Structure-activity relationships among derivatives of dicarboxylic acid esters of tropine

Pharmacology and Therapeutics

Volumn 96, Issue 1, 2002, Pages 1-21

  Gyermek, Laszlo ^a  

^a HARBOR UCLA MEDICAL CENTER   (United States)

Author keywords

Bisquateranary tropine diester derivatives; New muscle relaxants; Structure activity relationships of muscle relaxants; Ultrashort acting neuromuscular blocking agents

Indexed keywords

ATRACURIUM; BENZYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CATION; DRUG DERIVATIVE; ESTER DERIVATIVE; FAZADINIUM; MIVACURIUM; MUSCLE RELAXANT AGENT; NEUROMUSCULAR BLOCKING AGENT; RAPACURONIUM; ROCURONIUM; TROPANE DERIVATIVE; TROPINE; UNCLASSIFIED DRUG;

ANESTHESIA INDUCTION; ARTICLE; CHEMICAL STRUCTURE; DEPOLARIZATION; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; HISTORY; IN VIVO STUDY; NERVE BLOCK; NEUROMUSCULAR BLOCKING; NONHUMAN; PRIORITY JOURNAL; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0036810466     PISSN: 01637258     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0163-7258(02)00296-6     Document Type: Review

References (52)

1. Anderson K.A., Muir A. Studies on a rapid onset and short-acting neuromuscular blocking agent, TAAC3 in anaesthetized cats. Eur J Anaesth. 18(suppl. 23):2001;A-36.
2. Bolger L., Brittain R.T., Jack D., Jackson M.R., Martin L.E., Mills J., Poynter D., Tyers M.B. Short lasting, competitive neuromuscular blocking activity in a series of azobis-arylimidazo-(1,2-a)-pyridinium dihalides. Nature. 238:1972;354-355.
3. Bovet D. Some aspects of relationship between chemical constitution and curare-like activity. Ann N Y Acad Sci. 54:1951;407-437.
4. Brücke F. Dicholine esters of α,ω-dicarboxylic acids and related substances. Pharmacol Rev. 81:1956;265-335.
5. Corringer P.-J., Le Novère N., Changeux J.-P. Nicotinic receptors at the amino acid level. Annu Rev Pharmacol Toxicol. 40:2000;431-458.
6. Crum Brown A., Fraser T.R. On changes produced by direct chemical addition of physiological action of certain poisons. Trans R Soc Edinburgh. 25:1868-1869;151229-233693.
7. Engelhardt A. Pharmacology and toxicology of atrovent. Scand J Resp Dis. 103:1979;110-111.
8. Fodor G., Nádor K. Stereochemistry of tropine and pseudotropine. Nature. 69:1952;462-463.
9. Fodor G., Tóth J., Vincze I. The stereochemistry of the tropane alkaloids. Part VI. The configuration of the nitrogen atom in tropane 3-α: 6β diol. Oscine and the derived quaternary salts. J Chem Soc (Lond). 1955;3504-3510.
10. Gyermek, L. (1966). Ganglionic stimulant and blocking agents. In A. Burger (Ed.), Chemical Constitution and Pharmacodynamic Action, Vol. 1, Ch. 4 (pp. 149-326). New York: Marcel Dekker Inc.
11. Gyermek L., Nádor K. Studies on cholinergic blocking substances II. Correlations of the antimuscarine, antinicotine and curare-like effects of mono and bisquaternary tropeines. Acta Physiol Acad Sci Hung. 3:1952;283-293.
12. Gyermek L., Nádor K. Studies on cholinergic blocking substances III. Neuromuscular blocking tropeines. Acta Physiol Hung. 4:1953;159-174.
13. Gyermek L., Nádor K. The pharmacology of tropane compounds in relation to their steric structure. J Pharm Pharmacol. 9:1957;209-229.
14. Gyermek L., Nádor K. Pharmacology of (p-biphenylmethyl) dl-tropyl-tropinium bromide. Arch Int Pharmacodyn Ther. 113:1957;1-14.
15. Gyermek L., Nguyen N., Lee C. G-1-64, a new, rapidly acting nondepolarizing neuromuscular blocking agent. Anesthesiology. 73:1990;A-862.
