Patent US5015666A successfully refreshed from Google Patents.
US5015666A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Triarylcyclopropanes as antiestrogens and antitumor agents
Assignee: University of Oklahoma
•
Filing: 1989-09-22
•
Granted: 1991-05-14
•
Expires: 2009-09-22
Abstract
Abstract 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.
Inventors
- 👤 Robert A. Magarian
- 👤 Joseph T. Pento
- 👤 Billy W. Day
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 19:46
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/08; C07D295/084; C07D295/088; A; A61; A61K; A61K31/00; A61K31/02; A61K31/025; A61K31/03; C07C; C07C309/00; C07C309/63; C07C309/64; C07C309/65; C07C309/66; C07C2601/00; C07C2601/02
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
217 words
A compound having the formula: ##STR9## or any pharmaceutically acceptable salt thereof, in which: R 1 is hydrogen, a hydroxyl group, an alkoxy group or a substituted or unsubstituted arylalkoxy group (with the proviso that R 1 , R 2 and R 3 are not simultaneously arylalkoxy), and in which any substituent of the aryl group comprises an alkyl group; R 2 is hydrogen, a hydroxyl group (with the proviso that R 1 and R 3 are not simultaneously alkoxy when R 2 is hydroxyl), an alkoxy group or a substituted alkoxy group in which the substituent of the alkoxy group comprises either a dialkylamino group, a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group; R 3 is hydrogen, a hydroxyl group, an alkoxy group or a substituted alkoxy group and in which the substituent of the alkoxy group comprises either a dialkylamino group or a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group; R 4 is hydrogen; and X is a halogen or hydrogen.
Claim 2
Dependent Claim
217 words
A compound having the formula: ##STR9## or any pharmaceutically acceptable salt thereof, in which: R 1 is hydrogen, a hydroxyl group, an alkoxy group or a substituted or unsubstituted arylalkoxy group (with the proviso that R 1 , R 2 and R 3 are not simultaneously arylalkoxy), and in which any substituent of the aryl group comprises an alkyl group; R 2 is hydrogen, a hydroxyl group (with the proviso that R 1 and R 3 are not simultaneously alkoxy when R 2 is hydroxyl), an alkoxy group or a substituted alkoxy group in which the substituent of the alkoxy group comprises either a dialkylamino group, a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group; R 3 is hydrogen, a hydroxyl group, an alkoxy group or a substituted alkoxy group and in which the substituent of the alkoxy group comprises either a dialkylamino group or a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group; R 4 is hydrogen; and X is a halogen or hydrogen.
Claim 3
Dependent Claim
20 words
The compound of claim 1 in which R 2 is an alkoxy group, a beta-dialkylaminoalkoxy group, or an aryloxy group.
Claim 4
Dependent Claim
15 words
The compound of claim 2 in which R 1 is hydrogen or an alkoxy group.
Claim 5
Dependent Claim
15 words
The compound of claim 2 in which R 3 is hydrogen or an alkoxy group.
Claim 6
Dependent Claim
24 words
The compound of claim 2 in which: R 1 is hydrogen or an alkoxy group; and R 3 is hydrogen or an alkoxy group.
Claim 7
Dependent Claim
20 words
The compound of claim 1 in which R 2 is a methoxy group, a dimethylaminoethoxy group or an benzyloxy group.
Claim 8
Dependent Claim
24 words
The compound of claim 6 in which: R 1 is hydrogen or a methoxy group; and R 3 is hydrogen or a methoxy group.
Claim 9
Dependent Claim
11 words
The compound of claim 7 in which X is a halogen.
Claim 10
Dependent Claim
23 words
The compound of claim 1 in which R 1 is hydrogen, R 2 is methoxy, R 3 is hydrogen and X is chlorine.
Claim 11
Dependent Claim
23 words
The compound of claim 1 in which R 1 is hydrogen, R 2 is dimethylaminoethoxy, R 3 is hydrogen and X is chlorine.
