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Details for Patent: 4,780,127

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Details for Patent: 4,780,127

Title: Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as herbicides
Abstract:Compounds of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, cyano, nitro, S(O).sub.n R wherein R is C.sub.1 -C.sub.4 alkyl and n is the integer 0, 1 or 2; and R.sup.2 through R.sup.8 are hydrogen or certain substituents, their salts, herbicidal compositions containing the compound or salts and the herbicidal use thereof.
Inventor(s): Michaely; William J. (El Cerrito, CA), Kraatz; Gary W. (San Jose, CA)
Assignee: Stauffer Chemical Company (Westport, CT)
Filing Date:Jun 30, 1986
Application Number:06/880,370
Claims:1. Compounds having the structural formula ##STR95## wherein R and R.sup.1 are hydrogen, C.sub.1 -C.sub.4 alkyl, R.sup.a OC(O)--, where R.sup.a is C.sub.1 -C.sub.4 alkyl;

R.sup.2 is chlorine, bromine, or iodine; and

R.sup.3, R.sup.4 and R.sup.5 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, phenyl, benzyl, --NR.sup.d R.sup.e wherein R.sup.d and R.sup.e independently are hydrogen or C.sub.1 -C.sub.4 alkyl; and n is the integer 0, 1 or 2; ##STR96## wherein R.sup.c is C.sub.1 -C.sub.4 alkyl and R.sup.j is hydrogen; (11) R.sup.f C(O) wherein R.sup.f is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy; (12) --NR.sup.g R.sup.h wherein R.sup.g and R.sup.h independently are hydrogen or C.sub.1 -C.sub.4 alkyl; or (13) R.sup.3 and R.sup.4 together can form a ring structure with two adjacent carbon atoms of the phenyl ring; and their salts.

2. The compounds of claim 1 wherein R and R.sup.1 are hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is chlorine, bromine, or iodine; R.sup.3 and R.sup.4 independently are hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, trifluoromethoxy, cyano, nitro, C.sub.1 -C.sub.4 haloalkyl, R.sup.b SO.sub.n wherein R.sup.b is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, phenyl, benzyl, --NR.sup.d R.sup.e wherein R.sup.d and R.sup.e independently are hydrogen and C.sub.1 -C.sub.4 alkyl; and n is the integer 0, 1 or 2; R.sup.c C(O)NH-- wherein R.sup.c is C.sub.1 -C.sub.4 alkyl; R.sup.f C(O)-- wherein R.sup.f is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy; or --NR.sup.g R.sup.h wherein R.sup.g and R.sup.h independently are hydrogen or C.sub.1 -C.sub. 4 alkyl; and R.sup.5 is hydrogen and their salts.

3. The compounds of claim 1 wherein R and R.sup.1 are hydrogen or methyl; R.sup.2 is chlorine or bromine; R.sup.3 is hydrogen, chlorine, C.sub.1 -C.sub.4 alkoxy, R.sup.b SO.sub.n wherein R.sup.b is C.sub.1 -C.sub.4 alkyl and n is the integer 0; R.sup.4 is hydrogen, chlorine, cyano, nitro, R.sup.b SO.sub.n wherein R.sup.b is C.sub.1 -C.sub.4 alkyl and n is 0 or 2, SO.sub.2 N(CH.sub.3).sub.2 or trifluoromethyl; and R.sup.5 is hydrogen and their salts.

4. The compounds of claim 2 wherein R.sup.2 is chlorine, R.sup.3 is substituted at the 3-position, and R.sup.4 is substituted at the 4-position and their salts.

5. The compounds of claim 3 wherein R and R.sup.1 are hydrogen; R.sup.2 is chlorine; R.sup.3 is hydrogen, 3-chlorine, 3-methoxy, 3-ethoxy or 3-n-propoxy and R.sup.4 is 4-chlorine, 4-bromine, 4-CH.sub.3 SO.sub.2 -- or 4-C.sub.2 H.sub.5 SO.sub.2 ; and R.sup.5 is hydrogen and their salts.

6. The compounds of claim 1 wherein R and R.sup.1 are hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is chlorine, bromine, or iodine or; R.sup.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, C.sub.1 -C.sub.4 haloalkyl or R.sup.b SO.sub.n wherein R.sup.b is C.sub.1 -C.sub.4 alkyl and n is the integer 0; R.sup.4 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, cyano, nitro, C.sub.1 -C.sub.4 haloalkyl or R.sup.b SO.sub.n wherein R.sup.b is C.sub.1 -C.sub.4 alkyl and n is the integer 0, 1 or 2; and R.sup.5 is hydrogen and their salts.

