JP2016512256A5 - - Google Patents
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- Publication number
- JP2016512256A5 JP2016512256A5 JP2016500681A JP2016500681A JP2016512256A5 JP 2016512256 A5 JP2016512256 A5 JP 2016512256A5 JP 2016500681 A JP2016500681 A JP 2016500681A JP 2016500681 A JP2016500681 A JP 2016500681A JP 2016512256 A5 JP2016512256 A5 JP 2016512256A5
- Authority
- JP
- Japan
- Prior art keywords
- oxy
- ethyl
- quinolin
- quinoline
- carboxylate
- 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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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 19
- DJXNJVFEFSWHLY-UHFFFAOYSA-M quinoline-3-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)[O-])=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-M 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 14
- -1 -CH 2 OH Chemical group 0.000 claims 12
- 239000000126 substance Substances 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- RCZDLUYSRPUGDN-GFCCVEGCSA-N (1r)-1-[7-[(4-fluorophenyl)methoxy]quinolin-3-yl]ethanol Chemical compound C1=CC2=CC([C@H](O)C)=CN=C2C=C1OCC1=CC=C(F)C=C1 RCZDLUYSRPUGDN-GFCCVEGCSA-N 0.000 claims 1
- RCZDLUYSRPUGDN-LBPRGKRZSA-N (1s)-1-[7-[(4-fluorophenyl)methoxy]quinolin-3-yl]ethanol Chemical compound C1=CC2=CC([C@@H](O)C)=CN=C2C=C1OCC1=CC=C(F)C=C1 RCZDLUYSRPUGDN-LBPRGKRZSA-N 0.000 claims 1
- KUQFACDZEGHQOT-UHFFFAOYSA-N 1-[7-[(3-chlorophenyl)methoxy]quinolin-3-yl]-2-methylpropan-2-ol Chemical compound C1=CC2=CC(CC(C)(O)C)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 KUQFACDZEGHQOT-UHFFFAOYSA-N 0.000 claims 1
- RCZDLUYSRPUGDN-UHFFFAOYSA-N 1-[7-[(4-fluorophenyl)methoxy]quinolin-3-yl]ethanol Chemical compound C1=CC2=CC(C(O)C)=CN=C2C=C1OCC1=CC=C(F)C=C1 RCZDLUYSRPUGDN-UHFFFAOYSA-N 0.000 claims 1
- WEZGYEXQLLOXEL-UHFFFAOYSA-N 1-[7-[(4-fluorophenyl)methoxy]quinolin-3-yl]ethanone Chemical compound C1=CC2=CC(C(=O)C)=CN=C2C=C1OCC1=CC=C(F)C=C1 WEZGYEXQLLOXEL-UHFFFAOYSA-N 0.000 claims 1
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims 1
- KCBWNZSXZUMEEF-UHFFFAOYSA-N 2-[7-(3-fluorophenoxy)quinolin-3-yl]propan-2-ol Chemical compound FC=1C=C(OC2=CC=C3C=C(C=NC3=C2)C(C)(C)O)C=CC=1 KCBWNZSXZUMEEF-UHFFFAOYSA-N 0.000 claims 1
- IUPYYBDVEILKQA-UHFFFAOYSA-N 2-[7-[(3,4,5-trifluorophenyl)methoxy]quinolin-3-yl]propan-2-ol Chemical compound C1=CC2=CC(C(C)(O)C)=CN=C2C=C1OCC1=CC(F)=C(F)C(F)=C1 IUPYYBDVEILKQA-UHFFFAOYSA-N 0.000 claims 1
