Vasoconstrictive dihydrobenzopyran derivatives

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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514247, 514255, 544180, 544224, 544242, 544336, 5462821, A61K 3135, C07D49304, C07D40512, C07D31158

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058246827

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BRIEF SUMMARY
CROSS-REFERENCE TO RELATED APPLICATIONS

This application is based upon PCT Application Ser. No. PCT/EP 94/02703, filed Aug. 12, 1994, which claims priority from European Patent Application Ser. No. 93.202.443.3, filed on Aug. 19, 1993; European Patent Application Ser. No. 93.202.442.5, filed on Aug. 19, 1993; and European Patent Application Ser. No. 93.202.441.7, filed on Aug. 19, 1993.
The present invention relates to novel dihydrobenzopyran derivatives, processes for their preparations, pharmaceutical compositions containing them and their use as a medicine, in particular for the prevention and/or treatment of disorders characterized by excessive vasodilatation, especially migraine.
Migraine is a non-lethal disease suffered by one in ten individuals. The main symptom is headache; other symptoms include vomiting and photophobia. For many years the most widely used treatment for migraine involved the administration of ergotalkaloids, which show however several adverse side effects. Recently a tryptamine derivative, i.e. sumatriptan, was introduced as a novel antimigraine drug. We have now surprisingly found that the present novel dihydrobenzopyran derivatives show 5-HT.sub.1 -like agonistic activity and can thus be used in the treatment of disorders characterized by excessive vasodilatation, especially migraine.
The present invention is concerned with compounds of formula ##STR3## the pharmaceutically acceptable acid or base addition salts thereof, and the stereochemically isomeric forms thereof, wherein alkyl; aryloxy or arylmethoxy; radical, which is linked to the 7 and 8 position of the dihydrobenzopyran moiety, and has the formula


______________________________________ --CH.dbd.CH--CH.dbd.CH-- (a1), --(CH.sub.2).sub.n -- (a2), --(CH.sub.2).sub.m --X-- (a3), --X--(CH.sub.2).sub.m -- (a4), --CH.dbd.CH--X-- (a5), --X--CH.dbd.CH-- (a6), --O--(CH.sub.2).sub.t --Y-- (a7), --Y--(CH.sub.2).sub.t --O-- (a8), --(CH.sub.2).sub.t --Z-- (a9), --Z--(CH.sub.2).sub.t -- (a10), --CH.dbd.CH--Z-- (a11), --Z--CH.dbd.CH-- (a12), --NH--C(A).dbd.N-- (a13), --O--C(A).dbd.N-- (a14), --N.dbd.C(A)--O-- (a15); ______________________________________ with --NR.sup.7 --; --NR.sup.7 --; alkyl-S(O)--, hydrogen and R.sup.6b is hydroxyC.sub.1-6 alkyl, carboxylC.sub.1-6 alkyl, C.sub.1-6 alkyloxycarbonylC.sub.1-6 alkyl, trihalomethyl, C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkyloxycarbonylC.sub.1-6 alkyl-S--, carboxylC.sub.1-6 alkyl-S--, C.sub.1-6 alkyl-S--, C.sub.1-6 alkyl-S(O)--, aryl-S--, aryl-S(O)-- or R.sup.6b is a radical of formula ##STR4## R.sup.8 and R.sup.9 each independently are hydrogen, carboxyl, C.sub.1-6 alkyloxycarbonyl, aminocarbonyl, mono- or di(C.sub.1-6 alkyl)aminocarbonyl; R.sup.17 each independently are hydrogen, halo or C.sub.1-6 alkyl; R.sup.25 each independently are hydrogen or C.sub.1-6 alkyl; R.sup.4 can only mean hydrogen; and R.sup.5c and R.sup.6c each independently are hydrogen, halo, C.sub.1-6 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, hydroxy, C.sub.1-6 alkyloxy, cyano, aminoC.sub.1-6 alkyl, carboxyl, C.sub.1-6 alkyloxycarbonyl, nitro, amino, aminocarbonyl, C.sub.1-6 alkylcarbonylamino, or mono- or di(C.sub.1-6 alkyl)amino; ##STR5## wherein R.sup.26 is hydrogen, cyano, aminocarbonyl or C.sub.1-6 alkyl; alkynyl, C.sub.3-6 cycloalkyl or arylC.sub.1-6 alkyl --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, or a piperazine which is optionally substituted with C.sub.1-6 alkyl; R.sup.40, R.sup.41, R.sup.42, R.sup.43, R.sup.44, R.sup.45, R.sup.46, R.sup.53, R.sup.54 and C.sub.1-6 alkyloxy, aryloxy, arylC.sub.1-6 alkyl, C.sub.1-6 alkylthio, cyano, amino, mono- or di(C.sub.1-6 alkyl)amino, mono- or di(C.sub.3-6 cycloalkyl)amino, aminocarbonyl, C.sub.1-6 alkyloxycarbonylamino, C.sub.1-6 alkylaminocarbonylamino, piperidinyl, pyrrolidinyl; alkyl, C.sub.1-6 alkylcarbonyl, or arylC.sub.1-6 alkyl; atom to which they are connected they can form C(O); atom to which they are connected they can form C(O); taken together may fo

REFERENCES:
patent: 4405622 (1983-09-01), Kluge
patent: 5137901 (1992-08-01), Junge et al.
patent: 5541180 (1996-07-01), Van Lomment et al.

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