5, 6-fused and 6, 6-fused bicyclols and ethers and compositions as 15-prostaglandin dehydrogenase modulators
By developing 5,6-fused and 6,6-fused bicyclic alcohols and ethers with specific structures, the challenge of 15-PGDH regulation was solved, achieving effective treatment and tissue healing for related diseases.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-05-07
- Publication Date
- 2026-03-10
AI Technical Summary
Existing technologies are unable to effectively regulate 15-hydroxy-prostaglandin dehydrogenase (15-PGDH), which affects a variety of biological processes such as hair density, skin wound healing, and bone formation.
5,6-fused and 6,6-fused bicyclic alcohols and ethers with specific structures are provided as modulators of 15-PGDH for the treatment of related diseases.
These compounds can effectively regulate 15-PGDH and have the potential to treat inflammatory bowel disease, ulcerative colitis, Crohn's disease, and fibrotic diseases, promoting tissue healing and bone formation.
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Figure CN121646599A_ABST
Abstract
Description
Cross Reference to Related Applications
[0001] This application claims priority to U.S. Provisional Patent Application No. 63 / 501,059, filed May 9, 2023, and U.S. Provisional Patent Application No. 63 / 640,585, filed April 30, 2024, each of which is incorporated by reference herein in its entirety. TECHNICAL FIELD
[0002] Provided herein are novel compounds, pharmaceutical compositions comprising such compounds, and methods of using such compounds and compositions to treat 15-hydroxy-prostaglandin dehydrogenase-mediated diseases. Also provided are methods of making such compounds and intermediates thereto. BACKGROUND
[0003] Short-chain dehydrogenases (SCDs) are a family of dehydrogenases involved in the synthesis and degradation of fatty acids, steroids, and some prostaglandins. As such, they are implicated in a variety of disorders, such as lipid storage diseases, myopathies, SCD deficiency, and certain genetic disorders. SCD 15-hydroxy-prostaglandin dehydrogenase (15-PGDH) (also identified as 15-prostaglandin dehydrogenase or hydroxyprostaglandin dehydrogenase 15-(nicotinamide adenine dinucleotide)) represents a key enzyme in the inactivation of many active prostaglandins, leukotrienes, and hydroxyeicosatetraenoic acids (HETEs). Recent studies suggest that inhibitors of 15-PGDH and activators of 15-PGDH can have therapeutic value. 15-PGDH is responsible for the inactivation of prostaglandin E2 (PGE2), a downstream product of cyclooxygenase-2 (COX-2) metabolism. PGE2 has been shown to be beneficial in a variety of biological processes such as hair density, skin wound healing, and bone formation. SUMMARY
[0004] Provided herein are compounds of Formula (A):
[0005] (A)
[0006] or a pharmaceutically acceptable salt of the compound;
[0007] wherein is (i), (ii), or (iii);
[0008] m is 0 or 1;
[0009] X is N or CH;
[0010] Y is N or C-R 3 ;
[0011] Z is N or C-R 5 ;
[0012] b is N or C-R 4 ;
[0013] R 1a is -H, deuterium, C 1-6 alkyl, or C 1-6 haloalkyl;
[0014] wherein, when R 1a is C 1-6 alkyl or C 1-6 haloalkyl, then R 1a may be unsubstituted or substituted with one or more substituents each of which is independently halogen, -OH, -N(R b )2, C 1-3 alkyl, or C 1-3 alkoxy;
[0015] R 1b is -H, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 heteroalkyl, -(C 1-6 alkylene)-O-(C 1-6 alkyl), C 3-10 cycloalkyl, or heterocyclyl having from 3 to 10 ring members;
[0016] wherein, when R 1b is C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 heteroalkyl, -(C 1-6 alkylene)-O-(C 1-6 alkyl), C 3-10 cycloalkyl, or heterocyclyl having from 3 to 10 ring members, then R 1b may be unsubstituted or substituted with one or more substituents each of which is independently halogen, -OH, -N(R b )2, C 1-3 alkyl, or C 1-3 alkoxy; wherein each of the C 1-3 alkyl and C 1-3 alkoxy groups can be unsubstituted or substituted with 1 to 6 -F groups;
[0017] or alternatively, R 1a and R 1b together form C 3-10 cycloalkyl, C 3-10 cycloalkenyl, or heterocyclyl having from 3 to 10 ring members;
[0018] Where R 1a and R 1b The ring can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-3 Alkyl, C 1-3 Alkoxy, -CN, C 1-6 Heteroalkyl, C 3-10 Cycloalkyl, or heterocyclic group having 3 to 10 ring members; wherein the C 1-3 Alkyl and C 1-3 Each of the alkoxy groups can be unsubstituted or surrounded by 1 to 9 halogen groups or C. 1-3 Alkyl substitution;
[0019] R 1c It is -H, C 1-6 Alkyl, or C 3-6 cycloalkyl;
[0020] Where R 1c It is C 1-6 Alkyl or C 3-6 When cycloalkyl, then R 1c It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, -N(R) group, or a halogenated group. b 2. C 1-3 Alkyl, C 1-3 alkoxy, or C 1-6 Heteroalkyl;
[0021] R 2 It is C 3-20 cycloalkyl, C 3-20 Cycloalkenyl, C 6-18 Aryl, heteroaryl having 5 to 20 ring members, or heterocyclic having 3 to 20 ring members;
[0022] Where R 2 It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Alkoxy, C 1-6 alkylene-OH, C 1-6 Alkylene-OC 1-6 Alkyl, or C 1-6 Heteroalkyl;
[0023] R 3 It is -H, C 1-6 Alkyl, C1-6 Haloalkyl, C 3-6 Cycloalkyl, amino, C 1-4 Alkyl-amino, di-C 1-4 Alkyl-amino, C 6-10 Aryl, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members;
[0024] Where R 3 It is C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-6 cycloalkyl, C 1-4 Alkyl-amino, di-C 1-4 Alkyl-amino, C 6-10 When R is aryl, a heteroaryl having 5 to 10 ring members, or a heterocyclic group having 5 to 10 ring members, then R 3 It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 Alkoxy, C 1-3 Alkylene-C 1-3 Alkoxy, C 1-6 Heteroalkyl, or two R 3 Substituents together form C 3-6 Carbocyclic groups or heterocyclic groups having 3 to 6 ring members;
[0025] R 4 It is -H, C 1-3 Alkyl, C 1-3 Haloalkyl, -CN, halogen, or -N(R) a )2, where R a Each instance, when it exists, is independently -H, C. 1-6 Alkyl, or -C(O)C 1-6 Alkyl; or alternatively, two R a The substituents together form a heterocyclic group having 3 to 6 ring members;
[0026] Where R a It can be unsubstituted or substituted with one or more substituents, each of which is independently -F, -Cl, -OH, C. 1-3 Alkoxy;
[0027] R 5 It is -H, C 1-6 Alkyl, C 3-6 cycloalkyl, C 1-6 Halogenated alkyl, or C 1-6Heteroalkyl;
[0028] Where R 5 It is C 1-6 Alkyl, C 3-6 cycloalkyl, C 1-6 Halogenated alkyl, or C 1-6 When it is a heteroalkyl group, then R 5 It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, C 1-3 Alkyl, or C 1-3 Alkoxy;
[0029] Where R b Each instance, when it exists, is independently -H or C. 1-6 Alkyl; or alternatively, two R b The substituents together form a heterocyclic group having 3 to 6 ring members; and
[0030] Where R b It is C 1-6 Alkyl, or alternatively, two R b When the substituents together form a heterocyclic group having 3 to 6 ring members, then R b It can be unsubstituted or substituted with one or more substituents, each of which is independently -F, -Cl, -OH, C. 1-3 Alkyl group.
[0031] In several embodiments, R 1a It is -H, C 1-6 Alkyl, C 1-6 Halogenated alkyl, or C 1-6 Heteroalkyl. In several embodiments, R 1a It can be unsubstituted or substituted with 1, 2, 3 or 4 substituents, each of which is independently a halogen, -OH, alkyl or alkoxy group.
[0032] In several embodiments, R 1b It is -H, C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-10 Cycloalkyl groups, or heterocyclic groups having 3 to 10 ring members. In several embodiments, R 1b It can be unsubstituted or substituted with 1, 2, 3 or 4 substituents, each of which is independently a halogen, -OH, alkyl or alkoxy group.
[0033] In several embodiments, R 1a and R 1b Together they form C 3-10 cycloalkyl, C 3-10Cycloalkenyl, or heterocyclic group having 3 to 10 ring members. In several embodiments, R 1a and R 1b Together, they provide a ring, the R 1a and R 1b The ring can be unsubstituted or substituted with 1, 2, 3 or 4 substituents, each of which is independently a halogen, -OH, alkyl, oxo, alkoxy or heteroalkyl.
[0034] In several embodiments, R 1c It is -H, C 1-6 Alkyl, or C 3-6 Cycloalkyl. In several embodiments, R 1c It can be unsubstituted or substituted with 1, 2, 3 or 4 substituents, each of which is independently a halogen, -OH, alkyl, alkoxy or heteroalkyl.
[0035] In several embodiments, R 2 It is C 3-10 cycloalkyl, C 3-10 Cycloalkenyl, C 8-10 Cycloalkynyl, C 6-10 Aryl, heteroaryl having 5 to 10 ring members, or heterocyclic having 3 to 10 ring members. In several embodiments, R 2 It can be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents, each of which is independently a halogen, -OH, oxo, alkyl, haloalkyl, alkoxy, alkylene-OH, alkylene-O-alkyl, or heteroalkyl.
[0036] In several embodiments, R 3 It is -H, C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-6 Cycloalkyl, amino, C 1-4 Alkyl-amino, di-C 1-4 Alkyl-amino, C 6-10 Aryl, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members. In several embodiments, R 3 It can be unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents, each of which is independently a halogen, -OH, oxo, alkyl, haloalkyl, alkoxy, alkylene-alkoxy, heteroalkyl, or two R groups. 3 Substituents together form carbocyclic or heterocyclic groups.
[0037] In several embodiments, R 4 It is -H, C 1-3 Alkyl, or -N(R) a)2. In several embodiments, R a When present, it is independently -H, C 1-3 Alkyl, or C 1-6 Heteroalkyl. In several embodiments, R a It is -H or C independently when it exists. 1-3 Alkyl group. In several embodiments, R a It can be unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents, each of which is independently a halogen, -OH, C 1-3 Haloalkyl, C 1-3 alkoxy, or two R a Substituents together form C 3-6 Carbon cyclic groups or heterocyclic groups having 3 to 6 ring members.
[0038] In several embodiments, R 5 It is -H, C 1-6 Alkyl, C 3-6 cycloalkyl, C 1-6 Halogenated alkyl, or C 1-6 Heteroalkyl. In several embodiments, R 5 It can be unsubstituted or substituted with 1, 2, 3 or 4 substituents, each of which is independently a halogen, -OH, alkyl or alkoxy group.
[0039] In several embodiments, when R 2 If it is an unsubstituted cyclopropyl, an unsubstituted phenyl, or an unsubstituted or substituted cycloalkenyl, then R 1a R 1b and R 1c One of them is not -H.
[0040] Several embodiments relate to a pharmaceutical composition comprising a compound or salt having formula (A) (which may be further defined as a compound or salt having formula (I)) and a pharmaceutically acceptable excipient.
[0041] Several embodiments relate to compounds or salts having formula (A) (e.g., compounds or salts having formula (I)) or pharmaceutical compositions comprising compounds having formula (A) for use as a medicine.
[0042] Several embodiments relate to compounds or salts having formula (A) (which may be further defined as compounds or salts having formula (I)) or pharmaceutical compositions comprising compounds having formula (A) for use in 15-PGDH-mediated diseases or disorders.
[0043] Several embodiments relate to pharmaceutical compositions of formula (A) (e.g., including compounds or salts having formula (I)) or comprising compounds having formula (A) for use in the treatment of inflammatory bowel disease.
[0044] Several embodiments relate to compounds or salts having formula (A) (which may be further defined as compounds or salts having formula (I)) or pharmaceutical compositions comprising compounds having formula (A) for use in the treatment of ulcerative colitis.
[0045] Several embodiments relate to compounds or salts having formula (A) (which may be further defined as compounds or salts having formula (I)) or pharmaceutical compositions comprising compounds having formula (A) for use in the treatment of Crohn's disease.
[0046] Several embodiments relate to compounds or salts having formula (A) (which may be further defined as compounds or salts having formula (I)) or pharmaceutical compositions comprising compounds having formula (A) for use in the treatment of fibrotic diseases, disorders or conditions.
[0047] Several embodiments relate to a method of treating a subject with a 15-PGDH-mediated disease, the method comprising administering to the subject a therapeutically effective amount of a compound or salt having formula (A) (which may be further defined as a compound or salt having formula (I)) or a pharmaceutical composition comprising a compound having formula (A).
[0048] Several embodiments relate to a method of treating an intestinal, gastrointestinal, or intestinal disorder in a subject in need, the method comprising administering to the subject a therapeutically effective amount of a compound or salt having formula (A) (which may be further defined as a compound or salt having formula (I)) or a pharmaceutical composition comprising a compound having formula (A).
[0049] Other aspects and advantages will become apparent to those skilled in the art upon reading the following detailed description. The description below includes specific situations, embodiments, and examples, and it should be understood that this disclosure is illustrative and not intended to limit the embodiments of this disclosure to the specific situations, embodiments, and examples described herein. Rather, references to embodiments of this disclosure are intended to cover alternatives, modifications, and equivalents that may be included within the spirit and scope of the embodiments of this disclosure as defined by the appended claims. Attached Figure Description
[0050] Figures 1A-1D Data on colon length are provided for mice suffering from dextran sulfate sodium (DSS)-induced colitis and treated with one of four different compounds having formula (A). Figure 1AData are shown for mice treated with compound B15S compared to mice treated with the medium alone or mice receiving the experiment for the first time. Figure 1B Data are shown for mice treated with compound B15R compared to mice treated with the medium alone or mice receiving the experiment for the first time. Figure 1C Data are shown for mice treated with compound B30R compared to mice treated with the medium alone or mice receiving the experiment for the first time. Figure 1D Data are shown for mice treated with compound B41R compared to mice treated with the medium alone or mice receiving the experiment for the first time.
[0051] Figures 2A-2D Histopathological data were provided for mice with DSS-induced colitis treated with compound B15R, compared with mice that received the medium alone or mice that were first-time test subjects. Figure 2A It provides a sum of histopathological scores. Figure 2B An inflammation score was provided. Figure 2C An erosion score was provided. Figure 2D A glandular loss score was provided.
[0052] Figures 3A-3D Histopathological data were provided for mice with DSS-induced colitis treated with compound B30R, compared with mice that received the medium alone or mice that were first-time test subjects. Figure 3A It provides a sum of histopathological scores. Figure 3B An inflammation score was provided. Figure 3C An erosion score was provided. Figure 3D A glandular loss score was provided.
[0053] Figures 4A-4D Histopathological data were provided for mice with DSS-induced colitis treated with compound B41R, compared with mice that received the medium alone or mice that were first-time test subjects. Figure 4A It provides a sum of histopathological scores. Figure 4B An inflammation score was provided. Figure 4C An erosion score was provided. Figure 4D A glandular loss score was provided. Detailed Implementation
[0054] Multiple embodiments provide compounds and compositions, methods of using them, and methods of manufacturing them. In multiple embodiments, the compounds disclosed herein can be used to inhibit SCD and / or 15-PGDH and / or to treat SCD and / or 15-PGDH diseases, disorders, and conditions. In multiple embodiments, the compounds disclosed herein have the structure of formula (A). In multiple embodiments, the compounds disclosed herein have the structure of formula (I). In multiple embodiments, the compounds disclosed herein have a benzothiophene group or a 5,6-fused thienophene-heterocyclic group (e.g., thienophene-pyridyl) core structure. In multiple embodiments, the compound comprises an alcohol or ether moiety located on the α carbon at the 2-position of the benzothiophene group or the 5,6-fused thienophene-heterocyclic group (e.g., thienophene-pyridyl) core. In multiple embodiments, the compound comprises an alcohol located on the α carbon at the 2-position of the benzothiophene group or the 5,6-fused thienophene-heterocyclic group (e.g., thienophene-pyridyl) core. Elsewhere in this document, for brevity, these compounds may be referred to as benzothienyl alcohols or 5,6-fused thieno-heterocyclic alcohols (e.g., thieno-pyridyl alcohols). These compounds, and any other compounds disclosed herein, may generally be referred to as 15-PGDH inhibitors.
[0055] The following description provides context and examples, but should not be construed as limiting the scope of the invention as covered by the appended claims or any other application claiming priority to this specification. No single component or set of components is necessary or indispensable. Some headings used herein are for organizational purposes only and should not be considered as limiting the subject matter described. Features disclosed under one heading (such as composition or combination) may be combined with features disclosed under a different heading (such as method of treatment).
[0056] Definitions
[0057] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. All patents, applications, published applications and other publications cited herein are incorporated herein by reference in their entirety. Where there are multiple definitions for terms herein, the definitions provided herein shall prevail unless otherwise stated.
[0058] As used in this article, "C" a-b (or similar wording, such as C) a To C b(), where "a" and "b" are integers, referring to the number of carbon atoms in an alkyl, alkylene, alkenyl, alkenylene, ynyl, alkenylene, haloalkyl, alkoxy, thioalkyl, heteroalkyl, cycloalkyl, cycloalkenyl, cycloynyl, aryl, heteroaryl, or other group. That is, the ring of an alkyl, alkenyl, ynyl, cycloalkyl, cycloalkenyl, cycloynyl, aryl, or heteroaryl group can contain "a" to "b" carbon atoms, including the terminal values. Therefore, for example, "C 1-4 "Alkyl" groups (or C1 to C4 alkyl) refer to all alkyl groups having 1 to 4 (e.g., 1, 2, 3, or 4) carbons, namely CH3-, CH3CH2-, CH3CH2CH2-, (CH3)2CH-, CH3CH2CH2CH2-, CH3CH2CH(CH3)-, and (CH3)3C-. 1-6 The term "alkyl" refers to all alkyl groups having 1 to 6 carbons (e.g., 1, 2, 3, 4, 5, or 6). If "a" and "b" are not specified for a group, the range described in these definitions is assumed. Given the foregoing disclosure, it should be understood that, in the case of the disclosure range (for the alkyl groups or other groups disclosed herein), each individual member within the disclosed range is also assumed and disclosed. Therefore, when "C" is disclosed... 1-6 When "alkyl" is used, it provides all alkyl groups having 1 to 6 carbons and any alkyl group containing 1, 2, 3, 4, 5, or 6 carbons, or combinations of the foregoing groups (e.g., 1, 2, 3, or 5 carbons; 2, 3, 4, or 6 carbons; etc.). Similarly, when "C" is disclosed... 1-3 When “alkyl” is used, it provides all alkyl groups having 1 to 3 carbons and any alkyl group containing 1, 2, or 3 carbons, or combinations of the foregoing groups (e.g., 1 or 3; 1 or 2; 2 or 3; etc.).
[0059] The term "alkyl" refers to a fully saturated (i.e., without double or triple bonds) straight-chain or branched hydrocarbon chain. Examples of branched alkyl groups include, but are not limited to, isopropyl, sec-butyl, tert-butyl, etc. Examples of straight-chain alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, etc. The alkyl group can have 1 to 12 carbon atoms. "Alkyl" can also be a lower alkyl group having 1 to 6 carbon atoms. C 1-5 Alkyl groups include C5 alkyl, C4 alkyl, C3 alkyl, C2 alkyl, and C1 alkyl (i.e., methyl). 1-6 Alkyl groups include those targeting C. 1-5 Alkyl groups include all of the aforementioned portions, but also include C6 alkyl groups. 1-10 Alkyl groups include those targeting C. 1-5 Alkyl and C 1-6 Alkyl groups include all of the aforementioned portions, but also include C7, C8, C9, and C6 groups. 10Alkyl group. Similarly, C 1-12 Alkyl groups include all the foregoing portions, but also include C. 11 and C 12 Alkyl group. For example, "C 1-4 "Alkyl" indicates that the alkyl chain has one to four carbon atoms, that is, the alkyl chain is methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl. C 1-12 Non-limiting examples of alkyl groups include, but are in no way limited to, methyl (“Me” or -CH3), ethyl, n-propyl, i-propyl, sec-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, and n-dodecyl.
[0060] The term "alkylene" or "alkylene chain" refers to a fully saturated, straight-chain or branched divalent hydrocarbon chain group having one to twelve carbon atoms. Examples of alkylene include, but are not limited to, methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, and octylene. 1-12 Alkylenes include C 12 Alkylene, C 11 Alkylene, C 10 Alkylenes, C9 alkylenes, C8 alkylenes, C7 alkylenes, C6 alkylenes, C5 alkylenes, C4 alkylenes, C3 alkylenes, and C2 alkylenes, as well as C1 alkylenes (i.e., methylene). Alkylenes can be lower alkylenes having 1 to 6 carbon atoms. Lower alkylenes include C6 alkylenes, C5 alkylenes, C4 alkylenes, C3 alkylenes, and C2 alkylenes, as well as C1 alkylenes. It should also be understood that, depending on the context, certain divalent group naming conventions may include monovalent or divalent group naming conventions. For example, when an intramolecular substituent requires two attachment points to the rest of the molecule, the substituent should be understood as a divalent group. For example, substituents identified as alkyl but requiring two attachment points include alkylene divalent groups such as -CH2-, -CH2CH2-, -CH2CH(CH3)CH2-, etc.
[0061] The term "alkenyl" or "alkenyl group" refers to a straight-chain or branched hydrocarbon chain group having two to twelve carbon atoms and one or more carbon-carbon double bonds. Alkenyl groups containing a maximum of 12 carbon atoms are C64-C ... 2-12 Alkenyl groups, which contain a maximum of 10 carbon atoms, are C10 and C20. 2-10 Alkenyl groups, which contain a maximum of 6 carbon atoms, are C64-264-3 ... 2-6 Alkenyl groups, and alkenyl groups containing a maximum of 5 carbon atoms, are C1646 ... 2-5 Alkenyl. C 2-5 Alkenyl groups include C5 alkenyl, C4 alkenyl, C3 alkenyl, and C2 alkenyl.2-6 Alkenyl groups include those targeting C. 2-5 All of the alkenyl groups described herein, but also including the C6 alkenyl group. 2-10 Alkenyl groups include those targeting C. 2-5 alkenyl and C 2-6 The alkenyl group includes all the parts described, but also includes C7, C8, C9, and C6. 10 Alkenyl. C 2-12 The alkenyl group includes all the aforementioned parts, but also includes C. 11 and C 12 Alkenyl. C 2-12 Non-limiting examples of alkenyl groups include ethenyl (or vinyl), 1-propenyl, 2-propenyl (allyl), isopropenyl, 2-methyl-1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-heptenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 5-heptenyl, 6-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, 5-octenyl, 6-octenyl, 7-octenyl, 1-nonenyl, 2-nonenyl, 3-nonenyl, 4-nonenyl, 5-nonenyl. 6-Nonenyl, 7-Nonenyl, 8-Nonenyl, 1-Decenyl, 2-Decenyl, 3-Decenyl, 4-Decenyl, 5-Decenyl, 6-Decenyl, 7-Decenyl, 8-Decenyl, 9-Decenyl, 1-Undecenyl, 2-Undecenyl, 3-Undecenyl, 4-Undecenyl, 5-Undecenyl, 6-Undecenyl, 7-Undecenyl, 8-Undecenyl, 9-Undecenyl, 10-Undecenyl, 1-Dodecenyl, 2-Dodecenyl, 3-Dodecenyl, 4-Dodecenyl, 5-Dodecenyl, 6-Dodecenyl, 7-Dodecenyl, 8-Dodecenyl, 9-Dodecenyl, 10-Dodecenyl, and 11-Dodecenyl.
[0062] The term "alkynyl" or "alkynyl group" refers to a straight-chain or branched hydrocarbon chain group having two to twelve carbon atoms and one or more carbon-carbon triple bonds. The alkynyl group containing a maximum of 12 carbon atoms is C0. 2-12 The alkynyl group, which contains a maximum of 10 carbon atoms, is C. 2-10 The alkynyl group, which contains a maximum of 6 carbon atoms, is C. 2-6 The alkynyl group, and alkynyl groups containing a maximum of 5 carbon atoms, are C64-C ... 2-5 Alkynyl group. C 2-5 Alkynyl groups include C5-, C4-, C3-, and C2-. 2-6 Alkyne groups include those targeting C. 2-5All parts described by the ynyl group, but also including the C6 ynyl group. 2-10 Alkyne groups include those targeting C. 2-5 alkynyl group and C 2-6 All parts described by the alkynyl group, but also including C7, C8, C9, and C6. 10 Alkynyl group. C 2-12 The alkynyl group includes all the aforementioned parts, but also includes C. 11 and C 12 Alkynyl group. C 2-12 Non-limiting examples of alkynyl groups include ethynyl, propynyl, butynyl, pentylyl, etc.
[0063] As used in this article, the term "halogen" or "halogenated" refers to any of the radioactively stable atoms in column 7 of the periodic table, such as fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
[0064] The term "haloalkyl" refers to a straight-chain or branched alkyl group in which one or more or all of the hydrogen atoms (e.g., -H) are replaced by a halogen. Examples of haloalkyl groups include, but are not limited to, -CF3, -CHF2, -CH2F, -CH2CF3, -CH2CHF2, -CH2CH2F, -CH2CH2Cl, -CH2CF2CF3, and other groups that are considered equivalent to any of the foregoing examples according to those skilled in the art and the teachings provided herein. The haloalkyl group may be a lower haloalkyl group. The haloalkyl group may be perhalogenated (e.g., perfluorinated).
[0065] The term "alkoxy" refers to the formula -OR, where R is an alkyl group as defined elsewhere in this document. For illustrative purposes, "C..." 1-9 "Alkoxy" includes, but is not limited to, methoxy, ethoxy, n-propoxy, 1-methylethoxy (isopropoxy), n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, etc.
[0066] The term "heteroalkyl" refers to a straight-chain or branched hydrocarbon chain (e.g., an alkyl group) containing one or more heteroatoms, each of which is independently nitrogen (e.g., amino, etc.), oxygen (e.g., alkoxy, ether, hydroxy, etc.), or sulfur (e.g., thiol, sulfide, etc.). The heteroalkyl group can have 1 to 12 carbon atoms, but this definition also covers the occurrence of the term "heteroalkyl" where no numerical range is specified. The heteroalkyl group can also be a lower heteroalkyl group having 1 to 6 carbon atoms. In various embodiments, the heteroalkyl group can have 1 to 4 heteroatoms, 1 to 3 heteroatoms, 1 or 2 heteroatoms, or 1 heteroatom. The heteroalkyl group of the compound can be designated as "C". 1-4 "Heteroalkyl" or similar names. Heteroalkyl groups may contain one or more heteroatoms. For example only, "C..." 1-4"Heteroalkyl" indicates that there are one to four carbon atoms in the heteroalkyl chain and one or more additional heteroatoms in the main chain. As can be understood from the above, in an embodiment having one heteroatom, the heteroatom can be seen at any position along the alkyl portion of the heteroalkyl group, including at a first position (e.g., the heteroatom of the heteroalkyl group can serve as an atom that directly attaches the alkyl group to the rest of the molecule).
[0067] The term "aryl" refers to a hydrocarbon ring system group comprising hydrogen and at least one aromatic ring. The aryl group can have 6 to 18 carbon atoms, but this definition also covers instances where the term "aryl" is not specified within a numerical range. In some embodiments, the aryl group has 6 to 10 carbon atoms. An aryl group can be designated as "C". 6-10 "Aryl", "C6 or C" 10 "Aryl" or a similar name. For example, the aryl group can be C 6-14 aryl group, C 6-10 Aryl groups, or C6 aryl groups. For the purposes of this invention, aryl groups can be monocyclic, bicyclic, tricyclic, or tetracyclic ring systems, which may include fused or bridged ring systems, wherein at least one ring in the system is aromatic. Examples of aryl groups include, but are not limited to, phenyl, acetanyl, phenanthreneyl, anthraceneyl, azulel, phenanthreneyl, fluorenyl, asymmetric indole, symmetric indole, indenyl, naphthyl, phenatenyl, pleiadenyl, pyrene, and benzo[a]phenanthreneyl.
[0068] The term "carbocyclic group" refers to a ring system whose main chain contains only carbon atoms and includes 3 to 20 ring members (3 to 20 carbon atom ring members; C 3-20 A non-aromatic ring or ring system. When the carbocyclic group is a ring system, two or more rings can be linked together by fusion, bridging, or helical linkage. Carbocyclic groups include cycloalkyl, cycloalkenyl, and cycloynyl groups. Carbocyclic groups can be of medium size, having 3 to 10 carbon atoms. Carbocyclic groups can have 3 to 6 carbon atoms. Carbocyclic groups can be designated as "C". 3-6 "Carbocyclic" or similar names. Examples of carbocyclic rings include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, 2,3-dihydro-indene, bicyclo[2.2.2]octyl, adamantyl, and spiro[4.4]nonyl.
[0069] The term "cycloalkyl" refers to a non-aromatic monocyclic or polycyclic fully saturated hydrocarbon group consisting only of carbon and hydrogen atoms. It can include fused, bridged, or spirocyclic systems with 3 to 20 carbon atom ring members (e.g., 3 to 10 ring atoms, 3 to 8 ring atoms, etc.) attached to the rest of the molecule by single bonds. No ring in a cycloalkyl ring or ring system is aromatic. Monocyclic cycloalkyl groups include, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Polycyclic cycloalkyl groups include, for example, adamantyl, norcamphenyl, decalinyl, 7,7-dimethyl-bicyclo[2.2.1]heptyl, etc.
[0070] The term "cycloalkenyl" refers to a monocyclic or polycyclic hydrocarbon group consisting only of carbon and hydrogen atoms, having one or more carbon-carbon double bonds. It can include fused, bridged, or spirocyclic systems with 3 to 20 carbocyclic members (e.g., 3 to 10 ring atoms, 4 to 10 ring atoms, etc.), and is attached to the rest of the molecule by single bonds. None of the rings in a cycloalkenyl ring or ring system is aromatic. An example is cyclohexenyl. Cycloalkenyl groups can contain 4 to 10 atoms in one or more rings. Monocyclic cycloalkenyl groups include, for example, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, etc. Polycyclic cycloalkenyl groups include, for example, bicyclic [2.2.1]hept-2-enyl, etc.
[0071] The term "cycloalkynyl" refers to a monocyclic or polycyclic hydrocarbon group consisting only of carbon and hydrogen atoms, having one or more carbon-carbon triple bonds. It can include fused, bridged, or spirocyclic systems with 8 to 20 carbocyclic members (e.g., 8 to 10 ring atoms), and is attached to the rest of the molecule by single bonds. None of the rings in a cycloalkynyl ring or ring system are aromatic. Monocyclic cycloalkynyl groups include, for example, cycloheptynyl, cyclooctyynyl, etc.
[0072] The term "heterocyclic group" refers to a tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-, or up to 20-membered monocyclic, bicyclic, and tricyclic ring system, wherein a carbon atom is together with 1 to 5 heteroatoms (each of which is independently nitrogen (e.g., N, NH, NR, etc.), oxygen, or sulfur (e.g., S, S(O), S(O)2)) to form the ring system. Heterocyclic groups or heterocyclic rings include non-heteroaryl ring systems (e.g., those rings containing heteroatoms as ring members, which are not included in the definition of "heteroaryl"). Unless otherwise specified in this specification, a heterocyclic group can be a monocyclic, bicyclic, tricyclic, or tetracyclic ring system, which may include fused, bridged, and spirocyclic systems; and the nitrogen, carbon, or sulfur atom in the heterocyclic group may optionally be oxidized; the nitrogen atom may optionally be quaternized; and the heterocyclic group may be partially or fully saturated. Examples of such heterocyclic groups include, but are not limited to, azacyclobutane, acridine, 1,3-dioxin-yl, 1,3-dioxane-hexane, 1,4-dioxane-hexane, 1,3-oxothiohexane, 1,3-oxothiohexane, 1,3-oxothiohexane, 1,3-dithiohexane-pentane, 1,3-dithiopentane, 1,4-oxothiohexane, tetrahydro-1,4-thiazinyl, dioxane-pentane, decahydroisoquinolinyl, imidazoalkyl, isothiazolyl, and isoxazolidine. Heterocyclic groups, including maleimide, morpholino, octahydroindolyl, octahydroisoindolyl, oxobutane, 2-oxopiperidinyl, 2-oxopiperidinyl, 2-oxopiperidinyl, oxazolyl, piperidinyl, piperazine, 4-piperidinone, pyrrolyl, pyrazolyl, quinine, succinimide, thiazolyl, tetrahydrofuranyl, trithiaalkyl, tetrahydropyranyl, thiomorpholinyl, thiomorpholinyl, 1-oxo-thiomorpholinyl, 1,1-dioxo-thiomorpholinyl, etc., are used. The heterocyclic group, heterocyclic ring, or heterocycle attached to the rest of the molecule by a single bond is through a ring member atom, which can be carbon or nitrogen. The heterocycle may optionally contain one or more unsaturated bonds; however, the position of these unsaturated bonds ensures that a completely delocalized π-electron system does not appear in any ring of the ring system. The heterocyclic group can be a medium-sized heterocyclic group with 3 to 10 ring members. The heterocyclic group can also be a heterocyclic group having 3 to 6 ring members. The heterocyclic group can be specified as "3-6 membered heterocyclic group" or similar names (e.g., having 3 to 6 ring members or 3 to 6 membered heterocyclic group).
[0073] The term "heteroaryl" refers to a 5- to 20-membered ring system group having 1 to 19 carbon atoms and 1 to 6 heteroatoms (each of which is independently nitrogen (e.g., N, NH, NR, etc.), oxygen, or sulfur) as ring members. The heteroaryl group can be a monocyclic, bicyclic, tricyclic, or tetracyclic ring system, which may include fused or bridged ring systems, wherein at least one ring is aromatic. The nitrogen, carbon, or sulfur atom in the heteroaryl group may optionally be oxidized, and the nitrogen atom may optionally be quaternized. The heteroaryl group may contain 5 to 14 ring members (atoms in one or more rings), 5 to 10 ring members (atoms in one or more rings), 5 to 9 ring members (atoms in one or more rings), 5 to 7 ring members (atoms in one or more rings), or 5 to 6 ring members (atoms in one or more rings). The heteroaryl group can be a medium-sized heteroaryl group with 5 to 10 ring members. The heteroaryl group can also be a heteroaryl group with 5 to 6 ring members. The heteroaryl group can also be a heteroaryl group having 6 to 9 ring members. The heteroaryl group can also have 6 ring members. The heteroaryl group can also have 9 ring members. In various embodiments, the heteroaryl group contains 1 to 6 heteroatoms, 1 to 5 heteroatoms, 1 to 4 heteroatoms, 1 to 3 heteroatoms, 1 to 2 heteroatoms, or 1 heteroatom. For example, in various embodiments, the heteroaryl group contains 1 to 5 nitrogen atoms, 1 to 4 nitrogen atoms, 1 to 3 nitrogen atoms, 1 to 2 nitrogen atoms, 2 nitrogen atoms and 1 sulfur or oxygen atom, 1 nitrogen atom and 1 sulfur or oxygen atom, 1 sulfur or oxygen atom, etc. Examples include, but are not limited to, acridine, benzimidazolyl, benzothiazolyl, benzoindolyl, benzodioxazolyl, benzofuranyl, benzooxazolyl, benzothiazolyl, benzothiadiazolyl, benzo[b][1,4]oxazolyl, 1,4-benzodioxazolidinyl, benzonaphthofuranyl, benzooxazolyl, benzodioxazolyl, benzodioxinyl, benzopyranyl, benzopyranoneyl, benzofuranyl, benzofuranoneyl, benzothiopheneyl (benzothiophene-yl), benzotriazolyl, benzo[4,6]imidazo[1,2-a]pyridyl, carbazoleyl, cenylyl, dibenzofuranyl, dibenzothiophene-yl, furanyl, isothiazolyl, imidazoyl, imidazolyl [1,2-a]pyridyl, indole, indole, indole, isoindole, dihydroindole, isodihydroindole, isoquinolinyl, inazinyl, isoxazolyl, naphridyl, oxadiazolyl, oxazolyl, 1-oxypyridyl, 1-oxypyrimidinyl, 1-oxypyrazinyl, 1-oxypyridazinyl, phenazinyl, phenothiazinyl, phenothiazinyl, phthalazinyl, pteridinyl, purine, pyrroleyl, pyrazolyl, pyridyl, pyridinyl, pyridinyl, pyrazolopyridyl, pyridinyl, pyrazolopyridyl, pyridinyl-ketone, quinazolinyl, quinoxolinyl, quinolinyl, isoquinolinyl, tetrahydroquinolinyl, thiazolyl, thiadiazolyl, triazolyl, triazolopyridyl, tetrazolyl, triazinyl, and thiophene-yl (i.e., thiophene).
[0074] The term "hydroxyl" (or "hydroxyl") refers to the -OH group.
[0075] The term "cyano" refers to the "-CN" group.
[0076] The term "oxo" refers to the =O substituent.
[0077] The term "amino" refers to the NH2 group.
[0078] The term "alkyl-amino" refers to "-NR". A H” group, where R A It is an alkyl group.
[0079] The term "di-alkyl-amino" refers to "-NR". A R B "group, wherein R A and R B Each is an alkyl group independently. R A and R B They can provide heteroaryl or heterocyclic groups along with the nitrogen to which they are attached.
