Yoshitomi Pharmaceutical Industries, Ltd.

Mineo Tsuruda

Takanori Oe

Michio Nakanishi

Tsutomu Yamanaka

Kazuyuki Kawasaki

Hiroshi Yasuda

Hiroshi Mikashima

Shinro Setoguchi

Chiaki Kitami

Kazuhiro Goto

Masao Hisadome

The present invention provides an industrially valuable method for preparing an optically active 3,4-dihydro-3,4-epoxy-2H-1-benzopyran compound which is useful as a starting material for an optically active benzopyran compound with antihypertensive, coronary blood flow-increasing activities and the like, and also provides a diastereometric ester compound with a 3-halo-4-hydroxy-2H-1-benzopyran compound which is useful as an intermediate for said epoxy compound.

Processes for preparing optically active

The present invention provides an industrially valuable method for preparing an optically active 3,4-dihydro-3,4-epoxy-2H-1-benzopyran compound which is useful as a starting material for an optically active benzopyran compound with antihypertensive, coronary blood flow-increasing activities and the like, and also provides a diastereomeric ester compound with a 3-halo-4-hydroxy-2H-1-benzopyran compound which is useful as an intermediate for said epoxy compound.

.alpha.-(2,6-dimethyl-4-carboxyphenyl)-2-methyl-5-(1-imidazolyl)-benzenemet hanol, pharmaceutically acceptable metal salts forms thereof, acid addition salt forms thereof, amino acid addition salt forms thereof, hydrate forms thereof and mixtures thereof. Such compounds have inhibitory activities on biosynthesis of thromboxane A.sub.2, inhibitory activities on platelet aggregation, vasodilative activities and protective effects against liver disorders.

Imidazole derivatives

Bis-(aminoalkoxy)-phenyl, pyridyl ketones, and use as immunological

1H-Tetrazole derivatives of the formula: ##STR1## and pharmaceutically acceptable salts thereof, wherein the ring P is pyridine ring; A is carbonyl, methylene or C.sub.2-4 alkylidene; Y is oxygen, sulfur or --N(R.sup.1)-- wherein R.sup.1 is hydrogen or C.sub.1-4 alkyl; each of X.sup.1 and X.sup.2 is hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl or substituted phenyl, any substitutent on the phenyl being halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or trifluoromethy; and R is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, hydroxy-C.sub.1-4 alkyl, C.sub.1-4 alkoxy-C.sub.1-4 alkyl, carboxy-C.sub.1-4 alkyl, C.sub.1-4 alkoxycarbonyl-C.sub.1-4 alkyl or substituted or unsubstituted amino-C.sub.1-4 alkyl, any substituted amino being C.sub.1-4 alkyl- or di-C.sub.1-4 alkyl-amino, piperidino, 1-pyrrolidinyl, morpholino, 1-piperazinyl and 4-C.sub.1-4 alkyl-1-piperazinyl; are useful as antiallergic agents.

1H-tetrazole derivatives

Tricycle substituted acetones

Heterocyclic compounds of the formula: ##SPC1## Wherein A is a carbonyl group, a methylene group or an alkylidene group having 2 to 4 carbon atoms; B is an oxygen atom, a sulfur atom or --N(R')-- (wherein R' is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms); each of R.sup.1 and R.sup.2 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a phenyl group which may be substituted by a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; X is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or OM (wherein M is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a metal atom or NH.sub.4); and ring P represents a pyridine ring, are useful as anti-allergic agents.

Benzopyrano and benzothiopyrano [2,3-6] pyridines

Substituted alkanoic acids and derivatives thereof of the formula: ##SPC1## Wherein each of X.sup.1 and X.sup.2 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; each of R.sup.1 and R.sup.2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; A is a carbonyl group, a methylene group or an alkylidene group having 2 to 4 carbon atoms; Y is --O--, --S-- or --N(R)-- [wherein R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms]; Z is OH or Q--B--N(R.sup.3)(R.sup.4) [wherein Q is O (oxygen atom) or NH, B is an alkylene group having 1 to 4 carbon atoms and each of R.sup.3 and R.sup.4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, or R.sup.3 and R.sup.4 together with the adjacent nitrogen atom form a saturated heterocycle selected from the group consisting of pyrrolidine, piperidine, morpholine, piperazine and piperazine substituted by an alkyl group having 1 to 4 carbon atoms at the 4-position]; and ring P represents a pyridine or a pyridine N-oxide ring; and pharmaceutically acceptable salts thereof are useful as antirheumatics, analgesics, antipyretics and anti-inflammatory agents.

Growing community of inventors

Fukuoka, Japan

Mineo Tsuruda