JP2016507501A5 - - Google Patents
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- Publication number
- JP2016507501A5 JP2016507501A5 JP2015549744A JP2015549744A JP2016507501A5 JP 2016507501 A5 JP2016507501 A5 JP 2016507501A5 JP 2015549744 A JP2015549744 A JP 2015549744A JP 2015549744 A JP2015549744 A JP 2015549744A JP 2016507501 A5 JP2016507501 A5 JP 2016507501A5
- Authority
- JP
- Japan
- Prior art keywords
- piperazin
- cyclopropyl
- phenyl
- dimethoxy
- methoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 tautomer Chemical class 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 21
- 150000001204 N-oxides Chemical class 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 19
- 239000012453 solvate Substances 0.000 claims 19
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 5
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- TYVVZRKDKNAKQL-UHFFFAOYSA-N 2-cyclobutyl-6,7-dimethoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CCC2)CC1 TYVVZRKDKNAKQL-UHFFFAOYSA-N 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- ORGYRUPXWKPADU-UHFFFAOYSA-N 2-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]benzonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=CC=C1C#N ORGYRUPXWKPADU-UHFFFAOYSA-N 0.000 claims 2
- QVDWFOQAYDMZLC-UHFFFAOYSA-N 2-[4-[2-cyclopropyl-6-(dimethylamino)quinazolin-4-yl]piperazin-1-yl]benzonitrile Chemical compound C12=CC(N(C)C)=CC=C2N=C(C2CC2)N=C1N(CC1)CCN1C1=CC=CC=C1C#N QVDWFOQAYDMZLC-UHFFFAOYSA-N 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- HOHUZHPCXFCPMJ-UHFFFAOYSA-N 2-cyclobutyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC=CC=C3N=C(N=2)C2CCC2)CC1 HOHUZHPCXFCPMJ-UHFFFAOYSA-N 0.000 claims 2
- CIWKHKMZANVYGH-UHFFFAOYSA-N 2-cyclobutyl-6-methoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound C12=CC(OC)=CC=C2N=C(C2CCC2)N=C1N(CC1)CCN1C1=CC=CC=C1OC CIWKHKMZANVYGH-UHFFFAOYSA-N 0.000 claims 2
- RLNMVERRIAKFHG-UHFFFAOYSA-N 2-cyclobutyl-7-methoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound N=1C2=CC(OC)=CC=C2C(N2CCN(CC2)C=2C(=CC=CC=2)OC)=NC=1C1CCC1 RLNMVERRIAKFHG-UHFFFAOYSA-N 0.000 claims 2
- QJMSCKUDXSGMCI-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2,5-dimethoxyphenyl)piperazin-1-yl]-n,n-dimethylquinazolin-6-amine Chemical compound COC1=CC=C(OC)C(N2CCN(CC2)C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(C)C)=C1 QJMSCKUDXSGMCI-UHFFFAOYSA-N 0.000 claims 2
- RIXUQCJOFZKOAL-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]-n-methyl-n-(2-morpholin-4-ylethyl)quinazolin-6-amine Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(C)CCN2CCOCC2)CC1 RIXUQCJOFZKOAL-UHFFFAOYSA-N 0.000 claims 2
- PFRUEKPBGILXQJ-UHFFFAOYSA-N 2-cyclopropyl-6-methoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound C12=CC(OC)=CC=C2N=C(C2CC2)N=C1N(CC1)CCN1C1=CC=CC=C1OC PFRUEKPBGILXQJ-UHFFFAOYSA-N 0.000 claims 2
- HOVSFZZNTJPWJN-UHFFFAOYSA-N 2-cyclopropyl-n,n-diethyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]-7-methylquinazolin-6-amine Chemical compound N1=C2C=C(C)C(N(CC)CC)=CC2=C(N2CCC(CC2)C=2C(=CC=CC=2)OC)N=C1C1CC1 HOVSFZZNTJPWJN-UHFFFAOYSA-N 0.000 claims 2
