EP0000704A1 - Polyéthers; procédé pour leur préparation et leur application comme inhibiteurs de l'absorption des lipides - Google Patents
Polyéthers; procédé pour leur préparation et leur application comme inhibiteurs de l'absorption des lipides Download PDFInfo
- Publication number
- EP0000704A1 EP0000704A1 EP78100357A EP78100357A EP0000704A1 EP 0000704 A1 EP0000704 A1 EP 0000704A1 EP 78100357 A EP78100357 A EP 78100357A EP 78100357 A EP78100357 A EP 78100357A EP 0000704 A1 EP0000704 A1 EP 0000704A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- ethylene oxide
- oxide content
- polymeric
- molecular weight
- polyethers
- Prior art date
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
-
- 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
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
- A61K31/77—Polymers containing oxygen of oxiranes
Definitions
- the present invention relates to new polyethers, several processes for their preparation and their use as medicaments which influence the metabolism, in particular as lipid absorption inhibitors.
- polyethers consisting of ethylene oxide and propylene oxide groups (see US Pat. No. 2,674,619). It is also known that polyoxyalkylenes with molecular weights of approx. 1000 to approx. 11,000 have surface-active properties and can also be used in pharmaceutical preparations. US Pat. No. 3,641,240 claims and describes the use of polyoxyalkylenes with a molecular weight of approximately 2000 to 10,000 and an ethylene oxide content of 50 to 90% as antithrombotics. In this patent it is expressly pointed out that the applicable Polyoxyalkylene should contain at least 50% ethylene oxide.
- U.S. Patent 3,202,578 describes polyoxyalkylenes which can be used as laxatives. In addition to the laxative effect, this patent also mentions an effect on lowering cholesterol in the blood. According to the statements in this patent specification, such polyoxyalkylenes are particularly suitable as cholesterol-lowering compounds which have a molecular weight of 7,500 and contain 80% ethylene oxide.
- polyethers of general structure (I) with an average molecular weight of 4000, a propylene oxide content of 70% and an ethylene oxide content of 30%.
- the polyethers of the general structure (I) according to the invention are prepared by Propylene glycol in the presence of alkali hydroxide by polyaddition first with propylene oxide and then with a corresponding amount of ethylene oxide, the alkali metal hydroxide is then neutralized with aqueous mineral acid and, after dehydration of the polyether, removed by salt filtration.
- the polyethers according to the invention have a narrow molecular weight distribution.
- the characterization and composition of the polymeric oxyalkylene compounds is carried out analytically by determining the molecular weight from the hydroxyl number.
- the ethylene oxide content is determined from the H-NMR spectrum.
- the polyethers according to the invention surprisingly show very strong effects in the treatment of fat and carbohydrate metabolism disorders. In particular, they lower the elevated cholesterol in serum and tissue and at the same time reduce hypertriglyceridaemia.
- the compounds according to the invention are suitable for the treatment of hyperlipoproteinaemia, atherosclerosis, obesity and for the treatment of metabolic disorders triggered thereby.
- polyethers according to the invention of the present application have such a pronounced hypolipidemic effect in this molecular weight range from 3 to 5000, in particular 4000, and the special propylene oxide / ethylene oxide ratio. Since the compounds according to the invention are at the same time very well tolerated in addition to this strong action, they represent an enrichment of the pharmaceutical industry.
- the present invention includes pharmaceutical preparations which, in addition to non-toxic, inert pharmaceutically suitable excipients, contain one or more compounds of the above formula or which consist of one or more compounds of the above formula, and processes for the preparation of these preparations.
- the invention also includes pharmaceutical preparations in dosage units.
- the dosage units can e.g. 1, 2, 3 or 4 single doses or 1/2, 1/3 or 1/4 of a single dose.
- a single dose preferably contains the amount of active ingredient which is administered in one application and which usually corresponds to a whole, a half or a third or a quarter of a daily dose.
- Non-toxic, inert pharmaceutically suitable excipients are to be understood as solid, semisolid or liquid diluents, fillers and formulation auxiliaries of all kinds.
- Tablets, dragees, capsules, pills, granules, suppositories, solutions, suspensions and emulsions, pastes may be mentioned as preferred pharmaceutical preparations.
- Tablets, coated tablets, capsules, pills and granules can contain the active ingredient (s) in addition to the usual carriers, such as (a) fillers and extenders, for example starches, Milk sugar, cane sugar, glucose, mannitol and silica, (b) binders, e.g. carboxymethyl cellulose, alginates, gelatin, polyvinylpyrrolidone, (c) humectants, e.g. glycerin, (d) disintegrants, e.g. agar-agar, calcium carbonate and sodium bicarbonate, (e) dissolving agents , e.g. paraffin and (f) absorption accelerators, e.g.
