CA1180700A - Prostaglandin 1 in2 xx derivatives and process for their production - Google Patents
Prostaglandin 1 in2 xx derivatives and process for their productionInfo
- Publication number
- CA1180700A CA1180700A CA000308336A CA308336A CA1180700A CA 1180700 A CA1180700 A CA 1180700A CA 000308336 A CA000308336 A CA 000308336A CA 308336 A CA308336 A CA 308336A CA 1180700 A CA1180700 A CA 1180700A
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- group
- butyl
- octane
- oxabicyclo
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 145
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000003180 prostaglandins Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 180
- -1 1 to 3 Chemical group 0.000 claims abstract description 62
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 57
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 21
- 125000005843 halogen group Chemical group 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 17
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims abstract description 11
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims abstract description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 7
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 13
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 11
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 126
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 99
- 239000000243 solution Substances 0.000 claims description 95
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 89
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 84
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 77
- 239000000126 substance Substances 0.000 claims description 69
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 66
- 235000013350 formula milk Nutrition 0.000 claims description 57
- 239000002253 acid Substances 0.000 claims description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 38
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000012279 sodium borohydride Substances 0.000 claims description 24
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
- ZLPCARWBHSCIGF-UHFFFAOYSA-N n-(oxomethylidene)propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N=C=O ZLPCARWBHSCIGF-UHFFFAOYSA-N 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims description 7
- 239000012047 saturated solution Substances 0.000 claims description 7
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical class [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 claims description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 5
- 235000019270 ammonium chloride Nutrition 0.000 claims description 5
- 125000000468 ketone group Chemical group 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims 18
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 12
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims 12
- 229960004979 fampridine Drugs 0.000 claims 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 7
- OCKPROYBCPQWJO-UHFFFAOYSA-N acetyl isocyanate Chemical compound CC(=O)N=C=O OCKPROYBCPQWJO-UHFFFAOYSA-N 0.000 claims 6
- 125000006519 CCH3 Chemical group 0.000 claims 5
- FRJXKNXYTQNKNP-UHFFFAOYSA-N methane;sulfuryl diisocyanate Chemical compound C.O=C=NS(=O)(=O)N=C=O FRJXKNXYTQNKNP-UHFFFAOYSA-N 0.000 claims 5
- 150000003254 radicals Chemical class 0.000 claims 5
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims 4
- MAUQLEOPGOXIOT-OBZZXJSUSA-N methyl 5-[(2r,3ar,4r,5r,6as)-5-acetyloxy-4-[(1e)-7-methyl-3-oxoocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\C(=O)CCC=C(C)C MAUQLEOPGOXIOT-OBZZXJSUSA-N 0.000 claims 2
- XHFMNXSRIWXRTM-PTKKKFEJSA-N methyl 5-[(2r,3ar,4r,5r,6as)-5-acetyloxy-4-[(e)-3-oxooct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\C(=O)CCC#CC XHFMNXSRIWXRTM-PTKKKFEJSA-N 0.000 claims 2
- MAUQLEOPGOXIOT-CJNQNQSTSA-N methyl 5-[(2s,3ar,4r,5r,6as)-5-acetyloxy-4-[(1e)-7-methyl-3-oxoocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\C(=O)CCC=C(C)C MAUQLEOPGOXIOT-CJNQNQSTSA-N 0.000 claims 2
