2,5-Disubstituted pyrrolidine carboxylates as potent, orally active sphingosine-1-phosphate (S1P) receptor agonists

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 11, 2006, Pages 2905-2908

  Colandrea, Vincent J ^a   Legiec, Irene E ^a   Huo, Pei ^a   Yan, Lin ^a   Hale, Jeffrey J ^a   Mills, Sander G ^a   Bergstrom, James ^a   Card, Deborah ^a   Chebret, Gary ^a   Hajdu, Richard ^a   Keohane, Carol Ann ^a   Milligan, James A ^a   Rosenbach, Mark J ^a   Shei, Gan Ju ^a   Mandala, Suzanne M ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Immunosuppressants; Oxadiazole; Pyrrolidines; S1P receptor

Indexed keywords

HORMONE RECEPTOR STIMULATING AGENT; PROLINE DERIVATIVE; SPHINGOSINE 1 PHOSPHATE RECEPTOR STIMULATING AGENT; UNCLASSIFIED DRUG;

AGONIST; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG DETERMINATION; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; LYMPHOCYTE DEPLETION; MOUSE; NONHUMAN; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

ADMINISTRATION, ORAL; ANIMALS; CARBOXYLIC ACIDS; MOLECULAR STRUCTURE; PYRROLIDINES; RATS; RECEPTORS, LYSOSPHINGOLIPID; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA;

EID: 33646024260     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.03.038     Document Type: Article

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17. Chiral HPLC was performed on the N-tert-butoxycarbonylmethyl ester of compound 19 (Chiralpak OD column, 2 × 25 cm, 10% EtOH/heptane, 8.0 mL/min, λ = 254 nm, peak 1 = 21.9 min; peak 2 = 26.1 min). Sequential deprotection afforded compounds 20 and 21.