Synthesis and structure-activity relationship of potent, selective and orally active anthranilamide-based factor Xa inhibitors: Application of weakly basic sulfoximine group as novel S4 binding element

European Journal of Medicinal Chemistry

Volumn 58, Issue , 2012, Pages 136-152

  Pandya, Vrajesh ^a,b   Jain, Mukul ^a   Chakrabarti, Ganes ^a   Soni, Hitesh ^a   Parmar, Bhavesh ^a   Chaugule, Balaji ^a   Patel, Jigar ^a   Jarag, Tushar ^a   Joshi, Jignesh ^a   Joshi, Nirav ^a   Rath, Akshyaya ^a   Unadkat, Vishal ^a   Sharma, Bhavesh ^a   Ajani, Haresh ^a   Kumar, Jeevan ^a   Sairam, Kalapatapu V V M ^a   Patel, Harilal ^a   Patel, Pankaj ^a  

^a ZYDUS RESEARCH CENTRE   (India)

^b M S UNIVERSITY OF BARODA   (India)

Author keywords

Anthranilamide; Anticoagulant; Factor Xa; Sulfoximine

Indexed keywords

2 (4 (N ACETYL METHYLSULFONIMIDOYL)BENZAMIDO) 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) BENZAMIDE; 2 (4 (N CARBAMOYL METHYLSULFONIMIDOYL)BENZAMIDO) 5 CHLORO N (5 CHLOROPYRIDIN 2 YL)BENZAMIDE; 2 AMINOBENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 ((METHYL SULFONIMIDOYL)METHYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (2 HYDROXYETHYLSULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (ETHYLSULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (METHYL N (2 (4 METHYL 1,4 DIAZEPAN 1 YL)ACETYL)SULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (METHYL N (2 (4 METHYLPIPERAZIN 1 YL)ACETYL)SULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (METHYL N (2 (METHYLAMINO)ACETYL)SULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (METHYL N (2 (PIPERIDIN 1 YL)ACETYL)SULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (METHYL N (2 (PYRROLIDIN 1 YL)ACETYL) SULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (METHYL N (2 MORPHOLINOACETYL)SULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (METHYL N (METHYLSULFONYL)SULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (METHYL SULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (N (2 (4 AMINOCARBONYL 1 PIPERIDINYL)ACETYL)METHYLSULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (N (2 (4 HYDROXYPIPERIDIN 1 YL)ACETYL) METHYLSULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (N (2 (CYCLOPENTYLAMINO)ACETYL) METHYLSULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (N (2 (DIETHYLAMINO)ACETYL) METHYLSULFONIMIDOYL )BENZAMIDO) 3 METHOXYBENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (N (2 (DIETHYLAMINO)ACETYL) METHYLSULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (N (2 (DIISOPROPYLAMINO)ACETYL)METHYLSULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (N (2 (DIMETHYLAMINO)ACETYL)METHYLSULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (N (2 (ETHY AMINO)ACETYL) METHYLSULFONIMIDOYL) BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (N (2 (ISOPROPYLAMINO)ACETYL) METHYLSULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (N (2 METHOXYACETYL) METHYLSULFONIMIDOYL) BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 2 (4 (N CYANO METHYLSULFONIMIDOYL)BENZAMIDO)BENZAMIDE; 5 CHLORO N (5 CHLOROPYRIDIN 2 YL) 3 METHOXY 2 (4 (METHYLSULFONIMIDOYL)BENZAMIDO) BENZAMIDE; BLOOD CLOTTING FACTOR 10A INHIBITOR; N (5 CHLOROPYRIDIN 2 YL) 3 METHOXY 2 (4 (METHYL SULFONIMIDOYL)BENZAMIDO) BENZAMIDE; N (5 CHLOROPYRIDIN 2 YL) 5 METHOXY 2 (4 (METHYL SULFONIMIDOYL)BENZAMIDO)BENZAMIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTERY THROMBOSIS; ARTICLE; CONTROLLED STUDY; DRUG EFFICACY; DRUG METABOLISM; DRUG POTENCY; DRUG SYNTHESIS; EX VIVO STUDY; IN VIVO STUDY; MALE; NONHUMAN; PROTHROMBIN TIME; RAT; STRUCTURE ACTIVITY RELATION; VEIN THROMBOSIS;

ANIMALS; ANTICOAGULANTS; BINDING SITES; DISEASE MODELS, ANIMAL; DOSE-RESPONSE RELATIONSHIP, DRUG; FACTOR XA; HUMANS; IMINES; MALE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORTHO-AMINOBENZOATES; RATS; RATS, WISTAR; REFERENCE VALUES; SERINE PROTEASES; SERINE PROTEINASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFOXIDES; VENOUS THROMBOSIS;

EID: 84868234283     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.10.005     Document Type: Article

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