Patent US4550730A successfully refreshed from Google Patents.
US5422367A
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Diphenylcyclopropyl analogs as antiestrogenic and antitumor agents
Assignee: University of Oklahoma
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Filing: 1994-02-25
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Granted: 1995-06-06
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Expires: 2014-02-25
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 12:49
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: 52
Claim 1
Independent Claim
165 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, a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbons, 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 a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbons; and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 2
Dependent Claim
165 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, a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbons, 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 a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbons; and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 3
Dependent Claim
24 words
The compound of claim 1 in which R 1 is selected from a group consisting of: an alkylsulfonyloxy alkoxy group; and a dialkylaminoalkoxy 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
24 words
The compound of claim 1 in which R 2 is selected from a group consisting of: an alkylsulfonyloxy alkoxy group; and a dialkylaminoalkoxy 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
40 words
The compound of claim 1 in which X is chlorine, R 1 is a methanesulfonyloxyethoxy group or hydrogen and R 2 is a methanesulfonyloxyethoxy group or hydrogen with the proviso that R 1 and R 2 are not simultaneously hydrogen.
Claim 12
Dependent Claim
40 words
The compound of claim 1 in which X is chlorine, R 1 is a dimethylaminoethoxy group or hydrogen and R 2 is a dimethylaminoethoxy group or hydrogen, with the proviso that R 1 and R 2 are not simultaneously hydrogen.
Claim 13
Dependent Claim
40 words
The compound of claim 1 in which X is chlorine, R 1 is a diethylaminoethoxy group or hydrogen and R 2 is a diethylaminoethoxy group or hydrogen with the proviso that R 1 and R 2 are not simultaneously hydrogen.
Claim 14
Dependent Claim
186 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 substituted alkoxy group in which the substituent of the alkoxy group is selected from a group consisting of, a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbons; 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, a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbons; and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 15
Dependent Claim
186 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 substituted alkoxy group in which the substituent of the alkoxy group is selected from a group consisting of, a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbons; 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, a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbons; and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 16
Dependent Claim
24 words
The composition of matter claim 13 in which R 1 is selected from a group containing: an alkylsulfonyloxy alkoxy group; and a dialkylaminoalkoxy group.
Claim 17
Dependent Claim
13 words
The composition of matter of claim 14 in which R 2 is hydrogen.
Claim 18
Dependent Claim
23 words
The composition of matter of claim 15 in which the R 1 and the R 2 are each at the para ring position.
Claim 19
Dependent Claim
12 words
The composition of matter of claim 16 in which X is chlorine.
Claim 20
Dependent Claim
25 words
The composition of matter of claim 13 in which R 2 is selected from a group consisting of: an alkylsulfonyloxyalkoxy group; and a dialkylaminoalkoxy group.
Claim 21
Dependent Claim
13 words
The composition of matter of claim 18 in which R 1 is hydrogen.
Claim 22
Dependent Claim
23 words
The composition of matter of claim 19 in which the R 1 and the R 2 are each at the para ring position.
Claim 23
Dependent Claim
12 words
The composition of matter of claim 20 in which X is chlorine.
Claim 24
Dependent Claim
42 words
The composition of matter of claim 13 in which X is chlorine, R 1 is a methanesulfonyloxyethoxy group or hydrogen and R 2 is a methanesulfonyloxyethoxy group or hydrogen with the proviso that R 1 and R 2 are not simultaneously hydrogen.
Claim 25
Dependent Claim
42 words
The composition of matter of claim 13 in which X is chlorine, R 1 is a dimethylaminoethoxy group or hydrogen and R 2 is a dimethylaminoethoxy group or hydrogen, with the proviso that R 1 and R 2 are not simultaneously hydrogen.
Claim 26
Dependent Claim
42 words
The composition of matter of claim 13 in which X is chlorine, R 1 is a diethylaminoethoxy group or hydrogen and R 2 is a diethylaminoethoxy group or hydrogen with the proviso that R 1 and R 2 are not simultaneously hydrogen.
Claim 27
Independent Claim
183 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: X is selected from a group consisting of, halogen atoms and hydrogen 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 a group consisting of, a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbons; 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 comprises a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbons; and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 28
Independent Claim
183 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: X is selected from a group consisting of, halogen atoms and hydrogen 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 a group consisting of, a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbons; 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 comprises a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbons; and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 29
Dependent Claim
23 words
The method of claim 25 in which R 1 is selected from a group consisting of: an alkylsulfonyloxyalkoxy group, and a dialkylaminoalkoxy group.
