IP Library › Granted Patent US 8,785,639

Granted Patent B2

US 8,785,639 · App. 12/958,291 · Granted Jul 22, 2014

Substituted dihydropyrazolo[3,4-D]pyrrolo[2,3-B]pyridines and methods of use thereof

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Quick Facts

Patent No.: US 8,785,639
App. No.: 12/958,291
Granted: Jul 22, 2014
Kind: B2

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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 (195)

1. A compound of formula (Ie)

or pharmaceutically acceptable salts, or stereoisomers thereof wherein

R 1 is H, deuterium, halogen, CF 3 , CN, OR a , N(R a )(R b ), OCF 3 , —C(O)—N(R a )(R b ), —C(O)—OR a , —C(O)-optionally substituted (C 1 -C 6 )alkyl, —C(O)-optionally substituted (C 3 -C 6 )cycloalkyl, —C(O)-optionally substituted (C 6 -C 10 )aryl, —C(O)-optionally substituted (C 1 -C 10 )heteroaryl, —C(O)-optionally substituted (C 1 -C 10 )heterocyclyl, —S-optionally substituted (C 1 -C 6 )alkyl, —S(O)-optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 -optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 N(R a )(R b ), optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 1 -C 6 )alkoxy, optionally substituted (C 2 -C 6 )alkenyl, optionally substituted (C 2 -C 6 )alkynyl, optionally substituted (C 3 -C 10 )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

R 1 is —Z 101 -L 1 -Z 102 wherein

Z 101 is optionally substituted (C 1 -C 6 )alkylene, optionally substituted (C 1 -C 10 )heterocyclylene, or optionally substituted (C 6 -C 10 )arylene;

L 1 is —CH 2 C(O), —C(O)—, —C(O)CH 2 —, —N(R a )—, -optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)—, -optionally substituted (C 1 -C 4 )alkylene-C(O)N(R a )—, —C(O)N(R a )—, —N(R a )C(O)—, —C(O)N(R a )-optionally substituted (C 1 -C 4 )alkylene-, —N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene-, —C(O)N(R a )-optionally substituted (C 1 -C 4 )alkylene-C(O), —N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene-C(O)—, —C(O)-optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)—, —C(O)-optionally substituted (C 1 -C 4 )alkylene-C(O)N(R a )—, -optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)—, —N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene, -optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene-, -optionally substituted (C 1 -C 4 )alkylene-C(O)N(R a )-optionally substituted (C 1 -C 4 )alkylene-, -optionally substituted (C 1 -C 4 )alkylene-N(R a )S(O) 2 —, -optionally substituted (C 1 -C 4 )alkylene-S(O) 2 N(R a )—, —N(R a )S(O) 2 CH 2 —, —S(O) 2 N(R a )-optionally substituted (C 1 -C 4 )alkylene-, —C(O)N(R a )S(O) 2 —, —S(O) 2 N(R a )C(O)—, —S(O) 2 N(R a )—, —N(R a )S(O) 2 —, —O—(C 1 -C 4 )alkylene-, (C 1 -C 6 )alkylene-O—, —C(O)N(R a )—(C 1 -C 6 )alkylene-C(O)—, or —C(O)—(C 1 -C 6 )alkylene-N(R a )C(O)—;

Z 102 is H, —CN, —N(R a )(R b ), —OR a , optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 1 -C 4 )alkoxy, optionally substituted (C 3 -C 10 )cycloalkyl, optionally substituted (C 6 -C 10 )aryl, optionally substituted (C 1 -C 10 )heteroaryl, optionally substituted (C 1 -C 10 )heterocyclyl, optionally substituted bridged (C 5 -C 12 )cycloalkyl, or optionally substituted bridged (C 2 -C 10 )heterocyclyl;

