Pyridylfuran and pyridylthiophene compounds

Details Pyridylfuran and pyridylthiophene compounds Pyridylfuran and pyridylthiophene compounds

1998-01-06

2000-04-11

Rotman, Alan L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

514340, 546256, 5462804, C07D40504, C07D40514, A61K 314433, A61K 314436

Patent

active

060488808

ABSTRACT:
A compound of the formula: ##STR1## and its pharmaceutically effective salts, wherein R.sup.1 and R.sup.2 are independently selected from the following:
(a) hydrogen, halo, R.sup.5 --, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, hydroxy-R.sup.5 --, R.sup.5 --O--R.sup.5 --, or the like; (b) Ar--, Ar--R.sup.5 --, Ar--C.sub.2-6 alkenyl, Ar--C.sub.2-6 alkynyl, Ar--O--, Ar--O--R.sup.5 -- or the like; (c) R.sup.5 --C(O)--, --NO.sub.2, cyano, NH.sub.2 --C(O)--, R.sup.5 --NH--C(O)--, (R.sup.5).sub.2 --N--C(O)--, Ar--C(O)-- or the like; and (d) R.sup.5 --C(O)--NH--, Ar--C(O)--NH-- or the like; wherein Ar is optionally substituted aryl or heteroaryl such as phenyl and pyridyl; and wherein R.sup.5 is optionally halo-substituted C.sub.1-6 alkyl; R.sup.3 is selected from the following: (e) cyano, formyl, tetrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, R.sup.5 --C(O)--, C.sub.2-6 alkenyl-C(O)--, C.sub.2-6 alkynyl-C(O)--, R.sup.5 --C(O)--R.sup.5 --, or the like; (f) R.sup.5 --C(O)--NH--, Ar--C(O)--NH--, or the like; (g) R.sup.5 --S--, R.sup.5 --S(O)--, R.sup.5 --NH--S(O).sub.2 --, or the like; and (h) Ar--C(O)--, Ar--R.sup.5 --C(O)--, Ar--C.sub.2-6 alkenylene-C(O)-- or the like; or two of R.sup.1, R.sup.2 and R.sup.3 together form a group of the formula --A.sup.1 --B.sup.1 --A.sup.2 -- or --A.sup.1 --B.sup.1 --A.sup.3 --B.sup.2 --A.sup.2 -- such as cyclic alkyl optionally substituted with oxo; R.sup.4 is hydrogen, halo, R.sup.5 --C(O)-- and the like; X is O, S, S(O) or S(O).sub.2 ; m is 0, 1, 2, 3 or 4. The present invention also provides processes for the preparation thereof, the use thereof in treating cytokine mediated diseases and/or cell adhesion molecule (CAM) mediated diseases and pharmaceutical compositions for use in such therapy.

REFERENCES:
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Oda, Kazuaki et al.: "Benzannulation of heteroaromatics by photoreaction of arenecarbothiamides with 2 methoxyfuran", J. Chem. Soc., Chem. Commun., vol. 12, pp. 1477-1278, (1994).
Zhang, Yihua et al., "Pyridine-substituted hydroxythiophenes. II. Alkylation of 0-(2-, 3- and 4-pyridyl)-3-hydroxythiophenes", J. Heterocyclic Chem., vol. 30(5), pp. 1293-1299, (1993).
Bacon, Edward R. et al., "Synthesis of 7-ethyl-4,7-dihydro-4-oxo-2-(4-pyridinyl)thieno[2,3-b]pyridine-5-caboxylic acid", J. Heterocyclic Chem., vol. 28(8), pp. 1953-1955, 1991).
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