- ODNHVKCPQNXAJS-UHFFFAOYSA-N 2-[7-[(3,4-difluorophenyl)methoxy]-1,5-naphthyridin-3-yl]acetamide Chemical compound C1=NC2=CC(CC(=O)N)=CN=C2C=C1OCC1=CC=C(F)C(F)=C1 ODNHVKCPQNXAJS-UHFFFAOYSA-N 0.000 claims 1
- TYSMQVFYGQOIGF-UHFFFAOYSA-N 2-[7-[(3,4-difluorophenyl)methoxy]-1,5-naphthyridin-3-yl]acetonitrile Chemical compound C1=C(F)C(F)=CC=C1COC1=CN=C(C=C(CC#N)C=N2)C2=C1 TYSMQVFYGQOIGF-UHFFFAOYSA-N 0.000 claims 1
- PMVXEGFIJIEKDV-UHFFFAOYSA-N 2-[7-[(3,4-difluorophenyl)methoxy]-1,5-naphthyridin-3-yl]propan-2-ol Chemical compound C1=NC2=CC(C(C)(O)C)=CN=C2C=C1OCC1=CC=C(F)C(F)=C1 PMVXEGFIJIEKDV-UHFFFAOYSA-N 0.000 claims 1
- CSWSSWWZGPZRNB-UHFFFAOYSA-N 2-[7-[(3,5-difluorophenyl)methoxy]quinolin-3-yl]propan-2-ol Chemical compound C1=CC2=CC(C(C)(O)C)=CN=C2C=C1OCC1=CC(F)=CC(F)=C1 CSWSSWWZGPZRNB-UHFFFAOYSA-N 0.000 claims 1
- CIDMOUNSZQVIEG-UHFFFAOYSA-N 2-[7-[(3-chloro-4-fluorophenyl)methoxy]-1,5-naphthyridin-3-yl]propan-2-ol Chemical compound C1=NC2=CC(C(C)(O)C)=CN=C2C=C1OCC1=CC=C(F)C(Cl)=C1 CIDMOUNSZQVIEG-UHFFFAOYSA-N 0.000 claims 1
- UBYCQPPZJHLQQF-UHFFFAOYSA-N 2-[7-[(3-chloro-4-fluorophenyl)methoxy]-2-methylquinolin-3-yl]propan-2-ol Chemical compound C=1C=C2C=C(C(C)(C)O)C(C)=NC2=CC=1OCC1=CC=C(F)C(Cl)=C1 UBYCQPPZJHLQQF-UHFFFAOYSA-N 0.000 claims 1
- HIGSFBHYANKCKN-UHFFFAOYSA-N 2-[7-[(3-chlorophenyl)methoxy]-1,5-naphthyridin-3-yl]propan-2-ol Chemical compound C1=NC2=CC(C(C)(O)C)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 HIGSFBHYANKCKN-UHFFFAOYSA-N 0.000 claims 1
- BCQDXUBRLJRFPO-UHFFFAOYSA-N 2-[7-[(3-chlorophenyl)methoxy]-2-methylquinolin-3-yl]propan-2-ol Chemical compound C=1C=C2C=C(C(C)(C)O)C(C)=NC2=CC=1OCC1=CC=CC(Cl)=C1 BCQDXUBRLJRFPO-UHFFFAOYSA-N 0.000 claims 1
- WROVPIZEGDNQNH-UHFFFAOYSA-N 2-[7-[(3-chlorophenyl)methoxy]-2-oxo-1h-quinolin-3-yl]acetamide Chemical compound C1=C2NC(=O)C(CC(=O)N)=CC2=CC=C1OCC1=CC=CC(Cl)=C1 WROVPIZEGDNQNH-UHFFFAOYSA-N 0.000 claims 1
- MZNBSHRDLYUMHT-UHFFFAOYSA-N 2-[7-[(3-chlorophenyl)methoxy]-2-oxo-3,4-dihydro-1h-quinolin-3-yl]acetamide Chemical compound C1=C2NC(=O)C(CC(=O)N)CC2=CC=C1OCC1=CC=CC(Cl)=C1 MZNBSHRDLYUMHT-UHFFFAOYSA-N 0.000 claims 1
- MBXGTBWPHWWCJO-UHFFFAOYSA-N 2-[7-[(3-chlorophenyl)methoxy]quinolin-3-yl]-2-methylpropan-1-ol Chemical compound C1=CC2=CC(C(C)(CO)C)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 MBXGTBWPHWWCJO-UHFFFAOYSA-N 0.000 claims 1
- SKNJGEKTLRQOHK-UHFFFAOYSA-N 2-[7-[(3-chlorophenyl)methoxy]quinolin-3-yl]-2-methylpropanamide Chemical compound C1=CC2=CC(C(C)(C(N)=O)C)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 SKNJGEKTLRQOHK-UHFFFAOYSA-N 0.000 claims 1