- XHFMNXSRIWXRTM-ZAVPQDBASA-N methyl 5-[(2s,3ar,4r,5r,6as)-5-acetyloxy-4-[(e)-3-oxooct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\C(=O)CCC#CC XHFMNXSRIWXRTM-ZAVPQDBASA-N 0.000 claims 2
- FADCEKVWQLUANI-AVYIRHPKSA-N 5-[(2R,3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxy-7-methylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]furan-2-yl]-N-propan-2-ylsulfonylpentanamide Chemical compound C([C@H](O1)CCCCC(=O)NS(=O)(=O)C(C)C)[C@H]2[C@@H]1C[C@@H](O)[C@@H]2\C=C\[C@@H](O)CCC=C(C)C FADCEKVWQLUANI-AVYIRHPKSA-N 0.000 claims 1
- LHBRXWALKPXESN-IIFOHBGFSA-N 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(1e)-3-hydroxy-3,7-dimethylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical compound O1[C@H](CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/C(C)(O)CCC=C(C)C)[C@H](O)C[C@@H]21 LHBRXWALKPXESN-IIFOHBGFSA-N 0.000 claims 1
- XEMMTEIZAOAELZ-XTPNFOEUSA-N 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(1e,3r)-3-hydroxy-4,4,7-trimethylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]-n-acetylpentanamide Chemical compound O1[C@H](CCCCC(=O)NC(C)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(C)(C)CC=C(C)C)[C@H](O)C[C@@H]21 XEMMTEIZAOAELZ-XTPNFOEUSA-N 0.000 claims 1
- XKUVQOGTUAAETB-XBLMJNAKSA-N 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(1e,3s)-3-hydroxy-4,7-dimethylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]-n-acetylpentanamide Chemical compound O1[C@H](CCCCC(=O)NC(C)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(CC=C(C)C)C)[C@H](O)C[C@@H]21 XKUVQOGTUAAETB-XBLMJNAKSA-N 0.000 claims 1
- GTYOGPYMJPGEDO-OFVMCABWSA-N 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(1e,3s)-3-hydroxy-7-methylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]-n-acetylpentanamide Chemical compound O1[C@H](CCCCC(=O)NC(C)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCC=C(C)C)[C@H](O)C[C@@H]21 GTYOGPYMJPGEDO-OFVMCABWSA-N 0.000 claims 1
- GUPMKHVJTWBRDN-ZULSNFRPSA-N 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(1e,3s)-3-hydroxy-7-methylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical compound O1[C@H](CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCC=C(C)C)[C@H](O)C[C@@H]21 GUPMKHVJTWBRDN-ZULSNFRPSA-N 0.000 claims 1
- IDSSEHDEIFDOJX-LYBCRJTLSA-N 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(e)-3-hydroxy-3-methyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical compound O1[C@H](CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/C(C)(O)CCC#CC)[C@H](O)C[C@@H]21 IDSSEHDEIFDOJX-LYBCRJTLSA-N 0.000 claims 1
- JABWOOSPMCGOBY-OFRKORIRSA-N 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(e,3r)-3-hydroxy-4,4-dimethyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]-n-methylsulfonylpentanamide Chemical compound O1[C@H](CCCCC(=O)NS(C)(=O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(C)(C)CC#CC)[C@H](O)C[C@@H]21 JABWOOSPMCGOBY-OFRKORIRSA-N 0.000 claims 1
- UXCWNXNFHZJDCN-XGRZZQNMSA-N 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(e,3r)-3-hydroxy-4,4-dimethyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical compound O1[C@H](CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(C)(C)CC#CC)[C@H](O)C[C@@H]21 UXCWNXNFHZJDCN-XGRZZQNMSA-N 0.000 claims 1
- SDXSWURUHGJWRC-QVSSJXPLSA-N 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxy-4-methyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]-n-propan-2-ylsulfonylpentanamide Chemical compound O1[C@H](CCCCC(=O)NS(=O)(=O)C(C)C)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(C)CC#CC)[C@H](O)C[C@@H]21 SDXSWURUHGJWRC-QVSSJXPLSA-N 0.000 claims 1
- GRFGFANMMMLJKU-QJYVMWDWSA-N 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxyoct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]-n-acetylpentanamide Chemical compound O1[C@H](CCCCC(=O)NC(C)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCC#CC)[C@H](O)C[C@@H]21 GRFGFANMMMLJKU-QJYVMWDWSA-N 0.000 claims 1
- JUSLQXYLWNVJQU-BJCRGZTGSA-N 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxyoct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]-n-methylsulfonylpentanamide Chemical compound O1[C@H](CCCCC(=O)NS(C)(=O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCC#CC)[C@H](O)C[C@@H]21 JUSLQXYLWNVJQU-BJCRGZTGSA-N 0.000 claims 1
