CA1090255A - Stabilized compositions containing a prostaglandin e - Google Patents

Stabilized compositions containing a prostaglandin e

Info

Publication number: CA1090255A
Authority: CA; Canada
Prior art keywords: glycol; prostaglandin; monoester; cis; lower alkyl
Prior art date: 1977-05-12
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

Application number

CA303,253A

Other languages

English (en)

French (fr)

Inventor

Kazuhiro Tsukada

Seiji Tanaka

Shinsaku Kobayashi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sankyo Co Ltd

Original Assignee

Sankyo Co Ltd

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.)

1977-05-12

Filing date

1978-05-12

Publication date

1980-11-25

1978-05-12 Application filed by Sankyo Co Ltd filed Critical Sankyo Co Ltd

1980-11-25 Application granted granted Critical

1980-11-25 Publication of CA1090255A publication Critical patent/CA1090255A/en

Status Expired legal-status Critical Current

Links

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 title claims description 21
239000000203 mixture Substances 0.000 title claims description 17
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 52
-1 alkylene glycol Chemical compound 0.000 claims abstract description 42
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 33
150000003180 prostaglandins Chemical class 0.000 claims abstract description 18
239000000243 solution Substances 0.000 claims description 30
239000002253 acid Substances 0.000 claims description 25
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 24
238000000034 method Methods 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 14
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 12
239000007787 solid Substances 0.000 claims description 9
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 8
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 8
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
239000007864 aqueous solution Substances 0.000 claims description 6
229920001223 polyethylene glycol Polymers 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 5
229920001451 polypropylene glycol Polymers 0.000 claims description 5
PPPFYBPQAPISCT-UHFFFAOYSA-N 2-hydroxypropyl acetate Chemical compound CC(O)COC(C)=O PPPFYBPQAPISCT-UHFFFAOYSA-N 0.000 claims description 4
OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 4
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 4
OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 claims description 4
229940051250 hexylene glycol Drugs 0.000 claims description 4
GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 claims description 4
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 4
238000004108 freeze drying Methods 0.000 claims description 3
XVEOUOTUJBYHNL-UHFFFAOYSA-N heptane-2,4-diol Chemical compound CCCC(O)CC(C)O XVEOUOTUJBYHNL-UHFFFAOYSA-N 0.000 claims description 3
239000000155 melt Substances 0.000 claims description 2
229940113115 polyethylene glycol 200 Drugs 0.000 claims 6
229960004063 propylene glycol Drugs 0.000 claims 6
229940068886 polyethylene glycol 300 Drugs 0.000 claims 3
229940068918 polyethylene glycol 400 Drugs 0.000 claims 3
HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 claims 2
239000002202 Polyethylene glycol Substances 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 1
239000002904 solvent Substances 0.000 abstract description 24
229940094443 oxytocics prostaglandins Drugs 0.000 abstract description 12
230000001225 therapeutic effect Effects 0.000 abstract 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 18
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 17
230000000694 effects Effects 0.000 description 12
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
229960002986 dinoprostone Drugs 0.000 description 5
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
238000003379 elimination reaction Methods 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
STPUFZJFXIWGCZ-SIIFEQSASA-N (z)-7-[(1r,2r,3r)-3-hydroxy-2-[(1e,3s)-3-hydroxy-9-methyldeca-1,8-dienyl]-5-oxocyclopentyl]hept-5-enoic acid Chemical compound CC(C)=CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O STPUFZJFXIWGCZ-SIIFEQSASA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
230000032683 aging Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
210000003205 muscle Anatomy 0.000 description 3
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
230000003182 bronchodilatating effect Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
229960001340 histamine Drugs 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
BGKHCLZFGPIKKU-UHFFFAOYSA-N (13E,15S)-15-hydroxy-9-oxo-prosta-10,13-dienoic acid Natural products CCCCCC(O)C=CC1C=CC(=O)C1CCCCCCC(O)=O BGKHCLZFGPIKKU-UHFFFAOYSA-N 0.000 description 1
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
101100310593 Candida albicans (strain SC5314 / ATCC MYA-2876) SOD4 gene Proteins 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
MYHXHCUNDDAEOZ-UHFFFAOYSA-N Prostaglandin A&2% Natural products CCCCCC(O)C=CC1C=CC(=O)C1CC=CCCCC(O)=O MYHXHCUNDDAEOZ-UHFFFAOYSA-N 0.000 description 1
101100190148 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PGA2 gene Proteins 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000007796 conventional method Methods 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
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000007789 gas Substances 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
238000013101 initial test Methods 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
PRFXRIUZNKLRHM-UHFFFAOYSA-N l-prostaglandin B2 Natural products CCCCCC(O)C=CC1=C(CC=CCCCC(O)=O)C(=O)CC1 PRFXRIUZNKLRHM-UHFFFAOYSA-N 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
MYHXHCUNDDAEOZ-FOSBLDSVSA-N prostaglandin A2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O MYHXHCUNDDAEOZ-FOSBLDSVSA-N 0.000 description 1
PRFXRIUZNKLRHM-HKVRTXJWSA-N prostaglandin B2 Chemical compound CCCCC[C@H](O)\C=C\C1=C(C\C=C/CCCC(O)=O)C(=O)CC1 PRFXRIUZNKLRHM-HKVRTXJWSA-N 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000006104 solid solution Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1

Classifications

- 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
- 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
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA303,253A 1977-05-12 1978-05-12 Stabilized compositions containing a prostaglandin e Expired CA1090255A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP54679/1977		1977-05-12
JP52054679A JPS6019734B2 (ja)	1977-05-12	1977-05-12	安定なプロスタグランジンｅ類製剤の製法

