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 (https=) | 2017-03-30 |
| JP6346658B2 JP6346658B2 (ja) | 2018-06-20 |
Family
ID=51530146
Family Applications (1)
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| JP2016500681A Expired - Fee Related JP6346658B2 (ja) | 2013-03-14 | 2014-03-05 | Ｍａｏ阻害剤としての置換ナフチリジン及びキノリン化合物 |
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| EP (1) | EP2970125B1 (https=) |
| JP (1) | JP6346658B2 (https=) |
| KR (1) | KR20150127172A (https=) |
| CN (1) | CN105143190B (https=) |
| AU (1) | AU2014241759B2 (https=) |
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| MX (1) | MX2015011144A (https=) |
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| SG (1) | SG11201504704TA (https=) |
| TW (1) | TWI657078B (https=) |
| WO (1) | WO2014158916A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ711598A (en) | 2013-03-14 | 2016-09-30 | Dart Neuroscience Cayman Ltd | Substituted naphthyridine and quinoline compounds as mao inhibitors |
| MA39415A (fr) * | 2014-09-17 | 2016-03-24 | Dart Neuroscience Cayman Ltd | Inhibiteurs de mao-b et rééducation |
| 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 |
| WO2016125187A1 (en) | 2015-02-03 | 2016-08-11 | Council Of Scientific & Industrial Research | Novel quinoline derivatives and preparation thereof |
| WO2016179432A2 (en) | 2015-05-05 | 2016-11-10 | Dart Neuroscience, Llc | Systems and methods for cognitive testing |
| EP3411374B9 (en) * | 2016-02-04 | 2023-01-11 | Raynergy Tek Inc. | [1,5]naphthyridine compounds and polymers as semiconductors |
| EP3512840B1 (en) * | 2016-09-14 | 2024-03-06 | Yufeng Jane Tseng | Novel substituted benzimidazole derivatives as d-amino acid oxidase (daao) inhibitors |
| WO2018064465A1 (en) * | 2016-09-29 | 2018-04-05 | 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 |
| CN113784962B (zh) | 2019-02-27 | 2025-04-25 | 加利福尼亚大学董事会 | 用于治疗脑部疾病的氮杂环庚三烯并-吲哚类和其他杂环 |
| AU2020228289B2 (en) | 2019-02-27 | 2026-02-05 | The Regents Of The University Of California | N-substituted 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 |
| TW202333668A (zh) | 2021-12-15 | 2023-09-01 | 美商德利克斯醫療公司 | 經苯氧基及苄氧基取代之精神成形素(psychoplastogen)及其用途 |
| 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 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1138540A (en) * | 1966-09-19 | 1969-01-01 | Ici Ltd | Quinoline derivatives |
| SU550385A1 (ru) * | 1975-09-22 | 1977-03-15 | Институт Биологической И Медицинской Химии Амн Ссср | 8-( -Метил - -пропинил-2)-аминометилхинолин как ингибитор моноаминоксидазы и способ его получени |
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| JPH04295470A (ja) | 1991-03-22 | 1992-10-20 | Wakamoto Pharmaceut Co Ltd | モノアミンオキシダーゼ−ｂ酵素阻害活性を有する１，２，４−オキサジアゾール誘導体及びその製造法 |
| US5510361A (en) | 1994-10-20 | 1996-04-23 | The Procter & Gamble Company | Di-tert-butylphenol compounds with heterocyclic moiety, useful as anti-inflammatory agents |
| WO1998020871A1 (en) | 1996-11-08 | 1998-05-22 | Nippon Chemiphar Co., Ltd. | Visceral fat lowering agent |
| EP0994095A1 (en) | 1996-12-24 | 2000-04-19 | Nippon Chemiphar Co., Ltd. | Propionic acid derivatives |
| US9931318B2 (en) | 2003-04-08 | 2018-04-03 | Dart Neuroscience (Cayman) Ltd. | Phosphodiesterase 4 inhibitors for cognitive and motor rehabilitation |
| ATE526020T1 (de) | 2000-08-10 | 2011-10-15 | Cold Spring Harbor Lab | Gesteigertes kognitives training |
| US7868015B2 (en) | 2000-08-10 | 2011-01-11 | Cold Spring Harbor Laboratory | Phosphodiesesterase 4 inhibitors for the treatment of a cognitive deficit |
