Aminopyridazines as acetylcholinesterase inhibitors

Journal of Medicinal Chemistry

Volumn 42, Issue 4, 1999, Pages 730-741

  Contreras, Jean Marie ^a   Rival, Yveline M ^a   Chayer, Said ^a   Bourguignon, Jean Jacques ^a   Wermuth, Camille G ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 [2 (1 BENZYLPIPERIDIN 4 YL)ETHYLAMINO] 6 PHENYLPYRAZIDINE; ACETYLCHOLINESTERASE; AMINOPYRIDINE DERIVATIVE; CHOLINESTERASE INHIBITOR; ISONIAZID; MINAPRINE; MUSCARINIC AGENT; RIVASTIGMINE; TACRINE; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ANIMAL TISSUE; ARTICLE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; NEUROTRANSMISSION; NONHUMAN; RAT; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINESTERASE; ANIMALS; BUTYRYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; HUMANS; NEOSTRIATUM; PIPERIDINES; PYRIDAZINES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033602139     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm981101z     Document Type: Article

References (59)

1. Wermuth, C. G.; Exinger, A. Le dichlorhydrate de la morpholinoéthylamino-3 méthyl-4 phényl-6 pyridazine (Agr 1240). The dihydrochloride of the morpholinoethylamino-3 methyl-4 phenyl-6 pyridazine (Agr 1240).) Agressologie 1972, 13, 285-289.
2. Davies, P.; Maloney, A. J. F. Selective Loss of Cholinergic Neurones in Alzheimer's Disease. Lancet 1976, 2, 1403.
3. Avery, E. E.; Baker, L. D.; Asthana, S. Potential Role of Muscarinic Agonists in Alzheimer's Disease. Drugs Agings 1997, 11, 450-459.
4. Brufani, M.; Filocamo, L.; Lappa, S.; Maggi, A. New Acetylcholinesterase Inhibitors. Drugs Future 1997, 22, 397-410.
5. Parnetti, L.; Senin, U.; Mecocci, P. Cognitive Enhancement Therapy for Alzheimer's Disease. The Way Forward. Drugs Future 1997, 53, 752-768.
6. Giacobini, E. From Molecular Structure to Alzheimer Therapy. Jpn. J. Pharmacol. 1997, 74, 225-241.
7. Garattini, S.; Forloni, G. L.; Tirelli, S.; Ladinsky, H.; Consolo, S. Neurochemical effects of minaprine, a novel psychotropic drug, on the central cholinergic system of the rat. Psychopharmacology 1984, 82, 210-214.
8. Wermuth, C. G.; Contreras, J. M.; Chayer, S.; Pinto, J.; Guilbaud, P.; Rival, Y.; Bourguignon, J. J. 3-Aminopyridazines as a Source of Acetylcholinesterase Inhibitors. Acta Pharm. Hung. 1996, S3-S8.
9. Kan, J. P.; Steinberg, R.; Oury-Donat, F.; Michaud, J. C.; Thurneyssen, O.; Terranova, J. P.; Gueudet, C.; Souilhac, J.; Brodin, R.; Boigegrain, R.; Wermuth, C. G.; Worms, P.; Soubrié, P.; Le Fur, G. SR 46559 A: A novel and Potent Muscarinic Compound with no Cholinergic Syndrome. Psychopharmacology 1993, 112, 219-227.
10. Wermuth, C. G.; Bourguignon, J. J.; Hoffmann, R.; Boigegrain, R.; Brodin, R.; Kan, J. P.; Soubrié, P. SR 46559 A and Related Aminopyridazines are Potent Muscarinic Agonists with no Cholinergic Syndrome. Bioorganic & Med. Chem. Lett. 1992, 2, 833-838.
11. Boigegrain, R.; Kan, J. P.; Olliero, D.; Brodin, R.; Soubrié, P.; Bourguignon, J. J.; Wermuth, C. G. SR 46559 A, an atypical muscarinic compound with no cholinergic syndrome: chemical approach and pharmacological profile. In Proceedings of the XIIIth International Symposium on Medicinal Chemistry, Paris 1994, Muller, J. C., Ed.; Elsevier: New York, 1994; Suppl. Eur. J. Med. Chem. 1995, 30, 175s-185s.
12. Boigegrain, R.; Kan, J. P.; Olliero, D.; Brodin, R.; Soubrié, P.; Bourguignon, J. J.; Wermuth, C. G. SR 46559 A, an atypical muscarinic compound with no cholinergic syndrome: chemical approach and pharmacological profile. In Proceedings of the XIIIth International Symposium on Medicinal Chemistry, Paris 1994, Muller, J. C., Ed.; Elsevier: New York, 1994; Suppl. Eur. J. Med. Chem. 1995, 30, 175s-185s.
13. Wermuth, C. G. Aminopyridazines - An alternative route to potent muscarinic agonists with no cholinergic syndrome. Farmaco, Ed. Sci. 1993, 48, 253-274.
14. Biniecki, S.; Gora, D.; Moll, M.; Rylski, L.; Gogolmska, B.; Kurowska, H.; Pindor, E. Certain Heterocyclic Derivatives of Phenethylamine. Acta Polon. Pharmacol. 1961, 18, 261-268.
15. Lespagnol, A.; Deprey, J. Pyridazine derivatives II. Bull. Soc. Chim. Fr. 1962, II, 1117-1122.
16. Leclerc, G.; Wermuth, C. G. Dérivés pyridaziniques présentant un intérêt thérapeutique. VIII. Action du méthylure de diméthylsulfoxonium sur les phényl-6 pyridazones-3. (Pyridazine Derivatives Presenting a Therapeutic Interest. VIII. Action of Dimethylsulfoxonium Methylide on 6-Phenyl-3(2H)pyridazones.) Bull. Soc. Chim. Fr. 1968, 10, 4123-4126.
17. Maghioros, G.; Schlewer, G.; Wermuth, C. G. Obtention sélective d'hydroxy-4 pyridazinones-3 et de pyridazones-3. Etude des modalités de la cyclocondensation des acides β-acyl lactiques avec l'hydrazine. (Selective Access to 4-Hydroxy-3(2H)pyridazinones and to 3(2H)pyridazones. Study of the Cyclocondensation Modalities of β-Acyl Lactic Acids with Hydrazine.) Bull. Soc. Chim. Fr. 1985, 5, 865-870.
18. Leclerc, G.; Wermuth, C. G. Dérivés pyridaziniques présentant un intérêt thérapeutique. X. Nouvelles synthèses au départ de la méthyl-4 phényl-6 pyridazone-3. (Pyridazine Derivatives Presenting a Therapeutic Interest. X. New Syntheses starting from 4-Methyl-6-phenyl-3(2H)pyridazone.) Bull. Soc. Chim. Fr. 1971, 5, 1752-1756.
19. Bourguignon, J. J.; Wermuth, C. G. Lactone Chemistry. Synthesis of β-Substituted, γ-Functionalized Butanolides and Butenolides and Succinaldehydic Acids from Glyoxylic Acid. J. Org. Chem. 1981, 46, 4889-4894.
20. Wermuth, C. G.; Schlewer, G.; Bourguignon, J.-J.; Maghioros, G.; Bouchet, M.-J.; Moire, C.; Kan, J.-P.; Worms, P.; Biziere, K. 3-Aminopyridazine Derivatives with Atypical Antidepressant, Serotonergic, and Dopaminergic Activities. J. Med. Chem. 1989, 32, 528-537.
21. Coates, W. J.; McKillop, A. One-Pot Preparation of 6-Substituted 3(2H)-Pyridazinones from Ketones. Synthesis 1993, 3, 334-342.
22. Ates, C.; Janoussek, Z.; Viehe, H. G. Trifluoroethylidenation of Compounds with Activated Methylene Groups. Tetrahedron Lett. 1993, 34, 5711-5714.
23. Church, R.; Trust, R.; Albright, J. D.; Powell, D. W. New Synthetic Routes to 3-, 5-, and 6-Aryl-2-chloropyridines. J. Org. Chem. 1995, 60, 3750-3758.
24. Bohne, H.; Jutz, C.; Viehe, H. G. Imminium Salts in Organic Chemistry; Wiley-Interscience: New York, 1976; Vol. 1.
25. Coppola, G.; Hardtmann, G. E.; Huegi, B. S. Synthesis and Reactions of 2-Aryl-3-(dimethylamino)acroleins. J. Heterocycl. Chem. 1974, 11, 51-56.
26. Coppola, G. M.; Fraser, J. D.; Hardtmann, G. E.; Huegi, B. S.; Kathawala, F. G. Pyrimidinones 1. Synthesis of some 1-Substituted-5-aryl-and (4,5-Diaryl)-2(1H) pyrimidinones. J. Heterocycl. Chem. 1979, 16, 545-554.
