JP2016507501A5

JP2016507501A5 -

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Publication number: JP2016507501A5
Authority: JP; Japan
Prior art keywords: piperazin; cyclopropyl; phenyl; dimethoxy; methoxy
Prior art date: 2013-12-19
Legal status : Granted

Application number

JP2015549744A

Other languages

English (en)

Japanese (ja)

Other versions

JP2016507501A (ja

JP6391120B2 (ja

Filing date

2013-12-19

Publication date

2017-02-09

2013-12-19 Application filed filed Critical

2013-12-19 Priority claimed from PCT/US2013/076735 external-priority patent/WO2014100501A1/en

2016-03-10 Publication of JP2016507501A publication Critical patent/JP2016507501A/ja

2017-02-09 Publication of JP2016507501A5 publication Critical patent/JP2016507501A5/ja

2018-09-19 Application granted granted Critical

2018-09-19 Publication of JP6391120B2 publication Critical patent/JP6391120B2/ja

Status Active legal-status Critical Current

2033-12-19 Anticipated expiration legal-status Critical

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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
RZVUGBVEYJBPHL-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-methoxy-5-methylphenyl)piperazin-1-yl]-n,n-dimethylquinazolin-6-amine Chemical compound COC1=CC=C(C)C=C1N1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(C)C)CC1 RZVUGBVEYJBPHL-UHFFFAOYSA-N 0.000 claims 1
LRNKYCGBQXQMAH-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]-6-(4-methylpiperazin-1-yl)quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N2CCN(C)CC2)CC1 LRNKYCGBQXQMAH-UHFFFAOYSA-N 0.000 claims 1
VIGHBVDSYLJWEJ-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]-6-piperazin-1-ylquinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N2CCNCC2)CC1 VIGHBVDSYLJWEJ-UHFFFAOYSA-N 0.000 claims 1
RVEOQOXFFIQHHQ-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]-6-piperidin-1-ylquinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N2CCCCC2)CC1 RVEOQOXFFIQHHQ-UHFFFAOYSA-N 0.000 claims 1
RPVKCCYPXHLPCQ-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]-n,n,7-trimethylquinazolin-6-amine Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(=C(C)C=C3N=C(N=2)C2CC2)N(C)C)CC1 RPVKCCYPXHLPCQ-UHFFFAOYSA-N 0.000 claims 1
JAKXZOJZFFSCSQ-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]-n,n-dimethylquinazolin-7-amine Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC=C(C=C3N=C(N=2)C2CC2)N(C)C)CC1 JAKXZOJZFFSCSQ-UHFFFAOYSA-N 0.000 claims 1
FUWFXGWRZXHCBN-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]-n-methyl-n-propylquinazolin-6-amine Chemical compound C12=CC(N(C)CCC)=CC=C2N=C(C2CC2)N=C1N(CC1)CCN1C1=CC=CC=C1OC FUWFXGWRZXHCBN-UHFFFAOYSA-N 0.000 claims 1
UPBSYCNPFBASAM-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]-n-phenylquinazolin-6-amine Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(NC=4C=CC=CC=4)=CC=C3N=C(N=2)C2CC2)CC1 UPBSYCNPFBASAM-UHFFFAOYSA-N 0.000 claims 1
SKYLVNWNYAMRSI-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]pyrido[2,3-d]pyrimidine Chemical compound COc1ccccc1N1CCN(CC1)c1nc(nc2ncccc12)C1CC1 SKYLVNWNYAMRSI-UHFFFAOYSA-N 0.000 claims 1
AUUOZQFWVNCFOW-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC=CC=C3N=C(N=2)C2CC2)CC1 AUUOZQFWVNCFOW-UHFFFAOYSA-N 0.000 claims 1
PRJBXYRFMXTWEB-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]-n,n-dimethylquinazolin-6-amine Chemical compound COC1=CC=CC=C1C1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(C)C)CC1 PRJBXYRFMXTWEB-UHFFFAOYSA-N 0.000 claims 1