- PSPAULJADGGTIW-UHFFFAOYSA-N 2-[7-[(3-chlorophenyl)methoxy]quinolin-3-yl]acetamide Chemical compound C1=CC2=CC(CC(=O)N)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 PSPAULJADGGTIW-UHFFFAOYSA-N 0.000 claims 1
- FSCLFCJCGMVOII-UHFFFAOYSA-N 2-[7-[(3-chlorophenyl)methoxy]quinolin-3-yl]ethanol Chemical compound C1=CC2=CC(CCO)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 FSCLFCJCGMVOII-UHFFFAOYSA-N 0.000 claims 1
- FOJXOEMRCWIBBC-UHFFFAOYSA-N 2-[7-[(3-chlorophenyl)methoxy]quinolin-3-yl]propan-2-ol Chemical compound C1=CC2=CC(C(C)(O)C)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 FOJXOEMRCWIBBC-UHFFFAOYSA-N 0.000 claims 1
- QFMFQANQJHKZAS-UHFFFAOYSA-N 2-[7-[(3-fluorophenyl)methoxy]-1,5-naphthyridin-3-yl]propan-2-ol Chemical compound C1=NC2=CC(C(C)(O)C)=CN=C2C=C1OCC1=CC=CC(F)=C1 QFMFQANQJHKZAS-UHFFFAOYSA-N 0.000 claims 1
- LPLATYSPSNLEBV-UHFFFAOYSA-N 2-[7-[(3-fluorophenyl)methoxy]-2-methylquinolin-3-yl]propan-2-ol Chemical compound C=1C=C2C=C(C(C)(C)O)C(C)=NC2=CC=1OCC1=CC=CC(F)=C1 LPLATYSPSNLEBV-UHFFFAOYSA-N 0.000 claims 1
- JVUPLOMPRQVYBW-UHFFFAOYSA-N 2-[7-[(4-fluorophenyl)methoxy]-1,5-naphthyridin-3-yl]propan-2-ol Chemical compound C1=NC2=CC(C(C)(O)C)=CN=C2C=C1OCC1=CC=C(F)C=C1 JVUPLOMPRQVYBW-UHFFFAOYSA-N 0.000 claims 1
- LWJAAIDLXLUOKI-UHFFFAOYSA-N 2-[7-[(4-fluorophenyl)methoxy]-2-methylquinolin-3-yl]propan-2-ol Chemical compound C=1C=C2C=C(C(C)(C)O)C(C)=NC2=CC=1OCC1=CC=C(F)C=C1 LWJAAIDLXLUOKI-UHFFFAOYSA-N 0.000 claims 1
- LEUUWYVTPWYPGG-UHFFFAOYSA-N 2-[7-[(4-fluorophenyl)methoxy]quinolin-3-yl]propan-2-ol Chemical compound C1=CC2=CC(C(C)(O)C)=CN=C2C=C1OCC1=CC=C(F)C=C1 LEUUWYVTPWYPGG-UHFFFAOYSA-N 0.000 claims 1
- CEDPXOMRLDRRRS-UHFFFAOYSA-N 2-[7-[[2-(trifluoromethyl)pyridin-4-yl]methoxy]quinolin-3-yl]acetamide Chemical compound C1=CC2=CC(CC(=O)N)=CN=C2C=C1OCC1=CC=NC(C(F)(F)F)=C1 CEDPXOMRLDRRRS-UHFFFAOYSA-N 0.000 claims 1
- SDNPYSRYNPYNDS-UHFFFAOYSA-N 2-[7-[[6-(trifluoromethyl)pyridin-2-yl]methoxy]-1,5-naphthyridin-3-yl]acetamide Chemical compound C1=NC2=CC(CC(=O)N)=CN=C2C=C1OCC1=CC=CC(C(F)(F)F)=N1 SDNPYSRYNPYNDS-UHFFFAOYSA-N 0.000 claims 1
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- CAPHTKMPODBRJP-UHFFFAOYSA-N 3-[(4-fluorophenyl)methoxy]-7-(2-fluoropropan-2-yl)-1,5-naphthyridine Chemical compound C1=NC2=CC(C(C)(F)C)=CN=C2C=C1OCC1=CC=C(F)C=C1 CAPHTKMPODBRJP-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 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