R 2 is H, deuterium, halogen, CF 3 , CN, OR a , N(R a )(R b ), OCF 3 , —C(O)-optionally substituted (C 1 -C 6 )alkyl, —C(O)-optionally substituted (C 3 -C 6 )cycloalkyl, —S-optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 -optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 N(R a )(R b ), optionally substituted (C 1 -C 6 )alkoxy, —C(O)N(R a )(R b ), —S(O) 2 -optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 2 -C 6 )alkenyl, optionally substituted (C 2 -C 6 )alkynyl, optionally substituted (C 3 -C 10 )cycloalkyl, optionally substituted (C 6 -C 10 )aryl, optionally substituted (C 1 -C 10 )heteroaryl, or optionally substituted (C 1 -C 10 )heterocyclyl;

R 3 is H or methyl;

R 5 is H, deuterium, N(R a )(R b ), halogen, CN, CF 3 , OR a , optionally substituted (C 1 -C 6 )alkyl, OCF 3 , —C(O)-optionally substituted (C 1 -C 6 )alkyl, —C(O)-optionally substituted (C 3 -C 6 )cycloalkyl, —S-optionally substituted (C 1 -C 6 )alkyl, —S(O)-optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 -optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 N(R a )(R b ), optionally substituted (C 1 -C 6 )alkyl, or optionally substituted (C 1 -C 6 )alkoxy;

R 6 is H, deuterium, halogen, CF 3 , CN, —C(O)—N(R a )(R b ), —C(O)—OR a , —C(O)-optionally substituted (C 1 -C 6 )alkyl, —C(O)-optionally substituted (C 3 -C 6 )cycloalkyl, —C(O)-optionally substituted (C 6 -C 10 )aryl, —C(O)-optionally substituted (C 1 -C 10 )heteroaryl, —C(O)-optionally substituted (C 1 -C 10 )heterocyclyl, —S-optionally substituted (C 1 -C 6 )alkyl, —S(O)-optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 -optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 N(R a )(R b ), optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 2 -C 6 )alkenyl, optionally substituted (C 2 -C 6 )alkynyl, optionally substituted (C 3 -C 10 )cycloalkyl, optionally substituted (C 1 -C 10 )heteroaryl, optionally substituted (C 1 -C 10 ) heterocyclyl, or optionally substituted (C 6 -C 10 )aryl;

R 6 is —Z 201 -L 2 -Z 202 wherein

Z 201 is optionally substituted (C 1 -C 6 )alkylene, optionally substituted (C 1 -C 10 )heteroarylene, optionally substituted (C 1 -C 10 )heterocyclylene, or optionally substituted (C 6 -C 10 )arylene;

L 2 is a bond, optionally substituted (C 1 -C 4 )alkylene, —CH 2 C(O), —C(O)—, —C(O)CH 2 —, —N(R a )—, —O—, -optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)—, -optionally substituted (C 1 -C 4 )alkylene-C(O)N(R a )—, —C(O)N(R a )—, —N(R a )C(O)—, —C(O)N(R a )S(O) 2 —, —S(O) 2 N(R a )C(O)—, —C(O)N(R a )-optionally substituted (C 1 -C 4 )alkylene-, —N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene-, -optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene-, -optionally substituted (C 1 -C 4 )alkylene-C(O)N(R a )-optionally substituted (C 1 -C 4 )alkylene-, -optionally substituted (C 1 -C 4 )alkylene-N(R a )S(O) 2 —, -optionally substituted (C 1 -C 4 )alkylene-S(O) 2 N(R a )—, —N(R a )S(O) 2 CH 2 —, —S(O) 2 N(R a )-optionally substituted (C 1 -C 4 )alkylene-, —S(O) 2 —, —S(O) 2 N(R a )—, —N(R a )S(O) 2 —, —(C 1 -C 4 )alkylene-O—, or —O—(C 1 -C 4 )alkylene-;

Z 202 is H, —CN, —N(R a )(R b ), —OR a , optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 1 -C 4 )alkoxy, optionally substituted (C 3 -C 10 )cycloalkyl, optionally substituted (C 6 -C 10 )aryl, optionally substituted (C 1 -C 10 )heteroaryl, optionally substituted (C 1 -C 10 )heterocyclyl, optionally substituted bridged (C 5 -C 12 )cycloalkyl, or optionally substituted bridged (C 2 -C 10 )heterocyclyl;

