Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-06-27
2004-06-01
Powers, Fiona T. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S363000, C514S364000, C514S369000, C514S371000, C514S376000, C544S137000, C544S212000, C546S271400, C548S127000, C548S136000, C548S143000, C548S184000, C548S195000, C548S231000, C548S232000
Reexamination Certificate
active
06743811
ABSTRACT:
FIELD OF THE INVENTION
The present invention is directed to oxazolidinones, oxazolidinone compositions, and methods for their preparation and use.
BACKGROUND ART
Oxazolidinones are compounds where an amine group and a hydroxyl group on adjacent carbon atoms have been cyclized to form a 5-membered ring containing a carbonyl group. Certain oxazolidinones have been shown to exhibit a variety of biological activities. For example, some oxazolidinones are inhibitors of monoamine oxidase-B, an enzyme implicated in Parkinson's disease. See, for example, Ding et al.,
J. Med. Chem
. 36:3606-3610 (1993).
Scientists have reported that certain oxazolidinone derivatives exhibit beneficial antibacterial effects. For instance, N-[3-[3-fluoro-4-(morpholin-4-yl)phenyl]2-oxooxazolidin-5(s)-ylmethyl]acetamide (below) has been reported to be useful for the treatment of bacterial infections. Lizondo et al.,
Drugs of the Future
, 21:1116-1123 (1996).
A ten step synthesis of oxazolidinone antibiotics has been described. U.S. Pat. No. 5,547,950. A four step synthesis of the antibacterial compound U-100592 also has been reported. Schauss et al.,
Tetrahedron Letters
, 37:7937-7940 (1996). A five step preparation of enantiomerically pure cis- and trans-N-(propionyl)hexahydrobenzoxazolidin-2-ones further was reported. De Parrodi et al.,
Tetrahedron: Asymmetry
, 8:1075-1082 (1997).
The synthesis of the oxazolidinone antibacterial agent shown below has been reported. Wang et al.,
Tetrahedron
, 45:1323-1326 (1989). This oxazolidinone was made using a process that included the reaction of an aniline with glycidol to provide an amino alcohol, and the diethylcarbonate mediated cyclization of the amino alcohol to afford an oxazolidinone.
The synthesis of oxazolidinone antibacterial agents, including the compound shown below has been reported. U.S. Pat. No. 4,705,799. The process used to make the compound shown below included a metal mediated reduction of a sulfonyl chloride to provide a sulfide.
The synthesis of oxazolidinone antibacterial agents, including the pyridyl compound shown below has been reported. U.S. Pat. No. 4,948,801. The process used included an organometallic mediated coupling of an organotin compound and an aryl iodide.
Other reports of syntheses of oxazolidinone compounds are described in DE 196 01 264 A1, EP 0 789 026 A1, DE 196 04 223 A1, EP 0 738 726 A1, and PCT WO 98/54161.
The synthesis of oxazolidinone compounds also is described in U.S. patent application Ser. No. 09/012,535, filed Jan. 23, 1998, U.S. patent application Ser. No. 09/086,702, filed May 28, 1998, U.S. patent application Ser. No. 09/235,771, filed Jan. 22, 1999, and PCT/US99/01318, filed Jan. 22, 1999, the disclosures of which are incorporated herein by reference in their entirety.
SUMMARY OF INVENTION
Provided are oxazolidinones, compositions comprising oxazolidinones, as well as methods of their synthesis and use. Also provided are compositions for the treatment or prevention of an infectious disorder comprising an effective amount of any oxazolidinone compound disclosed herein and a pharmaceutically acceptable carrier. Methods are provided of treating or preventing an infectious disorder in a human or other animal subject, comprising administering to the subject an effective amount of any oxazolidinone compound disclosed herein.
REFERENCES:
patent: 4705799 (1987-11-01), Gregory
patent: 4948801 (1990-08-01), Carlson et al.
patent: 4977173 (1990-12-01), Brittelli et al.
patent: 5182403 (1993-01-01), Brickner
patent: 5225565 (1993-07-01), Brickner
patent: 5547950 (1996-08-01), Hutchinson et al.
patent: 5684023 (1997-11-01), Riedl et al.
patent: 5792765 (1998-08-01), Riedl et al.
patent: 5827857 (1998-10-01), Riedl et al.
patent: 5869659 (1999-02-01), Stolle et al.
patent: 5922708 (1999-07-01), Riedl et al.
patent: 5977373 (1999-11-01), Gadwood et al.
patent: 6069160 (2000-05-01), Stolle et al.
patent: 6441005 (2002-08-01), Gordeev et al.
patent: 196 01 264 (1997-07-01), None
patent: 196 04 223 (1997-08-01), None
patent: 789026 (1987-08-01), None
patent: 316594 (1989-05-01), None
patent: 359418 (1990-03-01), None
patent: 694544 (1996-01-01), None
patent: 738726 (1996-10-01), None
patent: 785200 (1997-07-01), None
patent: 785201 (1997-07-01), None
patent: 789025 (1997-08-01), None
patent: 789026 (1997-08-01), None
patent: 11 322 729 (1999-11-01), None
patent: WO 98/54161 (1998-12-01), None
patent: WO 99/02525 (1999-01-01), None
patent: WO 99/03846 (1999-01-01), None
patent: WO 99/12914 (1999-03-01), None
patent: WO 99/37630 (1999-07-01), None
patent: WO 99/37641 (1999-07-01), None
patent: WO 99/37652 (1999-07-01), None
patent: WO 99/40094 (1999-08-01), None
patent: WO 00/27830 (2000-05-01), None
patent: WO 00/29396 (2000-05-01), None
patent: WO 00/29409 (2000-05-01), None
Chia-Lin J. Wang et al., “Chiral Synthesis of Dup 721, A New Antibacterial Agent,” Tetrahedron, vol. 45, No. 5, pp. 1323-1326 (1989).
W.A. Gregory et al., “Antibacterials. Synthesis and Structure-Activities Studies of 3-aryl-2-oxooxazolidines”, J. of Med. Chem., vol. 32, No. 8, pp. 1673-1681 (Aug. 1989).
Charles Z. Ding et al. “Transformation of Heterocyclic Reversible Monamine Oxidase-B Inactivators into irreversible Inactivators by N-Methylation,” J. Med. Chem., vol. 36, pp. 3606-3610 (1993).
J. Lizondo et al., “Linezolid,” Drugs of the Future, vol. 21, No. 11, pp. 1116-1123 (1996).
Scott E. Schauss et al., “Dynamic Kinetic Resolution of Epichlorohydrin via Enantioselective Catalytic Ring Opening With TMSN“3”: Practival Syntehsis of Aryl Oxazolidinone Antibacterial Agents,” Tetrahedron Letters, vol. 37, No. 44, pp. 7937-7940 (1996).
Cecilia Anaye de Parrodi et al., “Preparation of Enantiomerically Pure cis- and trans-N-(propionyl)hexahydrobenzoxazolidin-2-ones,” Tetrahedron: Asymmetry, vol. 8, No. 7, pp. 1075-1082 (1997).
International Search Report in International Application No. PCT-US00/20332, dated Nov. 16, 2000.
Written Opinion in International Application No. PCT-US00/20332, dated May 2, 2001.
Gadwood Robert C.
Gordeev Mikhail F.
Luehr Gary W.
Patel Dinesh V.
Marshall & Gerstein & Borun LLP
Pharmacia & Upjohn Company
Powers Fiona T.
LandOfFree
Oxazalidinone compounds and methods of preparation and use... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Oxazalidinone compounds and methods of preparation and use..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Oxazalidinone compounds and methods of preparation and use... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3353172