DE2720999C2 - Postacyclin (bzw. (5Z)-5,6-Didehydro-9-desoxy-6,9α-epoxyprostaglandin F↓1↓↓α↓), Verfahren zu dessen Herstellung und diese Verbindung enthaltende pharmazeutische Formulierungen - Google Patents
Postacyclin (bzw. (5Z)-5,6-Didehydro-9-desoxy-6,9α-epoxyprostaglandin F↓1↓↓α↓), Verfahren zu dessen Herstellung und diese Verbindung enthaltende pharmazeutische FormulierungenInfo
- Publication number
- DE2720999C2 DE2720999C2 DE2720999A DE2720999A DE2720999C2 DE 2720999 C2 DE2720999 C2 DE 2720999C2 DE 2720999 A DE2720999 A DE 2720999A DE 2720999 A DE2720999 A DE 2720999A DE 2720999 C2 DE2720999 C2 DE 2720999C2
- Authority
- DE
- Germany
- Prior art keywords
- prostacyclin
- compound
- deoxy
- didehydro
- epoxyprostaglandin
- 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 12
- 150000001875 compounds Chemical class 0.000 title description 10
- 239000008194 pharmaceutical composition Substances 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title 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 claims description 40
- 229960001123 epoprostenol Drugs 0.000 claims description 40
- 238000004519 manufacturing process Methods 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 15
- 150000003180 prostaglandins Chemical class 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 210000001772 blood platelet Anatomy 0.000 description 12
- 210000001589 microsome Anatomy 0.000 description 12
- 241000283973 Oryctolagus cuniculus Species 0.000 description 11
- 230000002744 anti-aggregatory effect Effects 0.000 description 10
- 238000011534 incubation Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 210000001519 tissue Anatomy 0.000 description 8
- 230000002776 aggregation Effects 0.000 description 7
- 210000000709 aorta Anatomy 0.000 description 7
- 241000700159 Rattus Species 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- YIBNHAJFJUQSRA-YNNPMVKQSA-N prostaglandin H2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O YIBNHAJFJUQSRA-YNNPMVKQSA-N 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 5
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- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 241000282412 Homo Species 0.000 description 4
- SGUKUZOVHSFKPH-UHFFFAOYSA-N PGG2 Natural products C1C2OOC1C(C=CC(OO)CCCCC)C2CC=CCCCC(O)=O SGUKUZOVHSFKPH-UHFFFAOYSA-N 0.000 description 4
- 238000004220 aggregation Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- SGUKUZOVHSFKPH-YNNPMVKQSA-N prostaglandin G2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](OO)CCCCC)[C@H]2C\C=C/CCCC(O)=O SGUKUZOVHSFKPH-YNNPMVKQSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
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- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 230000004931 aggregating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000004087 circulation Effects 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 description 1
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- DKNPRRRKHAEUMW-UHFFFAOYSA-N Iodine aqueous Chemical compound [K+].I[I-]I DKNPRRRKHAEUMW-UHFFFAOYSA-N 0.000 description 1
- 235000010624 Medicago sativa Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- 206010050902 Postoperative thrombosis Diseases 0.000 description 1
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 239000010836 blood and blood product Substances 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 229940125691 blood product Drugs 0.000 description 1
- 239000003633 blood substitute Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000001595 contractor effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005555 hypertensive agent Substances 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 210000003975 mesenteric artery Anatomy 0.000 description 1
- 210000002445 nipple Anatomy 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 229940020414 potassium triiodide Drugs 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 230000029663 wound healing Effects 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (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)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB19384/76A GB1583961A (en) | 1976-05-11 | 1976-05-11 | Prostacyclin and derivatives thereof |
| GB3415176 | 1976-08-17 | ||
| GB3654776 | 1976-09-03 | ||
| GB4344576 | 1976-10-20 | ||
