US4036974A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1-{2'-[R'-Thio(oxy)]-3'-(R2 -thio(oxy)]propyl}imidazoles
Assignee: Syntex USA LLC
•
Filing: 1976-03-08
•
Granted: 1977-07-19
•
Expires: 1996-03-08
Abstract
Abstract Compounds of the formula <IMAGE> (I) wherein R1 and R2 are independently alkyl or the group <IMAGE> IN WHICH N IS 0 TO 3; X and Y are independently oxygen or sulfur; and the antimicrobial acid addition salts thereof are useful as antifungal, antibacterial and antiprotozoal agents.
Inventors
- 👤 Keith A. M. Walker
- 👤 Michael Marx
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 16:25
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
47 words
A compound of the formula ##STR17## wherein R 1 and R 2 are independently alkyl having 1 to 12 carbon atoms or the group ##STR18## in which n is 0 to 3; X and Y are independently oxygen or sulfur; and the antimicrobial acid addition salts thereof.
Claim 2
Dependent Claim
47 words
A compound of the formula ##STR17## wherein R 1 and R 2 are independently alkyl having 1 to 12 carbon atoms or the group ##STR18## in which n is 0 to 3; X and Y are independently oxygen or sulfur; and the antimicrobial acid addition salts thereof.
Claim 3
Dependent Claim
11 words
A compound of claim 1 wherein X and Y are oxygen.
Claim 4
Dependent Claim
13 words
A compound of claim 1 wherein X is sulfur and Y is oxygen.
Claim 5
Dependent Claim
13 words
A compound of claim 1 wherein X is oxygen and Y is sulfur.
Claim 6
Dependent Claim
11 words
A compound of claim 1 wherein X and Y are sulfur.
Claim 7
Dependent Claim
13 words
A compound of claim 1 wherein R 1 and R 2 are alkyl.
Claim 8
Dependent Claim
15 words
The compound of claim 6 which is 1-[2',3'-bis(n-octyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 9
Dependent Claim
15 words
The compound of claim 6 which is 1-[3'-(n-decyloxy)-2'-(n-hexyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 10
Dependent Claim
15 words
The compound of claim 6 which is 1-[3'-(n-decyloxy)-2'-(n-heptyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 11
Dependent Claim
15 words
The compound of claim 6 which is 1-[3'-(n-decyloxy)-2'-(n-octyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 12
Dependent Claim
15 words
The compound of claim 6 which is 1-[2'-(n-heptyloxy)-3'-(n-heptylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 13
Dependent Claim
15 words
The compound of claim 6 which is 1-[3'-(n-heptylthio)-2'-(n-octyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 14
Dependent Claim
15 words
The compound of claim 6 which is 1-[2'-(n-octyloxy)-3'-(n-octylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 15
Dependent Claim
15 words
The compound of claim 6 which is 1-[2'-(n-dodecylthio)-3'-(isopropoxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 16
Dependent Claim
15 words
The compound of claim 6 which is 1-[3'-(n-octyloxy)-2'-(n-octylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 17
Dependent Claim
15 words
The compound of claim 6 which is 1-[2'-(n-heptylthio)-3'-(n-octyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 18
Dependent Claim
15 words
The compound of claim 6 which is 1-[2'-(butylthio)-3'-(n-dodecyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 19
Dependent Claim
15 words
The compound of claim 6 which is 1-[2'-(n-dodecylthio)-3'-(methylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 20
Dependent Claim
15 words
The compound of claim 6 which is 1-[3'-(t-butylthio)-2'-(n-nonylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 21
Dependent Claim
15 words
The compound of claim 6 which is 1-[2',3'-bis(n-hexylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 22
Dependent Claim
15 words
The compound of claim 6 which is 1-[2',3'-bis-(n-heptylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 23
Dependent Claim
15 words
The compound of claim 6 which is 1-[2',3'-bis-(n-pentylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 24
Dependent Claim
72 words
A composition useful for inhibiting the growth of fungi, bacteria or protozoa which comprises an effective amount of a compound of the formula ##STR19## wherein R 1 and R 2 are independently alkyl having 1 to 12 carbon atoms or the group ##STR20## in which n is 0 to 3 and X and Y are independently oxygen or sulfur; or an antimicrobial acid addition salt thereof in admixture with a suitable carrier.
Claim 25
Dependent Claim
72 words
A composition useful for inhibiting the growth of fungi, bacteria or protozoa which comprises an effective amount of a compound of the formula ##STR19## wherein R 1 and R 2 are independently alkyl having 1 to 12 carbon atoms or the group ##STR20## in which n is 0 to 3 and X and Y are independently oxygen or sulfur; 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, nontoxic 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
89 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 ##STR21## wherein R 1 and R 2 are independently alkyl having 1 to 12 carbon atoms or the group ##STR22## in which n is 0 to 3 and X and Y are independently oxygen or sulfur; or an antimicrobial acid addition salt thereof or a composition containing same as an active ingredient.
Claim 29
Independent Claim
89 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 ##STR21## wherein R 1 and R 2 are independently alkyl having 1 to 12 carbon atoms or the group ##STR22## in which n is 0 to 3 and X and Y are independently oxygen or sulfur; 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)
US3531494A
Cited
US3940415A
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 |