- SIGJYCUBAYNBQQ-UHFFFAOYSA-N 3-chloro-4-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]benzoic acid Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(C(O)=O)C=C1Cl SIGJYCUBAYNBQQ-UHFFFAOYSA-N 0.000 claims 2
- CXGYDLQELLAJEO-UHFFFAOYSA-N 6,7-dimethoxy-2-(4-methoxycyclohexyl)-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound C1CC(OC)CCC1C1=NC(N2CCN(CC2)C=2C(=CC=CC=2)OC)=C(C=C(OC)C(OC)=C2)C2=N1 CXGYDLQELLAJEO-UHFFFAOYSA-N 0.000 claims 2
- RYVMOBRDKUBUSJ-UHFFFAOYSA-N 6-bromo-2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]-7-methylquinazoline Chemical compound COC1=CC=CC=C1C1CCN(C=2C3=CC(Br)=C(C)C=C3N=C(N=2)C2CC2)CC1 RYVMOBRDKUBUSJ-UHFFFAOYSA-N 0.000 claims 2
- PWJIZHGNECXEFM-UHFFFAOYSA-N 6-cyclobutyl-8-[4-(2-methoxyphenyl)piperazin-1-yl]-[1,3]dioxolo[4,5-g]quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC=4OCOC=4C=C3N=C(N=2)C2CCC2)CC1 PWJIZHGNECXEFM-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- COBQDTVRABHXMA-UHFFFAOYSA-N 1-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)-3-[2-(dimethylamino)phenyl]pyrrolidin-3-ol Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(C1)CCC1(O)C1=CC=CC=C1N(C)C COBQDTVRABHXMA-UHFFFAOYSA-N 0.000 claims 1
- XBZZFWPKMSJJJW-UHFFFAOYSA-N 1-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)-3-phenylpyrrolidin-3-ol Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(C1)CCC1(O)C1=CC=CC=C1 XBZZFWPKMSJJJW-UHFFFAOYSA-N 0.000 claims 1
- OPYKWQQCOLONPB-UHFFFAOYSA-N 1-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)-n-(2-methoxyphenyl)piperidin-4-amine Chemical compound COC1=CC=CC=C1NC1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 OPYKWQQCOLONPB-UHFFFAOYSA-N 0.000 claims 1
- FOCYXZGUGRNWPS-UHFFFAOYSA-N 2-(1,4-dimethylpyrrolidin-3-yl)-6,7-dimethoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2C(CN(C)C2)C)CC1 FOCYXZGUGRNWPS-UHFFFAOYSA-N 0.000 claims 1
- PHMXYMYAVOVEDU-UHFFFAOYSA-N 2-(cyclopropylmethyl)-6,7-dimethoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(CC3CC3)N=2)CC1 PHMXYMYAVOVEDU-UHFFFAOYSA-N 0.000 claims 1
- HRAIYDLPGBWBSN-UHFFFAOYSA-N 2-[(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)amino]-n-(2-methoxyphenyl)acetamide Chemical compound COC1=CC=CC=C1NC(=O)CNC1=NC(C2CC2)=NC2=CC(OC)=C(OC)C=C12 HRAIYDLPGBWBSN-UHFFFAOYSA-N 0.000 claims 1
- PEIVTHGTJRLALT-UHFFFAOYSA-N 2-[1-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)-3-fluoropyrrolidin-3-yl]-n,n-dimethylaniline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(C1)CCC1(F)C1=CC=CC=C1N(C)C PEIVTHGTJRLALT-UHFFFAOYSA-N 0.000 claims 1
- KEMJDTKTUYIYBE-UHFFFAOYSA-N 2-[1-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperidin-4-yl]-n,n-dimethylaniline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCC1C1=CC=CC=C1N(C)C KEMJDTKTUYIYBE-UHFFFAOYSA-N 0.000 claims 1
- DNQDVQFOGNTULS-UHFFFAOYSA-N 2-[1-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)pyrrolidin-3-yl]-n,n-dimethylaniline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(C1)CCC1C1=CC=CC=C1N(C)C DNQDVQFOGNTULS-UHFFFAOYSA-N 0.000 claims 1
