Nitrate esters of corticoid compounds and pharmaceutical applications thereof
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Patent Number: US7605151
Application Number: US12051434
Filing date: 03/19/2008
Issue date: 10/20/2009
Prior Publication Data:
US20080234242 - 09/25/2008
Predicted expiration date: 10/07/2017
Patent term adjustment: 5
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Inventor(s): Piero Del Soldato ·
Assignee(s): Nicox S.A. ·
Attorney/Agent(s): Arent Fox LLP ·
Primary Examiner: Barbara P Badio ·
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U.S. Classifications: 514/178 · 552/575 · 552/574 · 514/179 ·
International Classifications: A61K3156 · C07J500 ·
Related U.S. Application Data:
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a divisional of U.S. patent application Ser. No. 11/714,724, filed Mar. 7, 2007, now U.S. Pat. No. 7,368,442, which is a divisional of U.S. patent application Ser. No. 11/445,140, filed Jun. 2, 2006, now U.S. Pat. No. 7,205,288 B2, which is a divisional of U.S. patent application Ser. No. 10/462,637, filed Jun. 17, 2003, now U.S. Pat. No. 7,056,905 B2, which is a divisional of U.S. patent application Ser. No. 09/269,729, filed Apr. 2, 1999, now U.S. Pat. No. 6,610,676, which is a National Stage application of International Application No. PCT/EP97/05426, filed Oct. 2, 1997. The disclosures of the prior applications are hereby incorporated by reference herein in their entirety.
Foreign Priority: ITMI96A2048 - 10/04/1997 ·
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Abstract
Compounds of the formula and use of the compounds as medicaments.
References Cited
U.S. Patent Documents
Document Number Assignees Inventors Issue/Pub Date
US2990401 AMERICAN CYANAMID CO Bernstein et al. Jun 1961
US3183252 SYNTEX CORP Crabbe May 1965
US3209000 UPJOHN CO Babcock et al. Sep 1965
US3494941 AMERICAN HOME PROD Ledig et al. Feb 1970
US5824669 NitroMed, Inc. Garvey et al. Oct 1998
US5837698 G. D. Searle & Co. Tjoeng et al. Nov 1998
US6197762 NitroMed, Inc. Garvey et al. Mar 2001
US6579863 Nitromed, Inc. Garvey et al. Jun 2003
US6610676 Nicox S.A. Del Soldato Aug 2003
US7056905 Nicox S.A. Del Soldato Jun 2006
US20030199529 Garvey et al. Oct 2003
Foreign Patent Documents
Document Number Assignees Inventors Issue/Pub Date
DE1643034 C A SCHAEFER K G May 1971
DE2222491 Nov 1972
FR1561908 Feb 1969
FR2274309 PLURICHEMIE ANSTALT Jan 1976
GB1544512 SQUIBB & SONS INC Apr 1979
WO199404484 CORLAY SL Mar 1994
WO199412463 HCT HEALTH CARE TRADING LTD Jun 1994
WO199509831 NICOX LTD Apr 1995
WO199530641 NICOX LTD Nov 1995
WO199734871 NITROMED INC Sep 1997
WO199740836 SEARLE & CO Nov 1997
WO199741144 SEARLE & CO Nov 1997
Other Publications
Full Specification
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a divisional of U.S. patent application Ser. No. 11/714,724, filed Mar. 7, 2007, now U.S. Pat. No. 7,368,442, which is a divisional of U.S. patent application Ser. No. 11/445,140, filed Jun. 2, 2006, now U.S. Pat. No. 7,205,288 B2, which is a divisional of U.S. patent application Ser. No. 10/462,637, filed Jun. 17, 2003, now U.S. Pat. No. 7,056,905 B2, which is a divisional of U.S. patent application Ser. No. 09/269,729, filed Apr. 2, 1999, now U.S. Pat. No. 6,610,676, which is a National Stage application of International Application No. PCT/EP97/05426, filed Oct. 2, 1997. The disclosures of the prior applications are hereby incorporated by reference herein in their entirety.
The present invention relates to preparation of new corticoid compounds.
In particular it relates to steroid-structured compounds having anti-inflammatory, immunodepressive and angiostatic activities (the so-called steroid anti-inflammatory drugs).
The compounds according to the present invention are therapeutically useful in the treatment of pathologic conditions where generally corticosteroid (corticoids) preparations are used, but with increased benefits.
This represents an unexpected advantage over the known corticoids products. In fact, by taking into account the various defined therapeutic uses of a specific product, it is always possible, with the new products of the present invention, to find a better combination of results with respect to the known corticoids. Contrary to any expectation the products of the present invention are characterised by the fact that they show an improved therapeutic profile: high activity combined with low side-effects.
Corticoids are well known as a first-choice pharmacological measure in the treatment of inflammatory disease. Drugs in this category—which include, for example, hydrocortisone, cortisone, prednisolone, prednisone, fludrocortisone, desoxycorticosterone, methylprednisolone, triamcinolone, paramethasone, betametasone, dexamethasone, triamcinolone acetonide, fluocinolone acetonide, beclomethasone, acetoxypregnelone, etc.—have marked pharmacotoxicological effects on various organs. Because of this, the clinical use and discontinued use thereof cause a series of side effects, some of which are very severe. See for example Goodman & Gilman: “The Pharmaceutical Basis of Therapeutics”, 9th Ed., pages 1459-1465, 1998.