| US 7,517,878 B2 | ||
| Heteroarylaminopyrazole derivatives useful for the treatment of diabetes | ||
| Joachim Rudolph, Guilford, Conn. (US); Philip Wickens, Wallingford, Conn. (US); Chih-Yuan Chuang, San Mateo, Calif. (US); Libing Chen, Milford, Conn. (US); Steven Magnuson, Wallingford, Conn. (US); Alan Olague, Shelton, Conn. (US); and Ning Qi, Hamden, Conn. (US) | ||
| Assigned to Bayer Pharamceuticals Corporation, West Haven, Conn. (US) | ||
| Filed on Feb. 24, 2005, as Appl. No. 11/64,700. | ||
| Claims priority of provisional application 60/572906, filed on May 20, 2004. | ||
| Claims priority of provisional application 60/548331, filed on Feb. 27, 2004. | ||
| Prior Publication US 2005/0192294 A1, Sep. 01, 2005 | ||
| Int. Cl. C07D 403/12 (2006.01); A61K 31/4155 (2006.01) | ||
| U.S. Cl. 514—235.5 [514/341; 546/275.4; 544/124] | 9 Claims |
1. A heteroarylaminopyrazole compound of Formula (I)
  is a substituted heterocyclic aromatic ring radical selected from
 R is H, or (C1-C6)alkyl;
R1 is H,
(C1-C6)alkyl optionally substituted with phenyl, said phenyl being optionally substituted with halo, or [tri(C1-C4)alkyl]silyl,
(C3-C6)alkenyl,
(C3-C6)alkynyl,
(C3-C6)cycloalkyl optionally substituted with up to two substituents selected from the group consisting of (C1-C3)alkyl, CF3, and halo,
(C1-C3)haloalkyl, or
phenyl optionally substituted with up to two substituents selected from the group consisting of halo, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, (C1-C3)haloalkyl, (C1-C3)haloalkoxy, and cyano;
R2 is H,
halo,
(C1-C6)alkyl,
pyridyl optionally substituted with up to two substituents selected from the group consisting of (C1-C6)alkoxy, (C1-C6)alkylthio, halo, and (C1-C6)alkyl,
phenyl optionally substituted with up to two substituents selected from the group consisting of (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, cyano and halo,
pyrimidyl,
thienyl optionally substituted with up to two substituents selected from the group consisting of (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, cyano and halo,
benzothienyl, optionally substituted with up to two substituents selected from the group consisting of (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, cyano and halo,
or furyl optionally substituted with up to two substituents selected from the group consisting of (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, cyano and halo;
R3 is (C1-C6)alkyl,
(C3-C6)cycloalkyl,
(C2-C3)haloalkyl or
phenyl optionally substituted with up to four substituents selected from the group consisting of
(C1-C6)alkyl optionally substituted with one (C1-C4)alkoxy,
halo,
(C1-C3)haloalkyl,
(C1-C6)alkoxy,
(C1-C3)haloalkoxy,
(C1-C6)alkylthio, and
cyano;
R4 is (C1-C6)alkyl optionally substituted with one (C1-C4)alkoxy,
(C1-C6)alkoxy,
(C1-C6)alkylthio,
(C1-C3)haloalkyl,
(C1-C3)haloalkoxy, or
halo;
n =0, 1, 2, or 3;
X is CO2R7, CONR5R6, or SO2NH2;
R5 is H, (C1-C6)alkyl, phenyl optionally substituted with halo or benzyl optionally substituted on the phenyl ring with halo;
R6 is H or (C1-C6)alkyl;
or
R5 and R6, taken together with N atom to which they are attached, may form a piperidine, morpholine, thiomorpholine, or piperazine
ring said piperazine optionally substituted on N with (C1-C3)alkyl;
R7 is H,
(C1-C6)alkyl,
benzyl optionally substituted on the aryl ring with up to two substituents selected from the group consisting of
halo,
(C1-C6)alkyl,
(C1-C3)alkoxy,
(C1-C3)haloalkyl,
(C1-C3)haloalkoxy, and
(C1-C6)alkylthio;
phenyl optionally substituted with up to two substituents selected from the group consisting of
(C1-C6)alkyl,
halo,
(C1-C6)alkoxy,
(C1-C3)haloalkyl,
(C1-C3)haloalkoxy, and
(C1-C6)alkylthio;
or a pharmaceutically acceptable salt thereof;
provided that the compound of Formula (I) is not
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