TXOCLFUBPUBFHJ-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]-n-methyl-n-(2-morpholin-4-ylethyl)quinazolin-6-amine Chemical compound COC1=CC=CC=C1C1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(C)CCN2CCOCC2)CC1 TXOCLFUBPUBFHJ-UHFFFAOYSA-N 0.000 claims 1
UZLNDCSWMFJDMK-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]-n-methyl-n-propylquinazolin-6-amine Chemical compound C12=CC(N(C)CCC)=CC=C2N=C(C2CC2)N=C1N(CC1)CCC1C1=CC=CC=C1OC UZLNDCSWMFJDMK-UHFFFAOYSA-N 0.000 claims 1
CHRJGXFPIBZYHT-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(3-methoxyphenyl)piperazin-1-yl]-n,n-dimethylquinazolin-6-amine Chemical compound COC1=CC=CC(N2CCN(CC2)C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(C)C)=C1 CHRJGXFPIBZYHT-UHFFFAOYSA-N 0.000 claims 1
XSAHHOZQFIVPLE-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(F)C=C1OC XSAHHOZQFIVPLE-UHFFFAOYSA-N 0.000 claims 1
BRAWHGLODVOFRM-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]-n,n-dimethylquinazolin-6-amine Chemical compound COC1=CC(F)=CC=C1N1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(C)C)CC1 BRAWHGLODVOFRM-UHFFFAOYSA-N 0.000 claims 1
HKRHNOUEJZHBOY-UHFFFAOYSA-N 2-cyclopropyl-4-[4-(4-methoxyphenyl)piperazin-1-yl]-n,n-dimethylquinazolin-6-amine Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(C)C)CC1 HKRHNOUEJZHBOY-UHFFFAOYSA-N 0.000 claims 1
HQJBIXJIYUSYEC-UHFFFAOYSA-N 2-cyclopropyl-4-[4-[2-methoxy-4-(trifluoromethoxy)phenyl]piperazin-1-yl]-n,n-dimethylquinazolin-6-amine Chemical compound COC1=CC(OC(F)(F)F)=CC=C1N1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(C)C)CC1 HQJBIXJIYUSYEC-UHFFFAOYSA-N 0.000 claims 1
WOSHXEZAGBLDKI-UHFFFAOYSA-N 2-cyclopropyl-5,6-dimethoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=C(OC)C(OC)=CC=C3N=C(N=2)C2CC2)CC1 WOSHXEZAGBLDKI-UHFFFAOYSA-N 0.000 claims 1
FGKLKORWLMRIQK-UHFFFAOYSA-N 2-cyclopropyl-5,8-dimethoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=C(OC)C=CC(OC)=C3N=C(N=2)C2CC2)CC1 FGKLKORWLMRIQK-UHFFFAOYSA-N 0.000 claims 1
BELSQADEAVJJLS-UHFFFAOYSA-N 2-cyclopropyl-5-methoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=C(OC)C=CC=C3N=C(N=2)C2CC2)CC1 BELSQADEAVJJLS-UHFFFAOYSA-N 0.000 claims 1
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
DVDOSLYVJNUOAR-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-(3-methyl-4-phenylpiperazin-1-yl)quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1C)CCN1C1=CC=CC=C1 DVDOSLYVJNUOAR-UHFFFAOYSA-N 0.000 claims 1
IXUSZIYDDDIEIF-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-(3-phenylpyrrolidin-1-yl)quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(C1)CCC1C1=CC=CC=C1 IXUSZIYDDDIEIF-UHFFFAOYSA-N 0.000 claims 1
XXJBIZCGMPWYCF-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[1-(2-methoxyphenyl)piperidin-4-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1C(CC1)CCN1C1=CC=CC=C1OC XXJBIZCGMPWYCF-UHFFFAOYSA-N 0.000 claims 1
YYVVUOKNHGRTCA-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[3-(2-methoxyphenyl)pyrrolidin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1C1CN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 YYVVUOKNHGRTCA-UHFFFAOYSA-N 0.000 claims 1
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
HQPPYJROVWCCQS-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-(2-methoxy-5-methylphenyl)piperazin-1-yl]quinazoline Chemical compound COC1=CC=C(C)C=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 HQPPYJROVWCCQS-UHFFFAOYSA-N 0.000 claims 1
