NO327006B1 - Inhibitor av faktor XA og andre serinin proteaser involvert i koagulasjonskaskaden, samt anvendelse og fremgangsmate for fremstilling derav og farmasoytisk sammensetning - Google Patents
Inhibitor av faktor XA og andre serinin proteaser involvert i koagulasjonskaskaden, samt anvendelse og fremgangsmate for fremstilling derav og farmasoytisk sammensetning Download PDFInfo
- Publication number
- NO327006B1 NO327006B1 NO20042270A NO20042270A NO327006B1 NO 327006 B1 NO327006 B1 NO 327006B1 NO 20042270 A NO20042270 A NO 20042270A NO 20042270 A NO20042270 A NO 20042270A NO 327006 B1 NO327006 B1 NO 327006B1
- Authority
- NO
- Norway
- Prior art keywords
- amide
- phenyl
- pyrrolidine
- chloro
- dicarboxylic acid
- Prior art date
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- 108010074860 Factor Xa Proteins 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title description 28
- 230000015271 coagulation Effects 0.000 title description 8
- 238000005345 coagulation Methods 0.000 title description 8
- 239000003112 inhibitor Substances 0.000 title description 5
- 108091005804 Peptidases Proteins 0.000 title 1
- 102000035195 Peptidases Human genes 0.000 title 1
- 239000004365 Protease Substances 0.000 title 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 963
- -1 3-fluoro-2'-sulfamoyl-biphenyl-4-yl Chemical group 0.000 claims description 740
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- 150000001875 compounds Chemical class 0.000 claims description 320
- OAWXZFGKDDFTGS-UHFFFAOYSA-N pyrrolidine-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCN1C(O)=O OAWXZFGKDDFTGS-UHFFFAOYSA-N 0.000 claims description 144
- 150000001408 amides Chemical class 0.000 claims description 141
- QLEZWYHCXVFRKO-UHFFFAOYSA-N 4-methoxypyrrolidine-1,2-dicarboxylic acid Chemical compound COC1CC(C(O)=O)N(C(O)=O)C1 QLEZWYHCXVFRKO-UHFFFAOYSA-N 0.000 claims description 135
- 238000006243 chemical reaction Methods 0.000 claims description 123
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- ZNNRVGZFHOROJG-PHDIDXHHSA-N (2r,4r)-4-ethoxypyrrolidine-1,2-dicarboxylic acid Chemical compound CCO[C@@H]1C[C@H](C(O)=O)N(C(O)=O)C1 ZNNRVGZFHOROJG-PHDIDXHHSA-N 0.000 claims description 53
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
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- 125000000217 alkyl group Chemical group 0.000 claims description 13
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
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- LGLWSZNPYYMBRY-UHFFFAOYSA-N 3-[4-[[1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-2-oxoimidazolidine-4-carboxylic acid Chemical compound C1C(OC)CC(C(=O)NC=2C(=CC(=CC=2)N2C(NCC2C(O)=O)=O)F)N1C(=O)NC1=CC=C(Cl)C=C1 LGLWSZNPYYMBRY-UHFFFAOYSA-N 0.000 claims description 4
