Taiho Pharmaceutical Company Limited

Takaji Honna

Hidekazu Miyake

Makoto Kajitani

Hajime Fujimura

Takahiro Yabuuchi

Katsuo Takikawa

Masakatu Hisaki

Yasuzo Hiramatsu

Kazuo Ogawa

Mitsugi Yasumoto

Motoaki Tanaka

Syozo Yamada

Junji Yamamoto

Nobuo Kasahara

Etsuo Hasegawa

Akihiro Kawaguchi

Katsuo Toide

Shozo Yamada

Ichiro Yamawaki

Tomio Yamazaki

Naohiko Ono

Hajime Fujmura

Sekio Nagayama

Yasuzo Hiramatu

The present invention provides carbamoyl-2 -pyrrolidinone compounds useful as medicaments for improving cerebral functions and activating cerebral metabolism or protecting against anoxic brain damage.

Carbamoyl-2-pyrrolidinone compounds

Disclosed are a compound of the formula ##STR1## wherein R.sub.1 is lower alkyl, A is a group of the formula ##STR2## (in which R.sub.3 is hydrogen or lower alkyl) or methylene, and R.sub.2 is hydrogen or a group of the formula --(CH.sub.2).sub.n COOH (in which n is an integer of 1 to 6) or a salt of the derivative, and preparation thereof. The compounds have an excellent aldose reductase inhibitory action.

Rhodanine derivatives and process for preparing the same

A piperazine derivative represented by the formula (I) below ##STR1## wherein R.sup.1 is lower alkyl or phenyl, R.sup.2 is hydrogen or lower alkyl, n is an integer of 2 to 10, is useful as an effective component of anti-inflammatory agent or antiallergic agent.

Derivative of piperazine having anti-allergic and anti-inflammatory

An analgesic compositon containing as active ingredient an allophanoylpiperazine compound represented by the general formula ##STR1## wherein R.sup.1 represents a lower alkyl group or phenyl group; R.sup.2 and R.sup.3 each represents a hydrogen atom or a lower alkyl group; and R.sup.4 represents a phenyl group or a substituted phenyl group having as substituent a halogen atom or methyl, trifluoromethyl, hydroxyl, methoxy, methylenedioxy, nitro, or carboxyl group; pyridyl group, pyrimidyl group, thiazolyl group, benzyl group, cinnamyl group, cyclohexyl group, a lower alkyl group, a substituted lower alkyl group having chlorine atom or hydroxyl group as substituent; or a lower alkenyl group.

Allophanoylpiperazine compound and analgesic composition containing same

An analgesic composition containing as active ingredient a piperazine derivative represented by the general formula (1) ##STR1## wherein R.sub.1 represents a cyclopropylmethyl group, an isopropyl group or an allyl group and R.sub.2 represents a phenyl group having as substituent a halogen atom or a trifluoromethyl group.

Piperazine derivative and analgesic composition containing the same

An analgesic, anti-inflammatory or anti-pyretic composition containing 1,1,3,5-substituted biuret compound of the formula, ##STR1## wherein R.sup.1 is a lower alkyl group or a phenyl group; R.sup.2 is a lower alkyl group, a phenyl group or a substituted phenyl group having chlorine atom(s), methyl group(s) or methoxy group(s) as the substituent(s), further R.sup.1 and R.sup.2 may form a single ring containing one or two hetero atoms including the adjacent nitrogen atom; R.sup.3 is a hydrogen atom, a lower alkyl group or a phenyl group; R.sup.4 is a phenyl group, a substituted phenyl group having halogen atom(s), trifluoromethyl group(s), methyl group(s), methoxy group(s), dimethyl-amino group(s), nitro group(s), hydroxyl group(s), acetyl group(s), or methylthio group(s) as the substituent(s), a benzyl group, a cyclohexyl group or a lower alkyl group, as the active ingredient.

Pharmaceutical composition containing 1,1,3,5-substituted biuret compound

An analgesic, anti-inflammatory or anti-pyretic composition containing 1,3,5-substituted biuret compound of the formula, ##STR1## wherein R.sup.1 is a hydrogen atom, a lower alkyl group, a substituted lower alkyl group having chlorine atom(s), cyano group(s), dimethylamino group(s), hydroxy group(s), methoxy group(s) or carboxy group(s) as the substituent(s), a lower alkenyl group, a hydroxy group, a methoxy group, an acetyl group or a phenyl group; R.sup.2 is a hydrogen atom, a lower alkyl group or a phenyl group; R.sup.3 is a phenyl group, a substituted phenyl group having halogen atom(s), trifluoromethyl group(s), methyl group(s), methoxy group(s), methylenedioxy group(s), hydroxy group(s), dimethylamino group(s), carboxy group(s) or carboxymethyl group(s) as the substituent(s), a benzyl group, a pyridyl group, a substituted pyridyl group having methyl group(s) as the substituent(s), a pyridylmethyl group, pyrimidinyl group, a thiazolyl group or a thienyl group, as the active ingredient.

Pharmaceutical composition containing 1,3,5-substituted biuret compound

A novel 1,1,3,5-substituted biuret compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are respectively the same or different, and each are alkyl groups having 1 to 4 carbon atoms; R.sup.3 is a cyclohexyl group or a phenyl group which may be unsubstituted or may have at least one substituent selected from the group consisting of chlorine, bromine, fluorine, methyl, trifluoromethyl, dimethylamino, methoxy, methylthio, nitro and acetyl. The novel 1,1,3,5-substituted biuret compounds are useful as an analgesic, anti-inflammatory and/or anti-pyretic agent.

Novel 1,1,3,5-substituted biuret compound and a pharmaceutical

An analgesic, anti-inflammatory or anti-pyretic composition containing 1,1,3,5-substituted biuret compound of the formula, ##STR1## wherein R.sup.1 is a lower alkyl group or a phenyl group; R.sup.2 is a lower alkyl group, a phenyl group or a substituted phenyl group having chlorine atom(s), methyl group(s) or methoxy group(s) as the substituent(s), further R.sup.1 and R.sup.2 may form a single ring containing one or two hetero atoms including the adjacent nitrogen atom; R.sup.3 is a hydrogen atom, a lower alkyl group or a phenyl group; R.sup.4 is a phenyl group, a substituted phenyl group having halogen atom(s), trifluoromethyl group(s), methyl group(s), methoxy group(s), dimethylamino group(s), nitro group(s), hydroxyl group(s), acetyl group(s) or methylthio group(s) as the substituent(s), a benzyl group, a cyclohexyl group or a lower alkyl group, as the active ingredient.

Pharmaceutical composition and methods of use containing

Novel derivatives of glyoxal-2-oxim represented by the chemical formula ##STR1## wherein R is hydrogen or a lower alkyl or phenyl group, are provided in accordance with the present invention. These derivatives are prepared by reacting the corresponding isoxazole-5-carbaldehyde with nitromethane in the presence of a metal alkoxide, or the corresponding 5-acetylisoxazole with a nitrate. They have anti-inflammatory and/or analgesic activities.

Processes for the preparation of glyoxal-2-oxims

Novel derivatives of glyoxal-2-oxim represented by the chemical formula ##STR1## wherein R is hydrogen or a lower alkyl or phenyl group, are provided in accordance with the present invention. These derivatives are prepared by reacting the corresponding isoxazole-5-carbaldehyde with nitromethane in the presence of a metal alkoxide, or the corresponding 5-acetylisoxazole with a nitrite. They have anti-inflammatory and/or analgesic activities.

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Tokushima, Japan

Takaji Honna