JP2014511884A5

JP2014511884A5 -

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Publication number: JP2014511884A5
Authority: JP; Japan
Prior art keywords: pyrazolo; quinolin; methoxy; amine; phenyl
Prior art date: 2012-04-23
Legal status : Granted

Application number

JP2014505543A

Other languages

English (en)

Japanese (ja)

Other versions

JP6278406B2 (ja

JP2014511884A (ja

Filing date

2012-04-23

Publication date

2016-10-27

2012-04-23 Application filed filed Critical

2012-04-23 Priority claimed from PCT/EP2012/001736 external-priority patent/WO2012143143A1/en

2014-05-19 Publication of JP2014511884A publication Critical patent/JP2014511884A/ja

2016-10-27 Publication of JP2014511884A5 publication Critical patent/JP2014511884A5/ja

2018-02-14 Application granted granted Critical

2018-02-14 Publication of JP6278406B2 publication Critical patent/JP6278406B2/ja

Status Active legal-status Critical Current

2032-04-23 Anticipated expiration legal-status Critical

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FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 claims description 117
-1 3- (trifluoromethyl) phenyl Chemical group 0.000 claims description 100
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 29
125000001072 heteroaryl group Chemical group 0.000 claims description 26
150000001875 compounds Chemical class 0.000 claims description 25
125000006413 ring segment Chemical group 0.000 claims description 25
125000005842 heteroatom Chemical group 0.000 claims description 24
229910052717 sulfur Inorganic materials 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 20
229910052760 oxygen Inorganic materials 0.000 claims description 18
125000000753 cycloalkyl group Chemical group 0.000 claims description 16
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 14
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
125000003710 aryl alkyl group Chemical group 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 9
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
125000004475 heteroaralkyl group Chemical group 0.000 claims description 9
WVXADFXJVONWJY-UHFFFAOYSA-N 1,5-naphthyridin-2-amine Chemical compound N1=CC=CC2=NC(N)=CC=C21 WVXADFXJVONWJY-UHFFFAOYSA-N 0.000 claims description 8
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 8
VLCMRTMCMQJSKM-UHFFFAOYSA-N phenyl-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C1=CC=CC=C1 VLCMRTMCMQJSKM-UHFFFAOYSA-N 0.000 claims description 7
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 6
125000005605 benzo group Chemical group 0.000 claims description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
125000004404 heteroalkyl group Chemical group 0.000 claims description 6
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims description 4
HBICFWOEODDCMX-UHFFFAOYSA-N 8-methoxy-n-(4-thiomorpholin-4-ylphenyl)-3h-pyrazolo[3,4-c]quinolin-4-amine Chemical compound C1=2NN=CC=2C2=CC(OC)=CC=C2N=C1NC(C=C1)=CC=C1N1CCSCC1 HBICFWOEODDCMX-UHFFFAOYSA-N 0.000 claims description 4
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 4