- FVVNOZGLQYPFJC-UHFFFAOYSA-N 2-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-5-fluoro-n,n-dimethylaniline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(F)C=C1N(C)C FVVNOZGLQYPFJC-UHFFFAOYSA-N 0.000 claims 1
- HQXWXGDAVQFLSQ-UHFFFAOYSA-N 2-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-5-fluoroaniline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(F)C=C1N HQXWXGDAVQFLSQ-UHFFFAOYSA-N 0.000 claims 1
- UZBQNJGGBIRSMC-UHFFFAOYSA-N 2-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-5-methoxy-n,n-dimethylaniline Chemical compound CN(C)C1=CC(OC)=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 UZBQNJGGBIRSMC-UHFFFAOYSA-N 0.000 claims 1
- WSDVMENNDRMSOF-UHFFFAOYSA-N 2-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-5-methoxyaniline Chemical compound NC1=CC(OC)=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 WSDVMENNDRMSOF-UHFFFAOYSA-N 0.000 claims 1
- IFWDNQLVFWFJLO-UHFFFAOYSA-N 2-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-5-methoxybenzonitrile Chemical compound N#CC1=CC(OC)=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 IFWDNQLVFWFJLO-UHFFFAOYSA-N 0.000 claims 1
- HOCDRRJDXBGRFL-UHFFFAOYSA-N 2-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-5-nitrobenzonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C([N+]([O-])=O)C=C1C#N HOCDRRJDXBGRFL-UHFFFAOYSA-N 0.000 claims 1
- WHFIPLCENOKQSW-UHFFFAOYSA-N 2-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 WHFIPLCENOKQSW-UHFFFAOYSA-N 0.000 claims 1
- XUGQXSRSYRUBJJ-UHFFFAOYSA-N 2-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-n,n-dimethylaniline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=CC=C1N(C)C XUGQXSRSYRUBJJ-UHFFFAOYSA-N 0.000 claims 1
- DJKDTMZPMKYUFD-UHFFFAOYSA-N 2-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-n-ethylaniline Chemical compound CCNC1=CC=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 DJKDTMZPMKYUFD-UHFFFAOYSA-N 0.000 claims 1
- ZBZGLERENJHYTQ-UHFFFAOYSA-N 2-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-n-phenylaniline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=CC=C1NC1=CC=CC=C1 ZBZGLERENJHYTQ-UHFFFAOYSA-N 0.000 claims 1
- APPRHOSZXXDJGF-UHFFFAOYSA-N 2-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]aniline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=CC=C1N APPRHOSZXXDJGF-UHFFFAOYSA-N 0.000 claims 1
- OSBNYXDWZIADDX-UHFFFAOYSA-N 2-[4-[2-cyclopropyl-6-(dimethylamino)quinazolin-4-yl]piperazin-1-yl]benzamide Chemical compound C12=CC(N(C)C)=CC=C2N=C(C2CC2)N=C1N(CC1)CCN1C1=CC=CC=C1C(N)=O OSBNYXDWZIADDX-UHFFFAOYSA-N 0.000 claims 1
- RRQMTTVLMMRAEF-UHFFFAOYSA-N 2-[6,7-dimethoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazolin-2-yl]-n,n-dimethylethanamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC(CCN(C)C)=NC=1N(CC1)CCN1C1=CC=CC=C1OC RRQMTTVLMMRAEF-UHFFFAOYSA-N 0.000 claims 1
- HMQBEFCEIAINOM-UHFFFAOYSA-N 2-[[2-cyclopropyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazolin-6-yl]-(2-hydroxyethyl)amino]ethanol Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(CCO)CCO)CC1 HMQBEFCEIAINOM-UHFFFAOYSA-N 0.000 claims 1
