7-azoniabicyclo[2.2.1]heptane derivatives, methods of production, and pharmaceutical uses thereof

A stereochemically pure compound with a stereochemical purity of at least 80% selected from the group consisting of:

• (1S,2R)-2-(R)-2′-cyclopentyl-2′-hydroxy-2′-phenylacetoxy)-7,7-dimethyl-7-azoniabicyclo[2.2.1]heptane bromide;
• (1R,2S)-2-(R)-2′-cyclopentyl-2′-hydroxy-2′-phenylacetoxy)-7,7-dimethyl-7-azoniabicyclo[2.2.1]heptane bromide;
• and
• (1R,2R)-2-(R)-2′-cyclopentyl-2′-hydroxy-2′-phenylacetoxy)-7,7-dimethyl-7-azoniabicyclo[2.2.1]heptane bromide.

A pharmaceutical composition, comprising a stereochemically pure compound with a stereochemical purity of at least 80% selected from the group consisting of:

• (1S,2R)-2-(R)-2′-cyclopentyl-2′-hydroxy-2′-phenylacetoxy)-7,7-dimethyl-7-azoniabicyclo[2.2.1]heptane bromide;
• (1R,2S)-2-(R)-2′-cyclopentyl-2′-hydroxy-2′-phenylacetoxy)-7,7-dimethyl-7-azoniabicyclo[2.2.1]heptane bromide;
• and
• (1R,2R)-2-(R)-2′-cyclopentyl-2′-hydroxy-2′-phenylacetoxy)-7,7-dimethyl-7-azoniabicyclo[2.2.1]heptane bromide;
• and a pharmaceutically acceptable carrier.

A method of treating a subject with a disease wherein the disease is a respiratory disease, comprising administering to the subject a therapeutically effective amount of a pharmaceutical composition comprising a stereochemically pure compound with a stereochemical purity of at least 80% selected from the group consisting of:

• (1S,2R)-2-((R)-2′-cyclopentyl-2′-hydroxy-2′-phenylacetoxy)-7,7-dimethyl-7-azoniabicyclo[2.2.1]heptane bromide;
• (1R,2S)-2-((R)-2′-cyclopentyl-2′-hydroxy-2′-phenylacetoxy)-7,7-dimethyl-7-azoniabicyclo[2.2.1]heptane bromide;
• (1R,2R)-2-((R)-2′-cyclopentyl-2′-hydroxy-2′-phenylacetoxy)-7,7-dimethyl-7-azoniabicyclo[2.2.1]heptane bromide;
• and a pharmaceutically acceptable carrier.