Carbamic acid compounds comprising an ether linkage as HDAC...

Organic compounds -- part of the class 532-570 series – Organic compounds – Hydroxamic acids – chalcogen analogs or salts thereof

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C514S575000, C562S621000

Reexamination Certificate

active

06960685

ABSTRACT:
This invention pertains to certain active carbamic acid compounds which inhibit HDAC activity and which have the following formula:wherein: A is an aryl group; Q1is a covalent bond or an aryl leader group; J is an amide linkage selected from: —NR1C(═O)— and —C(═O)NR1—; R1is an amido substituent; X is an ether heteroatom, and is —O— or —S—; and, R2and R3are each independently an ether 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: 0 301 861 (1989-02-01), None
patent: 0 827 742 (1998-03-01), None
patent: 1 571 198 (1969-06-01), None
patent: 6122671 (1994-05-01), None
patent: 10-114681 (1998-05-01), None
patent: 10-182583 (1998-07-01), None
patent: 11 130761 (1999-05-01), None
patent: WO 93/12075 (1993-06-01), None
patent: 9410990 (1994-05-01), None
patent: 9505358 (1995-02-01), None
patent: WO 95/31977 (1995-11-01), None
patent: 9742217 (1997-11-01), None
patent: WO 98/55449 (1998-12-01), None
patent: 9905109 (1999-02-01), None
patent: 9911606 (1999-03-01), None
patent: 9919296 (1999-04-01), None
patent: 0000194 94 (2000-04-01), None
patent: WO 01/18171 (2001-03-01), None
patent: WO 01/38322 (2001-05-01), None
Database CA 'Online!, Chemical Abstracts Service, Columbus, Ohio, US; Mori, Toyoki et al; “Preparation of Benzothiazole Derivatives as Protein Kinase C Inhibitors”; Retrieved from STN Database Accession No. 130:352268, XP002185425, 1999.
Database CA 'Online!, Chemical Abstracts Service, Columbus, Ohio, US; Takahashi et al.; “Preparation of Aminobutanoic Acid Derivatives as Inhibitors of Matrix Metalloproteinases”; Retrieved from STN Database Accession No. 130:311803, XP02185426, 1999.
Database CA 'Online!, Chemical Abstracts Service, Columbus, Ohio, US; Larsen, Scott et al.; “Preparation of Substituted Phenylalanine Derivatives as Protein Tyrosine Phosphatase Inhibitors”; Retrieved from STN, Database Accession No. 130:223585, XP002185427, 1999.
Database CA 'Online!, Chemical Abstracts Service, Columbus, Ohio, US; Hasegawa, Yoshihiro et al; “Preparation OfPyridylacrylamide Derivatives as TGF-beta.Inhibitors and Therapeutic Agents for Nephritis”; Retrieved from STN Database Accession No. 130:124997, XP002185428, 1999.
Database CA 'Online!, Chemical Abstracts Service, Columbus, Ohio, US; Buchsbaum Donald et al; “Radiolabeled Fusion Toxins for Cancer Therapy”; Retrieved from STN Database Accession No. 128:11513, XP002185429, 1997.
Database CA 'Online!, Chemical Abstracts Service, Columbus, Ohio, US; Witte, Ernst-Christian et al.; “Preparation of Phenols, Phenoxydyalkanoates, and Analogs as Blood Fibrinoge Lowering Agents”; Retrieved from STN Database Accession No. 122:314276, XP002185430, 1995.
Database CA 'Online!, Chemical Abstracts Service, Columbus, Ohio, US; Ishizaki, Masahirko: “Manufacture of Thioether Derivative”; Retrieved from STN Database Accession No. 121:179098, XP002185431, 1994.
Database CA 'Online!, Chemical Abstracts Service, Columbus, Ohio, US; Pershadsingh, Harrihara et al; “Ophthalmic Uses of PPAR-gamma. Agonists and Antagonists”; Retrieved from STN Database Accession No. 132:73666; XP002185432, 2000.
Database CA 'Online!, Chemical Abstracts Service, Columbus, Ohio, US; Crimmin, Michael John et al; “Inhibition of Tumor Necrosis Factor (TNF) Production”; Retrieved from STN Database Accession No. 122:230797, XP002185433, 1994.
Manfred et al; “Amide Analogues of Trichostatin A As Inhibitors of Histone Deacetylase and Inducers of Terminal Cell Differentiation”; Journal of Medicinal Chemistry, American Chemical Society, Washington, US, vol. 42, No. 22 Nov. 4, 1999, pp. 4669-4679, XP002144226.
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. 199-2001.
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, “Diferential 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. USA,vol. 95, p. 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, p. 55-66.
Kijima et al., 1993, Trapoxin, an antitumor cyclic tetrapeptide, is an irreversible inhibitor of mammalian histone deacetylaseJ. Biol. Chem.,vol. 268, pp. 22429-22435.
Kim et al., 1999, “Oxamflatin is a novel antitumor compound that inhibits mammalian histone deacetylase”Onco

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

Carbamic acid compounds comprising an ether linkage as HDAC... 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 an ether linkage as HDAC..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Carbamic acid compounds comprising an ether linkage as HDAC... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3480838

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