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Details for Patent: 4,051,144

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Details for Patent: 4,051,144

Title: Sinister-3,5-disubstituted oxozolidines their preparation and use
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.
Inventor(s): Weinstock; Leonard M. (Belle Mead, NJ), Tull; Roger J. (Metuchen, NJ), Mulvey; Dennis M. (Whitehouse, NJ)
Assignee: Charles E. Frosst & Co. (Kirkland, CA)
Filing Date:Dec 04, 1974
Application Number:05/529,314
Claims:1. 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.

2. An oxazolidine as claimed in claim 1 wherein R.sup.1 is hydroxy.

3. An oxazolidine as claimed in claim 1 wherein R.sup.1 is R.sup.3 O--.

4. S-3-tert-butyl-5-hydroxymethyloxazolidine.

5. S-2-phenyl-3-tert-butyl-5-hydroxymethyloxazolidine.

6. S-3-tert-butyl-5-(p-toluenesulfonyloxymethyl)-oxazolidine.

7. S-3-tert-butyl-5-(p-nitrobenzenesulfonyloxy-methyl)oxazolidine.

8. S-3-tert-butyl-5-(p-bromobenzenesulfonyloxymethyl)oxazolidine.

9. 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.

10. S-3-Isopropyl-5-hydroxymethyloxazolidine.

11. S-3-(2,2-dimethylpropyl)-5-hydroxymethyloxazolidine.

12. S-3-(1,1-dimethyl-2-hydroxyethyl)-5-hydroxymethyl oxazolidine.

13. 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.

14. S-2-isopropyl-3-tert-butyl-5-hydroxymethyloxazolidine.

15. 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.

16. 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.

17. 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.
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