# US 8,785,639 B2 · Substituted dihydropyrazolo[3,4-D]pyrrolo[2,3-B]pyridines and methods of use thereof

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- Number: US 8,785,639 B2
- Document ID: US8785639B2
- Status: Granted
- Kind: B2
- Application number: 12/958,291
- Filed: 2010-12-01
- Published: 2011-08-04
- Granted: 2014-07-22
- Earliest claimed: 2009-12-01
- Assignees: AbbVie Inc.
- Applicants: Neil Wishart; Maria A. Argiriadi; David J. Calderwood; Anna M. Ericsson; Kristine E. Frank; Dawn M. George; Eric R. Goedken; Michael Friedman; Nathan S. Josephsohn; Biqin C. Li; Michael J. Morytko; Jeffrey W. Voss; Lu Wang; Eric C. Breinlinger; Kelly D. Mullen; Gagandeep Somal; Michael Z Hoemann
- Inventors: Neil Wishart; Maria A. Argiriadi; David J. Calderwood; Anna M. Ericsson; Kristine E. Frank; Dawn M. George; Eric R. Goedken; Michael Friedman; Nathan S. Josephsohn; Biqin C. Li; Michael J. Morytko; Jeffrey W. Voss; Lu Wang; Eric C. Breinlinger; Kelly D. Mullen; Gagandeep Somal; Michael Z Hoemann
- Web page: https://patentgrep.com/patent/US8785639B2

## CPC

- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- C07F 9/06: without P—C bonds
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 35/00: Antineoplastic agents
- A61P 37/00: Drugs for immunological or allergic disorders
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 471/14: Ortho-condensed systems
- C07D 487/14: Ortho-condensed systems
- C07D 498/14: Ortho-condensed systems
- C07D 513/14: Ortho-condensed systems
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention provides a compound of Formula (Ie), pharmaceutically acceptable salts, or stereoisomers thereof wherein the variables are defined herein. The compounds of the invention are useful for treating immunological and oncological conditions.

