cis-4a-Aryl-1,2,3,4,4a,9b-hexahydro-benzofuro[3,2-c]pyridines an

Details cis-4a-Aryl-1,2,3,4,4a,9b-hexahydro-benzofuro[3,2-c]pyridines an cis-4a-Aryl-1,2,3,4,4a,9b-hexahydro-benzofuro[3,2-c]pyridines an

1982-07-22

1985-03-26

Rotman, Alan L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

546 89, 546217, 546267, 546 15, C07D49114, A61K 31445

Patent

active

045073066

ABSTRACT:
cis-4a-Aryl-1,2,3,4,4a,9b-hexahydro-benzofuro[3,2-c]pyridines and methods of preparing same are described. On the nitrogen atom there may be a substituent including loweralkyl, loweralkenyl, phenylloweralkyl, hydrogen, cyanoloweralkyl, phenylcarbonylloweralkyl, phenoxyloweralkyl and cycloalkylloweralkyl. The 4a-aryl group may be a phenyl, mono-halogen substituted phenyl, tolyl, methoxyphenyl, hydroxyphenyl, or furyl. These compounds are useful as analgesic and anticonvulsant agents.
3-o-Fluorophenyl-1-methyl-4-aryl-4-piperidinols which are useful as intermediates for preparing the aforementioned compounds and methods for preparing same are also described.

REFERENCES:
patent: 2589378 (1949-11-01), Henecka
patent: 2809201 (1957-10-01), Koelsch
Henecka et al., "Synthesis with .beta.-Arylhydroacrylnitriles", Med. Chem., Abhandl. Me. Chem. Forschungestaetten Farbenfabriken Bayer A.G., 7, (1963), 197-214, (See also Chemical Abstract, vol. 60, (1964), 4121g).
Reese et al., "Preparation of 4a-alkoxy-1,2,3,4,4a,9b-hexahydro- and -1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridines", J. Chem. Soc., C 1971, (1).
Sharkova et al., "Ring Closure of Some O-Aryl Ethers of Ketoximes to Benzofurans", Khim, Geterotsikl. Soedin., 1971, 7(12), 1596-1600, (See also Chemical Abstract, vol. 72, (1972), 5386e).
Aksanova et al., "Synthesis and Pharmacological Study of Some Tetrahydrobenzofuropyridine Derivatives", Khim. Farm. Zh., 1975, 9(1), 7-9, (See also Chemical Abstract, vol. 82, (1975), 139982h).
Patchette et al., "Analgesics I. 4-Acyloxy-3,4-Diphenyl-1-Methylpipendines", J. Medicinal and Pharmaceutical Chemistry, vol. 4, No. 2, (1961), 385-392.

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