[0080] As used herein, any “R” group, such as but not limited to R 1 R 2 R 3 The "R" indicates a substituent that can be attached to the indicated atom. The R group can be unsubstituted or substituted. If two "R" groups are described as "together with" (or similar language), the R groups and the atom to which they are attached can form a ring (e.g., cycloalkyl, aryl, heteroaryl, heterocyclic). When two R groups are said to form a ring (e.g., carbocyclic, heterocyclic, aryl, or heteroaryl ring) "together with" the atom to which they are attached, it means that the common unit of the atom and the two R groups is the ring. When used individually, the ring is not further limited by the definition of each R group. For example, when the following substructure exists:
[0081]
[0082] Furthermore, each example of R is defined as being independently hydrogen or alkyl, or each example of R, together with the nitrogen to which it is attached, forms a heterocyclic group, meaning that each example of R can be independently hydrogen or alkyl, or alternatively, the substructure has the following structure:
[0083]
[0084] Wherein ring A is a heterocyclic base ring containing the nitrogen depicted. As a further illustration, but without limitation, if NR A R B R of the groupA and R B The instruction "together with" means that they are covalently bonded to each other to form a ring:
[0085] .
[0086] Ring structures can be represented using the following structures (or similar structures with different rings, heteroatoms, unsaturated bonds, etc.):
[0087] .
[0088] When cyclic structures are described using this type of description, it means that the R group can be attached to any position on the ring by replacing the -H group with -R. For example, for the following rings:
[0089]
[0090] This means including any of the following structures:
[0091]
[0092] in" "Indicates that it is bonded to the rest of the structure. Similarly, for the following structure:
[0093]
[0094] in" "Indicates that it is bonded to the rest of the structure, and n is 1 to 6, contemplating any of the following structures or other variations (as will be readily understood by those skilled in the art):"
[0095] .
[0096] Additionally, when a nitrogen atom is present in the ring, a hydrogen atom can be removed from the nitrogen atom to provide substitution. Therefore, for the following structures:
[0097]
[0098] in" "Indicates that it is bonded to the rest of the structure, and n is 1 to 6, contemplating any of the following structures or other variations (as will be readily understood by those skilled in the art):"
[0099] .
[0100] Under certain conditions, the nitrogen atom in the ring can provide a cation. Therefore, for the following structures:
[0101]
[0102] in" "Indicates that it is bonded to the rest of the structure, and n is 1 to 6, contemplating any of the following structures or other variations (as will be readily understood by those skilled in the art):"
[0103] .
[0104] When two “adjacent” R groups are said to form a ring “together with the atoms to which they are attached”, it means that the atoms, the intervening bonds, and the common unit of the two R groups constitute the ring. For example, this occurs when the following substructure is present:
[0105]
[0106] And R A and R B Each is independently hydrogen or alkyl, or R 1 and R 2 When they form aryl or carbocyclic groups together with the atoms to which they are attached, it means that R 1 and R 2 The substructure may be selected from hydrogen or alkyl groups, or alternatively, the substructure has the following structure:
[0107]
[0108] Where A is an aryl ring or carbocyclic group containing the described double bond.
[0109] Regardless of where a substituent is depicted as a divalent group (i.e., having two attachment sites with the rest of the molecule), it should be understood that, unless otherwise stated, the substituent can be attached in any oriented configuration. Thus, for example, depicted as -AE- or The substituents include substituents with the following orientations: such that “A” is attached to the leftmost attachment point of the molecule, and such that “A” is attached to the rightmost attachment point of the molecule.
[0110] As noted in the definition of alkylene, it should also be understood that, depending on the context, certain naming conventions for divalent groups may include either monovalent or divalent groups. For example, when a substituent (e.g., in a genus structure) requires two attachment sites with the remainder of the molecule, the substituent should be understood to be divalent. For example, alkyl groups identified as requiring two attachment sites include divalent groups such as -CH2-, -CH2CH2-, -CH2CH(CH3)CH2-, etc. Other examples of substituents that may require two attachment sites include alkoxy, aryl, heteroaryl, carbocyclic, heterocyclic, etc.
[0111] As used herein, a group indicates a substance having a single unpaired electron, allowing the substance containing that group to covalently bond to another substance. Therefore, in this context, a group is not necessarily a free radical. Instead, a group indicates a specific portion of a larger molecule.
[0112] When a particular group (e.g., the R group) is indicated as substituted, it should be understood that such substitution occurs where the valence allows. Therefore, if the group is R and R is -H or alkyl, where R is indicated as unsubstituted or substituted, it should be understood that the "-H" atom is unsubstituted because the valence does not allow it to be substituted. On the other hand, when R is alkyl, it can be either unsubstituted or substituted.
[0113] "Solvate" refers to a compound formed through the interaction of a solvent with the compound described herein, its metabolites, or salts. A solvate is defined as a solvation form containing stoichiometric or non-stoichiometric amounts of solvent. If the solvent is water, the solvate formed is a hydrate; when the solvent is an alcohol, the solvate formed is an alcohol. Hydrates are formed by the combination of one or more water molecules with a substance, wherein water retains its molecular state as H₂O; such combinations can form one or more hydrates. Non-limiting examples of hydrates include monohydrates, dihydrates, etc. Non-limiting examples of solvates include ethanol solvates, acetone solvates, etc. The scope of this disclosure should be understood to cover all solvents of the compounds disclosed herein, as well as their stereoisomers, tautomers, and isotopically labeled forms, or pharmaceutically acceptable salts of any of the aforementioned substances.
[0114] The term "pharmaceuticalally acceptable excipient" includes any and all solvents, dispersion media, coatings, antibacterial and antifungal agents, isotonic agents, and absorption-delaying agents. The use of such media and agents for pharmaceutically active substances is well known in the art. Unless any conventional media or agent is incompatible with the active ingredient, its use in therapeutic compositions is contemplated. Additionally, various adjuvants may be included, such as those commonly used in the art.
[0115] The term "pharmaceutically acceptable salt" refers to a salt that retains the biological efficacy and properties of a compound, which is not undesirable for use in pharmaceuticals in a biological or other sense. In many cases, the compounds described herein are capable of forming acidic and / or basic salts due to the presence of amino and / or carboxyl groups or similar groups. Pharmaceutically acceptable acid addition salts can be prepared using inorganic and organic acids and / or formed using inorganic and organic acids. Inorganic acids that can be derivatized into salts include, for example, hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, etc. Organic acids that can be derivatized into salts include, for example, acetic acid, propionic acid, glycolic acid, pyruvic acid, oxalic acid, camphorsulfonic acid, maleic acid, malonic acid, succinic acid, fumaric acid, formic acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid, salicylic acid, carbonic acid, etc. Pharmaceutically acceptable base addition salts can be prepared using inorganic and organic bases and / or formed using inorganic and organic bases. Inorganic bases that can be derivatized into salts include, for example, sodium, potassium, lithium, ammonium, calcium, magnesium, iron, zinc, copper, manganese, and aluminum. Organic bases that can be derivatized into salts include, for example, primary, secondary, and tertiary amines, substituted amines (including naturally occurring substituted amines), cyclic amines, and basic ion exchange resins, specifically such as isopropylamine, trimethylamine, diethylamine, triethylamine, triisopropylamine, and ethanolamine. Other organic bases that can be derivatized into salts include, for example, ethylenediamine, N-methylglucosamine, lysine, arginine, ornithine, choline, N,N'-dibenzylethylenediamine, chloroprocaine, diethanolamine, procaine, N-benzylphenethylamine, piperazine, tri-(hydroxymethyl)-aminomethane, tetramethylammonium hydroxide, dibenzylamine, ephedrine, dehydroabimethamine, N-ethylpiperidine, benzylamine, tetramethylammonium, tetraethylammonium, methylamine, dimethylamine, ethylamine, and basic amino acids. Other salts are known in the art, as described in International Publication No. WO87 / 05297 (which is incorporated herein by reference in its entirety). Additionally, salts of the compounds described herein may exist in hydrated or dehydrated (anhydrous) forms or as solvates with other solvent molecules.
[0116] As used herein, "intermediate" compounds include structures produced by the synthetic procedure prior to obtaining the final desired compound, whether isolated in situ or generated, or not isolated. These intermediates are included within the scope of this disclosure. Exemplary embodiments of such intermediate compounds are set forth elsewhere herein.
[0117] The compounds disclosed herein may contain, for example, double bonds, one or more asymmetric carbon atoms, and bonds with hindered rotation, and therefore may exist as stereoisomers, such as double bond isomers (i.e., geometric isomers (E / Z)), enantiomers, diastereomers, and restricted configuration isomers. Therefore, unless the stereochemistry is explicitly determined, the scope of this disclosure should be understood to cover all possible stereoisomers of the illustrated compounds, including pure stereoisomers (e.g., geometrically pure, enantiomerically pure (e.g., (R), (S), (R)(R), (S)(S) etc.), diastereomerically pure, and restricted configuration pure) and mixtures of stereoisomers (e.g., both (R) and (S), diastereomers and restricted configuration isomers, or any mixture of the foregoing substances).
[0118] The term "mammal" is used in its usual biological sense. Therefore, it specifically includes, but is not limited to, primates, including apes (chimpanzees, monkeys) and humans, cattle, horses, sheep, goats, pigs, rabbits, dogs, cats, rats, and mice, but also includes many other species.
[0119] Unless otherwise stated, all figures representing amounts of components, reaction conditions, etc., used in this specification and claims should be understood to be modified by the term "about" in all cases. Therefore, unless otherwise indicated, the numerical parameters set forth in the following specification and appended claims are approximate values that may vary according to the standard deviation found in their respective test measurements.
[0120] When referring to numerical values, the term "or including and / or spanning the aforementioned values" (and its variations) is intended to include any range that includes or spans the aforementioned values. For example, when a reaction temperature is expressed as "20°C, 30°C, 40°C, 50°C, or including and / or spanning the aforementioned values," this includes the specific temperature provided (e.g., 20°C, 30°C, 40°C, or 50°C) or a temperature range extended between 20°C and 50°C, 20°C and 40°C, 20°C and 30°C, 30°C and 50°C, 30°C and 40°C, or 40°C and 50°C.
[0121] Compounds
[0122] The example provided herein, as Example 1, is a compound having formula (A):
[0123] (A)
[0124] Or a pharmaceutically acceptable salt of the compound;
[0125] in yes (i) (ii) or (iii);
[0126] m is 0 or 1;
[0127] X is N or CH;
[0128] Y is N or CR 3 ;
[0129] Z is N or CR 5 ;
[0130] b is N or CR 4 ;
[0131] R 1a It is -H, deuterium, C 1-6 Alkyl, or C 1-6 Halogenated alkyl groups;
[0132] Where R 1a It is C 1-6 Alkyl or C 1-6 When it is a haloalkyl group, then R 1a It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, -N(R) group, or a halogenated group. b 2. C 1-3 Alkyl, or C 1-3 Alkoxy;
[0133] R 1b It is -H, C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Heteroalkyl, -(C 1-6 alkylene)-O-(C 1-6 Alkyl), C 3-10 Cycloalkyl groups, or heterocyclic groups having 3 to 10 ring members;
[0134] Where R 1b It is C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Heteroalkyl, -(C 1-6 alkylene)-O-(C 1-6 Alkyl), C 3-10 When it is a cycloalkyl group, or a heterocyclic group having 3 to 10 ring members, then R 1b It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, -N(R) group, or a halogenated group. b 2. C 1-3Alkyl, or C 1-3 alkoxy group; wherein the C 1-3 Alkyl and C 1-3 Each of the alkoxy groups may be unsubstituted or substituted with 1 to 6 -F groups;
[0135] Alternatively, R 1a and R 1b Together they form C 3-10 cycloalkyl, C 3-10 Cycloalkenyl groups, or heterocyclic groups having 3 to 10 ring members;
[0136] Where R 1a and R 1b The ring can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-3 Alkyl, C 1-3 Alkoxy, -CN, C 1-6 Heteroalkyl, C 3-10 Cycloalkyl, or heterocyclic group having 3 to 10 ring members; wherein the C 1-3 Alkyl and C 1-3 Each of the alkoxy groups can be unsubstituted or surrounded by 1 to 9 halogen groups or C. 1-3 Alkyl substitution;
[0137] R 1c It is -H, C 1-6 Alkyl, or C 3-6 cycloalkyl;
[0138] Where R 1c It is C 1-6 Alkyl or C 3-6 When cycloalkyl, then R 1c It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, -N(R) group, or a halogenated group. b 2. C 1-3 Alkyl, C 1-3 alkoxy, or C 1-6 Heteroalkyl;
[0139] R 2 It is C 3-20 cycloalkyl, C 3-20 Cycloalkenyl, C 6-18 Aryl, heteroaryl having 5 to 20 ring members, or heterocyclic having 3 to 20 ring members;
[0140] Where R 2 It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group.b 2. C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Alkoxy, C 1-6 alkylene-OH, C 1-6 Alkylene-OC 1-6 Alkyl, or C 1-6 Heteroalkyl;
[0141] R 3 It is -H, C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-6 Cycloalkyl, amino, C 1-4 Alkyl-amino, di-C 1-4 Alkyl-amino, C 6-10 Aryl, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members;
[0142] Where R 3 It is C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-6 cycloalkyl, C 1-4 Alkyl-amino, di-C 1-4 Alkyl-amino, C 6-10 When R is aryl, a heteroaryl having 5 to 10 ring members, or a heterocyclic group having 5 to 10 ring members, then R 3 It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 Alkoxy, C 1-3 Alkylene-C 1-3 Alkoxy, C 1-6 Heteroalkyl, or two R 3 Substituents together form C 3-6 Carbocyclic groups or heterocyclic groups having 3 to 6 ring members;
[0143] R 4 It is -H, C 1-3 Alkyl, C 1-3 Haloalkyl, -CN, halogen, or -N(R) a )2, where R a Each instance, when it exists, is independently -H, C. 1-6 Alkyl, or -C(O)C 1-6 Alkyl; or alternatively, two R a The substituents together form a heterocyclic group having 3 to 6 ring members;
[0144] Where R a It can be unsubstituted or substituted with one or more substituents, each of which is independently -F, -Cl, -OH, C. 1-3 Alkoxy;
[0145] R 5 It is -H, C 1-6 Alkyl, C 3-6 cycloalkyl, C 1-6 Halogenated alkyl, or C 1-6 Heteroalkyl;
[0146] Where R 5 It is C 1-6 Alkyl, C 3-6 cycloalkyl, C 1-6 Halogenated alkyl, or C 1-6 When it is a heteroalkyl group, then R 5 It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, C 1-3 Alkyl, or C 1-3 Alkoxy;
[0147] Where R b Each instance, when it exists, is independently -H or C. 1-6 Alkyl; or alternatively, two R b The substituents together form a heterocyclic group having 3 to 6 ring members; and
[0148] Where R b It is C 1-6 Alkyl, or alternatively, two R b When the substituents together form a heterocyclic group having 3 to 6 ring members, then R b It can be unsubstituted or substituted with one or more substituents, each of which is independently -F, -Cl, -OH, C. 1-3 Alkyl group. In several embodiments, R 1a and R 1b Not all are methyl groups. In several embodiments, R... 1a and R 1b Not all are -CF3. In several embodiments, R 1a It is not methyl, where R 1b It is CF3. In several embodiments, R 1a and R 1b Oxyhexacyclic butyl groups are not provided together. In several embodiments, R 1a and R 1b Piperidinyl is not provided together. In several embodiments, R 3Not an unsubstituted or substituted morpholino group. In several embodiments, R 2 It is not an unsubstituted or substituted phenyl group. In several embodiments, R 2 It is not an unsubstituted or substituted heteroaryl group having 6 ring members. In several embodiments, the structure having formula (A) is further represented by a structure having formula (I) (e.g., where Z is CR). 5 Y is CR 3 m is 1, and yes In several embodiments, R 1a and R 1b Not all are H. In several embodiments, R 1a It is -H, C 1-3 Alkyl, or C 1-3 Haloalkyl. In several embodiments, R 1a It is C 1-6 Alkyl or C 1-6 Haloalkyl. In several embodiments, R 1a Is it -H or C? 1-6 Alkyl group. In several embodiments, R 1a Is it -H or C? 1-6 Haloalkyl. In several embodiments, R 1a It is C 1-6 Alkyl group. In several embodiments, R 1a It is C 1-6 Haloalkyl. In several embodiments, R 1a Yes -H. In several embodiments, R 1b It is C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-10 Cycloalkyl groups, or heterocyclic groups having 3 to 10 ring members. In several embodiments, R 1b It is C 1-6 Alkyl or C 1-6 Haloalkyl. In several embodiments, R 1b It is C 3-10 Cycloalkyl or heterocyclic groups having 3 to 10 ring members. In several embodiments, R 1b It is C 1-6 Haloalkyl. In several embodiments, R 1b It is C 3-10 Cycloalkyl. In several embodiments, R 1b It is a heterocyclic group having 3 to 10 ring members. In several embodiments, when R 1b It is C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Heteroalkyl, -(C 1-6 alkylene)-O-(C1-6 Alkyl), C 3-10 When it is a cycloalkyl group, or a heterocyclic group having 3 to 10 ring members, then R 1b It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, -N(R) group, or a halogenated group. b 2. C 1-3 Alkyl, or C 1-3 alkoxy group; wherein the C 1-3 Alkyl and C 1-3 Each of the alkoxy groups can be unsubstituted or substituted with 1 to 6 halogen groups (e.g., -F). In several embodiments, R 1a and R 1b Together they form C 3-10 Cycloalkyl or heterocyclic groups having 3 to 10 ring members. In several embodiments, R 1a and R 1b Together they form C 3-6 Cycloalkyl. In several embodiments, R 1a and R 1b Together they form C 4-6 Cycloalkyl. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group having 4 to 6 ring members. In several embodiments, R 1a and R 1b The ring can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-3 Alkyl, or C 1-3 Alkyl group. In several embodiments, R 1c Yes -H. In several embodiments, R 2 It is C 3-10 cycloalkyl, C 6-10 Aryl, heteroaryl having 5 to 10 ring members, or heterocyclic having 3 to 10 ring members. In several embodiments, R 2 It is a heteroaryl group having 5 to 10 ring members or a heterocyclic group having 3 to 10 ring members. In several embodiments, R 2 It is a heteroaryl group having 5 to 10 ring members. In several embodiments, R 3 It is C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-6 Cycloalkyl, amino, C 1-4 Alkyl-amino, di-C 1-4 Alkyl-amino, C 6-10 Aryl, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members. In several embodiments, R3 It is C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-6 Cycloalkyl, amino, C 1-2 Alkyl-amino (e.g., -NH(C)) 1-2 Alkyl groups), di-C 1-2 Alkyl-amino (e.g., -N(C)) 1-2 Alkyl)2), C 6-10 Aryl, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members. In several embodiments, R 3 It is C 3-6 cycloalkyl, di-C 1-4 Alkyl-amino, C 6-10 Aryl, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members. In several embodiments, R 3 It is C 3-6 cycloalkyl, di-C 1-4 Alkyl-amino, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members. In several embodiments, R 3 It is C 3-6 cycloalkyl, di-C 1-4 Alkyl-amino, C 6-10 Aryl, or heteroaryl having 5 to 10 ring members. In several embodiments, R 3 It is C 3-6 Cycloalkyl. In several embodiments, R 3 It is -N(Me)2. In several embodiments, R 3 It is a heteroaryl group having 5 to 10 ring members. In several embodiments, R 4 It is -H, C 1-3 Alkyl, halogen, or -N(R) a )2. In several embodiments, R 4 Is it -H or C? 1-3 Alkyl group. In several embodiments, R 4 Is it -H or -N(R)? a )2. In several embodiments, R 4 It is -N(R) a )2, R 4 It can be acylated (e.g., -NHAc). In several embodiments, R 4 It can be CN. In several embodiments, R 5 It is -H, C 1-6 Alkyl, or C 1-6 Heteroalkyl. In several embodiments, R 5 It is -H, C 1-3 Alkyl, or C 1-3Heteroalkyl. In several embodiments, R 5 Yes -H. In several embodiments, R 5 It is C 1-6 Alkyl group. In several embodiments, R 5 It is C 1-6 Heteroalkyl groups. In several embodiments, R... 5 It is a group other than -H, R 3 It is -H. In several embodiments, R 3 It is a group other than -H, R 5 Yes -H. In several embodiments, R 3 and R 5 Each of the following is -H. In several embodiments, the haloalkyl group provided in the variables of Example 1 (or any of the other embodiments provided herein) may be fully halogenated, wherein each -H of the haloalkyl chain has been exchanged for a halogen. In several embodiments, the haloalkyl group provided in the variables of Example 1 (or any of the other embodiments provided herein) is not fully halogenated and one or more (e.g., 1, 2, 3, 4, 5, 6, 7, 8 or more) CH examples are present. In several embodiments, the CH examples appearing within the haloalkyl group may appear on the same carbon (e.g., providing CH2 or CH3). In several embodiments, the haloalkyl group contains at least one and optionally multiple halogens (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or more halogens, or fully halogenated). In several embodiments, each halogen of the haloalkyl group is independently -F, -Cl, -Br, or -I. In several embodiments, each halogen of the haloalkyl group is -F or -Cl. In several embodiments, each halogen of the haloalkyl group is -F. In several embodiments, the heteroalkyl group provided in the variables of Example 1 (or any of the other embodiments provided herein) comprises heteroatoms (or one or more heteroatoms) within the alkyl backbone. In several embodiments, each heteroatom of the heteroalkyl group is independently nitrogen, oxygen, or sulfur (e.g., S, SO, or SO2). In several embodiments, each heteroatom of the heteroalkyl group is independently nitrogen or oxygen. In several embodiments, each heteroatom of the heteroalkyl group is nitrogen. In several embodiments, each heteroatom of the heteroalkyl group is oxygen. In several embodiments, the heteroalkyl group may have 1 to 4 (e.g., 1, 2, 3, or 4) heteroatoms, 1 to 3 (e.g., 1, 2, or 3) heteroatoms, 1 or 2 heteroatoms, or 1 heteroatom. In several embodiments, a compound having formula (A) or a pharmaceutically acceptable salt of said compound is further represented by a compound having formula (I) or a pharmaceutically acceptable salt thereof. For example, a structure having formula (A) is further represented by a structure having formula (I), wherein Z is CR 5 Y is CR 3 m is 1, and yes In several embodiments, R 1a and R 1b Both can be -H. In several embodiments, R 1a and R 1b Not all of them are -H.
[0149] A compound having formula (A) or a pharmaceutically acceptable salt thereof may be further represented by a structure of any of the following formulas:
[0150] (I) (II) (III) (IV) (V) (VI) (VII) (VIII) (IX) (X), (XI), or (XII),
[0151] The variables in each of these equations are those provided in equation (A) or disclosed elsewhere in this document.
[0152] A compound having formula (A) or a pharmaceutically acceptable salt thereof may be further represented by a structure of any of the following formulas:
[0153] (IAi) (IAii) (IBi) (IBii) (IBiii) (ICi) (ICii) (ICiii) (IDi) (IDii) (I-1) (I-2) (I-3) (III-1) _(III-2) (III-3) (III-4) (III-5) (IV-1) (IV-2) (VI-3) (IV-4) (XI-1) (XI-2), or (XII-1),
[0154] The variables in each of these expressions are those provided in expression (A) or as disclosed elsewhere in this document (e.g., any other expression provided herein).
[0155] The example provided herein, as Example 2, is a compound having formula (A):
[0156] (A)
[0157] Or a pharmaceutically acceptable salt of the compound;
[0158] in yes (i) (ii) or (iii);
[0159] m is 0 or 1;
[0160] X is N or CH;
[0161] Y is N or CR 3 ;
[0162] Z is N or CR 5 ;
[0163] b is N or CR 4 ;
[0164] R 1a It is -H, deuterium, C 1-6 Alkyl, or C 1-6 Halogenated alkyl groups;
[0165] Where R 1a It is C 1-6 Alkyl or C 1-6 When it is a haloalkyl group, then R 1a It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, -N(R) group, or a halogenated group. b 2. C 1-3 Alkyl, or C 1-3 Alkoxy;
[0166] R 1b It is -H, C 1-6 Alkyl, C 1-6 Haloalkyl, -(C 1-6 alkylene)-O-(C1-6 Alkyl), C 3-10 Cycloalkyl groups, or heterocyclic groups having 3 to 10 ring members and 1 to 3 heteroatom ring members, each heteroatom ring member being independently nitrogen, oxygen, or -S(O). x -, where x is 0, 1, or 2;
[0167] Where R 1b It is C 1-6 Alkyl, C 1-6 Haloalkyl, -(C 1-6 alkylene)-O-(C 1-6 Alkyl), C 3-10 When it is a cycloalkyl group, or a heterocyclic group having 3 to 10 ring members, then R 1b It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, -N(R) group, or a halogenated group. b 2. C 1-3 Alkyl, or C 1-3 alkoxy group; wherein the C 1-3 Alkyl and C 1-3 Each of the alkoxy groups can be unsubstituted or substituted with 1 to 6 F groups;
[0168] Alternatively, R 1a and R 1b Together they form C 3-10 cycloalkyl, C 3-10 Cycloalkenyl groups, or heterocyclic groups having 3 to 10 ring members and 1 to 3 heteroatom ring members, each heteroatom ring member being independently nitrogen, oxygen, or -S(O). x -, where x is 0, 1, or 2;
[0169] Where R 1a and R 1b The ring can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-3 Alkyl, C 1-3 Alkoxy, -CN, C 3-10 Cycloalkyl groups, or heterocyclic groups having 3 to 10 ring members and 1 to 3 heteroatom ring members, each heteroatom ring member being independently nitrogen, oxygen, or -S(O). w -, where w is 0, 1, or 2; where C 1-3 Alkyl and C 1-3 Each of the alkoxy groups can be unsubstituted or surrounded by 1 to 9 halogen groups or C. 1-3 Alkyl substitution;
[0170] R 1c It is -H, C1-6 Alkyl, or C 3-6 cycloalkyl;
[0171] Where R 1c It is C 1-6 Alkyl or C 3-6 When cycloalkyl, then R 1c It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, -N(R) group, or a halogenated group. b 2. C 1-3 Alkyl, or C 1-3 Alkoxy;
[0172] R 2 It is C 3-20 cycloalkyl, C 3-20 Cycloalkenyl, C 6-18 Aryl groups, heteroaryl groups having 5 to 20 ring members and 1 to 5 heteroatoms, each heteroatom being independently nitrogen, oxygen, or -S(O). y -, where y is 0 to 2, or a heterocyclic group having 3 to 20 ring members and 1 to 5 heteroatoms, each heteroatom being independently nitrogen, oxygen, or -S(O). y -, where y is between 0 and 2;
[0173] Where R 2 It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Alkoxy, C 1-6 alkylene-OH, or C 1-6 Alkylene-OC 1-6 alkyl;
[0174] R 3 It is -H, C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-6 Cycloalkyl, amino, C 1-4 Alkyl-amino, di-C 1-4 Alkyl-amino, C 6-10 Aryl groups, heteroaryl groups having 5 to 10 ring members and 1 to 5 heteroatoms, each heteroatom being independently nitrogen, oxygen, or -S(O). z -, where z is 0 to 2, or a heterocyclic group having 5 to 10 ring members and 1 to 5 heteroatoms, each heteroatom being independently nitrogen, oxygen, or -S(O). z -, where z is between 0 and 2;
[0175] Where R3 It is C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-6 cycloalkyl, C 1-4 Alkyl-amino, di-C 1-4 Alkyl-amino, C 6-10 When R is aryl, a heteroaryl having 5 to 10 ring members, or a heterocyclic group having 5 to 10 ring members, then R 3 It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkoxy, or C 1-3 Alkylene-C 1-3 Alkoxy;
[0176] R 4 It is -H, C 1-3 Alkyl, halogen, or -N(R) a )2, where R a Each instance, when it exists, is independently -H or C. 1-6 Alkyl; or alternatively, two R a The substituents together form a heterocyclic group having 3 to 6 ring members and 1 to 2 heteroatom ring members, each heteroatom ring member being independently nitrogen or oxygen;
[0177] Where R a It can be unsubstituted or substituted with one or more substituents, each of which is independently -F, -Cl, -OH, C. 1-3 Alkoxy;
[0178] R 5 It is -H, C 1-6 Alkyl, C 3-6 cycloalkyl, or C 1-6 Halogenated alkyl groups;
[0179] Where R 5 It is C 1-6 Alkyl, C 3-6 cycloalkyl, or C 1-6 When it is a haloalkyl group, then R 5 It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, C 1-3 Alkyl, or C 1-3 Alkoxy;
[0180] Where R b Each instance, when it exists, is independently -H or C. 1-6Alkyl; or alternatively, two R b The substituents together form a heterocyclic group having 3 to 6 ring members and 1 to 2 heteroatoms, each heteroatom being independently nitrogen or oxygen; and
[0181] Where R b It is C 1-6 Alkyl, or alternatively, two R b When the substituents together form a heterocyclic group having 3 to 6 ring members, then R b It can be unsubstituted or substituted with one or more substituents, each of which is independently -F, -Cl, -OH, C. 1-3 Alkyl group.
[0182] The compound or salt provided as Example 3 in this document is as described in Example 1 or 2, wherein, when the compound having formula (A) is... When represented, b is CH or N, R 2 It is an unsubstituted or substituted pyridinyl, an unsubstituted or substituted pyrimidinyl, an unsubstituted or substituted pyrrolopyridinyl, an unsubstituted or substituted indazole, an unsubstituted or substituted imidazopyridinyl, or an unsubstituted or substituted quinolinyl, and 1) R 1a and R 1b Both are methyl or 2) R 1a and R 1b If oxobutyric compounds are supplied together, then R 3 It's not morpholino.
[0183] The compound or salt described in Examples 1 to 3 is provided as Example 4 in this document, wherein the compound having formula (A) is composed of... When represented, b is CH or N, R 2 It is an unsubstituted or substituted phenyl, an unsubstituted or substituted piperidinyl, an unsubstituted or substituted thiazolyl, an unsubstituted or substituted pyridinyl, an unsubstituted or substituted pyrimidinyl, an unsubstituted or substituted 2,3,4,5-tetrahydropyridinyl, an unsubstituted or substituted indolyl, an unsubstituted or substituted imidazopyridinyl, an unsubstituted or substituted indazole, an unsubstituted or substituted pyrrolopyridinyl, an unsubstituted or substituted pyrrolopyridinyl, an unsubstituted or substituted quinolinyl, an unsubstituted or substituted isoquinolinyl, or an unsubstituted or substituted quinolinyl, and R 1a and R 1b Each of the methyl groups in R is an independent methyl group. 3 It is neither an unsubstituted nor a substituted morpholino group.
[0184] The compound or salt provided herein as Example 5 is as described in any one of Examples 1 to 4, wherein, when the compound having formula (A) is... Indicates and R 1a and R 1b When all are methyl groups, then R 2 It is not an unsubstituted or substituted phenyl, unsubstituted naphthyl, unsubstituted pyridyl, unsubstituted benzothiophene, or unsubstituted phenanthrene.
[0185] The compound or salt provided herein as Example 6 is as described in any one of Examples 1 to 5, wherein, when the compound having formula (A) is... Indicates and R 1a and R 1b Both are methyl groups, R 1a and R 1b Both are -CF3, R 1a It is methyl and R 1b It's CF3, or R. 1a and R 1b If both unsubstituted and substituted piperidinyl groups are provided together, then R 2 It is not an unsubstituted or substituted phenyl, unsubstituted or substituted pyridyl, unsubstituted or substituted 2,3,4,5-tetrahydropyridyl, unsubstituted or substituted pyrimidinyl, unsubstituted or substituted naphthyl, or unsubstituted or substituted benzothiophene.
[0186] The compound or salt provided herein as Example 7 is as described in any one of Examples 1 to 6, wherein, when the compound having formula (A) is... Indicates and R 1a and R 1b All are methyl or R 1a and R 1b When both unsubstituted and substituted piperidinyl groups are provided together, then R 2 It is not an unsubstituted or substituted piperidinyl, an unsubstituted or substituted pyrimidinyl, or an unsubstituted or substituted 2,3,4,5-tetrahydropyridinyl.
[0187] The compound or salt provided herein as Example 8 is as described in any one of Examples 1 to 7, wherein, when the compound having formula (A) is... or When expressed, R 3 It's not morpholino.
[0188] The compound or salt provided herein as Example 9 is as described in any one of Examples 1 to 8, wherein, when the compound having formula (A) is... This indicates that b is CH or N, and R is R. 2 It is an unsubstituted or substituted pyrimidinyl group, an unsubstituted or substituted 2,3,4,5-tetrahydropyridinyl group, or an unsubstituted or substituted indazole group, and 1)R1a and R 1b Each of them is independently an unsubstituted or substituted methyl group, 2) R 1a and R 1b Each of them is independently an unsubstituted or substituted ethyl group, 3) R 1a and R 1b Together, provide unsubstituted or substituted piperidinyl groups, 4) R 1a and R 1b Together, provide oxetane butyl, or 5) R 1a and R 1b When provided together with unsubstituted or substituted thiaranyl groups, then R 3 It is neither an unsubstituted nor a substituted morpholino group.
[0189] The compound or salt provided herein as Example 10 is as described in any one of Examples 1 to 9, wherein R 3 It is neither an unsubstituted nor a substituted morpholino group.
[0190] The compound or salt provided herein as Example 11 is as described in any one of Examples 1 to 10, wherein R 1a Not -H.
[0191] The compound or salt provided herein as Example 12 is any one of Examples 1 to 11, wherein R 1b Not -H.
[0192] The compound or salt provided herein as Example 13 is as described in any one of Examples 1 to 12, wherein yes (i) or (ii).
[0193] The compound or salt provided herein as Example 14 is as described in any one of Examples 1 to 12, wherein yes (i).
[0194] The compound or salt provided herein as Example 15 is any one of Examples 1 to 12, wherein... yes (ii).
[0195] The compound or salt provided herein as Example 16 is as described in any one of Examples 1 to 12, wherein
[0196] yes (I) (II) (III) (IV) (V) (VI) (VII) (VIII) (IX) (X), (XI), or (XII).
[0197] The compound or salt provided herein as Example 17 is any one of Examples 1 to 16, wherein
[0198] yes For example, in several embodiments, m is 0.
[0199] The compound or salt provided herein as Example 18 is any one of Examples 1 to 16, wherein
[0200] yes For example, in several embodiments, m is 1.
[0201] The compound or salt provided herein as Example 19 is any one of Examples 1 to 18, wherein X is N.
[0202] The compound or salt provided herein as Example 20 is any one of Examples 1 to 18, wherein X is CH.
[0203] The compound or salt provided herein as Example 21 is as described in any one of Examples 1 to 20, wherein Y is N.
[0204] The compound or salt provided herein as Example 22 is any one of Examples 1 to 20, wherein Y is a CR 3 .
[0205] The compound or salt provided herein as Example 23 is as described in any one of Examples 1 to 22, wherein Z is N.
[0206] The compound or salt provided herein as Example 24 is any one of Examples 1 to 22, wherein Z is CR 5 .
[0207] The compound or salt provided herein as Example 25 is as described in any one of Examples 1 to 24, wherein b is N.
[0208] The compound or salt provided herein as Example 26 is as described in any one of Examples 1 to 24, wherein b is a CR4 .
[0209] The example provided herein, exemplified as Example 27, is a compound having formula (I).
