HU191264B - Process for production of derivatives of 7-oxo-prostacyclin with selective biological effect - Google Patents
Process for production of derivatives of 7-oxo-prostacyclin with selective biological effect Download PDFInfo
- Publication number
- HU191264B HU191264B HU84128A HU12884A HU191264B HU 191264 B HU191264 B HU 191264B HU 84128 A HU84128 A HU 84128A HU 12884 A HU12884 A HU 12884A HU 191264 B HU191264 B HU 191264B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- defined above
- oxo
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 230000008569 process Effects 0.000 title claims description 16
- ZHIHHYNLWRXTTN-GJUFTPBXSA-N (5z)-5-[(3ar,4r,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxyoct-1-enyl]-3-oxo-4,5,6,6a-tetrahydro-3ah-cyclopenta[b]furan-2-ylidene]pentanoic acid Chemical class O1\C(=C/CCCC(O)=O)C(=O)[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 ZHIHHYNLWRXTTN-GJUFTPBXSA-N 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 230000004071 biological effect Effects 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 150000001768 cations Chemical class 0.000 claims abstract description 4
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims description 14
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000003204 osmotic effect Effects 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims 1
- 239000003146 anticoagulant agent Substances 0.000 claims 1
- 229940127219 anticoagulant drug Drugs 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003433 contraceptive agent Substances 0.000 claims 1
- 230000002254 contraceptive effect Effects 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 239000000796 flavoring agent Substances 0.000 claims 1
- 235000019634 flavors Nutrition 0.000 claims 1
- 229910052711 selenium Inorganic materials 0.000 claims 1
- 239000011669 selenium Substances 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 230000002776 aggregation Effects 0.000 abstract description 2
- 238000004220 aggregation Methods 0.000 abstract description 2
- 230000001077 hypotensive effect Effects 0.000 abstract description 2
- 230000005764 inhibitory process Effects 0.000 abstract description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 210000001772 blood platelet Anatomy 0.000 abstract 1
- 229910052736 halogen Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 1
- 125000004665 trialkylsilyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 10
- 230000007935 neutral effect Effects 0.000 description 8
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000005055 short column chromatography Methods 0.000 description 4
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 4
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- 230000002744 anti-aggregatory effect Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000006196 drop Substances 0.000 description 2
- 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 2
- 229960001123 epoprostenol Drugs 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 description 1
- -1 2 -ethyl Chemical group 0.000 description 1
- FWFUSMMVFVVERM-UHFFFAOYSA-N 2-(1,4-dioxan-2-yl)acetic acid Chemical compound OC(=O)CC1COCCO1 FWFUSMMVFVVERM-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 241000021559 Dicerandra Species 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- 101001000733 Rhodococcus jostii (strain RHA1) Glucose-6-phosphate isomerase 3 Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000002959 anti-hypotensive effect Effects 0.000 description 1
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000002612 cardiopulmonary effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000001120 cytoprotective effect Effects 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 230000003480 fibrinolytic effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 235000015220 hamburgers Nutrition 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- WAHWCUPSBZVYPH-UHFFFAOYSA-N n,n-diethylethanamine;sodium Chemical compound [Na].CCN(CC)CC WAHWCUPSBZVYPH-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003815 prostacyclins Chemical class 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 231100000397 ulcer Toxicity 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- A61P9/08—Vasodilators for multiple indications
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Furan Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU84128A HU191264B (en) | 1984-01-13 | 1984-01-13 | Process for production of derivatives of 7-oxo-prostacyclin with selective biological effect |
| IL73945A IL73945A (en) | 1984-01-13 | 1984-12-27 | Selective biologically active 7-oxo-prostacycline derivatives,process for the preparation thereof and pharmaceutical compositions containing same |
| SU853837051A SU1376939A3 (ru) | 1984-01-13 | 1985-01-11 | Способ получени производных 7-оксо-простациклина или их солей |
| ES539474A ES8605229A1 (es) | 1984-01-13 | 1985-01-11 | Procedimiento de preparar derivados 7-oxoprostaciclinicos |
| EP85104957A EP0163905B1 (de) | 1984-01-13 | 1985-01-11 | Racemische und optisch aktive 7-Oxo-prostacyclin-Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Präparate |
| AT85104957T ATE40359T1 (de) | 1984-01-13 | 1985-01-11 | Racemische und optisch aktive 7-oxo-prostacyclin- derivate, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische praeparate. |