16. Gyermek L., Nguyen N., Lee C. A study of the role of interonium distances in the onset and duration of action of neuromuscular blocking tropinyl diesters in the rat. Anesthesiology. 77:1992;A-913.
17. Gyermek L., Nguyen N., Neumark A., Lee C. Anticholinergic spectrum of action of dicarboxylic acid esters of tropine in the rat. Anesth Analg. 74:1992;S-126.
18. Gyermek L., Nguyen N., Lee C. Structure activity relationships of neuromuscular blocking tropinyl diesters in the rabbit. Anesth Analg. 76:1993;S-131.
19. Gyermek L., Nguyen N., Lee C. Comparison of the neuromuscular blocking effects of tropine and pseudotropine diester derivatives in the rat and the rabbit. Anesthesiology. 79:1993;A-955.
20. Gyermek L., Nguyen N., Lee C. "Closed" chain derivatives of neuromuscular blocking tropinyl esters, a study in the rat. Anesth Analg. 76:1993;S-132.
21. Gyermek L., Lee C., Nguyen N. Neuromuscular blocking ethylquaternary tropinyl diesters: a structure-activity study. Anesth Analg. 78:1994;S-146.
22. Gyermek L., Lee C., Nguyen N., Cho Y.-M. Neuromuscular blocking N,N′polymethylene bistropanium, bis 3α-hydroxytropanium and bis-3-oxotropanium compounds. Life Sci. 63:1998;PL303-PL309.
23. Gyermek, L., Lee, C., & Cho, Y. -M. (1999a). Neuromuscular Relaxants. US Patents #5,990,124 November 23, 1999 and #6,376,510B1 April 23, 2002.
24. Gyermek L., Lee C., Nguyen N., Cho Y.-M. A structure-activity study of correlation of neuromuscular blocking bis-tropinyl diesters in the rat. Br J Anaesth. 82(suppl. 1):1999;A-384.
25. Gyermek L., Nguyen N., Lee C. Pharmacology of G-1-64, a new nondepolarizing neuromuscular blocking agent with rapid onset and short duration of action. Acta Anaesth Scand. 43:1999;651-657.
26. Gyermek L., Lee C., Cho Y.-M., Nguyen N. 2,6-Dichlorobenzyl quaternaries of tropinyl diesters. The functional role of the acid ester group in neuromuscular block. American Society of Anesthesiologists Annual Meeting, San Francisco, CA, October 14-18. 2000;A-1035 Lippincott Williams & Wilkins, Publ, Haggerstown.
27. Gyermek L., Lee C., Cho Y.-M., Nguyen N. Search for the optimal quaternizing moiety in ultrashort acting neuromuscular blocking agents I. 2,5-Dimenthoxybenzyl quaternariesof bis tropinyl diesters. American Society of Anesthesiologists Annual Meeting, San Francisco, CA, October 14-18. 2000;A-1036 Lippincott Williams & Wilkins, Publ, Haggerstown.
28. Gyermek L., Lee C., Cho Y.-M., Nguyen N. New, ultrashort acting muscle relaxants. Neuromuscular blocking profile on infusion administration in pigs. American Society of Anesthesiologists Annual Meeting, San Francisco, CA, October 14-18. 2000;A-1012 Lippincott Williams & Wilkins, Publ, Haggerstown.
29. Gyermek, L., Lee, C., Cho, Y. -M., Nguyen, N., Tsai, S. K. (2000d). A rat study of correlating neuromuscular blocking characteristics with stereochemical features. Proceedings 12th World Congress of Anesthesiologists, Montreal, June 4-9, Abstract #1214, Montreal, Quebec: Events International Inc.
30. Gyermek L., Nguyen N., Cho Y.-M. Time course of the breakdown in blood of two tropinyl diester type neuromuscular blocking agents. American Society of Anesthesiologists Annual Meeting, San Francisco, CA, October 14-18. 2000;A-1013 Lippincott Williams & Wilkins, Publ, Haggerstown.
31. Gyermek L., Lee C., Cho Y.-M., Nguyen N. Granatanol derivatives: ultrashort acting muscle relaxants. American Society of Anesthesiologists Annual Meeting, New Orleans, LA, October 13-17. 2001;A-1003 Lippincott Williams & Wilkins, Publ, Haggerstown.