- fillers and extenders for example starches, Milk sugar, cane sugar, glucose, mannitol and silica
- binders e.g. carboxymethyl cellulose, alginates, gelatin, polyvinylpyrrolidone
- humectants e.g
- quaternary ammonium compounds (g) wetting agents, e.g. cetycohol, glycerol monostearate, (h) adsorbents, e.g. kaolin and bentonite and (i) lubricants, e.g. talc, calcium and magnesium stearate and solid polyethylene glycols or mixtures of the substances listed under (a) - (i).
- wetting agents e.g. cetycohol, glycerol monostearate
- adsorbents e.g. kaolin and bentonite
- lubricants e.g. talc, calcium and magnesium stearate and solid polyethylene glycols or mixtures of the substances listed under (a) - (i).
- the tablets, dragees, capsules, pills and granules can be provided with the usual coatings and casings, optionally containing opacifying agents, and can also be composed such that they release the active ingredient (s) only or preferably in a certain part of the intestinal tract, if necessary with a delay , where as embedding compounds, for example Polymer substances and waxes can be used.
- the active ingredient (s) can optionally also be in microencapsulated form with one or more of the above-mentioned excipients.
- suppositories can contain the usual water-soluble or water-insoluble carriers, for example polyethylene glycols, fats, for example cocoa fat, and higher esters (for example C 14 alcohol with C 16 fatty acid) or mixtures of these substances.
- water-soluble or water-insoluble carriers for example polyethylene glycols, fats, for example cocoa fat, and higher esters (for example C 14 alcohol with C 16 fatty acid) or mixtures of these substances.
- solutions and emulsions can contain the usual carriers, such as solvents, solubilizers and emulsifiers, e.g. Water, ethyl alcohol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butylene glycol, dimethylformamide, oils, in particular cottonseed oil, peanut oil, corn oil, olive oil, castor oil and sesame oil, glycerin, glycerol formate, fatty alcohol ester fatty acid, tetrahydrofuran desorbate or mixtures of these substances.
- solvents e.g. Water, ethyl alcohol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butylene glycol, dimethylformamide, oils, in particular cottonseed
- solutions and emulsions can also be in sterile and blood isotonic form.
- suspensions can contain the usual carriers, such as liquid diluents, e.g. Water, ethyl alcohol, propylene glycol, suspending agents e.g. contain ethoxylated isostearyl alcohols, polyoxyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminum methoxide, bentonite, agar and tragacanth or mixtures of these substances.
- liquid diluents e.g. Water, ethyl alcohol, propylene glycol
- suspending agents e.g. contain ethoxylated isostearyl alcohols, polyoxyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminum methoxide, bentonite, agar and tragacanth or mixtures of these substances.
- the formulation forms mentioned can also contain colorants, preservatives and additives which improve the smell and taste, for example peppermint oil and eucalyptus oil, and sweeteners, for example saccharin.
- the therapeutically active compounds should be present in the pharmaceutical preparations listed above in a concentration of about 0.1 to 99.5, preferably about 0.5 to 95 percent by weight of the total mixture.
- the pharmaceutical preparations listed above can also contain other active pharmaceutical ingredients.
- the pharmaceutical preparations listed above are prepared in a conventional manner by known methods, e.g. by mixing the active substance or substances with the carrier substance or substances.
- the present invention also includes the use of the compounds of the above formula and the use of pharmaceutical preparations which contain one or more compounds of the above formula in human and veterinary medicine for preventing, ameliorating and / or curing the above-mentioned diseases.
- the active substances or the pharmaceutical preparations can be administered orally, parenterally, intraperitoneally and / or rectally, preferably orally.
- the active ingredient (s) in amounts of about 0.05 to about 500, preferably 0.5 to 200 mg / kg body weight per 24 hours. , to be applied over 1 to 6 administrations, namely before or / and during or / and after the meal.
- a single dose ent holds the active ingredient (s) preferably in amounts of about 0.1 to about 100 mg / kg body weight.
- ea may be sufficient to make do with less than the above-mentioned amount of active ingredient, while in other cases the amount of active ingredient mentioned above must be exceeded.
