# US 10,766,894 B2 · Aza-indazole compounds for use in tendon and/or ligament injuries

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- Number: US 10,766,894 B2
- Document ID: US10766894B2
- Status: Granted
- Kind: B2
- Application number: 16/335,496
- Filed: 2017-09-21
- Published: 2019-10-03
- Granted: 2020-09-08
- Earliest claimed: 2016-09-23
- Assignees: Novartis AG
- Applicants: Novartis AG
- Inventors: Badry Bursulaya; Andreas Fisch; James Paul Lajiness; Rainer Machauer; Swapnil Malekar; Hank Michael James Petrassi; Farshad Ramazani; Anne-Catherine Remond; Thomas Ullrich; Peggy Usselmann; Eric Vangrevelinghe
- Web page: https://patentgrep.com/patent/US10766894B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 9/5031: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poly(lactide-co-glycolide)}
- A61K 31/437: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A61K 31/496: Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A61K 31/538: ortho- or peri-condensed with carbocyclic ring systems
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 19/04: for non-specific disorders of the connective tissue
- A61P 21/00: Drugs for disorders of the muscular or neuromuscular system
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides a compound of formula (I) in free form or in pharmaceutically acceptable salt form, a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

## Claims

### Claim 1

A compound of formula (I) or a pharmaceutically acceptable salt thereof
wherein,
R1 is selected from C1-C3alkyl and halogen;
R2 is selected from NHSO2(CH2)nR3 and SO2NR5R6;
n is 0 or 1;
R3 is selected from phenyl optionally substituted once or more than once with R4; C3-C6cycloalkyl optionally substituted with hydroxyl; and a fused bicyclic aromatic ring system;
R4 is independently selected from halogen, C1-C3alkoxy, cyano, C1-C3alkyl, hydroxyl, haloC1-C3alkyl, NHC(O)CH3, haloC1-C3alkoxy, and SO2NH(CH3); or
two R4 at adjacent carbon atoms form a 5- or 6-membered heterocyclic non-aromatic ring comprising at least one heteroatom selected from N, O, or S said heterocyclic ring being fused to the phenyl ring and being optionally substituted with C(O)CH3;
R5 is selected from H and C1-C3alkyl;
R6 is selected from a C3-C6cycloalkyl optionally substituted once or more than once with R7; phenyl optionally substituted once or more than once with halogen; C1-C6alkyl optionally substituted with hydroxyl; 4- to 6-membered heterocyclic non-aromatic ring comprising at least one heteroatom selected from N, O or S optionally substituted once or more than once with oxo; and benzyl;
R7 is independently selected from hydroxyl, haloC1-C3alkyl, halogen, C1-C3alkyl, C(O)OH, and hydroxyC1-C3alkyl;
or
R5 and R6 together with the N atom to which they are attached form a 4-, 5- or 6-membered heterocyclic non-aromatic ring optionally comprising one additional heteroatom selected from N, O or S, said ring being optionally substituted once or more than once with R8; a 6- to 8-membered saturated bicyclic ring system;
R8 is independently selected from halogen; hydroxyC1-C3alkyl; C(O)NH2; hydroxyl; haloC1-C3alkyl optionally substituted with hydroxyl; phenoxy; and SO2C1-C3alkyl.

### Claim 2 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof wherein,
R1 is chloro or methyl; and
R2 is SO2NR5R6.

### Claim 3 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof wherein
R5 is H or methyl; and
R6 is C4-C6cycloalkyl optionally substituted once or more than once with R7; and
R7 is independently selected from hydroxyl, haloC1-C3alkyl, halogen, and C1-C3alkyl, hydroxyC1-C3alkyl.

### Claim 4 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof wherein
R5 and R6 together with the N atom to which they are attached form a 4-, 5- or 6-membered heterocyclic non-aromatic ring optionally comprising one additional heteroatom selected from N, O or S, said ring being optionally substituted once or more than once with R8; and
R8 is independently selected from halogen and hydroxyC1-C3alkyl.

### Claim 5 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein
R1 is chloro or methyl;
R2 is NHSO2R3; and
R3 is selected from phenyl optionally substituted once or more than once with R4; and C3-C6cycloalkyl optionally substituted with hydroxyl.

### Claim 6 (depends on 5)

The compound according to claim 5 or a pharmaceutically acceptable salt thereof, wherein
R4 is independently selected from halogen, C1-C3alkoxy, cyano, C1-C3alkyl, hydroxyl, and haloC1-C3alkyl; or
two R4 at adjacent carbon atoms form a 5- or 6-membered heterocyclic non-aromatic ring comprising at least one heteroatom selected from N, O, or S said heterocyclic ring being fused to the phenyl ring and being optionally substituted with C(O)CH3.