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 4
125000005549 heteroarylene group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
ASLOLYWDRZZUPZ-UHFFFAOYSA-N n-(1h-indazol-6-yl)-8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-amine Chemical compound C1=C2C=NNC2=CC(NC2=NC3=CC=C(C=C3C3=CNN=C32)OC)=C1 ASLOLYWDRZZUPZ-UHFFFAOYSA-N 0.000 claims description 4
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
UZZAFECARSHHEF-UHFFFAOYSA-N 4-chloro-2-[(4-methoxyphenyl)methyl]pyrazolo[3,4-c][1,7]naphthyridine Chemical compound C1=CC(OC)=CC=C1CN1N=C(C(Cl)=NC=2C3=CC=NC=2)C3=C1 UZZAFECARSHHEF-UHFFFAOYSA-N 0.000 claims description 3
YKTDVSIYAGSDGJ-UHFFFAOYSA-N 4-chloro-8-iodo-2-[(4-methoxyphenyl)methyl]pyrazolo[3,4-c]quinoline Chemical compound C1=CC(OC)=CC=C1CN1N=C(C(Cl)=NC=2C3=CC(I)=CC=2)C3=C1 YKTDVSIYAGSDGJ-UHFFFAOYSA-N 0.000 claims description 3
JQTMGOLZSBTZMS-UHFFFAOYSA-N 4-methylpiperazine-1-carbaldehyde Chemical compound CN1CCN(C=O)CC1 JQTMGOLZSBTZMS-UHFFFAOYSA-N 0.000 claims description 3
GCNHPJQIHUQNDZ-UHFFFAOYSA-N 6-chloro-2-methoxy-8-[(4-methoxyphenyl)methyl]pyrazolo[3,4-c][1,5]naphthyridine Chemical compound C1=CC(OC)=CC=C1CN1N=C(C(Cl)=NC=2C3=NC(OC)=CC=2)C3=C1 GCNHPJQIHUQNDZ-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
NJUANFRHJWYJGN-UHFFFAOYSA-N (1h-indazol-6-yl)-(1-methyl-7h-3-thia-2,4,6,7-tetraaza-as-indacen-5-yl)-amine Chemical compound C1=C2C=NNC2=CC(NC2=NC=3SN=C(C=3C3=CNN=C32)C)=C1 NJUANFRHJWYJGN-UHFFFAOYSA-N 0.000 claims description 2
OAZQJVYWJJCCSA-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decan-8-yl-[4-[(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)amino]phenyl]methanone Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC(C=C1)=CC=C1C(=O)N(CC1)CCC21OCCO2 OAZQJVYWJJCCSA-UHFFFAOYSA-N 0.000 claims description 2
PHFKUTFUFKZJMV-UHFFFAOYSA-N 1,7-naphthyridin-4-amine Chemical compound N1=CC=C2C(N)=CC=NC2=C1 PHFKUTFUFKZJMV-UHFFFAOYSA-N 0.000 claims description 2
VZGZJACXVNKYSI-UHFFFAOYSA-N 1-[3-[(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)amino]phenyl]ethanone Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC1=CC=CC(C(C)=O)=C1 VZGZJACXVNKYSI-UHFFFAOYSA-N 0.000 claims description 2
IIEUAUWNYBTDEN-UHFFFAOYSA-N 1-[4-[(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)amino]benzoyl]piperidin-4-one Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC(C=C1)=CC=C1C(=O)N1CCC(=O)CC1 IIEUAUWNYBTDEN-UHFFFAOYSA-N 0.000 claims description 2
XGBGMBLEFHXNQN-UHFFFAOYSA-N 1-[4-[(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)amino]phenyl]pyrrolidin-2-one Chemical compound C1=2NN=CC=2C2=CC(OC)=CC=C2N=C1NC(C=C1)=CC=C1N1CCCC1=O XGBGMBLEFHXNQN-UHFFFAOYSA-N 0.000 claims description 2
UYRAICOUFWRQLG-UHFFFAOYSA-N 1-[4-[4-[(8-fluoro-3h-pyrazolo[3,4-c]quinolin-4-yl)amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC2=CC=C(F)C=C2C2=C1NN=C2 UYRAICOUFWRQLG-UHFFFAOYSA-N 0.000 claims description 2
QHCZXRSPQDTHHA-UHFFFAOYSA-N 1-n-(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)-3-n,3-n-dimethylbenzene-1,3-diamine Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC1=CC=CC(N(C)C)=C1 QHCZXRSPQDTHHA-UHFFFAOYSA-N 0.000 claims description 2
