Sumitomo Chemical Company, Limited

Hiroyuki Mizote

Hisao Yamamoto

Junki Katsube

Shigeho Inaba

Kenji Kobayashi

Toshitsugu Fukumaru

Naohito Ohashi

Kikuo Ishizumi

Isamu Maruyama

Shoji Nagata

Shuichi Harada

A process for the optical resolution of DL-.alpha.-methyl-.beta.-acylthiopropionic acid, which comprises contacting a DL-.alpha.-methyl-.beta.-acylthiopropionic acid of the formula, ##STR1## wherein R.sub.1 is acetyl or benzoyl which may be substituted with a C.sub.1 -C.sub.3 alkyl or a halogen atom, with an optically active amine of the formula, ##STR2## wherein R.sub.2 is methyl, isopropyl or isobutyl, to form diastereoisomeric salts, subjecting the formed diastereoisomeric salts to the fractional crystallization in a solvent to separate the D-acid salt from the L-acid salt, and then contacting the individual diastereoisomeric salt with acid to give D-.alpha.-methyl-.beta.-acylthiopropionic acid and L-.alpha.-methyl-.beta.-acylthiopropionic acid, the former being useful as an intermediate for synthesizing captopril useful as an antihypertensive agent.

Optical resolution of acylthiopropionic acid

2-Substituted-2'-methyl-6,7-benzomorphan derivatives of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen or C.sub.1 -C.sub.3 alkyl; and R.sub.3 is hydrogen, halogen or C.sub.1 -C.sub.3 alkyl, and pharmaceutically acceptable salts thereof, which are useful as non-addicting analgesics with sedative effects, are prepared by the reaction of a 6,7-benzomorphan derivative of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are as defined above, with a reactive derivative of an alcohol compound of the formula: ##STR3## wherein X is an optionally protected carbonyl group; and R.sub.3 is as defined above, optionally followed by the elimination of the protective group of the carbonyl group, or by the oxidation of a 6,7-benzomorphan derivative of the formula: ##STR4## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above.

Analgesic benzomorphan derivatives

Novel 2-substituted 6,7-benzomorphan derivatives of the formula: ##SPC1## And acid addition salts thereof, which are useful as non-addicting analgesics, pain relieving agents and antitussives and can be prepared by reacting 6,7-benzomorphan derivatives of the formula: ##SPC2## With the reactive derivatives of alcohols of the formula: ##EQU1## [wherein R is a hydrogen atom, a hydroxyl group, an alkoxy group or an alkanoyloxy group; R.sub.1 is a hydrogen atom, an alkyl group, an alkoxyalkyl group or a substituted or unsubstituted aryl group; R.sub.3 is a hydrogen atom or a hydroxyl group; R.sub.4 is a hydrogen atom, an alkyl group or a substituted or unsubstituted aryl group, or R.sub.3 and R.sub.4 may form an alkylidene group or a carbonyl group together with the carbon atom to which these substituents are bonded; R.sub.2, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are each a hydrogen atom or an alkyl group; A is an alkylene group; and m is an integer of 0 to 2].

Novel 2-substituted 6,7-benzomorphan derivatives and salts thereof in

A novel 2-substituted-6,7-benzomorphan derivative of the formula: ##SPC1## And its acid addition salts, which are useful as non-addicting analgesics and antitussives and can be prepared by reacting a 2-unsubstituted-6,7-benzomorphan derivative of the formula: ##SPC2## With the reactive derivative of an alcohol of the formula:

6,7-Benzomorphan derivatives

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Takarazuka, Japan

Hiroyuki Mizote