Antimuscarinic bronchodilators

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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514826, 546137, C07D45300, A61K 31435

Patent

active

052927490

ABSTRACT:
##STR1## 3-Quinuclidinyl butanoate and propanoate antimuscarinic bronchodilators, particularly useful in the treatment of chronic obstructive airways disease and asthma, of formula (1), and their pharmaceutically acceptable salts, wherein X is either (a) a phenyl group optionally substituted by one or two substituents each independently selected from halo. CF.sub.3, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and hydroxy or (b) a thienyl group; and "Het" is either (a) a 5-membered nitrogen-containing heterocyclic group attached to the adjacent carbon atom either by a carbon or a ring nitrogen atom and which is selected from imidazolyl, pyrazolyl, triazolyl and tetrazolyl. (b) an oxadiazolyl or thiadiazolyl group attached to the adjacent carbon atom by a carbon atoms, or (c) a 6-membered nitrogen-containing heterocyclic group attached to the adjacent carbon atom by a carbon atom and selected from pyridinyl, pyrazinyl, pyrimidinyl and pyridazinyl, "Het" being optionally substituted by up to two substituents each independently selected from halo, CF.sub.3, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, amino and azido; and m is 1 or 2.

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Chemical Abstracts, vol. 96, No. 5, 1 Feb. 1982 (Columbus, Ohio, US) E. E. Mikhlina et al.: "Synthesis and cholinolytic properties of 3-hydroxyquinuclidine esters", see p. 647, abstract 35045c, & Khim.-Farm.Zh. 1981, 15(8), 51-5.
J. Med. Chem., vol. 26, 1983, E. R. Atkinson et al.: "Parasympatholytic (anticholinergic) esters of the isomeric 2-tropanols. 2. Non-glycolates", see pp. 1772-1775, especially compound 17.

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