Publications (1)

Publication Number	Publication Date
CA1090255A true CA1090255A (en)	1980-11-25

Family

ID=12977466

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA303,253A Expired CA1090255A (en)	1977-05-12	1978-05-12	Stabilized compositions containing a prostaglandin e

Country Status (7)

Country	Link
JP (1)	JPS6019734B2 (da)
CA (1)	CA1090255A (da)
CH (1)	CH635513A5 (da)
DK (1)	DK210778A (da)
ES (1)	ES469822A1 (da)
NL (1)	NL7805180A (da)
SE (1)	SE435898B (da)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0084865A1 (en) *	1982-01-21	1983-08-03	Syntex (U.S.A.) Inc.	Propylene glycol diester solutions of PGE-type compounds
US8071577B2 (en)	2004-04-20	2011-12-06	Bayer Pharma Aktiengesellschaft	Multi-phase contraceptive preparation based on a natural estrogen

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4310543A (en) *	1980-10-09	1982-01-12	Hoffmann-La Roche Inc.	Prostaglandin compositions
DE19541815B4 (de) *	1995-11-09	2008-04-10	Bannert, Christian, Dr.	Verwendung einer Lösung von Polyethylenglykol in Wasser als wässrige Spüllösung zur Prävention oder Behandlung von zähem Schleim, der in Verbindung mit Strahlen- oder/und Chemotherapie-induzierten Erkrankungen der Schleimhäute auftritt
AT515356B1 (de) *	2014-01-30	2015-11-15	Gebro Holding Gmbh	Stabile alkoholische Lösung von Alprostadil

1977
- 1977-05-12 JP JP52054679A patent/JPS6019734B2/ja not_active Expired
1978
- 1978-05-11 CH CH515878A patent/CH635513A5/de not_active IP Right Cessation
- 1978-05-12 CA CA303,253A patent/CA1090255A/en not_active Expired
- 1978-05-12 DK DK210778A patent/DK210778A/da not_active Application Discontinuation
- 1978-05-12 NL NL7805180A patent/NL7805180A/xx not_active Application Discontinuation
- 1978-05-12 ES ES469822A patent/ES469822A1/es not_active Expired
- 1978-05-12 SE SE7805499A patent/SE435898B/sv not_active IP Right Cessation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0084865A1 (en) *	1982-01-21	1983-08-03	Syntex (U.S.A.) Inc.	Propylene glycol diester solutions of PGE-type compounds
US8071577B2 (en)	2004-04-20	2011-12-06	Bayer Pharma Aktiengesellschaft	Multi-phase contraceptive preparation based on a natural estrogen

Also Published As

Publication number	Publication date
CH635513A5 (en)	1983-04-15
NL7805180A (nl)	1978-11-14
SE435898B (sv)	1984-10-29
JPS53139716A (en)	1978-12-06
ES469822A1 (es)	1978-12-16
DK210778A (da)	1978-11-13
JPS6019734B2 (ja)	1985-05-17
SE7805499L (sv)	1978-11-13

Legal Events

Date	Code	Title	Description
1997-11-25	MKEX	Expiry

Publication	Publication Date	Title
US2515898A (en)	1950-07-18	Procaine penicillin and therapeutic compositions
CA1203172A (en)	1986-04-15	Propylene glycol diester solutions of pge-type compounds
US5646181A (en)	1997-07-08	Method and compositions for treating impotence
US6960346B2 (en)	2005-11-01	Vehicles for delivery of biologically active substances
CA1176567A (en)	1984-10-23	Pharmaceutical preparation
EP0063367A1 (en)	1982-10-27	Acetal stabilized prostaglandin compositions
HU230484B1 (hu)	2016-07-28	Egy biciklusos vegyületet és egy gliceridet tartalmazó új kompozíció
IE39898L (en)	1974-12-16	Xanthine derivatives
CA1090255A (en)	1980-11-25	Stabilized compositions containing a prostaglandin e
JPS61501775A (ja)	1986-08-21	心臓障害の処置または予防用の医薬組成物および方法
US4036954A (en)	1977-07-19	Stable prostaglandin E group-containing formulation
WO1996021453A1 (de)	1996-07-18	Enrofloxacin-injektions- oder infusionslösungen
US4335139A (en)	1982-06-15	Pharmaceutical formulations containing prostacyclin compounds
BRPI0707333A2 (pt)	2011-05-03	composição farmacêutica que compreende um composto bicìclico e método de estabilização do composto bicìclico
US4092428A (en)	1978-05-30	Process of preparing stable prostaglandin E group-containing formulation
NO790059L (no)	1979-07-18	Fremgangsmaate for fremstilling av prostaglandinholdige terapeutiske preparater
US4696814A (en)	1987-09-29	Parenteral phenytoin compositions
Morris et al.	1946	The higher fatty alcohol esters of gallic acid
US4431833A (en)	1984-02-14	Prostaglandin and hydroxylated fatty acid ester formulations
JPH0643437B2 (ja)	1994-06-08	レベカマイシン類似体の安定な溶液およびその製造
US4235900A (en)	1980-11-25	Cephradine compositions
JPH07157431A (ja)	1995-06-20	安定なプロスタグランジンｅ製剤
US5420124A (en)	1995-05-30	Stable, painless piroxicam potassium injectable composition
US2898373A (en)	1959-08-04	Stabilization of panthenol
Shafiroff et al.	1952	Intravenous infusions into human subjects of fractionated coconut oil emulsions

CA1090255A - Stabilized compositions containing a prostaglandin e - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=12977466

Family Applications (1)

Country Status (7)

Cited By (2)

Families Citing this family (3)

Cited By (2)

Also Published As

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Legal Events