WO2009152917A4 - Stabilization of the composition of a mixture - Google Patents
Stabilization of the composition of a mixture Download PDFInfo
- Publication number
- WO2009152917A4 WO2009152917A4 PCT/EP2009/003666 EP2009003666W WO2009152917A4 WO 2009152917 A4 WO2009152917 A4 WO 2009152917A4 EP 2009003666 W EP2009003666 W EP 2009003666W WO 2009152917 A4 WO2009152917 A4 WO 2009152917A4
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- petasin
- extract
- formula
- carbon atoms
- neopetasin
- Prior art date
Links
Classifications
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/62—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Medicines Containing Plant Substances (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Described is a method for slowing the speed of the isomerisation of petasin and neopetasin to isopetasin, and the isomerisation of S-petasin and neo-S-petasin to iso-S-petasin, especially in extracts from plants of the genus Petasites, preferably Petasites hybridus, by the addition of at least one suitable stabilizer and/or the removal of at least one destabilizing substance, e.g. a fatty acid.
Claims
1. Method for slowing the speed of the isomerisation of petasin and neopetasin to isopetasin, and the isomerisation of S-petasin and neo-S-petasin to iso-S-petasin in extracts from plants of Petasites hybridus, said extracts comprising petasin, neopetasin and isopetasin, by the addition of at least one suitable stabilizer and the removal of at least one destabilizing substance, wherein the stabilizer is selected from a) a compound of formula I
R1KCH2)H-OH (I) wherein n is 1, R1 represents alkyl having 2 to 30 carbon atoms wherein one or more non- adjacent carbon atoms may be replaced by oxygen; or R1 represents cycloalkyl, phenyl, or phenoxymethyl, each of which is unsubstituted or substituted in the cyclic moiety by Ci- Cγ-alkyl or Ci-C7-alkoxy, b) a glycol of the formula HO-[CHR2-CH2-O]m-H, wherein R2 is hydrogen or methyl and m is 1 to 500, or of the formula HO-[CH2-CH2-O]x-[CH2-CH(CH3)-0]y-[CH2-CH2-O]z-H wherein x is 50-125, y is 20-70 and z is 50-125, c) dibenzylether, and d) hydrogenated castor oil, and wherein the destabilizing substance is a fatty acid in free and/or bound form.
2. Pharmaceutical formulation comprising an extract from plants of Petasites hybridus, said extract comprising petasin, neopetasin and isopetasin, wherein the amount of fatty acids has been reduced below 50 % of the natural occurrence in the extract, together with a stabilizer selected from a) a compound of formula I
R1KCH2VOH (I) wherein n is 1, R1 represents alkyl having 2 to 30 carbon atoms wherein one or more non- adjacent carbon atoms may be replaced by oxygen; or R1 represents cycloalkyl, phenyl, or phenoxymethyl, each of which is unsubstituted or substituted in the cyclic moiety by Cj- C7-alkyl or Ci-C7-alkoxy, b) a glycol of the formula HO-[CHR2-CH2-O]m-H, wherein R is hydrogen or methyl and m is 1 to 500, or of the formula HO-[CH2-CH2-O]x-[CH2-CH(CH3)-O]y-[CH2-CH2-O]z-H wherein x is 50-125, y is 20-70 and z is 50-125, c) dibenzylether, and d) a hydrogenated plant oil, like hydrogenated castor oil, and a pharmaceutical excipient.
3. Pharmaceutical formulation according to claim 2, wherein the stabilizer is selected from a) a compound of formula I
R^(CH2)H-OH (I) wherein n is 1, R1 represents alkyl having 2 to 30 carbon atoms wherein one or more non- adjacent carbon atoms may be replaced by oxygen; or R1 represents cycloalkyl, phenyl, or phenoxymethyl, each of which is unsubstituted or substituted in the cyclic moiety by Q- Cyalkyl or Ci-C7-alkoxy, b) dibenzylether, and c) a hydrogenated plant oil, like hydrogenated castor oil.
