3-substituted piperidines comprising urea functionality, and methods of use thereof
AssigneeSepracor Inc.
InventorsBrian M. Aquila, Gregory D. Cuny, James R. Hauske, Liming Shao, Xinhe Wu
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Abstract
One aspect of the present invention relates to novel heterocyclic compounds comprising urea functionality. A second aspect of the present invention relates to the use of the novel heterocyclic compounds comprising urea functionality as ligands for various cellular receptors, including opioid receptors, other G-protein-coupled receptors and ion channels. An additional aspect of the present invention relates to the use of the novel heterocyclic compounds comprising urea functionality as analgesics.
Claims52
A compound represented by general structure A:
- 44
- wherein
- X represents CH2, NR, O or S;
- Z represents O, S or NR;
- R represents independently for each occurrence H, alkyl, aryl or heteroaryl;
- and two geminal instances of R taken together may represent O;
- R1 represents H, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aralkyl or heteroaralkyl;
- R2 represents independently for each occurrence H, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aralkyl or heteroaralkyl, or the two instances of R2 taken together represent an aryl or heteroaryl moiety or a —CH2—, —CH2CH2—, —CH2CH2CH2—, or —CH2CH2CH2CH2-tether between the two nitrogens of the urea moiety;
- R3 represents H, alkyl, fluoroalkyl, aryl, alkenyl, alkynyl, heteroaryl, aralkyl or heteroaralkyl;
- m is an integer in the range 1 to 4 inclusive;
- n is an integer in the range 0 to 2 inclusive;
- p is an integer in the range 0 to 3 inclusive;
- and
- the stereochemical configuration at any stereocenter of a compound represented by A may be R, S, or a mixture of these configurations.
A compound represented by general structure B:
- 45
- X represents CH2, NR, O or S;
- Z represents O, S or NR;
- R represents independently for each occurrence H, alkyl, aryl or heteroaryl;
- and two geminal instances of R taken together may represent O;
- R1 represents H, alkyl, alkenyl, alkynyl, aryl, heteroaryl, aralkyl or heteroaralkyl;
- R2 represents H, alkyl, fluoroalkyl, alkenyl, alkynyl, aryl, heteroaryl, aralkyl or heteroaralkyl;
- R3 is absent or present 1, 2, 3 or 4 times;
- R3 represents independently for each occurrence alkyl, aryl, alkenyl, alkynyl, heteroaryl, aralkyl, heteroaralkyl, halogen, —N(R)2, formyl, acyl, —CO2R, —CONR2, —O2CR, acylamino, —SR, or —OR;
- m is an integer in the range 1 to 4 inclusive;
- n is an integer in the range 0 to 2 inclusive;
- p is an integer in the range 0 to 3 inclusive;
- and
- the stereochemical configuration at any stereocenter of a compound represented by B may be R, S, or a mixture of these configurations.
Dependencies are inferred from the claim text.