US4863911A
Expired / Lapsed
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Method for treating male sexual dysfunction
Assignee: University of Florida
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Filing: 1986-08-04
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Granted: 1989-09-05
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Expires: 2006-08-04
Abstract
Abstract The invention provides a method for treating sexual dysfunction in male mammals using a compound of the formula [E-DHC](I) or a non-toxic pharmaceutically acceptable salt thereof, wherein [E] is an estrogen and [DHC] is the reduced, biooxidizable, blood-brain barrier-penetrating, lipoidal form of a dihydropridine-><-pyridinium salt redox carrier. Compositions for use in the subject method are also disclosed. A preferred compound for use in the method and compositions is an estradiol derivative, namely, 17 beta -[(1-methyl-1,4-dihydro-3-pyridinyl)carbonyloxy]estra-1,3,5(10)-trien- 3-ol.
Inventors
- 👤 Wesley R. Anderson, Jr.
- 👤 Nicholas S. Bodor
- 👤 James W. Simpkins
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 22:14
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/56; A61K31/565; A61K31/33; A61K31/395; A61K31/435; A61K31/44; A61K47/00; A61K47/50; A61K47/51; A61K47/54; A61K47/559; A61P; A61P13/00; A61P13/02; A61P15/00
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
67 words
A method for treating male sexual dysfunction, said method comprising administering to a male mammal in need of such treatment, an amount effective to treat said dysfunction in said male mammal of a compound of the formula [E--DHC] (I) or a non-toxic pharmaceutically acceptable salt thereof, wherein [E] is an estrogen and [DHC] is the reduced, biooxidizable, blood-brain barrier-penetrating, lipoidal form of a dihydropyridine⃡pyridinium salt redox carrier.
Claim 2
Independent Claim
67 words
A method for treating male sexual dysfunction, said method comprising administering to a male mammal in need of such treatment, an amount effective to treat said dysfunction in said male mammal of a compound of the formula [E--DHC] (I) or a non-toxic pharmaceutically acceptable salt thereof, wherein [E] is an estrogen and [DHC] is the reduced, biooxidizable, blood-brain barrier-penetrating, lipoidal form of a dihydropyridine⃡pyridinium salt redox carrier.
Claim 3
Dependent Claim
120 words
A method according to claim 1, said method comprising administering to a male mammal in need of such treatment, an amount effective to treat said dysfunction in said male mammal of a compound of the formula E--DHC].sub.n (Ia) or a non-toxic pharmaceuticaly acceptable salt thereof, wherein E-- is the residue of an estrogen containing at least one reactive hydroxyl functional group, said residue being characterized by the absence of a hydrogen atom from at least one of said reactive functional groups in said estrogen; n is a positive integer equal to the number of said functional groups from which a hydrogen atom is absent; and [DHC] is the reduced, biooxidizable, blood-brain barrier-penetrating, lipoidal form of a dihydropyridine⃡pyridinium salt redox carrier.
Claim 4
Dependent Claim
12 words
A method according to claim 2, wherein n is 1 or 2.
Claim 5
Dependent Claim
17 words
A method according to claim 2, wherein E-- is the residue of a natural or semisynthetic estrogen.
Claim 6
Dependent Claim
22 words
A method according to claim 2, wherein E-- is the residue of a 3-monohydroxy, 17-monohydroxy or 3,17-dihydroxy steroid having an aromatic A-ring.
Claim 7
Dependent Claim
13 words
A method according to claim 2, wherein E-- is a residue of estradiol.
Claim 8
Dependent Claim
18 words
A method according to claim 2, wherein E-- is the residue of a 3- or 17-monoester of estradiol.
Claim 9
Dependent Claim
27 words
A method according to claim 2, wherein E-- is the residue of estradiol benzoate, estradiol cypionate, estradiol enanthate, estradiol undecylate, estradiol valerate, estradiol propionate or estradiol undecenylate.
Claim 10
Dependent Claim
13 words
A method according to claim 2, wherein E-- is the residue of estrone.
Claim 11
Dependent Claim
13 words
A method according to claim 2, wherein E-- is a residue of estriol.
Claim 12
Dependent Claim
14 words
A method according to claim 2, wherein E-- is a residue of ethinyl estradiol.
Claim 13
Dependent Claim
13 words
A method according to claim 2, wherein E-- is the residue of mestranol.
