JP2014500252A5 - - Google Patents
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- JP2014500252A5 JP2014500252A5 JP2013538052A JP2013538052A JP2014500252A5 JP 2014500252 A5 JP2014500252 A5 JP 2014500252A5 JP 2013538052 A JP2013538052 A JP 2013538052A JP 2013538052 A JP2013538052 A JP 2013538052A JP 2014500252 A5 JP2014500252 A5 JP 2014500252A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- methyl
- ylamino
- phenoxy
- methylsulfonyl
- 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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- 150000001875 compounds Chemical class 0.000 claims 31
- 229910052757 nitrogen Inorganic materials 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- -1 6- (methoxymethyl) pyridin-3-yloxy Chemical group 0.000 claims 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000007942 carboxylates Chemical class 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- LTVXRMDSQZMXSR-UHFFFAOYSA-N 1-[2-[[2-(4-methylsulfonylphenoxy)-5-(pyrazin-2-ylamino)phenyl]methyl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCCC1CC1=CC(NC=2N=CC=NC=2)=CC=C1OC1=CC=C(S(C)(=O)=O)C=C1 LTVXRMDSQZMXSR-UHFFFAOYSA-N 0.000 claims 1
- HDCIFOMMIXJNQZ-UHFFFAOYSA-N 1-[2-[[2-(4-methylsulfonylphenoxy)-5-[[5-(trifluoromethyl)pyridin-2-yl]amino]phenyl]methyl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCCC1CC1=CC(NC=2N=CC(=CC=2)C(F)(F)F)=CC=C1OC1=CC=C(S(C)(=O)=O)C=C1 HDCIFOMMIXJNQZ-UHFFFAOYSA-N 0.000 claims 1
- GGFFJTWKEJFDFK-UHFFFAOYSA-N 1-[[2-(5-chloro-6-methylpyridin-3-yl)oxy-5-[(5-chloropyridin-2-yl)amino]phenyl]methyl]pyrrolidin-2-one Chemical compound C1=C(Cl)C(C)=NC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(Cl)C=N1 GGFFJTWKEJFDFK-UHFFFAOYSA-N 0.000 claims 1
- QUFOWARVMDUBPC-UHFFFAOYSA-N 1-[[2-(6-methylsulfonylpyridin-3-yl)oxy-5-(pyrazin-2-ylamino)phenyl]methyl]pyrrolidin-2-one Chemical compound C1=NC(S(=O)(=O)C)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CN=CC=N1 QUFOWARVMDUBPC-UHFFFAOYSA-N 0.000 claims 1
- VLNCVNYQKBAVSD-UHFFFAOYSA-N 1-[[2-(6-methylsulfonylpyridin-3-yl)oxy-5-(pyridin-2-ylamino)phenyl]methyl]pyrrolidin-2-one Chemical compound C1=NC(S(=O)(=O)C)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=CC=N1 VLNCVNYQKBAVSD-UHFFFAOYSA-N 0.000 claims 1
- JVEAZPHPKYFEQV-UHFFFAOYSA-N 1-[[2-(6-methylsulfonylpyridin-3-yl)oxy-5-[(5-methyl-1,3-thiazol-2-yl)amino]phenyl]methyl]pyrrolidin-2-one Chemical compound S1C(C)=CN=C1NC(C=C1CN2C(CCC2)=O)=CC=C1OC1=CC=C(S(C)(=O)=O)N=C1 JVEAZPHPKYFEQV-UHFFFAOYSA-N 0.000 claims 1
- ZLAKPJHVODSQLN-UHFFFAOYSA-N 1-[[2-(6-methylsulfonylpyridin-3-yl)oxy-5-[(5-phenylpyridin-2-yl)amino]phenyl]methyl]pyrrolidin-2-one Chemical compound C1=NC(S(=O)(=O)C)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(C=2C=CC=CC=2)C=N1 ZLAKPJHVODSQLN-UHFFFAOYSA-N 0.000 claims 1
