US4045568A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Derivatives of substituted N-alkyl imidazoles
Assignee: Syntex USA LLC
•
Filing: 1976-03-08
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Granted: 1977-08-30
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Expires: 1996-03-08
Abstract
Abstract Compounds of the formula (I) <IMAGE> wherein one of R1 and R2 is 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; the other of R1 and R2 is alkyl, cyclohexyl, cyclohexyl lower alkyl or cyclohexyl substituted with from 1 to 3 lower alkyl groups; 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
2026-11-09 19:47
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07C; C07C45/00; C07C45/61; C07C45/63; C07C45/67; C07C45/68; 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: 59
Claim 1
Independent Claim
48 words
A compound of the formula ##STR16## wherein R 1 is straight chain alkyl of from 1 to 12 carbon atoms, R 2 is halo-substituted phenyl or benzyl, X is oxygen or sulfur, n is an integer of from 1 to 8; and the antimicrobial acid addition salts thereof.
Claim 2
Dependent Claim
48 words
A compound of the formula ##STR16## wherein R 1 is straight chain alkyl of from 1 to 12 carbon atoms, R 2 is halo-substituted phenyl or benzyl, X is oxygen or sulfur, n is an integer of from 1 to 8; and the antimicrobial acid addition salts thereof.
Claim 3
Dependent Claim
19 words
The compound of claim 1 wherein R 2 is 4-chloro-, 4-bromo-, 4-fluoro-, 2,4-dichloro- or 3,4-dichloro- substituted phenyl or benzyl.
Claim 4
Dependent Claim
9 words
The compound of claim 2 wherein n is 1.
Claim 5
Dependent Claim
27 words
The compound of claim 3 wherein R 2 is 4-chlorophenyl, X is sulfur and R 1 is straight chain alkyl of from 4 to 11 carbon atoms.
Claim 6
Dependent Claim
15 words
The compound of claim 4 which is 1-[2-(4-chlorophenylthio)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 7
Dependent Claim
29 words
The compound of claim 3 wherein R 2 is 2,4- or 3,4-dichlorophenyl, X is sulfur and R 1 is straight chain alkyl of from 4 to 10 carbon atoms.
Claim 8
Dependent Claim
15 words
The compound of claim 6 which is 1-[2-(2,4-dichlorophenylthio)heptyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 9
Dependent Claim
15 words
The compound of claim 6 which is 1-[2-(2,4-dichlorophenylthio)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 10
Dependent Claim
15 words
The compound of claim 6 which is 1-[2-(3,4-dichlorophenylthio)heptyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 11
Dependent Claim
15 words
The compound of claim 6 which is 1-[2-(3,4-dichlorophenylthio)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 12
Dependent Claim
24 words
The compound of claim 3 wherein R 2 is 4-chlorobenzyl and R 1 is straight chain alkyl of from 4 to 11 carbon atoms.
Claim 13
Dependent Claim
15 words
The compound of claim 11 which is 1-[2-(4-chlorobenzylthio)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 14
Dependent Claim
15 words
The compound of claim 11 which is 1-[2-(4-chlorobenzyloxy)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 15
Dependent Claim
26 words
The compound of claim 3 wherein R 2 is 2,4- or 3,4-dichlorobenzyl and R 1 is straight chain alkyl of from 4 to 10 carbon atoms.
Claim 16
Dependent Claim
15 words
The compound of claim 14 which is 1-[2-(2,4-dichlorobenzylthio)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 17
Dependent Claim
16 words
The compound of claim 14 which is 1-[2-(2,4-dichlorobenzyloxy)octyl ]imidazole and the antimicrobial acid addition salts thereof.
Claim 18
Dependent Claim
15 words
The compound of claim 14 which is 1-[2-(3,4-dichlorobenzylthio)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 19
Dependent Claim
15 words
The compound of claim 14 which is 1-[2-(3,4-dichlorobenzyloxy)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 20
Dependent Claim
9 words
The compound of claim 2 wherein n is 2.
