Carbamates derived from arylalkylamines

3-Quinuclidinyl N-(arylmethyl, cycloalkylmethyl or heteroarylmethyl)-N-phenylcarbamates (I) are new. Carbamates of formula (I) and their N-(1-4C alkyl)-quinuclidinium salt or quinuclidine-N-oxide derivatives, stereoisomers, stereoisomer mixtures, salts and solvates are new. [Image] R 1 - R 3H, OH, S...

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Hauptverfasser: CAROLINA SALCEDO ROCA, IGNACIO JOSE MIQUEL BONO, ANNA FERNANDEZ SERRAT, ANDRES FERNANDEZ GARCIA, JOSE IGNACIO BONILLA NAVARRO, CARLES FARRERONS GALLEMI, CARMEN LAGUNAS ARNAL, DOLORS BALSA LOPEZ, JUAN LORENZO CATENA RUIZ
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Sprache:eng
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Zusammenfassung:3-Quinuclidinyl N-(arylmethyl, cycloalkylmethyl or heteroarylmethyl)-N-phenylcarbamates (I) are new. Carbamates of formula (I) and their N-(1-4C alkyl)-quinuclidinium salt or quinuclidine-N-oxide derivatives, stereoisomers, stereoisomer mixtures, salts and solvates are new. [Image] R 1 - R 3H, OH, SH, CN, F, Cl, Br, I, ST, OT (optionally substituted by one or more F), NHCONH 2 or T (optionally substituted by one or more of F and OH); or R 1 + R 2 or R 2 + R 3(CH 2) 3 or (CH 2) 4; T : 1-4C alkyl; R 43-6C cycloalkyl, cyclohexenyl, norbornenyl, bicyclo (2.2.1) heptanyl, 2- or 3-thienyl, 2- or 3-furyl, 2-, 3- or 4-pyridyl, 1- or 2-naphthyl, 1- or 2-benzodioxolanyl, 1- or 2-benzodioxanyl or phenyl (optionally substituted by one or more of OH, SH, CN, F, Cl, Br, I, NHCONH 2, COOH, COOT, ST, OT (optionally substituted by one or more F) or T (optionally substituted by one or more of F and OH)); the quinuclidinyl group preferably has 3(R)-configuration. ACTIVITY : Uropathic; antiinflammatory; antiasthmatic; antiallergic; ophthalmological MECHANISM OF ACTION : Muscarinic receptor antagonist. In particular (I) are selective M 3 receptor antagonists. 3(R)-Quinuclidinyl N-(cyclohexylmethyl)-N-(4-fluorophenyl)-carbamate (Ia) had K i 0.025 nM for M 3 receptors and a selectivity for the M 3 relative to the M 2 receptor of 300.