Cryptolepine analogs with hypoglycemic activity

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

546 61, 546 62, C07D51900

Patent

active

056819587

ABSTRACT:
Novel cryptolepine analogs useful as hypoglycemic agents and methods for their use as hypoglycemic agents, for example, in the treatment of diabetes, and a method for their synthesis are described. As hypoglycemic agents, the novel crytolepine analogs are useful for the treatment of insulin-dependent diabetes mellitus (IDDM or Type I) and non-insulin dependent diabetes mellitus (NIDDM or Type II).

REFERENCES:
patent: 3374264 (1968-03-01), Uskokovic et al.
patent: 4826850 (1989-05-01), Yamato
patent: 4841063 (1989-06-01), Virgilio et al.
patent: 5070088 (1991-12-01), Atwal
patent: 5223506 (1993-06-01), Luzzio et al.
patent: 5428040 (1995-06-01), Magolda et al.
Ablordeppey et al., 1990, ".sup.1 H-NMR and .sup.13 C-NMR Assignments of cryptolepine, A 3:4-benz-.delta.-carboline derivative isolated from Cryptolepis sanguinolentai", Planta Medica 56:416-417.
Anon, 1982, "Cryptolepine hydrochloride", Drugs of the Future 7:466.
Armit and Robinson, 1922, "Polynuclear heterocyclic aromatic types. Part I. Some indenoquinoline derivatives", J Chem Soc pp. 827-839.
Baldwin and Magnus (eds.), 1994, in Organic Synthesis Based on Name Reactions and Unnamed Reactions, vol. 11, pp. 36.
Bamgbose and Noamesi, 1981, "Studies on Cryptolepine", Planta Medica 41:392-396.
Blount et al., 1929, "Stereoisomerism in polycyclic systems. Part VI", J Chem Soc 1975-1987.
Boakye-Yiadom and Heman-Ackah, 1979, "Cryptolepine hydrochloride effect on Staphylococcus aureus", J Pharm Sci 68(12):1510-1514. derivatives", Heterocycle 33(1):147-152.
Cimanga et al., 1991, "Biological Activities of Cryptolepine, An Alkaloid from Cryptolepis sanguinolenta", Planta Medica 57 Supp. 2 A98-A99.
Clinquart et al., 1929, "Sur la compesition chimique de Cryptolepis triangularis plante congolaise", Bull. Acad. R. Med. Belg. 12:627-635.
Degutis and Ezyarskaite, 1986, "Alkylation of quindoline and quindoline-11-carboxyic acid", Khimiya Geterotsiklicheskikh Soedinenii 10:1375-1379.
Desearbre and Merour, 1994, "Synthesis and reactivity of 35(13):1995-1998.
Dwuma-Badu et al., 1978, "Constituents of West African medicinal plants XX: Quindoline from Cryptolepis sanguinolenta", J Pharm Sci 67(3):433-434.
Ezyarskaite, 1989, "On the synthesis of 7-bromoquindoline derivatives", Izv Khim 22:101-105.
Fichter and Boehreinger, 1906, "Ueber chindolin", Diese Berichte 3932-3942.
Fichter and Rohner, 1910, "Uber einige derivate des chindolins", Chem Ber 43:3489-3499.
Fichter and Probst, 1907, "Zur kenntnis des methyl-chindolanols", Diese Berichte 40:3478.
Galun et al., 1979, "Derivatives of Indole-3-oxyacetic acid", J Heterocyclic Chem 16:641-643.
Gellert et al., 1951, "Die konstitution des alkaloids cryptolepin", Helvetica Chimica Acta 34:642-651.
Giraud, 1879, "Sur quelques derives de l'indigotine", Comptes Rendus pp. 104-105.
Giraud, 1880, "Preparation de l'indoline et de ses composes", Comptes Rendus pp. 1429-1430.
Gorlitzer and Weber, 1981, "Hemmung der thrombocytenaggregation dutch anellierte chinoline mit 3-dimethylaminopropylmercapto-substituenten", Arch Phar 315:532-537.
Gorlitzer et al., 1994, "Anti-malaria active the amodiaquine and cycloquine type", Pharmazie 49:231-235. (`Dioxychindolin`)", Arch Pharm 314:850-852. 314:852-861.
Gorlitzer et al., 1995, "Gegen malaria wirksame
Gorlitzer, 1976, "Untersuchungen an 1,3-dicarbonylverbindungen, 6. Mitt. Anerllierte Chinolone", Arch Pharm 309:18-25. chinoline, s,s-dioxide und thionierungsprodukte", Arch Pharm 314:76-84.
Gorlitzer and Weber, 1980, "Anellierte chinoline III), 313:27-34.
Gorlitzer, 1979, "Anellierte chinolone II, N- und O-alkylierungs produkte", Arch Pharm 312:254-261.
Gunatilaka et al., 1980, "Studies on the medicinal plants of Sri Lanka", Planta Medica 39:66-72.
Holt and Petrow, 1948, "Carbazoles, carbolines, and related compounds. Part II. Transformations of some quarternary salts of quindoline", pp. 919-922.
Holt and Petrow, 1947, "Carbazoles, carbolines, and related compounds. Part I. Quindoline derivatives", pp. 607-611.
Holt and Petrow, 1948, "Carbazoles, carbolines, and related compounds. Part III. Quinindoline derivatives", pp. 922-924.
Jezerskaite et al., 1989, "New heterocyclic sensitizers for electrophotography", Izv Khim 22:113-121.
