cyclopropyl-1H-indol-3-yl)-3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-benzimidazole-5-sulfonamide, N,1',3'-trimethyl-2,2'-dioxo-2,2',3,3'-tetrahydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N-[4-[1-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-6-(methylsulfamoyl)benzimidazol-2-yl]-3-methyl-phenyl]acetamide, 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-[5-(trifluoromethyl)-1H-indol-3-yl]benzimidazole-5-sulfonamide, 2-(6-Bromo-1H-pyrrolo[3,2-c]pyridin-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(1H-pyrrolo[3,2-c]pyridin-3-yl)benzimidazole-5-sulfonamide, 3-(1,3-Dimethyl-2-oxo-benzimidazol-5-yl)-2-(4-formyl-1-naphthyl)-N-methyl-benzimidazole-5-sulfonamide, 1,3-Dimethyl-5-[2-(6-methyl-1H-indol-3-yl)imidazo[4,5-c]pyridin-3-yl]benzimidazol-2-one, 2-(4-(difluoromethyl)naphthalen-1-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N-Methyl-2-(6-methyl-1H-indol-3-yl)-3-(1,3,3-trimethyl-2-oxo-indolein-5-yl)benzimidazole-5-sulfonamide, 1',3'-Dimethyl-6-(N-methylsulfamoyl)-2'-oxo-N-(pyridin-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-2-carboxamide, 1-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-6-(methylsulfamoyl)-N-(4-pyridyl)benzimidazole-2-carboxamide, 3-(1,3-dimethyl-2-oxo-benzimidazol-4-yl)-N-methyl-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-sulfonamide, 3-(1,3-dimethyl-2-oxo-benzimidazol-4-yl)-N-methyl-2-(3-methylimidazol-4-yl)benzimidazole-5-sulfonamide, N-Methyl-2-(6-methyl-1H-indol-3-yl)-3-(2-oxo-3,4-dihydro-1H-quinolin-7-yl)benzimidazole-5-sulfonamide, 3-(1,3-Dimethyl-2-oxo-benzimidazol-5-yl)-2-(1H-indazol-3-yl)-N-methyl-benzimidazole-5-sulfonamide, Methyl 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-carboxylate, 3-(1,3-Dimethyl-2-oxo-benzimidazol-5-yl)-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-carboxylic acid, 3-[3-(3,5-dimethylisoxazol-4-yl)phenyl]-N-methyl-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-sulfonamide, 1,1,3-Trimethyl-3-[3-[2-(6-methyl-1H-indol-3-yl)-6-(methylsulfamoyl)benzimidazol-1-yl]phenyl]urea, N-Methyl-5-[2-(6-methyl-1H-indol-3-yl)-6-(methylsulfamoyl)benzimidazol-1-yl]-1H-indole-3-carboxamide, 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(2-pyridyl)benzimidazole-5-sulfonamide, 3-(1,4-dimethyl-2,3-dioxo-quinoxalin-5-yl)-N-methyl-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-sulfonamide, N-[3-[2-(6-methyl-1H-indol-3-yl)-6-(methylsulfamoyl)benzimidazol-1-yl]-5-tetrahydropyran-4-yl-phenyl]acetamide, 3-[3-(3,5-dimethylisoxazol-4-yl)phenyl]-N-methyl-2-(3-methylimidazol-4-yl)benzimidazole-5-sulfonamide, N-[3-[2-(6-methyl-1H-indol-3-yl)-6-(methylsulfamoyl)benzimidazol-1-yl]phenyl]acetamide, N-Methyl-5-[2-(6-methyl-1H-indol-3-yl)-6-(methylsulfamoyl)benzimidazol-1-yl]-7-tetrahydropyran-4-yl-1H-indole-3-carboxamide, 3-(3-hydroxy-5-tetrahydropyran-4-yl-phenyl)-N-methyl-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-sulfonamide, 1-(3-(3,5-dimethylisoxazol-4-yl)-5-(tetrahydro-2H-pyran-4-yl)phenyl)-N-methyl-2-(6-methyl-1H-indol-3-yl)-1H-benzo[d]imidazole-6-sulfonamide, Methyl 3-(3-acetamido-5-tetrahydropyran-4-yl-phenyl)-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-carboxylate, 3-(3-acetamido-5-tetrahydropyran-4-yl-phenyl)-2-(6-methyl-1H-indol-3-yl)benzimidazole-5-carboxylic acid, N-Methyl-2-(3-methylimidazol-4-yl)-3-(2-oxo-1,3-dihydrobenzimidazol-5-yl)benzimidazole-5-sulfonamide, 3-(1,3-dimethyl-2-oxo-benzimidazol-5-yl)-N-methyl-2-(1-methylimidazol-4-yl)benzimidazole-5-sulfonamide, 1',3'-Dimethyl-2-phenyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazole]-2'-one, 2-(3-bromophenyl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one, 2-(4-bromophenyl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazol]-2'-one, 2-(1H-imidazol-5-yl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazole]-2'-one, 2-(1H-Indol-3-yl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazole]-2'-one, 1',3'-Dimethyl-2-(6-methyl-1H-indol-3-yl)-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazole]-2'-one, 2-(1H-Indol-2-yl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazole]-2'-one, 2-(1,6-dimethyl-1H-indol-3-yl)-1',3'-dimethyl-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazole]-2'-one, 