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US5658927A
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Diphenylcyclopropyl analogs
Assignee: University of Oklahoma
•
Filing: 1995-06-07
•
Granted: 1997-08-19
•
Expires: 2015-06-07
Abstract
Abstract 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.
Inventors
- 👤 Robert A. Magarian
- 👤 Joseph T. Pento
- 👤 Lynette Overacre
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 23:35
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; C07C217/00; C07C217/02; C07C217/04; C07C217/06; C07C217/14; C07C217/18; C07C309/00; C07C309/63; C07C309/64; C07C309/65; C07C309/66; C07C2601/00; C07C2601/02
Claims Analysis
Total Claims: 80
Claim 1
Independent Claim
213 words
A compound having the formula: ##STR30## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; R 2 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration.
Claim 2
Dependent Claim
213 words
A compound having the formula: ##STR30## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; R 2 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration.
Claim 3
Dependent Claim
33 words
The compound of claim 1 in which R 2 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 3 is a hydrogen.
Claim 4
Dependent Claim
19 words
The compound of claim 2 wherein at least one of R 1 and R 4 is a methyl group.
Claim 5
Dependent Claim
14 words
The compound of claim 3 wherein R 1 and R 4 are methyl groups.
Claim 6
Dependent Claim
16 words
The compound of claim 4 wherein the R 2 group is in the para ring position.
Claim 7
Dependent Claim
33 words
The Compound of claim 1 in which R 3 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 2 is a hydrogen.
Claim 8
Dependent Claim
19 words
The compound of claim 6 wherein at least one of R 1 and R 4 is a methyl group.
Claim 9
Dependent Claim
14 words
The compound of claim 7 wherein R 1 and R 4 are methyl groups.
Claim 10
Dependent Claim
16 words
The compound of claim 8 wherein the R 3 group is in the para ring position.
Claim 11
Dependent Claim
12 words
The compound of claim 1 wherein the X is a chlorine atom.
Claim 12
Dependent Claim
199 words
A compound having the formula: ##STR31## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or a methyl group; R 2 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or a methyl group; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration.
Claim 13
Dependent Claim
199 words
A compound having the formula: ##STR31## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or a methyl group; R 2 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or a methyl group; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration.
Claim 14
Dependent Claim
33 words
The compound of claim 11 in which R 2 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 3 is a hydrogen.
Claim 15
Dependent Claim
14 words
The compound of claim 12 wherein R 1 and R 4 are methyl groups.
Claim 16
Dependent Claim
16 words
The compound of claim 13 wherein the R 2 group is in the para ring position.
Claim 17
Dependent Claim
33 words
The compound of claim 11 in which R 2 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 3 is a hydrogen.
Claim 18
Dependent Claim
14 words
The compound of claim 15 wherein R 1 and R 4 are methyl groups.
Claim 19
Dependent Claim
16 words
The compound of claim 16 wherein the R 2 group is in the para ring position.
Claim 20
Dependent Claim
12 words
The compound of claim 11 wherein the X is a chlorine atom.
Claim 21
Dependent Claim
230 words
A composition of matter comprising: a compound having the formula: ##STR32## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; R 2 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration; and a pharmaceutically acceptable carrier of sufficient quantity to solubilize the compound.
Claim 22
Dependent Claim
230 words
A composition of matter comprising: a compound having the formula: ##STR32## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; R 2 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration; and a pharmaceutically acceptable carrier of sufficient quantity to solubilize the compound.
Claim 23
Dependent Claim
33 words
The composition of claim 19 in which R 2 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 3 is a hydrogen.
Claim 24
Dependent Claim
19 words
The composition of claim 20 wherein at least one of R 1 and R 4 is a methyl group.
Claim 25
Dependent Claim
14 words
The composition of claim 21 wherein R 1 and R 4 are methyl groups.
Claim 26
Dependent Claim
16 words
The composition of claim 22 wherein the R 2 group is in the para ring position.
Claim 27
Dependent Claim
33 words
The composition of claim 19 in which R 3 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 2 is a hydrogen.
Claim 28
Dependent Claim
19 words
The composition of claim 24 wherein at least one of R 1 and R 4 is a methyl group.
Claim 29
Dependent Claim
14 words
The composition of claim 25 wherein R 1 and R 4 are methyl groups.
Claim 30
Dependent Claim
16 words
The composition of claim 26 wherein the R 3 group is in the para ring position.
Claim 31
Dependent Claim
12 words
The composition of claim 19 wherein the X is a chlorine atom.
Claim 32
Dependent Claim
216 words
A composition of matter, comprising: a compound having the formula: ##STR33## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or a methyl group; R 2 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or a methyl group; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration; and a pharmaceutically acceptable carrier of sufficient quantity to solubilize the compound.
Claim 33
Dependent Claim
216 words
A composition of matter, comprising: a compound having the formula: ##STR33## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or a methyl group; R 2 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or a methyl group; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration; and a pharmaceutically acceptable carrier of sufficient quantity to solubilize the compound.
Claim 34
Dependent Claim
33 words
The composition of claim 29 in which R 2 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 3 is a hydrogen.
Claim 35
Dependent Claim
14 words
The composition of claim 30 wherein R 1 and R 4 are methyl groups.
Claim 36
Dependent Claim
16 words
The composition of claim 31 wherein the R 2 group is in the para ring position.
Claim 37
Dependent Claim
33 words
The composition of claim 29 in which R 2 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 3 is a hydrogen.
Claim 38
Dependent Claim
14 words
The composition of claim 33 wherein R 1 and R 4 are methyl groups.
Claim 39
Dependent Claim
16 words
The composition of claim 34 wherein the R 2 group is in the para ring position.