SBJDGZBSKSDYQT-UHFFFAOYSA-N 1-n-(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)-4-n-methyl-4-n-(1-methylpiperidin-4-yl)benzene-1,4-diamine Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC(C=C1)=CC=C1N(C)C1CCN(C)CC1 SBJDGZBSKSDYQT-UHFFFAOYSA-N 0.000 claims description 2
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
XOYKSILZWFFIJF-UHFFFAOYSA-N 2,2,2-trifluoro-n-[4-[(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)amino]phenyl]acetamide Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC1=CC=C(NC(=O)C(F)(F)F)C=C1 XOYKSILZWFFIJF-UHFFFAOYSA-N 0.000 claims description 2
125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
JQFYYHVQNQYZEP-UHFFFAOYSA-N 2-[3-[(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)amino]phenyl]sulfonylethanol Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC1=CC=CC(S(=O)(=O)CCO)=C1 JQFYYHVQNQYZEP-UHFFFAOYSA-N 0.000 claims description 2
YZIWDOXEDGOSFY-UHFFFAOYSA-N 2-[4-[(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)amino]phenoxy]acetic acid Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC1=CC=C(OCC(O)=O)C=C1 YZIWDOXEDGOSFY-UHFFFAOYSA-N 0.000 claims description 2
PFXUDEZPRKXWRO-UHFFFAOYSA-N 2-[4-[(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)amino]phenyl]acetic acid Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC1=CC=C(CC(O)=O)C=C1 PFXUDEZPRKXWRO-UHFFFAOYSA-N 0.000 claims description 2
LOIUZOXTMORDOF-UHFFFAOYSA-N 2-[4-[4-[(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)amino]phenyl]piperazin-1-yl]acetic acid Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC(C=C1)=CC=C1N1CCN(CC(O)=O)CC1 LOIUZOXTMORDOF-UHFFFAOYSA-N 0.000 claims description 2
KLVPPPZHHSQTAJ-UHFFFAOYSA-N 2-methoxy-5-[(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)amino]phenol Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC1=CC=C(OC)C(O)=C1 KLVPPPZHHSQTAJ-UHFFFAOYSA-N 0.000 claims description 2
JGTIMOUMDVVHQO-UHFFFAOYSA-N 2-n-(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)cyclohexane-1,2-diamine Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC1CCCCC1N JGTIMOUMDVVHQO-UHFFFAOYSA-N 0.000 claims description 2
DSLQTADPZAAGPW-UHFFFAOYSA-N 2-n-[2-(dimethylamino)ethyl]-5-n-(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)pyrimidine-2,5-diamine Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC1=CN=C(NCCN(C)C)N=C1 DSLQTADPZAAGPW-UHFFFAOYSA-N 0.000 claims description 2
FNIXVMDYYJNLEO-UHFFFAOYSA-N 3-[(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2C3=NNC=C3C3=CC(OC)=CC=C3N=2)=C1 FNIXVMDYYJNLEO-UHFFFAOYSA-N 0.000 claims description 2
RLUFCINFWBGRSP-UHFFFAOYSA-N 3-[(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)amino]benzoic acid Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC1=CC=CC(C(O)=O)=C1 RLUFCINFWBGRSP-UHFFFAOYSA-N 0.000 claims description 2
RAQXXATXBALYSX-UHFFFAOYSA-N 4-(1h-indazol-6-ylamino)-1-methyl-2h-pyrazolo[3,4-c]quinoline-7-carbonitrile Chemical compound N#CC1=CC=C2C3=C(C)NN=C3C(NC=3C=C4NN=CC4=CC=3)=NC2=C1 RAQXXATXBALYSX-UHFFFAOYSA-N 0.000 claims description 2
