.

Pharmaceutical Business Intelligence

  • Anticipate P&T budget requirements
  • Evaluate market entry opportunities
  • Find generic sources and suppliers
  • Predict branded drug patent expiration

► Plans and Pricing

Upgrade to enjoy subscriber-only features like email alerts and data export. See the Plans and Pricing

DrugPatentWatch Database Preview

Claims for Patent: 4,138,581

« Back to Dashboard

Claims for Patent: 4,138,581

Title: 3(Hydroxy or hydroxymethyl)-4(hydroxy)-.alpha.-(aminomethyl)benzyl alcohols
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. (Laurel Park, NC), Conway; Walter D. (Amherst, NY)
Assignee: Sterling Drugs Inc. (New York, NY)
Application Number:05/654,700
Patent Claims: 1. An ester of 3,4-dihydroxy-alpha-(amino- and N-substituted amino-methyl)benzyl alcohol having the formula ##STR13## wherein R is hydrogen, alkyl having 1-4 carbon atoms, or cycloalkyl having 3-6 carbon atoms;

R' is hydrogen or ethyl;

Y is an acyl member which is alkanoyl having 1-22 carbon atoms, alkenoyl having one or two double bonds and having 4-22 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, halo, or trifluoromethyl; and

Y.sup.1 and Y.sup.2 are the same or different and are hydrogen or one of the acyl members defined by Y, at least one of Y and Y.sup.1 being Z--C.sub.n H.sub.2n --CO-- or a pharmaceutically acceptable acid-addition salt thereof.

2. A compound according to claim 1, wherein Y and Y.sup.1 are the same or different and each is Z--C.sub.n H.sub.2n --CO--.

3. A compound according to claim 2 wherein Y.sup.2 and R' are hydrogen.

4. A compound according to claim 2 wherein n is zero.

5. A compound having the formula ##STR14## wherein R is hydrogen, alkyl having 1-4 carbon atoms, or cycloalkyl having 3-6 carbon atoms;

R' is hydrogen or ethyl;

Y and Y.sup.1 are the same or different and each is Z--C.sub.n H.sub.2n --CO-- wherein n is zero, and Z is phenyl or phenyl substituted by 1-3 members of the group consisting of alkyl having 1-4 carbon atoms, halo or trifluoromethyl or a pharmaceutically acceptable acid-addition salt thereof.

6. A compound according to claim 5 wherein R' is hydrogen.

7. A compound according to claim 6 wherein R is isopropyl.

8. A compound according to claim 5 wherein R' is ethyl.

9. A compound according to claim 8 wherein R is tertbutyl.

10. A compound having the formula ##STR15## wherein Y and Y.sup.1 are the same or different and each is Z--C.sub.n H.sub.2n --CO-- wherein n is zero, and Z is phenyl or phenyl substituted by 1-3 members of the group consisting of alkyl having 1-4 carbon atoms, halo, or trifluoromethyl or a pharmaceutically acceptable acid-addition salt thereof.

11. A compound according to claim 10 wherein each of Y and Y.sup.1 is alkylbenzoyl.

12. A compound according to claim 11 wherein alkylbenzoyl is toluyl.

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

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

15. A compound having the formula ##STR16## wherein R is hydrogen, alkyl having 1-4 carbon atoms, or cycloalkyl having 3-6 carbon atoms;

R' is hydrogen or ethyl;

one of Y and Y.sup.1 is an acyl member which is alkanoyl having 1-22 carbon atoms, and the other is Z--C.sub.n H.sub.2n --CO-- wherein n is zero, and Z is phenyl or phenyl substituted by 1-3 members of the group consisting of alkyl having 1-4 carbon atoms, halo, or trifluoromethyl or a pharmaceutically acceptable acid-addition salt thereof.

16. A compound according to claim 15 wherein R'is hydrogen.

17. A compound according to claim 15 wherein R' is ethyl.

18. A compound having the formula ##STR17## wherein one of Y and Y.sup.1 is an acyl member which is alkanoyl having 1-22 carbon atoms, and the other is Z--C.sub.n H.sub.2n --CO-- wherein n is zero, and Z is phenyl or phenyl substituted by 1-3 members of the group consisting of alkyl having 1-4 carbon atoms, halo, or trifluoromethyl or a pharmaceutically acceptable acid-addition salt thereof.

