US5189212A
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Triarylethylene carboxylic acids with estrogenic activity
Assignee: University of Georgia Research Foundation Inc
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Filing: 1990-09-07
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Granted: 1993-02-23
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Expires: 2010-09-07
Abstract
Abstract Nonsteroidal estrogenic triarylethylene carboxylic acids of the formula <IMAGE> wherein R is (CH2)mO or (CH2)n, where m is an integer from 1 to 4 and n is an integer from 0 to 4, X is hydrogen or hydroxyl, Y is methyl, ethyl, chlorine, or bromine, and wherein the RCOOH and X moieties are either meta or para to the phenyl ethylene linkage. Examples of active compounds include 4-hydroxytamoxifen acid, 3-hydroxytamoxifen acid, 4-[1-(p-hydroxyphenyl)-2-phenyl-1-butenyl]benzoic acid and 4-[1-(p-hydroxyphenyl)-2-phenyl-1-butenyl]phenylacetic acid. Compositions containing these triarylethylene carboxylic acids can be administered to patients to alleviate medical conditions associated with a deficiency of estrogen, including osteoporosis, premenstrual syndrome, vasomotor symptoms associated with menopause, atrophic vaginitis, Kraurosis vulvae, female hypogonadism, primary ovarian failure, excessive hair growth and prostatic cancer.
Inventors
- 👤 Peter C. Ruenitz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 05:11
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/185; A61K31/19; A61P; A61P13/00; A61P13/02; A61P15/00; A61P19/00; A61P19/08; A61P19/10; A61P25/00; A61P25/04; A61P35/00; A61P43/00; C; C07; C07C; C07C59/00; C07C59/40; C07C59/42; C07C59/52; C07C59/58; C07C59/64; C07C59/66; C07C59/68; C07C59/70; C07C65/00; C07C65/01; C07C65/19
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
80 words
A triarylethylene carboxylic acid of the structure: ##STR3## wherein R is (CH 2 ) m O or (CH 2 ) n , m is 1, 2, 3, or 4, and n is 0, 1, 2, 3, or 4; X is hydrogen or hydroxyl, Y is methyl, ethyl, chlorine, or bromine, wherein the RCOOH an X moieties are either metal or para to the phenyl ethylene linkage, and wherein when X is hydrogen, R is not (CH 2 ) n O.
Claim 2
Dependent Claim
80 words
A triarylethylene carboxylic acid of the structure: ##STR3## wherein R is (CH 2 ) m O or (CH 2 ) n , m is 1, 2, 3, or 4, and n is 0, 1, 2, 3, or 4; X is hydrogen or hydroxyl, Y is methyl, ethyl, chlorine, or bromine, wherein the RCOOH an X moieties are either metal or para to the phenyl ethylene linkage, and wherein when X is hydrogen, R is not (CH 2 ) n O.
Claim 3
Dependent Claim
17 words
The compound of claim 1 wherin Y is selected from the group consisting of ethyl and chloro.
Claim 4
Dependent Claim
9 words
The compound of claim 1 wherein X is hydroxyl.
Claim 5
Dependent Claim
11 words
The compound of claim 1 wherein R is CH 2 O.
Claim 6
Dependent Claim
9 words
The compound of claim 1 in the Z configuration.
Claim 7
Dependent Claim
14 words
The compound of claim 1 that is a mixture of Z and E isomers.
Claim 8
Dependent Claim
9 words
The compound of claim 1 in the E configuration.
Claim 9
Dependent Claim
12 words
The compound of claim 1 wherein X is in the para position.
Claim 10
Dependent Claim
10 words
The compound of claim 1 that is 4-hydroxy tamoxifen acid.
Claim 11
Dependent Claim
17 words
The compound of claim 1 selected from the group consisting of 3-HTA, 4-[1-(p-hydroxyphenyl)-2-phenyl-1-butenyl]benzoic acid and 4-[1-(p-hydroxyphenyl)-2-phenyl-1-butenyl]phenylacetic acid.
Claim 12
Dependent Claim
98 words
A pharmaceutical composition comprising an effective amount of a triarylethylene carboxylic acid of the formula ##STR4## wherein R is (CH 2 ) m O or (CH 2 ) n , m is 1, 2, 3, or 4, and n is 0, 1, 2, 3, or 4; X is hydrogen or hydroxyl, Y is methyl, ethyl, chlorine, or bromine; wherein the RCOOH and X moieties are either meta or para to the phenyl ethylene linkage, and wherein when X is H, R is not (CH 2 ) n O; or its pharmaceutically acceptable salt, in a pharmaceutically acceptable carrier.