Claim 40
Dependent Claim
12 words
The composition of claim 29 wherein the X is a chlorine atom.
Claim 41
Independent Claim
241 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 of the compounds having the formula: ##STR34## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; R 2 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration.
Claim 42
Independent Claim
241 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 of the compounds having the formula: ##STR34## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; R 2 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration.
Claim 43
Dependent Claim
33 words
The method of claim 37 in which R 2 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 3 is a hydrogen.
Claim 44
Dependent Claim
19 words
The method of claim 38 wherein at least one of R 1 and R 4 is a methyl group.
Claim 45
Dependent Claim
14 words
The method of claim 39 wherein R 1 and R 4 are methyl groups.
Claim 46
Dependent Claim
16 words
The method of claim 40 wherein the R 2 group is in the para ring position.
Claim 47
Dependent Claim
33 words
The method of claim 37 in which R 3 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 2 is a hydrogen.
Claim 48
Dependent Claim
19 words
The method of claim 42 wherein at least one of R 1 and R 4 is a methyl group.
Claim 49
Dependent Claim
14 words
The method of claim 43 wherein R 1 and R 4 are methyl groups.
Claim 50
Dependent Claim
16 words
The method of claim 44 wherein the R 3 group is in the para ring position.
Claim 51
Dependent Claim
12 words
The method of claim 37 wherein the X is a chlorine atom.
Claim 52
Independent Claim
227 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 of the compounds having the formula: ##STR35## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or a methyl group; R 2 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or a methyl group; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration.
Claim 53
Independent Claim
227 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 of the compounds having the formula: ##STR35## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or a methyl group; R 2 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or a methyl group; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration.
Claim 54
Dependent Claim
33 words
The method of claim 47 in which R 2 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 3 is a hydrogen.
Claim 55
Dependent Claim
14 words
The method of claim 48 wherein R 1 and R 4 are methyl groups.
Claim 56
Dependent Claim
16 words
The method of claim 49 wherein the R 2 group is in the para ring position.
Claim 57
Dependent Claim
33 words
The method of claim 47 in which R 2 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 3 is a hydrogen.
Claim 58
Dependent Claim
14 words
The method of claim 51 wherein R 1 and R 4 are methyl groups.
Claim 59
Dependent Claim
16 words
The method of claim 52 wherein the R 2 group is in the para ring position.
Claim 60
Dependent Claim
12 words
The method of claim 47 wherein the X is a chlorine atom.
Claim 61
Independent Claim
244 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 of the compounds having the formula: ##STR36## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; R 2 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen, and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration.
Claim 62
Independent Claim
244 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 of the compounds having the formula: ##STR36## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; R 2 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen, and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration.
Claim 63
Dependent Claim
33 words
The method of claim 55 in which R 2 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 3 is a hydrogen.
Claim 64
Dependent Claim
19 words
The method of claim 56 wherein at least one of R 1 and R 4 is a methyl group.
Claim 65
Dependent Claim
14 words
The method of claim 57 wherein R 1 and R 4 are methyl groups.
Claim 66
Dependent Claim
16 words
The method of claim 58 wherein the R 2 group is in the para ring position.
Claim 67
Dependent Claim
33 words
The method of claim 55 in which R 3 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 2 is a hydrogen.
Claim 68
Dependent Claim
19 words
The method of claim 60 wherein at least one of R 1 and R 4 is a methyl group.
Claim 69
Dependent Claim
14 words
The method of claim 61 wherein R 1 and R 4 are methyl groups.
Claim 70
Dependent Claim
16 words
The method of claim 62 wherein the R 3 group is in the para ring position.
Claim 71
Dependent Claim
12 words
The method of claim 55 wherein the X is a chlorine atom.
Claim 72
Independent Claim
230 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 of the compounds having the formula: ##STR37## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or a methyl group; R 2 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or a methyl group; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen, and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration.
Claim 73
Independent Claim
230 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 of the compounds having the formula: ##STR37## or any pharmaceutically acceptable salt thereof, in which: X is a hydrogen or halogen atom; R 1 is a hydrogen atom or a methyl group; R 2 is selected from the 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 piperidine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; R 3 is selected from the 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 piperazine and a substituted piperidine in which the substituent is an alkyl group containing from 1 to six carbon atoms; and R 4 is a hydrogen atom or a methyl group; and with the proviso that R 1 and R 4 cannot simultaneously be hydrogen, and further with the proviso that R 2 and R 3 cannot simultaneously be hydrogen, and wherein the bonds designated by () represent that the compound can be in the cis- or trans- isomer configuration.
Claim 74
Dependent Claim
33 words
The method of claim 65 in which R 2 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 3 is a hydrogen.
Claim 75
Dependent Claim
14 words
The method of claim 66 wherein R 1 and R 4 are methyl groups.
Claim 76
Dependent Claim
16 words
The method of claim 67 wherein the R 2 group is in the para ring position.
Claim 77
Dependent Claim
33 words
The method of claim 65 in which R 2 is selected from a group consisting of: an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group; and R 3 is a hydrogen.
Claim 78
Dependent Claim
14 words
The method of claim 69 wherein R 1 and R 4 are methyl groups.
Claim 79
Dependent Claim
16 words
The method of claim 70 wherein the R 2 group is in the para ring position.
Claim 80
Dependent Claim
12 words
The method of claim 65 wherein the X is a chlorine atom.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 2000-08-18 | 2001-02-17 | 2001-08-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-08-18 | 2005-02-17 | 2005-08-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-08-18 | 2009-02-17 | 2009-08-19 | $7700.00 | Window Closed / Lapsed |