Abstract: A reproducible process for preparing a substantially single enantiomer (R or S) of 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexanoic acid, or an analogue thereof, thereby providing single enantiomer acid for the first time, proceeds by means of a classical salt resolution employing a resolving agent selected from an enantiomer (R or S) of a 1-arylalkylamine and (-)-quinine, and provides novel salts that are readily convertible to verapamil.
Type:
Grant
Filed:
February 7, 1997
Date of Patent:
April 6, 1999
Assignee:
Darwin Discovery Limited
Inventors:
Robin Mark Bannister, Graham Robert Evans, Benjamin Mark Skead
Abstract: Compounds of formula (I) ##STR1## wherein n=1 or 2;R.sup.1 is H, NH.sub.2 or halogen;R.sup.2 is H or NH.sub.2 ;R.sup.3 represents the group ##STR2## where m=0 or 1; R.sup.4 and R.sup.5 are the same or different and are each H, CO.sub.2 H, CO.sub.2 C.sub.1-6 alkyl, NHSO.sub.2 CF.sub.3, tetrazole, (CR.sup.6 R.sup.7).sub.p (Y).sub.q (CR.sup.6 R.sup.7).sub.t Z where (CR.sup.6 R.sup.7)p or (CR.sup.6 R.sup.7).sub.t may be straight or branched chain bearing the substituents R.sup.6 and R.sup.7 when p and t>1; R.sup.6 and R.sup.7 are the same or different and are each C.sub.0-6 alkyl-Z;p=1-3;q=0 or 1;t=0-4, provided that t>0 wgeb q=1;Y is NH, O, S(O)u where u=0-2;Z is H, CN, CO.sub.2 H, CO.sub.2 C.sub.1-6 alkyl, NHSO.sub.2 CF.sub.3, tetrazole, triazole, CONH.sub.2, CON(C.sub.1-6 alkyl).sub.2, CONH(C.sub.1-6 alkyl), SO.sub.2 NH (C.sub.1-6 alkyl) or SO.sub.2 N(C.sub.1-6 alkyl).sub.2 ; or a salt, soluate or hydrate thereof.
Type:
Grant
Filed:
May 19, 1997
Date of Patent:
January 26, 1999
Assignee:
Darwin Discovery Limited
Inventors:
Steven Colin Beasley, John Gary Montana, David Thomas Manallack
Abstract: A process for the preparation of a compound of formula (VI), optionally in enantiomerically-enriched form (R or S), comprises chemoselective reduction of a novel compound of formula (V), wherein Ar.sup.1 and Ar.sup.2 are independently selected from optionally-substituted aromatic or heteroaromatic groups having upto 20 C atoms, Ak is C.sub.1-20 alkyl, and R is H or C.sub.1-20 alkyl.
Abstract: Levobupivacaine ((S)-1-butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide) is useful as an anesthetic, particularly in a patient who is CNS-compromised or predisposed to CNS side-effects. It is also useful as an anesthetic in obstetrics.
Type:
Grant
Filed:
October 27, 1995
Date of Patent:
December 15, 1998
Assignee:
Darwin Discovery Limited
Inventors:
Hazel Judith Bardsley, Robert William Gristwood, Andrew John McGlashan Richards