A new class of non-thiazolidinedione, non-carboxylic-acid-based highly selective peroxisome proliferator-activated receptor (PPAR) γ agonists: Design and synthesis of benzylpyrazole acylsulfonamides

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 2, 2012, Pages 714-733

  Rikimaru, Kentaro ^a,d   Wakabayashi, Takeshi ^a,d   Abe, Hidenori ^a,d   Imoto, Hiroshi ^a,d   Maekawa, Tsuyoshi ^a,d   Ujikawa, Osamu ^a,d   Murase, Katsuhito ^b   Matsuo, Takanori ^a,e   Matsumoto, Mitsuharu ^a,e   Nomura, Chisako ^a,e   Tsuge, Hiroko ^a,e   Arimura, Naoto ^a,e   Kawakami, Kazutoshi ^a,f   Sakamoto, Junichi ^a,f   Funami, Miyuki ^a,f   Mol, Clifford D ^c   Snell, Gyorgy P ^c   Bragstad, Kenneth A ^c   Sang, Bi Ching ^c   Dougan, Douglas R ^c   Tanaka, Toshimasa ^a,f   Katayama, Nozomi ^a,e   Horiguchi, Yoshiaki ^a,e,h   Momose, Yu ^a,g   more..

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

^b Takeda Pharmaceuticals International Inc   (United States)

^c Takeda San Diego Inc   (United States)

^d Medicinal Chemistry Research Laboratories   (Japan)

^e Pharmacology Research Laboratories   (Japan)

^f Discovery Research Center   (Japan)

^g Strategic Research Planning Department   (Japan)

^h Umicore Precious Metals Japan Company Ltd   (Japan)

Author keywords

Acylsulfonamide; Diabetes mellitus; Isosteric replacement; PPAR agonist; SBDD

Indexed keywords

(1 BENZYLPYRAZOL 5 YL)PROPANOIC ACID; 2,4 THIAZOLIDINEDIONE DERIVATIVE; 3 [1 (2,4 DICHLOROBENZYL) 3 (2 METHOXYETHOXY) 1H PYRAZOL 5 YL] N (PENTYLSULFONYL)PROPANAMIDE; 3 [1 (2,4 DICHLOROBENZYL) 3 (PYRIDIN 2 YLMETHOXY) 1H PYRAZOL 5 YL] N (PENTYLSULFONYL)PROPANAMIDE; 3 [1 (2,4 DICHLOROBENZYL) 3 ISOPROPOXY 1H PYRAZOL 5 YL] N (HEXYLSULFONYL)PROPANAMIDE; 3 [1 (2,4 DICHLOROBENZYL) 3 ISOPROPOXY 1H PYRAZOL 5 YL] N (PENTYLSULFONYL)PROPANAMIDE; 3 [1 (2,4 DICHLOROBENZYL) 3 ISOPROPOXY 1H PYRAZOL 5 YL] N (PENTYLSULFONYL)PROPENAMIDE; 3 [1 (2,4 DICHLOROBENZYL) 3 ISOPROPOXY 1H PYRAZOL 5 YL] N (PHENYLSULFONYL)PROPANAMIDE; 3 [1 (2,4 DICHLOROBENZYL) 3 ISOPROPOXY 1H PYRAZOL 5 YL] N [(3 METHYLBUTYL)SULFONYL]PROPANAMIDE; 3 [1 (2,4 DICHLOROBENZYL) 3 ISOPROPYL 1H PYRAZOL 5 YL] N (PENTYLSULFONYL)PROPANAMIDE; 3 [1 (2,4 DICHLOROBENZYL) 3 PHENYL 1H PYRAZOL 5 YL] N (PENTYLSULFONYL)PROPANAMIDE; 3 [1 [2 CHLORO 4 (TRIFLUOROMETHYL)BENZYL] 3 (2 METHOXYETHOXY) 1H PYRAZOL 5 YL] N [(3 METHYLBUTYL)SULFONYL]PROPENAMIDE; 3 [1 [2 CHLORO 4 (TRIFLUOROMETHYL)BENZYL] 3 CYCLOPROPYL 1H PYRAZOL 5 YL] N (PENTYLSULFONYL)PROPANAMIDE; 3 [1 [2 CHLORO 4 (TRIFLUOROMETHYL)BENZYL] 3 CYCLOPROPYL 1H PYRAZOL 5 YL] N (PENTYLSULFONYL)PROPENAMIDE; 3 [1 [2 CHLORO 4 (TRIFLUOROMETHYL)BENZYL] 3 ISOPROPOXY 1H PYRAZOL 5 YL] N (PENTYLSULFONYL)PROPENAMIDE; 3 [1 [2 CHLORO 4 (TRIFLUOROMETHYL)BENZYL] 3 ISOPROPOXY 1H PYRAZOL 5 YL] N [(3 METHYLBUTYL)SULFONYL]PROPENAMIDE; 3 [1 [2 CHLORO 4 (TRIFLUOROMETHYL)BENZYL] 3 ISOPROPYL 1H PYRAZOL 5 YL] N (PENTYLSULFONYL)PROPANAMIDE; 3 [3 (BENZYLOXY) 1 (2,4 DICHLOROBENZYL) 1H PYRAZOL 5 YL] N (PENTYLSULFONYL)PROPANAMIDE; 3 [3 BUTOXY 1 (2,4 DICHLOROBENZYL) 1H PYRAZOL 5 YL] N (PENTYLSULFONYL)PROPANAMIDE; [1 (2,4 DICHLOROBENZYL) 3 ISOPROPYL 1H PYRAZOL 5 YL] N (PENTYLSULFONYL)PROPANAMIDE; ALKYL GROUP; ANTIDIABETIC AGENT; BENZYLPYRAZOLE ACYLSULFONAMIDE DERIVATIVE; BENZYLPYRAZOLE PHENYLACETIC ACID; CARBOXYLIC ACID DERIVATIVE; N (BUTYLSULFONYL) 3 [1 (2,4 DICHLOROBENZYL) 3 ISOPROPOXY 1H PYRAZOL 5 YL]PROPANAMIDE; N (CYCLOHEXYLSULFONYL) 3 [1 (2,4 DICHLOROBENZYL) 3 ISOPROPOXY 1H PYRAZOL 5 YL]PROPANAMIDE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIDIABETIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG CLEARANCE; DRUG DESIGN; DRUG METABOLISM; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LIGAND BINDING; MALE; MOLECULAR DOCKING; MOLECULAR MODEL; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; PROTEIN DOMAIN; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; BINDING SITES; CARBOXYLIC ACIDS; COMPUTER SIMULATION; DIABETES MELLITUS, EXPERIMENTAL; DISEASE MODELS, ANIMAL; DRUG DESIGN; HUMANS; HYPOGLYCEMIC AGENTS; PPAR GAMMA; PROTEIN STRUCTURE, TERTIARY; PYRAZOLES; RATS; SULFONAMIDES; THIAZOLIDINEDIONES;

EID: 84855797701     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.12.008     Document Type: Article

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