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- LYDIFOZLKWKCBD-UHFFFAOYSA-N 1-[4-[[1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]pyrrole-2-carboxylic acid Chemical compound C1C(OC)CC(C(=O)NC=2C(=CC(=CC=2)N2C(=CC=C2)C(O)=O)F)N1C(=O)NC1=CC=C(Cl)C=C1 LYDIFOZLKWKCBD-UHFFFAOYSA-N 0.000 claims description 2
- FJOKYRVDIZBBKP-UHFFFAOYSA-N 1-[4-[[1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]phenyl]pyrrolidine-2-carboxylic acid Chemical compound C1C(OC)CC(C(=O)NC=2C=CC(=CC=2)N2C(CCC2)C(O)=O)N1C(=O)NC1=CC=C(Cl)C=C1 FJOKYRVDIZBBKP-UHFFFAOYSA-N 0.000 claims description 2
- TVHNYAFDTVZTEL-UHFFFAOYSA-N 2-(hydroxymethyl)-4-methoxypyrrolidine-1,2-dicarboxylic acid Chemical compound COC1CN(C(O)=O)C(CO)(C(O)=O)C1 TVHNYAFDTVZTEL-UHFFFAOYSA-N 0.000 claims description 2
- ALNVAFHLHROPIK-OMKBGSMGSA-N 2-[(4r)-1-[4-[[(2r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]phenyl]-2,5-dioxoimidazolidin-4-yl]acetic acid Chemical compound N1([C@H](CC(C1)OC)C(=O)NC=1C=CC(=CC=1)N1C([C@@H](CC(O)=O)NC1=O)=O)C(=O)NC1=CC=C(Cl)C=C1 ALNVAFHLHROPIK-OMKBGSMGSA-N 0.000 claims description 2
- UEKMPJXVWPUNCX-YJEKIOLLSA-N 2-[(4r)-1-[4-[[(2r)-1-[(5-chloropyridin-2-yl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]phenyl]-2,5-dioxoimidazolidin-4-yl]acetic acid Chemical compound N1([C@H](CC(C1)OC)C(=O)NC=1C=CC(=CC=1)N1C([C@@H](CC(O)=O)NC1=O)=O)C(=O)NC1=CC=C(Cl)C=N1 UEKMPJXVWPUNCX-YJEKIOLLSA-N 0.000 claims description 2
- STDUPIADNDLYQU-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)carbamoyl]-2-[[2-fluoro-4-(2-oxopiperidin-1-yl)phenyl]carbamoyl]-4-methoxypyrrolidin-2-yl]acetic acid Chemical compound C=1C=C(N2C(CCCC2)=O)C=C(F)C=1NC(=O)C1(CC(O)=O)CC(OC)CN1C(=O)NC1=CC=C(Cl)C=C1 STDUPIADNDLYQU-UHFFFAOYSA-N 0.000 claims description 2
- RBPYHURAXHAQLL-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)carbamoyl]-5-[[2-fluoro-4-(2-oxopiperidin-1-yl)phenyl]carbamoyl]pyrrolidin-3-yl]acetic acid Chemical compound C1C(CC(=O)O)CC(C(=O)NC=2C(=CC(=CC=2)N2C(CCCC2)=O)F)N1C(=O)NC1=CC=C(Cl)C=C1 RBPYHURAXHAQLL-UHFFFAOYSA-N 0.000 claims description 2
- JLMAPPKOALEWAR-OXQOHEQNSA-N 2-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]pyrazole-3-carboxylic acid Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(=CC=N1)C(O)=O)F)C(=O)NC1=CC=C(Cl)C=C1 JLMAPPKOALEWAR-OXQOHEQNSA-N 0.000 claims description 2
