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United States Patent (19) 11 Patent Number: 6,117,412 Klaveness Et Al

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United States Patent (19) 11 Patent Number: 6,117,412 Klaveness Et Al USOO6117412A United States Patent (19) 11 Patent Number: 6,117,412 Klaveness et al. (45) Date of Patent: *Sep. 12, 2000 54) NON-CLUSTER TYPE BISMUTH 5,417,958 5/1995 Deutsch et al. ........................ 424/9.42 COMPOUNDS 5,482,669 1/1996 Shah. 5,482,700 1/1996 Deutsch et al.. 75 Inventors: Jo Klaveness, Oslo; Ame Berg, 5,730,953 3/1998 Suzuki et al. .......................... 424/9.42 Sandvika, both of Norway; Torsten 5,817,289 10/1998 Klaveness et al. .................... 424/1.11 Almen, Falstorbo, Sweden; Klaes FOREIGN PATENT DOCUMENTS Golman, Rungsted Kyst, Denmark; 809388 5/1974 Belgium. Michael Droege, Livermore; Shi-bao O O217 577 Yu, Campbell, both of Calif. A2 9/1986 European Pat. Off.. O 230 893 A2 1/1987 European Pat. Off.. 73 Assignee: Nycomed Imaging AS, Norway O 445 743 A2 9/1991 European Pat. Off.. 0 480 691 A2 4/1992 European Pat. Off.. * Notice: This patent is Subject to a terminal dis O OS33 281 claimer. A1 9/1992 European Pat. Off.. 0 716 091 A1 8/1994 European Pat. Off.. 21 Appl. No.: 08/875,305 2216725 10/1973 Germany. 63-225381 9/1988 Japan. 22 PCT Filed: Jan. 26, 1996 81/7456 4/1983 South Africa. 86 PCT No.: PCT/GB9600183 1003685 9/1965 United Kingdom. 1341331 12/1973 United Kingdom. S371 Date: Oct. 22, 1997 2 248 185 1/1992 United Kingdom. 2 262 036 6/1993 United Kingdom. S 102(e) Date: Oct. 22, 1997 WO 89/00557 1/1989 WIPO. WO 89/03219 4/1989 WIPO. 87 PCT Pub. No.: WO96/22994 WO 91/03241 3/1991 WIPO. PCT Pub. Date: Aug. 1, 1996 WO 92/O1457 2/1992 WIPO. WO 92/17215 10/1992 WIPO. Related U.S. Application Data WO 93/02713 2/1993 WIPO. WO95/06053 3/1995 WIPO. 63 Continuation-in-part of application No. 08/.486,225, Jun. 7, WO 96/16677 6/1996 WIPO. 1995, Pat. No. 5,817,289. WO 96/16678 6/1996 WIPO. 30 Foreign Application Priority Data OTHER PUBLICATIONS Jan. 26, 1995 GB United Kingdom ................... 95O1560 Ashana, A., “Reactions of triphenyl antimony, bismuth and their dibromides with pentacholorophenol and pentachlo 51 Int. Cl." ........................... A61K 51/00; A61M 36/14 rothiophenol”, Chemical Abstracts, OrganometallicS Vol. 52 U.S. Cl. ......................... 424/1.11; 424/1.65; 424/9.1; 121, 1994, 157769. 424/9.3; 424/9.4; 556/30 Sharutin et al., “Reactions of Vanadocene and Cobaltocene 58 Field of Search ................................... 424/1.11, 1.37, with Dichlorotriphenyl-Antimony and with Dichlorotriph 424/1.65, 1.81, 1.85, 9.1, 9.3, 9.36, 9.4, enylbismuth', J. of General Chem., USSR, vol. 61, No. 9.42, 9.44, 9.45, 9.451, 95; 534/10-16: 6–1357–1359, Jun. 1991. 556/1, 28, 30, 64, 70, 71, 76 Suzuki et al., “Ultrasonic Reaction of Triarylbismuthines and Trarylstibines with Iodosylbenzene.”, Tetrahedron Let 56) References Cited ters, vol. 35, No. 44, pp. 8197-8200, 1994. U.S. PATENT DOCUMENTS Primary Examiner Jose' G. Dees ASSistant Examiner-Dameron Jones 3.239,411 3/1966 Leebrick. 3.247,050 4/1966 Leebrick. Attorney, Agent, or Firm Fish & Richardson P.C. 3,466,366 9/1969 Leebrick. 57 ABSTRACT 3,753,990 8/1973 Curry. 3,824,307 7/1974 Curry. A method of generating an image of a human or non-human 4,153,685 5/1979 Serfontein. animal body which comprises administering to Said body a 4,588,589 5/1986 Sheth et al.. physiologically tolerable contrast enhancing amount of a 4,647,447 3/1987 Gries et al.. 4,652,519 3/1987 Warshawsky et al.. non-cluster type bismuth compound, and methods of treat 4,687,659 8/1987 Quay. ing gastrointestinal disorders using the Same. Diagnostic 4,826,673 5/1989 Dean et al.. imaging contrast media comprising non-cluster type bis 5,008.256 4/1991 Clitherow. muth compounds are also disclosed, together with novel 5,013,560 5/1991 Stentz et al.. covalent non-cluster type bismuth compounds. 5,229,418 7/1993 Collington et al. 5,273,984 12/1993 Clitherow. 15 Claims, No Drawings 6,117,412 1 2 NON-CLUSTER TYPE BISMUTH The most frequently used bismuth compounds as gas COMPOUNDS trointestinal drugs today are bismuth Subnitrate and bismuth Subsalicylate. Bismuth Subnitrate or bismuth hydroxide This is a 371 of International Patent Application No. nitrate oxide (BiO(OH)(NO) is prepared by hydrolysis PCT/GB96/00183, with an international filing date of Jan. 5 of bismuth nitrate and is practically insoluble in water. It is 26, 1996, now pending, which is a continuation-in-part of usually used as a Suspension (milk of bismuth). Bismuth Subnitrate is also used topically in lotions and ointments. U.S. Ser. No. 08/486,225 filed Jun. 7, 1995, now U.S. Pat. Bismuth subsalicylate or basic bismuth salicylate No. 5,817,289, which all claim priority from Great Britain (C7HBiO) is also practically insoluble in water and is 9501560.8, filed