JP2013501064A - リゾホスファチジン酸受容体アンタゴニストとしての化合物 - Google Patents
リゾホスファチジン酸受容体アンタゴニストとしての化合物 Download PDFInfo
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- JP2013501064A JP2013501064A JP2012523709A JP2012523709A JP2013501064A JP 2013501064 A JP2013501064 A JP 2013501064A JP 2012523709 A JP2012523709 A JP 2012523709A JP 2012523709 A JP2012523709 A JP 2012523709A JP 2013501064 A JP2013501064 A JP 2013501064A
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- Prior art keywords
- phenyl
- compound
- methyl
- isoxazol
- ethoxycarbonylamino
- Prior art date
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- GLGVPYOYFUCHCB-UHFFFAOYSA-N 1-[4-[4-[5-methyl-4-(phenylmethoxycarbonylamino)-1,2-oxazol-3-yl]phenyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound CC=1ON=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C2(CC2)C(O)=O)C=1NC(=O)OCC1=CC=CC=C1 GLGVPYOYFUCHCB-UHFFFAOYSA-N 0.000 claims 2
- FQTXKQZWLUTAHT-UHFFFAOYSA-N 1-[4-[4-[5-methyl-4-(propan-2-yloxycarbonylamino)-1,2-oxazol-3-yl]phenyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound CC(C)OC(=O)NC1=C(C)ON=C1C1=CC=C(C=2C=CC(=CC=2)C2(CC2)C(O)=O)C=C1 FQTXKQZWLUTAHT-UHFFFAOYSA-N 0.000 claims 2
- UDOVTTSBJPJRCL-UHFFFAOYSA-N 1-[4-[4-[5-methyl-4-[1-[4-(trifluoromethyl)phenyl]ethoxycarbonylamino]-1,2-oxazol-3-yl]phenyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C(C=C1)=CC=C1C1(C(O)=O)CC1 UDOVTTSBJPJRCL-UHFFFAOYSA-N 0.000 claims 2
- UQMQYXBVLXXFIW-LJQANCHMSA-N 1-[4-[4-[5-methyl-4-[[(1r)-1-(2-methylphenyl)ethoxy]carbonylamino]-1,2-oxazol-3-yl]phenyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)C)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C(C=C1)=CC=C1C1(C(O)=O)CC1 UQMQYXBVLXXFIW-LJQANCHMSA-N 0.000 claims 2
- FEOFMGBTMIXBAD-LJQANCHMSA-N 1-[4-[4-[5-methyl-4-[[(1r)-1-(3-methylphenyl)ethoxy]carbonylamino]-1,2-oxazol-3-yl]phenyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound O([C@H](C)C=1C=C(C)C=CC=1)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C(C=C1)=CC=C1C1(C(O)=O)CC1 FEOFMGBTMIXBAD-LJQANCHMSA-N 0.000 claims 2
- AEYYBRANOZMSPA-QGZVFWFLSA-N 1-[4-[4-[5-methyl-4-[[(1r)-1-[2-(trifluoromethyl)phenyl]ethoxy]carbonylamino]-1,2-oxazol-3-yl]phenyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)C(F)(F)F)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C(C=C1)=CC=C1C1(C(O)=O)CC1 AEYYBRANOZMSPA-QGZVFWFLSA-N 0.000 claims 2
- KEMCYAQORZMSGE-GOSISDBHSA-N 1-[4-[4-[5-methyl-4-[[(1r)-1-phenylethoxy]carbonylamino]-1,2-oxazol-3-yl]phenoxy]phenyl]cyclopropane-1-carboxylic acid Chemical compound O([C@H](C)C=1C=CC=CC=1)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1OC(C=C1)=CC=C1C1(C(O)=O)CC1 KEMCYAQORZMSGE-GOSISDBHSA-N 0.000 claims 2
- WBGPXUNBQGMPRK-LJQANCHMSA-N 1-[4-[4-[5-methyl-4-[[(1r)-1-phenylethoxy]carbonylamino]-1,2-oxazol-3-yl]phenyl]phenyl]cyclobutane-1-carboxylic acid Chemical compound O([C@H](C)C=1C=CC=CC=1)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C(C=C1)=CC=C1C1(C(O)=O)CCC1 WBGPXUNBQGMPRK-LJQANCHMSA-N 0.000 claims 2
- CYNRAOWZWAHONU-HXUWFJFHSA-N 1-[4-[4-[5-methyl-4-[[(1r)-1-phenylethoxy]carbonylamino]-1,2-oxazol-3-yl]phenyl]phenyl]cyclopentane-1-carboxylic acid Chemical compound O([C@H](C)C=1C=CC=CC=1)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C(C=C1)=CC=C1C1(C(O)=O)CCCC1 CYNRAOWZWAHONU-HXUWFJFHSA-N 0.000 claims 2