Claim 12
Dependent Claim
23 words
The compound of claim 1 in which R 1 is methoxy, R 2 is dimethylaminoethoxy, R 3 is hydrogen and X is chlorine.
Claim 13
Dependent Claim
23 words
The compound of claim 1 in which R 1 is methoxy, R 2 is benzyloxy, R 3 is hydrogen and X is chlorine.
Claim 14
Dependent Claim
23 words
The compound of claim 1 in which R 1 is methoxy, R 2 is benzyloxy, R 3 is methoxy and X is chlorine.
Claim 15
Dependent Claim
227 words
A compound of matter comprising a pharmaceutically acceptable carrier and a compound having the formula: ##STR10## or any pharmaceutically acceptable salt thereof, in which: R 1 is hydrogen, a hydroxyl group, alkoxy group or a substituted or unsubstituted arylalkoxy group (with the proviso that R 1 , R 2 , and R 3 are not simultaneously arylalkoxy), and in which any substituent of the aryl group comprises an alkyl group; R 2 is hydrogen, a hydroxyl group (with the proviso that R 1 and R 3 are not simultaneously alkoxy when R 2 is hydroxyl), an alkoxy group or a substituted alkoxy group in which the substituent of the alkoxy group comprises either a dialkylamino group, a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group; R 3 is hydrogen, a hydroxyl group, an alkoxy group or a substituted alkoxy group and in which the substituent of the alkoxy group comprises either a dialkylamino group or a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group; R 4 is hydrogen; and X is a halogen or hydrogen.
Claim 16
Dependent Claim
227 words
A compound of matter comprising a pharmaceutically acceptable carrier and a compound having the formula: ##STR10## or any pharmaceutically acceptable salt thereof, in which: R 1 is hydrogen, a hydroxyl group, alkoxy group or a substituted or unsubstituted arylalkoxy group (with the proviso that R 1 , R 2 , and R 3 are not simultaneously arylalkoxy), and in which any substituent of the aryl group comprises an alkyl group; R 2 is hydrogen, a hydroxyl group (with the proviso that R 1 and R 3 are not simultaneously alkoxy when R 2 is hydroxyl), an alkoxy group or a substituted alkoxy group in which the substituent of the alkoxy group comprises either a dialkylamino group, a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group; R 3 is hydrogen, a hydroxyl group, an alkoxy group or a substituted alkoxy group and in which the substituent of the alkoxy group comprises either a dialkylamino group or a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group; R 4 is hydrogen; and X is a halogen or hydrogen.
Claim 17
Dependent Claim
20 words
The compound of claim 14 in which R 2 is an alkoxy group, a beta-dialkyaminoalkoxy group, or an aryloxy group.
Claim 18
Dependent Claim
15 words
The compound of claim 15 in which R 1 is hydrogen or an alkoxy group.
Claim 19
Dependent Claim
15 words
The compound of claim 15 in which R 3 is hydrogen or an alkoxy group.
Claim 20
Dependent Claim
24 words
The compound of claim 15 in which: R 1 is hydrogen or an alkoxy group; and R 3 is hydrogen or an alkoxy group.
