US4059705A
Expired / Lapsed
US
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Derivatives of substituted n-alkyl imidazoles
Assignee: Syntex USA LLC
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Filing: 1976-03-08
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Granted: 1977-11-22
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Expires: 1996-03-08
Abstract
Abstract Compounds of the formula <IMAGE> (I) wherein R1 and R2 are each independently alkyl, cyclohexyl substituted with from one to three lower alkyl groups, or a group of the formula <IMAGE> WHEREIN M IS AN INTEGER OF FROM 0 TO 3 AND P IS AN INTEGER OF FROM 1 TO 3; X is sulfur or oxygen; n is an integer of from 1 to 8; 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 18:47
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07C; C07C45/00; C07C45/61; C07C45/63; C07C45/67; C07C45/68; C07C49/00; C07C49/29; C07C49/303; C07C49/327; C07C49/527; C07C49/567; 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: 37
Claim 1
Independent Claim
60 words
A compound of the formula ##STR18## wherein X is sulfur, n is 1 or 2, and R 1 and R 2 are each independently straight chain alkyl of from 1 to 12 carbon atoms such that the total number of carbon atoms in R 1 and R 2 is between 7 and 18; and the antimicrobial acid addition salts thereof.
Claim 2
Dependent Claim
60 words
A compound of the formula ##STR18## wherein X is sulfur, n is 1 or 2, and R 1 and R 2 are each independently straight chain alkyl of from 1 to 12 carbon atoms such that the total number of carbon atoms in R 1 and R 2 is between 7 and 18; and the antimicrobial acid addition salts thereof.
Claim 3
Dependent Claim
15 words
The compound of claim 1 which is 1-(2-heptylthiooctyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 4
Dependent Claim
15 words
The compound of claim 1 which is 1-(2-octylthiooctyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 5
Dependent Claim
15 words
The compound of claim 1 which is 1-(2-nonylthiooctyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 6
Dependent Claim
15 words
The compound of claim 1 which is 1-(2-hexylthiodecyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 7
Dependent Claim
15 words
The compound of claim 1 which is 1-(2-butylthiododecyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 8
Dependent Claim
15 words
The compound of claim 1 which is 1-(2-ethylthiotetradecyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 9
Dependent Claim
15 words
The compound of claim 1 which is 1-(3-octylthiooctyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 10
Dependent Claim
15 words
The compound of claim 1 which is 1-(3-heptylthiooctyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 11
Dependent Claim
15 words
The compound of claim 1 which is 1-(3-nonylthiooctyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 12
Dependent Claim
15 words
The compound of claim 1 which is 1-(3-heptylthiononyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 13
Dependent Claim
15 words
The compound of claim 1 which is 1-(3-hexylthiodecyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 14
Dependent Claim
15 words
The compound of claim 1 which is 1-(3-pentylthioundecyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 15
Dependent Claim
15 words
The compound of claim 1 which is 1-(3-butylthiododecyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 16
Dependent Claim
15 words
The compound of claim 1 which is 1-(3-ethylthiotetradecyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 17
Dependent Claim
60 words
A compound of the formula ##STR19## wherein X is oxygen, n is 1 or 2, and R 1 and R 2 are each independently straight chain alkyl of from 1 to 12 carbon atoms such that the total number of carbon atoms in R 1 and R 2 is between 8 and 20; and the antimicrobial acid addition salts thereof.
Claim 18
Dependent Claim
60 words
A compound of the formula ##STR19## wherein X is oxygen, n is 1 or 2, and R 1 and R 2 are each independently straight chain alkyl of from 1 to 12 carbon atoms such that the total number of carbon atoms in R 1 and R 2 is between 8 and 20; and the antimicrobial acid addition salts thereof.
Claim 19
Dependent Claim
15 words
The compound of claim 16 which is 1-(2-nonyloxyoctyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 20
Dependent Claim
15 words
The compound of claim 16 which is 1-(2-decyloxyoctyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 21
Dependent Claim
15 words
The compound of claim 16 which is 1-(2-octyloxydecyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 22
Dependent Claim
15 words
The compound of claim 16 which is 1-(2-hexyloxydodecyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 23
Dependent Claim
15 words
The compound of claim 16 which is 1-(2-butoxytetradecyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 24
Dependent Claim
15 words
The compound of claim 16 which is 1-(3-decyloxyoctyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 25
Dependent Claim
15 words
The compound of claim 16 which is 1-(3-decyloxynonyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 26
Dependent Claim
15 words
The compound of claim 16 which is 1-(3-octyloxydecyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 27
Dependent Claim
15 words
The compound of claim 16 which is 1-(3-heptyloxyundecyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 28
Dependent Claim
15 words
The compound of claim 16 which is 1-(3-hexyloxydodecyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 29
Dependent Claim
15 words
The compound of claim 16 which is 1-(3-butoxytetradecyl)imidazole and the antimicrobial acid addition salts thereof.
Claim 30
Dependent Claim
100 words
A composition useful for inhibiting the growth of fungi, bacteria or protozoa which comprises an effective amount of a compound of the formula ##STR20## wherein X is sulfur or oxygen, n is 1 or 2, and R 1 and R 2 are each independently straight chain alkyl of from 1 to 12 carbon atoms, such that the total number of carbon atoms in R 1 and R 2 is between 7 and 18 when X is sulfur and between 8 and 20 when X is oxygen; or an antimicrobial acid addition salt thereof; in an admixture with a suitable carrier.
Claim 31
Dependent Claim
100 words
A composition useful for inhibiting the growth of fungi, bacteria or protozoa which comprises an effective amount of a compound of the formula ##STR20## wherein X is sulfur or oxygen, n is 1 or 2, and R 1 and R 2 are each independently straight chain alkyl of from 1 to 12 carbon atoms, such that the total number of carbon atoms in R 1 and R 2 is between 7 and 18 when X is sulfur and between 8 and 20 when X is oxygen; or an antimicrobial acid addition salt thereof; in an admixture with a suitable carrier.
Claim 32
Dependent Claim
18 words
The composition of claim 28 suitable for pharmaceutical use wherein the carrier is a pharmaceutically acceptable, non-toxic carrier.
Claim 33
Dependent Claim
27 words
The composition of claim 29 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
130 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 each independently alkyl of from 1 to 12 carbon atoms, cyclohexyl substituted with from one to three lower alkyl groups each having from 1 to 4 carbon atoms, or a group of the formula ##STR22## wherein m is an integer of from 0 to 3 and p is an integer of from 1 to 3; X is sulfur or oxygen; n is an integer of from 1 to 8; or an antimicrobial acid addition salt thereof; or a composition containing same as an active ingredient.
Claim 35
Independent Claim
130 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 each independently alkyl of from 1 to 12 carbon atoms, cyclohexyl substituted with from one to three lower alkyl groups each having from 1 to 4 carbon atoms, or a group of the formula ##STR22## wherein m is an integer of from 0 to 3 and p is an integer of from 1 to 3; X is sulfur or oxygen; n is an integer of from 1 to 8; 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 31 wherein the compound of Formula (I) is administered topically.
Claim 37
Dependent Claim
16 words
The method of claim 31 wherein the compound of Formula (I) is administered, orally or parenterally.
References Cited (Backward Citations)
US3531494A
Cited
US3551444A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-11-21 | 1981-05-23 | 1981-11-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-11-21 | 1985-05-23 | 1985-11-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-11-21 | 1989-05-23 | 1989-11-22 | $7700.00 | Window Closed / Lapsed |