JP2006522033A5 - - Google Patents
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- Publication number
- JP2006522033A5 JP2006522033A5 JP2006504581A JP2006504581A JP2006522033A5 JP 2006522033 A5 JP2006522033 A5 JP 2006522033A5 JP 2006504581 A JP2006504581 A JP 2006504581A JP 2006504581 A JP2006504581 A JP 2006504581A JP 2006522033 A5 JP2006522033 A5 JP 2006522033A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- oxomorpholin
- chlorophenyl
- dicarboxamide
- carboxamide
- 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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- -1 3-oxomorpholin-4-yl Chemical group 0.000 claims description 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 40
- RVEDFFORAVMBLV-UHFFFAOYSA-N pyrrolidine-1,2-dicarboxamide Chemical compound NC(=O)C1CCCN1C(N)=O RVEDFFORAVMBLV-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 3
- HVHPEBUXEYCYLB-RTBURBONSA-N (2r,4r)-1-n-(4-chlorophenyl)-4-hydroxy-2-n-[4-(2-imino-5-methyl-1,3-thiazol-3-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound N=C1SC(C)=CN1C(C=C1)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 HVHPEBUXEYCYLB-RTBURBONSA-N 0.000 claims description 2
- YYBKOFKTRQCDEW-UYAOXDASSA-N (2r,4r)-1-n-(4-chlorophenyl)-4-hydroxy-2-n-[4-(2-iminopyrrolidin-1-yl)-3-methylphenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C([C@H](O)C[C@@H]1C(=O)NC=2C=C(C(=CC=2)N2C(CCC2)=N)C)N1C(=O)NC1=CC=C(Cl)C=C1 YYBKOFKTRQCDEW-UYAOXDASSA-N 0.000 claims description 2
- QKGVCFWQZGNPBC-RTBURBONSA-N (2r,4r)-1-n-(4-chlorophenyl)-4-hydroxy-2-n-[4-(2-iminopyrrolidin-1-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound N1([C@H](C[C@H](C1)O)C(=O)NC=1C=CC(=CC=1)N1C(CCC1)=N)C(=O)NC1=CC=C(Cl)C=C1 QKGVCFWQZGNPBC-RTBURBONSA-N 0.000 claims description 2
- PPWOXIYNZVZCTN-VQIMIIECSA-N (2r,4r)-2-n-[2-carbamoyl-4-(3-oxomorpholin-4-yl)phenyl]-1-n-(4-chlorophenyl)-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound C([C@H](O)C[C@@H]1C(=O)NC2=CC=C(C=C2C(=O)N)N2C(COCC2)=O)N1C(=O)NC1=CC=C(Cl)C=C1 PPWOXIYNZVZCTN-VQIMIIECSA-N 0.000 claims description 2
- LHJVCEMMLRHHSK-HNAYVOBHSA-N (2r,4s)-4-amino-1-n-(4-chlorophenyl)-2-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound N1([C@H](C[C@@H](C1)N)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)NC1=CC=C(Cl)C=C1 LHJVCEMMLRHHSK-HNAYVOBHSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims 3
- DVAWMFRCYCIUAC-VQIMIIECSA-N (2r,4r)-1-n-(4-chlorophenyl)-2-n-[2-fluoro-4-(3-oxomorpholin-4-yl)phenyl]-4-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound N1([C@H](C[C@H](C1)O)C(=O)NC=1C(=CC(=CC=1)N1C(COCC1)=O)F)C(=O)NC1=CC=C(Cl)C=C1 DVAWMFRCYCIUAC-VQIMIIECSA-N 0.000 claims 2
- DMYZJLOWGSRVKP-RTBURBONSA-N (2r,4r)-1-n-(4-chlorophenyl)-4-hydroxy-2-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound N1([C@H](C[C@H](C1)O)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)NC1=CC=C(Cl)C=C1 DMYZJLOWGSRVKP-RTBURBONSA-N 0.000 claims 2
