NO792313L - Fremgangsmaate for fremstilling av 20-metyl-13,14-didehydro-pgi2-derivater - Google Patents
Fremgangsmaate for fremstilling av 20-metyl-13,14-didehydro-pgi2-derivaterInfo
- Publication number
- NO792313L NO792313L NO792313A NO792313A NO792313L NO 792313 L NO792313 L NO 792313L NO 792313 A NO792313 A NO 792313A NO 792313 A NO792313 A NO 792313A NO 792313 L NO792313 L NO 792313L
- Authority
- NO
- Norway
- Prior art keywords
- salt
- methyl
- pgi2
- didehydro
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 40
- 150000001447 alkali salts Chemical class 0.000 claims description 10
- 159000000000 sodium salts Chemical class 0.000 claims description 7
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 8
- 101000862089 Clarkia lewisii Glucose-6-phosphate isomerase, cytosolic 1A Proteins 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229960001123 epoprostenol Drugs 0.000 description 6
- 238000001802 infusion Methods 0.000 description 5
- 230000000304 vasodilatating effect Effects 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 238000004220 aggregation Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 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 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000002744 anti-aggregatory effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 210000004351 coronary vessel Anatomy 0.000 description 3
- 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 3
- 229960002986 dinoprostone Drugs 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 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
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000010255 intramuscular injection Methods 0.000 description 2
- 239000007927 intramuscular injection Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 210000003975 mesenteric artery Anatomy 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- -1 potassium alkoxide Chemical class 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 230000002997 prostaglandinlike Effects 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229940124549 vasodilator Drugs 0.000 description 2
- 239000003071 vasodilator agent Substances 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 108010051913 15-hydroxyprostaglandin dehydrogenase Proteins 0.000 description 1
- QLVKECUOHNDWOI-UHFFFAOYSA-N 2-oxo-1,3,2$l^{5}-diazaphosphonan-2-amine Chemical compound NP1(=O)NCCCCCCN1 QLVKECUOHNDWOI-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 101710129448 Glucose-6-phosphate isomerase 2 Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 206010000891 acute myocardial infarction Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 239000003146 anticoagulant agent 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
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000001631 haemodialysis Methods 0.000 description 1
- 230000000322 hemodialysis Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000007574 infarction Effects 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
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229960004393 lidocaine hydrochloride Drugs 0.000 description 1
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 230000007505 plaque formation Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002792 vascular 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
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25903/78A IT1099575B (it) | 1978-07-20 | 1978-07-20 | 20-metil-13,14-deidro-pgi2' suoi sali e suoi 16s- e 16r-metil derivati |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO792313L true NO792313L (no) | 1980-01-22 |
Family
ID=11218084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO792313A NO792313L (no) | 1978-07-20 | 1979-07-11 | Fremgangsmaate for fremstilling av 20-metyl-13,14-didehydro-pgi2-derivater |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5517389A (fr) |
| AT (1) | AT367758B (fr) |
| AU (1) | AU520750B2 (fr) |
| BE (1) | BE877687A (fr) |
| CA (1) | CA1183531A (fr) |
| CH (1) | CH640522A5 (fr) |
| CS (1) | CS208668B2 (fr) |
| DE (1) | DE2922110A1 (fr) |
| DK (1) | DK304479A (fr) |
| FR (1) | FR2431492A1 (fr) |
| GB (1) | GB2025972B (fr) |
| HU (1) | HU182727B (fr) |
| IE (1) | IE48593B1 (fr) |
| IL (1) | IL57552A (fr) |
| IT (1) | IT1099575B (fr) |
| NL (1) | NL7905259A (fr) |
| NO (1) | NO792313L (fr) |
| SE (1) | SE446002B (fr) |
| SU (1) | SU884569A3 (fr) |
| YU (1) | YU152979A (fr) |
| ZA (1) | ZA793123B (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3029984C2 (de) * | 1980-08-08 | 1983-12-15 | Grünenthal GmbH, 5190 Stolberg | 2-Oxabicyclo [3.3.0] octanderivate und diese enthaltende Arzneimittel |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL51189A (en) * | 1976-02-04 | 1985-08-30 | Upjohn Co | Prostaglandin analogs |
