CA2551038A1 - Triazole derivatives as vasopressin antagonists - Google Patents

Triazole derivatives as vasopressin antagonists Download PDF

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CA2551038A1
CA2551038A1 CA002551038A CA2551038A CA2551038A1 CA 2551038 A1 CA2551038 A1 CA 2551038A1 CA 002551038 A CA002551038 A CA 002551038A CA 2551038 A CA2551038 A CA 2551038A CA 2551038 A1 CA2551038 A1 CA 2551038A1
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phenyl
compound
triazol
derivative
nitrogen atoms
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CA2551038C (en
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Justin Stephen Bryans
Patrick Stephen Johnson
Lee Richard Roberts
Thomas Ryckmans
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Pfizer Inc
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Abstract

Compounds of formula (I), or pharmaceutically acceptable derivatives thereof, wherein: V represents a direct link or -O-; Ring A represents an optionally substituted 5- to 7-membered saturated heterocyclic ring, or a phenylene group.

Claims (53)

1. ~A compound of formula (I), or a pharmaceutically acceptable derivative thereof, wherein:
X represents -[CH2]a-R or -[CH2]a-O-[CH2]b-R;
a represents a number selected from 0 to 6;
b represents a number selected from 0 to 6;
R represents H, CF3 or Het;
Het represents a 5- or 6-membered saturated, partially saturated or aromatic heterocyclic ring comprising either (a) 1 to 4 nitrogen atoms, (b) 1 oxygen atom or 1 sulphur atom, or (c) 1 oxygen atom ar 1 sulphur atom and 1 or 2 nitrogen atoms, optionally substituted with one or more groups independently selected from W;

Y and Y' independently represent one or more substituents independently selected from -[O]c-[CH2]d-R1 , which may be the same or different at each occurrence;
c at each occurrence independently represents a number selected from 0 or 1;
d at each occurrence independently represents a number selected from 0 to 6;
R1 at each occurrence independently represents H, halo, CF3, CN ar Het1;
Het1 at each occurrence independently represents a 5- or 6-membered unsaturated heterocyclic ring, comprising either (a) 1 to 4 nitrogen atoms, {b) 1 oxygen atom or 1 sulphur atom, or (c) 1 oxygen atom or 1 sulphur atom and 1 or 2 nitrogen atoms;
V represents a direct link or -O-;
Ring A represents a 5- to 7-membered saturated heterocyclic ring comprising either (a) 1 to 4 nitrogen atoms, (b) 1 oxygen atom or 1 sulphur atom, or (c) 1 oxygen atom or 1 sulphur atom and 1 or 2 nitrogen atoms; ring A being optionally substituted with one or more groups selected from C1-6 alkyl, phenyl or hydroxy;

Q represents a direct link or -N(R2)-;
R2 represents hydrogen or C1-6 alkyl;
Z represents -[O]e-[CH2]f-R3, a phenyl ring (optionally fused to a benzene ring or Het2, and the group as a whole being optionally substituted with one or more groups independently selected from W), or Het3 (optionally fused to an benzene ring or Het4, and the group as a whole being optionally substituted with one or more groups independently selected from W);
R3 represents C1-6 alkyl (optionally substituted with one or more groups independently selected from W), C3-6 cycloalkyl, C3-6 cycloalkenyl, phenyl (optionally substituted with one or more groups independently selected from W), Het25 or NR4R5;
e represents a number selected from 0 or 1;
f represents a number selected from 0 to 6;
Het2 and Het5 independently represent a 5- or 6-membered saturated, partially saturated or aromatic heterocyclic ring, comprising either (a) 1 to 4 nitrogen atoms, (b) 1 oxygen atom or 1 sulphur atom, or (c) 1 oxygen atom or 1 sulphur atom and 1 or
2 nitrogen atoms, optionally substituted with one or more groups selected from W;
Het3 represents a 4 to 6-membered saturated, partially saturated or aromatic heterocyclic ring, comprising either (a) 1 to 4 nitrogen atoms, (b) 1 oxygen atom or 1 sulphur atom, or (c) 1 oxygen atom or 1 sulphur atom and 1 or 2 nitrogen atoms, optionally substituted with one or more groups selected from W;
Het4 represents a 6-membered aromatic heterocyclic ring, comprising either (a) to 4 nitrogen atoms, (b) 1 oxygen atom or 1 sulphur atom, or (c) 1 oxygen atom or 1 sulphur atom and 1 or 2 nitrogen atoms, optionally substituted with one or more groups selected from W;
R4 and R5 independently represent hydrogen, C1-6 alkyl, C1-6 alkyloxy, C3-8 cycloalkyl (optionally fused to C3-8 cycloalkyl) or Het6;
R4 and R5 being optionally independently substituted with one of more groups selected from C1-6 alkyl, C1-6 alkyloxy, C3-8 cycloalkyl (optionally fused to C3-8 cycloalkyl), or phenyl;
Het6 represents a 5- or 6-membered saturated, partially saturated or aromatic heterocyclic ring, comprising either (a) 1 to 4 nitrogen atoms, (b) 1 oxygen atom or 1 sulphur atom, or (c) 1 oxygen atom or 1 sulphur atom and 1 or 2 nitrogen atoms, optionally substituted with one or more groups selected from W;