R 7 is H, deuterium, optionally substituted-(CH 2 ) n —P(═O)(OR a )(OR a ), optionally substituted —(CH 2 ) n —O—P(═O)(OR a )(OR a ), optionally substituted-(CH 2 ) n —P(═O)(OR a )(R a ), or —CH═CH—P(═O)(OR a )(OR a );

R a and R b are each independently H, deuterium, an optionally substituted (C 1 -C 10 )alkyl, optionally substituted (C 2 -C 10 )alkenyl, optionally substituted (C 2 -C 10 )alkynyl, an optionally substituted (C 1 -C 10 )alkyl-O—(C 1 -C 10 )alkyl, optionally substituted (C 3 -C 10 )cycloalkyl, an optionally substituted (C 6 -C 10 )aryl, optionally substituted (C 1 -C 10 )heteroaryl, optionally substituted (C 1 -C 10 )heterocyclyl, optionally substituted —(C 1 -C 6 )alkylene-(C 3 -C 10 )cycloalkyl, an optionally substituted —(C 1 -C 6 )alkylene-(C 6 -C 10 )aryl, optionally substituted —(C 1 -C 6 )alkylene-(C 1 -C 10 )heteroaryl, or optionally substituted —(C 1 -C 6 )alkylene-(C 1 -C 10 )heterocyclyl;

R e for each occurrence is independently a bond, an optionally substituted (C 1 -C 10 )alkylene, an optionally substituted (C 2 -C 10 )alkenylene, an optionally substituted (C 2 -C 10 )alkynylene, an optionally substituted —(C 1 -C 10 )alkylene-O—(C 1 -C 10 )alkylene group, an optionally substituted (C 3 -C 10 )cycloalkylene, an optionally substituted (C 6 -C 10 )arylene, an optionally substituted (C 1 -C 10 )heteroarylene, or an optionally substituted (C 1 -C 10 )heterocyclylene; and

n is 1, 2 or 3;

wherein the optional substituent is selected from the group consisting of: (C 1 -C 8 )alkyl groups, (C 2 -C 8 )alkenyl groups, (C 2 -C 8 )alkynyl groups, (C 3 -C 10 )cycloalkyl groups, halogen, halogenated (C 1 -C 8 )alkyl groups, —OH, —S—(C 1 -C 8 )alkyl groups, —SH, —NH(C 1 -C 8 )alkyl groups, —N((C 1 -C 8 )alkyl) 2 groups, —NH 2 , —C(O)NH 2 , —C(O)NH(C 1 -C 8 )alkyl groups, —C(O)N((C 1 -C 8 )alkyl) 2 , —NHC(O)H, —NHC(O)(C 1 -C 8 )alkyl groups, —NHC(O)(C 3 -C 8 )cycloalkyl groups, —N((C 1 -C 8 )alkyl)C(O)H, —N((C 1 -C 8 )alkyl)C(O)(C 1 -C 8 )alkyl groups, —NHC(O)NH 2 , —NHC(O)NH(C 1 -C 8 )alkyl groups, —N((C 1 -C 8 )alkyl)C(O)NH 2 groups, —NHC(O)N((C 1 -C 8 )alkyl) 2 groups, —N((C 1 -C 8 )alkyl)C(O)N((C 1 -C 8 )alkyl) 2 groups, —N((C 1 -C 8 )alkyl)C(O)NH((C 1 -C 8 )alkyl), —C(O)H, —C(O)(C 1 -C 8 )alkyl groups, —CN, —NO 2 , —S(O)(C 1 -C 8 )alkyl groups, —S(O) 2 N((C 1 -C 8 )alkyl) 2 groups, —S(O) 2 NH(C 1 -C 8 )alkyl groups, —S(O) 2 NH(C 3 -C 8 )cycloalkyl groups, —S(O) 2 NH 2 groups, —NHS(O) 2 (C 1 -C 8 )alkyl groups, —N((C 1 -C 8 )alkyl)S(O) 2 (C 1 -C 8 )alkyl groups, —(C 1 -C 8 )alkyl-O—(C 1 -C 8 )alkyl groups, —O—(C 1 -C 8 )alkyl-O—(C 1 -C 8 )alkyl groups, —C(O)OH, —C(O)O(C 1 -C 8 )alkyl groups, NHOH, NHO(C 1 -C 8 )alkyl groups, —O-halogenated (C 1 -C 8 )alkyl groups, —S(O) 2 -halogenated (C 1 -C 8 )alkyl groups, —S-halogenated (C 1 -C 8 )alkyl groups, —(C 1 -C 6 ) heterocyclyl, —(C 1 -C 6 ) heteroaryl, -phenyl, —NHC(O)O—(C 1 -C 6 )alkyl groups, —N((C 1 -C 6 )alkyl)C(O)O—(C 1 -C 6 )alkyl groups, —C(═NH)—(C 1 -C 6 )alkyl groups, —C(═NOH)—(C 1 -C 6 )alkyl groups, and —C(═N—O—(C 1 -C 6 )alkyl)-(C 1 -C 6 )alkyl groups;