7. The compounds of claim 1 wherein R and R.sup.1 are hydrogen or methyl; R.sup.2 is chlorine, bromine, or iodine; R.sup.3 is hydrogen, halogen, methyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl or methylthio; R.sup.4 is hydrogen, halogen, methyl, methoxy, cyano, nitro, trifluoromethyl, methylthio or CH.sub.3 SO.sub.2 ; and R.sup.5 is hydrogen and their salts.

8. The compounds of claim 6 wherein R.sup.3 is in the 3-position and R.sup.4 is in the 4-position and their salts.

9. The compounds of claim 7 wherein R.sup.3 is in the 3-position and R.sup.4 is in the 4-position and their salts.

10. The compounds of claim 1 wherein R and R.sup.1 are hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is chlorine, bromine, or iodine or; R.sup.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkoxy, or R.sup.b SO.sub.n wherein R.sup.b is C.sub.1 -C.sub.4 alkyl and n is the integer 0; R.sup.4 is R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alkyl and n is the integer 2; and R.sup.5 is hydrogen.

11. The compounds of claim 1 wherein R and R.sup.1 are hydrogen or methyl; R.sup.2 is chlorine or bromine; R.sup.3 is hydrogen, halogen, methoxy or methylthio; R.sup.4 is R.sup.b SO.sub.n -- wherein R.sup.b is methyl and n is the integer 2; and R.sup.5 is hydrogen.

12. The compounds of claim 10 wherein R.sup.3 is in the 3-position and R.sup.4 is in the 4-position.

13. The compounds of claim 11 wherein R.sup.3 is in the 3-position and R.sup.4 is in the 4-position.

14. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is hydrogen, R.sup.4 is 4-chlorine and R.sup.5 is hydrogen and its salts.

15. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-chlorine, R.sup.4 is 4-chlorine and R.sup.5 is hydrogen and its salts.

16. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-chlorine, R.sup.4 is 4-methoxy and R.sup.5 is hydrogen and its salts.

17. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is hydrogen, R.sup.4 is 4-bromine and R.sup.5 is hydrogen and its salts.

18. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is hydrogen, R.sup.4 is 4-CH.sub.3 SO.sub.2 and R.sup.5 is hydrogen and its salts.

19. The sodium, isopropylamine, triethylamine and potassium salts of the compound of claim 15.

20. The method of controlling undesirable vegetation comprising applying to the area where control is desired, an herbicidally effective amount of a compound having the formula ##STR97##

wherein

R and R.sup.1 are hydrogen, C.sub.1 -C.sub.4 alkyl, R.sup.a OC(O)--, where R.sup.a is C.sub.1 -C.sub.4 alkyl;

R.sup.2 is chlorine, bromine, iodine or C.sub.1 -C.sub.4 alkoxy; and

R.sup.3, R.sup.4 and R.sup.5 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, phenyl, benzyl, --NR.sup.d R.sup.e wherein R.sup.d and R.sup.e independently are hydrogen or C.sub.1 -C.sub.4 alkyl; and n is the integer 0, 1 or 2; ##STR98## wherein R.sup.c is C.sub.1 -C.sub.4 alkyl and R.sup.j is hydrogen; (11) R.sup.f C(O) wherein R.sup.f is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy; (12) --NR.sup.g R.sup.h wherein R.sup.g and R.sup.h independently are hydrogen or C.sub.1 -C.sub.4 alkyl; or (13) R.sup.3 and R.sup.4 together can form a ring structure with two adjacent carbon atoms of the phenyl ring; and their salts.

21. The method of claim 20 wherein R and R.sup.1 are hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is chlorine, bromine, iodine or C.sub.1 -C.sub.4 alkoxy; R.sup.3 and R.sup.4 independently are hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, trifluoromethoxy; cyano, nitro, C.sub.1 -C.sub.4 haloalkyl, R.sup.b SO.sub.n wherein R.sup.b is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, phenyl, benzyl, --NR.sup.d R.sup.e wherein R.sup.d and R.sup.e independently are hydrogen and C.sub.1 -C.sub.4 alkyl; and n is the integer 0, 1 or 2; R.sup.c C(O)NH-- wherein R.sup.c is C.sub.1 -C.sub.4 alkyl; R.sup.f C(O)-- wherein R.sup.f is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy; or --NR.sup.g R.sup.h wherein R.sup.g and R.sup.h independently are hydrogen or C.sub.1 -C.sub.4 alkyl; and R.sup.5 is hydrogen and their salts.