QBSZPFWZNWVGNJ-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-(2-methoxy-5-nitrophenyl)piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC([N+]([O-])=O)=CC=C1OC QBSZPFWZNWVGNJ-UHFFFAOYSA-N 0.000 claims 1
ANKXJCOOQIAFLN-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-(2-methoxyphenyl)-1,4-diazepan-1-yl]quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CCC1 ANKXJCOOQIAFLN-UHFFFAOYSA-N 0.000 claims 1
GTFKQERXVDOLKA-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-(2-methoxyphenyl)-2-methylpiperazin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1N1CC(C)N(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 GTFKQERXVDOLKA-UHFFFAOYSA-N 0.000 claims 1
HVNRUGQDUAKEDF-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-(2-methoxyphenyl)-3,6-dihydro-2h-pyridin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1C1=CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 HVNRUGQDUAKEDF-UHFFFAOYSA-N 0.000 claims 1
SWEOAXMICIJCQC-UHFFFAOYSA-N 2-cyclopropyl-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)C2CC2)CC1 SWEOAXMICIJCQC-UHFFFAOYSA-N 0.000 claims 1
ACAKVRBXJQGKGD-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(C=2)C2CC2)CC1 ACAKVRBXJQGKGD-UHFFFAOYSA-N 0.000 claims 1
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
YCUSYDFEWHMORT-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-(2-nitrophenyl)piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=CC=C1[N+]([O-])=O YCUSYDFEWHMORT-UHFFFAOYSA-N 0.000 claims 1
KLPOZAJBHRGIRQ-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-(2-piperidin-1-ylphenyl)piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=CC=C1N1CCCCC1 KLPOZAJBHRGIRQ-UHFFFAOYSA-N 0.000 claims 1
DEYAIQUROLDSDJ-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-(2-pyrrolidin-1-ylphenyl)piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=CC=C1N1CCCC1 DEYAIQUROLDSDJ-UHFFFAOYSA-N 0.000 claims 1
DEBSLCPUWLPWJL-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-(4-methoxy-2-nitrophenyl)piperazin-1-yl]quinazoline Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 DEBSLCPUWLPWJL-UHFFFAOYSA-N 0.000 claims 1
UEXZCLTYAROOFY-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-[(2-methoxyphenyl)methyl]piperazin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1CN1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 UEXZCLTYAROOFY-UHFFFAOYSA-N 0.000 claims 1
NTOIAIPOJUIVOK-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-[(4-methylphenyl)methyl]piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1CC1=CC=C(C)C=C1 NTOIAIPOJUIVOK-UHFFFAOYSA-N 0.000 claims 1
DUEODDHSICEEOT-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-[2-(4-methylpiperazin-1-yl)phenyl]piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=CC=C1N1CCN(C)CC1 DUEODDHSICEEOT-UHFFFAOYSA-N 0.000 claims 1
ASJSUGPUWQZYRZ-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-[2-methoxy-4-(trifluoromethoxy)phenyl]piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(OC(F)(F)F)C=C1OC ASJSUGPUWQZYRZ-UHFFFAOYSA-N 0.000 claims 1
NKQAWAXQDXSYQB-UHFFFAOYSA-N 2-cyclopropyl-6,7-dimethoxy-4-[4-[2-methoxy-4-(trifluoromethyl)phenyl]piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(C(F)(F)F)C=C1OC NKQAWAXQDXSYQB-UHFFFAOYSA-N 0.000 claims 1
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