[0210] (I)
[0211] Or a pharmaceutically acceptable salt of the compound;
[0212] in
[0213] X is N or CH;
[0214] R 1a It is -H, C 1-6 Alkyl, or C 1-6 Halogenated alkyl groups;
[0215] Where R 1a It is C 1-6 Alkyl or C 1-6 When it is a haloalkyl group, then R 1a It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, -N(R) group, or a halogenated group. b 2. C 1-3 Alkyl, or C 1-3 Alkoxy;
[0216] R 1b It is -H, C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Heteroalkyl, -(C 1-6 alkylene)-O-(C 1-6 Alkyl), C 3-10 Cycloalkyl groups, or heterocyclic groups having 3 to 10 ring members;
[0217] Where R 1b It is C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Heteroalkyl, C 3-10 When it is a cycloalkyl group, or a heterocyclic group having 3 to 10 ring members, then R 1b It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, -N(R) group, or a halogenated group. b 2. C 1-3 Alkyl, or C 1-3 alkoxy group; wherein the C 1-3 Alkyl and C 1-3 Each of the alkoxy groups may be unsubstituted or substituted with 1 to 6 -F groups;
[0218] Alternatively, R1a and R 1b Together they form C 3-10 cycloalkyl, C 3-10 Cycloalkenyl groups, or heterocyclic groups having 3 to 10 ring members;
[0219] Where R 1a and R 1b The ring can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-3 Alkyl, C 1-3 alkoxy, or C 1-6 Heteroalkyl; wherein the C 1-3 Alkyl and C 1-3 Each of the alkoxy groups can be unsubstituted or surrounded by 1 to 9 halogen groups or C. 1-3 Alkyl substitution;
[0220] R 1c It is -H, C 1-6 Alkyl, or C 3-6 cycloalkyl;
[0221] Where R 1c It is C 1-6 Alkyl or C 3-6 When cycloalkyl, R 1c It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, -N(R) group, or a halogenated group. b 2. C 1-3 Alkyl, C 1-3 alkoxy, or C 1-6 Heteroalkyl;
[0222] R 2 It is C 3-20 cycloalkyl, C 3-20 Cycloalkenyl, C 6-18 Aryl, heteroaryl having 5 to 20 ring members, or heterocyclic having 3 to 20 ring members;
[0223] Where R 2 It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Alkoxy, C 1-6 alkylene-OH, C 1-6 Alkylene-OC 1-6 Alkyl, or C 1-6 Heteroalkyl;
[0224] R 3 It is -H, C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-6 Cycloalkyl, amino, C 1-4 Alkyl-amino, di-C 1-4 Alkyl-amino, C 6-10 Aryl, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members;
[0225] Where R 3 It is C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-6 cycloalkyl, C 1-4 Alkyl-amino, di-C 1-4 Alkyl-amino, C 6-10 When R is aryl, a heteroaryl having 5 to 10 ring members, or a heterocyclic group having 5 to 10 ring members, then R 3 It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 Alkoxy, C 1-3 Alkylene-C 1-3 Alkoxy, C 1-6 Heteroalkyl, or two R 3 Substituents together form C 3-6 Carbocyclic groups or heterocyclic groups having 3 to 6 ring members;
[0226] R 4 Is it -H or -N(R)? a )2, where R a Each instance, when it exists, is independently -H or C. 1-6 Alkyl; or alternatively, two R a The substituents together form a heterocyclic group having 3 to 6 ring members;
[0227] Where R a It can be unsubstituted or substituted with one or more substituents, each of which is independently -F, -Cl, -OH, C. 1-3 Alkoxy;
[0228] R 5 It is -H, C 1-6 Alkyl, C 3-6 cycloalkyl, C 1-6 Halogenated alkyl, or C 1-6 Heteroalkyl;
[0229] Where R 5 It is C 1-6 Alkyl, C 3-6 cycloalkyl, C 1-6 Halogenated alkyl, or C 1-6 When it is a heteroalkyl group, then R 5 It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, C 1-3 Alkyl, or C 1-3 Alkoxy;
[0230] Where R b Each instance, when it exists, is independently -H or C. 1-6 Alkyl; or alternatively, two R b The substituents together form a heterocyclic group having 3 to 6 ring members; and
[0231] Where R b It is C 1-6 Alkyl, or alternatively, two R b When the substituents together form a heterocyclic group having 3 to 6 ring members, then R b It can be unsubstituted or substituted with one or more substituents, each of which is independently -F, -Cl, -OH, C. 1-3 Alkyl group. In several embodiments, R 1a It is -H, C 1-3 Alkyl, or C 1-3 Haloalkyl. In several embodiments, R 1a It is C 1-6 Alkyl or C 1-6 Haloalkyl. In several embodiments, R 1a Is it -H or C? 1-6 Alkyl group. In several embodiments, R 1a Is it -H or C? 1-6 Haloalkyl. In several embodiments, R 1a It is C 1-6 Alkyl group. In several embodiments, R 1a It is C 1-6 Haloalkyl. In several embodiments, R 1a Yes -H. In several embodiments, R 1b It is C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Heteroalkyl, C 3-10 Cycloalkyl groups, or heterocyclic groups having 3 to 10 ring members. In several embodiments, R 1b It is C 1-6 Alkyl, C 1-6Halogenated alkyl, or C 1-6 Heteroalkyl. In several embodiments, R 1b It is C 3-10 Cycloalkyl or heterocyclic groups having 3 to 10 ring members. In several embodiments, R 1b It is C 1-6 Haloalkyl. In several embodiments, R 1b It is C 3-10 Cycloalkyl. In several embodiments, R 1b It is a heterocyclic group having 3 to 10 ring members. In several embodiments, R 1a and R 1b Together they form C 3-10 Cycloalkyl or heterocyclic groups having 3 to 10 ring members. In several embodiments, R 1a and R 1b Together they form C 3-6 Cycloalkyl. In several embodiments, R 1a and R 1b Together they form C 4-6 Cycloalkyl. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group having 4 to 6 ring members. In several embodiments, R 1a and R 1b The ring can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-3 Alkyl, or C 1-3 Alkyl group. In several embodiments, R 1c Yes -H. In several embodiments, R 2 It is C 3-10 cycloalkyl, C 6-10 Aryl, heteroaryl having 5 to 10 ring members, or heterocyclic having 3 to 10 ring members. In several embodiments, R 2 It is a heteroaryl group having 5 to 10 ring members or a heterocyclic group having 3 to 10 ring members. In several embodiments, R 2 It is a heteroaryl group having 5 to 10 ring members. In several embodiments, R 3 It is C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-6 Cycloalkyl, amino, C 1-4 Alkyl-amino, di-C 1-4 Alkyl-amino, C 6-10 Aryl, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members. In several embodiments, R 3 It is C 1-6Alkyl, C 1-6 Haloalkyl, C 3-6 Cycloalkyl, amino, C 1-2 Alkyl-amino (e.g., -NH(C)) 1-2 Alkyl groups), di-C 1-2 Alkyl-amino (e.g., -N(C)) 1-2 Alkyl)2), C 6-10 Aryl, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members. In several embodiments, R 3 It is C 3-6 cycloalkyl, di-C 1-4 Alkyl-amino, C 6-10 Aryl, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members. In several embodiments, R 3 It is C 3-6 cycloalkyl, di-C 1-4 Alkyl-amino, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members. In several embodiments, R 3 It is C 3-6 cycloalkyl, di-C 1-4 Alkyl-amino, C 6-10 Aryl, or heteroaryl having 5 to 10 ring members. In several embodiments, R 3 It is C 3-6 Cycloalkyl. In several embodiments, R 3 It is -N(Me)2. In several embodiments, R 3 It is a heteroaryl group having 5 to 10 ring members. In several embodiments, R 4 Is it -H or -N(R)? a )2. In several embodiments, R 4 It is -N(R) a ) 22 R 4 It can be acylated (e.g., -NHAc). In several embodiments, R 4 It can be CN. In several embodiments, R 5 It is -H, C 1-6 Alkyl, or C 1-6 Heteroalkyl. In several embodiments, R 5 It is -H, C 1-3 Alkyl, or C 1-3 Heteroalkyl. In several embodiments, R 5 Yes -H. In several embodiments, R 5 It is C 1-6 Alkyl group. In several embodiments, R 5 It is C 1-6 Heteroalkyl groups. In several embodiments, R...5 It is a group other than -H, R 3 It is -H. In several embodiments, R 3 It is a group other than -H, R 5 Yes -H. In several embodiments, R 3 and R 5 Each of the following is -H. In several embodiments, the haloalkyl group provided in the variables of Example 27 (or any of the other embodiments provided herein) may be fully halogenated, wherein each -H of the haloalkyl chain has been exchanged for a halogen. In several embodiments, the haloalkyl group provided in the variables of Example 27 (or any of the other embodiments provided herein) is not fully halogenated and one or more (e.g., 1, 2, 3, 4, 5, 6, 7, 8 or more) CH examples are present. In several embodiments, the CH examples appearing within the haloalkyl group may appear on the same carbon (e.g., providing CH2 or CH3). In several embodiments, the haloalkyl group contains at least one and optionally multiple halogens (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or more halogens, or fully halogenated). In several embodiments, each halogen of the haloalkyl group is independently -F, -Cl, -Br, or -I. In several embodiments, each halogen of the haloalkyl group is -F or -Cl. In several embodiments, each halogen of the haloalkyl group is -F. In several embodiments, the heteroalkyl group provided in the variables of Example 27 (or any of the other embodiments provided herein) comprises heteroatoms (or one or more heteroatoms) within the alkyl backbone. In several embodiments, each heteroatom of the heteroalkyl group is independently nitrogen, oxygen, or sulfur (e.g., S, SO, or SO2). In several embodiments, each heteroatom of the heteroalkyl group is independently nitrogen or oxygen. In several embodiments, each heteroatom of the heteroalkyl group is nitrogen. In several embodiments, each heteroatom of the heteroalkyl group is oxygen. In several embodiments, the heteroalkyl group may have 1 to 4 (e.g., 1, 2, 3, or 4) heteroatoms, 1 to 3 (e.g., 1, 2, or 3) heteroatoms, 1 or 2 heteroatoms, or 1 heteroatom. In several embodiments, a compound having formula (A) or a pharmaceutically acceptable salt of said compound is further represented by a compound having formula (I) or a pharmaceutically acceptable salt thereof. For example, a structure having formula (A) is further represented by a structure having formula (I), wherein Z is CR 5 Y is CR 3 m is 1, and yes In several embodiments, R 1a and R 1b Both can be -H. In several embodiments, R 1a and R 1b Not all of them are -H.
[0232] The example provided herein, exemplified as Example 28, is a compound having formula (I).
[0233] (I)
[0234] Or a pharmaceutically acceptable salt of the compound;
[0235] in
[0236] X is N or CH;
[0237] R 1a It is -H, C 1-6 Alkyl, or C 1-6 Halogenated alkyl groups;
[0238] Where R 1a It is C 1-6 Alkyl or C 1-6 When it is a haloalkyl group, then R 1a It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, -N(R) group, or a halogenated group. b 2. C 1-3 Alkyl, or C 1-3 Alkoxy;
[0239] R 1b It is -H, C 1-6 Alkyl, C 1-6 Haloalkyl, -(C 1-6 alkylene)-O-(C 1-6 Alkyl), C 3-10 Cycloalkyl groups, or heterocyclic groups having 3 to 10 ring members and 1 to 3 heteroatom ring members, each heteroatom ring member being independently nitrogen, oxygen, or -S(O). x -, where x is 0, 1, or 2;
[0240] Where R 1b It is C 1-6 Alkyl, C 1-6 Haloalkyl, -(C 1-6 alkylene)-O-(C 1-6 Alkyl), C 3-10 When it is a cycloalkyl group, or a heterocyclic group having 3 to 10 ring members, then R 1b It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, -N(R) group, or a halogenated group. b 2. C 1-3 Alkyl, or C 1-3 alkoxy group; wherein the C 1-3 Alkyl and C 1-3Each of the alkoxy groups may be unsubstituted or substituted with 1 to 6 -F groups;
[0241] Alternatively, R 1a and R 1b Together they form C 3-10 cycloalkyl, C 3-10 Cycloalkenyl groups, or heterocyclic groups having 3 to 10 ring members and 1 to 3 heteroatom ring members, each heteroatom ring member being independently nitrogen, oxygen, or -S(O). x -, where x is 0, 1, or 2;
[0242] Where R 1a and R 1b The ring can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-3 Alkyl, or C 1-3 alkoxy group; wherein the C 1-3 Alkyl and C 1-3 Each of the alkoxy groups can be unsubstituted or surrounded by 1 to 9 halogen groups or C. 1-3 Alkyl substitution;
[0243] R 1c It is -H, C 1-6 Alkyl, or C 3-6 cycloalkyl;
[0244] Where R 1c It is C 1-6 Alkyl or C 3-6 When cycloalkyl, R 1c It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, -N(R) group, or a halogenated group. b 2. C 1-3 Alkyl, or C 1-3 Alkoxy;
[0245] R 2 It is C 3-20 cycloalkyl, C 3-20 Cycloalkenyl, C 6-18 Aryl groups, heteroaryl groups having 5 to 20 ring members and 1 to 5 heteroatoms, each heteroatom being independently nitrogen, oxygen, or -S(O). y -, where y is 0 to 2, or a heterocyclic group having 3 to 20 ring members and 1 to 5 heteroatoms, each heteroatom being independently nitrogen, oxygen, or -S(O). y -, where y is between 0 and 2;
[0246] Where R 2It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Alkoxy, C 1-6 alkylene -OH or -C 1-6 Alkylene-OC 1-6 alkyl;
[0247] R 3 It is -H, C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-6 Cycloalkyl, amino, C 1-4 Alkyl-amino, di-C 1-4 Alkyl-amino, C 6-10 Aryl groups, heteroaryl groups having 5 to 10 ring members and 1 to 5 heteroatoms, each heteroatom being independently nitrogen, oxygen, or -S(O). z -, where z is 0 to 2, or a heterocyclic group having 5 to 10 ring members and 1 to 5 heteroatoms, each heteroatom being independently nitrogen, oxygen, or -S(O). z -, where z is between 0 and 2;
[0248] Where R 3 It is C 1-6 Alkyl, C 1-6 Haloalkyl, C 3-6 cycloalkyl, C 1-4 Alkyl-amino, di-C 1-4 Alkyl-amino, C 6-10 When R is aryl, a heteroaryl having 5 to 10 ring members, or a heterocyclic group having 5 to 10 ring members, then R 3 It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, oxo, -N(R) group. b 2. C 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 Alkoxy, C 1-3 Alkylene-C 1-3 Alkoxy, C 1-6 Heteroalkyl, or two R 3 Substituents together form C 3-6 A carbocyclic group or a heterocyclic group having 3 to 6 ring members and 1 to 2 heteroatom ring members, each heteroatom ring member being independently nitrogen or oxygen;
[0249] R 4 Is it -H or -N(R)? a )2, where Ra Each instance, when it exists, is independently -H or C. 1-6 Alkyl; or alternatively, two R a The substituents together form a heterocyclic group having 3 to 6 ring members and 1 to 2 heteroatom ring members, each heteroatom ring member being independently nitrogen or oxygen;
[0250] Where R a It can be unsubstituted or substituted with one or more substituents, each of which is independently -F, -Cl, -OH, C. 1-3 Alkoxy;
[0251] R 5 It is -H, C 1-6 Alkyl, C 3-6 cycloalkyl, or C 1-6 Halogenated alkyl groups;
[0252] Where R 5 It is C 1-6 Alkyl, C 3-6 cycloalkyl, or C 1-6 When it is a haloalkyl group, then R 5 It can be unsubstituted or substituted with one or more substituents, each of which is independently a halogen, -OH, C 1-3 Alkyl, or C 1-3 Alkoxy;
[0253] Where R b Each instance, when it exists, is independently -H or C. 1-6 Alkyl; or alternatively, two R b The substituents together form a heterocyclic group having 3 to 6 ring members and 1 to 3 heteroatoms, each heteroatom being independently nitrogen or oxygen; and
[0254] Where R b It is C 1-6 Alkyl, or alternatively, two R b When the substituents together form a heterocyclic group having 3 to 6 ring members, then R b It can be unsubstituted or substituted with one or more substituents, each of which is independently -F, -Cl, -OH, C. 1-3 Alkyl group.
[0255] The compound or salt described in Examples 27 or 28 provided herein as Example 29 is a compound or salt having Formula (I) that is not 6-phenyl-4-(trifluoromethyl)thieno[2,3-b]pyridine-2-methanol, 6-cyclopropylbenzo[b]thieno-2-methanol, 6-phenylbenzo[b]thieno-2-methanol, or 6-[3-[(dimethylamino)methyl]bicyclo[2.2.1]hept-2-en-2-yl]benzo[b]thieno-2-methanol. For example, in several examples, the compound having Formula (I) is not 6-phenyl-4-(trifluoromethyl)thieno[2,3-b]pyridine-2-methanol. In several examples, the compound having Formula (I) is not 6-cyclopropylbenzo[b]thieno-2-methanol. In several examples, the compound having Formula (I) is not 6-phenylbenzo[b]thieno-2-methanol. In several embodiments, the compound having formula (I) is not 6-[3-[(dimethylamino)methyl]bicyclo[2.2.1]hept-2-en-2-yl]benzo[b]thiophene-2-methanol.
[0256] The compound or salt provided herein as Example 30 is as described in any one of Examples 27 to 29, wherein R 2 It is not an unsubstituted phenyl group.
[0257] The compound or salt provided herein as Example 31 is as described in any one of Examples 27 to 30, wherein, when R 2 If it is an unsubstituted cyclopropyl, an unsubstituted phenyl, or an unsubstituted or substituted cycloalkenyl, then R 1a R 1b and R 1c One of them is not -H.
[0258] The compound or salt provided herein as Example 32 is any one of Examples 27 to 31, wherein X is N.
[0259] The compound or salt provided herein as Example 33 is any one of Examples 27 to 31, wherein X is CH.
[0260] The compound or salt provided herein as Example 34 is any one of Examples 1 to 33, wherein R 1a It is -H, deuterium, unsubstituted or substituted C 1-3 Alkyl, or unsubstituted or substituted C 1-3 Haloalkyl. For example, in several embodiments, R 1a It is -H, unsubstituted or substituted C 1-3 Alkyl or unsubstituted or substituted C 1-3 Haloalkyl. In several embodiments, R 1aIt is -H or unsubstituted or substituted C 1-3 Haloalkyl. In several embodiments, R 1a Is it unsubstituted or substituted C? 1-3 Alkyl or unsubstituted or substituted C 1-3 Haloalkyl. In several embodiments, R 1a It is -H, deuterium, or unsubstituted or substituted C. 1-3 Haloalkyl. In several embodiments, R 1a It is deuterium, unsubstituted or substituted C. 1-3 Alkyl or unsubstituted or substituted C 1-3 Haloalkyl. In several embodiments, R 1a It is -H, deuterium, or unsubstituted or substituted C. 1-3 Alkyl group. In several embodiments, R 1a It is -H or deuterium. In several embodiments, R 1a Is it unsubstituted or substituted C? 1-2 Alkyl group. In several embodiments, R 1a It is a methyl group. In several embodiments, R... 1a It is an unsubstituted or substituted C2 alkyl group. In several embodiments, R 1a It is an unsubstituted or substituted C3 alkyl group. In several embodiments, R 1a Is it unsubstituted or substituted C? 1-2 Haloalkyl. In several embodiments, R 1a It is an unsubstituted or substituted C1 haloalkyl group (e.g., -CF3). In several embodiments, R 1a It is an unsubstituted or substituted C2 haloalkyl group. In several embodiments, R 1a It is an unsubstituted or substituted C3 haloalkyl group.
[0261] The compound or salt provided herein as Example 35 is any one of Examples 1 to 33, wherein R 1a Is it unsubstituted or substituted C? 1-3 Alkyl group. For example, in several embodiments, R 1a It is unreplaced C 1-2 Alkyl group. In several embodiments, R 1a It is unreplaced C 2-3 Alkyl group. In several embodiments, R 1a It is an unsubstituted C1 alkyl group. In several embodiments, R 1a It is an unsubstituted C2 alkyl group. In several embodiments, R 1a It is an unsubstituted C3 alkyl group. In several embodiments, R 1a It is the replacement of C 1-2 Alkyl group. In several embodiments, R 1a It is the replacement of C2-3 Alkyl group. In several embodiments, R 1a It is a substituted C1 alkyl group. In several embodiments, R 1a It is a substituted C2 alkyl group. In several embodiments, R 1a It is a substituted C3 alkyl group.
[0262] The compound or salt provided herein as Example 36 is as described in any one of Examples 1 to 33, wherein R 1a Is it unsubstituted or substituted C? 1-3 Haloalkyl. For example, in several embodiments, R 1a It is unreplaced C 1-2 Haloalkyl. In several embodiments, R 1a It is unreplaced C 2-3 Haloalkyl. In several embodiments, R 1a It is an unsubstituted C1 haloalkyl group (e.g., -CF3). In several embodiments, R 1a It is an unsubstituted C2 haloalkyl group. In several embodiments, R 1a It is an unsubstituted C3 haloalkyl group. In several embodiments, R 1a It is the replacement of C 1-2 Haloalkyl. In several embodiments, R 1a It is the replacement of C 2-3 Haloalkyl. In several embodiments, R 1a It is a substituted C1 haloalkyl group (e.g., -CF3). In several embodiments, R 1a It is a substituted C2 haloalkyl group. In several embodiments, R 1a It is a substituted C3 haloalkyl group.
[0263] The compound or salt provided herein as Example 37 is any one of Examples 1 to 36, wherein R 1a It is substituted by 1, 2, 3, or 4 substituents. For example, in several embodiments, R 1a It is substituted with 1 to 4 substituents. In several embodiments, R 1a It is substituted with 1 to 3 substituents. In several embodiments, R 1a It is substituted with 1 to 2 substituents. In several embodiments, R 1a It is substituted with 2 to 4 substituents. In several embodiments, R 1a It is substituted with 3 to 4 substituents. In several embodiments, R 1a It is substituted by 2 to 3 substituents.
[0264] The compound or salt provided herein as Example 38 is as described in any one of Examples 27 to 37, wherein R 1a It is substituted by 1, 2 or 3 substituents.
[0265] The compound or salt provided herein as Example 39 is any one of Examples 1 to 38, wherein R 1a It is substituted by one or two substituents.
[0266] The compound or salt provided herein as Example 40 is any one of Examples 1 to 39, wherein R 1a It is replaced by one substituent.
[0267] The compound or salt provided herein as Example 41 is as described in any one of Examples 1 to 40, wherein, when R 1a When replaced, each R 1a The substituents are independently -F, -OH, or C. 1-3 Alkyl groups. For example, in several embodiments, each R 1a The substituents are independently -F or -OH. In several embodiments, each R 1a The substituents are independently -OH or C. 1-3 Alkoxy. In several embodiments, each R 1a The substituent is independently -F or C. 1-3 Alkyl group. In several embodiments, R 1a It is substituted with -F, -OH, C1 alkoxy, C2 alkoxy, and / or C3 alkoxy. In several embodiments, each R 1a The substituents are independently -C1 alkoxy, C2 alkoxy, or C3 alkoxy. In several embodiments, R 1a Substituted with a -C1 alkoxy group. In several embodiments, R 1a Replaced by a C2 alkoxy group. In several embodiments, R... 1a Replaced by a C3 alkoxy group. In several embodiments, R... 1a Replaced by -F. In several embodiments, R 1a It is replaced by -OH.
[0268] The compound or salt provided herein as Example 42 is any one of Examples 1 to 36, wherein R 1a It is not replaced.
[0269] The compound or salt provided herein as Example 43 is any one of Examples 1 to 33, wherein R 1a It is -H, methyl, or -CF3. For example, in several embodiments, R 1a It is -H or methyl. In several embodiments, R 1a It is -H or -CF3. In several embodiments, R 1a It is methyl or -CF3. In several embodiments, R 1aYes -H. In several embodiments, R 1a It is a methyl group. In several embodiments, R... 1a It is -CF3.
[0270] The compound or salt provided herein as Example 44 is any one of Examples 1 to 33, wherein R 1a Yes, it's -H.
[0271] The compound or salt provided herein as Example 45 is any one of Examples 1 to 33, wherein R 1a It is -CH3.
[0272] The compound or salt provided herein as Example 46 is any one of Examples 1 to 33, wherein R 1a It is -CF3.
[0273] The compound or salt provided herein as Example 47 is any one of Examples 1 to 46, wherein R 1b It is -H, unsubstituted or substituted C 1-3 Alkyl, unsubstituted or substituted C 1-3 Halogenated alkyl, unsubstituted or substituted C 3-6 Cycloalkyl groups, or unsubstituted or substituted heterocyclic groups having 3 to 6 ring members. For example, in several embodiments, R 1b Is it unsubstituted or substituted C? 1-3 Alkyl, unsubstituted or substituted C 1-3 Halogenated alkyl, unsubstituted or substituted C 3-6 Cycloalkyl, or unsubstituted or substituted heterocyclic groups having 3 to 6 ring members. In several embodiments, R 1b Is it unsubstituted or substituted C? 1-3 Halogenated alkyl, unsubstituted or substituted C 3-6 Cycloalkyl, or unsubstituted or substituted heterocyclic groups having 3 to 6 ring members. In several embodiments, R 1b Is it unsubstituted or substituted C? 1-3 Alkyl, unsubstituted or substituted C 3-6 Cycloalkyl, or unsubstituted or substituted heterocyclic groups having 3 to 6 ring members. In several embodiments, R 1b Is it unsubstituted or substituted C? 1-3 Alkyl, unsubstituted or substituted C 1-3 Halogenated alkyl groups, or unsubstituted or substituted C4 groups 3-6 Cycloalkyl. In several embodiments, R 1b Is it unsubstituted or substituted C? 1-3 Alkyl or unsubstituted or substituted C 3-6 Cycloalkyl. In several embodiments, R1b Is it unsubstituted or substituted C? 1-3 Alkyl or unsubstituted or substituted C 1-3 Haloalkyl. In several embodiments, R 1b Is it unsubstituted or substituted C? 3-6 Cycloalkyl or heterocyclic groups having 3 to 6 ring members. In several embodiments, R 1b Is it unsubstituted or substituted C? 1-3 Halogenated alkyl groups or unsubstituted or substituted heterocyclic groups having 3 to 6 ring members. In several embodiments, R 1b Is it unsubstituted or substituted C? 1-3 Halogenated alkyl or unsubstituted or substituted C 3-6 Cycloalkyl. In several embodiments, wherein R 1b It is an unsubstituted or substituted alkyl group, R 1b Is it unsubstituted or substituted C? 1-2 Alkyl group. In several embodiments, R... 1b It is an unsubstituted or substituted alkyl group, R 1b Is it unsubstituted or substituted C? 2-3 Alkyl group. In several embodiments, R... 1b It is an unsubstituted or substituted alkyl group, R 1b It is an unsubstituted or substituted C1 alkyl group (e.g., methyl). In several embodiments, R... 1b It is an unsubstituted or substituted alkyl group, R 1b It is an unsubstituted or substituted C2 alkyl group (e.g., ethyl). In several embodiments, R... 1b It is an unsubstituted or substituted alkyl group, R 1b It is an unsubstituted or substituted C3 alkyl group (e.g., isopropyl or propyl). In several embodiments, R... 1b It is an unsubstituted or substituted haloalkyl group, R 1b Is it unsubstituted or substituted C? 1-2 Halogenated alkyl groups. In several embodiments, R... 1b It is an unsubstituted or substituted haloalkyl group, R 1b Is it unsubstituted or substituted C? 2-3 Halogenated alkyl groups. In several embodiments, R... 1b It is an unsubstituted or substituted haloalkyl group, R 1b It is an unsubstituted or substituted C1 haloalkyl group (e.g., -CF3, etc.). In several embodiments, R... 1b It is an unsubstituted or substituted haloalkyl group, R 1b It is an unsubstituted or substituted C2 haloalkyl group. In several embodiments, R... 1b It is an unsubstituted or substituted haloalkyl group, R 1bIt is an unsubstituted or substituted C3 haloalkyl group (e.g., -CH2CH2CF3, etc.). In several embodiments, R... 1b It is an unsubstituted or substituted cycloalkyl group, R 1b Is it unsubstituted or substituted C? 4-6 Cycloalkyl. In several embodiments, wherein R 1b It is an unsubstituted or substituted cycloalkyl group, R 1b Is it unsubstituted or substituted C? 3-5 Cycloalkyl. In several embodiments, wherein R 1b It is an unsubstituted or substituted cycloalkyl group, R 1b It is an unsubstituted or substituted C3 cycloalkyl group (e.g., cyclopropyl). In several embodiments, R... 1b It is an unsubstituted or substituted cycloalkyl group, R 1b It is an unsubstituted or substituted C4 cycloalkyl group (e.g., cyclobutyl). In several embodiments, R... 1b It is an unsubstituted or substituted cycloalkyl group, R 1b It is an unsubstituted or substituted C5 cycloalkyl group (e.g., cyclopentyl). In several embodiments, R... 1b It is an unsubstituted or substituted cycloalkyl group, R 1b It is an unsubstituted or substituted C6 cycloalkyl group. In several embodiments, R... 1b It is an unsubstituted or substituted heterocyclic group, R 1b It is an unsubstituted or substituted heterocyclic group having 4 to 6 ring members. In several embodiments, R 1b It is an unsubstituted or substituted heterocyclic group, R 1b It is an unsubstituted or substituted heterocyclic group having 3 to 5 ring members. In several embodiments, R 1b It is an unsubstituted or substituted heterocyclic group, R 1b It is an unsubstituted or substituted heterocyclic group having three ring members. In several embodiments, R 1b It is an unsubstituted or substituted heterocyclic group, R 1b It is an unsubstituted or substituted heterocyclic group (e.g., oxobutyryl) having four ring members. In several embodiments, R... 1b It is an unsubstituted or substituted heterocyclic group, R 1b It is an unsubstituted or substituted heterocyclic group having 5 ring members. In several embodiments, R 1b It is an unsubstituted or substituted heterocyclic group, R 1b It is an unsubstituted or substituted heterocyclic group having 6 ring members. In several embodiments, R 1b It is a tetrahydropyranyl group. In several embodiments, R... 1b It is tetrahydrofuranyl. In several embodiments, R... 1bIt is piperidinyl. In several embodiments, R... 1b It is a pyrrolidinyl alkyl group. In several embodiments, R... 1b It is a nitrogen-containing heterocyclic butyl group. In several embodiments, R 1b yes:
[0274] , , , ,or .
[0275] The compound or salt provided herein as Example 48 is any one of Examples 1 to 47, wherein R 1b It is an unsubstituted or substituted cycloalkyl spirocyclic system or an unsubstituted or substituted heterocyclic spirocyclic system. For example, in several embodiments, R 1b It is an unsubstituted or substituted cycloalkyl spirocyclic system. In several embodiments, R 1b It is an unsubstituted or substituted heterocyclic spirocyclic system. In several embodiments, R 1b It is an unsubstituted or substituted spiro[3.3]heptyl group. In several embodiments, R 1b It is an unsubstituted or substituted spiro[3,4]octyl group. In several embodiments, R 1b It is an unsubstituted or substituted spiro[3,5]nonyl group. In several embodiments, R 1b It is an unsubstituted or substituted oxaspiro[3.3]heptyl group.
[0276] The compound or salt provided herein as Example 49 is as described in any one of Examples 1 to 47, wherein R 1b It is an unsubstituted or substituted bridged cycloalkyl ring system or an unsubstituted or substituted bridged heterocyclic ring system. For example, in several embodiments, R 1b It is an unsubstituted or substituted bridging cycloalkyl ring system. In several embodiments, R 1b It is an unsubstituted or substituted bridging heterocyclic base ring system.
[0277] The compound or salt provided herein as Example 50 is any one of Examples 1 to 49, wherein R 1b It is a double-ring system.
[0278] The compound or salt provided herein as Example 51 is any one of Examples 1 to 50, wherein R 1b It is an unsubstituted or substituted heterocyclic group having one, two, or three heteroatom ring members, each of which is independently nitrogen, oxygen, or -S(O). x - where x is 0, 1, or 2. For example, in several embodiments, the R 1bHeterocyclic groups contain one, two, or three heteroatom ring members, each of which is independently nitrogen, oxygen, or -S(O). x - where x is 0, 1, or 2. In several embodiments, this R 1b The heterocyclic group comprises one or three heteroatom ring members. In several embodiments, the R... 1b The heterocyclic group contains 2 or 3 heteroatom ring members. In several embodiments, x is 0. In several embodiments, x is 1. In several embodiments, x is 2.
[0279] The compound or salt provided herein as Example 52 is as described in any one of Examples 1 to 51, wherein R 1b It is an unsubstituted or substituted heterocyclic group having one, two, or three heteroatom ring members, each heteroatom ring member being independently nitrogen or oxygen. For example, in several embodiments, multiple heteroatom ring members are present, each of which may be oxygen, or a combination of oxygen and nitrogen may be present. In several embodiments, multiple heteroatom ring members are present, each of which may be nitrogen, or a combination of oxygen and nitrogen may be present. In several embodiments, one heteroatom is present, which may be oxygen. In several embodiments, one heteroatom is present, which may be nitrogen.
[0280] The compound or salt provided herein as Example 53 is any one of Examples 1 to 52, wherein R 1b It is a heterocyclic group having one or two heteroatom ring members.
[0281] The compound or salt provided herein as Example 54 is as described in any one of Examples 1 to 53, wherein R 1b It is a heterocyclic group with one heteroatom ring member.
[0282] The compound or salt provided herein as Example 55 is any one of Examples 1 to 54, wherein R 1b It is a heterocyclic group and R 1b Each heteroatom ring member is nitrogen.
[0283] The compound or salt provided herein as Example 56 is as described in any one of Examples 1 to 54, wherein R 1b It is a heterocyclic group and R 1b Each heteroatom ring member is oxygen.
[0284] The compound or salt provided herein as Example 57 is any one of Examples 1 to 56, wherein R 1b It is an unsubstituted or substituted heterocyclic group having 3 to 6 ring members. For example, in several embodiments, R 1bIt is an unsubstituted or substituted heterocyclic group having 3 to 5 ring members. In several embodiments, R 1b It is an unsubstituted or substituted heterocyclic group having 3 to 4 ring members. In several embodiments, R 1b It is an unsubstituted or substituted heterocyclic group having 4 to 6 ring members. In several embodiments, R 1b It is an unsubstituted or substituted heterocyclic group having 4 to 5 ring members. In several embodiments, R 1b It is an unsubstituted or substituted heterocyclic group having 5 to 6 ring members. In several embodiments, R 1b It is an unsubstituted or substituted heterocyclic group having three ring members. In several embodiments, R 1b It is an unsubstituted or substituted heterocyclic group having four ring members. In several embodiments, R 1b It is an unsubstituted or substituted heterocyclic group having 5 ring members. In several embodiments, R 1b It is an unsubstituted or substituted heterocyclic group having 6 ring members. In several embodiments, R 1b It is an unsubstituted heterocyclic group. In several embodiments, R 1b It is a substituted heterocyclic group.
[0285] The compound or salt provided herein as Example 58 is any one of Examples 1 to 47, wherein R 1b Is it unsubstituted or substituted C? 1-3 Alkyl group. For example, in several embodiments, R 1b Is it unsubstituted or substituted C? 1-2 Alkyl group. In several embodiments, R 1b Is it unsubstituted or substituted C? 2-3 Alkyl group. In several embodiments, R 1b It is an unsubstituted or substituted C1 alkyl group. In several embodiments, R 1b It is an unsubstituted or substituted C2 alkyl group. In several embodiments, R 1b It is an unsubstituted or substituted C3 alkyl group. In several embodiments, the R... 1b The alkyl group is unsubstituted. In several embodiments, the R... 1b Alkyl groups are substituted.
[0286] The compound or salt provided herein as Example 59 is any one of Examples 1 to 47, wherein R 1b Is it unsubstituted or substituted C? 1-3 Haloalkyl. For example, in several embodiments, R 1b Is it unsubstituted or substituted C? 1-2 Haloalkyl. In several embodiments, R 1b Is it unsubstituted or substituted C?2-3 Haloalkyl. In several embodiments, R 1b It is an unsubstituted or substituted C1 haloalkyl group. In several embodiments, R 1b It is an unsubstituted or substituted C2 haloalkyl group. In several embodiments, R 1b It is an unsubstituted or substituted C3 haloalkyl group. In several embodiments, the R... 1b The haloalkyl group is unsubstituted. In several embodiments, the R... 1b The haloalkyl group is substituted. In several embodiments, the R... 1b The haloalkyl group is perhalogenated (e.g., perfluorinated). In several embodiments, R... 1b It is C 1-3 A haloalkyl group, which may contain 1, 2, 3, 4, 5, 6, or 7 halogen atoms (e.g., -F).
[0287] The compound or salt provided herein as Example 60 is any one of Examples 1 to 47, wherein R 1b Is it unsubstituted or substituted C? 3-6 Cycloalkyl. For example, in several embodiments, R 1b Is it unsubstituted or substituted C? 3-5 Cycloalkyl. In several embodiments, R 1b Is it unsubstituted or substituted C? 3-4 Cycloalkyl. In several embodiments, R 1b Is it unsubstituted or substituted C? 4-6 Cycloalkyl. In several embodiments, R 1b Is it unsubstituted or substituted C? 5-6 Cycloalkyl. In several embodiments, R 1b It is an unsubstituted or substituted C3 cycloalkyl group. In several embodiments, R 1b It is an unsubstituted or substituted C4 cycloalkyl group. In several embodiments, R 1b It is an unsubstituted or substituted C5 cycloalkyl group. In several embodiments, R 1b It is an unsubstituted or substituted C6 cycloalkyl group. In several embodiments, the R... 1b The cycloalkyl group is unsubstituted. In several embodiments, the R... 1b Halogenated alkyl groups are cycloalkyl groups.
[0288] The compound or salt provided herein as Example 61 is any one of Examples 1 to 46, wherein R 1b Is it unsubstituted or substituted - (C 1-6 alkylene)-O-(C 1-6 Alkyl group). For example, in several embodiments, R 1b Is it unsubstituted or substituted - (C1-6 Alkylene)-O-(C1 alkyl) (e.g., -CH2CH2OCH3, -CH2OCH3, etc.). In several embodiments, R 1b Is it unsubstituted or substituted - (C 1-6 (alkylene)-O-(C2 alkyl). In several embodiments, R 1b Is it unsubstituted or substituted - (C 1-6 (alkylene)-O-(C3 alkyl). In several embodiments, R 1b Is it unsubstituted or substituted - (C 1-6 (alkylene)-O-(C4 alkyl). In several embodiments, R 1b Is it unsubstituted or substituted - (C 1-6 (alkylene)-O-(C5 alkyl). In several embodiments, R 1b Is it unsubstituted or substituted - (C 1-6 (alkylene)-O-(C6 alkyl). In several embodiments, R 1b Is it unsubstituted or substituted - (C 1-6 alkylene)-O-(C 1-2 Alkyl group). In several embodiments, R 1b Is it unsubstituted or substituted - (C 1-6 alkylene)-O-(C 1-3 Alkyl group). In several embodiments, as disclosed elsewhere herein, the R... 1b Alkylene is C 1-2 Alkylene. In several embodiments, the R 1b Alkylene is C 2-3 Alkylene. In several embodiments, the R 1b Alkylene is C 1-3 Alkylene. In several embodiments, the R 1b Alkylene is C 2-4 Alkylene. In several embodiments, the R 1b Alkylene is C 2-5 Alkylene. In several embodiments, the R 1b The alkylene group is a C1 alkylene group. In several embodiments, the R... 1b The alkylene group is a C2 alkylene group. In several embodiments, the R... 1b The alkylene group is a C3 alkylene group. In several embodiments, the R... 1b The alkylene group is a C4 alkylene group. In several embodiments, the R... 1b The alkylene group is a C5 alkylene group. In several embodiments, R 1b Is it unsubstituted or substituted - (C 1-3 alkylene)-O-(C 1-3 Alkyl group). In several embodiments, R 1bIs it unsubstituted or substituted - (C 1-2 alkylene)-O-(C 1-2 Alkyl group). In several embodiments, R 1b Is it unsubstituted or substituted - (C 1-3 alkylene)-O-(C 1-2 Alkyl group). In several embodiments, R 1b Is it unsubstituted or substituted - (C 1-3 (alkylene)-OMe. In several embodiments, the alkylene-O-alkyl is unsubstituted. In several embodiments, the alkylene-O-alkyl is substituted. In several embodiments, R 1b It is -CH2-O-CH3. In several embodiments, R 1b It can be represented by one of the following structures: , , ,or In several embodiments, R 1b Yes - (C 1-3 alkylene)-O-(C 1-3 alkyl) and wherein R 1b If R is replaced by 2 or 3 substituents (e.g., -F), then 1b They can be respectively or .