## Claims

### Claim 1

A compound of formula (Ie)
or pharmaceutically acceptable salts, or stereoisomers thereof wherein
R1 is H, deuterium, halogen, CF3, CN, ORa, N(Ra)(Rb), OCF3, —C(O)—N(Ra)(Rb), —C(O)—ORa, —C(O)-optionally substituted (C1-C6)alkyl, —C(O)-optionally substituted (C3-C6)cycloalkyl, —C(O)-optionally substituted (C6-C10)aryl, —C(O)-optionally substituted (C1-C10)heteroaryl, —C(O)-optionally substituted (C1-C10)heterocyclyl, —S-optionally substituted (C1-C6)alkyl, —S(O)-optionally substituted (C1-C6)alkyl, —S(O)2-optionally substituted (C1-C6)alkyl, —S(O)2N(Ra)(Rb), optionally substituted (C1-C6)alkyl, optionally substituted (C1-C6)alkoxy, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted (C3-C10)cycloalkyl, optionally substituted azaindolyl, optionally substituted azepinyl, optionally substituted azetidinyl, optionally substituted benzo(b)thienyl, optionally substituted benzofuranyl, optionally substituted benzimidazolyl, optionally substituted benzoxazolyl, optionally substituted benzothiazolyl, optionally substituted benzothiadiazolyl, optionally substituted benzoxadiazolyl, optionally substituted 6,7-dihydro-5H-cyclopentapyrimidinyl, optionally substituted furanyl, optionally substituted imidazolyl, optionally substituted imidazopyridinyl, optionally substituted 5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazinyl, optionally substituted 5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazinyl, optionally substituted 5,6,7,8-tetrahydro[1,2,4]-triazolo[4,3-a]pyrazinyl, optionally substituted indazolyl, optionally substituted indolinyl, optionally substituted indolyl, optionally substituted isoindolinyl, optionally substituted isoxazolyl, optionally substituted isothiazolyl, optionally substituted morpholinyl, optionally substituted oxadiazolyl, optionally substituted oxazolyl, optionally substituted phenyl, optionally substituted piperazinyl, optionally substituted piperidinyl, optionally substituted purinyl, optionally substituted pyranyl, optionally substituted pyrazolo[3,4-d]pyrimidinyl, optionally substituted pyridinyl, optionally substituted pyrimidinyl, optionally substituted pyrrolidinyl, optionally substituted 6,7-dihydro-5H-pyrrolo[1,2-a]imidazolyl, optionally substituted pyrrolyl, optionally substituted pyrrolo[3,2-c]pyrimidinyl, optionally substituted pyrrolo[2,3-d]pyrimidinyl, optionally substituted pyrrolo[2,3-b]pyridinyl, optionally substituted octahydropyrrolo[3,4-c]pyrrolyl, optionally substituted quinazolinyl, optionally substituted quinolinyl, optionally substituted quinuclidinyl, optionally substituted quinoxalinyl, optionally substituted thiomorpholinyl, optionally substituted tetrahydropyranyl, optionally substituted tetrahydrofuranyl, optionally substituted tetrahydroindolyl, optionally substituted thiazolyl, optionally substituted thienyl, optionally substituted tetrazolyl, optionally substituted thiadiazolyl, optionally substituted [1,3,5]triazinyl, optionally substituted triazolyl, or optionally substituted tropanyl; or
R1 is —Z101-L1-Z102 wherein
Z101 is optionally substituted (C1-C6)alkylene, optionally substituted (C1-C10)heterocyclylene, or optionally substituted (C6-C10)arylene;
L1 is —CH2C(O), —C(O)—, —C(O)CH2—, —N(Ra)—, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)—, -optionally substituted (C1-C4)alkylene-C(O)N(Ra)—, —C(O)N(Ra)—, —N(Ra)C(O)—, —C(O)N(Ra)-optionally substituted (C1-C4)alkylene-, —N(Ra)C(O)-optionally substituted (C1-C4)alkylene-, —C(O)N(Ra)-optionally substituted (C1-C4)alkylene-C(O), —N(Ra)C(O)-optionally substituted (C1-C4)alkylene-C(O)—, —C(O)-optionally substituted (C1-C4)alkylene-N(Ra)C(O)—, —C(O)-optionally substituted (C1-C4)alkylene-C(O)N(Ra)—, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)—, —N(Ra)C(O)-optionally substituted (C1-C4)alkylene, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-C(O)N(Ra)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-N(Ra)S(O)2—, -optionally substituted (C1-C4)alkylene-S(O)2N(Ra)—, —N(Ra)S(O)2CH2—, —S(O)2N(Ra)-optionally substituted (C1-C4)alkylene-, —C(O)N(Ra)S(O)2—, —S(O)2N(Ra)C(O)—, —S(O)2N(Ra)—, —N(Ra)S(O)2—, —O—(C1-C4)alkylene-, (C1-C6)alkylene-O—, —C(O)N(Ra)—(C1-C6)alkylene-C(O)—, or —C(O)—(C1-C6)alkylene-N(Ra)C(O)—;
Z102 is H, —CN, —N(Ra)(Rb), —ORa, optionally substituted (C1-C6)alkyl, optionally substituted (C1-C4)alkoxy, optionally substituted (C3-C10)cycloalkyl, optionally substituted (C6-C10)aryl, optionally substituted (C1-C10)heteroaryl, optionally substituted (C1-C10)heterocyclyl, optionally substituted bridged (C5-C12)cycloalkyl, or optionally substituted bridged (C2-C10)heterocyclyl;
R2 is H, deuterium, halogen, CF3, CN, ORa, N(Ra)(Rb), OCF3, —C(O)-optionally substituted (C1-C6)alkyl, —C(O)-optionally substituted (C3-C6)cycloalkyl, —S-optionally substituted (C1-C6)alkyl, —S(O)2-optionally substituted (C1-C6)alkyl, —S(O)2N(Ra)(Rb), optionally substituted (C1-C6)alkoxy, —C(O)N(Ra)(Rb), —S(O)2-optionally substituted (C1-C6)alkyl, optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted (C3-C10)cycloalkyl, optionally substituted (C6-C10)aryl, optionally substituted (C1-C10)heteroaryl, or optionally substituted (C1-C10)heterocyclyl;