JGMVZGBNLHLHLK-UHFFFAOYSA-N 2-cyclopropyl-6-fluoro-4-[4-(2-methoxyphenyl)piperazin-1-yl]-n,n-dimethylquinazolin-7-amine Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(F)=C(N(C)C)C=C3N=C(N=2)C2CC2)CC1 JGMVZGBNLHLHLK-UHFFFAOYSA-N 0.000 claims 1
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
DWYLWHCPKQJGEK-UHFFFAOYSA-N 2-cyclopropyl-6-methoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]pyrido[3,4-d]pyrimidine Chemical compound N1=C2C=NC(OC)=CC2=C(N2CCN(CC2)C=2C(=CC=CC=2)OC)N=C1C1CC1 DWYLWHCPKQJGEK-UHFFFAOYSA-N 0.000 claims 1
LWOOFEWPFCGPLQ-UHFFFAOYSA-N 2-cyclopropyl-7-fluoro-4-[4-(2-methoxyphenyl)piperazin-1-yl]-n,n-dimethylquinazolin-6-amine Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(=C(F)C=C3N=C(N=2)C2CC2)N(C)C)CC1 LWOOFEWPFCGPLQ-UHFFFAOYSA-N 0.000 claims 1
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
ATXXDRVTTGKTAX-UHFFFAOYSA-N 2-cyclopropyl-8-methoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC=CC(OC)=C3N=C(N=2)C2CC2)CC1 ATXXDRVTTGKTAX-UHFFFAOYSA-N 0.000 claims 1
UAZRGMMWRDQHMA-UHFFFAOYSA-N 2-cyclopropyl-n,n-diethyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazolin-6-amine Chemical compound C12=CC(N(CC)CC)=CC=C2N=C(C2CC2)N=C1N(CC1)CCN1C1=CC=CC=C1OC UAZRGMMWRDQHMA-UHFFFAOYSA-N 0.000 claims 1
YXVXPIJCCLBGEJ-UHFFFAOYSA-N 2-cyclopropyl-n,n-diethyl-6-fluoro-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazolin-7-amine Chemical compound C=12C=C(F)C(N(CC)CC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=CC=C1OC YXVXPIJCCLBGEJ-UHFFFAOYSA-N 0.000 claims 1
JYNGJSHCRYGPND-UHFFFAOYSA-N 2-cyclopropyl-n,n-diethyl-7-fluoro-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazolin-6-amine Chemical compound N1=C2C=C(F)C(N(CC)CC)=CC2=C(N2CCN(CC2)C=2C(=CC=CC=2)OC)N=C1C1CC1 JYNGJSHCRYGPND-UHFFFAOYSA-N 0.000 claims 1
BQXFAIRPIUPSDZ-UHFFFAOYSA-N 2-cyclopropyl-n,n-dimethyl-4-[4-(2-methylphenyl)piperazin-1-yl]quinazolin-6-amine Chemical compound C12=CC(N(C)C)=CC=C2N=C(C2CC2)N=C1N(CC1)CCN1C1=CC=CC=C1C BQXFAIRPIUPSDZ-UHFFFAOYSA-N 0.000 claims 1
KLQMEMWPTJRSDO-UHFFFAOYSA-N 2-cyclopropyl-n-(2-methoxyethyl)-4-[4-(2-methoxyphenyl)piperazin-1-yl]-n-methylquinazolin-6-amine Chemical compound C12=CC(N(C)CCOC)=CC=C2N=C(C2CC2)N=C1N(CC1)CCN1C1=CC=CC=C1OC KLQMEMWPTJRSDO-UHFFFAOYSA-N 0.000 claims 1
DROZWECPKCAFDI-UHFFFAOYSA-N 2-cyclopropyl-n-(2-methoxyethyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]-n-methylquinazolin-6-amine Chemical compound C12=CC(N(C)CCOC)=CC=C2N=C(C2CC2)N=C1N(CC1)CCC1C1=CC=CC=C1OC DROZWECPKCAFDI-UHFFFAOYSA-N 0.000 claims 1
NARMSPHKTYOPTK-UHFFFAOYSA-N 2-cyclopropyl-n-ethyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]-n,7-dimethylquinazolin-6-amine Chemical compound N1=C2C=C(C)C(N(C)CC)=CC2=C(N2CCN(CC2)C=2C(=CC=CC=2)OC)N=C1C1CC1 NARMSPHKTYOPTK-UHFFFAOYSA-N 0.000 claims 1
NVIPRMJCYCQETI-UHFFFAOYSA-N 2-cyclopropyl-n-ethyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]-n-methylquinazolin-6-amine Chemical compound C12=CC(N(C)CC)=CC=C2N=C(C2CC2)N=C1N(CC1)CCC1C1=CC=CC=C1OC NVIPRMJCYCQETI-UHFFFAOYSA-N 0.000 claims 1
UFOKSVRATXOQOA-UHFFFAOYSA-N 2-ethenyl-6,7-dimethoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C=C)=NC=1N(CC1)CCN1C1=CC=CC=C1OC UFOKSVRATXOQOA-UHFFFAOYSA-N 0.000 claims 1
PDEAKHQWPNWDTL-UHFFFAOYSA-N 2-ethyl-6,7-dimethoxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(CC)=NC=1N(CC1)CCN1C1=CC=CC=C1OC PDEAKHQWPNWDTL-UHFFFAOYSA-N 0.000 claims 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
