Novel imidazo based heterocycles 机翻标题: 暂无翻译,请尝试点击翻译按钮。

公开号/公开日
WO2007028051 A2 2007-03-08 [WO200728051]WO2007028051 A3 2007-11-01 [WO200728051] / 2007-03-082007-11-01
申请号/申请日
2006WO-US34275 / 2006-09-01
发明人
BREINLINGER ERIC C;CALDERWOOD DAVID J;FRANK KRISTINE E;BETSCHMANN PATRICK;HIRST GAVIN C;MORYTKO MICHAEL J;DIXON RICHARD W;
申请人
ABBOTT LABORATORIES;
主分类号
IPC分类号
A01N-043/50
摘要
(WO200728051) The present invention is directed to novel imidazopyrazine and imidazopyrimidine compounds of formula (I), wherein the variables are as defined herein.  The compounds of formula (I) are useful as kinase inhibitors and as such would be useful in treating certain conditions and diseases, especially inflammatory conditions and diseases and proliferative disorders and conditions, for example, cancers.
机翻摘要
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地址
代理人
代理机构
;
优先权号
2005US-60714016 2005-09-02 2006US-60837560 2006-08-14
主权利要求
(WO200728051) What is claimed is: 1. A compound of formula (I),  (I) pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein Z is an optionally substituted aryl or heteroaryl; X and Y are each independently N, CR4or N-oxide, provided that X and Y cannot both be CR4or X and Y cannot both be N-oxide; A is N, CR4or N-oxide; R1and R10is each independently H, OH, F, Cl, Br, I, CF3, CN, OCF3, nitro or amino; or R1and R10is each independently selected from the optionally substituted group consisting of aryloxy, (CrC6)alkyl, (CrC6)alkoxy, (CrC6)alkyl-O-(C1-C6)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C3-C3)cycloalkyl, (C3-C3)cycloalkyl(CrC6)alkyl, heterocyclyl, aryl, -CO2(Ci-C6)alkyl, -CONR5R6, -SO2NR5R6, S0(n)alkyl, -NHCOR5, -NHSO2R5, -N((CrC4)alkyl)CORs, -N(CC1-C4)^yI)SO2R5, NR5R6, O(CrC6)alkyl-R7and (CrC6)alkylR7; Q is N(R2), O, S or is a bond; L is a bond, (CrC6)alkyl, C(O), -C(O)-O-, -C(O)-N(H)-, SO or SO2; R3is selected from the group consisting of H, -C(O)NR5R6, -NR2C(O)R5, -NR2C(O)2R5, C(O)OR2, R3is selected from the optionally substituted group consisting of aryl, heterocyclyl, heterocyclylalkylaryl, l,4-dioxaspiro[4.5]decane, azabicyclo[3.2.1]octane and azabicyclo[2.2.2] octane; or R3is selected from the optionally substituted group consisting of (CrC9)alkyl and (C3- C8)cycloalkyl; wherein the (Ci-C9)alkyl and (C3-C8)cycloalkyl are optionally substituted with one or more (CrC6)alkyl, (CrC6)alkyl-OR2,- OR2or N(R2)2; R2for each occurrence is independently H or (Q-GOalkyl; R4is H, OH, F, Cl, Br, I, CF3, CN, OCF3, nitro or amino; or R4is selected from optionally substituted group consisting of (Ci-C6)alkyl, (CrC6)alkoxy, aryloxy, (C2-C8)alkenyl, (C2-C8)alkynyl, heterocyclyl, aryl, -CONR5R6, -SO2NR5R6, -S0(n)alkyl, -NR2COR5, -NR2SO2R5, -NR5R6, -CO2(C1-C6)alkyl, -N((CrC4)alkyl)CO-R5, or -N((CrC4)alkyl)SO2-R5; R5and R6are each independently H, or are independently selected from the optionally substituted group consisting of (Ci-C6)alkyl, (Ci-C6)alkoxy, (C2-C6)hydroxyalkyl, (C2-C6)aminoalkyl, (C3- C8)cycloalkyl, aryl and heterocyclyl; or R5and R6are taken together with the N atom to which they are attached to form an optionally substituted heteroaryl or heterocyclyl ring; R7is CF3, NR5R6, OH, (Q-C6)alkoxy or optionally substituted (C3-C8)cycloalkyl; m is 0, 1 or 2; n is O, 1, 2; and p is 1, 2, 3 or 4. 