- the optimum dosage and type of application of the active ingredients required in each case can easily be determined by any person skilled in the art on the basis of his specialist knowledge.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2732929 | 1977-07-21 | ||
DE19772732929 DE2732929A1 (de) | 1977-07-21 | 1977-07-21 | Polyaether, verfahren zu ihrer herstellung sowie ihre verwendung als lipidabsorptionshemmer |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0000704A1 true EP0000704A1 (fr) | 1979-02-21 |
Family
ID=6014492
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP78100357A Withdrawn EP0000704A1 (fr) | 1977-07-21 | 1978-07-11 | Polyéthers; procédé pour leur préparation et leur application comme inhibiteurs de l'absorption des lipides |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP0000704A1 (fr) |
JP (1) | JPS5422497A (fr) |
AU (1) | AU3806878A (fr) |
CA (1) | CA1111453A (fr) |
DE (1) | DE2732929A1 (fr) |
DK (1) | DK324678A (fr) |
ES (1) | ES471900A1 (fr) |
FI (1) | FI782284A (fr) |
IL (1) | IL55160A0 (fr) |
IT (1) | IT1097831B (fr) |
NO (1) | NO782332L (fr) |
PT (1) | PT68307A (fr) |
ZA (1) | ZA784129B (fr) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0011237A1 (fr) * | 1978-11-18 | 1980-05-28 | Bayer Ag | Dérivés de polyéthers, procédé pour leur préparation et leur application comme médicaments |
EP0018591A1 (fr) * | 1979-04-25 | 1980-11-12 | BASF Aktiengesellschaft | Masses à mouler renfermant des copolymères styrène-acrylonitrile et des copolymères en blocs triséquencés à base d'oxyde d'éthylène/oxyde de propylène, leur utilisation et corps moulés à partir de ces masses à mouler |
EP0103290A2 (fr) * | 1982-09-14 | 1984-03-21 | Intermedicat Gmbh | Compositions pharmaceutiques pour le traitement de coalescence indésirable et leur utilisation |
EP0166958A1 (fr) * | 1984-06-02 | 1986-01-08 | Hoechst Aktiengesellschaft | Polyétylène-glycols |
WO1988006038A1 (fr) * | 1987-02-20 | 1988-08-25 | Emory University | Composes anti-infectieux et procede d'utilisation |
EP0576612A1 (fr) * | 1991-03-19 | 1994-01-05 | Cytrx Corporation | Copolymeres de polyoxypropylene/polyoxyethylene presentant une activite biologique amelioree |
US5674911A (en) * | 1987-02-20 | 1997-10-07 | Cytrx Corporation | Antiinfective polyoxypropylene/polyoxyethylene copolymers and methods of use |
US5811088A (en) * | 1987-02-20 | 1998-09-22 | Emory University | Antiinfective compounds and methods of use |
USRE38558E1 (en) | 1991-03-19 | 2004-07-20 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
US6933286B2 (en) | 1991-03-19 | 2005-08-23 | R. Martin Emanuele | Therapeutic delivery compositions and methods of use thereof |
US7202225B1 (en) | 1993-10-15 | 2007-04-10 | Emanuele R Martin | Therapeutic delivery compositions and methods of use thereof |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6030650B2 (ja) * | 1979-10-26 | 1985-07-17 | 日本油脂株式会社 | 座薬基剤組成物 |
EP0907666A1 (fr) | 1996-06-27 | 1999-04-14 | G.D. Searle & Co. | Particules comprenant des copolymeres amphiphiles, possedant un domaine de reticulation croisee et un domaine de noyau interne, utilisables en pharmacologie et autres applications |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB610505A (en) * | 1944-02-08 | 1948-10-18 | Carbide & Carbon Chem Corp | A method for making polyoxyalkylene glycols |
FR1116M (fr) * | 1961-02-02 | 1962-02-12 | Bernard Andre Francois Mirande | Utilisation de substances tensio-actives provenant de la condensation de l'oxyde d'éthylene sur les propylenes-glycols dans la résorption des oedemes locaux ou tissulaires systématisés. |
NL6618108A (fr) * | 1965-12-23 | 1967-06-26 |
-
1977
- 1977-07-21 DE DE19772732929 patent/DE2732929A1/de active Pending
-
1978
- 1978-07-04 NO NO782332A patent/NO782332L/no unknown
- 1978-07-11 EP EP78100357A patent/EP0000704A1/fr not_active Withdrawn
- 1978-07-17 AU AU38068/78A patent/AU3806878A/en active Pending
- 1978-07-17 PT PT68307A patent/PT68307A/pt unknown
- 1978-07-18 IL IL55160A patent/IL55160A0/xx unknown
- 1978-07-19 JP JP8721378A patent/JPS5422497A/ja active Pending
- 1978-07-19 FI FI782284A patent/FI782284A/fi not_active Application Discontinuation
- 1978-07-19 IT IT25897/78A patent/IT1097831B/it active
- 1978-07-20 DK DK324678A patent/DK324678A/da unknown
- 1978-07-20 ZA ZA00784129A patent/ZA784129B/xx unknown
- 1978-07-20 CA CA307,799A patent/CA1111453A/fr not_active Expired
