US4359475A
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Thioketal substituted N-alkyl imidazoles
Assignee: Syntex USA LLC
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Filing: 1981-12-21
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Granted: 1982-11-16
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Expires: 2001-12-21
Abstract
Abstract Compounds of the formula: <IMAGE> (I) wherein R1 is phenyl optionally substituted with one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halo, or trifluoromethyl; Z is ethylene or propylene, optionally substituted with a single substituent which is lower alkyl; A is the integer 0, 1, 2, or 3; B is the integer 1, 2, or 3; and wherein the sum of A and B is 1, 2, 3 or 4; and the pharmaceutically acceptable acid addition salts thereof, said compounds being useful as spermicidal, antimicrobial and anticonvulsant agents.
Inventors
- 👤 Keith A. M. Walker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 11:33
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/64; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/56; C07D249/00; C07D249/02; C07D249/08; Y; Y10; Y10S; Y10S424/00; Y10S424/14
Claims Analysis
Total Claims: 49
Claim 1
Independent Claim
87 words
A compound having the general formula ##STR7## wherein R 1 is phenyl optionally substituted with one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halo, or trifluoromethyl; Z is ethylene or propylene, optionally substituted with a single substituent which is lower alkyl; A is the integer 0, 1, 2, or 3; B is the integer 1, 2, or 3; and wherein the sum of A and B is 1, 2, 3 or 4; and the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
87 words
A compound having the general formula ##STR7## wherein R 1 is phenyl optionally substituted with one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halo, or trifluoromethyl; Z is ethylene or propylene, optionally substituted with a single substituent which is lower alkyl; A is the integer 0, 1, 2, or 3; B is the integer 1, 2, or 3; and wherein the sum of A and B is 1, 2, 3 or 4; and the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
16 words
A compound according to claim 1 wherein A is 2 or 3 and B is 1.
Claim 4
Dependent Claim
22 words
A compound according to claim 2 wherein Z is ethylene or ethylene optionally substituted with a single substituent which is lower alkyl.
Claim 5
Dependent Claim
10 words
The compound of claim 3 wherein R 1 is phenyl.
Claim 6
Dependent Claim
18 words
A compound according to claim 3 wherein R 1 is phenyl substituted with one or more halo substituents.
Claim 7
Dependent Claim
12 words
The compound according to claim 5 wherein phenyl is substituted with chloro.
Claim 8
Dependent Claim
16 words
A compound according to claim 6 which is 1-[[2-(2-(4-chlorophenyl)ethyl)-1,3-dithiolan-2-yl]methyl]imidazole and its pharmaceutically acceptable acid addition salts.
Claim 9
Dependent Claim
16 words
A compound according to claim 6 which is 1-[[2-(2-(4-chlorophenyl)ethyl)-4-methyl-1,3-dithiolan-2-yl]methyl]imidazole and its pharmaceutically acceptable acid addition salts.
Claim 10
Dependent Claim
16 words
A compound according to claim 6 which is 1-[[2-(2-(4-chlorophenyl)ethyl)-4-ethyl-1,3-dithiolan-2-yl]methyl]imidazole and it pharmaceutically acceptable acid addition salts.
Claim 11
Dependent Claim
20 words
The compound of claim 3 wherein R 1 is phenyl substituted with one or more substituents which are lower alkyl.
Claim 12
Dependent Claim
15 words
A compound according to claim 10 wherein phenyl is substituted with methyl, ethyl or propyl.
Claim 13
Dependent Claim
16 words
A compound according to claim 11 which is 1-[[2-(2-(4-methylphenyl)ethyl)-1,3-dithiolan-2-yl]methyl]imidazole and the pharmaceutically acceptable acid addition salts.
Claim 14
Dependent Claim
16 words
A compound according to claim 11 which is 1-[[2-(2-(4-methylphenyl)ethyl)-4-methyl-1,3-dithiolan-2-yl]methyl]imidazole and the pharmaceutically acceptable acid addition salts.
Claim 15
Dependent Claim
21 words
A compound according to claim 3 wherein R 1 is phenyl substituted with one or more substituents which are lower alkoxy.
Claim 16
Dependent Claim
16 words
A compound according to claim 14 which is 1-[[2-(2-(4-methoxyphenyl)ethyl)-1,3-dithiolan-2-yl]methyl]imidazole and its pharmaceutically acceptable acid addition salts.
Claim 17
Dependent Claim
16 words
A compound according to claim 14 which is 1-[[2-(2-(4-methoxyphenyl)ethyl)-4-methyl-1,3-dithiolan-2-yl]methyl]imidazole and its pharmaceutically acceptable acid addition salts.
Claim 18
Dependent Claim
17 words
A compound according to claim 2 wherein Z is propylene or propylene optionally substituted by lower alkyl.
Claim 19
Dependent Claim
11 words
A compound according to claim 17 where R 1 is phenyl.
Claim 20
Dependent Claim
18 words
A compound according to claim 17 wherein R 1 is phenyl substituted with one or more halo substituents.
Claim 21
Dependent Claim
12 words
A compound according to claim 19 wherein said said substituents are chloro.
Claim 22
Dependent Claim
16 words
A composition according to claim 20 which is 1-[[2-(2-(4-chlorophenyl)ethyl)-1,3-dithian-2-yl]methyl]imidazole and its pharmaceutically acceptable acid addition salts.
Claim 23
Dependent Claim
16 words
The compound according to claim 20 which is 1-[[2-(2-(4-chlorophenyl)ethyl)-4-methyl-1,3-dithian-2-yl]methyl]imidazole and its pharmaceutically acceptable acid addition salts.
Claim 24
Dependent Claim
16 words
A compound according to claim 20 which is 1-[[2-(2-(4-chlorophenyl)ethyl)-5-methyl-1,3-dithian-2-yl]methyl]imidazole and its pharmaceutically acceptable acid addition salts.
Claim 25
Dependent Claim
21 words
A compound according to claim 17 wherein R 1 is phenyl substituted with one or more substituents which are lower alkyl.
Claim 26
Dependent Claim
15 words
A compound according to claim 24 wherein phenyl is substituted with methyl, ethyl or propyl.
Claim 27
Dependent Claim
16 words
A compound according to claim 25 which is 1-[[2-(2-(4-methylphenyl)ethyl)-1,3-dithian-2-yl]methyl]imidazole and its pharmaceutically acceptable acid addition salts.
Claim 28
Dependent Claim
16 words
A compound according to claim 25 which is 1-[[2-(2-(4-methylphenyl)ethyl)-4-methyl-1,3-dithian-2-yl]methyl]imidazole and its pharmaceutically acceptable acid addition salts.
Claim 29
Dependent Claim
16 words
A compound according to claim 25 which is 1-[[2-(2-(4-methylphenyl)ethyl)-5-methyl-1,3-dithian-2-yl]methyl]imidazole and its pharmaceutically acceptable acid addition salts.
Claim 30
Dependent Claim
21 words
A compound according to claim 17 wherein R 1 is phenyl substituted with one or more substituents which are lower alkoxy.
Claim 31
Dependent Claim
14 words
A compound according to claim 29 wherein phenyl is substituted with methoxy or ethoxy.
Claim 32
Dependent Claim
16 words
A compound according to claim 30 which is 1-[[2-(2-(4-methoxyphenyl)ethyl)-1,3-dithian-2-yl]methyl]imidazole and its pharmaceutically acceptable acid addition salts.
Claim 33
Dependent Claim
16 words
A compound according to claim 30 which is 1-[[2-(2-(4-methoxyphenyl)ethyl)-4-methyl-1,3-dithian-2-yl]methyl]imidazole and its pharmaceutically acceptable acid addition salts.
Claim 34
Dependent Claim
111 words
A composition useful for combating and controlling the growth of fungi, bacteria or protozoa which comprises an excipient and an effective amount of at least one compound of the formula ##STR8## wherein R 1 is phenyl optionally substituted with one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halo, or trifluoromethyl; Z is ethylene or propylene, optionally substituted with a single substituent which is lower alkyl; A is the integer 0, 1, 2, or 3; B is the integer 1, 2, or 3; and wherein the sum of A and B is 1, 2, 3 or 4; and the pharmaceutically acceptable acid addition salts thereof.
Claim 35
Dependent Claim
111 words
A composition useful for combating and controlling the growth of fungi, bacteria or protozoa which comprises an excipient and an effective amount of at least one compound of the formula ##STR8## wherein R 1 is phenyl optionally substituted with one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halo, or trifluoromethyl; Z is ethylene or propylene, optionally substituted with a single substituent which is lower alkyl; A is the integer 0, 1, 2, or 3; B is the integer 1, 2, or 3; and wherein the sum of A and B is 1, 2, 3 or 4; and the pharmaceutically acceptable acid addition salts thereof.
Claim 36
Dependent Claim
28 words
The composition of claim 33 for topical administration wherein a compound of Formula I is present in an amount between 0.1 and 10 weight percent of the composition.
Claim 37
Dependent Claim
30 words
The composition of claim 33 for oral or parenteral administration wherein a compound of Formula I is present in an amount between 0.1 and 90 weight percent of the composition.
Claim 38
Independent Claim
112 words
A method of combating and controlling the growth of fungi, bacteria and protozoa which comprises administering to a subject host an effective amount of at least one compound of the formula ##STR9## wherein R 1 is phenyl optionally substituted with one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halo, or trifluoromethyl; Z is ethylene or propylene, optionally substituted with a single substituent which is lower alkyl; A is the integer 0, 1, 2, or 3; B is the integer 1, 2, or 3; and wherein the sum of A and B is 1, 2, 3 or 4; and the pharmaceutically acceptable acid addition salts thereof.
Claim 39
Independent Claim
112 words
A method of combating and controlling the growth of fungi, bacteria and protozoa which comprises administering to a subject host an effective amount of at least one compound of the formula ##STR9## wherein R 1 is phenyl optionally substituted with one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halo, or trifluoromethyl; Z is ethylene or propylene, optionally substituted with a single substituent which is lower alkyl; A is the integer 0, 1, 2, or 3; B is the integer 1, 2, or 3; and wherein the sum of A and B is 1, 2, 3 or 4; and the pharmaceutically acceptable acid addition salts thereof.
Claim 40
Dependent Claim
14 words
The method of claim 36 wherein a compound of Formula I is administered topically.
Claim 41
Dependent Claim
16 words
The method of claim 36 wherein a compound of Formula I is administered orally or parenterally.
Claim 42
Dependent Claim
109 words
A spermicidal composition useful for effecting contraception in a male or female mammal which comprises a suitable excipient and an effective amount of a compound of the formula ##STR10## wherein R 1 is phenyl optionally substituted with one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halo, or trifluoromethyl; Z is ethylene or propylene, optionally substituted with a single substituent which is lower alkyl; A is the integer 0, 1, 2, or 3; B is the integer 1, 2, or 3; and wherein the sum of A and B is 1, 2, 3 or 4; and the pharmaceutically acceptable acid addition salts thereof.
Claim 43
Dependent Claim
109 words
A spermicidal composition useful for effecting contraception in a male or female mammal which comprises a suitable excipient and an effective amount of a compound of the formula ##STR10## wherein R 1 is phenyl optionally substituted with one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halo, or trifluoromethyl; Z is ethylene or propylene, optionally substituted with a single substituent which is lower alkyl; A is the integer 0, 1, 2, or 3; B is the integer 1, 2, or 3; and wherein the sum of A and B is 1, 2, 3 or 4; and the pharmaceutically acceptable acid addition salts thereof.
Claim 44
Dependent Claim
28 words
The composition of claim 39 for intravaginal administration wherein a compound of Formula I is present in an amount between 0.1 and 10 weight percent of the composition.
Claim 45
Dependent Claim
34 words
The composition of claim 39 for oral or parenteral administration to a male mammal wherein a compound of Formula I is present in an amount between 0.1 and 90 weight percent of the composition.
Claim 46
Independent Claim
114 words
A method for effecting contraception in a male or female mammal by rendering spermatozoa ineffective, which method comprises administering to a subject an effective amount of at least one compound of the formula ##STR11## wherein R 1 is phenyl optionally substituted with one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halo, or trifluoromethyl; Z is ethylene or propylene, optionally substituted with a single substituent which is lower alkyl; A is the integer 0, 1, 2, or 3; B is the integer 1, 2, or 3; and wherein the sum of A and B is 1, 2, 3 or 4; and the pharmaceutically acceptable acid addition salts thereof.
Claim 47
Independent Claim
114 words
A method for effecting contraception in a male or female mammal by rendering spermatozoa ineffective, which method comprises administering to a subject an effective amount of at least one compound of the formula ##STR11## wherein R 1 is phenyl optionally substituted with one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halo, or trifluoromethyl; Z is ethylene or propylene, optionally substituted with a single substituent which is lower alkyl; A is the integer 0, 1, 2, or 3; B is the integer 1, 2, or 3; and wherein the sum of A and B is 1, 2, 3 or 4; and the pharmaceutically acceptable acid addition salts thereof.
Claim 48
Dependent Claim
18 words
The method of claim 42 wherein a compound of Formula I is administered intravaginally to a female mammal.
Claim 49
Dependent Claim
20 words
The method of claim 42 wherein a compound of Formula I is administered orally or parenterally to a male mammal.
References Cited (Backward Citations)
US3575999A
Cited
US4150153A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-11-15 | 1986-05-17 | 1986-11-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-11-15 | 1990-05-17 | 1990-11-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-11-15 | 1994-05-17 | 1994-11-16 | $7700.00 | Window Closed / Lapsed |