Methods for synthesis of acyloxyalkyl compounds

Details Methods for synthesis of acyloxyalkyl compounds Methods for synthesis of acyloxyalkyl compounds

2004-07-15

2010-02-16

Andres, Janet L. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C546S029000, C546S032000, C546S033000

Reexamination Certificate

active

07662987

ABSTRACT:
Disclosed herein are methods for synthesizing 1-(acyloxy)-alkyl prodrug derivatives of drugs through oxidation of 1-acyl-alkyl derivatives of drugs under anhydrous reaction conditions. The methods typically proceed stereospecifically, in high yield, do not require the use of activated intermediates and/or toxic compounds and are readily amenable to scale-up.

REFERENCES:
patent: 4426391 (1984-01-01), Alexander et al.
patent: 4760057 (1988-07-01), Alexander
patent: 4916230 (1990-04-01), Alexander
patent: 5401868 (1995-03-01), Lund
patent: 5481032 (1996-01-01), Pfirmann
patent: 5733907 (1998-03-01), Alexander et al.
patent: 6350738 (2002-02-01), Savage et al.
patent: 6927036 (2005-08-01), Gallop et al.
patent: 7232924 (2007-06-01), Raillard et al.
patent: 7423169 (2008-09-01), Raillard
patent: 2003/0083382 (2003-05-01), Cundy
patent: 2005/0239725 (2005-10-01), Gallop
patent: 2008/0058546 (2008-03-01), Raillard et al.
patent: 0416689 (1991-03-01), None
patent: 1178034 (2002-02-01), None
patent: WO 02/28411 (2002-04-01), None
patent: WO 03/077902 (2003-09-01), None
Jol. of Med. chem. vol. 46 No. 25 pp. 5402-5415 (2003).
Jol. Am. Chem. Soc. vol. 119 No. 19 pp. 4541-4542 (1997).
Astudillo et al., “A Very Simple Oxidation of Olefins and Ketones With UHP-Maleic Anhydride,”Heterocycles1993, 36, 1075-1080.
Baliski et al., “Mild and Efficient Conversion of Nitriles to Amides with Basic Urea-Hydrogen Peroxide Adduct,”Synth. Commun. 1993, 23, 3149-3155.
Cooper et al., “Oxidation Reactions Using Urea-Hydrogen Peroxide; A Safe Alternative to Anhydrous Hydrogen Peroxide,”Synlett. 1990, 533-535.
Guzzo et al., “Preparation of Optically Active (acyloxy)Alkyl Esters from Optically ActiveO-Axyl-α-Hydroxy Acids,”Tetraheddron Lett.,2002, 43, 5685-5689.
Ikeda et al., “The Assembly of β-Methylene-TAD, a Metablically Stable Analogue of the Antitumor Agent TAD, By the Stepwise Esterification of Monodeprotected Methylenebis-(Phosphonate) Benzyl Esters Under Mitsonubu Conditions,”Bioorg. Med. Chem. Lett., 1999, 9, 3069-3074.
Klecker et al., “Stereoselective Metabolism of Fenoldopam and Its Metabolites in Human Liver Microsomes, Cytosol and Slices,”J. Cardiovasc. Pharmacol. 1997, 30, 69-74.
List et al., “The Proline-Catalyzed Direct Asymmetric Three-Component Mannich Reaction: Scope, Optimization, and Application to the Highly Enatioselective Synthesis of 1,2-Amino Alcohols,”J. Am. Chem. Soc. 2002, 124, 827-833.
Odinokov et al., “Synthesis of Racemic Analogue of the Naturally Occurring Dihydrorecifeiolide,”Isvest. Akad. Nauk, Ser. Khim. 1993, 7, 1301-1302.
Oszezapowicz et al., “Esters of Ephalosporins. Part III Separation and Properties of the R. and S isomers of the 1-Acetoxyethyl Esther of Cefuroxime,”Acta Pol Pharm. 1995, 52, 471-476.
Rannard et al., “Controlled Synthesis of Asymmetric Dialkyl and Cyclic Carbonates Using the Highly Selective Reactions of Imidazole Carboxylic Esters,”Organic Lett. 1999, 6, 933-936.
Uchida et al., “Cationic Co(III)(Salen)-Catalyzed Enantioselective Baeyer-Villiger Oxidation of J-Arylcyclobutanones Using Hydrogen Peroxide as the Terminal Oxidant,”Tetrahedron Lett. 2001, 42, 6911-6914.
Varie et al.; “Bioreduction of (R)-Carvone and Regioselective Baeyer Villiger Oxidations; Application to the Asymmetric Synthesis of Cryptophycin Fragment A,” TetraheddronLett. 1998, 39, 8405-8408.
Varma et al., “The Urea-Hydrogen Peroxide Complex: Solid-State Oxidative Protocols for the Hydroxylated Aldehydes and Ketones (Dankin Reaction), Nitriles, Sulfides, and Nitrogen Heterocycles,”Organic Lett. 1999, 1, 189-191.
Watanabe et al., “Highly Enantioselective Bayer-Villiger Oxidation Using Zr(Salen) Complex as Catalyst,”Tetrahedron Lett. 2002,43, 4481-4485.
Ziegler et al., “A Selective Baeyer-Villiger Oxidation: A Total Synthesis of (-)-Acetomycin,”Tetrahedron Lett. 1993, 34, 7669-7672.
Jeffs et al., Synthesis of 1-Substituted cis-Bicyclo [4.2.0] octanones through [2+2] Cycloaddtions of Dichloreketene to Alkene. Structural Characterization of Cycloadducts by Oxa-Ring Expansion. Journal of Organic Chemistry, 1982, 47, 3871-3875.
Sasaki et al., Reaction of carbon dioxide with propargyl alcohol catalyzed by a combination of Ru3(CO)12and Et3N.Tetrahedron Letters, 27(24), 1573-1574, 1984.
International Preliminary Examination Report on the International Searching Authority, issued Feb. 12, 2004 for International Application No. PCT/US2003/18495, 3 pages.
International Preliminary Examination Report of the International Searching Authority, issued Jun. 9, 2004 for International Application No. PCT/US2002/18691, 3 pages.
International Search Report, Written Opinion, and International Preliminary Report on Patentability of the International Searching Authority for International Application No. PCT/US2004/023066, 10 pages.

Affiliated with

Also associated with

Rating

Methods for synthesis of acyloxyalkyl compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Methods for synthesis of acyloxyalkyl compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Methods for synthesis of acyloxyalkyl compounds will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4225834