- HIBXHEVZWKXTQG-UHFFFAOYSA-N 2-[[2-cyclopropyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(C)CCO)CC1 HIBXHEVZWKXTQG-UHFFFAOYSA-N 0.000 claims 1
- AULHLHISOZNPLP-UHFFFAOYSA-N 2-[[2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound COC1=CC=CC=C1C1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(C)CCO)CC1 AULHLHISOZNPLP-UHFFFAOYSA-N 0.000 claims 1
- TWKQXPMKDQQWCX-UHFFFAOYSA-N 2-benzyl-6,7-dimethoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(CC=3C=CC=CC=3)N=2)CC1 TWKQXPMKDQQWCX-UHFFFAOYSA-N 0.000 claims 1
- ACIJHJRFDXXOKP-UHFFFAOYSA-N 2-cyclobutyl-4-[4-(2,4-dimethoxyphenyl)piperazin-1-yl]-6,7-dimethoxyquinazoline Chemical compound COC1=CC(OC)=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CCC2)CC1 ACIJHJRFDXXOKP-UHFFFAOYSA-N 0.000 claims 1
- GNFDMFYTUKMSND-UHFFFAOYSA-N 2-cyclobutyl-4-[4-(2-fluorophenyl)piperazin-1-yl]-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CCC2)=NC=1N(CC1)CCN1C1=CC=CC=C1F GNFDMFYTUKMSND-UHFFFAOYSA-N 0.000 claims 1
- RABPYCTZPIOHBV-UHFFFAOYSA-N 2-cyclobutyl-6,7-dimethoxy-4-(4-phenylpiperazin-1-yl)quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CCC2)=NC=1N(CC1)CCN1C1=CC=CC=C1 RABPYCTZPIOHBV-UHFFFAOYSA-N 0.000 claims 1
- GPLGXZOMVXBMDO-UHFFFAOYSA-N 2-cyclobutyl-6,7-dimethoxy-4-(4-pyridin-2-ylpiperazin-1-yl)quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CCC2)=NC=1N(CC1)CCN1C1=CC=CC=N1 GPLGXZOMVXBMDO-UHFFFAOYSA-N 0.000 claims 1
- QAHFFKCDOYHKTJ-UHFFFAOYSA-N 2-cyclobutyl-6,7-dimethoxy-4-[4-(2-methylphenyl)piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CCC2)=NC=1N(CC1)CCN1C1=CC=CC=C1C QAHFFKCDOYHKTJ-UHFFFAOYSA-N 0.000 claims 1
- IOIVOCWFSGHJDB-UHFFFAOYSA-N 2-cyclobutyl-6,7-dimethoxy-4-[4-(2-nitrophenyl)piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CCC2)=NC=1N(CC1)CCN1C1=CC=CC=C1[N+]([O-])=O IOIVOCWFSGHJDB-UHFFFAOYSA-N 0.000 claims 1
- YLCQYVWUXXVXPS-UHFFFAOYSA-N 2-cyclobutyl-6,7-dimethoxy-4-[4-(3-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound COC1=CC=CC(N2CCN(CC2)C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CCC2)=C1 YLCQYVWUXXVXPS-UHFFFAOYSA-N 0.000 claims 1
- QMNQEIUIXDQYDW-UHFFFAOYSA-N 2-cyclobutyl-6,7-dimethoxy-4-[4-(4-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CCC2)CC1 QMNQEIUIXDQYDW-UHFFFAOYSA-N 0.000 claims 1
- LNDSEFGPZZDKQX-UHFFFAOYSA-N 2-cyclohexyl-6,7-dimethoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CCCCC2)=NC=1N(CC1)CCN1C1=CC=CC=C1OC LNDSEFGPZZDKQX-UHFFFAOYSA-N 0.000 claims 1
- VEWIAFHMDFXVFL-UHFFFAOYSA-N 2-cyclopentyl-6,7-dimethoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CCCC2)CC1 VEWIAFHMDFXVFL-UHFFFAOYSA-N 0.000 claims 1
- CESKIGMDKSXTJT-UHFFFAOYSA-N 2-cyclopropyl-4-(3-fluoro-3-phenylpyrrolidin-1-yl)-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(C1)CCC1(F)C1=CC=CC=C1 CESKIGMDKSXTJT-UHFFFAOYSA-N 0.000 claims 1
- OBXBPCQXHNIMOD-UHFFFAOYSA-N 2-cyclopropyl-4-[3-fluoro-3-(3-methoxyphenyl)pyrrolidin-1-yl]-6,7-dimethoxyquinazoline Chemical compound COC1=CC=CC(C2(F)CN(CC2)C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)=C1 OBXBPCQXHNIMOD-UHFFFAOYSA-N 0.000 claims 1
