Sinister-3,5-disubstituted oxozolidines their preparation and use
AssigneeCharles E. Frosst & Co.
InventorsLeonard M. Weinstock, Roger J. Tull, Dennis M. Mulvey
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Abstract
Preparation of S-3-X-4-(3-substituted amino-2-hydroxypropoxy)-1,2,5-thiadiazole beta adrenergic blocking agents using as starting material an optically active alkalmine in the sinister configuration, or a derivative of said alkamine, which is reacted with an 3-X-4-chloro(or RO-where R is hydrogen or an alkali metal)-1,2,5-thiadiazole. Certain3-morpholino-4-chloro(or RO-)-1,2,5-thiadiazoles and certain alkamines and their preparation also are described. Preferred alkamines are S-3,5-disubstituted oxazolidines.
Claims17
An optically active oxazolidine in the sinister configuration having the structure:
- ##STR6## wherein R.sup.1 is hydroxy or R.sup.3 O-- wherein R.sup.3 is C.sub.1-16 alkylsulfonyl, benzenesulfonyl optionally having substituents selected from the group consisting of
- a. an amino group,
- b. 1-3 bromo groups,
- c. 1-3 chloro groups,
- d. a chloro and a nitro group,
- e. a fluoro group,
- f. a methoxy group,
- g. 1-3 methyl groups and
- h. a nitro group;
- Z is hydrogen, benzyl, C.sub.1 -C.sub.3 alkyl, phenyl optionally having substituents selected from the group consisting of
- a. 1-3- bromo groups,
- b. 1-3 chloro groups,
- c. 1-3 methyl groups,
- d. a methoxy group and
- e. 1-3 hydroxy groups,
- or Z can be furfuryl;
- and Y is a straight or branched chain C.sub.1 -C.sub.5 alkyl or hydroxy substituted straight or branched chain C.sub.1 -C.sub.5 alkyl.
S-3-tert-butyl-5-hydroxymethyloxazolidine.
S-2-phenyl-3-tert-butyl-5-hydroxymethyloxazolidine.
S-3-tert-butyl-5-(p-toluenesulfonyloxymethyl)-oxazolidine.
S-3-tert-butyl-5-(p-nitrobenzenesulfonyloxy-methyl)oxazolidine.
S-3-tert-butyl-5-(p-bromobenzenesulfonyloxymethyl)oxazolidine.
An optically active 3-Y-5-hydroxymethyloxazolidine in the sinister configuration wherein Y is a straight or branched chain C.sub.1 -C.sub.5 alkyl or hydroxy substituted straight or branched chain C.sub.1 -C.sub.5 alkyl.
S-3-Isopropyl-5-hydroxymethyloxazolidine.
S-3-(2,2-dimethylpropyl)-5-hydroxymethyloxazolidine.
S-3-(1,1-dimethyl-2-hydroxyethyl)-5-hydroxymethyl oxazolidine.
An optically active 2- C.sub.1 -C.sub.3 alkyl-3-Y-5-hydroxymethyloxazolidine in the sinister configuration wherein Y is a straight or branched chain C.sub.1 -C.sub.5 alkyl or hydroxy substituted straight or branched chain C.sub.1 -C.sub.5 alkyl.
S-2-isopropyl-3-tert-butyl-5-hydroxymethyloxazolidine.
An optically active 2-aryl-3-Y-5-hydroxymethyloxazolidine in the sinister configuration wherein aryl is phenyl optionally having 1 to 3 substituents selected from the group consisting of
- a. 1-3 bromo groups,
- b. 1-3 -chloro groups,
- c. 1-3 methyl groups,
- d. 1-3 -hydroxy groups,
- and
- e. a methoxy group
- and Y is a straight or branched chain C.sub.1 -C.sub.5 alkyl or hydroxy substituted straight or branched chain C.sub.1 -C.sub.5 alkyl.
An optically active 3-Y-5-(C.sub.1-16 alkylsulfonyloxymethyl)oxazolidine in the sinister configuration wherein Y is a straight or branched chain C.sub.1 -C.sub.5 alkyl or hydroxy substituted straight or branched chain C.sub.1 -C.sub.5 alkyl.
An optically active 3-Y-5 benzene-or substituted benzenesulfonyloxymethyl oxazolidine in the sinister configuration wherein said benzene substituents are selected from the group consisting of
- a. an amino group,
- b. 1-3 bromo groups,
- c. 1-3 chloro groups,
- d. a chloro and a nitro group,
- e. a fluoro group,
- f. a methoxy group,
- g. 1-3 methyl groups
- and
- h. a nitro group,
- and Y is a straight or branched chain C.sub.1 -C.sub.5 alkyl or hydroxy substituted straight or branched chain C.sub.1 -C.sub.5 alkyl.
Dependencies are inferred from the claim text.