US4123542A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Derivatives of N-alkyl imidazoles
Assignee: Syntex USA LLC
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Filing: 1977-01-19
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Granted: 1978-10-31
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Expires: 1997-01-19
Abstract
Abstract Compounds of the formula ##STR1## wherein R is lower alkyl; R 1 is substituted or unsubstituted phenyl or phenyl straight chain lower alkyl; R 2 is substituted or unsubstituted phenyl, phenyl straight chain lower alkyl or phenyl straight chain lower alkenyl; and wherein said substitution, solely in the phenyl ring of the aforesaid groups, comprises one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halo and trifluoromethyl; X is oxygen or sulfur; n is an integer of from 1 to 4 with the proviso that n cannot be 1 when X is oxygen and R 1 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
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 10:47
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; A; A01; A01N; A01N43/00; A01N43/48; A01N43/50; A61; A61P; A61P31/00; A61P31/04; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
51 words
A compound of the formula: ##STR14## wherein R is lower alkyl; R 1 is 4-halo or 2,4-dihalo substituted phenethyl or phenylpropyl; R 2 is halo and/or methoxy substituted benzyl or phenyl; X is oxygen or sulfur; n is an integer of from 1 to 4; and the antimicrobial addition salts thereof.
Claim 2
Dependent Claim
51 words
A compound of the formula: ##STR14## wherein R is lower alkyl; R 1 is 4-halo or 2,4-dihalo substituted phenethyl or phenylpropyl; R 2 is halo and/or methoxy substituted benzyl or phenyl; X is oxygen or sulfur; n is an integer of from 1 to 4; and the antimicrobial addition salts thereof.
Claim 3
Dependent Claim
9 words
A compound of claim 1 wherein X is sulfur.
Claim 4
Dependent Claim
9 words
A compound of claim 1 wherein X is oxygen.
Claim 5
Dependent Claim
35 words
A compound of claim 1 wherein R 1 is 4-halo substituted phenethyl and R 2 is halo and/or methoxy substituted benzyl or phenyl wherein said substitution includes a substitution in an ortho or para position.
Claim 6
Dependent Claim
9 words
A compound of claim 4 wherein n is 1.
Claim 7
Dependent Claim
14 words
The compound of claim 5 which is 1-[2-(2,5-dichlorophenylthio)-2-methyl-4-(4-fluorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 8
Dependent Claim
14 words
The compound of claim 5 which is 1-[2-(2,4,6-trichlorophenylthio)-2-methyl-4-(4-fluorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 9
Dependent Claim
14 words
The compound of claim 5 which is 1-[2-(2,6-dichlorophenylthio)-2-methyl-4-(4-fluorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 10
Dependent Claim
14 words
The compound of claim 5 which is 1-[2-(2,4-dichlorophenylthio)-2-methyl-4-(4-fluorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 11
Dependent Claim
14 words
The compound of claim 5 which is 1-[2-(2-chlorophenylthio)-2-methyl-4-(4-chlorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 12
Dependent Claim
14 words
The compound of claim 5 which is 1-[2-(2,6-dichlorophenylthio)-2-methyl-4-(4-chlorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 13
Dependent Claim
14 words
The compound of claim 5 which is 1-[2-(2,5-dichlorophenylthio)-2-methyl-4-(4-chlorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 14
Dependent Claim
14 words
The compound of claim 5 which is 1-[2-(2,4-dichlorophenylthio)-2-methyl-4-(4-chlorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 15
Dependent Claim
14 words
The compound of claim 5 which is 1-[2-(4-chlorophenylthio)-2-methyl-4-(4-chlorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 16
Dependent Claim
14 words
The compound of claim 5 which is 1-[2-(2-bromophenylthio)-2-methyl-4-(4-chlorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 17
Dependent Claim
14 words
The compound of claim 5 which is 1-[2-(2-methoxyphenylthio)-2-methyl-4-(4-chlorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 18
Dependent Claim
23 words
A compound of claim 1 wherein R 1 is 2,4-dihalo substituted phenethyl and R 2 is 4-halo or 4-methoxy substituted benzyl or phenyl.
Claim 19
Dependent Claim
9 words
A compound of claim 17 wherein n is 1.
Claim 20
Dependent Claim
14 words
The compound of claim 18 which is 1-[2-(4-chlorophenylthio)-2-methyl-4-(2,4-dichlorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 21
Dependent Claim
14 words
The compound of claim 18 which is 1-[2-(4-methoxyphenylthio)-2-methyl-4-(2,4-dichlorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 22
Dependent Claim
14 words
The compound of claim 18 which is 1-[2-(4-fluorophenylthio)-2-methyl-4-(2,4-dichlorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 23
Dependent Claim
14 words
The compound of claim 18 which is 1-[2-(4-bromophenylthio)-2-methyl-4-(2,4-dichlorophenyl)-n-butyl]imidazole and the acid addition salts thereof.
Claim 24
Dependent Claim
75 words
A composition useful for inhibiting the growth of fungi, bacteria or protozoa which comprises an effective amount of a compound of the formula: ##STR15## wherein R is lower alkyl; R 1 is 4-halo or 2,4-dihalo substituted phenethyl or phenylpropyl; R 2 is halo and/or methoxy substituted benzyl or phenyl; X is oxygen or sulfur; n is an integer of from 1 to 4; or an antimicrobial addition salt thereof; in admixture with a suitable carrier.
Claim 25
Dependent Claim
75 words
A composition useful for inhibiting the growth of fungi, bacteria or protozoa which comprises an effective amount of a compound of the formula: ##STR15## wherein R is lower alkyl; R 1 is 4-halo or 2,4-dihalo substituted phenethyl or phenylpropyl; R 2 is halo and/or methoxy substituted benzyl or phenyl; X is oxygen or sulfur; n is an integer of from 1 to 4; or an antimicrobial addition salt thereof; in admixture with a suitable carrier.
Claim 26
Dependent Claim
18 words
The composition of claim 23 suitable for pharmaceutical use wherein the carrier is a pharmaceutically acceptable, non-toxic carrier.
Claim 27
Dependent Claim
27 words
The composition of claim 24 for topical administration wherein the compound of formula I is present as between about 0.1 and 10.0 weight percent of the composition.
Claim 28
Independent Claim
93 words
A method of inhibiting the growth of fungi, bacteria or protozoa which comprises applying to a host object containing, or subject to attach by, fungi, bacteria or protozoa, an effective amount of a compound of the formula: ##STR16## wherein R is lower alkyl; R 1 is 4-halo or 2,4-dihalo substituted phenethyl or phenylpropyl; R 2 is halo and/or methoxy substituted benzyl or phenyl; X is oxygen or sulfur; n is an integer of from 1 to 4; or an antimicrobial acid addition salt thereof, or a composition containing same as an active ingredient.
Claim 29
Independent Claim
93 words
A method of inhibiting the growth of fungi, bacteria or protozoa which comprises applying to a host object containing, or subject to attach by, fungi, bacteria or protozoa, an effective amount of a compound of the formula: ##STR16## wherein R is lower alkyl; R 1 is 4-halo or 2,4-dihalo substituted phenethyl or phenylpropyl; R 2 is halo and/or methoxy substituted benzyl or phenyl; X is oxygen or sulfur; n is an integer of from 1 to 4; 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)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-30 | 1982-05-01 | 1982-10-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-30 | 1986-05-01 | 1986-10-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-30 | 1990-05-01 | 1990-10-31 | $7700.00 | Window Closed / Lapsed |