SXPZEDAIRKHEJQ-UHFFFAOYSA-N 2-tert-butyl-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)C(C)(C)C)CC1 SXPZEDAIRKHEJQ-UHFFFAOYSA-N 0.000 claims 1
JGWXIKALIWFLGL-UHFFFAOYSA-N 2-tert-butyl-6,7-dimethoxy-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazoline Chemical compound COC1=CC=CC=C1C1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C(C)(C)C)CC1 JGWXIKALIWFLGL-UHFFFAOYSA-N 0.000 claims 1
OUGPSNYKQPVPCC-UHFFFAOYSA-N 3-[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(N(C)C)=C1 OUGPSNYKQPVPCC-UHFFFAOYSA-N 0.000 claims 1
QRQQWRNDYWHYJF-UHFFFAOYSA-N 3-[3-chloro-4-[4-[2-cyclopropyl-6-(dimethylamino)quinazolin-4-yl]piperazin-1-yl]phenyl]-1,1-dimethylurea Chemical compound ClC1=CC(NC(=O)N(C)C)=CC=C1N1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(C)C)CC1 QRQQWRNDYWHYJF-UHFFFAOYSA-N 0.000 claims 1
RCXVLPLOBRKTRJ-UHFFFAOYSA-N 3-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-4-methoxy-n,n-dimethylaniline Chemical compound COC1=CC=C(N(C)C)C=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 RCXVLPLOBRKTRJ-UHFFFAOYSA-N 0.000 claims 1
VDIWQEMEZRSNQK-UHFFFAOYSA-N 3-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-4-methoxy-n-methylaniline Chemical compound CNC1=CC=C(OC)C(N2CCN(CC2)C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)=C1 VDIWQEMEZRSNQK-UHFFFAOYSA-N 0.000 claims 1
IVYWZGNOAMAYSG-UHFFFAOYSA-N 3-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-4-methoxyaniline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC(N)=CC=C1OC IVYWZGNOAMAYSG-UHFFFAOYSA-N 0.000 claims 1
ZHYUNIYHCVLKSQ-UHFFFAOYSA-N 3-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=CC(N2CCN(CC2)C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)=C1 ZHYUNIYHCVLKSQ-UHFFFAOYSA-N 0.000 claims 1
JERGNPJWFAMAEL-UHFFFAOYSA-N 3-[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(N(C)C)=C1 JERGNPJWFAMAEL-UHFFFAOYSA-N 0.000 claims 1
FDWGNCRYRQWVKH-UHFFFAOYSA-N 3-amino-4-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]phenol Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(O)C=C1N FDWGNCRYRQWVKH-UHFFFAOYSA-N 0.000 claims 1
IMJRNZXGJFASNR-UHFFFAOYSA-N 3-chloro-4-[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=C(N)C=C1Cl IMJRNZXGJFASNR-UHFFFAOYSA-N 0.000 claims 1
YBXNJTGGPZRHOW-UHFFFAOYSA-N 3-chloro-4-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]benzamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(C(N)=O)C=C1Cl YBXNJTGGPZRHOW-UHFFFAOYSA-N 0.000 claims 1
FUOCTPWXRHVQIE-UHFFFAOYSA-N 3-chloro-4-[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=C(C#N)C=C1Cl FUOCTPWXRHVQIE-UHFFFAOYSA-N 0.000 claims 1
BHQRUBIYKLQCAH-UHFFFAOYSA-N 3-chloro-4-[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=C(C(N)=O)C=C1Cl BHQRUBIYKLQCAH-UHFFFAOYSA-N 0.000 claims 1
NKKXCSLQVCBRAU-UHFFFAOYSA-N 3-cyclopropyl-6,7-dimethoxy-1-[4-(2-methoxyphenyl)piperazin-1-yl]isoquinoline Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3C=C(N=2)C2CC2)CC1 NKKXCSLQVCBRAU-UHFFFAOYSA-N 0.000 claims 1
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
QPBOFOLPPKASSX-UHFFFAOYSA-N 4-[2-cyclopropyl-4-[4-(2-methoxyphenyl)piperazin-1-yl]quinazolin-6-yl]morpholine Chemical compound COC1=CC=CC=C1N1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N2CCOCC2)CC1 QPBOFOLPPKASSX-UHFFFAOYSA-N 0.000 claims 1
YMFZSYNNPNUDQN-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenyl)piperazin-1-yl]-2-cyclopropyl-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(F)C=C1Cl YMFZSYNNPNUDQN-UHFFFAOYSA-N 0.000 claims 1