### Claim 7 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof, which is selected from
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(3-hydroxy-3-(trifluoromethyl)cyclobutyl)benzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-(3-hydroxy-3-(trifluoromethyl)cyclobutyl)-3-methylbenzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-4-chlorobenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(3,3-difluorocyclobutyl)benzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-4-methoxybenzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-4-fluorobenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(2-hydroxycyclopentyl)benzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-(3,3-difluorocyclobutyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-(3-hydroxy-3-(trifluoromethyl)cyclobutyl)-N,3-dimethylbenzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-3,4-difluorobenzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)benzo[d][1,3]dioxole-5-sulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(2-hydroxycyclohexyl)benzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-4-chloro-3-fluorobenzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-2-hydroxycyclohexane-1-sulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)cyclohexanesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-methyl-N-phenylbenzenesulfonamide;
1-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)sulfonyl)-4,4-difluoropyrrolidin-2-yl)methanol;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-(3-hydroxycyclopentyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-(2-hydroxycyclopentyl)-3-methylbenzenesulfonamide;
5-(4-((hexahydrocyclopenta[c]pyrrol-2(1H)-yl)sulfonyl)-2-methylphenyl)-1H-pyrazolo[4,3-b]pyridin-3-amine;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-3-cyanobenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(3-hydroxycyclopentyl)benzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(4,4-dimethylcyclohexyl)benzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-4-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-(1-(hydroxymethyl)cyclopentyl)-3-methylbenzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-3-chloro-4-fluorobenzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-3-chlorobenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(1-(hydroxymethyl)cyclopentyl)benzenesulfonamide);
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(1,1-dioxidotetrahydrothiophen-3-yl)benzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-2-hydroxy-5-methylbenzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-methylphenyl)-3-fluorobenzenesulfonamide;
1-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-methylphenyl)sulfonyl)-4,4-difluoropyrrolidine-2-carboxamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(;2-hydroxycyclopentyl)benzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(4-methylcyclohexyl)benzenesulfonamide;
1-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-methylphenyl)sulfonyl)-4,4-difluoropyrrolidin-2-yl)methanol;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-phenylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-cyclohexyl-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-cyclohexyl-3-methylbenzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-3-fluorobenzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-methylphenyl)-3-chlorobenzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-3,4-dichlorobenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(3-hydroxycyclohexyl)benzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(4-hydroxycyclohexyl)benzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)benzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-(3-(hydroxymethyl)cyclobutyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-fluoro-N-phenylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)benzenesulfonamide;
5-(2-chloro-4-((hexahydrocyclopenta[c]pyrrol-2(1H)-yl)sulfonyl)phenyl)-1H-pyrazolo[4,3-b]pyridin-3-amine;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(3-chloro-2-fluorophenyl)benzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-sulfonamide;
1-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)sulfonyl)-4-fluoropyrrolidine-2-carboxamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(2,3-dichlorophenyl)benzenesulfonamide;
1-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)sulfonyl)pyrrolidin-3-ol;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(4-hydroxy-4-methylcyclohexyl)benzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-1-phenylmethanesulfonamide;
N-(5-(N-(4-(3-amino-H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)sulfamoyl)-2-methoxyphenyl)acetamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-3-(trifluoromethyl)benzenesulfonamide;
5-(4-(3-azabicyclo[3.1.0]hexan-3-ylsulfonyl)-2-chlorophenyl)-1H-pyrazolo[4,3-b]pyridin-3-amine;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-(3-hydroxycyclobutyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-(3-hydroxycyclohexyl)-3-methylbenzenesulfonamide;
1-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-methylphenyl)sulfonyl)-3-(trifluoromethyl)azetidin-3-ol;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-3-methoxybenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-(4-hydroxy-4-(trifluoromethyl)cyclohexyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-(4-hydroxycyclohexyl)-3-methylbenzenesulfonamide;
1-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-methylphenyl)sulfonyl)pyrrolidin-2-yl)methanol;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(2-hydroxyethyl)benzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-benzyl-3-chlorobenzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)pyridine-3-sulfonamide;
5-(2-chloro-4-((3,3-difluoroazetidin-1-yl)sulfonyl)phenyl)-1H-pyrazolo[4,3-b]pyridin-3-amine;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-tert-butyl-3-fluorobenzenesulfonamide;
N1-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-N4-methylbenzene-1,4-disulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-4-(trifluoromethyl)benzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-3,4-dimethoxybenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-(4-hydroxy-4-methylcyclohexyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(2,3-difluorophenyl)benzenesulfonamide;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)naphthalene-2-sulfonamide;
2-(1-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-methylphenyl)sulfonyl)pyrrolidin-3-yl)ethanol;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(3-(hydroxymethyl)cyclobutyl)benzenesulfonamide;
4-acetyl-N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-sulfonamide;
5-(2-chloro-4-((3-phenoxyazetidin-1-yl)sulfonyl)phenyl)-1H-pyrazolo[4,3-b]pyridin-3-amine;
N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-4-(trifluoromethoxy)benzenesulfonamide;
2-(4-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)sulfonyl)piperazin-2-yl)-1,1,1-trifluoropropan-2-ol;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(3-chlorophenyl)benzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-(2-hydroxycyclohexyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(1,1-dioxidothietan-3-yl)benzenesulfonamide; and
5-(2-chloro-4-((3-(methylsulfonyl)azetidin-1-yl)sulfonyl)phenyl)-1H-pyrazolo[4,3-b]pyridin-3-amine.