- GKGWERVBDCNFHU-HXUWFJFHSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[2-fluoro-4-(2-oxopyridin-1-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C([C@@H]1C(=O)NC2=CC=C(C=C2F)N2C(C=CC=C2)=O)CCN1C(=O)NC1=CC=C(Cl)C=C1 GKGWERVBDCNFHU-HXUWFJFHSA-N 0.000 claims 1
- JWMWLAIBJDOWAB-LJQANCHMSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[2-fluoro-4-(3-oxomorpholin-4-yl)phenyl]-2,5-dihydropyrrole-1,2-dicarboxamide Chemical compound C([C@@H]1C(=O)NC2=CC=C(C=C2F)N2C(COCC2)=O)=CCN1C(=O)NC1=CC=C(Cl)C=C1 JWMWLAIBJDOWAB-LJQANCHMSA-N 0.000 claims 1
- QAEPOQNAPBZBFO-LJQANCHMSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[2-fluoro-4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C([C@@H]1C(=O)NC2=CC=C(C=C2F)N2C(COCC2)=O)CCN1C(=O)NC1=CC=C(Cl)C=C1 QAEPOQNAPBZBFO-LJQANCHMSA-N 0.000 claims 1
- NFLNBMYZGDHTIO-LJQANCHMSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[3-fluoro-4-(3-oxomorpholin-4-yl)phenyl]-2,5-dihydropyrrole-1,2-dicarboxamide Chemical compound C([C@@H]1C(=O)NC=2C=C(C(=CC=2)N2C(COCC2)=O)F)=CCN1C(=O)NC1=CC=C(Cl)C=C1 NFLNBMYZGDHTIO-LJQANCHMSA-N 0.000 claims 1
- GOOGYBKROAIFSP-LJQANCHMSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[3-fluoro-4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C([C@@H]1C(=O)NC=2C=C(C(=CC=2)N2C(COCC2)=O)F)CCN1C(=O)NC1=CC=C(Cl)C=C1 GOOGYBKROAIFSP-LJQANCHMSA-N 0.000 claims 1
- KGRFFJZSQMZGNV-OAQYLSRUSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]piperidine-1,2-dicarboxamide Chemical compound C([C@@H]1C(=O)NC=2C=C(C(=CC=2)N2C(COCC2)=O)C)CCCN1C(=O)NC1=CC=C(Cl)C=C1 KGRFFJZSQMZGNV-OAQYLSRUSA-N 0.000 claims 1
- FJDROJBPSMOTGQ-HXUWFJFHSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C([C@@H]1C(=O)NC=2C=C(C(=CC=2)N2C(COCC2)=O)C)CCN1C(=O)NC1=CC=C(Cl)C=C1 FJDROJBPSMOTGQ-HXUWFJFHSA-N 0.000 claims 1
- GGHPMOKDRZKXAP-LJQANCHMSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[4-(2-oxopyrazin-1-yl)phenyl]-2,5-dihydropyrrole-1,2-dicarboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1[C@@H](C(=O)NC=2C=CC(=CC=2)N2C(C=NC=C2)=O)C=CC1 GGHPMOKDRZKXAP-LJQANCHMSA-N 0.000 claims 1
- XRNPHSUEJXAARO-LJQANCHMSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[4-(2-oxopyrazin-1-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1[C@@H](C(=O)NC=2C=CC(=CC=2)N2C(C=NC=C2)=O)CCC1 XRNPHSUEJXAARO-LJQANCHMSA-N 0.000 claims 1
- FTKRIFCRKDQKHX-HXUWFJFHSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[4-(2-oxopyridin-1-yl)phenyl]-2,5-dihydropyrrole-1,2-dicarboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1[C@@H](C(=O)NC=2C=CC(=CC=2)N2C(C=CC=C2)=O)C=CC1 FTKRIFCRKDQKHX-HXUWFJFHSA-N 0.000 claims 1
- ZVRFEMHCIFXPIH-HXUWFJFHSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[4-(2-oxopyridin-1-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1[C@@H](C(=O)NC=2C=CC(=CC=2)N2C(C=CC=C2)=O)CCC1 ZVRFEMHCIFXPIH-HXUWFJFHSA-N 0.000 claims 1
- WYJQOESFPMHBHQ-HXUWFJFHSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[4-(3-methoxy-2-oxopyridin-1-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound O=C1C(OC)=CC=CN1C(C=C1)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)CCC1 WYJQOESFPMHBHQ-HXUWFJFHSA-N 0.000 claims 1