provided that R 1 and R 6 are not both H.

2. The compound of claim 1 wherein

R 1 is H, halogen, CF 3 , CN, OH, N(R a )(R b ), OCF 3 , —C(O)-optionally substituted (C 1 -C 6 )alkyl, —C(O)-optionally substituted (C 3 -C 6 )cycloalkyl, —S-optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 -optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 N(R a )(R b ), optionally substituted (C 1 -C 6 )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

R 1 is —Z 101 -L 1 -Z 102 wherein

Z 101 is optionally substituted (C 1 -C 6 )alkylene, optionally substituted (C 1 -C 10 )heterocyclylene, or optionally substituted (C 6 -C 10 )arylene;

L 1 is —CH 2 C(O), —C(O)—, —C(O)CH 2 —, N(R a )—, -optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)—, -optionally substituted (C 1 -C 4 )alkylene-C(O)N(R a )—, —C(O)N(R a )—, —N(R a )C(O)—, —C(O)N(R a )-optionally substituted (C 1 -C 4 )alkylene-, —N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene-, -optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)—, -optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene-, -optionally substituted (C 1 -C 4 )alkylene-C(O)N(R a )-optionally substituted (C 1 -C 4 )alkylene-, -optionally substituted (C 1 -C 4 )alkylene-N(R a )S(O) 2 —, -optionally substituted (C 1 -C 4 )alkylene-S(O) 2 N(R a )—, —N(R a )S(O) 2 CH 2 —, —S(O) 2 N(R a )-optionally substituted (C 1 -C 4 )alkylene-, —S(O) 2 N(R a )—, —N(R a )S(O) 2 — or —O—(C 1 -C 4 )alkylene-; and

Z 102 is —N(R a )(R b ), -optionally substituted (C 1 -C 4 )alkyl, optionally substituted (C 1 -C 4 )alkoxy, optionally substituted (C 1 -C 10 )heteroaryl, or optionally substituted (C 1 -C 10 )heterocyclyl.

3. The compound of claim 2 wherein R 1 is H, halogen, CF 3 , CN, OH, N(R a )(R b ), OCF 3 , —C(O)-optionally substituted (C 1 -C 6 )alkyl, —C(O)-optionally substituted (C 3 -C 6 )cycloalkyl, —S-optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 -optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 N(R a )(R b ), optionally substituted (C 1 -C 6 )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

R 1 is —Z 101 -L 1 -Z 102 wherein

Z 101 is optionally substituted (C 1 -C 6 )alkylene, optionally substituted (C 1 -C 10 )heterocyclylene, or optionally substituted (C 6 -C 10 ) arylene;