- JONBGRIISISFFD-LIEAFCKCSA-N 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxyoct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]-n-propan-2-ylsulfonylpentanamide Chemical compound O1[C@H](CCCCC(=O)NS(=O)(=O)C(C)C)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCC#CC)[C@H](O)C[C@@H]21 JONBGRIISISFFD-LIEAFCKCSA-N 0.000 claims 1
- HNODBRJDAVVSNY-GVDALNIKSA-N 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxyoct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid;2-amino-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(N)(CO)CO.O1[C@H](CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCC#CC)[C@H](O)C[C@@H]21 HNODBRJDAVVSNY-GVDALNIKSA-N 0.000 claims 1
- LHBRXWALKPXESN-JZCOHXQXSA-N 5-[(2s,3ar,4r,5r,6as)-5-hydroxy-4-[(1e)-3-hydroxy-3,7-dimethylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical compound O1[C@@H](CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/C(C)(O)CCC=C(C)C)[C@H](O)C[C@@H]21 LHBRXWALKPXESN-JZCOHXQXSA-N 0.000 claims 1
- JBYPTEPLJVIGTK-NJHQXWEDSA-N 5-[(2s,3ar,4r,5r,6as)-5-hydroxy-4-[(1e,3r)-3-hydroxy-4,4,7-trimethylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical compound O1[C@@H](CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(C)(C)CC=C(C)C)[C@H](O)C[C@@H]21 JBYPTEPLJVIGTK-NJHQXWEDSA-N 0.000 claims 1
- KARVAUQJFMOOSI-VRZRGHAYSA-N 5-[(2s,3ar,4r,5r,6as)-5-hydroxy-4-[(1e,3s)-3-hydroxy-4,7-dimethylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical compound O1[C@@H](CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(CC=C(C)C)C)[C@H](O)C[C@@H]21 KARVAUQJFMOOSI-VRZRGHAYSA-N 0.000 claims 1
- CFHKRCMJTZQLKR-KCZAODCISA-N 5-[(2s,3ar,4r,5r,6as)-5-hydroxy-4-[(1e,3s)-3-hydroxy-7-methylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]-n-methylsulfonylpentanamide Chemical compound O1[C@@H](CCCCC(=O)NS(C)(=O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCC=C(C)C)[C@H](O)C[C@@H]21 CFHKRCMJTZQLKR-KCZAODCISA-N 0.000 claims 1
- GUPMKHVJTWBRDN-OLYMBLLOSA-N 5-[(2s,3ar,4r,5r,6as)-5-hydroxy-4-[(1e,3s)-3-hydroxy-7-methylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical compound O1[C@@H](CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCC=C(C)C)[C@H](O)C[C@@H]21 GUPMKHVJTWBRDN-OLYMBLLOSA-N 0.000 claims 1
- IDSSEHDEIFDOJX-OFHFOSFXSA-N 5-[(2s,3ar,4r,5r,6as)-5-hydroxy-4-[(e)-3-hydroxy-3-methyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical compound O1[C@@H](CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/C(C)(O)CCC#CC)[C@H](O)C[C@@H]21 IDSSEHDEIFDOJX-OFHFOSFXSA-N 0.000 claims 1
- UXCWNXNFHZJDCN-VXMFSAKJSA-N 5-[(2s,3ar,4r,5r,6as)-5-hydroxy-4-[(e,3r)-3-hydroxy-4,4-dimethyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical compound O1[C@@H](CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(C)(C)CC#CC)[C@H](O)C[C@@H]21 UXCWNXNFHZJDCN-VXMFSAKJSA-N 0.000 claims 1
- HSXPOEKQVKUEFO-AEPKWNAHSA-N 5-[(2s,3ar,4r,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxy-4-methyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical compound O1[C@@H](CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(C)CC#CC)[C@H](O)C[C@@H]21 HSXPOEKQVKUEFO-AEPKWNAHSA-N 0.000 claims 1
- MJQPWCSJWKJPGG-CBIPHORWSA-N 5-[(2s,3ar,4r,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxyoct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical compound O1[C@@H](CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCC#CC)[C@H](O)C[C@@H]21 MJQPWCSJWKJPGG-CBIPHORWSA-N 0.000 claims 1
- GAVHEKKTHKQZSS-BPVPLAGTSA-N methyl 5-[(2r,3ar,4r,5r,6as)-5-acetyloxy-4-[(1e)-3-hydroxy-3,7-dimethylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\C(C)(O)CCC=C(C)C GAVHEKKTHKQZSS-BPVPLAGTSA-N 0.000 claims 1
- ULUZCRULDDBELF-JAGOUTKISA-N methyl 5-[(2r,3ar,4r,5r,6as)-5-acetyloxy-4-[(1e)-4,7-dimethyl-3-oxoocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\C(=O)C(C)CC=C(C)C ULUZCRULDDBELF-JAGOUTKISA-N 0.000 claims 1
