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US4150153A
Expired / Lapsed
US
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1-(Naphthylethyl)imidazole derivatives
Assignee: Syntex USA LLC
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Filing: 1977-11-04
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Granted: 1979-04-17
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Expires: 1997-11-04
Abstract
Abstract Compounds of the formula <IMAGE> (I) wherein Z is hydroxymethylene, esterified hydroxymethylene, carbonyl, or ketal-, thioketal- or hemithioketal- protected carbonyl, and the pharmaceutically acceptable acid addition salts thereof, are useful as anticonvulsant and anti-secretory agents.
Inventors
- 👤 Keith A. M. Walker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 21:23
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: 19
Claim 1
Independent Claim
144 words
A compound of the formula ##STR8## wherein Z is hydroxymethylene, hydroxymethylene esterified with an alkanoic acid having from one to eight carbon atoms or with benzoic acid, carbonyl, carbonyl protected as an acyclic ketal derived from a monohydric straight chain alkanol having from one to 4 carbon atoms, carbonyl protected as a cyclic ketal derived from a dihydric alcohol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, carbonyl protected as an acyclic thioketal derived from a straight or branched alkylthiol having from one to four carbon atoms, carbonyl protected as a cyclic thioketal derived from an alkylene dithiol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, or carbonyl protected as a cyclic hemithioketal derived from 2-mercaptoethanol or 3-mercapto-1-propanol; and the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
144 words
A compound of the formula ##STR8## wherein Z is hydroxymethylene, hydroxymethylene esterified with an alkanoic acid having from one to eight carbon atoms or with benzoic acid, carbonyl, carbonyl protected as an acyclic ketal derived from a monohydric straight chain alkanol having from one to 4 carbon atoms, carbonyl protected as a cyclic ketal derived from a dihydric alcohol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, carbonyl protected as an acyclic thioketal derived from a straight or branched alkylthiol having from one to four carbon atoms, carbonyl protected as a cyclic thioketal derived from an alkylene dithiol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, or carbonyl protected as a cyclic hemithioketal derived from 2-mercaptoethanol or 3-mercapto-1-propanol; and the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
9 words
The compound of claim 1 wherein Z is carbonyl.
Claim 4
Dependent Claim
16 words
The compound of claim 2 which is 1-(2-naphthoylmethyl)imidazole and the pharmaceutically acceptable acid addition salts thereof.
Claim 5
Dependent Claim
9 words
The compound of claim 1 wherein Z is hydroxymethylene.
Claim 6
Dependent Claim
16 words
The compound of claim 4 which is 1-[2-hydroxy-2-(1-naphthyl)ethyl]imidazole and the pharmaceutically acceptable acid addition salts thereof.
Claim 7
Dependent Claim
56 words
The compound of claim 1 wherein Z is carbonyl-protected as an acyclic ketal derived from a monohydric straight chain alkanol having from one to four carbon atoms or carbonyl protected as a cyclic ketal derived from a dihydric alcohol having two or three carbon atoms which may optionally be substituted by one or more methyl groups.
Claim 8
Dependent Claim
16 words
The compound of claim 6 which is 1-[2,2-ethylenedioxy-2-(2-naphthyl)ethyl]imidazole and the pharmaceutically acceptable acid addition salts thereof.
Claim 9
Dependent Claim
16 words
The compound of claim 6 which is 1-[2,2-(1,3-propylenedioxy)-2-(2-naphthyl)ethyl]imidazole and the pharmaceutically acceptable acid addition salts thereof.
Claim 10
Dependent Claim
16 words
The compound of claim 6 which is 1-[2,2-ethylenedioxy-2-(1-naphthyl)ethyl]imidazole and the pharmaceutically acceptable acid addition salts thereof.
Claim 11
Dependent Claim
58 words
The compound of claim 1 wherein Z is carbonyl protected as an acyclic thioketal derived from a straight or branched chain alkylthiol having from one to four carbon atoms or carbonyl protected as a cyclic thioketal derived from an alkylene dithiol having two or three carbon atoms which may optionally be substituted by one or more methyl groups.
Claim 12
Dependent Claim
16 words
The compound of claim 10 which is 1-[2,2-bis(methylthio)-2-(2-naphthyl)ethyl]imidazole and the pharmaceutically acceptable acid addition salts thereof.
Claim 13
Dependent Claim
16 words
The compound of claim 10 which is 1-[2,2-bis(ethylthio)-2-(2-naphthyl)ethyl]imidazole and the pharmaceutically acceptable acid addition salts thereof.
Claim 14
Independent Claim
170 words
A method for treating and preventing convulsions in a mammalian subject in need of such treatment comprising administering to said subject a therapeutically effective amount of a compound of the formula ##STR9## wherein Z is hydroxymethylene, hydroxymethylene esterified with an alkanoic acid having from one to eight carbon atoms or with benzoic acid, carbonyl, carbonyl protected as an acyclic ketal derived from a monohydric straight chain alkanol having from one to 4 carbon atoms, carbonyl protected as a cyclic ketal derived from a dihydric alcohol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, carbonyl protected as an acyclic thioketal derived from a straight or branched alkylthiol having from one to four carbon atoms, carbonyl protected as a cyclic thioketal derived from an alkylene dithiol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, or carbonyl protected as a cyclic hemithioketal derived from 2-mercaptoethanol or 3-mercapto-1-propanol, and the pharmaceutically acceptable acid addition salts thereof.