4. Pharmaceutical formulation according to claim 2 substantially free from free fatty acids.
5. Pharmaceutical formulation according to any one of claims 2 -4 in a non- liquid form.
6. Pharmaceutical formulation according to any one of claims 2-4 wherein the amount by weight of the stabilizer is 3-6fold the amount by weight of the native extract.
7. Pharmaceutical formulation according to any one of claims 2-4 wherein the extract from plants of Petasites hybridus has been obtained by extraction with carbon dioxide.
8. Extract from plants of Petasites hybridus, said extract comprising petasin, neopetasin and isopetasin, wherein the amount of fatty acids has been reduced below 50 % of the natural occurrence in the extract, and further comprising a stabilizer slowing the speed of the isomerisation of petasin and neopetasin to isopetasin, and the isomerisation of S- petasin and neo-S-petasin to iso-S-petasin selected from a) a compound of formula I
R'-(CH2)n-OH (I) wherein n is 1, R1 represents alkyl having 2 to 30 carbon atoms wherein one or more non- adjacent carbon atoms may be replaced by oxygen; or R1 represents cycloalkyl, phenyl, or phenoxymethyl, each of which is unsubstituted or substituted in the cyclic moiety by C1- C7-alkyl or Ci-C7-alkoxy, b) a glycol of the formula HO-[CHR2-CH2-O]m-H, wherein R2 is hydrogen or methyl and m is 1 to 500, or of the formula HO-[CH2-CH2-O]x-[CH2-CH(CH3)-O]y-[CH2-CH2-O]z-H wherein x is 50-125, y is 20-70 and z is 50-125, c) dibenzylether, and d) hydrogenated castor oil.
9. Extract according to claim 8 which has been obtained by extraction with carbon dioxide.
10. Extract according to claim 8 substantially free from free fatty acids.
11. Process for the manufacture of an extract as claimed in any one of claims 8-10 by removing from an extract from plants of Petasites hybridus, said extract comprising petasin, neopetasin and isopetasin, fatty acids promoting the isomerisation of petasin and neopetasin to isopetasin by passing a solution comprising said extract through a suitable weakly alkaline ion exchanger or by neutralizing said fatty acid in said extract with a suitable base and extracting it with water followed by addition of a stabilizer as defined in claim 7.
12. Extract obtainable by the process according to claim 11.
13. Use of a stabilizer selected from a) a compound of formula I
R'-CCHΛ-OH (I) wherein n 1, R1 represents alkyl having 2 to 30 carbon atoms wherein one or more non- adjacent carbon atoms may be replaced by oxygen; or R1 represents cycloalkyl, phenyl, or phenoxymethyl, each of which is unsubstituted or substituted in the cyclic moiety by Cj- C7-alkyl or Ci-C7-alkoxy, b) a glycol of the formula HO-[CHR2-CH2-O]m-H, wherein R2 is hydrogen or methyl and m is 1 to 500, or of the formula HO-[CH2-CH2-O]x-[CH2-CH(CH3)-O]y-[CH2-CH2-O]z-H wherein x is 50-125, y is 20-70 and z is 50-125, c) dibenzylether, and d) hydrogenated castor oil, for slowing the speed of the isomerisation of petasin and neopetasin to isopetasin, and the isomerisation of S-petasin and neo-S-petasin to iso-S-petasin in an extract from plants of Petasites hybridus, wherein said extract comprises petasin, neopetasin and isopetasin, and wherein the amount of fatty acids has been reduced below 50 % of the natural occurrence in the extract.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09765497A EP2285767A2 (en) | 2008-05-29 | 2009-05-23 | Stabilization of the composition of a mixture |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08009760.3 | 2008-05-29 | ||
