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Use of Bismuth Compounds for the Manufacture of Medicaments for The Europäisches Patentamt *EP000805815B1* (19) European Patent Office Office européen des brevets (11) EP 0 805 815 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: A61K 33/24, C07F 9/94, of the grant of the patent: A61K 49/04 10.04.2002 Bulletin 2002/15 (86) International application number: (21) Application number: 96901066.9 PCT/GB96/00183 (22) Date of filing: 26.01.1996 (87) International publication number: WO 96/22994 (01.08.1996 Gazette 1996/35) (54) Use of bismuth compounds for the manufacture of medicaments for the treatment of gastric disorders caused by Helicobacter pylori Verwendung von WISMUTVERBINDUNGEN zur Herstellung eines Arzneimittels zur Behandlung von Magenverstimmungen, die durch Helicobacter pylori verursacht werden Utilisation de COMPOSES DE BISMUTH pour la fabrication de médicaments pour le traitement de troubles gastriques associées avec Helicobacter pylori (84) Designated Contracting States: EP-A- 0 480 691 EP-A- 0 716 091 DE DK ES FR GB IE IT SE WO-A-91/03241 WO-A-93/02713 WO-A-95/06053 WO-A-96/16677 (30) Priority: 26.01.1995 GB 9501560 WO-A-96/16678 BE-A- 782 105 07.06.1995 US 486225 DE-A- 2 216 725 (43) Date of publication of application: • TETRAHEDRON LETT. (TELEAY,00404039);94; 12.11.1997 Bulletin 1997/46 VOL.35 (44); PP.8197-200, KYOTO UNIV.;FAC. SCI.; KYOTO; 606-01; JAPAN (JP), SUZUKI H ET (73) Proprietor: NYCOMED IMAGING A/S AL ’Ultrasonic reaction of triarylbismuthines 0401 Oslo (NO) and triarylstibines with iodosylbenzene. Mild oxidizing ability of the organobismuth oxide (72) Inventors: function for organic substrates’ • KLAVENESS, Jo • DATABASE CHEMABS CHEMICAL ABSTRACTS N-1166 Oslo (NO) SERVICE, COLUMBUS, OHIO, US ASTHANA A • BERG, Arne ’Reactions of triphenyl antimony, bismuth and N-1300 Sandvika (NO) their dibromides with pentachlorophenol and • ALMEN, Torsten pentachlorothiophenol’ & INDIAN J. CHEM., S-239 40 Falsterbo (SE) SECT. A: INORG., BIO-INORG., PHYS., THEOR. • GOLMAN, Klaes ANAL. CHEM. (ICACEC,03764710);94; VOL.33A DK-2960 Rungsted Kyst (DK) (7); PP.687-8, UNIV. LUCKNOW;DEP. CHEM.; • DROEGE, Michael LUCKNOW; INDIA (IN), Livermore, CA 94550 (US) • ZH. OBSHCH. KHIM. (ZOKHA4,0044460X);91; • YU, Shi-bao VOL.61 (6); PP.1357-9, BLAGOVESHCHENSK. Campbell, CA 95008 (US) TEKHNOL. INST.;BLAGOVESHCHENSK; USSR (SU), SHARUTIN V V ET AL ’Reactions of (74) Representative: Matthews, Derek Peter vanadocene and cobaltocene with Frank B. Dehn & Co., triphenylantimony dichloride and European Patent Attorneys, triphenylbismuth dichloride’ 179 Queen Victoria Street • Scand. J. Gastroenterol 1999 (2), pp. 135-137: London EC4V 4EL (GB) Dahlgren,A. et al. "Organobismuth Compounds: Activity against Helicobacter Pylori" (56) References cited: 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 0 805 815 B1 Printed by Jouve, 75001 PARIS (FR) EP 0 805 815 B1 Description [0001] The present invention relates to the use of bismuth compounds in therapy, in particular as antiulcer agents. [0002] Bismuth compounds have a long history in therapeutic medicine specially in treatment of gastrointestinal 5 diseases such as ulcers. Although antiulcer agents such as the H2-antagonists cimetidine and ranitidine, and more recently proton pump inhibitors such as omeprazole, have been developed, there is still medical use of bismuth com- pounds in ulcer treatment. [0003] The most frequently used bismuth compounds as gastrointestinal drugs today are bismuth subnitrate and bismuth subsalicylate. Bismuth subnitrate or bismuth hydroxide nitrate oxide (Bi5O(OH)9(NO3)4 is prepared by hydrol- 10 ysis of bismuth nitrate and is practically insoluble in water. It is usually used as a suspension (milk of bismuth). Bismuth subnitrate is also used topically in lotions and ointments. Bismuth subsalicylate or basic bismuth salicylate (C7H5BiO4) is also practically insoluble in water and is administered as a suspension or in the form of tablets. Products containing bismuth subsalicylate are used against indigestion, nausea and diarrhea. As an antidiarrheal agent it shows good activity against Salmonella with less activity versus E. coli. 15 [0004] Several bismuth compounds are known to be biologically active and have been suggested as active ingredi- ents in various drug formulations. For example, WO-A-91/03241 describes Bi2O3 and its use in medicaments for the treatment of ulcers, whilst EP-A-445743 discloses Bi-chelates of azitromycin and its use in medicaments for the erad- ication of Helicobacter pylori. Organobismuth compounds can be used as antibacterial agents, for example against infections caused