Urocanic acid derivatives

Details Urocanic acid derivatives Urocanic acid derivatives

2000-08-03

2001-10-30

Shah, Mukund J. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S253010, C514S254050, C514S259500, C514S370000, C514S397000, C514S399000, C514S400000, C544S284000, C544S286000, C544S360000, C544S370000, C548S190000, C548S312100, C548S314700, C548S335100, C548S335500, C548S336100, C548S341500, C549S059000, C549S065000, C549S066000, C549S068000

Reexamination Certificate

active

06310067

ABSTRACT:

TECHNICAL FIELD
The present invention relates to novel urocanic acid derivatives, a method of preparation thereof, and antiallergic medicaments containing thereof.
BACKGROUND ART
Urocanic acid, first discovered in dog urine in 1874 by Jaffe and later confirmed to occur also in human urine and epidermis, is a compound of the following formula (II).
Urocanic acid is thought to act as an ultraviolet absorbent and thus serve to protect the slin. Urocanic acid is also reported to have a suppressive effect on delayed allergy [The Allergy In Practice, 15(9):1995]. In addition, urocanic acid bound by ascorbic acid (Japanese Laid-Open Patent Application No. S56-161314) and thiol urocanic acid (Japanese Laid-Open Patent Application No. S60-16907) are known to have a skin brightening effect.
With its antiallergic effect, however, urocanic acid has its own shortcomings that it is only poorly soluble in water and organic solvents, thereby maling itself hard to be formulated into pharmaceutical preparations, and that its suppressive effect on delayed allergy is by no means satisfactory.
Upon the above background, the present inventors investigated to obtain urocanic acid derivatives that have sufficient solubility in water or organic solvents and having potent antiallergic effects. As a result, certain urocanic acid derivatives were found to have potent antiallergic effects and, at the same time, sufficient solubility in water or organic solvents. The present inventors completed the present invention through further investigation based on this finding.
The present invention provides urocanic acid derivatives having sufficient solubility in water or organic solvents and having potent antiallergic effects.
DISCLOSURE OF INVENTION
Thus, the present invention relates to (1) a urocanic acid derivative represented by the following formula (I) or a phannacologically acceptable salt thereof (hereinafter referred to as the “present compound”):
wherein R
2
denotes hydrogen or lower alkyl, R
3
denotes nitro, amino, cyano or COOR
2
,
wherein R
2
included in said COOR
2
is as defined above, and Q denotes carbon or nitrogen,
(2) a method for preparation thereof, and
(3) an antiallergic medicament comprised thereof.
Examples of the present compound include the following specific compounds and their pharmacologically acceptable salts.
(1) l-(diphenylmethylpiperazinylethyl)urocanic acid methyl ester
(2) 1- (diphenylmethylpiperazinylethyl)urocanic acid
(3) 1-[phenyl(2-pyridyl)methylpiperazinylethyl]urocanic acid methyl ester
(4) 1-(4-nitrophenyl)urocanic acid methyl ester
(5) 1-(4-aminophenyl)urocanic acid methyl ester
(6) 1-(diphenylmethylpiperaiinylethyl)urocanic acid ethyl ester
(7) 1-(4-cyanophenyl)urocanic acid methyl ester
(8) 1-(4-cyanophenyl)urocanic acid
(9) 1-(2,5-thiazolyl)urocanic acid methyl ester
(10) 1-(4-carboethoxyphenyl)urocanic acid methyl ester
(11) 1-(4-carboxyphenyl)urocanic acid
(12) 1-(4-carboethoxyphenyl)urocanic acid ethyl ester
(13) 1-((4-carbomethoxymethylphenyl)methyl)urocanic acid methyl ester
(14) 1-((2-methoxyphenyl)piperazinylethyl)urocanic acid ethyl ester
(15) 1-(2-(2,4-dioxo-1,3-dihydroquinazoline-3-yl)ethyl)urocanic acid ethyl ester
(16) 1-(carboethoxymethyl)urocanic acid ethyl ester
(17) 1-(3-phenyl-2-propenyl)urocanic acid methyl ester


REFERENCES:
patent: 56-161314 A (1981-12-01), None
patent: 60-16907 A (1985-01-01), None
patent: 97/39748 (1997-10-01), None
patent: WO 97/39748 (1997-10-01), None

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