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Details for Patent: 7,498,321

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Details for Patent: 7,498,321

Title:17.beta.-carbothioate 17.alpha.-arylcarbonyloxyloxy androstane derivative as anti-inflammatory agents
Abstract: There are provided according to the invention compounds of formula (I) wherein R.sub.1 represents C.sub.1-6 alkyl or C.sub.1-6 haloalkyl; R.sub.2 represents --C(.dbd.O)-aryl or --C(.dbd.O)-heteroaryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and----represents a single or a double bond; and salts and solvates thereof. There are also provided processes for preparing compounds of formula (I) and use of the compounds in therapy especially in the treatment of inflammatory and allergic conditions.
Inventor(s): Biggadike; Keith (Stevenage, GB), Jones; Paul (Stevenage, GB), Payne; Jeremy John (Stevenage, GB)
Assignee: Glaxo Group Limited (Greenford, Middlesex, GB)
Filing Date:Aug 03, 2001
Application Number:10/343,842
Claims:1. A compound of formula (I) ##STR00024## wherein R.sub.1 represents C.sub.1-6 alkyl or C.sub.1-6 haloalkyl; R.sub.2 represents --C(.dbd.O)-aryl or --C(.dbd.O)-heteroaryl, wherein said heteroaryl is a 5 member heterocyclic aromatic ring containing 1-3 hetero atoms selected from N and S, or a 5 member heterocyclic aromatic ring containing 2-3 hetero atoms selected from N, O and S, or a 6 member heterocyclic aromatic ring containing 1-3 hetero atoms selected from N, O and S; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond; or a salt or a solvate thereof.

2. A compound according to claim 1 in which R.sub.1 represents fluoromethyl, chloromethyl, bromomethyl or 2'-fluoroethyl.

3. A compound according to claim 2 in which R.sub.1 represents fluoromethyl.

4. A compound according to claim 1 in which R.sub.2 represents --C(.dbd.O)-heteroaryl, wherein said heteroaryl is a 5 member heterocyclic aromatic ring containing 1-3 hetero atoms selected from N and S, or a 5 member heterocyclic aromatic ring containing 2-3 hetero atoms selected from N, O and S, or a 6 member heterocyclic aromatic ring containing 1-3 hetero atoms selected from N, O and S.

5. A compound according to claim 4 wherein heteroaryl represents a 5-membered heterocyclic aromatic ring containing 1 to 3 heteroatoms selected from N and S which may optionally be substituted.

6. A compound according to claim 5 wherein the heterocyclic ring is substituted with one or more substituents selected from C.sub.1-6alkyl, C.sub.1-6alkoxy and halogen.

7. A compound according to claim 5 in which the heterocyclic ring is pyrrolyl or thiophenyl.

8. A compound according to claim 7 in which the heterocyclic ring is thiophenyl.

9. A compound according to claim 5 in which the 5-membered heterocyclic ring contains 2 heteroatoms selected from N and S.

10. A compound according to claim 9 wherein the heterocyclic ring is selected from thiazolyl, isothiazolyl, pyrazolyl and imidazolyl.

11. A compound according to claim 5 in which the 5-membered heterocyclic ring contains 3 heteroatoms selected from N and S.

12. A compound according to claim 11 wherein the heterocycle is thiadiazolyl.

13. A compound according to claim 5 wherein the heterocyclic ring is substituted with one or more substituents selected from C.sub.1-6alkyl and halogen.

14. A compound according to claim 1 in which R.sub.3 is methyl.

15. A compound according to claim 1 in which R.sub.4 and R.sub.5 are the same or different and each represents hydrogen, fluorine or chlorine.

16. A compound according to claim 1 in which R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or fluorine.

17. A compound according to claim 1 in which both R.sub.4 and R.sub.5 are fluorine.

18. A compound according to claim 1 in which represents a double bond.

19. A compound according to claim 1 which is: 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-17.alp- ha.-[(2-thienylcarbonyl)oxy]-androsta -1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-17.alp- ha.-[(3-thienylcarbonyl)oxy]-androsta -1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 17.beta.-(Benzoyl)oxy-6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alph- a.-methyl-3-oxo-androsta-1,4-diene -17.beta.-carbothioic acid S-fluoromethyl ester; or a salt or solvate of any one thereof.

