US4036973A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Imidazol-1-yl propane derivatives
Assignee: Syntex USA LLC
•
Filing: 1976-03-08
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Granted: 1977-07-19
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Expires: 1996-03-08
Abstract
Abstract Compounds of the formula <IMAGE> wherein one of R1 and R2 is alkyl or the group <IMAGE> IN WHICH N IS 0 TO 3 AND THE OTHER OF R1 and R2 is benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with one or more substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl; X and Y are independently oxygen or sulfur with the proviso that Y is not oxygen when R2 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
- 👤 Michael Marx
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 05:46
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: 44
Claim 1
Independent Claim
109 words
A compound of the formula: ##STR20## wherein: one of R 1 and R 2 is alkyl having 1 to 12 carbon atoms or the group ##STR21## in which n is 0 to 3, and the other of R 1 and R 2 is benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with one or more substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl; X and Y are independently oxygen or sulfur with the proviso that Y is not oxygen when R 2 is phenyl or substituted phenyl; and the antimicrobial acid addition salts thereof.
Claim 2
Dependent Claim
109 words
A compound of the formula: ##STR20## wherein: one of R 1 and R 2 is alkyl having 1 to 12 carbon atoms or the group ##STR21## in which n is 0 to 3, and the other of R 1 and R 2 is benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with one or more substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl; X and Y are independently oxygen or sulfur with the proviso that Y is not oxygen when R 2 is phenyl or substituted phenyl; 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
61 words
A compound of claim 1 selected from the group consisting of: a. those wherein R 1 is halo substituted benzyl or halo substituted phenyl and R 2 is alkyl; b. those wherein R 1 is alkyl and R 2 is halo substituted benzyl; or c. those wherein R 1 is alkyl, R 2 is halo substituted phenyl and Y is sulfur.
Claim 8
Dependent Claim
43 words
A compound of claim 6 wherein halo substituted benzyl or halo substituted phenyl group is 4-, 2,4-di- or 3,4-dichloro substituted benzyl or 4-, 2,4-di- or 3,4-dichloro substituted phenyl and the alkyl group is a straight chain alkyl having 3 to 8 carbon atoms.
Claim 9
Dependent Claim
16 words
The compound of claim 7 which is 1-[3'-(4"-chlorophenoxy)-2'-(n-pentylthio)propyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 10
Dependent Claim
16 words
The compound of claim 7 which is 1-[3'-(4"-chlorophenoxy)-2'-(n-hexylthio)propyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 11
Dependent Claim
16 words
The compound of claim 7 which is 1-[3'-(4"-chlorophenoxy)-2'-(n-heptylthio)propyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 12
Dependent Claim
16 words
The compound of claim 7 which is 1-[3'-(4"-chlorophenoxy)-2'-(n-hexyloxy)propyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 13
Dependent Claim
16 words
The compound of claim 7 which is 1-[3'-(4"-chlorophenoxy)-2'-(n-heptyloxy)propyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 14
Dependent Claim
16 words
The compound of claim 7 which is 1-[3'-(4"-chlorophenoxy)-2'-(n-octyloxy)propyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 15
Dependent Claim
16 words
The compound of claim 7 which is 1-[2'-(n-butylthio)-3'-(2",4"-dichlorophenoxy)propyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 16
Dependent Claim
16 words
The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenoxy)-2'-(n-pentylthio)propyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 17
Dependent Claim
16 words
The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenoxy)-2'-(n-hexylthio)propyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 18
Dependent Claim
16 words
The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenoxy)-2'-(n-pentyloxy)propyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 19
Dependent Claim
16 words
The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenoxy)-2'-(n-hexyloxy)propyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 20
Dependent Claim
16 words
The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenoxy)-2'-(n-heptyloxy)propyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 21
Dependent Claim
16 words
The compound of claim 7 which is 1-[3'-(4"-chlorophenylthio)-2'-(n-pentylthio)propyl] imidazole and the antimicrobial acid addition salts thereof.