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- BLFBQEGMHIZRFA-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=C=CC=C[N]1 BLFBQEGMHIZRFA-UHFFFAOYSA-N 0.000 claims 1
- QCMZKZRSKLBTEB-UHFFFAOYSA-N 7-[(3,4-difluorophenyl)methoxy]-1,5-naphthyridine-3-carboxamide Chemical compound C1=NC2=CC(C(=O)N)=CN=C2C=C1OCC1=CC=C(F)C(F)=C1 QCMZKZRSKLBTEB-UHFFFAOYSA-N 0.000 claims 1
- CEAYLXHUHJJEKH-UHFFFAOYSA-N 7-[(3-chloro-4-fluorophenyl)methoxy]-1,5-naphthyridine-3-carboxamide Chemical compound C1=NC2=CC(C(=O)N)=CN=C2C=C1OCC1=CC=C(F)C(Cl)=C1 CEAYLXHUHJJEKH-UHFFFAOYSA-N 0.000 claims 1
- VSFIFIZCGYLPQY-UHFFFAOYSA-N 7-[(3-chlorophenyl)methoxy]-1,5-naphthyridine-3-carboxamide Chemical compound C1=NC2=CC(C(=O)N)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 VSFIFIZCGYLPQY-UHFFFAOYSA-N 0.000 claims 1
- HHFRAUXFRYHDFR-UHFFFAOYSA-N 7-[(3-chlorophenyl)methoxy]-3-(methoxymethyl)quinoline Chemical compound C1=CC2=CC(COC)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 HHFRAUXFRYHDFR-UHFFFAOYSA-N 0.000 claims 1
- AMUMOXUVOKKKQE-UHFFFAOYSA-N 7-[(3-chlorophenyl)methoxy]-n-methyl-1,5-naphthyridine-3-carboxamide Chemical compound C1=NC2=CC(C(=O)NC)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 AMUMOXUVOKKKQE-UHFFFAOYSA-N 0.000 claims 1
- AXIXQDVICKRSNI-UHFFFAOYSA-N 7-[(3-chlorophenyl)methoxy]-n-methylquinoline-3-carboxamide Chemical compound C1=CC2=CC(C(=O)NC)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 AXIXQDVICKRSNI-UHFFFAOYSA-N 0.000 claims 1
- GXJPTALKFXFJPB-UHFFFAOYSA-N 7-[(3-fluorophenyl)methoxy]-1,5-naphthyridine-3-carboxamide Chemical compound C1=NC2=CC(C(=O)N)=CN=C2C=C1OCC1=CC=CC(F)=C1 GXJPTALKFXFJPB-UHFFFAOYSA-N 0.000 claims 1
- JCEAANRNMUECLL-UHFFFAOYSA-N 7-[(4-fluorophenyl)methoxy]-1,5-naphthyridine-3-carboxamide Chemical compound C1=NC2=CC(C(=O)N)=CN=C2C=C1OCC1=CC=C(F)C=C1 JCEAANRNMUECLL-UHFFFAOYSA-N 0.000 claims 1
- QOKJIQQYTPFNKH-UHFFFAOYSA-N 7-[(4-fluorophenyl)methoxy]-3-(2-fluoropropan-2-yl)quinoline Chemical compound C1=CC2=CC(C(C)(F)C)=CN=C2C=C1OCC1=CC=C(F)C=C1 QOKJIQQYTPFNKH-UHFFFAOYSA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- NYYBTJQTLDRCRZ-UHFFFAOYSA-N [7-[(3,4,5-trifluorophenyl)methoxy]quinolin-3-yl]methanol Chemical compound C1=CC2=CC(CO)=CN=C2C=C1OCC1=CC(F)=C(F)C(F)=C1 NYYBTJQTLDRCRZ-UHFFFAOYSA-N 0.000 claims 1
- IJWHNVNZIZUEOA-UHFFFAOYSA-N [7-[(3,4-difluorophenyl)methoxy]-1,5-naphthyridin-3-yl]methanol Chemical compound C1=NC2=CC(CO)=CN=C2C=C1OCC1=CC=C(F)C(F)=C1 IJWHNVNZIZUEOA-UHFFFAOYSA-N 0.000 claims 1