[0289] The compound or salt provided herein as Example 62 is any one of Examples 1 to 46, wherein R 1b Is it unsubstituted or substituted - (C 1-3 alkylene)-O-(C 1-3 alkyl).
[0290] The compound or salt provided herein as Example 63 is as described in any one of Examples 1 to 62, wherein R 1b It is substituted by 1, 2, 3, or 4 substituents. For example, in several embodiments, R 1b It is substituted with 1 to 4 substituents. In several embodiments, R 1b It is substituted with 1 to 3 substituents. In several embodiments, R 1b It is substituted with 1 to 2 substituents. In several embodiments, R 1b It is substituted with 2 to 4 substituents. In several embodiments, R 1b It is substituted with 3 to 4 substituents. In several embodiments, R 1b It is substituted by 2 to 3 substituents.
[0291] The compound or salt provided herein as Example 64 is any one of Examples 1 to 62, wherein R 1bIt is substituted by 1, 2 or 3 substituents.
[0292] The compound or salt provided herein as Example 65 is any one of Examples 1 to 62, wherein R 1b It is substituted by one or two substituents.
[0293] The compound or salt provided herein as Example 66 is any one of Examples 1 to 62, wherein R 1b It is replaced by one substituent.
[0294] The compound or salt provided herein as Example 67 is as described in any one of Examples 1 to 66, wherein, when R 1b When replaced, each R 1b The substituents are independently halogenated, unsubstituted, or substituted C. 1-3 Alkyl, or unsubstituted or substituted C 1-3 Alkyl groups. For example, in several embodiments, each R 1b The substituents are independently halogenated, unsubstituted, or substituted C. 1-3 Alkyl or unsubstituted C 1-3 Alkoxy. In several embodiments, each R 1b The substituent is independently a halogen, and the substituted C 1-3 Alkyl or substituted C 1-3 Alkoxy. In several embodiments, each R 1b The substituents are independently halogens or C. 1-3 Alkoxy. In several embodiments, each R 1b The substituents are independently halogens or C. 1-3 Alkyl group. In several embodiments, each R 1b The substituent is C independently 1-3 Alkyl or C 1-3 Alkoxy. In several embodiments, each R 1b The substituents are independently -F, -Cl, or -Br. In several embodiments, each R 1b The substituent is independently -F or -Cl. In several embodiments, R 1b Replaced by -F. In several embodiments, R 1b C 1-2 Alkyl substitution. In several embodiments, R 1b C 2-3 Alkyl substitution. In several embodiments, R 1b Replaced by a methyl group. In several embodiments, R 1b Replaced by a C2 alkyl group. In several embodiments, R 1b Replaced by a C3 alkyl group. In several embodiments, R 1b C 1-2Alkyl substitution. In several embodiments, R 1b C 2-3 Alkyl substitution. In several embodiments, R 1b It is substituted with a C1 alkoxy group. In several embodiments, R 1b Replaced by a C2 alkoxy group. In several embodiments, R... 1b It is substituted with a C3 alkoxy group. In several embodiments, R... 1b C that is not replaced or replaced 1-3 Alkyl or unsubstituted or substituted C 1-3 Alkoxy substitution, each C 1-3 Alkyl or C 1-3 The alkoxy group can be unsubstituted, or surrounded by 1 to 9 halogen groups or C. 1-3 Alkoxy substitution 。 In several embodiments, R 1b C that is not replaced or replaced 1-3 Alkyl or unsubstituted or substituted C 1-3 Alkoxy substitution, each C 1-3 Alkyl or C 1-3 The alkoxy group can be unsubstituted, or surrounded by 1 to 9 -F groups or C groups. 1-3 Alkyl substitution. In several embodiments, R 1b It is replaced by one or more substituents, each of which is independently:
[0295] , , , , , , ,or .
[0296] In several embodiments, R 1b Along with its substituents, it is difluorocyclobutyl (e.g., 3,3-difluorocyclobutyl) or difluorocyclohexyl (e.g., 4,4-difluorocyclohexyl). In several embodiments, R 1b Along with its substituents, it is N-methylpiperidinyl. In several embodiments, R 1b Along with its substituents, it is an N-methylpyrrolidinyl group. In several embodiments, R 1b Together with its substituents, it is an N-methylazacyclobutane. In several embodiments, R 1b Together with its substituents (when present) , , , , , , , , , , , , , , , , , , , , , , , , , , ,or .
[0297] The compound or salt provided herein as Example 68 is as described in any one of Examples 1 to 67, wherein, when R 1b When replaced, each R 1b The substituents are independently -F, -OH, methyl, or -OMe. For example, in several embodiments, each R 1b The substituents are independently -OH, methyl, or -OMe. In several embodiments, each R 1b The substituents are independently -F, methyl, or -OMe. In several embodiments, each R 1b The substituents are independently -F, -OH, or -OMe. In several embodiments, each R 1b The substituents are independently -F, -OH, or methyl. In several embodiments, each R 1b The substituents are independently -F or -OH. In several embodiments, each R 1b The substituent is independently -F or methyl. In several embodiments, each R 1b The substituent is independently -F or -OMe. In several embodiments, each R 1b The substituents are independently -OH or methyl. In several embodiments, each R 1b The substituents are independently -OH or -OMe. In several embodiments, each R 1b The substituents are independently methyl or -OMe.
[0298] The compound or salt provided herein as Example 69 is any one of Examples 1 to 62, wherein R 1b It is not replaced.
[0299] The compound or salt provided herein as Example 70 is any one of Examples 1 to 46, wherein R1b Yes, it's -H.
[0300] The compound or salt provided herein as Example 71 is as described in any one of Examples 1 to 33, wherein R 1a and R 1b Together they form unsubstituted or substituted C 3-10 Cycloalkyl or unsubstituted or substituted heterocyclic groups having 3 to 10 ring members. For example, in several embodiments, R 1a and R 1b Together they form C 4-6 Cycloalkyl. In several embodiments, R 1a and R 1b Together they form C 3-5 Cycloalkyl. In several embodiments, R 1a and R 1b Together they form C 4-6 Cycloalkyl. In several embodiments, R 1a and R 1b Together they form C 3-4 Cycloalkyl. In several embodiments, R 1a and R 1b Together they form C 5-6 Cycloalkyl. In several embodiments, R 1a and R 1b Together they form C 5-10 Cycloalkyl. In several embodiments, R 1a and R 1b Together they form a C3 cycloalkyl group (e.g., cyclopropyl). In several embodiments, R 1a and R 1b Together they form a C4 cycloalkyl group (e.g., a cyclobutyl group). In several embodiments, R 1a and R 1b Together they form C5 cycloalkyl groups (e.g., cyclopentyl, bicyclo[1.1.1]pent-1-yl, etc.). In several embodiments, R 1a and R 1b Together they form C6 cycloalkyl groups (e.g., cyclohexyl, spiro[2.3]hexyl, etc.). In several embodiments, R 1a and R 1b Together they form C7 cycloalkyl groups (e.g., cycloheptyl, spiro[3.3]heptyl, etc.). In several embodiments, R 1a and R 1b Together they form C8 cycloalkyl groups (e.g., spiro[3.4]octyl, etc.). In several embodiments, R 1a and R 1b Together they form C9 cycloalkyl groups (e.g., spiro[3.5]nonyl, etc.). In several embodiments, R 1a and R 1bTogether, they form a heterocyclic group having 4 to 6 ring members. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group having 5 to 6 ring members. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group having 3 to 5 ring members. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group having 3 to 4 ring members. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group having 4 to 5 ring members. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group with three ring members. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group having four ring members (e.g., azaheterobutyl, oxobutyl, etc.). In several embodiments, R 1a and R 1b Together, they form a heterocyclic group having five ring members (e.g., pyrrolidinyl, tetrahydrofuranyl, etc.). In several embodiments, R 1a and R 1b Together, they form a heterocyclic group having six ring members (e.g., piperidinyl, tetrahydropyranyl, tetrahydro-2H-thiaran-1,1-dioxide, etc.). In several embodiments, R 1a and R 1b Together they form a heterocyclic group having 7 ring members (e.g., oxaspiro[3.3]heptyl, etc.). In several embodiments, R 1a and R 1b Together they form unsubstituted or substituted C 3-9 Cycloalkyl or unsubstituted heterocyclic groups or groups having 3 to 9 ring members. In several embodiments, R 1a and R 1b Together they form unsubstituted or substituted C 3-9 Cycloalkyl or unsubstituted or substituted heterocyclic groups having 4 to 8 ring members. In several embodiments, R 1a and R 1b Together they form unsubstituted or substituted C 3-9 Cycloalkyl or unsubstituted or substituted heterocyclic groups having 4 to 7 ring members. In several embodiments, R 1a and R 1b When they form unsubstituted cycloalkyl or heterocyclic groups, then It can be represented as: , , , , , , , , , , ,or In several embodiments, when R 1a and R 1b When they together form substituted cycloalkyl or heterocyclic groups, then It can be represented as: , , , , , , , , , , , , , , , , , , , , , , , , , ,or In several embodiments, R 1c It is H and when R 1a and R 1b Together they form unsubstituted cycloalkyl or heterocyclic groups. It can be represented as: , , , , , , , , , , , ,or In several embodiments, R 1c It is H and when R 1a and R 1b When they together form substituted cycloalkyl or heterocyclic groups, It can be represented as: , , , , , , , , , , , , , , , , , , , , , , , , , ,or In several embodiments, R 1a and R 1b The substituents on the formed cycloalkyl or heterocyclic groups relative to -OR 1c The group can be cis-configured. In several embodiments, R... 1a and R 1b The substituents on the formed cycloalkyl or heterocyclic groups relative to -OR 1c The group can be trans. In several embodiments, more than one substituent is provided in the form of R. 1a and R 1b On the formed cycloalkyl or heterocyclic group, each of these substituents can be independently relative to -OR. 1c The groups are either cis or trans. For example, in this structure, -CH3 and -OH are trans relative to each other and -CF3 and -OH are cis relative to each other: .
[0301] The compound or salt provided herein as Example 72 is any one of Examples 1 to 33, wherein R 1a and R 1b Together, they form an unsubstituted or substituted heterocyclic group having 3 to 10 ring members. For example, in several embodiments, R 1a and R 1b Together, they form an unsubstituted or substituted 3-membered heterocyclic group (e.g., an unsubstituted or substituted heterocyclic group having 3 ring members). In several embodiments, R 1a and R 1b Together, they form an unsubstituted or substituted 4-membered heterocyclic group (e.g., an unsubstituted or substituted heterocyclic group having 4 ring members). In several embodiments, R 1a and R 1b Together, they form an unsubstituted or substituted 5-membered heterocyclic group (e.g., an unsubstituted or substituted heterocyclic group having 5 ring members). In several embodiments, R1a and R 1b Together, they form an unsubstituted or substituted 6-membered heterocyclic group (e.g., an unsubstituted or substituted heterocyclic group having 6 ring members). In several embodiments, R 1a and R 1b Together, they form an unsubstituted or substituted 7-membered heterocyclic group (e.g., an unsubstituted or substituted heterocyclic group having 7 ring members). In several embodiments, R 1a and R 1b Together, they form an unsubstituted or substituted 8-membered heterocyclic group (e.g., an unsubstituted or substituted heterocyclic group having 8 ring members). In several embodiments, R 1a and R 1b Together, they form an unsubstituted or substituted 9-membered heterocyclic group (e.g., an unsubstituted or substituted heterocyclic group having 9 ring members). In several embodiments, R 1a and R 1b Together they form an unsubstituted or substituted 10-membered heterocyclic group (e.g., an unsubstituted or substituted heterocyclic group having 10 ring members).
[0302] The compound or salt provided herein as Example 73 is any one of Examples 1 to 33, wherein R 1a and R 1b Together they form unsubstituted or substituted heterocyclic groups with 5 to 10 ring members.
[0303] The compound or salt provided herein as Example 74 is any one of Examples 1 to 33, wherein R 1a and R 1b Together, they form an unsubstituted or substituted heterocyclic group having 7 to 10 ring members. For example, in several embodiments, R 1a and R 1b Together, they form an unsubstituted or substituted 7-membered heterocyclic group. In several embodiments, R 1a and R 1b Together, they form unsubstituted or substituted 8-membered heterocyclic groups. In several embodiments, R 1a and R 1b Together, they form an unsubstituted or substituted 9-membered heterocyclic group. In several embodiments, R 1a and R 1b Together, they form an unsubstituted or substituted 10-membered heterocyclic group. In several embodiments, the heterocyclic group may be spirocyclic. In several embodiments, the heterocyclic group may be a bridged polycyclic ring.
[0304] The compound or salt provided herein as Example 75 is any one of Examples 1 to 33, wherein R 1a and R 1bTogether, they form an unsubstituted or substituted heterocyclic group having 4 to 6 ring members. For example, in several embodiments, R 1a and R 1b Together, they form an unsubstituted or substituted 4-membered heterocyclic group (e.g., a substituted heterocyclic group having 4 ring members). In several embodiments, R 1a and R 1b Together, they form an unsubstituted or substituted 5-membered heterocyclic group (e.g., a substituted heterocyclic group having 5 ring members). In several embodiments, R 1a and R 1b Together they form an unsubstituted or substituted 6-membered heterocyclic group (e.g., a heterocyclic group with 6 ring members, such as a tetrahydropyranyl group, etc.).
[0305] The compound or salt provided herein as Example 76 is any one of Examples 1 to 33 and 71 to 75, wherein, when R 1a and R 1b When they are combined to form an unsubstituted or substituted heterocyclic group, the heterocyclic group contains one, two, or three heteroatom ring members, each of which is independently nitrogen, oxygen, or -S(O). x - where x is 0, 1, or 2. For example, in several embodiments, R 1a and R 1b Together, they form a heterocyclic group having one or three heteroatom ring members. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group having 2 or 3 heteroatom ring members. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group having one or two heteroatom ring members. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group having one or three heteroatom ring members. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group with S(O)2 as a ring member. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group with N as a ring member. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group having two N-ring members. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group with three N-ring members. In several embodiments, R 1a and R 1b Together, they form a heterocyclic group with O as a ring member. In several embodiments, R 1a and R 1bTogether, they form a heterocyclic group having S as a ring member. In several embodiments, x is 0. In several embodiments, x is 1. In several embodiments, x is 2.
[0306] The compound or salt provided herein as Example 77 is any one of Examples 1 to 33 and 71 to 75, wherein, when R 1a and R 1b When they are combined to form an unsubstituted or substituted heterocyclic group, the heterocyclic group contains one, two or three heteroatom ring members, each of which is independently nitrogen or oxygen.
[0307] The compound or salt provided herein as Example 78 is any one of Examples 1 to 33 and 71 to 77, wherein, when R 1a and R 1b When they are combined to form an unsubstituted or substituted heterocyclic group, the heterocyclic group contains one or two heteroatom ring members.
[0308] The compound or salt provided herein as Example 79 is any one of Examples 1 to 33 and 71 to 78, wherein, when R 1a and R 1b When they are combined to form an unsubstituted or substituted heterocyclic group, the heterocyclic group contains one heteroatom ring member.
[0309] The compound or salt provided herein as Example 80 is any one of Examples 1 to 33 and 71 to 79, wherein R 1a and R 1b Together they form unsubstituted or substituted heterocyclic groups, R 1a and R 1b One or more heteroatom ring members contain nitrogen or are composed of nitrogen.
[0310] The compound or salt provided herein as Example 81 is any one of Examples 1 to 33 and 71 to 80, wherein R 1a and R 1b Together they form unsubstituted or substituted heterocyclic groups, and R 1a and R 1b One or more heteroatom ring members contain oxygen or are composed of oxygen.
[0311] The compound or salt provided herein as Example 82 is any one of Examples 1 to 33 and 71, wherein R 1a and R 1b Together they form unsubstituted or substituted C 3-10 Cycloalkyl. For example, in several embodiments, R 1a and R 1b Together they form C 5-10 Cycloalkyl. In several embodiments, R1a and R 1b Together they form C 7-10 Cycloalkyl. In several embodiments, R 1a and R 1b Together they form C 3-6 Cycloalkyl group. In several embodiments, the cycloalkyl group may be spirocyclic. In several embodiments, the cycloalkyl group may be a bridged polycyclic ring.
[0312] The compound or salt provided herein as Example 83 is any one of Examples 1 to 33 and 71, wherein R 1a and R 1b Together they form unsubstituted or substituted C 5-10 Cycloalkyl.
[0313] The compound or salt provided herein as Example 84 is any one of Examples 1 to 33 and 71, wherein R 1a and R 1b Together they form unsubstituted or substituted C 7-10 Cycloalkyl.
[0314] The compound or salt provided herein as Example 85 is any one of Examples 1 to 33 and 71, wherein R 1a and R 1b Together they form unsubstituted or substituted C 3-6 Cycloalkyl. For example, in several embodiments, R 1a and R 1b Together, they form unsubstituted or substituted cyclopropyl groups. In several embodiments, R 1a and R 1b Together, they form unsubstituted or substituted cyclobutyl groups. In several embodiments, R 1a and R 1b Together, they form unsubstituted or substituted cyclopentyl groups. In several embodiments, R 1a and R 1b Together they form unsubstituted or substituted cyclohexyl groups.
[0315] The compound or salt provided herein as Example 86 is any one of Examples 1 to 33 and 71 to 85, wherein R 1a and R 1b Together they form a helical ring system. For example, in several embodiments, when R 1c It's H. It can be represented as: , , , , ,or In several embodiments, when R 1aand R 1b Together they form a replacement helical ring system and R 1c When it is H, It can be represented as: or .
[0316] The compound or salt provided herein as Example 87 is any one of Examples 1 to 33 and 71 to 86, wherein R 1a and R 1b Together they form a double-ring system.
[0317] The compound or salt provided herein as Example 88 is any one of Examples 1 to 33 and 71 to 87, wherein R 1a and R 1b Together they form a ring that is substituted by 1, 2, 3 or 4 substituents.
[0318] The compound or salt provided herein as Example 89 is any one of Examples 1 to 33 and 71 to 87, wherein R 1a and R 1b Together they form a ring substituted with one, two, or three substituents. For example, in several embodiments, the R... 1a and R 1b The ring is substituted with 2 to 3 substituents. In several embodiments, the R... 1a and R 1b The ring is substituted with one or three substituents. In several embodiments, the R... 1a and R 1b The ring is substituted by one or two substituents.
[0319] The compound or salt provided herein as Example 90 is any one of Examples 1 to 33 and 71 to 87, wherein R 1a and R 1b Together they form a ring that is substituted by one or two substituents.
[0320] The compound or salt provided herein as Example 91 is any one of Examples 1 to 33 and 71 to 87, wherein R 1a and R 1b Together they form a ring substituted by one substituent.
[0321] The compound or salt provided herein as Example 92 is any one of Examples 1 to 33 and 71 to 91, wherein R 1a and R 1b Together they form -(C 1-3 alkylene)-O-(C 1-3 Alkyl)-substituted ring. For example, in several embodiments, R... 1a and R1b Together they form C that are used as heteroalkyl groups 1-3 Alkylene-OC 1-3 Alkyl-substituted ring, the C 1-3 Alkylene-OC 1-3 Alkyl groups can be represented by one of the following structures:
[0322] .
[0323] For example, in several embodiments, R 1a and R 1b Together they form an alkyl-substituted ring, which is substituted with a C1 alkoxy group. In several embodiments, R 1a and R 1b Together they form an alkyl-substituted ring, which is substituted with a C2 alkoxy group. In several embodiments, R 1a and R 1b Together, they form an alkyl-substituted ring, which is substituted with a C3 alkoxy group. In several embodiments, the R... 1a and R 1b The alkyl substituent of the ring is C 1-2 Alkyl group. In several embodiments, the R... 1a and R 1b The alkyl substituent of the ring is C 1-3 Alkyl group. In several embodiments, the R... 1a and R 1b The alkyl substituent of the ring is methyl. In several embodiments, this R 1a and R 1b The alkyl substituent of the ring is a C2 alkyl group (e.g., ethyl). In several embodiments, this R 1a and R 1b The alkyl substituent of the ring is a C3 alkyl group (e.g., propyl or isopropyl).
[0324] The compound or salt provided herein as Example 93 is any one of Examples 1 to 33 and 71 to 91, wherein R 1a and R 1b Together they form a substituted ring, and each substituent in the ring is independently a halogen, -OH, oxo, or -N(R) group. b 2. Unsubstituted or substituted C 1-3 Alkyl, unsubstituted or substituted C 1-3 Alkoxy, -CN, C 3-10 Cycloalkyl groups, or heterocyclic groups having 3 to 10 ring members and 1, 2, or 3 heteroatom ring members, each heteroatom ring member being independently nitrogen, oxygen, or -S(O). w -, where w is 0, 1, or 2, and C 1-3 Alkyl and C 1-3Each of the alkoxy groups can be unsubstituted or surrounded by 1 to 6 halogen groups or C. 1-3 Alkyl substitution. For example, in several embodiments, the R... 1a and R 1b Ring C 3-6 The substituent is a cycloalkyl group or a heterocyclic group having 3 to 10 ring members and 1 or 2 heteroatom ring members. In several embodiments, the substituent is C10. 3-6 Cycloalkyl. In several embodiments, the substituent is a heterocyclic substituent having 3 to 6 ring members. In several embodiments, the heterocyclic substituent comprises 1 or 2 heteroatom ring members, each heteroatom ring member being independently nitrogen or oxygen. In several embodiments, the R... 1a and R 1b The ring is replaced by a halogen (e.g., -F). In several embodiments, this R... 1a and R 1b The ring is replaced by -OH. In several embodiments, this R 1a and R 1b The ring is replaced by an oxo group. In several embodiments, this R 1a and R 1b -N(R) b )2 is replaced. In several embodiments, the R 1a and R 1b Ring C 1-3 Alkyl substitution. In several embodiments, the R 1a and R 1b The ring is replaced by -CN. In several embodiments, this R 1a and R 1b Ring C 1-3 Alkyl substitution. In several embodiments, this R 1a and R 1b Ring C 1-3 Alkyl or C 1-3 Alkyl substitution. In several embodiments, this R 1a and R 1b C of the ring 1-3 Alkyl or C 1-3 The alkoxy substituent is further replaced by 1-6 halogens. In several embodiments, R 1a and R 1b C of the ring 1-3 The alkyl substituent is 1-6 halogen (e.g., provided in R...). 1a and R 1b (Substituents such as -CH2F, -CHF2, or -CF3 on the ring, etc.). In several embodiments, R 1a and R 1b C of the ring 1-3 The alkoxy substituent is provided with 1-6 halogens (e.g., in R...). 1a and R1b -OCF3 on the ring, etc.). In several embodiments, this R 1a and R 1b C of the ring 1-3 Alkyl or C 1-3 The alkoxy substituent is further replaced by 1-3 halogens. In several embodiments, this R 1a and R 1b C of the ring 1-3 Alkyl or C 1-3 The alkoxy substituent is further replaced by 1-6 -F atoms. In several embodiments, this R 1a and R 1b C of the ring 1-3 Alkyl or C 1-3 The alkoxy substituent is further replaced by 1-3 -F atoms. In several embodiments, this R 1a and R 1b C of the ring 1-3 The alkyl substituent can be further replaced by 1-6 halogens. In several embodiments, the R... 1a and R 1b C of the ring 1-3 The alkyl substituent can be further replaced by 1-3 halogens. In several embodiments, the R... 1a and R 1b C of the ring 1-3 The alkyl substituent can be further replaced by 1-6 -F atoms. In several embodiments, the R... 1a and R 1b C of the ring 1-3 The alkyl substituent may be further replaced by 1-3 -F atoms. In several embodiments, the R... 1a and R 1b C of the ring 1-3 The alkyl substituent may be further replaced by 1, 2, 3, 4, 5, or 6 -F atoms. In several embodiments, the R... 1a and R 1b C of the ring 1-3 The alkyl substituent may be further replaced by one, two, or three -F atoms. In several embodiments, the R... 1a and R 1b The ring is substituted with a C1 alkyl substituent, and the R 1a and R 1b The C1 alkyl substituent of the ring can be further replaced by one, two, or three -F atoms. In several embodiments, this R... 1a and R 1b C of the ring 1-3 The alkoxy substituent can be further replaced by 1-6 halogens. In several embodiments, this R... 1a and R 1b C of the ring 1-3The alkoxy substituent can be further replaced by 1-3 halogens. In several embodiments, this R... 1a and R 1b C of the ring 1-3 The alkoxy substituent can be further replaced by 1-6 -F atoms. In several embodiments, the R... 1a and R 1b C of the ring 1-3 The alkoxy substituent can be further replaced by 1-3 -F atoms. In several embodiments, the R... 1a and R 1b C of the ring 1-3 The alkoxy substituent can be further replaced by 1, 2, 3, 4, 5, or 6 -F atoms. In several embodiments, the R... 1a and R 1b C of the ring 1-3 The alkoxy substituent may be further replaced by one, two, or three -F atoms. In several embodiments, the R... 1a and R 1b The ring is substituted with a C1 alkoxy substituent, and the R 1a and R 1b The C1 alkoxy substituent of the ring can be further replaced by one, two, or three -F atoms. In several embodiments, this R 1a and R 1b C of the ring 1-3 Alkyl substituents can be further C 1-3 Alkyl substitution. In several embodiments, this R 1a and R 1b C of the ring 1-3 The alkyl substituents may be further substituted with C1 alkoxy, C2 alkoxy, or C3 alkoxy groups (providing, for example, C1 alkoxy, C2 alkoxy, or C3 alkoxy groups). 1-3 alkylene-C1 alkoxy, C 1-3 alkylene-C2 alkoxy, C 1-3 Alkylene-C3 alkoxy, C1 alkylene-C1 alkoxy, C2 alkylene-C1 alkoxy, etc.). In several embodiments, this R 1a and R 1b C of the ring 1-3 The alkoxy substituent can be further converted to C 1-3 Alkyl substitution. In several embodiments, this R 1a and R 1b C of the ring 1-3 The alkoxy substituent can be further substituted with a C1 alkoxy, a C2 alkoxy, or a C3 alkoxy. As disclosed elsewhere herein, R 1a and R 1b The ring can be cycloalkyl, cycloalkenyl, or heterocyclic. In several embodiments, the R... 1a and R 1bThe ring is replaced by one or more substituents, each of which is independently:
[0325] , , , , , , ,or .
[0326] In several embodiments, the R 1a and R 1b The ring is replaced by one or more substituents, each of which is independently:
[0327] , , , ,or .
[0328] In several embodiments, the R 1a and R 1b The ring is replaced by one or more substituents, each of which is independently:
[0329] , , , , ,or .
[0330] In several embodiments, the R 1a and R 1b The ring is replaced by one or more substituents, each of which is independently:
[0331] , , ,or .
[0332] The compound or salt provided herein as Example 94 is any one of Examples 1 to 33 and 71 to 93, wherein R 1a and R 1b Together they form a substituted ring, and each substituent in the ring is independently a halogen, -OH, oxo, or -N(R) group. b 2. C 1-3 Alkyl, or C 1-3 alkoxy group, wherein the C 1-3 Alkyl and C 1-3 Each of the alkoxy groups can be unsubstituted or surrounded by 1 to 6 halogen groups or C. 1-3Alkyl-substituted.
[0333] The compound or salt provided herein as Example 95 is any one of Examples 1 to 33 and 71 to 94, wherein R 1a and R 1b Together they form a substituted ring, and each substituent in the ring is independently C. 1-3 Alkyl or C 1-3 alkoxy group, wherein the C 1-3 Alkyl and C 1-3 Each of the alkoxy groups can be unsubstituted or surrounded by 1 to 3 halogen groups or C. 1-3 Alkyl-substituted.
[0334] The compound or salt provided herein as Example 96 is any one of Examples 1 to 33 and 71 to 95, wherein R 1a and R 1b Together they form a substituted ring, and each substituent in the ring is independently -F, -OH, oxo, methyl, methoxy, or -OCF3. For example, in several embodiments, the R... 1a and R 1b Each substituent in the ring is independently -OH, methyl, or -OMe. In several embodiments, the R 1a and R 1b Each substituent in the ring is independently -F, methyl, or -OMe. In several embodiments, the R... 1a and R 1b Each substituent in the ring is independently -F, methyl, or -OCF3. In several embodiments, the R... 1a and R 1b Each substituent in the ring is independently -F, -OH, or -OMe. In several embodiments, the R... 1a and R 1b Each substituent in the ring is independently -F, -OH, or methyl. In several embodiments, the R... 1a and R 1b Each substituent in the ring is independently -F or -OH. In several embodiments, the R... 1a and R 1b Each substituent in the ring is independently -F or methyl. In several embodiments, the R 1a and R 1b Each substituent in the ring is independently -F or -OMe. In several embodiments, the R 1a and R 1b Each substituent in the ring is independently either -OH or methyl. In several embodiments, the R 1a and R 1b Each substituent in the ring is independently -OH or -OMe. In several embodiments, the R 1aand R 1b Each substituent in the ring is independently methyl or -OMe. In several embodiments, the R 1a and R 1b The ring is replaced by -F. In several embodiments, this R 1a and R 1b The ring is replaced by -OMe. In several embodiments, this R 1a and R 1b The ring is replaced by a methyl group (-Me). In several embodiments, this R 1a and R 1b The ring, together with its substituents, forms a 4,4-difluorohexyl group. In several embodiments, this R... 1a and R 1b The ring, together with its substituents, forms an N-methyl-piperidinyl group. In several embodiments, this R... 1a and R 1b The ring, together with its substituents, forms an N-methyl-pyrrolidinyl group. In several embodiments, this R... 1a and R 1b The ring, together with its substituents, forms an N-methyl-azacyclobutane.
[0335] The compound or salt provided herein as Example 97 is any one of Examples 1 to 33 and 71 to 91, wherein R 1a and R 1b Together they form an unreplaced ring.
[0336] The compound or salt provided herein as Example 98 is any one of Examples 1 to 97, wherein R 1c It is substituted by 1, 2, 3, or 4 substituents. In several embodiments, these substituents are each identical. In several embodiments, these substituents are each different. In several embodiments, one of the substituents is different from the others.
[0337] The compound or salt provided herein as Example 99 is any one of Examples 1 to 97, wherein R 1c It is substituted by 1, 2 or 3 substituents.
[0338] The compound or salt provided herein as Example 100 is any one of Examples 1 to 97, wherein R 1c It is substituted by one or two substituents.
[0339] The compound or salt provided herein as Example 101 is as described in any one of Examples 1 to 97, wherein R 1c It is replaced by one substituent.
[0340] The compound or salt provided herein as Example 102 is as described in any one of Examples 1 to 97, wherein R 1c It is not replaced.
[0341] The compound or salt provided herein as Example 103 is any one of Examples 1 to 97, wherein R 1c Yes, it's -H.
[0342] The compound or salt provided herein as Example 104 is as described in any one of Examples 1 to 102, wherein R 1c It is C 1-3 alkyl.
[0343] The compound or salt provided herein as Example 105 is as described in any one of Examples 1 to 102, wherein R 1c It is -CF3.
[0344] The compound or salt provided herein as Example 106 is any one of Examples 1 to 97, wherein R 1c It is -CH3.
[0345] The compound or salt provided herein as Example 107 is any one of Examples 1 to 106, wherein R 2 Is it unsubstituted or substituted C? 3-6 Cycloalkyl, unsubstituted or substituted C 6-10 Aryl, unsubstituted or substituted heteroaryl, or unsubstituted or substituted heterocyclic. For example, in several embodiments, R 2 It is C 3-6 Cycloalkyl, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members. In several embodiments, R 2 It is a heteroaryl group having 5 to 10 ring members or a heterocyclic group having 5 to 10 ring members. In several embodiments, R 2 It is a heteroaryl group having 5 to 10 ring members. In several embodiments, R 2 It is C 3-6 Cycloalkyl, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members. In several embodiments, R 2 It is C 6-10 Aryl or heteroaryl having 5 to 10 ring members. In several embodiments, R 2 It is C 3-6 Cycloalkyl or heteroaryl groups having 5 to 10 ring members. In several embodiments, R 2 It is C 3-6 cycloalkyl, C 6-10 Aryl, or heteroaryl having 5 to 10 ring members. In several embodiments, R2 It is pyrazolopyridyl (e.g., pyrazolo[3,4-b]pyridyl, 1H-pyrazolo[3,4-b]pyridin-5-yl, etc.). In several embodiments, R 2 It is a pyrazole group. In several embodiments, R 2 It is an indazole group. In several embodiments, R 2 It is a triazolopyridyl group (e.g., 3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl, etc.). In several embodiments, R 2 It is imidazopyridyl (e.g., imidazo[1,2-a]pyridin-6-yl, etc.). In several embodiments, R 2 It is a benzoxazolyl group. In several embodiments, R 2 It is imidazo[1,2-a]pyridyl. In several embodiments, R 2 It is a pyrimidinone group (e.g., pyrimidin-4(3H)-one). In several embodiments, R 2 It is isoquinoline-1(2H)-one. In several embodiments, R 2 It is a quinoxalinyl group. In several embodiments, R... 2 It is a pyrimidinyl group.
[0346] The compound or salt provided herein as Example 108 is any one of Examples 1 to 107, wherein R 2 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 2 The heteroaryl or heterocyclic group comprises 1, 2, 3, 4, or 5 heteroatom ring members. For example, in several embodiments, it comprises 5 heteroatom ring members. In several embodiments, it comprises 4 heteroatom ring members. In several embodiments, it comprises 2 heteroatom ring members. In several embodiments, it comprises 2 heteroatom ring members. In several embodiments, it comprises 1 heteroatom ring member. In several embodiments, R 2 It contains 1 to 5 heteroatom ring members. In several embodiments, R 2 It contains 1 to 4 heteroatom ring members. In several embodiments, R 2 It contains 1 to 3 heteroatom ring members. In several embodiments, R 2 It contains one or two heteroatom ring members. In several embodiments, R 2 It contains 2 to 5 heteroatom ring members. In several embodiments, R 2 It contains 3 to 5 heteroatom ring members. In several embodiments, R 2 It contains 3 to 4 heteroatom ring members. In several embodiments, R 2 It contains a nitrogen atom as the only cyclic heteroatom. In several embodiments, R 2 It contains a nitrogen atom as a cyclic heteroatom. In several embodiments, R2 It contains two nitrogen atoms as cyclic heteroatoms. In several embodiments, R 2 It contains three nitrogen atoms as cyclic heteroatoms. In several embodiments, R 2 It contains four nitrogen atoms as cyclic heteroatoms. In several embodiments, R 2 It contains five nitrogen atoms as cyclic heteroatoms. In several embodiments, R 2 It contains one oxygen ring heteroatom and the remaining ring heteroatoms are nitrogen atoms. In several embodiments, R 2 It contains an oxygen atom as the only cyclic heteroatom.
[0347] The compound or salt provided herein as Example 109 is as described in any one of Examples 1 to 107, wherein R 2 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 2 Heteroaryl or heterocyclic groups contain 1, 2, 3 or 4 heterocyclic members.
[0348] The compound or salt provided herein as Example 110 is as described in any one of Examples 1 to 107, wherein R 2 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 2 Heteroaryl or heterocyclic groups contain one, two, or three heterocyclic members.
[0349] The compound or salt provided herein as Example 111 is as described in any one of Examples 1 to 107, wherein R 2 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 2 A heteroaryl or heterocyclic group contains one or two heterocyclic members.
[0350] The compound or salt provided herein as Example 112 is as described in any one of Examples 1 to 107, wherein R 2 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 2 A heteroaryl or heterocyclic group contains one heteroatom ring member.
[0351] The compound or salt provided herein as Example 113 is as described in any one of Examples 1 to 112, wherein R 2 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 2 Each heteroatom in the ring is independently nitrogen, oxygen, or -S(O). y - where y is 0, 1, or 2.
[0352] The compound or salt provided herein as Example 114 is as described in any one of Examples 1 to 113, wherein R 2 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 2 Each heteroatom in the ring is either nitrogen or oxygen.
[0353] The compound or salt provided herein as Example 115 is as described in any one of Examples 1 to 113, wherein R 2 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 2 Each heteroatom in the ring is nitrogen.
[0354] The compound or salt provided herein as Example 116 is any one of Examples 1 to 107 and 113 to 115, wherein R 2 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group containing four nitrogen ring atoms.
[0355] The compound or salt provided herein as Example 117 is any one of Examples 1 to 110 and 113 to 115, wherein R 2 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group containing three nitrogen ring atoms.
[0356] The compound or salt provided herein as Example 118 is any one of Examples 1 to 111 and 113 to 115, wherein R 2 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group containing two nitrogen ring atoms.
[0357] The compound or salt provided herein as Example 119 is as described in any one of Examples 1 to 115, wherein R 2 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group containing a nitrogen ring atom.
[0358] The compound or salt provided herein as Example 120 is as described in any one of Examples 1 to 114, wherein R 2 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 2 Each heteroatom in the ring is an oxygen atom.
[0359] The compound or salt provided herein as Example 121 is as described in any one of Examples 1 to 120, wherein R 2 It is an unsubstituted or substituted fused bicyclic heteroaryl group or an unsubstituted or substituted fused bicyclic heterocyclic group. For example, in several embodiments, R 2It is a fused bicyclic heteroaryl group. In several embodiments, the fused bicyclic R... 2 It contains a 6-membered ring. In several embodiments, this fused bi-ring R 2 It contains a 5-membered ring. In several embodiments, R 2 It comprises fused 6-membered and 5-membered rings. In several embodiments, the fused bicyclic ring R 2 It is a 5,6-membered fused ring. In several embodiments, this fused bicyclic R 2 It is a 6,6-membered fused ring.