- VKSGQOJQICOTAN-LJQANCHMSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[4-(3-oxomorpholin-4-yl)-3-(trifluoromethyl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C([C@@H]1C(=O)NC=2C=C(C(=CC=2)N2C(COCC2)=O)C(F)(F)F)CCN1C(=O)NC1=CC=C(Cl)C=C1 VKSGQOJQICOTAN-LJQANCHMSA-N 0.000 claims 1
- YULBOJOPWIZXBD-LJQANCHMSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[4-(3-oxomorpholin-4-yl)phenyl]-2,5-dihydropyrrole-1,2-dicarboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1[C@@H](C(=O)NC=2C=CC(=CC=2)N2C(COCC2)=O)C=CC1 YULBOJOPWIZXBD-LJQANCHMSA-N 0.000 claims 1
- NMWKHENLIDHRCM-LJQANCHMSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1[C@@H](C(=O)NC=2C=CC(=CC=2)N2C(COCC2)=O)CCC1 NMWKHENLIDHRCM-LJQANCHMSA-N 0.000 claims 1
- QAFUBLOZJSGCNC-HXUWFJFHSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[4-(5-oxo-1,4-oxazepan-4-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1[C@@H](C(=O)NC=2C=CC(=CC=2)N2C(CCOCC2)=O)CCC1 QAFUBLOZJSGCNC-HXUWFJFHSA-N 0.000 claims 1
- WNLPRJBAOOQMBC-FOIQADDNSA-N (2r)-1-n-(4-chlorophenyl)-2-n-[4-[(2r)-2-methyl-3-oxomorpholin-4-yl]phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound O=C1[C@@H](C)OCCN1C(C=C1)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)CCC1 WNLPRJBAOOQMBC-FOIQADDNSA-N 0.000 claims 1
- WNLPRJBAOOQMBC-MGPUTAFESA-N (2r)-1-n-(4-chlorophenyl)-2-n-[4-[(2s)-2-methyl-3-oxomorpholin-4-yl]phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound O=C1[C@H](C)OCCN1C(C=C1)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)CCC1 WNLPRJBAOOQMBC-MGPUTAFESA-N 0.000 claims 1
- VQXISNMZTFPINL-LJQANCHMSA-N (2r)-1-n-(4-chlorophenyl)-4,4-difluoro-2-n-[4-(2-oxopyridin-1-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound N1([C@H](CC(C1)(F)F)C(=O)NC=1C=CC(=CC=1)N1C(C=CC=C1)=O)C(=O)NC1=CC=C(Cl)C=C1 VQXISNMZTFPINL-LJQANCHMSA-N 0.000 claims 1
- QBXCMKKONVCHGK-OAQYLSRUSA-N (2r)-1-n-(4-chlorophenyl)-4,4-dimethoxy-2-n-[4-(2-oxopyridin-1-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound N1([C@H](CC(C1)(OC)OC)C(=O)NC=1C=CC(=CC=1)N1C(C=CC=C1)=O)C(=O)NC1=CC=C(Cl)C=C1 QBXCMKKONVCHGK-OAQYLSRUSA-N 0.000 claims 1
- XTPRCZLXYJLWRE-LJQANCHMSA-N (2r)-1-n-(4-chlorophenyl)-4-oxo-2-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1[C@@H](C(=O)NC=2C=CC(=CC=2)N2C(COCC2)=O)CC(=O)C1 XTPRCZLXYJLWRE-LJQANCHMSA-N 0.000 claims 1
- IWEQFIGHZBYXAF-LJQANCHMSA-N (2r)-1-n-(5-chloropyridin-2-yl)-4,4-dimethoxy-2-n-[4-(2-oxopyridin-1-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound N1([C@H](CC(C1)(OC)OC)C(=O)NC=1C=CC(=CC=1)N1C(C=CC=C1)=O)C(=O)NC1=CC=C(Cl)C=N1 IWEQFIGHZBYXAF-LJQANCHMSA-N 0.000 claims 1
- RKFPRGWDNCNMCT-GOSISDBHSA-N (2r)-1-n-(5-chloropyridin-2-yl)-4,4-dimethoxy-2-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound N1([C@H](CC(C1)(OC)OC)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)NC1=CC=C(Cl)C=N1 RKFPRGWDNCNMCT-GOSISDBHSA-N 0.000 claims 1
- RSTITRFVOKEISD-LJQANCHMSA-N (2r)-2-n-(4-chlorophenyl)-1-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(=CC=2)N2C(COCC2)=O)CCC1 RSTITRFVOKEISD-LJQANCHMSA-N 0.000 claims 1
