A number of arylcycloalkane carboxylic esters, including arylcyclopropane, arylcyclobutane, arylcyclopentane and arylcyclohexane carboxylic acid esters, are known to possess anticholinergic activity. Some of them have a pronounced spasmolytic or anticonvulsant activity and have therefore been proposed to be used as substitutes for atropine in the treatment of sarin poisoning (sarin is an organophosphorous anticholinesterase agent acting as a nerve gas). Other activities related to that type of compounds are antipsychotic, anti-ischemic, anti-stroke and antidementia.
Specific arylcyclopropane carboxylic esters having anticholinergic activities are, for example, described in Beres, J. A., et al., J. Pa. Acad. Sci. (1992), 66(1), 2; U.S. Pat. No. 4,418,202; Mnjoyan, A. L., et al., Arm. Khim. Zh. (1976), 29(2) 194-9; Kuzuna, S., et al., Takeda Kenyosho Hu (1975), 34(4), 467-73; and WO 92/02481.
Arylcyclobutane carboxylic esters having anticholinergic activities are, for example, described in Bannard, R. A. B., et al., Can. J. Phys. Pharm. 47 (1969) 1036 (2',2'-diisopropylaminoethyl 1-phenylcyclobutane-carboxylate, 1'-methylpiperidyl-4' 1-phenylcyclobutane-carboxylate); CH--B--240160 (diethylaminoethyl 1-phenylcyclobutanecarboxylate); Parkkari, J. H., et al., Can. J. Chem. 43 (1965) 3119 (N-methyl-4-piperidyl 1-p-methylphenylcyclobutanecarboxylate, N-methyl-4-piperidyl 1-p-methoxyphenylcyclobutanecarboxylate); and Mnoyan, A.L. et al., supra (dimethylaminoethyl and diethylaminoethyl 1-benzophenylcyclobutylcarboxylates).
Arylcyclopentane carboxylic esters having anticholinergic activities are, for example, described in Bannard, R. A. B., et al., Can. J. Chem. 40 (1962) 1909-1916; Stubbins, J. F., et al, Med. Chem. Res. 2 (1992) 384-393; JP-A-02062823; U.S. Pat. No. 3,317,526; FR-A-1461314; FR-A-2155927; DD-A-289411 and FR-A-2168881.
Arylcyclohexane carboxylic esters having anticholinergic activities are, for example, described in Zbigniew, J., et al., Pol. J. Pharmacol. Pharm. 35 (1983) 103-107; Tsung-Ping Su et al., Pharmacology and Exp. Therapeutics 259 (1991) 543-550; Wolinski, J., and Cessak, M., Acta Pol. Pharm. 36 (1979) 635-40; WO 92/02481 and FR-A-2155927.