Carbamic acid compounds comprising a bicyclic heteroaryl...

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C546S159000, C546S163000

Reexamination Certificate

active

08071620

ABSTRACT:
This invention pertains to certain carbamic acid compounds of the following formula, which inhibit HDAC (histone deacetylase) activity wherein: A is independently an unsubstituted or substituted bicyclic C9-10heteroaryl group (e.g., quinolinyl; quinoxalinyl; benzoxazolyl; benzothiazolyl); Q is an acid leader group, and is independently an unsubstituted or substituted, saturated or unsaturated C1-7alkylene group having a backbone length of 4 or less; with the proviso that if A is unsubstituted benzothiazol-2-yl, then Q is an unsaturated group; and with the proviso that if A is unsubstituted quinolin-6-yl, then Q is unsubstituted at the α-position; and with the proviso that A is not benzimidazol-2-yl; 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 in the treatment of conditions mediated by HDAC, cancer, proliferative conditions, psoriasis, etc.

REFERENCES:
patent: 3912748 (1975-10-01), Evans et al.
patent: 4285962 (1981-08-01), Franzone
patent: 4769461 (1988-09-01), Musser et al.
patent: 5804593 (1998-09-01), Warpehoski et al.
patent: 5834249 (1998-11-01), Furukawa et al.
patent: 6172057 (2001-01-01), Venkatesan et al.
patent: 6235753 (2001-05-01), Bailey et al.
patent: 6420427 (2002-07-01), Takahashi et al.
patent: 6444704 (2002-09-01), Venkatesan et al.
patent: 7446118 (2008-11-01), Iyer et al.
patent: 2006/0079528 (2006-04-01), Finn et al.
patent: 1974-2404413 (1974-08-01), None
patent: 0 342 682 (1989-11-01), None
patent: 0 570 594 (1993-11-01), None
patent: 0 737 671 (1996-10-01), None
patent: 0 827 742 (1998-03-01), None
patent: 0 887 348 (1998-12-01), None
patent: 2338041 (1977-08-01), None
patent: 10114681 (1998-05-01), None
patent: WO 96/11917 (1996-04-01), None
patent: WO 97/43249 (1997-11-01), None
patent: WO 99/67201 (1999-12-01), None
patent: WO 00/05218 (2000-02-01), None
patent: WO 00/34313 (2000-06-01), None
patent: WO 00/69827 (2000-11-01), None
patent: WO 01/38322 (2001-05-01), None
patent: WO 01/70675 (2001-09-01), None
patent: WO 02/22577 (2002-03-01), None
patent: WO 02/26696 (2002-04-01), None
patent: WO 02/26703 (2002-04-01), None
patent: WO 02/30879 (2002-04-01), None
patent: WO 02/076941 (2002-10-01), None
patent: WO 02/090534 (2002-11-01), None
patent: WO 03/082288 (2003-10-01), None
Bailey et al, “Selective Inhibition of Low Affinity IgE Receptor (CD23) Processing: P1' Bicyclomethyl Substituents”, Bioorg & Med Chem Lett, vol. 9(21), pp. 3165-3170, 1999.
McLaughlin et al, “Histone deacetylase inhibitors in psoriasis therapy”, Current Drug Targets Inflamm Allergy, vol. 3(2), pp. 213-219, Jun. 2004.
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.
Babichev et al., 1968, “Benzo-2-thiazolyl)alkane(arene)carboxylic acids and their derivatives. VII. Hydrazides, hydroxamic acids, nitriles and thioamides from (benzo-2-thiazolyl)alkanecarboxylic acids,”Ukrainskii Khimicheskii Zhurnal, vol. 34, No. 9, pp. 933-936 (with English abstract).
Badaev, F.A. et al., 1973, “Antiviral activity of synthetic compounds”,Veterinariya, vol. 6, pp. 44-46 (with English abstract).
Barbier, C. et al., 2000, Preparation of Lavendamycin Analogues,Heterocycles, vol. 5, pp. 37-48.
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.
Buchi, von J. et al., 1956, “Synthese and pharmakologische wirkung einiger thiosemicarbazone von 8-hydroxychinolin-derivaten,”Helv. Chim. Acta, vol. 39, pp. 1676-1683 (with English language summary).
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.
Conte, M., et al., 1967, “Synthèse et propriétés physico-chimiques de bases de Schiff en série benzothiazolique”,Bull. Soc. Chim. Fr., pp. 2834-2841 (with English abstract—CA 68:78190k).
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 leukemia-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,”Proceedings of the American Association for Cancer Research, Pevention/Basic Science and Clinical Studies 4, vol. 40, p. 362, Abstract No. 2396.
Desmarets, C. et al., 2001, “Nickel-catalysed sequential amination of aryl- and heteroaryl di- and trichlorides,”Tetrahedron, vol. 57, pp. 7657-7664.
Emiliani, S., et al., 1998, “Characterization of a human RPD3 ortholog, HDAC3,”Proc. Natl. Acad. Sci. 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.
Frank, W.C. et al., 1978, “Palladium-catalyzed vinylic substitution reactions with heterocyclic bromides”,J. Org. Chem., vol. 43, pp. 2947-2949.
Gall, von R. et al., 1955, “Über einige derivate heterocyclischer carbonsäuren IV,”Helv. Chim. Acta., vol. 38, pp. 1421-1423 (with English language summary).
Gordon, M. et al., 1964, “The swamping catalyst effect. VI. The Halogenation of isoquinoline and quinoline”,J. Org. Chem., vol. 39, pp. 329-332.
Grozinger et al., 1999, “Three proteins define a class of human histone deacetylases related to yeast Hdalp,”Proc. Natl. Acad. Sci. USA, vol. 96, pp. 4868-4873.
Günes, H.S. et al., 1992, “Synthesis of some hydroxamic acid derivatives of benzimidazole and their antibacterial and antifungal activities,”Arzneimittel-Forschung, vol. 42, No. 8, pp. 1045-1048.
Hartwig, J.F., et al., 1999, “Room-Temperature Palladium-Catalyzed Amination of Aryl Bromides and Chlorides and Extended Scope of Aromatic C-N Bond Formation with a Commercial Ligand,”J. Org. Chem., vol. 64, pp. 5575-5580.
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 β Repression ofcdc25Aduring Keratinocyte Cell Cycle Arrest,”Mol. Cell Biol., vol. 19, No. 1, pp. 916-922.
Iwao, M. et al., 1978, “The facile synthesis of some N-heteroarylacetic esters”,J. Heteroc. Chem., vol. 15, pp. 1425-1430.
Kao et al., 2000, “Isolation of a novel histone deacetylase reveals that class I and class II deacetyl

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 a bicyclic heteroaryl... 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 bicyclic heteroaryl..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Carbamic acid compounds comprising a bicyclic heteroaryl... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4315136

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