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1. EP0869941 - MODIFIED POLYUNSATURATED FATTY ACIDS

Office European Patent Office
Application Number 95933988
Application Date 13.10.1995
Publication Number 0869941
Publication Date 14.10.1998
Publication Kind B1
IPC
A61K 31/195
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
185Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
19Carboxylic acids, e.g. valproic acid
195having an amino group
A61K 31/20
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
185Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
19Carboxylic acids, e.g. valproic acid
20having a carboxyl group bound to an acyclic chain of seven or more carbon atoms, e.g. stearic, palmitic or arachidic acid
A61K 31/21
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
21Esters, e.g. nitroglycerine, selenocyanates
A61P 29/00
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
29Non-central analgesic, antipyretic or antiinflammatory agents, e.g antirheumatic agents; Non-steroidal antiinflammatory drugs (NSAIDs)
B01J 31/04
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
31Catalysts comprising hydrides, coordination complexes or organic compounds
02containing organic compounds or metal hydrides
04containing carboxylic acids or their salts
C07B 61/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
61Other general methods
CPC
A61P 29/00
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
29Non-central analgesic, antipyretic or anti-inflammatory agents, e.g antirheumatic agents; Non-steroidal anti-inflammatory drugs (NSAIDs)
A61P 33/06
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
33Antiparasitic agents
02Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
06Antimalarials
C07C 59/60
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
59Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
40Unsaturated compounds
58containing ether groups, groups, groups, or groups
60the non-carboxylic part of the ether being unsaturated
C07C 69/708
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
69Esters of carboxylic acids; Esters of carbonic or haloformic acids
66Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
67of saturated acids
708Ethers
C07C 323/52
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
323Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
50containing thio groups and carboxyl groups bound to the same carbon skeleton
51having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
52the carbon skeleton being acyclic and saturated
C07C 409/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
409Peroxy compounds
02the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
04the carbon atom being acyclic
Applicants PEPTECH LTD
WOMENS & CHILDRENS HOSPITAL
Inventors FERRANTE ANTONIO
POULOS ALFRED
EASTON CHRISTOPHER JOHN
PITT MICHAEL JOSEPH
ROBERTSON THOMAS ALISTAIR
RATHJEN DEBORAH ANN
Designated States
Priority Data 9500677 13.10.1995 AU
PM878194 13.10.1994 AU
PM906694 26.10.1994 AU
Title
(DE) MODIFIZIERTE MEHRFACH UNGESÄTTIGTE FETTSÄUREN
(EN) MODIFIED POLYUNSATURATED FATTY ACIDS
(FR) ACIDES GRAS POLYINSATURES MODIFIES
Abstract
(EN)
The present invention provides polyunsaturated fatty acid compounds having antimalarial and/or neutrophil stimulatory activity. The polyunsaturated fatty acids contain 18-25 carbons and 1-6 double bonds and are characterized in that they have one or two substitutions selected from the group consisting of $g(b) oxa, $g(g) oxa, $g(b) thia and $g(g) thia. It is also preferred that the polyunsaturated fatty acid compound includes a further substitution selected from the group consisting of hydroxy, hydroperoxy, peroxy, carboxymethyl substitutions or attached to an amino acid. The invention also provides a method of producing an unsaturated oxa substituted fatty acid comprising reacting an unsaturated fatty acid alcohol with a carbene that is inserted in the OH bond of the alcohol. The invention further provides a method of treating inflammation with a composition comprising at least one hydroxy, hydroperoxy or peroxy derivative of a polyunsaturated fatty acid having a C18-24 carbon chain and 1-6 cis or trans double bonds.

(FR)
La présente invention concerne des composés d'un acide gras polyinsaturé ayant une action antipaludéenne et/ou stimulante des neutrophiles. Les acides gras polyinsaturés, qui contiennent entre 18 et 25 atomes de carbone et une à six liaisons doubles, se caractérisent par le fait qu'ils ont un ou deux substituants sélectionnés à partir du groupe formé de $g(b) oxa, $g(g) oxa, $g(b) thia et $g(g) thia. Il est préférable que le composé d'acide gras polyinsaturé comprenne un substituant supplémentaire sélectionné à partir du groupe formé des susbstituants hydroxy, hydroperoxy, peroxy ou carboxyméthyl ou attaché à un acide aminé. L'invention porte également sur un procédé de production d'un acide gras insaturé substitué par oxa et qui consiste à faire réagir un alcool gras insaturé avec un carbène inséré dans la liaison OH de l'alcool. Cette invention présente, de surcroît, une technique de traitement anti-inflammatoire sous la forme d'une composition comprenant au moins un dérivé hydroxy, hydropéroxy ou péroxy d'un acide gras polyinsaturé ayant une chaîne carbonée C18-24 et une à six liaisons doubles cis ou trans.