[0360] The compound or salt provided herein as Example 122 is as described in any one of Examples 1 to 120, wherein R 2 It is an unsubstituted or substituted heteroaryl group having 5 to 9 ring members, or an unsubstituted or substituted heterocyclic group having 5 to 9 ring members. In several embodiments, the fused bicyclic R 2 It is a 5- or 6-membered fused ring.
[0361] The compound or salt provided herein as Example 123 is as described in any one of Examples 1 to 120, wherein R 2 It is an unsubstituted or substituted heteroaryl group having 5 to 10 ring members, or an unsubstituted or substituted heterocyclic group having 5 to 10 ring members. In several embodiments, the fused bicyclic R 2 It is a 6,6-membered fused ring.
[0362] The compound or salt provided herein as Example 124 is as described in any one of Examples 1 to 121, wherein R 2 It is an unsubstituted or substituted heteroaryl group having 8 to 10 ring members or an unsubstituted or substituted heterocyclic group having 8 to 10 ring members.
[0363] The compound or salt provided herein as Example 125 is as described in any one of Examples 1 to 121, wherein R 2 It is an unsubstituted or substituted heteroaryl group having 9 to 10 ring members or an unsubstituted or substituted heterocyclic group having 9 to 10 ring members.
[0364] The compound or salt provided herein as Example 126 is as described in any one of Examples 1 to 121, wherein R 2 It is an unsubstituted or substituted heteroaryl group having 9 ring members or an unsubstituted or substituted heterocyclic group having 9 ring members.
[0365] The compound or salt provided herein as Example 127 is as described in any one of Examples 1 to 121, wherein R 2 It is an unsubstituted or substituted heteroaryl group having 10 ring members or an unsubstituted or substituted heterocyclic group having 10 ring members.
[0366] The compound or salt provided herein as Example 128 is any one of Examples 1 to 120, wherein R 2 It is a heteroaryl group with 6 ring members or a heterocyclic group with 6 ring members.
[0367] The compound or salt provided herein as Example 129 is any one of Examples 1 to 107 and 109 to 120, wherein R 2 It is an unsubstituted or substituted heteroaryl group having 5 ring members or an unsubstituted or substituted heterocyclic group having 5 ring members.
[0368] The compound or salt provided herein as Example 130 is as described in any one of Examples 1 to 129, wherein R 2 It is an unsubstituted or substituted heteroaryl group.
[0369] The compound or salt provided herein as Example 131 is as described in any one of Examples 1 to 129, wherein R 2 It is an unsubstituted or substituted heterocyclic group.
[0370] The compound or salt provided herein as Example 132 is as described in any one of Examples 1 to 106, wherein R 2 Is it unsubstituted or substituted C? 3-6 Cycloalkyl. For example, in several embodiments, R 2 It is C 4-6 Cycloalkyl. In several embodiments, R 2 It is C 3-5 Cycloalkyl. In several embodiments, R 2 It is C 4-6 Cycloalkyl. In several embodiments, R 2 It is C 3-4 Cycloalkyl. In several embodiments, R 2 It is C 5-6 Cycloalkyl. In several embodiments, R 2 It is a C3 cycloalkyl group (e.g., cyclopropyl). In several embodiments, R 2 It is a C4 cycloalkyl group (e.g., cyclobutyl). In several embodiments, R 2 It is a C5 cycloalkyl group. In several embodiments, R 2 It is a C6 cycloalkyl group.
[0371] The compound or salt provided herein as Example 133 is as described in any one of Examples 1 to 106, wherein R 2 Is it unsubstituted or substituted C? 3-10 Cycloalkenyl. For example, in several embodiments, R 2 It is C 4-6Cycloalkenyl. In several embodiments, R 2 It is C 3-5 Cycloalkenyl. In several embodiments, R 2 It is C 4-6 Cycloalkenyl. In several embodiments, R 2 It is C 3-4 Cycloalkenyl. In several embodiments, R 2 It is C 5-6 Cycloalkenyl. In several embodiments, R 2 It is C 5-10 Cycloalkenyl. In several embodiments, R 2 It is a C3 cycloalkenyl group. In several embodiments, R 2 It is a C4 cycloalkenyl group. In several embodiments, R 2 It is a C5 cycloalkenyl group. In several embodiments, R 2 It is a C6 cycloalkenyl group. In several embodiments, R 2 It is a C7 cycloalkenyl group. In several embodiments, R 2 It is a C8 cycloalkenyl group. In several embodiments, R 2 It is a C9 cycloalkenyl group. In several embodiments, R 2 It is C 10 Cycloalkenyl.
[0372] The compound or salt provided herein as Example 134 is as described in any one of Examples 1 to 106, wherein R 2 Is it unsubstituted or substituted C? 6-10 Aryl. For example, in several embodiments, R 2 It is a C6 aryl group (e.g., phenyl). In several embodiments, R 2 It is C 10 Aryl.
[0373] The compound or salt provided herein as Example 135 is as described in any one of Examples 1 to 134, wherein R 2 It is substituted by 1, 2, 3, 4, or 5 substituents. For example, in several embodiments, R 2 It is substituted with 1 to 5 substituents. In several embodiments, R 2 It is substituted with 1 to 4 substituents. In several embodiments, R 2 It is substituted with 1 to 3 substituents. In several embodiments, R 2 It is substituted with 1 to 2 substituents. In several embodiments, R 2 It is substituted with 2 to 4 substituents. In several embodiments, R 2 It is substituted with 2 to 5 substituents. In several embodiments, R 2 It is substituted with 3 to 5 substituents. In several embodiments, R 2It is substituted with 4 to 5 substituents. In several embodiments, R 2 It is substituted with 3 to 4 substituents. In several embodiments, R 2 It is substituted by 2 to 3 substituents.
[0374] The compound or salt provided herein as Example 136 is as described in any one of Examples 1 to 134, wherein R 2 It can be substituted by 1, 2, 3 or 4 substituents.
[0375] The compound or salt provided herein as Example 137 is any one of Examples 1 to 134, wherein R 2 It is substituted by 1, 2 or 3 substituents.
[0376] The compound or salt provided herein as Example 138 is any one of Examples 1 to 134, wherein R 2 It is substituted by one or two substituents.
[0377] The compound or salt provided herein as Example 139 is as described in any one of Examples 1 to 134, wherein R 2 It is replaced by one substituent.
[0378] The compound or salt provided herein as Example 140 is any one of Examples 1 to 139, wherein, when R 2 When replaced, each R 2 The substituents are independently halogen, -OH, oxo, C 1-3 Alkyl, or C 1-3 Alkyl groups. For example, in several embodiments, each R 2 The substituents are independently halogens, -OH, oxo groups, or C. 1-3 Alkyl group. In several embodiments, each R 2 The substituents are independently halogen, -OH, oxo, C 1-3 Alkyl, or C 1-3 Alkoxy. In several embodiments, each R 2 The substituents are independently halogens, -OH, oxo groups, or C. 1-3 Alkoxy. In several embodiments, each R 2 The substituents are independently halogen, -OH, C 1-3 Alkyl, or C 1-3 Alkoxy. In several embodiments, each R 2 The substituents are independently halogen, oxo, C 1-3 Alkyl, or C 1-3 Alkoxy. In several embodiments, each R 2 The substituents are independently -OH, oxo, C 1-3 Alkyl, or C1-3 Alkoxy. In several embodiments, each R 2 The substituents are independently oxo, C 1-3 Alkyl, or C 1-3 Alkoxy. In several embodiments, each R 2 The substituents are independently halogens, C 1-3 Alkyl, or C 1-3 Alkoxy. In several embodiments, each R 2 The substituents are independently halogens, -OH, or C. 1-3 Alkoxy. In several embodiments, each R 2 The substituents are independently halogens, -OH groups, or oxo groups. In several embodiments, each R 2 The substituents are independently halogen, -OH, oxo, C 1-3 Alkyl, or C 1-3 Alkoxy. In several embodiments, each R 2 The substituents are independently halogenated, oxo-substituted, or C-substituted. 1-3 Alkyl group. In several embodiments, each R 2 The substituents are independently halogens or C. 1-3 Alkyl group. In several embodiments, each R 2 The substituents are independently oxo or C. 1-3 Alkyl group. In several embodiments, each R 2 The substituents are independently halogenated or oxolated. In several embodiments, each R 2 The substituent is independently a halogen. In several embodiments, R 2 The halogen substituent (or one or more substituents independently) is -F, -Cl, or -Br. In several embodiments, R 2 The halogen substituent (or one or more substituents independently) is -F or -Cl. In several embodiments, R 2 Replaced by -F. In several embodiments, R 2 C 1-3 Alkyl substitution. In several embodiments, R 2 C 1-2 Alkyl substitution. In several embodiments, R 2 C 2-3 Alkyl substitution. In several embodiments, R 2 Replaced by a methyl group. In several embodiments, R 2 It is substituted with a C2 alkyl group (e.g., ethyl). In several embodiments, R 2 Replaced by a C3 alkyl group. In several embodiments, R 2 C 1-2 Alkyl substitution. In several embodiments, R 2 C 2-3Alkyl substitution. In several embodiments, R 2 Replaced with a methoxy group. In several embodiments, R 2 Replaced by a C2 alkoxy group. In several embodiments, R... 2 Replaced by a C3 alkoxy group. In several embodiments, R... 2 Together with its substituents, it forms an N-methyl-pyrazolyl group. In several embodiments, R 2 Together with its substituents, it forms alkyl-pyrazolo[3,4-b]pyridine (e.g., 2-methyl-2H-pyrazolo[3,4-b]pyridinyl, 2-ethyl-2H-pyrazolo[3,4-b]pyridin-5-yl, 2-(2-propyl)-2H-pyrazolo[3,4-b]pyridin-5-yl, 1-(2-propyl)-1H-pyrazolo[3,4-b]pyridin-5-yl, etc.). In several embodiments, R 2 Together with its substituents, it forms methyl-pyrazolo[3,4-b]pyridine. In several embodiments, R 2 Together with its substituents, it forms an alkyl-indazole group (e.g., 1-methyl-1H-indazole-5-yl, 3-methyl-1H-indazole-5-yl, 6-methyl-1H-indazole-5-yl, 2-isopropyl-2H-indazole-5-yl, etc.). In several embodiments, R 2 Together with its substituents, it forms a methyl-indazole group. In several embodiments, R 2 Together with its substituents, it forms a methyl-triazolopyridyl group (e.g., 2-methyl-2H-triazolo[4,5-b]pyridin-6-yl, 3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl, etc.). In several embodiments, R 2 Together with its substituents, it forms a methyl-benzoxazolyl group (e.g., 1,2-benzoxazol-5-yl, 2-methyl-1,3-benzoxazol-5-yl, etc.). In several embodiments, together with its substituents, it forms a methyl-imidazo[1,2-a]pyridyl group (e.g., 2-methylimidazo[1,2-a]pyridin-6-yl, etc.). In several embodiments, R 2 Together with its substituents, it forms a methyl-pyrimidinone group (e.g., 3-methylpyrimidin-4(3H)-one). In several embodiments, R 2 Together with its substituents, it forms a methyl-isoquinoline-one group (e.g., 2-methylisoquinoline-1(2H)-one).
[0379] The compound or salt provided herein as Example 141 is as described in any one of Examples 1 to 139, wherein, when R 2 When replaced, each R 2 The substituents are independently methyl, ethyl, or isopropyl.
[0380] The compound or salt provided herein as Example 142 is as described in any one of Examples 1 to 139, wherein, when R 2 When replaced, R 2 It is replaced by a methyl group.
[0381] The compound or salt provided herein as Example 143 is as described in any one of Examples 1 to 139, wherein, when R 2 When replaced, R 2 It is replaced by an ethyl group.
[0382] The compound or salt provided herein as Example 144 is as described in any one of Examples 1 to 139, wherein, when R 2 When replaced, R 2 It is replaced by isopropyl.
[0383] The compound or salt provided herein as Example 145 is as described in any one of Examples 1 to 134, wherein R 2 It is not replaced.
[0384] The compound or salt provided herein as Example 146 is as described in any one of Examples 1 to 106, wherein R 2 yes
[0385] , , , , ,or ;
[0386] in
[0387] “ "Indicators can contain either double or single keys;"
[0388] X a Each example is independently nitrogen, oxygen, or carbon;
[0389] Each instance of n, when it exists, is an integer selected from 1, 2, 3, 4, or 5;
[0390] Each instance of n', when it exists, is an integer selected from 1, 2, 3, 4, or 5;
[0391] Each instance of p, when it exists, is an integer selected from 0, 1, 2, 3, or 4;
[0392] Each instance of r, when it exists, is an integer selected from 0, 1, 2, 3, 4, or 5, where two instances of r appear in the same R. 2 When on a group, the combined total value of the two r values does not exceed 5;
[0393] R12 Each example where it exists and is attached to a member of the N-ring is C. 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 alkylene-OH, or C 1-6 Alkylene-OC 1-6 Alkyl; and
[0394] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or -N(R) group. b 2. C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Alkoxy, C 1-6 alkylene-OH, or C 1-6 Alkylene-OC 1-6 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 12 To provide cations. In several embodiments, R 12 Each example where it exists and is attached to a member of the N-ring is C. 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 alkylene-OH, or C 1-6 Alkylene-OC 1-6 Alkyl group. In several embodiments, R 12 Each example where it exists and is attached to a member of the N-ring is C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, R 12 Each example where it exists and is attached to a member of the N-ring is C. 1-3 Alkyl, C 1-3 Halogenated alkyl, or C 1-3 Alkylene-OH. In several embodiments, R 12 Each example where it exists and is attached to a member of the N-ring is C. 1-3 Alkyl, C 1-3 Halogenated alkyl, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, R 12 Each example where it exists and is attached to a member of the N-ring is C. 1-3 Alkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3Alkyl group. In several embodiments, R 12 Each example where it exists and is attached to a member of the N-ring is C. 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, R 12 Each example where it exists and is attached to a member of the N-ring is C. 1-3 Alkyl or C 1-3 Haloalkyl. In several embodiments, R 12 An example of this is C, which exists and is attached to a member of the N-ring. 1-3 Alkyl (e.g., methyl, ethyl, propyl, or isopropyl). In several embodiments, R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or -N(R) group. b 2. C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 alkoxy, or C 1-6 Alkylene-OH. In several embodiments, R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or -N(R) group. b 2. C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 alkoxy, or C 1-6 Alkylene-OC 1-6 Alkyl group. In several embodiments, R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or -N(R) group. b 2. C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 alkylene-OH, or C 1-6 Alkylene-OC 1-6 Alkyl group. In several embodiments, R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or -N(R) group. b 2. C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 alkylene-OH, or C 1-6 Alkylene-OC 1-6 Alkyl group. In several embodiments, R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or -N(R) group. b 2. C1-6 Haloalkyl, C 1-6 Alkoxy, C 1-6 alkylene-OH, or C 1-6 Alkylene-OC 1-6 Alkyl group. In several embodiments, R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or C-ring. 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Alkoxy, C 1-6 alkylene-OH, or C 1-6 Alkylene-OC 1-6 Alkyl group. In several embodiments, R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or -N(R) b 2. C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Alkoxy, C 1-6 alkylene-OH, or C 1-6 Alkylene-OC 1-6 Alkyl group. In several embodiments, R 12 Each example, when present and attached to a C-ring member, is independently halogenated, oxo-, -N(R) b 2. C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Alkoxy, C 1-6 alkylene-OH, or C 1-6 Alkylene-OC 1-6 Alkyl group. In several embodiments, R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or -N(R) group. b 2. C 1-6 Alkyl, C 1-6 Halogenated alkyl, or C 1-6 Alkyl group. In several embodiments, R 12 Each example that exists and is attached to a member of ring C is C. 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 alkylene-OH, or C 1-6 Alkylene-OC 1-6 Alkyl group. In several embodiments, R 12 Each example that exists and is attached to a member of ring C is C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3Alkylene-OC 1-3 Alkyl group. In several embodiments, R 12 Each example that exists and is attached to a member of ring C is C. 1-3 Alkyl, C 1-3 Halogenated alkyl, or C 1-3 Alkylene-OH. In several embodiments, R 12 Each example that exists and is attached to a member of ring C is C. 1-3 Alkyl, C 1-3 Halogenated alkyl, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, R 12 Each example that exists and is attached to a member of ring C is C. 1-3 Alkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, R 12 Each example that exists and is attached to a member of ring C is C. 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, R 12 Each example that exists and is attached to a member of ring C is C. 1-3 Alkyl or C 1-3 Haloalkyl. In several embodiments, R 12 An example of this is C when it exists and is attached to a member of ring C. 1-3 Alkyl group. In several embodiments, R 12 An example of this is C when it exists and is attached to a member of ring C. 1-2 Alkyl group. In several embodiments, R 12 An example of this is C when it exists and is attached to a member of ring C. 2-3 Alkyl group. In several embodiments, R 12 An example of this is methyl when it is present and attached to a C-ring member. In several embodiments, R 12 An example of this is the presence and attachment to a C-ring member, specifically a C2 alkyl group. In several embodiments, R... 12 An example of this is the presence and attachment to a C-ring member, specifically a C3 alkyl group. In several embodiments, R... 12 An example of this is C when it exists and is attached to a member of ring C. 1-2 Haloalkyl. In several embodiments, R 12 An example of this is a C1 haloalkyl group when it is present and attached to a C-ring member. In several embodiments, R 12 An example of this is a C2 haloalkyl group when it is present and attached to a C-ring member. In several embodiments, R12 An example of this is a C3 haloalkyl group present and attached to a C-ring member. In several embodiments, the R... 12 The halogen is -F, -Cl, or -Br. In several embodiments, the R... 12 The halogen is -F or -Cl. In several embodiments, the R... 12 Halogens are -F.
[0395] The compound or salt provided herein as Example 147 is any one of Examples 1 to 17, 19 to 106, and 146, wherein formula (A) is further represented by a compound having formula (A2i):
[0396] (A2i);
[0397] in
[0398] “ "Indicators can contain either double or single keys;"
[0399] X a Each example is independently nitrogen, oxygen, or carbon;
[0400] Each instance of n, when it exists, is an integer selected from 1, 2, 3, 4, or 5; and
[0401] Each instance of n', when it exists, is an integer selected from 1, 2, 3, 4, or 5;
[0402] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0403] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or C-ring. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 12 To provide cations. In several embodiments, the variable of compounds having formula (A2i) is as defined in any of Examples 1 to 17, 19 to 106, and 146.
[0404] The compound or salt provided herein as Example 148 is any one of Examples 1 to 17, 19 to 106, and 146, wherein formula (A) is further represented by a compound having formula (A2ii):
[0405] (A2ii);
[0406] in
[0407] “ "Indicators can contain either double or single keys;"
[0408] X a Each example is independently nitrogen, oxygen, or carbon;
[0409] Each example of p is an integer selected from 0, 1, 2, 3, or 4;
[0410] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0411] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or C-ring. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 12 To provide cations. In several embodiments, the variable of compounds having formula (A2ii) is as defined in any one of Examples 1 to 17, 19 to 106, and 146.
[0412] The compound or salt provided herein as Example 149 is any one of Examples 1 to 17, 19 to 106, and 146, wherein formula (A) is further represented by a compound having formula (A2iii):
[0413] (A2iii);
[0414] in
[0415] “ "Indicators can contain either double or single keys;"
[0416] X a Each example is independently nitrogen, oxygen, or carbon;
[0417] Each example of r is an integer selected from 0, 1, 2, 3, 4 or 5, wherein when two examples of r appear on the compound of formula (A2iii), the total value of the combination of the two r values does not exceed 5;
[0418] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0419] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or C-ring. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 12 To provide cations. In several embodiments, the variable of compounds having formula (A2iii) is as defined in any of Examples 1 to 17, 19 to 106, and 146.
[0420] The compound or salt provided herein as Example 150 is any one of Examples 1 to 17, 19 to 106, and 146, wherein formula (A) is further represented by a compound having formula (A2iv):
[0421] (A2iv);
[0422] in
[0423] “ "Indicators can contain either double or single keys;"
[0424] X a Each example is independently nitrogen, oxygen, or carbon;
[0425] Each example of r is an integer selected from 0, 1, 2, 3, 4 or 5, wherein when two examples of r appear on the compound of formula (A2iv), the total value of the combination of the two r values does not exceed 5;
[0426] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0427] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or C-ring. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 12 To provide cations. In several embodiments, the variable of compounds having formula (A2iv) is as defined in any one of Examples 1 to 17, 19 to 106, and 146.
[0428] The compound or salt provided herein as Example 151 is any one of Examples 1 to 17, 19 to 106, and 146, wherein formula (A) is further represented by a compound having formula (A2v):
[0429] (A2v);
[0430] in
[0431] “ "Indicators can contain either double or single keys;"
[0432] X a Each example is independently nitrogen, oxygen, or carbon;
[0433] Each example of r is an integer selected from 0, 1, 2, 3, 4 or 5, wherein when two examples of r appear on the compound of formula (A2v), the total value of the combination of the two r values does not exceed 5;
[0434] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0435] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or C-ring. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 12 To provide cations. In several embodiments, the variable of compounds having formula (A2v) is as defined in any one of Examples 1 to 17, 19 to 106, and 146.
[0436] The compound or salt provided herein as Example 152 is as described in any one of Examples 1 to 106 and 146, wherein R 2 yes
[0437] , , , , , , , , , , , , ,or
[0438] in
[0439] Each instance of n, when it exists, is an integer selected from 1, 2, 3, 4, or 5;
[0440] Each instance of n', when it exists, is an integer selected from 0, 1, 2, 3, 4, or 5;
[0441] Each instance of p, when it exists, is an integer selected from 0, 1, 2, 3, or 4;
[0442] Each instance of q, when it exists, is an integer selected from 0, 1, 2, 3, 4, or 5;
[0443] Each instance of r, when it exists, is an integer selected from 0, 1, 2, 3, 4, or 5, where two instances of r appear in the same R. 2 When on a group, the combined total value of the two r values does not exceed 5;
[0444] Each instance of s, when it exists, is an integer selected from 0, 1, or 2;
[0445] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 alkyl;
[0446] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 alkyl;
[0447] -H on any ring member can be R 12 Alternatively, in several embodiments, -N=cyclic nitrogen can be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 12 To provide cations. In several embodiments, each R provided is... 2 The variables of the structure are defined as in any of Examples 1 to 106 and 146.
[0448] The compound or salt provided herein as Example 153 is any one of Examples 1 to 106 and 146, wherein R 2 yes:
[0449]
[0450] in
[0451] n is an integer selected from 1, 2, 3, 4 or 5;
[0452] n' is an integer selected from 0, 1, 2, 3, 4 or 5;
[0453] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 alkyl.
[0454] The compound or salt provided herein as Example 154 is as described in any one of Examples 1 to 106 and 146, wherein R 2 yes:
[0455]
[0456] in
[0457] p is an integer selected from 0, 1, 2, 3 or 4;
[0458] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0459] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 alkyl.
[0460] The compound or salt provided herein as Example 155 is any one of Examples 1 to 106 and 146, wherein R 2 yes:
[0461]
[0462] in
[0463] q is an integer selected from 0, 1, 2, 3, 4, or 5;
[0464] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0465] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R.12 To provide cations.
[0466] The compound or salt provided herein as Example 156 is as described in any one of Examples 1 to 106 and 146, wherein R 2 yes:
[0467]
[0468] in
[0469] Each example of r is an integer selected from 0, 1, 2, or 3;
[0470] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0471] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 12 To provide cations.
[0472] The compound or salt provided herein as Example 157 is any one of Examples 1 to 106 and 146, wherein R 2 yes:
[0473]
[0474] in
[0475] Each example of r is an integer selected from 0, 1, 2, or 3;
[0476] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0477] R12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 12 To provide cations.
[0478] The compound or salt provided herein as Example 158 is any one of Examples 1 to 106 and 146, wherein R 2 yes:
[0479]
[0480] in
[0481] Each example of r is an integer selected from 0, 1, 2, or 3;
[0482] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0483] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 12 To provide cations.
[0484] The compound or salt provided herein as Example 159 is any one of Examples 1 to 106 and 146, wherein R 2 yes
[0485]
[0486] in
[0487] Each example of r is an integer selected from 0, 1, 2, or 3;
[0488] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0489] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 12 To provide cations.
[0490] The compound or salt provided herein as Example 160 is any one of Examples 1 to 106 and 146, wherein R 2 yes:
[0491]
[0492] in
[0493] Each example of r is an integer selected from 0, 1, 2, or 3;
[0494] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0495] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R.12 To provide cations.
[0496] The compound or salt provided herein as Example 161 is as described in any one of Examples 1 to 106 and 146, wherein R 2 yes:
[0497]
[0498] in
[0499] Each instance of r, when it exists, is an integer selected from 0, 1, 2, or 3;
[0500] Each instance of s, when it exists, is an integer selected from 0, 1, or 2;
[0501] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0502] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 12 To provide cations.
[0503] The compound or salt provided herein as Example 162 is any one of Examples 1 to 106 and 146, wherein R 2 yes:
[0504]
[0505] in
[0506] Each instance of r, when it exists, is an integer selected from 0, 1, or 2;
[0507] Each instance of s, when it exists, is an integer selected from 0 or 1;
[0508] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0509] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 12 To provide cations.
[0510] The compound or salt provided herein as Example 163 is any one of Examples 1 to 106 and 146, wherein R 2 yes:
[0511]
[0512] in
[0513] Each instance of r, when it exists, is an integer selected from 0, 1, 2, or 3;
[0514] Each instance of s, when it exists, is an integer selected from 0, 1, or 2;
[0515] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0516] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 alkyl.
[0517] The compound or salt provided herein as Example 164 is any one of Examples 1 to 106 and 146, wherein R 2 yes:
[0518]
[0519] in
[0520] Each instance of p, when it exists, is an integer selected from 0, 1, 2, 3, or 4;
[0521] Each instance of r, when it exists, is an integer selected from 0, 1, 2, or 3;
[0522] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0523] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 alkyl;
[0524] Where R 12 It can be attached to an =N-ring member to provide an ammonium cation.
[0525] The compound or salt provided herein as Example 165 is any one of Examples 1 to 106 and 146, wherein R 2 yes:
[0526]
[0527] in
[0528] Each instance of p, when it exists, is an integer selected from 0, 1, 2, 3, or 4;
[0529] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0530] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl group. In several embodiments, -N=cyclonitrogen group may be bonded to R. 12 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 12 To provide cations.
[0531] The compound or salt provided herein as Example 166 is any one of Examples 1 to 106 and 146, wherein R 2 yes:
[0532]
[0533] in
[0534] Each instance of r, when it exists, is an integer selected from 0, 1, 2, or 3;
[0535] R 12 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 Alkyl; and
[0536] R 12 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, or C. 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 alkylene-OH, or C 1-3 Alkylene-OC 1-3 alkyl.
[0537] The compound or salt provided herein as Example 167 is any one of Examples 1 to 106 and 146, wherein R 2 yes
[0538] , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,or For example, in several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is In several embodiments, R 2 (including its substituents) is Considering the aforementioned R 2 Any combination of substituents.
[0539] The compound or salt provided herein as Example 168 is any one of Examples 1 to 106 and 146, wherein R 2 yes
[0540] , , , , , , , , , , , , , , , , , , , , ,or .
[0541] The compound or salt provided herein as Example 169 is any one of Examples 1 to 20 and 22 to 168, wherein R 3 It is C 3-6 cycloalkyl, C 3-10 Cycloalkenyl, C 6-10 Aryl, heteroaryl having 5 to 10 ring members, or heterocyclic having 5 to 10 ring members. For example, in several embodiments, R 3 It is C 3-6 Cycloalkyl. In several embodiments, R 3 It is C 4-6 Cycloalkyl. In several embodiments, R 3 It is C 3-5 Cycloalkyl. In several embodiments, R 3 It is C 4-6 Cycloalkyl. In several embodiments, R 3 It is C 3-4 Cycloalkyl. In several embodiments, R 3 It is C 5-6 Cycloalkyl. In several embodiments, R 3 It is a C3 cycloalkyl group (e.g., cyclopropyl). In several embodiments, R 3 It is a C4 cycloalkyl group (e.g., cyclobutyl). In several embodiments, R 3 It is a C5 cycloalkyl group. In several embodiments, R 3 It is a C6 cycloalkyl group.
[0542] The compound or salt provided herein as Example 170 is any one of Examples 1 to 20 and 22 to 169, wherein R 3 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 3 Heteroaryl or heterocyclic groups contain 1, 2, 3, 4 or 5 heterocyclic members.
[0543] The compound or salt provided herein as Example 171 is any one of Examples 1 to 20 and 22 to 169, wherein R 3 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 3 Heteroaryl or heterocyclic groups contain 1, 2, 3 or 4 heterocyclic members.
[0544] The compound or salt provided herein as Example 172 is any one of Examples 1 to 20 and 22 to 169, wherein R 3 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 3 Heteroaryl or heterocyclic groups contain one, two, or three heterocyclic members.
[0545] The compound or salt provided herein as Example 173 is any one of Examples 1 to 20 and 22 to 169, wherein R 3 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 3 A heteroaryl or heterocyclic group contains one or two heterocyclic members.
[0546] The compound or salt provided herein as Example 174 is any one of Examples 1 to 20 and 22 to 169, wherein R 3 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 3 A heteroaryl or heterocyclic group contains one heteroatom ring member.
[0547] The compound or salt provided herein as Example 175 is any one of Examples 1 to 20 and 22 to 174, wherein R 3 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 3 Each heteroatom in the ring is independently nitrogen, oxygen, or -S(O). z - where z is 0, 1 or 2.
[0548] The compound or salt provided herein as Example 176 is any one of Examples 1 to 20 and 22 to 174, wherein R 3 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 3 Each heteroatom in the ring is either nitrogen or oxygen.
[0549] The compound or salt provided herein as Example 177 is any one of Examples 1 to 20 and 22 to 174, wherein R 3 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R3 Each heteroatom in the ring is nitrogen.
[0550] The compound or salt provided herein as Example 178 is any one of Examples 1 to 20, 22 to 171 and 175 to 177, wherein R 3 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group containing four nitrogen heteroatomic ring atoms.
[0551] The compound or salt provided herein as Example 179 is any one of Examples 1 to 20, 22 to 172, and 175 to 177, wherein R 3 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group containing three nitrogen atoms.
[0552] The compound or salt provided herein as Example 180 is any one of Examples 1 to 20, 22 to 173, and 175 to 177, wherein R 3 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group containing two nitrogen atoms.
[0553] The compound or salt provided herein as Example 181 is any one of Examples 1 to 20 and 22 to 177, wherein R 3 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group containing a nitrogen atom.
[0554] The compound or salt provided herein as Example 182 is any one of Examples 1 to 20 and 22 to 176, wherein R 3 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group, and the R 3 Each heteroatom in the ring is an oxygen atom.
[0555] The compound or salt provided herein as Example 183 is any one of Examples 1 to 20 and 22 to 182, wherein R 3 It is an unsubstituted or substituted fused bicyclic heteroaryl group or an unsubstituted or substituted fused bicyclic heterocycle.
[0556] The compound or salt provided herein as Example 184 is any one of Examples 1 to 20 and 22 to 182, wherein R 3 It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group containing 5 to 9 ring members.
[0557] The compound or salt provided herein as Example 185 is any one of Examples 1 to 20 and 22 to 182, wherein R 3It is an unsubstituted or substituted heteroaryl group or an unsubstituted or substituted heterocyclic group containing 5 to 10 ring members.
[0558] The compound or salt provided herein as Example 186 is any one of Examples 1 to 20 and 22 to 183, wherein R 3 It is an unsubstituted or substituted heteroaryl group containing 8 to 10 ring members or an unsubstituted or substituted heterocyclic group containing 8 to 10 ring members.
[0559] The compound or salt provided herein as Example 187 is any one of Examples 1 to 20 and 22 to 183, wherein R 3 It is an unsubstituted or substituted heteroaryl group containing 9 to 10 ring members or an unsubstituted or substituted heterocyclic group containing 9 to 10 ring members.
[0560] The compound or salt provided herein as Example 188 is any one of Examples 1 to 20 and 22 to 183, wherein R 3 It is an unsubstituted or substituted heteroaryl group containing 9 ring members or an unsubstituted or substituted heterocyclic group containing 9 ring members.
[0561] The compound or salt provided herein as Example 189 is any one of Examples 1 to 20 and 22 to 183, wherein R 3 It is an unsubstituted or substituted heteroaryl group containing 10 ring members or an unsubstituted or substituted heterocyclic group containing 10 ring members.
[0562] The compound or salt provided herein as Example 190 is any one of Examples 1 to 20, 22 to 169, and 171 to 182, wherein R 3 It is an unsubstituted or substituted heteroaryl group containing 6 ring members or an unsubstituted or substituted heterocyclic group containing 6 ring members.
[0563] The compound or salt provided herein as Example 191 is any one of Examples 1 to 20, 22 to 169, and 171 to 182, wherein R 3 It is an unsubstituted or substituted heteroaryl group containing 5 ring members or an unsubstituted or substituted heterocyclic group containing 5 ring members.
[0564] The compound or salt provided herein as Example 192 is any one of Examples 1 to 20 and 22 to 191, wherein R 3 It is an unsubstituted or substituted heteroaryl group.
[0565] The compound or salt provided herein as Example 193 is any one of Examples 1 to 20 and 22 to 191, wherein R3 It is an unsubstituted or substituted heterocyclic group.
[0566] As another embodiment provided herein is a compound or salt as described in any one of Examples 1 to 20 and 22 to 168, wherein R 3 Is it unsubstituted or substituted C? 3-4 Cycloalkyl.
[0567] The compound or salt provided herein as Example 194 is any one of Examples 1 to 20 and 22 to 168, wherein R 3 Is it unsubstituted or substituted C? 3-4 Cycloalkyl. For example, in several embodiments, R 3 It is cyclopropyl. In several embodiments, R 3 It is cyclobutyl.
[0568] The compound or salt provided herein as Example 195 is any one of Examples 1 to 20 and 22 to 168, wherein R 3 Is it unsubstituted or substituted C? 1-6 alkyl.
[0569] The compound or salt provided herein as Example 196 is any one of Examples 1 to 20 and 22 to 168, wherein R 3 Is it unsubstituted or substituted C? 6-10 Aryl.
[0570] The compound or salt provided herein as Example 197 is any one of Examples 1 to 20 and 22 to 196, wherein R 3 It can be substituted by 1, 2, 3, 4 or 5 substituents.
[0571] The compound or salt provided herein as Example 198 is any one of Examples 1 to 20 and 22 to 197, wherein R 3 It can be substituted by 1, 2, 3 or 4 substituents.
[0572] The compound or salt provided herein as Example 199 is any one of Examples 1 to 20 and 22 to 198, wherein R 3 It is substituted by 1, 2 or 3 substituents.
[0573] The compound or salt provided herein as Example 200 is any one of Examples 1 to 20 and 22 to 199, wherein R 3 It is substituted by one or two substituents.
[0574] The compound or salt provided herein as Example 201 is any one of Examples 1 to 20 and 22 to 200, wherein R3 It is substituted by one substituent. For example, in several embodiments, R 3 yes , ,or In several embodiments, R 3 Together with its substituents, it forms alkyl-pyrazolo[3,4-b]pyridine (e.g., 2-methyl-2H-pyrazolo[3,4-b]pyridyl, etc.).
[0575] The compound or salt provided herein as Example 202 is any one of Examples 1 to 20 and 22 to 201, wherein, when R 3 When replaced, each R 3 The substituent is C independently 1-3 Alkyl, C 1-3 alkoxy, or C 1-3 Alkylene-C 1-3 Alkyl groups. For example, in several embodiments, when R... 3 When replaced, R 3 The substituent can be -CH2OCH3.
[0576] The compound or salt provided herein as Example 203 is any one of Examples 1 to 20 and 22 to 196, wherein, when R 3 When replaced, each R 3 The substituents are independently methyl, ethyl, or isopropyl.
[0577] The compound or salt provided herein as Example 204 is any one of Examples 1 to 20 and 22 to 203, wherein, when R 3 When replaced, R 3 It is replaced by a methyl group.
[0578] The compound or salt provided herein as Example 205 is any one of Examples 1 to 20 and 22 to 203, wherein, when R 3 When replaced, R 3 It is replaced by an ethyl group.
[0579] The compound or salt provided herein as Example 206 is any one of Examples 1 to 20 and 22 to 203, wherein, when R 3 When replaced, R 3 It is replaced by isopropyl.
[0580] The compound or salt provided herein as Example 207 is any one of Examples 1 to 20 and 22 to 196, wherein R 3 It is not replaced.
[0581] The compound or salt provided herein as Example 208 is any one of Examples 1 to 20 and 22 to 168, wherein R 3 Yes, it's -H.
[0582] The compound or salt provided herein as Example 209 is any one of Examples 1 to 20 and 22 to 168, wherein R 3 yes
[0583] , , , , ,or ;
[0584] in
[0585] “ "Indicators can contain either double or single keys;"
[0586] X b Each example is independently nitrogen, oxygen, or carbon;
[0587] Each instance of t, when it exists, is an integer selected from 1, 2, 3, 4, or 5;
[0588] Each instance of t' when it exists is an integer selected from 1, 2, 3, 4, or 5;
[0589] Each instance of v, when it exists, is an integer selected from 0, 1, 2, 3, 4, or 5, where two instances of v occur in the same R. 3 When on a group, the combined total value of the two v values does not exceed 5;
[0590] R 13 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Halogenated alkyl, or C 1-3 Alkylene-C 1-3 alkoxy groups; and
[0591] R 13 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or -N(R) group. b 2. C 1-3 Alkyl, C 1-3 Halogenated alkyl, or C 1-3 Alkylene-OC 1-3 alkyl;
[0592] Alternatively, R 13 The two examples together form a C with 3 to 6 ring members. 3-6 cycloalkyl or heterocyclic groups, when R3 When it is a ring structure, it can provide a fused ring system or a spiro ring system. In several embodiments, -N=cyclic nitrogen can be bonded to R. 13 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 13 To provide cations.