- QJMOGGHSUCRKLB-UHFFFAOYSA-N 1-[[2-(6-methylsulfonylpyridin-3-yl)oxy-5-[[5-(trifluoromethyl)pyridin-2-yl]amino]phenyl]methyl]pyrrolidin-2-one Chemical compound C1=NC(S(=O)(=O)C)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(C(F)(F)F)C=N1 QJMOGGHSUCRKLB-UHFFFAOYSA-N 0.000 claims 1
- MKUVNIYWWVEOGR-UHFFFAOYSA-N 1-[[2-(6-morpholin-4-ylsulfonylpyridin-3-yl)oxy-5-[[5-(trifluoromethyl)pyridin-2-yl]amino]phenyl]methyl]pyrrolidin-2-one Chemical compound N1=CC(C(F)(F)F)=CC=C1NC(C=C1CN2C(CCC2)=O)=CC=C1OC1=CC=C(S(=O)(=O)N2CCOCC2)N=C1 MKUVNIYWWVEOGR-UHFFFAOYSA-N 0.000 claims 1
- INHBBNSVPHXBTC-UHFFFAOYSA-N 1-[[2-[6-(methoxymethyl)pyridin-3-yl]oxy-5-(pyrazin-2-ylamino)phenyl]methyl]pyrrolidin-2-one Chemical compound C1=NC(COC)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CN=CC=N1 INHBBNSVPHXBTC-UHFFFAOYSA-N 0.000 claims 1
- LJSXFMKJRNWTBT-UHFFFAOYSA-N 1-[[2-[6-(methoxymethyl)pyridin-3-yl]oxy-5-(pyridin-2-ylamino)phenyl]methyl]pyrrolidin-2-one Chemical compound C1=NC(COC)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=CC=N1 LJSXFMKJRNWTBT-UHFFFAOYSA-N 0.000 claims 1
- ZEZWUIDOZZEYLK-UHFFFAOYSA-N 1-[[2-[6-(methoxymethyl)pyridin-3-yl]oxy-5-[(5-methyl-1,3-thiazol-2-yl)amino]phenyl]methyl]pyrrolidin-2-one Chemical compound C1=NC(COC)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=NC=C(C)S1 ZEZWUIDOZZEYLK-UHFFFAOYSA-N 0.000 claims 1
- WNWKDPVHKWIRKI-UHFFFAOYSA-N 1-[[2-[6-(methoxymethyl)pyridin-3-yl]oxy-5-[(5-methylpyridin-2-yl)amino]phenyl]methyl]pyrrolidin-2-one Chemical compound C1=NC(COC)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(C)C=N1 WNWKDPVHKWIRKI-UHFFFAOYSA-N 0.000 claims 1
- LPSBJYKYVDWTGE-UHFFFAOYSA-N 1-[[2-[6-(methoxymethyl)pyridin-3-yl]oxy-5-[(5-phenylpyridin-2-yl)amino]phenyl]methyl]pyrrolidin-2-one Chemical compound C1=NC(COC)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(C=2C=CC=CC=2)C=N1 LPSBJYKYVDWTGE-UHFFFAOYSA-N 0.000 claims 1
- UNKRZHQNKZUENO-UHFFFAOYSA-N 1-[[2-[6-(methoxymethyl)pyridin-3-yl]oxy-5-[[5-(trifluoromethyl)pyridin-2-yl]amino]phenyl]methyl]pyrrolidin-2-one Chemical compound C1=NC(COC)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(C(F)(F)F)C=N1 UNKRZHQNKZUENO-UHFFFAOYSA-N 0.000 claims 1
- ZMFFIGGQSFTJIM-UHFFFAOYSA-N 1-[[5-(1h-imidazol-5-ylamino)-2-(6-methylsulfonylpyridin-3-yl)oxyphenyl]methyl]pyrrolidin-2-one Chemical compound C1=NC(S(=O)(=O)C)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CNC=N1 ZMFFIGGQSFTJIM-UHFFFAOYSA-N 0.000 claims 1
- BNAWXFBWNNQVHB-UHFFFAOYSA-N 1-[[5-(1h-imidazol-5-ylamino)-2-[6-(methoxymethyl)pyridin-3-yl]oxyphenyl]methyl]pyrrolidin-2-one Chemical compound C1=NC(COC)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CNC=N1 BNAWXFBWNNQVHB-UHFFFAOYSA-N 0.000 claims 1