- 1978-07-20 ES ES471900A patent/ES471900A1/es not_active Expired
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB610505A (en) * | 1944-02-08 | 1948-10-18 | Carbide & Carbon Chem Corp | A method for making polyoxyalkylene glycols |
FR1116M (fr) * | 1961-02-02 | 1962-02-12 | Bernard Andre Francois Mirande | Utilisation de substances tensio-actives provenant de la condensation de l'oxyde d'éthylene sur les propylenes-glycols dans la résorption des oedemes locaux ou tissulaires systématisés. |
NL6618108A (fr) * | 1965-12-23 | 1967-06-26 |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0011237A1 (fr) * | 1978-11-18 | 1980-05-28 | Bayer Ag | Dérivés de polyéthers, procédé pour leur préparation et leur application comme médicaments |
EP0018591A1 (fr) * | 1979-04-25 | 1980-11-12 | BASF Aktiengesellschaft | Masses à mouler renfermant des copolymères styrène-acrylonitrile et des copolymères en blocs triséquencés à base d'oxyde d'éthylène/oxyde de propylène, leur utilisation et corps moulés à partir de ces masses à mouler |
EP0103290A2 (fr) * | 1982-09-14 | 1984-03-21 | Intermedicat Gmbh | Compositions pharmaceutiques pour le traitement de coalescence indésirable et leur utilisation |
EP0103290A3 (fr) * | 1982-09-14 | 1984-09-05 | Intermedicat Gmbh | Compositions pharmaceutiques pour le traitement de coalescence indésirable et leur utilisation |
EP0166958A1 (fr) * | 1984-06-02 | 1986-01-08 | Hoechst Aktiengesellschaft | Polyétylène-glycols |
US5674911A (en) * | 1987-02-20 | 1997-10-07 | Cytrx Corporation | Antiinfective polyoxypropylene/polyoxyethylene copolymers and methods of use |
WO1988006038A1 (fr) * | 1987-02-20 | 1988-08-25 | Emory University | Composes anti-infectieux et procede d'utilisation |
US5811088A (en) * | 1987-02-20 | 1998-09-22 | Emory University | Antiinfective compounds and methods of use |
EP0576612A1 (fr) * | 1991-03-19 | 1994-01-05 | Cytrx Corporation | Copolymeres de polyoxypropylene/polyoxyethylene presentant une activite biologique amelioree |
EP0576612A4 (fr) * | 1991-03-19 | 1994-11-09 | Cytrx Corp | Copolymeres de polyoxypropylene/polyoxyethylene presentant une activite biologique amelioree. |
US5990241A (en) * | 1991-03-19 | 1999-11-23 | Cytrx, Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
USRE36665E (en) * | 1991-03-19 | 2000-04-18 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
USRE37285E1 (en) | 1991-03-19 | 2001-07-17 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolmers with improved biological activity |
US6359014B1 (en) | 1991-03-19 | 2002-03-19 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
US6747064B2 (en) | 1991-03-19 | 2004-06-08 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
USRE38558E1 (en) | 1991-03-19 | 2004-07-20 | Cytrx Corporation | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
US6933286B2 (en) | 1991-03-19 | 2005-08-23 | R. Martin Emanuele | Therapeutic delivery compositions and methods of use thereof |
US7202225B1 (en) | 1993-10-15 | 2007-04-10 | Emanuele R Martin | Therapeutic delivery compositions and methods of use thereof |
Also Published As
Publication number | Publication date |
---|---|
IT7825897A0 (it) | 1978-07-19 |
FI782284A (fi) | 1979-01-22 |
IL55160A0 (en) | 1978-09-29 |
NO782332L (no) | 1979-01-23 |
JPS5422497A (en) | 1979-02-20 |
DE2732929A1 (de) | 1979-02-01 |
ES471900A1 (es) | 1979-02-01 |
CA1111453A (fr) | 1981-10-27 |
IT1097831B (it) | 1985-08-31 |
ZA784129B (en) | 1979-07-25 |
PT68307A (de) | 1978-08-01 |
AU3806878A (en) | 1980-01-17 |
DK324678A (da) | 1979-01-22 |
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Legal Events
Date | Code | Title | Description |
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PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
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17P | Request for examination filed | ||
AK | Designated contracting states |
Designated state(s): BE CH DE FR GB LU NL SE |
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STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
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18W | Application withdrawn | ||
RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: SITT, RUEDIGER, DR. Inventor name: PLUS, WALTER, DR. Inventor name: KRAUSE, HANS PETER, DR. Inventor name: STEINERT, GERD, DR. Inventor name: HORSTMANN, HARALD, DR. |