- JLMAPPKOALEWAR-UHFFFAOYSA-N 2-[4-[[1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]pyrazole-3-carboxylic acid Chemical compound C1C(OC)CC(C(=O)NC=2C(=CC(=CC=2)N2C(=CC=N2)C(O)=O)F)N1C(=O)NC1=CC=C(Cl)C=C1 JLMAPPKOALEWAR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- NPLGZUMLQJXKJZ-PXDATVDWSA-N 2-methylpropyl 5-bromo-1-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-2-oxopyridine-3-carboxylate Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C(C(=O)OCC(C)C)=CC(Br)=C1)=O)F)C(=O)NC1=CC=C(Cl)C=C1 NPLGZUMLQJXKJZ-PXDATVDWSA-N 0.000 claims description 2
- JFNYQZNYQLHHHB-AUSIDOKSSA-N 2-methylpropyl 5-bromo-1-[4-[[(2r,4r)-1-[(5-chloropyridin-2-yl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-2-oxopyridine-3-carboxylate Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C(C(=O)OCC(C)C)=CC(Br)=C1)=O)F)C(=O)NC1=CC=C(Cl)C=N1 JFNYQZNYQLHHHB-AUSIDOKSSA-N 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 description 2
- GGFPXUIJPQUKQD-DNVCBOLYSA-N 3-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-1,2-oxazole-4-carboxylic acid Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)C=1C(=CON=1)C(O)=O)F)C(=O)NC1=CC=C(Cl)C=C1 GGFPXUIJPQUKQD-DNVCBOLYSA-N 0.000 claims description 2
- CZLLJOSDIAEUCM-UHFFFAOYSA-N 3-[4-[[1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-1h-pyrrole-2-carboxylic acid Chemical compound C1C(OC)CC(C(=O)NC=2C(=CC(=CC=2)C2=C(NC=C2)C(O)=O)F)N1C(=O)NC1=CC=C(Cl)C=C1 CZLLJOSDIAEUCM-UHFFFAOYSA-N 0.000 claims description 2
- WCOCGGNMEZTHDY-UHFFFAOYSA-N 3-[4-[[1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]furan-2-carboxylic acid Chemical compound C1C(OC)CC(C(=O)NC=2C(=CC(=CC=2)C2=C(OC=C2)C(O)=O)F)N1C(=O)NC1=CC=C(Cl)C=C1 WCOCGGNMEZTHDY-UHFFFAOYSA-N 0.000 claims description 2
- LBPNHDJWKKLZPO-UHFFFAOYSA-N 3-[4-[[1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]thiophene-2-carboxylic acid Chemical compound C1C(OC)CC(C(=O)NC=2C(=CC(=CC=2)C2=C(SC=C2)C(O)=O)F)N1C(=O)NC1=CC=C(Cl)C=C1 LBPNHDJWKKLZPO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- GVZLWFKDTYITCE-UHFFFAOYSA-N 4-(2h-tetrazol-5-yl)pyrrolidine-1,2-dicarboxylic acid Chemical compound C1N(C(O)=O)C(C(=O)O)CC1C1=NN=NN1 GVZLWFKDTYITCE-UHFFFAOYSA-N 0.000 claims description 2
- SOZZGZRWAJRTOI-UHFFFAOYSA-N 4-(methanesulfonamido)pyrrolidine-1,2-dicarboxylic acid Chemical compound CS(=O)(=O)NC1CC(C(O)=O)N(C(O)=O)C1 SOZZGZRWAJRTOI-UHFFFAOYSA-N 0.000 claims description 2
- VFJIWTBLVMNGIM-UHFFFAOYSA-N 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylic acid Chemical compound COCC1CC(C(O)=O)N(C(O)=O)C1 VFJIWTBLVMNGIM-UHFFFAOYSA-N 0.000 claims description 2
- MFHGRSMAIMOMED-UHFFFAOYSA-N 4-(methylamino)pyrrolidine-1,2-dicarboxylic acid Chemical compound CNC1CC(C(O)=O)N(C(O)=O)C1 MFHGRSMAIMOMED-UHFFFAOYSA-N 0.000 claims description 2