Claim 13
Dependent Claim
98 words
A pharmaceutical composition comprising an effective amount of a triarylethylene carboxylic acid of the formula ##STR4## wherein R is (CH 2 ) m O or (CH 2 ) n , m is 1, 2, 3, or 4, and n is 0, 1, 2, 3, or 4; X is hydrogen or hydroxyl, Y is methyl, ethyl, chlorine, or bromine; wherein the RCOOH and X moieties are either meta or para to the phenyl ethylene linkage, and wherein when X is H, R is not (CH 2 ) n O; or its pharmaceutically acceptable salt, in a pharmaceutically acceptable carrier.
Claim 14
Dependent Claim
36 words
The pharmaceutical composition of claim 11 comprising a pharmaceutically acceptable carrier selected from the group consisting of topical carriers, subcutaneously injectable carriers, intravenously injectable carriers, orally ingestible carriers, and implantable extended release biocompatible and biodegradable carriers.
Claim 15
Dependent Claim
19 words
The pharmaceutical composition of claim 11 that includes between approximately 10 and 1000 mg of the triarylethylene carboxylic acid.
Claim 16
Dependent Claim
19 words
The pharmaceutical composition of claim 11 that includes between approximately 20 and 40 mg of the triarylethylene carboxylic acid.
Claim 17
Independent Claim
94 words
A method to alleviate a condition treatable with estrogen comprising: administering to a mammalian patient an effective amount of a compound having the structure of ##STR5## wherein R is (CH 2 ) m O or (CH 2 ) n , m is 1, 2, 3, or 4, and n is 0, 1, 2, 3, or 4; X is hydrogen or hydroxyl, Y is methyl, ethyl, chlorine, or bromine; wherein the RCOOH and X moieties are either meta or para to the phenyl ethylene linkage, or its pharmaceutically acceptable salt, in a pharmaceutically acceptable carrier.
Claim 18
Independent Claim
94 words
A method to alleviate a condition treatable with estrogen comprising: administering to a mammalian patient an effective amount of a compound having the structure of ##STR5## wherein R is (CH 2 ) m O or (CH 2 ) n , m is 1, 2, 3, or 4, and n is 0, 1, 2, 3, or 4; X is hydrogen or hydroxyl, Y is methyl, ethyl, chlorine, or bromine; wherein the RCOOH and X moieties are either meta or para to the phenyl ethylene linkage, or its pharmaceutically acceptable salt, in a pharmaceutically acceptable carrier.
Claim 19
Dependent Claim
17 words
The method of claim 15 wherein Y is selected from the group consisting of ethyl and chloro.
Claim 20
Dependent Claim
9 words
The method of claim 15 wherein X is hydroxyl.
Claim 21
Dependent Claim
11 words
The method of claim 15 wherein R is CH 2 O.
Claim 22
Dependent Claim
15 words
The method of claim 15 wherein the triarylethylene carboxylic acid is in the Z configuration.
Claim 23
Dependent Claim
18 words
The method of claim 15 wherein the triarylethylene carboxylic acid is a mixture of Z and E isomers.
Claim 24
Dependent Claim
15 words
The method of claim 15 wherein the triarylethylene carboxylic acid is in the E configuration.
Claim 25
Dependent Claim
12 words
The method of claim 15 wherein X is in the para position.
Claim 26
Dependent Claim
23 words
The method of claim 15 wherein the triarylethylene carboxylic acid is selected from the group consisting of 4-hydroxy tamoxifen acid and tamoxifen acid.
Claim 27
Dependent Claim
23 words
The method of claim 15 wherein the triarylethylene carboxylic acid is selected from the group consisting of 3-HTA, -[1-(p-hydroxyphenyl)-2-phenyl-1-butenyl]benzoic acid and 4-[1-p-hydroxyphenyl)-2-phenyl-1-butenyl]phenylacetic acid.
Claim 28
Dependent Claim
36 words
The method of claim 15 wherein the pharmaceutically acceptable carrier is selected from the group consisting of topical carriers, subcutaneously injectable carriers, intravenously injectable carriers, orally ingestible carriers and implantable extended release biocompatible and biodegradable carriers.
Claim 29
Dependent Claim
23 words
The method of claim 15 wherein the amount of triarylethylene carboxylic acid administered is in the range of 10 mg/day to 1000 mg/day.
Claim 30
Dependent Claim
23 words
The method of claim 15 wherein the amount of triarylethylene carboxylic acid administered is in the range of 20 mg/day to 40 mg/day.
Claim 31
Dependent Claim
27 words
The method of claim 15 wherein the amount of triarylethylene carboxylic acid administered is in the range of 0.15 to 15 mg/kg of body weight per day.
Claim 32
Dependent Claim
27 words
The method of claim 15 wherein the amount of triarylethylene carboxylic acid administered is in the range of 0.29 to 0.58 mg/kg of body weight per day.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1996-02-23 | 1996-08-24 | 1997-02-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-02-23 | 2000-08-24 | 2001-02-23 | $3760.00 | Window Closed / Lapsed |
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