Pyrazolo[1,5-a]pyridines and medicines containing the same

1. A compound represented by the general formula:

wherein R 1 represents a hydrogen, halogen, nitro, cyano or the formula —G 1 —R 1a (wherein G 1 represents a single bond, methylene, oxygen, sulfur, sulfinyl, sulfonyl, —C(O)—, —C(O)O—, —OC(O)—, —NR 1b —, —C(O)—NR 1b —, —S(O) 2 —NR 1b —, —NR 1b —C(O)— or —NR 1b —S(O) 2 —; and R 1a and R 1b each independently represent hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 3-8 cycloalkyl or C 5-8 cycloalkenyl);

R 2 , R 3 and R 4 each independently represents a hydrogen, halogen, cyano, nitro, hydroxyl, C 6-14 aryl, a 5- to 14-membered heteroaryl group or the formula —G 2 —R 2a (wherein G 2 represents a single bond, C 1-6 alkylene, oxygen, sulfur, sulfinyl, sulfonyl, —C(O)—, —C(O)O—, —OC(O)—, —NR 2b —, —C(O)—NR 2b —, —S(O) 2 —NR 2b —, —NR 2b —C(O)— or —NR 2b —S(O) 2 —; R 2a and R 2b each independently represent hydrogen, C 1-6 alkyl optionally substituted with 1–3 halogen, C 2-10 alkenyl, C 2-10 alkynyl, C 3-8 cycloalkyl or C 5-8 cycloalkenyl);

R 2 and R 3 or R 3 and R 4 may bond together to form a 5- to 7-membered ring optionally containing 1 to 4 hetero atoms in the ring and optionally containing carbonyl in the ring;

R 5 and R 6 each independently represents a formula —X 5 —X 6 —X 7 (wherein X 5 represents a single bond or —CO—; X 6 represents a single bond, —NR 3a —, oxygen, sulfur, sulfinyl, sulfonyl, C 1-10 alkylene, C 2-10 alkenylene or C 2-10 alkynylene; and X 7 and R 3a each independently represent hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 3-8 cycloalkyl, C 5-8 cycloalkenyl, C 6-14 aryl, a 5- to 14-membered heteroaryl group, a 4- to 14-membered heterocyclic group, a 9- to 11-membered benzene fused ring group, an 8- to 11-membered heteroaryl fused ring group or a bicyclic 7- to 12-membered hydrocarbon ring group);

R 5 and R 6 may bond together to form a 5- to 10-membered ring optionally containing 1 to 4 hetero atoms in the ring and optionally containing carbonyl in the ring;

R 6 and R 2 may bond together to form a 6- to 7-membered ring optionally containing 1 or 2 hetero atoms in the ring and optionally containing carbonyl in the ring; and

Ar represents a C 6-14 aryl, a 5- to 14-membered heteroaryl group, a 9- to 11-membered benzene fused ring group or an 8- to 11-membered heteroaryl fused ring group; with the proviso that R 1a , R 1b , R 3a , X 6 , X 7 and Ar may each independently have 1 to 4 groups selected from the group consisting of a halogen, cyano, hydroxyl, nitro, C 1-6 alkoxy, C 3-8 cycloalkyl, C 1-6 alkyl, dimethylamino, methylenedioxy, ethylenedioxy, a formula —V 1 —V 2 —V 3 (wherein V 1 represents a single bond, C 1-6 alkylene, C 2-6 alkenylene, C 2-6 alkynylene, oxygen, sulfur, carbonyl,—CO—O—, —O—CO— or —NR 3b —; V 2 represents a single bond or C 1-6 alkylene; and V 3 and R 3b each independently represent C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-8 cycloalkyl, C 5-8 cycloalkenyl, C 6-14 aryl, a 5- to 14-membered heteroaryl group, a 4- to 14-membered heterocyclic group, hydrogen, halogen, hydroxyl, cyano, C 1-6 alkoxy or a formula —N(R 3c )R 3d (wherein R 3c and R 3d each independently represent hydrogen or C 1-6 alkyl)), a formula —V 4 —V 5 (wherein V 4 represents a single bond, oxygen, sulfur, sulfinyl or sulfonyl and V 5 represents C 1-6 alkyl optionally substituted with 1 to 3 halogen or C 3-8 cycloalkyl) and a formula —N(R 5a )R 5b (wherein R 5a and R 5b each independently represent hydrogen or C 1-6 alkyl); a salt thereof or a hydrate of the foregoing.

2. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein R 1 is a formula —G 10 —R 10 (wherein G 10 represents a single bond, methylene, oxygen, sulfur, sulfinyl or sulfonyl and R 10 represents C 1-6 alkyl optionally substituted with 1 to 3 halogen, C 2-6 alkenyl, C 26 alkynyl or C 3-8 cycloalkyl).

3. The compound according to claim 2 , a salt of the compound or a hydrate of the foregoing, wherein R 10 is methyl, ethyl, n-propyl, iso-propyl, trifluoromethyl, difluoromethyl, monofluoromethyl, cyclopropyl or cyclobutyl.

4. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein R 1 is methoxy.

5. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein R 1 is ethyl.

6. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein R 1 is methylthio.

7. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein R 2 , R 3 and R 4 each independently represents hydrogen, halogen, cyano, nitro, hydroxyl, or the formula —G 20 —R 20 (wherein G 20 represents a single bond, oxygen, sulfur, sulfinyl or sulfonyl, and R 20 represents C 1-6 alkyl optionally substituted with 1 to 3 halogen, C 2-10 alkenyl, C 2-10 alkynyl or C 3-8 cycloalkyl).

8. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein R 2 , R 3 and R 4 are hydrogen.

9. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein Ar is phenyl, 1,3-benzodioxolyl, naphthyl, pyridyl, pyrazyl, pyrimidyl, pyridazyl, thienyl, furanyl, imidazolyl, thiazolyl, quinolinyl, isoquinolinyl, indolinyl, benzofuranyl, benzothienyl, oxazolyl or isoxazolyl, and Ar may have 1 to 4 groups selected from the group consisting of halogen, cyano, hydroxyl, nitro, methylenedioxy, ethylenedioxy, the formula —V 4 —V 5 and the formula —N(R 5a )R 5b .

10. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein Ar is phenyl or pyridyl, and Ar may optionally have 1 to 3 groups selected from the group consisting of halogen, cyano, hydroxyl, nitro, methylenedioxy, ethylenedioxy, the formula —V 4 —V 5 and the formula —N(R 5a )R 5b .

11. The compound according to claim 9 , a salt of the compound or a hydrate of the foregoing, wherein Ar may have 1 to 4 groups selected from the group consisting of halogen, cyano, C 1-6 alkyl optionally substituted with 1 to 3 halogen, C 3-8 cycloalkyl, dimethylamino and C 1-6 alkoxy optionally substituted with 1 to 3 halogen.

12. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein Ar is the formula:

(wherein R 40 and R 41 each independently represent methoxy, ethoxy, ethyl, methyl, dimethylamino or halogen, R 42 represents hydrogen, methoxy, methyl, dimethylamino or halogen, and Z 1 and Z 2 each independently represent methine or nitrogen).

13. The compound according to claim 12 , a salt of the compound or a hydrate of the foregoing, wherein Z 1 and Z 2 are methine.

14. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein

X 5 is a single bond, and

X 6 is a single bond, C 1-6 alkylene optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 , C 2-6 alkenylene optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 , or C 2-6 alkynylene optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 .

15. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein

X 5 is a single bond, and

X 6 is a single bond or C 1-6 alkylene optionally having 1 to 3 groups selected from the group consisting of halogen, hydroxyl, C 1-6 alkoxy, cyano, C 3-8 cycloalkyl, and C 1-6 alkyl.

16. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein

X 5 is a single bond, and

X 6 is a single bond, 1,2-ethylene or methylene.

17. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein X 7 is C 1-10 alkyl optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 , C 2-10 alkenyl optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 , C 2-10 alkynyl optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 , C 3-8 cycloalkyl optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 , C 5-8 cycloalkenyl optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 , C 6-14 aryl optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 , a 5- to 14-membered heteroaryl group optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 , a 4- to 14-membered heterocyclic group optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 , or a bicyclic 7- to 12-membered hydrocarbon ring group optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 .

18. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein X 7 is C 1-10 alkyl optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 , C 3-8 cycloalkyl optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 , a 5- to 6-membered heteroaryl group optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 , or a 4- to 7-membered heterocyclic group optionally having 1 to 3 groups selected from the group consisting of methylenedioxy, ethylenedioxy and the formula —V 1 —V 2 —V 3 .

19. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein X 7 is C 1-10 alkyl optionally having 1 to 3 groups selected from below, the group consisting of halogen, hydroxyl, C 1-6 alkoxy, cyano, C 3-8 cycloalkyl, dimethylamino and C 1-6 alkyl, C 3-8 cycloalkyl optionally having 1 to 3 groups selected from the group consisting of halogen, hydroxyl, C 1-6 alkoxy, cyano, C 3-8 cycloalkyl, dimethylamino and C 1-6 alkyl, a 5- to 6-membered heteroaryl group optionally having 1 to 3 groups selected from the group consisting of halogen, hydroxyl, C 1-6 alkoxy, cyano, C 3-8 cycloalkyl, dimethylamino and C 1-6 alkyl, or a 4- to 7-membered heterocyclic group optionally having 1 to 3 groups selected from the group consisting of halogen, hydroxyl, C 1-6 alkoxy, cyano, C 3-8 cycloalkyl, dimethylamino and C 1-6 alkyl.

20. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein X 7 is hydrogen, C 1-10 alkyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, C 3-8 cycloalkyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, tetrahydrofuranyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, tetrahydrothiophenyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, dihydropyranyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, tetrahydropyranyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, dioxolanyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, pyrrolidin-2-onyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, dihydrofuran-2-onyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, furanyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, thienyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, pyrrolidinyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, piperidyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, oxazolyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, isoxazolyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, thiazolyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, pyrrolyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, pyrazolyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, morpholinyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, dioxanyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine, or pyridyl optionally having 1 or 2 groups selected from the group consisting of hydroxyl, methyl, ethyl, methoxy, dimethylamino, cyano, chlorine and fluorine.

21. The compound according to claim 20 , a salt of the compound or a hydrate of the foregoing, wherein the optional group is selected from the group consisting of methyl, methoxy, dimethylamino, chlorine and fluorine.

22. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein X 7 is hydrogen, C 1-10 alkyl, C 3-8 cycloalkyl, tetrahydrofuranyl, tetrahydrothiophenyl, dihydropyranyl, tetrahydropyranyl, dioxolanyl, pyrrolidin-2-onyl, dihydrofuran-2-onyl, furanyl, thienyl, pyrrolidinyl, piperidyl, oxazolyl, isoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, morpholinyl, dioxanyl or pyridyl.

23. The compound according to claim 1 , a salt of the compound or a hydrate of the foregoing, wherein X 7 is hydrogen, C 1-10 alkyl, C 3-8 cycloalkyl, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyranyl, dioxolanyl, furanyl, thienyl, oxazolyl, dioxanyl, pyridyl, piperidyl or thiazolyl.

24. A pharmaceutical composition comprising a therapeutically effective dose of the compound according to claim 1 , or the salt thereof or hydrate thereof; and

a pharmaceutically acceptable carrier.