- WUTDVDFPWHYFOI-LCHPTHGDSA-N methyl 5-[(2r,3ar,4r,5r,6as)-5-acetyloxy-4-[(1e,3r)-3-hydroxy-4,4,7-trimethylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\[C@@H](O)C(C)(C)CC=C(C)C WUTDVDFPWHYFOI-LCHPTHGDSA-N 0.000 claims 1
- ACGCKWSMQOHGER-JCDLTJMCSA-N methyl 5-[(2r,3ar,4r,5r,6as)-5-acetyloxy-4-[(1e,3s)-3-hydroxy-4,7-dimethylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\[C@@H](O)C(C)CC=C(C)C ACGCKWSMQOHGER-JCDLTJMCSA-N 0.000 claims 1
- BNKUNKGXCLFIOJ-AVYIRHPKSA-N methyl 5-[(2r,3ar,4r,5r,6as)-5-acetyloxy-4-[(1e,3s)-3-hydroxy-7-methylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\[C@@H](O)CCC=C(C)C BNKUNKGXCLFIOJ-AVYIRHPKSA-N 0.000 claims 1
- GJUHDDLTHPFBPZ-KZQJCQJESA-N methyl 5-[(2r,3ar,4r,5r,6as)-5-acetyloxy-4-[(e)-3-hydroxy-3-methyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\C(C)(O)CCC#CC GJUHDDLTHPFBPZ-KZQJCQJESA-N 0.000 claims 1
- PPYMIQCGJTVSLS-PTKKKFEJSA-N methyl 5-[(2r,3ar,4r,5r,6as)-5-acetyloxy-4-[(e)-4,4-dimethyl-3-oxooct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\C(=O)C(C)(C)CC#CC PPYMIQCGJTVSLS-PTKKKFEJSA-N 0.000 claims 1
- JSEWMZWVABBZIW-LIEAFCKCSA-N methyl 5-[(2r,3ar,4r,5r,6as)-5-acetyloxy-4-[(e,3s)-3-hydroxyoct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\[C@@H](O)CCC#CC JSEWMZWVABBZIW-LIEAFCKCSA-N 0.000 claims 1
- XDSMSKUPWZSGBC-ZGCHDHQESA-N methyl 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(1e,3r)-3-hydroxy-4,4,7-trimethylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](O)[C@@H]2\C=C\[C@@H](O)C(C)(C)CC=C(C)C XDSMSKUPWZSGBC-ZGCHDHQESA-N 0.000 claims 1
- GOBZYUCTVFXJNQ-QJYVMWDWSA-N methyl 5-[(2r,3ar,4r,5r,6as)-5-hydroxy-4-[(1e,3s)-3-hydroxy-7-methylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](O)[C@@H]2\C=C\[C@@H](O)CCC=C(C)C GOBZYUCTVFXJNQ-QJYVMWDWSA-N 0.000 claims 1
- CZZCAOVXGSRPER-HUOSKOSRSA-N methyl 5-[(2s,3ar,4r,5r,6as)-5-acetyloxy-4-[(1e)-4,4,7-trimethyl-3-oxoocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\C(=O)C(C)(C)CC=C(C)C CZZCAOVXGSRPER-HUOSKOSRSA-N 0.000 claims 1
- ACGCKWSMQOHGER-ZFBGGBANSA-N methyl 5-[(2s,3ar,4r,5r,6as)-5-acetyloxy-4-[(1e,3s)-3-hydroxy-4,7-dimethylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\[C@@H](O)C(C)CC=C(C)C ACGCKWSMQOHGER-ZFBGGBANSA-N 0.000 claims 1
- BNKUNKGXCLFIOJ-JZNWQUTLSA-N methyl 5-[(2s,3ar,4r,5r,6as)-5-acetyloxy-4-[(1e,3s)-3-hydroxy-7-methylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\[C@@H](O)CCC=C(C)C BNKUNKGXCLFIOJ-JZNWQUTLSA-N 0.000 claims 1
- GJUHDDLTHPFBPZ-XWAYJZTOSA-N methyl 5-[(2s,3ar,4r,5r,6as)-5-acetyloxy-4-[(e)-3-hydroxy-3-methyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\C(C)(O)CCC#CC GJUHDDLTHPFBPZ-XWAYJZTOSA-N 0.000 claims 1
- PPYMIQCGJTVSLS-ZAVPQDBASA-N methyl 5-[(2s,3ar,4r,5r,6as)-5-acetyloxy-4-[(e)-4,4-dimethyl-3-oxooct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\C(=O)C(C)(C)CC#CC PPYMIQCGJTVSLS-ZAVPQDBASA-N 0.000 claims 1
- YZHQVWQQSOZCKM-VSNAEHKTSA-N methyl 5-[(2s,3ar,4r,5r,6as)-5-acetyloxy-4-[(e)-4-methyl-3-oxooct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\C(=O)C(C)CC#CC YZHQVWQQSOZCKM-VSNAEHKTSA-N 0.000 claims 1
- XWIZJUHFBBBFOX-GBFJTJNWSA-N methyl 5-[(2s,3ar,4r,5r,6as)-5-acetyloxy-4-[(e,3s)-3-hydroxy-4-methyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\[C@@H](O)C(C)CC#CC XWIZJUHFBBBFOX-GBFJTJNWSA-N 0.000 claims 1
- JSEWMZWVABBZIW-ZLXSTKBVSA-N methyl 5-[(2s,3ar,4r,5r,6as)-5-acetyloxy-4-[(e,3s)-3-hydroxyoct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\[C@@H](O)CCC#CC JSEWMZWVABBZIW-ZLXSTKBVSA-N 0.000 claims 1
- GOBZYUCTVFXJNQ-KCZAODCISA-N methyl 5-[(2s,3ar,4r,5r,6as)-5-hydroxy-4-[(1e,3s)-3-hydroxy-7-methylocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](O)[C@@H]2\C=C\[C@@H](O)CCC=C(C)C GOBZYUCTVFXJNQ-KCZAODCISA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 238000004809 thin layer chromatography Methods 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
- 230000036772 blood pressure Effects 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 83
- 239000003921 oil Substances 0.000 description 69
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- 229940073584 methylene chloride Drugs 0.000 description 27
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 21