R3 is H or methyl;
R5 is H, deuterium, N(Ra)(Rb), halogen, CN, CF3, ORa, optionally substituted (C1-C6)alkyl, OCF3, —C(O)-optionally substituted (C1-C6)alkyl, —C(O)-optionally substituted (C3-C6)cycloalkyl, —S-optionally substituted (C1-C6)alkyl, —S(O)-optionally substituted (C1-C6)alkyl, —S(O)2-optionally substituted (C1-C6)alkyl, —S(O)2N(Ra)(Rb), optionally substituted (C1-C6)alkyl, or optionally substituted (C1-C6)alkoxy;
R6 is H, deuterium, halogen, CF3, CN, —C(O)—N(Ra)(Rb), —C(O)—ORa, —C(O)-optionally substituted (C1-C6)alkyl, —C(O)-optionally substituted (C3-C6)cycloalkyl, —C(O)-optionally substituted (C6-C10)aryl, —C(O)-optionally substituted (C1-C10)heteroaryl, —C(O)-optionally substituted (C1-C10)heterocyclyl, —S-optionally substituted (C1-C6)alkyl, —S(O)-optionally substituted (C1-C6)alkyl, —S(O)2-optionally substituted (C1-C6)alkyl, —S(O)2N(Ra)(Rb), optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted (C3-C10)cycloalkyl, optionally substituted (C1-C10)heteroaryl, optionally substituted (C1-C10) heterocyclyl, or optionally substituted (C6-C10)aryl;
or
R6 is —Z201-L2-Z202 wherein
Z201 is optionally substituted (C1-C6)alkylene, optionally substituted (C1-C10)heteroarylene, optionally substituted (C1-C10)heterocyclylene, or optionally substituted (C6-C10)arylene;
L2 is a bond, optionally substituted (C1-C4)alkylene, —CH2C(O), —C(O)—, —C(O)CH2—, —N(Ra)—, —O—, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)—, -optionally substituted (C1-C4)alkylene-C(O)N(Ra)—, —C(O)N(Ra)—, —N(Ra)C(O)—, —C(O)N(Ra)S(O)2—, —S(O)2N(Ra)C(O)—, —C(O)N(Ra)-optionally substituted (C1-C4)alkylene-, —N(Ra)C(O)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-C(O)N(Ra)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-N(Ra)S(O)2—, -optionally substituted (C1-C4)alkylene-S(O)2N(Ra)—, —N(Ra)S(O)2CH2—, —S(O)2N(Ra)-optionally substituted (C1-C4)alkylene-, —S(O)2—, —S(O)2N(Ra)—, —N(Ra)S(O)2—, —(C1-C4)alkylene-O—, or —O—(C1-C4)alkylene-;
Z202 is H, —CN, —N(Ra)(Rb), —ORa, optionally substituted (C1-C6)alkyl, optionally substituted (C1-C4)alkoxy, optionally substituted (C3-C10)cycloalkyl, optionally substituted (C6-C10)aryl, optionally substituted (C1-C10)heteroaryl, optionally substituted (C1-C10)heterocyclyl, optionally substituted bridged (C5-C12)cycloalkyl, or optionally substituted bridged (C2-C10)heterocyclyl;
R7 is H, deuterium, optionally substituted-(CH2)n—P(═O)(ORa)(ORa), optionally substituted —(CH2)n—O—P(═O)(ORa)(ORa), optionally substituted-(CH2)n—P(═O)(ORa)(Ra), or —CH═CH—P(═O)(ORa)(ORa);
Ra and Rb are each independently H, deuterium, an optionally substituted (C1-C10)alkyl, optionally substituted (C2-C10)alkenyl, optionally substituted (C2-C10)alkynyl, an optionally substituted (C1-C10)alkyl-O—(C1-C10)alkyl, optionally substituted (C3-C10)cycloalkyl, an optionally substituted (C6-C10)aryl, optionally substituted (C1-C10)heteroaryl, optionally substituted (C1-C10)heterocyclyl, optionally substituted —(C1-C6)alkylene-(C3-C10)cycloalkyl, an optionally substituted —(C1-C6)alkylene-(C6-C10)aryl, optionally substituted —(C1-C6)alkylene-(C1-C10)heteroaryl, or optionally substituted —(C1-C6)alkylene-(C1-C10)heterocyclyl;
Re for each occurrence is independently a bond, an optionally substituted (C1-C10)alkylene, an optionally substituted (C2-C10)alkenylene, an optionally substituted (C2-C10)alkynylene, an optionally substituted —(C1-C10)alkylene-O—(C1-C10)alkylene group, an optionally substituted (C3-C10)cycloalkylene, an optionally substituted (C6-C10)arylene, an optionally substituted (C1-C10)heteroarylene, or an optionally substituted (C1-C10)heterocyclylene; and
n is 1, 2 or 3;
wherein the optional substituent is selected from the group consisting of: (C1-C8)alkyl groups, (C2-C8)alkenyl groups, (C2-C8)alkynyl groups, (C3-C10)cycloalkyl groups, halogen, halogenated (C1-C8)alkyl groups, —OH, —S—(C1-C8)alkyl groups, —SH, —NH(C1-C8)alkyl groups, —N((C1-C8)alkyl)2 groups, —NH2, —C(O)NH2, —C(O)NH(C1-C8)alkyl groups, —C(O)N((C1-C8)alkyl)2, —NHC(O)H, —NHC(O)(C1-C8)alkyl groups, —NHC(O)(C3-C8)cycloalkyl groups, —N((C1-C8)alkyl)C(O)H, —N((C1-C8)alkyl)C(O)(C1-C8)alkyl groups, —NHC(O)NH2, —NHC(O)NH(C1-C8)alkyl groups, —N((C1-C8)alkyl)C(O)NH2 groups, —NHC(O)N((C1-C8)alkyl)2 groups, —N((C1-C8)alkyl)C(O)N((C1-C8)alkyl)2 groups, —N((C1-C8)alkyl)C(O)NH((C1-C8)alkyl), —C(O)H, —C(O)(C1-C8)alkyl groups, —CN, —NO2, —S(O)(C1-C8)alkyl groups, —S(O)2N((C1-C8)alkyl)2 groups, —S(O)2NH(C1-C8)alkyl groups, —S(O)2NH(C3-C8)cycloalkyl groups, —S(O)2NH2 groups, —NHS(O)2(C1-C8)alkyl groups, —N((C1-C8)alkyl)S(O)2(C1-C8)alkyl groups, —(C1-C8)alkyl-O—(C1-C8)alkyl groups, —O—(C1-C8)alkyl-O—(C1-C8)alkyl groups, —C(O)OH, —C(O)O(C1-C8)alkyl groups, NHOH, NHO(C1-C8)alkyl groups, —O-halogenated (C1-C8)alkyl groups, —S(O)2-halogenated (C1-C8)alkyl groups, —S-halogenated (C1-C8)alkyl groups, —(C1-C6) heterocyclyl, —(C1-C6) heteroaryl, -phenyl, —NHC(O)O—(C1-C6)alkyl groups, —N((C1-C6)alkyl)C(O)O—(C1-C6)alkyl groups, —C(═NH)—(C1-C6)alkyl groups, —C(═NOH)—(C1-C6)alkyl groups, and —C(═N—O—(C1-C6)alkyl)-(C1-C6)alkyl groups;
provided that R1 and R6 are not both H.

