US4172141A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-(naphthylethyl)imidazole derivatives
Assignee: Syntex USA LLC
•
Filing: 1978-06-19
•
Granted: 1979-10-23
•
Expires: 1998-06-19
Abstract
Abstract Compounds of the formula <IMAGE> (I) wherein R is alkyl, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl; X is oxygen or sulfur; and the pharmaceutically acceptable acid addition salts thereof are CNS-active agents, inhibitors of gastric secretion and antifungal, antibacterial and antiprotozoal agents.
Inventors
- 👤 Keith A. M. Walker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 01:47
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: 35
Claim 1
Independent Claim
74 words
A compound of the formula ##STR14## and the pharmaceutically acceptable, acid addition salts thereof, wherein: R is alkyl having from 1 to 12 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl having from 1 to 4 carbon atoms, and trifluoromethyl; and X is oxygen or sulfur.
Claim 2
Dependent Claim
74 words
A compound of the formula ##STR14## and the pharmaceutically acceptable, acid addition salts thereof, wherein: R is alkyl having from 1 to 12 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl having from 1 to 4 carbon atoms, and trifluoromethyl; and X is oxygen or sulfur.
Claim 3
Dependent Claim
9 words
A compound of claim 1 wherein X is oxygen.
Claim 4
Dependent Claim
9 words
A compound of claim 1 wherein X is sulfur.
Claim 5
Dependent Claim
28 words
A compound of claim 1 wherein R is alkyl having from 1 to 12 carbon atoms, benzyl, phenyl, or benzyl or phenyl substituted with methyl, chloro or fluoro.
Claim 6
Dependent Claim
17 words
A compound of claim 4 wherein R is lower alkyl having from 1 to 4 carbon atoms.
Claim 7
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(1-naphthyl)-2-(methoxy)ethyl]imidazole.
Claim 8
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(2-naphthyl)-2-(methoxy)ethyl]imidazole.
Claim 9
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(1-naphthyl)-2-(ethoxy)ethyl]imidazole.
Claim 10
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(2-naphthyl)-2-(ethoxy)ethyl]imidazole.
Claim 11
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(1-naphthyl)-2-(phenoxy)ethyl]imidazole.
Claim 12
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(2-naphthyl)-2-(phenoxy)ethyl]imidazole.
Claim 13
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(1-naphthyl)-2-(2,4-dichlorobenzyloxy)ethyl]imidazole.
Claim 14
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(2-naphthyl)-2-(2,4-dichlorobenzyloxy)ethyl]imidazole.
Claim 15
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(1-naphthyl)-2-(4-chlorobenzyloxy)ethyl]imidazole.
Claim 16
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(2-naphthyl)-2-(4-chlorobenzyloxy)ethyl]imidazole.
Claim 17
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(2-naphthyl)-2-(2,4-dichlorobenzylthio)ethyl]imidazole.
Claim 18
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(2-naphthyl)-2-(4-chlorobenzylthio)ethyl]imidazole.
Claim 19
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(2-naphthyl)-2-(2,4,6-trichlorophenylthio)ethyl]imidazole.
Claim 20
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(2-naphthyl)-2-(2,5-dichlorophenylthio)ethyl]imidazole.
Claim 21
Dependent Claim
8 words
The compound of claim 4 which is 1-[2-(2-naphthyl)-2-(2,6-dichlorophenylthio)ethyl]imidazole.
Claim 22
Independent Claim
106 words
A method for treating and preventing convulsions in a mammalian subject comprising administering to said subject a therapeutically effective amount of a compound of the formula ##STR15## and the pharmaceutically acceptable, acid addition salts thereof, wherein: R is alkyl having from 1 to 12 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl having from 1 to 4 carbon atoms, and trifluoromethyl; and X is oxygen or sulfur; or a pharmaceutical composition containing such compound as an active ingredient.
Claim 23
Independent Claim
106 words
A method for treating and preventing convulsions in a mammalian subject comprising administering to said subject a therapeutically effective amount of a compound of the formula ##STR15## and the pharmaceutically acceptable, acid addition salts thereof, wherein: R is alkyl having from 1 to 12 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl having from 1 to 4 carbon atoms, and trifluoromethyl; and X is oxygen or sulfur; or a pharmaceutical composition containing such compound as an active ingredient.
Claim 24
Dependent Claim
100 words
A pharmaceutical composition for the prevention and treatment of convulsions in mammals comprising a therapeutically effective amount of a compound of the formula ##STR16## and the pharmaceutically acceptable, acid addition salts thereof, wherein: R is alkyl having from 1 to 12 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl having from 1 to 4 carbon atoms, and trifluoromethyl; and X is oxygen or sulfur; in admixture with a pharmaceutically acceptable, non-toxic carrier.