- 235000019341 magnesium sulphate Nutrition 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- 235000019441 ethanol Nutrition 0.000 description 18
- 235000017557 sodium bicarbonate Nutrition 0.000 description 17
- 229960001407 sodium bicarbonate Drugs 0.000 description 17
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 16
- 239000012267 brine Substances 0.000 description 16
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 14
- 230000007935 neutral effect Effects 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- 230000000875 corresponding effect Effects 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 9
- 229910021653 sulphate ion Inorganic materials 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 229960004756 ethanol Drugs 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- 229960004132 diethyl ether Drugs 0.000 description 7
- 229960004592 isopropanol Drugs 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 4
- QHINYJQPBCMLCJ-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan Chemical compound C1COC2CCCC21 QHINYJQPBCMLCJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 210000001772 blood platelet Anatomy 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000013375 chromatographic separation Methods 0.000 description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229940100892 mercury compound Drugs 0.000 description 3
- 150000002731 mercury compounds Chemical class 0.000 description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 229940086542 triethylamine Drugs 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 101100310593 Candida albicans (strain SC5314 / ATCC MYA-2876) SOD4 gene Proteins 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- YVHAIVPPUIZFBA-UHFFFAOYSA-N Cyclopentylacetic acid Chemical compound OC(=O)CC1CCCC1 YVHAIVPPUIZFBA-UHFFFAOYSA-N 0.000 description 2
- 101710198144 Endopolygalacturonase I Proteins 0.000 description 2
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 101710191566 Probable endopolygalacturonase I Proteins 0.000 description 2
- MYHXHCUNDDAEOZ-UHFFFAOYSA-N Prostaglandin A&2% Natural products CCCCCC(O)C=CC1C=CC(=O)C1CC=CCCCC(O)=O MYHXHCUNDDAEOZ-UHFFFAOYSA-N 0.000 description 2
- 101100190148 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PGA2 gene Proteins 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- 229940076134 benzene Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 235000001465 calcium Nutrition 0.000 description 2
- 229960005069 calcium Drugs 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 235000011116 calcium hydroxide Nutrition 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 229940095643 calcium hydroxide Drugs 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 2
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 2
- 229960002986 dinoprostone Drugs 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 229940057952 methanol Drugs 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 229940095574 propionic acid Drugs 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- MYHXHCUNDDAEOZ-FOSBLDSVSA-N prostaglandin A2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O MYHXHCUNDDAEOZ-FOSBLDSVSA-N 0.000 description 2
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 2
- UKVVPDHLUHAJNZ-PMACEKPBSA-N prostane Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC UKVVPDHLUHAJNZ-PMACEKPBSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
- VXBBXTLIXJOCET-UHFFFAOYSA-N (3,6-dimethyl-2-oxohept-5-enyl)phosphonic acid Chemical compound CC(C)=CCC(C)C(=O)CP(O)(O)=O VXBBXTLIXJOCET-UHFFFAOYSA-N 0.000 description 1
- NSMXQKNUPPXBRG-SECBINFHSA-N (R)-lisofylline Chemical group O=C1N(CCCC[C@H](O)C)C(=O)N(C)C2=C1N(C)C=N2 NSMXQKNUPPXBRG-SECBINFHSA-N 0.000 description 1
- AEBWATHAIVJLTA-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropentalene Chemical compound C1CCC2CCCC21 AEBWATHAIVJLTA-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 1
- FQMVLQNNAODGQV-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3,3-dimethylhept-5-yn-2-one Chemical compound COP(=O)(OC)CC(=O)C(C)(C)CC#CC FQMVLQNNAODGQV-UHFFFAOYSA-N 0.000 description 1