L 1 is —CH 2 C(O), —C(O)—, —C(O)CH 2 —, N(R a )—, -optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)—, -optionally substituted (C 1 -C 4 )alkylene-C(O)N(R a )—, —C(O)N(R a )—, —N(R a )C(O)—, —C(O)N(R a )-optionally substituted (C 1 -C 4 )alkylene-, —N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene-, —C(O)N(R a )-optionally substituted (C 1 -C 4 )alkylene-C(O), —N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene-C(O)—, —C(O)-optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)—, —C(O)-optionally substituted (C 1 -C 4 )alkylene-C(O)N(R a )—, -optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene-, -optionally substituted (C 1 -C 4 )alkylene-C(O)N(R a )-optionally substituted (C 1 -C 4 )alkylene-, -optionally substituted (C 1 -C 4 )alkylene-N(R a )S(O) 2 —, -optionally substituted (C 1 -C 4 )alkylene-S(O) 2 N(R a )—, —N(R a )S(O) 2 CH 2 —, —S(O) 2 N(R a )-optionally substituted (C 1 -C 4 )alkylene-, —C(O)N(R a )S(O) 2 —, —S(O) 2 N(R a )C(O—), —S(O) 2 N(R a )—, —N(R a )S(O) 2 — or —O—(C 1 -C 4 )alkylene-; and

Z 102 is, —N(R a )(R b ), -optionally substituted (C 1 -C 4 )alkyl, optionally substituted (C 1 -C 4 )alkoxy, optionally substituted (C 1 -C 10 )heteroaryl, or optionally substituted (C 1 -C 10 )heterocyclyl.

4. The compound of claim 3 wherein Z 101 is optionally substituted phenyl.

5. The compound of claim 4 wherein Z 102 is —N(R a )(R b ), -optionally substituted (C 1 -C 4 )alkyl, optionally substituted morpholinyl, optionally substituted piperazinyl, optionally substituted piperidinyl, or optionally substituted pyrrolidinyl.

6. The compound of claim 1 wherein R 2 is H, halogen, CF 3 , CN, OR a , N(R a )(R b ), OCF 3 , —C(O)-optionally substituted (C 1 -C 6 )alkyl, —C(O)-optionally substituted (C 3 -C 6 )cycloalkyl, —S-optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 -optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 N(R a )(R b ), optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 1 -C 6 )alkoxy, —C(O)N(R a )(R b ), optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 2 -C 6 )alkenyl, optionally substituted (C 2 -C 6 )alkynyl, optionally substituted (C 3 -C 10 )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.

7. The compound of claim 1 wherein R 6 is optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 2 -C 6 )alkenyl, optionally substituted (C 3 -C 6 )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;

R 6 is —Z 201 -L 2 -Z 202 wherein

Z 201 is optionally substituted (C 1 -C 6 )alkylene, optionally substituted phenyl, optionally substituted piperidinyl, optionally substituted pyrazolyl, optionally substituted thienyl, or optionally substituted tetrhydropyridinyl;

L 2 is a bond, —CH 2 C(O)—, —C(O)CH 2 , —C(O)—, —C(O)N(R a )—, —N(R a )C(O), —S(O) 2 , optionally substituted (C 1 -C 6 )alkylene, -optionally substituted (C 1 -C 4 )alkylene-S(O) 2 N(R a )—, -optionally substituted (C 1 -C 4 )alkylene-N(R a )S(O) 2 —, —S(O) 2 N(R a )-optionally substituted (C 1 -C 4 )alkylene-, or —O—(C 1 -C 4 )alkylene-; and

Z 202 is —CN, —N(R a )(R b ), —OR a , optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 3 -C 6 )cycloalkyl, optionally substituted morpholinyl, optionally substituted oxetanyl, optionally substituted piperazinyl or optionally substituted piperidinyl.

8. A compound of formula (Ie)

or pharmaceutically acceptable salts, or stereoisomers thereof wherein

R 1 is —Z 101 -L 1 -Z 102 wherein

Z 101 is optionally substituted (C 1 -C 6 )alkylene, optionally substituted (C 1 -C 10 )heteroarylene, optionally substituted (C 1 -C 10 )heterocyclylene, or optionally substituted (C 6 -C 10 )arylene;