20. A compound of formula (I) according to claim 1 which is: 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-17.alpha.-[(isoxazole-5-carbo- nyl)oxy]-16.alpha.-methyl-3-oxo -androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyi ester; 17.alpha.-[(5-Chlorothiophene-2-carbonyl)oxy]-6.alpha.,9.alpha.-difluoro-- 11.beta.-hydroxy-16.alpha.-methyl-3-oxo -androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-17.alpha.-[(3,5-dimethylisoxazole-4-carbonyl)o- xy]-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androsta-1,4-diene-17.beta.-ca- rbothioic acid S-fluoromethyl ester; 17.alpha.-[(5-Chloro-4-methoxy-thiophene-3-carbonyl)oxy]-6.alpha., 9.alpha.-difluoro-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androsta-1,4-di- ene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(- 4-methyl-1,2,3-thiadiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.bet- a.-carbothioic acid S-fluoromethyl ester; 17.alpha.-[(3-Bromothiophene-2-carbonyl)oxy]-6.alpha.,9.alpha.-difluoro-1- 1.beta.-hydroxy-16.alpha.-methyl-3-oxo -androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 17.alpha.-[(2,5-Dichlorothiophene-3-carbonyl)oxy]-6.alpha.,9.alpha.-diflu- oro-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androsta-1,4-diene-17.beta.-ca- rbothioic acid S-fluoromethyl ester; 17.alpha.-[(3-Chlorothiophene-2-carbonyl)oxy]-6.alpha.,9.alpha.-difluoro-- 11.beta.-hydroxy-16.alpha.-methyl-3-oxo -androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(- 5-methylisoxazole-4-carbonyl)oxy]-3-oxo -androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(- 1-methyl-1H-pyrrole-2-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carb- othioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-17.alp- ha.-[(1,3-thiazoie-4-carbonyl)oxy]-androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-17.alpha.-[(2,4-dimethyl-1,3-thiazole-5-carbon- yl)oxy]-11.beta.-hydroxy-16.alpha.-methyl -3-oxo-androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(- 5-methylisoxazole-3-carbonyl)oxy]-3-oxo -androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(- 3-methylisoxazole-5-carbonyl)oxy]-3-oxo -androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-17.alpha.-[(1,3-dimethyl-1H-pyrazole-5-carbony- i)oxy]-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androsta-1,4-diene-17.beta.- -carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-17.alpha.-[(isoxazole-3-carbo- nyl)oxy]-16.alpha.-methyl-3-oxo -androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-17.alpha.-[(4-methoxy-thiophe- ne-3-carbonyi)oxy]-16.alpha.-methyl-3-oxo-androsta-1,4-diene-17.beta.-carb- othioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(- 2-methyl-1,3-thiazole-4-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-ca- rbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-17.alpha.-[(3-ethoxy-thiophene-2-carbonyl)oxy]- -11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androsta-1,4-diene-17.beta.-carbo- thicic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-17.alp- ha.-[(1,2,3-thiadiazole-4-carbonyt)oxy]-androsta-1,4-diene-17.beta.-carbot- hioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-17.alp- ha.-[(1H-pyrrole-2-carbonyl)oxy]-androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-17.alp- ha.-[(1,3-thiazole-5-carbonyl)oxy]-androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-17.alp- ha.-[(1,2,5-thiadiazole-3-carbonyl)oxy]-androsta-1,4-diene-17.beta.-carbot- hioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-17.alpha.-[(isothiazole-3-car- bonyl)oxy]-16.alpha.-methyl-3-oxo -androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-17.alpha.-[(isothiazole-5-car- bonyl)oxy]-16.alpha.-methyl-3-oxo -androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(- 5-methylthiophene-2-carbonyl)oxy]-3-oxo -androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(- 3-methylthiophene-2-carbonyl)oxy]-3-oxo -androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(- 4-methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-ca- rbothioic acid S-fluoromethyl ester; 17.alpha.-[(1-Ethyl-3-methyl-1H-pyrazole-5-carbonyl)oxy]-6.alpha., 9.alpha.-difluoro-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androsta-1,4-di- ene-17.beta.-carbothioic acid 5-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-17.alpha.-[(1-methyl-1H-imidazole-5-carbonyl)o- xy]-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androsta-1,4-diene-17.beta.-ca- rbothioic acid S-fluoromethyl ester; 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-17.alp- ha.-[(1,2,3-thiadiazole-5-carbonyl)oxy]-androsta-1,4-diene-17.beta.-carbot- hioic acid S-fluoromethyl ester; or a salt or solvate of any one thereof.

21. A compound of claim 1 wherein when R.sub.1 is a C.sub.1 fluoroalkyl, and R.sub.3 is methyl, and R.sub.4 and R.sub.5 are both fluorine, R.sub.2 represents --C(.dbd.O)-aryl or --C(.dbd.O)-heteroaryl, wherein heteroaryl is a 5 member heterocyclic aromatic ring containing 1-3 hetero atoms selected from N and S, or a 5 member heterocyclic aromatic ring containing 2-3 heteroatoms selected from N, O and S, or a 6 member heterocyclic aromatic ring containing 1-3 hetero atoms selected from N, O and S.

22. A compound according to claim 1 which is 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(- 4-methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-ca- rbothioic acid S-fluoromethyl ester.

