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Details for Patent: 3,904,671

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Details for Patent: 3,904,671

Title: Esters of 3-(hydroxy or hydroxymethyl)-4-hydroxyphenyl aminomethyl ketones
Abstract:Mono-, di- and tri-esters of 3-(hydroxy or hydroxymethyl)-4-hydroxy-alpha-(aminomethyl)benzyl alcohols, obtained by methods involving reduction of the corresponding mono- and di-ester ketones, are useful for producing sympathomimetic effects, such as bronchodilation, of long duration with low cardiovascular stimulating effect, in warm-blooded mammals.
Inventor(s): Minatoya; Hiroaki (East Greenbush, NY), Tullar; Benjamin F. (Chathan, NY), Conway; Walter D. (Amherst, NY)
Assignee: Sterling Drug Inc. (New York, NY)
Filing Date:Mar 12, 1971
Application Number:05/123,834
Claims:1. A compound of the group consisting of:

3-(Y.sup.1 -O-)-4-(Y-O-)phenyl (R-NH-)(R')methyl ketones having the formula ##EQU6## and 3-(Y-O-CH.sub.2 -)-4-(Y.sup.1 -O-)phenyl (R-NH-)(R')methyl ketones having the formula ##EQU7## wherein, in each formula: R is hydrogen, alkyl having 1-4 carbon atoms, or cycloalkyl having 3-6 carbon atoms;

R' is hydrogen or alkyl having 1-3 carbon atoms;

Y.sup.1 is hydrogen or an acyl member which is alkanoyl having 1-22 carbon atoms, cycloalkyl-C.sub.n H.sub.2n --CO-- having a total of 4-10 carbon atoms of which 3-7 are ring carbon atoms in cycloalkyl and wherein n is zero, one, or two, 1- or 2-adamantanecarbonyl, phenoxyacetyl, naphthalenecarbonyl, or Z--C.sub.n H.sub.2n --CO-- wherein n is zero, one or two and Z is phenyl or phenyl substituted by 1-3 members of the group consisting of alkyl having 1-4 carbon atoms, alkoxy having 1-4 carbon atoms, halo, or trifluoromethyl;

Y is one of the acyl members defined by Y.sup.1, at least one of Y and Y.sup.1 being Z--C.sub.n H.sub.2n --CO--; and

wherein in Formula III at least one of Y and Y.sup.1 contains no less than four carbon atoms when R is tert-butyl or cycloalkyl and no less than seven carbon atoms when R is hydrogen or alkyl other than tert-butyl; and in Formula IV at least one of Y and Y.sup.1 contains no less than four carbon atoms; and acid-addition salts thereof.

2. A 3-(Y.sup.1 -O-)-4-(Y-O-)phenyl (R-NH-)(R')methyl ketone according to claim 1.

3. A compound according to claim 2 wherein R' is hydrogen.

4. A compound according to claim 3 wherein R is alkyl.

5. A compound according to claim 4 wherein R is tert-butyl.

6. A 3-(Y-O-CH.sub.2 -)-4-(Y.sup.1 -O-)phenyl (R-NH-)(R')methyl ketone according to claim 1.

7. A compound according to claim 6 wherein R' is hydrogen.

8. A compound according to claim 7 wherein R is alkyl.

9. A compound according to claim 8 wherein R is tert-butyl.

10. A compound according to claim 9 wherein one of Y and Y.sup.1 is alkanoyl.

11. A compound according to claim 9 wherein Y.sup.1 is hydrogen.

12. A compound according to claim 5 wherein each of Y and Y.sup.1 is Z-C.sub.n H.sub.2n --CO--.

13. A compound according to claim 12 wherein n is zero.

14. A compound according to claim 13 wherein each of Y and Y.sup.1 is alkylbenzoyl.

15. A compound according to claim 14 wherein each of Y and Y.sup.1 is toluyl.

16. A compound according to claim 13 wherein each of Y and Y.sup.1 is anisoyl.

17. A compound according to claim 5 wherein one of Y and Y.sup.1 is alkanoyl and the other is Z--C.sub.n H.sub.2n --CO--.

18. A compound according to claim 17 wherein n is zero.

19. A compound according to claim 18 wherein one of Y and Y.sup.1 is alkylbenzoyl.

20. A compound according to claim 19 wherein one of Y and Y.sup.1 is toluyl.

21. A compound according to claim 18 wherein one of Y and Y.sup.1 is anisoyl.

22. A compound according to claim 5 wherein Y.sup.1 is hydrogen.

23. A compound according to claim 22 wherein n is zero.

24. A compound according to claim 23 wherein Y is toluyl.

25. A compound according to claim 23 wherein Y is anisoyl.

26. A compound according to claim 9 wherein each of Y and Y.sup.1 is Z--C.sub.n H.sub.2n --CO--.

27. A compound according to claim 26 wherein n is zero.
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