- UUIOFIANMNWRJK-GOSISDBHSA-N 1-[4-[4-[5-methyl-4-[[(1r)-1-phenylethoxy]carbonylamino]-1,2-oxazol-3-yl]phenyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound O([C@H](C)C=1C=CC=CC=1)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C(C=C1)=CC=C1C1(C(O)=O)CC1 UUIOFIANMNWRJK-GOSISDBHSA-N 0.000 claims 2
- LHAKWYHIHXLEKL-CYBMUJFWSA-N 2-[2-[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]phenyl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(N=1)=CSC=1C1=CC=CC=C1CC(O)=O LHAKWYHIHXLEKL-CYBMUJFWSA-N 0.000 claims 2
- ICHVPLBCVOZVSU-MRXNPFEDSA-N 2-[2-[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]sulfanylphenyl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1SC1=CC=CC=C1CC(O)=O ICHVPLBCVOZVSU-MRXNPFEDSA-N 0.000 claims 2
- LKSROZNQOKESMA-QGZVFWFLSA-N 2-[2-[4-[5-methyl-4-[[(1r)-1-phenylethoxy]carbonylamino]-1,2-oxazol-3-yl]phenyl]phenyl]acetic acid Chemical compound O([C@H](C)C=1C=CC=CC=1)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=CC=C1CC(O)=O LKSROZNQOKESMA-QGZVFWFLSA-N 0.000 claims 2
- QTZZROJDHUBSEE-UHFFFAOYSA-N 2-[2-[[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methoxy]phenyl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1COC1=CC=CC=C1CC(O)=O QTZZROJDHUBSEE-UHFFFAOYSA-N 0.000 claims 2
- SQSZLPOGHAWFDF-UHFFFAOYSA-N 2-[3-[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]-4-fluorophenyl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC(CC(O)=O)=CC=C1F SQSZLPOGHAWFDF-UHFFFAOYSA-N 0.000 claims 2
- BDGJXIZTNIOUFV-UHFFFAOYSA-N 2-[3-[4-[4-[1-(2-fluorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenoxy]phenyl]acetic acid Chemical compound C=1C=CC=C(F)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1OC1=CC=CC(CC(O)=O)=C1 BDGJXIZTNIOUFV-UHFFFAOYSA-N 0.000 claims 2
- GXTZBFHPXXZCFC-MRXNPFEDSA-N 2-[3-[4-[4-[[(1r)-1-(2-chlorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenoxy]phenyl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)Cl)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1OC1=CC=CC(CC(O)=O)=C1 GXTZBFHPXXZCFC-MRXNPFEDSA-N 0.000 claims 2
- HBKDJQRLQZUSSX-CYBMUJFWSA-N 2-[3-[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]phenyl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(N=1)=CSC=1C1=CC=CC(CC(O)=O)=C1 HBKDJQRLQZUSSX-CYBMUJFWSA-N 0.000 claims 2
- FBJJGGDZAXGORA-MRXNPFEDSA-N 2-[3-[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]sulfanylphenyl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1SC1=CC=CC(CC(O)=O)=C1 FBJJGGDZAXGORA-MRXNPFEDSA-N 0.000 claims 2
- NPACGXSQIUJGTJ-QGZVFWFLSA-N 2-[3-[4-[5-methyl-4-[[(1r)-1-phenylethoxy]carbonylamino]-1,2-oxazol-3-yl]phenyl]phenyl]acetic acid Chemical compound O([C@H](C)C=1C=CC=CC=1)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=CC(CC(O)=O)=C1 NPACGXSQIUJGTJ-QGZVFWFLSA-N 0.000 claims 2
- MSLBJICXPHPALI-UHFFFAOYSA-N 2-[3-[[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methyl]phenyl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1CC1=CC=CC(CC(O)=O)=C1 MSLBJICXPHPALI-UHFFFAOYSA-N 0.000 claims 2
- IJRMMVBFZVJAAS-UHFFFAOYSA-N 2-[3-[[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methylsulfonyl]phenyl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1CS(=O)(=O)C1=CC=CC(CC(O)=O)=C1 IJRMMVBFZVJAAS-UHFFFAOYSA-N 0.000 claims 2