Claim 21
Independent Claim
369 words
A method of inducing antiestrogenic activity in a mammal in need of such therapy comprising administering to the mammal an antiestrogenically effective amount of one or more compounds having the formula: ##STR11## or any pharmaceutically acceptable salt thereof, in which: R 1 is hydrogen, a hydroxyl group, an alkoxy group containing from 1 to about 3 carbon atoms, or a substituted or unsubstituted arylalkoxy group (with the proviso that R 1 , R 2 and R 3 are not simultaneously arylalkoxy), in which the alkyl group attached to the oxygen atom contains from 1 to about 3 carbon atoms, and in which any substituent of the aryl group comprises an alkyl group containing from 1 to about 3 carbon atoms; R 2 is hydrogen, a hydroxyl group (with the proviso that R 1 and R 3 are not simultaneously alkoxy), an alkoxy group containing from 1 to about 3 carbon atoms, or a substituted alkoxy group in which the alkyl group attached to the oxygen atom contains from 1 to about 3 carbon atoms and in which the substituent of the alkoxy group comprises either a dialkylamino group in which each alkyl substituent thereof contains from 1 to about 3 carbon atoms, a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group containing from 1 to about 3 carbon atoms; R 3 is hydrogen, a hydroxyl group, an alkoxy group containing from 1 to about 3 carbon atoms, or a substituted alkoxy group in which the alkyl group attached to the oxygen atom contains from 1 to about 3 carbon atoms and in which the substituent of the alkoxy group comprises either a dialkylamino group in which each alkyl substituent thereof contains from 1 to about 3 carbon atoms, or a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group containing from 1 to about 3 carbon atoms; R 4 is hydrogen; and X is a halogen or hydrogen.
Claim 22
Independent Claim
369 words
A method of inducing antiestrogenic activity in a mammal in need of such therapy comprising administering to the mammal an antiestrogenically effective amount of one or more compounds having the formula: ##STR11## or any pharmaceutically acceptable salt thereof, in which: R 1 is hydrogen, a hydroxyl group, an alkoxy group containing from 1 to about 3 carbon atoms, or a substituted or unsubstituted arylalkoxy group (with the proviso that R 1 , R 2 and R 3 are not simultaneously arylalkoxy), in which the alkyl group attached to the oxygen atom contains from 1 to about 3 carbon atoms, and in which any substituent of the aryl group comprises an alkyl group containing from 1 to about 3 carbon atoms; R 2 is hydrogen, a hydroxyl group (with the proviso that R 1 and R 3 are not simultaneously alkoxy), an alkoxy group containing from 1 to about 3 carbon atoms, or a substituted alkoxy group in which the alkyl group attached to the oxygen atom contains from 1 to about 3 carbon atoms and in which the substituent of the alkoxy group comprises either a dialkylamino group in which each alkyl substituent thereof contains from 1 to about 3 carbon atoms, a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group containing from 1 to about 3 carbon atoms; R 3 is hydrogen, a hydroxyl group, an alkoxy group containing from 1 to about 3 carbon atoms, or a substituted alkoxy group in which the alkyl group attached to the oxygen atom contains from 1 to about 3 carbon atoms and in which the substituent of the alkoxy group comprises either a dialkylamino group in which each alkyl substituent thereof contains from 1 to about 3 carbon atoms, or a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group containing from 1 to about 3 carbon atoms; R 4 is hydrogen; and X is a halogen or hydrogen.
Claim 23
Dependent Claim
20 words
The method of claim 19 in which R 2 is an alkoxy group, a beta-dialkyaminoalkoxy group, or an aryloxy group.
Claim 24
Dependent Claim
15 words
The method of claim 20 in which R 1 is hydrogen or an alkoxy group.
Claim 25
Dependent Claim
15 words
The method of claim 20 in which R 3 is hydrogen or an alkoxy group.
Claim 26
Dependent Claim
24 words
The method of claim 20 in which: R 1 is hydrogen or an alkoxy group; and R 3 is hydrogen or an alkoxy group.
