Quaternary ammonium compounds useful as muscarinic receptor antagonists

A compound having the formula IId:

• where
• X− is an anion of a pharmaceutically acceptable acid;
• R3 is selected from H and —C0-1alkylene-OH;
• or R3 can form a double bond with the carbon atom on the cyclopentyl group;
• Z is selected from a bond, —O—, —S—, —S(O)—, —SO2—, —SO2—NRZ1—, —NRZ1—SO2—, —C(O)—, —OC(O)—, —C(O)O—, —NRZ1C(O)—, —C(O)NRZ1—, —NRZ2—C(O)—NRZ3—, —NRZ2—C(S)—NRZ3—, —CH(OH)—, and —C(═N—O—RZ4)—;
• where RZ1 is selected from H and —C1-4alkyl;
• RZ2 and RZ3 are independently selected from H, —C1-4alkyl, and —C3-6cycloalkyl, or RZ2 and RZ3 are taken together to form —C2-4alkylene- or —C2-3alkenylene-;
• and RZ4 is selected from —C1-4alkyl and benzyl;
• wherein the cyclopentyl group is optionally substituted with 1 to 5 R groups independently selected from —C1-4alkyl, —C2-4alkenyl, —C2-4alkynyl, —C3-6 cycloalkyl, cyano, halo, —ORa, —SRa, —S(O)Ra, —S(O)2Ra, and —NRbRc;
• where each Ra is independently selected from H, —C1-4alkyl, —C2-4alkenyl, —C2-4alkynyl, and —C3-6cycloalkyl;
• and each Rb and Rc is independently selected from H, —C1-4alkyl, —C2-4alkenyl, —C2-4alkynyl, and —C3-6cycloalkyl;
• wherein RQ is selected from halo, —C1-4alkyl, —C0-4alkylene-OH, cyano, —C0-2 alkylene-COOH, —C(O)O—C1-4alkyl, —O—C1-4alkyl, —S—C1-4alkyl, —NH—C(O)—C1-4alkyl, —N-di-C1-4alkyl, and —N+(O)O;
• wherein each alkyl, alkylene, alkenyl, alkenylene, alkynyl, and cycloalkyl group in R, R3, Z, and RQ, is optionally substituted with 1 to 5 fluoro atoms;
• and
• each —CH2— group in —(CH2)1-4— is optionally substituted with 1 or 2 substituents independently selected from —C1-2 alkyl, —OH, fluoro, and phenyl;
• or a pharmaceutically acceptable salt thereof.

A compound having the formula IIe:

• where
• X− is an anion of a pharmaceutically acceptable acid;
• R3 is selected from H and —C0-1alkylene-OH;
• Z is selected from a bond, —O—, —S—, —S(O)—, —SO2—, —SO2—NRZ1—, —NRZ1—SO2—, —C(O)—, —OC(O)—, —C(O)O—, —NRZ1C(O)—, —C(O)NRZ1—, —NRZ2—C(O)—NRZ3—, —NRZ2—C(S)—NRZ3—, —CH(OH)—, and —C(═N—O—RZ4)—;
• where RZ1 is selected from H and —C1-4alkyl;
• RZ2 and RZ3 are independently selected from H, —C1-4alkyl, and —C3-6cycloalkyl, or RZ2 and RZ3 are taken together to form —C2-4alkylene- or —C2-3alkenylene-;
• and RZ4 is selected from —C1-4alkyl and benzyl;
• Q is an aryl or heteroaryl group;
• wherein the aryl in Q is optionally substituted with 1 to 5 RQ groups independently selected from halo, —C1-4alkyl, —C0-4alkenyl-OH, cyano, —C0-2alkylene-COOH, —C(O)O—C1-4alkyl, —O—C1-4alkyl, —S—C1-4alkyl, —NH—C(O)—C1-4alkyl, —N-di-C1-4alkyl, and —N+(O)O;
• wherein each alkyl, alkylene, alkenyl, alkenylene, alkynyl, and cycloalkyl group in R3, Z, Q, and RQ, is optionally substituted with 1 to 5 fluoro atoms;
• and
• each —CH2— group in —(CH2)1-4— is optionally substituted with 1 or 2 substituents independently selected from —C1-2 alkyl, —OH, fluoro, and phenyl;
• or a pharmaceutically acceptable salt thereof.