| JP2002322163A (ja) * | 2001-04-20 | 2002-11-08 | Sumitomo Pharmaceut Co Ltd | ピペラジン誘導体 |
| FR2834640B1 (fr) | 2002-01-11 | 2004-09-24 | Lipha | Composition pharmaceutique comprenant une glitazone et un acide 4-oxobutanoique et son utilisation pour traiter le diabete |
| DK1466912T3 (da) * | 2002-01-18 | 2013-07-01 | Astellas Pharma Inc | 2-acylaminothiazolderivat eller salt deraf |
| US6761089B2 (en) | 2002-07-01 | 2004-07-13 | Proqual, Llc | Tool for removing screws with damaged heads |
| MY134480A (en) | 2002-09-20 | 2007-12-31 | Hoffmann La Roche | 4-pyrrolidino-phenyl-benzyl ether derivatives |
| EP1643352A4 (en) | 2003-07-02 | 2009-03-04 | Satoshi Yamatake | DATABASE SYSTEM |
| BRPI0415842A (pt) | 2003-10-23 | 2007-01-02 | Hoffmann La Roche | derivativos de benzapepina como inibidores de mao-b |
| US7501528B2 (en) | 2005-03-15 | 2009-03-10 | Hoffmann-La Roche Inc. | Method for preparing enantiomerically pure 4-pyrrolidino phenylbenzyl ether derivatives |
| EP1863784A1 (en) | 2005-03-29 | 2007-12-12 | Newron Pharmaceuticals S.p.A. | Substituted aminoalkyl- and amidoalkyl-benzopyran derivatives |
| US8138209B2 (en) | 2005-07-13 | 2012-03-20 | Jenrin Discovery, Inc. | Substituted picolinamides as MAO-B inhibitors useful for treating obesity |
| CN101484424B (zh) | 2006-02-28 | 2014-05-14 | 达特神经科学(开曼)有限公司 | 治疗化合物 |
| JP2010527243A (ja) | 2007-05-15 | 2010-08-12 | ヘリコン セラピューティクス，インコーポレイテッド | 低分子干渉ＲＮＡ（ｓｉＲＮＡ）を用いた記憶形成に関わる遺伝子の同定方法 |
| AU2008293542B9 (en) | 2007-08-27 | 2014-08-07 | Dart Neuroscience (Cayman) Ltd. | Therapeutic isoxazole compounds |
| ES2401679T3 (es) * | 2008-06-20 | 2013-04-23 | Rottapharm S.P.A. | Derivados de 6-1H-imidazo-quinazolina y de quinolinas, nuevos inhibidores de MAO y ligandos del receptor de imidazolina |
| JP2012507534A (ja) | 2008-10-31 | 2012-03-29 | メルク・シャープ・エンド・ドーム・コーポレイション | 新規置換アザベンゾオキサゾール類 |
| ES2343347B2 (es) | 2009-01-27 | 2011-12-07 | Universidade De Santiago De Compostela | Uso de derivados de 3-fenilcumarinas 6-sustituidas y preparacion de nuevos derivados. |
| KR101220182B1 (ko) | 2009-02-25 | 2013-01-11 | 에스케이바이오팜 주식회사 | 치환된 아졸 유도체 화합물, 이를 포함하는 약제학적 조성물 및 이를 이용한 파킨슨씨 병 치료방법 |
| NZ711598A (en) | 2013-03-14 | 2016-09-30 | Dart Neuroscience Cayman Ltd | Substituted naphthyridine and quinoline compounds as mao inhibitors |
-
2014
- 2014-03-05 NZ NZ711598A patent/NZ711598A/en not_active IP Right Cessation
- 2014-03-05 MX MX2015011144A patent/MX2015011144A/es unknown
- 2014-03-05 EP EP14773144.2A patent/EP2970125B1/en active Active
- 2014-03-05 WO PCT/US2014/020881 patent/WO2014158916A1/en not_active Ceased
- 2014-03-05 SG SG11201504704TA patent/SG11201504704TA/en unknown
- 2014-03-05 RU RU2015137619A patent/RU2661156C2/ru not_active IP Right Cessation
- 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 CA CA2895287A patent/CA2895287A1/en not_active Abandoned
- 2014-03-05 CN CN201480023943.4A patent/CN105143190B/zh not_active Expired - Fee Related
- 2014-03-05 JP JP2016500681A patent/JP6346658B2/ja not_active Expired - Fee Related
- 2014-03-11 US US14/205,195 patent/US9150572B2/en not_active Expired - Fee Related
- 2014-03-11 US US14/204,738 patent/US9102674B2/en not_active Expired - Fee Related
- 2014-03-14 TW TW103109326A patent/TWI657078B/zh not_active IP Right Cessation
-
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
-
2017
- 2017-05-23 US US15/603,286 patent/US9956213B2/en not_active Expired - Fee Related
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