A-ring annulated heterocycles, the isoxazole 6, the pyrazoles 8 and the pyrimidines 9 are prepared starting from 2-hydroxymethylene canrenone 1. Binding studies were carried out with the compounds 1 and 6-8 using estrogen, progesterone, androgen, gluco- and mineralocorticoid receptors as well as the serum proteins SHBG and CBG: the substances were inactive on the receptor level. 1, 7 and 8a show weak binding affinity to CBG.

Starting from the Mannich salt 1 of the aldosterone antagonist canrenone or from 2-methylene-canrenone (2) the A-ring annulated hetero- and carbocycles 5, 6, 8-13 were prepared. Receptor (estradiol, progesterone, androgen, gluco- and mineralocorticoid) binding studies and competition studies with the serum proteins SHBG and CBG were carried out using the compounds 2, 3, 4b, 5, 6b, 8 and 12. The relative binding affinities with CBG are below 1%, in all other cases lower than 0.01%.

Heterocyclic Annulated Steroids from 2-Hydroxymethylene Canrenone.-A-ring annulated heterocycles, e.g. (II) or (V), are prepared starting from the title compound (I). Most of the synthesized compounds are inactive on the receptor level. (I) and (III) show weak binding affinity to the serum protein CBG. -(GOERLITZER, K.; MOORMANN, P.; POLLOW, K.; SCHAFFRATH, M.; Arch. Pharm. (Weinheim, Ger.) 328 (1995) 2, 157-160; Inst. Pharm. Chem., TU Braunschweig, D-38106 Braunschweig, Germany; DE)

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Synthesis and Reactions of 2-Methylenecanrenone.-Starting from the Mannich salt (III) of the aldosterone antagonist canrenone (I), the title compound (IV) and a variety of A-ring annulated hetero-and carbocyclic analogues such as (VI) or (VIII) are prepared. Receptor binding and competition studies with the serum proteins SHBG and CBG are described. -(GOERLITZER, K.; MOORMANN, P.; POLLOW, K.; SCHAFFRATH, M.; Arch. Pharm. (Weinheim, Ger.) 328 (1995) 2, 149-155; Inst. Pharm. Chem.,