US4078071A
Expired / Lapsed
US
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Derivatives of substituted N-alkyl imidazoles
Assignee: Syntex USA LLC
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Filing: 1977-01-10
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Granted: 1978-03-07
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Expires: 1997-01-10
Abstract
Abstract Compounds of the formula <IMAGE> (I) wherein R1 and R2 are each independently phenyl, phenyl straight chain lower alkyl or phenyl straight chain lower alkenyl or one of the above substituted in the phenyl ring with one or more substituents independently selected from the group consisting of lower alkyl of from one to four carbon atoms, halo and trifluoromethyl; X is oxygen or sulfur; n is an integer of from 1 to 8 with the proviso that n is not 1 when R1 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
2026-10-29 15:14
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; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/645; C07F9/6503; C07F9/6506
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
90 words
A compound of the formula ##STR16## wherein R 1 is phenethyl, phenylpropyl or styryl and R 2 is phenyl, phenyl straight chain lower alkyl or phenyl straight chain alkenyl, wherein the phenyl rings of R 1 and R 2 may independently be unsubstituted or substituted with one or more substituents independently selected from the group consisting of lower akyl of from one to four carbon atoms, halo and trifluoromethyl; X is oxygen or sulfur; n is an integer of from one to three; and the antimicrobial acid addition salts therof.
Claim 2
Dependent Claim
90 words
A compound of the formula ##STR16## wherein R 1 is phenethyl, phenylpropyl or styryl and R 2 is phenyl, phenyl straight chain lower alkyl or phenyl straight chain alkenyl, wherein the phenyl rings of R 1 and R 2 may independently be unsubstituted or substituted with one or more substituents independently selected from the group consisting of lower akyl of from one to four carbon atoms, halo and trifluoromethyl; X is oxygen or sulfur; n is an integer of from one to three; and the antimicrobial acid addition salts therof.
Claim 3
Dependent Claim
9 words
The compound of claim 1 wherein n is 1.
Claim 4
Dependent Claim
13 words
The compound of claim 1 wherein R 1 is halo-substituted phenethyl or styryl.
Claim 5
Dependent Claim
12 words
The compound of claim 3 wherein R 1 has a 4-halo substituent.
Claim 6
Dependent Claim
22 words
The compound of claim 3 wherein, when R 1 has more than one halo substituent, all such substituents are the same halo.
Claim 7
Dependent Claim
14 words
The compound of claim 3 wherein the halo substituent on R 1 is chloro.
Claim 8
Dependent Claim
15 words
The compound of claim 3 wherein R 2 is substituted or unsubstituted phenyl or benzyl.
Claim 9
Dependent Claim
13 words
The compound of claim 7 wherein R 2 is halo-substituted phenyl or benzyl.
Claim 10
Dependent Claim
16 words
The compound of claim 8 wherein R 2 is phenyl having at least one ortho-halo substituent.
Claim 11
Dependent Claim
22 words
The compound of claim 9 wherein, when R 2 has more than one halo substituent, all such substituents are the same halo.
Claim 12
Dependent Claim
14 words
The compound of claim 8 wherein the halo substituent on R 2 is chloro.
Claim 13
Dependent Claim
9 words
The compound of claim 9 wherein X is sulfur.
Claim 14
Dependent Claim
11 words
The compound of claim 8 wherein R 2 is halo-substituted benzyl.
Claim 15
Dependent Claim
11 words
The compound of claim 13 wherein R 2 is chloro-substituted benzyl.
