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AssigneeOno Pharmaceutical Co., Ltd.
InventorsSetsuro Fujii, Tsuyoshi Watanabe, Masashi Shiota, Itsuo Okumoto, Naohiro Kayama
Estimating the term…
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 represented by the formula [I] ##STR14## wherein Z represents a SO.sub.2 group or Z'--CO group wherein Z' represents a single bond or a methylene, ethylene or vinylene group, and R.sup.1 and R.sup.2, which may be the same or different, each represent a hydrogen atom or a lower alkyl group, and the acid addition salts thereof.
A compound as claimed in any preceding claim, wherein said acid addition salt is a salt of hydrochloric acid, sulfuric acid, phosphoric acid, hydrobromic acid, nitric acid, acetic acid, lactic acid, oxalic acid, maleic acid, fumaric acid, succinic acid, tartaric acid, malic acid, citric acid, benzenesulfonic acid, toluenesulfonic acid or methanesulfonic acid.
Dependencies are inferred from the claim text.
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Amines: amidines , e.g. guanidine , isourea , isothiourea
Amides, e.g. hydroxamic acids: having aromatic rings, e.g. colchicine, atenolol, progabide
Amides, e.g. hydroxamic acids: sulfonamides
Having an aromatic ring attached to a carboxyl group: having an amino or nitro group
Term ended 22 Feb 2000 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
1. Field of the Invention
This invention relates to novel guanidinobenzoic acid derivatives and process for their preparation.
2. Description of the Prior Art
2.7 g of p-guanidinobenzoic acid was heated with 25 ml of thionylchloride at 70.degree.-75.degree. C. for 30 minutes with stirring. To the reaction mixture was added petroleum ether to precipitate crystals of p-guanidinobenzoyl chloride hydrochloride, which were filtered and washed with petroleum ether.
The crystals thus obtained were added to a solution of 3.0 g of N,N-dimethyl-p-hydroxybenzenesulfonamide in 20 ml of pyridine at 0.degree. C. and the mixture was stirred for 2 hours. To the reaction mixture was added a saturated aqueous solution of sodium bicarbonate and the resulting crystals were filtered out, washed with water and acetone, and dried. The crystals thus obtained were suspended in methanol and dissolved by adding of methanesulfonic acid, the mixture was filtered and diethyl ether was added to the filtrate. The resulting crystals were filtered out, dried and recrystallized from dimethylformamide to obtain 2.75 g of the title compound.
Melting point: 211.degree.-213.degree. C.