Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1993-07-19
1995-04-11
Gerstl, Robert
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548125, 546277, 544405, 514252, 514340, C07D27300, A61K 3141
Patent
active
054058570
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PcT/DK92/00043 Feb. 11.1992
1. Technical Field
The present invention relates to hitherto unknown 3-substituted 1,2,3,4-oxatriazole-5-imine compounds which have proved to have biological effects making them suitable for treatment of cardiovascular diseases (blood clots) and asthma, a process for the preparation thereof and a pharmaceutical preparation containing said compounds.
2. Background Art
K. Masuda et al., Chem. Pharm. Bull. 19 (3) pages 559-563 (1971) discloses 3-aryl-1,2,3,4-oxatriazole-5-imine compounds and acyl derivatives thereof, wherein the acyl group can be monosubstituted by methyl or halogen. Even though these compounds were synthesized in the hope of finding new hypotensive agents, no biological effects of the compounds are described.
C. Christophersen et al., Acta Chemica Scandinavica 25 pages 625-630 (1971), discloses 3-substituted 1,2,3,4-oxatriazole-5-imino compounds, where the 3-substituent can be propyl or phenyl or cyclohexyl. However, no biological effects of said compounds are described.
Hanley et al., J. C. S. Perkin Trans I, 736-740 (1979), discloses 3-aryl-1,2,3,4-oxatrizole-5-imine compounds, where the aryl group can be monosubstituted by methyl or halogen. However, no biological effects of the compounds are described.
The JP Patents Nos. 20904/70 and 21102/70 disclose 3-substituted 1,2,3,4-oxatriazole-5-imine salts and acyl derivatives thereof, wherein the 3-substituent can be aryl optionally monosubstituted by chloride or methyl. These compounds are stated to exhibit vasodepressor activity.
GB published specification number 2 015 878 discloses 3-phenyl-1,2,3,4-oxatriazole-5-imine compounds, for which a pesticidal and/or pest ovicidal and/or hebicidal activity has been found.
U.S. Pat. No. 4,329,355 discloses anhydro-5-imino-1,2,3,4-oxatriazolium hydroxides of a structure similar to the structure of the compounds of the present invention. However, the compounds known from this patent specification are only mentioned as being useful in the treatment of cancer.
Furthermore, from J. C. S. Perkin Trans I, 747-751 (1979) compounds of a structure similar to the structure of the compounds of the present invention are known. However, no biological effects of said compounds have been stated.
DISCLOSURE OF THE INVENTION
The present invention relates to hitherto unknown 3-substituted 1,2,3,4-oxatriazole-5-imine compounds of the general formula I and acid addition salts thereof ##STR1## wherein R.sup.1 is the same or different alkyl or alkoxy groups having 1 to 3 carbon atoms, halogen, trifluoromethyl, nitro, cyano, phenyl or alkylsulphonyl groups, n is 1 to 5, and R.sup.2 is hydrogen or a group of the formula II bond, Y is an alkylene group having 1 to 4 carbon atoms or a direct bond, and Q is alkyl, cycloalkyl, alkoxy or a phenyl, pyridyl, furanyl, thienyl, or pyrazinyl group being optionally substituted by Z, where Z is alkyl or alkoxy groups having 1 to 3 carbon atoms, halogen, hydroxy, acyloxy, trifluoromethyl, nitro, cyano or alkylsulphonyl, and m is 1 to 3, whereby Z also, when X is --C(O)--or --C(O)NH--, Y is a direct bond, and Q is substituted phenyl, can mean the structure I, wherein R.sup.2 has the same meaning with respect to X, Y, and Q with the proviso that R.sup.2 is not hydrogen, alkyl, benzoyl, trifluoroacetyl or an optionally substituted phenyl group, when R.sup.1 is methyl or chlorine and n is 1, and R.sup.2 is not hydrogen or an optionally substituted phenyl group, when R.sup.1 is nitro, alkoxy, fluorine or bromine, and n is 1.
These compounds differ from the above known compounds by their chemical constitution, as they have a different substitution in the 3-position and/or in the 5-position of the oxatriazole ring, and they differ from the compounds known from the above patents by their biological effect, as they inhibit the blood platelet aggregation and have relaxation effect on trachea.
Accordingly, the invention also relates to a pharmaceutical preparation characterized by comprising as an active ingredient a compound of the formu
REFERENCES:
patent: 4329355 (1982-05-01), Henry et al.
Chemical Abstracts, vol. 73, No. 17, Oct. 26, 1970, (Columbus, Ohio, U.S.), p. 361, Abstract No. 87922f, & JP,A, 7021102 (N-acyl-anhydro-1,2,3,4-oxatriazole-5-imines) Jul. 17, 1970.
Chemical Abstracts, vol. 73, No. 17, Oct. 26, 1970, (Columbus, Ohio, U.S.), p. 362, Abstract No. 87930g, & JP,A, 7020904 (Mesoionic compounds) Jul. 15, 1970.
Journal of Organic Chemistry, vol. 30, Feb. 1965, William G. Finnegan et al: "Synthesis And Reactions Of 1-Nitroso-1-Alkyl-2-Guanyl- and -2-Carbamylhydrazines", pp. 567-575.
Chemical Society, London, Journal Perkin transactions I, 1979, Robert N. Hanley et al: "Cyclic Mesoionic Compounds. Part 17. Synthesis, Spectroscopic Properties, and Chemistry of 1,2,3,4-Oxatriazolium-5-Aminides and 1,2,3,4-Tetrazolium-5-Olates", pp. 736-740.
Chemical Society, London, Journal Perkin transactions I, 1979, Robert N. Hanley et al: "Cyclic Meso-Ionic Compounds. Part 20. Mass Spectra of Meso-Ionic Heterocycles", pp. 747-751.
Acta Chemica Scandinavica, vol. 25, 1971 Carsten Christophersen et al: "The Reaction of 1-Substituted and 1,4-Disubstituted Thio-Semicarbazides with Nitrous Acid. 3-Substituted N-/5-(1,2,3,4-Oxatriazolo)/Amides", pp. 625-630.
Chemical Pharm. Bull., vol. 19, No. 3, 1971 Katsutada Masuda et al: "Studies on Mesoionic Compounds. III. Synthesis of -3-Aryl-5-Imino-3,5-Dihydro-1-Oxa-2,3,4-Triazole Hydrochlorides and Their Derivatives", pp. 559-563.
Alhede Borge I. F.
Clausen Finn P.
Corell Tim N.
Karup Gunnar L.
Lissau Bodil G.
A/S Gea Farmaceutisk Fabrik
Gerstl Robert
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