23. A pharmaceutical composition comprising a compound of formula (I) as defined in claim 1 or a physiologically acceptable salt or solvate thereof in admixture with one or more physiologically acceptable diluents or carriers.

24. A method for the treatment of a human or animal subject with an inflammatory and/or allergic condition, which method comprises administering to said human or animal subject an effective amount of a compound of formula (I) as defined in claim 1 or a physiologically acceptable salt or solvate thereof.

25. A process for preparing a compound of formula (I) according to claim 1 which comprises alkylation of a compound of formula (II) ##STR00025## wherein R.sub.2, R.sub.3, R.sub.4, R.sub.5 and are as defined in claim 1.

26. A process according to claim 25 wherein alkylation is performed by reacting the compound of formula (II) with an alkyl or haloalkyl halide.

27. A compound of formula (II) ##STR00026## wherein R.sub.2 represents --C(.dbd.O)-aryl or --C(.dbd.O)-heteroaryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond; or a salt or a solvate thereof.

28. A compound of formula (XV) ##STR00027## wherein P represents a hydroxy protecting group and wherein R.sub.1 represents C.sub.1-6 alkyl or C.sub.1-6 haloalkyl; R.sub.2 represents --C(.dbd.O)-aryl or --C(.dbd.O)-heteroaryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond; or a salt or a solvate thereof.

29. A compound of formula (XVI) ##STR00028## or a derivative thereof wherein the 11-ketone is masked and wherein R.sub.1 represents C.sub.1-6 alkyl or C.sub.1-6 haloalkyl; R.sub.2 represents --C(.dbd.O)-aryl or --C(.dbd.O)-heteroaryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond; or a salt or a solvate thereof.

30. A compound of formula (I) ##STR00029## wherein R.sub.1 represents C.sub.1-6 alkyl; R.sub.2 represents --C(.dbd.O)-aryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond; or a salt or a solvate thereof.

31. The compound according to claim 30, wherein: R.sub.3 represents methyl (which may be in either the .alpha. or .beta. configuration); R.sub.4 and R.sub.5 are the same or different and each represents halogen; and represents a single or a double bond; and or a salt or a solvate thereof.

32. The compound according to claim 30, wherein is methyl.

33. The compound according to claim 30, wherein R.sub.4 and R.sub.5 are the same or different and each represents hydrogen, fluorine or chlorine.

34. The compound according to claim 30, wherein R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or fluorine.

35. The compound according to claim 30, wherein both R.sub.4 and R.sub.5 are fluorine.

36. The compound according to claim 30, wherein represents a double bond.

37. A method for the treatment of at least one condition selected from the group consisting of inflammatory and allergic conditions in a human or animal subject, which comprises administering an effective amount of the compound of formula (I) or a physiologically acceptable salt or solvate thereof as defined in claim 30 to said human or animal subject in need thereof for the treatment of said at least one condition.

38. A pharmaceutical composition comprising a compound of formula (I) as defined in claim 30 or a physiologically acceptable salt or solvate thereof in admixture with one or more physiologically acceptable diluents or carriers.

39. A process for preparing a compound of formula (I) according to claim 30 which comprises alkylation of a compound of formula (II) ##STR00030## wherein R.sub.2 represents --C(.dbd.O)-aryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond; or a salt or a solvate thereof.

40. The process according to claim 39, wherein alkylation is performed by reacting the compound of formula (II) with an alkyl halide.

41. A compound of formula (II) ##STR00031## wherein R.sub.2 represents --C(.dbd.O)-aryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond; or a salt or a solvate thereof.

42. A compound of formula (XV) ##STR00032## wherein P represents a hydroxy protecting group and wherein R.sub.1 represents C.sub.1-6 alkyl; R.sub.2 represents --C(.dbd.O)-aryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond; or a salt or a solvate thereof.

43. A compound of formula (XVI) ##STR00033## or a derivative thereof wherein the 11-ketone is masked and wherein R.sub.1 represents C.sub.1-6 alkyl; R.sub.2 represents --C(.dbd.O)-aryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond; or a salt or a solvate thereof.

44. A compound of formula (I) ##STR00034## wherein R.sub.1 represents C.sub.1-6 haloalkyl; R.sub.2 represents --C(.dbd.O)-heteroaryl, wherein said heteroaryl is a 5 member heterocyclic aromatic ring containing 1-3 hereto atoms selected from the N and S, or a 5 member heterocyclic aromatic ring containing 2-3 hetero atoms selected from the N, O and S, or a 6 member heterocyclic aromatic ring containing 1-3 hetero atoms selected from N, O and S; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond; or a salt or a solvate thereof.

45. The compound according to claim 44, wherein: R.sub.3 represents methyl (which may be in either the .alpha. or .beta. configuration); R.sub.4 and R.sub.5 are the same or different and each represents halogen; and represents a single or a double bond; or a salt or a solvate thereof.

