Ono Pharmaceutical Co., Ltd.

Sumitomo Chemical Company, Limited

Itsuo Okumoto

Yasunobu Miyamoto

Susumu Ohtsuka

Hiroaki Hibino

Tsuyoshi Watanabe

Naohiro Kayama

Masashi Shiota

Setsuro Fujii

Tomoyasu Yoshida

Yoshiaki Uegai

A process for producing a dicarboxylic acid compound represented by the formula (4): wherein Rand Rare the same or different and each represents lower alkyl and the wavy line indicates that this compound is the E- or Z-isomer or a mixture of them, characterized by reacting a compound represented by the formula (2): wherein R, Rand the wavy line have the same meanings as the above, and one of Xand Xrepresents hydrogen and the other represents halogen, with nitrophenol represented by the formula (3): in the presence of a base; a process for producing a nitrochromone compound represented by the formula (5): wherein Rhas the same meaning as the above, characterized by reacting the dicarboxylic acid compound or carboxylic acid thereof with an acid; a process for producing an aminochromone compound which comprises reducing the nitrochromone compound; and a process for producing an amidochromone compound which comprises acylating the aminochromone compound are provided.

Process for producing chromone compound

There is provided an industrially advantageous process for producing a 1-chloro-4-arylbutane represented by the general formula (2):wherein R represents hydrogen, lower alkyl, or lower alkoxy, characterized by reacting 1-bromo-3-chloropropane with a compound represented by the general formula (1):wherein R is as defined above; and X represents chlorine, bromine, or iodine, in a solvent.

Process for producing 1-chloro-4-arylbutane

The guanidinobenzoic acid derivatives of the general formula: ##STR1## wherein Z represents a carbon-carbon covalent bond, or a methylene, ethylene or vinylene group, R.sup.1 represents a hydrogen atom, or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, R.sup.2 represents a straight- or branched-chain alkyl group containing from 4 to 10 carbon atoms, or a cycloalkyl or cycloalkenyl or straight- or branched-chain alkenyl group containing from 3 to 8 carbon atoms, or a phenyl or benzyl group, or NR.sup.1 R.sup.2 represents a 4- to 8-membered heterocyclic ring, and acid addition salts thereof, have anti-plasmin and anti-trypsin activities.

Guanidinobenzoic acid derivatives

Guanidinobenzoic acid derivatives represented by the general formula [I] ##STR1## wherein R.sup.1, R.sup.2 and Z are as defined hereinafter, having antiplasmin and anti-trypsin activities and process for their preparation as well as a pharmaceutical composition and a method of inhibiting the activity of plasmin and trypsin is disclosed.

Guanidinobenzoic acid derivatives and process for their preparation

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Sakai-gun, Japan

Itsuo Okumoto