Jan. 26, 1995. administered as a Suspension or in the form of tablets. The present invention relates to the use in diagnostic Products containing bismuth Subsalicylate are used against imaging, in particular X-ray, MRI, ultrasound and indigestion, nausea and diarrhea. AS an antidiarrheal agent it Scintigraphy, of contrast agents comprising bismuth clusters shows good activity against Salmonella with less activity and/or organic bismuth compounds, and to contrast media versus E. coli. containing Such bismuth compounds. Another aspect of the Several bismuth compounds are known to be biologi present invention is the use of the bismuth compounds in 15 cally active and have been Suggested as active ingredients in therapy, in particular as antiulcer agents. various drug formulations. Organobismuth compounds can All diagnostic imaging is based on the achievement of be used as antibacterial agents, for example against infec different signal levels from different structures within the tions caused by highly resistant gram-negative bacteria (U.S. body. Thus in X-ray imaging, for example, for a given body Pat. No. 3,466,366 of M&T Chem Inc); a protein-type Structure to be visible in the image the X-ray attenuation by bismuth complex is Suggested for treatment of inflammation that structure must differ from that of the surrounding and infections in the gastrointestinal system in U.S. Pat. No. tissues. The difference in Signal between the body Structure 4,153,685 (Schering Corp); bismuthyl prostanoate deriva and its Surroundings is frequently termed contrast and much tives for ulcer control are suggested in BE 809388 (Aries R); effort has been devoted to means of enhancing contrast in phenylbismuth bis(2-pyridinethiol) 1-oxide as an antibacte diagnostic imaging Since the greater the contrast between a 25 rial and antifungal agent is disclosed in U.S. Pat. No. body Structure and its Surroundings the higher the quality of 3,824.307 (Procter & Gamble Co); an antiinflammatory and the images and the greater their value to the physician antiulcer bismuth composition containing a mixture of triva performing the diagnosis. Moreover, the greater the contrast lent bismuth, water-Soluble protein, an organic acid anion the smaller the body structures that may be visualized in the and an alkali in ZA 8107456 (Schering Corp); bismuth imaging procedure, i.e. increased contrast can lead to Subsalicylate in combination with other agents in a Syner increased spatial resolution. gistic formulation for diarrhoea treatment in U.S. Pat. No. The diagnostic quality of imageS is strongly dependent 4.588,589 (Richardson Vicks); treatment of non-ulcer dys on the inherent noise level in the imaging procedure—the pepsia associated with Campylobacter pyloridis infection ratio of the contrast level to the noise level can thus be seen with bismuth Salts. Such as tripotassium dicitrato-bismuthate to represent an effective diagnostic quality factor for diag 35 in WO 89/03219 (Borody T.J.); organo-bismuth compounds nostic images. useful as anti-coccidium agents for poultry; and as insecti Achieving improvement in Such a diagnostic quality cides in J63225391 (Nitto Kasei and Shionogi); pharmaceu factor has long been and Still remains an important goal. In tical compositions for treatment of gastrointestinal disorders techniques Such as X-ray and ultrasound, one approach to asSociated with Campylobacter pylori infections comprising improve the diagnostic quality factor has been to introduce 40 a pharmaceutically acceptable bismuth compound and first contrast enhancing materials, contrast agents, into the body and second antibiotic or antimicrobial agents in EP 439453 region being imaged. (Capability Services et al.); salts formed between rantidine Thus in X-ray, for instance, early examples of contrast and bismuth carboxylic acid complexes for treatment of agents were insoluble inorganic barium Salts which gastrointestinal disorders in U.S. Pat. No. 5,008,256 enhanced X-ray attenuation in the body Zones into which 45 (Glaxo); further salts formed between an H-receptor they distributed. More recently the field of X-ray contrast antagonist and a complex of bismuth with a carboxylic acid agents has been dominated by Soluble iodine containing with activity against gastrointestinal conditions and against compounds Such as those markedet by Nycomed AS under Campylobacter pylori in U.S. Pat. No. 5,273,984 (Glaxo); a the trade names Omnipaque(E) and Visipaque(R). Suspension for oral administration comprising a bismuth Much recent work on X-ray contrast agents has concen 50 containing pharmaceutical agent, benzoic acid and Sorbic trated on aminopolycarboxylic acid (APCA) chelates of acid, polymer and water for use against various gastrointes heavy metal ions and, recognising that effective imaging of tinal disorders in U.S. Pat.
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