| AU37624/85A AU576815B2 (en) | 1984-01-13 | 1985-01-11 | 7-oxo-prostacyclines |
| GR850078A GR850078B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-01-13 | 1985-01-11 | |
| FI850123A FI850123A0 (fi) | 1984-01-13 | 1985-01-11 | Selektiva, biologiskt aktiva 7-oxo-prostacyklinderivat samt framstaellningsfoerfarande foer dessa samt dessa innehaollande farmaceutiska kompositioner. |
| DE8585104957T DE3567862D1 (en) | 1984-01-13 | 1985-01-11 | Racemic and optically active 7-oxo-prostacyclin derivatives, process for their preparation and pharmaceutical compositions containing these compounds |
| DK014985A DK165920C (da) | 1984-01-13 | 1985-01-11 | Selektive biologisk aktive 7-oxo-prostacyclinderivater og fremgangsmaade til fremstilling deraf og farmaceutiske praeparater indeholdende disse |
| US06/691,340 US4588713A (en) | 1984-01-13 | 1985-01-14 | Selective biologically active 7-oxo-prostacyclin derivatives and pharmaceutical compositions containing same |
| JP60081510A JPH0643413B2 (ja) | 1984-01-13 | 1985-04-18 | ７−オキソ−プロスタサイクリン誘導体、その製法および医薬組成物 |
| SU853912355A SU1421741A1 (ru) | 1984-01-13 | 1985-06-13 | Оптически активные производные 7-оксопростациклина,обладающие антиагрегатным и гипотензивным действием |
| FI852465A FI83645C (fi) | 1984-01-13 | 1985-06-20 | Foerfarande foer framstaellning av terapeutiskt anvaenbara racemiska eller optiskt aktiva 7-oxo- prostacyklin-derivat. |
| ES549967A ES8701153A1 (es) | 1984-01-13 | 1985-12-16 | Procedimiento de preparar derivados 7-oxo-prostaciclinicos |
| SU864008367A SU1424735A3 (ru) | 1984-01-13 | 1986-01-17 | Способ получени производных 7-оксопростациклина |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU84128A HU191264B (en) | 1984-01-13 | 1984-01-13 | Process for production of derivatives of 7-oxo-prostacyclin with selective biological effect |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT35658A HUT35658A (en) | 1985-07-29 |
| HU191264B true HU191264B (en) | 1987-01-28 |
Family
ID=10948057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU84128A HU191264B (en) | 1984-01-13 | 1984-01-13 | Process for production of derivatives of 7-oxo-prostacyclin with selective biological effect |
Country Status (12)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU197733B (en) * | 1985-05-29 | 1989-05-29 | Chinoin Gyogyszer Es Vegyeszet | Process for producing ephedrin-salts of 7-oxo-prosta-cyclin derivatives |
| US4808734A (en) * | 1986-12-01 | 1989-02-28 | Hoffmann-La Roche Inc. | 16-cycloalkyl-7-fluoro-prostacyclins |
| DE102004024504A1 (de) * | 2004-05-18 | 2006-02-16 | Bayer Healthcare Ag | Neue Cylopenta[b]benzofuran-Derivate und ihre Verwendung |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4178367A (en) * | 1977-02-21 | 1979-12-11 | Ono Pharmaceutical Co. Ltd. | Prostaglandin I2 analogues |
| US4330553A (en) * | 1979-11-12 | 1982-05-18 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. | 7-Oxo-PGI2 -derivatives and process for the preparation thereof and pharmaceutical compositions containing same |
| DE3035454A1 (de) * | 1980-09-18 | 1982-04-22 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 7-oxoprostacyclinderivate und verfahren zu ihrer herstellung |
| DE3308561A1 (de) * | 1983-03-08 | 1984-09-13 | Schering AG, 1000 Berlin und 4709 Bergkamen | 19,20-methylenprostacyclinderivate und verfahren zu ihrer herstellung |
-
1984
- 1984-01-13 HU HU84128A patent/HU191264B/hu not_active IP Right Cessation
- 1984-12-27 IL IL73945A patent/IL73945A/xx not_active IP Right Cessation
-
1985
- 1985-01-11 GR GR850078A patent/GR850078B/el unknown
- 1985-01-11 FI FI850123A patent/FI850123A0/fi not_active Application Discontinuation
- 1985-01-11 DK DK014985A patent/DK165920C/da not_active IP Right Cessation
- 1985-01-11 ES ES539474A patent/ES8605229A1/es not_active Expired
- 1985-01-11 AU AU37624/85A patent/AU576815B2/en not_active Ceased
- 1985-01-11 AT AT85104957T patent/ATE40359T1/de not_active IP Right Cessation
- 1985-01-11 SU SU853837051A patent/SU1376939A3/ru active
- 1985-01-11 EP EP85104957A patent/EP0163905B1/de not_active Expired
- 1985-01-14 US US06/691,340 patent/US4588713A/en not_active Expired - Fee Related
- 1985-04-18 JP JP60081510A patent/JPH0643413B2/ja not_active Expired - Lifetime
- 1985-06-13 SU SU853912355A patent/SU1421741A1/ru active
- 1985-12-16 ES ES549967A patent/ES8701153A1/es not_active Expired
-
1986
- 1986-01-17 SU SU864008367A patent/SU1424735A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| HUT35658A (en) | 1985-07-29 |
| EP0163905A1 (de) | 1985-12-11 |
| ATE40359T1 (de) | 1989-02-15 |
| EP0163905B1 (de) | 1989-01-25 |
| SU1424735A3 (ru) | 1988-09-15 |
| DK165920B (da) | 1993-02-08 |
| SU1376939A3 (ru) | 1988-02-23 |
| ES8701153A1 (es) | 1986-12-01 |
| FI850123A0 (fi) | 1985-01-11 |
| JPH0643413B2 (ja) | 1994-06-08 |
| AU3762485A (en) | 1985-07-18 |
| ES549967A0 (es) | 1986-12-01 |
| US4588713A (en) | 1986-05-13 |
| DK165920C (da) | 1993-06-28 |
| SU1421741A1 (ru) | 1988-09-07 |
| IL73945A (en) | 1988-05-31 |
| ES539474A0 (es) | 1986-04-01 |
| DK14985A (da) | 1985-07-14 |
| IL73945A0 (en) | 1985-03-31 |
| ES8605229A1 (es) | 1986-04-01 |
| GR850078B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-05-13 |
| DK14985D0 (da) | 1985-01-11 |
| JPS61243073A (ja) | 1986-10-29 |
| AU576815B2 (en) | 1988-09-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |