Organic compounds -- part of the class 532-570 series – Organic compounds – Hydroxamic acids – chalcogen analogs or salts thereof
Reexamination Certificate
2005-05-03
2005-05-03
Killos, Paul J. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Hydroxamic acids, chalcogen analogs or salts thereof
C558S048000, C558S061000, C514S575000
Reexamination Certificate
active
06888027
ABSTRACT:
This invention pertains to certain active carbamic acid compounds which inhibit HDAC activity and which have the following formula: (I) A is an aryl group; Q1is a covalent bond or an aryl leader group; J is a sulfonamide linkage selected from: —S(═O)2NR1— and —NR1S(═O)2—; R1 is a sulfonamido substituent; and, Q2is an acid leader group; with the proviso that if J is —S(═O)2NR1—, then Q1is an aryl leader group; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC, and, e.g., to inhibit proliferative conditions, such as cancer and psoriasis.
REFERENCES:
patent: 5369108 (1994-11-01), Breslow
patent: 5700811 (1997-12-01), Breslow
patent: 5804601 (1998-09-01), Kato
patent: 5834249 (1998-11-01), Furukawa
patent: 6541661 (2003-04-01), Delorme et al.
patent: 0 301 861 (1989-02-01), None
patent: 0 570 594 (1993-11-01), None
patent: 0 827 742 (1998-03-01), None
patent: 0 931 788 (1999-07-01), None
patent: 2 312 674 (1997-11-01), None
patent: 10-114681 (1998-05-01), None
patent: 10-182583 (1998-07-01), None
patent: WO 9312075 (1993-06-01), None
patent: WO 9531977 (1995-11-01), None
patent: 9838859 (1998-09-01), None
patent: WO 9855449 (1998-12-01), None
patent: 9924399 (1999-05-01), None
patent: 0056704 (2000-09-01), None
patent: 0069819 (2000-11-01), None
patent: WO 0118171 (2001-03-01), None
patent: WO 0138322 (2001-05-01), None
patent: 0138322 (2001-05-01), None
patent: WO 0138322 (2001-05-01), None
Kim et al; “Oxamflation is a Novel Antitumor Compounds that Inhibits Mammalian Histone Deacetylase”; Chemical Abstracts+Indexes, American Chemical Society, Columbus, US, vol. 131, No. 8, Aug. 23, 1999, XP002162155.
Barlaam et al; “New Hydroxylamines for the synthesis of Hydroxamic Acids”; Tetrahedron Letters, Elsevier Science Publishers, Amsterdam, NL, vol. 39, No. 43, Oct. 22, 1998, pp. 7865-7868, XP004137828.
Decicco et al; “Amide Surrogates of Matrix Metalloproteinase Inhibitors: Urea and Sulfonamide Mimics”; Bioorganic & Medicinal Chemistry Letters, Oxford, GB, vol. 7, No. 18, Sep. 23, 1997, pp. 2331-2336, XP004136439.
Andrews et al., 2000, “Anti-malarial effect of histone deacetylation inhibitors and mammalian tumour cytodifferentiating agents”Int. J. Parasitol., vol. 30, No. 6, pp. 761-768.
Bernhard, D. et al., 1999, “Apoptosis induced by the histone deacetylase inhibitor sodium butyrate in human leukemic lymphoblasts,” FASEB J., vol. 13, No. 14, pp. 1991-2001.
Bernstein et al., 2000,“Genomewide studies of histone deacetylase function in yeast”Proc. Natl. Acad. Sci. USA, vol. 97, No. 25, pp. 13708-13713.
Brehm, A., et al., 1998, “Retinoblastoma protein recruits histone deacetylase to repress transcription,”Nature, 1998, vol. 391, pp. 597-601.
Chang et al., 2000,“Activation of the BRLF1 promoter and lytic cycle of Epstein-Barr virus by histone acetylation.”Nucleic Acids. Res., vol. 28, No. 20, pp. 3918-3925.
Dangond et al., 1998, “Differential display cloning of a novel human histone deacetylase (HDAC3) cDNA from PHA-activated immune cells,”Biochem. Biophys. Res. Commun., vol. 242, No. 3, pp. 648-652.
David, G., et al., 1998, “Histone deacetylase associated with mSin3A mediates repression by the acute promyelocytic leukaemia-associated PLZF protein,”Oncogene, vol. 16(19), pp. 2549-2556.
Davie, J.R., 1998, “Covalent modifications of histones: expression from chromatic templates,”Curr. Opin. Genet. Dev., vol. 8, pp. 173-178.
Desai, D et al., 1999, “Chemopreventive efficacy of suberanilohydroxamic acid (SAHA), a cytodifferentiating agent, against tobacco-specific nitrosamine 4-(-methylnitros-amino)-1-(3-pyridyl)-1-butanone (NNK)-induced lung tumorigenesis in female A/J mice,”Proc. AACR, vol. 40, abstract #2396.
Emiliani, S., et al., 1998, “Characterization of a human RPD3 ortholog, HDAC3,”Proc. Natl. Acad. Sci. USA, vol. 95, pp. 2795-2800.
Finnin et al., 1999, “Structures of a histone deacetylase homologue bound to the TSA and SAHA inhibitors”Nature, vol. 401, pp. 188-193.
Glick, R.D., et al., 1999, “Hybrid polar histone deacetylase inhibitor induces apoptosis and CD95/CD95 ligand expression in human neuroblastoma,”Cancer Research, vol. 59, No. 17, pp. 4392-4399.
Grozinger et al., 1999, “Three proteins define a class of human histone deacetylases related to yeast Hda1p”Proc. Natl. Acad. Sci. USA, vol. 96, pp. 4868-4873.
Hoshikawa, Y., et al., 1994, “Trichostatin A induces morphological changes and gelsolin expression by inhibiting histone deacetylase in human carcinoma cell lines,”Exp. Cell. Res., vol. 214(1), pp. 189-197.
Howe, L., et al., 1999, “Histone acetyltransferase complexes and their link to transcription”Crit. Rev. Eukaryot. Gene Expr., vol. 9(3-4), pp. 231-243.
Iavarone et al., 1999, “E2F and histone deacetylase mediate transforming growth factor beta repression of cdc25A during keratinocyte cell cycle arrest”,Mol. Cell. Biol., vol. 19, No. 1, pp. 916-922.
Jung et al., 1997, “Analogues of trichostatin A and trapoxin B as histone deacetylase inhibitors”Bioorg. Med. Chem. Lett., vol. 7, No. 13, pp. 1655-1658.
Jung et al., 1999, “Amide analogues of trichostatin A as inhibitors of histone deacetylase and inducers of terminal cell differentiation”J. Med. Chem., vol. 42, pp. 4669-4679.
Kao et al., 2000, “Isolation of a novel histone deacetylase reveals that class I and class II deacetylases promote SMRT-mediated repression”Genes Dev., vol. 14, pp. 55-66.
Kijima et al., 1993, Trapoxin, an antitumor cyclic tetrapeptide, is an irreversible inhibitor of mammalian histone deacetylasesJ. Biol. Chem., vol. 268, pp. 22429-22435.
Kim et al., 1999, “Oxamflatin is a novel antitumor compound that inhibits mammalian histone deacetylase”Oncogene, vol. 18(15), pp. 2461-2470.
Kim, M.S., et al., 2001 “Histone deacetytlases induce angiogenesis by negative regulation of tumour suppressor genes,”Nature Medicine, vol. 7, No. 4 pp. 437-443.
Kimura et al., 1994, “Dual modes of action of platelet-derived growth factor and its inhibition by trichostatin-A for DNA synthesis in primary cultured smooth muscle cells of rat aorta”,Biol. Pharm. Bull., vol. 17, No. 3, pp. 399-402.
Kitamura, K., et al., 2000, “Histone deacetylase inhibitor but not arsenic trioxide differentiates acute promyelocytic leukaemia cells with t(11:17) in combination with all-trans retinoic acid”Br. J. Haematol., vol. 108(4), pp. 696-702.
Kouzarides, T., 1999, “Histone acetylases and deacetylases in cell proliferation,”Curr. Opin. Genet. Dev., vol. 9, No. 1, pp. 40-48.
Kuusisto et al., 2001, “Ubiquitin-binding protein p62 expression is induced during apoptosis and proteasomal inhibition in neuronal cells,”Biochem. Biophys. Res. Commun., vol. 280, No. 1, pp. 223-228.
Kwon et al., 1998, “Depudecin induces morphological reversion of transformed fibroblasts via the inhibition of histone deacetylase”Proc. Natl. Acad. Sci. USA, vol. 95, pp. 3356-3361.
Laherty, C.D., et al., 1997, Histone deacetylases associated with the mSin3 corepressor mediate mad transcriptional repressionCell, vol. 89(3), pp. 349-356.
Lea et al., 1999, “Increased acetylation of histones induced by diallyl disulfide and structurally related molecules”Int. J. Oncol., vol. 2, pp. 347-352.
Lin, R.J., et al., 1998, “Role of the histone deacetylase complex in acute promyelocytic leukaemia”Nature, vol. 391(6669), pp. 811-814.
Massa et al., 2001,J. Med. Chem., “3-(4-aroyl-1H-pyrrol-2-yl)-N-hydroxy-2-propenamides, a new class of synth
Andrianov Victor
Dikovska Klara
Duffy James E. S.
Finn Paul W
Gailite Vija
Killos Paul J.
Nixon & Vanderhye P.C.
Topotarget UK Limited
LandOfFree
Carbamic acid compounds comprising a sulfonamide linkage as... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Carbamic acid compounds comprising a sulfonamide linkage as..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Carbamic acid compounds comprising a sulfonamide linkage as... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3429831