- LHHCWDJUFLRMSJ-QGZVFWFLSA-N 2-[3-[[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methyl]phenyl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1CC1=CC=CC(CC(O)=O)=C1 LHHCWDJUFLRMSJ-QGZVFWFLSA-N 0.000 claims 2
- OCVBMTVEVXKSLI-OAHLLOKOSA-N 2-[4-[2-chloro-4-[4-[[(1r)-1-(2-chlorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)Cl)C(=O)NC1=C(C)ON=C1C(C=C1Cl)=CC=C1C1=CC=C(CC(O)=O)C=C1 OCVBMTVEVXKSLI-OAHLLOKOSA-N 0.000 claims 2
- HMCABEARYUIMAL-OAHLLOKOSA-N 2-[4-[3-chloro-4-[4-[[(1r)-1-(2-chlorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)Cl)C(=O)NC1=C(C)ON=C1C(C(=C1)Cl)=CC=C1C1=CC=C(CC(O)=O)C=C1 HMCABEARYUIMAL-OAHLLOKOSA-N 0.000 claims 2
- DNOWPFLHVDBRSW-UHFFFAOYSA-N 2-[4-[4-[4-[1-(2,3-difluorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]acetic acid Chemical compound C=1C=CC(F)=C(F)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(CC(O)=O)C=C1 DNOWPFLHVDBRSW-UHFFFAOYSA-N 0.000 claims 2
- UIFMNDYVKMBUNB-UHFFFAOYSA-N 2-[4-[4-[4-[1-(2,6-difluorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]acetic acid Chemical compound FC=1C=CC=C(F)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(CC(O)=O)C=C1 UIFMNDYVKMBUNB-UHFFFAOYSA-N 0.000 claims 2
- OIPIOGBLKYRDIU-UHFFFAOYSA-N 2-[4-[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]propanoic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(C(C)C(O)=O)C=C1 OIPIOGBLKYRDIU-UHFFFAOYSA-N 0.000 claims 2
- JZGDATWSMIDXEA-UHFFFAOYSA-N 2-[4-[4-[4-[1-(2-fluorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]-2-methylpropanoic acid Chemical compound C=1C=CC=C(F)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(C(C)(C)C(O)=O)C=C1 JZGDATWSMIDXEA-UHFFFAOYSA-N 0.000 claims 2
- NLUAABYBJYQYKT-UHFFFAOYSA-N 2-[4-[4-[4-[1-(2-fluorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]propanoic acid Chemical compound C=1C=CC=C(F)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(C(C)C(O)=O)C=C1 NLUAABYBJYQYKT-UHFFFAOYSA-N 0.000 claims 2
- SOZPXFQIVKKUGZ-QGZVFWFLSA-N 2-[4-[4-[4-[[(1r)-1-(2-chlorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]-2-methylpropanoic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)Cl)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(C(C)(C)C(O)=O)C=C1 SOZPXFQIVKKUGZ-QGZVFWFLSA-N 0.000 claims 2
- COBYXCXDUVTKFP-LIXIDFRTSA-N 2-[4-[4-[4-[[(1r)-1-(2-chlorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]butanoic acid Chemical compound C1=CC(C(C(O)=O)CC)=CC=C1C1=CC=C(C=2C(=C(C)ON=2)NC(=O)O[C@H](C)C=2C(=CC=CC=2)Cl)C=C1 COBYXCXDUVTKFP-LIXIDFRTSA-N 0.000 claims 2
- IZQCMHUHINPDDF-CYBMUJFWSA-N 2-[4-[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]phenyl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(N=1)=CSC=1C1=CC=C(CC(O)=O)C=C1 IZQCMHUHINPDDF-CYBMUJFWSA-N 0.000 claims 2
- YMWKAZHGWHSZEV-QRWMCTBCSA-N 2-[4-[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]-2-methylphenyl]phenyl]propanoic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(C=C1C)=CC=C1C1=CC=C(C(C)C(O)=O)C=C1 YMWKAZHGWHSZEV-QRWMCTBCSA-N 0.000 claims 2
- CQKMDHILFWVVEJ-FXBVVIMESA-N 2-[4-[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]-2-hydroxyacetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(C(O)C(O)=O)C=C1 CQKMDHILFWVVEJ-FXBVVIMESA-N 0.000 claims 2
- CAIXJNGREPLJPB-MRXNPFEDSA-N 2-[4-[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(CC(O)=O)C=C1 CAIXJNGREPLJPB-MRXNPFEDSA-N 0.000 claims 2
