Research Corporation Technologies, Inc.

University of Oklahoma

Robert A Magarian

Joseph T Pento

Lynette Overacre

Kwasi S Avor

May T Griffin

Billy W Day

Gem-Dichlorocyclopropanes (Analog II derivatives) which demonstrate antiproliferative activity toward MCF-7 cells, in vitro and are generally not reversed by estradiol or having intrinsic estrogenicity (except the hydroxyphenyl derivative Compound 30). In general the cyclopropane compounds have the formula: ##STR1## or any pharmaceutically acceptable salt thereof. X is selected from a group consisting of hydrogen and halogen atoms. The group R.sub.1 may he a hydrogen atom, an alkyl group, an acyl group, or an arylalkyl group. The group R.sub.2 may be a hydrogen atom, an unsubstituted aryl group or a substituted aryl group. The group R.sub.3 may be a hydrogen atom, an alkyl group, a cycloalkyl group, a substituted aryl group or an unsubstituted aryl group. The group R.sub.4 may be a hydrogen atom, an unsubstituted aryl group or a substituted aryl group. The R.sub.4 is absent when R.sub.3 is a cycloalkyl group having a first position carbon and a terminal position carbon bonded to the same carbon of the cyclopropane. Further, no more than any two of R.sub.2, R.sub.3 and R.sub.4 has an aryl group.

Gem-dichlorocyclopropanes as antitumor agents

Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.

Diphenylcyclopropyl analogs

Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes substituents comprising a hydroxy group, a hydrogen atom, an acetate group or a substituted or unsubstituted alkoxy group. The compounds are useful as antiestrogens and anti-tumor agents.

Diphenylcyclopropyl analogs as antiestrogenic and antitumor agents

Gem-Dichlorocyclopropanes (Analog II derivatives) which demonstrate antiproliferative activity toward MCF-7 cells, in vitro and are generally not reversed by estradiol or having intrinsic estrogenicity (except the hydroxyphenyl derivative Compound 30). In general the cyclopropane compounds have the formula: ##STR1## or any pharmaceutically acceptable salt thereof. X is selected from a group consisting of hydrogen and halogen atoms. The group R.sub.1 may be a hydrogen atom, an alkyl group, an acyl group, or an arylalkyl group. The group R.sub.2 may be a hydrogen atom, an unsubstituted aryl group or a substituted aryl group. The group R.sub.3 may be a hydrogen atom, an alkyl group, a cycloalkyl group, a substituted aryl group or an unsubstituted aryl group. The group R.sub.4 may be a hydrogen atom, an unsubstituted aryl group or a substituted aryl group. The R.sub.4 is absent when R.sub.3 is a cycloalkyl group having a first position carbon and a terminal position carbon bonded to the same carbon of the cyclopropane. Further, no more than any two of R.sub.2, R.sub.3 and R.sub.4 has an aryl group.

Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes substituents comprising a hydroxy group, a hydrogen atom, an acetate group or a substituted or unsubstituted alkoxy group. The compounds are useful as antiestrogens and antitumor agents.

Triarylcyclopropane derivatives in which one or more of the aryl groups includes a hydroxy as a substituted or unsubstituted or alkoxy or side chain substituent. The compounds are useful as antiestrogens and anti-tumor agents.

Triarylcyclopropanes as antiestrogens and antitumor agents

Anti-estrogenic cyclopropyl analogs such as 1,1-dichlorocis-2,3-diphenylcyclopropane, when administered to a subject function as anti-tumor agents to prevent the development of estrogen-dependent tumors in the subject and substantially arrest the growth and metastatic involvement of existing estrogen-dependent tumors in the subject. Further, the anti-estrogenic cyclopropyl analogs may be used as anti-estrogenic agents and as fertility agents in the treatment of female infertility. The cyclopropyl analogs useful as anti-tumor, anti-estrogenic and female fertility agents have the general structure ##STR1## wherein: X is a halogen or hydrogen atom;

Cyclopropyl analogs as anti-estrogenic, anti-tumor and female fertility

Estrogenic cyclopropyl analogs, when administered to a female subject, function as anti-fertility agents to prevent pregnancy in the subject. Further, the estrogenic cyclopropyl analogs may be used as estrogenic agents to produce an estrogenic response in a female subject. The estrogenic cyclopropyl analogs useful as estrogenic agents have the general structure: ##STR1## wherein: X is a halogen or hydrogen atom:

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Norman, OK, United States of America

Robert A Magarian