Derivatives of 4- or 5-aminosalicylic acid

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Acyclic nitrogen double bonded to acyclic nitrogen – acyclic...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C514S163000, C514S165000, C562S439000, C562S453000

Reexamination Certificate

active

07879827

ABSTRACT:
The present invention provides new derivatives of 4- or 5-aminosalicylic acid, and a pharmaceutical composition containing these derivatives of 4- or 5-aminosalicylic acid as active ingredients, useful for the treatment of intestinal diseases such as inflammatory bowel disease (IBD) and irritable bowel syndrome (IBS) and for the prevention/treatment of colon cancer. More particularly, these derivatives comprise a hydrogen sulfide releasing moiety linked via an azo, an ester, an anhydride, a thioester or an amide linkage to a molecule of 4- or 5-aminosalicylic acid. Furthermore, the present invention provides a process for preparing these compounds and their use for treating IBD and IBS and the prevention/treatment of colon cancer.

REFERENCES:
patent: 4412992 (1983-11-01), Chan et al.
patent: 4440763 (1984-04-01), Lover
patent: 5013727 (1991-05-01), Halskov
patent: 6197341 (2001-03-01), Freiss et al.
patent: 6458776 (2002-10-01), Ekwuribe et al.
patent: 6602915 (2003-08-01), Uhrich et al.
patent: 2204747 (1997-03-01), None
patent: WO 2005/072113 (2005-08-01), None
patent: WO 2006/037623 (2006-04-01), None
patent: WO 2006/066894 (2006-06-01), None
Pellicciari, et al., “Brush-Border-Enzyme-Mediated Intestine-Specific Drug Delivery, Amino Acid Prodrugs of 5-Aminosalicylic Acid”, J. Med. Chem, 1993, vol. 36, pp. 4201-4207.
Distrutti, et al., “Evidence That Hydrogen Sulfide Exerts Antinocicieptive Effects in the Gastrointestinal Tract by Activating KATP Channels”, J. Pharm. and Exp. Ther., 2005, vol. 316, pp. 325-335.
Teague, et al., “The Smooth Muscle Relaxant Effect of Hydrogen Sulfide In Vitro: Evidence for a Physiological Role to Control Intestinal Contractility”, Br. J. Pharmacol, vol. 137, pp. 139-145.
Dzierzewicz, et al., “Susceptibility of Desulfovibrio desulfuuricans intestinal strains to sulfasalazine and its biotransformation products”, Med. Sci. Monit, 2004, vol. 10, No. 6, BR185-190.
Edmond, et al., “The effect of 5-aminosalicylic acid-containing drugs on sulfide production by sulfate-reducing bacteria and amino acid-fermenting bacteria”, Inflammatory Bowel Diseases, 2003, vol. 9, No. 1, pp. 10-17.
Fiorucci, et al., :Inhibition of Hydrogen Sulfide Generation Contributes to Gastric Injury Caused by Anti-Inflammmatory Nonsteroidal Drugs, Gastroenterology, Oct. 2005, vol. 129, No. 4, pp. 1210-1224.
Sidhu, et al., “L-Cysteine and Sodium Hydrogensulfide Inhibit Spontaneous Contractibility in Isolaged Pregnant Rat Uterine Strips in Vivo”, Pharmacology & Toxicology, 2001, vol. 88, pp. 198-203.
Zhao, et al., “The vasorelaxant effect of H2S as a novel endogenous gaseous KATP channel opener”, EMBO Journal, 2001, vol. 2, No. 21, pp. 6008-6016.
Zhao, et al., “H2S-Induced vasolrelaxation and underlying cellular and molecular mechanisms”, Am. J. Physiol. Heart Circ. Physiol., 2002, vol. 283: H474-480.
Abe, et al., “The possible role of hydrogen sulfide as an endogenous neuromodulator”, The Journal of Neuroscience, 1996, vol. 16, No. 3, pp. 1066-1071.
Carceller, et al., “Novel Azo derivatives as prodrugs of 5-aminosalicylic acid and amino derivatives with potent platelet activating factor antagonist activity”, J. Med. Chem., 2001, vol. 44, No. 18, pp. 3001-3013.
M C L Pitcher, et al., “The contribution of sulphate reducing bacteria and 5-aminosalicylic acid to faecal sulphide in patients with ulcerative colitis”, Gut 2000, vol. 46, pp. 64 through 72.
Xu, Xi-Ming, et al., “Effects of garlicin on apoptosis in rat model of colitis”, World J Gastoenterol, Aug. 7, 2005, vol. 11, No. 29, pp. 4579 through 4582.
Galvez, Julio, et al., “Intestinal anti-inflammatory activity of UR-12746, a novel 5-ASA conjugate, on acute and chronic experimental colitis in the rat”, British Journal of Pharmacology, 2000, vol. 130, No. 8, pp. 1949 through 1959.
Wahl, Christian, et al., “Sulfasalazine: a Potent and Specific Inhibitor of Nuclear Factor Kappa B”, The American Society for Clinical Investigation, Inc., vol. 101, No. 5, Mar. 1998, pp. 1163 through 1174.
Bai, Ai-Ping, et al., “Diallyl Trisulfide Inhibits Tumor Necrosis Factor-α Expression in Inflammed Mucosa of Ulcerative Colitis”, Digestive Diseases and Sciences, vol. 50, No. 8, Aug. 2005, pp. 1426 through 1431.
Li, Ling, et al., “Hydrogen sulphide—a novel mediator of inflammation?”, Current Opinion in Pharmacology 2006, No. 6, pp. 125 through 129.
Ohge, Hiroki, et al., “Association Between Fecal Hydrogen Sulfide Production and Pouchitis”, Dis Colon Rectum, Mar. 2005, vol. 48, No. 3, pp. 469 through 475.
Schmedes, Anne, et al., “Low S-adenosylmethionine concentrations found in patients with sever inflammatory bowel disease”, Clin Chem Lab Med, 2004, vol. 42, No. 6, pp. 648 through 653.
Wang, Rui, “Two's company, three's a crowd: can H2S be the third endogenous gaseous transmitter?”, the FASEB Journal, vol. 16, Nov. 2002, pp. 1792 through 1798.
Aharonowitz et al. Journal of Bacteriology, vol. 175, 1993, p. 623-629.
Google search results under term “hydrogen sulfide relseasing moiety” (in part).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Derivatives of 4- or 5-aminosalicylic acid does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Derivatives of 4- or 5-aminosalicylic acid, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Derivatives of 4- or 5-aminosalicylic acid will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2631375

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.