IP Library Granted Patent US 6,927,230
Granted Patent B2
US 6,927,230 · App. 10/344,416 · Granted Aug 9, 2005

Triazole derivatives

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Quick Facts
Patent No.
US 6,927,230
App. No.
10/344,416
Granted
Aug 9, 2005
Kind
B2
Abstract

A compound of the formula (I): wherein R 1 is lower alkyl which is optionally substituted with halogen, cyano, N,N-di(lower)alkylcarbamoyl, phenyl optionally substituted with halogen, or heterocyclic group, cyclo(lower)alkyl, lower alkynyl, or N,N-di(lower)alkylcarbamoyl; R 2 is lower alkyl, lower alkoxy, cyano, or 1H-pyrrol-1-yl; R 3 is lower alkyl, lower alkoxy, or cyano; X is O, S, SO or SO 2 ; Y and Z are each CH or N; and m is 0 or 1; or salts thereof, which are useful as a medicament.

Claims (43)

1. A compound of the formula (I):

wherein R 1 is lower alkyl which is optionally substituted with halogen, Cyano, N,N-di(lower)alkylcarbamoyl or phenyl optionally substituted with halogen

R 2 is lower alkyl, lower alkoxy, or cyano;

R 3 is lower alkyl, lower alkoxy, or cyano;

X is O;

Y and Z are each CH; and

m is 1;

or a salt thereof.

2. The compound of claim 1 , wherein

R 1 is lower alkyl,

lower alkyl substituted with halogen, cyano, or N,N-di(lower)alkylcarbamoyl;

R 2 is lower alkoxy;

R 3 is lower alkoxy;

X is O; Y and Z are each CH; and m is 0 or 1.

3. The compound of claim 2 , wherein

R 1 is lower alkyl or lower alkyl substituted with halogen;

R 2 is lower alkoxy;

R 3 is lower alkoxy;

X is O; Y and Z are each CH; and

m is 1.

4. The compound of claim 3 , wherein

R 1 is lower alkyl.

5. The compound of claim 1 , which is 3-methoxy-1,5-bis(4-methoxyphenyl)-1H-1,2,4-triazole.

6. A process for preparing a compound (I),

wherein R 1 is lower alkyl which is optionally substituted with halogen, cyano, N,N-di(lower)alkylcarbamoyl, or

phenyl optionally substituted with halogen;

R 2 is lower alkyl, lower alkoxy, or cyano;

R 3 is lower alkyl, lower alkoxy, or cyano;

X is O;

Y and Z are each CH; and

m is 1;

or a salt thereof, which comprises reacting a compound (VI) of a following formula:

wherein R 1 , X and m are each as defined above,

or a salt thereof, with a compound (VII) of a following formula:

wherein R 2 and Y are each as defined above, and L 3 is a leaving group,

or a salt thereof to give a compound (VIII) of a following formula:

wherein R 1 , R 2 , X, Y and m are each as defined above, or a salt thereof, and further reacting with a compound of (IX) of a following formula:

wherein R 3 and Z are each as defined above,

or a salt thereof to give a compound (I) or a salt thereof.

7. A pharmaceutical composition comprising the compound (I) of claim 1 or a salt thereof, as an active ingredient, and a pharmaceutically non-toxic carrier or excipient.

8. A method of treating pains caused by or associated with osteoarthritis comprising administering to a patient in need thereof an effective amount of the compound of claim 1 or a salt thereof.

9. A pharmaceutical composition comprising the compound of claim 5 or a salt thereof; and a pharmaceutically non-toxic carrier or excipient.

10. A method of treating pains caused by or associated with osteoarthritis comprising administering to a patient in need thereof an effective amount of the compound of claim 5 or a salt thereof.

Assignments (2)
MERGER Recorded Dec 12, 2005
From: FUJISAWA PHARMACEUTICAL CO., LTD.
To: ASTELLAS PHARMA INC.
Reel/Frame 017073/0257 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 1, 2003
From: AOKI, SATOSHI; NAKAGAWA, TOSHIYA; KONISHI, NOBUKIYO; NAKAMURA, KATSUYA; OMORI, HIROKI; KUBOTA, ARIYOSHI; HASHIMOTO, NORIO
To: FUJISAWA PHARMACEUTICAL CO., LTD.
Reel/Frame 013908/0245 →