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2,4-Dichlorobenzyl Alcohol and Amylmetacresol

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2,4-Dichlorobenzyl Alcohol and Amylmetacresol Europäisches Patentamt *EP000821584B1* (19) European Patent Office Office européen des brevets (11) EP 0 821 584 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: A61K 31/05, A61K 31/45 of the grant of the patent: // (A61K31/05, 31:045) 30.03.2005 Bulletin 2005/13 (86) International application number: (21) Application number: 96910102.1 PCT/GB1996/000928 (22) Date of filing: 18.04.1996 (87) International publication number: WO 1996/032934 (24.10.1996 Gazette 1996/47) (54) 2,4-DICHLOROBENZYL ALCOHOL AND AMYLMETACRESOL AGAINST HIV INFECTION 2,4-DICHLORBENZYLALKOHOL UND AMYLMETAKRESOL GEGEN HIV-INFEKTION UTILISATION D’ALCOOL 2,4-DICHLOROBENZYLIQUE ET D’AMYLMETACRESOL POUR LE TRAITEMENT DES INFECTIONS DUES AU VIH (84) Designated Contracting States: (56) References cited: AT BE CH DE DK ES FI FR GB GR IE IT LI LU MC EP-A- 0 427 997 DE-A- 2 333 849 NL PT SE DE-A- 4 120 296 US-A- 5 252 606 (30) Priority: 18.04.1995 GB 9507883 • S. BUDAVARI ET AL.: "THE MERCK INDEX" 1989 , MERCK & CO., INC. , RAHWAY, N.J., USA (43) Date of publication of application: XP002013317 see no. 643: "6-n-Amyl-m-cresol" 04.02.1998 Bulletin 1998/06 • "DICTIONNAIRE VIDAL" 1987 , O.V.P. , PARIS XP002013318 see page 1474 see "STREPSILS" (73) Proprietor: The Boots Company PLC • BUNDESVERB. D. PHARM. IND. E.V.: "Rote Nottingham, Nottinghamshire NG2 3AA (GB) Liste" 1987 , EDITIO CANTOR , AULENDORF/WÜRTT. XP002013319 se no. (72) Inventor: OXFORD, John, Sidney 62130: "Neo-angin" London E12AD (GB) • J.E.F. REYNOLDS ET AL.: "MARTINDALE, The Extra Pharmacopoeia" 1993 , THE (74) Representative: Frith, Richard William et al PHARMACEUTICAL PRESS , 1LONDON Appleyard Lees XP002013320 see page 785 see 15 Clare Road "Amylmetacresol" Halifax HX1 2HY (GB) • DR. W. FORTH ET AL.: "Allg. und spezielle Pharmakologie und Toxikologie" 1983 , BIBLIOGRAPHISCHES INSTITUT , MANNHEIM/WIEN/ZÜRICH XP002013321 see page 613 - page 618 see page 613 - page 615 • ZBL. BAKT. HYG., I. ABT. ORIG. B 174, 1981, pages 151-159, XP002013316 L. BRADE ET AL.: "Zur relativen Wirksamkeit von Desinfektionsmitteln gegenüber Rotaviren" & DATABASE CA SEARCH Dialog Accession no. 96082520; CA: 96(11)82520p, Remarks: The file contains technical information submitted after the application was filed and not included in this specification 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). EP 0 821 584 B1 Printed by Jouve, 75001 PARIS (FR) EP 0 821 584 B1 Description [0001] The present invention relates to the use of formulations of 2,4-dichlorobenzyl alcohol (or 2,4 DCBA) and amylmetacresol (or AMC) for the manufacture of a medicament for the treatment or prevention of Human Immunode- 5 ficiency Virus (HIV) viral infections. [0002] HIV infections are now found in every country in the world and the most important method of transmission is sexual. The virus is present as free virus particles or as intracellular virions in monocyte cells in semen. The virus is thereby transmitted relatively easily from male to female or male to male. Alternatively, in an infected female, virus either free or cell bound is found in fluid in the vagina. 10 [0003] Existing antivirals have been found which inhibit important enzymes of the virus such as reverse transcriptase (RT), protease or integrase. The first clinically used drug namely AZT (or zidovudine, Retrovir™), inhibits the virus RT enzyme. However, AZT does not represent a cure of infection and has not been demonstrated to prevent person to person spread. Indeed one of the clinical problems with the drug, apart from toxicity, is the emergence of drug resistant virus and the actual spread of the drug resistant virus in the community. A new approach against HIV is therefore to 15 search for novel compounds which may destroy or inactivate free virus and/or cell associated virus directly on contact. These are so-called virucidal compounds. Such molecules have been described in the past (Oxford et al in App. Micro- biology 21 606-610 (1971)), but have been little investigated recently. [0004] Since the HIV virion is surrounded by a lipid bilayer it would be logical to test detergent like molecules for their ability to disrupt and dissolve the lipid membrane of the virus. For example the non-ionic surfactant nonoxynol-9 has 20 been used in clinical practice as a spermicide and has direct anti-HIV activity (Malkovsky et al in The Lancet 645 (1988)). However, it has little selective anti-HIV effect and because it causes toxicity and cell destruction following application to the vagina its use may actually enhance infection with HIV (Kreiss et al in J.A.M.A. 268 477-482 (1992)). [0005] The compound 2,4 -dichlorobenzyl alcohol is known as an antiseptic agent i.e. as an antibacterial and anti- fungal agent, see for example Martindale "The Extra Pharmacopoeia" 28th edition, page 561, The