### Claim 8 (depends on 7)

The compound according to claim 7 or a pharmaceutically acceptable salt thereof, which is selected from
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-((1 s,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)benzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-((1 s,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-((1R,2S)-2-hydroxycyclopentyl)benzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-((1 s,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)-N,3-dimethylbenzenesulfonamide;
(1S,2R)-N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-2-hydroxycyclohexane-1-sulfonamide;
(S)-(1-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)sulfonyl)-4,4-difluoropyrrolidin-2-yl)methanol;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-((1R,3 S)-3-hydroxycyclopentyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-((1R,2S)-2-hydroxycyclopentyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-((1R,3S)-3-hydroxycyclopentyl)benzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-((1R,2R)-2-hydroxycyclopentyl)benzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-((1S,2R)-2-hydroxycyclopentyl)benzenesulfonamide;
(S)-(1-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-methylphenyl)sulfonyl)-4,4-difluoropyrrolidin-2-yl)methanol;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-((1r,4r)-4-hydroxycyclohexyl)benzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-((1 s,3s)-3-(hydroxymethyl)cyclobutyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-((1 s,4s)-4-hydroxycyclohexyl)benzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-((1 r,4r)-4-hydroxycyclohexyl)-3-methylbenzenesulfonamide;
(2R,4R)-1-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)sulfonyl)-4-fluoropyrrolidine-2-carboxamide;
(R)-1-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)sulfonyl)pyrrolidin-3-ol;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-((1 r,4r)-4-hydroxy-4-methylcyclohexyl)benzenesulfonamide;
(1R,2S)-N-(4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)-2-hydroxycyclohexane-1-sulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-((1 s,3s)-3-hydroxycyclobutyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-((1r,4r)-4-hydroxy-4-(trifluoromethyl)cyclohexyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-((1 s,4s)-4-hydroxycyclohexyl)-3-methylbenzenesulfonamide;
(S)-(1-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-methylphenyl)sulfonyl)pyrrolidin-2-yl)methanol;
(S)-1-((4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chlorophenyl)sulfonyl)pyrrolidin-3-ol;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-((1 r,3r)-3-hydroxycyclobutyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-3-methylbenzenesulfonamide;
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-((1s,3s)-3-(hydroxymethyl)cyclobutyl)benzenesulfonamide; and
4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-((1S,2S)-2-hydroxycyclopentyl)benzenesulfonamide.

### Claim 9 (depends on 1)

A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable carriers.

### Claim 10 (depends on 9)

The pharmaceutical composition according to claim 9, wherein the composition is in the form of a sustained release formulation.

### Claim 11 (depends on 9)

The pharmaceutical composition according to claim 9, wherein the composition is formulated for injection.

### Claim 12 (depends on 9)

The pharmaceutical composition according to claim 9, wherein the composition is in the form of a microparticle formulation and comprises one or more polylactide-co-glycolide polymers (PLGAs).

### Claim 13 (depends on 1)

A combination comprising a therapeutically effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof, and one or more therapeutically active agents.

### Claim 14 (depends on 1)

A method for the treatment of tendon injury, the method comprising administering to a subject in need thereof a compound according to claim 1 or a pharmaceutically acceptable salt thereof.

### Claim 15 (depends on 1)

A method for the treatment of ligament injury, the method comprising administering to a subject in need thereof a compound according to claim 1 or a pharmaceutically acceptable salt thereof.

### Claim 16 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof, which is 4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-((1s,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)benzenesulfonamide.

### Claim 17 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof, which is 4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-(3,3-difluorocyclobutyl)-3-methylbenzenesulfonamide.

### Claim 18 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof, which is 4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-N-((1s,3s)-3-hydroxy-3-(trifluoromethyl)cyclobutyl)-N,3-dimethylbenzenesulfonamide.

### Claim 19 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof, which is 4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-(1,1-dioxidothietan-3-yl)benzenesulfonamide.

### Claim 20 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof, which is 4-(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-chloro-N-phenylbenzenesulfonamide.

### Claim 21 (depends on 1)

The compound according to claim 1 or a pharmaceutically acceptable salt thereof, which is 1-((4(3-amino-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-methylphenyl)sulfonyl)-3-(trifluoromethyl)azetidin-3-ol.