- JIJYRHDGXGCDJY-HXUWFJFHSA-N (2r)-n-(4-chlorophenyl)-1-[2-[4-(3-oxomorpholin-4-yl)phenyl]acetyl]pyrrolidine-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)[C@@H]1N(C(=O)CC=2C=CC(=CC=2)N2C(COCC2)=O)CCC1 JIJYRHDGXGCDJY-HXUWFJFHSA-N 0.000 claims 1
- MRTFUFLCZKAPAP-UYAOXDASSA-N (2r,3r)-1-n-(4-chlorophenyl)-2-n-[3-fluoro-4-(3-oxomorpholin-4-yl)phenyl]-3-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound O=C([C@@H]1N(CC[C@H]1O)C(=O)NC=1C=CC(Cl)=CC=1)NC(C=C1F)=CC=C1N1CCOCC1=O MRTFUFLCZKAPAP-UYAOXDASSA-N 0.000 claims 1
- MRTFUFLCZKAPAP-AZUAARDMSA-N (2r,3s)-1-n-(4-chlorophenyl)-2-n-[3-fluoro-4-(3-oxomorpholin-4-yl)phenyl]-3-hydroxypyrrolidine-1,2-dicarboxamide Chemical compound O=C([C@@H]1N(CC[C@@H]1O)C(=O)NC=1C=CC(Cl)=CC=1)NC(C=C1F)=CC=C1N1CCOCC1=O MRTFUFLCZKAPAP-AZUAARDMSA-N 0.000 claims 1
- OOLHEGBMCONDON-MISYRCLQSA-N (2r,3s,4r)-1-n-(4-chlorophenyl)-3,4-dihydroxy-2-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-1,2-dicarboxamide Chemical compound O=C([C@@H]1N(C[C@H]([C@H]1O)O)C(=O)NC=1C=CC(Cl)=CC=1)NC(C=C1)=CC=C1N1CCOCC1=O OOLHEGBMCONDON-MISYRCLQSA-N 0.000 claims 1
- OGSANWVJXQAIRN-RTBURBONSA-N (2r,4r)-1-(4-chlorobenzoyl)-4-hydroxy-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@H](C[C@H](C1)O)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)C=C1 OGSANWVJXQAIRN-RTBURBONSA-N 0.000 claims 1
- OJCLBINXHNLSGK-LVLPYEQSSA-N (2r,4r)-1-[(e)-3-(1h-imidazol-5-yl)prop-2-enoyl]-4-methoxy-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)\C=C\C1=CNC=N1 OJCLBINXHNLSGK-LVLPYEQSSA-N 0.000 claims 1
- VRENKQPFVKSKNL-POVKHUTMSA-N (2r,4r)-1-[(e)-3-(3,4-dichlorophenyl)prop-2-enoyl]-4-ethoxy-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@H](C[C@H](C1)OCC)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)\C=C\C1=CC=C(Cl)C(Cl)=C1 VRENKQPFVKSKNL-POVKHUTMSA-N 0.000 claims 1
- DIZATURBOIZCLQ-SQHZKEONSA-N (2r,4r)-1-[(e)-3-(3,4-dichlorophenyl)prop-2-enoyl]-4-hydroxy-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@H](C[C@H](C1)O)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)\C=C\C1=CC=C(Cl)C(Cl)=C1 DIZATURBOIZCLQ-SQHZKEONSA-N 0.000 claims 1
- IMCBDNWDQMOASV-OJACVWAZSA-N (2r,4r)-1-[(e)-3-(3,4-dichlorophenyl)prop-2-enoyl]-4-methoxy-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)\C=C\C1=CC=C(Cl)C(Cl)=C1 IMCBDNWDQMOASV-OJACVWAZSA-N 0.000 claims 1
- YRXKBVOWOCXRGZ-WKQNUPFUSA-N (2r,4r)-1-[(e)-3-(4-bromothiophen-2-yl)prop-2-enoyl]-4-ethoxy-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@H](C[C@H](C1)OCC)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)\C=C\C1=CC(Br)=CS1 YRXKBVOWOCXRGZ-WKQNUPFUSA-N 0.000 claims 1
- XZFHNWZOWYTEIX-IBMJZYDUSA-N (2r,4r)-1-[(e)-3-(4-bromothiophen-2-yl)prop-2-enoyl]-4-hydroxy-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@H](C[C@H](C1)O)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)\C=C\C1=CC(Br)=CS1 XZFHNWZOWYTEIX-IBMJZYDUSA-N 0.000 claims 1
- WVSUJZMCQUKNIS-OWCINNQBSA-N (2r,4r)-1-[(e)-3-(4-chlorophenyl)prop-2-enoyl]-4-ethoxy-n-[2-fluoro-4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@H](C[C@H](C1)OCC)C(=O)NC=1C(=CC(=CC=1)N1C(COCC1)=O)F)C(=O)\C=C\C1=CC=C(Cl)C=C1 WVSUJZMCQUKNIS-OWCINNQBSA-N 0.000 claims 1
