FI62220C - Foerfarande foer stabilisering av en prostaglandin av e-serieninnehaollande farmaseutisk blandning - Google Patents
Foerfarande foer stabilisering av en prostaglandin av e-serieninnehaollande farmaseutisk blandning Download PDFInfo
- Publication number
- FI62220C FI62220C FI751108A FI751108A FI62220C FI 62220 C FI62220 C FI 62220C FI 751108 A FI751108 A FI 751108A FI 751108 A FI751108 A FI 751108A FI 62220 C FI62220 C FI 62220C
- Authority
- FI
- Finland
- Prior art keywords
- prostaglandin
- alcohol
- methyl
- blandning
- serieninnehaollande
- Prior art date
Links
- 150000003180 prostaglandins Chemical class 0.000 title claims description 31
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 230000000087 stabilizing effect Effects 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000003380 propellant Substances 0.000 claims description 9
- -1 saturated aliphatic tertiary alcohol Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 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 10
- 229960002986 dinoprostone Drugs 0.000 description 9
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 5
- 230000001766 physiological effect Effects 0.000 description 5
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- 150000003509 tertiary alcohols Chemical class 0.000 description 4
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 3
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 2
- RFCAUADVODFSLZ-UHFFFAOYSA-N 1-Chloro-1,1,2,2,2-pentafluoroethane Chemical compound FC(F)(F)C(F)(F)Cl RFCAUADVODFSLZ-UHFFFAOYSA-N 0.000 description 2
- IKECULIHBUCAKR-UHFFFAOYSA-N 2,3-dimethylbutan-2-ol Chemical compound CC(C)C(C)(C)O IKECULIHBUCAKR-UHFFFAOYSA-N 0.000 description 2
- RFZHJHSNHYIRNE-UHFFFAOYSA-N 2,3-dimethylpentan-3-ol Chemical compound CCC(C)(O)C(C)C RFZHJHSNHYIRNE-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- XKIRHOWVQWCYBT-UHFFFAOYSA-N 3-ethylpentan-3-ol Chemical compound CCC(O)(CC)CC XKIRHOWVQWCYBT-UHFFFAOYSA-N 0.000 description 2
- 206010000234 Abortion spontaneous Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000010835 comparative analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229930007744 linalool Natural products 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 208000015994 miscarriage Diseases 0.000 description 2
- 208000000995 spontaneous abortion Diseases 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- CAKWRXVKWGUISE-UHFFFAOYSA-N 1-methylcyclopentan-1-ol Chemical compound CC1(O)CCCC1 CAKWRXVKWGUISE-UHFFFAOYSA-N 0.000 description 1
- SXSWMAUXEHKFGX-UHFFFAOYSA-N 2,3-dimethylbutan-1-ol Chemical compound CC(C)C(C)CO SXSWMAUXEHKFGX-UHFFFAOYSA-N 0.000 description 1
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 1
- KRIMXCDMVRMCTC-UHFFFAOYSA-N 2-methylhexan-2-ol Chemical compound CCCCC(C)(C)O KRIMXCDMVRMCTC-UHFFFAOYSA-N 0.000 description 1
- UYOPRNGQFQWYER-UHFFFAOYSA-N 2-methylpent-4-en-2-ol Chemical compound CC(C)(O)CC=C UYOPRNGQFQWYER-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- IFRGTDNXZCHDEP-UHFFFAOYSA-N CC(C)C(CC)(O)C.CC(COC(C)CO)O.CC(C)(C(C)C)O.CO.CC(C)(C=C)O.C(C)(C)O Chemical compound CC(C)C(CC)(O)C.CC(COC(C)CO)O.CC(C)(C(C)C)O.CO.CC(C)(C=C)O.C(C)(C)O IFRGTDNXZCHDEP-UHFFFAOYSA-N 0.000 description 1
- NVOSUCDLAQFSMC-UHFFFAOYSA-N CC(O)CO.CCCCC(C)O Chemical compound CC(O)CO.CCCCC(C)O NVOSUCDLAQFSMC-UHFFFAOYSA-N 0.000 description 1
