US5324736A
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Diphenylcyclopropyl analogs as antiestrogenic and antitumor agents
Assignee: University of Oklahoma
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Filing: 1993-08-16
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Granted: 1994-06-28
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Expires: 2013-08-16
Abstract
Abstract 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.
Inventors
- 👤 Robert A. Magarian
- 👤 Joseph T. Pento
- 👤 Kwasi S. Avor
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 19:25
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: 48
Claim 1
Independent Claim
151 words
A compound having the formula: ##STR9## or any pharmaceutically acceptable salt thereof, in which: X is selected from a group consisting of, halogen atoms and hydrogen atoms; R 1 is selected from a group consisting of, a hydrogen atom, and a substituted alkoxy group in which the substituent of the alkoxy group is selected from a group consisting of, an unsubstituted piperidino, and a substituted piperidino in which the substitutent is an alkyl group containing from 1 to 6 carbon atoms; and R 2 is selected from a group consisting of a hydrogen atom, and a substituted alkoxy group, and in which the substituent of the alkoxy group is selected from a group consisting of, an unsubstituted piperidino, and a substituted piperidino in which the substituent is an alkyl group containing from 1 to 6 carbon atoms; and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 2
Dependent Claim
151 words
A compound having the formula: ##STR9## or any pharmaceutically acceptable salt thereof, in which: X is selected from a group consisting of, halogen atoms and hydrogen atoms; R 1 is selected from a group consisting of, a hydrogen atom, and a substituted alkoxy group in which the substituent of the alkoxy group is selected from a group consisting of, an unsubstituted piperidino, and a substituted piperidino in which the substitutent is an alkyl group containing from 1 to 6 carbon atoms; and R 2 is selected from a group consisting of a hydrogen atom, and a substituted alkoxy group, and in which the substituent of the alkoxy group is selected from a group consisting of, an unsubstituted piperidino, and a substituted piperidino in which the substituent is an alkyl group containing from 1 to 6 carbon atoms; and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 3
Dependent Claim
48 words
The compound of claim 1 in which R 1 is selected from a group consisting of; a substituted alkoxy in which the substituent is a piperidino; and a substituted alkoxy in which the substituent is a substituted piperidino and in which the piperidino substituent is an alkyl group.
Claim 4
Dependent Claim
11 words
The compound of claim 2 in which R 2 is hydrogen.
Claim 5
Dependent Claim
20 words
The compound of claim 3 in which R 1 and the R 2 are each at the para ring position.
Claim 6
Dependent Claim
10 words
The compound of claim 4 in which X is chlorine.
Claim 7
Dependent Claim
49 words
The compound of claim 1 in which R 2 is selected from a group consisting of: a substituted alkoxy group in which the substituent is a piperidino and a substituted alkoxy in which the substituent is a substituted piperidino and in which the piperidino substituent is an alkyl group.
Claim 8
Dependent Claim
11 words
The compound of claim 6 in which R 1 is hydrogen.
Claim 9
Dependent Claim
21 words
The compound of claim 7 in which the R 1 and the R 2 are each at the para ring position.
Claim 10
Dependent Claim
10 words
The compound of claim 8 in which X is chlorine.
Claim 11
Dependent Claim
176 words
A composition of matter comprising: a pharmaceutically acceptable carrier; and a compound having the formula: ##STR10## or any pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier of sufficient quantity to solubilize the compound, in which: X is selected from a group consisting of, halogen atoms and hydrogen atoms; R 1 is selected from a group consisting of, a hydrogen atom, a hydroxyl group, and a substituted alkoxy group in which the substituent of the alkoxy group is selected from a group consisting of, an unsubstituted piperidino, and a substituted piperidino in which the substituent is an alkyl group containing from 1 to 6 carbon atoms; and R 2 is selected from a group consisting of, a hydrogen atom, and a substituted alkoxy group, and in which the substituent of the alkoxy group is selected from a group consisting of, an unsubstituted piperidino, and a substituted piperidino in which the substituent is an alkyl group containing from 1 to 6 carbon atoms; and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 12
Dependent Claim
176 words
A composition of matter comprising: a pharmaceutically acceptable carrier; and a compound having the formula: ##STR10## or any pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier of sufficient quantity to solubilize the compound, in which: X is selected from a group consisting of, halogen atoms and hydrogen atoms; R 1 is selected from a group consisting of, a hydrogen atom, a hydroxyl group, and a substituted alkoxy group in which the substituent of the alkoxy group is selected from a group consisting of, an unsubstituted piperidino, and a substituted piperidino in which the substituent is an alkyl group containing from 1 to 6 carbon atoms; and R 2 is selected from a group consisting of, a hydrogen atom, and a substituted alkoxy group, and in which the substituent of the alkoxy group is selected from a group consisting of, an unsubstituted piperidino, and a substituted piperidino in which the substituent is an alkyl group containing from 1 to 6 carbon atoms; and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 13
Dependent Claim
47 words
The compound of claim 10 in which R 1 is selected from a group containing: a substituted alkoxy in which the substituent is a piperidino; and a substituted alkoxy in which the substituent is a substituted piperidino and in which the piperidino substituent is an alkyl group.