1',3'-Dimethyl-2-(1-methyl-1H-imidazol-5-yl)-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazole]-2'-one, 2-(1H-imidazol-5-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1H-Indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1,6-dimethyl-1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1H-Indol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 5-(6-chloro-8-(1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(6-chloro-8-(1H-indol-2-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(6-chloro-8-(6-methyl-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(6-chloro-8-(1H-imidazol-5-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, N,1',3'-Trimethyl-2-(3-(1-methyl-1H-pyrazol-4-yl)phenyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2-(4-(1-methyl-1H-pyrazol-4-yl)phenyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1-(cyclopropylmethyl)-6-methyl-1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2-(6-methyl-1-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2-(6-methyl-1-(2-morpholinoethyl)-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(Benzofuran-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(Benzo[b]thiophen-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2-(2-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(4-fluoro-1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(5-Fluoro-1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(6-Fluoro-1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(5,6-Difluoro-1H-indol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2'-oxo-2-(4,5,6,7-tetrafluoro-1H-indol-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 5-(6-(dimethylamino)-8-(1-methyl-1H-imidazol-5-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(6-(dimethylamino)-8-(4-fluoro-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(6-(dimethylamino)-8-(5-fluoro-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(6-(dimethylamino)-8-(6-fluoro-1H-indol-3-yl)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 5-(8-(5,6-difluoro-1H-indol-3-yl)-6-(dimethylamino)-9H-purin-9-yl)-1,3-dimethyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, 1',3'-Diethyl-2-(4-fluoro-1H-indol-3-yl)-N-methyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 1',3'-Dicyclopropyl-2-(4-fluoro-1H-indol-3-yl)-N-methyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 1',3'-Dimethyl-2-(6-methyl-1H-indol-3-yl)-N-(2-morpholinoethyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 1',3'-Dimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N-(Cyclopropylmethyl)-1',3'-dimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 1',3'-Dimethyl-2-(6-methyl-1H-indol-3-yl)-6-(morpholinosulfonyl)-1',3'-dihydro-2'H-[1,5'-bibenzo[d]imidazole]-2'-one, 1',3'-Dimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N-Ethyl-1',3'-dimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N-Benzyl-1',3'-dimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N-Isopropyl-1',3'-dimethyl-2-(6-methyl-1H-indol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(5-Fluoro-1H-indol-3-yl)-1',3'-dimethyl-N-(2-morpholinoethyl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(4-fluoro-1H-indol-3-yl)-1',3'-dimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2'-oxo-2-(1H-pyrrol-3-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1-Benzyl-1H-pyrrol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2'-oxo-2-(1H-pyrrol-2-yl)-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1-(cyclopropylmethyl)-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1-(cyclopropylmethyl)-1H-pyrrol-3-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, N,1',3'-Trimethyl-2-(1-methyl-1H-pyrrol-3-yl)-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1-Benzyl-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1-(3-Fluorobenzyl)-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1-(4-fluorobenzyl)-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1-(2,4-difluorobenzyl)-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1-(2,6-difluorobenzyl)-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1-(4-methoxybenzyl)-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide, 2-(1-(2-Bromo-5-methoxybenzyl)-1H-pyrrol-2-yl)-N,1',3'-trimethyl-2'-oxo-2',3'-dihydro-1'H-[1,5'-bibenzo[d]imidazole]-6-sulfonamide.