- FLNKNIOVIFBTDO-UHFFFAOYSA-N CC1(CCCC1)O.C(C)O Chemical compound CC1(CCCC1)O.C(C)O FLNKNIOVIFBTDO-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- BXDZOYLPNAIDOC-UHFFFAOYSA-N N-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-[2-[2-[2-[2-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethoxy]ethoxy]ethoxy]ethylamino]-2-oxoethyl]piperidine-4-carboxamide Chemical compound CC(C)(C)c1cnc(CSc2cnc(NC(=O)C3CCN(CC(=O)NCCOCCOCCOCCNc4cccc5C(=O)N(C6CCC(=O)NC6=O)C(=O)c45)CC3)s2)o1 BXDZOYLPNAIDOC-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- JWOLLWQJKQOEOL-UHFFFAOYSA-N OOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOO JWOLLWQJKQOEOL-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 229960000711 alprostadil Drugs 0.000 description 1
- 238000002266 amputation Methods 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000035606 childbirth Effects 0.000 description 1
- 235000019406 chloropentafluoroethane Nutrition 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- DZUXGQBLFALXCR-CDIPTNKSSA-N prostaglandin F1alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CCCCCCC(O)=O DZUXGQBLFALXCR-CDIPTNKSSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 230000035884 vasodepression Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US462213A US3927197A (en) | 1974-04-19 | 1974-04-19 | Tertiary alcohol stabilized E-series prostaglandins |
| US46221374 | 1974-04-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI751108A FI751108A (nl) | 1975-10-20 |
| FI62220B FI62220B (fi) | 1982-08-31 |
| FI62220C true FI62220C (fi) | 1982-12-10 |
Family
ID=23835600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI751108A FI62220C (fi) | 1974-04-19 | 1975-04-15 | Foerfarande foer stabilisering av en prostaglandin av e-serieninnehaollande farmaseutisk blandning |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3927197A (nl) |
| JP (1) | JPS5337408B2 (nl) |
| AR (1) | AR213271A1 (nl) |
| AT (1) | AT348130B (nl) |
| AU (1) | AU470631B2 (nl) |
| BE (1) | BE828065A (nl) |
| BG (1) | BG35326A3 (nl) |
| CA (1) | CA1034044A (nl) |
| CS (1) | CS191244B2 (nl) |
| DD (1) | DD119131A5 (nl) |
| DE (1) | DE2516105C3 (nl) |
| DK (1) | DK138161B (nl) |
| ES (1) | ES436613A1 (nl) |
| FI (1) | FI62220C (nl) |
| FR (1) | FR2267760B1 (nl) |
| GB (1) | GB1474852A (nl) |
| HU (1) | HU175405B (nl) |
| IE (1) | IE40829B1 (nl) |
| IL (1) | IL46994A (nl) |
| LU (1) | LU72320A1 (nl) |
| NL (1) | NL158384B (nl) |
| PH (1) | PH11697A (nl) |
| SE (1) | SE428528B (nl) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197257A (en) * | 1976-02-04 | 1980-04-08 | The Upjohn Company | 6-Keto prostaglandin derivatives |
| US4169895A (en) * | 1976-09-28 | 1979-10-02 | Pfizer Inc. | Antisecretory 16,16-dimethyl-17-oxaprostaglandins |
| US4098805A (en) * | 1977-04-11 | 1978-07-04 | The Upjohn Company | 9-deoxy-9-methylene-pgf-type amides |
| ZA831186B (en) * | 1982-03-22 | 1983-11-30 | Upjohn Ltd | Gelled pge2/triacetin solutions |
| ZA837627B (en) * | 1982-10-15 | 1984-06-27 | Procter & Gamble | Storage stable topical pharmaceutical composition containing low dielectric solvents |
| US5409911A (en) * | 1992-09-11 | 1995-04-25 | Merck & Co., Inc. | Prostaglandin analog for treating osteoporosis |
| ES2142409T3 (es) * | 1993-10-27 | 2000-04-16 | Upjohn Co | Prostaglandina e 1 estabilizada. |
| HN1996000101A (es) | 1996-02-28 | 1997-06-26 | Inc Pfizer | Terapia combinada para la osteoporosis |
| US6121253A (en) * | 1998-11-20 | 2000-09-19 | Merck Frosst Canada & Co. | Prostaglandin conjugates for treating or preventing bone disease |
| US20050203086A1 (en) * | 2004-03-04 | 2005-09-15 | Pfizer Inc. | Methods of treatment using an EP2 selective receptor agonist |
| US20100099640A1 (en) * | 2007-05-04 | 2010-04-22 | Joannes Geuns | Tissue degeneration protection |
