Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Radical -xh acid – or anhydride – acid halide or salt thereof...
Patent
1995-05-19
1998-05-19
Cook, Rebecca
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Radical -xh acid, or anhydride, acid halide or salt thereof...
514558, 514547, 514613, 514616, 514706, 514738, 514859, C07C 5713, A61K 748
Patent
active
057537046
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of PCT/GB93/02006 filed Aug. 27, 1993 published as WO94/07837 Apr. 14, 1994.
FIELD OF THE INVENTION
This invention relates to unsaturated dioic acids, that is, unsaturated aliphatic dicarboxylic acids, especially C.sub.8 -C.sub.22 compounds, particularly, but not exclusively, C.sub.16 and C.sub.18 unsaturated dioic acids (i.e. those having 16 or 18 carbon atoms), and concerns certain novel C.sub.8 -C.sub.16 dioic acids, a method of producing dioic acids, and their use in the treatment of skin for medical and cosmetic purposes, such as acne treatment and skin lightening.
BACKGROUND OF THE INVENTION
It is known to use saturated dioic acids (having the general formula COOH (CH.sub.2).sub.n COOH) for the treatment of skin for medical and cosmetic purposes. For example, U.S. Pat. No. 4,386,104 (Nazzaro-Porro) discloses saturated dioic acids, containing 7 to 13 carbon atoms, for the treatment of acne and other skin conditions.
In particular, the C.sub.9 saturated dioic acid ("azelaic" acid) having the formula COOH(CH.sub.2).sub.7 COOH, is frequently cited as being effective in the treatment of acne and other skin conditions, and in the lightening of skin.
Thus far, unsaturated dioic acids have not been readily commercially available, although a method of synthesising certain unsaturated dioic acids is disclosed in EP 0229252. Indeed some of this class of molecules have not previously been described. However, it is known that certain unsaturated dioic acids, particularly certain C.sub.6, C.sub.8, C.sub.10 and C.sub.12 mono-unsaturated dioic acids can be detected in the urine of patients with medium chain acyl-CoA dehydrogenase deficiency (Jin & Tserng Journal of Lipid Research 31, 763-771). Certain other unsaturated dioic acids are disclosed in various other publications.
EP 0341796 discloses a microbial route using Candida cloacae beta-oxidation mutants for the production of saturated dioic acids from longer chain saturated fatty acids (monocarboxylic acids) or triglycerides. The present inventors have now produced, using the mutants disclosed in EP0341796, certain unsaturated dioic acids, some of which are novel per se, which have been found to have surprisingly enhanced properties for use in the treatment of skin for medical and cosmetic purposes.
SUMMARY OF THE INVENTION
In a first aspect the invention provides a poly-unsaturated dioic acid (i.e. a dioic acid comprising 2 or more carbon/carbon double bonds) having between 8 and 16 carbon atoms (inclusive), excluding those compounds in the group consisting of: 2,5 octadienedioic acid; 1,7 octadienedioic acid; 2,4,6 octatrienedioic acid; 1,3,5,7 nonatetraene dioic acid 2,5,8 decatrienedioic acid; 3,6 dodecadienedioic acid; and 3,13 hexadecadienedioic acid.
The compounds specifically excluded above are known from various prior art publications (e.g. Grundman, 1937 Ber. 70B, 1148-1153).
The novel compounds claimed are all capable of being synthesised by means of a novel method, detailed further below.
It is preferred that the compound is a dioic acid with an even-length hydrocarbon chain. Particularly preferred are the C.sub.16 compounds.
Another preferred feature is that the carbon/carbon double bonds are separated by two carbon/carbon single bonds (i.e. double bonds may preferably be situated at carbon atoms 3 and 6, or 2 and 5 etc.), as such compounds are those most readily produced by the novel method.
Surprisingly, it has been found by the present inventors that the novel unsaturated dioic acids, and indeed unsaturated dioic acids in general (especially C.sub.16 and C.sub.18 unsaturated dioic acids) possess much greater activity than their saturated dioic acid counterparts, as anti-microbial agents and as cosmetic agents.
The prior art teaches that conditions susceptible to treatment with dioic acids include: acne (U.S. Pat. No. 4,386,104); wrinkles (EP 336880); malignant melanoma (U.S. Pat. No. 4,818,768); dermatoses (EP 229654); hyperpigmentary dermatosis and eczema (U.S. Pat. No. 4,292,326); rosacea (EP 890308); lentigo (JP 91024412
REFERENCES:
patent: 2957907 (1960-10-01), Payne et al.
patent: 3497435 (1970-02-01), Wimer et al.
patent: 3793367 (1974-02-01), Diekman
Otieno, et al: "Thermal Acid-Catalysed Rearrangements of Natural Chrysanthemic Acid", Journal of the Chemical Society, Perkin Transactions I, No. 2, 1977, pp. 196-201.
Casey John
Lindner Nigel
Cook Rebecca
Unichema Chemie B.V.
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