- NLUAABYBJYQYKT-ZYMOGRSISA-N 2-[4-[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]propanoic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(C(C)C(O)=O)C=C1 NLUAABYBJYQYKT-ZYMOGRSISA-N 0.000 claims 2
- HHTGDDRDWUWWLN-MRXNPFEDSA-N 2-[4-[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]sulfanylphenyl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1SC1=CC=C(CC(O)=O)C=C1 HHTGDDRDWUWWLN-MRXNPFEDSA-N 0.000 claims 2
- VTOLOLFIARHIQS-INIZCTEOSA-N 2-[4-[4-[4-[[(1s)-1-(2-chlorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]acetic acid Chemical compound O([C@@H](C)C=1C(=CC=CC=1)Cl)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(CC(O)=O)C=C1 VTOLOLFIARHIQS-INIZCTEOSA-N 0.000 claims 2
- CAIXJNGREPLJPB-INIZCTEOSA-N 2-[4-[4-[4-[[(1s)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]acetic acid Chemical compound O([C@@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(CC(O)=O)C=C1 CAIXJNGREPLJPB-INIZCTEOSA-N 0.000 claims 2
- YXUPKMKYXSZDHZ-GOSISDBHSA-N 2-[4-[4-[5-methyl-4-[[(1r)-1-(2-methylphenyl)ethoxy]carbonylamino]-1,2-oxazol-3-yl]phenyl]phenyl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)C)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(CC(O)=O)C=C1 YXUPKMKYXSZDHZ-GOSISDBHSA-N 0.000 claims 2
- PNUVDGKGKXWASR-CYBMUJFWSA-N 2-[4-[5-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]phenyl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(S1)=CN=C1C1=CC=C(CC(O)=O)C=C1 PNUVDGKGKXWASR-CYBMUJFWSA-N 0.000 claims 2
- WTZXRUIRDPQNBR-UHFFFAOYSA-N 2-[4-[6-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]pyridin-3-yl]phenyl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(N=C1)=CC=C1C1=CC=C(CC(O)=O)C=C1 WTZXRUIRDPQNBR-UHFFFAOYSA-N 0.000 claims 2
- BOAMWHKMHAWUBE-UHFFFAOYSA-N 2-[4-[[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methyl]phenyl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1CC1=CC=C(CC(O)=O)C=C1 BOAMWHKMHAWUBE-UHFFFAOYSA-N 0.000 claims 2
- WNKDDEOCVYNIJH-UHFFFAOYSA-N 2-[4-[[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methylsulfonyl]phenyl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1CS(=O)(=O)C1=CC=C(CC(O)=O)C=C1 WNKDDEOCVYNIJH-UHFFFAOYSA-N 0.000 claims 2
- QBOKCUFZFCALQX-QGZVFWFLSA-N 2-[4-[[4-[4-[[(1r)-1-(2-chlorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methoxy]phenyl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)Cl)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1COC1=CC=C(CC(O)=O)C=C1 QBOKCUFZFCALQX-QGZVFWFLSA-N 0.000 claims 2
- FYXNUNOICCOJKT-UHFFFAOYSA-N 2-[5-[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]pyridin-3-yl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CN=CC(CC(O)=O)=C1 FYXNUNOICCOJKT-UHFFFAOYSA-N 0.000 claims 2
- KLQZPEUOQAEWDW-UHFFFAOYSA-N 2-[6-[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]pyridin-3-yl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(CC(O)=O)C=N1 KLQZPEUOQAEWDW-UHFFFAOYSA-N 0.000 claims 2
- SLZGXMJAWDJHQM-OAHLLOKOSA-N 2-[6-[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]sulfanylpyridin-3-yl]acetic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1SC1=CC=C(CC(O)=O)C=N1 SLZGXMJAWDJHQM-OAHLLOKOSA-N 0.000 claims 2
- PNCNYZLSMZXBGX-UHFFFAOYSA-N 3-[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]benzoic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=CC(C(O)=O)=C1 PNCNYZLSMZXBGX-UHFFFAOYSA-N 0.000 claims 2