L 1 is a bond, optionally substituted (C 1 -C 4 )alkylene, —CH 2 C(O), —C(O)—, —C(O)CH 2 —, —N(R a )—, —O—, -optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)—, -optionally substituted (C 1 -C 4 )alkylene-C(O)N(R a )—, —C(O)N(R a )—, —N(R a )C(O)—, —C(O)N(R a )-optionally substituted (C 1 -C 4 )alkylene-, —N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene-, —C(O)N(R a )-optionally substituted (C 1 -C 4 )alkylene-C(O), —N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene-C(O)—, —C(O)-optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)—, —C(O)-optionally substituted (C 1 -C 4 )alkylene-C(O)N(R a )—, -optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)—, —N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene, -optionally substituted (C 1 -C 4 )alkylene-N(R a )C(O)-optionally substituted (C 1 -C 4 )alkylene-, -optionally substituted (C 1 -C 4 )alkylene-C(O)N(R a )-optionally substituted (C 1 -C 4 )alkylene-, -optionally substituted (C 1 -C 4 )alkylene-N(R a )S(O) 2 —, -optionally substituted (C 1 -C 4 )alkylene-S(O) 2 N(R a )—, —N(R a )S(O) 2 CH 2 —, —S(O) 2 N(R a )-optionally substituted (C 1 -C 4 )alkylene-, —C(O)N(R a) S(O) 2 —, —S(O) 2 N(R a )C(O)—, —S(O) 2 —, —S(O) 2 N(R a )—, —N(R a) S(O) 2 —, —O—(C 1 -C 4 )alkylene-, (C 1 -C 6 )alkylene-O—, —C(O)N(R a )—(C 1 -C 6 )alkylene-C(O)—, or —C(O)—(C 1 -C 6 )alkylene-N(R a )C(O)—;

Z 102 is H, —CN, —N(R a )(R b ), —OR a , optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 1 -C 4 )alkoxy, optionally substituted (C 3 -C 10 )cycloalkyl, optionally substituted (C 6 -C 10 )aryl, optionally substituted (C 1 -C 10 )heteroaryl, optionally substituted (C 1 -C 10 )heterocyclyl, optionally substituted bridged (C 1 -C 12 )cycloalkyl, or optionally substituted bridged (C 2 -C 10 )heterocyclyl;

R 3 is -A-D-E-G, wherein:

A is a bond;

D is an optionally substituted nitrogen-containing (C 2 -C 10 )heterocyclylene;

E is —R e —C(O)—R e -, where in all cases, E is linked to a nitrogen atom in D;

G is H;

R 6 is H, deuterium, halogen, CF 3 , CN, —C(O)—N(R a )(R b ), —C(O)—OR a , —C(O)-optionally substituted (C 1 -C 6 )alkyl, —C(O)-optionally substituted (C 3 -C 6 )cycloalkyl, —C(O)-optionally substituted (C 6 -C 10 )aryl, —C(O)-optionally substituted (C 1 -C 10 )heteroaryl, —C(O)-optionally substituted (C 1 -C 10 )heterocyclyl, —S-optionally substituted (C 1 -C 6 )alkyl, —S(O)-optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 -optionally substituted (C 1 -C 6 )alkyl, —S(O) 2 N(R a )(R b ), optionally substituted (C 1 -C 6 )alkyl, optionally substituted (C 2 -C 6 )alkenyl, optionally substituted (C 2 -C 6 )alkynyl, optionally substituted (C 3 -C 10 )cycloalkyl, optionally substituted (C 1 -C 10 )heteroaryl, optionally substituted (C 1 -C 10 )heterocyclyl, or optionally substituted (C 6 -C 10 )aryl;

R 6 is —Z 201 -L 2 -Z 202 wherein

n is 1, 2 or 3;