### Claim 2 (depends on 1)

The compound of claim 1 wherein
R1 is H, halogen, CF3, CN, OH, N(Ra)(Rb), OCF3, —C(O)-optionally substituted (C1-C6)alkyl, —C(O)-optionally substituted (C3-C6)cycloalkyl, —S-optionally substituted (C1-C6)alkyl, —S(O)2-optionally substituted (C1-C6)alkyl, —S(O)2N(Ra)(Rb), optionally substituted (C1-C6)alkoxy, optionally substituted azaindolyl, optionally substituted azepinyl, optionally substituted azetidinyl, optionally substituted benzo(b)thienyl, optionally substituted benzofuranyl, optionally substituted benzimidazolyl, optionally substituted benzoxazolyl, optionally substituted benzothiazolyl, optionally substituted benzothiadiazolyl, optionally substituted benzoxadiazolyl, optionally substituted 6,7-dihydro-5H-cyclopentapyrimidinyl, optionally substituted furanyl, optionally substituted imidazolyl, imidazopyridinyl, 5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazinyl, 5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazinyl, 5,6,7,8-tetrahydro[1,2,4]-triazolo[4,3-a]pyrazinyl, optionally substituted indazolyl, optionally substituted indolinyl, optionally substituted indolyl, optionally substituted isoindolinyl, optionally substituted isoxazolyl, optionally substituted isothiazolyl, optionally substituted morpholinyl, optionally substituted oxadiazolyl, optionally substituted oxazolyl, optionally substituted phenyl, optionally substituted piperazinyl, optionally substituted piperidinyl, optionally substituted purinyl, optionally substituted pyranyl, optionally substituted pyrazolo[3,4-d]pyrimidinyl, optionally substituted pyridinyl, optionally substituted pyrimidinyl, optionally substituted pyrrolidinyl, 6,7-dihydro-5H-pyrrolo[1,2-a]imidazolyl, optionally substituted pyrrolyl, optionally substituted pyrrolo[3,2-c]pyrimidinyl, optionally substituted pyrrolo[2,3-d]pyrimidinyl, optionally substituted pyrrolo[2,3-b]pyridinyl, optionally substituted octahydropyrrolo[3,4-c]pyrrolyl, optionally substituted quinazolinyl, optionally substituted quinolinyl, optionally substituted quinuclidinyl, optionally substituted quinoxalinyl, optionally substituted thiomorpholinyl, optionally substituted tetrahydropyranyl, optionally substituted tetrahydrofuranyl, optionally substituted tetrahydroindolyl, optionally substituted thiazolyl, optionally substituted thienyl, optionally substituted tetrazolyl, optionally substituted thiadiazolyl, optionally substituted [1,3,5]triazinyl, optionally substituted triazolyl, or optionally substituted tropanyl; or
R1 is —Z101-L1-Z102 wherein
Z101 is optionally substituted (C1-C6)alkylene, optionally substituted (C1-C10)heterocyclylene, or optionally substituted (C6-C10)arylene;
L1 is —CH2C(O), —C(O)—, —C(O)CH2—, N(Ra)—, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)—, -optionally substituted (C1-C4)alkylene-C(O)N(Ra)—, —C(O)N(Ra)—, —N(Ra)C(O)—, —C(O)N(Ra)-optionally substituted (C1-C4)alkylene-, —N(Ra)C(O)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)—, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-C(O)N(Ra)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-N(Ra)S(O)2—, -optionally substituted (C1-C4)alkylene-S(O)2N(Ra)—, —N(Ra)S(O)2CH2—, —S(O)2N(Ra)-optionally substituted (C1-C4)alkylene-, —S(O)2N(Ra)—, —N(Ra)S(O)2— or —O—(C1-C4)alkylene-; and
Z102 is —N(Ra)(Rb), -optionally substituted (C1-C4)alkyl, optionally substituted (C1-C4)alkoxy, optionally substituted (C1-C10)heteroaryl, or optionally substituted (C1-C10)heterocyclyl.

### Claim 3 (depends on 2)

The compound of claim 2 wherein R1 is H, halogen, CF3, CN, OH, N(Ra)(Rb), OCF3, —C(O)-optionally substituted (C1-C6)alkyl, —C(O)-optionally substituted (C3-C6)cycloalkyl, —S-optionally substituted (C1-C6)alkyl, —S(O)2-optionally substituted (C1-C6)alkyl, —S(O)2N(Ra)(Rb), optionally substituted (C1-C6)alkoxy, optionally substituted benzofuranyl, optionally substituted benzo[b]thienyl, optionally substituted furanyl, optionally substituted imidazolyl, imidazopyridinyl, 5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazinyl, 5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazinyl, 5,6,7,8-tetrahydro[1,2,4]-triazolo[4,3-a]pyrazinyl, optionally substituted indazolyl, optionally substituted indolinyl, optionally substituted indolyl, optionally substituted isoxazolyl, optionally substituted oxadiazolyl, optionally substituted oxazolyl, optionally substituted phenyl, optionally substituted pyrazolo[3,4-d]pyrimidinyl, optionally substituted pyridinyl, optionally substituted pyrimidinyl, optionally substituted pyrrolyl, optionally substituted octahydropyrrolo[3,4-c]pyrrolyl, optionally substituted pyrrolo[2,3-c]pyridinyl, optionally substituted quinolinyl, optionally substituted thiazolyl, optionally substituted thienyl, or optionally substituted tetrazolyl; or
R1 is —Z101-L1-Z102 wherein
Z101 is optionally substituted (C1-C6)alkylene, optionally substituted (C1-C10)heterocyclylene, or optionally substituted (C6-C10) arylene;
L1 is —CH2C(O), —C(O)—, —C(O)CH2—, N(Ra)—, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)—, -optionally substituted (C1-C4)alkylene-C(O)N(Ra)—, —C(O)N(Ra)—, —N(Ra)C(O)—, —C(O)N(Ra)-optionally substituted (C1-C4)alkylene-, —N(Ra)C(O)-optionally substituted (C1-C4)alkylene-, —C(O)N(Ra)-optionally substituted (C1-C4)alkylene-C(O), —N(Ra)C(O)-optionally substituted (C1-C4)alkylene-C(O)—, —C(O)-optionally substituted (C1-C4)alkylene-N(Ra)C(O)—, —C(O)-optionally substituted (C1-C4)alkylene-C(O)N(Ra)—, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-C(O)N(Ra)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-N(Ra)S(O)2—, -optionally substituted (C1-C4)alkylene-S(O)2N(Ra)—, —N(Ra)S(O)2CH2—, —S(O)2N(Ra)-optionally substituted (C1-C4)alkylene-, —C(O)N(Ra)S(O)2—, —S(O)2N(Ra)C(O—), —S(O)2N(Ra)—, —N(Ra)S(O)2— or —O—(C1-C4)alkylene-; and
Z102 is, —N(Ra)(Rb), -optionally substituted (C1-C4)alkyl, optionally substituted (C1-C4)alkoxy, optionally substituted (C1-C10)heteroaryl, or optionally substituted (C1-C10)heterocyclyl.

### Claim 4 (depends on 3)

The compound of claim 3 wherein Z101 is optionally substituted phenyl.

### Claim 5 (depends on 4)

The compound of claim 4 wherein Z102 is —N(Ra)(Rb), -optionally substituted (C1-C4)alkyl, optionally substituted morpholinyl, optionally substituted piperazinyl, optionally substituted piperidinyl, or optionally substituted pyrrolidinyl.

