Histamine H.sub.3 -receptor antagonists and therapeutic uses thereof
AssigneeThe University of Toledo
InventorsGraham J. Durant, Amin M. Khan
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Abstract
The present invention provides novel compounds having activity as histamine H.sub.3 -receptor antagonists. The novel compounds include 4-imidazolyl-N-substituted pyrrolidines, piperidines, and cycloheptimides. The preferred compounds are 4-imidazolyl-N-(cycloalkyl/aryl-alkyl-carbonyl) piperidines such as 4-(1-cyclohexylvaleryol-4-piperidyl)-1H-imidazole.
Claims26
A compound of the formula:
- ##STR31## wherein R.sub.1 represents hydrogen or an in vivo hydrolyzable group;
- D is CH.sub.2 CH.sub.2 ;
- Z is S or O;
- x is 0 or 1;
- n is an integer from 0 to 6;
- and R.sub.2 represents a substituted or unsubstituted linear or branched chain alkyl group of up to about 20 carbon atoms, a substituted or unsubstituted carbocyclic group of up to about 20 atoms, or a substituted or unsubstituted aryl group of up to about 20 carbon atoms, and salts thereof, with the provisos that if R.sub.2 is tert-butyl, cyclohexyl, or dicyclohexylmethyl, x or n must not be 0;
- and if R.sub.2 is adamantane, the sum of x and n must be greater than 1.
A compound of the formula:
- ##STR32## wherein x is 0 or 1;
- n is an interger from 0 to 6;
- and R represents a substituted or unsubstituted linear chain or branched chain alkyl group of up to about 20 carbon atoms, a substituted or unsubstituted carbocyclic group of up to about 20 carbon atoms, or substituted or unsubstituted aryl group of up to about 20 carbon atoms, and salts thereof with the provisos that if R is tert-butyl, cyclohexyl, or dicyclohexylmethyl, x or n must not be 0;
- and if R is adamantane, the sum of x and n must be greater than 1.
A compound of the formula:
- ##STR33## in which n is 1.
A compound of the formula:
- ##STR34##
A compound of the formula:
- ##STR35## wherein n is 0, 1, 2, 3 or 4.
A compound of the formula:
- ##STR36##
A compound of the formula:
- ##STR37##
A compound of the formula:
- ##STR38## in which n=2.
A compound of the formula:
- ##STR39## in which n=3.
A compound of the formula:
- ##STR40## in which n=4.
A compound of the formula:
- ##STR41## wherein R.sub.1 represents hydrogen or an in vivo hydrolyzable group, an alkyl group, an cyclic alkyl group, or an aryl group;
- D is CH.sub.2 CH.sub.2 ;
- Z is S or O;
- x is 0 or 1;
- n is an integer from 0 to 6;
- and R.sub.2 represents a substituted or unsubstituted linear or branched chain alkyl group of up to about 20 carbon atoms, a substituted or unsubstituted carbocyclic group of up to about 20 atoms, or a substituted or unsubstituted aryl group of up to about 20 carbon atoms, and salts thereof, with the provisos that if R.sub.2 is tert-butyl, cyclohexyl, or dicyclohexylmethyl, x or n must not be 0;
- and if R.sub.2 is adamantane, the sum of x and n must be greater than 1.
Dependencies are inferred from the claim text.