- ZDAWCNMYUPYKFY-UHFFFAOYSA-N [7-[(3,5-difluorophenyl)methoxy]quinolin-3-yl]methanol Chemical compound C1=CC2=CC(CO)=CN=C2C=C1OCC1=CC(F)=CC(F)=C1 ZDAWCNMYUPYKFY-UHFFFAOYSA-N 0.000 claims 1
- MCQZTWVYBVBACG-UHFFFAOYSA-N [7-[(3-chlorophenyl)methoxy]quinolin-3-yl]methanamine Chemical compound C1=CC2=CC(CN)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 MCQZTWVYBVBACG-UHFFFAOYSA-N 0.000 claims 1
- BKEGJHKXJZNTTG-UHFFFAOYSA-N [7-[(3-chlorophenyl)methoxy]quinolin-3-yl]methanol Chemical compound C1=CC2=CC(CO)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 BKEGJHKXJZNTTG-UHFFFAOYSA-N 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- CBOYMBMRQBAPOU-UHFFFAOYSA-N ethyl 2-[7-[(3-chlorophenyl)methoxy]quinolin-3-yl]-2-methylpropanoate Chemical compound C1=CC2=CC(C(C)(C)C(=O)OCC)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 CBOYMBMRQBAPOU-UHFFFAOYSA-N 0.000 claims 1
- CKYCYIJKKOHKDN-UHFFFAOYSA-N ethyl 7-[(3-chloro-4-fluorophenyl)methoxy]-2-methylquinoline-3-carboxylate Chemical compound C1=C2N=C(C)C(C(=O)OCC)=CC2=CC=C1OCC1=CC=C(F)C(Cl)=C1 CKYCYIJKKOHKDN-UHFFFAOYSA-N 0.000 claims 1
- ASKYBHHJBVSRQM-UHFFFAOYSA-N ethyl 7-[(3-chlorophenyl)methoxy]-2-methylquinoline-3-carboxylate Chemical compound C1=C2N=C(C)C(C(=O)OCC)=CC2=CC=C1OCC1=CC=CC(Cl)=C1 ASKYBHHJBVSRQM-UHFFFAOYSA-N 0.000 claims 1
- IOZNWXDZZUWDKK-UHFFFAOYSA-N ethyl 7-[(3-chlorophenyl)methoxy]quinoline-3-carboxylate Chemical compound C1=CC2=CC(C(=O)OCC)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 IOZNWXDZZUWDKK-UHFFFAOYSA-N 0.000 claims 1
- GIGRZXSDCGDWMK-UHFFFAOYSA-N ethyl 7-[(3-fluorophenyl)methoxy]-2-methylquinoline-3-carboxylate Chemical compound C1=C2N=C(C)C(C(=O)OCC)=CC2=CC=C1OCC1=CC=CC(F)=C1 GIGRZXSDCGDWMK-UHFFFAOYSA-N 0.000 claims 1
- ZCRHMKCDFXDXFU-UHFFFAOYSA-N ethyl 7-[(3-fluorophenyl)methoxy]quinoline-3-carboxylate Chemical compound C1=CC2=CC(C(=O)OCC)=CN=C2C=C1OCC1=CC=CC(F)=C1 ZCRHMKCDFXDXFU-UHFFFAOYSA-N 0.000 claims 1
- BBDQTYFWMGQAFW-UHFFFAOYSA-N ethyl 7-[(4-chlorophenyl)methoxy]quinoline-3-carboxylate Chemical compound C1=CC2=CC(C(=O)OCC)=CN=C2C=C1OCC1=CC=C(Cl)C=C1 BBDQTYFWMGQAFW-UHFFFAOYSA-N 0.000 claims 1
- XUKJQYNSKLQWDY-UHFFFAOYSA-N ethyl 7-[(4-fluorophenyl)methoxy]-2-methylquinoline-3-carboxylate Chemical compound C1=C2N=C(C)C(C(=O)OCC)=CC2=CC=C1OCC1=CC=C(F)C=C1 XUKJQYNSKLQWDY-UHFFFAOYSA-N 0.000 claims 1
