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A number of imidazolinone derivatives are known to be antagonists of angiotensin II. Bernhart, C. A.; Perreaut, P. M.; Ferrari, B. P.; Muneaux, Y. A.; Assens, J.-L. A.; Clément, J.; Haudricourt, F.; Muneaux, C. F.; Taillades, J. E.; Vignal, M.-A.; Gougat, J.; Guiraudou, P. R.; Lacour, C. A.; Roccon, A.; Cazaubon, C. F.; Brelière, J.-C.; Le Fur, G.; Nisato, D. J. Med. Chem. 1993, 36, 3371.
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A compound with a spirocyclopropane-annelated imidazoline moiety inhibits the specific binding of angiotensin II at a concentration of less than 50 nM. Cremer, G.; Muller, J. C. (Synthelabo S. A., Fr). U.S. (1995), 7 pp. Cont.-in-part in U.S. Ser. No. 2,502, abandoned. CODEN: USXXAM US 5457112 A 19951010. Application: US 93-165648 19931213. Priority: FR 92-15038 19921214; US 93-2502 19930106. CAN 124:117321 AN 1995:913758.
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Crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-163584 (3a) and CCDC-163585 (9a). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, U.K. (a) Sheldrick, G. M. Acta Crystallogr., Sect A 1990, 46, 467.
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The in situ [4 + 2] cycloaddition of o-quinodimethanes from benzocyclobutenes is a well-established synthetic method. For a review, see: Michellys, P. Y.; Pellisier, H.; Santelli, M. Org. Prep. Proced. Int. 1996, 28, 545.
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2 extrusion from corresponding substituted pyrimidone-fused 3-sulfolenes which are accessible in two steps from methyl 4-oxotetrahydrothiophene-3-carboxylate. Cf. Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1723.
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