13. A compound used as a CBP / p300 inhibitor in claim 1.

14. An isomer of the compound according to paragraph 1, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof.

15. A pharmaceutical composition for preventing or treating cancer, inflammatory disorders or autoimmune diseases, comprising as an active ingredient at least one of the compound according to paragraph 1, an isomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof.

16. A pharmaceutical composition according to claim 15, wherein the cancer is a cancer dependent on the oncogene MYC, a tumor harboring a loss of function mutation of CBP or p300, or a cancer with activation of CBP and / or p300 function.

17. A pharmaceutical composition according to claim 15, wherein the cancer disease is at least one selected from the group consisting of blood cancer, prostate cancer, breast cancer, lung cancer, pancreatic cancer, colorectal cancer, and melanoma.

18. In the 15th paragraph, the cancer disease is acoustic neuroma, acute leukemia, acute lymphoblastic leukemia, acute myeloid leukemia, acute T-cell leukemia, basal cell carcinoma, cholangiocarcinoma, bladder cancer, brain cancer, breast cancer, bronchial carcinoma, cervical cancer, chondrosarcoma, chordoma, choriocarcinoma, chronic leukemia, chronic lymphocytic leukemia, chronic myeloid leukemia, chronic myeloid leukemia, colon cancer, colon cancer, craniopharyngioma, cystadenocarcinoma, diffuse large B-cell lymphoma, proliferative changes, embryonal carcinoma, endometrial cancer, endothelioma, ependymoma, epithelial carcinoma, erythroleukemia, esophageal cancer, estrogen receptor-positive breast cancer, essential thrombocythemia, Ewing's tumor, fibrosarcoma, follicular lymphoma, germ cell testicular cancer, glioma, glioblastoma, pedunculation, heavy chain disease head and neck cancer, Hemangioblastoma, hepatoma, hepatocellular carcinoma, hormone-insensitive prostate cancer, leiomyosarcoma, leukemia, liposarcoma, lung cancer, lymphoendothelioma, lymphangiosarcoma, lymphocytic leukemia, lymphoma, lymphoid malignancy of T-cell or B-cell origin, medullary carcinoma, medulloblastoma, melanoma, meningioma, mesothelioma, multiple myeloma, myeloid leukemia, myeloma, myxosarcoma, neuroblastoma, NUT midline carcinoma (NMC), non-small cell lung cancer, oligodendroglioma, oral cancer, osteosarcoma, ovarian cancer, pancreatic cancer, papillary adenocarcinoma, papillary carcinoma, pinealoma, polycythemia vera, prostate cancer, rectal cancer, renal cell carcinoma, retinoblastoma, rhabdomyosarcoma, sarcoma, sebaceous carcinoma, seminoma, skin cancer, small cell lung carcinoma, solid tumors (carcinomas and sarcomas), small cell lung cancer, A pharmaceutical composition comprising at least one selected from the group consisting of gastric cancer, squamous cell carcinoma, synovial tumor, sweat gland carcinoma, thyroid cancer, Waldenstrom macroglobulinemia, testicular tumor, uterine cancer, and Wilms tumor.

19. In paragraph 15, the inflammatory disorder or autoimmune disease is Addison's disease, acute gout, ankylosing spondylitis, asthma, atherosclerosis, Behcet's disease, bullous skin disease, chronic obstructive pulmonary disease, Crohn's disease, dermatitis, eczema, giant cell arteritis, fibrosis, glomerulonephritis, hepatic vascular occlusion, hepatitis, hypophysitis, immunodeficiency syndrome, inflammatory bowel disease, Kawasaki disease, lupus nephritis, multiple sclerosis, myocarditis, myositis, nephritis, organ transplant rejection, osteoarthritis, pancreatitis, pericarditis, polyarteritis nodosa pneumonia, primary biliary cirrhosis, psoriasis, psoriatic arthritis, rheumatoid arthritis, scleritis, sclerosing cholangitis, sepsis, systemic lupus erythematosus, Takayasu's arteritis, toxic shock, thyroiditis, type 1 diabetes, ulcerative colitis, uveitis, vitiligo, A pharmaceutical composition comprising at least one selected from the group consisting of vasculitis and Wegener's granulomatosis.

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