Pyrazolopyridines and analogs thereof 机翻标题: 暂无翻译,请尝试点击翻译按钮。

公开号/公开日
US2006100229 A1 2006-05-11 [US20060100229]US7544697 B2 2009-06-09 [US7544697] / 2006-05-112009-06-09
申请号/申请日
2004US-11097715 / 2004-10-01
发明人
HAYS DAVID S;DANIELSON MICHAEL E;GERSTER JOHN F;NIWAS SHRI;PRINCE RYAN B;KSHIRSAGAR TUSHAR A;HEPPNER PHILIP D;MOSER WILLIAM H;MOSEMAN JOAN T;RADMER MATTHEW R;KAVANAGH MAUREEN A;STRONG SARAH A;BONK JASON D;
申请人
3M INNOVATIVE PROPERTIES;
主分类号
IPC分类号
A01N-043/42A61K-031/44C07D-471/00C07D-491/00C07D-498/00C07D-513/00C07D-515/00
摘要
(US7544697) Pyrazolopyridin-4-amines, pyrazoloquinolin-4-amines, pyrazolonaphthyridin-4-amines, and 6,7,8,9-tetrahydropyrazoloquinolin-4-amines, pharmaceutical compositions containing the compounds, intermediates, methods of making, and methods of use of these compounds as immunomodulators, for inducing or inhibiting cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases, are disclosed.
机翻摘要
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地址
代理人
代理机构
;
优先权号
2003US-60508352 2003-10-03 2004US-60554680 2004-03-19 2004US-60603303 2004-08-20 2004WO-US32480 2004-10-01 2005US-11097715 2005-04-01
主权利要求
(US7544697) What is claimed is: 1.  A compound of the formula (I): wherein: RA and RB make a phenyl ring;  R' is selected from the group consisting of hydrogen and non-interfering substitutents;R'' is selected from the group consisting of:  -- R4, -- X -- R4, -- X -- Y -- R4, and -- X -- R5;X is selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, heteroarylene, and heterocyclylene wherein the alkylene, alkenylene, and alkynylene groups can be optionally interrupted or terminated by arylene, heteroarylene orheterocyclylene and optionally interrupted by one or more  -- O --  groups;Y is selected from the group consisting of:  -- O -- , -- S(O)0-2 -- , -- S(O)2 -- N(R8) -- , -- C(R6) -- , -- C(R6) -- O -- , -- O -- C(R6) -- , -- O -- C(O) -- O -- , -- N(R8)-Q-, -- C(R6) -- N(R8) -- , -- O -- C(R6) -- N(R8) -- , -- C(R6) -- N(OR9) -- , -- O -- N(R8)-Q-, -- O -- N.dbd.C(R4) -- , -- C(.dbd.N -- O -- R8) -- , -- C(.dbd.N -- O -- R8) -- NH -- , -- CH( -- N( -- O -- R8)-Q-R4) -- , R4 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkyiheteroarylenyl, and heterocyclyl wherein the alkyl, alkenyl, alkynyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkyiheteroarylenyl, and heterocyclyl groups can be unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, hydroxyalkyl, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, mercapto, cyano, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, heteroarylalkyleneoxy, heterocyclyl, amino, alkylamino, dialkylamino, (dialkylamino)alkyleneoxy, and in the case of alkyl, alkenyl, alkynyl, and heterocyclyl, oxo;R5 is selected from the group consisting of R6 is selected from the group consisting of .dbd.O and .dbd.S;R7 is C2-7 alkylene;  R8 is selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, hydroxyalkylenyl, arylalkylenyl, and heteroarylalkylenyl;R9 is selected from the group consisting of hydrogen and alkyl;R10 is C3-8 alkylene;A is selected from the group consisting of  -- O -- ,  -- C(O) -- ,  -- S(O)0-2 -- , and  -- N(R4) -- ;A' is selected from the group consisting of  -- O -- ,  -- S(O)0-2 -- ,  -- N(-Q-R4) -- , and  -- CH2 -- ;Q is selected from the group consisting of a bond,  -- C(R6) -- ,  -- C(R6) -- C(R6) -- ,  -- S(O)2 -- ,  -- C(R6) -- N(R8) -- W -- ,  -- S(O)2 -- N(R8) -- ,  -- C(R6) -- O -- ,  -- C(R6) -- S -- , and  -- C(R6) -- N(OR9) -- ;V is selected from the group consisting of  -- C(R6) -- ,  -- O -- C(R6) -- ,  -- N(R8) -- C(R6) -- , and  -- S(O)2 -- ;W is selected from the group consisting of a bond,  -- C(O) -- ;and  -- S(O)2 -- ;  and a and b are independently integers from 1 to 6 with the proviso that a+b is <= 7;  with the proviso that at least one of RA1, RB1, R1, or R2 is other than hydrogen;  and with the further proviso that when RA1 and RB1 form a fused benzene ring unsubstituted or substituted with chloro, and RI is hydrogen, then R2 is other than phenyl or phenyl substituted with methyl, methoxy, chloro, or fluoro; or a pharmaceutically acceptable salt thereof;  R''' is a non-interfering substitutent;  and    with the proviso that at least one of RA, RB, R', or R'' is other than hydrogen;  and with the further proviso that when RA and RB form a benzene ring unsubstituted or substituted with chloro, and R' is hydrogen, then R'' is other than phenyl or phenyl substituted with methyl, methoxy, chloro, or fluoro; or a pharmaceutically acceptable salt thereof. 2. A compound of the formula (II): wherein: RA1 and RB1 make a phenyl ring;  R1 is selected from the group consisting of:  -- R4, -- X -- R4, -- X -- Y -- R4, -- X -- Y -- X -- Y -- R4, and -- X -- R5;R2 is selected from the group consisting of:  -- R4, -- X -- R4, -- X -- Y -- R4, and -- X -- R5;X is selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, heteroarylene, and heterocyclylene wherein the alkylene, alkenylene, and alkynylene groups can be optionally interrupted or terminated by arylene, heteroarylene orheterocyclylene and optionally interrupted by one or more  -- O --  groups;Y is selected from the group consisting of:  -- O -- , -- S(O)0-2 -- , -- S(O)2 -- N(R8) -- , -- C(R6) -- , -- C(R6) -- O -- , -- O -- C(R6) -- , -- O -- C(O) -- O -- , -- N(R8)-Q-, -- C(R6) -- N(R8) -- , -- O -- C(R6) -- N(R8) -- , -- C(R6) -- N(OR9) -- , -- O -- N(R8)-Q-, -- O -- N.dbd.C(R4) -- , -- C(.dbd.N -- O -- R8) -- , -- C(.dbd.N -- O -- R8) -- NH -- , -- CH( -- N( -- O -- R8)-Q-R4) -- , Z is a bond or  -- O -- ;  R4 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkyiheteroarylenyl, and heterocyclyl wherein the alkyl, alkenyl, alkynyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkyiheteroarylenyl, and heterocyclyl groups can be unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, hydroxyalkyl, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, mercapto, cyano, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, heteroarylalkyleneoxy, heterocyclyl, amino, alkylamino, dialkylamino, (dialkylamino)alkyleneoxy, and in the case of alkyl, alkenyl, alkynyl, and heterocyclyl, oxo;R5 is selected from the group consisting of R6 is selected from the group consisting of .dbd.O and .dbd.S;R7 is C2-7 alkylene;R8 is selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, hydroxyalkylenyl, arylalkylenyl, and heteroarylalkylenyl;R9 is selected from the group consisting of hydrogen and alkyl;R10 is C3-8 alkylene;A is selected from the group consisting of  -- O -- ,  -- C(O) -- ,  -- S(O)0-2 -- , and  -- N(R4) -- ;A' is selected from the group consisting of  -- O -- ,  -- S(O)0-2 -- ,  -- N(-Q-R4) -- , and  -- CH2 -- ;Q is selected from the group consisting of a bond,  -- C(R6) -- ,  -- C(R6) -- C(R6) -- ,  -- S(O)2 -- ,  -- C(R6) -- N(R8) -- W -- ,  -- S(O)2 -- N(R8) -- ,  -- C(R6) -- O -- ,  -- C(R6) -- S -- , and  -- C(R6) -- N(OR9) -- ;V is selected from the group consisting of  -- C(R6) -- ,  -- O -- C(R6) -- ,  -- N(R8) -- C(R6) -- , and  -- S(O)2 -- ;W is selected from the group consisting of a bond,  -- C(O) -- , and  -- S(O)2 -- , anda and b are independently integers from 1 to 6 with the proviso that a+b is <= 7;  with the proviso that at least one of RA1, RB1, R1, or R2 is other than hydrogen;  and with the further proviso that when RA1 and RB1 form a fused benzene ring unsubstituted or substituted with chloro, and RI is hydrogen, then R2 is other than phenyl or phenyl substituted with methyl, methoxy, chloro, or fIuoro; or a pharmaceutically acceptable salt thereof. 