2. The compound according to claim 1, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein Z is optionally substituted aryl. 3. The compound according to claim 2, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, R1is H, Cl, methoxy, methyl, ethyl, isopropyl, OCH(CH3)2, OCH2CF3, OCF3, OCH2-cyclopropyl, CH2-cyclopropyl, NHCH3, N(CH3)2, NH2, OCH2CH2OCH3, OCH2CH(CH3)2or cyclopropyl; R10Js H; X is N or N-oxide; Y is CR4; Z is optionally substituted naphthyl or optionally substituted phenyl wherein one or more substituents are selected from the group consisting of F, Cl, CF3and CH3; A is N; Q is N(R2); L is a bond, CH(CH3), (CrC4)alkyl or C(O); R3is selected from the optionally substituted group consisting of (C2-C5)alkyl, cyclopropyl, cyclopentyl and cyclohexyl wherein the alkyl, cyclopropyl, cyclopentyl and cyclohexyl are optionally substituted with one or more alkyl, OR2or N(R2)2; or R3is selected from NHC(O)R5or the optionally substituted group consisting of azepanyl, phenyl, piperidinyl, pyrimidinyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiopyranyl, thienyl, C(O)OR2, tetrahydropyranyl, l,4-dioxaspiro[4.5]decane, azabicyclo[2.2.2]octane, azabicyclo[3.2.1]octane, wherein one or more substituents are selected from the group consisting of alkyl, alkyl-OR2, OR2, NR2, S(O)2-CH3, C(O)CH3, C(O)OC(CH3)3, C(O)CH2OH, methyl, oxo and COOH; R2is H, methyl or t-butyl; R4is H, methyl, ethyl, OCH3or Cl; and R5is methyl or OC(CH3)3. 4. The compound according to claim 3, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein R1is H, methoxy, methyl, ethyl, isopropyl, OCH(CH3)2, OCH2CF3, OCH2-cyclopropyl, CH2- cyclopropyl, NHCH3, N(CH3)2, NH2, OCH2CH2OCH3or OCH2CH(CH3)2; X is N; Z is unsubstituted naphthyl or phenyl optionally substituted with one or more F, Cl, CF3or methyl; L is a bond, CH(CH3), or CH2; R3is selected from the optionally substituted group consisting of cyclopropyl, cyclopentyl, cyclohexyl and (C3-C5)alkyl wherein one or more substituents are selected from the group consisting of alkyl, alkyl-OR2, OR2and N(R2)2; or R3is selected from the optionally substituted group consisting of phenyl, piperidinyl, tetrahydropyranyl, tetrahydrothiopyranyl, thienyl, l,4-dioxaspiro[4.5]decane, azabicyclo[3.2.1]octane ,  wherein one or more substituents are selected from the group consisting of alkyl, alkylOR2, OR2, S(O)2-CH3, C(O)CH3, C(O)OC(CH3)3, C(O)CH2OH, methyl and COOH; R2is H or t-butyl; and R4is H, methyl or ethyl. 5. The compound according to claim 4, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein R1is H, methoxy, methyl, ethyl, OCH(CH3)2or CH2-cyclopropyl; Y is CH; Z is phenyl optionally substituted with one or more F, Cl, CF3or methyl; wherein the substituents can be meta, para or disubstituted ortho, para; R3is selected from the group consisting of unsubstituted cyclopropyl, unsubstituted phenyl, unsubstituted cyclopentyl, unsubstituted cyclohexyl, unsubstituted thienyl, ,OH V0HV (C3-C5)alkyl substituted with one or more alkyl, alkyl-OR2or OR2, and piperidinyl substituted with S(O)2-CH3, C(O)CH3, C(O)OC(CH3)3, C(O)CH2OH or COOH; and R2is H or t-butyl. 6. The compound according to claim 5, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein R1is H, methoxy, methyl, OCH(CHj)2or -CH2-cyclopropyl; Q is N(H); L is a bond or CH(CH3); and R3is selected from the group consisting of unsubstituted cyclopropyl, unsubstituted cyclopentyl, unsubstituted cyclohexyl, unsubstituted phenyl, > and piperidinyl wherein the piperidinyl is substituted with S(O)2-CH3or C(O)CH3. 