3,6-Disubstituted azabicyclo [3.1.0] hexane derivatives useful as muscarinic receptor

A compound selected from the group consisting of:

• 1-(3-azabicyclo[3.1.0]hex-3-yl)-3-(2-benzyloxy-5-methylphenyl)-3-phenyl propane (Compound No. 1),
• 1-(3-azabicyclo[3.1.0]hex-3-yl)-3-(2-hydroxy-5-methylphenyl)-3-phenyl propane (Compound No.2),
• 1-(1,5-dimethyl-3-azabicyclo[3.1.0]hex-3-yl)-3-(2-benzyloxy-5-methylphenyl)-3-phenyl propane (Compound No.3),
• 1-(1,5-dimethyl-3-azabicyclo[3.1.0]hex-3-yl)-3-(2-hydroxy-5-methylphenyl)-3-phenyl propane (Compound No.4),
• 1-(1-methyl-3-azabicyclo[3.1.0]hex-3-yl)-3-(2-benzyloxy-5-methylphenyl)-3-phenyl propane (Compound No.5),
• 1-(1-methyl-3-azabicyclo[3.1.0]hex-3-yl)-3-(2-hydroxy-5-methylphenyl)-3-phenyl propane (Compound No.6),
• 1-(2-methyl-3-azabicyclo[3.1.0]hex-3-yl)-3-(2-benzyloxy-5-methylphenyl)-3-phenyl propane (Compound No.7),
• 1-(2-methyl-3-azabicyclo[3.1.0]hex-3-yl)-3-(2-hydroxy-5-methylphenyl)-3-phenyl propane (Compound No.8),
• 1-(2-methyl-3-azabicyclo[3.1.0]hex-3-yl)-3-(2-hydroxy-5-methylphenyl)-3-phenyl propane (Compound No.9).

A method for treatment or prophylaxis of an animal or a human suffering from a disease or disorder of the respiratory, urinary and gastrointestinal systems, wherein the disease or disorder is mediated through muscarinic receptors, comprising administering to said mammal or human, a therapeutically effective amount of a compound having the structure of Formula I,

• or its pharmaceutically acceptable salts, pharmaceutically acceptable solvates, esters, enantiomers, diastereomers, N-oxides, polymorphs, prodrugs or metabolites, wherein
• R1 represents hydrogen, lower (C1-C4) alkyl, lower perhaloalkyl (C1-C4), aryl or aralkyl;
• R2 represents hydrogen, lower (C1-C4) alkyl, lower perhaloalkyl (C1-C4), aralkyl, alkylamino, alkoxyalkyl, alkoxyaryl or alkoxycarbonyl;
• and
• R3, R4, R5 and R6 independently represent hydrogen, lower (C1-C4) alkyl, lower perhaloalkyl (C1-C4), cyano, hydroxy, nitro, lower alkoxycarbonyl, halogen (e.g., F, Cl, Br, I) lower alkoxy (C1-C4), lower perhaloalkoxy (C1-C4), amino or lower alkylamino.

A process of preparing a compound of Formula I,

• or its pharmaceutically acceptable salts, pharmaceutically acceptable solvates, esters, enantiomers, diastereomers, N-oxides, polymorphs, prodrugs or metabolites, wherein
• R1 represents hydrogen, lower (C1-C4) alkyl, lower perhaloalkyl (C1-C4), aryl or aralkyl;
• R2 represents hydrogen, lower (C1-C4) alkyl, lower perhaloalkyl (C1-C4), aralkyl, alkylamino, alkoxyalkyl, alkoxyaryl or alkoxycarbonyl;
• and
• R3, R4, R5 and R6 independently represent hydrogen, lower (C1-C4) alkyl, lower perhaloalkyl (C1-C4), cyano, hydroxy, nitro, lower alkoxycarbonyl, halogen (e.g., F, Cl, Br, I), lower alkoxy (C1-C4), lower perhaloalkoxy (C1-C4), amino or lower alkylamino, said process comprising:
• condensing a compound of Formula II with a compound of Formula III
• wherein R7 is a leaving group,
• in the presence of a condensing agent to give a protected compound of Formula IV,
• which is further deprotected in the presence of a deprotecting agent to a compound of Formula V (Formula I, R1=hydrogen).