| US9005183B2 (en) * | 2007-05-16 | 2015-04-14 | Health Knight, Llc | System and method for treating erectile dysfunction |
| AT515356B1 (de) * | 2014-01-30 | 2015-11-15 | Gebro Holding Gmbh | Stabile alkoholische Lösung von Alprostadil |
| RU2020130837A (ru) | 2018-02-21 | 2022-03-21 | ЭйАй ТЕРАПЬЮТИКС, ИНК. | Комбинационная терапия апилимодом и глутаматергическими агентами |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3644638A (en) * | 1970-08-24 | 1972-02-22 | American Home Prod | Compositions and methods for relieving bronchial spasm with prostanoic acids and esters |
| US3749800A (en) * | 1971-11-01 | 1973-07-31 | Upjohn Co | Stable composition for dispensing pge2 |
| US3833725A (en) * | 1972-12-08 | 1974-09-03 | Syntex Corp | Dialkylated glycol compositions and medicament preparations containing same |
-
1974
- 1974-04-19 US US462213A patent/US3927197A/en not_active Expired - Lifetime
-
1975
- 1975-03-14 IE IE564/75A patent/IE40829B1/xx unknown
- 1975-04-01 SE SE7503723A patent/SE428528B/xx unknown
- 1975-04-01 IL IL46994A patent/IL46994A/xx unknown
- 1975-04-03 GB GB1375075A patent/GB1474852A/en not_active Expired
- 1975-04-07 PH PH17025A patent/PH11697A/en unknown
- 1975-04-07 AU AU79877/75A patent/AU470631B2/en not_active Expired
- 1975-04-10 NL NL7504274.A patent/NL158384B/nl not_active IP Right Cessation
- 1975-04-11 AT AT278875A patent/AT348130B/de not_active IP Right Cessation
- 1975-04-12 DE DE2516105A patent/DE2516105C3/de not_active Expired
- 1975-04-15 ES ES436613A patent/ES436613A1/es not_active Expired
- 1975-04-15 FI FI751108A patent/FI62220C/fi not_active IP Right Cessation
- 1975-04-17 BG BG029696A patent/BG35326A3/xx unknown
- 1975-04-17 BE BE1006596A patent/BE828065A/xx not_active IP Right Cessation
- 1975-04-17 CS CS752679A patent/CS191244B2/cs unknown
- 1975-04-18 AR AR258417A patent/AR213271A1/es active
- 1975-04-18 CA CA224,982A patent/CA1034044A/en not_active Expired
- 1975-04-18 DK DK167075AA patent/DK138161B/da not_active IP Right Cessation
- 1975-04-18 HU HU75PI465A patent/HU175405B/hu unknown
- 1975-04-18 LU LU72320A patent/LU72320A1/xx unknown
- 1975-04-18 DD DD185553A patent/DD119131A5/xx unknown
- 1975-04-18 JP JP4736775A patent/JPS5337408B2/ja not_active Expired
- 1975-04-18 FR FR7512160A patent/FR2267760B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| LU72320A1 (nl) | 1976-03-17 |
| PH11697A (en) | 1978-05-24 |
| JPS5337408B2 (nl) | 1978-10-09 |
| IE40829B1 (en) | 1979-08-29 |
| CS191244B2 (en) | 1979-06-29 |
| ES436613A1 (es) | 1977-04-16 |
| FI751108A (nl) | 1975-10-20 |
| SE428528B (sv) | 1983-07-11 |
| DK138161B (da) | 1978-07-24 |
| SE7503723L (sv) | 1975-10-20 |
| IL46994A0 (en) | 1975-06-25 |
| AT348130B (de) | 1979-01-25 |
| ATA278875A (de) | 1978-06-15 |
| US3927197A (en) | 1975-12-16 |
| AR213271A1 (es) | 1979-01-15 |
| DE2516105A1 (de) | 1975-10-23 |
| GB1474852A (en) | 1977-05-25 |
| BE828065A (fr) | 1975-10-17 |
| DK167075A (nl) | 1975-10-20 |
| JPS50145515A (nl) | 1975-11-21 |
| AU470631B2 (en) | 1976-03-25 |
| NL7504274A (nl) | 1975-10-21 |
| NL158384B (nl) | 1978-11-15 |
| CA1034044A (en) | 1978-07-04 |
| DE2516105B2 (de) | 1981-01-08 |
| IL46994A (en) | 1979-10-31 |
| FR2267760A1 (nl) | 1975-11-14 |
| BG35326A3 (en) | 1984-03-15 |
| FR2267760B1 (nl) | 1978-08-04 |
| IE40829L (en) | 1975-10-19 |
| HU175405B (hu) | 1980-07-28 |
| DE2516105C3 (de) | 1982-01-07 |
| FI62220B (fi) | 1982-08-31 |
| DD119131A5 (nl) | 1976-04-12 |
| AU7987775A (en) | 1976-03-25 |
| DK138161C (nl) | 1979-01-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: PFIZER INC. |