3. A compound of the formula (III): wherein: R is selected from the group consisting of: halogen,hydroxy,alkyl,alkenyl,haloalkyl,alkoxy,alkylthio, and -- N(R9)2;R1 is selected from the group consisting of:  -- R4, -- X -- R4, -- X -- Y -- R4, -- X -- Y -- X -- Y -- R4, and -- X -- R5;R2 is selected from the group consisting of:  -- R4, -- X -- R4, -- X -- Y -- R4, and -- X -- R5;R3 is selected from the group consisting of: -Z-R4,-Z-X -- R4,-Z-X -- Y -- R4,-Z-X -- Y -- X -- Y -- R4, and-Z-X -- R5,n is 0;m is 0;  X is selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, heteroarylene, and heterocyclylene wherein the alkylene, alkenylene, and alkynylene groups can be optionally interrupted or terminated by arylene, heteroarylene or heterocyclylene and optionally interrupted by one or more  -- O --  groups;Y is selected from the group consisting of: -- O -- , -- S(O)0-2 -- , -- S(O)2 -- N(R8) -- , -- C(R6) -- , -- C(R6) -- O -- , -- O -- C(R6) -- , -- O -- C(O) -- O -- , -- N(R8)-Q-, -- C(R6) -- N(R8) -- , -- O -- C(R6) -- N(R8) -- , -- C(R6) -- N(OR9) -- , -- O -- N(R8)-Q-, -- O -- N.dbd.C(R4) -- , -- C(.dbd.N -- O -- R8) -- , -- C(.dbd.N -- O -- R8) -- NH -- , -- CH( -- N( -- O -- R8)-Q-R4) -- , Z is a bond or  -- O -- ;R4 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkyiheteroarylenyl, and heterocyclyl wherein the alkyl, alkenyl, alkynyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkyiheteroarylenyl, and heterocyclyl groups can be unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, hydroxyalkyl, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, mercapto, cyano, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, heteroarylalkyleneoxy, heterocyclyl, amino, alkylamino, dialkylamino, (dialkylamino)alkyleneoxy, and in the case of alkyl, alkenyl, alkynyl, and heterocyclyl, oxo;R5 is selected from the group consisting of R6 is selected from the group consisting of .dbd.O and .dbd.S;R7 is C2-7 alkylene;  R8 is selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, hydroxyalkylenyl, arylalkylenyl, and heteroarylalkylenyl;R9 is selected from the group consisting of hydrogen and alkyl;R10 is C3-8 alkylene;A is selected from the group consisting of  -- O -- ,  -- C(O) -- ,  -- S(O)0-2 -- , and  -- N(R4) -- ;A' is selected from the group consisting of  -- O -- ,  -- S(O)0-2 -- ,  -- N(-Q-R4) -- , and  -- CH2 -- ;Q is selected from the group consisting of a bond,  -- C(R6) -- ,  -- C(R6) -- C(R6) -- ,  -- S(O)2 -- ,  -- C(R6) -- N(R8) -- W -- ,  -- S(O)2 -- N(R8) -- ,  -- C(R6) -- O -- ,  -- C(R6) -- S -- , and  -- C(R6) -- N(OR9) -- ;V is selected from the group consisting of  -- C(R6) -- ,  -- O -- C(R6) -- ,  -- N(R8) -- C(R6) -- ;  and  -- S(O)2 -- ;W is selected from the group consisting of a bond,  -- C(O) -- , and  -- S(O)0-2 -- ;  and    a and b are independently integers from 1 to 6 with the proviso that a+b is <= 7;with the proviso that when R1 is hydrogen, m is 0, and R is chloro, then R2 is other than phenyl or phenyl substituted with methyl, methoxy, chloro, or fluoro; or a pharmaceutically acceptable salt thereof. 