- HXJIWXAJAMTILQ-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2,3-dichlorophenyl)piperazin-1-yl]-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=CC(Cl)=C1Cl HXJIWXAJAMTILQ-UHFFFAOYSA-N 0.000 claims 1
- FAZGVHSNNNNFLG-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2,4-dichlorophenyl)piperazin-1-yl]-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(Cl)C=C1Cl FAZGVHSNNNNFLG-UHFFFAOYSA-N 0.000 claims 1
- FELRNVDAQNZPFW-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2,4-dimethoxyphenyl)piperazin-1-yl]-6,7-dimethoxyquinazoline Chemical compound COC1=CC(OC)=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 FELRNVDAQNZPFW-UHFFFAOYSA-N 0.000 claims 1
- GQJGULGBECTZEF-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-fluorophenyl)piperazin-1-yl]-n,n-dimethylquinazolin-6-amine Chemical compound C12=CC(N(C)C)=CC=C2N=C(C2CC2)N=C1N(CC1)CCN1C1=CC=CC=C1F GQJGULGBECTZEF-UHFFFAOYSA-N 0.000 claims 1
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- IIFQIPBILWDGJY-UHFFFAOYSA-N 2-cyclopropyl-6,7-difluoro-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(F)=C(F)C=C3N=C(N=2)C2CC2)CC1 IIFQIPBILWDGJY-UHFFFAOYSA-N 0.000 claims 1
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- IPIQGWLIJGMUDW-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[3-(3-methoxyphenyl)cyclopentyl]quinazoline Chemical compound COC1=CC=CC(C2CC(CC2)C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)=C1 IPIQGWLIJGMUDW-UHFFFAOYSA-N 0.000 claims 1
- UNCDMDBJROBZPF-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-(2-methoxy-4-nitrophenyl)piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C([N+]([O-])=O)C=C1OC UNCDMDBJROBZPF-UHFFFAOYSA-N 0.000 claims 1
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- KSEPWCUCBVMLMT-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCC1C1=CC=CC=C1OC KSEPWCUCBVMLMT-UHFFFAOYSA-N 0.000 claims 1
- ZBTDJODZERKVEQ-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-(2-nitro-4-phenylmethoxyphenyl)piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C(C(=C1)[N+]([O-])=O)=CC=C1OCC1=CC=CC=C1 ZBTDJODZERKVEQ-UHFFFAOYSA-N 0.000 claims 1
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- NYQIUURACBALAT-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-piperazin-1-ylquinazoline;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N1CCNCC1 NYQIUURACBALAT-UHFFFAOYSA-N 0.000 claims 1
- KDXFWXFNLAOASN-UHFFFAOYSA-N 2-cyclopropyl-6,8-dimethoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound C12=CC(OC)=CC(OC)=C2N=C(C2CC2)N=C1N(CC1)CCN1C1=CC=CC=C1OC KDXFWXFNLAOASN-UHFFFAOYSA-N 0.000 claims 1
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- ACGNRJGRDMUEKJ-UHFFFAOYSA-N 2-cyclopropyl-6-fluoro-7-methoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound C=12C=C(F)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=CC=C1OC ACGNRJGRDMUEKJ-UHFFFAOYSA-N 0.000 claims 1
