Aminoethanol derivatives

1. A compound represented by the formula

wherein

Ar 1 is an aromatic ring group optionally having substituents,

Ar 2 is an aromatic ring group having substituents,

OR″ is an optionally protected hydroxyl group,

R is an acyl group, and

R' is a hydrogen atom or a hydrocarbon group optionally having substituents, or a salt thereof;

except tert-butyl benzyl-[2(S)-hydroxy-2-thiazol-2-yl-1(S)-(4-trifluoromethyl-benzyl)-ethyl]-carbamate.

2. The compound of claim 1 , wherein Ar 1 is a 5- or 6-membered aromatic ring group optionally having substituents.

3. The compound of claim 1 , wherein Ar 1 is a phenyl group optionally having substituents.

4. The compound of claim 1 , wherein Ar 2 is a 5- or 6-membered aromatic ring group having substituents.

5. The compound of claim 1 , wherein Ar 2 is a phenyl group having substituents.

6. The compound of claim 1 , wherein R is a group represented by the formula R 1N CO— (R 1N is a hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents).

7. The compound of claim 6 , wherein R 1N is a cyclic hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents.

8. The compound of claim 1 , wherein R″ is a hydrogen atom or an acyl group.

9. The compound of claim 1 , wherein R″ is a group represented by the formula R 10 CO— (R 10 is a hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents).

10. The compound of claim 8 , wherein R 10 is an alkyl group optionally having substituents.

11. The compound of claim 1 , wherein R″ is a hydrogen atom.

12. The compound of claim 1 , wherein R′ is a hydrogen atom.

13. The compound of claim 1 , wherein R is a group represented by the formula R 1N CO— (R 1N is a cyclic hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents), R″ is a hydrogen atom and R′ is a hydrogen atom.

14. The compound of claim 1 , wherein Ar 1 is a 5- or 6-membered aromatic ring group optionally having substituents selected from halogen atom, optionally halogenated lower alkyl group, optionally halogenated lower alkoxy group and aryloxy group optionally having substituents, Ar 2 is a 5- or 6-membered aromatic ring group having substituents selected from halogen atom, optionally halogenated lower alkyl group and optionally halogenated lower alkoxy group, R is a C 1-6 alkoxy-carbonyl, a C 1-6 alkyl-carbonyl, a C 6-10 aryl-carbonyl, dihydronaphthalenecarbonyl, tetrahydronaphthalenecarbonyl, benzocycloheptenecarbonyl or benzocyclooctenecarbonyl, each of which may have substituent(s) selected from halogen atom, optionally halogenated C 1-6 alkoxy and optionally halogenated C 1-6 alkyl, R″ is a hydrogen atom, and R′ is a hydrogen atom.

15. The compound of claim 14 , wherein the 5- or 6-membered aromatic ring group is a phenyl group, a pyridyl group, a thienyl group, a furyl group or a thiazolyl group.

16. The compound of claim 14 , wherein the 5- or 6-membered aromatic ring group is a phenyl group, a pyridyl group or a thienyl group, and R is naphthalenecarbonyl, dihydronaphthalenecarbonyl, tetrahydronaphthalenecarbonyl, benzocycloheptenecarbonyl or benzocyclooctenecarbonyl, each of which may have substituent(s) selected from halogen atom, optionally halogenated C 1-6 alkoxy and optionally halogenated C 1-6 alkyl.

