CH635513A5 - Process for the preparation of stable preparations of prostaglandins E - Google Patents

Process for the preparation of stable preparations of prostaglandins E Download PDF

Info

Publication number: CH635513A5
Authority: CH; Switzerland
Prior art keywords: glycol; prostaglandin; prostaglandins; preparation; isopropylidene
Prior art date: 1977-05-12

Application number

CH515878A

Other languages

German (de)

English (en)

Inventor

Kazuhiro Tsukada

Seiji Tanaka

Shinsaku Kobayashi

Original Assignee

Sankyo Co

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

1978-05-11

Publication date

1983-04-15

1978-05-11 Application filed by Sankyo Co filed Critical Sankyo Co

1983-04-15 Publication of CH635513A5 publication Critical patent/CH635513A5/de

Links

238000002360 preparation method Methods 0.000 title claims abstract description 30
150000003180 prostaglandins Chemical class 0.000 title claims abstract description 27
229940094443 oxytocics prostaglandins Drugs 0.000 title claims abstract description 19
238000000034 method Methods 0.000 title claims description 28
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 33
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 claims abstract description 31
150000001875 compounds Chemical class 0.000 claims abstract description 19
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 15
239000000243 solution Substances 0.000 claims abstract description 15
239000002904 solvent Substances 0.000 claims abstract description 15
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 12
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims abstract description 10
229940113115 polyethylene glycol 200 Drugs 0.000 claims abstract description 10
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims abstract description 8
HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 claims abstract description 5
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims abstract description 5
229940051250 hexylene glycol Drugs 0.000 claims abstract description 5
229920001451 polypropylene glycol Polymers 0.000 claims abstract description 5
239000007787 solid Substances 0.000 claims abstract description 5
PPPFYBPQAPISCT-UHFFFAOYSA-N 2-hydroxypropyl acetate Chemical compound CC(O)COC(C)=O PPPFYBPQAPISCT-UHFFFAOYSA-N 0.000 claims abstract description 4
OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims abstract description 4
OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 claims abstract description 4
GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 claims abstract description 4
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims abstract description 4
239000003814 drug Substances 0.000 claims abstract description 3
239000002504 physiological saline solution Substances 0.000 claims abstract description 3
239000002253 acid Substances 0.000 claims description 20
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 claims description 12
229960002986 dinoprostone Drugs 0.000 claims description 8
230000000694 effects Effects 0.000 claims description 8
-1 organic acid esters Chemical class 0.000 claims description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
229940068886 polyethylene glycol 300 Drugs 0.000 claims description 6
229940068918 polyethylene glycol 400 Drugs 0.000 claims description 6
229960004063 propylene glycol Drugs 0.000 claims description 5
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 claims description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
229960000711 alprostadil Drugs 0.000 claims description 4
229940124630 bronchodilator Drugs 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 4
230000000144 pharmacologic effect Effects 0.000 claims description 4
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 claims description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
239000005977 Ethylene Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 2
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 claims description 2
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 2
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
235000019483 Peanut oil Nutrition 0.000 claims description 2
238000000354 decomposition reaction Methods 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 2
150000002632 lipids Chemical class 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 claims description 2
239000000312 peanut oil Substances 0.000 claims description 2
239000003495 polar organic solvent Substances 0.000 claims description 2
239000008159 sesame oil Substances 0.000 claims description 2
235000011803 sesame oil Nutrition 0.000 claims description 2
150000003509 tertiary alcohols Chemical class 0.000 claims description 2
229940124549 vasodilator Drugs 0.000 claims description 2
239000003071 vasodilator agent Substances 0.000 claims description 2
235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
239000008158 vegetable oil Substances 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
239000007864 aqueous solution Substances 0.000 abstract description 3
XVEOUOTUJBYHNL-UHFFFAOYSA-N heptane-2,4-diol Chemical compound CCCC(O)CC(C)O XVEOUOTUJBYHNL-UHFFFAOYSA-N 0.000 abstract description 2
230000003182 bronchodilatating effect Effects 0.000 abstract 1
238000004108 freeze drying Methods 0.000 abstract 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
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 11
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
238000003379 elimination reaction Methods 0.000 description 4
210000003205 muscle Anatomy 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
238000012360 testing method Methods 0.000 description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
229960001340 histamine Drugs 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
241000700199 Cavia porcellus Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
230000008602 contraction Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000013101 initial test Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000000087 stabilizing effect Effects 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)

CH515878A 1977-05-12 1978-05-11 Process for the preparation of stable preparations of prostaglandins E CH635513A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
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
CH635513A5 true CH635513A5 (en)	1983-04-15

Family

ID=12977466

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH515878A CH635513A5 (en)	1977-05-12	1978-05-11	Process for the preparation of stable preparations of prostaglandins 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 (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT515356A1 (de) *	2014-01-30	2015-08-15	Gebro Holding Gmbh	Stabile alkoholische Lösung von Alprostadil

Families Citing this family (4)

* 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
US4409239A (en) *	1982-01-21	1983-10-11	Syntex (U.S.A.) Inc.	Propylene glycol diester solutions of PGE-type compounds
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
DE102004019743B4 (de)	2004-04-20	2008-11-27	Bayer Schering Pharma Aktiengesellschaft	Mehrphasenpräparat zur Kontrazeption auf der Basis eines natürlichen Estrogens

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
AT515356A1 (de) *	2014-01-30	2015-08-15	Gebro Holding Gmbh	Stabile alkoholische Lösung von Alprostadil
AT515356B1 (de) *	2014-01-30	2015-11-15	Gebro Holding Gmbh	Stabile alkoholische Lösung von Alprostadil

Also Published As

Publication number	Publication date
NL7805180A (nl)	1978-11-14
CA1090255A (en)	1980-11-25
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
1995-01-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

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