Organic compounds -- part of the class 532-570 series – Organic compounds – Carbonate esters
Patent
1998-10-22
1999-10-26
Ambrose, Michael G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbonate esters
558275, C07C 6996
Patent
active
059731826
ABSTRACT:
A process for the preparation of optically active phenylcyclohexylglycolate esters is described. The process utilizes carboxylic acid activation to couple (R)- or (S)-cyclohexylphenylglycolic acid (CHPGA) with 4-N,N-diethylamino butynol or other propargyl alcohol derivatives. The preparation of the hydrochloride salt is also described. In addition, a resolution process employing tyrosine methyl ester enantiomers for preparing a single enantiomer of CHPGA from racemic CHPGA is disclosed.
REFERENCES:
patent: 2837525 (1958-06-01), Ruddy et al.
Barlow et al., "Studies on the Stereospecificity of Closely Related Compounds Which Block Postganglionic Acetylcholine Receptors in the Guinea-Pig Ileum", J. Medic. Chem. 16, 439-446 (1973).
L. Schjelderup and A.J. Aasen, "The Absolute Configuration of Oxyphencyclimine, a Parasympatholytic Drug, of Both Enantiomers", Acta Chem. Scand. B 40, 601-603 (1986).
Inch et al., "Asymmetric Synthesis: Part III. Stereospecific Synthesis of (R)-2-Hydroxy-2-Phenylpropionic (R)-and (S)-2-Cyclohexyl-2-hydroxy-2phenylacetic Acid. Configurational Relationship between (R)(-)-2-Hydroxy-2-phenylpropionic Acid and (S) (+)-2-Phenylpropionic Acid", J. Chem. Soc. (C), 1693-1699 (1968).
Majewski et al., ;"Anticholinergic Agents. Esters of 4-Dialkyl- (or 4-Polymethylene-) amino-2-butynols", J. Chem. Soc., 19-720 (1965).
S.G. Kuznetsov and Z.I. Bobysheva, "Optical Isomers of Some Cholinolytic Substances", J. General Chem. (US (1962).
Take et al., "Agents for the Treatment of Overactive Detrusor.III. Synthesis and Structure-Activi Relationships of N-(4-Amino-2-butynyl)acetamide Derivatives", Chem. Pharm. Bull., 40 1415-1423 (1992).
K.G. Feitsma, "Enantiomeren Van Oxyfenoniumbromide", Pharm. Weekbl. 124, 383-387 (1989).
Atkinson et al., "Parasympatholytic (Anticholinergic) Esters of the Isomeric 2-Tropanols. 1. Glycolate", J. Med. Chem. 20, 1612-1617 (1977).
Katchur et al., "R and S Enantiomers of Oxybutynin: Pharmacological Effects in Guinea Pig Bladder and Intestine", J. Pharmacol. Exp. Ther., 247, 867-872 (1988).
Bakale Roger P.
Lopez Jorge L.
McConville Francis X.
Senanayake Chris Hugh
Vandenbossche Charles P.
Ambrose Michael G.
Sepracor Inc.
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