- QAQKMSOVMMCNSE-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-methylhept-5-yn-2-one Chemical compound COP(=O)(OC)CC(=O)C(C)CC#CC QAQKMSOVMMCNSE-UHFFFAOYSA-N 0.000 description 1
- ZXNCLYVHPBPHNZ-UHFFFAOYSA-N 1-dimethoxyphosphorylbutan-2-one Chemical compound CCC(=O)CP(=O)(OC)OC ZXNCLYVHPBPHNZ-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- LEELWLKZRKDMAS-UHFFFAOYSA-N 2-(2,4-dimethoxy-3-methylsulfanylphenyl)ethanamine Chemical compound COC1=CC=C(CCN)C(OC)=C1SC LEELWLKZRKDMAS-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- KVVDRQDTODKIJD-UHFFFAOYSA-N 2-cyclopropylacetic acid Chemical compound OC(=O)CC1CC1 KVVDRQDTODKIJD-UHFFFAOYSA-N 0.000 description 1
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- VRDBIJCCXDEZJN-UHFFFAOYSA-N 2-piperidin-1-ylacetic acid Chemical compound OC(=O)CN1CCCCC1 VRDBIJCCXDEZJN-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- IRGLXUPKBNSARU-UHFFFAOYSA-N 3,3,6-trimethyl-1-(triphenyl-$l^{5}-phosphanylidene)hept-5-en-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)C(C)(C)CC=C(C)C)C1=CC=CC=C1 IRGLXUPKBNSARU-UHFFFAOYSA-N 0.000 description 1
- BVGDAZBTIVRTGO-UONOGXRCSA-N 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[4-methoxy-6-[(2s)-2-methylpiperazin-1-yl]pyridin-3-yl]pyridin-2-amine Chemical compound C1([C@@H](C)OC=2C(N)=NC=C(C=2)C2=CN=C(C=C2OC)N2[C@H](CNCC2)C)=C(Cl)C=CC(F)=C1Cl BVGDAZBTIVRTGO-UONOGXRCSA-N 0.000 description 1
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 1
- RJADQDXZYFCVHV-JQMWNLLFSA-N 5-[(2s,4r,5r,6ar)-5-hydroxy-4-[(e,3s)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical compound O1[C@@H](CCCCC(O)=O)CC2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@H]21 RJADQDXZYFCVHV-JQMWNLLFSA-N 0.000 description 1
- AQQKUXIHQCDSST-UHFFFAOYSA-N 7-dimethoxyphosphoryl-2,3-dimethylhept-2-ene Chemical compound COP(OC)(=O)CCCCC(=C(C)C)C AQQKUXIHQCDSST-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000012027 Collins reagent Substances 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SGXDXUYKISDCAZ-UHFFFAOYSA-N N,N-diethylglycine Chemical compound CCN(CC)CC(O)=O SGXDXUYKISDCAZ-UHFFFAOYSA-N 0.000 description 1
- VIWZVFVJPXTXPA-UHFFFAOYSA-N N-(2-Carboxymethyl)-morpholine Chemical compound OC(=O)CN1CCOCC1 VIWZVFVJPXTXPA-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 description 1
- 241000219289 Silene Species 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 229940022682 acetone Drugs 0.000 description 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
- NFMLWRCAFGMYPI-UHFFFAOYSA-N butanedioic acid;2-hydroxypropanoic acid Chemical compound CC(O)C(O)=O.OC(=O)CCC(O)=O NFMLWRCAFGMYPI-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 101150111293 cor-1 gene Proteins 0.000 description 1
- LMKPHJYTFHAGHK-UHFFFAOYSA-N cyclodrine Chemical compound C1CCCC1(O)C(C(=O)OCCN(CC)CC)C1=CC=CC=C1 LMKPHJYTFHAGHK-UHFFFAOYSA-N 0.000 description 1
- YAIKGZQRXQYYJZ-UHFFFAOYSA-N cyclopentanesulfonic acid Chemical compound OS(=O)(=O)C1CCCC1 YAIKGZQRXQYYJZ-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical group C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- YLFBFPXKTIQSSY-UHFFFAOYSA-N dimethoxy(oxo)phosphanium Chemical compound CO[P+](=O)OC YLFBFPXKTIQSSY-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- YGNOYUCUPMACDT-UHFFFAOYSA-N dimethylsulfamic acid Chemical compound CN(C)S(O)(=O)=O YGNOYUCUPMACDT-UHFFFAOYSA-N 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 1
- 229960001123 epoprostenol Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- BYAFLXZJJBQDEU-UHFFFAOYSA-N hept-5-yn-2-one Chemical compound CC#CCCC(C)=O BYAFLXZJJBQDEU-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- IZXGZAJMDLJLMF-UHFFFAOYSA-N methylaminomethanol Chemical compound CNCO IZXGZAJMDLJLMF-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FDUNKCCEGPJHLK-UHFFFAOYSA-N morpholine-2-sulfonic acid Chemical compound OS(=O)(=O)C1CNCCO1 FDUNKCCEGPJHLK-UHFFFAOYSA-N 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- OUPLTJDZPQZRBW-UHFFFAOYSA-N n-(oxomethylidene)methanesulfonamide Chemical compound CS(=O)(=O)N=C=O OUPLTJDZPQZRBW-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical compound CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