ZTISFASVSWFXAS-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenyl)piperazin-1-yl]-2-cyclopropyl-n,n-dimethylquinazolin-6-amine Chemical compound C12=CC(N(C)C)=CC=C2N=C(C2CC2)N=C1N(CC1)CCN1C1=CC=C(F)C=C1Cl ZTISFASVSWFXAS-UHFFFAOYSA-N 0.000 claims 1
MDTDZNDWIWDNOE-UHFFFAOYSA-N 4-[4-(2-chloro-4-methoxyphenyl)piperazin-1-yl]-2-cyclopropyl-6,7-dimethoxyquinazoline Chemical compound ClC1=CC(OC)=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 MDTDZNDWIWDNOE-UHFFFAOYSA-N 0.000 claims 1
XZJHQQAKXCETJR-UHFFFAOYSA-N 4-[4-(2-chloro-4-methylphenyl)piperazin-1-yl]-2-cyclopropyl-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(C)C=C1Cl XZJHQQAKXCETJR-UHFFFAOYSA-N 0.000 claims 1
NUTTXJCRQFOFFM-UHFFFAOYSA-N 4-[4-(2-chloro-4-methylphenyl)piperazin-1-yl]-2-cyclopropyl-n,n-dimethylquinazolin-6-amine Chemical compound C12=CC(N(C)C)=CC=C2N=C(C2CC2)N=C1N(CC1)CCN1C1=CC=C(C)C=C1Cl NUTTXJCRQFOFFM-UHFFFAOYSA-N 0.000 claims 1
JGPZWZBSUPPTRX-UHFFFAOYSA-N 4-[4-(2-chloro-4-nitrophenyl)piperazin-1-yl]-2-cyclopropyl-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C([N+]([O-])=O)C=C1Cl JGPZWZBSUPPTRX-UHFFFAOYSA-N 0.000 claims 1
GCVVIGBCICNSIY-UHFFFAOYSA-N 4-[4-(2-chlorophenyl)piperazin-1-yl]-2-cyclobutyl-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CCC2)=NC=1N(CC1)CCN1C1=CC=CC=C1Cl GCVVIGBCICNSIY-UHFFFAOYSA-N 0.000 claims 1
KMQHCXSTAQSUDR-UHFFFAOYSA-N 4-[4-(2-chlorophenyl)piperazin-1-yl]-2-cyclopropyl-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=CC=C1Cl KMQHCXSTAQSUDR-UHFFFAOYSA-N 0.000 claims 1
WUEHUVHNRGAPCA-UHFFFAOYSA-N 4-[4-(2-chlorophenyl)piperazin-1-yl]-2-cyclopropyl-n,n-dimethylquinazolin-6-amine Chemical compound C12=CC(N(C)C)=CC=C2N=C(C2CC2)N=C1N(CC1)CCN1C1=CC=CC=C1Cl WUEHUVHNRGAPCA-UHFFFAOYSA-N 0.000 claims 1
UKCACNHYQQFMNR-UHFFFAOYSA-N 4-[4-(2-chlorophenyl)piperazin-1-yl]-6,7-dimethoxy-2-phenylquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C=2C=CC=CC=2)=NC=1N(CC1)CCN1C1=CC=CC=C1Cl UKCACNHYQQFMNR-UHFFFAOYSA-N 0.000 claims 1
RVABNDJVWVNUNC-UHFFFAOYSA-N 4-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-3-(dimethylamino)benzoic acid Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(C(O)=O)C=C1N(C)C RVABNDJVWVNUNC-UHFFFAOYSA-N 0.000 claims 1
ZZLJGWBUUIMDMM-UHFFFAOYSA-N 4-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-3-methoxy-n,n-dimethylaniline Chemical compound COC1=CC(N(C)C)=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 ZZLJGWBUUIMDMM-UHFFFAOYSA-N 0.000 claims 1
QBUZKISNCUOWMB-UHFFFAOYSA-N 4-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-3-methoxyaniline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(N)C=C1OC QBUZKISNCUOWMB-UHFFFAOYSA-N 0.000 claims 1
ZBHRWWDNZVJBDP-UHFFFAOYSA-N 4-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-3-methoxybenzamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(C(N)=O)C=C1OC ZBHRWWDNZVJBDP-UHFFFAOYSA-N 0.000 claims 1
MOUJJKHMZPUTOJ-UHFFFAOYSA-N 4-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-3-methoxybenzoic acid Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(C(O)=O)C=C1OC MOUJJKHMZPUTOJ-UHFFFAOYSA-N 0.000 claims 1
COYMUXAWMIXTDV-UHFFFAOYSA-N 4-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-3-methoxybenzonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(C#N)C=C1OC COYMUXAWMIXTDV-UHFFFAOYSA-N 0.000 claims 1
ARGYIMCZSKSQHN-UHFFFAOYSA-N 4-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 ARGYIMCZSKSQHN-UHFFFAOYSA-N 0.000 claims 1