W independently at each occurrence represents halo, [O]g R6, SO2 R6, SR6, SO2NR6R7, [O]h(CH2]i CF3, [O]j CHF2, phenyl (optionally substituted with halo, C1-6 alkyl or C1-6 alkyloxy), CN, phenoxy (optionally substituted with halo), OH, benzyl, NR6R7, NCOR6, benzyloxy, oxo, CONHR6, NSO2R6R7, COR6, C1-6alkylene-NCOR7, Het7;
R6 represents hydrogen, C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkenyl or C1-6alkylene-0-C1-6alkyl;
R7 represents hydrogen or C1-6alkyl;
i represents a number selected from 0 to 6;
h represents a number selected from 0 or 1;
g represents a number selected from 0 or 1;
j represents a number selected from 0 or 1;
Het7 represents a 5- or 6-membered saturated, partially saturated or aromatic heterocyclic ring, comprising either (a) 1 to 4 nitrogen atoms, (b) 1 oxygen atom or 1 sulphur atom, or (c) 1 oxygen atom or 1 sulphur atom and 1 or 2 nitrogen atoms, optionally substituted by R6 and/or R7 and/or an oxo group.

2. ~The compound or derivative according to claim 1, wherein X represents -[CH2]a-R.
3. ~The compound or derivative according to claim 1 or 2, wherein R represents Het.
4. ~The compound or derivative according to any one of claims 1 to 3, wherein Y represents halo.
5. ~The compound or derivative according to any one of claims 1 to 4, wherein V represents a direct link.
6. ~The compound or derivative according to any one of claims 1 to 5, wherein Q represents a direct link.
7. ~The compound or derivative according to any one of claims 1 to 6, wherein ring A represents a six-membered ring.
8. ~The compound or derivative according to any one of claims 1 to 7, wherein Z represents phenyl.
9. ~The compound or derivative according to any one of claims 1 to 8, wherein Z is substituted with halo.
10. ~A compound of formula (I'):
or a pharmaceutically acceptable derivative thereof, wherein:
X represents -[CH2]a-R or -[CH2]a-O-[CH2]b-R;
a represents a number selected from 0 to 6;
b represents a number selected from 0 to 6;
R represents H, CF3 or Het;
Het represents a 5- or 6-membered heterocyclic ring comprising either (a) 1 to 4 nitrogen atoms, (b) 1 oxygen atom or 1 sulphur atom, or (c) 1 oxygen atom or 1 sulphur atom and 1 or 2 nitrogen atoms;
Y represents -[O]c-[CH2]d-R1;