| GB5306076 | 1976-12-20 | ||
| GB1338977 | 1977-03-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2720999A1 DE2720999A1 (de) | 1977-11-24 |
| DE2720999C2 true DE2720999C2 (de) | 1986-09-18 |
Family
ID=27546654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2720999A Expired DE2720999C2 (de) | 1976-05-11 | 1977-05-10 | Postacyclin (bzw. (5Z)-5,6-Didehydro-9-desoxy-6,9α-epoxyprostaglandin F↓1↓↓α↓), Verfahren zu dessen Herstellung und diese Verbindung enthaltende pharmazeutische Formulierungen |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS52136161A (enExample) |
| BE (1) | BE854463A (enExample) |
| CH (1) | CH637948A5 (enExample) |
| DE (1) | DE2720999C2 (enExample) |
| DK (1) | DK149953C (enExample) |
| FR (1) | FR2351111A1 (enExample) |
| GB (1) | GB1583961A (enExample) |
| IE (1) | IE46036B1 (enExample) |
| IL (1) | IL52053A (enExample) |
| NL (1) | NL181973C (enExample) |
| NZ (1) | NZ184057A (enExample) |
| SE (1) | SE436647B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI71138C (fi) * | 1976-12-31 | 1986-11-24 | Erba Farmitalia | Foerfarande foer framstaellning av terapeutiskt aktiva bisykliska prostaglandiner |
| US4178367A (en) | 1977-02-21 | 1979-12-11 | Ono Pharmaceutical Co. Ltd. | Prostaglandin I2 analogues |
| HU182583B (en) * | 1977-03-01 | 1984-02-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing prostacyclin and analogues thereof |
| DE2743283A1 (de) * | 1977-09-27 | 1979-04-05 | Hoechst Ag | Neue prostacyclin-analoga |
| IT1088036B (it) | 1977-11-25 | 1985-06-04 | Erba Carlo Spa | 15-epi-prostaciclina e prostaciclina analoghi |
| DE2811950A1 (de) * | 1978-03-18 | 1979-12-13 | Hoechst Ag | Neue analoga von prostacyclin |
| ZA787353B (en) * | 1978-05-17 | 1980-08-27 | Wellcome Found | Pharmaceutical formulations |
| US4430340A (en) * | 1978-07-17 | 1984-02-07 | The Upjohn Company | Stabilization of PGI2 compounds with surfactants |
| IL58384A0 (en) | 1978-10-14 | 1980-01-31 | Beecham Group Ltd | 12-aza analogues of prostcyclin their preparation and pharmaceutical composition containing them |
| ZA815504B (en) * | 1980-09-15 | 1982-08-25 | Upjohn Co | Crystalline pgi2 methyl ester |
| CH651033A5 (de) * | 1981-03-11 | 1985-08-30 | Hoffmann La Roche | Fluorprostacycline. |
| DE3438870A1 (de) * | 1983-12-13 | 1985-06-13 | Stellmacher, Gerhard, Ing.(grad.), 8501 Schwaig | Spannvorrichtung fuer holzbearbeitungsmaschinen |
| JP5697260B2 (ja) | 2009-11-13 | 2015-04-08 | 東レ株式会社 | 糖尿病の治療または予防薬 |
| HU231031B1 (hu) | 2016-03-23 | 2019-12-30 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Megnövelt stabilitású epoprostenol nátrium és eljárás előállítására |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL51189A (en) * | 1976-02-04 | 1985-08-30 | Upjohn Co | Prostaglandin analogs |
-
1976
- 1976-05-11 GB GB19384/76A patent/GB1583961A/en not_active Expired
-
1977
- 1977-04-07 FR FR7710593A patent/FR2351111A1/fr not_active Withdrawn
- 1977-05-10 IE IE950/77A patent/IE46036B1/en not_active IP Right Cessation
- 1977-05-10 BE BE177444A patent/BE854463A/xx not_active IP Right Cessation
- 1977-05-10 DK DK205377A patent/DK149953C/da not_active IP Right Cessation
- 1977-05-10 SE SE7705423A patent/SE436647B/xx not_active IP Right Cessation
- 1977-05-10 IL IL52053A patent/IL52053A/xx unknown
- 1977-05-10 NZ NZ184057A patent/NZ184057A/xx unknown
- 1977-05-10 DE DE2720999A patent/DE2720999C2/de not_active Expired
- 1977-05-10 NL NLAANVRAGE7705141,A patent/NL181973C/xx not_active IP Right Cessation
- 1977-05-10 JP JP5361977A patent/JPS52136161A/ja active Granted
- 1977-05-10 CH CH583777A patent/CH637948A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IE46036L (en) | 1977-11-11 |
| JPS52136161A (en) | 1977-11-14 |
| GB1583961A (en) | 1981-02-04 |
| IE46036B1 (en) | 1983-02-09 |
| NL181973B (nl) | 1987-07-16 |
| SE7705423L (sv) | 1977-11-12 |
| IL52053A (en) | 1983-09-30 |
| DE2720999A1 (de) | 1977-11-24 |
| SE436647B (sv) | 1985-01-14 |
| NZ184057A (en) | 1979-10-25 |
| DK149953C (da) | 1987-06-29 |
| JPS619953B2 (enExample) | 1986-03-27 |
| NL181973C (nl) | 1987-12-16 |
| IL52053A0 (en) | 1977-07-31 |
| FR2351111A1 (fr) | 1977-12-09 |
| NL7705141A (nl) | 1977-11-15 |
| CH637948A5 (en) | 1983-08-31 |
| BE854463A (fr) | 1977-11-10 |
| DK149953B (da) | 1986-11-03 |
| DK205377A (da) | 1977-11-12 |
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