- REBBFEZJTFPBIX-UHFFFAOYSA-N 4-(methylaminomethyl)pyrrolidine-1,2-dicarboxylic acid Chemical compound CNCC1CC(C(O)=O)N(C(O)=O)C1 REBBFEZJTFPBIX-UHFFFAOYSA-N 0.000 claims description 2
- VLITYUNEECNVNB-UHFFFAOYSA-N 4-(trifluoromethyl)pyrrolidine-1,2-dicarboxylic acid Chemical compound OC(=O)C1CC(C(F)(F)F)CN1C(O)=O VLITYUNEECNVNB-UHFFFAOYSA-N 0.000 claims description 2
- RTMCNXDSXSHACI-UHFFFAOYSA-N 4-[(dimethylamino)methyl]pyrrolidine-1,2-dicarboxylic acid Chemical compound CN(C)CC1CC(C(O)=O)N(C(O)=O)C1 RTMCNXDSXSHACI-UHFFFAOYSA-N 0.000 claims description 2
- ANIBQQUCFTZYCJ-UHFFFAOYSA-N 4-[4-[[1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-1h-pyrrole-3-carboxylic acid Chemical compound C1C(OC)CC(C(=O)NC=2C(=CC(=CC=2)C=2C(=CNC=2)C(O)=O)F)N1C(=O)NC1=CC=C(Cl)C=C1 ANIBQQUCFTZYCJ-UHFFFAOYSA-N 0.000 claims description 2
- UOADAZXJPZNVBE-UHFFFAOYSA-N 4-[4-[[1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]furan-3-carboxylic acid Chemical compound C1C(OC)CC(C(=O)NC=2C(=CC(=CC=2)C=2C(=COC=2)C(O)=O)F)N1C(=O)NC1=CC=C(Cl)C=C1 UOADAZXJPZNVBE-UHFFFAOYSA-N 0.000 claims description 2
- TVWFOCLZKWPBEV-UHFFFAOYSA-N 4-[4-[[1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]thiophene-3-carboxylic acid Chemical compound C1C(OC)CC(C(=O)NC=2C(=CC(=CC=2)C=2C(=CSC=2)C(O)=O)F)N1C(=O)NC1=CC=C(Cl)C=C1 TVWFOCLZKWPBEV-UHFFFAOYSA-N 0.000 claims description 2
- BPMKDLRAYMTVSR-UHFFFAOYSA-N 4-acetamidopyrrolidine-1,2-dicarboxylic acid Chemical compound CC(=O)NC1CC(C(O)=O)N(C(O)=O)C1 BPMKDLRAYMTVSR-UHFFFAOYSA-N 0.000 claims description 2
- HIOZNSQWNQNLGA-UHFFFAOYSA-N 4-acetylpyrrolidine-1,2-dicarboxylic acid Chemical compound CC(=O)C1CC(C(O)=O)N(C(O)=O)C1 HIOZNSQWNQNLGA-UHFFFAOYSA-N 0.000 claims description 2
- SLJSRCNCQDNSEY-UHFFFAOYSA-N 4-aminopyrrolidine-1,2-dicarboxylic acid Chemical compound NC1CC(C(O)=O)N(C(O)=O)C1 SLJSRCNCQDNSEY-UHFFFAOYSA-N 0.000 claims description 2
- JCINQOYGBLWVGB-UHFFFAOYSA-N 4-cyanopyrrolidine-1,2-dicarboxylic acid Chemical compound OC(=O)C1CC(C#N)CN1C(O)=O JCINQOYGBLWVGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- LBPDNXPDIQWRKX-UHFFFAOYSA-N 4-methoxy-2-(methoxymethyl)pyrrolidine-1,2-dicarboxylic acid Chemical compound COCC1(C(O)=O)CC(OC)CN1C(O)=O LBPDNXPDIQWRKX-UHFFFAOYSA-N 0.000 claims description 2
- ZPWSZKGQDXWSGQ-UHFFFAOYSA-N 4-methylidenepyrrolidine-1,2-dicarboxylic acid Chemical compound OC(=O)C1CC(=C)CN1C(O)=O ZPWSZKGQDXWSGQ-UHFFFAOYSA-N 0.000 claims description 2
- CJHPBOZCFOEIAO-UHFFFAOYSA-N 4-propan-2-yloxypyrrolidine-1,2-dicarboxylic acid Chemical compound CC(C)OC1CC(C(O)=O)N(C(O)=O)C1 CJHPBOZCFOEIAO-UHFFFAOYSA-N 0.000 claims description 2
- XTCRVHGRTFHROD-CRAIPNDOSA-N 5-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-1,3-oxazole-4-carboxylic acid Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)C1=C(N=CO1)C(O)=O)F)C(=O)NC1=CC=C(Cl)C=C1 XTCRVHGRTFHROD-CRAIPNDOSA-N 0.000 claims description 2
- LXZFDZBNPRZYMY-HZPDHXFCSA-N 5-[6-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]pyridin-3-yl]-1,3-oxazole-4-carboxylic acid Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1N=CC(=CC=1)C1=C(N=CO1)C(O)=O)C(=O)NC1=CC=C(Cl)C=C1 LXZFDZBNPRZYMY-HZPDHXFCSA-N 0.000 claims description 2
- GGGAJYNPBMYSIC-DYESRHJHSA-N 5-chloro-1-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-2-oxopyridine-3-carboxylic acid Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C(C(O)=O)=CC(Cl)=C1)=O)F)C(=O)NC1=CC=C(Cl)C=C1 GGGAJYNPBMYSIC-DYESRHJHSA-N 0.000 claims description 2
- PDTOYNIMJHUBLB-DNVCBOLYSA-N 5-chloro-1-[4-[[(2r,4r)-1-[(5-chloropyridin-2-yl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-2-oxopyridine-3-carboxylic acid Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C(C(O)=O)=CC(Cl)=C1)=O)F)C(=O)NC1=CC=C(Cl)C=N1 PDTOYNIMJHUBLB-DNVCBOLYSA-N 0.000 claims description 2
- BJLLOMORJCWXON-UHFFFAOYSA-N 5-oxopyrrolidine-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC(=O)N1C(O)=O BJLLOMORJCWXON-UHFFFAOYSA-N 0.000 claims description 2
- PDVFKFREJYBDKZ-DENIHFKCSA-N N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C(OC(C)=O)=CC=C1)=O)F)C(=O)NC1=CC=C(Cl)C=C1 Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C(OC(C)=O)=CC=C1)=O)F)C(=O)NC1=CC=C(Cl)C=C1 PDVFKFREJYBDKZ-DENIHFKCSA-N 0.000 claims description 2
- QADCCVIARZTMAQ-YLJYHZDGSA-N N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C(OC(C)=O)=CC=C1)=O)F)C(=O)NC1=CC=C(Cl)C=N1 Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C(OC(C)=O)=CC=C1)=O)F)C(=O)NC1=CC=C(Cl)C=N1 QADCCVIARZTMAQ-YLJYHZDGSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- KSTOJMGYXABJEH-UHFFFAOYSA-N ethyl 1-[(4-chlorophenyl)carbamoyl]-5-[[2-fluoro-4-(2-oxopiperidin-1-yl)phenyl]carbamoyl]pyrrolidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CC(C(=O)NC=2C(=CC(=CC=2)N2C(CCCC2)=O)F)N1C(=O)NC1=CC=C(Cl)C=C1 KSTOJMGYXABJEH-UHFFFAOYSA-N 0.000 claims description 2
- FBKNKRVOQGMRCR-GGFVOEBESA-N ethyl 1-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-2-oxopiperidine-3-carboxylate Chemical compound O=C1C(C(=O)OCC)CCCN1C(C=C1F)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](OC)C1 FBKNKRVOQGMRCR-GGFVOEBESA-N 0.000 claims description 2