EP08009760 | 2008-05-29 |
Publications (3)
Publication Number | Publication Date |
---|---|
WO2009152917A2 WO2009152917A2 (en) | 2009-12-23 |
WO2009152917A3 WO2009152917A3 (en) | 2010-08-19 |
WO2009152917A4 true WO2009152917A4 (en) | 2010-10-21 |
Family
ID=40010721
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2009/003666 WO2009152917A2 (en) | 2008-05-29 | 2009-05-23 | Stabilization of the composition of a mixture |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP2285767A2 (en) |
WO (1) | WO2009152917A2 (en) |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR8351M (en) * | 1967-01-27 | 1971-02-08 | ||
CH537420A (en) * | 1969-02-24 | 1973-05-31 | Clausmann Otto | Process for obtaining a stabilized, therapeutically highly active petasites extract with a content of 50 to 55% genuine petasin |
CH660966A5 (en) * | 1984-02-29 | 1987-06-30 | Amo Pharm Ag | Process for obtaining a petasites extract with high therapeutic activity from Petasites hybridus, with a content of from 60 to 75% petasin |
RO90371A2 (en) * | 1984-08-11 | 1986-09-30 | Directia Sanitara A Judetului Neamt,Laboratorul"Plantavorel",Ro | MEDICINAL PRODUCT PHYTOTHERAPY ANXIOLITIS TRANQUILIZING AND SPASMOLYTIC |
JPS61206449A (en) * | 1985-03-09 | 1986-09-12 | 松下電工株式会社 | Deodorant |
JPS62360A (en) * | 1985-06-25 | 1987-01-06 | 松下電工株式会社 | Deodorizing filter |
ES2044848T3 (en) * | 1987-03-12 | 1994-01-16 | Plantamed Arzneimittel Gmbh | USE OF PETASITE EXTRACTS TO PREPARE A MEDICATION FOR THE TREATMENT OF GASTROINTESTINAL DISEASES. |
JPH02180267A (en) * | 1988-12-30 | 1990-07-13 | Matsushita Electric Works Ltd | Deodorant |
JPH0430855A (en) * | 1990-05-28 | 1992-02-03 | Matsushita Electric Works Ltd | Mousse-like deodorant |
JP2804822B2 (en) * | 1990-05-28 | 1998-09-30 | 松下電工株式会社 | Deodorants |
JPH0693909B2 (en) * | 1990-11-27 | 1994-11-24 | 松下電工株式会社 | Deodorant for shaver |
DE4208300C2 (en) * | 1992-03-16 | 1994-01-13 | Plantamed Arzneimittel Gmbh | Use of oxopetasin as a component of medicines for the treatment of gastrointestinal diseases |
DE19838848A1 (en) * | 1998-08-26 | 2000-03-02 | Weber & Weber Gmbh & Co Kg | Composition containing pyrrolizidine alkaloid-free petasites |
KR100438322B1 (en) * | 2001-11-14 | 2004-07-02 | 한불화장품주식회사 | A cosmetic composition containing an extract of petasites japonicus |
KR100535655B1 (en) * | 2003-03-14 | 2005-12-08 | 충남대학교산학협력단 | Extract of Petasites japonicus having neuroprotective effect and antioxidant activity |
JP2005179308A (en) * | 2003-12-22 | 2005-07-07 | Oriza Yuka Kk | Antiallergy composition |
DE102004039011A1 (en) * | 2004-08-11 | 2006-03-30 | Max Zeller Söhne Ag | Extract, useful to prepare a medicament to treat e.g. gastrointestinal pain, cramps of urogenital tracts, asthma, cough and headache, comprises Petasites hybridus extract, that is free of pyrrolizidine alkaloid and furanoeremophilane |
-
2009
- 2009-05-23 EP EP09765497A patent/EP2285767A2/en not_active Withdrawn
- 2009-05-23 WO PCT/EP2009/003666 patent/WO2009152917A2/en active Application Filing
Also Published As
Publication number | Publication date |
---|---|
EP2285767A2 (en) | 2011-02-23 |
WO2009152917A3 (en) | 2010-08-19 |
WO2009152917A2 (en) | 2009-12-23 |
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