Claim 15
Independent Claim
170 words
A method for treating and preventing convulsions in a mammalian subject in need of such treatment comprising administering to said subject a therapeutically effective amount of a compound of the formula ##STR9## wherein Z is hydroxymethylene, hydroxymethylene esterified with an alkanoic acid having from one to eight carbon atoms or with benzoic acid, carbonyl, carbonyl protected as an acyclic ketal derived from a monohydric straight chain alkanol having from one to 4 carbon atoms, carbonyl protected as a cyclic ketal derived from a dihydric alcohol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, carbonyl protected as an acyclic thioketal derived from a straight or branched alkylthiol having from one to four carbon atoms, carbonyl protected as a cyclic thioketal derived from an alkylene dithiol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, or carbonyl protected as a cyclic hemithioketal derived from 2-mercaptoethanol or 3-mercapto-1-propanol, and the pharmaceutically acceptable acid addition salts thereof.
Claim 16
Dependent Claim
176 words
A pharmaceutical composition for the prevention and treatment of convulsions for the inhibition of gastric secretion in mammals comprising a therapeutically effective amount of a compound of the formula ##STR10## wherein Z is hydroxymethylene, hydroxymethylene esterified with an alkanoic acid having from one to eight carbon atoms or with benzoic acid, carbonyl, carbonyl protected as an acyclic ketal derived from a monohydric straight chain alkanol having from one to 4 carbon atoms, carbonyl protected as a cyclic ketal derived from a dihydric alcohol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, carbonyl protected as an acyclic thioketal derived from a straight or branched alkylthiol having from one to four carbon atoms, carbonyl protected as a cyclic thioketal derived from an alkylene dithiol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, or carbonyl protected as a cyclic hemithioketal derived from 2-mercaptoethanol or 3-mercapto-1-propanol, or a pharmaceutically acceptable acid addition salt thereof; in admixture with a pharmaceutically acceptable, non-toxic carrier.
Claim 17
Dependent Claim
176 words
A pharmaceutical composition for the prevention and treatment of convulsions for the inhibition of gastric secretion in mammals comprising a therapeutically effective amount of a compound of the formula ##STR10## wherein Z is hydroxymethylene, hydroxymethylene esterified with an alkanoic acid having from one to eight carbon atoms or with benzoic acid, carbonyl, carbonyl protected as an acyclic ketal derived from a monohydric straight chain alkanol having from one to 4 carbon atoms, carbonyl protected as a cyclic ketal derived from a dihydric alcohol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, carbonyl protected as an acyclic thioketal derived from a straight or branched alkylthiol having from one to four carbon atoms, carbonyl protected as a cyclic thioketal derived from an alkylene dithiol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, or carbonyl protected as a cyclic hemithioketal derived from 2-mercaptoethanol or 3-mercapto-1-propanol, or a pharmaceutically acceptable acid addition salt thereof; in admixture with a pharmaceutically acceptable, non-toxic carrier.
Claim 18
Independent Claim
169 words
A method for inhibiting gastric secretion in a mammalian subject in need of such treatment comprising administering to said subject a therapeutically effective amount of a compound of the formula ##STR11## wherein Z is hydroxymethylene, hydroxymethylene esterified with an alkanoic acid having from one to eight carbon atoms or with benzoic acid, carbonyl, carbonyl protected as an acyclic ketal derived from a monohydric straight chain alkanol having from one to 4 carbon atoms, carbonyl protected as a cyclic ketal derived from a dihydric alcohol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, carbonyl protected as an acyclic thioketal derived from a straight or branched alkylthiol having from one to four carbon atoms, carbonyl protected as a cyclic thioketal derived from an alkylene dithiol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, or carbonyl protected as a cyclic hemithioketal derived from 2-mercaptoethanol or 3-mercapto-1-propanol, and the pharmaceutically acceptable acid addition salts thereof.
Claim 19
Independent Claim
169 words
A method for inhibiting gastric secretion in a mammalian subject in need of such treatment comprising administering to said subject a therapeutically effective amount of a compound of the formula ##STR11## wherein Z is hydroxymethylene, hydroxymethylene esterified with an alkanoic acid having from one to eight carbon atoms or with benzoic acid, carbonyl, carbonyl protected as an acyclic ketal derived from a monohydric straight chain alkanol having from one to 4 carbon atoms, carbonyl protected as a cyclic ketal derived from a dihydric alcohol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, carbonyl protected as an acyclic thioketal derived from a straight or branched alkylthiol having from one to four carbon atoms, carbonyl protected as a cyclic thioketal derived from an alkylene dithiol having two or three carbon atoms which may optionally be substituted by one or more methyl groups, or carbonyl protected as a cyclic hemithioketal derived from 2-mercaptoethanol or 3-mercapto-1-propanol, and the pharmaceutically acceptable acid addition salts thereof.
References Cited (Backward Citations)
US3575999A
Cited
US3658813A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-04-16 | 1982-10-16 | 1983-04-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-04-16 | 1986-10-16 | 1987-04-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-04-16 | 1990-10-16 | 1991-04-17 | $7700.00 | Window Closed / Lapsed |