Linear amides as substance P antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 13, 1996, Pages 1585-1588

  Teall, M ^a   Harrison, T ^a   Moseley, J D ^a   Owens, A P ^a   Sadowski, S ^b   Cascieri, M A ^b  

^a NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SUBSTANCE P ANTAGONIST; TACHYKININ RECEPTOR ANTAGONIST;

ARTICLE; BINDING AFFINITY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HYDROGEN BOND; METHYLATION; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

EID: 0030576287     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00280-6     Document Type: Article

References (7)

1. 1. Williams, BJ.; Teall, M.; McKenna, J.; Harrison, T.; Swain, C.J.; Cascieri, M.A.; Sadowski, S.; Strader, C.; Baker, R. BioMed. Chem. Lett. 1994, 4, 1903.
2. 2.The amine (5 mmol) was stirred overnight with the acid (10 mmol), carbodiimide (10 mmol), hydroxybenzotriazole (10 mmol) and triethylamine (20 mmol) in dichloromethane (50 mL). After aqueous work up and sequential washing with HCl, brine and water, the crude concentrate was recrystallized from hexane/ethyl acetate.
3. 4) and evaporated to dryness. The product was purified by flash silica chromatography using hexane/ethyl acetate mixtures.
4. 1H NMR was approximately 17.6 kcal/mol, for method see: Smith, R.J.; Williams, D.H.; James, K. J. Chem. Soc. Chem. Commun. 1989, 682.
5. 5. Swain, C.J.; Seward, E.M.; Cascieri, M.A.; Fong, T.M.; Herbert, R.; MacIntyre, D.E.; Merchant, K.J.; Owen, S.N.; Owens, A.P.; Sabin, V.; Teall, M.; VanNiel, M.B.; Williams, B.J.; Sadowski, S.; Strader, C.; Ball, R.G. and Baker, R. J. Med. Chem. 1995, 38.
6. 50 values ± SEM): see (i) Cascieri, M.A.; Ber, E.; Fong, T.M.; Sadowski, S.; Bansal, A.; Swain, C.J.; Seward, E.; Frances, B.; Burns, D.; Strader, C.D. Mol. Pharm. 1992, 42, 458.
7. (ii) Fong, T.M.; Anderson, S.A.; Yuh, H.; Huang, R.R.C.; Strader, C.D. Mol. Pharm. 1992, 41, 24.