Claim 14
Dependent Claim
10 words
The compound of claim 11 in which R2 is hydrogen.
Claim 15
Dependent Claim
20 words
The compound of claim 12 in which the R 1 and the R2 are each at the para ring position.
Claim 16
Dependent Claim
10 words
The compound of claim 13 in which X is chlorine.
Claim 17
Dependent Claim
48 words
The compound of claim 10 in which R 2 is selected from a group consisting of: a substituted alkoxy in which the substituent is a piperidino and a substituted alkoxy in which the substituent is a substituted piperidino and in which the piperidino substitutent is an alkyl group.
Claim 18
Dependent Claim
10 words
The compound of claim 15 in which R1 is hydrogen.
Claim 19
Dependent Claim
21 words
The compound of claim 16 in which the R 1 and the R 2 are each at the para ring position.
Claim 20
Dependent Claim
10 words
The compound of claim 17 in which X is chlorine.
Claim 21
Independent Claim
176 words
A method of inducing antiestrogenic activity in a mammal in need of each 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: X is selected from a group consisting of, halogen atoms and hydrogen atoms; R 1 is selected from a group consisting of, a hydrogen atom, and a substituted alkoxy group in which the substituent of the alkoxy group is selected from a group consisting of, an unsubstituted piperidino, and a substituted piperidino in which the substituent is an alkyl group containing from 1 to 6 carbon atoms; and R 2 is selected from a group consisting of, a hydrogen atom, a substituted alkoxy group in which the substituent of the alkoxy group is selected from a group consisting of an unsubstituted piperidino, and a substituted piperidino in which the substituent is an alkyl group containing from 1 to about 6 carbon atoms, and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 22
Independent Claim
176 words
A method of inducing antiestrogenic activity in a mammal in need of each 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: X is selected from a group consisting of, halogen atoms and hydrogen atoms; R 1 is selected from a group consisting of, a hydrogen atom, and a substituted alkoxy group in which the substituent of the alkoxy group is selected from a group consisting of, an unsubstituted piperidino, and a substituted piperidino in which the substituent is an alkyl group containing from 1 to 6 carbon atoms; and R 2 is selected from a group consisting of, a hydrogen atom, a substituted alkoxy group in which the substituent of the alkoxy group is selected from a group consisting of an unsubstituted piperidino, and a substituted piperidino in which the substituent is an alkyl group containing from 1 to about 6 carbon atoms, and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 23
Dependent Claim
48 words
The method of claim 19 in which R 1 is selected from a group consisting of: a substituted alkoxy in which the substituent is a piperidino, and A substituted alkoxy in which the substituent is a substituted piperidino and in which the piperidino substituent is an alkyl group.
Claim 24
Dependent Claim
11 words
The method of claim 20 in which R 2 is hydrogen.
Claim 25
Dependent Claim
21 words
The method of claim 21 in which the R 1 and the R 2 are each at the para ring position.
Claim 26
Dependent Claim
10 words
The method of claim 22 in which X is chlorine.
Claim 27
Dependent Claim
48 words
The method of claim 19 in which R 2 is selected from a group consisting of: a substituted alkoxy in which the substituent is a piperidino and a substituted alkoxy in which the substituent is a substituted piperidino and in which the piperidino substituent is an alkyl group.
