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Details for Patent: 3,723,443

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Details for Patent: 3,723,443

Title: 4-(3-SUBSTITUTED AMINO)-2-HYDROXYPROPOXY)-1,2,5-THIADIAZOLES
Abstract:4-[3-(Substituted amino)-2-hydroxypropoxyl]-1,2,5-thiadiazole compounds, substituted by a nitrogen containing group in the 3-position of the thiadiazole nucleus which exhibit .beta.-adrenergic blocking properties and thus are useful in the management of angina pectoris are described. The products are prepared by one of three principal methods (1) reaction of a 4-hydroxy-1,2,5-thiadiazole with epihalohydrin to provide 4-(3-halo-2-hydroxypropoxy)-1,2,5-thiadiazole which, upon treatment with alkali, forms the epoxide which is then reacted with an amine to provide the desired product; (2) reaction of a 3-chloro(or bromo)-4-(3-substituted amino-2-hydroxypropoxy)-1,2,5-thiadiazole with an amine or an N-containing heterocycle that replaces the 3-chloro group; and (3) reductive alkylation of an ##SPC1## Wherein R is the 1,2,5-thiadiazole-4-yl group.
Inventor(s): Wasson; Burton Kendall (Valois, Quebec, CA)
Assignee: Charles E. Frosst & Co. (Kirkland, Quebec, CA)
Filing Date:Sep 09, 1971
Application Number:05/179,147
Claims:1. A 1,2,5-thiadiazole having the structure

and pharmacologically acceptable salts thereof wherein

R is a nitrogen-containing group of the structure --NR.sup.7 R.sup.8 wherein

R.sup.7 is selected from hydrogen, lower alkyl and hydroxy substituted lower alkyl,

R.sup.8 is selected from hydrogen, lower alkyl and hydroxy substituted lower alkyl, or

R.sup.7 and R.sup.8 when lower alkyl can be linked directly together to form a 3- to 7-membered ring with the nitrogen to which they are attached or a substituted 3- to 7-membered ring wherein the substituent groups are selected from lower alkyl, hydroxy, or hydroxy-lower alkyl;

R.sup.5 is selected from the group consisting of hydrogen and lower alkyl;

R.sup.6 is selected from the group consisting of

1. C.sub.1.sub.-10 alkyl,

2. substituted C.sub.1.sub.-10 alkyl wherein the substituent groups are selected from (a) hydroxy, (b) di-lower alkylamino, (c) pyrrolidinyl, (d) piperazinyl, (e) piperidinyl, (f) phenyl, (g) halophenyl, (h) lower alkoxyphenyl, (i) phenoxy, (j) lower alkoxyphenoxy, (k) lower alkylphenoxy, and

3. C.sub.3.sub.-6 cycloalkyl; and

R.sup.5 and R.sup.6 can be joined together to form with the nitrogen atom to which they are attached the pyrrolidyl, piperidino, hexahydroazepinyl.

2. A 1,2,5-thiadiazole as claimed in claim 1 wherein R is piperidino of the structure

wherein X is selected from the group consisting of hydrogen, hydroxy, lower alkyl and hydroxy-lower alkyl.

3. A 1,2,5-thiadiazole having the structure

or a pharmacologically acceptable salt thereof wherein X is selected from the group consisting of hydrogen, hydroxy, lower alkyl and hydroxy-lower alkyl.

4. A 1,2,5-thiadiazole having the structure

or a pharmacologically acceptable salt thereof.

5. A 1,2,5-thiadiazole as claimed in claim 4 wherein the (C.sub.1.sub.-10 alkyl) is tert-butyl.

6. A 1,2,5-thiadiazole as claimed in claim 4 wherein the (C.sub.1.sub.-10 alkyl) is isopropyl.

7. A 1,2,5-thiadiazole having the structure

or a pharmacologically acceptable salt thereof.

8. A 1,2,5-thiadiazole as claimed in claim 7 wherein the (C.sub.1.sub.-10 alkyl) is tert-butyl.
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