7. The compound according to claim 6 pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein the compound is  A compound of formula (I),  (I) pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein Z is an optionally substituted aryl or heteroaryl; X and Y are each independently N, CR4or N-oxide, provided that X and Y cannot both be CR4or X and Y cannot both be N-oxide; A is N, CR4or N-oxide; R1and R10is each independently H, OH, F, Cl, Br, I, CF3, CN, OCF3, nitro or amino; or R1and R10is each independently selected from the optionally substituted group consisting of aryloxy, (CrC6)alkyl, (d-C6)alkoxy, (CrC6)alkyl-O-(CrC6)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl(CrC6)alkyl, heterocyclyl, aryl, -CO2(C1-C6)alkyl, -CONR5R6, -SO2NR5R6, S0(n)alkyl, -NHCOR5, -NHSO2R5, -N((CrC4)alky.l)COR5, -N((CrC4)alkyl)SO2R5, NR5R6, O(CrC6)alkyl-R7and (CrC6)alkylR7; Q is N(R2), O, S or is a bond; L is a bond, (CrC6)alkyl, C(O), -C(O)-O-, -C(O)-N(H)-, SO or SO2; R3is selected from the group consisting of H, -C(O)NR5R6, -NR2C(O)R5, -NR2C(O)2R5,  R3is selected from the optionally substituted group consisting of aryl, heterocyclyl, heterocyclylalkylaryl, l,4-dioxaspiro[4.5]decane, azabicyclo[3.2. ljoctane, azabicyclo[2.2.2]octane, (Ci-C9)alkyl and (C3-C8)cycloalkyl; wherein the (Q -Chalky 1 and (C3-C8)cycloalkyl are optionally substituted with one or more (Q-QOalkyl, (CrC6)alkyl-OR2, OR2or N(R2)2; R2for each occurrence is independently H or (CrC4)alkyl; R4is H, OH, F, Cl, Br, I, CF3, CN, OCF3, nitro or amino; or R4is selected from optionally substituted group consisting of (CrC6)alkyl, (Ci-C6)alkoxy, aryloxy, (CrC8)alkenyl, (C2-C8)alkynyl, heterocyclyl, aryl, -CONR5R6, -SO2NR5R6, -S0(n)alkyl, -NR2COR5, -NR2SO2R5, -NR5R6, -CO2(CrC6)alkyl, -N((CrC4)alkyl)CO-R5, or -N((C1-C4)alkyl)SO2-R5; R5and R6are each independently H, or are independently selected from the optionally substituted group consisting of (Cj-C6)alkyl, (Ci-C6)alkoxy, (C2-C6)hydroxyalkyl, (C2-C6)aminoalkyl, (C3- C8)cycloalkyl, aryl and heterocyclyl; or R5and R6are taken together with the N atom to which they are attached to form an optionally substituted heteroaryl or heterocyclyl ring; R7is CF3, NR5R6, OH, (CrC6)alkoxy or optionally substituted (C3-C8)cycloalkyl; m is O, 1 or 2; n is 0, 1, 2; and p is 1, 2, 3 or 4. 9. The compound according to claim 8, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein Z is optionally substituted aryl. 10. The compound according to claim 9, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, R1is H, methoxy, methyl, ethyl, isopropyl, OCH(CH3)2, OCH2CF3, OCH2-cyclopropyl, CH2- cyclopropyl, NHCH3, N(CH3)2, NH2, OCH2CH2OCH3, OCH2CH(CH3)2or cyclopropyl; R10Is H; X is N or N-oxide; Y is CR4; Z is optionally substituted naphthyl or optionally substituted phenyl wherein one or more substituents are selected from the group consisting of F, Cl, CF3and CH3; A is N; Q Js N(R2); L is a bond, CH(CH3), (CrC4)alkyl or C(O); R3is selected from the optionally substituted group consisting of (C2-C5)alkyl, cyclopropyl, cyclopentyl and cyclohexyl wherein the alkyl, cyclopropyl, cyclopentyl and cyclohexyl are optionally substituted with one or more alkyl, OR2or N(R2)2; or R3is selected from NHC(O)R5or the optionally substituted group consisting of azepanyl,phenyl, piperidinyl, pyrimidinyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiopyranyl, thienyl, tetrahydropyranyl, l,4-dioxaspiro[4.5]decane, azabicyclo[2.2.2]octane, azabicyclo[3.2.1] octane, wherein one or more substituents are selected from the group consisting of alkyl, alkyl-OR2, OR2, NR2, S(O)2-CH3, C(O)CH3, C(O)OC(CH3)3, C(O)CH2OH, methyl, oxo and COOH; R2is H, methyl or t-butyl; R4is H, ethyl , OCH3or Cl; and R5is methyl or OC(CH3)3. 