Design, synthesis, and structure-activity relationships of novel pyrazolo[5,1-b]thiazole derivatives as potent and orally active corticotropin-releasing factor 1 receptor antagonists

Journal of Medicinal Chemistry

Volumn 55, Issue 19, 2012, Pages 8450-8463

  Takahashi, Yoshinori ^a   Hashizume, Minako ^a   Shin, Kogyoku ^a   Terauchi, Taro ^a   Takeda, Kunitoshi ^a   Hibi, Shigeki ^a   Murata Tai, Kaoru ^a   Fujisawa, Masae ^a   Shikata, Kodo ^a   Taguchi, Ryota ^a   Ino, Mitsuhiro ^a   Shibata, Hisashi ^a   Yonaga, Masahiro ^a  

^a EISAI CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 [2 CHLORO 6 METHOXY 4 (METHOXYMETHYL)PHENYL] 6 METHOXY N PROPYL N (TETRAHYDRO 2H PYRAN 4 YL)PYRAZOLO[5,1 B] [1,3]THIAZOLE 7 AMINE; 3 [2,6 DIMETHOXY 4 (METHOXYMETHYL)PHENYL] 6 METHOXY N PROPYL N (TETRAHYDRO 2H PYRAN 4 YL)PYRAZOLO[5,1 B][1,3] THIAZOLE 7 AMINE; 3 [2,6 DIMETHOXY 4 (METHOXYMETHYL)PHENYL] N ETHYL 6 METHIXY N (TETRAHYDRO 2H PYRAN 4 YL)PYRAZOLO[5,1 B][1,3] THIAZOL 7 AMINE; 3 [2,6 DIMETHOXY 4 (METHOXYMETHYL)PHENYL] N ISOBUTYL 6 METHOXY N (TETRAHYDRO 2H PYRAN 4 YL)PYRAZOLO[5,1 B]THIAZOL 7 AMINE; 3 [2,6 DIMETHOXY 4 (METHOXYMETHYL)PHENYL] N ISOPROPYL 6 METHOXY N (TETRAHYDRO 2H PYRAN 4 YL)PYRAZOLO[5,1 B][1,3] THIAZOL 7 AMINE; 3 [4 (ETHOXYMETHYL) 2,6 DIMETHOXYPHENYL] 6 METHOXY N PROPYL N (TETRAHYDRO 2H PYRAN 4 YL)PYRAZOLO[5,1 B][1,3] THIAZOL 7 AMINE; 3,5 DIMETHOXY 4 [6 METHOXY 7 [PROPYL(TETRAHYDRO 2H PYRAN 4 YL)AMINO]PYRAZOLO[5,1 B][1,3]THIAZOL 3 YL]BENZONITRILE; 4 [7 [BUTYL(TETRAHYDRO 2H PYRAN 4 YL)AMINO] 6 METHOXYPYRAZOLO[5,1 B]THIAZOL 3 YL] 3,5 DIMETHOXYBENZONITRILE; 4 [[(CYCLOPROYLMETHYL) [3 [2,6 DIMETHOXY 4 (METHOXYMETHYL)PHENYL] 6 METHOXYPYRAZOLO[5,1 B][1,3]THIAZOL 7 YL}AMINO]METHYL]TETRAHYDRO 2H PYRAN 4 OL; 6 METHOXY 3 [2 METHOXY 4 (METHOXYMETHYL)PHENYL] N PROPYL N (TETRAHYDRO 2H PYRAN 4 YL)PYRAZOLO[5,1 B][1,3] THIAZOL 7 AMINE; 6 METHOXYPYRAZOLO[5,1 B][1,3]THIAZOLE; CORTICOTROPIN RELEASING FACTOR ANTAGONIST; ETHYL 6 METHOXYPYRAZOLO[5,1 B][1,3]THIAZOLE 7 CARBOXYLATE; ETHYL 6 OXO 5,6 DIHYDROPYRAZOLO[5,1 B][1,3]THIAZOLE 7 CARBOXYLATE; N (2 CYCLOPROPYLETHYL) 3 [4 (ETHOXYMETHYL) 2,6 DIMETHOXYPHENYL] 6 METHOXY N (TETRAHYDRO 2H PYRAN 4 YL)PYRAZOLO[5,1 B][1,3]THIAZOLE 7 AMINE; N (CYCLOPROYLMETHYL) 3 [2,6 DIMETHOXY 4 (METHOXYMETHYL)PHENYL] 