Identification of novel 1,2,3,6-tetrahydropyridyl-substituted benzo[d]thiazoles: Lead generation and optimization toward potent and orally active EP1 receptor antagonists

Bioorganic and Medicinal Chemistry

Volumn 25, Issue 13, 2017, Pages 3406-3430

  Umei, Kentaro ^a   Nishigaya, Yosuke ^a   Tatani, Kazuya ^b   Kohno, Yasushi ^a   Tanaka, Nobuyuki ^b   Seto, Shigeki ^a  

^a KYORIN PHARMACEUTICAL CO LTD   (Japan)

^b KISSEI PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Benzo d thiazole; EP1 antagonist; Ligand lipophilicity efficiency

Indexed keywords

(5 CHLORO 2 PHENYLBENZO[D]THIAZOL 7 YL)METHANOL; (6 CHLORO 2 PHENYLBENZO[D]OXAZOL 4 YL)METHANOL; 1 [(5 CHLORO 2 PHENYLBENZO[D]OXAZOL 7 YL)METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLIC ACID; 1 [(5 CHLORO 2 PHENYLBENZO[D]THIAZOL 7 YL)METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLIC ACID; 1 [(6 CHLORO 2 PHENYLBENZO[D]OXAZOL 4 YL)METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLIC ACID; 1 [(6 CHLORO 2 PHENYLBENZO[D]THIAZOL 4 YL)METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLIC ACID; 1,2,3,6 TETRAHYDROPYRIDYL BENZO[D]THIAZOLE DERIVATIVE; 5 CHLORO 7 (CHLOROMETHYL) 2 PHENYLBENZO[D]THIAZOLE; 6 CHLORO 2 IODO 4 METHYLBENZO[D]THIAZOLE; 6 CHLORO 2 PHENYLBENZO[D]OXAZOLE 4 CARBALDEHYDE; 6 CHLORO 4 (CHLOROMETHYL) 2 PHENYLBENZO[D]OXAZOLE; ETHYL 1 [(5 CHLORO 2 PHENYLBENZO[D]OXAZOL 7 YL)METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLATE; ETHYL 1 [(5 CHLORO 2 PHENYLBENZO[D]THIAZOL 7 YL)METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLATE; ETHYL 1 [(6 CHLORO 2 CYCLOHEXYLBENZO[D]THIAZOL 4 YL)METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLATE; ETHYL 1 [(6 CHLORO 2 IODOBENZO[D]THIAZOL 4 YL)METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLATE; ETHYL 1 [(6 CHLORO 2 PHENYLBENZO[D]OXAZOL 4 YL)METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLATE; ETHYL 1 [[6 CHLORO 2 (CYCLOHEX 1 EN 1 YL)BENZO[D]THIAZOL 4 YL]METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLATE; ETHYL 1 [[6 CHLORO 2 (DIETHYLAMINO)BENZO[D]THIAZOL 4 YL]METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLATE; ETHYL 1 [[6 CHLORO 2 (DIMETHYLAMINO)BENZO[D]THIAZOL 4 YL]METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLATE; ETHYL 1 [[6 CHLORO 2 (METHYLAMINO)BENZO[D]THIAZOL 4 YL]METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLATE; ETHYL 1 [[6 CHLORO 2 (PROP 1 EN 2 YL)BENZO[D]THIAZOL 4 YL]METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLATE; ETHYL 1 [[6 CHLORO 2 [ETHYL(METHYL)AMINO]BENZO[D]THIAZOL 4 YL]METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLATE; ETHYL 1 [[6 CHLORO 2 [ETHYL(PROPYL)AMINO]BENZO[D]THIAZOL 4 YL]METHYL] 5 METHYL 1H PYRAZOLE 3 CARBOXYLATE; ETHYL 5 METHYL 1 [(6 CHLORO 2 PHENYLBENZO[D]THIAZOL 4 YL)METHYL] 1H PYRAZOLE 3 CARBOXYLATE; METHYL 2,5 DICHLORO 3 PHENYLTHIOAMIDOBENZOATE; METHYL 3 BENZAMIDO 2,5 DICHLOROBENZOATE; METHYL 5 CHLORO 2 PHENYLBENZO[D]THIAZOLE 7 CARBOXYLATE; PROSTAGLANDIN E RECEPTOR 1; PROSTAGLANDIN RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG; 17-PHENYLTRINORPROSTAGLANDIN E2; BENZOTHIAZOLE DERIVATIVE; LIGAND; PROSTAGLANDIN E2;

ANIMAL EXPERIMENT; ANIMAL MODEL; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DRUG ABSORPTION; DRUG EFFICACY; DRUG HALF LIFE; DRUG IDENTIFICATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; HYDROPHOBICITY; IC50; LIPOPHILICITY; NONHUMAN; NUCLEOPHILICITY; PROCESS OPTIMIZATION; RAT; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; ANALOGS AND DERIVATIVES; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMICALLY INDUCED; CHEMISTRY; DISEASE MODEL; DOSE RESPONSE; ORAL DRUG ADMINISTRATION; URINARY BLADDER, OVERACTIVE;

ADMINISTRATION, ORAL; ANIMALS; BENZOTHIAZOLES; DINOPROSTONE; DISEASE MODELS, ANIMAL; DOSE-RESPONSE RELATIONSHIP, DRUG; LIGANDS; MOLECULAR STRUCTURE; RATS; RECEPTORS, PROSTAGLANDIN E, EP1 SUBTYPE; STRUCTURE-ACTIVITY RELATIONSHIP; URINARY BLADDER, OVERACTIVE;

EID: 85018770853     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2017.04.028     Document Type: Article

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