Substituted dibenz (A F)azulenes and methods of preparation
AssigneeOrtho Pharmaceutical Corporation
InventorsJohn H. Dodd, Lisa A. Dixon, James L. Bullington, Charles F. Schwender
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Abstract
Tetracyclic compounds having the following structure are described: ##STR1## wherein R.sub.1 -R.sub.10 are as defined. The tetracyclic compounds are capable of potent effects on steroid sensitive tissues and have demonstrated increased uterine weight, antiovulatory effects and potent steroid receptor binding. The compounds have therapeutic utility in reproductive applications such as fertility control, labor induction, ovulation induction and spermatogenesis. Methods for preparing the tetracyclic compounds from substituted indanones are also described.
Claims12
A compound of the formula:
- ##STR38## wherein R.sub.1 is selected from the group consisting of hydrogen, halo, alkoxy (C.sub.1 -C.sub.6) and hydroxy;
- R.sub.2 is alkyl (C.sub.1 -C.sub.6);
- R.sub.3, R.sub.4 and R.sub.5 are selected from the group consisting of hydrogen, alkyl (C.sub.1 -C.sub.6), alkoxy (C.sub.1 -C.sub.6), benzyloxy, acyl (C.sub.2 -C.sub.6), acyloxy (C.sub.2 -C.sub.6), alkoxycarboxy wherein the alkoxy group has 1-5 carbon atoms, amino, acylamino (C.sub.2 -C.sub.6), halo, nitro, hydroxy, cyano, alkylaminoalkoxy wherein the alkyl and alkoxy groups each contain 1-5 carbons, nitroso, dialkylphosphoryloxy, hydroxyalkyl (C.sub.1 -C.sub.6), and phenyltetrazoyloxy;
- R.sub.6 and R.sub.7 are selected from hydrogen, alkyl (C.sub.1 -C.sub.6), hydroxy, and when taken together alkylene (C.sub.1 -C.sub.6) and carbonyl;
- R.sub.8 is selected from hydrogen, alkyl, hydroxy or acyloxy (C.sub.2 -C.sub.6);
- R.sub.9 and R.sub.10 are hydrogen or together form a double bond, and R.sub.8 and R.sub.9 taken together form a carbonyl group, when R.sub.10 is hydrogen.
The process for preparing a compound of the formula:
- ##STR39## wherein R.sub.1 is selected from hydrogen, halogen and alkoxy(C.sub.1 -C.sub.6);
- R.sub.2 is alkyl(C.sub.1 -C.sub.6);
- R.sub.3, R.sub.4 and R.sub.5 are selected from alkyl(C.sub.1 -C.sub.6), acylamino(C.sub.2 -C.sub.6), alkoxy(C.sub.1 -C.sub.6) and hydroxy;
- and R.sub.6, R.sub.7 and R.sub.8 are selected from hydrogen and alkyl(C.sub.1 -C.sub.6);
- which comprises reacting a substituted indanone of the formula:
- ##STR40## with a substituted metal halide in a suitable solvent and reacting the intermediate 2,3-dihydroindan-1-ol which forms with a cyclizing agent.
Dependencies are inferred from the claim text.