- FIPWLWTWDQTUCA-UHFFFAOYSA-N 3-[4-[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]propanoic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(CCC(O)=O)C=C1 FIPWLWTWDQTUCA-UHFFFAOYSA-N 0.000 claims 2
- KGOCGOARWWJYCH-UHFFFAOYSA-N 3-[[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methyl]imidazole-4-carboxylic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1CN1C=NC=C1C(O)=O KGOCGOARWWJYCH-UHFFFAOYSA-N 0.000 claims 2
- NXWNZVYNYWNVGC-UHFFFAOYSA-N 4-[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]cyclohex-3-ene-1-carboxylic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CCC(C(O)=O)CC1 NXWNZVYNYWNVGC-UHFFFAOYSA-N 0.000 claims 2
- UDEHKDMFTIVCRJ-UHFFFAOYSA-N 4-[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]cyclohexane-1-carboxylic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1CCC(C(O)=O)CC1 UDEHKDMFTIVCRJ-UHFFFAOYSA-N 0.000 claims 2
- QVQNJNNGWXPBHZ-UHFFFAOYSA-N 4-[4-[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]butanoic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(CCCC(O)=O)C=C1 QVQNJNNGWXPBHZ-UHFFFAOYSA-N 0.000 claims 2
- VHBATFRPLJDCNN-OAHLLOKOSA-N 4-[4-[4-[[(1r)-1-(2-chlorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]benzoic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)Cl)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(C(O)=O)C=C1 VHBATFRPLJDCNN-OAHLLOKOSA-N 0.000 claims 2
- KHEIXGXOOTVYNG-MRXNPFEDSA-N 4-[[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenoxy]methyl]benzoic acid Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1OCC1=CC=C(C(O)=O)C=C1 KHEIXGXOOTVYNG-MRXNPFEDSA-N 0.000 claims 2
- BUYAJOKDUPTFGK-QGZVFWFLSA-N [(1R)-1-(2-fluorophenyl)ethyl] N-[3-[4-[4-(2-acetamido-2-iminoethyl)phenyl]phenyl]-5-methyl-1,2-oxazol-4-yl]carbamate Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(CC(=N)NC(C)=O)C=C1 BUYAJOKDUPTFGK-QGZVFWFLSA-N 0.000 claims 2
- XABWVJCDBGXRSI-MRXNPFEDSA-N [(1R)-1-(2-fluorophenyl)ethyl] N-[3-[4-[4-(2-amino-2-iminoethyl)phenyl]phenyl]-5-methyl-1,2-oxazol-4-yl]carbamate Chemical compound O([C@H](C)C=1C(=CC=CC=1)F)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(CC(N)=N)C=C1 XABWVJCDBGXRSI-MRXNPFEDSA-N 0.000 claims 2
- LTWVZLZIDSRILG-LJQANCHMSA-N [(1r)-1-phenylethyl] n-[3-[4-[4-(dimethoxyphosphorylmethyl)phenyl]phenyl]-5-methyl-1,2-oxazol-4-yl]carbamate Chemical compound C1=CC(CP(=O)(OC)OC)=CC=C1C1=CC=C(C=2C(=C(C)ON=2)NC(=O)O[C@H](C)C=2C=CC=CC=2)C=C1 LTWVZLZIDSRILG-LJQANCHMSA-N 0.000 claims 2
- VZDAGSFPGLYODC-UHFFFAOYSA-N ethyl 2-[4-[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]propanoate Chemical compound C1=CC(C(C)C(=O)OCC)=CC=C1C1=CC=C(C=2C(=C(C)ON=2)NC(=O)OC(C)C=2C(=CC=CC=2)Cl)C=C1 VZDAGSFPGLYODC-UHFFFAOYSA-N 0.000 claims 2
- LLCBIXIGWLDLIZ-GOSISDBHSA-N ethyl 2-[4-[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenoxy]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OC1=CC=C(C=2C(=C(C)ON=2)NC(=O)O[C@H](C)C=2C(=CC=CC=2)F)C=C1 LLCBIXIGWLDLIZ-GOSISDBHSA-N 0.000 claims 2
- 238000001802 infusion Methods 0.000 claims 2
- RKPIIFMVOMWBQO-CYBMUJFWSA-N methyl 2-[5-[4-[4-[[(1r)-1-(2-fluorophenyl)ethoxy]carbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]tetrazol-2-yl]acetate Chemical compound COC(=O)CN1N=NC(C=2C=CC(=CC=2)C=2C(=C(C)ON=2)NC(=O)O[C@H](C)C=2C(=CC=CC=2)F)=N1 RKPIIFMVOMWBQO-CYBMUJFWSA-N 0.000 claims 2