22. The method of claim 20 wherein R and R.sup.1 are hydrogen or methyl; R.sup.2 is chlorine or bromine; R.sup.3 is hydrogen, chlorine, C.sub.1 -C.sub.4 alkoxy, R.sup.b SO.sub.n wherein R.sup.b is C.sub.1 -C.sub.4 alkyl and n is the integer 0; R.sup.4 is hydrogen, chlorine, cyano, nitro, R.sup.b SO.sub.n wherein R.sup.b is C.sub.1 -C.sub.4 alkyl and n is 0 or 2, SO.sub.2 N(CH.sub.3).sub.2 or trifluoromethyl; and R.sup.5 is hydrogen and their salts.

23. The method of claim 21 wherein R.sup.2 is chlorine, R.sup.3 is substituted at the 3-position, and R.sup.4 is substituted at the 4-position and their salts.

24. The method of claim 20 wherein R and R.sup.1 are hydrogen; R.sup.2 is chlorine; R.sup.3 is hydrogen, 3-chlorine, 3-methoxy, 3-ethoxy or 3-n-propoxy and R.sup.4 is 4-chlorine, 4-bromine, 4-CH.sub.3 SO.sub.2 -- or 4-C.sub.2 H.sub.5 SO.sub.2 ; and R.sup.5 is hydrogen and their salts.

25. The method of claim 20 wherein R an R.sup.1 are hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is chlorine, bromine, iodine or C.sub.1 -C.sub.4 alkoxy; R.sup.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, C.sub.1 -C.sub.4 haloalkyl or R.sup.b SO.sub.n wherein R.sup.b is C.sub.1 -C.sub.4 alkyl and n is the integer 0; R.sup.4 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, cyano, nitro, C.sub.1 -C.sub.4 haloalkyl or R.sup.b SO.sub.n wherein R.sup.b is C.sub.1 -C.sub.4 alkyl and n is the integer 0, 1 or 2; and R.sup.5 is hydrogen and their salts.

26. The method of claim 20 wherein R and R.sup.1 are hydrogen or methyl; R.sup.2 is chlorine, bromine, iodine or methoxy; R.sup.3 is hydrogen, halogen methyl, C.sub.1 -C.sub.4 alkoxy, nitro, trifluoromethyl or methylthio; R.sup.4 is hydrogen, halogen, methyl, methoxy, cyano, nitro, trifluoromethyl, methylthio or CH.sub.3 SO.sub.2 ; and R.sup.5 is hydrogen and their salts.

27. The method of claim 25 wherein R.sup.3 is in the 3-position and R.sup.4 is in the 4-position and their salts.

28. The method of claim 26 wherein R.sup.3 is in the 3-position and R.sup.4 is in the 4-position and their salts.

29. The method of claim 20 wherein R and R.sup.1 are hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is chlorine, bromine, iodine or C.sub.1 -C.sub.4 alkoxy; R.sup.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, C.sub.1 -C.sub.4 haloalkyl or R.sup.b SO.sub.n wherein R.sup.b is C.sub.1 -C.sub.4 alkyl and n is the integer 0; R.sup.4 is R.sup.b SO.sub.n -- wherein R.sup.b is C.sub.1 -C.sub.4 alkyl and n is the integer 2; and R.sup.5 is hydrogen and their salts.

30. The method of claim 20 wherein R and R.sup.1 are hydrogen or methyl; R.sup.2 is chlorine, bromine, iodine or methoxy; R.sup.3 is hydrogen, halogen, methyl, methoxy, nitro, trifluoromethyl, or methylthio; R.sup.4 is R.sup.b SO.sub.n -- wherein R.sup.b is methyl and n is the integer 2; and R.sup.5 is hydrogen and their salts.

31. The method of claim 29 wherein R.sup.3 is in the 3-position and R.sup.4 is in the 4-position and their salts.

32. The method of claim 30 wherein R.sup.3 is in the 3-position and R.sup.4 is in the 4-position and their salts.

33. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is hydrogen, R.sup.4 is 4-chlorine and R.sup.5 is hydrogen and its salts.

34. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-chlorine, R.sup.4 is 4-chlorine and R.sup.5 is hydrogen and its salts.

35. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is hydrogen, R.sup.4 is 4-bromine and R.sup.5 is hydrogen and its salts.

36. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is hydrogen, R.sup.4 is 4-CH.sub.3 SO.sub.2 and R.sup.5 is hydrogen and its salts.

37. The method of claim 34 wherein the salts are the sodium, isopropylamine, triethylamine and potassium salts.

38. An herbicidal composition comprising an herbicidally active 2-(2-chlorine, bromine, iodine or C.sub.1 -C.sub.4 alkoxy)benzoyl-1,3-cyclohexanedione or its salts and an inert carrier therefor.

39. The herbicidal composition of claim 38 wherein the 2-position of the benzoyl moiety is substituted with chlorine, bromine or C.sub.1 -C.sub.4 alkoxy.

40. The herbicidal composition of claim 39 wherein the 2-position of the benzoyl moiety is substituted with chlorine, bromine or methoxy.

41. The herbicidal composition of claim 38 wherein the 2-position of the benzoyl moiety is substituted with chlorine, bromine or C.sub.1 -C.sub.4 alkoxy and the 5-position of the 1,3-cyclohexanedione moiety is substituted with one or two C.sub.1 -C.sub.4 alkyl groups.

42. The herbicidal composition of claim 38 wherein the 2-position of the benzoyl moiety is substituted with chlorine, bromine, iodine or methoxy and the 5-position of the 1,3-cyclohexanedione moiety is substituted with one or two methyl groups.

43. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-chlorine, R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2, and R.sup.5 is hydrogen and its salts.

44. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is is chlorine, R.sup.3 is 3-methoxy, R.sup.4 is 4-CH.sub.3 SO.sub.2, R.sup.5 is hydrogen and its salts.

45. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-chlorine, R.sup.4 is 4-n-C.sub.3 H.sub.7 SO.sub.2, and R.sup.5 is hydrogen and its salts.

46. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-methoxy, R.sup.4 is 4-bromine and R.sup.5 is hydrogen and its salts.

47. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-ethoxy, R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2 and R.sup.5 is hydrogen and its salts.

48. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-methoxy, R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2 and R.sup.5 is hydrogen and its salts.

49. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-n-C.sub.3 H.sub.7 O, R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2 and R.sup.5 is hydrogen and its salts.

50. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-n-C.sub.3 H.sub.7 O, R.sup.4 is 4-CH.sub.3 SO.sub.2 and R.sup.5 is hydrogen and its salts.

51. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-ethylthio, R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2 and R.sup.5 is hydrogen and its salts.

52. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-n-C.sub.4 H.sub.9 O, R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2, and R.sup.5 is hydrogen and its salts.

53. The compound of claim 1 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is is chlorine, R.sup.3 is hydrogen, R.sup.4 is 4-methylthio, R.sup.5 is hydrogen and its salts.

54. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-chlorine, R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2 and R.sup.5 is hydrogen and its salts.

55. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-methoxy, R.sup.4 is 4-CH.sub.3 SO.sub.2 and R.sup.5 is hydrogen and its salts.

56. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-chlorine, R.sup.4 is 4-n-C.sub.3 H.sub.7 SO.sub.2 and R.sup.5 is hydrogen and its salts.

57. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-methoxy, R.sup.4 is 4-bromine and R.sup.5 is hydrogen and its salts.

58. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-ethoxy, R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2, R.sup.5 is hydrogen and its salts.

59. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-methoxy, R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2 and R.sup.5 is hydrogen and its salts.

60. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-n-C.sub.3 H.sub.7 O, R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2 and R.sup.5 is hydrogen and its salts.

61. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-n-C.sub.3 H.sub.7 O, R.sup.4 is 4-CH.sub.3 SO.sub.2 and R.sup.5 is hydrogen and its salts.

62. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-ethylthio, R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2 and R.sup.5 is hydrogen and its salts.

63. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is 3-n-C.sub.4 H.sub.9 O, R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2 and R.sup.5 is hydrogen and its salts.

64. The method of claim 20 wherein R is hydrogen, R.sup.1 is hydrogen, R.sup.2 is chlorine, R.sup.3 is hydrogen, R.sup.4 is 4-methylthio and R.sup.5 is hydrogen and its salts.
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