[0593] The compound or salt provided herein as Example 210 is any one of Examples 1 to 20 and 22 to 168, wherein R 3 yes:
[0594] , , ,or ;
[0595] in
[0596] Each instance of t, when it exists, is an integer selected from 1, 2, 3, 4, or 5;
[0597] Each instance of t' when it exists is an integer selected from 1, 2, 3, 4, or 5;
[0598] Each instance of v, when it exists, is an integer selected from 0, 1, 2, 3, 4, or 5, where two instances of v occur in the same R. 3 When on a group, the combined total value of the two v values does not exceed 5;
[0599] R 13 Each instance, when it exists and is attached to a member of the N-ring, is independently C. 1-3 Alkyl, C 1-3 Halogenated alkyl, or C 1-3 Alkylene-C 1-3 alkoxy groups; and
[0600] R 13 Each example, when present and attached to a C-ring member, is independently a halogen, -OH, oxo, or C-ring. 1-3 Alkyl, C 1-3 Halogenated alkyl, or C 1-3 Alkylene-OC 1-3 alkyl;
[0601] Alternatively, R 13 The two examples together form a C with 3 to 6 ring members. 3-6 cycloalkyl or heterocyclic groups, when R 3 When it is a ring structure, it can provide a fused ring system or a spiro ring system. In several embodiments, -N=cyclic nitrogen can be bonded to R. 13 To provide cations. In several embodiments, no -N= cyclic nitrogen is bonded to R. 13 To provide cations.
[0602] The compound or salt provided herein as Example 211 is any one of Examples 1 to 20 and 22 to 168, wherein R 3 Together with its substituents, it is
[0603] , , , ,or .
[0604] The compound or salt provided herein as Example 212 is any one of Examples 1 to 20 and 22 to 168, wherein R 3 yes:
[0605] .
[0606] The compound or salt provided herein as Example 213 is any one of Examples 1 to 20 and 22 to 168, wherein R 3 yes:
[0607] .
[0608] The compound or salt provided herein as Example 214 is any one of Examples 1 to 20 and 22 to 168, wherein R 3 yes:
[0609] .
[0610] The compound or salt provided herein as Example 215 is any one of Examples 1 to 20 and 22 to 168, wherein R 3 yes:
[0611] .
[0612] The compound or salt provided herein as Example 216 is any one of Examples 1 to 20 and 22 to 168, wherein R 3 yes:
[0613] .
[0614] The compound or salt provided herein as Example 217 is as described in any one of Examples 1 to 216, wherein R b Each example is independently substituted by 1, 2, 3, 4 or 5 substituents.
[0615] The compound or salt provided herein as Example 218 is as described in any one of Examples 1 to 217, wherein Rb Each example is independently substituted by 1, 2, 3 or 4 substituents.
[0616] The compound or salt provided herein as Example 219 is as described in any one of Examples 1 to 218, wherein R b Each example is independently substituted by 1, 2, or 3 substituents.
[0617] The compound or salt provided herein as Example 220 is as described in any one of Examples 1 to 219, wherein R b Each example is independently substituted by one or two substituents.
[0618] The compound or salt provided herein as Example 221 is as described in any one of Examples 1 to 220, wherein R b Each example is independently substituted by one substituent.
[0619] The compound or salt provided herein as Example 222 is as described in any one of Examples 1 to 230, wherein R b Each example is unreplaced.
[0620] The compound or salt provided herein as Example 223 is any one of Examples 1 to 24 and 26 to 222, wherein R 4 It is -H, C 1-3 Alkyl, halogen, or -N(R) a )2, where R a Each instance, when it exists, is independently -H or C. 1-6 alkyl.
[0621] The compound or salt provided herein as Example 224 is any one of Examples 1 to 24 and 26 to 223, and is any one of Examples 1 to 24 and 26 to 222, wherein R 4 It is -N(R) a )2.
[0622] The compound or salt provided herein as Example 225 is as described in any one of Examples 1 to 24 and 26 to 224, wherein R a Each example is independently substituted by 1, 2, 3, 4 or 5 substituents.
[0623] The compound or salt provided herein as Example 226 is as described in any one of Examples 1 to 24 and 26 to 224, wherein R a Each example is independently substituted by 1, 2, 3 or 4 substituents.
[0624] The compound or salt provided herein as Example 227 is any one of Examples 1 to 24 and 26 to 224, wherein R a Each example is independently substituted by 1, 2, or 3 substituents.
[0625] The compound or salt provided herein as Example 228 is as described in any one of Examples 1 to 24 and 26 to 224, wherein R a Each example is independently substituted by one or two substituents.
[0626] The compound or salt provided herein as Example 229 is as described in any one of Examples 1 to 24 and 26 to 224, wherein R a Each example is independently substituted by one substituent.
[0627] The compound or salt provided herein as Example 230 is any one of Examples 1 to 24 and 26 to 224, wherein R a Each example is unreplaced.
[0628] The compound or salt provided herein as Example 231 is as described in any one of Examples 1 to 24 and 26 to 230, wherein R a At least one example is C 1-3 alkyl.
[0629] The compound or salt provided herein as Example 232 is any one of Examples 1 to 24, 26 to 223, and 231, wherein R a At least one example is -CH3.
[0630] The compound or salt provided herein as Example 233 is any one of Examples 1 to 24, 26 to 223, and 231 to 232, wherein R a At least one example is -H.
[0631] The compound or salt provided herein as Example 234 is any one of Examples 1 to 24, 26 to 223, and 231 to 233, wherein R a Each example is -H.
[0632] The compound or salt provided herein as Example 235 is any one of Examples 1 to 24 and 26 to 223, wherein R 4 It is C 1-3 alkyl.
[0633] The compound or salt provided herein as Example 236 is any one of Examples 1 to 24 and 26 to 223, wherein R 4 It is a methyl group.
[0634] The compound or salt provided herein as Example 237 is any one of Examples 1 to 24 and 26 to 223, wherein R 4 It is halogen.
[0635] The compound or salt provided herein as Example 238 is any one of Examples 1 to 24 and 26 to 223, wherein R 4 It is -Cl.
[0636] The compound or salt provided herein as Example 239 is any one of Examples 1 to 24 and 26 to 223, wherein R 4 Yes, it's -H.
[0637] The compound or salt provided herein as Example 240 is any one of Examples 1 to 239, wherein R 5 It can be independently substituted by 1, 2, 3, or 4 substituents. For example, in several embodiments, R 5 It is substituted with 1 to 4 substituents. In several embodiments, R 5 It is substituted with 1 to 3 substituents. In several embodiments, R 5 It is substituted with 1 to 2 substituents. In several embodiments, R 5 It is substituted with 2 to 4 substituents. In several embodiments, R 5 It is substituted with 3 to 4 substituents. In several embodiments, R 5 It is substituted with 2 to 3 substituents. In several embodiments, R 5 It is substituted by 1, 2 or 4 substituents.
[0638] The compound or salt provided herein as Example 241 is any one of Examples 1 to 22 and 24 to 239, wherein R 5 It can be independently substituted by 1, 2 or 3 substituents.
[0639] The compound or salt provided herein as Example 242 is any one of Examples 1 to 22 and 24 to 239, wherein R 5 It can be independently substituted by one or two substituents.
[0640] The compound or salt provided herein as Example 243 is any one of Examples 1 to 22 and 24 to 239, wherein R 5 It can be independently substituted by one substituent.
[0641] The compound or salt provided herein as Example 244 is any one of Examples 1 to 22 and 24 to 239, wherein R 5 It is not replaced.
[0642] The compound or salt provided herein as Example 245 is as described in any one of Examples 1 to 22 and 24 to 244, wherein R 5 It is -H or unsubstituted or substituted C 1-6 alkyl.
[0643] The compound or salt provided herein as Example 246 is any one of Examples 1 to 22 and 24 to 239, wherein R 5 It is -H or -CH2OH.
[0644] The compound or salt provided herein as Example 247 is any one of Examples 1 to 22 and 24 to 239, wherein R 5 Yes, it's -H.
[0645] The compound or salt provided herein as Example 248 is any one of Examples 1 to 22 and 24 to 239, wherein R 5 It is -CH2OCH3.
[0646] The compound or salt provided herein as Example 249 is any one of Examples 1, 2, 10 to 13, 15 to 20, and 34 to 248, wherein the compound having formula (A) is a compound having formula (II):
[0647] (II).
[0648] The compound or salt provided herein as Example 250 is any one of Examples 1 to 3, 5, 8, 10 to 14, 16 to 248, wherein the compound having formula (A) is a compound having formula (III):
[0649] (III).
[0650] The compound or salt provided herein as Example 251 is any one of Examples 1, 2, 4, 6 to 13, 15 to 26, and 34 to 248, wherein the compound having formula (A) is a compound having formula (IV):
[0651] (IV).
[0652] The compound or salt provided herein as Example 252 is any one of Examples 1, 2, 5, 10 to 14, 16 to 22, 25, 26, and 34 to 239, wherein the compound having formula (A) is a compound having formula (V):
[0653] (V).
[0654] The compound or salt provided herein as Example 253 is any one of Examples 1, 2, 4, 6, 7, 10 to 13, 15 to 22, 25, 26, and 34 to 239, wherein the compound having formula (A) is a compound having formula (VI):
[0655] (VI).
[0656] The compound or salt provided herein as Example 254 is any one of Examples 1 to 5, 8, 10 to 14, 16 to 20, 23 to 26, 34 to 168, and 217 to 248, wherein the compound having formula (A) is a compound having formula (VII):
[0657] (VII)
[0658] The compound or salt provided herein as Example 255 is any one of Examples 1, 2, 4, 6 to 13, 15 to 20, 23 to 26, 34 to 168, and 217 to 248, wherein the compound having formula (A) is a compound having formula (VIII):
[0659] (VIII)
[0660] The compound or salt provided herein as Example 256 is any one of Examples 1, 2, 5, 10 to 14, 16 to 20, 25 to 168, and 217 to 239, wherein the compound having formula (A) is a compound having formula (IX):
[0661] (IX).
[0662] The compound or salt provided herein as Example 257 is any one of Examples 1, 2, 6, 7, 10 to 13, 15 to 20, 25, 26, 34 to 168, and 217 to 239, wherein the compound having formula (A) is a compound having formula (X):
[0663] (X).
[0664] The compound or salt provided herein as Example 258 is any one of Examples 1, 2, 10 to 12, 16 to 22, and 34 to 222, wherein the compound having formula (A) is a compound having formula (XI):
[0665] (XI).
[0666] The compound or salt provided herein as Example 259 is any one of Examples 1, 2, 10 to 12, 16 to 22, and 34 to 222, wherein the compound having formula (A) is a compound having formula (XII):
[0667] (XII).
[0668] The compound or salt provided herein as Example 260 is any one of Examples 1, 27 to 97, 107 to 222, and 240 to 248, wherein the compound having formula (A) is a compound having formula (IAi):
[0669] (IAi).
[0670] The compound or salt provided herein as Example 261 is any one of Examples 1, 2, 10-14, 16, 19, 20, 27 to 97, 107 to 222, and 240 to 248, wherein the compound having formula (A) is a compound having formula (IAii):
[0671] (IAii).
[0672] The compound or salt provided herein as Example 262 is any one of Examples 1, 2, 10-14, 16, 19, 20, 22, 24, 26 to 97, and 107 to 239, wherein the compound having formula (A) is a compound having formula (IBi):
[0673] (IBi).
[0674] The compound or salt provided herein as Example 263 is any one of Examples 1, 2, 10-14, 16, 19, 20, 22, 26 to 96, and 107 to 222, wherein the compound having formula (A) is a compound having formula (IBii):
[0675] (IBii).
[0676] The compound or salt provided herein as Example 264 is any one of Examples 1, 2, 10-14, 16, 19, 20, 22, 26 to 96, and 107 to 222, wherein the compound having formula (A) is a compound having formula (IBiii):
[0677] (IBiii)
[0678] The compound or salt provided herein as Example 265 is any one of Examples 1, 2, 11-14, 16, 19, 20, 24, 26 to 97, 107 to 168, and 217 to 248, wherein the compound having formula (A) is a compound having formula (ICi):
[0679] (ICi).
[0680] The compound or salt provided herein as Example 266 is any one of Examples 1, 2, 11-14, 16, 19, 20, 24, 26 to 97, and 107 to 168, 217 to 222, and 240 to 248, wherein the compound having formula (A) is a compound having formula (ICii):
[0681] (ICii).
[0682] The compound or salt provided herein as Example 267 is any one of Examples 1, 2, 11-14, 16, 19, 20, 24, 27 to 97, 103, 107 to 168, 217 to 222, and 240 to 248, wherein the compound having formula (A) is a compound having formula (ICiii):
[0683] (ICiii)
[0684] The compound or salt provided herein as Example 268 is any one of Examples 1, 2, 11-14, 16, 19, 20, 27 to 97, 107 to 168, and 217 to 239, wherein the compound having formula (A) is a compound having formula (IDi):
[0685] (IDi).
[0686] The compound or salt provided herein as Example 269 is any one of Examples 1, 2, 11-14, 16, 19, 20, 27 to 97, 107 to 168, and 217 to 222, wherein the compound having formula (A) is a compound having formula (IDii):
[0687] (IDii).
[0688] The compound or salt provided herein as Example 270 is any one of Examples 1, 2, 11-14, 16, 27 to 97, 107 to 168, and 217 to 222, wherein the compound having formula (A) is a compound having formula (I-1):
[0689] (I-1).
[0690] The compound or salt provided herein as Example 271 is any one of Examples 1, 2, 11-14, 16, 27 to 97, 107 to 168, and 217 to 239, wherein the compound having formula (A) is a compound having formula (I-2):
[0691] (I-2).
[0692] The compound or salt provided herein as Example 272 is any one of Examples 1, 2, 11-14, 16, 27 to 97, 107 to 168, and 217 to 222, wherein the compound having formula (A) is a compound having formula (I-3):
[0693] (I-3).
[0694] The compound or salt provided herein as Example 273 is any one of Examples 1, 2, 11-14, 16, 34 to 97, 107 to 168, and 217 to 222, wherein the compound having formula (A) is a compound having formula (III-1):
[0695] (III-1)
[0696] The compound or salt provided herein as Example 274 is any one of Examples 1, 2, 11-14, 16, 34 to 97, 107 to 168, and 217 to 222, wherein the compound having formula (A) is a compound having formula (III-2):
[0697] (III-2)
[0698] The compound or salt provided herein as Example 275 is any one of Examples 1, 2, 11-14, 16, 34 to 97, 107 to 168, and 217 to 222, wherein the compound having formula (A) is a compound having formula (III-3):
[0699] (III-3)
[0700] The compound or salt provided herein as Example 276 is any one of Examples 1, 2, 11-14, 16, 34 to 97, 107 to 168, and 217 to 222, wherein the compound having formula (A) is a compound having formula (III-4):
[0701] (III-4)
[0702] The compound or salt provided herein as Example 277 is any one of Examples 1, 2, 11-14, 16, 34 to 97, 107 to 168, and 217 to 239, wherein the compound having formula (A) is a compound having formula (III-5):
[0703] (III-5)
[0704] The compound or salt provided herein as Example 278 is any one of Examples 1, 2, 11-13, 15, 16, 34 to 97, 107 to 168, and 217 to 222, wherein the compound having formula (A) is a compound having formula (IV-1):
[0705] (IV-1)
[0706] The compound or salt provided herein as Example 279 is any one of Examples 1, 2, 11-13, 15, 16, 34 to 97, 107 to 168, and 217 to 222, wherein the compound having formula (A) is a compound having formula (IV-2):
[0707] (IV-2).
[0708] The compound or salt provided herein as Example 280 is any one of Examples 1, 2, 11-13, 15, 16, 34 to 97, 107 to 168, and 217 to 222, wherein the compound having formula (A) is a compound having formula (IV-3):
[0709] (IV-3)
[0710] The compound or salt provided herein as Example 281 is any one of Examples 1, 2, 11-13, 15, 16, 34 to 97, 107 to 168, and 217 to 222, wherein the compound having formula (A) is a compound having formula (IV-4):
[0711] (IV-4)
[0712] The compound or salt provided herein as Example 282 is any one of Examples 1, 2, 34 to 97, 107 to 168, and 217 to 222, wherein the compound having formula (A) is a compound having formula (XI-1):
[0713] (XI-1).
[0714] The compound or salt provided herein as Example 283 is any one of Examples 1, 2, 34 to 97, 107 to 168, and 217 to 222, wherein the compound having formula (A) is a compound having formula (XI-2):
[0715] (XI-2).
[0716] The compound or salt provided herein as Example 284 is any one of Examples 1, 2, 34 to 97, 107 to 168, and 217 to 222, wherein the compound having formula (A) is a compound having formula (XII-1):
[0717] (XII-1).
[0718] The compound or salt described in Examples 1 to 284 provided herein as Example 285 is an N, wherein no more than two of X, Y and Z are N.
[0719] The compound or salt provided herein as Example 286 is as described in Example 1 or 16, wherein the compound is:
[0720]
[0721]
[0722]
[0723]
[0724]
[0725]
[0726]
[0727]
[0728]
[0729]
[0730]
[0731]
[0732]
[0733]
[0734]
[0735]
[0736]
[0737]
[0738]
[0739] The compound or salt described in Example 1 is provided as Example 287 herein, wherein the compound is:
[0740]
[0741]
[0742]
[0743]
[0744]
[0745]
[0746]
[0747]
[0748]
[0749]
[0750]
[0751]
[0752]
[0753]
[0754]
[0755]
[0756]
[0757]
[0758]
[0759]
[0760] The compound or salt described in Example 1 is provided as Example 288 herein, wherein the compound is:
[0761] 5-(4-Cyclobutyl-2-(methoxymethyl)thieno[2,3-b]pyridin-6-yl)-2-methyl-2H-pyrazolo[3,4-b]pyridine;
[0762] 5-(2-(methoxymethyl)-4-(1-(methoxymethyl)cyclobutyl)thieno[2,3-b]pyridin-6-yl)-2-methyl-2H-pyrazolo[3,4-b]pyridine;
[0763] (R)-(4,6-bis(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)(cyclobutyl)methanol;
[0764] (S)-(4,6-bis(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)(cyclobutyl)methanol;
[0765] (R)-Cyclobutyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0766] (S)-Cyclobutyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0767] (R)-Cyclobutyl(4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0768] (S)-Cyclobutyl(4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0769] 5-(2-((R)-cyclobutyl(methoxy)methyl)-4-(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-6-yl)-2-methyl-2H-pyrazol[3,4-b]pyridine;
[0770] 5-(2-((S)-cyclobutyl(methoxy)methyl)-4-(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-6-yl)-2-methyl-2H-pyrazol[3,4-b]pyridine;
[0771] (1R)-1-Cyclobutyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0772] (1S)-1-Cyclobutyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0773] (1R)-1-Cyclobutyl-2,2,2-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0774] (1S)-1-Cyclobutyl-2,2,2-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0775] (1R)-1-(4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0776] (1S)-1-(4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0777] (1R)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0778] (1S)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0779] (R)-Cyclobutyl(6-cyclopropyl-4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0780] (S)-Cyclobutyl(6-cyclopropyl-4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0781] (R)-Cyclobutyl(4-cyclopropyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0782] (S)-Cyclobutyl(4-cyclopropyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0783] (4-(dimethylamino)-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2,5-diyl)diethanol;
[0784] (1R)-1-(4,6-bis(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0785] (1S)-1-(4,6-bis(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0786] (1R)-1-(4,6-bis(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0787] (1S)-1-(4,6-bis(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0788] (1R)-1-(4-Cyclopropyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0789] (1S)-1-(4-Cyclopropyl-6-(2-Methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0790] (1R)-1-(6-cyclopropyl-4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0791] (1S)-1-(6-Cyclopropyl-4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0792] (1R)-1-(4-Cyclopropyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol;
[0793] (1S)-1-(4-Cyclopropyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol;
[0794] (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0795] (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0796] (R)-Cyclopropyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0797] (S)-Cyclopropyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0798] (R)-Cyclobutyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0799] (S)-Cyclobutyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0800] (3R)-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)tetrahydro-3-furanol;
[0801] (3S)-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)tetrahydro-3-furanol;
[0802] 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[0803] 4-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)tetrahydro-2H-pyran-4-ol;
[0804] (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3R)-tetrahydro-3-furanyl)methanol;
[0805] (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3S)-tetrahydro-3-furanyl)methanol;
[0806] (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3R)-tetrahydro-3-furanyl)methanol;
[0807] (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3S)-tetrahydro-3-furanyl)methanol;
[0808] 3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-oxetanebutanol;
[0809] 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclopentanol;
[0810] (1R)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol;
[0811] (1S)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol;
[0812] (6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0813] (1R)-2,2,2-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0814] (1S)-2,2,2-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0815] (1R)-2-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol;
[0816] (1S)-2-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol;
[0817] (1R)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0818] (1S)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0819] (1R)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-butanol;
[0820] (1S)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-butanol;
[0821] (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3-oxetanebutyl)methanol;
[0822] (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3-oxetanebutyl)methanol;
[0823] (1R)-3-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol;
[0824] (1S)-3-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol;
[0825] 4,4-Difluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclohexanol;
[0826] (2R)-1,1,1-trifluoro-3-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol;
[0827] (2S)-1,1,1-trifluoro-3-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol;
[0828] (1R)-1-Cyclopropyl-2,2,2-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)ethanol;
[0829] (1S)-1-Cyclopropyl-2,2,2-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0830] (R)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0831] (S)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0832] (R)-(4,4-difluorocyclohexyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0833] (S)-(4,4-difluorocyclohexyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0834] 1-Methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-azacyclobutanol;
[0835] (3R)-1-methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-piperidinol;
[0836] (3S)-1-methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-piperidinol;
[0837] (2R)-1,1,1-trifluoro-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-butanol;
[0838] (2S)-1,1,1-trifluoro-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-butanol;
[0839] (1R)-2-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0840] (1S)-2-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0841] 4-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)tetrahydro-2H-thiaran-4-ol 1,1-dioxide;
[0842] 2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol;
[0843] (2R)-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-butanol;
[0844] (2S)-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-butanol;
[0845] (1R)-1-Cyclopropyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0846] (1S)-1-Cyclopropyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0847] 1-Methyl-4-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-4-piperidinol;
[0848] (2R)-1-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol;
[0849] (2S)-1-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol;
[0850] 3,3-Difluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[0851] (3R)-1-methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-pyrrolidone;
[0852] (3S)-1-methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-pyrrolidone;
[0853] (R)-(1-methyl-4-piperidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0854] (S)-(1-methyl-4-piperidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0855] (S)-(6-(1-methyl-1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0856] (R)-(6-(1-methyl-1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0857] (S)-(6-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0858] (R)-(6-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0859] (2R)-1,1,1-trifluoro-4-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-butanol;
[0860] (2S)-1,1,1-trifluoro-4-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-butanol;
[0861] (S)-(6-(1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0862] (R)-(6-(1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0863] (S)-(6-(6-methyl-1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0864] (R)-(6-(6-methyl-1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0865] (2R)-1,1,1-trifluoro-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol;
[0866] (2S)-1,1,1-trifluoro-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol;
[0867] (S)-(6-(2-methyl-2H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0868] (R)-(6-(2-methyl-2H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0869] (S)-(6-(3-methyl-1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0870] (R)-(6-(3-methyl-1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0871] (2R)-4-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-butanol;
[0872] (2S)-4-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-butanol;
[0873] (R)-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0874] (S)-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0875] (R)-(1-methyl-3-azacyclobutane)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0876] (S)-(1-Methyl-3-azacyclobutane)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0877] (S)-(6-(1,2-benzoxazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0878] (R)-(6-(1,2-benzoxazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[0879] (S)-Tetrahydro-2H-pyran-4-yl(6-(3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0880] (R)-Tetrahydro-2H-pyran-4-yl(6-(3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0881] (R)-((2R)-1-methyl-2-azacyclobutane)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0882] (R)-((2S)-1-methyl-2-azacyclobutane)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0883] (S)-((2R)-1-methyl-2-azacyclobutane)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0884] (S)-((2S)-1-methyl-2-azacyclobutane)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0885] (S)-(3,3-difluorocyclobutyl)(6-(2-methyl-1,3-benzoxazol-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0886] (R)-(3,3-difluorocyclobutyl)(6-(2-methyl-1,3-benzoxazol-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0887] (S)-(3,3-difluorocyclobutyl)(6-(1H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0888] (R)-(3,3-difluorocyclobutyl)(6-(1H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0889] (S)-(3,3-difluorocyclobutyl)(6-(2-methylimidazo[1,2-a]pyridin-6-yl)thienozo[2,3-b]pyridin-2-yl)methanol;
[0890] (R)-(3,3-difluorocyclobutyl)(6-(2-methylimidazo[1,2-a]pyridin-6-yl)thienozo[2,3-b]pyridin-2-yl)methanol;
[0891] 6-(2-((R)-(3,3-difluorocyclobutyl)(hydroxy)methyl)thieno[2,3-b]pyridin-6-yl)-3-methyl-4(3H)-pyrimidinone;
[0892] 6-(2-((S)-(3,3-difluorocyclobutyl)(hydroxy)methyl)thieno[2,3-b]pyridin-6-yl)-3-methyl-4(3H)-pyrimidinone;
[0893] 6-(2-((S)-(3,3-difluorocyclobutyl)(hydroxy)methyl)thieno[2,3-b]pyridin-6-yl)-2-methyl-1(2H)-isoquinolinone;
[0894] 6-(2-((R)-(3,3-difluorocyclobutyl)(hydroxy)methyl)thieno[2,3-b]pyridin-6-yl)-2-methyl-1(2H)-isoquinolinone;
[0895] (S)-(3,3-difluorocyclobutyl)(6-(2-methyl-1,3-benzoxazol-6-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0896] (R)-(3,3-difluorocyclobutyl)(6-(2-methyl-1,3-benzoxazol-6-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0897] (S)-(3,3-difluorocyclobutyl)(6-(6-quinoxalinyl)thieno[2,3-b]pyridin-2-yl)methanol;
[0898] (R)-(3,3-difluorocyclobutyl)(6-(6-quinoxalinyl)thieno[2,3-b]pyridin-2-yl)methanol;
[0899] (S)-(3,3-difluorocyclobutyl)(6-(2-ethyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0900] (R)-(3,3-difluorocyclobutyl)(6-(2-ethyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0901] (1S)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)-1-butanol;
[0902] (1R)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)-1-butanol;
[0903] (S)-(3,3-difluorocyclobutyl)(6-(2-methylimidazo[1,2-a]pyridin-7-yl)thienozo[2,3-b]pyridin-2-yl)methanol;
[0904] (R)-(3,3-difluorocyclobutyl)(6-(2-methylimidazo[1,2-a]pyridin-7-yl)thienozo[2,3-b]pyridin-2-yl)methanol;
[0905] (S)-(3,3-difluorocyclobutyl)(6-(2-(2-propyl)-2H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0906] (R)-(3,3-difluorocyclobutyl)(6-(2-(2-propyl)-2H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0907] (S)-(3,3-difluorocyclobutyl)(6-(5-pyrimidinyl)thieno[2,3-b]pyridin-2-yl)methanol;
[0908] (R)-(3,3-difluorocyclobutyl)(6-(5-pyrimidinyl)thieno[2,3-b]pyridin-2-yl)methanol;
[0909] (S)-Cyclopentyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)methanol;
[0910] (R)-Cyclopentyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)methanol;
[0911] (1S)-3-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)-1-propanol;
[0912] (1R)-3-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)-1-propanol;
[0913] (1S)-4,4,4-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)-1-butanol;
[0914] (1R)-4,4,4-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)-1-butanol;
[0915] (S)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)methanol;
[0916] (R)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)methanol;
[0917] (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3R)-1-methyl-3-pyrrolidinyl)methanol;
[0918] (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3S)-1-methyl-3-pyrrolidinyl)methanol;
[0919] (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3R)-1-methyl-3-pyrrolidinyl)methanol;
[0920] (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3S)-1-methyl-3-pyrrolidinyl)methanol;
[0921] (R)-((3R)-1-methyl-3-piperidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)methanol;
[0922] (R)-((3S)-1-methyl-3-piperidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)methanol;
[0923] (S)-((3R)-1-methyl-3-piperidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)methanol;
[0924] (S)-((3S)-1-methyl-3-piperidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)methanol;
[0925] (S)-(3,3-difluorocyclobutyl)(6-(2-(2-propyl)-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0926] (R)-(3,3-difluorocyclobutyl)(6-(2-(2-propyl)-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0927] (S)-(3,3-difluorocyclobutyl)(6-(1-(2-propyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0928] (R)-(3,3-difluorocyclobutyl)(6-(1-(2-propyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0929] (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methane-d-ol;
[0930] (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methane-d-ol;
[0931] (R)-(3-amino-6-(5-pyrimidinyl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol;
[0932] (S)-(3-amino-6-(5-pyrimidinyl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol;
[0933] 2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienro[2,3-b]pyridin-2-yl)spiro[3,3]hepta-2-ol;
[0934] 3,3-Dimethyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[0935] 6,6-Difluoro-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienro[2,3-b]pyridin-2-yl)spiro[3,3]hepta-2-ol;
[0936] 6-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-oxaspiro[3.3]hepta-6-ol;
[0937] cis-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[0938] cis-3-(difluoromethyl)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[0939] cis-3-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[0940] (S)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)methanol;
[0941] (R)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)methanol;
[0942] 1-(6-(2-ethyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3,3-difluorocyclobutanol;
[0943] (S)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)methanol;
[0944] (R)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)methanol;
[0945] 3,3-Difluoro-1-(6-(3-methyl-3H-imidazo[4,5-b]pyridin-6-yl)thienro[2,3-b]pyridin-2-yl)cyclobutanol;
[0946] 3,3-Difluoro-1-(6-(2-methyl[1,3]oxazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[0947] 3,3-Difluoro-1-(6-(2-methyl-3H-imidazo[4,5-b]pyridin-6-yl)thienro[2,3-b]pyridin-2-yl)cyclobutanol;
[0948] 3,3-Difluoro-1-(6-(1H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[0949] 3,3-Difluoro-1-(6-(2-methylimidazo[1,2-a]pyridin-6-yl)thienzo[2,3-b]pyridin-2-yl)cyclobutanol;
[0950] 1-(6-(2-amino-5-pyrimidinyl)thieno[2,3-b]pyridin-2-yl)-3,3-difluorocyclobutanol;
[0951] (S)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[4,5-b]pyridin-2-yl)methanol;
[0952] (R)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[4,5-b]pyridin-2-yl)methanol;
[0953] 3,3-Difluoro-1-(6-(2-methyl-1,3-benzoxazol-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[0954] trans-3-fluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[0955] (R)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)methanol;
[0956] (S)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)methanol;
[0957] (S)-(3-chloro-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol;
[0958] (R)-(3-chloro-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol;
[0959] 3,3-Difluoro-1-(6-(3H-imidazo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[0960] 3,3-Difluoro-1-(6-(1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[0961] (R)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0962] (S)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0963] (S)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)methanol;
[0964] (R)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)methanol;
[0965] 3,3-Difluoro-1-(6-(2-(methylamino)-5-pyrimidinyl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[0966] (R)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methyl-d-ol;
[0967] (S)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methyl-d-ol;
[0968] 3,3-Difluoro-1-(6-(2-methylimidazo[1,2-a]pyridin-7-yl)thienzo[2,3-b]pyridin-2-yl)cyclobutanol;
[0969] 3,3-Difluoro-1-(6-(2-methylimidazo[1,2-a]pyrimidin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[0970] (2R)-2-(3,3-difluorocyclobutyl)-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0971] (2S)-2-(3,3-difluorocyclobutyl)-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[0972] 3,3-Difluoro-1-(6-(5-pyrimidinyl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[0973] 3,3-Difluoro-1-(6-(pyrido[2,3-b]pyrazin-7-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[0974] (S)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7-quinolinyl)methanol;
[0975] (R)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7-quinolinyl)methanol;
[0976] 3,3-Difluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)cyclobutanol;
[0977] 3,3-Difluoro-1-(6-(2-methyl-2H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[0978] 1-(6-(1,2-benzoxazol-5-yl)thieno[2,3-b]pyridin-2-yl)-3,3-difluorocyclobutanol;
[0979] 3,3-Difluoro-1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thienro[2,3-b]pyridin-2-yl)cyclobutanol;
[0980] 2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[3,5]non-2-ol;
[0981] 2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[3,4]oct-2-ol;
[0982] 3,3-Difluoro-1-(6-(2-methylimidazo[1,2-b]pyridazin-7-yl)thienro[2,3-b]pyridin-2-yl)cyclobutanol;
[0983] 3,3-Difluoro-1-(6-(3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[0984] (R)-(3,3-difluorocyclobutyl)(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0985] (S)-(3,3-difluorocyclobutyl)(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0986] trans-6-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-oxaspiro[3,3]hepta-6-ol;
[0987] cis-6-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-oxaspiro[3,3]hepta-6-ol;
[0988] 3,3-Dimethyl-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol;
[0989] cis-3-(methoxymethyl)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[0990] trans-3-methoxy-3-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[0991] cis-3-methoxy-3-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[0992] (R)-(3,3-difluorocyclobutyl)(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)methanol;
[0993] (S)-(3,3-difluorocyclobutyl)(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[0994] 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclopropanol;
[0995] 5-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[2,3]hexane-5-ol;
[0996] cis-3-cyclopropyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[0997] trans-3-hydroxy-1-methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutyronitrile;
[0998] cis-3-hydroxy-1-methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutyronitrile;
[0999] (1S,2R)-2-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1000] (1R,2S)-2-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1001] (1S)-2,2-dimethyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1002] (1R)-2,2-Dimethyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1003] trans-3-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1004] cis-3-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1005] cis-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-(trifluoromethoxy)cyclobutanol;
[1006] 3,3-Dimethyl-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)cyclobutanol;
[1007] cis-1-(3-chloro-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-methoxycyclobutanol;
[1008] (1R,2R)-2-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1009] (1R,2S)-2-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1010] (1S,2R)-2-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1011] cis-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1012] (1S,2S)-2-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1013] 1-(3-chloro-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3,3-dimethylcyclobutanol;
[1014] cis-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1015] (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((cis)-3-(trifluoromethyl)cyclobutyl)methanol;
[1016] (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((cis)-3-(trifluoromethyl)cyclobutyl)methanol;
[1017] (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((trans)-3-(trifluoromethyl)cyclobutyl)methanol;
[1018] (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((trans)-3-(trifluoromethyl)cyclobutyl)methanol;
[1019] cis-1-(3-chloro-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1020] (R)-((1R)-2,2-difluorocyclopropyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1021] (S)-((1S)-2,2-difluorocyclopropyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1022] (S)-((1R)-2,2-difluorocyclopropyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1023] (R)-((1S)-2,2-difluorocyclopropyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1024] (R)-(3,3-difluoro-1-methylcyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1025] (S)-(3,3-difluoro-1-methylcyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1026] (R)-Bicyclo[1.1.1]pent-1-yl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1027] (S)-Bicyclo[1.1.1]pent-1-yl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1028] (S)-((cis)-3-methoxycyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1029] cis-3-(difluoromethyl)-1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thienro[2,3-b]pyridin-2-yl)cyclobutanol;
[1030] (R)-((cis)-3-methoxycyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1031] (S)-((trans)-3-methoxycyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1032] (R)-((trans)-3-methoxycyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1033] 3,3-Dimethyl-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7-quinolinyl)cyclobutanol;
[1034] 3,3-Difluoro-1-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1035] cis-1-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1036] cis-1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1037] cis-3-(difluoromethyl)-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1038] (R)-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)-7-quinolinyl)(tetrahydro-2H-pyran-4-yl)methanol;
[1039] (S)-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)-7-quinolinyl)(tetrahydro-2H-pyran-4-yl)methanol;
[1040] (R)-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7-quinolinyl)(tetrahydro-2H-pyran-4-yl)methanol;
[1041] (S)-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7-quinolinyl)(tetrahydro-2H-pyran-4-yl)methanol;
[1042] cis-3-(difluoromethyl)-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)cyclobutanol;
[1043] cis-3-(difluoromethyl)-1-(5-(3-methyl-3H-[1,2,3]thiazo[4,5-b]pyridin-6-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)cyclobutanol;
[1044] (R)-(3-methyl-6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1045] (S)-(3-methyl-6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1046] (R)-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1047] (S)-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1048] cis-3-(difluoromethyl)-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7-quinolinyl)cyclobutanol;
[1049] (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3-(trifluoromethyl)bicyclo[1.1.1]pent-1-yl)methanol;
[1050] (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3-(trifluoromethyl)bicyclo[1.1.1]pent-1-yl)methanol;
[1051] cis-3-fluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1052] cis-3-(difluoromethyl)-1-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1053] cis-3-(difluoromethyl)-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-quinolinyl)cyclobutanol;
[1054] cis-3-(difluoromethyl)-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[3,2-b]pyridin-2-yl)cyclobutanol;
[1055] cis-3-(difluoromethyl)-1-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thienro[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1056] cis-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1057] (S)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-quinolinyl)methanol;
[1058] (R)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-quinolinyl)methanol;
[1059] cis-3-(difluoromethyl)-1-(6-(2-ethyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1060] (trans)-1,1-difluoro-5-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[2,3]hexane-5-ol;
[1061] (cis)-1,1-difluoro-5-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[2,3]hexane-5-ol;
[1062] cis-3-(difluoromethyl)-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-6-yl)cyclobutanol;
[1063] cis-3-(difluoromethyl)-1-(5-methyl-2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1064] trans-3-hydroxy-1-methyl-3-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)cyclobutyronitrile;
[1065] Cis-3-hydroxy-1-methyl-3-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)cyclobutyronitrile;
[1066] cis-3-(difluoromethyl)-1-(6-(2-methylimidazo[1,2-b]pyridazin-7-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1067] cis-3-(difluoromethyl)-1-(6-(2-methyl-3H-imidazo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1068] (R)-(3,3-difluorocyclobutyl)(3-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyrazin-6-yl)methanol;
[1069] (S)-(3,3-difluorocyclobutyl)(3-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyrazin-6-yl)methanol;
[1070] (2S)-2-(3,3-difluorocyclobutyl)-2-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)ethanol;
[1071] (2R)-2-(3,3-difluorocyclobutyl)-2-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)ethanol;
[1072] cis-3-methoxy-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1073] cis-1-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1074] cis-3-hydroxy-1-methyl-3-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-d]pyrimidin-6-yl)cyclobutyronitrile;
[1075] trans-3-hydroxy-1-methyl-3-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-d]pyrimidin-6-yl)cyclobutyronitrile;
[1076] cis-3-(difluoromethyl)-1-(6-(2-methylimidazo[1,2-a]pyrimidin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1077] trans-3-hydroxy-1-methyl-3-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thienro[2,3-d]pyrimidin-6-yl)cyclobutyronitrile;
[1078] cis-3-hydroxy-1-methyl-3-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thienro[2,3-d]pyrimidin-6-yl)cyclobutyronitrile;
[1079] cis-3-cyclopropyl-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1080] cis-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethoxy)cyclobutanol;
[1081] cis-1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)-3-(trifluoromethoxy)cyclobutanol;
[1082] cis-3-methoxy-3-methyl-1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thienro[2,3-b]pyridin-2-yl)cyclobutanol;
[1083] cis-3-(difluoromethyl)-1-(6-(3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1084] trans-3-hydroxy-1-methyl-3-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutyronitrile;
[1085] cis-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)-3-(trifluoromethoxy)cyclobutanol;
[1086] trans-3-hydroxy-1-methyl-3-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[3,2-b]pyridin-2-yl)cyclobutyronitrile;
[1087] cis-3-hydroxy-1-methyl-3-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[3,2-b]pyridin-2-yl)cyclobutyronitrile;
[1088] 5-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)spiro[2,3]hexane-5-ol;
[1089] 5-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)spiro[2,3]hexane-5-ol;
[1090] (R)-((1S)-2,2-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1091] (S)-((1R)-2,2-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1092] (R)-((1R)-2,2-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1093] (S)-((1S)-2,2-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1094] cis-3-(difluoromethyl)-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-d]pyrimidin-2-yl)cyclobutanol;
[1095] cis-3-hydroxy-1-methyl-3-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutyronitrile;
[1096] cis-1-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethoxy)cyclobutanol;
[1097] cis-1-(5-(3-methyl-3H-[1,2,3]thiazo[4,5-b]pyridin-6-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)-3-(trifluoromethoxy)cyclobutanol;
[1098] trans-3-methoxy-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1099] cis-3-methoxy-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1100] trans-1,1-difluoro-5-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)spiro[2,3]hexane-5-ol;
[1101] cis-1,1-difluoro-5-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienro[2,3-d]pyrimidin-6-yl)spiro[2,3]hexane-5-ol;
[1102] trans-1,1-difluoro-5-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)spiro[2,3]hexane-5-ol;
[1103] cis-1,1-difluoro-5-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)spiro[2,3]hexane-5-ol;
[1104] 6,6-Difluoro-2-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienro[2,3-d]pyrimidin-6-yl)spiro[3,3]hepta-2-ol;
[1105] cis-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)-3-(trifluoromethoxy)cyclobutanol;
[1106] trans-3-methoxy-3-methyl-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1107] cis-3-methoxy-3-methyl-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1108] cis-3-(methoxymethyl)-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1109] cis-1-(2-(1-methyl-1H-pyrazol-4-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1110] (S)-(3-amino-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol;
[1111] (R)-(3-amino-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol;
[1112] trans-3-methoxy-3-methyl-1-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thienro[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1113] cis-3-methoxy-3-methyl-1-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thienro[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1114] cis-1-(2-(3-pyridyl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1115] cis-1-(2-(6-quinoxalinyl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1116] cis-1-(2-(imidazo[1,2-a]pyrimidin-6-yl)thienzo[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1117] trans-3-methoxy-3-methyl-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)cyclobutanol;
[1118] cis-3-methoxy-3-methyl-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)cyclobutanol;
[1119] trans-3-methoxy-3-methyl-1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1120] cis-1-(2-(4-pyridazinyl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1121] cis-3-methoxy-3-methyl-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[3,2-b]pyridin-2-yl)cyclobutanol;
[1122] 3-(6-(cis-1-hydroxy-3-(trifluoromethyl)cyclobutyl)thieno[2,3-d]pyrimidin-2-yl)-5,6-dihydro-7H-pyrrolo[3,4-b]pyridin-7-one;
[1123] cis-1-(2-([1,2,4]triazolo[4,3-a]pyrimidin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1124] (R)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyrazin-6-yl)methanol;
[1125] (S)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyrazin-6-yl)methanol;
[1126] trans-3-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1127] cis-3-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1128] cis-1-(2-(2-methyl-2H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1129] cis-1-(2-(1-methyl-1H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1130] cis-1-(2-(1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1131] cis-1-(2-(1,8-naphthidin-3-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1132] trans-3-(difluoromethyl)-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thiazo[5,4-b]pyridin-2-yl)cyclobutanol;
[1133] trans-3-methoxy-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol; or
[1134] cis-1-(2-([1,2,4]triazolo[1,5-a]pyrimidin-6-yl)thienro[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobut-1-ol.