27. Coppola, G. M.; Hardtmann, G. E.; Huegi, B. S. Pyrimidinones 2. Synthesis and Reactions of 2-Chloropyrimidines. J. Heterocycl. Chem. 1980, 17, 1479-1482.
28. Andersen, T. P.; Ghattas, A. B. A.; Lawesson, S. O. Studies on Amino Acids and Peptides-IV-1,2,4-Triazines from Thioacylated Amino Acid Esters. Tetrahedron 1983, 39 (20), 3419-3427.
29. Fatiadi, A. J. Active Manganese Dioxide Oxidation in Organic Chemistry-Part I and Part II. Synthesis 1976, 65-104 and 133-167.
30. Sircar, I.; Duell, B. L.; Bobowski, G.; Bristol, J. A.; Evans, D. B. Cardiotonic Agents. 2. Synthesis and Structure-Activity Relationships of 4,5-Dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones: A New Class of Positive Inotropic Agents. J. Med. Chem. 1985, 28 (10), 1405-1413.
31. Saito, T.; Saheki, N.; Hatanaka, M.; Ishimaru, T. Synthesis of 1,3,4-Thiadiazol-2-ylacetic Acid Derivatives. J. Heterocycl. Chem. 1983, 20, 73-75.
32. Paudler, W. W.; Chen, T. K. 1,2,4-Triazines III. A Convenient Synthesis of 1,2,4-Triazines and Their Covalent Hydratation. J. Heterocycl. Chem. 1970, 7, 767-769.
33. 1A Serotonin Ligands. J. Med. Chem. 1988, 31, 1968-1971.
34. Dutta, A. K.; Xu, C.; Reith, M. E. A. Structure-Activity Relationship Studies of Novel 4-[2-[Bis(4-fluorophenyl)methoxy]-ethyl]-1-(3-phenylpropyl)piperidine Analogues: Synthesis and Biological Evaluation at the Dopamine and Serotonin Transporter Sites. J. Med. Chem. 1996, 39, 749-756.
35. Profitt, J. A.; Watt, D. S. A reagent for the α, β-Reduction of Conjugated Nitriles. J. Org. Chem. 1975, 40, 127-128.
36. Sussman, J. L.; Harel, M.; Frolow, F.; Oefner, C.; Goldman, A.; Toker, L.; Silman, I. Atomic Structure of Acetylcholinesterase from Torpedo californica: A Prototypic Acetylcholine-Binding Protein. Science 1991, 253, 872-879.
37. Ellman, G. L.; Courtney, K. D.; Andres, V.; Featherstone, J.; Featherstone, R. M. A New and Rapid Colorimetric Determination of Acetylcholinesterase Activity. Biochem. Pharmacol. 1961, 7, 88-95.
38. Freeman, S. E.; Dawson, R. M. Tacrine: A Pharmacological Review. Prog. Neurobiol. 1991, 36, 257-277.
39. Bryson, H. M.; Benfield, P. Donepezil. Drugs Aging 1997, 10, 234-239.
40. Sugimoto, H.; Iimura, Y.; Yamanishi, Y.; Yamatsu, K. Synthesis and Structure-Activity Relationship of Acetylcholinesterase Inhibitors: 1-Benzyl-4-[(5,6-dimethoxy-1-oxoindan-2-yl)methyl]-piperidine Hydrochloride and Related Compounds. J. Med. Chem. 1996, 38, 4821-4829.
41. Beylin, V. G.; Colbry, N. L.; Goel, O. P.; Haky, J. E.; Johnson, D. R.; Johnson, J. L.; Kanter, G. D.; Leeds, R. L.; Leja, B.; Anticancer Anthrapyrazoles. Improved Syntheses of Clinical Agents CI-937, CI-941 and Piroxanthrone Hydrochloride. J. Heterocycl. Chem. 1989, 26, 85-96.
42. Benarab, A.; Boye, S.; Savelon, L.; Guillaumet, G. Utilisation de Groupement Cyanométhyle Motif Protecteur des Phénols, Amines et Carbamates. (Utilization of the Cyanomethyl Group Motif Protector of Phenols, Amines, and Carbamates.) Tetrahedron Lett. 1993, 34, 7567-7568.