- C07D307/937—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans with hydrocarbon or substituted hydrocarbon radicals directly attached in position 2, e.g. prostacyclins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772734791 DE2734791A1 (de) | 1977-07-29 | 1977-07-29 | Neue prostaglandin-i tief 2 -derivate und verfahren zu ihrer herstellung |
| DEP2734791.7 | 1977-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1180700A true CA1180700A (en) | 1985-01-08 |
Family
ID=6015442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000308336A Expired CA1180700A (en) | 1977-07-29 | 1978-07-28 | Prostaglandin 1 in2 xx derivatives and process for their production |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4191694A (en, 2012) |
| JP (1) | JPS5427556A (en, 2012) |
| AT (1) | AT371454B (en, 2012) |
| AU (1) | AU523593B2 (en, 2012) |
| BE (1) | BE869372A (en, 2012) |
| CA (1) | CA1180700A (en, 2012) |
| CH (1) | CH636354A5 (en, 2012) |
| CS (1) | CS207640B2 (en, 2012) |
| DD (1) | DD138904A5 (en, 2012) |
| DE (1) | DE2734791A1 (en, 2012) |
| DK (1) | DK149954C (en, 2012) |
| ES (1) | ES472099A1 (en, 2012) |
| FR (1) | FR2398741A1 (en, 2012) |
| GB (1) | GB2001650B (en, 2012) |
| GR (1) | GR72256B (en, 2012) |
| HU (1) | HU179346B (en, 2012) |
| IE (1) | IE47304B1 (en, 2012) |
| IL (1) | IL55236A (en, 2012) |
| IT (1) | IT1097554B (en, 2012) |
| LU (1) | LU80043A1 (en, 2012) |
| NL (1) | NL7806861A (en, 2012) |
| NZ (1) | NZ187849A (en, 2012) |
| SE (1) | SE443978B (en, 2012) |
| SU (1) | SU921465A3 (en, 2012) |
| YU (1) | YU41595B (en, 2012) |
| ZA (1) | ZA784307B (en, 2012) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4264523A (en) * | 1979-04-02 | 1981-04-28 | The Upjohn Company | 19,20-Didehydro-13,14-dihydro-PG1 amides |
| US4264524A (en) * | 1979-04-02 | 1981-04-28 | The Upjohn Company | 19,20-Didehydro-PG1 amides |
| US4278815A (en) * | 1979-04-02 | 1981-07-14 | The Upjohn Company | 19-Keto-PG amides |
| US4283350A (en) * | 1979-04-02 | 1981-08-11 | The Upjohn Company | 19,20-Didehydro-PG2 amides |
| US4283351A (en) * | 1979-04-02 | 1981-08-11 | The Upjohn Company | 19,20-Didehydro-13,14-dihydro-PG2 amides |
| US4281191A (en) * | 1979-04-02 | 1981-07-28 | The Upjohn Company | 19-Hydroxy-19-methyl-PG amides |
| US4276436A (en) * | 1979-04-02 | 1981-06-30 | The Upjohn Company | 19-Keto-PG sulfonylamides |
| US4267371A (en) * | 1979-07-05 | 1981-05-12 | The Upjohn Company | 19-Hydroxy-6a-carba-PGI2 amides |
| US4289904A (en) * | 1979-07-05 | 1981-09-15 | The Upjohn Company | 19-Hydroxy-6a-carba-PGI2 sulfonylamides |
| US4312997A (en) * | 1979-07-05 | 1982-01-26 | The Upjohn Company | 19-Hydroxy-6-oxo-PGF1 amides |
| US4267352A (en) * | 1979-07-05 | 1981-05-12 | The Upjohn Company | 19-Hydroxy-19-methyl-6-oxo-PGF1 sulfonylamides |
| US4281150A (en) * | 1979-07-05 | 1981-07-28 | The Upjohn Company | 19-Hydroxy-19-methyl-6a-carba-PGI2 sulfonylamides |
| JPS6033429B2 (ja) * | 1980-04-28 | 1985-08-02 | 小野薬品工業株式会社 | プロスタグランジン類似化合物 |
| DE3041602A1 (de) * | 1980-10-31 | 1982-06-16 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue 5-cyan-prostacyclinderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3107100A1 (de) * | 1981-02-20 | 1982-09-09 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Azaprostacycline, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung |
| JPS58124778A (ja) * | 1982-01-20 | 1983-07-25 | Toray Ind Inc | ５，６，７−トリノル−４，８−インタ−ｍ−フエニレンＰＧＩ↓２誘導体 |
| US4539433A (en) * | 1982-11-24 | 1985-09-03 | Tdk Corporation | Electromagnetic shield |
| JPH0284398U (en, 2012) * | 1988-12-20 | 1990-06-29 | ||
| JPH0397493U (en, 2012) * | 1990-01-23 | 1991-10-07 | ||
| JPH0726876Y2 (ja) * | 1990-07-02 | 1995-06-14 | 日立フェライト株式会社 | 電波暗室用電波吸収体 |
| KR930011548B1 (ko) * | 1991-08-13 | 1993-12-10 | 한국과학기술연구원 | 적층형 전파흡수체 |