Y' represents -[O]c'-[CH2]d'-R1';
c and c' independently represent a number selected from 0 or 1;
d and d' independently represent a number selected from 0 to 6;
R1 and R1' independently represent H, halo, CF3 or Het1;
Het1 represents a 5- or 6-membered unsaturated heterocyclic ring comprising either (a) 1 to 4 nitrogen atoms, (b) 1 oxygen atom or 1 sulphur atom, or (c) 1 oxygen atom or 1 sulphur atom and 1 or 2 nitrogen atoms;
Ring A represents a 5- or 6-membered saturated heterocyclic ring comprising at least one nitrogen atom;
Z represents -[O]e-[CH2]f-R2, a phenyl ring (optionally fused to a phenyl ring or a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, and/or optionally substituted with one or more groups independently selected from W), or a 6-membered aromatic heterocyclic ring (optionally fused to a phenyl ring or a 6-membered aromatic heterocyclic ring, and/or optionally substituted with one or more groups independently selected from W);
R2 represents C1-6alkyl or C3-6cycloalkyl;
e represents a number selected from 0 or 1;
f represents a number selected from 0 to 6;
W represents halo, [O]g R3, SO2R3, SR3, SO2NR3R4, [O]h[CH2]i CF3, OCHF2, phenyl, CN, phenoxy (optionally substituted with halo), OH, benzyl, NCOR3, benzyloxy, oxy, CONHR3, NSO2R3R4, COR3, C1-6alkylene-NCOR3, Het2;
R3 represents hydrogen, C1-6alkyl, C3-6cycloalkyl or C1-6alkylene-O-C1-6alkyl;
R4 represents hydrogen or C1-6alkyl;
i represents a number selected from 0 to 6;
h represents a number selected from 0 or 1;
g represents a number selected from 0 or 1;
Het2 represents a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic group comprising either (a) 1 to 4 nitrogen atoms, (b) 1 oxygen atom or sulphur atom, or (c) 1 oxygen atom or 1 sulphur atom and 1 or 2 nitrogen atoms, the heterocyclic group being optionally substituted by R3 and/or R4 and/or an oxy group.
11. ~A compound (3-chloro-phenyl)-{4-[4-(4-chloro-phenyl)-5-[1,2,3]triazol-2-ylmethyl-4H-[1,2,4]triazol-3-yl]-piperidin-1-yl}-methanone, or a pharmaceutically derivative thereof.
12. ~A compound (4-chloro-phenyl)-{4-[4-(4-chloro-phenyl)-5-[1,2,3]triazol-2-ylmethyl-4H-[1,2,4]triazol-3-yl]-piperidin-1-yl}-methanone, or a pharmaceutically derivative thereof.
13. ~A compound (5-chloro-2-fluoro-phenyl)-{4-[4-(4-chloro-phenyl)-5-[1,2,3]triazol-2-ylmethyl-4H-[1,2,4]triazol-3-yl]-piperidin-1-yl}-methanone, or a pharmaceutically derivative thereof.
14. ~A compound {4-[4-(4-chloro-phenyl)-5-[1,2,3]triazol-2-ylmethyl-4H-[1,2,4]triazol-3-yl]-piperidin-1-yl}-(3,5-difluoro-phenyl)-methanone, or a pharmaceutically derivative thereof.
15. ~A compound {4-[4-(4-chloro-phenyl)-5-[1,2,3]triazol-2-ylmethyl-4H-[1,2,4]triazol-3-yl]-piperidin-1-yl}-(3-fluoro-phenyl)-methanone, or a pharmaceutically derivative thereof.
16. ~A compound {4-[4-(4-chloro-phenyl)-5-[1,2,3]triazol-2-ylmethyl-4H-[1,2,4]triazol-3-yl]-piperidin-1-yl}-(2,3-difluoro-phenyl)-methanone, or a pharmaceutically derivative thereof.~
17. ~A compound (3-chloro-2-fluoro-phenyl)-{4-[4-(4-chloro-phenyl)-5-[1,2,3]triazol-2-ylmethyl-4H-[1,2,4]triazol-3-yl]-piperidin-1-yl}-methanone, or a pharmaceutically derivative thereof.
18. ~A compound (3-chloro-4-fluoro-phenyl)-{4-[4-(4-chloro-phenyl)-5-[1,2,3]triazol-2-ylmethyl-4H-[1,2,4]triazol-3-yl]-piperidin-1-yl}-methanone, or a pharmaceutically derivative thereof.
19. ~A compound {4-[4-(4-chloro-phenyl)-5-[1,2,3]triazol-2-ylmethyl-4H-[1,2,4]triazol-3-yl]-piperidin-1-yl}-(4-trifluoromethyl-phenyl)-methanone, or a pharmaceutically derivative thereof.
20. ~A compound {4-[4-(4-chloro-phenyl)-5-[1,2,3]triazol-2-ylmethyl-4H-[1,2,4]triazol-3-yl]-piperidin-1-yl}-(3-trifluoromethyl-phenyl)-methanone, or a pharmaceutically derivative thereof.
21. ~A compound {4-[4-(4-chloro-phenyl)-5-[1,2,3]triazol-2-ylmethyl-4H-[1,2,4]triazol-3-yl]-piperidin-~
1-yl}-(2-trifluoromethyl-phenyl)-methanone, or a~~
pharmaceutically derivative thereof.
22. ~A compound (3-chloro-5-fluoro-phenyl)-{4-[4-(4-chloro-phenyl)-5-[1,2,3]triazol-2-ylmethyl-4H-[1,2,4]triazol-3-yl]-piperidin-1-yl}-methanone, or a pharmaceutically derivative thereof.
23. ~A compound {4-[4-(4-chloro-phenyl)-5-[1,2,3]triazol-2-ylmethyl-4H-[1,2,4]triazol-3-yl]-piperidin-1-yl}-(4-difluoromethyl-phenyl)-methanone, or a pharmaceutically derivative thereof.
24. ~A compound {4-[4-(4-chloro-phenyl)-5-[1,2,3]triazol-2-ylmethyl-4H-[1,2,4]triazol-3-yl]-piperidin-1-yl}-(1H-indazol-3-yl)-methanone, or a pharmaceutically derivative thereof.
