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Use of Gamma-Linolenic Acid and Related Compounds for the Manufacture of a Medicament for the Treatment of Endometriosis

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Use of Gamma-Linolenic Acid and Related Compounds for the Manufacture of a Medicament for the Treatment of Endometriosis ~" ' MM II II II II I II Ml Ml Ml I II I II J European Patent Office ooo Ats*% n i © Publication number: 0 222 483 B1 Office_„. europeen des brevets © EUROPEAN PATENT SPECIFICATION © Date of publication of patent specification: 18.03.92 © Int. CI.5: A61 K 31/20, A61 K 31/1 6, A61K 31/23 © Application number: 86307533.9 @ Date of filing: 01.10.86 Use of gamma-linolenic acid and related compounds for the manufacture of a medicament for the treatment of endometriosis. © Priority: 02.10.85 GB 8524276 © Proprietor: EFAMOL HOLDINGS PLC Efamol House Woodbridge Meadows @ Date of publication of application: Guildford Surrey GU1 1BA(GB) 20.05.87 Bulletin 87/21 @ Inventor: Horrobin, David Frederick © Publication of the grant of the patent: c/o Efamol Ltd, Efamol House Woodbridge 18.03.92 Bulletin 92/12 Meadows Guildford, Surrey, GU1 1BA(GB) © Designated Contracting States: Inventor: Casper, Robert AT BE CH DE ES FR GB GR IT LI LU NL SE University Hospital 339 Windermere Road London Ontario N6A 5AS(CA) © References cited: EP-A- 0 003 407 EP-A- 0 115 419 © Representative: Miller, Joseph EP-A- 0 132 089 J. MILLER & CO. Lincoln House 296-302 High EP-A- 0 181 689 Holborn London WC1V 7JH(GB) J. GYNECOL. OBSTET. BIOL. REPROD. vol. 10, no. 5, 1981, pages 465-471 Masson, Paris, FR PH. CALLGARIS et al.: "Endometriose de la paroi abdominale" 00 00 CLINICAL OBSTETRICS AND GYNECOLOGY, 00 vol. 23, no. 3, Sept. 1980, pages 895-900 J.C. WEED: "Prostaglandins as related to en- CM dometriosis" CM CM Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid (Art. 99(1) European patent convention). Rank Xerox (UK) Business Services EP 0 222 483 B1 FERTILITY AND STERILITY; vol. 44, no. 2, Au- gust 1985, pages 157-173 C.L. SCHMIDT: "Endometriosis: a reappraisal of pathogene- sis and treatment" INT. J. FERTIL. vol. 30, no. 2, 1985, pages 48-52 S.Z.A. BADAWAY et al.: "Peritoneal flu- Id prostaglandins In various stages of the menstrual cycle: role In Infertile patients with endometriosis" 2 EP 0 222 483 B1 Description This invention relates to the prevent or treatment of endometriosis. The essential fatty acids (EFAs) are of two types, the n-3 (or omega-3) series derived from alpha- linolenic acid and the n-6 (or omega-6) series derived from linoleic acid. Linoleic acid and alpha-linolenic acid are like vitamins in that they cannot be manufactured in the body and therefore must be provided in the diet. The body can metabolise them along the pathways below and such metabolism is believed to be essential if they are to fulfil their functions. The pathways, sharing it is believed common enzymes, are: 10 n-6 n-3 18:2 delta-9,1 2 (linoleic acid) 18:3 de lta-9,1 2,15 (a Ipha- linolenic acid) 4- delta-6 desaturase 4 15 18:3 delta-6, 9,1 2 (gamma- li noleni c 18:4 delta-6, 9,12, 15 acid) 4- elongation 4 20 20:3 de It a-8, 11,1 4 (di homo-gamma- 20:4 de lta-8,11 ,14,17 linolenic acid) 4 delta-5 desaturase 4 20:4 delta-5,8,11,14(arachidonic 20:5 de lta-5, 8,1 1 ,1 4,17 25 acid) 4- elongation 4 22:4 delta-7,10,13,16(adrenic 22:5 de lta-7, 10,13,16,19 acid) 30 4- delta-4 desaturase 22:5 delta-4,7, 10,13,16 22:6 delta-4,7, 10, 13,16,19 35 The pathways are not normally reversible nor, in man, are n-3 and n-6 series acid interconvertible. The acids, which naturally are of the all-cis configuration, are systematically named as derivatives of the corresponding octadecanoic, eicosanoic or docosanoic acids, e.g. delta-9,1 2-octadecadienoic acid or delta- 4,7,1 0,1 3,1 6,1 9-docosahexaenoic acid, but numerical designation such as, correspondingly, 18:2 n-6 or 22:6 n-3 is convenient. Initials, for example, DHA for 22:6 n-3 (docosahexaenoic acid), are also used but do not 40 serve when n-3 and n-6 acids of the same chain length and degree of unsaturation exist. Trivial names in more or less common use in the n-6 series are as shown. Of the n-3 series only 18:3 n-3 has a commonly used trivial name, alpha-linolenic acid. It was characterised earlier than gamma-linolenic acid and reference in the literature simply to linolenic acid, especially in the earlier literature is to the alpha-acid. In the body, the n-3 acids are metabolised preferentially and as a result, in plasma for example, levels 45 of alpha-linolenic acid (18:3 n-3) are low and 18:4 n-3 and 20:4 n-3 are in trace amounts only. In contrast the n-6 acids are normally present in moderate amounts, though gamma-linolenic acid (GLA) is at low levels, being apparently converted to dihomo-gamma-linolenic acid (DGLA) more rapidly than its relatively slow production from linoleic acid. In both series the elongation stages in the metabolic pathways are much more rapid that the desaturations. 