| JP3340732B1 (ja) * | 2001-10-05 | 2002-11-05 | 日本医薬品工業株式会社 | シクロペンタベンゾフラン誘導体の製造方法及びその製造原料となる新規化合物 |
-
1977
- 1977-07-29 DE DE19772734791 patent/DE2734791A1/de active Granted
-
1978
- 1978-06-26 NL NL7806861A patent/NL7806861A/xx not_active Application Discontinuation
- 1978-07-17 SU SU782636446A patent/SU921465A3/ru active
- 1978-07-24 YU YU1762/78A patent/YU41595B/xx unknown
- 1978-07-25 CH CH801778A patent/CH636354A5/de not_active IP Right Cessation
- 1978-07-26 US US05/928,126 patent/US4191694A/en not_active Expired - Lifetime
- 1978-07-26 IT IT26113/78A patent/IT1097554B/it active
- 1978-07-26 CS CS784966A patent/CS207640B2/cs unknown
- 1978-07-27 SE SE7808184A patent/SE443978B/sv not_active IP Right Cessation
- 1978-07-27 IL IL55236A patent/IL55236A/xx unknown
- 1978-07-27 ES ES472099A patent/ES472099A1/es not_active Expired
- 1978-07-27 GR GR56881A patent/GR72256B/el unknown
- 1978-07-27 LU LU80043A patent/LU80043A1/xx unknown
- 1978-07-27 DD DD78206979A patent/DD138904A5/xx unknown
- 1978-07-28 DK DK336878A patent/DK149954C/da not_active IP Right Cessation
- 1978-07-28 JP JP9308978A patent/JPS5427556A/ja active Granted
- 1978-07-28 BE BE189587A patent/BE869372A/xx not_active IP Right Cessation
- 1978-07-28 IE IE1538/78A patent/IE47304B1/en unknown
- 1978-07-28 CA CA000308336A patent/CA1180700A/en not_active Expired
- 1978-07-28 HU HU78SCHE654A patent/HU179346B/hu unknown
- 1978-07-28 ZA ZA00784307A patent/ZA784307B/xx unknown
- 1978-07-28 FR FR7822401A patent/FR2398741A1/fr active Granted
- 1978-07-28 AT AT0551578A patent/AT371454B/de not_active IP Right Cessation
- 1978-07-28 AU AU38439/78A patent/AU523593B2/en not_active Expired
- 1978-07-28 GB GB787831581A patent/GB2001650B/en not_active Expired
- 1978-07-29 NZ NZ187849A patent/NZ187849A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1180700A (en) | Prostaglandin 1 in2 xx derivatives and process for their production | |
| US4692464A (en) | Novel prostacyclin derivatives and a process for the preparation thereof | |
| CA1223255A (en) | Carbacyclin derivatives, process for their preparation and their use as medicaments | |
| US4446147A (en) | Azaprostacyclins, their preparation and pharmaceutical use | |
| CA1248525A (en) | Carbacyclins, process for their manufacture and their use as medicaments | |
| US4497830A (en) | Carbacyclins, their preparation and pharmacological use | |
| HU187466B (en) | Process for producing new 5-cyano-prostacycline derivatives and pharmaceutical compositions containing them | |
| CA1220471A (en) | Carbacyclines, process for their preparation and their use as medicaments | |
| NO156524B (no) | Analogifremgangsmaate ved fremstilling av terapeutisk aktive carbacyclinderivater. | |
| HU191150B (en) | Process for producing new prostacycline derivatives | |
| EP0059756B1 (en) | 7-oxoprostacyclin derivatives and process for the preparation thereof | |
| CA1215362A (en) | Carbacyclins, process for their preparation thereof, and use thereof as medicinal agents | |
| US4532236A (en) | Certain prostacyclins and their blood-pressure-lowering and thrombocyte-aggregation-inhibiting compositions and methods | |
| US4721729A (en) | Novel carbacyclins, process for the preparation thereof, and their use as medicinal agents | |
| EP0098794B1 (de) | Neue Carbacycline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel | |
| US4827017A (en) | Novel carbacyclins, processes for their production and their use as medicinal agents | |
| US5190973A (en) | 20-alkyl-7-oxoprostacyclin derivatives useful as pharmaceuticals | |
| HU207715B (en) | Process for producing 9-substituted carbacyclin derivatives and pharmaceutical compositions containing them as active components | |
| HU206317B (en) | Process for producing carbacyclines and pharmaceutical compositions containing them | |
| HU191111B (en) | Process for producing 5-fluoro-carbacyclines | |
| HU187643B (en) | Process for preparing /13e/-/8r,11r,12r,15r/-11,15-dihydroxy-16,16,19-trimethyl-9-oxo-13,18-prostadienic acid derivatives and salts thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |