US4544663A
Expired / Lapsed
US
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Indolamine derivatives as anti-fertility agents
Assignee: Sandoz Inc
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Filing: 1984-05-07
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Granted: 1985-10-01
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Expires: 2004-05-07
Abstract
Abstract This disclosure relates to the aspermatogenesis activity of (a) compounds of the formula: <IMAGE> (1) where m is an integer from 1 to 4 X represents hydrogen or -OH R represents Ar, <IMAGE> Ar represents <IMAGE> <IMAGE> +TR <IMAGE> R1 represents hydrogen, fluoro, chloro, lower alkyl or lower alkoxy, R2 and R3 each, independently, represent lower alkyl, or R2 and R3 together with N represent <IMAGE> wherein n is 1, 2 or 3, R4 represents hydrogen or lower alkyl, and R5 represents hydrogen or lower alkyl, unsubstituted phenyl or phenyl mono- or di-substituted with fluoro, chloro, lower alkyl or lower alkoxy, or (b) compounds of the formula: <IMAGE> IIb where R' is Ar or <IMAGE> Ar, R1, R2, R3, R4 and R5 are as defined above, or a pharmaceutically acceptable acid addition salt thereof.
Inventors
- 👤 Robert E. Manning
- 👤 Jeffrey Nadelson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 08:43
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/41; A61K31/42; A61K31/40
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
161 words
A method of inducing aspermatogenesis in male mammals requiring anti-fertility treatment which comprises administering to the mammal an anti-fertility therapeutically effective amount of (a) a compound of the formula: ##STR17## where m is an integer from 1 to 4 X represents hydrogen or --OH R represents Ar, ##STR18## Ar represents ##STR19## R 1 represents hydrogen, fluoro, chloro, lower alkyl or lower alkoxy, R 2 and R 3 each, independently, represent lower alkyl, or R 2 and R 3 together with N represent ##STR20## wherein n is 1, 2 or 3, R 4 represents hydrogen or lower alkyl, and R 5 represents hydrogen or lower alkyl, unsubstituted phenyl or phenyl mono- or di-substituted with fluoro, chloro, lower alkyl or lower alkoxy, or (b) a compound of the formula: ##STR21## where R' is Ar or ##STR22## Ar, R 1 , R 2 , R 3 , R 4 and R 5 are as defined above, or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Independent Claim
161 words
A method of inducing aspermatogenesis in male mammals requiring anti-fertility treatment which comprises administering to the mammal an anti-fertility therapeutically effective amount of (a) a compound of the formula: ##STR17## where m is an integer from 1 to 4 X represents hydrogen or --OH R represents Ar, ##STR18## Ar represents ##STR19## R 1 represents hydrogen, fluoro, chloro, lower alkyl or lower alkoxy, R 2 and R 3 each, independently, represent lower alkyl, or R 2 and R 3 together with N represent ##STR20## wherein n is 1, 2 or 3, R 4 represents hydrogen or lower alkyl, and R 5 represents hydrogen or lower alkyl, unsubstituted phenyl or phenyl mono- or di-substituted with fluoro, chloro, lower alkyl or lower alkoxy, or (b) a compound of the formula: ##STR21## where R' is Ar or ##STR22## Ar, R 1 , R 2 , R 3 , R 4 and R 5 are as defined above, or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
18 words
A method according to claim 1 in which 200 to 2000 milligrams of the compound are administered daily.
Claim 4
Dependent Claim
18 words
A method according to claim 1 in which 500 to 1000 milligrams of the compound are administered daily.
Claim 5
Dependent Claim
20 words
A method according to claim 1 in which 100 to 1000 milligrams of the compound are administered per unit dose.
Claim 6
Dependent Claim
20 words
A method according to claim 1 in which 250 to 500 milligrams of the compound are administered per unit dose.
Claim 7
Dependent Claim
11 words
A method according to claim 1 in which X is hydroxy.
Claim 8
Dependent Claim
11 words
A method according to claim 1 in which m is 1.
Claim 9
Dependent Claim
23 words
A method according to claim 1 in which R is ##STR23## where R 4 and R 5 are as defined in claim 1.
Claim 10
Dependent Claim
23 words
A method according to claim 1 in which R is ##STR24## where R 4 and R 5 are as defined in claim 1.
Claim 11
Dependent Claim
11 words
A method according to claim 1 in which R is ##STR25##
Claim 12
Dependent Claim
16 words
A method according to claim 1 in which R 2 and R 3 are lower alkyl.
Claim 13
Dependent Claim
16 words
A method according to claim 1 in which R 4 and R 5 are lower alkyl.
Claim 14
Dependent Claim
12 words
A method according to claim 1 in which R 1 is fluoro.
Claim 15
Dependent Claim
29 words
A method according to claim 6 in which R 1 is hydrogen or fluoro and R 3 , R 4 , R 5 and R 6 are lower alkyl.
Claim 16
Dependent Claim
18 words
The method according to claim 1 in which the compound is α-(dimethylaminomethyl)-2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indole-3-methanol, or a pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim
18 words
The method according to claim 1 in which the compound is α-(pyrrolidinomethyl)-2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indole-3-methanol, or a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
18 words
The method according to claim 1 in which the compound is α-(dimethylaminomethyl)-5-fluoro-2-(3,5-dimethyl-4-isoxazolyl)-1H-indole-3-methanol, or a pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim
18 words
The method according to claim 1 in which the compound is 2-(2-naphthyl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indole or a pharmaceutically acceptable salt thereof.
Claim 20
Dependent Claim
18 words
The method according to claim 1 in which the compound is 2-(3-ethyl-5-methyl-4-isoxazolyl)-3-(3-dimethylaminopropyl)-indole or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
18 words
The method according to claim 1 in which the compound is 4-amino-3-[3-(2-dimethylamino-1-hydroxyethyl)-1H-indol-2-yl]-3-hexen-2-one or a pharmaceutically acceptable salt thereof.
Claim 22
Dependent Claim
20 words
The method according to claim 1 in which the compound is α-(dimethylaminomethyl)-2-(5-ethyl-3-methyl-4-isoxazolyl)-1H-indole-3-methanol or 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanone, or a pharmaceutically acceptable salt thereof.
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) | 1988-09-30 | 1989-04-01 | 1989-10-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-30 | 1993-04-01 | 1993-10-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-30 | 1997-04-01 | 1997-10-01 | $7700.00 | Window Closed / Lapsed |