32. Gyermek L., Lee C., Cho Y.-M., Nguyen N. TAAC 3: an ultrashort acting nondepolarizing muscle relaxant in animals. Anesth Analg. 92:2001;S-200.
33. Gyermek L., Lee C., Cho Y.-M., Nguyen N. Alkoxy-acetoxy benzyl quaternary derivatives of tropinyl diesters. Ultrashort acting nondepolarizing muscle relaxants. Eur J Anesth. 18(suppl. 23):2001;A-29.
34. Gyermek L., Lee C., Nguyen N., Cho Y.-M. Effects on infusion administration of new, ultrashort acting muscle relaxants in pigs. Anesth Analg. 92:2001;S-201.
35. Gyermek L., Lee C., Cho Y.-M., Nguyen N., Tsai S.K. Neuromuscular pharmacology of TAAC3, a new nondepolarizing muscle relaxant with rapid onset and ultrashort duration of action. Anesth Analg. 94:2002;879-885.
36. Gyermek L., Lee C., Nguyen N., Cho Y.-M. Ultrashort acting neuromuscular blocking agents. I. Di- and tri-substituted benzyl quaternary ammonium derivatives of (bis-tropane α-ol) diesters. Med Chem Res. 111:2002;316-336.
37. Haining C.G., Johnston R.G. Neuromuscular blocking properties of some bistropinium esters. Br J Pharmacol. 18:1962;275-286.
38. Haining C.G., Johnston R.G., Smith J.M. The neuromuscular blocking properties of a series of bisquaternary tropeines. Br J Pharmacol. 15:1960;71-81.
39. Hansch C., Leo A. Exploring QSAR. 1995; American Chemical Society, Washington, D.C.
40. Issekutz B. Die wirkung einiger neuen quatenären ammonoium basen auf die neuromuskulären und ganglionären synapsen. Arch Exp Path Pharmak. 215:1952;283-298.
41. Just O. Belladonnin- bromäthylate, ein neues muskelrelaxans. Anaesthesist. 2:1953;170-171.
42. Kimura K.K., Unna R.K. Curare like action of decamethylene-bis-(atropinium) Iodide. J Pharmacol Exp Ther. 98:1950;286-292.
43. Kimura K.K., Unna R.K., Pfeiffer C.C. Diatropine derivatives as proof that d-tubocurarine is blocking moiety containing twin atropine-acetylcholine prosthetic groups. J Pharmacol Exp Ther. 95:1949;149-154.
44. Lee C. Structure, conformation, and action of neuromuscular blocking drugs. Br J Anaesth. 87:2001;755-769.
45. Lee C., Cho Y.M., Gyermek L., Nguyen N. Conformation potency relationship of phtalate isomers of TAAC3. American Society of Anesthesiologists Annual Meeting, New Orleans, LA, October 13-17. 2001;A-1004 Lippincott Williams & Wilkins, Publ, Haggerstown.
46. Lee C., Gyermek L., Cho Y.-M., Nguyen N. Di-acetoxy benzyl quaternized ultrashort acting tropinyl diester muscle relaxants. Eur J Anaesth. 18(suppl. 23):2001;A-30.
47. Nádor K. Kurarinhatsú bisz-kvaternér tropeinek. Magy Tud Akad Biol Orvosi Oszt Közlményei. 10:1959;221-232.
48. Nádor K., Gyermek L. Attempts to find new compounds with curare-like effects III. Quaternary derivatives of dicarboxylic acid tropine esters. Acta Chim Hung. 2:1952;369-374.
49. Nádor K., Scheiber P., Karpati E., Grober K. Synthese und Farmakologie von N-stereoisomeren quartären Tropan Verbindungen. Arzneimittelforsch. 37:1987;1324-1327.
50. Unwin N. Acetylcholine receptor channel imaged in the open state. Nature. 373:1995;37-43.
51. van Egmond J., van de Pol F., Booji L., Muir A., Bom A. New fast neuromuscular blocking agent TAAC3 in the anaesthetized monkey. Eur J Anaesth. 18(suppl. 23):2001;A-2.
52. van Egmond J., van de Pol F., Booji L., Muir A., Bom A. New fast neuromuscular blocking agent TAAC3 in the anaesthetized dog. Eur J Anaesth. 18(suppl. 23):2001;A-3.