by highly resistant gram-negative bacteria (US 3,466,366 of M&T Chem Inc); a protein-type bismuth 20 complex is suggested for treatment of inflammation and infections in the gastrointestinal system in US 4,153,685 (Schering Corp); bismuthyl prostanoate derivatives for ulcer control are suggested in BE 809388 (Aries R); phenylbis- muth bis(2-pyridinethiol) 1-oxide as an antibacterial and antifungal agent is disclosed in US 3,824,307 (Procter & Gam- ble Co); an antiinflammatory and antiulcer bismuth composition containing a mixture of trivalent bismuth, water-soluble protein, an organic acid anion and an alkali in ZA 8107456 (Schering Corp); bismuth subsalicylate in combination with 25 other agents in a synergistic formulation for diarrhoea treatment in US 4,588,589 (Richardson Vicks); treatment of non- ulcer dyspepsia associated with Campylobacter pyloridis infection with bismuth salts such as tripotassium dicitrato- bismuthate in WO 89/03219 (Borody T.J.); organo-bismuth compounds useful as anti-coccidium agents for poultry, and as insecticides in J63225391 (Nitto Kasei and Shionogi); pharmaceutical compositions for treatment of gastroin- testinal disorders associated with Campylobacter pylori infections comprising a pharmaceutically acceptable bismuth 30 compound and first and second antibiotic or antimicrobial agents in EP 439453 (Capability Services et al.); salts formed between ranitidine and bismuth carboxylic acid complexes for treatment of gastrointestinal disorders in US 5,008,256 (Glaxo); further salts formed between an H2-receptor antagonist and a complex of bismuth with a carboxylic acid with activity against gastrointestinal conditions and against Campylobacter pylori in US 5,273,984 (Glaxo); a suspension for oral administration comprising a bismuth-containing pharmaceutical agent, benzoic acid and sorbic acid, polymer 35 and water for use against various gastrointestinal disorders in US 5,013,560 (Procter & Gamble); furan derivatives with bismuth carboxylic acid complexes for treatment of various gastrointestinal disorders including activity against Helio- bacter pylori in US 5,229,418 (Glaxo); bismuth polyacrylate complexes for treating gastrointestinal disorders like in- flammatory bowel disease or Heliobacter pylori infections in WO 92/01457 (Evans B. K. et al.); salts of ranitidine with a bismuth carboxylate complex and alkali salt for treatment of various gastrointestinal disorders in GB 2248185 (Glaxo); 40 use of rantidine bismuth citrate and antibiotics to inhibit Heliobacter pylori in EP 533281 (Glaxo); and ranitidine bismuth citrate and non-steroidal anti-inflammatory drugs for the treatment of inflammation diseases in GB 2262036 (Glaxo). We have now found that certain bismuth compounds can be used in the treatment of various gastrointestinal disorders. [0005] The invention provides the use of a physiologically tolerable compound of formula I, 45 50 55 where the groups R1-R3 may be the same or different and are defined as any group forming a hydrolytically stable 2 EP 0 805 815 B1 bond to bismuth, for the manufacture of a therapeutic agent for treatment of gastrointestinal disorders caused by Heli- cobacter pylori. Typical R1-3 groups are preferably aryl groups. [0006] In formula I above, R1-R3 may be the same or different and may be any group forming a hydrolytically stable bond to bismuth. Typical R1-R3 groups can for example be aryl groups. 5 [0007] The bond from bismuth to one of the R1-3 groups may for example be of the following types: Bi-C, Bi-O, Bi- S and Bi-N. Some of these bonds are more stable than others and it is known in the literature on the chemistry of bismuth that the stability of the bismuth molecule is very dependent on the chemical nature of this bond and the sub- stituents (see for example Chapter 28 in G. Wilkinson (ed) Comprehensive Coordination Chemistry; Gmelin Handbuch der Anorganischen Chemie Volume 47; L.D. Freedman and G. O. Doak in Chem. Rev (1982) 82 15-57; Methoden der 10 Organischen Chemie (Houben-Weyl) Volume XIII/8; Comprehensive Organometallic Chemistry, Chapter 13; Kirk-Oth- mer: Encyclopedia of Chemical Technology Volume 3 p 921-936). [0008] Some trialkylbismuth compounds are known to be very hydrolytically unstable, however, we have shown that triarylbismuth compounds are surprisingly stable against hydrolysis: triphenylbismuth dissolved in aqueous (25%) tet- rahydrofuran is stable under reflux for many days. When the R1-3-groups form Bi-C bonds, aryl groups are generally 15 preferred. At least one of the R1-5-groups should be an aryl group or substituted aryl group. The term "aryl group" here means
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