- YRZDOSOFJFYUMZ-UHFFFAOYSA-N ethyl 7-[(4-fluorophenyl)methoxy]quinoline-3-carboxylate Chemical compound C1=CC2=CC(C(=O)OCC)=CN=C2C=C1OCC1=CC=C(F)C=C1 YRZDOSOFJFYUMZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- ZFYJSBYSNKDDJP-UHFFFAOYSA-N methyl 2-[7-[(3-chlorophenyl)methoxy]quinolin-3-yl]acetate Chemical compound C1=CC2=CC(CC(=O)OC)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 ZFYJSBYSNKDDJP-UHFFFAOYSA-N 0.000 claims 1
- QGEWIIVTKSVQAU-UHFFFAOYSA-N methyl 7-[(3-chlorophenyl)methoxy]quinoline-3-carboxylate Chemical compound C1=CC2=CC(C(=O)OC)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 QGEWIIVTKSVQAU-UHFFFAOYSA-N 0.000 claims 1
- RWYBOUFQHCEISJ-UHFFFAOYSA-N n-(2-aminoethyl)-7-[(3-chlorophenyl)methoxy]quinoline-3-carboxamide Chemical compound C1=CC2=CC(C(=O)NCCN)=CN=C2C=C1OCC1=CC=CC(Cl)=C1 RWYBOUFQHCEISJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361785872P | 2013-03-14 | 2013-03-14 | |
| US61/785,872 | 2013-03-14 | ||
| PCT/US2014/020881 WO2014158916A1 (en) | 2013-03-14 | 2014-03-05 | Substituted naphthyridine and quinoline compounds as mao inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016512256A JP2016512256A (ja) | 2016-04-25 |
| JP2016512256A5 true JP2016512256A5 (enExample) | 2017-03-30 |
| JP6346658B2 JP6346658B2 (ja) | 2018-06-20 |
Family
ID=51530146
Family Applications (1)
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| CA2895287A1 (en) | 2013-03-14 | 2014-10-02 | Dart Neuroscience, Llc | Substituted naphthyridine and quinoline compounds as mao inhibitors |
| US20170273968A1 (en) * | 2014-09-17 | 2017-09-28 | Dart Neuroscience (Cayman) Ltd. | Mao-b inhibitors and rehabilitation |
| CN104496998B (zh) * | 2014-12-15 | 2017-07-11 | 陕西嘉禾生物科技股份有限公司 | 一种1′‑苄基‑2′‑酮‑5′，7′，8′‑三氢‑螺‑[1，3‑二氧五环‑2]‑喹啉的制备方法 |
| US10227355B2 (en) | 2015-02-03 | 2019-03-12 | Council Of Scientific And Industrial Research | Quinoline derivatives and preparation thereof |
| WO2016179434A1 (en) | 2015-05-05 | 2016-11-10 | Dart Neuroscience, Llc | Systems and methods for cognitive testing |
| CN108602826A (zh) * | 2016-02-04 | 2018-09-28 | 默克专利有限公司 | 作为半导体的[1,5]二氮杂萘化合物和聚合物 |
| CA3207747A1 (en) * | 2016-09-14 | 2018-03-22 | Yufeng Jane Tseng | Novel substituted benzimidazole derivatives as d-amino acid oxidase (daao) inhibitors |
| US12343337B2 (en) | 2016-09-29 | 2025-07-01 | The Regents Of The University Of California | Compounds for increasing neural plasticity |
| CN107216331B (zh) * | 2017-07-07 | 2019-06-18 | 华南理工大学 | 一种四氢萘啶并四氢喹唑啉衍生物及其合成方法和应用 |
| KR102005019B1 (ko) * | 2018-04-04 | 2019-07-31 | 한국과학기술연구원 | 뇌졸중의 예방 및 치료용 조성물 |
| CN108658977A (zh) * | 2018-04-12 | 2018-10-16 | 苏州康润医药有限公司 | 一种7-溴-1,5-萘啶-3-甲酸的合成方法 |