50 Particular significance of the n-6 series acids lies in prostaglandin (PG) synthesis, the outline of which is believed to be as shown in the following diagram: 55 3 EP 0 222 483 B1 cis-Linoleic Acid ( 9,12 — octadecadienoic acid) 10 GLA (6,9,12-octadecatrienoic acid) 15 DGLA I series 20 DGLA ester ; ^ (8,11, 14 -eicosatrienoic acid) endoperoxides reserves \ 25 (small) series PG's Large AA 30 AA ester =^ (Arachidonic acid i.e. reserves 5, 8, II, 14 -eicosatetraenoic acid) 35 2 series 40 endoperoxides 45 Adrenic acid 2 Series PG s 50 The broad outline of this pathway is well known, and it brings out clearly that a major function of essential fatty acids is to act as precursors for 1 -series PGs formed from DGLA and 2-series PGs formed from arachidonic acid. Further, it has recently been found that the 22:4 n-6 acid produced from arachidonic acid gives rise to a series of homo-2-series PGs, though their importance is as yet unknown. DGLA is the key substance. GLA is almost completely and very rapidly converted in the body to DLGA 55 and so for practical purposes the oral administration of DGLA and GLA amounts to the same thing. DGLA can be converted to a storage form or to PGs of the 1 -series or, through arachidonic acid, to PGs of the 2- series. Considering dietary requirements, it is well known, for example, that linoleic acid cannot be made by 4 EP 0 222 483 B1 the body and so must be taken in the diet. However, it has been generally thought that the body can metabolise linoleic acid to all the other n-6 acids and therefore that provided linoleic acid intake is adequate, no lack of the other n-6 acids will be found. In previous patent applications (for example Published European Patent Application No. A 0 003 407, 5 U.S. Patent No. 4,415,554; Published European Patent Application No. A 0 004 770, U.S. Patent No. 4 309 415; Published European Patent Application No. 0 019 423, U.S. Patent No. 4 388 324) it has, however, been pointed out that the first enzyme in the pathway, the delta-6 desaturase which, for example, converts linoleic acid to GLA, is not fully effective in a variety of conditions. The administration of GLA or DGLA or both has been suggested and has been successful in treating a variety of clinical conditions. io In the above patent applications attention is primarily paid to the function of essential fatty acids in prostaglandin metabolism and in particular to their role in securing a proper balance between 1 -series and 2-series PGs. Attention is primarily paid therefore to the n-6 acids. The applicants are, however, becoming increasingly aware of the significance of the essential fatty acids in themselves as set out above. Considerable general interest has been shown in them in recent is years, primarily in the acids of the n-6 series both as such and in relation to prostaglandin metabolism, but also in the acids of the n-3 series. The n-6 acids in particular are believed to be required in the body for the structure of membranes in and around cells, for maintaining normal flexibility, fluidity and permeability of such membranes and the n-3 acids are unlikely to have a more passive role. Endometriosis is a common condition affecting women of reproductive age. For unknown reasons, 20 endometrial tissue migrates from its normal position lining the uterus to other parts of the body, primarily within the abdominal cavity. The ovaries and gut wall are commonly affected. The endometrial tissue, like that in its normal position, grows and declines according to the menstrual cycle as a result of the actions of the ovarian hormones. Endometriosis causes many symptoms including abdominal and back pain, gastroin- testinal upsets, infertility and menstrual disturbance. Since endometrial tissue requires ovarian hormones for 25 growth, symptoms of endometriosis normally decline and disappear after menopause.
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