46. The compound according to claim 44, wherein R.sub.1 represents fluoromethyl, chloromethyl, bromomethyl or 2'-fluoroethyl.

47. The compound according to claim 44, wherein R.sub.1 represents fluoromethyl.

48. The compound according to claim 44, wherein the heteroaryl of R.sub.2 represents a 5-member heterocyclic aromatic ring containing 1-3 hetero atoms selected from N and S, or a 5 member heterocyclic aromatic ring containing 2-3 hetero atoms selected from N, O and S which may optionally be substituted.

49. The compound according to claim 48, wherein the 5-membered heterocyclic aromatic ring is substituted with one or more substituents selected from the group consisting of C.sub.1-6alkyl, C.sub.1-6alkoxy and halogen.

50. The compound according to claim 49, wherein the 5-membered heterocyclic aromatic ring is selected from the group consisting of pyrrolyl and thiophenyl.

51. The compound according to claim 50, wherein the 5-membered heterocyclic ring is thiophenyl.

52. The compound according to claim 48, wherein the 5-membered heterocyclic ring contains 2 heteroatoms and each of said 2 heteroatoms is independently selected from the group consisting of O, N and S.

53. The compound according to claim 48, wherein the 5-membered heterocyclic ring is selected from the group consisting of thiazolyl, isothiazolyl, pyrazolyl and imidazolyl.

54. The compound according to claim 48, wherein the 5-membered heterocyclic ring contains 3 heteroatoms and each of said 3 heteroatoms is independently selected from the group consisting of O, N and S.

55. The compound according to claim 48, wherein the heterocycle of the 5-membered heterocyclic ring is thiadiazolyl.

56. The compound according to claim 48, wherein the 5-membered heterocyclic ring is substituted with one or more substituents selected from the group consisting of C.sub.1-6alkyl and halogen.

57. The compound according to claim 44, wherein R.sub.3 is methyl.

58. The compound according to claim 44, wherein R.sub.4 and R.sub.5 are the same or different and each represents hydrogen, fluorine or chlorine.

59. The compound according to claim 44, wherein R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or fluorine.

60. The compound according to claim 44, wherein both R.sub.4 and R.sub.5 are fluorine.

61. The compound according to claim 44, wherein represents a double bond.

62. A method for the treatment of at least one condition selected from the group consisting of inflammatory and allergic conditions in a human or animal subject, which comprises administering an effective amount of the compound of formula (I) or a physiologically acceptable salt or solvate thereof as defined in claim 44 to said human or animal subject in need thereof for the treatment of said at least one condition.

63. A pharmaceutical composition comprising a compound of formula (I) as defined in claim 44 or a physiologically acceptable salt or solvate thereof in admixture with one or more physiologically acceptable diluents or carriers.

64. A process for preparing a compound of formula (I) according to claim 44 which comprises alkylation of a compound of formula (II) ##STR00035## wherein R.sub.2 represents --C(.dbd.O)-heteroaryl, wherein said heteroaryl is a 5 member heterocyclic aromatic ring containing 1-3 hetero atoms selected from N and S, or a 5 member heterocyclic aromatic ring containing 2-3 hetero atoms selected from N, O and S, or a 6 member heterocyclic aromatic ring containing 1-3 hetero atoms selected from N, O and S; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond; or a salt or a solvate thereof.

65. The process according to claim 64, wherein alkylation is performed by reacting the compound of formula (II) with a haloalkyl halide.

66. A compound of formula (II) ##STR00036## wherein R.sub.2 represents --C(.dbd.O)-heteroaryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond; or a salt or a solvate thereof.

67. A compound of formula (XV) ##STR00037## wherein P represents a hydroxy protecting group and wherein R.sub.1 represents C.sub.1-6 haloalkyl; R.sub.2 represents --C(.dbd.O)-heteroaryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond; or a salt or a solvate thereof.

68. A compound of formula (XVI) ##STR00038## or a derivative thereof wherein the 11-ketone is masked and wherein R.sub.1 represents C.sub.1-6 haloalkyl; R.sub.2 represents --C(.dbd.O)-heteroaryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond; or a salt or a solvate thereof.

69. 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha- .-[(4-methyl-1,3-thiazole- 5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl ester or a salt or solvate thereof.

70. A method for the treatment of at least one condition selected from the group consisting of inflammatory and allergic conditions in a human or animal subject, which comprises administering an effective amount of the compound of claim 69 or a physiologically acceptable salt or solvate thereof to said human or animal subject in need thereof for the treatment of said at least one condition.

71. A pharmaceutical composition comprising the compound of claim 69 or a physiologically acceptable salt or solvate thereof in admixture with one or more physiologically acceptable diluents or carriers.
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