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US4036975A
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1-[2-(1-Adamantyl)-2-(R-thio)ethyl]imidazoles and 1-[2-(1-adamantyl)-2-(R-oxy)ethyl]imidazoles
Assignee: Syntex USA LLC
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Filing: 1976-03-08
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Granted: 1977-07-19
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Expires: 1996-03-08
Abstract
Abstract Compounds of the formula <IMAGE> (I) wherein R is alkyl, cycloalkyl, cycloalkyl lower alkyl, phenyl or phenyl lower alkyl, said phenyl and phenyl lower alkyl optionally substituted on the phenyl ring with one or more substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl; and X is oxygen or sulfur with the proviso that X is not oxygen when R is phenyl or substituted phenyl; and the antimicrobial acid addition salts thereof are useful as antifungal, antibacterial and antiprotozoal agents.
Inventors
- 👤 Keith A. M. Walker
- 👤 Stefan Howard Unger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 17:58
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
100 words
A compound of the formula: ##STR7## wherein R is alkyl, cycloalkyl, cycloalkyl lower alkyl, phenyl or phenyl lower alkyl, said phenyl and phenyl lower alkyl optionally substituted on the phenyl ring with one or more substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl and wherein lower alkyl has 1 to 4 carbon atoms, alkyl has 1 to 12 carbon atoms and cycloalkyl has 5 to 7 carbon atoms; X is oxygen or sulfur with the proviso that X is not oxygen when R is phenyl or substituted phenyl; and the antimicrobial acid addition salts thereof.
Claim 2
Dependent Claim
100 words
A compound of the formula: ##STR7## wherein R is alkyl, cycloalkyl, cycloalkyl lower alkyl, phenyl or phenyl lower alkyl, said phenyl and phenyl lower alkyl optionally substituted on the phenyl ring with one or more substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl and wherein lower alkyl has 1 to 4 carbon atoms, alkyl has 1 to 12 carbon atoms and cycloalkyl has 5 to 7 carbon atoms; X is oxygen or sulfur with the proviso that X is not oxygen when R is phenyl or substituted phenyl; and the antimicrobial acid addition salts thereof.
Claim 3
Dependent Claim
9 words
A compound of claim 1 wherein X is oxygen.
Claim 4
Dependent Claim
9 words
A compound of claim 1 wherein X is sulfur.
Claim 5
Dependent Claim
9 words
A compound of claim 1 wherein R is alkyl.
Claim 6
Dependent Claim
15 words
The compound of claim 4 which is 1-[2-(1-adamantyl)-2-(methoxy)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 7
Dependent Claim
15 words
The compound of claim 4 which is 1-[2-(1-adamantyl)-2-(n-hexyloxy)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 8
Dependent Claim
15 words
The compound of claim 4 which is 1-[2-(1-adamantyl)-2-(n-dodecyloxy)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 9
Dependent Claim
15 words
The compound of claim 4 which is 1-[2-(1-adamantyl)-2-(ethylthio)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 10
Dependent Claim
15 words
The compound of claim 4 which is 1-[2-(1-adamantyl)-2-(heptylthio)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 11
Dependent Claim
15 words
The compound of claim 4 which is 1-[2-(1-adamantyl)-2-(n-dodecylthio)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 12
Dependent Claim
15 words
A compound of claim 1 wherein R is halo substituted benzyl or halo substituted phenyl.
Claim 13
Dependent Claim
15 words
A compound of claim 11 wherein R is chloro substituted benzyl or chloro substituted phenyl.
Claim 14
Dependent Claim
16 words
A compound of claim 12 wherein the chloro substitution in R is 4-chloro, 2,4-dichloro or 3,4-dichloro.
Claim 15
Dependent Claim
15 words
The compound of claim 13 which is 1-[2-(1-adamantyl)-2-(4-chlorobenzyloxy)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 16
Dependent Claim
15 words
The compound of claim 13 which is 1-[2(1-adamantyl)-2-(2,4-dichlorobenzyloxy)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 17
Dependent Claim
15 words
The compound of claim 13 which is 1-[2-(1-adamantyl)-2-(3,4-dichlorobenzyloxy)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 18
Dependent Claim
16 words
The compound of claim 13 which is 1-[2-(1-adamantyl)-2-(4, -chlorophenylthio)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 19
Dependent Claim
15 words
The compound of claim 13 which is 1-[2-(1-adamantyl)-2-(2,4-dichlorophenylthio)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 20
Dependent Claim
15 words
The compound of claim 13 which is 1-[2-(1-adamantyl)-2-(3,4-dichlorophenylthio)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 21
Dependent Claim
15 words
The compound of claim 13 which is 1-[2-(1-adamantyl)-2-(4-chlorobenzylthio)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 22
Dependent Claim
15 words
The compound of claim 13 which is 1-[2-(1-adamantyl)-2-(2,4-dichlorobenzylthio)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 23
Dependent Claim
15 words
The compound of claim 13 which is 1-[2-(1-adamantyl)-2-(3,4-dichlorobenzylthio)ethyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 24
Dependent Claim
124 words
A composition useful for inhibiting the growth of fungi, bacteria or protozoa which comprises an effective amount of a compound of the formula ##STR8## wherein R is alkyl, cycloalkyl, cycloalkyl lower alkyl, phenyl or phenyl lower alkyl, said phenyl and phenyl lower alkyl optionally substituted on the phenyl ring with one or more substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl and wherein lower alkyl has 1 to 4 carbon atoms, alkyl has 1 to 12 carbon atoms and cycloalkyl has 5 to 7 carbon atoms; X is oxygen or sulfur with the provisio that X is not oxygen when R is phenyl and substituted phenyl; or an antimicrobial acid addition salt thereof in admixture with a suitable carrier.
Claim 25
Dependent Claim
124 words
A composition useful for inhibiting the growth of fungi, bacteria or protozoa which comprises an effective amount of a compound of the formula ##STR8## wherein R is alkyl, cycloalkyl, cycloalkyl lower alkyl, phenyl or phenyl lower alkyl, said phenyl and phenyl lower alkyl optionally substituted on the phenyl ring with one or more substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl and wherein lower alkyl has 1 to 4 carbon atoms, alkyl has 1 to 12 carbon atoms and cycloalkyl has 5 to 7 carbon atoms; X is oxygen or sulfur with the provisio that X is not oxygen when R is phenyl and substituted phenyl; or an antimicrobial acid addition salt thereof in admixture with a suitable carrier.
Claim 26
Dependent Claim
17 words
A composition of claim 23 for pharmaceutical use wherein the carrier is a pharmaceutically acceptable, non-toxic carrier.
Claim 27
Dependent Claim
29 words
A composition of claim 24 for topical administration wherein the compound of Formula (I) is present in an amount ranging between 0.1 and 10.0 weight percent of the composition.
Claim 28
Independent Claim
141 words
A method of inhibiting the growth of fungi, bacteria or protozoa which comprises applying to a host object containing or subject to attack by fungi, bacteria or protozoa an effective amount of a compound of the formula ##STR9## wherein R is alkyl, cycloalkyl, cycloalkyl lower alkyl, phenyl or phenyl lower alkyl, said phenyl and phenyl lower alkyl optionally substituted on the phenyl ring with one or more substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl and wherein lower alkyl has 1 to 4 carbon atoms, alkyl has 1 to 12 carbon atoms and cycloalkyl has 5 to 7 carbon atoms; X is oxygen or sulfur with the proviso that X is not oxygen when R is phenyl or substituted phenyl; or an antimicrobial acid addition salt thereof or a composition containing same as an active ingredient.
Claim 29
Independent Claim
141 words
A method of inhibiting the growth of fungi, bacteria or protozoa which comprises applying to a host object containing or subject to attack by fungi, bacteria or protozoa an effective amount of a compound of the formula ##STR9## wherein R is alkyl, cycloalkyl, cycloalkyl lower alkyl, phenyl or phenyl lower alkyl, said phenyl and phenyl lower alkyl optionally substituted on the phenyl ring with one or more substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl and wherein lower alkyl has 1 to 4 carbon atoms, alkyl has 1 to 12 carbon atoms and cycloalkyl has 5 to 7 carbon atoms; X is oxygen or sulfur with the proviso that X is not oxygen when R is phenyl or substituted phenyl; or an antimicrobial acid addition salt thereof or a composition containing same as an active ingredient.
Claim 30
Dependent Claim
14 words
The method of claim 26 wherein the compound of Formula (I) is administered topically.
Claim 31
Dependent Claim
16 words
The method of claim 26 wherein the compound of Formula (I) is administered orally or parenterally.
References Cited (Backward Citations)
US3682951A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-18 | 1981-01-17 | 1981-07-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-18 | 1985-01-17 | 1985-07-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-18 | 1989-01-17 | 1989-07-19 | $7700.00 | Window Closed / Lapsed |