| JP7636796B2 (ja) | 2019-02-27 | 2025-02-27 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 脳障害を治療するためのｎ－置換インドール及び他の複素環化合物 |
| EP3931189B1 (en) | 2019-02-27 | 2025-12-24 | The Regents Of The University Of California | Azepino-indoles and other heterocycles for treating brain disorders |
| CN112939952A (zh) * | 2021-02-02 | 2021-06-11 | 深圳市第二人民医院(深圳市转化医学研究院) | 一种3-羟基查尔酮衍生物及其用途 |
| CN112898276A (zh) * | 2021-02-02 | 2021-06-04 | 深圳市第二人民医院(深圳市转化医学研究院) | 一种查尔酮衍生物及其用途 |
| WO2023114313A1 (en) | 2021-12-15 | 2023-06-22 | Delix Therapeutics, Inc. | Phenoxy and benzyloxy substituted psychoplastogens and uses thereof |
| CN114437068A (zh) * | 2022-02-21 | 2022-05-06 | 深圳市儿童医院 | 一种萘啶衍生物及其作为单胺氧化酶抑制剂的用途 |
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| CA2895287A1 (en) | 2013-03-14 | 2014-10-02 | Dart Neuroscience, Llc | Substituted naphthyridine and quinoline compounds as mao inhibitors |
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2014
- 2014-03-05 CA CA2895287A patent/CA2895287A1/en not_active Abandoned
- 2014-03-05 RU RU2015137619A patent/RU2661156C2/ru not_active IP Right Cessation
- 2014-03-05 CN CN201480023943.4A patent/CN105143190B/zh not_active Expired - Fee Related
- 2014-03-05 MX MX2015011144A patent/MX2015011144A/es unknown
- 2014-03-05 NZ NZ711598A patent/NZ711598A/en not_active IP Right Cessation
- 2014-03-05 SG SG11201504704TA patent/SG11201504704TA/en unknown
- 2014-03-05 AU AU2014241759A patent/AU2014241759B2/en not_active Ceased
- 2014-03-05 BR BR112015022202A patent/BR112015022202A2/pt active Search and Examination
- 2014-03-05 KR KR1020157027858A patent/KR20150127172A/ko not_active Ceased
- 2014-03-05 JP JP2016500681A patent/JP6346658B2/ja not_active Expired - Fee Related
- 2014-03-05 WO PCT/US2014/020881 patent/WO2014158916A1/en not_active Ceased
- 2014-03-05 EP EP14773144.2A patent/EP2970125B1/en active Active
- 2014-03-11 US US14/204,738 patent/US9102674B2/en not_active Expired - Fee Related
- 2014-03-11 US US14/205,195 patent/US9150572B2/en not_active Expired - Fee Related
- 2014-03-14 TW TW103109326A patent/TWI657078B/zh not_active IP Right Cessation
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2015
- 2015-08-25 IL IL240805A patent/IL240805B/en active IP Right Grant
- 2015-09-23 US US14/862,874 patent/US9675605B2/en not_active Expired - Fee Related
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2017
- 2017-05-23 US US15/603,286 patent/US9956213B2/en not_active Expired - Fee Related