New diarylacetic acid quaternized azabicycloheptyl esters, useful e.g. for treating asthma, chronic obstructive pulmonary disease, arrhythmia or menstrual disorders, are anticholinergic agents

摘要

Quaternized 1-azabicyclo-(2.2.1)-hept-4-yl esters (I) and their non-quaternized intermediates (IV) are new. Quaternized 1-azabicyclo-(2.2.1)-hept-4-yl esters of formula (I) and their optical isomers, enantiomer mixtures, racemates and acid addition salts are new. X- = monovalent anion, preferably chloride, bromide, iodide, sulfate, phosphate, methanesulfonate, nitrate, maleate, acetate, citrate, fumarate, tartrate, oxalate, succinate, benzoate or p-toluenesulfonate; A, A' = O, S, NH, CH2, CH=CH or N(alkyl); R = H, OH, alkyl, alkoxy, haloalkyl, haloalkoxy, hydroxyalkyl, CF3, CHF2, alkoxyalkyl, alkylcarbonyloxy, haloalkylcarbonyloxy, (3-6C) cycloalkylalkyl, OCOF3 or halo; R1 = 1-5C alkyl (optionally substituted by 3-6C cycloalkyl, OH or halo); R2, R3, R21, R31, Rx, Ry = H, alkyl, alkoxy, OH, CF3, CHF2, CN, NO2 or halo; or R1+R2 = 3-5C alkylene; or Rx + Ry = bond, O, S, NH, CH2, CH2CH2, N(alkyl), CH(alkyl) or C(alkyl)2; alkyl moieties have 1-4C unless specified otherwise. Independent claims are also included for: (1) new non-quaternized intermediates of formula (IV) (optionally in acid addition salt form); and (2) use of the tropanol compound of formula (II) or its acid addition salts in the preparation of (IV).