4. A compound of the formula (IX): wherein: RA2 and RB2 make a phenyl ring;R1 is selected from the group consisting of: -- R4,  -- X -- R4, -- X -- Y -- R4, -- X -- Y -- X -- Y -- R4, and -- X -- R5;R2 is selected from the group consisting of:  -- R4, -- X -- R4, -- X -- Y -- R4, and -- X -- R5;X is selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, heteroarylene, and heterocyclylene wherein the alkylene, alkenylene, and alkynylene groups can be optionally interrupted or terminated by arylene, heteroarylene or heterocyclylene and optionally interrupted by one or more  -- O --  groups;Y is selected from the group consisting of:  -- O -- , -- S(O)0-2 -- , -- S(O)2 -- N(R8) -- , -- C(R6) -- , -- C(R,6) -- O -- , -- O -- C(R6) -- , -- O -- C(O) -- O -- , -- N(R8)-Q-, -- C(R6) -- N(R8) -- , -- O -- C(R6) -- N(R8) -- , -- C(R6) -- N(OR9) -- , -- O -- N(R8)-Q-, -- O -- N.dbd.C(R4) -- , -- C(N -- O -- R8) -- , -- C(.dbd.N -- O -- R8) -- NH -- , -- CH( -- N( -- O -- R8)-Q-R4) -- , R4 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, aryloxyalkylenyl, al kylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkyiheteroarylenyl, and heterocyclyl wherein the alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, aryloxyalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkyiheteroarylenyl, and heterocyclyl groups can be unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, hydroxyalkyl, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, mercapto, cyano, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, heteroarylalkyleneoxy, heterocyclyl, amino, alkylamino, dialkylamino, (dialkylamino)alkyleneoxy, and in the case of alkyl, alkenyl, alkynyl, and heterocyclyl, oxo;R5 is selected from the group consisting of R6 is selected from the group consisting of .dbd.O and .dbd.S;R7 is C2-7alkylene;R8 is selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, hydroxyalkylenyl, arylalkylenyl and heteroarylalkylenyl;R9 is selected from the group consisting of hydrogen and alkyl;R10 is C3-8 alkylene;A is selected from the group consisting of  -- O -- ,  -- C(O) -- ,  -- S(O)0-2 -- , and  -- N(R4) -- ;A' is selected from the group consisting of  -- O -- ,  -- S(O)0-2 -- ,  -- N(-Q-R4) -- , and  -- CH2 -- ;Q is selected from the group consisting of a bond,  -- C(R6) -- ,  -- C(R6) -- C(R6) -- ,  -- S(O)2 -- C(R6) -- N(R8) -- W -- ,  -- S(O)2 -- N(R8) -- ,  -- C(R6) -- O -- ,  -- C(R6) -- S -- , and  -- C(R6) -- N(OR9)V is selected from the group consisting of  -- C(R6) -- ,  -- O -- C(R6) -- ,  -- N(R8) -- C(R6) -- , and  -- S(O)2 -- ;  W is selected from the group consisting of a bond,  -- C(O) -- , and  -- S(O)2 -- ;  and    a and b are independently integers from 1 to 6 with the proviso that a+b is <= 7;  with the proviso that at least one of RA2, RB2, R1, or R2 is other than hydrogen;  or a pharmaceutically acceptable salt thereof. 5. The compound or salt of claim 4 wherein R1 is selected from the group consisting of methyl, ethyl, propyl, butyl, 2-methylpropyl, 2,2-dimethylpropyl, 2-cyclohexylethyl, 2-hydroxy-2-methylpropyl, 2-(propylsulfonyl)ethyl, 2-methanesulfonylethyl, 2-methyl-2-[(methylsulfonyl)amino]propyl, 2-[(cyclohexylcarbonyl)amino]-2-methylpropyl, 2-{[(isopropylamino)carbonyl]amino)ethyl, 4-[(morpholin-4-ylcarbonyl)amino]butyl, 2-(benzoylamino)ethyl, 3-amino-2,2-dimethyl-3-oxopropyl, 2,2-dimethyl-4-oxopentyl, and 4-methanesulfonylaminobutyl;  R2 is selected from the group consisting of methyl, ethyl, propyl, butyl, 2-methoxyethyl, 2-hydroxyethyl, and benzyl. 6. A compound of the formula (Ia): wherein: RA3 and RB3 make a phenyl ring;R1 and R2 are independently selected from the group consisting of hydrogen and non-interfering substitutents;  and with the proviso that at least one of RA3, RB3, R1, or R2 is other than hydrogen;  and with the further proviso that when RA3 and RB3 form a benzene ring unsubstituted or substituted with chloro, and R1 is hydrogen, then R2 is other than phenyl or phenyl substituted with methyl, methoxy, chloro, or fluoro; or a pharmaceutically acceptable salt thereof. 