- YFEUTRWLXYFNHE-NFBKMPQASA-N ethyl 1-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-6-oxopyridine-3-carboxylate Chemical compound C1=C(C(=O)OCC)C=CC(=O)N1C(C=C1F)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](OC)C1 YFEUTRWLXYFNHE-NFBKMPQASA-N 0.000 claims description 2
- QHOZOINOLLHGTH-WIYYLYMNSA-N ethyl 1-[4-[[(2r,4r)-1-[(5-chloropyridin-2-yl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-6-oxopyridine-3-carboxylate Chemical compound C1=C(C(=O)OCC)C=CC(=O)N1C(C=C1F)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2N=CC(Cl)=CC=2)C[C@H](OC)C1 QHOZOINOLLHGTH-WIYYLYMNSA-N 0.000 claims description 2
- NBBPIEIZVXKKCH-UHFFFAOYSA-N ethyl 2-[(4-chlorophenyl)carbamoyl]-3-[[2-fluoro-4-(2-methylsulfonylphenyl)phenyl]carbamoyl]-3,4-dihydropyrazole-5-carboxylate Chemical compound C1C(C(=O)OCC)=NN(C(=O)NC=2C=CC(Cl)=CC=2)C1C(=O)NC(C(=C1)F)=CC=C1C1=CC=CC=C1S(C)(=O)=O NBBPIEIZVXKKCH-UHFFFAOYSA-N 0.000 claims description 2
- JADRUIVIEYALFE-VQIMIIECSA-N ethyl 5-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-1,3-oxazole-4-carboxylate Chemical compound N1=COC(C=2C=C(F)C(NC(=O)[C@@H]3N(C[C@H](O)C3)C(=O)NC=3C=CC(Cl)=CC=3)=CC=2)=C1C(=O)OCC JADRUIVIEYALFE-VQIMIIECSA-N 0.000 claims description 2
- ILIKTNXDUXMWGZ-YLJYHZDGSA-N ethyl 5-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-1,3-oxazole-4-carboxylate Chemical compound N1=COC(C=2C=C(F)C(NC(=O)[C@@H]3N(C[C@@H](C3)OC)C(=O)NC=3C=CC(Cl)=CC=3)=CC=2)=C1C(=O)OCC ILIKTNXDUXMWGZ-YLJYHZDGSA-N 0.000 claims description 2
- RXFJCXXMRKTHKA-QZTJIDSGSA-N ethyl 5-[6-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]pyridin-3-yl]-1,3-oxazole-4-carboxylate Chemical compound N1=COC(C=2C=NC(NC(=O)[C@@H]3N(C[C@@H](C3)OC)C(=O)NC=3C=CC(Cl)=CC=3)=CC=2)=C1C(=O)OCC RXFJCXXMRKTHKA-QZTJIDSGSA-N 0.000 claims description 2
- XEWVCXILHAUGCV-UHFFFAOYSA-N methyl 1-[(4-chlorophenyl)carbamoyl]-5-[[2-fluoro-4-(2-methylsulfonylphenyl)phenyl]carbamoyl]pyrrolidine-3-carboxylate Chemical compound C1C(C(=O)OC)CC(C(=O)NC=2C(=CC(=CC=2)C=2C(=CC=CC=2)S(C)(=O)=O)F)N1C(=O)NC1=CC=C(Cl)C=C1 XEWVCXILHAUGCV-UHFFFAOYSA-N 0.000 claims description 2
- VCUPXGLUFKHEQP-UHFFFAOYSA-N methyl 1-[(4-chlorophenyl)carbamoyl]-5-[[2-fluoro-4-(2-oxopiperidin-1-yl)phenyl]carbamoyl]pyrrolidine-3-carboxylate Chemical compound C1C(C(=O)OC)CC(C(=O)NC=2C(=CC(=CC=2)N2C(CCCC2)=O)F)N1C(=O)NC1=CC=C(Cl)C=C1 VCUPXGLUFKHEQP-UHFFFAOYSA-N 0.000 claims description 2
- USKGFCLNMINYBF-XMSQKQJNSA-N methyl 1-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-2-oxopyridine-3-carboxylate Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C(C(=O)OC)=CC=C1)=O)F)C(=O)NC1=CC=C(Cl)C=C1 USKGFCLNMINYBF-XMSQKQJNSA-N 0.000 claims description 2