- NCKNDZSBOAHYCM-UHFFFAOYSA-N 2-cyclopropyl-6-methoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]-7-(trifluoromethyl)quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(OC)=C(C=C3N=C(N=2)C2CC2)C(F)(F)F)CC1 NCKNDZSBOAHYCM-UHFFFAOYSA-N 0.000 claims 1
- STFABVUAJKVNPC-UHFFFAOYSA-N 2-cyclopropyl-6-methoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]-7-methylquinazoline Chemical compound N1=C2C=C(C)C(OC)=CC2=C(N2CCN(CC2)C=2C(=CC=CC=2)OC)N=C1C1CC1 STFABVUAJKVNPC-UHFFFAOYSA-N 0.000 claims 1
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- GEMQYWIUIQISOA-UHFFFAOYSA-N 2-cyclopropyl-7-fluoro-6-methoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound N1=C2C=C(F)C(OC)=CC2=C(N2CCN(CC2)C=2C(=CC=CC=2)OC)N=C1C1CC1 GEMQYWIUIQISOA-UHFFFAOYSA-N 0.000 claims 1
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| PL3505157T3 (pl) | 2017-12-29 | 2022-04-11 | Celon Pharma S.A. | Kompozycja ketaminy w postaci suchego proszku do podawania dopłucnego w leczeniu depresji opornej na leczenie |
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| JPS58172379A (ja) | 1982-04-02 | 1983-10-11 | Showa Denko Kk | 新規なキナゾリン誘導体 |
| US5624926A (en) * | 1993-02-18 | 1997-04-29 | Kyowa Hakko Kogyo Co., Ltd. | Piperidinyl-dioxoquinazolines as adenosine reuptake inhibitors |
| US5866562A (en) | 1996-10-25 | 1999-02-02 | Bayer Aktiengesellschaft | Ring-bridged bis-quinolines |
| WO2002024667A1 (en) | 2000-09-20 | 2002-03-28 | Merck Patent Gmbh | 4-amino-quinazolines |
| US7713983B2 (en) | 2003-03-03 | 2010-05-11 | Vertex Pharmaceuticals Incorporated | Quinazolines useful as modulators of ion channels |
| BRPI0415683A (pt) * | 2003-11-03 | 2006-12-19 | Warner Lambert Co | inibidores da reabsorção de norepinefrina para o tratamento de distúrbios do sistema nervoso central |
| WO2006007864A1 (en) | 2004-07-17 | 2006-01-26 | Max Planck Geselllschaft Zur Förderung Der Wissenschaft | Treating neurodegenerative conditions |
| EP1968968A1 (en) * | 2005-12-21 | 2008-09-17 | PainCeptor Pharma Corp. | Compositions and methods for modulating gated ion channels |
| US8153803B2 (en) * | 2006-07-18 | 2012-04-10 | The General Hospital Corporation | Compositions and methods for modulating sirtuin activity |
| CA2709784A1 (en) * | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| WO2011153553A2 (en) | 2010-06-04 | 2011-12-08 | The Regents Of The University Of California | Methods and compositions for kinase inhibition |
| CN102786483B (zh) * | 2011-05-19 | 2016-03-30 | 复旦大学 | 4-（4-苯基哌嗪基）喹唑啉类衍生物的药用用途 |
| US9914730B2 (en) | 2012-09-28 | 2018-03-13 | Cancer Research Technology Limited | Azaquinazoline inhibitors of Atypical protein Kinase C |
| WO2014100501A1 (en) | 2012-12-20 | 2014-06-26 | Sanford-Burnham Medical Research Institute | Small molecule agonists of neurotensin receptor 1 |
| JP6599908B2 (ja) | 2014-06-25 | 2019-10-30 | サンフォード−バーンハム メディカル リサーチ インスティテュート | ニューロテンシン受容体１の小分子アゴニスト |
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- 2013-12-19 US US14/652,705 patent/US9868707B2/en active Active
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