Dihydrophenazinecarboxylic acid derivatives
AssigneeNippon Chemiphar Co., Ltd.
InventorsToshihiro Takahashi, Yutaka Nomura, Haruo Seto, Kazuo Shin-ya
Life of this patent
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Abstract
Dihydrophenazinecarboxylic acid derivatives of the formula (I) wherein R.sup.1 represents hydrogen, linear or branched alkyl, etc., each of R.sup.2 and R.sup.3 represents hydrogen, 3-methyl-2-butenyl, etc., and each of R.sup.4 and R.sup.5 represents hydrogen, alkyl, alkenyl, aralkyl, aryl, hydroxyl, alkoxy, aryloxy, aralkyloxy, halogen, nitro, cyano, alkylsulfonyl, arylsulfonyl, alkylcarbonyl, arylcarbonyl, etc., provided that there is no case that both of R.sup.4 and R.sup.5 are hydrogen. The dihydrophenazinecarboxylic acid derivatives are excellent in the inhibition of glutamic acid toxicity. ##STR1##
Claims6
A dihydrophenazinecarboxylic acid derivative having the formula (I):
- in which ##STR15## in which R.sup.1 represents a hydrogen atom, a linear or branched chain alkyl group, an aralkyl group or an aryl group;
- each of R.sup.2 and R.sup.3 is the same or different from each other and represents a hydrogen atom, an alkenyl group having 2 to 5 carbon atoms, an alkyl group, an aralkyl group, an aryl group, or a group represented by the formula (II):
- ##STR16## wherein each of R.sup.6 and R.sup.7 is the same or different from each other and represents a hydrogen atom, a linear or branched chain alkyl group, an aralkyl group or an aryl group, or R.sup.6 and R.sup.7 are combined together to form a nitrogen atom-containing 5- to 7-membered ring in conjunction with the adjacent nitrogen atom, and m is 2, 3 or 4;
- each of R.sup.4 and R.sup.5 is the same or different from each other and represents a hydrogen atom, a linear or branched chain alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group, a hydroxyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, a halogen atom, a nitro group, a cyano group, an alkylsulfonyl group, an arylsulfonyl group, an alkylcarbonyl group, an arylcarbonyl group, an aralkylcarbonyl group, a halo-alkyl group, a halo-alkoxy group, or a group represented by --NR.sup.8 R.sup.9 or --SO.sub.2 NR.sup.10 R.sup.11 wherein each of R.sup.8 and R.sup.9 is the same or different from each other and represents a hydrogen atom, a linear or branched chain alkyl group, an aralkyl group or an aryl group, and each R.sup.10 and R.sup.11 is the same or different from each other and represents a hydrogen atom, a linear or branched chain alkyl group, an aralkyl group or an aryl group;
- provided that at least one of R.sup.4 and R.sup.5 is a group selected from the group consisting of a nitro group, a cyano group, an alkylsulfonyl group, an arylsulfonyl group, an alkylcarbonyl group, an arylcarbonyl group, an aralkylcarbonyl group, a trifluoromethyl group, a trifluoromethoxy group, and a group represented by --SO.sub.2 NR.sup.10 R.sup.11 wherein each of R.sup.10 and R.sup.11 is the same or different from each other and represents a hydrogen atom, a linear or branched chain alkyl group, an aralkyl group or an aryl group.
A method for treating a patient suffering from glutamic acid toxicity which comprises administering to the patient an effective amount of a dihydrophenazinecarboxylic acid derivative of the following formula (V):
- ##STR17## in which R.sup.41 represents a hydrogen atom, a linear or branched chain alkyl group, an aralkyl group or an aryl group;
- each of R.sup.42 and R.sup.43 is the same or different from each other and represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, an alkenyl group having 2 to 5 carbon atoms, or a group represented by the formula (VI):
- ##STR18## wherein each of R.sup.46 and R.sup.47 is the same or different from each other and represents a hydrogen atom, a linear or branched chain alkyl group, an aralkyl group or an aryl group, or R.sup.46 and R.sup.47 are combined together to form a nitrogen atom-containing 5- to 7-membered ring in conjunction with the adjacent nitrogen atom, and p is 2, 3 or 4;
- each of R.sup.44 and R.sup.45 is the same or different from each other and represents a hydrogen atom, a linear or branched chain alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group, a hydroxyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, a halogen atom, a nitro group, a cyano group, an alkylsulfonyl group, an arylsulfonyl group, an alkylcarbonyl group, an arylcarbonyl group, an aralkylcarbonyl group, a halo-alkyl group, a halo-alkoxy group, a carboxyl group, an alkoxycarbonyl group, an aralkyloxycarbonyl group, a formyl group, or a group represented by --NR.sup.48 R.sup.49 or --SO.sub.2 NR.sup.50 R.sup.51 wherein each of R.sup.48 and R.sup.49 is the same or different from each other and represents a hydrogen atom, a linear or branched chain alkyl group, an aralkyl group or an aryl group, and each of R.sup.50 and R.sup.51 is the same or different from each other and represents a hydrogen atom, a linear or branched chain alkyl group, an aralkyl group or an aryl group.
A dihydrophenazinecarboxylic acid derivative having the formula (III):
- ##STR19## in which R.sup.21 represents a hydrogen atom, a linear or branched chain alkyl group, an aralkyl group or an aryl group;
- each of R.sup.22 and R.sup.23 is the same or different from each other and represents a hydrogen atom, an alkenyl group having 2 to 5 carbon atoms, an alkyl group, an aralkyl group, an aryl group, or a group represented by the formula (IV):
- ##STR20## wherein each of R.sup.26 and R.sup.27 is the same or different from each other and represents a hydrogen atom, a linear or branched chain alkyl group, an aralkyl group or an aryl group, or R.sup.26 and R.sup.27 are combined together to form a nitrogen atom-containing 5- to 7-membered ring in conjunction with the adjacent nitrogen atom, and n is 2, 3 or 4;
- each of R.sup.20, R.sup.24 and R.sup.25 is the same or different from each other and represents a hydrogen atom, a linear or branched chain alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group, a hydroxyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, a halogen atom, a nitro group, a cyano group, an alkylsulfonyl group, an arylsulfonyl group, a halo-alkyl group, a halo-alkoxy group, or a group represented by --NR.sup.28 R.sup.29 or --SO.sub.2 NR.sup.30 R.sup.31 wherein each of R.sup.28 and R.sup.29 is the same or different from each other and represents a hydrogen atom, a linear or branched chain alkyl group, an aralkyl group or an aryl group, and each of R.sup.30 and R.sup.31 is the same or different from each other and represents a hydrogen atom, a linear or branched chain alkyl group, an aralkyl group or an aryl group.
Dependencies are inferred from the claim text.