7. A pharmaceutical composition comprising a therapeutically effective amount of a compound or salt of any one of claim 1 in combination with a pharmaceutically acceptable carrier. 8. A compound of the formula (II-1): wherein: Y'' is selected from the group consisting of  -- C(O) -- ,  -- C(O) -- O -- , and  -- C(.dbd.NR9) -- ;  R11 is alkyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, hydroxy, nitro, cyano, carboxy, C1-4 alkoxy, aryl, heteroaryl, arylC1-4alkylenyl, heteroarylC1-4alkylenyl, haloC1-4alkyl, haloC1-4alkoxy,  -- O -- C(O) -- CH3,  -- CO2CH3,  -- CONH2,  -- O -- CH2 -- CONH2,  -- NH2, and  -- SO2 -- NH2;RA1 and RB1 make a phenyl ring;R1 is selected from the group consisting of:  -- R4, -- X -- R4, -- X -- Y -- R4, -- X -- Y -- X -- Y -- R4, and -- X -- R5;R2 is selected from the group consisting of:  -- R4, -- X -- R4, -- X -- Y -- R4, and -- X -- R5;X is selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, heteroarylene, and heterocyclylene wherein the alkylene, alkenylene, and alkynylene groups can be optionally interrupted or terminated by arylene, heteroarylene or heterocyclylene and optionally interrupted by one or more  -- O --  groups;Y is selected from the group consisting of:  -- O -- , -- S(O)0-2 -- , -- S(O)2 -- N(R8) -- , -- C(R6) -- , -- C(R6) -- O -- , -- O -- C(R6) -- , -- O -- C(O) -- O -- , -- N(R8)-Q-, -- C(R6) -- N(R8) -- , -- O -- C(R6) -- N(R8) -- , -- C(R6) -- N(OR9) -- , -- O -- N(R8)-Q-, -- O -- N.dbd.C(R4) -- , -- C(.dbd.N -- O -- R8) -- , -- C(.dbd.N -- O -- R8) -- NH -- , -- CH( -- N( -- O -- R8)-Q-R4) -- , Z is a bond or  -- O -- ;  R4 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkyiheteroarylenyl, and heterocyclyl wherein the alkyl, alkenyl, alkynyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkyiheteroarylenyl, and heterocyclyl groups can be unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, hydroxyalkyl, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, mercapto, cyano, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, heteroarylalkyleneoxy, heterocyclyl, amino, alkylamino, dialkylamino, (dialkylamino)alkyleneoxy, and in the case of alkyl, alkenyl, alkynyl, and heterocyclyl, oxo;R5 is selected from the group consisting of R6 is selected from the group consisting of .dbd.O and .dbd.S;R7 is C2-7 alkylene;  R8 is selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, hydroxyalkylenyl, arylalkylenyl, and heteroarylalkylenyl;R9 is selected from the group consisting of hydrogen and alkyl;R10 is C3-8 alkylene;A is selected from the group consisting of  -- O -- ,  -- C(O) -- ,  -- S(O)0-2 -- , and  -- N(R4) -- ;A' is selected from the group consisting of  -- O -- ,  -- S(O)0-2 -- ,  -- N(-Q-R4) -- , and  -- CH2 -- ;Q is selected from the group consisting of a bond,  -- C(R6) -- ,  -- C(R6) -- C(R6) -- ,  -- S(O)2 -- ,  -- C(R6) -- N(R8) -- W -- ,  -- S(O)2 -- N(R8) -- ,  -- C(R6) -- O -- ,  -- C(R6) -- S -- , and  -- C(R6) -- N(OR9) -- ;V is selected from the group consisting of  -- C(R6) -- ,  -- O -- C(R6) -- ,  -- N(R8) -- C(R6) -- , and  -- S(O)2 -- ;W is selected from the group consisting of a bond,  -- C(O) -- , and  -- S(O)2 -- ;  and    a and b are independently integers from 1 to 6 with the proviso that a+b is <= 7;with the proviso that at least one of RA1, RB1, R1, or R2 is other than hydrogen;  and with the further proviso that when RA1 and RB1 form a fused benzene ring unsubstituted or substituted with chloro, and R1 is hydrogen, then R2 is other than phenyl or phenyl substituted with methyl, methoxy, chloro, or fluoro; or a pharmaceutically acceptable salt thereof. 