Claim 21
Dependent Claim
27 words
The compound of claim 19 wherein R 2 is 4-chlorophenyl, X is sulfur and R 1 is straight chain alkyl of from 3 to 10 carbon atoms.
Claim 22
Dependent Claim
16 words
The compound of claim 20 which is 1-[3-(4-chlorophenylthio) heptyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 23
Dependent Claim
15 words
The compound of claim 20 which is 1-[3-(4-chlorophenylthio)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 24
Dependent Claim
29 words
The compound of claim 20 wherein R 2 is 2,4- or 3,4-dichlorophenyl, X is sulfur and R 1 is straight chain alkyl of from 3 to 9 carbon atoms.
Claim 25
Dependent Claim
15 words
The compound of claim 20 which is 1-[3-(2,4-dichlorophenylthio)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 26
Dependent Claim
15 words
The compound of claim 20 which is 1-[3-(2,4-dichlorophenylthio)heptyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 27
Dependent Claim
15 words
The compound of claim 20 which is 1-[3-(3,4-dichlorophenylthio)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 28
Dependent Claim
15 words
The compound of claim 20 which is 1-[3-(3,4-dichlorophenylthio)heptyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 29
Dependent Claim
24 words
The compound of claim 19 wherein R 2 is 4-chlorobenzyl and R 1 is straight chain alkyl of from 3 to 10 carbon atoms.
Claim 30
Dependent Claim
15 words
The compound of claim 28 which is 1-[3-(4-chlorobenzylthio)heptyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 31
Dependent Claim
15 words
The compound of claim 28 which is 1-[3-(4-chlorobenzyloxy)nonyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 32
Dependent Claim
15 words
The compound of claim 28 which is 1-[3-(4-chlorobenzylthio)octyl]imidazole and the anitmicrobial acid addition salts thereof.
Claim 33
Dependent Claim
15 words
The compound of claim 28 which is 1-[3-(4-chlorobenzyloxy)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 34
Dependent Claim
26 words
The compound of claim 19 wherein R 2 is 2,4- or 3,4-dichlorobenzyl and R 1 is straight chain alkyl of from 3 to 9 carbon atoms.
Claim 35
Dependent Claim
15 words
The compound of claim 33 which is 1-[3-(2,4-dichlorobenzylthio)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 36
Dependent Claim
15 words
The compound of claim 33 which is 1-[3-(2,4-dichlorobenzylthio)heptyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 37
Dependent Claim
15 words
The compound of claim 33 which is 1-[3-(2,4-dichlorobenzyloxy)nonyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 38
Dependent Claim
15 words
The compound of claim 33 which is 1-[3-(2,4-dichlorobenzyloxy)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 39
Dependent Claim
15 words
The compound of claim 33 which is 1-[3-(3,4-dichlorobenzylthio)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 40
Dependent Claim
15 words
The compound of claim 33 which is 1-[3-(3,4-dichlorobenzylthio)heptyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 41
Dependent Claim
15 words
The compound of claim 33 which is 1-[3-(3,4-dichlorobenzyloxy)nonyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 42
Dependent Claim
15 words
The compound of claim 33 which is 1-[3-(3,4-dichlorobenzyloxy)octyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 43
Dependent Claim
45 words
A compound of the formula ##STR17## wherein R 1 is unsubstituted or halo-substituted phenethyl or styryl, R 2 is straight chain alkyl of from 1 to 12 carbon atoms, X is oxygen or sulfur and n is 1; and the antimicrobial acid addition salts thereof.
Claim 44
Dependent Claim
45 words
A compound of the formula ##STR17## wherein R 1 is unsubstituted or halo-substituted phenethyl or styryl, R 2 is straight chain alkyl of from 1 to 12 carbon atoms, X is oxygen or sulfur and n is 1; and the antimicrobial acid addition salts thereof.
Claim 45
Dependent Claim
15 words
The compound of claim 42 wherein R 1 is unsubstituted or 4-monohalo-substituted phenethyl or styryl.
