Orally active and selective benzylidene ketal M2 muscarinic receptor antagonists for the treatment of Alzheimer's disease

Drug Development Research

Volumn 56, Issue 3, 2002, Pages 310-320

  Boyle, Craig D ^a   Lachowicz, Jean E ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Acetylcholine; Alzheimer's disease; Microdialysis; Muscarinic antagonist; Passive avoidance

Indexed keywords

3ALPHA CHLOROIMPERIALINE; 4 CYCLOHEXYL ALPHA [4 [(4 METHOXYPHENYL)SULFINYL]PHENYL] 1 PIPERAZINEACETONITRILE; ACETAL; ACETYLCHOLINE; BENZODIAZEPINE DERIVATIVE; BENZYLIDENE DERIVATIVE; BIBN 99; CHOLINESTERASE INHIBITOR; HIMBACINE; MUSCARINIC M2 RECEPTOR ANTAGONIST; NATURAL PRODUCT; PIPERAZINE DERIVATIVE; PIPERIDINE DERIVATIVE; SCH 72788; TRIPITRAMINE; UNCLASSIFIED DRUG; YM 59981;

ACETYLCHOLINE RELEASE; ALZHEIMER DISEASE; CHOLINERGIC SYSTEM; COGNITIVE DEFECT; DRUG ACTIVITY; DRUG SELECTIVITY; HUMAN; MICRODIALYSIS; NONHUMAN; RECEPTOR AFFINITY; REVIEW;

EID: 0036660001     PISSN: 02724391     EISSN: None     Source Type: Journal    
DOI: 10.1002/ddr.10084     Document Type: Review

References (64)

1. Araujo DM, Lapchak PA, Robitaille Y, Gauthier S, Quirion R. 1988. Differential alteration of various cholinergie markers in cortical and subcortical regions of human brain in Alzheimer's disease. J Neurochem 50:1914-1923.
2. Aubert I, Araujo DM, Cécyre D, Robitaille Y, Gauthier S, Quirion R. 1992. Comparative alterations of nicotinic and muscarinic binding sites in Alzheimer's and Parkinson's diseases. J Neurochem 58:529-541.
3. 1 preferring agonist. J Pharmacol Exp Ther 292:584-596.
4. 2-selective muscarinic receptor antagonist that penetrates into brain. Eur J Pharmacol 251:315-317.
5. 2 through a correlation of in vivo microdialysis and in vitro receptor binding data. J Pharmacol Exp Ther 273:273-279.
6. 2 selectivity and improved potency. Bioorg Med Chem Lett 10:2209-2212.
7. Bodick NC, Offen WW, Levey AI, Cutler NR, Gauthier SG, Satlin A, Shannon HE, Tollefson GD, Rasmussen K, Bymaster FP, Hurley DJ, Potter WZ, Paul SM. 1997. Effects of xanomeline, a selective muscarinic receptor agonist, on cognitive function and behavioral symptoms in A]zheimer disease. Arch Neurol 54:465-473.
8. Bolognesi ML, Minarini A, Budriesi R, Cacciaguerra S, Chiarini A, Spampinato S, Tumiatti V, Melchiorre C. 1998. Universal template approach to drug design: polyamines as selective muscarinic receptor antagonists. J Med Chem 41:4150-4160.
9. Bonner TI, Buckley NJ, Young AC, Brann MR. 1987. Identification of a family of muscarinic acetylcholine receptor genes. Science 237:527-532, 4822 (erratum).
10. Bonner TI, Young AC, Brann MR, Buckley NJ, 1988. Cloning and expression of the human and rat m5 mnscarinic acetycholine receptor genes. Neuron 1:403-410.
11. 2 muscarinic receptor antagonists. Bioorg Med Chem Lett 10:2727-2730.
12. 2 muscarinic receptor antagonists via halonaphthoic acid substitution. Bioorg Med Chem Lett t1 11:2311-2314.
13. 2 muscarinic receptor antagonists via aryl amide modification (Abstract). 222nd American Chemical Society National Meeting, Chicago, IL.
14. 2 receptor antagonist, releases acetylcholine and produces cognitive enhancement in laboratory animals. Eur J Pharm 431:189-200.
15. Chackalamannil S, Davies RJ, Asberom T, Doller D, Leone D. 1996. A highly efficient total synthesis of (+)- himbacine. J Am Chem Soc 118:9812-9813.
16. Clader JW. 1999. Recent advances in cholinergic drugs for Alzheimer's disease. Curr Opin Drug Disc Dev 2:311-320.
17. Cox KA, Dunn-Meynell K, Korfmacher WA, Broske L, Nomeir AA, Lin CC, Cayen MN, Barr WH. 1999. Novel in vivo procedure for rapid pharmacokinetic screening of discovery compounds in rats. Drug Discov Today 4:232-237.
18. Doller D, Chackalamannil S, Czarniecki M, MeQuade R, Ruperto V. 1999. Design, synthesis, and structure-activity relationship studies of himbacine derived muscarinic receptor antagonists. Bioorg Med Chem Lett 9:901-906.
19. 2 antagonists as potential drugs for cognitive disorders. Drugs Fut 20:157-164.
20. 2 antagonists: novel structures and pharmacology. Life Sci 52:497-503.
21. Doody RS, Dunn JK, Clark CM, Farlow M, Foster NJ, Lioa T, Gonzales N, Lai E, Massman P. 2001a. Chronic donepezil treatment is associated with slowed cognitive decline in Alzheimer's disease. Dement Geriatr Cogn Disord 12:295-300.
22. Doody RS, Geldmacher DS, Gordon B, Perdomo CA, Pratt RD. 2001b. Open-label, multicenter, phase 3 extension study of the safety and efficacy of donepezil in patients with Alzheimer disease. Arch Neurol 58:427-433.
23. Dunn NR, Pearce GL, Shakir SA. 2000. Adverse effects associated with the use of donepezil in general practice in England. J Psychopharmacol 14:406-408.
24. Felder CC, Bymaster FP, Ward J, DeLapp N. 2000. Therapeutic opportunities for muscarinic receptors in the central nervous system. J Med Chem 43:4333-4353.
25. Forette F, Anand R, Gharabawi G. 1999. A phase II study in patients with Alzheimer's disease to assess the preliminary efficacy and maximum tolerated dose of rivastigmine (Exelon). Eur J Neurol 6:423-429.
26. 2 receptor antagonist. Life Sci 38:1663-1672.
27. 2 subtype. Life Sci 53:1743-1751.
28. Greene YM, Tariot PN, Wishart H, Cox C, Holt CJ, Schwid S, Noviasky J. 2000. A 12-week, open trial of donepezil hydrochloride in patients with, multiple sclerosis and associated cognitive impairments. J Clin Psychopharmacol 20:350-356.
29. Greenlee W, Clader J, Asberom T, McCombie S, Ford J, Guzik H, Kozlowski J, Li S, Liu C, Lowe D, Vice S, Zhou H, Zhou G, Billard W, Binch H, Crosby R, Duffy R, Lachowicz J, Coffin V, Watkins R, Ruperto V, Strader C, Taylor L, Cox K. 2001. Muscarinic agonists and antagonists in the treatment of Alzheimer's disease. I1 Farmaco 56:247-250.
30. Hart DJ, Wu WL, Kozikowski AP. 1995. Total synthesis of (+)-himbacine and (+)-himbaline. J Am Chem Soc 117:9369-9370.
31. Hecht SS, Chen CB, Hoffman D. 1978. Evidence for metabolic α-hydroxylation of N-nitrosopyrrolidine. Cancer Res 38:215-218.
32. Jacobsen FM, Comas-Diaz L. 1999. Donepezil for psychotropic-induced memory loss. J Clin Psychiatry 60:698-704.
33. 4 receptors impairs memory in the rat. Neuroreport 9:1407-1411.
34. Kozikowki AP, Fauq AH, Miller JH, McKinney M. 1992. Alzheimer's therapy: an approach to novel muscarinic ligands based upon the naturally occurring alkaloid himbacine. Bioorg Med Chem Lett 2:797-802.
35. 2 receptor. Bioorg Med Chem Lett 10:2255-2257.
36. 2 selective ligands. Bioorg Med Chem Lett 12:791-794.
37. Kubo T, Fukuda K, Mikami A, Maeda A, Takahashi H, Mishina M, Haga T, Haga K, Ichiyama A, Kangawa K, et aL. 1986. Cloning, sequencing and expression of complementary DNA encoding the muscarinic, acetylcholine receptor. Nature 323:411-416.
38. Kumagai Y, Fukoto JM, Cho AK. 1994. The biochemical disposition of methylenedioxyphenyl compounds. Curr Med Chem 4:254-261.
39. 2 receptor selective antagonist. Life Sci 64:535-539.
40. 2 muscarinic antagonist, SCH 72788. Life Sci 68:2585-2592.
41. Lapchak PA, Araujo DM, Quirion R, Collier B. 1989. Binding sites for [3H]AF-DX 116 and effect of AF-DX 116 on endogenous acetylcholine release from rat brain slices. Brain Res 496:285-294.
42. Malaska MJ, Fauq AH, Kozikowski AP, Aagaard PJ, McKinney M. 1993. Simplified analogs of himbacine displaying potent binding affinity for muscarinic receptors. Bioorg Med Chem Lett 3:1247-1252.
43. 2-selectivity. Bioorg Med Chem Lett 5:61-66.
44. 2 muscarinic receptor antagonists. Chem Pharm Bull 48:1611-1622.
45. Masanic CA, Bayley MT, VanReekum R, Simard M. 2001. Open-label study of donepezil in traumatic brain injury. Arch Phys Med Rehabil 82:896-901.
46. 2 muscarine receptors in the cerebral cortex in A]zheimer's disease and experimental cholinergic denervation. Science 228:1115-1117.
47. 2-selective muscarinic receptor ligands in the 1-[4-(4-arylsulfonyl)-phenylmethyl]-4-(4-piperidinyl)-piperazine family. Bioorg Med Chem Lett 12:795-798.
48. 2-antagonists. Med Res Rev 10:327-349.
49. Messer WS, Thomas GJ, Hoss W. 1987. Selectivity of pirenzepine in the central nervous system: II. Differential effects of pirenzepine and scopolamine on performance of a representational memory task. Brain Res 407:37-45.
50. Murdoch I, Nicoll JA, Graham DI, Dewar D. 2002. Nucleus basalis of Meynert pathology in the human brain after fatal head injury. J Neurotrauma 19:279-284.
51. Nakamura S, Ishihara T. 1990. Task-dependent memory loss and recovery following unilateral nucleus basalis lesion: behavioral and neurochemical correlation. Behav Brain Res 39:113-122.
52. Pohorecki R, Head R, Domino EF. 1998. Effects of selected muscarinic cholinergic antagonists on [3H] acetylcholine release from rat hippocampal slices. J Pharmacol Exp Ther 244:213-217.
53. Rouse ST, Mariano MJ, Potter LT, Conn PJ, Levey AI. 1999. Muscarinic receptor subtypes involved in hippocampal circuits. Life Sci 64:501-509.
54. Silverman RB. 1992. The organic chemistry of drug design and drug action. San Diego: Academic. p 297.
55. Smith RD, Kistler MK, Cohen-Williams M, Coffin VL. 1996. Cholinergic improvement of a naturally-occurring memory deficit in the young rat. Brain Res 707:13-21.
56. Tagat JR, McCombie SW, Nazareno DV, Boyle CD, Kozlowski JA, Chackalamannil S, Josien H, Wang Y, Zhou G. 2002. Synthesis of mono- and difluoronaphthoic acids. J Org Chem 67:1171-1177.
57. Tohyama M, Takatsuji K, editors. 1998. Atlas of neuroactive substances and their receptors in the rat. Oxford: Oxford University Press. p 66-67.
58. 2 receptor alterations in the cerebral cortex of patients with senile dementia of the Alzheimer's type (SDAT). Int Congr Ser-Excerpta Med 750:83-86.
59. 2 muscarinic receptor antagonists. Bioorg Med Chem Lett 10:2247-2250.
60. 2 muscarinic receptor antagonists. Bioorg Med Chem Lett 11:891-894.
61. 2 muscarinic receptor antagonists. Chem Pharm Bull 46:53-68.
62. Whitehouse PJ, Price DL, Struble RG, Clarke AW, Coyle JT, Delong MR. 1982. Alzheimer's disease and senile dementia: loss of neurons in the basal forebrain. Science 215:1237-1239.
63. Wilkinson D, Murray J. 2001. Galantamine: a randomized, double-blind, dose comparison in patients with Alzheimer's disease. Int J Geriatr Psychiatry 16:852-857.
64. Zhang W, Basile AS, Gomeza J, Volpicelli LA, Levey AI, Wess J. 2002. Characterization of central inhibitory muscarinic autoreceptors by the use of muscarinic acetylcholine receptor knock-out mice. J Neurosci 22:1709-1717.