Claim 30
Dependent Claim
11 words
The method of claim 26 in which R 2 is hydrogen.
Claim 31
Dependent Claim
21 words
The method of claim 27 in which the R 1 and the R 2 are each at the para ring position.
Claim 32
Dependent Claim
10 words
The method of claim 28 in which X is chlorine.
Claim 33
Dependent Claim
23 words
The method of claim 25 in which R 2 is selected from a group consisting of: an alkylsulfonyloxyalkoxy group, and a dialkylaminoalkoxy group.
Claim 34
Dependent Claim
11 words
The method of claim 30 in which R 1 is hydrogen.
Claim 35
Dependent Claim
19 words
The compound of claim 31 in which R 1 and R 2 are each at the para ring position.
Claim 36
Dependent Claim
10 words
The compound of claim 32 in which X is chlorine.
Claim 37
Dependent Claim
40 words
The method of claim 25 in which X is chlorine, R 1 is a methanesulfonyloxyethoxy group or hydrogen and R 2 is a methanesulfonyloxyethoxy group or hydrogen with the proviso that R 1 and R 2 are not simultaneously hydrogen.
Claim 38
Dependent Claim
40 words
The method of claim 25 in which X is chlorine, R 1 is a dimethylaminoethoxy group or hydrogen and R 2 is a dimethylaminoethoxy group or hydrogen, with the proviso that R 1 and R 2 are not simultaneously hydrogen.
Claim 39
Dependent Claim
40 words
The method of claim 25 in which X is chlorine, R 1 is a diethylaminoethoxy group or hydrogen and R 2 is a diethylaminoethoxy group or hydrogen with the proviso that R 1 and R 2 are not simultaneously hydrogen.
Claim 40
Independent Claim
179 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 comprises a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbon; 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 comprises a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbons; and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 41
Independent Claim
179 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 comprises a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbon; 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 comprises a dialkylamino group in which the alkyl substituent contains from 1 to 6 carbons, and an alkylsulfonyloxy group in which the alkyl substituent contains from 1 to 6 carbons; and with the proviso that R 1 and R 2 cannot be simultaneously hydrogen.
Claim 42
Dependent Claim
23 words
The method of claim 37 in which R 1 is selected from a group consisting of: an alkylsulfonyloxyalkoxy group; and a dialkylaminoalkoxy group.
Claim 43
Dependent Claim
13 words
The method of claim 38 in which R 2 R 2 is hydrogen.
Claim 44
Dependent Claim
19 words
The method of claim 39 in which R 1 and R 2 are each at the para ring position.
Claim 45
Dependent Claim
10 words
The method of claim 40 in which X is chlorine.
Claim 46
Dependent Claim
23 words
The method of claim 37 in which R 2 is selected from a group consisting of: an alkylsulfonyloxyalkoxy group; and a dialkylaminoalkoxy group.
Claim 47
Dependent Claim
11 words
The method of claim 42 in which R 1 is hydrogen.
Claim 48
Dependent Claim
19 words
The compound of claim 43 in which R 1 and R 2 are each at the para ring position.
Claim 49
Dependent Claim
10 words
The compound of claim 44 in which X is chlorine.
Claim 50
Dependent Claim
40 words
The method of claim 37 in which X is chlorine, R 1 is a methanesulfonyloxyethoxy group or hydrogen and R 2 is a methanesulfonyloxyethoxy group or hydrogen with the proviso that R 1 and R 2 are not simultaneously hydrogen.
Claim 51
Dependent Claim
40 words
The method of claim 37 in which X is chlorine R 1 is a dimethylaminoethoxy group or hydrogen and R 2 is a dimethylaminoethoxy group or hydrogen, with the proviso that R 1 and R 2 are not simultaneously hydrogen.
Claim 52
Dependent Claim
40 words
The method of claim 37 in which X is chlorine, R 1 is a diethylaminoethoxy group or hydrogen and R 2 is a diethylaminoethoxy group or hydrogen with the proviso that R 1 and R 2 are not simultaneously hydrogen.
References Cited (Backward Citations)
US3646146A
Cited
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