Yamanouchi Pharmaceutical Company Ltd.

Hiroshige Homma

Yasuo Isomura

Kazuo Kubo

Noriki Ito

Isao Souzu

Masuo Murakami

Shuichi Sakamoto

Novel 3,5-di-tert-butyl-4-hydroxyphenyl-substituted heterocyclic compounds shown by the formula ##STR1## wherein .circle.Het -- represents a specific heterocyclic group and the salts thereof. The compounds have an anti-inflammatory, an anti-pyretic, an analgesic, an anti-arthritic, and an immunoregulatory activity. Hence, they are particularly useful as an antirheumatics.

3,5-di-tert-butyl-4-hydroxyphenyl-substituted heterocyclic compounds

Nitrogen containing heterocyclic compounds shown by the formula ##STR1## wherein Y represents an oxygen atom, a sulfur atom, or a group shown by ##STR2## (wherein m is 1 or 2); n represents 0 or 1; R.sub.1 and R.sub.4, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, or a lower alkenyl group; R.sub.2 and R.sub.3, which may be the same or different, each represents a hydrogen atom, a hydroxyl groups, a lower alkanoyloxy group, a lower alkyl group or a lower alkenyl group; said R.sub.2 and R.sub.3 may further form together a double bond; R.sub.5 and R.sub.6, which may be the same or different, each represents by hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, an amino group, a lower alkoxy group, a mono or di lower alkylamino group, or a lower alkyl group; said R.sub.5 and R.sub.6 may further form together a lower alkylenedioxy group; and R.sub.7 represents a hydrogen atom, a halogen atom, a lower alkanoyl group, a phenyl group, a phenyl lower alkyl group, a lower alkyl group, a hydroxy lower alkyl group, a di lower alkylamino lower alkyl group, a pyrrolidino lower alkyl group, a piperidino lower alkyl group, a morpholino lower alkyl group, or a 4-lower alkylpiperazino lower alkyl group;

Thiazolo[3,2-6]isoquinolines, compositions and use thereof

Novel nitrogen-containing heterocyclic compounds shown by the formula ##STR1## wherein Y represents an oxygen atom, a sulfur atom, or a group shown by ##STR2## (wherein m is 1 or 2); n represents 0 or 1; R.sub.1 and R.sub.4, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, or a lower alkenyl group; R.sub.2 and R.sub.3, which may be the same or different, each represents a hydrogen atom, a hydroxyl group, a lower alkanoyloxy group, a lower alkyl group or a lower alkenyl group; said R.sub.2 and R.sub.3 may further form together a double bond; R.sub.5 and R.sub.6, which may be the same or different, each represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, an amino group, a lower alkoxy group, a mono or di lower alkylamino group, or a lower alkyl group; said R.sub.5 and R.sub.6 may further form together a lower alkylenedioxy group; and R.sub.7 represents a hydrogen atom, a halogen atom, a lower alkanoyl group, a phenyl group, a phenyl lower alkyl group, a lower alkyl group, a hydroxy lower alkyl group, a di lower alkylamino lower alkyl group, a pyrrolidino lower alkyl group, a piperidino lower alkyl group, a morpholino lower alkyl group, or a 4-lower alkylpiperazino lower alkyl group;

1,3-Oxazino(3,2-b)isoquinoline-6-ones

Novel nitrogen-containing heterocyclic compounds shown by the formula ##STR1## wherein one of R.sub.1 and R.sub.2 represents a lower alkyl group, a phenyl group, a halophenyl group, or a lower alkoxyphenyl group and the other of them represents a hydrogen atom, a lower alkyl group, or a phenyl lower alkyl group; said R.sub.1 and R.sub.2 may combine with each other to form a trimethylene group or a tetramethylene group; R.sub.3 represents a hydrogen atom, a lower alkyl group, a phenyl group, or a phenyl lower alkyl group; X represents an oxygen atom, a sulfur atom, an imino group, or a group shown by ##STR2## (wherein m represents 1 or 2 and R.sub.4 represents a lower alkyl group, a hydroxy lower alkyl group, a cycloalkyl group or a phenyl lower alkyl group); and Y represents an ethylene group which may be substituted by lower alkyl group, a trimethylene group, a tetramethylene group, a vinylene group which may be substituted by a lower alkyl group, or ##STR3## (wherein R.sub.5 represents a hydrogen atom, a lower alkyl group, a trifluoromethyl group, or a phenyl group); said X is the group shown by ##STR4## when one of said R.sub.1 and R.sub.2 is a lower alkyl group and the other is a hydrogen atom, and said Y is an ethylene group, and the pharmacologically acceptable non-toxic salts thereof. The compounds described above are strong analgesic anti-inflammatory agents.

Nitrogen-containing heterocyclic ring derivatives and analgesic and

Novel nitrogen-containing heterocyclic compounds shown by the formula ##STR1## wherein one of R.sub.1 and R.sub.2 represents a lower alkyl group, a phenyl group, a halophenyl group, or a lower alkoxyphenyl group and the other of them represents a hydrogen atom, a lower alkyl group, or a phenyl lower alkyl group; said R.sub.1 and R.sub.2 may combine with each other to form a trimethylene group or a tetramethylene group; R.sub.3 represents a hydrogen atom, a lower alkyl group, a phenyl group, or a phenyl lower alkyl group; X represents an oxygen atom, a sulfur atom, an imino group, or a group shown by ##STR2## wherein m represents 1 or 2 and R.sub.4 represents a lower alkyl group, a hydroxy lower alkyl group, a cycloalkyl group or a phenyl lower alkyl group; and Y represents an ethylene group which may be substituted by a lower alkyl group, a trimethylene group, a tetramethylene group, a vinylene group which may be substituted by lower alkyl group, or ##STR3## wherein R.sub.5 represents a hydrogen atom, a lower alkyl group, a trifluoromethyl group, or a phenyl group; said X is the group shown by ##STR4## when one of said R.sub.1 and R.sub.2 is a lower alkyl group and the other is a hydrogen atom, and said Y is an ethylene group, and the pharmacologically acceptable non-toxic salts thereof. The compound described above are strong analgesic anti-inflammatory agents.

