Synthesis of 2,5-thiazole butanoic acids as potent and selective αvβ3 integrin receptor antagonists with improved oral pharmacokinetic properties

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 4, 2006, Pages 845-849

  Wendt, John A ^a   Wu, Hongwei ^a   Stenmark, Heather G ^a   Boys, Mark L ^a   Downs, Victoria L ^a   Penning, Thomas D ^a   Chen, Barbara B ^a   Wang, Yaping ^a   Duffin, Tiffany ^a   Finn, Mary Beth ^a   Keene, Jeffery L ^a   Engleman, V Wayne ^a   Freeman, Sandra K ^a   Hanneke, Melanie L ^a   Shannon, Kristen E ^a   Nickols, Maureen A ^a   Steininger, Christina N ^a   Westlin, Marissa ^a   Klover, Jon A ^a   Westlin, William ^a   Nickols, G Allen ^a   Russell, Mark A ^a   more..

^a PFIZER INC   (United States)

Author keywords

v 3 integrin receptor; Angiogenesis; Antagonists; SAR; Synthesis; Vitronectin

Indexed keywords

ALPHA2 INTEGRIN; ALPHA5 INTEGRIN; BUTYRIC ACID; VITRONECTIN RECEPTOR;

AREA UNDER THE CURVE; ARTICLE; DRUG BINDING; DRUG BIOAVAILABILITY; DRUG SYNTHESIS; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; ANIMALS; ANTIGENS, NEOPLASM; BIOLOGICAL AVAILABILITY; BUTYRIC ACIDS; DOGS; DRUG EVALUATION, PRECLINICAL; HAPLORHINI; INTEGRIN ALPHAVBETA3; INTEGRINS; MOLECULAR STRUCTURE; PLATELET GLYCOPROTEIN GPIIB-IIIA COMPLEX; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 30344433739     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.11.017     Document Type: Article

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26. General procedure for the isolation of S-isomer half ester: diethyl ester in phosphate buffer (pH 7.4) is stirred with Chirazyme L-2 for 140 h followed by filtration of catalyst, addition of brine, acidification, and ethyl acetate extraction to afford of the desired single enantiomer. The absolute configuration was assigned from the X-ray analysis of (S)-8.
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28. Unpublished results.
29. Compound 25 is rac-3-benzo[1,3]dioxol-5-yl-4-{3-[3-(5,6,7,8-tetrahydro- [1,8]naphthyridin- 2-yl)-propyl]-[1,2,4]oxadiazol-5-yl}-butyric acid.