### Claim 6 (depends on 1)

The compound of claim 1 wherein R2 is H, halogen, CF3, CN, ORa, N(Ra)(Rb), OCF3, —C(O)-optionally substituted (C1-C6)alkyl, —C(O)-optionally substituted (C3-C6)cycloalkyl, —S-optionally substituted (C1-C6)alkyl, —S(O)2-optionally substituted (C1-C6)alkyl, —S(O)2N(Ra)(Rb), optionally substituted (C1-C6)alkyl, optionally substituted (C1-C6)alkoxy, —C(O)N(Ra)(Rb), optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted (C3-C10)cycloalkyl, optionally substituted azetidinyl, optionally substituted morpholinyl, optionally substituted piperazinyl, optionally substituted piperidinyl, optionally substituted pyranyl, optionally substituted pyrrolidinyl, optionally substituted thiomorpholinyl, optionally substituted tetrahydropyranyl, optionally substituted tetrahydrofuranyl, optionally substituted tetrahydroindolyl, optionally substituted tetrahydropyridinyl or optionally substituted tropanyl.

### Claim 7 (depends on 1)

The compound of claim 1 wherein R6 is optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C3-C6)cycloalkyl, optionally substituted dihydrobenzofuranyl, optionally substituted benzo[b]thienyl, optionally substituted furanyl, optionally substituted indolyl, optionally substituted isoquinolinyl, optionally substituted phenyl, optionally substituted piperidinyl, optionally substituted pyridinyl, optionally substituted pyrido[3,2-b]oxazin-3-(4H)-one, optionally substituted pyrimidinyl, optionally substituted pyrazolyl, optionally substituted quinolinyl, optionally substituted quinoxalinyl, optionally substituted tetrahydropyridinyl, or optionally substituted thienyl;
or
R6 is —Z201-L2-Z202 wherein
Z201 is optionally substituted (C1-C6)alkylene, optionally substituted phenyl, optionally substituted piperidinyl, optionally substituted pyrazolyl, optionally substituted thienyl, or optionally substituted tetrhydropyridinyl;
L2 is a bond, —CH2C(O)—, —C(O)CH2, —C(O)—, —C(O)N(Ra)—, —N(Ra)C(O), —S(O)2, optionally substituted (C1-C6)alkylene, -optionally substituted (C1-C4)alkylene-S(O)2N(Ra)—, -optionally substituted (C1-C4)alkylene-N(Ra)S(O)2—, —S(O)2N(Ra)-optionally substituted (C1-C4)alkylene-, or —O—(C1-C4)alkylene-; and
Z202 is —CN, —N(Ra)(Rb), —ORa, optionally substituted (C1-C6)alkyl, optionally substituted (C3-C6)cycloalkyl, optionally substituted morpholinyl, optionally substituted oxetanyl, optionally substituted piperazinyl or optionally substituted piperidinyl.