Nitrogen-containing heterocyclic ring derivatives

Novel nitrogen-containing heterocyclic compounds shown by the formula ##STR1## wherein one of R.sub.1 and R.sub.2 represents a lower alkyl group, a phenyl group, a halophenyl group, or a lower alkoxyphenyl group and the other of them represents a hydrogen atom, a lower alkyl group, or a phenyl lower alkyl group; said R.sub.1 and R.sub.2 may combine with each other to form a trimethylene group or a tetramethylene group; R.sub.3 represents a hydrogen atom, a lower alkyl group, a phenyl group, or a phenyl lower alkyl group; X represents an oxygen atom, a sulfur atom, an imino group, or a group shown by ##STR2## wherein m represents 1 or 2 and R.sub.4 represents a lower alkyl group, a hydroxy lower alkyl group, a cycloalkyl group or a phenyl lower alkyl group; and Y represents an ethylene group which may be substituted by lower alkyl group, a trimethylene group, a tetramethylene group, a vinylene group which may be substituted by a lower alkyl group, or ##STR3## wherein R.sub.5 represents a hydrogen atom, a lower alkyl group, a trifluoromethyl group, or a phenyl group; said X is the group shown by ##STR4## when one of said R.sub.1 and R.sub.2 is a lower alkyl group and the other is a hydrogen atom, and said Y is an ethylene group, 1/7 and the pharmacologically acceptable non-toxic salts thereof. The compounds described above are strong analgesic anti-inflammatory agents.

Nitrogen-containing heterocyclic compounds

Novel 1-oxo-1,2-dihydroisoquinoline compounds of the formula ##STR1## wherein R.sub.1 represents a lower alkyl group or a phenyl lower alkyl group; R.sub.2 represents a lower alkyl group; R.sub.3 represents a hydrogen atom, a lower alkanoyl group, a lower alkyl group or a hydroxy lower alkyl group; and n is 0, 1 or 2 and the pharmacologically acceptable non-toxic salts thereof. The compounds of this invention are strong analgesic anti-inflammatory agents.

1-Oxo-1,2-dihydroisoquinoline derivatives

Novel nitrogen-containing heterocyclic compounds shown by the formula ##STR1## wherein one of R.sub.1 and R.sub.2 represents a lower alkyl group, a phenyl group, a halophenyl group, or a lower alkoxyphenyl group and the other of them represents a hydrogen atom, a lower alkyl group, or a phenyl lower alkyl group; said R.sub.1 and R.sub.2 may combine with each other to form a trimethylene group or a tetramethylene group; R.sub.3 represents a hydrogen atom, a lower alkyl group, a phenyl group, or a phenyl lower alkyl group; X represents an oxygen atom, a sulfur atom, an imino group, or a group shown by ##STR2## wherein m represents 1 or 2 and R.sub.4 represents a lower alkyl group, a hydroxy lower alkyl group, a cycloalkyl group or a phenyl lower alkyl group; and Y represents an ethylene group which may be substituted by lower alkyl group, a trimethylene group, a tetramethylene group, a vinylene group which may be substituted by a lower alkyl group, or ##STR3## wherein R.sub.5 represents a hydrogen atom, a lower alkyl group, a trifluoromethyl group, or a phenyl group; said X is the group shown by ##STR4##

Novel fused derivatives of 2-pyridones

Novel nitrogen-containing heterocyclic compounds shown by the formula ##STR1## wherein Y represents an oxygen atom, a sulfur atom, or a group shown by ##STR2## (wherein m is 1 or 2); n represents 0 or 1; R.sub.1 and R.sub.4, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, or a lower alkenyl group; R.sub.2 and R.sub.3, which may be the same or different, each represents a hydrogen atom, a hydroxyl group, a lower alkanoyloxy group, a lower alkyl group or a lower alkenyl group; said R.sub.2 and R.sub.3 may further form together a double bond; R.sub.5 and R.sub.6, which may be the same or different, each represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, an amino group, a lower alkoxy group, a mono or di lower alkylamino group, or a lower alkyl group; said R.sub.5 and R.sub.6 may further form together a lower alkylenedioxy group; and R.sub.7 represents a hydrogen atom, a halogen atom, a lower alkanoyl group, a phenyl group, a phenyl lower alkyl group, a lower alkyl group, a hydroxy lower alkyl group, a di lower alkylamino lower alkyl group, a pyrrolidino lower alkyl group, a piperidino lower alkyl group, a morpholino lower alkyl group, or a 4-lower alkylpiperazino lower alkyl group; (1) when said R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are hydrogen atom and n is 0, said Y is a group shown by ##STR3## and (2) when said R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.7 are hydrogen atom, at least one of said R.sub.5 and R.sub.6 is the aforesaid group other than hydrogen atom, and n is 0, said Y is oxygen atom or a group shown by ##STR4## and the pharmacologically acceptable non-toxic salts thereof. The compounds are strong analgesic anti-inflammatory agents.

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Omiya, Japan

Hiroshige Homma