- WLLRTWTWIVPGKA-UHFFFAOYSA-N 1-[[5-[(5-methoxypyridin-2-yl)amino]-2-(6-methylsulfonylpyridin-3-yl)oxyphenyl]methyl]pyrrolidin-2-one Chemical compound N1=CC(OC)=CC=C1NC(C=C1CN2C(CCC2)=O)=CC=C1OC1=CC=C(S(C)(=O)=O)N=C1 WLLRTWTWIVPGKA-UHFFFAOYSA-N 0.000 claims 1
- LRLIZXVXQXACEY-UHFFFAOYSA-N 1-[[5-[(5-methylpyridin-2-yl)amino]-2-(6-methylsulfonylpyridin-3-yl)oxyphenyl]methyl]pyrrolidin-2-one Chemical compound N1=CC(C)=CC=C1NC(C=C1CN2C(CCC2)=O)=CC=C1OC1=CC=C(S(C)(=O)=O)N=C1 LRLIZXVXQXACEY-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- DSRLBHGRJVWYKJ-UHFFFAOYSA-N 2-[6-[3-[(1-acetylpyrrolidin-2-yl)methyl]-4-[4-(dimethylcarbamoyl)phenoxy]anilino]pyridin-3-yl]acetic acid Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2N(CCC2)C(C)=O)=CC=C1NC1=CC=C(CC(O)=O)C=N1 DSRLBHGRJVWYKJ-UHFFFAOYSA-N 0.000 claims 1
- QXFMFGSNQRBBRR-UHFFFAOYSA-N 2-[6-[4-(6-methylsulfonylpyridin-3-yl)oxy-3-[(2-oxopyrrolidin-1-yl)methyl]anilino]pyridin-3-yl]acetic acid Chemical compound C1=NC(S(=O)(=O)C)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(CC(O)=O)C=N1 QXFMFGSNQRBBRR-UHFFFAOYSA-N 0.000 claims 1
- CFKMLKZFSOJNHJ-UHFFFAOYSA-N 2-[6-[4-[4-(dimethylcarbamoyl)phenoxy]-3-(oxan-4-ylmethyl)anilino]pyridin-3-yl]acetic acid Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2CCOCC2)=CC=C1NC1=CC=C(CC(O)=O)C=N1 CFKMLKZFSOJNHJ-UHFFFAOYSA-N 0.000 claims 1
- FUJWNXLHPIKXCY-UHFFFAOYSA-N 2-[6-[4-[6-(dimethylcarbamoyl)pyridin-3-yl]oxy-3-[(2-oxopyrrolidin-1-yl)methyl]anilino]pyridin-3-yl]acetic acid Chemical compound C1=NC(C(=O)N(C)C)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(CC(O)=O)C=N1 FUJWNXLHPIKXCY-UHFFFAOYSA-N 0.000 claims 1
- VEQNMWXAZFNTKD-UHFFFAOYSA-N 2-[6-[4-[6-(methoxymethyl)pyridin-3-yl]oxy-3-[(2-oxopyrrolidin-1-yl)methyl]anilino]pyridin-3-yl]acetic acid Chemical compound C1=NC(COC)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(CC(O)=O)C=N1 VEQNMWXAZFNTKD-UHFFFAOYSA-N 0.000 claims 1
- VJFGMLNMDJEWFQ-UHFFFAOYSA-N 2-[6-[[6-[4-(dimethylcarbamoyl)phenoxy]-5-(oxolan-3-ylmethyl)pyridin-3-yl]amino]pyridin-3-yl]acetic acid Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2COCC2)=NC=C1NC1=CC=C(CC(O)=O)C=N1 VJFGMLNMDJEWFQ-UHFFFAOYSA-N 0.000 claims 1
- BDXJTQWQCQIXNA-UHFFFAOYSA-N 3-[6-[3-[(1-acetylpyrrolidin-2-yl)methyl]-4-[4-(dimethylcarbamoyl)phenoxy]anilino]pyridin-3-yl]propanoic acid Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2N(CCC2)C(C)=O)=CC=C1NC1=CC=C(CCC(O)=O)C=N1 BDXJTQWQCQIXNA-UHFFFAOYSA-N 0.000 claims 1
- AXXRMULPISHBIZ-UHFFFAOYSA-N 3-[6-[4-(6-methylsulfonylpyridin-3-yl)oxy-3-[(2-oxopyrrolidin-1-yl)methyl]anilino]pyridin-3-yl]propanoic acid Chemical compound C1=NC(S(=O)(=O)C)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(CCC(O)=O)C=N1 AXXRMULPISHBIZ-UHFFFAOYSA-N 0.000 claims 1
- YGBNRXAQPZYEHV-UHFFFAOYSA-N 3-[6-[4-[4-(dimethylcarbamoyl)phenoxy]-3-(oxan-4-ylmethyl)anilino]pyridin-3-yl]propanoic acid Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2CCOCC2)=CC=C1NC1=CC=C(CCC(O)=O)C=N1 YGBNRXAQPZYEHV-UHFFFAOYSA-N 0.000 claims 1
- UQGGNOAQMJSJGS-UHFFFAOYSA-N 3-[6-[4-[6-(dimethylcarbamoyl)pyridin-3-yl]oxy-3-[(2-oxopyrrolidin-1-yl)methyl]anilino]pyridin-3-yl]propanoic acid Chemical compound C1=NC(C(=O)N(C)C)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(CCC(O)=O)C=N1 UQGGNOAQMJSJGS-UHFFFAOYSA-N 0.000 claims 1
- APMAUEXRWGWXEZ-UHFFFAOYSA-N 3-[6-[4-[6-(methoxymethyl)pyridin-3-yl]oxy-3-[(2-oxopyrrolidin-1-yl)methyl]anilino]pyridin-3-yl]propanoic acid Chemical compound C1=NC(COC)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(CCC(O)=O)C=N1 APMAUEXRWGWXEZ-UHFFFAOYSA-N 0.000 claims 1
- XUCDRHIBIXMSCU-UHFFFAOYSA-N 3-[6-[[6-[4-(dimethylcarbamoyl)phenoxy]-5-(oxolan-3-ylmethyl)pyridin-3-yl]amino]pyridin-3-yl]propanoic acid Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2COCC2)=NC=C1NC1=CC=C(CCC(O)=O)C=N1 XUCDRHIBIXMSCU-UHFFFAOYSA-N 0.000 claims 1
- BAVATAKQLFMZSI-UHFFFAOYSA-N 3-[[2-(4-methylsulfonylphenoxy)-5-(pyrazin-2-ylamino)phenyl]methyl]cyclopentan-1-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC(C(=C1)CC2CC(=O)CC2)=CC=C1NC1=CN=CC=N1 BAVATAKQLFMZSI-UHFFFAOYSA-N 0.000 claims 1
- UMXOMJUHDJQIML-UHFFFAOYSA-N 3-[[2-(4-methylsulfonylphenoxy)-5-[(5-methyl-1,3-thiazol-2-yl)amino]phenyl]methyl]cyclopentan-1-one Chemical compound S1C(C)=CN=C1NC(C=C1CC2CC(=O)CC2)=CC=C1OC1=CC=C(S(C)(=O)=O)C=C1 UMXOMJUHDJQIML-UHFFFAOYSA-N 0.000 claims 1
- ZEQHSWVZIZHZGM-UHFFFAOYSA-N 3-[[2-(4-methylsulfonylphenoxy)-5-[[5-(trifluoromethyl)pyridin-2-yl]amino]phenyl]methyl]cyclopentan-1-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC(C(=C1)CC2CC(=O)CC2)=CC=C1NC1=CC=C(C(F)(F)F)C=N1 ZEQHSWVZIZHZGM-UHFFFAOYSA-N 0.000 claims 1
- LWRBCBWRGYXKQJ-UHFFFAOYSA-N 4-(4-methylsulfonylphenoxy)-3-n-(oxan-4-yl)-1-n-[5-(trifluoromethyl)pyridin-2-yl]benzene-1,3-diamine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC(C(=C1)NC2CCOCC2)=CC=C1NC1=CC=C(C(F)(F)F)C=N1 LWRBCBWRGYXKQJ-UHFFFAOYSA-N 0.000 claims 1
- JJOGSDYXKYYTFL-UHFFFAOYSA-N 4-(4-methylsulfonylphenoxy)-3-n-(oxan-4-yl)-1-n-pyridin-2-ylbenzene-1,3-diamine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC(C(=C1)NC2CCOCC2)=CC=C1NC1=CC=CC=N1 JJOGSDYXKYYTFL-UHFFFAOYSA-N 0.000 claims 1
- SGBSEWKVQLFXDI-UHFFFAOYSA-N 4-[2-[(1-acetylpyrrolidin-2-yl)methyl]-4-(pyrazin-2-ylamino)phenoxy]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2N(CCC2)C(C)=O)=CC=C1NC1=CN=CC=N1 SGBSEWKVQLFXDI-UHFFFAOYSA-N 0.000 claims 1