ROSZIKLOFQWICZ-UHFFFAOYSA-N 4-[(8-methoxy-3H-pyrazolo[3,4-c]quinolin-4-yl)amino]benzene-1,2-diol Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC1=CC=C(O)C(O)=C1 ROSZIKLOFQWICZ-UHFFFAOYSA-N 0.000 claims description 2
XPDWZPMHPHENAR-UHFFFAOYSA-N 4-chloro-1-(trifluoromethyl)-2h-pyrazolo[3,4-c]quinoline Chemical compound C1=CC=C2C3=C(C(F)(F)F)NN=C3C(Cl)=NC2=C1 XPDWZPMHPHENAR-UHFFFAOYSA-N 0.000 claims description 2
ILURWBKRBGJUSP-UHFFFAOYSA-N 4-chloro-1-methyl-2h-pyrazolo[3,4-c]quinoline Chemical compound C1=CC=C2C3=C(C)NN=C3C(Cl)=NC2=C1 ILURWBKRBGJUSP-UHFFFAOYSA-N 0.000 claims description 2
KWKDNKIGCYXVOV-UHFFFAOYSA-N 4-chloro-1-nitro-3h-pyrazolo[3,4-c]quinoline Chemical compound C1=CC=C2C3=C([N+](=O)[O-])NN=C3C(Cl)=NC2=C1 KWKDNKIGCYXVOV-UHFFFAOYSA-N 0.000 claims description 2
SKCCYIOYXVYJKH-UHFFFAOYSA-N 4-chloro-2-[(4-methoxyphenyl)methyl]-1-(trifluoromethyl)pyrazolo[3,4-c]quinoline Chemical compound C1=CC(OC)=CC=C1CN1C(C(F)(F)F)=C2C3=CC=CC=C3N=C(Cl)C2=N1 SKCCYIOYXVYJKH-UHFFFAOYSA-N 0.000 claims description 2
VUPCZHLVQAMOOK-UHFFFAOYSA-N 4-chloro-2-[(4-methoxyphenyl)methyl]-1-methylpyrazolo[3,4-c]quinoline Chemical compound C1=CC(OC)=CC=C1CN1C(C)=C2C3=CC=CC=C3N=C(Cl)C2=N1 VUPCZHLVQAMOOK-UHFFFAOYSA-N 0.000 claims description 2
JFIGGKRYWPZHIJ-UHFFFAOYSA-N 4-chloro-2-[(4-methoxyphenyl)methyl]-1-methylpyrazolo[3,4-c]quinoline-7-carbonitrile Chemical compound C1=CC(OC)=CC=C1CN1C(C)=C2C3=CC=C(C#N)C=C3N=C(Cl)C2=N1 JFIGGKRYWPZHIJ-UHFFFAOYSA-N 0.000 claims description 2
WWZDAPKGXRWUJK-UHFFFAOYSA-N 4-chloro-2-[(4-methoxyphenyl)methyl]-1-nitropyrazolo[3,4-c]quinoline Chemical compound C1=CC(OC)=CC=C1CN1C([N+]([O-])=O)=C2C3=CC=CC=C3N=C(Cl)C2=N1 WWZDAPKGXRWUJK-UHFFFAOYSA-N 0.000 claims description 2
LSYCCOBPNJGDHH-UHFFFAOYSA-N 4-chloro-2-[(4-methoxyphenyl)methyl]pyrazolo[3,4-c]quinoline Chemical compound C1=CC(OC)=CC=C1CN1N=C(C(Cl)=NC=2C3=CC=CC=2)C3=C1 LSYCCOBPNJGDHH-UHFFFAOYSA-N 0.000 claims description 2
FSEQPPRZXLUNKA-UHFFFAOYSA-N 4-chloro-2-[(4-methoxyphenyl)methyl]pyrazolo[3,4-c]quinoline-8-carbonitrile Chemical compound C1=CC(OC)=CC=C1CN1N=C(C(Cl)=NC=2C3=CC(=CC=2)C#N)C3=C1 FSEQPPRZXLUNKA-UHFFFAOYSA-N 0.000 claims description 2
PUMAZEJARLTRJL-UHFFFAOYSA-N 4-chloro-3h-pyrazolo[3,4-c][1,7]naphthyridine Chemical compound N1=CC=C2C3=CNN=C3C(Cl)=NC2=C1 PUMAZEJARLTRJL-UHFFFAOYSA-N 0.000 claims description 2
SMLVLIPXMISHKV-UHFFFAOYSA-N 4-chloro-3h-pyrazolo[3,4-c]quinoline Chemical compound C1=CC=C2C3=CNN=C3C(Cl)=NC2=C1 SMLVLIPXMISHKV-UHFFFAOYSA-N 0.000 claims description 2
USXMYUMEBLSSFM-UHFFFAOYSA-N 4-chloro-6,8-dimethoxy-3h-pyrazolo[3,4-c]quinoline Chemical compound N1=C(Cl)C2=NNC=C2C2=CC(OC)=CC(OC)=C21 USXMYUMEBLSSFM-UHFFFAOYSA-N 0.000 claims description 2
AOVMKGVPKHPXLG-UHFFFAOYSA-N 4-chloro-6-methoxy-2-[(4-methoxyphenyl)methyl]pyrazolo[3,4-c]quinoline Chemical compound C1=CC(OC)=CC=C1CN1N=C(C(Cl)=NC=2C3=CC=CC=2OC)C3=C1 AOVMKGVPKHPXLG-UHFFFAOYSA-N 0.000 claims description 2
