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 PDF

Info

Publication number: FI62220C
Authority: FI; Finland
Prior art keywords: prostaglandin; alcohol; methyl; blandning; serieninnehaollande
Prior art date: 1974-04-19

Application number

FI751108A

Other languages

English (en)

Finnish (fi)

Other versions

FI62220B (fi

FI751108A (sv

Inventor

Donald Charles Monkhouse

Original Assignee

Pfizer

Priority date (The priority date 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 date listed.)

1974-04-19

Filing date

1975-04-15

Publication date

1982-12-10

1975-04-15 Application filed by Pfizer filed Critical Pfizer

1975-10-20 Publication of FI751108A publication Critical patent/FI751108A/fi

1982-08-31 Publication of FI62220B publication Critical patent/FI62220B/fi

1982-12-10 Application granted granted Critical

1982-12-10 Publication of FI62220C publication Critical patent/FI62220C/fi

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)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (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)

FI751108A 1974-04-19 1975-04-15 Foerfarande foer stabilisering av en prostaglandin av e-serieninnehaollande farmaseutisk blandning FI62220C (fi)

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 (sv)	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 (sv)
JP (1)	JPS5337408B2 (sv)
AR (1)	AR213271A1 (sv)
AT (1)	AT348130B (sv)
AU (1)	AU470631B2 (sv)
BE (1)	BE828065A (sv)
BG (1)	BG35326A3 (sv)
CA (1)	CA1034044A (sv)
CS (1)	CS191244B2 (sv)
DD (1)	DD119131A5 (sv)
DE (1)	DE2516105C3 (sv)
DK (1)	DK138161B (sv)
ES (1)	ES436613A1 (sv)
FI (1)	FI62220C (sv)
FR (1)	FR2267760B1 (sv)
GB (1)	GB1474852A (sv)
HU (1)	HU175405B (sv)
IE (1)	IE40829B1 (sv)
IL (1)	IL46994A (sv)
LU (1)	LU72320A1 (sv)
NL (1)	NL158384B (sv)
PH (1)	PH11697A (sv)
SE (1)	SE428528B (sv)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
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
NZ273752A (en) *	1993-10-27	1998-03-25	Upjohn Co	Stabilised prostaglandin e1 lyophilisate using tertiary butanol and lactose carriers
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
WO2008134828A2 (en)	2007-05-04	2008-11-13	Katholieke Universiteit Leuven	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
TW202000205A (zh)	2018-02-21	2020-01-01	美商Ａｉ治療公司	使用阿吡莫德與麩胺酸性劑的組合治療

Family Cites Families (3)

* Cited by examiner, † Cited by third party
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 IL IL46994A patent/IL46994A/xx unknown
- 1975-04-01 SE SE7503723A patent/SE428528B/sv unknown
- 1975-04-03 GB GB1375075A patent/GB1474852A/en not_active Expired
- 1975-04-07 AU AU79877/75A patent/AU470631B2/en not_active Expired
- 1975-04-07 PH PH17025A patent/PH11697A/en unknown
- 1975-04-10 NL NL7504274.A patent/NL158384B/xx 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 BG7529696A patent/BG35326A3/xx unknown
- 1975-04-17 CS CS752679A patent/CS191244B2/cs unknown
- 1975-04-17 BE BE1006596A patent/BE828065A/xx not_active IP Right Cessation
- 1975-04-18 DD DD185553A patent/DD119131A5/xx unknown
- 1975-04-18 LU LU72320A patent/LU72320A1/xx unknown
- 1975-04-18 DK DK167075AA patent/DK138161B/da not_active IP Right Cessation
- 1975-04-18 CA CA224,982A patent/CA1034044A/en not_active Expired
- 1975-04-18 JP JP4736775A patent/JPS5337408B2/ja not_active Expired
- 1975-04-18 AR AR258417A patent/AR213271A1/es active
- 1975-04-18 HU HU75PI465A patent/HU175405B/hu unknown
- 1975-04-18 FR FR7512160A patent/FR2267760B1/fr not_active Expired

Also Published As

Publication number	Publication date
JPS5337408B2 (sv)	1978-10-09
HU175405B (hu)	1980-07-28
AU470631B2 (en)	1976-03-25
AU7987775A (en)	1976-03-25
FI62220B (fi)	1982-08-31
DK138161B (da)	1978-07-24
CS191244B2 (en)	1979-06-29
FI751108A (sv)	1975-10-20
PH11697A (en)	1978-05-24
JPS50145515A (sv)	1975-11-21
SE7503723L (sv)	1975-10-20
SE428528B (sv)	1983-07-11
FR2267760A1 (sv)	1975-11-14
FR2267760B1 (sv)	1978-08-04
CA1034044A (en)	1978-07-04
NL158384B (nl)	1978-11-15
DE2516105C3 (de)	1982-01-07
DE2516105A1 (de)	1975-10-23
DD119131A5 (sv)	1976-04-12
GB1474852A (en)	1977-05-25
ATA278875A (de)	1978-06-15
IE40829B1 (en)	1979-08-29
AT348130B (de)	1979-01-25
IL46994A (en)	1979-10-31
IE40829L (en)	1975-10-19
DK167075A (sv)	1975-10-20
ES436613A1 (es)	1977-04-16
DK138161C (sv)	1979-01-02
LU72320A1 (sv)	1976-03-17
BE828065A (fr)	1975-10-17
DE2516105B2 (de)	1981-01-08
BG35326A3 (en)	1984-03-15
AR213271A1 (es)	1979-01-15
IL46994A0 (en)	1975-06-25
NL7504274A (nl)	1975-10-21
US3927197A (en)	1975-12-16

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: PFIZER INC.

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