- AGFWNTDVNNXOAL-UHFFFAOYSA-N 4-[2-[(1-acetylpyrrolidin-2-yl)methyl]-4-[[5-(trifluoromethyl)pyridin-2-yl]amino]phenoxy]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2N(CCC2)C(C)=O)=CC=C1NC1=CC=C(C(F)(F)F)C=N1 AGFWNTDVNNXOAL-UHFFFAOYSA-N 0.000 claims 1
- OHJOPXBCGXRBRD-UHFFFAOYSA-N 4-[4-(1h-imidazol-5-ylamino)-2-(oxan-4-ylmethyl)phenoxy]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2CCOCC2)=CC=C1NC1=CNC=N1 OHJOPXBCGXRBRD-UHFFFAOYSA-N 0.000 claims 1
- DXQLXRKGTSAGGN-UHFFFAOYSA-N 4-[4-(1h-imidazol-5-ylamino)-2-[(3-oxocyclopentyl)methyl]phenoxy]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2CC(=O)CC2)=CC=C1NC1=CNC=N1 DXQLXRKGTSAGGN-UHFFFAOYSA-N 0.000 claims 1
- BFEISNSIJOLCQI-UHFFFAOYSA-N 4-[5-[(5-cyanopyridin-2-yl)amino]-3-(oxolan-3-ylmethyl)pyridin-2-yl]oxy-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2COCC2)=NC=C1NC1=CC=C(C#N)C=N1 BFEISNSIJOLCQI-UHFFFAOYSA-N 0.000 claims 1
- QBPJGNLJRBLHIH-UHFFFAOYSA-N 5-[4-(1h-imidazol-5-ylamino)-2-[(2-oxopyrrolidin-1-yl)methyl]phenoxy]-n,n-dimethylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)N(C)C)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CNC=N1 QBPJGNLJRBLHIH-UHFFFAOYSA-N 0.000 claims 1
- DSYNIKWVJPVBSO-UHFFFAOYSA-N 5-[4-[(5-cyanopyridin-2-yl)amino]-2-[(2-oxopyrrolidin-1-yl)methyl]phenoxy]-n,n-dimethylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)N(C)C)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(C#N)C=N1 DSYNIKWVJPVBSO-UHFFFAOYSA-N 0.000 claims 1
- OAMYWEBCPWCKBQ-UHFFFAOYSA-N 5-[4-[(5-methoxypyridin-2-yl)amino]-2-[(2-oxopyrrolidin-1-yl)methyl]phenoxy]-n,n-dimethylpyridine-2-carboxamide Chemical compound N1=CC(OC)=CC=C1NC(C=C1CN2C(CCC2)=O)=CC=C1OC1=CC=C(C(=O)N(C)C)N=C1 OAMYWEBCPWCKBQ-UHFFFAOYSA-N 0.000 claims 1
- TZIOWIFCCKHRQU-UHFFFAOYSA-N 5-methyl-n-[4-(4-methylsulfonylphenoxy)-3-(oxan-4-ylmethyl)phenyl]-1,3-thiazol-2-amine Chemical compound S1C(C)=CN=C1NC(C=C1CC2CCOCC2)=CC=C1OC1=CC=C(S(C)(=O)=O)C=C1 TZIOWIFCCKHRQU-UHFFFAOYSA-N 0.000 claims 1
- NPYQVQAZGNWZSX-UHFFFAOYSA-N 5-methyl-n-[4-(4-methylsulfonylphenyl)sulfanyl-3-(oxan-4-yloxy)phenyl]-1,3-thiazol-2-amine Chemical compound S1C(C)=CN=C1NC(C=C1OC2CCOCC2)=CC=C1SC1=CC=C(S(C)(=O)=O)C=C1 NPYQVQAZGNWZSX-UHFFFAOYSA-N 0.000 claims 1
- QLZKTRFXUQRARM-UHFFFAOYSA-N 6-(4-methylsulfonylphenoxy)-5-(oxolan-3-ylmethyl)-n-(5-phenylpyridin-2-yl)pyridin-3-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC(C(=C1)CC2COCC2)=NC=C1NC1=CC=C(C=2C=CC=CC=2)C=N1 QLZKTRFXUQRARM-UHFFFAOYSA-N 0.000 claims 1
- YJWAUYPAHSTZAT-UHFFFAOYSA-N 6-(4-methylsulfonylphenoxy)-5-(oxolan-3-ylmethyl)-n-[5-(trifluoromethyl)pyridin-2-yl]pyridin-3-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC(C(=C1)CC2COCC2)=NC=C1NC1=CC=C(C(F)(F)F)C=N1 YJWAUYPAHSTZAT-UHFFFAOYSA-N 0.000 claims 1
- LJNHUGBNRAVAFO-UHFFFAOYSA-N 6-(4-methylsulfonylphenoxy)-5-(oxolan-3-ylmethyl)-n-pyridin-2-ylpyridin-3-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC(C(=C1)CC2COCC2)=NC=C1NC1=CC=CC=N1 LJNHUGBNRAVAFO-UHFFFAOYSA-N 0.000 claims 1