Pharmaceutical 25 Press (1982) . Amylmetacresol or 6-pentyl-m-cresol is also known as a disinfectant used in mouth-washes or lozenges in combination with 2,4-dichlorobenzyl alcohol to treat mouth infections, see for example Martindale "The Extra Phar- macopoeia'' 28th edition, page 549, The Pharmaceutical Press (1982). An antiseptic is defined in The Concise Oxford Dictionary (Oxford University Press, Oxford (1982)) as an agent which counters the development of sepsis, especially by preventing the growth of bacteria. Sepsis is defined in Black's Medical Dictionary (A & C Black, London (1990)) as 30 poisoning by the products of the growth of micro-organisms in the body, and the general symptoms which accompany it are those of inflammation. Neither 2,4-dichlorobenzyl alcohol or amylmetacresol has previously been shown to dem- onstrate anti-viral or anti-retroviral activity and, in particular, anti-HIV activity. [0006] European patent application 0,427,997 A relates to coating a condom with 2,4-dichlorobenzyl alcohol which is active against the AIDS virus. 35 [0007] Unexpectedly it has now been discovered that a formulation of 2,4-dichlorobenzyl alcohol and amylmetacresol has anti-retroviral activity and causes inactivation of HIV infectivity. [0008] According to the present invention there is provided the use of a composition comprising 2,4- dichlorobenzyl alcohol and amylmetacresol in combination in an acidic sucrose base in the preparation of a medicament for the treat- ment or prevention of HIV viral infections. 40 [0009] In a particularly preferred embodiment of the present invention there is provided the use of a Strepsil™-like formulation of 2,4-dichlorobenzyl alcohol and amylmetacresol in the preparation of a medicament for the treatment or prevention of HIV viral infections. [0010] The pharmaceutical composition may be adapted for administration by any appropriate route, for example by the vaginal, rectal or oral routes. Such compositions may be prepared by any method known in the art of pharmacy, 45 for example by admixing the active ingredient with the carrier (s) or excipient (8) under sterile conditions. [0011] For the preparation of solutions and syrups used in formulating the composition, excipients which may be used include for example water, polyols and sugars. For the preparation of suspensions oils (e.g. vegetable oils) may be used to provide oil-in-water or water in oil suspensions. Other suitable excipients include for example vegetable oils, waxes, fats, semi-solid, or liquid polyols etc. 50 [0012] Alternatively the composition may be formulated as an ointment, cream, suspension, lotion, powder, solution, paste, gel, spray, aerosol or oil. When formulated in an ointment, the active ingredients may be employed with either a paraffinic or a water-miscible ointment base. The active ingredients may also be formulated in a cream with an oil- in-water cream base or a water-in-oil base. Compositions may be further prepared in which the active ingredients are dissolved or suspended in a suitable carrier, especially an aqueous solvent. 55 [0013] Pharmaceutical compositions adapted for vaginal administration may be presented as pessaries, tampons, creams, gels, pastes, foams or spray formulations. Pharmaceutical compositions adapted for rectal administration may be presented as suppositories or enemas. [0014] It also contemplated that the compositions may include anti-oxidants, buffers, bacteriostats, solutes, suspend- 2 EP 0 821 584 B1 ing agents and thickening agents. Excipients which may be used include water, alcohols, polyols, glycerine and veg- etable oils, for example. [0015] The pharmaceutical compositions may contain preserving agents, solubilising agents, stabilising agents, wet- ting agents, emulsifiers, sweeteners, colourants, odourants, salts (substances of the present invention may themselves 5 be provided in the form of a pharmaceutically acceptable salt), buffers, coating agents or antioxidants. They may also contain therapeutically active agents in addition to the substance of the present invention. [0016] Dosages of the substance of the present invention can vary between wide limits, depending upon the age and condition of the individual to be treated, etc. and a physician will ultimately determine appropriate dosages to be used. However, without being bound by any particular dosages, it is believed that, for vaginal, rectal or oral adminis- 10 tration, an effective composition in accordance with the present invention (usually present as part of a pharmaceutical composition as discussed above) may be suitable in treatments of the present invention as follows: [0017] Suitable concentration ranges for the compounds present in the composition may be as follows. 2,4-dichlo- robenzyl alcohol may be present in the composition in a concentration of from 10µg/ml to 10mg/ml, preferably of from 0.1mg/ml to 5mg/ml and particularly of from 1.0mg/ml to 5mg/ml.
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