- VJLYHTOSFSGXGH-CQSZACIVSA-N (2R)-1-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]pyrrolidine-2-carboxylic acid Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)N2[C@H](CCC2)C(=O)O)C=CC=1 VJLYHTOSFSGXGH-CQSZACIVSA-N 0.000 claims 1
- ZXAQFYZQHPGMMN-BZSJEYESSA-N (3R)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylcyclohexane-1-carboxamide Chemical compound C1C[C@H](CC(C1)C(=O)NC2=CC=CC=C2)OC3=CC(=CC(=N3)C(F)(F)F)CN ZXAQFYZQHPGMMN-BZSJEYESSA-N 0.000 claims 1
- ZWHOTPNCEFWATE-CQSZACIVSA-N (3R)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylpyrrolidine-1-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@H]1CN(CC1)C(=O)NC1=CC=CC=C1 ZWHOTPNCEFWATE-CQSZACIVSA-N 0.000 claims 1
- ZWHOTPNCEFWATE-AWEZNQCLSA-N (3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylpyrrolidine-1-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CC1)C(=O)NC1=CC=CC=C1 ZWHOTPNCEFWATE-AWEZNQCLSA-N 0.000 claims 1
- SNAKUPLQASYKTC-AWEZNQCLSA-N (3S)-3-[[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxymethyl]-N-phenylpiperidine-1-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC[C@@H]1CN(CCC1)C(=O)NC1=CC=CC=C1 SNAKUPLQASYKTC-AWEZNQCLSA-N 0.000 claims 1
- RAVIQFQJZMTUBX-AWEZNQCLSA-N 1-[(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-2-(3,4-dichlorophenyl)ethanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(CC1=CC(=C(C=C1)Cl)Cl)=O RAVIQFQJZMTUBX-AWEZNQCLSA-N 0.000 claims 1
- XAOMFUPJQYNDEG-LBPRGKRZSA-N 1-[(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-2-methylpropan-1-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(C(C)C)=O XAOMFUPJQYNDEG-LBPRGKRZSA-N 0.000 claims 1
- JZSHKZABPPZQLV-UHFFFAOYSA-N 1-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyridin-2-one Chemical compound NCC1=CC(OC2=CC=CC(=C2)N2C=CC=CC2=O)=NC(=C1)C(F)(F)F JZSHKZABPPZQLV-UHFFFAOYSA-N 0.000 claims 1
- KHKQQQLOLBEJES-UHFFFAOYSA-N 1-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]pyridin-2-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)N1C(C=CC=C1)=O KHKQQQLOLBEJES-UHFFFAOYSA-N 0.000 claims 1
- KJJYKTPTWOMQBQ-UHFFFAOYSA-N 1-[4-[4-[5-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]-1,2-oxazol-3-yl]phenyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound CC(C)(C)OC(=O)NC1=C(C)ON=C1C1=CC=C(C=2C=CC(=CC=2)C2(CC2)C(O)=O)C=C1 KJJYKTPTWOMQBQ-UHFFFAOYSA-N 0.000 claims 1
- VXAFFDNJPRCPMM-LJQANCHMSA-N 1-[4-[4-[5-methyl-4-[[(1r)-1-(4-methylphenyl)ethoxy]carbonylamino]-1,2-oxazol-3-yl]phenyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound O([C@H](C)C=1C=CC(C)=CC=1)C(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C(C=C1)=CC=C1C1(C(O)=O)CC1 VXAFFDNJPRCPMM-LJQANCHMSA-N 0.000 claims 1
- QJQGFIUCAQOASM-UHFFFAOYSA-N 1-[[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methyl]-1,2,4-triazole-3-carboxylic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1CN1C=NC(C(O)=O)=N1 QJQGFIUCAQOASM-UHFFFAOYSA-N 0.000 claims 1
- FZZKXHLEIKNESO-UHFFFAOYSA-N 1-[[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methyl]imidazole-4-carboxylic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1CN1C=NC(C(O)=O)=C1 FZZKXHLEIKNESO-UHFFFAOYSA-N 0.000 claims 1