- DPDOMOXXDWPJEX-UHFFFAOYSA-N 6-[3-[(1-acetylpyrrolidin-2-yl)methyl]-4-[4-(dimethylcarbamoyl)phenoxy]anilino]pyridine-3-carboxylic acid Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2N(CCC2)C(C)=O)=CC=C1NC1=CC=C(C(O)=O)C=N1 DPDOMOXXDWPJEX-UHFFFAOYSA-N 0.000 claims 1
- IKGBIZQNPKJTSS-UHFFFAOYSA-N 6-[4-(6-methylsulfonylpyridin-3-yl)oxy-3-[(2-oxopyrrolidin-1-yl)methyl]anilino]pyridine-3-carbonitrile Chemical compound C1=NC(S(=O)(=O)C)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(C#N)C=N1 IKGBIZQNPKJTSS-UHFFFAOYSA-N 0.000 claims 1
- ISVQLFKEZJXRNG-UHFFFAOYSA-N 6-[4-(6-methylsulfonylpyridin-3-yl)oxy-3-[(2-oxopyrrolidin-1-yl)methyl]anilino]pyridine-3-carboxylic acid Chemical compound C1=NC(S(=O)(=O)C)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(C(O)=O)C=N1 ISVQLFKEZJXRNG-UHFFFAOYSA-N 0.000 claims 1
- XZKWCJXJIQMTBA-UHFFFAOYSA-N 6-[4-[4-(dimethylcarbamoyl)phenoxy]-3-(oxan-4-ylmethyl)anilino]pyridine-3-carboxylic acid Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2CCOCC2)=CC=C1NC1=CC=C(C(O)=O)C=N1 XZKWCJXJIQMTBA-UHFFFAOYSA-N 0.000 claims 1
- SOMDWWATDHVDAS-UHFFFAOYSA-N 6-[4-[6-(dimethylcarbamoyl)pyridin-3-yl]oxy-3-[(2-oxopyrrolidin-1-yl)methyl]anilino]-n-ethylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NCC)=CC=C1NC(C=C1CN2C(CCC2)=O)=CC=C1OC1=CC=C(C(=O)N(C)C)N=C1 SOMDWWATDHVDAS-UHFFFAOYSA-N 0.000 claims 1
- LXPRGWBGHVXQTM-UHFFFAOYSA-N 6-[4-[6-(dimethylcarbamoyl)pyridin-3-yl]oxy-3-[(2-oxopyrrolidin-1-yl)methyl]anilino]pyridine-3-carboxylic acid Chemical compound C1=NC(C(=O)N(C)C)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(C(O)=O)C=N1 LXPRGWBGHVXQTM-UHFFFAOYSA-N 0.000 claims 1
- ZGNBPFKBMMEHFD-UHFFFAOYSA-N 6-[4-[6-(methoxymethyl)pyridin-3-yl]oxy-3-[(2-oxopyrrolidin-1-yl)methyl]anilino]pyridine-3-carbonitrile Chemical compound C1=NC(COC)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(C#N)C=N1 ZGNBPFKBMMEHFD-UHFFFAOYSA-N 0.000 claims 1
- GWGANBHBGKEKRV-UHFFFAOYSA-N 6-[4-[6-(methoxymethyl)pyridin-3-yl]oxy-3-[(2-oxopyrrolidin-1-yl)methyl]anilino]pyridine-3-carboxylic acid Chemical compound C1=NC(COC)=CC=C1OC(C(=C1)CN2C(CCC2)=O)=CC=C1NC1=CC=C(C(O)=O)C=N1 GWGANBHBGKEKRV-UHFFFAOYSA-N 0.000 claims 1
- ASHBMSPFVCPUST-UHFFFAOYSA-N 6-[[6-(4-methylsulfonylphenoxy)-5-(oxolan-3-ylmethyl)pyridin-3-yl]amino]pyridine-3-carbonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC(C(=C1)CC2COCC2)=NC=C1NC1=CC=C(C#N)C=N1 ASHBMSPFVCPUST-UHFFFAOYSA-N 0.000 claims 1
- TWDOJBVMHFSJCA-UHFFFAOYSA-N 6-[[6-(4-methylsulfonylphenoxy)-5-(oxolan-3-ylmethyl)pyridin-3-yl]amino]pyridine-3-carboxylic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC(C(=C1)CC2COCC2)=NC=C1NC1=CC=C(C(O)=O)C=N1 TWDOJBVMHFSJCA-UHFFFAOYSA-N 0.000 claims 1