9. The compound or salt of claim 2 wherein R1 is selected from the group consisting of methyl, ethyl, propyl, butyl, 2-methylpropyl, 2,2-dimethylpropyl, 2-hydroxy-2-methylpropyl, 2-(propylsulfonyl)ethyl, 2-methanesulfonylethyl, 2-methyl-2-[(methylsulfonyl)amino]propyl, 2-[(cyclohexylcarbonyl)amino]-2-methylpropyl, 2-{[(isopropylamino)carbonyl]amino}ethyl, 4-[(morpholin-4-ylcarbonyl)amino]butyl, 2-(benzoylamino)ethyl, 3-amino-2,2-dimethyl-3oxopropyl, 2,2-dimethyl-4-oxopentyl, and 4-methanesulfonylaminobutyl;  and R2 is selected from the group consisting of methyl, ethyl, propyl, butyl, 2-methoxyethyl, 2-hydroxyethyl, and benzyl. 10. The compound or salt of claim 8 wherein R1 is selected from the group consisting of methyl, ethyl, propyl, butyl, 2-methylpropyl, 2,2-dimethylpropyl, 2-hydroxy-2-methylpropyl, 2-(propylsulfonyl)ethyl, 2-methanesulfonylethyl, 2-methyl-2-[(methylsulfonyl)amino]propyl, 2-[(cyclohexylcarbonyl)amino]-2-methylpropyl, 2-{[(isopropylamino)carbonyl]amino}ethyl, 4-[(morpholin-4-ylcarbonyl)amino]butyl, 2-(benzoylamino)ethyl, 3-amino-2,2-dimethyl-3oxopropyl, 2,2-dimethyl-4-oxopentyl, and 4-methanesulfonylaminobutyl;  and R2 is selected from the group consisting of methyl, ethyl, propyl, butyl, 2-methoxyethyl, 2-hydroxyethyl, and benzyl. 11. the compound or salt of claim 3 wherein the compounds is 1-(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)-2-methylpropan-2-ol.
法律状态
(US7544697) LEGAL DETAILS FOR US2006100229  Actual or expected expiration date=2025-10-28    Legal state=ALIVE    Status=GRANTED     Event publication date=2005-04-01  Event code=US/APP  Event indicator=Pos  Event type=Examination events  Application details  Application country=US US11097715  Application date=2005-04-01  Standardized application number=2004US-11097715     Event publication date=2005-04-01  Event code=US/EXMR  Event type=Administrative notifications  USPTO Examiner Name Primary Examiner: RAHMANI, NILOOFAR    Event publication date=2005-04-01  Event code=US/ART  Event type=Administrative notifications  USPTO Art Group  ART=1625     Event publication date=2005-04-01  Event code=US/ENT  Event type=Administrative notifications  Entity Status Set to Undiscounted Business Entity Status: UNDISCOUNTED    Event publication date=2005-04-01  Event code=US/AIA  Event type=Administrative notifications  First Inventor File Indicated:  AIA=No     Event publication date=2005-04-01  Event code=US/DK  Event type=Examination events  Attorney Docket Number Docket Nbr: 59050US015    Event publication date=2005-04-01  Event code=US/CUST  Event type=Examination events  Attorney/Agent Customer Number Customer Nbr: 32692    Event publication date=2005-04-01  Event code=US/APE  Event type=Corrections  Preliminary amendments    Event publication date=2005-05-06  Event code=US/INCD  Event type=Examination events  Event type=OAO  Notice Mailed--Application Incomplete--Filing Date Assigned    Event publication date=2005-05-31  Event code=US/AS  Event type=Change of name or address  Event type=Reassignment  Assignment ASSIGNMENT OF ASSIGNORS INTEREST ASSIGNORS:HAYS, DAVID S. DANIELSON, MICHAEL E. GERSTER, JOHN F. AND OTHERS REEL/FRAME:016285/0932 SIGNING DATES FROM 20050518 TO 20050519     Event publication date=2005-07-28  Event code=US/IDS  Event type=Examination events  Event type=OAI  Information Disclosure Statement Filed    Event publication date=2005-12-29  Event code=US/AS  Event type=Change of name or address  Event type=Reassignment  Assignment CORRECT MIDDLE INITIAL OF SEVENTH INVENTOR 'PHILIP D. HEPPNER' ON A PREVIOUSLY RECORDED AT REEL 16285/FRAME 0932. DOCUMENT NUMBERS 700219842 AND 700183575 ASSIGNORS:HAYS, DAVID S. DANIELSON, MICHAEL E. GERSTER, JOHN F. 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