[1135] The compound or salt described in Example 1 is provided as Example 289 herein, wherein the compound is:
[1136] 5-(4-Cyclobutyl-2-(methoxymethyl)thieno[2,3-b]pyridin-6-yl)-2-methyl-2H-pyrazolo[3,4-b]pyridine;
[1137] 5-(2-(methoxymethyl)-4-(1-(methoxymethyl)cyclobutyl)thieno[2,3-b]pyridin-6-yl)-2-methyl-2H-pyrazolo[3,4-b]pyridine;
[1138] (4,6-bis(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)(cyclobutyl)methanol;
[1139] Cyclobutyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1140] Cyclobutyl(4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1141] 5-(2-(cyclobutyl(methoxy)methyl)-4-(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-6-yl)-2-methyl-2H-pyrazol[3,4-b]pyridine;
[1142] 1-Cyclobutyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[1143] 1-Cyclobutyl-2,2,2-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[1144] 1-(4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[1145] 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazolo-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[1146] Cyclobutyl(6-cyclopropyl-4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1147] Cyclobutyl(4-cyclopropyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1148] (4-(dimethylamino)-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2,5-diyl)diethanol;
[1149] 1-(4,6-bis(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[1150] 1-(4,6-bis(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[1151] 1-(4-Cyclopropyl-6-(2-Methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[1152] 1-(6-Cyclopropyl-4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[1153] 1-(4-Cyclopropyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol;
[1154] (6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1155] Cyclopropyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1156] Cyclobutyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1157] 3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)tetrahydro-3-furanol;
[1158] 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1159] 4-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)tetrahydro-2H-pyran-4-ol;
[1160] (6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-3-furanyl)methanol;
[1161] 3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-oxetanebutanol;
[1162] 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclopentanol;
[1163] 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol;
[1164] (6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1165] 2,2,2-Trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[1166] 2-Methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)-1-propanol;
[1167] 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[1168] 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-butanol;
[1169] (6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3-oxetanebutyl)methanol;
[1170] 3-Methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)-1-propanol;
[1171] 4,4-Difluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclohexanol;
[1172] 1,1,1-Trifluoro-3-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol;
[1173] 1-Cyclopropyl-2,2,2-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)ethanol;
[1174] (3,3-Difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1175] (4,4-Difluorocyclohexyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1176] 1-Methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-azacyclobutanol;
[1177] 1-Methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-piperidinol;
[1178] 1,1,1-Trifluoro-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-butanol;
[1179] 2-Methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienro[2,3-b]pyridin-2-yl)ethanol;
[1180] 4-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)tetrahydro-2H-thiaran-4-ol 1,1-dioxide;
[1181] 2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol;
[1182] 2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-butanol;
[1183] 1-Cyclopropyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)ethanol;
[1184] 1-Methyl-4-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-4-piperidinol;
[1185] 1-Methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol;
[1186] 3,3-Difluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1187] 1-Methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)-3-pyrrolidone;
[1188] (1-Methyl-4-piperidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1189] (6-(1-methyl-1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1190] (6-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1191] 1,1,1-Trifluoro-4-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-butanol;
[1192] (6-(1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1193] (6-(6-methyl-1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1194] 1,1,1-Trifluoro-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol;
[1195] (6-(2-methyl-2H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1196] (6-(3-methyl-1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1197] 4-Methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-butanol;
[1198] (6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1199] (1-Methyl-3-azacyclobutane)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1200] (6-(1,2-benzoxazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1201] Tetrahydro-2H-pyran-4-yl(6-(3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1202] (1-Methyl-2-azacyclobutane)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1203] (3,3-Difluorocyclobutyl)(6-(2-methyl-1,3-benzoxazol-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1204] (3,3-Difluorocyclobutyl)(6-(1H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1205] (3,3-Difluorocyclobutyl)(6-(2-methylimidazo[1,2-a]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1206] 6-(2-((3,3-difluorocyclobutyl)(hydroxy)methyl)thieno[2,3-b]pyridin-6-yl)-3-methyl-4(3H)-pyrimidinone;
[1207] 6-(2-((3,3-difluorocyclobutyl)(hydroxy)methyl)thieno[2,3-b]pyridin-6-yl)-2-methyl-1(2H)-isoquinolinone;
[1208] (3,3-Difluorocyclobutyl)(6-(2-methyl-1,3-benzoxazol-6-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1209] (3,3-Difluorocyclobutyl)(6-(6-quinoxalinyl)thieno[2,3-b]pyridin-2-yl)methanol;
[1210] (3,3-Difluorocyclobutyl)(6-(2-ethyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1211] 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)-1-butanol;
[1212] (3,3-Difluorocyclobutyl)(6-(2-methylimidazo[1,2-a]pyridin-7-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1213] (3,3-Difluorocyclobutyl)(6-(2-(2-propyl)-2H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1214] (3,3-Difluorocyclobutyl)(6-(5-pyrimidinyl)thieno[2,3-b]pyridin-2-yl)methanol;
[1215] Cyclopentyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)methanol;
[1216] 3-Methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)-1-propanol;
[1217] 4,4,4-Trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)-1-butanol;
[1218] (3,3-Difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)methanol;
[1219] (6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(1-methyl-3-pyrrolidinyl)methanol;
[1220] (1-Methyl-3-piperidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1221] (3,3-Difluorocyclobutyl)(6-(2-(2-propyl)-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1222] (3,3-Difluorocyclobutyl)(6-(1-(2-propyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1223] (6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methane-d-ol;
[1224] (3-amino-6-(5-pyrimidinyl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol;
[1225] 2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienro[2,3-b]pyridin-2-yl)spiro[3,3]hepta-2-ol;
[1226] 3,3-Dimethyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1227] 6,6-Difluoro-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienro[2,3-b]pyridin-2-yl)spiro[3,3]hepta-2-ol;
[1228] 6-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-oxaspiro[3.3]hepta-6-ol;
[1229] 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1230] 3-(difluoromethyl)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1231] 3-Methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1232] (3,3-Difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)methanol;
[1233] 1-(6-(2-ethyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3,3-difluorocyclobutanol;
[1234] (3,3-Difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)methanol;
[1235] 3,3-Difluoro-1-(6-(3-methyl-3H-imidazo[4,5-b]pyridin-6-yl)thienro[2,3-b]pyridin-2-yl)cyclobutanol;
[1236] 3,3-Difluoro-1-(6-(2-methyl[1,3]oxazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1237] 3,3-Difluoro-1-(6-(2-methyl-3H-imidazo[4,5-b]pyridin-6-yl)thienro[2,3-b]pyridin-2-yl)cyclobutanol;
[1238] 3,3-Difluoro-1-(6-(1H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1239] 3,3-Difluoro-1-(6-(2-methylimidazo[1,2-a]pyridin-6-yl)thienzo[2,3-b]pyridin-2-yl)cyclobutanol;
[1240] 1-(6-(2-amino-5-pyrimidinyl)thieno[2,3-b]pyridin-2-yl)-3,3-difluorocyclobutanol;
[1241] (3,3-Difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[4,5-b]pyridin-2-yl)methanol;
[1242] 3,3-Difluoro-1-(6-(2-methyl-1,3-benzoxazol-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1243] 3-Fluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1244] (3,3-Difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)methanol;
[1245] (3-chloro-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol;
[1246] 3,3-Difluoro-1-(6-(3H-imidazo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1247] 3,3-Difluoro-1-(6-(1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1248] (3,3-Difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1249] (3,3-Difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)methanol;
[1250] 3,3-Difluoro-1-(6-(2-(methylamino)-5-pyrimidinyl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1251] (3,3-Difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methyl-d-ol;
[1252] 3,3-Difluoro-1-(6-(2-methylimidazo[1,2-a]pyridin-7-yl)thienzo[2,3-b]pyridin-2-yl)cyclobutanol;
[1253] 3,3-Difluoro-1-(6-(2-methylimidazo[1,2-a]pyrimidin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1254] 2-(3,3-difluorocyclobutyl)-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol;
[1255] 3,3-Difluoro-1-(6-(5-pyrimidinyl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1256] 3,3-Difluoro-1-(6-(pyrido[2,3-b]pyrazin-7-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1257] (3,3-Difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7-quinolinyl)methanol;
[1258] 3,3-Difluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)cyclobutanol;
[1259] 3,3-Difluoro-1-(6-(2-methyl-2H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1260] 1-(6-(1,2-benzoxazol-5-yl)thieno[2,3-b]pyridin-2-yl)-3,3-difluorocyclobutanol;
[1261] 3,3-Difluoro-1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thienro[2,3-b]pyridin-2-yl)cyclobutanol;
[1262] 2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[3,5]non-2-ol;
[1263] 2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[3,4]oct-2-ol;
[1264] 3,3-Difluoro-1-(6-(2-methylimidazo[1,2-b]pyridazin-7-yl)thienro[2,3-b]pyridin-2-yl)cyclobutanol;
[1265] 3,3-Difluoro-1-(6-(3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1266] (3,3-Difluorocyclobutyl)(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1267] 6-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-oxaspiro[3.3]hepta-6-ol;
[1268] 3,3-Dimethyl-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1269] 3-(methoxymethyl)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1270] 3-Methoxy-3-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1271] (3,3-Difluorocyclobutyl)(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)methanol;
[1272] 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclopropanol;
[1273] 5-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[2,3]hexane-5-ol;
[1274] 3-Cyclopropyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1275] 3-Hydroxy-1-methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutyronitrile;
[1276] 2-Methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1277] 2,2-Dimethyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1278] 3-Methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1279] 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-(trifluoromethoxy)cyclobutanol;
[1280] 3,3-Dimethyl-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)cyclobutanol;
[1281] 1-(3-chloro-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-methoxycyclobutanol;
[1282] 2-Methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1283] 1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1284] 1-(3-chloro-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3,3-dimethylcyclobutanol;
[1285] 1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1286] 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-(trifluoromethoxy)cyclobut-1-ol;
[1287] (6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3-(trifluoromethyl)cyclobutyl)methanol;
[1288] 1-(3-chloro-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1289] (2,2-Difluorocyclopropyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1290] (3,3-Difluoro-1-methylcyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1291] Bicyclo[1.1.1]pent-1-yl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1292] (3-Methoxycyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1293] 3-(difluoromethyl)-1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1294] 3,3-Dimethyl-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7-quinolinyl)cyclobutanol;
[1295] 3,3-Difluoro-1-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1296] 1-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1297] 1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1298] 3-(difluoromethyl)-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1299] (2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)-7-quinolinyl)(tetrahydro-2H-pyran-4-yl)methanol;
[1300] (2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7-quinolinyl)(tetrahydro-2H-pyran-4-yl)methanol;
[1301] 3-(difluoromethyl)-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)cyclobutanol;
[1302] 3-(difluoromethyl)-1-(5-(3-methyl-3H-[1,2,3]thiazo[4,5-b]pyridin-6-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)cyclobutanol;
[1303] (3-Methyl-6-(3-Methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1304] (3-Methyl-6-(2-Methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol;
[1305] 3-(difluoromethyl)-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7-quinolinyl)cyclobutanol;
[1306] (6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3-(trifluoromethyl)bicyclo[1.1.1]pent-1-yl)methanol;
[1307] 3-(difluoromethyl)-1-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1308] 3-(difluoromethyl)-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-quinolinyl)cyclobutanol;
[1309] 3-(difluoromethyl)-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[3,2-b]pyridin-2-yl)cyclobutanol;
[1310] 3-(difluoromethyl)-1-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1311] 3-Fluoro-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1312] 1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1313] (3,3-Difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-quinolinyl)methanol;
[1314] 3-(difluoromethyl)-1-(6-(2-ethyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)cyclobutanol;
[1315] 1,1-Difluoro-5-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)spiro[2,3]hexane-5-ol;
[1316] 3-(difluoromethyl)-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-6-yl)cyclobutanol;
[1317] 3-(difluoromethyl)-1-(5-methyl-2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1318] 3-Hydroxy-1-methyl-3-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)cyclobutyronitrile;
[1319] 3-(difluoromethyl)-1-(6-(2-methylimidazo[1,2-b]pyridazin-7-yl)thienro[2,3-b]pyridin-2-yl)cyclobutanol;
[1320] 3-(difluoromethyl)-1-(6-(2-methyl-3H-imidazo[4,5-b]pyridin-6-yl)thienro[2,3-b]pyridin-2-yl)cyclobutanol;
[1321] (3,3-Difluorocyclobutyl)(3-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyrazin-6-yl)methanol;
[1322] 2-(3,3-Difluorocyclobutyl)-2-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)ethanol;
[1323] 3-Methoxy-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1324] 1-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1325] 3-Hydroxy-1-methyl-3-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-d]pyrimidin-6-yl)cyclobutyronitrile;
[1326] 3-(difluoromethyl)-1-(6-(2-methylimidazo[1,2-a]pyrimidin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1327] 3-Hydroxy-1-methyl-3-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thienro[2,3-d]pyrimidin-6-yl)cyclobutyronitrile;
[1328] 3-Cyclopropyl-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1329] 1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethoxy)cyclobutanol;
[1330] 1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)-3-(trifluoromethoxy)cyclobutanol;
[1331] 3-Methoxy-3-methyl-1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thienro[2,3-b]pyridin-2-yl)cyclobutanol;
[1332] 3-(difluoromethyl)-1-(6-(3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol;
[1333] 3-Hydroxy-1-methyl-3-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thienro[2,3-b]pyridin-2-yl)cyclobutyronitrile;
[1334] 1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)-3-(trifluoromethoxy)cyclobutanol;
[1335] 3-Hydroxy-1-methyl-3-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[3,2-b]pyridin-2-yl)cyclobutyronitrile;
[1336] 5-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)spiro[2,3]hexane-5-ol;
[1337] 5-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)spiro[2,3]hexane-5-ol;
[1338] 2,2-Difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol;
[1339] 3-(difluoromethyl)-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-d]pyrimidin-2-yl)cyclobutanol;
[1340] 1-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethoxy)cyclobutanol;
[1341] 1-(5-(3-methyl-3H-[1,2,3]thiazo[4,5-b]pyridin-6-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)-3-(trifluoromethoxy)cyclobutanol;
[1342] 3-Methoxy-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1343] 1,1-Difluoro-5-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)spiro[2,3]hexane-5-ol;
[1344] 1,1-Difluoro-5-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)spiro[2,3]hexane-5-ol;
[1345] 6,6-Difluoro-2-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienro[2,3-d]pyrimidin-6-yl)spiro[3,3]hepta-2-ol;
[1346] 1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)-3-(trifluoromethoxy)cyclobutanol;
[1347] 3-Methoxy-3-methyl-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1348] 3-(methoxymethyl)-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1349] 1-(2-(1-methyl-1H-pyrazol-4-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1350] (3-amino-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol;
[1351] 3-Methoxy-3-methyl-1-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thienro[2,3-d]pyrimidin-6-yl)cyclobutanol;
[1352] 1-(2-(3-pyridyl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1353] 1-(2-(6-quinoxalinyl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1354] 1-(2-(imidazo[1,2-a]pyrimidin-6-yl)thienzo[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1355] 3-Methoxy-3-methyl-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazo[5,4-b]pyridin-2-yl)cyclobutanol;
[1356] 1-(2-(4-pyridazinyl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1357] 3-Methoxy-3-methyl-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[3,2-b]pyridin-2-yl)cyclobutanol;
[1358] 3-(6-(1-hydroxy-3-(trifluoromethyl)cyclobutyl)thieno[2,3-d]pyrimidin-2-yl)-5,6-dihydro-7H-pyrrolo[3,4-b]pyridin-7-one;
[1359] 1-(2-([1,2,4]triazolo[4,3-a]pyrimidin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1360] (3,3-Difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyrazin-6-yl)methanol;
[1361] 3-Methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thienolo[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol;
[1362] 1-(2-(2-methyl-2H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1363] 1-(2-(1-methyl-1H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol;
[1364] 1-(2-(1-methyl-1H-imid...
Claims
1. A compound of formula (A) (A) or a pharmaceutically acceptable salt of the compound; wherein is (i), (ii), or (iii); m is 0 or 1 ; X is N or CH; Y is N or C-R 3 ; Z is N or C-R 5 ; b is N or C-R 4 ; R 1a is -H, deuterium, C 1-6 alkyl, or C 1-6 haloalkyl; wherein When R 1a is C 1-6 alkyl or C 1-6 haloalkyl, then R 1a may be unsubstituted or substituted with one or more substituents, each of which is independently halogen, -OH, -N(R b )2, C 1-3 alkyl, or C 1-3 alkoxy; R 1b is -H, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 heteroalkyl, -(C 1-6 alkylene)-O-(C 1-6 alkyl), C 3-10 cycloalkyl, or heterocyclyl having 3 to 10 ring members; wherein when R 1b is C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 heteroalkyl, -(C 1-6 alkylene)-O-(C 1-6 alkyl), C 3-10 cycloalkyl, or heterocyclyl having from 3 to 10 ring members, then R 1b may be unsubstituted or substituted by one or more substituents, each of which is independently halogen, -OH, -N(R b )2, C 1-3 alkyl, or C 1-3 alkoxy; wherein each of the C 1-3 alkyl and C 1-3 alkoxy groups can be unsubstituted or substituted by 1 to 6 -F groups; or alternatively, R 1a and R 1b together form a C 3-10 cycloalkyl, C 3-10 cycloalkenyl, or heterocyclyl having 3 to 10 ring members; wherein the R 1a and R 1b ring can be unsubstituted or substituted with one or more substituents, each of which is independently halogen, -OH, oxo, -N(R b )2, C 1-3 alkyl, C 1-3 alkoxy, -CN, C 1-6 heteroalkyl, C 3-10 cycloalkyl, or heterocyclyl having from 3 to 10 ring members; wherein each of the C 1-3 alkyl and C 1-3 alkoxy groups can be unsubstituted or substituted with from 1 to 9 halogen groups or C 1-3 alkoxy groups; R 1c is -H, C 1-6 alkyl, or C 3-6 cycloalkyl; wherein when R 1c is C 1-6 alkyl or C 3-6 cycloalkyl, then R 1c may be unsubstituted or substituted with one or more substituents, each of which is independently halogen, -OH, -N(R b )2, C 1-3 alkyl, C 1-3 alkoxy, or C 1-6 heteroalkyl; R 2 is C 3-20 cycloalkyl, C 3-20 cycloalkenyl, C 6-18 aryl, heteroaryl having 5 to 20 ring members, or heterocyclyl having 3 to 20 ring members; wherein R 2 may be unsubstituted or substituted by one or more substituents, each of which is independently halogen, -OH, oxo, -N(R b )2, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 alkylene-OH, C 1-6 alkylene-O-C 1-6 alkyl, or C 1-6 heteroalkyl; R 3 is -H, C 1-6 alkyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, amino, C 1-4 alkyl-amino, di-C 1-4 alkyl-amino, C 6-10 aryl, heteroaryl having 5 to 10 ring members, or heterocyclyl having 5 to 10 ring members; wherein, when R 3 is C 1-6 alkyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 1-4 alkyl-amino, di-C 1-4 alkyl-amino, C 6-10 aryl, heteroaryl having 5 to 10 ring members, or heterocyclyl having 5 to 10 ring members, then R 3 may be unsubstituted or substituted by one or more substituents, each of which is independently halogen, -OH, oxo, -N(R b )2, C 1-3 alkyl, C 1-3 haloalkyl, C 1-3 alkoxy, C 1-3 alkylene-C 1-3 alkoxy, C 1-6 heteroalkyl, or two R 3 substituents together form a C 3-6 carbocyclyl or heterocyclyl having 3 to 6 ring members; R 4 is -H, C 1-3 alkyl, C 1-3 haloalkyl, -CN, halogen, or -N(R a )2, where each instance of R a is, independently at each occurrence, -H, C 1-6 alkyl, or -C(O)C 1-6 alkyl; or alternatively, two R a substituents together form a heterocyclyl having from 3 to 6 ring members; wherein R a may be unsubstituted or substituted with one or more substituents, each of which is independently -F, -CI, -OH, C 1-3 alkoxy; R 5 is -H, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 haloalkyl, or C 1-6 heteroalkyl; wherein when R 5 is C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 haloalkyl, or C 1-6 heteroalkyl, then R 5 may be unsubstituted or substituted by one or more substituents, each of which is independently halogen, -OH, C 1-3 alkyl, or C 1-3 alkoxy; wherein R b each instance of R 1-6 alkyl; or alternatively, two R b substituents together form a heterocyclyl having 3 to 6 ring members; and wherein when R b is C 1-6 alkyl, or alternatively, two R b substituents together form a heterocyclyl having 3 to 6 ring members, then R b may be unsubstituted or substituted by one or more substituents, each of which is independently -F, -Cl, -OH, C 1-3 alkoxy; with the proviso that: a) if (A) is or , then R 3 is not unsubstituted or substituted morpholinyl; and b) if (A) is , then R 1a and R 1b are not both methyl, R 1a and R 1b are not both -CF3, when R 1b is methyl, R 1a is not -CF3, when R 1a is methyl, R 1b is not -CF3, and R 1a and R 1b together do not provide unsubstituted or substituted piperidinyl.
2. The compound or salt of claim 1, wherein, is (i).
3. The compound or salt of claim 1 or 2, wherein, is (ii).
4. The compound or salt of any one of claims 1 to 3, wherein, is (I), (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), or (XII).
5. The compound or salt of any one of claims 1 to 4, wherein, is .
6. The compound of any one of claims 1 to 5, wherein, the compound of formula (A) is a compound of formula (I) (I) or a pharmaceutically acceptable salt of the compound; wherein X is N or CH; R 1a is -H, C 1-6 alkyl, or C 1-6 haloalkyl; wherein when R 1a is C 1-6 alkyl or C 1-6 haloalkyl, then R 1a may be unsubstituted or substituted with one or more substituents, each of which is independently halogen, -OH, -N(R b )2, C 1-3 alkyl, or C 1-3 alkoxy; R 1b is -H, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 heteroalkyl, -(C 1-6 alkylene)-O-(C 1-6 alkyl), C 3-10 cycloalkyl, or heterocyclyl having 3 to 10 ring members; wherein when R 1b is C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 heteroalkyl, C 3-10 cycloalkyl, or heterocyclyl having from 3 to 10 ring members, then R 1b may be unsubstituted or substituted by one or more substituents, each of which is independently halogen, -OH, -N(R b )2, C 1-3 alkyl, or C 1-3 alkoxy; wherein each of the C 1-3 alkyl and C 1-3 alkoxy groups can be unsubstituted or substituted with 1 to 6 -F groups; or alternatively, R 1a and R 1b together form a C 3-10 cycloalkyl, C 3-10 cycloalkenyl, or heterocyclyl having 3 to 10 ring members; wherein the R 1a and R 1b ring can be unsubstituted or substituted with one or more substituents, each of which is independently halogen, -OH, oxo, -N(R b )2, C 1-3 alkyl, C 1-3 alkoxy, or C 1-6 heteroalkyl; wherein each of the C 1-3 alkyl and C 1-3 alkoxy groups can be unsubstituted or substituted with 1 to 9 halogen groups or C 1-3 alkoxy groups; R 1c is -H, C 1-6 alkyl, or C 3-6 cycloalkyl; wherein when R 1c is C 1-6 alkyl or C 3-6 cycloalkyl, R 1c may be unsubstituted or substituted with one or more substituents, each of which is independently halogen, -OH, -N(R b )2, C 1-3 alkyl, C 1-3 alkoxy, or C 1-6 heteroalkyl; R 2 is C 3-20 cycloalkyl, C 3-20 cycloalkenyl, C 6-18 aryl, heteroaryl having 5 to 20 ring members, or heterocyclyl having 3 to 20 ring members; wherein R 2 may be unsubstituted or substituted by one or more substituents, each of which is independently halogen, -OH, oxo, -N(R b )2, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 alkylene-OH, C 1-6 alkylene-O-C 1-6 alkyl, or C 1-6 heteroalkyl; R 3 is -H, C 1-6 alkyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, amino, C 1-4 alkyl-amino, di-C 1-4 alkyl-amino, C 6-10 aryl, heteroaryl having 5 to 10 ring members, or heterocyclyl having 5 to 10 ring members; wherein, when R 3 is C 1-6 alkyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, C 1-4 alkyl-amino, di-C 1-4 alkyl-amino, C 6-10 aryl, heteroaryl having 5 to 10 ring members, or heterocyclyl having 5 to 10 ring members, then R 3 may be unsubstituted or substituted by one or more substituents, each of which is independently halogen, -OH, oxo, -N(R b )2, C 1-3 alkyl, C 1-3 haloalkyl, C 1-3 alkoxy, C 1-3 alkylene-C 1-3 alkoxy, C 1-6 heteroalkyl, or two R 3 substituents together form a C 3-6 carbocyclyl or heterocyclyl having 3 to 6 ring members; R 4 is -H or -N(R a )2, wherein R a at each occurrence when present is independently -H or C 1-6 1-6 alkyl; or alternatively, two R a substituents together form a heterocyclyl having 3 to 6 ring members; wherein R a may be unsubstituted or substituted with one or more substituents, each of which is independently -F, -CI, -OH, C 1-3 alkoxy; R 5 is -H, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 haloalkyl, or C 1-6 heteroalkyl; wherein when R 5 is C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 haloalkyl, or C 1-6 heteroalkyl, then R 5 may be unsubstituted or substituted by one or more substituents, each of which is independently halogen, -OH, C 1-3 alkyl, or C 1-3 alkoxy; wherein R b each instance of R is independently -H or C 1-6 alkyl; or alternatively, two R b substituents together form a heterocyclyl having 3 to 6 ring members; and wherein when R b is C 1-6 alkyl, or alternatively, two R b substituents together form a heterocyclyl having 3 to 6 ring members, then R b may be unsubstituted or substituted by one or more substituents, each of which is independently -F, -Cl, -OH, C 1-3 alkoxy; with the proviso that the compound is not: 6-phenyl-4-(trifluoromethyl)thieno[2,3-b]pyridine-2-methanol; 6-cyclopropylbenzo[b]thiophene-2-methanol; 6-phenylbenzo[b]thiophene-2-methanol; or 6-[3-[(dimethylamino)methyl]bicyclo[2.2.1]hept-2-en-2-yl]benzo[b]thiophene-2- methanol.
7. The compound or salt of any one of claims 1 to 6, wherein, X is N.
8. The compound or salt of any one of claims 1 to 7, wherein, X is CH.
9. The compound or salt of any one of claims 1 to 8, wherein, R 1a is -H, unsubstituted or substituted C 1-3 alkyl, or unsubstituted or substituted C 1-3 haloalkyl.
10. The compound or salt of any one of claims 1 to 9, wherein, R 1a substituted with 1, 2, 3, or 4 substituents.
11. The compound or salt of any one of claims 1 to 10, wherein, when R 1a each R 1a substituent is independently -F, -OH, or C 1-3 alkoxy.
12. The compound or salt of any one of claims 1 to 9, wherein, R 1a is unsubstituted.
13. The compound or salt of any one of claims 1 to 9, wherein, R 1a is -H, -CH3, or -CF3.
14. The compound or salt of any one of claims 1 to 13, wherein, R 1b is -H, unsubstituted or substituted C 1-3 alkyl, unsubstituted or substituted C 1-3 haloalkyl, unsubstituted or substituted C 3-6 cycloalkyl, or unsubstituted or substituted heterocyclyl having 3 to 6 ring members.
15. The compound or salt of any one of claims 1 to 14, wherein, R 1b is an unsubstituted or substituted cycloalkyl spiro ring system or an unsubstituted or substituted heterocyclyl spiro ring system.
16. The compound or salt of any one of claims 1 to 15, wherein, R 1b is a bicyclic ring system.
17. The compound or salt of any one of claims 1 to 16, wherein, R 1b is unsubstituted or substituted heterocyclyl having 1, 2, or 3 heteroatom ring members, each heteroatom ring member independently being nitrogen, oxygen, or -S(O) x - wherein x is 0, 1, or 2.
18. The compound or salt of any one of claims 1 to 17, wherein, R 1b is unsubstituted or substituted heterocyclyl having 1, 2 or 3 heteroatom ring members, each heteroatom ring member being independently nitrogen or oxygen.
19. The compound or salt of any one of claims 1 to 18, wherein, R 1b is unsubstituted or substituted heterocyclyl having 3 to 6 ring members.
20. The compound or salt of any one of claims 1 to 19, wherein, R 1b substituted by 1 or 2 substituents.
21. The compound or salt of any one of claims 1 to 20, wherein, R 1b each R 1b is independently halogen, unsubstituted or substituted C 1-3 alkyl, or unsubstituted or substituted C 1-3 alkoxy.
22. The compound or salt of any one of claims 1 to 21, wherein, When R 1b each R 1b is independently -F, -OH, methyl, or -OMe.
23. The compound or salt of any one of claims 1 to 19, wherein, R 1b is unsubstituted.
24. The compound or salt of any one of claims 1 to 8, wherein, R 1a and R 1b together form an unsubstituted or substituted C 3-10 cycloalkyl or an unsubstituted or substituted 3- to 10-membered heterocyclyl.
25. The compound or salt of any one of claims 1 to 8 and 24, wherein, R 1a and R 1b together form an unsubstituted or substituted 3- to 10-membered heterocyclyl.
26. The compound or salt of any one of claims 1 to 8 and 24 to 25, wherein, when R 1a and R 1b together form an unsubstituted or substituted heterocyclyl, the heterocyclyl comprises 1, 2, or 3 heteroatom ring members, each heteroatom ring member is independently nitrogen, oxygen, or -S(O) x - wherein x is 0, 1, or 2.
27. The compound or salt of any one of claims 1 to 8 and 24 to 26, wherein, R 1a and R 1b together form unsubstituted or substituted C 3-10 cycloalkyl.
28. The compound or salt of any one of claims 1 to 8 and 24 to 27, wherein, R 1a and R 1b together form a spiro system.
29. The compound or salt of any one of claims 1 to 8 and 24 to 28, wherein, R 1a and R 1b together form a bicyclic ring system.
30. The compound or salt of any one of claims 1 to 8 and 24 to 29, wherein, R 1a and R 1b together form a ring which is substituted with 1, 2 or 3 substituents.
31. The compound or salt of any one of claims 1 to 8 and 24 to 30, wherein, R 1a and R 1b together form a ring substituted with -(C 1-3 alkylene)-O-(C 1-3 alkyl).
32. The compound or salt of any one of claims 1 to 8 and 24 to 31, wherein, R 1a and R 1b together form a substituted ring, and each substituent of the ring is independently halogen, -OH, oxo, -N(R b )2, C 1-3 alkyl, or C 1-3 alkoxy, wherein each of the C 1-3 alkyl and C 1-3 alkoxy can be unsubstituted or substituted with 1 to 6 halogen groups or C 1-3 alkoxy groups.
33. The compound or salt of any one of claims 1 to 8 and 24 to 32, wherein, R 1a and R 1b together form a substituted ring, and each substituent of the ring is independently -F, -OH, oxo, methyl, methoxy, or -OCF3.
34. The compound or salt of any one of claims 1 to 8 and 24 to 29, wherein, R 1a and R 1b together form an unsubstituted ring.
35. The compound or salt of any one of claims 1 to 34, wherein, R 1c is -H.
36. The compound or salt of any one of claims 1 to 34, wherein, R 1c is -CF3.
37. The compound or salt of any one of claims 1 to 34, wherein, R 1c is methyl.
38. The compound or salt of any one of claims 1 to 37, wherein, R 2 is unsubstituted or substituted C 3-6 cycloalkyl, unsubstituted or substituted C 6-10 aryl, unsubstituted or substituted heteroaryl, or unsubstituted or substituted heterocyclyl.