### Claim 8

A compound of formula (Ie)
or pharmaceutically acceptable salts, or stereoisomers thereof wherein
R1 is H, deuterium, halogen, CF3, CN, ORa, N(Ra)(Rb), OCF3, —C(O)—N(Ra)(Rb), —C(O)—ORa, —C(O)-optionally substituted (C1-C6)alkyl, —C(O)-optionally substituted (C3-C6)cycloalkyl, —C(O)-optionally substituted (C6-C10)aryl, —C(O)-optionally substituted (C1-C10)heteroaryl, —C(O)-optionally substituted (C1-C10)heterocyclyl, —S-optionally substituted (C1-C6)alkyl, —S(O)-optionally substituted (C1-C6)alkyl, —S(O)2-optionally substituted (C1-C6)alkyl, —S(O)2N(Ra)(Rb), optionally substituted (C1-C6)alkyl, optionally substituted (C1-C6)alkoxy, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted (C3-C10)cycloalkyl, optionally substituted (C1-C10)heteroaryl, optionally substituted (C1-C10) heterocyclyl, or optionally substituted (C6-C10)aryl; or
R1 is —Z101-L1-Z102 wherein
Z101 is optionally substituted (C1-C6)alkylene, optionally substituted (C1-C10)heteroarylene, optionally substituted (C1-C10)heterocyclylene, or optionally substituted (C6-C10)arylene;
L1 is a bond, optionally substituted (C1-C4)alkylene, —CH2C(O), —C(O)—, —C(O)CH2—, —N(Ra)—, —O—, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)—, -optionally substituted (C1-C4)alkylene-C(O)N(Ra)—, —C(O)N(Ra)—, —N(Ra)C(O)—, —C(O)N(Ra)-optionally substituted (C1-C4)alkylene-, —N(Ra)C(O)-optionally substituted (C1-C4)alkylene-, —C(O)N(Ra)-optionally substituted (C1-C4)alkylene-C(O), —N(Ra)C(O)-optionally substituted (C1-C4)alkylene-C(O)—, —C(O)-optionally substituted (C1-C4)alkylene-N(Ra)C(O)—, —C(O)-optionally substituted (C1-C4)alkylene-C(O)N(Ra)—, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)—, —N(Ra)C(O)-optionally substituted (C1-C4)alkylene, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-C(O)N(Ra)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-N(Ra)S(O)2—, -optionally substituted (C1-C4)alkylene-S(O)2N(Ra)—, —N(Ra)S(O)2CH2—, —S(O)2N(Ra)-optionally substituted (C1-C4)alkylene-, —C(O)N(Ra)S(O)2—, —S(O)2N(Ra)C(O)—, —S(O)2—, —S(O)2N(Ra)—, —N(Ra)S(O)2—, —O—(C1-C4)alkylene-, (C1-C6)alkylene-O—, —C(O)N(Ra)—(C1-C6)alkylene-C(O)—, or —C(O)—(C1-C6)alkylene-N(Ra)C(O)—;
Z102 is H, —CN, —N(Ra)(Rb), —ORa, optionally substituted (C1-C6)alkyl, optionally substituted (C1-C4)alkoxy, optionally substituted (C3-C10)cycloalkyl, optionally substituted (C6-C10)aryl, optionally substituted (C1-C10)heteroaryl, optionally substituted (C1-C10)heterocyclyl, optionally substituted bridged (C1-C12)cycloalkyl, or optionally substituted bridged (C2-C10)heterocyclyl;
R2 is H, deuterium, halogen, CF3, CN, ORa, N(Ra)(Rb), OCF3, —C(O)-optionally substituted (C1-C6)alkyl, —C(O)-optionally substituted (C3-C6)cycloalkyl, —S-optionally substituted (C1-C6)alkyl, —S(O)2-optionally substituted (C1-C6)alkyl, —S(O)2N(Ra)(Rb), optionally substituted (C1-C6)alkoxy, —C(O)N(Ra)(Rb), —S(O)2-optionally substituted (C1-C6)alkyl, optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted (C3-C10)cycloalkyl, optionally substituted (C6-C10)aryl, optionally substituted (C1-C10)heteroaryl, or optionally substituted (C1-C10)heterocyclyl;
R3 is -A-D-E-G, wherein:
A is a bond;
D is an optionally substituted nitrogen-containing (C2-C10)heterocyclylene;
E is —Re—C(O)—Re-, where in all cases, E is linked to a nitrogen atom in D;
G is H;
Re for each occurrence is independently a bond, an optionally substituted (C1-C10)alkylene, an optionally substituted (C2-C10)alkenylene, an optionally substituted (C2-C10)alkynylene, an optionally substituted —(C1-C10)alkylene-O—(C1-C10)alkylene group, an optionally substituted (C3-C10)cycloalkylene, an optionally substituted (C6-C10)arylene, an optionally substituted (C1-C10)heteroarylene, or an optionally substituted (C1-C10)heterocyclylene;
R5 is H, deuterium, N(Ra)(Rb), halogen, CN, CF3, ORa, optionally substituted (C1-C6)alkyl, OCF3, —C(O)-optionally substituted (C1-C6)alkyl, —C(O)-optionally substituted (C3-C6)cycloalkyl, —S-optionally substituted (C1-C6)alkyl, —S(O)-optionally substituted (C1-C6)alkyl, —S(O)2-optionally substituted (C1-C6)alkyl, —S(O)2N(Ra)(Rb), optionally substituted (C1-C6)alkyl, or optionally substituted (C1-C6)alkoxy;
