Synthesis and evaluation of N-3 substituted phenoxypropyl piperidine benzimidazol-2-one analogues as NOP receptor agonists with analgesic and sedative properties

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 4, 2007, Pages 1828-1847

  Palin, Ronald ^a   Bom, Anton ^a   Clark, John K ^a   Evans, Louise ^a   Feilden, Helen ^a   Houghton, Andrea K ^a   Jones, Philip S ^a   Montgomery, Brian ^a   Weston, Mark A ^a   Wishart, Grant ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Analgesic; Antinociception; Benzimidazolone; NOP; ORL1; Sedative

Indexed keywords

1 (2 DIMETHYLAMINOETHYL) 3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 1,3 DIHYDROBENZIMIDAZOL 2 ONE; 1 (2 HYDROXYETHYL) 3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 1,3 DIHYDROBENZIMIDAZOL 2 ONE; 1 (2 METHOXYETHYL) 3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 1,3 DIHYDROBENZIMIDAZOL 2 ONE; 1 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 3 (2 METHYLAMINOETHYL) 1,3 DIHYDROBENZIMIDAZOL 2 ONE; 1 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 3 (2 OXOBUTYL) 1,3 DIHYDROBENZIMIDAZOL 2 ONE METHANESULFONATE; 1 [2 (BENZYLMETHYLAMINO)ETHYL] 3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 1,3 DIHYDROBENZIMIDAZOL 2 ONE; 1 ETHOXYMETHYL 3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL] PIPERIDIN 4 YL] 1,3 DIHYDROBENZIMIDAZOL 2 ONE; 1 METHANESULFINYLMETHYL 3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 1,3 DIHYDROBENZIMIDAZOL 2 ONE METHYLSULFONATE; 1 METHANESULFONYLMETHYL 3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 1,3 DIHYDROBENZIMIDAZOL 2 ONE METHANESULFONATE; 1 METHOXYMETHYL 3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 1,3 DIHYDROBENZIMIDAZOL 2 ONE; 2 [3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 2 OXO 2,3 DIHYDROBENZIMIDAZOL 1 YL] N METHYLACETAMIDE METHANESULFONATE; 2 [3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 2 OXO 2,3 DIHYDROBENZIMIDAZOL 1 YL]ACETAMIDE; 3 [3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 2 OXO 2,3 DIHYDROBENZIMIDAZOL 1 YL] N METHYLPROPIONAMIDE; [3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 2 OXO 2,3 DIHYDROBENZIMIDAZOL 1 YL]ACETIC ACID; [3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 2 OXO 2,3 DIHYDROBENZIMIDAZOL 1 YL]ACETIC ACID METHYL ESTER; ACETIC ACID 2 [3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL] PIPERIDIN 4 YL] 2 OXO 2,3 DIHYDROBENZIMIDAZOL 1 YL]ETHYL ESTER; ANALGESIC AGENT; MORPHINE; N (2 HYDROXYETHYL) 2 [3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 2 OXO 2,3 DIHYDROBENZIMIDAZOL 1 YL]ACETAMIDE; N (2 METHOXYETHYL) 2 [3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 2 OXO 2,3 DIHYDROBENZIMIDAZOL 1 YL]ACETAMIDE; N BENZYL 2 [3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 2 OXO 2,3 DIHYDROBENZIMIDAZOL 1 YL]ACETAMIDE; N BUTYL 2 [3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 2 OXO 2,3 DIHYDROBENZIMIDAZOL 1 YL]ACETAMIDE; N CYCLOBUTYL 2 [3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 2 OXO 2,3 DIHYDROBENZIMIDAZOL 1 YL]ACETAMIDE; N CYCLOPROPYL 2 [3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 2 OXO 2,3 DIHYDROBENZIMIDAZOL 1 YL]ACETAMIDE; N CYCLOPROPYLMETHYL 2 [3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 2 OXO 2,3 DIHYDROBENZIMIDAZOL 1 YL]ACETAMIDE; N ETHYL 2 [3 [1 [3 (5 METHOXY 2 METHYLPHENOXY) 4 METHYLPENTYL]PIPERIDIN 4 YL] 2 OXO 2,3 DIHYDROBENZIMIDAZOL 1 YL]ACETAMIDE; NALOXONE; OPIATE AGONIST; SEDATIVE AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINOCICEPTION; ARTICLE; CONTROLLED STUDY; DRUG DOSE INCREASE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; GUINEA PIG; HUMAN; MALE; MOUSE; NONHUMAN; RODENT; SEDATION; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANALGESICS; ANIMALS; BENZIMIDAZOLES; HYPNOTICS AND SEDATIVES; RECEPTORS, OPIOID; RODENTIA; STRUCTURE-ACTIVITY RELATIONSHIP;

RODENTIA;

EID: 33847794821     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.11.030     Document Type: Article

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