39. The compound or salt of any one of claims 1 to 38, wherein, R 2 is unsubstituted or substituted heteroaryl or unsubstituted or substituted heterocyclyl, and the R 2 heteroaryl or heterocyclyl comprises 1, 2, 3 or 4 heteroatom ring members.
40. The compound or salt of any one of claims 1 to 39, wherein, R 2 is unsubstituted or substituted heteroaryl or unsubstituted or substituted heterocyclyl, and each ring member heteroatom of this R 2 is independently nitrogen, oxygen, or -S(O) y - wherein y is 0, 1 or 2.
41. The compound or salt of any one of claims 1 to 40, wherein, R 2 is unsubstituted or substituted fused bicyclic heteroaryl or unsubstituted or substituted fused bicyclic heterocyclyl.
42. The compound or salt of any one of claims 1 to 41, wherein, R 2 is unsubstituted or substituted heteroaryl having 8 to 10 ring members or unsubstituted or substituted heterocyclyl having 8 to 10 ring members.
43. The compound or salt of any one of claims 1 to 42, wherein, R 2 is unsubstituted or substituted heteroaryl.
44. The compound or salt of any one of claims 1 to 43, wherein, R 2 substituted with 1, 2, or 3 substituents.
45. The compound or salt of any one of claims 1 to 44, wherein, when R 2 is substituted, each R 2 substituent is independently halogen, -OH, oxo, C 1-3 alkyl, or C 1-3 alkoxy.
46. The compound or salt of any one of claims 1 to 45, wherein, When R 2 each R 2 is independently methyl, ethyl, or isopropyl.
47. The compound or salt of any one of claims 1 to 44, wherein, R 2 is unsubstituted.
48. The compound or salt of any one of claims 1 to 47, wherein, R 2 is , , , , , ; wherein "indicates that a double bond or a single bond can be present; X a each instance of X is independently nitrogen, oxygen, or carbon; n at each occurrence when present is an integer selected from 1, 2, 3, 4, or 5; n' at each occurrence when present is an integer selected from 1, 2, 3, 4, or 5; p at each occurrence when present is an integer selected from 0, 1, 2, 3, or 4; r, at each occurrence when present, is an integer selected from 0, 1, 2, 3, 4, or 5, wherein, when two instances of r occur on the same R 2 group, the combined value of the two r values does not exceed 5; R 12 each instance of R in the presence of and attached to a ring member of N is C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkylene-OH, or C 1-6 alkylene-O-C 1-6 alkyl; and R 12 each instance of R is independently halogen, -OH, oxo, -N(R b )2, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 alkylene-OH, or C 1-6 alkylene-O-C 1-6 alkyl.
49. The compound or salt of any one of claims 1 to 37, wherein, R 2 is , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,or .
50. The compound or salt of any one of claims 1 to 37, wherein, R 2 is 、 , , , , , , , , , , , , , , , , , , , , 51. The compound or salt of any one of claims 1 to 50, wherein, R 3 is unsubstituted or substituted C 3-6 cycloalkyl, unsubstituted or substituted C 3-10 cycloalkenyl, unsubstituted or substituted C 6-10 aryl, unsubstituted or substituted heteroaryl having 5 to 10 ring members, or unsubstituted or substituted heterocyclyl having 5 to 10 ring members.
52. The compound or salt of any one of claims 1 to 51, wherein, R 3 is unsubstituted or substituted heteroaryl or unsubstituted or substituted heterocyclyl, and the R 3 heteroaryl or heterocyclyl comprises 1, 2, 3 or 4 heteroatom ring members.
53. The compound or salt of any one of claims 1 to 52, wherein, R 3 is unsubstituted or substituted heteroaryl or unsubstituted or substituted heterocyclyl, and the R 3 each heteroatom of the ring is independently nitrogen, oxygen, or -S(O) z - wherein z is 0, 1, or 2.
54. The compound or salt of any one of claims 1 to 53, wherein, R 3 is unsubstituted or substituted heteroaryl.
55. The compound or salt of any one of claims 1 to 51, wherein, R 3 is unsubstituted or substituted C 3-4 cycloalkyl.
56. The compound or salt of any one of claims 1 to 51, wherein, R 3 is unsubstituted or substituted C 1-6 alkyl.
57. The compound or salt of any one of claims 1 to 56, wherein, R 3 substituted by 1, 2 or 3 substituents.
58. The compound or salt of any one of claims 1 to 57, wherein, R 3 each R 3 is independently C 1-3 alkyl, C 1-3 alkoxy, or C 1-3 alkylene-C 1-3 alkoxy.
59. The compound or salt of any one of claims 1 to 56, wherein, R 3 is unsubstituted.
60. The compound or salt of any one of claims 1 to 50, wherein, R 3 is -H.
61. The compound or salt of any one of claims 1 to 60, wherein, R 4 is -H, C 1-3 alkyl, halogen, or -N(R a )2, wherein R a is, at each occurrence when present, independently -H or C 1-6 alkyl.
62. The compound or salt of any one of claims 1 to 61, wherein, R 4 is -N(R a )2.
63. The compound or salt of any one of claims 1 to 61, wherein, R 4 is methyl.
64. The compound or salt of any one of claims 1 to 61, wherein, R 4 is -H.
65. The compound or salt of any one of claims 1 to 64, wherein, R 5 is -H or unsubstituted or substituted C 1-6 alkyl.
66. The compound or salt of any one of claims 1 to 65, wherein, R 5 is -H.
67. The compound or salt of claim 1 or 4, wherein, the compound is: 5-(4-cyclobutyl-2-(methoxymethyl)thieno[2,3-b]pyridin-6-yl)-2-methyl-2H-pyrazolo[3,4- b]pyridine; 5-(2-(methoxymethyl)-4-(l-(methoxymethyl)cyclobutyl)thieno[2,3-b]pyridin-6-yl)-2- methyl-2H-pyrazolo[3,4-b]pyridine; (R)-(4,6-bis(l-methyl-lH-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)(cyclobutyl)methanol; (S)-(4,6-bis(l-methyl-lH-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)(cyclobutyl)methanol; (R)-cyclobutyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(l-methyl-lH-pyrazol-5- yl)thieno[2,3-b]pyridin-2-yl)methanol; (S)-cyclobutyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(l-methyl-lH-pyrazol-5- yl)thieno[2,3-b]pyridin-2-yl)methanol; (R)-cyclobutyl(4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-(l-methyl-lH-pyrazol-5- yl)thieno[2,3-b]pyridin-2-yl)methanol; (S)-cyclobutyl(4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-(l-methyl-lH-pyrazol-5- yl)thieno[2,3-b]pyridin-2-yl)methanol; 5-(2-((R)-cyclobutyl(methoxy)methyl)-4-(l-methyl-lH-pyrazol-5-yl)thieno[2,3-b]pyridin- 6-yl)-2-methyl-2H-pyrazolo[3,4-b]pyridine; 5-(2-((S)-cyclobutyl(methyloxy)methyl)-4-(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-6-yl)-2-methyl-2H-pyrazolo[3,4-b]pyridine; (1R)-1-cyclobutyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1S)-1-cyclobutyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1R)-1-cyclobutyl-2,2,2-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1S)-1-cyclobutyl-2,2,2-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1R)-1-(4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1S)-1-(4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1R)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1S)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-4-(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (R)-cyclobutyl(6-cyclopropyl-4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methyl alcohol; (S)-cyclobutyl(6-cyclopropyl-4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methyl alcohol; (R)-cyclobutyl(4-cyclopropyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methyl alcohol; (S)-cyclobutyl(4-cyclopropyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methyl alcohol; (4-(dimethylamino)-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridine-2,5-diyl)dimethanol; (1R)-1-(4,6-bis(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1S)-1-(4,6-bis(1-methyl-1H-pyrazol-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1R)-1-(4,6-bis(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1S)-1-(4,6-bis(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1R)-1-(4-cyclopropyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1S)-1-(4-cyclopropyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1R)-1-(6-cyclopropyl-4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1S)-1-(6-cyclopropyl-4-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1R)-1-(4-cyclopropyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol; (1S)-1-(4-cyclopropyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol; (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (R)-cyclopropyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; (S)-cyclopropyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; (R)-cyclobutyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; (S)-cyclobutyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)methanol; (3R)-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)tetrahydro- 3-furanol; (3S)-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)tetrahydro- 3-furanol; 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; 4-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)tetrahydro-2H- pyran-4-ol; (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3R)- tetrahydro-3-furanyl)methanol; (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3S)- tetrahydro-3-furanyl)methanol; (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3R)- tetrahydro-3-furanyl)methanol; (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3S)- tetrahydro-3-furanyl)methanol; 3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3- oxacyclobutanol; 1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclopentanol; (1R)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1- propanol; (1S)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1- propanol; (6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; (1R)-2,2,2-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin- 2-yl)ethanol; (1S)-2,2,2-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin- 2-yl)ethanol; (1R)-2-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol; (1S)-2-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol; (1R)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1S)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1R)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-butanol; (1S)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-butanol; (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3-oxetanyl)methanol; (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3-oxetanyl)methanol; (1R)-3-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol; (1S)-3-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1-propanol; 4,4-difluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclohexanol; (2R)-1,1,1-trifluoro-3-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol; (2S)-1,1,1-trifluoro-3-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol; (1R)-1-cyclopropyl-2,2,2-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1S)-1-cyclopropyl-2,2,2-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (R)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (R)-(4,4-difluorocyclohexyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-(4,4-difluorocyclohexyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; 1-methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3- azetidinol; (3R)-1-methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)-3-piperidinol; (3S)-1-methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)-3-piperidinol; (2R)-1,1,1-trifluoro-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin- 2-yl)-2-butanol; (2S)-1,1,1-trifluoro-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin- 2-yl)-2-butanol; (1R)-2-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)ethanol; (1S)-2-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)ethanol; 4-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)tetrahydro-2H- thiopyran-4-ol 1,1-dioxide; 2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol; (2R)-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2- butanol; (2S)-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2- butanol; (1R)-1-cyclopropyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (1S)-1-cyclopropyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; 1-methyl-4-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-4-piperidinol; (2R)-1-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol; (2S)-1-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-propanol; 3,3-difluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; (3R)-1-methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-pyrrolidinol; (3S)-1-methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-pyrrolidinol; (R)-(1-methyl-4-piperidyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; (S)-(1-methyl-4-piperidyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; (S)-(6-(1-methyl-1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (R)-(6-(1-methyl-1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (R)-(6-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (2R)-1,1,1-trifluoro-4-methoxy-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-butanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(6-(lH-indol-5-yl)thieno[ (R)-( 1 -methyl-3-azetidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-( 1 -methyl-3-azetidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-(6-( 1,2-benzoxazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4- yl)methanol; (R)-(6-( 1,2-benzoxazol-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4- yl)methanol; (S)-tetrahydro-2H-pyran-4-yl(6-(3H-[ 1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3- b]pyridin-2-yl)methanol; (R)-tetrahydro-2H-pyran-4-yl(6-(3H-[ 1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3- b]pyridin-2-yl)methanol; (R)-((2R)- 1 -methyl-2-azetidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (R)-((2S)- 1 -methyl-2-azetidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-((2R)- 1 -methyl-2-azetidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-((2S)- 1 -methyl-2-azetidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-(3,3-difluorocyclobutyl)(6-(2-methyl- 1,3-benzoxazol-5-yl)thieno[2,3-b]pyridin-2- yl)methanol; (R)-(3,3-difluorocyclobutyl)(6-(2-methyl- 1,3-benzoxazol-5-yl)thieno[2,3-b]pyridin-2- yl)methanol; (S)-(3,3-difluorocyclobutyl)(6-( 1 H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)methanol; (R)-(3,3-difluorocyclobutyl)(6-( 1 H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)methanol; (S)-(3,3-difluorocyclobutyl)(6-(2-methylimidazo[ 1,2-a]pyridin-6-yl)thieno[2,3-b]pyridin-2- yl)methanol; (R)-(3,3-difluorocyclobutyl)(6-(2-methylimidazo[l,2-a]pyridin-6-yl)thieno[2,3- b]pyridin-2-yl)methanol; 6-(2-((R)-(3,3-difluorocyclobutyl)(hydroxy)methyl)thieno[2,3-b]pyridin-6-yl)-3- methyl-4(3H)-pyrimidinone; 6-(2-((S)-(3,3-difluorocyclobutyl)(hydroxy)methyl)thieno[2,3-b]pyridin-6-yl)-3- methyl-4(3H)-pyrimidinone; 6-(2-((S)-(3,3-difluorocyclobutyl)(hydroxy)methyl)thieno[2,3-b]pyridin-6-yl)-2- methyl-l(2H)-isoquinolinone; 6-(2-((R)-(3,3-difluorocyclobutyl)(hydroxy)methyl)thieno[2,3-b]pyridin-6-yl)-2- methyl-l(2H)-isoquinolinone; (S)-(3,3-difluorocyclobutyl)(6-(2-methyl-l,3-benzoxazol-6-yl)thieno[2,3-b]pyridin-2- yl)methanol; (R)-(3,3-difluorocyclobutyl)(6-(2-methyl-l,3-benzoxazol-6-yl)thieno[2,3-b]pyridin-2- yl)methanol; (S)-(3,3-difluorocyclobutyl)(6-(6-quinoxalinyl)thieno[2,3-b]pyridin-2-yl)methanol; (R)-(3,3-difluorocyclobutyl)(6-(6-quinoxalinyl)thieno[2,3-b]pyridin-2-yl)methanol; (S)-(3,3-difluorocyclobutyl)(6-(2-ethyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (R)-(3,3-difluorocyclobutyl)(6-(2-ethyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (lS)-l-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-l-benzothiophen-2-yl)-l- butanol; (lR)-l-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-l-benzothiophen-2-yl)-l- butanol; (S)-(3,3-difluorocyclobutyl)(6-(2-methylimidazo[l,2-a]pyridin-7-yl)thieno[2,3- b]pyridin-2-yl)methanol; (R)-(3,3-difluorocyclobutyl)(6-(2-methylimidazo[l,2-a]pyridin-7-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-(3,3-difluorocyclobutyl)(6-(2-(2-propyl)-2H-indazol-5-yl)thieno[2,3-b]pyridin-2- yl)methanol; (R)-(3,3-difluorocyclobutyl)(6-(2-(2-propyl)-2H-indazol-5-yl)thieno[2,3-b]pyridin-2- yl)methanol; (S)-(3,3-difluorocyclobutyl)(6-(5-imidazolyl)thieno[2,3-b]pyridin-2-yl)methanol; (R)-(3,3-difluorocyclobutyl)(6-(5-imidazolyl)thieno[2,3-b]pyridin-2-yl)methanol; (S)-cyclopentyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)methanol; (R)-cyclopentyl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)methanol; (1S)-3-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)-1-propanol; (1R)-3-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)-1-propanol; (1S)-4,4,4-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)-1-butanol; (1R)-4,4,4-trifluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)-1-butanol; (S)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)methanol; (R)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-1-benzothiophen-2-yl)methanol; (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3R)-1-methyl-3-pyrrolidinyl)methanol; (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3S)-1-methyl-3-pyrrolidinyl)methanol; (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3R)-1-methyl-3-pyrrolidinyl)methanol; (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((3S)-1-methyl-3-pyrrolidinyl)methanol; (R)-((3R)-1-methyl-3-piperidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; (R)-((3S)-1-methyl-3-piperidinyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; (S)-((3R)-1-methyl-3-piperidyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-((3S)-1-methyl-3-piperidyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-(3,3-difluorocyclobutyl)(6-(2-(2-propyl)-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (R)-(3,3-difluorocyclobutyl)(6-(2-(2-propyl)-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-(3,3-difluorocyclobutyl)(6-(1-(2-propyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (R)-(3,3-difluorocyclobutyl)(6-(1-(2-propyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H- pyran-4-yl)methanol; (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H- pyran-4-yl)methanol; (R)-(3-amino-6-(5-imidazolyl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol; (S)-(3-amino-6-(5-imidazolyl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol; 2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[3.3]heptan-2- ol; 3,3-dimethyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; 6,6-difluoro-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[3.3]heptan-2-ol; 6-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-2-oxaspiro[3.3]heptan-6-ol; cis-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol; Cis-3-(difluoromethyl)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)cyclobutanol; Cis-3-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; (S)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazolo[5,4- b]pyridin-2-yl)methanol; (R)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazolo[5,4- b]pyridin-2-yl)methanol; 1-(6-(2-ethyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3,3-difluorocyclobutanol; (S)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2- b]pyridin-2-yl)methanol; (R)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2- b]pyridin-2-yl)methanol; 3,3-difluoro-1-(6-(3-methyl-3H-imidazo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; 3,3-difluoro-1-(6-(2-methyl[1,3]oxazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; 3,3-difluoro-1-(6-(2-methyl-3H-imidazo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; 3,3-difluoro-1-(6-(1H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; 3,3-difluoro-1-(6-(2-methylimidazo[1,2-a]pyridin-6-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; 1-(6-(2-amino-5-pyrimidinyl)thieno[2,3-b]pyridin-2-yl)-3,3-difluorocyclobutanol; (S)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazolo[4,5- b]pyridin-2-yl)methanol; (R)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazolo[4,5- b]pyridin-2-yl)methanol; 3,3-difluoro-1-(6-(2-methyl-1,3-benzoxazol-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; Trans-3-fluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; (R)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)methanol; (S)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)methanol; (S)-(3-chloro-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol; (R)-(3-chloro-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol; 3,3-difluoro-1-(6-(3H-imidazo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; 3,3-difluoro-1-(6-(1H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; (R)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; (S)-(3,3-difluorocyclobutyl)(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; (S)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)methanol; (R)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)methanol; 3,3-difluoro-1-(6-(2-(methylamino)-5-pyrimidinyl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; (R)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; (S)-(3,3-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; 3,3-difluoro-1-(6-(2-methylimidazo[1,2-a]pyridin-7-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; 3,3-difluoro-1-(6-(2-methylimidazo[1,2-a]pyrimidin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; (2R)-2-(3,3-difluorocyclobutyl)-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)ethanol; (2S)-2-(3,3-difluorocyclobutyl)-2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)ethanol; 3,3-difluoro-l-(6-(5-imidazolyl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; 3,3-difluoro-l-(6-(pyrido[2,3-b]pyrazin-7-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; (S)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7- quinolinyl)methanol; (R)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7- quinolinyl)methanol; 3,3-difluoro-l-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-l-benzothiophen-2- yl)cyclobutanol; 3,3-difluoro-l-(6-(2-methyl-2H-indazol-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; l-(6-(l,2-benzoxazol-5-yl)thieno[2,3-b]pyridin-2-yl)-3,3-difluorocyclobutanol; 3,3-difluoro-l-(6-(3-methyl-3H-[l,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; 2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[3.5]nonan-2- ol; 2-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[3.4]octan-2- ol; 3,3-difluoro-l-(6-(2-methylimidazo[l,2-b]pyridazin-7-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; 3,3-difluoro-l-(6-(3H-[l,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; (R)-(3,3-difluorocyclobutyl)(6-(3-methyl-3H-[l,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-(3,3-difluorocyclobutyl)(6-(3-methyl-3H-[l,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3- b]pyridin-2-yl)methanol; Trans-6-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1- oxaspiro[3.3]heptan-6-ol; Cis-6-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-1- oxaspiro[3.3]heptan-6-ol; 3,3-Dimethyl-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6- yl)cyclobutanol; Cis-3-(Methoxymethyl)-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)cyclobutanol; Trans-3-Methoxy-3-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)cyclobutanol; Cis-3-Methoxy-3-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)cyclobutanol; (R)-(3,3-Difluorocyclobutyl)(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-(3,3-Difluorocyclobutyl)(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; 1-(6-(2-Methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclopropanol; 5-(6-(2-Methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[2.3]hexan-5- ol; Cis-3-Cyclopropyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; Trans-3-Hydroxy-1-methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)cyclobutanenitrile; Cis-3-Hydroxy-1-methyl-3-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)cyclobutanenitrile; (1S,2R)-2-Methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; (1R,2S)-2-Methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; (1S)-2,2-dimethyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; (1R)-2,2-dimethyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; Trans-3-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)- 3-(trifluoromethyl)cyclobutanol; Cis-3-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)- 3-(trifluoromethyl)cyclobutanol; Cis-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3- (trifluoromethoxy)cyclobutanol; 3,3-dimethyl-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazolo[5,4-b]pyridin-2- yl)cyclobutanol; Cis-1-(3-chloro-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3- methoxycyclobutanol; (1R,2R)-2-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; (1R,2S)-2-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; (1S,2R)-2-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; Cis-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)-3- (trifluoromethyl)cyclobutanol; (1S,2S)-2-methoxy-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; 1-(3-chloro-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3,3- dimethylcyclobutanol; Cis-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazolo[5,4-b]pyridin-2-yl)-3- (trifluoromethyl)cyclobutanol; (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((cis)-3- (trifluoromethyl)cyclobutyl)methanol; (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((cis)-3- (trifluoromethyl)cyclobutyl)methanol; (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((trans)-3- (trifluoromethyl)cyclobutyl)methanol; (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)((trans)-3- (trifluoromethyl)cyclobutyl)methanol; Cis-1-(3-chloro-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)-3- (trifluoromethyl)cyclobutanol; (R)-((1R)-2,2-difluorocyclopropyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-((1S)-2,2-difluorocyclopropyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-((1R)-2,2-difluorocyclopropyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (R)-((1S)-2,2-difluorocyclopropyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (R)-(3,3-difluoro-1-methylcyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-(3,3-difluoro-1-methylcyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (R)-bicyclo[1.1.1]pentan-1-yl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-bicyclo[1.1.1]pentan-1-yl(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-((cis)-3-methoxycyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; Cis-3-(difluoromethyl)-1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3- b]pyridin-2-yl)cyclobutanol; (R)-((cis)-3-methoxycyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (S)-((trans)-3-methoxycyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; (R)-((trans)-3-methoxycyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- b]pyridin-2-yl)methanol; 3,3-dimethyl-l-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7-quinolinyl)cyclobutanol; 3,3-difluoro-l-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin- 2-yl)cyclobutanol; cis- 1 -(3 -methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5 -yl)thieno[2,3 -b]pyridin-2-yl)-3 -(trif luoromethyl)cyclobutanol; cis- 1 -(6-(3 -methyl-3H-[ 1,2,3 ]triazolo[4,5 -b]pyridin-6-yl)thieno[2,3 -b]pyridin-2-yl)-3 -(trif luoromethyl)cyclobutanol; cis-3-(difluoromethyl)-l-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin- 6-yl)cyclobutanol; (R)-(2-(3-methyl-3H-[l,2,3]triazolo[4,5-b]pyridin-6-yl)-7-quinolinyl)(tetrahydro-2H-pyran-4- yl)methanol; (S)-(2-(3-methyl-3H-[l,2,3]triazolo[4,5-b]pyridin-6-yl)-7-quinolinyl)(tetrahydro-2H-pyran-4- yl)methanol; (R)-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7-quinolinyl)(tetrahydro-2H-pyran-4- yl)methanol; (S)-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7-quinolinyl)(tetrahydro-2H-pyran-4- yl)methanol; cis-3-(difluoromethyl)-l-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[l,3]thiazolo[5,4- b]pyridin-2-yl)cyclobutanol; cis-3-(difluoromethyl)-l-(5-(3-methyl-3H-[l,2,3]thiazolo[4,5-b]pyridin-6-yl)[l,3]thiazolo[5,4- b]pyridin-2-yl)cyclobutanol; (R)-(3-methyl-6-(3-methyl-3H-[l,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2- yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(3-methyl-6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (R)-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; (S)-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(tetrahydro-2H-pyran-4-yl)methanol; Cis-3-(difluoromethyl)-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-7-quinolinyl)cyclobutanol; (R)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3-(trifluoromethyl)bicyclo[1.1.1]pentan-1-yl)methanol; (S)-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3-(trifluoromethyl)bicyclo[1.1.1]pentan-1-yl)methanol; Cis-3-fluoro-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; Cis-3-(difluoromethyl)-1-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; Cis-3-(difluoromethyl)-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-quinolinyl)cyclobutanol; Cis-3-(difluoromethyl)-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)cyclobutanol; Cis-3-(difluoromethyl)-1-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol; Cis-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)-3-(trifluoromethyl)cyclobutanol; (S)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-quinolinyl)methanol; (R)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)-6-quinolinyl)methanol; Cis-3-(difluoromethyl)-1-(6-(2-ethyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; (trans)-1,1-difluoro-5-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[2.3]hexan-5-ol; (cis)-1,1-difluoro-5-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)spiro[2.3]hexan-5-ol; (cis)-3-(difluoromethyl)-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-6-yl)cyclobutanol; (cis)-3-(difluoromethyl)-1-(5-methyl-2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol; (trans)-3-hydroxy-1-methyl-3-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazolo[5,4-b]pyridin-2-yl)cyclobutanenitrile; (cis)-3-hydroxy-1-methyl-3-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazolo[5,4-b]pyridin-2-yl)cyclobutanenitrile; (cis)-3-(difluoromethyl)-1-(6-(2-methylimidazo[1,2-b]pyridazin-7-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; (cis)-3-(difluoromethyl)-1-(6-(2-methyl-3H-imidazo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanol; (R)-(3,3-difluorocyclobutyl)(3-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyrazin-6-yl)methanol; (S)-(3,3-difluorocyclobutyl)(3-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyrazin-6-yl)methanol; (2S)-2-(3,3-difluorocyclobutyl)-2-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (2R)-2-(3,3-difluorocyclobutyl)-2-(3-methyl-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)ethanol; (cis)-3-methoxy-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol; (cis)-1-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol; Cis-3-hydroxy-1-methyl-3-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- d]pyrimidin-6-yl)cyclobutanecarbonitrile; Trans-3-hydroxy-1-methyl-3-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3- d]pyrimidin-6-yl)cyclobutanecarbonitrile; Cis-3-(difluoromethyl)-1-(6-(2-methylimidazo[1,2-a]pyrimidin-6-yl)thieno[2,3-b]pyridin- 2-yl)cyclobutanol; Trans-3-hydroxy-1-methyl-3-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2, 3-b]pyridin-2-yl)cyclobutanecarbonitrile; Cis-3-hydroxy-1-methyl-3-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2, 3-b]pyridin-2-yl)cyclobutanecarbonitrile; Cis-3-cyclopropyl-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin- 6-yl)cyclobutanol; Cis-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)-3- (trifluoromethoxy)cyclobutanol; Cis-1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)-3- (trifluoromethoxy)cyclobutanol; Cis-3-methoxy-3-methyl-1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2, 3-b]pyridin-2-yl)cyclobutanol; Cis-3-(difluoromethyl)-1-(6-(3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2- yl)cyclobutanol; Trans-3-hydroxy-1-methyl-3-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2, 3-b]pyridin-2-yl)cyclobutanecarbonitrile; Cis-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazolo[5,4-b]pyridin-2-yl)-3- (trifluoromethoxy)cyclobutanol; Trans-3-hydroxy-1-methyl-3-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2- b]pyridin-2-yl)cyclobutanecarbonitrile; Cis-3-hydroxy-1-methyl-3-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2- b]pyridin-2-yl)cyclobutanecarbonitrile; 5-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)spiro[2.3]hexan-5-ol; 5-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazolo[5,4-b]pyridin-2-yl)spiro[2.3]hexan-5-ol; (R)-((1S)-2,2-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; (S)-((1R)-2,2-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; (R)-((1R)-2,2-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; (S)-((1S)-2,2-difluorocyclobutyl)(6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)methanol; cis-3-(difluoromethyl)-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-2-yl)cyclobutanol; cis-3-hydroxy-1-methyl-3-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-b]pyridin-2-yl)cyclobutanecarbonitrile; cis-1-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethoxy)cyclobutanol; cis-1-(5-(3-methyl-3H-[1,2,3]thiazolo[4,5-b]pyridin-6-yl)[1,3]thiazolo[5,4-b]pyridin-2-yl)-3-(trifluoromethoxy)cyclobutanol; trans-3-methoxy-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol; cis-3-methoxy-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol; trans-1,1-difluoro-5-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)spiro[2.3]hexan-5-ol; cis-1,1-difluoro-5-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)spiro[2.3]hexan-5-ol; Trans-1,1-difluoro-5-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazolo[5,4-b]pyridin-2-yl)spiro[2.3]hexan-5-ol; Cis-1,1-difluoro-5-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)[1,3]thiazolo[5,4-b]pyridin-2-yl)spiro[2.3]hexan-5-ol; 6,6-difluoro-2-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)spiro[3.3]heptan-2-ol; Cis-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[3,2-b]pyridin-2-yl)-3-(trifluoromethoxy)cyclobutanol; Trans-3-methoxy-3-methyl-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol; Cis-3-methoxy-3-methyl-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol; Cis-3-methoxy-3-methyl-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol; Cis-3-(methoxymethyl)-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol; Cis-1-(2-(1-methyl-1H-pyrazol-4-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol; (S)-(3-amino-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol; (R)-(3-amino-6-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-b]pyridin-2-yl)(3,3-difluorocyclobutyl)methanol; Trans-3-methoxy-3-methyl-1-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol; Cis-3-methoxy-3-methyl-1-(2-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-6-yl)thieno[2,3-d]pyrimidin-6-yl)cyclobutanol; Cis-1-(2-(3-pyridyl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol; Cis-1-(2-(6-quinoxalinyl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol; Cis-1-(2-(imidazo[1,2-a]pyrimidin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol; Trans-3-methoxy-3-methyl-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridine-5-yl)[1,3]thiazolo[5,4-b]pyridine-2-yl)cyclobutanol; Cis-3-methoxy-3-methyl-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridine-5-yl)[1,3]thiazolo[5,4-b]pyridine-2-yl)cyclobutanol; Trans-3-methoxy-3-methyl-1-(6-(3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridine-6-yl)thieno[2,3-b]pyridine-2-yl)cyclobutanol; Cis-1-(2-(4-pyridazinyl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol; Cis-3-methoxy-3-methyl-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridine-5-yl)thieno[3,2-b]pyridine-2-yl)cyclobutanol; 3-(6-(Cis-1-hydroxy-3-(trifluoromethyl)cyclobutyl)thieno[2,3-d]pyrimidin-2-yl)-5,6-dihydro-7H-pyrrolo[3,4-b]pyridin-7-one; Cis-1-(2-([1,2,4]triazolo[4,3-a]pyrimidin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol; (R)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridine-5-yl)thieno[2,3-b]pyrazin-6-yl)methanol; (S)-(3,3-difluorocyclobutyl)(2-(2-methyl-2H-pyrazolo[3,4-b]pyridine-5-yl)thieno[2,3-b]pyrazin-6-yl)methanol; Trans-3-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridine-5-yl)thieno[2,3-b]pyridine-2-yl)-3-(trifluoromethyl)cyclobutanol; Cis-3-methyl-1-(6-(2-methyl-2H-pyrazolo[3,4-b]pyridine-5-yl)thieno[2,3-b]pyridine-2-yl)-3-(trifluoromethyl)cyclobutanol; Cis-1-(2-(2-methyl-2H-[1,2,3]triazolo[4,5-b]pyridine-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol; Cis-1-(2-(1-methyl-1H-[1,2,3]triazolo[4,5-b]pyridine-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol; Cis-1-(2-(1-methyl-1H-imidazo[4,5-b]pyridine-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol; Cis-1-(2-(1,8-naphthyridin-3-yl)thieno[2,3-d]pyrimidin-6-yl)-3-(trifluoromethyl)cyclobutanol; Trans-3-(difluoromethyl)-1-(5-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thiazolo[5,4- b]pyridin-2-yl)cyclobutanol; Trans-3-methoxy-1-(2-(2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6- yl)cyclobutanol; Cis-1-(2-([1,2,4]triazolo[1,5-a]pyrimidin-6-yl)thieno[2,3-d]pyrimidin-6-yl)-3- (trifluoromethyl)cyclobutanol.
68. The compound or salt of claim 1, wherein, The compound is: A1。 69. The compound or salt of claim 1, wherein, The compound is: B2。 70. The compound or salt of claim 1, wherein, The compound is: B8。 71. The compound or salt of claim 1, wherein, The compound is: B6R.
72. The compound or salt of claim 1, wherein, The compound is: B18。 73. The compound or salt of claim 1, wherein, The compound is: B15R.
74. The compound or salt of claim 1, wherein, The compound is: B30R.
75. The compound or salt of claim 1, wherein, The compound is: B41R.
76. The compound or salt of claim 1, wherein, The compound is: B48R.
77. The compound or salt of claim 1, wherein, The compound is: B49R.
78. The compound or salt of claim 1, wherein, The compound is: B58R.
79. The compound or salt of claim 1, wherein, The compound is: B61。 80. The compound or salt of claim 1, wherein, The compound is: B66。 81. The compound or salt of claim 1, wherein, The compound is: B71。 82. The compound or salt of claim 1, wherein, The compound is: B79R.
83. The compound or salt of claim 1, wherein, The compound is: C5。 84. The compound or salt of claim 1, wherein, The compound is: C30 C.
85. The compound or salt of claim 1, wherein, The compound is: C59C.
86. The compound or salt of claim 1, wherein, The compound is: C67C.
87. The compound or salt of claim 1, wherein, The compound is: C71C.
88. The compound or salt of claim 1, wherein, The compound is: C74C.
89. The compound or salt of claim 1, wherein, The compound is: C94C.
90. The compound or salt of claim 1, wherein, The compound is: C100C. The compound is: The compound is:
91. The compound of any one of claims 1 to 90.
92. A pharmaceutical composition comprising the compound of any one of claims 1 to 90 or the compound of claim 91 and a pharmaceutically acceptable excipient.
93. The compound of any one of claims 1 to 90, the compound of claim 91, or the pharmaceutical composition of claim 92, for use as a medicament.
94. The compound of any one of claims 1 to 90, the compound of claim 91, or the pharmaceutical composition of claim 92, for use in treating a 15-PGDH-mediated disease or disorder.
95. The compound of any one of claims 1 to 90, the compound of claim 91, or the pharmaceutical composition of claim 92, for use in treating inflammatory bowel disease.
96. The compound of any one of claims 1 to 90 or the compound of claim 91, for use in the manufacture of a medicament for treating a 15-PGDH-mediated disease or disorder.
97. A method of treating an intestinal, gastrointestinal, or bowel disorder in a subject in need thereof, the method comprising: administering to the subject a therapeutically acceptable amount of the compound or salt of any one of claims 1 to 90, the compound of claim 91, or the pharmaceutical composition of claim 92. (A-int-b) 98. A method of manufacturing the compound or salt of claim 1 or 6, the method comprising: (R2-B); performing a Suzuki coupling between a compound of formula (A-int-b) X H is -Br or -Cl; B a is a boronic acid group or boronic ester group; "indicates that a double bond or a single bond can be present; X a each instance of X is independently nitrogen, oxygen, or carbon; r, at each occurrence when present, is an integer selected from 0, 1, 2, 3, 4, or 5, wherein, when two instances of r occur on the same R 2 group, the combined value of the two r values does not exceed 5; R 12 each instance of R is independently C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkylene-OH, or C 1-6 alkylene-O-C 1-6 alkyl; and R 12 each instance of R is independently -OH, oxo, -N(R b )2, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 alkylene-OH, or C 1-6 alkylene-O-C 1-6 alkyl; wherein R b each instance of R, when present, is independently -H or C 1-6 alkyl; or alternatively, two R b substituents together form a heterocyclyl having 3 to 6 ring members; and wherein when R b is C 1-6 alkyl, or alternatively, two R b substituents together form a heterocyclyl having 3 to 6 ring members, then R b may be unsubstituted or substituted by one or more substituents, each of which is independently -F, -Cl, -OH, C 1-3 alkoxy. and a compound of formula (R2-B): wherein (A-int-b) 99. The compound or salt of claim 1, made by a method comprising: (R2-B); performing a Suzuki coupling between a compound of formula (A-int-b) and a compound of formula (R2-B): wherein 99. The compound or salt of claim 1, made by a method comprising: performing a Suzuki coupling between a compound of formula (A-int-b) and a compound of formula (R2-B): wherein X H is -Br or -Cl; B a is a boronic acid group or boronic ester group; "indicates that a double bond or a single bond can be present; X a each instance of X is independently nitrogen, oxygen, or carbon; r, at each occurrence when present, is an integer selected from 0, 1, 2, 3, 4, or 5, wherein, when two instances of r appear on the same R 2 the combined total of the two r values is no more than 5; R 12 each instance of R is independently C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkylene-OH, or C 1-6 alkylene-O-C 1-6 alkyl; and R 12 each instance of R is independently -OH, oxo, -N(R b )2, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 alkylene-OH, or C 1-6 alkylene-O-C 1-6 alkyl; wherein R b each instance of R, when present, is independently -H or C 1-6 alkyl; or alternatively, two R b substituents together form a heterocyclyl having 3 to 6 ring members; and wherein when R b is C 1-6 alkyl, or alternatively, two R b substituents together form a heterocyclyl having 3 to 6 ring members, then R b may be unsubstituted or substituted by one or more substituents, each of which is independently -F, -Cl, -OH, C 1-3 alkoxy.
100. A method of manufacturing the compound or salt of claim 1 or 27, comprising using a compound of formula (A-int-a) as an intermediate: (A-int-a) or a pharmaceutically acceptable salt of the compound; wherein X H1 is -CI, -Br, or -I; and X H2 is -CI, -Br, -OTf, -OTs, or -OMs.
101. A method of manufacturing the compound or salt of claim 1 or 6, comprising using a compound of formula (A-int-b) as an intermediate: (A-int-b) wherein X H2 is -Cl, -Br, -OTf, -OTs, or -OMs.
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Patent Citations
Cephalosporin derivatives
WO1987005297A1