- WWESTBCNCBYVAH-UHFFFAOYSA-N 1-[[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methyl]pyrazole-4-carboxylic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1CN1C=C(C(O)=O)C=N1 WWESTBCNCBYVAH-UHFFFAOYSA-N 0.000 claims 1
- RNIUHIHTGPHJEN-AWEZNQCLSA-N 2-[(3S)-1-[2-(3,4-dichlorophenyl)acetyl]piperidin-3-yl]oxy-6-(trifluoromethyl)pyridine-4-carbonitrile Chemical compound ClC=1C=C(C=CC=1Cl)CC(=O)N1C[C@H](CCC1)OC=1C=C(C#N)C=C(N=1)C(F)(F)F RNIUHIHTGPHJEN-AWEZNQCLSA-N 0.000 claims 1
- DCGQVDFBDSTUML-AWEZNQCLSA-N 2-[(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidine-1-carbonyl]chromen-4-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)C=1OC2=CC=CC=C2C(C=1)=O DCGQVDFBDSTUML-AWEZNQCLSA-N 0.000 claims 1
- APDYPEOKIUKUQV-UHFFFAOYSA-N 2-[1-(2-oxo-2-piperidin-1-ylethyl)indol-4-yl]oxy-6-(trifluoromethyl)pyridine-4-carbonitrile Chemical compound O=C(CN1C=CC2=C(C=CC=C12)OC=1C=C(C#N)C=C(N=1)C(F)(F)F)N1CCCCC1 APDYPEOKIUKUQV-UHFFFAOYSA-N 0.000 claims 1
- MBBVINHIEJNJHZ-UHFFFAOYSA-N 2-[2-[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=CC=C1CC(O)=O MBBVINHIEJNJHZ-UHFFFAOYSA-N 0.000 claims 1
- XDNUQPIVYCJLNG-UHFFFAOYSA-N 2-[2-[[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methyl]phenyl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1CC1=CC=CC=C1CC(O)=O XDNUQPIVYCJLNG-UHFFFAOYSA-N 0.000 claims 1
- KZJYFEKWPFNHEN-UHFFFAOYSA-N 2-[3-[3-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]-4-fluorophenyl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=1)=CC=CC=1C1=CC(CC(O)=O)=CC=C1F KZJYFEKWPFNHEN-UHFFFAOYSA-N 0.000 claims 1
- AVCXOQNNCFFCDK-UHFFFAOYSA-N 2-[3-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]benzoic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=1)=CC=CC=1C1=CC=CC=C1C(O)=O AVCXOQNNCFFCDK-UHFFFAOYSA-N 0.000 claims 1
- WCGYSSHZESSPGO-UHFFFAOYSA-N 2-[3-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]pyridine-4-carboxylic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=1)=CC=CC=1C1=CC(C(O)=O)=CC=N1 WCGYSSHZESSPGO-UHFFFAOYSA-N 0.000 claims 1
- RIWNJDYXFNNYMK-UHFFFAOYSA-N 2-[3-[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=CC(CC(O)=O)=C1 RIWNJDYXFNNYMK-UHFFFAOYSA-N 0.000 claims 1
- LUPXPXGWTGBSPV-UHFFFAOYSA-N 2-[3-[[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methyl]-4-methoxyphenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1CC1=CC=C(C=2C(=C(C)ON=2)NC(=O)OC(C)C=2C(=CC=CC=2)Cl)C=C1 LUPXPXGWTGBSPV-UHFFFAOYSA-N 0.000 claims 1
- KTPPIIRRIKZBPJ-UHFFFAOYSA-N 2-[3-[[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methylsulfanyl]phenyl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1CSC1=CC=CC(CC(O)=O)=C1 KTPPIIRRIKZBPJ-UHFFFAOYSA-N 0.000 claims 1
- BVKRPQCDGACLPX-UHFFFAOYSA-N 2-[4-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyindol-1-yl]-N-methyl-N-phenylacetamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC1=C2C=CN(C2=CC=C1)CC(=O)N(C1=CC=CC=C1)C BVKRPQCDGACLPX-UHFFFAOYSA-N 0.000 claims 1
- AIOSOYCTGNJOCE-UHFFFAOYSA-N 2-[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]benzoic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=CC=C1C(O)=O AIOSOYCTGNJOCE-UHFFFAOYSA-N 0.000 claims 1
- HRFQWNYYDHTNSX-UHFFFAOYSA-N 2-[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]pyridine-4-carboxylic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC(C(O)=O)=CC=N1 HRFQWNYYDHTNSX-UHFFFAOYSA-N 0.000 claims 1