Kempter et al., 1963, Z Chem 3:352-353.
Merour et al., 1982, "Syntheses of 2(5)-substituted 1-acetyl-3-oxo-2,3-dihydroindoles, 3-acetoxy-1-acetylindoles, and of 2-methyl-5-methoxyindole-3-acetic acid", Synthesis 12: 1053-1056.
Mooradian et al., 1949, "'A new series of testosterone esters", J Amer Chem Soc 71:3372-3374.
Nenitzescu and Raileanu, 1958, "Synthesen des heteroauxins, des tryptamins und des serotonins", Chem Ber 91:1141-1145.
Oyekan, 1994, "Role of the Endothelium and Cyclic GMP in Renal Vasodilator Responses to Cryptolepine in Rats", J. Cardiovasc. Pharmacol. 23:602-611.
Ossman et al., 1988, "Synthesis of 2-cyanomethyl-3, 1-benzoxazin-4(H)-one", Egypt J Chem 31 (3):381-385.
Oyekan and Ablordeppey, 1993, "The mechanism(s) of the antiaggregatory effects of cryptolepine: The role of cyclic adenosine monophosphate and cellular Ca.sup.2+ ", Gen Pharmacol 24(2):461-469.
Oyekan and Ablordeppey, 1993, "Effects of cryptolepine on collagen-induced aggregation and on the mobilization and metabolism of arachidonic acid by rabbit platelets", Gert Pharmacol 24(5):1285-1290.
Oyekan and Okafor, 1989, "Effects of cryptolepine alone and in combination with dipyridamole on a mouse model of arterial thrombosis", J Ethnopharmacol 27:141-148.
Paulo et al., 1994, "In vitro antibacterial screening of Cryptolepis sanguinolenta alkaloids", J Ethnopharmacol 44:127-130.
Potential Antimalarial in Ghanian Plant, IMS Pharmaceutical Marketletter, May 7, 1984, p., 13.
Proceeding from the First International Seminar on Cryptolepine at the University of Science and Technology Kumasi, July 27-30 1983, Boakye-Yiadom and Bamgbose (eds.), pp.1-82.
Rauwald et al., 1992, "Cryptolepis sanguinolenta:Antimuscarinic Properties of Cryptolepine and the Alkaloid Fraction at M1, M2 and M3 Receptors," Planta Medica, 58:486-488.
Raymond-Hamet et al., 1938, "Pharmacologie--Sur les Effects Hypotenseurs et Vaso-dilatateurs de la Cryptolepine", C.R. Acad. Sci. 207:1015-1018.
Raymond-Hamet et al., 1937, "Sur Quelques Proprietes Physiologiques des Alcaloides du Crytloepis sanguinolenta Schlechter", C.R. Soc. Biol. 126:768-770.
Schoen and Bogdanowicz-Szwed, 1964, "The reaction of .alpha.-indanone anils with phenylisocyanate. Anilides of 1-arylamino-indene-2-carboxylic acids", Roczniki Chemii Ann Soc Chim Polonorum 38:425-435.
Schulte et al., 1971, "Kondensierte indole aus 2-chlorindoaldehyd-(3)", Arch Pharmaz 305:523-533.
Schutzenberger, 1877, "Note sur un nouveau derive de l'indigotine", Comptes Rendus pp. 147-149.
Sevodin et al., 1984, "New method of synthesis of quindolines from 1,5-diketones of the indoline series", Chem Heterocyclic Comp 20(12):1374-131380.
Sevodin et al., 1982, "New methods for the synthesis of quindolines on the basis of 1,5-diketones of the indolinone series", Chem Heterocyclic Compounds 18(8):865.
Spitzer et al., 1991, "Total assignment of the proton and carbon NMR spectra of the alkaloid quindoline--Utilization of HMQC-TOCSY to indirectly establish protonated carbon-protonated carbon connectivities", J Heterocyclic Chem 28:2065-2070. and derivatives", J Heterocyclic Chem 15:1379-1382.
Tackie et al., 1991, "Assignment of the proton and carbon NMR spectra of the indoloquinoline alkaloid cryptolepine", J Heterocyclic Chem 28:1429-1435.
Takeuchi et al., 1992, "Synthesis and antitumor activity of fused quinoline Pharm Bull 40(6):1481-1485.
Takeuchi et al., 1991, "Synthesis and antitumor activity of 39(6):1629-1631.
Yamato et al., 1990, "Synthesis and antitumor activity of fused quinoline derivatives", Chem Pharm Bull 38(11 ):3048-3052.
Yamato et al., 1989, "Synthesis and antitumor activity of fused tetracyclic quinoline derivatives", J Med Chem 32:1295-1300.
Yamato et al., 1992, "Synthesis and antitumor activity of fused quinoline Bull 40(2):528-530.
Noamesi et al., 1980, "The alpha-adrenoceptor blocking properties of cryptolepine on the rat isolated vas deferens", P

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Cryptolepine analogs with hypoglycemic activity does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Cryptolepine analogs with hypoglycemic activity, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Cryptolepine analogs with hypoglycemic activity will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1027297

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.