R6 is H, deuterium, halogen, CF3, CN, —C(O)—N(Ra)(Rb), —C(O)—ORa, —C(O)-optionally substituted (C1-C6)alkyl, —C(O)-optionally substituted (C3-C6)cycloalkyl, —C(O)-optionally substituted (C6-C10)aryl, —C(O)-optionally substituted (C1-C10)heteroaryl, —C(O)-optionally substituted (C1-C10)heterocyclyl, —S-optionally substituted (C1-C6)alkyl, —S(O)-optionally substituted (C1-C6)alkyl, —S(O)2-optionally substituted (C1-C6)alkyl, —S(O)2N(Ra)(Rb), optionally substituted (C1-C6)alkyl, optionally substituted (C2-C6)alkenyl, optionally substituted (C2-C6)alkynyl, optionally substituted (C3-C10)cycloalkyl, optionally substituted (C1-C10)heteroaryl, optionally substituted (C1-C10)heterocyclyl, or optionally substituted (C6-C10)aryl;
or
R6 is —Z201-L2-Z202 wherein
Z201 is optionally substituted (C1-C6)alkylene, optionally substituted (C1-C10)heteroarylene, optionally substituted (C1-C10)heterocyclylene, or optionally substituted (C6-C10)arylene;
L2 is a bond, optionally substituted (C1-C4)alkylene, —CH2C(O), —C(O)—, —C(O)CH2—, —N(Ra)—, —O—, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)—, -optionally substituted (C1-C4)alkylene-C(O)N(Ra)—, —C(O)N(Ra)—, —N(Ra)C(O)—, —C(O)N(Ra)S(O)2—, —S(O)2N(Ra)C(O)—, —C(O)N(Ra)-optionally substituted (C1-C4)alkylene-, —N(Ra)C(O)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-N(Ra)C(O)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-C(O)N(Ra)-optionally substituted (C1-C4)alkylene-, -optionally substituted (C1-C4)alkylene-N(Ra)S(O)2—, -optionally substituted (C1-C4)alkylene-S(O)2N(Ra)—, —N(Ra)S(O)2CH2—, —S(O)2N(Ra)-optionally substituted (C1-C4)alkylene-, —S(O)2—, —S(O)2N(Ra)—, —N(Ra)S(O)2—, —(C1-C4)alkylene-O—, or —O—(C1-C4)alkylene-;
Z202 is H, —CN, —N(Ra)(Rb), —ORa, optionally substituted (C1-C6)alkyl, optionally substituted (C1-C4)alkoxy, optionally substituted (C3-C10)cycloalkyl, optionally substituted (C6-C10)aryl, optionally substituted (C1-C10)heteroaryl, optionally substituted (C1-C10)heterocyclyl, optionally substituted bridged (C5-C12)cycloalkyl, or optionally substituted bridged (C2-C10)heterocyclyl;
R7 is H, deuterium, optionally substituted-(CH2)n—P(═O)(ORa)(ORa), optionally substituted —(CH2)n—O—P(═O)(ORa)(ORa), optionally substituted-(CH2)n—P(═O)(ORa)(Ra), or —CH═CH—P(═O)(ORa)(ORa);
Ra and Rb are each independently H, deuterium, an optionally substituted (C1-C10)alkyl, optionally substituted (C2-C10)alkenyl, optionally substituted (C2-C10)alkynyl, an optionally substituted (C1-C10)alkyl-O—(C1-C10)alkyl, optionally substituted (C3-C10)cycloalkyl, an optionally substituted (C6-C10)aryl, optionally substituted (C1-C10)heteroaryl, optionally substituted (C1-C10)heterocyclyl, optionally substituted —(C1-C6)alkylene-(C3-C10)cycloalkyl, an optionally substituted —(C1-C6)alkylene-(C6-C10)aryl, optionally substituted —(C1-C6)alkylene-(C1-C10)heteroaryl, or optionally substituted —(C1-C6)alkylene-(C1-C10)heterocyclyl;
n is 1, 2 or 3;
wherein the optional substituent is selected from the group consisting of: (C1-C8)alkyl groups, (C2-C8)alkenyl groups, (C2-C8)alkynyl groups, (C3-C10)cycloalkyl groups, halogen, halogenated (C1-C8)alkyl groups, —O—(C1-C8)alkyl groups, —OH, —S—(C1-C8)alkyl groups, —SH, —NH(C1-C8)alkyl groups, —N((C1-C8)alkyl)2 groups, —NH2, —C(O)NH2, —C(O)NH(C1-C8)alkyl groups, —C(O)N((C1-C8)alkyl)2, —NHC(O)H, —NHC(O)(C1-C8)alkyl groups, —NHC(O)(C3-C8)cycloalkyl groups, —N((C1-C8)alkyl)C(O)H, —N((C1-C8)alkyl)C(O)(C1-C8)alkyl groups, —NHC(O)NH2, —NHC(O)NH(C1-C8)alkyl groups, —N((C1-C8)alkyl)C(O)NH2 groups, —NHC(O)N((C1-C8)alkyl)2 groups, —N((C1-C8)alkyl)C(O)N((C1-C8)alkyl)2 groups, —N((C1-C8)alkyl)C(O)NH((C1-C8)alkyl), —C(O)H, —C(O)(C1-C8)alkyl groups, —CN, —NO2, —S(O)(C1-C8)alkyl groups, —S(O)2(C1-C8)alkyl groups, —S(O)2N((C1-C8)alkyl)2 groups, —S(O)2NH(C1-C8)alkyl groups, —S(O)2NH(C3-C8)cycloalkyl groups, —S(O)2NH2 groups, —NHS(O)2(C1-C8)alkyl groups, —N((C1-C8)alkyl)S(O)2(C1-C8)alkyl groups, —(C1-C8)alkyl-O—(C1-C8)alkyl groups, —O—(C1-C8)alkyl-O—(C1-C8)alkyl groups, —C(O)OH, —C(O)O(C1-C8)alkyl groups, NHOH, NHO(C1-C8)alkyl groups, —O-halogenated (C1-C8)alkyl groups —S(O)2-halogenated (C1-C8)alkyl groups, —S-halogenated (C1-C8)alkyl groups, —(C1-C6) heterocyclyl, —(C1-C6) heteroaryl, -phenyl, —NHC(O)O—(C1-C6)alkyl groups, —N((C1-C6)alkyl)C(O)O—(C1-C6)alkyl groups, —C(═NH)—(C1-C6)alkyl groups, —C(═NOH)—(C1-C6)alkyl groups, and —C(═N—O—(C1-C6)alkyl)-(C1-C6)alkyl groups;
provided that R1 and R6 are not both H.