11. The compound according to claim 10, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein R1is H, methoxy, methyl, ethyl, isopropyl, OCH(CH3)2, OCH2CF3, OCH2-cyclopropyl, CH2- cyclopropyl, NHCH3, N(CH3)2, NH2, OCH2CH2OCH3or OCH2CH(CH3)2; X is N; Z is unsubstituted naphthyl or phenyl optionally substituted with one or more F, Cl, CF3or methyl; L is a bond, CH(CH3), or CH2; R3is selected from the optionally substituted group consisting of cyclopropyl, cyclopentyl, cyclohexyl and (C3-C5)alkyl wherein one or more substituents are selected from the group consisting of alkyl, alkyl-OR2, OR2and N(R2)2; or R3is selected from the optionally substituted group consisting of phenyl, piperidinyl, tetrahydropyranyl, tetrahydrothiopyranyl, thienyl, l,4-dioxaspiro[4.5]decane and azabicyclo[3.2.1]octane or wherein one or more substituents are selected from the group consisting of alkyl, alkylOR2, OR2, S(O)2-CH3, C(O)CH3, C(O)OC(CHj)3, C(O)CH2OH, COOH and methyl; R2is H or t-butyl; and R4is H or ethyl. 12. The compound according to claim 11, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein R1is H, methoxy, methyl, ethyl, OCH(CH3)2or CH2-cyclopropyl; Y is CH; Z is phenyl optionally substituted with one or more F, Cl, CF3or methyl; wherein the substituents can be meta, para or disubstituted ortho, para; R3is selected from the group consisting of unsubstituted cyclopropyl, (C3-Cs)alkyl substituted with one or more alkyl, alkyl-OR2or OR2, unsubstituted phenyl, unsubstituted cyclopentyl, unsubstituted cyclohexyl, unsubstituted thienyl and piperidinyl substituted with S(O)2-CH3, C(O)CH3, C(O)OC(CH3)3, C(O)CH2OH or COOH,; and R2is H or t-butyl. 13. The compound according to claim 12, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein R1is H, methoxy, methyl, OCH(CH3)2or -CEk-cyclopropyl; Q is N(H); L is a bond or CH(CH3); and R3is selected from the group consisting of unsubstituted cyclopropyl, unsubstituted cyclopentyl, unsubstituted cyclohexyl, unsubstituted phenyl, and piperidinyl wherein the piperidinyl is substituted with S(O)2-CH3or C(O)CH3. 14. The compound according to claim 13 pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein the compound is  15. A compound of formula (I),  (D pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein Z is an optionally substituted aryl or heteroaryl; X and Y are each independently N, CR4or N-oxide, provided that X and Y cannot both be CR4or X and Y cannot both be N-oxide; A is N or CR4; R4is H, F, Cl, Br, I, CF3, CN, OCF3, (CrC6)alkyl, (CrC6)alkoxy, nitro, amino, aryloxy, (C2-C8)alkenyl, (C2-C8)alkynyl, heterocyclyl, aryl, -CONR5R6, -SO2NR5R6, -SO(n)alkyl, - NR2COR5, -NR2SO2R5, or -NR5R6; R1and R10is each independently H, F, Cl, Br, I, CF3, CN, OCF3, nitro, amino, aryloxy, (CrC6)alkyl, (CrC6)alkoxy, (C2-C8)alkenyl, (C2-C8)alkynyl, heterocyclyl, aryl, -CO2(C1-C6)alkyl, -CONR5R6, - SO2NR5R6, SO(n)alkyl, -NHCOR5, -NHSO2R5, -NC(C1-C4)alkyl)COR5, -N((CrC4)alkyl)SO2R5, or NR5R6; R5and R6are each independently H, (CrC6)alkyl, (C2-C6)hydroxyalkyl, (C2-C6)aminoalkyl, (C3-C8)cycloalkyl, aryl or heterocyclyl; or R5and R6are taken together with the N atom to which they are attached to form a heteroaryl or heterocyclyl ring; Q is N(R2), O, S or is a bond; R2is H or (CrC4)alkyl; L is a bond, (CrC4)alkyl, C(O), -C(O)-O-, -C(O)-N(H)- or SO2; R3is H, (CrC6)alkyl optionally substituted with one or more OR2or N(R2)2, (C3-C8)cycloalkyl optionally substituted with one or more OR2or N(R2)2, optionally substituted aryl, or optionally substituted heterocyclyl; and n is 0, 1, 2. 