(1) Field of the Invention
The present invention relates to novel N-(.omega.-cyanoalkyl)aminophenols, a process for the preparation thereof, and the use of said aminophenols as agents which inhibit lipoxygenase activity.
(2) Information Disclosure Statement
S. A. Heininger U.S. Pat. No. 2,809,983 issued Oct. 15, 1957 discloses 3-(p-hydroxyanilino)propionitrile, 3-(o-hydroxyanilino)propionitrile, and 3-(m-hydroxyanilino)propionitrile as agricultural antifungals, rubber additives, chemical intermediates and biological toxicants. S. A. Heininger J. Org. Chem. 22, 1213-1217 (1957) makes substantially the same disclosure.
D'Amico et al., J. Am. Chem. Soc. 81, 5957-5963 (1959) discloses without utility at page 5961 3-(2-hydroxy-5-nitrosoanilino)propionitrile.
D. F. Scully U.S. Pat. No. 3,743,668 issued July 3, 1973, discloses 3-(p-hydroxyanilino)propionitrile, 3-(o-hydroxyanilino)propionitrile, and 3-(m-hydroxyanilino)propionitrile and a process for their preparation.
Aliev et al. Uzb. Khim. Ch. 1981, 45-49 (C.A. 96: 217407e) discloses 3-(o-hydroxyanilino)propionitrile. Similarly Peshakova et al. Khim. Geterotsikl. Soedin. 1981, 1420 (C.A. 96: 52211w) and D. A. Simov et al. Doklady Bolganskoj Akademija Nauk 32, 1365-1368 (1979) disclose only as starting material 3-(o-hydroxyanilino)propionitrile.
H. J. Peterli U.S. Pat. No. 3,213,601 issued Jan. 25, 1966 discloses 3-(p-hydroxyanilino)propionitrile, 3-(o-hydroxyanilino)propionitrile, and 3-(m-hydroxyanilino)propionitrile and a process for their production. J. M. Ross U.S. Pat. No. 3,496,213 issued Feb. 17, 1970 discloses the same three hydroxyanilinopropionitriles and a different process for their production.
British Pat. No. 1,326,824 published Aug. 15, 1973, which is equivalent to Ger. Offen. 2,000,509, discloses as a coupling component for azo dyes 3-(2-hydroxy-5-nitroanilino)propionitrile and a process for its production.
Mukhamedov et al. Uzb. Khm. Zh. 1983, 53 (CA 99: 5304f) discloses without utility 3-[(5-chloro-2-hydroxyphenyl)amino]propanenitrile.
Nitzschke and Budka Chem. Ber. 88, 264 (1955) discloses without utility 7-anilinoheptanenitrile.
Hilboll et al. U.S. Pat. No. 4,386,031 issued May 31, 1983 discloses N-benzoyl-.omega.-anilinoalkanecarboxylic acids and their derivatives of the general formula ##STR2## wherein n is a positive integer ranging from 7 to 10,
R.sup.1 and R.sup.2, which may be identical or different from each other, represent the unsubstituted phenyl group or the phenyl groups substituted by one to four equal or different radicals selected from the group of halogen, in particular chlorine or fluorine; C.sub.1-4 alkyl, in particular methyl; C.sub.1-4 alkoxy, in particular methoxy or ethoxy; C.sub.1-4 alkylthio, in particular methylmercapto or ethylmercapto; acyloxy, in particular C.sub.1-4 alkanacyl, most preferably acetoxy, propionyloxy or benzoyloxy; halo C.sub.1-4 alkyl, in particular trifluoromethyl; hydroxy; phenoxy; benzyloxy; di-C.sub.1-4 alkylamino, in particular dimethylamino; R.sup.3 is hydrogen, an alkali metal ion, in particular the sodium metal ion or a straight or branched saturated hydrocarbon group having from one to seven carbon atoms such as and in particular ethyl, isopropyl or heptyl; or the benzyl group. In most pertinent part U.S. Pat. No. 4,386,031 discloses at columns 14-16 (Example 13) 8-[4-chloro-N-(4-hydroxyphenyl)-benzamido]caprylic acid. The patent discloses that the benzoyl anilinoalkane carboxylic acids and their derivatives possess antiallergic activity and are useful for the treatment of allergic and asthmatic diseases.
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