WXDIOORVGABOSY-UHFFFAOYSA-N 4-[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=C(N(C)C)C=C1 WXDIOORVGABOSY-UHFFFAOYSA-N 0.000 claims 1
DXODZTAGDLSJLS-UHFFFAOYSA-N 4-[4-(2-fluorophenyl)piperazin-1-yl]-6,7-dimethoxy-2-phenylquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C=2C=CC=CC=2)=NC=1N(CC1)CCN1C1=CC=CC=C1F DXODZTAGDLSJLS-UHFFFAOYSA-N 0.000 claims 1
CMXQXTSJKVBANJ-UHFFFAOYSA-N 4-[4-(2-methoxyphenyl)piperidin-1-yl]-n-methyl-2-(1-methylcyclopropyl)-n-(2-morpholin-4-ylethyl)quinazolin-6-amine Chemical compound COC1=CC=CC=C1C1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2(C)CC2)N(C)CCN2CCOCC2)CC1 CMXQXTSJKVBANJ-UHFFFAOYSA-N 0.000 claims 1
SXHWHQMMOSSPNM-UHFFFAOYSA-N 4-[4-(4-chloro-2-methoxyphenyl)piperazin-1-yl]-2-cyclopropyl-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(Cl)C=C1OC SXHWHQMMOSSPNM-UHFFFAOYSA-N 0.000 claims 1
MHQQNOHIVBYRIZ-UHFFFAOYSA-N 4-[4-(4-chloro-2-methoxyphenyl)piperazin-1-yl]-2-cyclopropyl-n,n-dimethylquinazolin-6-amine Chemical compound COC1=CC(Cl)=CC=C1N1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(C)C)CC1 MHQQNOHIVBYRIZ-UHFFFAOYSA-N 0.000 claims 1
QJSSVXHQDQGEIJ-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)piperazin-1-yl]-6,7-dimethoxy-2-phenylquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C=2C=CC=CC=2)=NC=1N(CC1)CCN1C1=CC=C(F)C=C1 QJSSVXHQDQGEIJ-UHFFFAOYSA-N 0.000 claims 1
POGQVBAOVIQAQL-UHFFFAOYSA-N 4-[4-(6-bromo-2-cyclopropylquinazolin-4-yl)piperazin-1-yl]-3-methoxybenzonitrile Chemical compound COC1=CC(C#N)=CC=C1N1CCN(C=2C3=CC(Br)=CC=C3N=C(N=2)C2CC2)CC1 POGQVBAOVIQAQL-UHFFFAOYSA-N 0.000 claims 1
MHFYXZJTMQZPBR-UHFFFAOYSA-N 4-[4-(benzenesulfonyl)piperazin-1-yl]-2-cyclopropyl-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 MHFYXZJTMQZPBR-UHFFFAOYSA-N 0.000 claims 1
CUDYELMNWGZXLH-UHFFFAOYSA-N 4-[4-[2-(azetidin-1-yl)phenyl]piperazin-1-yl]-2-cyclopropyl-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=CC=C1N1CCC1 CUDYELMNWGZXLH-UHFFFAOYSA-N 0.000 claims 1
XYSFJLQDGBVEHC-UHFFFAOYSA-N 4-[4-[2-(azetidin-1-yl)phenyl]piperazin-1-yl]-2-cyclopropyl-n,n-dimethylquinazolin-6-amine Chemical compound C12=CC(N(C)C)=CC=C2N=C(C2CC2)N=C1N(CC1)CCN1C1=CC=CC=C1N1CCC1 XYSFJLQDGBVEHC-UHFFFAOYSA-N 0.000 claims 1
BSPLRGZYYFIPOV-UHFFFAOYSA-N 4-[4-[2-(azetidin-1-yl)phenyl]piperazin-1-yl]-2-cyclopropyl-n-ethyl-n-methylquinazolin-6-amine Chemical compound C12=CC(N(C)CC)=CC=C2N=C(C2CC2)N=C1N(CC1)CCN1C1=CC=CC=C1N1CCC1 BSPLRGZYYFIPOV-UHFFFAOYSA-N 0.000 claims 1
GHZZFAYWMCAQOU-UHFFFAOYSA-N 4-[4-[2-(azetidin-1-yl)phenyl]piperidin-1-yl]-2-cyclopropyl-n,n-dimethylquinazolin-6-amine Chemical compound C12=CC(N(C)C)=CC=C2N=C(C2CC2)N=C1N(CC1)CCC1C1=CC=CC=C1N1CCC1 GHZZFAYWMCAQOU-UHFFFAOYSA-N 0.000 claims 1
NORWFQRUVULURR-UHFFFAOYSA-N 4-[4-[2-(aziridin-1-yl)phenyl]piperazin-1-yl]-2-cyclopropyl-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=CC=C1N1CC1 NORWFQRUVULURR-UHFFFAOYSA-N 0.000 claims 1
HOIGYCQMCUQTNI-UHFFFAOYSA-N 4-[4-[2-chloro-4-(trifluoromethyl)phenyl]piperazin-1-yl]-2-cyclopropyl-6,7-dimethoxyquinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(C(F)(F)F)C=C1Cl HOIGYCQMCUQTNI-UHFFFAOYSA-N 0.000 claims 1
OTYHCZQROYAKMG-UHFFFAOYSA-N 4-[4-[2-cyclopropyl-6-(dimethylamino)quinazolin-4-yl]piperazin-1-yl]-3-methoxybenzonitrile Chemical compound COC1=CC(C#N)=CC=C1N1CCN(C=2C3=CC(=CC=C3N=C(N=2)C2CC2)N(C)C)CC1 OTYHCZQROYAKMG-UHFFFAOYSA-N 0.000 claims 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 1