- DOOXGEMWPVXYBQ-UHFFFAOYSA-N 2-[4-[4-[4-[1-(2,4-dichlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]acetic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(CC(O)=O)C=C1 DOOXGEMWPVXYBQ-UHFFFAOYSA-N 0.000 claims 1
- FSUKLLHHCNWZFQ-UHFFFAOYSA-N 2-[4-[4-[4-[1-(2,6-dichlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]phenyl]acetic acid Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1C1=CC=C(CC(O)=O)C=C1 FSUKLLHHCNWZFQ-UHFFFAOYSA-N 0.000 claims 1
- MASQQWAXAJKJEO-UHFFFAOYSA-N 2-[4-[[4-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]methylsulfanyl]phenyl]acetic acid Chemical compound C=1C=CC=C(Cl)C=1C(C)OC(=O)NC1=C(C)ON=C1C(C=C1)=CC=C1CSC1=CC=C(CC(O)=O)C=C1 MASQQWAXAJKJEO-UHFFFAOYSA-N 0.000 claims 1
- JAAYKMDVVYEHKG-UHFFFAOYSA-N 2-[5-[3-[4-[1-(2-chlorophenyl)ethoxycarbonylamino]-5-methyl-1,2-oxazol-3-yl]phenyl]-6-methoxypyridin-3-yl]acetic acid Chemical compound COC1=NC=C(CC(O)=O)C=C1C1=CC=CC(C=2C(=C(C)ON=2)NC(=O)OC(C)C=2C(=CC=CC=2)Cl)=C1 JAAYKMDVVYEHKG-UHFFFAOYSA-N 0.000 claims 1
- CJYDQTAWSHWBIT-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-hydroxy-2-methylpropyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC(C)(C)O)C=CC=1 CJYDQTAWSHWBIT-UHFFFAOYSA-N 0.000 claims 1
- SHBHYINHXNTBRP-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-methylsulfonylethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCS(=O)(=O)C)C=CC=1 SHBHYINHXNTBRP-UHFFFAOYSA-N 0.000 claims 1
- LIDBMZYKSAXTQG-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-sulfamoylethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCS(N)(=O)=O)C=CC=1 LIDBMZYKSAXTQG-UHFFFAOYSA-N 0.000 claims 1
- VTNULXUEOJMRKZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2H-tetrazol-5-ylmethyl)benzamide Chemical compound N=1NN=NC=1CNC(C1=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)=O VTNULXUEOJMRKZ-UHFFFAOYSA-N 0.000 claims 1
- GDSLUYKCPYECNN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(4-fluorophenyl)methyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC=C(C=C2)F)C=CC=1 GDSLUYKCPYECNN-UHFFFAOYSA-N 0.000 claims 1
- ISXSUKUXUPLGTD-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(5-oxopyrrolidin-2-yl)methyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2NC(CC2)=O)C=CC=1 ISXSUKUXUPLGTD-UHFFFAOYSA-N 0.000 claims 1
- FJPUKTJEFOXMJX-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[1-(hydroxymethyl)cyclopropyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2(CC2)CO)C=CC=1 FJPUKTJEFOXMJX-UHFFFAOYSA-N 0.000 claims 1
- ZMCQQCBOZIGNRV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[2-(1,2,4-triazol-1-yl)ethyl]benzamide Chemical compound NCC1=CC(OC2=CC=CC(=C2)C(=O)NCCN2C=NC=N2)=NC(=C1)C(F)(F)F ZMCQQCBOZIGNRV-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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| JP (1) | JP2013501064A (en:Method) |
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| WO (1) | WO2011017350A2 (en:Method) |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2462128B1 (en) | 2016-09-21 |
| US20120196839A1 (en) | 2012-08-02 |
| EP2462128A4 (en) | 2012-10-03 |
| WO2011017350A2 (en) | 2011-02-10 |
| EP2462128A2 (en) | 2012-06-13 |
| IN2012DN00754A (en:Method) | 2015-06-19 |
| WO2011017350A3 (en) | 2011-06-30 |
| US8592402B2 (en) | 2013-11-26 |
| CN102574822A (zh) | 2012-07-11 |
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