6 METHOXY N (2 METHOXYETHYL) PYRAZOLO[5,1 B][1,3]THIAZOL 7 AMINE; N (CYCLOPROYLMETHYL) 3 [2,6 DIMETHOXY 4 (METHOXYMETHYL)PHENYL] 6 METHOXY N (TETRAHYDRO 2H PYRAN 4 YL)PYRAZOLO[5,1 B][1,3]THIAZOLE 7 AMINE; N (CYCLOPROYLMETHYL) 3 [2,6 DIMETHOXY 4 (METHOXYMETHYL)PHENYL] 6 METHOXY N [(TETRAHYDRO 2H PYRAN 2 YL)METHYL)PYRAZOLO[5,1 B][1,3]THIAZOL 7 AMINE; N (CYCLOPROYLMETHYL) 3 [2,6 DIMETHOXY 4 (METHOXYMETHYL)PHENYL] 6 METHOXY N [(TETRAHYDRO 2H PYRAN 3 YL)METHYL)PYRAZOLO[5,1 B][1,3]THIAZOL 7 AMINE; N (CYCLOPROYLMETHYL) 3 [2,6 DIMETHOXY 4 (METHOXYMETHYL)PHENYL] 6 METHOXY N [(TETRAHYDRO 2H PYRAN 4 YL)METHYL]PYRAZOLO[5,1 B][1,3]THIAZOL 7 AMINE; N (CYCLOPROYLMETHYL) 3 [2,6 DIMETHOXY 4 (METHOXYMETHYL)PHENYL] 6 METHOXY N [(TETRAHYDROFURAN 2 YL)METHYL]PYRAZOLO[5,1 B][1,3]THIAZOL 7 AMINE; N (CYCLOPROYLMETHYL) 3 [2,6 DIMETHOXY 4 (METHOXYMETHYL)PHENYL] 6 METHOXY N [(TETRAHYDROFURAN 3 YL)METHYL]PYRAZOLO[5,1 B][1,3]THIAZOL 7 AMINE; N (CYCLOPROYLMETHYL) 3 [2,6 DIMETHOXY 4 (METHOXYMETHYL)PHENYL] 6 METHYL N (TETRAHYDRO 2H PYRAN 4YLMETHYL)PYRAZOLO[5,1 B][1,3]THIAZOL 7 AMINE; N BUTYL 3 [2,6 DIMETHOXY 4 (METHOXYMETHYL)PHENYL] 6 METHOXY N (TETRAHYDRO 2H PYRAN 4 YL)PYRAZOLO[5,1 B][1,3] THIAZOLE 7 AMINE; N BUTYL 3 [4 (ETHOXYMETHYL) 2,6 DIMETHOXYPHENYL] 6 METHOXY N (TETRAHYDRO 2H PYRAN 4 YL)PYRAZOLO [5,1 B][1,3]THIAZOLE 7 AMINE; N BUTYL 3 [4 (ETHOXYMETHYL) 2,6 DIMETHOXYPHENYL] 6 METHOXY N(TETRAHYDRO 2H PYRAN 4 YL)PYRAZOLO[5,1 B][1,3] THIAZOLE 7 AMINE; PYRAZOLO[5,1 B]THIAZOLE DERIVATIVE; TERT BUTYL (3 BROMO 6 METHOXYPYRAZOLO[5,1 B][1,3]THIAZOL7 YL)CARBAMATE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG MECHANISM; DRUG SYNTHESIS; IC 50; MALE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; ADRENOCORTICOTROPIC HORMONE; ANIMALS; ANTI-ANXIETY AGENTS; CELL LINE, TUMOR; CORTICOTROPIN-RELEASING HORMONE; CYCLIC AMP; DEFECATION; DRUG DESIGN; HEK293 CELLS; HUMANS; MALE; MICE; MICE, INBRED BALB C; MODELS, MOLECULAR; PYRAZOLES; RADIOLIGAND ASSAY; RATS; RATS, INBRED F344; RATS, SPRAGUE-DAWLEY; RECEPTORS, CORTICOTROPIN-RELEASING HORMONE; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 84867378507     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300864p     Document Type: Article

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