TREA

Antiatherosclerotic aminoethenyl furochromones

Follow

Information

  • Patent Grant
  • 4540798
  • Patent Number
    4,540,798
  • Date Filed
    Thursday, October 27, 1983
    40 years ago
  • Date Issued
    Tuesday, September 10, 1985
    38 years ago
Information
Abstract
The present invention provides certain novel aminoethanyl furochromones which are useful for antiatherosclerotic purposes.
Description

BACKGROUND OF THE INVENTION
The present invention provides novel anti-atherosclerotic aminoethenyl furochromones. The use and preparation of these compounds is described in U.S. Pat. No. 4,438,274, which is expressly incorporated by reference herein.
PRIOR ART
Extensive pharmacological uses for khellin and related substances are known, as indicated in Appendix A, Khellin analogs are also known in the art. See, e.g., U.S. Pat. No. 4,284,569 and the review by Mustafa, "furopyrans and Furopyrones," John Wiley and Sons, Inc., N.Y., N.Y. (1976) pages 102-159 and U.S. Pat. No. 2,680,119 which describes 6 and/or 7-substituted furochromones, i.e., alkyl, alkoxyalkyl, and phenylalkyl substituted compounds.
SUMMARY OF THE INVENTION
The present invention provides:
a furochromone of formula II
wherein R.sub.7 is --CH.sub.2 --R.sub.11, wherein R.sub.11 is hydrogen or C.sub.1 -C.sub.5 thioalkyl;
wherein R.sub.8 is --CH.dbd.CH--NR.sub.12 R.sub.13 wherein R.sub.12 and R.sub.13, being the same or different, are C.sub.1 -C.sub.3 alkyl; and
wherein one of R.sub.5 and R.sub.6 is methoxy and the other is hydrogen or R.sub.5 and R.sub.6 are both methoxy.





DESCRIPTION OF THE PREFERRED EMBODIMENTS
The present invention particularly provides (2'E)-4,9-dimethoxy-6-[(methylthio)methyl]-7-(1',N,N-dimethylamino-ethen-2'-yl)-5M-furo[3,2-g]-benzopyran-5-one.
Claims
  • 1. A furochromone of formula II ##STR1## wherein R.sub.7 is --CH.sub.2 --R.sub.11, wherein R.sub.11 is hydrogen or C.sub.1 -C.sub.5 thioalkyl;
  • wherein R.sub.8 is --CH.dbd.CH--NR.sub.12 R.sub.13 wherein R.sub.12 and R.sub.13, being the same or different, are C.sub.1 -C.sub.3 alkyl; and
  • wherein one of R.sub.5 and R.sub.6 is methoxy and the other is hydrogen or both R.sub.5 and R.sub.6 are methoxy.
  • 2. (2'E)-4,9-Dimethoxy-6-[(methylthio)methyl]-7-(1',N,N-dimethylamino-ethen-2'-yl)-5M-furo[3,2-g]-benzopyran-5-one, a furochromone according to claim 1.
CROSS REFERENCE TO RELATED APPLICATIONS

This application is a divisional of co-pending application Ser. No. 378,700, filed May 17, 1982, now U.S. Pat. No. 4,438,274.

