Toyo Jozo Kabushiki Kaisha

Eiichi Hayashi

Yukio Suzuki

Masao Yaso

Kensuke Shibata

Noriyasu Takayanagi

Daisuke Mochizuki

Tetsu Saito

Eiichi Honda

Hiroyuki Kinoshita

Katsumi Nishimura

Kenzi Saeki

Katumi Nisimura

A compound of the formula ##STR1## wherein Q is --CO-- or --CH.sub.2 --, R is hydroxyl, lower alkoxy, halogen, --NH-lower alkylene-OH, --NH-lower alkylene-arylthio, --NH-lower alkylene-halogen, ##STR2## is dilower alkylamino, cycloalkylamino, morpholino, ##STR3## in which R.sub.9 is hydrogen, lower alkyl or aryl, R.sub.10 is hydrogen, lower alkyl, hydroxy-lower alkyl, hydroxy-lower alkoxy-lower alkyl or di(aryl)-lower alkyl, m is an integer from 4 to 6, n is 2 or 3, R.sub.1 is alkyl or aryl-lower alkyl, R.sub.2 and R.sub.3 are each lower alkyl, or together form tetramethylene, and R.sub.4 is hydrogen, lower alkyl or aryl, in which aryl is phenyl which is optionally substituted with a group selected from the group consisting of 1-3 halogen, nitro, lower alkyl and lower alkoxy, or a pharmaceutically acceptable salt thereof, inhibits blood platelet aggregation, has vasodilating activity and inhibits lipoperoxide generation.

2-substituted alkoxy-3-substituted-pyrazines

A compound of the formula ##STR1## wherein Q is --CO-- or --CH.sub.2 --, R is hydroxyl, lower alkoxy, halogen, --NH-lower alkylene-OH, --NH-lower alkylene-arylthio, --NH-lower alkylene-halogen, ##STR2## in which ##STR3## is dilower alkylamino, cycloalkylamino, morpholino, ##STR4## in which R.sub.9 is hydrogen, lower alkyl or aryl, R.sub.10 is hydrogen, lower alkyl, hydroxy-lower alkyl, hydroxy-lower alkoxy-lower alkyl or di(aryl)-lower alkyl, m is an integer from 4 to 6, n is 2 or 3, R.sub.1 is alkyl or aryl-lower alkyl, R.sub.2 and R.sub.3 are each lower alkyl, or together form tetramethylene, and R.sub.4 is hydrogen, lower alkyl or aryl, in which aryl is phenyl which is optionally substituted with a group selected from the group consisting of 1-3 halogen, nitro, lower alkyl and lower alkoxy, or a pharmaceutically acceptable salt thereof, inhibits blood platelet aggregation, has vasodilating activity and inhibits lipoperoxide generation.

1-Substituted alkyl-2-oxo-hexahydroquinoxaline derivatives of the formula ##STR1## wherein A is lower alkylene; R.sub.1 is selected from the group consisting of alkyl, phenyl-lower alkyl, and substituted phenyl-lower alkyl; and R is selected from the group consisting of 1-methyltetrazole-5-yl-thio, 1-imidazolyl, morpholino, ##STR2## in which R.sub.5 is hydrogen, lower alkyl or aryl, R.sub.6 is hydrogen, lower alkyl, hydroxy-lower alkyl, aryl, aryl-lower alkanoyl, arylcarbonyl, arylsulfonyl or thienyl-lower alkanoyl, Ar is phenyl or phenyl substituted with C.sub.1-3 alkyl, halogen, nitro, or lower alkoxy, A and R.sub.1 are as defined above, R.sub.2 and R.sub.3 are each lower alkyl or together form tetramethylene, m is an integer from 4-6, and n is 2 or 3; and pharmaceutically acceptable salts thereof. The compounds are useful as agents for platelet aggregation inhibition, vasodilation and anti-lipoperoxide generation.

1-Substituted alkyl-2-oxo-hexahydroquinoxaline derivatives

1-Substituted alkyl-2-oxo-hexahydroquinoxaline derivatives of the formula ##STR1## wherein A is lower alkylene; R.sub.1 is selected from the group consisting of alkyl, phenyl-lower alkyl, and substituted phenyl-lower alkyl; and R is selected from the group consisting of hydroxyl, halogen, lower alkanocyloxy, R.sub.4 -carbamoyloxy and arylthio, in which R.sub.4 is lower alkyl or aryl; and pharmaceutically acceptable salts thereof. The compounds are useful as agents for platelet aggregation inhibition, vasodilation and anti-lipoperoxide generation.