Claim 25
Dependent Claim
100 words
A pharmaceutical composition for the prevention and treatment of convulsions in mammals comprising a therapeutically effective amount of a compound of the formula ##STR16## and the pharmaceutically acceptable, acid addition salts thereof, wherein: R is alkyl having from 1 to 12 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl having from 1 to 4 carbon atoms, and trifluoromethyl; and X is oxygen or sulfur; in admixture with a pharmaceutically acceptable, non-toxic carrier.
Claim 26
Dependent Claim
10 words
The composition of claim 22 wherein R is lower alkyl.
Claim 27
Independent Claim
105 words
A method for inhibiting gastric secretion in a mammalian subject comprising administering to said subject a therapeutically effective amount of a compound of the formula ##STR17## and the pharmaceutically acceptable, acid addition salts thereof, wherein: R is alkyl having from 1 to 12 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl having from 1 to 4 carbon atoms, and trifluoromethyl; and X is oxygen or sulfur or a pharmaceutical composition containing such compound as an active ingredient.
Claim 28
Independent Claim
105 words
A method for inhibiting gastric secretion in a mammalian subject comprising administering to said subject a therapeutically effective amount of a compound of the formula ##STR17## and the pharmaceutically acceptable, acid addition salts thereof, wherein: R is alkyl having from 1 to 12 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl having from 1 to 4 carbon atoms, and trifluoromethyl; and X is oxygen or sulfur or a pharmaceutical composition containing such compound as an active ingredient.
Claim 29
Dependent Claim
97 words
A pharmaceutical composition for inhibiting gastric secretion in mammals comprising a therapeutically effective amount of a compound of the formula ##STR18## and the pharmaceutically acceptable, acid addition salts thereof, wherein: R is alkyl having from 1 to 12 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl having from 1 to 4 carbon atoms, and trifluoromethyl; and X is oxygen or sulfur; in admixture with a pharmaceutically acceptable, non-toxic carrier.
Claim 30
Dependent Claim
97 words
A pharmaceutical composition for inhibiting gastric secretion in mammals comprising a therapeutically effective amount of a compound of the formula ##STR18## and the pharmaceutically acceptable, acid addition salts thereof, wherein: R is alkyl having from 1 to 12 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl having from 1 to 4 carbon atoms, and trifluoromethyl; and X is oxygen or sulfur; in admixture with a pharmaceutically acceptable, non-toxic carrier.
Claim 31
Independent Claim
107 words
A method of inhibiting the growth of fungi, bacteria or protozoa which comprises applying to a host subject an antimicrobially effective amount of a compound of the formula ##STR19## wherein: R is alkyl having from 1 to 12 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl having from 1 to 4 carbon atoms, and trifluoromethyl; and X is oxygen or sulfur; or a pharmaceutically acceptable acid addition salt thereof; or a composition containing such compound as an active ingredient.
Claim 32
Independent Claim
107 words
A method of inhibiting the growth of fungi, bacteria or protozoa which comprises applying to a host subject an antimicrobially effective amount of a compound of the formula ##STR19## wherein: R is alkyl having from 1 to 12 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl having from 1 to 4 carbon atoms, and trifluoromethyl; and X is oxygen or sulfur; or a pharmaceutically acceptable acid addition salt thereof; or a composition containing such compound as an active ingredient.
Claim 33
Dependent Claim
14 words
The method of claim 26 wherein the compound of formula (I) is administered topically.
Claim 34
Dependent Claim
100 words
A pharmaceutical composition for inhibiting the growth of fungi, bacteria or protozoa which comprises an antimicrobially effective amount of a compound of the formula ##STR20## wherein: R is alkyl having from 1 to 12 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl having from 1 to 4 carbon atoms, and trifluoromethyl; X is oxygen or sulfur; or a pharmaceutically acceptable acid addition salt thereof; in admixture with a pharmaceutically acceptable, non-toxic carrier.
Claim 35
Dependent Claim
100 words
A pharmaceutical composition for inhibiting the growth of fungi, bacteria or protozoa which comprises an antimicrobially effective amount of a compound of the formula ##STR20## wherein: R is alkyl having from 1 to 12 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl having from 1 to 4 carbon atoms, and trifluoromethyl; X is oxygen or sulfur; or a pharmaceutically acceptable acid addition salt thereof; in admixture with a pharmaceutically acceptable, non-toxic carrier.
References Cited (Backward Citations)
US3575999A
Cited
US3717655A
Cited
US3839574A
Cited
US3658813A
Cited
US3755349A
Cited
US3796704A
Cited
US3812142A
Cited
US3764690A
Cited
DE2504114A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-10-22 | 1983-04-23 | 1983-10-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-10-22 | 1987-04-23 | 1987-10-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-10-22 | 1991-04-23 | 1991-10-23 | $7700.00 | Window Closed / Lapsed |