Yamanouchi Pharmaceutical Company Ltd.

Isao Souzu

Yasuo Isomura

Noriki Ito

Kazuo Kubo

Hiroshige Homma

Masuo Murakami

Yukiyasu Murakami

Ichiro Isaka

Akio Koda

Teruaki Ozasa

Teruya Kashiwagi

Khozi Nakano

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.

The penicillin derivatives represented by the formula ##SPC1## Wherein ring A represents a 5- or 6-membered single or fused ring which may contain one or more nitrogen atoms, an oxygen atom, or a sulfur atom; R.sup.1, R.sup.2, and R.sup.3, which may be the same or different, each represents a hydrogen atom, a hydroxy group, a lower alkyl group, a nitro group, a halogen atom, or an oxo group; and B represents a p-hydroxyphenyl group or a 1,4-cyclohexadien -1-yl group, and their nontoxic pharmaceutically acceptable salts. The compounds are antibiotics having excellent antibacterial activity in particular with respect to the Pseudomonas genus.

Growing community of inventors

Urawa, Japan

Isao Souzu