43. Surrey, A. R.; Olivet, A. J.; Hoppe, J. O. The Synthesis of Bisquaternary Salts of Some 1,7-Phenanthroline Derivatives. J. Am. Chem. Soc. 1954, 76, 4920-4923.
44. Mokrosz, J. L.; Dern-Wesolek, A.; Tatarczynska, E.; Duszynska, B.; Bojarski, A. J.; Mokrosz, M. J.; Chojnacka-Wojcik, E. 8-[4-[2-(1,2,3,4-tetrahydroisoquinolinyl)]butyl]-8-azaspiro[4.5]decane-7,9- dione: A New 5HT1A Receptor Ligand with the Same Activity Profile as Buspirone. J. Med. Chem. 1996, 39, 1125-1129.
45. Shapiro, S. L.; Rose, I. M.; Freedman, L. Aminoalkylamides and Oxazolidinediones. J. Am. Chem. Soc. 1959, 81, 3083-3088.
46. Ueda, T.; Ishizaki, K. Syntheses of (3-Aminopropyl)guanidine Derivatives. Chem. Pharm. Bull. 1967, 15, 228-232.
47. Finch, N.; Gemenden, C. W. Intramolecular Cyclization of N-(ω-Aminoalkyl)-1,2-dihydroisoqunolines. J. Org. Chem. 1973, 38, 437-440.
48. 14C]-N-methylputrescine. J. Labeled Compd. Radiopharm. 1994, 34, 421-426.
49. George, P.; Severin, M.; Mangane, M.; Merly, J. P.; Bigg, D. Dérivés de [(pipéridinyl-4)méthyl]-2-dihydro-2,3-1H-isoindole et tétrahydro-2,3,4,5-1H-benzazépines, leur préparation et leur application en thérapeutique; EP 0351 283, France, 1989.
50. Valenta, V.; Holubek, J.; Svatek, E.; Matousova, O.; Metysova, J.; Protiva, M. Potential Neuroleptics of the Orthopramide Series; Synthesis of Heterocyclic 5-Amino-2-methoxybenzamides and of Some Related Compounds. Collect. Czech. Chem. Commun. 1990, 55, 1297-1310.
51. Wagner, S.; Scheve, B. J. Absence of Intramolecular charge-transfer Quenching in Photoexcited 4-benzoylpiperidines. J. Am. Chem. Soc. 1977, 99, 1858-1862.
52. Eckhardt, W.; Grob, C. A. Synthese und Basizität 4-heterosubstituierter Chinuclidine. (Synthesis and Basicity of 4-Heterosubstituted Quinuclidines.) Helv. Chim. Acta 1974, 57, 2339-2345.
53. Garratt, P. J.; Doecke, C. W.; Weber, J. C.; Paquette, L. A. Intramolecular Anionic Cyclization to Capped [3]Peristylanes. J. Org. Chem. 1986, 51, 449-552.
54. Sugimoto, H.; Tsuchiya, Y.; Sugumi, H.; Higurashi, K.; Karibe, N.; Limura, Y.; Sasaki, A.; Kawakami, Y.; Nakumura, T.; Araki, S.; Yamanishi, Y.; Yamatsu, K. Novel Piperidine Derivatives. Synthesis and Anti-Acetylcholinesterase Activity of 1-Benzyl-4-[2-(N-benzoylamino)ethyl]piperidine Derivatives. J. Med. Chem. 1990, 33, 1880-1887.
55. New, J. S.; Yevich, J. P. Applications of Lithium Aluminium Hydride in the Synthesis of Substituted Ethyl-and Propylamines. Synthesis 1983, 388-389.
56. Beyer, H.; Liebenow, W.; Pyl, T. Thiazolyl-(2)-Hydrazone und Thiosemicarbazone Des p-Benzochinons. Chem. Ber. 1957, 90, 1738-1742.
57. Malinauskas, A. A.; Mozolis, V. V.; Gurkliene, M. P. Sulfoalkylation of Organosulfur Compounds. Zh. Org. Khim. 1988, 24, 1529-1531.
58. Arnaud-Neu, F.; Bourguignon, J. J.; Mehta, S. K.; Wermuth, C. G. Acid-base Characteristic 3-Alkylaminopyridazine derivatives. J. Chem. Res. Minipr. 1994, 120-139.
59. Bourguignon, J. J.; Wermuth, C. G.; Worms, P. Imidazo[1,2-b]-pyridazines, procédé pou leur préparation et compositions pharmaceutiques les contenant EP 0351 283, SANOFI, France, 1988.