17. The compound of claim 1 , which is

N[(1RS2SR)-2-(4-fluorophenyl)-2-hydroxy-1-[4-fluoromethyl)benzyl]ethyl]-6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxamide,

4-fluoro-N-((1R,2S)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-1-naphthalenecarboxamide,

N-[(1R,2S)-2-(4-fluorophenyl)-2-hydroxy-1-[3-1,1,2,2-tetrafluoroethoxy)benzyl]ethyl]-6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxamide,

N-[(1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]ethyl]-5,6-dihydronaphthalene-1-carboxamide,

N-[(1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]ethyl]-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene-1-carboxamide,

4-fluoro-N-[(1R,2S)-2-(4-fluorophenyl)-2-hydroxy-1-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]ethyl]naphthalene-1-carboxamide,

N-[(1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]ethyl]-5,6,7,8-tetrahydrobenzo[a]cyclooctene-1-carboxamide,

N-[(1RS2SR)2-(4-fluorophenyl)-2-hydroxy-1-(4-isopropylbenzyl)ethyl]-6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxamide,

N-((1RS,2SR)-2-(3-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxamide,

N-((1RS,2SR)-2-hydroxy-2-(4-phenoxyphenyl)-1-((4(trifluoromethyl)phenyl)methyl)ethyl)-6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxamide,

N-((1RS,2SR)-2-(4-chlorophenyl)-2-hydroxy-1-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]ethyl-6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxamide,

N-((1RS,2SR)-2-hydroxy-2-(4-(phenyloxy)phenyl)-1-((3-((1,1,2,2-tetrafluoroethoxy)phenyl)methyl)ethyl)-6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxamide,

N-((1RS,2SR)-2-(4-((4-chloro-3-ethylphenyl)oxy)phenyl)-2-hydroxy-1-((3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)methyl)ethyl)-6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxamide,

N-((1RS,2SR)-2-(2-fluoropyridin-4-yl)-2-hydroxy-1-((3-(1,1,2,2-tetrafluoroetoxy)phenyl)mehyl)ethyl)-6,7-dihydro-5H-benzo[a]cycloheptene 1-carboxamide,

N-((1RS,2RS)-2-(6-fluoropyridin2-yl)-2-hydroxy-1-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)ethyl)-6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxamide,

N-[(1RS,2SR)-1-(4-tert-butylbenzyl)-2-(3-chorophenyl)-2-hydroxyethyl]-5- chlorol-1-naphthamide,

4-fluoro-N-{(1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methyl]ethyl}-1-naphthamide or a salt thereof.

18. A prodrug of a compound represented by the formula

wherein

Ar 1 is an aromatic ring group optionally having substituents

Ar 2 is an aromatic ring group having substituents,

OR″ is an optionally protected hydroxyl group,

R is an acyl group, and R′ is a hydrogen atom or a hydrocarbon group optionally having substituents, or a salt thereof,

except tert-butyl benzyl-[2(S)-hydroxy-2-thiazol-2-yl-1(S)-(4-trifluoromethyl-benzyl)-ethyl]-carbamate.

19. A pharmaceutical composition comprising a compound represented by the formula

wherein

Ar 1 is an aromatic ring group optionally having substituents,

Ar 2 is an aromatic ring group having substituents,

OR″ is an optionally protected hydroxyl group,

R is an acyl group, and

R′ is a hydrogen atom or a hydrocarbon group optionally having substituents,

or a salt thereof of a prodrug thereof.

20. The composition of claim 19 , which is a cholesteryl ester transfer protein inhibitor.

21. The composition of claim 19 , which is a high density lipoprotein-cholesterol elevating agent.

22. The composition of claim 19 , which is a low density lipoprotein-cholesterol lowering agent.

23. The composition of claim 19 , which is an very low density lipoprotein-cholesterol lowering agent.

24. The composition of claim 19 , which is a triglyceride lowering agent.

25. The composition of claim 19 , which is a prophylactic or therapeutic agent of acute coronart syndrome.

26. The composition of claim 19 , which is a prophylactic or therapeutic agent of acute cardiac infarction.

27. The composition of claim 19 , which is a prophylactic or therapeutic agent of unstable angina pectoris.

28. The composition of claim 19 , which is a prophylactic or therapeutic agent of PTCA or arterial restenosis after stent placement.