- NUKDURHKWVHYHM-HFFNVBOQSA-N (2r,4r)-1-[(e)-3-(4-chlorophenyl)prop-2-enoyl]-4-ethoxy-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@H](C[C@H](C1)OCC)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)\C=C\C1=CC=C(Cl)C=C1 NUKDURHKWVHYHM-HFFNVBOQSA-N 0.000 claims 1
- NDORMENFKGUSCW-RVPUNCECSA-N (2r,4r)-1-[(e)-3-(4-chlorophenyl)prop-2-enoyl]-4-hydroxy-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@H](C[C@H](C1)O)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)\C=C\C1=CC=C(Cl)C=C1 NDORMENFKGUSCW-RVPUNCECSA-N 0.000 claims 1
- UBNHTTMGXFRXQW-IADXMVKGSA-N (2r,4r)-1-[(e)-3-(4-chlorophenyl)prop-2-enoyl]-4-methoxy-n-[4-(3-oxomorpholin-4-yl)phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)\C=C\C1=CC=C(Cl)C=C1 UBNHTTMGXFRXQW-IADXMVKGSA-N 0.000 claims 1
- SCPDUNMFRMJEGW-OPASBBJXSA-N (2r,4r)-1-[(e)-3-(4-chlorophenyl)prop-2-enoyl]-n-[2-fluoro-4-(3-oxomorpholin-4-yl)phenyl]-4-hydroxypyrrolidine-2-carboxamide Chemical compound N1([C@H](C[C@H](C1)O)C(=O)NC=1C(=CC(=CC=1)N1C(COCC1)=O)F)C(=O)\C=C\C1=CC=C(Cl)C=C1 SCPDUNMFRMJEGW-OPASBBJXSA-N 0.000 claims 1
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2004
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- 2004-03-08 AT AT04718299T patent/ATE430139T1/de not_active IP Right Cessation
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- 2004-03-08 DE DE502004009440T patent/DE502004009440D1/de not_active Expired - Lifetime
- 2004-03-08 EP EP04718299A patent/EP1720844B1/de not_active Expired - Lifetime
- 2004-03-08 WO PCT/EP2004/002350 patent/WO2004087646A2/de not_active Ceased
- 2004-03-08 CA CA2521069A patent/CA2521069C/en not_active Expired - Fee Related
- 2004-03-08 US US10/551,557 patent/US7906516B2/en not_active Expired - Fee Related
- 2004-03-08 JP JP2006504581A patent/JP4705015B2/ja not_active Expired - Fee Related
- 2004-03-08 PL PL377633A patent/PL377633A1/pl not_active Application Discontinuation
- 2004-03-08 AU AU2004226278A patent/AU2004226278B2/en not_active Ceased
- 2004-03-08 KR KR1020057018638A patent/KR20050118708A/ko not_active Withdrawn
- 2004-03-08 NZ NZ543366A patent/NZ543366A/en unknown
- 2004-03-08 ES ES04718299T patent/ES2325077T3/es not_active Expired - Lifetime
- 2004-03-31 TW TW093108890A patent/TW200512200A/zh unknown
- 2004-03-31 MY MYPI20041185A patent/MY140031A/en unknown
- 2004-04-02 PE PE2004000350A patent/PE20050015A1/es not_active Application Discontinuation
- 2004-04-02 CL CL200400720A patent/CL2004000720A1/es unknown
- 2004-04-02 AR ARP040101114A patent/AR043832A1/es not_active Application Discontinuation
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2005
- 2005-09-29 IL IL171214A patent/IL171214A/en not_active IP Right Cessation
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- 2005-10-28 EC EC2005006131A patent/ECSP056131A/es unknown
-
2010
- 2010-06-17 US US12/817,314 patent/US8129373B2/en not_active Expired - Fee Related
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