US Referenced Citations (2)
Number Name Date Kind
2680119 Robertson et al. Jun 1954
4284569 Gammill Aug 1981
Non-Patent Literature Citations (29)
Entry
Abu-Shady, H., Experiments with Khellin VII., UAR J. Pharm. Sci., 11:283-288, (1970).
Abu-Shady, H., et al., Experiments with Khellin--VIII., J. Pharm. Belg., 33:397-399, (1978).
Anrep, G. V., et al., Therapeutic Uses of Khellin, The Lancet, pp. 557-558, Apr. 26, 1947.
Anrep, G. V., et al., The Coronary Vasodilator Action of Khellin, Amer. Heart J., 37:531-542, (1949).
Apffel, C. A., Die Zytostatische Wirkung von Chinonen und Ihren Derivaten, Deut. Med. Wochschr., 80:414-416, (1955).
Aubertin, E., La Khelline, Agent de Relachement de la Musculature Lisse, J. Med. Bordeaux, 127:821-823, (1950).
Baytop, O. T., Khellin'in Yer Solucanlarina Tesiri Hakkinda, Folia Pharm., (Turkey), 1:48-49, (1949).
Best, M. M., et al., Effects of Dioxyline Phosphate and Enteric-Coated Khellin on Coronary Artery Insufficiency, Amer. J. Med. Sci., 222:35-39, (1951).
Chen, G., et al., The Central Nervous Depressive Effect of Khellin, Proc. Soc. Expetl. Biol. Med., 78:305-307, (1951).
Colombo, G., et al., Sulla Attivita di Alcune Sostanze del Gruppo Della Kellina Sulla Motilita Ureterale--in vitro--, Arch. Sci. Med., 97:71-81, (1954).
Day, C. E., et al., Utility of a Selected Line (SEA) of the Japanese Quail for the Discovery of New Anti-Atherosclerosis Drugs, Laboratory Animal Science, 27:817-821, (1977).
Eaton, R. P., High Density Lipoprotein--Key to Anti-Atherogenesis, J. Chron. Dis., 31:131-135, (1978).
Haust, M. D., Reaction Patterns of Intimal Mesenchyme to Injury, and Repair in Atherosclerosis, Adv. Exp. Med. Biol., 43:35-57, (1974).
Huttrer, C. P., et al., The Chemistry and Physiological Action of Khellin and Related Products, Chem. Revs., 48:543-579, (1951).
Jordan, H., Cardiovasculare Wirkungen Intravenoser Khellin-Injektionen, Arzneimittel-Forsch, 7:82-85, (1957).
LaBarre, J., et al., A Propos de l'Action Inhibitrice de la Khelline dans l'Ulcere Gastrique Experimental Provoque par Administration Journaliare de Phenylbutazone, Compt. Rend. Soc. Biol., 150:1806-1807, (1956).
Montorsi, W., et al., Sur l'Activite de Certaines Substances du Groupe de la Khelline, Presse Med., 63:81, (1955).
Musante, C., et al., Furil E. Isossazol-Furo-Cromoni e Derivati, Pharmaco. (Pavie) Ed. Sci., 15:81-94, (1960).
Mustafa, A., et al., Experiments with Furochromones, Synthesis of Ammiol and Khellol, J. Org., Chem., 26:886-890, (1961).
Mustafa, A., Furopyrans and Furopyrones, John Wiley and Sons, Inc., NY, (1967), pp. 102-159, (Chapter III: Furochromones).
Osher, H. L. et al., Khellin in the Treatment of Angina Pectoris, New England J. Med., 224:315-321, (1951).
Raymond-Hamet, M., Compt. Rend., 238:1624-1626, (1954).
Samaan, K., et al., The Response of the Heart to Visammin and to Khellinin, J. Pharm. Pharmacol., 1:538-544, (1949).
Samaan, K., et al., The Existence in Ammi Visnaga of a Cardiac Depressant Principle Visammin and a Cardiac Stimulant Glycoside Khellinin, J. Roy, Egypt Med. Assoc., 33:953-960, (1950).
Schonberg, A., et al., Khellin and Allied Compounds, JACS, 72:1611-1617, (1950).
Schonberg, et al., Furo-Chromones and -Coumarins, XIV., JACS, 77:5439-5440, (1955).
Schurr, P. E., High Volume Screening Procedure for Hypobetalipoproteinemia Activity in Rats, Adv. Exp. Med. Biol. 67: Atherosclerotic Drug Discovery, pp. 215-229, Plenum Press, (1975).
Silber, E. N., The Effect of Khellin on Cardio-Pulmonary Function in Chronic Pulmonary Disease, published in 1951, pp. 1046-1054.
Swayne, V. R., et al., Spermicidal Action of Khellin, Amer. J. Pharm., 125:295-298, (1953).
Divisions (1)
Number Date Country
Parent 378700 May 1982