BCKMMPMEQSUETA-UHFFFAOYSA-N 4-chloro-7,8-diethoxy-3h-pyrazolo[3,4-c]quinoline Chemical compound N1=C(Cl)C2=NNC=C2C2=C1C=C(OCC)C(OCC)=C2 BCKMMPMEQSUETA-UHFFFAOYSA-N 0.000 claims description 2
SMRIQHWHXFOMHM-UHFFFAOYSA-N 4-chloro-7,8-dimethoxy-2-[(4-methoxyphenyl)methyl]pyrazolo[3,4-c]quinoline Chemical compound C1=CC(OC)=CC=C1CN1N=C(C(Cl)=NC=2C3=CC(OC)=C(OC)C=2)C3=C1 SMRIQHWHXFOMHM-UHFFFAOYSA-N 0.000 claims description 2
LCHXBXWPNFRMIB-UHFFFAOYSA-N 4-chloro-7,8-dimethoxy-3h-pyrazolo[3,4-c]quinoline Chemical compound N1=C(Cl)C2=NNC=C2C2=C1C=C(OC)C(OC)=C2 LCHXBXWPNFRMIB-UHFFFAOYSA-N 0.000 claims description 2
AMFKJXZXFVGUNB-UHFFFAOYSA-N 4-chloro-7-fluoro-2-[(4-methoxyphenyl)methyl]pyrazolo[3,4-c]quinoline Chemical compound C1=CC(OC)=CC=C1CN1N=C(C(Cl)=NC=2C3=CC=C(F)C=2)C3=C1 AMFKJXZXFVGUNB-UHFFFAOYSA-N 0.000 claims description 2
HOONRXVCTYDVSQ-UHFFFAOYSA-N 4-chloro-7-methoxy-2-[(4-methoxyphenyl)methyl]pyrazolo[3,4-c]quinoline Chemical compound C1=CC(OC)=CC=C1CN1N=C(C(Cl)=NC=2C3=CC=C(OC)C=2)C3=C1 HOONRXVCTYDVSQ-UHFFFAOYSA-N 0.000 claims description 2
VHENDQLERILTQI-UHFFFAOYSA-N 4-chloro-7-methoxy-3h-pyrazolo[3,4-c]quinoline Chemical compound ClC1=NC2=CC(OC)=CC=C2C2=CNN=C21 VHENDQLERILTQI-UHFFFAOYSA-N 0.000 claims description 2
LHDFTHUQZOUQME-UHFFFAOYSA-N 4-chloro-8-fluoro-3h-pyrazolo[3,4-c]quinoline Chemical compound N1=C(Cl)C2=NNC=C2C2=CC(F)=CC=C21 LHDFTHUQZOUQME-UHFFFAOYSA-N 0.000 claims description 2
WNLPTEAHOYWKGU-UHFFFAOYSA-N 4-chloro-8-methoxy-2-[(4-methoxyphenyl)methyl]pyrazolo[3,4-c]quinoline Chemical compound C1=CC(OC)=CC=C1CN1N=C(C(Cl)=NC=2C3=CC(OC)=CC=2)C3=C1 WNLPTEAHOYWKGU-UHFFFAOYSA-N 0.000 claims description 2
MZKDVYQRJZCOFT-UHFFFAOYSA-N 4-chloro-8-methoxy-3h-pyrazolo[3,4-c]quinoline Chemical compound N1=C(Cl)C2=NNC=C2C2=CC(OC)=CC=C21 MZKDVYQRJZCOFT-UHFFFAOYSA-N 0.000 claims description 2
NPUMHPQAEKDCOC-UHFFFAOYSA-N 4-chloro-9-fluoro-2-[(4-methoxyphenyl)methyl]pyrazolo[3,4-c]quinoline Chemical compound C1=CC(OC)=CC=C1CN1N=C(C(Cl)=NC=2C3=C(F)C=CC=2)C3=C1 NPUMHPQAEKDCOC-UHFFFAOYSA-N 0.000 claims description 2
PSFLUVBVNNOAFK-UHFFFAOYSA-N 4-chloro-9-methoxy-2-[(4-methoxyphenyl)methyl]pyrazolo[3,4-c]quinoline Chemical compound C1=CC(OC)=CC=C1CN1N=C(C(Cl)=NC=2C3=C(OC)C=CC=2)C3=C1 PSFLUVBVNNOAFK-UHFFFAOYSA-N 0.000 claims description 2
KHDOKQSQNCXUDM-UHFFFAOYSA-N 4-methyl-1,4-diazepane-1-carbaldehyde Chemical compound CN1CCCN(C=O)CC1 KHDOKQSQNCXUDM-UHFFFAOYSA-N 0.000 claims description 2
UMAWBOLROKHYMR-UHFFFAOYSA-N 4-n,4-n-diethyl-1-n-(8-methoxy-3h-pyrazolo[3,4-c]quinolin-4-yl)benzene-1,4-diamine Chemical compound C1=CC(N(CC)CC)=CC=C1NC1=NC2=CC=C(OC)C=C2C2=CNN=C12 UMAWBOLROKHYMR-UHFFFAOYSA-N 0.000 claims description 2
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SPOLTYRJYYIZHH-UHFFFAOYSA-N 8-methoxy-n-(3-methylsulfinylphenyl)-3h-pyrazolo[3,4-c]quinolin-4-amine Chemical compound C12=NNC=C2C2=CC(OC)=CC=C2N=C1NC1=CC=CC(S(C)=O)=C1 SPOLTYRJYYIZHH-UHFFFAOYSA-N 0.000 claims description 2
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JP2014505543A 2011-04-21 2012-04-23 キナーゼ・インヒビターとしての複素環化合物 Active JP6278406B2 (ja)