### Claim 9

A compound selected from
2-(4-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenyl)propan-2-ol,
4-(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzyl)morpholine,
7-(5-fluoro-1-methyl-1H-indol-3-yl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
7-(benzofuran-3-yl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
7-(5-methoxy-1H-indol-3-yl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
1-methyl-7-(1-methyl-1H-indol-3-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
N-(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzyl)acetamide,
N-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzamide,
3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzonitrile,
7-(3-fluorophenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
2-(5-methoxy-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-1-yl)-1-morpholinoethanone,
2-(5-methoxy-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-1-yl)acetic acid,
4-(2-(5-methoxy-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-1-yl)ethyl)morpholine,
2-(5-methoxy-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-1-yl)ethanol,
(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenyl)methanamine,
2-(5-methoxy-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-1-yl)-N,N-dimethylethanamine,
2-(dimethylamino)-N-(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzyl)acetamide,
3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-N-(2-morpholinoethyl)benzamide,
N-(3-methoxypropyl)-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzamide,
3-methoxy-N-(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzyl)propanamide,
N-(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzyl)methanesulfonamide,
(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenyl)(pyrrolidin-1-yl)methanone,
2-(5-methoxy-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-1-yl)-1-(4-methylpiperazin-1-yl)ethanone,
N-(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzyl)-3-morpholinopropanamide,
7-(6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
N-methyl-2-(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenyl)acetamide,
N-(3-hydroxy-2,2-dimethylpropyl)-2-(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenyl)acetamide,
N-(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzyl)pentanamide,
1-(dimethylamino)-3-(5-methoxy-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-1-yl)propan-2-ol,
N-(3-methoxypropyl)-2-(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenyl)acetamide,
2-(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenyl)-N-(2-(4-methylpiperazin-1-yl)ethyl)acetamide,
1-methyl-7-(pyridin-4-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
1-methyl-7-(pyridin-3-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
2-(5-methoxy-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-1-yl)-N,N-dimethylacetamide,
2-(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenyl)-N-(2-morpholinoethyl)acetamide,
N,N-dimethyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzenesulfonamide,
2-(4-(8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenyl)propan-2-ol,
8-ethyl-1-methyl-7-(3-(methylsulfonyl)phenyl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
2-(5-methoxy-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-1-yl)-N-(2-methoxyethyl)acetamide,
N-(2-(dimethylamino)ethyl)-2-(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenyl)acetamide,
N-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzenesulfonamide,
3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzenesulfonamide,
N-(2-hydroxyethyl)-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzenesulfonamide,
7-(4-methoxyphenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
3-(5-methoxy-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-1-yl)propane-1,2-diol,
N,N-dimethyl-2-(4-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenoxy)ethanamine,
4-(2-(4-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenoxy)ethyl)morpholine,
4-(3-(4-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenoxy)propyl)morpholine,
1-methyl-7-(quinolin-5-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
1-methyl-7-(quinolin-6-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
1-methyl-7-(quinoxalin-6-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
3-(8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-N-(2-morpholinoethyl)benzamide,
8-ethyl-1-methyl-7-(1-methyl-1H-indol-5-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
8-ethyl-1-methyl-7-(1-methyl-1H-indol-4-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
4-(4-(8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenyl)morpholine,
7-(1,3-dimethyl-1H-pyrazol-4-yl)-8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
7-(1,5-dimethyl-1H-pyrazol-4-yl)-8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
8-ethyl-7-(5-methoxy-1-methyl-1H-indol-3-yl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
4-(8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-N-(2-morpholinoethyl)benzamide,
3-(8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-N-propylbenzamide,
N,N-diethyl-3-(8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzenesulfonamide,
3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-N-(2-morpholinoethyl)benzenesulfonamide,
N-(2-methoxyethyl)-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzenesulfonamide,
8-ethyl-7-(4-methoxyphenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
8-ethyl-1-methyl-7-(1-methyl-1H-pyrazol-4-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
4-(2-(4-(8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenoxy)ethyl)morpholine,
8-ethyl-7-(4-(2-methoxyethoxy)phenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
2-(4-(8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenoxy)-N,N-dimethylethanamine,
1-methyl-7-(1-methyl-1H-indol-5-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
2-(4-(8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenyl)propan-2-amine,
7-(2,4-dimethylphenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
7-(1-isopropyl-5-methoxy-1H-indol-3-yl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
7-(1-isopropyl-1H-indol-3-yl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
1-methyl-7-(1-methyl-1H-pyrrolo[3,2-c]pyridin-3-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
7-(5-methoxy-1-methyl-1H-indazol-3-yl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
2-(1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-5-yl)propan-2-ol,
1-methyl-7-(3-methyl-4-(4-methylpiperazin-1-yl)phenyl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-N-(2-morpholinoethyl)-1H-indole-5-carboxamide,
N-(1-hydroxy-2-methylpropan-2-yl)-1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-5-carboxamide,
1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-5-carboxylic acid,
N-(3-hydroxy-2,2-dimethylpropyl)-1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-5-carboxamide,
7-(1,5-dimethyl-1H-indol-3-yl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
1-methyl-7-(1H-pyrrol-2-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-pyrrol-1-yl)-1-(4-methylpiperazin-1-yl)ethanone,
N-(3-ethoxypropyl)-2-(2-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-pyrrol-1-yl)acetamide,
2-(2-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-pyrrol-1-yl)-1-morpholinoethanone,
N-(2-hydroxyethyl)-1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-5-carboxamide,
2-(2-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-pyrrol-1-yl)acetic acid,
N-(2-(dimethylamino)ethyl)-1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-5-carboxamide,
(4-(hydroxymethyl)piperidin-1-yl)(1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-5-yl)methanone,
N,N,1-trimethyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-5-carboxamide,
N-(3-hydroxy-2,2-dimethylpropyl)-N,1-dimethyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-5-carboxamide,
1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-6-carboxylic acid,
4-(2-(1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-5-yloxy)ethyl)morpholine,
1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-N-(2-(4-methylpiperazin-1-yl)-2-oxoethyl)-1H-indole-5-carboxamide,
N,N,1-trimethyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-6-carboxamide,
N-(3-hydroxy-2,2-dimethylpropyl)-1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-6-carboxamide,
N-(1-hydroxy-2-methylpropan-2-yl)-1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-6-carboxamide,
1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-N-(2-morpholinoethyl)-1H-indole-6-carboxamide,
1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-N-(methylsulfonyl)-1H-indole-5-carboxamide,
2-(4-(8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-3-yl)phenyl)propan-2-ol,
7-(5-methoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
1-methyl-7-(5-methyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
3-(4-methoxyphenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
7-(5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
7-(5-methoxy-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
3-(4-methoxyphenyl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
7-(4-(2-hydroxypropan-2-yl)phenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine-8-carbonitrile,
1-methyl-3-(4-(methylthio)phenyl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
8-bromo-3-(4-methoxyphenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
1-methyl-3-(4-(methylsulfonyl)phenyl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
1-(4-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-3-yl)phenyl)ethanone,
2-(4-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-3-yl)phenyl)propan-2-ol,
3-(4-methoxyphenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine-8-carbonitrile,
8-ethyl-3-(3-fluoro-4-methoxyphenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
8-ethyl-1-methyl-3-(quinoxalin-6-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
8-ethyl-3-(4-isopropoxyphenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
N-cyclopropyl-4-(8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-3-yl)benzamide,
(4-(8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-3-yl)phenyl)methanol,
4-(8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-3-yl)benzenesulfonamide,
8-ethyl-1-methyl-3-(thiophen-3-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
8-ethyl-3-(4-methoxyphenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
8-ethyl-1-methyl-3-(pyridin-3-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
8-ethyl-1-methyl-3-(1-methyl-1H-pyrazol-4-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
8-ethyl-1-methyl-3-(3,4,5-trimethoxyphenyl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine,
or pharmaceutically acceptable salts or stereoisomers thereof.