25. ~The use of a compound or derivative according to any one of claims 1 to 24 as a medicament.
26. ~Use of a compound or derivative according to any one of claims 1 to 24 in the manufacture of a medicament for the treatment of a disorder for which a V1a receptor antagonist is indicated.
27. ~Use of a compound or derivative according to any one of claims 1 to 24 in the manufacture of a medicament for the treatment of anxiety, cardiovascular disease, dysmenorrhoea, endometriosis, emesis, intrauterine growth retardation, inflammation, mittlesmerchz, preclampsia, premature ejaculation, premature labour or Raynaud's disease.
28. ~Use according to claim 27, wherein the cardiovascular disease is angina, atherosclerosis, hypertension, heart failure, edema or hypernatremia.
29. ~Use according to claim 27, wherein the dysmenorrhoea is primary dysmenorrhea.
30. ~Use according to claim 27, wherein the dysmenorrhea is secondary dysmenorrhea.
31. ~Use according to claim 27, wherein the emesis is motion sickness.
32. ~Use according to claim 27, wherein the inflammation is rheumatoid arthritis.
33. ~A pharmaceutical formulation comprising a compound or derivative according to any one of claims 1 to 24, together with a pharmaceutically acceptable excipient, diluent or carrier.
34. ~The pharmaceutical composition according to claim 33 for treating a disorder in a mammal for which a V1a antagonist is indicated.
35. ~The pharmaceutical composition according to claim 33 for treating anxiety, cardiovascular disease, dysmenorrhoea, endometriosis, emesis, intrauterine growth retardation, inflammation, mittlesmerchz, preclampsia, premature ejaculation, premature labour or Raynaud's disease in a mammal.
36. ~The pharmaceutical composition according to claim 35, wherein the cardiovascular disease is angina,~
atherosclerosis, hypertension, heart failure, edema or hypernatremia.
37. The pharmaceutical composition according to claim 35, wherein the dysmenorrhoea is primary dysmenorrhea.
38. The pharmaceutical composition according to claim 35, wherein the dysmenorrhea is secondary dysmenorrhea.
39. The pharmaceutical composition according to claim 35, wherein the emesis is motion sickness.
40. The pharmaceutical composition according to claim 35, wherein the inflammation is rheumatoid arthritis.
41. The pharmaceutical composition according to any one of claims 34 to 40, wherein the mammal is a human being.
42. Use of a therapeutically effective amount of a compound or derivative according to any one of claims 1 to 24 for treating anxiety, cardiovascular disease, dysmenorrhoea, endometriosis, emesis, intrauterine growth retardation, inflammation, mittlesmerchz, preclampsia, premature ejaculation, premature labour or Raynaud's disease in a mammal.
43. Use according to claim 42, wherein the cardiovascular disease is angina, atherosclerosis, hypertension, heart failure, edema or hypernatremia.
44. Use according to claim 42, wherein the dysmenorrhoea is primary dysmenorrhea.
45. Use according to claim 42, wherein the dysmenorrhea is secondary dysmenorrhea.
46. Use according to claim 42, wherein the emesis is motion sickness.
47. ~Use according to claim 42, wherein the inflammation is rheumatoid arthritis.
48. ~Use according to any one of claims 42 to 47, wherein the mammal is a human being.
49. ~A combination of (A) a compound or derivative according to any one of claims 1 to 24, and (B) another pharmacologically active ingredient.
50. ~A combination according to claim 49, wherein (B) is an oral contraceptive, PDEV inhibitor, COX inhibitor, NO-donor or L-arginine.
51. ~Use of a combination according to claim 49 or 50, for the manufacture of a medicament for combination therapy by simultaneous, sequential or separate administration, in the treatment of dysmenorrhoea.
52. ~Use, for treating dysmenorrhoea in a subject in need of such treatment, of a combination according to claim 49 or 50, wherein (A) and (B) are used in amounts which are together effective in treating the dysmenorrhea.
53. ~A pharmaceutical product containing a combination of (A) and (B) according to claim 49 or 50 as a combined preparation for simultaneous, separate or sequential use in treating primary or secondary dysmenorrhea.
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