Claim 46
Dependent Claim
15 words
The compound of claim 43 which is 1-(2-heptylthio-4-phenylbutyl)imidazole and the anitmicrobial acid addition salts thereof.
Claim 47
Dependent Claim
15 words
The compound of claim 43 which is 1-(2-octyloxy-4-phenylbutyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 48
Dependent Claim
15 words
The compound of claim 43 which is 1-[2-heptylthio4-(4-fluorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 49
Dependent Claim
15 words
The compound of claim 43 which is 1-[2-octyloxy4-(4-fluorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 50
Dependent Claim
15 words
The compound of claim 43 which is 1-[2-hexylthio-4-(4-chlorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 51
Dependent Claim
15 words
The compound of claim 43 which is 1-[2-heptyloxy4-(4-chlorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 52
Dependent Claim
107 words
A composition useful for inhibiting the growth of fungi, bacteria or protozoa which comprises an effective amount of a compound of the formula ##STR18## wherein (a) R 1 is straight chain alkyl of from 1 to 12 carbon atoms, R 2 is halo-substituted phenyl or benzyl, X is oxygen or sulfur and n is an integer of from 1 to 8, or (b) R 1 is unsubstituted or halo-substituted phenethyl or styryl, R 2 is straight chain alkyl of from 1 to 12 carbon atoms, X is oxygen or sulfur and n is 1, or an antimicrobial acid addition salt thereof; in admixture with a suitable carrier.
Claim 53
Dependent Claim
107 words
A composition useful for inhibiting the growth of fungi, bacteria or protozoa which comprises an effective amount of a compound of the formula ##STR18## wherein (a) R 1 is straight chain alkyl of from 1 to 12 carbon atoms, R 2 is halo-substituted phenyl or benzyl, X is oxygen or sulfur and n is an integer of from 1 to 8, or (b) R 1 is unsubstituted or halo-substituted phenethyl or styryl, R 2 is straight chain alkyl of from 1 to 12 carbon atoms, X is oxygen or sulfur and n is 1, or an antimicrobial acid addition salt thereof; in admixture with a suitable carrier.
Claim 54
Dependent Claim
18 words
The composition of claim 50 suitable for pharmaceutical use wherein the carrier is a pharmaceutically acceptable non-toxic carrier.
Claim 55
Dependent Claim
27 words
The composition of claim 51 for topical administration wherein the compound of formula (I) is present at between about 0.1 and 10.0 weight percent of the composition.
Claim 56
Independent Claim
122 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 ##STR19## wherein (a) R 1 is straight chain alkyl of from 1 to 12 carbon atoms, R 2 is halo-substituted phenyl or benzyl, X is oxygen or sulfur and n is an integer of from 1 to 8, or (b) R 1 is unsubstituted phenethyl or styryl, R 2 is straight chain alkyl of from 1 to 12 carbon atoms, X is oxygen or sulfur and n is 1, or an antimicrobial acid addition salt thereof, or a composition containing same as an active ingredient.
Claim 57
Independent Claim
122 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 ##STR19## wherein (a) R 1 is straight chain alkyl of from 1 to 12 carbon atoms, R 2 is halo-substituted phenyl or benzyl, X is oxygen or sulfur and n is an integer of from 1 to 8, or (b) R 1 is unsubstituted phenethyl or styryl, R 2 is straight chain alkyl of from 1 to 12 carbon atoms, X is oxygen or sulfur and n is 1, or an antimicrobial acid addition salt thereof, or a composition containing same as an active ingredient.
Claim 58
Dependent Claim
14 words
The method of claim 53 wherein the compound of Formula (I) is administered topically.
Claim 59
Dependent Claim
16 words
The method of claim 53 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) | 1980-08-29 | 1981-02-28 | 1981-08-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-08-29 | 1985-02-28 | 1985-08-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-08-29 | 1989-02-28 | 1989-08-30 | $7700.00 | Window Closed / Lapsed |