| AU3583378A (en) * | 1977-06-06 | 1979-11-08 | Chicago The University Of | Prostacyclin analogs |
-
1978
- 1978-07-20 IT IT25903/78A patent/IT1099575B/it active
-
1979
- 1979-05-31 DE DE19792922110 patent/DE2922110A1/de not_active Withdrawn
- 1979-06-13 AU AU48034/79A patent/AU520750B2/en not_active Ceased
- 1979-06-13 IL IL57552A patent/IL57552A/xx unknown
- 1979-06-14 FR FR7915298A patent/FR2431492A1/fr active Granted
- 1979-06-20 AT AT0435479A patent/AT367758B/de not_active IP Right Cessation
- 1979-06-22 ZA ZA793123A patent/ZA793123B/xx unknown
- 1979-06-27 YU YU01529/79A patent/YU152979A/xx unknown
- 1979-07-05 NL NL7905259A patent/NL7905259A/nl not_active Application Discontinuation
- 1979-07-11 NO NO792313A patent/NO792313L/no unknown
- 1979-07-13 BE BE0/196287A patent/BE877687A/fr not_active IP Right Cessation
- 1979-07-19 SE SE7906234A patent/SE446002B/sv unknown
- 1979-07-19 SU SU792790905A patent/SU884569A3/ru active
- 1979-07-19 DK DK304479A patent/DK304479A/da not_active Application Discontinuation
- 1979-07-19 HU HU79EA195A patent/HU182727B/hu unknown
- 1979-07-19 CA CA000332125A patent/CA1183531A/fr not_active Expired
- 1979-07-20 JP JP9172979A patent/JPS5517389A/ja active Pending
- 1979-07-20 CH CH677779A patent/CH640522A5/de not_active IP Right Cessation
- 1979-07-20 CS CS795112A patent/CS208668B2/cs unknown
- 1979-07-20 GB GB7925488A patent/GB2025972B/en not_active Expired
- 1979-08-08 IE IE1360/79A patent/IE48593B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2922110A1 (de) | 1980-01-31 |
| CH640522A5 (de) | 1984-01-13 |
| CA1183531A (fr) | 1985-03-05 |
| ATA435479A (de) | 1981-12-15 |
| GB2025972B (en) | 1982-09-15 |
| ZA793123B (en) | 1980-06-25 |
| SE7906234L (sv) | 1980-01-21 |
| JPS5517389A (en) | 1980-02-06 |
| AU4803479A (en) | 1980-01-24 |
| IE791360L (en) | 1980-01-20 |
| IL57552A0 (en) | 1979-10-31 |
| IT1099575B (it) | 1985-09-18 |
| CS208668B2 (en) | 1981-09-15 |
| FR2431492A1 (fr) | 1980-02-15 |
| SU884569A3 (ru) | 1981-11-23 |
| IL57552A (en) | 1983-02-23 |
| GB2025972A (en) | 1980-01-30 |
| SE446002B (sv) | 1986-08-04 |
| DK304479A (da) | 1980-01-21 |
| BE877687A (fr) | 1980-01-14 |
| IE48593B1 (en) | 1985-03-20 |
| HU182727B (en) | 1984-03-28 |
| NL7905259A (nl) | 1980-01-22 |
| FR2431492B1 (fr) | 1982-07-16 |
| AU520750B2 (en) | 1982-02-25 |
| IT7825903A0 (it) | 1978-07-20 |
| YU152979A (en) | 1983-01-21 |
| AT367758B (de) | 1982-07-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7473704B2 (en) | Cyclohexyl prostaglandin analogs as EP4-receptor agonists | |
| KR0125931B1 (ko) | 기관내 허혈병의 치료용 조성물 | |
| US8623918B2 (en) | Amino acid salts of prostaglandins | |
| IE914248A1 (en) | New use of organic compounds | |
| US5190926A (en) | 3'-azido-2',3'-dideoxypyrimidines and related compounds as antiviral agents | |
| AU2001297521B2 (en) | Co-cycloalkyl 17-heteroaryl prostaglandin E2 analogs as EP2-receptor agonists | |
| NO792313L (no) | Fremgangsmaate for fremstilling av 20-metyl-13,14-didehydro-pgi2-derivater | |
| EP0302263B1 (fr) | Composition thérapeutique pour combattre le SIDA | |
| WO2018231841A1 (fr) | Molécules de libération du monoxyde de carbone déclenchée par une enzyme | |
| JPS6334865B2 (fr) | ||
| KR880001028B1 (ko) | 세포 보호 유도방법 | |
| JP2642198B2 (ja) | 胃粘膜障害治療剤 | |
| FR2729668A1 (fr) | Nouveaux derives de mercaptoalcanoyldipeptides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| JP2714678B2 (ja) | 虚血性臓器障害予防・治療剤 | |
| IL44617A (en) | Pyrimido (1,2-a) benzimidazole and 1,4-diazepino (1,2-a)benzimidazole derivatives and a process for their preparation | |
| US4588713A (en) | Selective biologically active 7-oxo-prostacyclin derivatives and pharmaceutical compositions containing same | |
| US5869526A (en) | δ-(S-methylisothioureido)-L-norvaline therapeutic for cerebrovascular diseases having nitric oxide synthase inhibiting factor | |
| BE896621A (fr) | Nouvelle utilisation therapeutique d'analogues de prostaglandines | |
| US5491146A (en) | Hydroxylated erythro-hydroxynonyladenines and related analogs | |
| HUT64472A (en) | Method for producing pharmaceutical preparatives containing xantine derivatives | |
| KR870001002B1 (ko) | 선택적으로 생리활성인 7-옥소-프로스타사이클린 유도체의 제조방법 | |
| IE921658A1 (en) | The use of 1-(5-oxohexyl)-3-methyl-7-n-propylxanthine in vascular surgery | |
| US5824675A (en) | Preventive and therapeutic agent for kidney diseases | |
| CN112239443A (zh) | 二羟基二甲基异色满-3-甲酰非极性氨基酸,其制备,抗栓活性和应用 | |
| JP3881061B2 (ja) | 腎臓疾患予防・治療剤 |