Claim 22
Dependent Claim
15 words
The compound of claim 7 which is 1-[3'-(4"-chlorophenylthio)-2'-(n-hexylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 23
Dependent Claim
15 words
The compound of claim 7 which is 1-[3'-(4"-chlorophenylthio)-2'-(n-hexyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 24
Dependent Claim
15 words
The compound of claim 7 which is 1-[3'-(4"-chlorophenylthio)-2'-(n-heptyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 25
Dependent Claim
15 words
The compound of claim 7 which is 1-[2'-(n-butylthio)-3'-(2",4"-dichlorophenylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 26
Dependent Claim
15 words
The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenylthio)-2'-(n-pentylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 27
Dependent Claim
15 words
The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenylthio)-2'-(n-pentyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 28
Dependent Claim
15 words
The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenylthio)-2'-(n-hexyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 29
Dependent Claim
15 words
The compound of claim 7 which is 1-[3'-(n-butylthio)-2'-(4"-chlorobenzyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 30
Dependent Claim
15 words
The compound of claim 7 which is 1-[2'-(4"-chlorobenzyloxy)-3'-(n-pentylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 31
Dependent Claim
15 words
The compound of claim 7 which is 1-[2'-(4"-chlorobenzyloxy)-3'-(n-hexylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 32
Dependent Claim
15 words
The compound of claim 7 which is 1-[3'-(n-butylthio)-2'-(2",4"-dichlorobenzyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 33
Dependent Claim
15 words
The compound of claim 7 which is 1-[2'-(2",4"-dichlorobenzyloxy)-3'-(n-pentylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 34
Dependent Claim
15 words
The compound of claim 7 which is 1-[2'-(2",4"-dichlorophenylthio)-3'-(n-propylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 35
Dependent Claim
15 words
The compound of claim 7 which is 1-[3'-(n-butylthio)-2'-(2",4"-dichlorophenylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 36
Dependent Claim
16 words
The compound of claim 7 which is 1-[2'( 2",4"-dichlorophenylthio)-3'-(n-pentylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
Claim 37
Dependent Claim
133 words
A composition useful for inhibiting the growth of fungi, bacteria or protozoa which comprises an effective amount of a compound of the formula ##STR22## wherein: one of R 1 and R 2 is alkyl having 1 to 12 carbon atoms or the group ##STR23## in which n to 0 to 3, and the other of R 1 and R 2 is benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with one or more substitutents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl; X and Y are independently oxygen or sulfur with the proviso that Y is not oxygen when R 2 is phenyl or substituted phenyl; or an antimicrobial acid addition salt thereof in admixture with a suitable carrier.
Claim 38
Dependent Claim
133 words
A composition useful for inhibiting the growth of fungi, bacteria or protozoa which comprises an effective amount of a compound of the formula ##STR22## wherein: one of R 1 and R 2 is alkyl having 1 to 12 carbon atoms or the group ##STR23## in which n to 0 to 3, and the other of R 1 and R 2 is benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with one or more substitutents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl; X and Y are independently oxygen or sulfur with the proviso that Y is not oxygen when R 2 is phenyl or substituted phenyl; or an antimicrobial acid addition salt thereof in admixture with a suitable carrier.
Claim 39
Dependent Claim
17 words
A composition of claim 36 for pharmaceutical use wherein the carrier is a pharmaceutically acceptable non-toxic carrier.
Claim 40
Dependent Claim
29 words
A composition of claim 37 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 41
Independent Claim
150 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 ##STR24## wherein: one of R 1 and R 2 is alkyl having 1 to 12 carbon atoms or the group ##STR25## in which n is 0 to 3, and the other of R 1 and R 2 is benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with one or more substitutents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl; X and Y are independently oxygen or sulfur with the proviso that Y is not oxygen when R 2 is phenyl or substituted phenyl; or an antimicrobial acid addition salt thereof or a composition containing same as an active ingredient.
Claim 42
Independent Claim
150 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 ##STR24## wherein: one of R 1 and R 2 is alkyl having 1 to 12 carbon atoms or the group ##STR25## in which n is 0 to 3, and the other of R 1 and R 2 is benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with one or more substitutents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl; X and Y are independently oxygen or sulfur with the proviso that Y is not oxygen when R 2 is phenyl or substituted phenyl; or an antimicrobial acid addition salt thereof or a composition containing same as an active ingredient.
Claim 43
Dependent Claim
14 words
The method of claim 39 wherein the compound of Formula (I) is administered topically.
Claim 44
Dependent Claim
16 words
The method of claim 39 wherein the compound of Formula (I) is administered orally or parenternally.
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 |