wherein the optional substituent is selected from the group consisting of: (C 1 -C 8 )alkyl groups, (C 2 -C 8 )alkenyl groups, (C 2 -C 8 )alkynyl groups, (C 3 -C 10 )cycloalkyl groups, halogen, halogenated (C 1 -C 8 )alkyl groups, —O—(C 1 -C 8 )alkyl groups, —OH, —S—(C 1 -C 8 )alkyl groups, —SH, —NH(C 1 -C 8 )alkyl groups, —N((C 1 -C 8 )alkyl) 2 groups, —NH 2 , —C(O)NH 2 , —C(O)NH(C 1 -C 8 )alkyl groups, —C(O)N((C 1 -C 8 )alkyl) 2 , —NHC(O)H, —NHC(O)(C 1 -C 8 )alkyl groups, —NHC(O)(C 3 -C 8 )cycloalkyl groups, —N((C 1 -C 8 )alkyl)C(O)H, —N((C 1 -C 8 )alkyl)C(O)(C 1 -C 8 )alkyl groups, —NHC(O)NH 2 , —NHC(O)NH(C 1 -C 8 )alkyl groups, —N((C 1 -C 8 )alkyl)C(O)NH 2 groups, —NHC(O)N((C 1 -C 8 )alkyl) 2 groups, —N((C 1 -C 8 )alkyl)C(O)N((C 1 -C 8 )alkyl) 2 groups, —N((C 1 -C 8 )alkyl)C(O)NH((C 1 -C 8 )alkyl), —C(O)H, —C(O)(C 1 -C 8 )alkyl groups, —CN, —NO 2 , —S(O)(C 1 -C 8 )alkyl groups, —S(O) 2 (C 1 -C 8 )alkyl groups, —S(O) 2 N((C 1 -C 8 )alkyl) 2 groups, —S(O) 2 NH(C 1 -C 8 )alkyl groups, —S(O) 2 NH(C 3 -C 8 )cycloalkyl groups, —S(O) 2 NH 2 groups, —NHS(O) 2 (C 1 -C 8 )alkyl groups, —N((C 1 -C 8 )alkyl)S(O) 2 (C 1 -C 8 )alkyl groups, —(C 1 -C 8 )alkyl-O—(C 1 -C 8 )alkyl groups, —O—(C 1 -C 8 )alkyl-O—(C 1 -C 8 )alkyl groups, —C(O)OH, —C(O)O(C 1 -C 8 )alkyl groups, NHOH, NHO(C 1 -C 8 )alkyl groups, —O-halogenated (C 1 -C 8 )alkyl groups —S(O) 2 -halogenated (C 1 -C 8 )alkyl groups, —S-halogenated (C 1 -C 8 )alkyl groups, —(C 1 -C 6 ) heterocyclyl, —(C 1 -C 6 ) heteroaryl, -phenyl, —NHC(O)O—(C 1 -C 6 )alkyl groups, —N((C 1 -C 6 )alkyl)C(O)O—(C 1 -C 6 )alkyl groups, —C(═NH)—(C 1 -C 6 )alkyl groups, —C(═NOH)—(C 1 -C 6 )alkyl groups, and —C(═N—O—(C 1 -C 6 )alkyl)-(C 1 -C 6 )alkyl groups;

provided that R 1 and R 6 are not both H.

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.

Assignments (4)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2013

From: ABBOTT LABORATORIES

To: ABBVIE INC.

Reel/Frame 030237/0588 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 23, 2012

From: HOEMANN, MICHAEL Z.

To: ABBOTT LABORATORIES

Reel/Frame 028836/0578 →

CORRECTIVE ASSIGNMENT TO CORRECT THE RECEIVING PARTY NAME CORRECTION FROM ABBOTT LABORTORIES TO ABBOTT LABORATORIES. PREVIOUSLY RECORDED ON REEL 026366 FRAME 0876. ASSIGNOR(S) HEREBY CONFIRMS THE RECEIVING PARTY NAME CORRECTION.. Recorded Jun 3, 2011

From: WISHART, NEIL; ARGIRIADI, MARIA A; CALDERWOOD, DAVID J; ERICSSON, ANNA M; FIAMENGO, BRYAN A; FRANK, KRISTINE E; FRIEDMAN, MICHAEL; GEORGE, DAWN M; GOEDKEN, ERIC R; JOSEPHSOHN, NATHAN S; LI, BIQIN C; MORYTKO, MICHAEL J; STEWART, KENT D; VOSS, JEFFREY W; WALLACE, GRIER A; WANG, LU; WOLLER, KEVIN R; BREINLINGER, ERIC C; MULLEN, KELLY D; SOMAL, GAGANDEEP

To: ABBOTT LABORATORIES

Reel/Frame 026390/0475 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 1, 2011

To: ABBOTT LABORTORIES

Reel/Frame 026366/0876 →