PGORYKGTHYXBJM-UHFFFAOYSA-N 5-amino-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=C(N)C=C1C#N PGORYKGTHYXBJM-UHFFFAOYSA-N 0.000 claims 1
ACEKIZYISACNLE-UHFFFAOYSA-N 5-amino-2-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]phenol Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(N)C=C1O ACEKIZYISACNLE-UHFFFAOYSA-N 0.000 claims 1
NWEFVBAAZKQMDO-UHFFFAOYSA-N 5-bromo-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=C(Br)C=C1N(C)C NWEFVBAAZKQMDO-UHFFFAOYSA-N 0.000 claims 1
HVQNRXKKQBOFRE-UHFFFAOYSA-N 5-chloro-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=C(Cl)C=C1N(C)C HVQNRXKKQBOFRE-UHFFFAOYSA-N 0.000 claims 1
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125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
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NBMNEQHJUQGRSD-UHFFFAOYSA-N n-(2-cyclopropyl-6,7-dimethoxyquinazolin-5-yl)-n'-(2-methoxyphenyl)-n'-methylethane-1,2-diamine Chemical compound COC1=CC=CC=C1N(C)CCNC1=C(OC)C(OC)=CC2=NC(C3CC3)=NC=C12 NBMNEQHJUQGRSD-UHFFFAOYSA-N 0.000 claims 1
GAFZAZDKGOUAOO-UHFFFAOYSA-N n-[3-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-4-methoxyphenyl]acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 GAFZAZDKGOUAOO-UHFFFAOYSA-N 0.000 claims 1
NUDVGIWWHKSXLY-UHFFFAOYSA-N n-[3-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]-4-methoxyphenyl]methanesulfonamide Chemical compound COC1=CC=C(NS(C)(=O)=O)C=C1N1CCN(C=2C3=CC(OC)=C(OC)C=C3N=C(N=2)C2CC2)CC1 NUDVGIWWHKSXLY-UHFFFAOYSA-N 0.000 claims 1
DEJIFBLSXZGKPQ-UHFFFAOYSA-N n-[3-chloro-4-[4-(2-cyclopropyl-6,7-dimethoxyquinazolin-4-yl)piperazin-1-yl]phenyl]acetamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C2CC2)=NC=1N(CC1)CCN1C1=CC=C(NC(C)=O)C=C1Cl DEJIFBLSXZGKPQ-UHFFFAOYSA-N 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
208000004296 neuralgia Diseases 0.000 claims 1
208000021722 neuropathic pain Diseases 0.000 claims 1
PCJGZPGTCUMMOT-ISULXFBGSA-N neurotensin Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 PCJGZPGTCUMMOT-ISULXFBGSA-N 0.000 claims 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
125000001715 oxadiazolyl group Chemical group 0.000 claims 1
125000002971 oxazolyl group Chemical group 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
125000004193 piperazinyl group Chemical group 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
125000003373 pyrazinyl group Chemical group 0.000 claims 1
125000003226 pyrazolyl group Chemical group 0.000 claims 1
125000002098 pyridazinyl group Chemical group 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
125000000714 pyrimidinyl group Chemical group 0.000 claims 1
125000000168 pyrrolyl group Chemical group 0.000 claims 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
201000000980 schizophrenia Diseases 0.000 claims 1
208000011117 substance-related disease Diseases 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
238000003419 tautomerization reaction Methods 0.000 claims 1
125000003831 tetrazolyl group Chemical group 0.000 claims 1
125000001113 thiadiazolyl group Chemical group 0.000 claims 1
125000000335 thiazolyl group Chemical group 0.000 claims 1
125000004306 triazinyl group Chemical group 0.000 claims 1
125000001425 triazolyl group Chemical group 0.000 claims 1
229920002554 vinyl polymer Polymers 0.000 claims 1

JP2015549744A 2012-12-20 2013-12-19 ニューロテンシン受容体１の小分子アゴニスト Active JP6391120B2 (ja)