1-substituted alkyl-2-oxo-hexahydroquinoxaline derivatives

1-Substituted alkyl-1,2-dihydro-2-pyrazinone derivatives of the formula ##STR1## wherein A is lower alkylene; R.sub.1 is selected from the group consisting of alkyl, phenyl-lower alkyl, and substituted phenyl-lower alkyl; R.sub.2 and R.sub.3 are each lower alkyl; and R is selected from the group consisting of hydroxyl, halogen, lower alkanoyloxy, R.sub.4 -carbamoyloxy and arylthio, in which R.sub.4 is lower alkyl or aryl; and pharmaceutically acceptable salts thereof. The compounds are useful as agents for platelet aggregation inhibition, vasodilation and anti-lipoperoxide generation.

1-Substituted alkyl-1,2-dihydro-2-pyrazinone derivatives

A compound of the formula ##STR1## wherein R.sup.1 is hydrogen or lower alkyl, R.sup.2 is hydrogen, lower alkoxy or halogen, and A is lower alkylene, or a pharmacologically acceptable salt thereof, has sympatholytic .alpha.-receptor blocking activity and is useful for the treatment of hypertension.

1-Substituted alkyl-2-oxo-1,2-dihydroquinoxaline derivatives

A compound of the formula ##STR1## wherein Z is N or NH,  is a single or double bond, R.sub.1 is hydrogen, C.sub.1-20 alkyl or optionally substituted phenyl, A is lower alkylene, R is carboxyl, lower alkoxycarbonyl, ##STR2## or 1-cycloalkyl-tetrazole-5-yl, R.sub.2 is lower alkyl, hydroxy-lower alkyl or optionally substituted phenyl-lower alkyl, R.sub.3 is lower alkyl or cycloalkyl, or R.sub.2 and R.sub.3 together constitute ##STR3## and R.sub.5 and R.sub.6 are hydrogen or optionally substituted phenyl, or a pharmacologically acceptable salt thereof, has platelet aggregation inhibitory activity and/or cyclic AMP/phosphodiesterase inhibitory activity.

6-substituted alkoxy-2-oxo-1,2-dihydroquinoxaline derivatives

1-Substituted alkyl-1,2-dihydro-2-pyrazinone derivatives of the formula ##STR1## wherein A is lower alkyl; R.sub.1 is selected from the group consisting of alkyl, phenyl-lower alkyl, and substituted phenyl-lower alkyl; R.sub.2 and R.sub.3 are each lower alkyl, or together form tetramethylene and R is selected from the group consisting of hydroxyl, hologen, lower alkanoyloxy R.sub.4 -carbamoyloxy, arylthio, 1-methyltetrazole-5-yl-thio, 1-imidazole, morpholino, ##STR2## in which R.sub.4 is lower alkyl or aryl, R.sub.5 is lhydrogen, lower alkyl or aryl, R.sub.6 is hydrogen, lower alkyl, hydroxy-lower alkyl, aryl, aryl-lower alkanoyl, arylcarbonyl, arylsulfonyl or thienyl-lower alkanoyl, Ar is phenyl or phenyl substituted with C.sub.1-3 alkyl, halogen, nitro, or lower alkoxy, A, R.sub.1, R.sub.2 and R.sub.3 are as defined above, m is an integer from 4-6, and n is 2 or 3; and pharmaceutically acceptable salts thereof. The compounds are useful as agents for platelet aggregation inhibition, vasodilation and anti-lipoperoxide generation.

1-substituted alkyl-1,2-dihydro-2-pyrazinone derivatives

A method for inhibiting blood platelet aggregation in humans, and promoting vasodilation in humans, by administering to a human in need of the same an effective amount of 2-hydroxy-3-isopropyl-5,6-dimethylpyrazine or a hydrate or a pharmaceutically acceptable non-toxic salt thereof. Administration can be orally in an amount of about 0.02-12 mg/kg body weight per day, or parenterally in an amount of about 0.01-6 mg/kg of body weight per day.

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Shizuoka, Japan

Eiichi Hayashi