- FKUQMUZULTTYNR-UHFFFAOYSA-N 6-[[6-[4-(dimethylcarbamoyl)phenoxy]-5-(oxolan-3-ylmethyl)pyridin-3-yl]amino]-n-ethylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NCC)=CC=C1NC(C=C1CC2COCC2)=CN=C1OC1=CC=C(C(=O)N(C)C)C=C1 FKUQMUZULTTYNR-UHFFFAOYSA-N 0.000 claims 1
- JKAMWLGADXJDTJ-UHFFFAOYSA-N 6-[[6-[4-(dimethylcarbamoyl)phenoxy]-5-(oxolan-3-ylmethyl)pyridin-3-yl]amino]pyridine-3-carboxylic acid Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2COCC2)=NC=C1NC1=CC=C(C(O)=O)C=N1 JKAMWLGADXJDTJ-UHFFFAOYSA-N 0.000 claims 1
- PZXWOUAXLLCKSN-UHFFFAOYSA-N CS(C(C=C1)=CC=C1OC(C=C1)=C(CC(CCC2)C2=O)C=C1NC1=CNC=N1)(=O)=O Chemical compound CS(C(C=C1)=CC=C1OC(C=C1)=C(CC(CCC2)C2=O)C=C1NC1=CNC=N1)(=O)=O PZXWOUAXLLCKSN-UHFFFAOYSA-N 0.000 claims 1
- NWGZGJQVELKVEK-UHFFFAOYSA-N Cc1cnc(Nc2ccc(Oc3ccc(cc3)S(C)(=O)=O)c(CC3CCCN3CC=O)c2)s1 Chemical compound Cc1cnc(Nc2ccc(Oc3ccc(cc3)S(C)(=O)=O)c(CC3CCCN3CC=O)c2)s1 NWGZGJQVELKVEK-UHFFFAOYSA-N 0.000 claims 1
- 102000030595 Glucokinase Human genes 0.000 claims 1
- 108010021582 Glucokinase Proteins 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000013522 chelant Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- MUHTZEJBTZCITA-UHFFFAOYSA-N n,n-dimethyl-4-[2-[(3-oxocyclopentyl)methyl]-4-(pyrazin-2-ylamino)phenoxy]benzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(C(=C1)CC2CC(=O)CC2)=CC=C1NC1=CN=CC=N1 MUHTZEJBTZCITA-UHFFFAOYSA-N 0.000 claims 1
- RXUZWUVDMZTGQI-UHFFFAOYSA-N n-[4-(4-methylsulfonylphenoxy)-3-(oxan-4-ylmethyl)phenyl]-1h-imidazol-5-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC(C(=C1)CC2CCOCC2)=CC=C1NC1=CNC=N1 RXUZWUVDMZTGQI-UHFFFAOYSA-N 0.000 claims 1
- GPEMNNLNNDQKTF-UHFFFAOYSA-N n-[4-(4-methylsulfonylphenoxy)-3-(oxan-4-ylmethyl)phenyl]-5-(trifluoromethyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC(C(=C1)CC2CCOCC2)=CC=C1NC1=CC=C(C(F)(F)F)C=N1 GPEMNNLNNDQKTF-UHFFFAOYSA-N 0.000 claims 1
- SOZZASBCFNJNQZ-UHFFFAOYSA-N n-[4-(4-methylsulfonylphenoxy)-3-(oxan-4-ylmethyl)phenyl]pyrazin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC(C(=C1)CC2CCOCC2)=CC=C1NC1=CN=CC=N1 SOZZASBCFNJNQZ-UHFFFAOYSA-N 0.000 claims 1
- BOUBFICICDVSNZ-UHFFFAOYSA-N n-[4-(4-methylsulfonylphenyl)sulfanyl-3-(oxan-4-yloxy)phenyl]-1h-imidazol-5-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1SC(C(=C1)OC2CCOCC2)=CC=C1NC1=CNC=N1 BOUBFICICDVSNZ-UHFFFAOYSA-N 0.000 claims 1
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- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
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- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
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| CN201010535640.4 | 2010-11-09 | ||