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 alkylbenzoyl is toluyl.

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

22. A compound according to claim 21 wherein n is zero.

23. A compound according to claim 22 wherein Y.sup.2 is hydrogen.

24. A compound having the formula ##STR18## wherein R is hydrogen, alkyl having 1-4 carbon atoms, or cycloalkyl having 3-6 carbon atoms;

R' is hydrogen or ethyl;

Y is Z--C.sub.n H.sub.2n --CO-- wherein n is zero, and Z is phenyl or phenyl substituted by 1-3 members of the group consisting of alkyl having 1-4 carbon atoms, halo, or trifluoromethyl or a pharmaceutically acceptable acid-addition salt thereof.

25. A compound according to claim 24 wherein R' is ethyl.

26. A compound according to claim 24 wherein R' is hydrogen.

27. A compound according to claim 26 wherein R is tert-butyl.

28. A compound selected from the group consisting of:

3,4-bis(p-toluyloxy)-alpha-[1-(tert-butylamino)ethyl]benzyl alcohol hydrochloride,

3,4-bis(p-toluyloxy)-alpha-[1-(isopropylamino)ethyl]benzyl alcohol hydrochloride.

29. An ester of 3-hydroxymethyl-4-hydroxy-alpha-(amino-and N-substituted amino-methyl)benzyl alcohol having the formula ##STR19## wherein 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 is an acyl member which is alkanoyl having 1-22 carbon atoms, alkenoyl having one or two double bonds and having 4-22 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, halo, or trifluoromethyl; and

Y.sup.1 and Y.sup.2 are the same or different and are hydrogen or one of the acyl members defined by Y,

at least one of Y and Y.sup.1 being Z--C.sub.n H.sub.2n --CO-- or a pharmaceutically acceptable acid-addition salt thereof.

30. A compound according to claim 29 wherein Y.sup.2 is hydrogen.

31. A compound according to claim 30 wherein R' is alkyl.

32. A compound according to claim 30 wherein R' is hydrogen.

33. A compound according to claim 32 wherein R is alkyl.

34. A compound according to claim 33 wherein R is tert-butyl.

35. A compound according to claim 34 wherein Y and Y.sup.1 are the same or different and each is Z--C.sub.n H.sub.2n --CO--.

36. A compound according to claim 35 wherein n is zero.

37. A compound according to claim 34 wherein one of Y and Y.sup.1 is alkanoyl and the other is Z--C.sub.n H.sub.2n --CO--.

38. A compound according to claim 37 wherein n is zero.

39. A compound according to claim 34 wherein Y.sup.1 is hydrogen.

40. 3,4-Bis(p-toluyloxy)-alpha-[(isopropylamino)methyl]benzyl alcohol methanesulfonate according to claim 7.

41. 3-Benzoyloxy-4-p-toluyloxy-alpha-[(tert-butylamino)methyl]benzyl alcohol methanesulfonate according to claim 10.

42. 3,4-Bis(benzoyloxy)-alpha-[(tert-butylamino)methyl]benzyl alcohol hydrochloride according to claim 10.

43. 3,4-Bis(p-toluyloxy)-alpha-[(tert-butylamino)methyl]benzyl alcohol methanesulfonate according to claim 12.

44. 3,4-Bis(m-toluyloxy)-alpha-[(tert-butylamino)methyl]benzyl alcohol methanesulfonate according to claim 12.

45. 3-Acetoxy-4-p-toluyloxy-alpha-[(tert-butylamino)methyl]benzyl alcohol methanesulfonate according to claim 20.

46. 3-Hydroxy-4-m-toluyloxy-alpha-[(tert-butylamino)methyl]benzyl alcohol methanesulfonate according to claim 27.
« Back to Dashboard

For more information try a trial or see the database preview and plans and pricing

Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verifification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.

`abc