Claim 28
Dependent Claim
11 words
The compound of claim 24 in which R 1 is hydrogen.
Claim 29
Dependent Claim
19 words
The compound of claim 25 in which R 1 and R 2 are each at the para ring position.
Claim 30
Dependent Claim
10 words
The compound of claim 26 in which X is chlorine.
Claim 31
Independent Claim
178 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: X is selected from a group consisting of, halogen atoms and hydrogen atoms; R 1 is selected from a group consisting of, a hydrogen atom, a substituted alkoxy group in which the substituent of the alkoxy group is selected from a group consisting of and an unsubstituted piperidino and a substituted piperidino in which the substituent is an alkyl group containing from 1 to 6 carbon atoms; R 2 is selected from a group consisting of, a hydrogen atom, and a substituted alkoxy group in which the substituent of the alkoxy group is selected from the group consisting of, an unsubstituted piperidino and a substituted piperidino in which the substituent is an alkyl group containing from 1 to 6 carbon atoms; and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 32
Independent Claim
178 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: X is selected from a group consisting of, halogen atoms and hydrogen atoms; R 1 is selected from a group consisting of, a hydrogen atom, a substituted alkoxy group in which the substituent of the alkoxy group is selected from a group consisting of and an unsubstituted piperidino and a substituted piperidino in which the substituent is an alkyl group containing from 1 to 6 carbon atoms; R 2 is selected from a group consisting of, a hydrogen atom, and a substituted alkoxy group in which the substituent of the alkoxy group is selected from the group consisting of, an unsubstituted piperidino and a substituted piperidino in which the substituent is an alkyl group containing from 1 to 6 carbon atoms; and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 33
Dependent Claim
48 words
The method of claim 28 in which R 1 is selected from a group consisting of: a substituted alkoxy in which the substituent is a piperidino and a substituted alkoxy in which the substituent is a substituted piperidino and in which the piperidino substituent is an alkoxy group.
Claim 34
Dependent Claim
10 words
The method of claim 29 in which R2 is hydrogen.
Claim 35
Dependent Claim
19 words
The method of claim 30 in which R 1 and R 2 are each at the para ring position.
Claim 36
Dependent Claim
10 words
The method of claim 31 in which X is chlorine.
Claim 37
Dependent Claim
26 words
The method of claim 28 in which R 2 is selected from a group consisting of: a substituted alkoxy in which the substituent is a piperidino.
Claim 38
Dependent Claim
10 words
The compound of claim 33 in which R1 is hydrogen.
Claim 39
Dependent Claim
19 words
The compound of claim 34 in which R 1 and R 2 are each at the para ring position.
Claim 40
Dependent Claim
10 words
The compound of claim 35 in which X is chlorine.
Claim 41
Dependent Claim
21 words
The compound of claim 1 in which X is chlorine, R 1 is a piperidinoethoxy group, and R 2 is hydrogen.
Claim 42
Dependent Claim
21 words
The compound of claim 1 in which X is chlorine, R 1 is hydrogen and R 2 is a piperidinoethoxy group.
Claim 43
Dependent Claim
21 words
The compound of claim 10 in which X is chlorine, R 1 is a piperidinoethoxy group, and R 2 is hydrogen.
Claim 44
Dependent Claim
21 words
The compound of claim 10 in which X is chlorine, R 1 is hydrogen and R 2 is a piperidinoethoxy group.
Claim 45
Dependent Claim
21 words
The compound of claim 19 in which X is chlorine, R 1 is a piperidinoethoxy group, and R 2 is hydrogen.
Claim 46
Dependent Claim
21 words
The compound of claim 19 in which X is chlorine, R 1 is hydrogen and R 2 is a piperidinoethoxy group.
Claim 47
Dependent Claim
21 words
The compound of claim 28 in which X is chlorine, R 1 is a piperidinoethoxy group, and R 2 is hydrogen.
Claim 48
Dependent Claim
21 words
The compound of claim 28 in which X is chlorine, R 1 is hydrogen and R 2 is a piperidinoethoxy group.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-06-27 | 1997-12-27 | 1998-06-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-06-27 | 2001-12-27 | 2002-06-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-06-27 | 2005-12-27 | 2006-06-28 | $7700.00 | Window Closed / Lapsed |