Claim 14
Dependent Claim
21 words
A method according to claim 2, wherein E-- is the residue of quinestrol, estrazinol or estrofurate or a residue of nylestriol.
Claim 15
Dependent Claim
283 words
A method according to claim 2, wherein [DHC] is ##STR110## wherein the alkylene group can be straight or branched and having 1 to 3 carbon atoms; R o is a radical identical to the corresponding portion of a natural amino acid; p is 0, 1 or 2, provided that, when p is 2, then the alkylene groups can be the same or different and the R o radicals can be the same or different; the dotted line in formulas (a'), (b') and (c') indicates the presence of a double bond in either the 4 or 5 position of the dihydropyridine ring; the dotted line in formulas (d'), (e') and (f') indicates the presence of a double bond in either the 2 or 3 position of the dihydroquinoline ring; R 1 is C 1 -C 7 alkyl, C 1 -C 7 haloalkyl or C 7 -C 10 aralkyl; R 3 is C 1 -C 3 alkylene; X is --CONR'R" wherein R' and R", which can be the same or different, are each H or C 1 -C 7 alkyl, or X is --CH═NOR'" wherein R'" is H or C 1 -C 7 alkyl; the carbonyl-containing groupings in formulas (a') and (c') and the X substituent in formula (b') can each be attached at the 2, 3 or 4 position of the dihydropyridine ring; the carbonyl-containing groupings in formulas (d') and (f') and the X substituent in formula (e') can each be attached at the 2, 3 or 4 position of the dihydroquinoline ring; and the carbonyl-containing groupings in formulas (g') and (j') and the X substituent in formula (h') can each be attached at the 1, 3 or 4 position of the dihydroisoquinoline ring.
Claim 16
Dependent Claim
10 words
A method according to claim 14, wherein p is 0.
Claim 17
Dependent Claim
10 words
A method according to claim 14, wherein p is 1.
Claim 18
Dependent Claim
57 words
A method according to claim 14, wherein p is 1 or 2, alkylene is --CH 2 -- and R o is H, --CH 3 , --CH(CH 3 ) 2 , --CH 2 --CH(CH 3 ) 2 , ##STR111## --(CH 2 ) 2 --SCH 3 , --CH 2 --CONH 2 or --CH 2 CH 2 --CONH 2 .
Claim 19
Dependent Claim
13 words
A method according to claim 14, wherein R 1 is --CH 3 .
Claim 20
Dependent Claim
15 words
A method according to claim 14, wherein R 3 is --CH 2 CH 2 --.
Claim 21
Dependent Claim
12 words
A method according to claim 14, wherein X is --CONH 2 .
Claim 22
Dependent Claim
83 words
A method according to claim 14, wherein the depicted carbonyl-containing groupings in formulas (a') and (c') and the X substituent in formula (b') are attached at the 3-position of the dihydropyridine ring; the depicted carbonyl-containing groupings in formulas (d') and (f') and the X substituent in formula (e') are attached at the 3-position of the dihydroquinoline ring; and the depicted carbonyl-containing groupings in formulas (g') and (j') and the X substituent in formula (h') are attached at the 4-position of the dihydroisoquinoline ring.
Claim 23
Dependent Claim
69 words
A method according to claim 14, wherein [DHC] is ##STR112## wherein R 1 is C 1 -C 7 alkyl, C 1 -C 7 haloalkyl or C 7 -C 10 aralkyl, the dotted line indicates the presence of a double bond in either the 4 or 5 position of the dihydropyridine ring and the carbonyl group can be attached at the 2, 3 or 4 position of the dihydropyridine ring.
Claim 24
Dependent Claim
10 words
A method according to claim 22, wherein [DHC] is ##STR113##
Claim 25
Dependent Claim
13 words
A method according to claim 23, wherein E-- is a residue of estradiol.
Claim 26
Dependent Claim
15 words
A method according to claim 2, wherein the compound of formula (Ia) is 17 β-[(1-methyl-1,4-dihydro-3-pyridinyl)carbonyloxy]estra-1,3,5(10)-trien-3-ol.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-09-04 | 1993-03-06 | 1993-09-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-09-04 | 1997-03-06 | 1997-09-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-09-04 | 2001-03-06 | 2001-09-05 | $7700.00 | Window Closed / Lapsed |