- JRMNYBWGCDWAOK-OXQOHEQNSA-N methyl 1-[4-[[(2r,4r)-1-[(5-chloropyridin-2-yl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-6-oxopyridine-2-carboxylate Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C=CC=C1C(=O)OC)=O)F)C(=O)NC1=CC=C(Cl)C=N1 JRMNYBWGCDWAOK-OXQOHEQNSA-N 0.000 claims description 2
- KSFFFIDGIKOTBP-UHFFFAOYSA-N methyl 2-[1-[(4-chlorophenyl)carbamoyl]-2-[[2-fluoro-4-(2-oxopiperidin-1-yl)phenyl]carbamoyl]-4-methoxypyrrolidin-2-yl]acetate Chemical compound C=1C=C(N2C(CCCC2)=O)C=C(F)C=1NC(=O)C1(CC(=O)OC)CC(OC)CN1C(=O)NC1=CC=C(Cl)C=C1 KSFFFIDGIKOTBP-UHFFFAOYSA-N 0.000 claims description 2
- LRKHFVRWDVXQRV-UHFFFAOYSA-N methyl 2-[1-[(4-chlorophenyl)carbamoyl]-5-[[2-fluoro-4-(2-oxopiperidin-1-yl)phenyl]carbamoyl]pyrrolidin-3-yl]acetate Chemical compound C1C(CC(=O)OC)CC(C(=O)NC=2C(=CC(=CC=2)N2C(CCCC2)=O)F)N1C(=O)NC1=CC=C(Cl)C=C1 LRKHFVRWDVXQRV-UHFFFAOYSA-N 0.000 claims description 2
- YWAIKSSOLKLFIP-NTKDMRAZSA-N methyl 2-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]benzoate Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)C=1C(=CC=CC=1)C(=O)OC)F)C(=O)NC1=CC=C(Cl)C=C1 YWAIKSSOLKLFIP-NTKDMRAZSA-N 0.000 claims description 2
- QBVYNMSHKSKFLF-DYESRHJHSA-N methyl 2-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]pyrazole-3-carboxylate Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(=CC=N1)C(=O)OC)F)C(=O)NC1=CC=C(Cl)C=C1 QBVYNMSHKSKFLF-DYESRHJHSA-N 0.000 claims description 2
- DNSNMEBHXMKCSU-UHFFFAOYSA-N methyl 2-[[1-[(4-chlorophenyl)carbamoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-5-(2-methylsulfonylphenyl)benzoate Chemical compound COC(=O)C1=CC(C=2C(=CC=CC=2)S(C)(=O)=O)=CC=C1NC(=O)C1CC(O)CN1C(=O)NC1=CC=C(Cl)C=C1 DNSNMEBHXMKCSU-UHFFFAOYSA-N 0.000 claims description 2
- YSJDRXBPNDLIGW-UHFFFAOYSA-N methyl 2-[[1-[(4-chlorophenyl)carbamoyl]pyrrolidine-2-carbonyl]amino]-5-(2-methylsulfonylphenyl)benzoate Chemical compound COC(=O)C1=CC(C=2C(=CC=CC=2)S(C)(=O)=O)=CC=C1NC(=O)C1CCCN1C(=O)NC1=CC=C(Cl)C=C1 YSJDRXBPNDLIGW-UHFFFAOYSA-N 0.000 claims description 2
- UXPZJMFFNMTOKH-OXQOHEQNSA-N methyl 3-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-1,2-oxazole-4-carboxylate Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)C=1C(=CON=1)C(=O)OC)F)C(=O)NC1=CC=C(Cl)C=C1 UXPZJMFFNMTOKH-OXQOHEQNSA-N 0.000 claims description 2
- OJJMHJWJGWRJOE-VQIMIIECSA-N methyl 4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-3-(dimethylamino)benzoate Chemical compound CN(C)C1=CC(C(=O)OC)=CC=C1NC(=O)[C@@H]1N(C(=O)NC=2C=CC(Cl)=CC=2)C[C@H](O)C1 OJJMHJWJGWRJOE-VQIMIIECSA-N 0.000 claims description 2
