9-Hydroxydibenzo[b,d]pyrans useful as analgesics, hypotensives, immunosuppressants, tranquilizers; as anti-secretory and anti-anxiety drugs; intermediates therefor and derivatives thereof having the formulae ##STR1## wherein R is hydrogen or alkanoyl having from one to five carbon atoms; R.sub.1 is hydrogen, alkanoyl having from one to five carbon atoms or --CO--(CH.sub.2).sub.p --NR.sub.2 R.sub.3 wherein p is 0 or an integer from 1 to 4; each of R.sub.2 and R.sub.3 when taken individually is hydrogen or alkyl having from one to four carbon atoms; R.sub.2 and R.sub.3 when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from one to four carbon atoms in the alkyl group; each of R.sub.4 and R.sub.5 is hydrogen, methyl or ethyl; R.sub.0 is oxo or alkylenedioxy having from two to four carbon atoms; Z is (a) alkylene having from one to nine carbon atoms; (b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n -- wherein each of (alk.sub.1) and (alk.sub.2) has from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 9; each of m and n is 0 or 1; X is O, S, SO or SO.sub.2 ; and W is methyl, phenyl, p-chlorophenyl, p-fluorophenyl, pyridyl, piperidyl, cycloalkyl having from 3 to 7 carbon atoms, or monosubstituted cycloalkyl wherein the substituent is phenyl, p-chlorophenyl or p-fluorophenyl; with the proviso that when W is methyl, Z is --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n --.
CROSS-REFERENCE TO RELATED APPLICATION
This application is a continuation of application Ser. No. 819,471 filed July 27, 1977, now U.S. Pat. No. 4,143,139 granted Mar. 6, 1979, which in turn is a continuation of application Ser. No. 730,672 filed Oct. 7, 1976 and now abandoned which in turn is a continuation-in-part of application Ser. No. 628,210 filed Nov. 3, 1975 and now abandoned.
Methods of treating an immune disease, cell proliferation, restenosis and vascular smooth muscle cells using the pharmaceutical compounds of the formula ##STR1## in which R.sup.2 is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R.sup.2 is furanyl optionally substituted with C.sub.1-4 alkyl; and salts thereof.
Pharmaceutical compound of the formula ##STR1## R.sup.1 is phenyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl and heteroaryl groups being optionally substituted, or R.sup.1 is furanyl optionally substituted with C.sub.1-4 alkyl; R.sup.2 is nitrile, carboxy, --COOR.sup.4 where R.sup.4 is an ester group, --CONR.sup.5 R.sup.6 where R.sup.5 and R.sup.6 are each hydrogen or C.sub.1-4 alkyl, or R.sup.7 SO.sub.2 -- where R.sup.7 is C.sub.1-4 alkyl or optionally substituted phenyl; R.sup.3 is --NR.sup.8 R.sup.9, --NHCOR.sup.8, --N(COR.sup.8).sub.2, --N.dbd.CHOR.sup.8 where R.sup.8 and R.sup.9 are each hydrogen or C.sub.1-4 alkyl, or --NHSO.sub.2 R.sup.10 where R.sup.10 is C.sub.1-4 alkyl or optionally substituted phenyl; or ##STR2## where X is C.sub.2-4 alkylene; and the group ##STR3## represents a pyridine ring fused to the benzopyran nucleus; and salts thereof.
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