29. The composition of claim 19 , which is a prophylactic or therapeutic agent of peripheral arterial occlusion.

30. The composition of claim 19 , which is a prophylactic or therapeutic agent of hyperlipidemia.

31. The composition of claim 19 , which is a prophylactic or therapeutic agent of cerebral infarction.

32. The composition of claim 19 , which is a prophylactic or therapeutic agent of stroke.

33. The composition of claim 19 , which is a suppressor of progression of focal arteriosclerosis.

34. A cholesteryl ester transfer protein inhibitor comprising a compound represented by the formula

wherein

Ar 1 is an aromatic ring group optionally having substituents,

Ar 2 is an aromatic ring group optionally having substituents,

OR″ is an optionally protected hydroxyl group,

R is an acyl group, and

R′ is a hydrogen atom or a hydrocarbon group optionally having substituents,

or a salt thereof or a prodrug thereof.

35. The agent of claim 34 , which is a prophylactic or therapeutic agent of hyperlipidemia.

36. The agent of claim 34 , which is a prophylactic or therapeutic agent of acute coronary syndrome.

37. The agent of claim 34 , which is a prophylactic or therapeutic agent of acute cardiac infarction.

38. The agent of claim 34 , which is a prophylactic or therapeutic agent of unstable angina pectoris.

39. The agent of claim 34 , which is a prophylactic or therapeutic agent of PTCA or arterial restenosis after stent placement.

40. The agent of claim 34 , which is a prophylactic or therapeutic agent of peripheral arterial occlusion.

41. The agent of claim 34 , which is a prophylactic or therapeutic agent of cerebral infarction.

42. The agent of claim 34 , which is a prophylactic or therapeutic agent of stroke.

43. The agent of claim 34 , which is a suppressor of progression of focal arteriosclerosis.

44. A method of inhibiting cholesteryl ester transfer protein in a mammal, which comprises administering an effective amount of a compound of claim 1 or a salt thereof to the mammal.

45. A method for the prophylaxis or treatment of hyperlipidemia in a mammal, which comprises administering an effective amount of a compound of claim 1 or a salt thereof to the mammal.

46. A method for the prophylaxis or treatment of acute coronary syndrome in a mammal, which comprises administering an effective amount of a compound of claim 1 or a salt thereof to the mammal.

47. A method for the prophylaxis or treatment of acute cardiac infarction in a mammal, which comprises administering an effective amount of a compound of claim 1 or a salt thereof to the mammal.

48. A method for the prophylaxis or treatment of unstable angina pectoris in a mammal, which comprises administering an effective amount of a compound of claim 1 or a salt thereof to the mammal.

49. A method for the prophylaxis or treatment of PTCA or coronary resteiiosis after stent placement in a mammal, which comprises administering an effective amount of a compound of claim 1 or a salt thereof to the mammal.

50. A method for the prophylaxis or treatment of peripheral arterial occlusion in a mammal, which comprises administering an effective amount of a compound of claim 1 or a salt thereof to the mammal.

51. A method for the prophylaxis or treatment of cerebral infarction in a mammal, which comprises administering an effective amount of a compound of claim 1 or a salt thereof to the mammal.

52. A method for the prophylaxis or treatment of stroke in a mammal, which comprises admimistering an effective amount of a compound of claim 1 or a salt thereof to the mammal.

53. A method of suppressing progression of focal arteriosclerosis in a mammal, which comprises administering an effective amount of a compound of claim 1 or a salt thereof to the mammal.

54. A method of inhibiting cholesteryl ester transfer protein in a mammal, which comprises administering an effective amount of a compound represented by the formula (I′) of claim 34 or a salt thereof or a prodrug thereof to the mammal.

55. A production method of claim 1 or a salt thereof, which comprises subjecting a compound represented by the formula

wherein each symbol is as defined in claim 1 , or a salt thereof to an acylation reaction to give a compound represented by the formula

wherein each symbol is as defined in claim 1 , or a salt thereof, and, where desired, subjecting the compound to a hydroxyl group-protecting reaction.