- SAWSFOQKHXWPDP-WIYYLYMNSA-N methyl 4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-3-pyrrolidin-1-ylbenzoate Chemical compound C([C@H](O)C[C@@H]1C(=O)NC2=CC=C(C=C2N2CCCC2)C(=O)OC)N1C(=O)NC1=CC=C(Cl)C=C1 SAWSFOQKHXWPDP-WIYYLYMNSA-N 0.000 claims description 2
- DXOXBNDJEPHRCL-XMSQKQJNSA-N methyl 5-chloro-1-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-2-oxopyridine-3-carboxylate Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C(C(=O)OC)=CC(Cl)=C1)=O)F)C(=O)NC1=CC=C(Cl)C=C1 DXOXBNDJEPHRCL-XMSQKQJNSA-N 0.000 claims description 2
- HGFOJQDNWMFXAU-OXQOHEQNSA-N methyl 5-chloro-1-[4-[[(2r,4r)-1-[(5-chloropyridin-2-yl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-2-oxopyridine-3-carboxylate Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C(C(=O)OC)=CC(Cl)=C1)=O)F)C(=O)NC1=CC=C(Cl)C=N1 HGFOJQDNWMFXAU-OXQOHEQNSA-N 0.000 claims description 2
- BDJBQJAZHHLNLK-UHFFFAOYSA-N morpholine-3,4-dicarboxylic acid Chemical compound OC(=O)C1COCCN1C(O)=O BDJBQJAZHHLNLK-UHFFFAOYSA-N 0.000 claims description 2
- IEYMNLYRGAFFMR-UHFFFAOYSA-N piperazine-1,2-dicarboxylic acid Chemical compound OC(=O)C1CNCCN1C(O)=O IEYMNLYRGAFFMR-UHFFFAOYSA-N 0.000 claims description 2
- SMCWNPAVVQIDBM-UHFFFAOYSA-N piperidine-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCN1C(O)=O SMCWNPAVVQIDBM-UHFFFAOYSA-N 0.000 claims description 2
- NFBOGDUOBMRIIN-HYBUGGRVSA-N tert-butyl 1-[4-[[(2r,4r)-1-[(4-chlorophenyl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-2-oxopyridine-3-carboxylate Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C(C(=O)OC(C)(C)C)=CC=C1)=O)F)C(=O)NC1=CC=C(Cl)C=C1 NFBOGDUOBMRIIN-HYBUGGRVSA-N 0.000 claims description 2
- GQHPHXSMTMHOQK-XMSQKQJNSA-N tert-butyl 1-[4-[[(2r,4r)-1-[(5-chloropyridin-2-yl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-2-oxopyridine-3-carboxylate Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C(C(=O)OC(C)(C)C)=CC=C1)=O)F)C(=O)NC1=CC=C(Cl)C=N1 GQHPHXSMTMHOQK-XMSQKQJNSA-N 0.000 claims description 2
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- QNJRGCLOCPIILY-OXQOHEQNSA-N methyl 1-[4-[[(2r,4r)-1-[(5-chloropyridin-2-yl)carbamoyl]-4-methoxypyrrolidine-2-carbonyl]amino]-3-fluorophenyl]-2-oxopyridine-3-carboxylate Chemical compound N1([C@H](C[C@H](C1)OC)C(=O)NC=1C(=CC(=CC=1)N1C(C(C(=O)OC)=CC=C1)=O)F)C(=O)NC1=CC=C(Cl)C=N1 QNJRGCLOCPIILY-OXQOHEQNSA-N 0.000 claims 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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NO20042270A NO327006B1 (no) | 2001-11-29 | 2004-06-01 | Inhibitor av faktor XA og andre serinin proteaser involvert i koagulasjonskaskaden, samt anvendelse og fremgangsmate for fremstilling derav og farmasoytisk sammensetning |
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