Claim 16
Dependent Claim
15 words
The compound of claim 8 which is 1-[2-(2,6-dichlorophenylthio)-4-(4-chlorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 17
Dependent Claim
15 words
The compound of claim 8 which is 1-[2-(2,5-dichlorophenylthio)-4-(4-chlorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 18
Dependent Claim
15 words
The compound of claim 8 which is 1-[2-(2,4-dichlorophenylthio)-4-(4-chlorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 19
Dependent Claim
15 words
The compound of claim 8 which is 1-[2-(2-chorophenylthio)-4-(4-chlorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 20
Dependent Claim
15 words
The compound of claim 8 which is 1-[2-(2,3-dichlorophenylthio)-4-(4-chorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 21
Dependent Claim
15 words
The compound of claim 8 which is 1-[2-(2-bromophenylthio)-4-(4-chlorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 22
Dependent Claim
15 words
The compound of claim 8 which is 1-[2-(2,6-dibromophenylthio)-4-(4-chorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 23
Dependent Claim
16 words
The compound of claim 8 which is 1-[2-(2,4,6-trichlorophenylthio)-4-(4-fluorophenyl)butyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 24
Dependent Claim
16 words
The compound of claim 8 which is 1-[2-(2,6-dichlorophenylthio)-4-(4-fluorophenyl)butyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 25
Dependent Claim
16 words
The compound of claim 8 which is 1-[2-(2,6-dichlorophenylthio)-4-(4-chlorophenyl)but-3-enyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 26
Dependent Claim
16 words
The compound of claim 8 which is 1-[3-(2,6-dichlorophenylthio)-5-(4-chlorophenyl)pentyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 27
Dependent Claim
16 words
The compound of claim 8 which is 1-[2-(2,5-dichlorophenylthio)-4-(4-fluorophenyl)butyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 28
Dependent Claim
16 words
The compound of claim 8 which is 1-[2-(2,4,5-trichlorophenylthio)-4-(4-fluorophenyl)butyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 29
Dependent Claim
16 words
The compound of claim 8 which is 1-[2-(2,4,5-trichlorophenylthio)-4-(4-chlorophenyl)butyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 30
Dependent Claim
115 words
A composition useful for inhibiting the growth of fungi, bacteria or portozoa which comprises an effective amount of a compound of the formula ##STR17## wherein R 1 is phenethyl, phenylpropyl or styryl and R 2 is phenyl, phenyl straight chain lower alkyl or phenyl straight chain lower alkenyl, wherein the phenyl rings of R 1 and R 2 may independently be unsubstituted or substituted with one or more substituents independently selected from the group consisting of lower alkyl of from one to four carbon atoms, halo and trifluoromethyl; X is oxygen or sulfur, n is an integer of from 1 to 3; or an anti-microbial acid addition salt thereof; in admixture with a suitable carrier.
Claim 31
Dependent Claim
115 words
A composition useful for inhibiting the growth of fungi, bacteria or portozoa which comprises an effective amount of a compound of the formula ##STR17## wherein R 1 is phenethyl, phenylpropyl or styryl and R 2 is phenyl, phenyl straight chain lower alkyl or phenyl straight chain lower alkenyl, wherein the phenyl rings of R 1 and R 2 may independently be unsubstituted or substituted with one or more substituents independently selected from the group consisting of lower alkyl of from one to four carbon atoms, halo and trifluoromethyl; X is oxygen or sulfur, n is an integer of from 1 to 3; or an anti-microbial acid addition salt thereof; in admixture with a suitable carrier.
Claim 32
Dependent Claim
18 words
The composition of claim 29 suitable for pharmaceutical use wherein the carrier is a pharmaceutically acceptable, non-toxic carrier.
Claim 33
Dependent Claim
27 words
The composition of claim 30 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 34
Independent Claim
132 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 ##STR18## wherein R 1 is phenyl, phenylpropyl or styryl and R 2 is phenyl, phenyl straight chain lower alkyl or phenyl straight chain lower alkenyl wherein the phenyl rings of R 1 and R 2 may independently be unsubstituted or substituted with one or more substituents independently selected from the group consisting of lower alkyl of from one to four carbon atoms, halo and trifluoromethyl; X is oxygen or sulfur; n is a integer of from 1 to 3; or an antimicrobial acid addition salt thereof, or a composition containing same as an active ingredient.
Claim 35
Independent Claim
132 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 ##STR18## wherein R 1 is phenyl, phenylpropyl or styryl and R 2 is phenyl, phenyl straight chain lower alkyl or phenyl straight chain lower alkenyl wherein the phenyl rings of R 1 and R 2 may independently be unsubstituted or substituted with one or more substituents independently selected from the group consisting of lower alkyl of from one to four carbon atoms, halo and trifluoromethyl; X is oxygen or sulfur; n is a integer of from 1 to 3; or an antimicrobial acid addition salt thereof, or a composition containing same as an active ingredient.
Claim 36
Dependent Claim
14 words
The method of claim 32 wherein the compound of Formula I is administered topically.
Claim 37
Dependent Claim
16 words
The method of claim 32 wherein the compound of Formula I is administered orally or parenterally.
Claim 38
Dependent Claim
11 words
The compound 1-[3-(2,6-dichlorophenylthio)-4-(4-chlorophenyl)butyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 39
Dependent Claim
11 words
The compound 1-[3-(2,6-dichlorophenylthio)-4-(4-chlorophenyl)butyl] imidazole and the antimicrobial acid addition salts 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) | 1981-03-06 | 1981-09-05 | 1982-03-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-03-06 | 1985-09-05 | 1986-03-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-03-06 | 1989-09-05 | 1990-03-07 | $7700.00 | Window Closed / Lapsed |