Claim 27
Independent Claim
372 words
A method of inhibiting the development of an estrogen-dependent tumor in a mammal in need of such therapy comprising administering to the mammal an effective amount of one or more compounds having the formula: ##STR12## or any pharmaceutically acceptable salt thereof, in which: R 1 is hydrogen, a hydroxyl group, an alkoxy group containing from 1 to about 3 carbon atoms, or a substituted or unsubstituted arylalkoxy group (with the proviso that R 1 , R 2 and R 3 are not simultaneously arylalkoxy), in which the alkyl group attached to the oxygen atom contains from 1 to about 3 carbon atoms, and in which any substituent of the aryl group comprises an alkyl group containing from 1 to about 3 carbon atoms; R 2 is hydrogen, a hydroxyl group (with the proviso that R 1 and R 3 are not simultaneously alkoxy), an alkoxy group containing from 1 to about 3 carbon atoms, or a substituted alkoxy group in which the alkyl group attached to the oxygen atom contains from 1 to about 3 carbon atoms and in which the substituent of the alkoxy group comprises either a dialkylamino group in which each alkyl substituent thereof contains from 1 to about 3 carbon atoms, a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group containing from 1 to about 3 carbon atoms; R 3 is hydrogen, a hydroxyl group, an alkoxy group containing from 1 to about 3 carbon atoms, or a substituted alkoxy group in which the alkyl group attached to the oxygen atom contains from 1 to about 3 carbon atoms and in which the substituent of the alkoxy group comprises either a dialkylamino group in which each alkyl substituent thereof contains from 1 to about 3 carbon atoms, or a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group containing from 1 to about 3 carbon atoms; R 4 is hydrogen; and X is a halogen or hydrogen.
Claim 28
Independent Claim
372 words
A method of inhibiting the development of an estrogen-dependent tumor in a mammal in need of such therapy comprising administering to the mammal an effective amount of one or more compounds having the formula: ##STR12## or any pharmaceutically acceptable salt thereof, in which: R 1 is hydrogen, a hydroxyl group, an alkoxy group containing from 1 to about 3 carbon atoms, or a substituted or unsubstituted arylalkoxy group (with the proviso that R 1 , R 2 and R 3 are not simultaneously arylalkoxy), in which the alkyl group attached to the oxygen atom contains from 1 to about 3 carbon atoms, and in which any substituent of the aryl group comprises an alkyl group containing from 1 to about 3 carbon atoms; R 2 is hydrogen, a hydroxyl group (with the proviso that R 1 and R 3 are not simultaneously alkoxy), an alkoxy group containing from 1 to about 3 carbon atoms, or a substituted alkoxy group in which the alkyl group attached to the oxygen atom contains from 1 to about 3 carbon atoms and in which the substituent of the alkoxy group comprises either a dialkylamino group in which each alkyl substituent thereof contains from 1 to about 3 carbon atoms, a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group containing from 1 to about 3 carbon atoms; R 3 is hydrogen, a hydroxyl group, an alkoxy group containing from 1 to about 3 carbon atoms, or a substituted alkoxy group in which the alkyl group attached to the oxygen atom contains from 1 to about 3 carbon atoms and in which the substituent of the alkoxy group comprises either a dialkylamino group in which each alkyl substituent thereof contains from 1 to about 3 carbon atoms, or a heterocycle containing between about 5 and 6 members, at least one of which is nitrogen, or a substituted or unsubstituted aryl group, in which any substituent of the aryl group comprises an alkyl group containing from 1 to about 3 carbon atoms; R 4 is hydrogen; and X is a halogen or hydrogen.
Claim 29
Dependent Claim
20 words
The method of claim 24 in which R 2 is an alkoxy group, a beta-dialkyaminoalkoxy group, or an aryloxy group.
Claim 30
Dependent Claim
15 words
The method of claim 25 in which R 1 is hydrogen or an alkoxy group.
Claim 31
Dependent Claim
15 words
The method of claim 25 in which R 3 is hydrogen or an alkoxy group.
Claim 32
Dependent Claim
24 words
The method of claim 25 in which: R 1 is hydrogen or an alkoxy group; and R 3 is hydrogen or an alkoxy group.
References Cited (Backward Citations)
US4879315A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-05-13 | 1994-11-12 | 1995-05-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-05-13 | 1998-11-12 | 1999-05-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-05-13 | 2002-11-12 | 2003-05-14 | $7700.00 | Window Closed / Lapsed |