| PCT/CN2011/082004 WO2012062210A1 (en) | 2010-11-09 | 2011-11-09 | Compound for increasing kinase active and application thereof |
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| JPS62212378A (ja) * | 1986-03-08 | 1987-09-18 | バイエル・アクチエンゲゼルシヤフト | ジアリ−ルスルフイド誘導体 |
| DE3632042A1 (de) | 1986-03-08 | 1987-09-10 | Bayer Ag | Diarylsulfidderivate |
| EP1119548B1 (en) * | 1998-10-08 | 2004-12-08 | SmithKline Beecham plc | 3-(3-chloro-4-hydroxyphenylamino)-4-(2-nitrophenyl)-1h-pyrrole-2,5-dione as glycogen synthase kinase-3 inhibitor (gsk-3) |
| US6719520B2 (en) | 1998-10-08 | 2004-04-13 | Smithkline Beecham Corporation | Method and compounds |
| UA71945C2 (en) * | 1999-01-27 | 2005-01-17 | Pfizer Prod Inc | Substituted bicyclic derivatives being used as anticancer agents |
| EP1127882A1 (en) | 2000-01-25 | 2001-08-29 | Pfizer Products Inc. | Tetrazole compounds as thyroid receptor ligands |
| GB0008264D0 (en) * | 2000-04-04 | 2000-05-24 | Smithkline Beecham Plc | Novel method and compounds |
| JP3598994B2 (ja) * | 2000-07-10 | 2004-12-08 | セイコーエプソン株式会社 | 電気光学装置の製造方法 |
| ES2263743T3 (es) * | 2001-04-13 | 2006-12-16 | Pfizer Products Inc. | Derivados de 4-aminopiridopirimidina sustituidos con un grupo biciclico. |
| WO2003026664A1 (en) * | 2001-09-26 | 2003-04-03 | Bayer Corporation | 2-phenylamino-4- (5-pyrazolylamino) -pyramidine derivatives as kinase inhibitors, in particular, src kinase inhibitors |
| DE10153396A1 (de) | 2001-11-01 | 2003-05-28 | Siemens Ag | Einrichtung zur Ansteuerung einer elektrischen Kraftstoffpumpe |
| MXPA06000269A (es) * | 2003-07-09 | 2006-04-07 | Hoffmann La Roche | Tiofenilaminoimidazolinas. |
| RU2398773C2 (ru) * | 2004-11-02 | 2010-09-10 | Баниу Фармасьютикал Ко., Лтд. | Арилоксизамещенное производное бензимидазола |
| EP2205077A4 (en) * | 2007-09-24 | 2010-12-29 | Tragara Pharmaceuticals Inc | THERAPIES FOR THE TREATMENT OF CANCER BASED ON COMBINATIONS OF COX-2 INHIBITORS AND ANTI-HER2 (ERBB2) ANTIBODIES OR COMBINATIONS OF COX-2 INHIBITORS AND HER2 (ERBB2) RECEPTOR TYROSINE KINASE INHIBITORS |
| US8377924B2 (en) * | 2009-01-21 | 2013-02-19 | Rigel Pharmaceuticals Inc. | Protein kinase C inhibitors and uses thereof |
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- 2011-11-09 EP EP11839459.2A patent/EP2638036B1/en active Active
- 2011-11-09 CN CN201180053876.7A patent/CN103502244B/zh active Active
- 2011-11-09 SG SG2013036041A patent/SG190784A1/en unknown
- 2011-11-09 AU AU2011328673A patent/AU2011328673B2/en not_active Ceased
- 2011-11-09 WO PCT/CN2011/082004 patent/WO2012062210A1/en not_active Ceased
- 2011-11-09 US US13/884,470 patent/US9409900B2/en active Active
- 2011-11-09 KR KR1020137014756A patent/KR20140016245A/ko not_active Ceased
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