16. A compound according to claim 15, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein Z is selected from the optionally substituted group consisting of phenyl, naphthyl, azaindolyl, benzo(b)thienyl, benzimidazolyl, benzofuranyl, benzoxazolyl, benzothiazolyl, benzothiadiazolyl, benzothiophenyl, benzoxadiazolyl, furanyl, imidazolyl, imidazopyridinyl, indolyl, indolinyl, indazolyl, isoindolinyl, isoxazolyl, isothiazolyl, oxadiazolyl, oxazolyl, purinyl, pyranyl pyrazinyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrrolyl, pyrrolo[2,3-d]pyrimidinyl, pyrazolo[3,4-d]pyrimidinyl, quinolinyl, quinazolinyl, triazolyl, thiazolyl, tetrahydroindolyl, tetrazolyl, thiadiazolyl, thienyl, thiomorpholinyl, thiophenyl, triazolyl and tropanyl. 17. A compound according to claim 16, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein Z is optionally substituted with one or more substituents, each independently selected from the group consisting of F, Cl, Br, I, CF3, CN, OCF3, nitro, amino, aryloxy, (Ci-C6)alkyl, (Q- C5)alkoxy, (C2-C8)alkenyl, (C2-C8)alkynyl, heterocyclyl, aryl, -CONR5R6, -SO2NR5R6, -S0(n)alkyl, -NHCOR5, -NHSO2R5, -N((CrC4)alkyl)COR5, -NC(C1-C4)alkyl)SO2R5, or -NR5R6 . 18. A compound according to claim 17, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein Z is optionally substituted phenyl, naphthyl, furanyl or thiophenyl. 19. A compound according to claim 18, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein Z is phenyl or naphthyl optionally substituted with one or more substituents each independently selected from the group consisting of F, Cl, methyl, CF3, and OCF3. 20. A compound according to claim 19, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein Z is optionally substituted phenyl, substituted at either the meta- or para- position by F, Cl, methyl, CF3, and OCF3 . 21. A compound according to claim 18, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein R1is H or halo. 22. A compound according to claim 19, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein R10is H, halo or -NR5R6. 23. A compound according to claim 22, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein R10is H. 24. A compound according to claim 18, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein A is N. 25. A compound according to claim 18, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein R2is H. 26. A compound according to claim 18, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein L is a bond or CO. 27. A compound according to claim 18, pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, or pro-drugs thereof, wherein R3is selected from the optionally substituted group consisting of methyl, ethyl, propyl, isopropyl, butyl, iso-butyl, sec-butyl, tert- butyl, pentyl, isopentyl, hexyl, isohexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, - C(H)(CH3)phenyl, -C(H)(CH2CH3)phenyl, piperidinyl, N-acylpiperidinyl, tetrahydropyranyl, (C2- C5) alkyl, azabicyclo[2.2.2]octane, azabicyclo[3.2.1]octane, azepanyl l,4-dioxaspiro[4.5]decane, pyridinyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiopyranyl, thienyl, and NHC(O)R5 .
法律状态
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