IP Library Granted Patent US 7,183,306
Granted Patent B2
US 7,183,306 · App. 10/706,999 · Granted Feb 27, 2007

Pyrazole derivatives

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Quick Facts
Patent No.
US 7,183,306
App. No.
10/706,999
Granted
Feb 27, 2007
Kind
B2
Abstract

A compound of the formula (I): wherein R 1 is hydrogen or lower alkyl; R 2 is lower alkyl, etc.; R 3 is lower alkoxy, etc.; R 4 is hydroxy, etc.; X is O, S, etc.; Y is CH or N; Z is lower alkylene or lower alkenylene; and m is 0 or 1; or salts thereof, which are useful as a medicament.

Claims (37)

1. A compound of the formula (I):

wherein R 1 is hydrogen or lower alkyl;

R 2 is lower alkyl optionally substituted with halogen, hydroxy, lower alkoxyimino or lower alkoxy; lower alkenyl; cycloalkyl; cyano; lower alkanoyl; cycloalkylcarbonyl; N,N-di(lower)alkylcarbamoyl; carbamoyl; N-lower alkoxy-N-lower alkylcarbamoyl; amino; di(lower)alkylamino; lower alkoxycarbonylamino; N,N-di(lower)alkylcarbamoylamino; N-(N,N-di(lower)alkylcarbamoyl)-N-lower alkylamino; halogen; hydroxy; carboxy; lower alkoxycarbonyl; aroyl; lower alkylsulfonyl; lower alkoxy optionally substituted with lower alkoxy, N,N-di(lower)alkylcarbamoyl or halogen; cycloalkyloxy; lower alkylthio; or lower alkylsufinyl;

R 3 is lower alkyl optionally substituted with amino, carbamoylamino or lower alkylsulfonylamino; halogen; cyano; hydroxy; lower alkanoyloxy; lower alkylenedioxy;lower alkoxy optionally substituted with aryl, hydroxy, cyano, amino, lower alkoxycarbonylamino, lower alkylsulfonylamino or carbamoylamino; nitro; amino; lower alkylthio; lower alkylsulfinyl; or lower alkylsufonyl;

R 4 is a group of the formula:

R 5 —G—J—

in which G is —CO—;

J is —N (R 6 )—

(wherein R 6 is hydrogen or lower alkyl); and

 R 5 is amino optionally substituted with lower alkoxycarbonyl or lower alkyl; lower alkyl optionally substituted with hydroxy, lower alkoxycarbonylamino, lower alkanoyloxy, amino or halogen; lower alkoxy; hydrogen; or aryl;

X is O, S, SO or SO 2 ;

Y is CH;

Z is lower alkylene or lower alkenylene; and

m is 0 or 1;

or a salt thereof.

2. The compound of claim 1 , wherein

R 1 is hydrogen;

R 2 is lower alkyl optionally substituted with halogen, hydroxy, lower alkyoxyimino or lower alkoxy; cycloalkyl; halogen; lower alkoxy optionally substituted with halogen; or lower alkylthio;

R 3 is lower alkoxy optionally substituted with aryl, hydroxy, cyano, amino, lower alkoxyxcarbonylamino, lower alkylsulfonylamino or carbamoylamino;

X is O or S; and

Z is lower alkylene.

3. The compound of claim 2 , wherein

R 2 is lower alkyl optionally substituted with halogen; cycloalkyl; halogen; or lower alkoxy optionally substituted with halogen;

R 3 is lower alkoxy;

J is —NH— and

R 5 is amino or lower alkyl; and

X is O.

4. The compound of claim 3 , which is

N-(2-(4-[3-chloro-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]-phenoxy)ethyl)urea,

N-(4-[3-(difluoromethyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]benzyl)methanesulfonamide,

N-(4-[3-(difluoromethyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]benzyl)urea,

N-(2-(4-[3-(difluoromethyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenoxy)ethyl)urea,

N-(2-(4-[1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenoxy)ethyl)urea,

N-(2-(4-[3-cyclopropyl-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenoxy)ethyl)urea, or

N-(2-(4-[1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenoxylethyl)acetamide.

5. A pharmaceutical composition comprising the compound of claim 1 , as an active ingredient, in association with a pharmaceutically non-toxic carrier or excipient.

6. The compound of claim 4 , which is N-(2-(4-[1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenoxy)ethyl)urea.

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 Feb 23, 2004
From: SHIRAI, FUMIYUKI; AZAMI, HIDENORI; KAYAKIRI, NATSUKO; OKUMURA, KAZUO; NAKAMURA, KATSUYA
To: FUJISAWA PHARMACEUTICAL CO., LTD
Reel/Frame 015002/0164 →