The chemistry of catechol-O-methyltransferase inhibitors

International Review of Neurobiology

Volumn 95, Issue C, 2010, Pages 119-162

  Learmonth, David A ^a   Kiss, László E ^a   Soares da Silva, Patrício ^a  

^a DEPARTMENT OF RESEARCH AND DEVELOPMENT   (Portugal)

Author keywords

COMT inhibitors; L dopa; Medicinal chemistry; Parkinson's disease; Physicochemical properties; Selectivity; Toxicity

Indexed keywords

(3,4 DIHYDROXY 2 NITROPHENYL)(PHENYL)METHANONE; 1 (3 HYDROXY 4 METHOXY 5 NITROPHENYL) 2 PHENYLETHANONE; 1 (3,4 DIHYDROXY 5 NITROPHENYL) 2 PHENYLETHANONE; 1 (3,4 DIHYDROXY 5 NITROPHENYL) 3 [4 (3 (TRIFLUOROMETHYL)PHENYL)PIPERAZIN 1 YL]PROPAN 1 ONE HYDROCHLORIDE; 1 (4 HYDROXY 3 METHOXY 5 NITROPHENYL) 2 PHENYLETHANONE; 2' FLUORO 3,4 DIHYDROXY 5 NITROBENZOPHENONE; 3',4' DIHYDROXY 2 METHYLPROPIOPHENONE; 3,5 DINITROPYROCATECHOL; BENSERAZIDE; BIA 3 335; BIA 3 465; BIA 3 467; BIA 3 475; BIA 8 176; BIA 8 477; CARBAMIC ACID DERIVATIVE; CARBIDOPA; CATECHOL METHYLTRANSFERASE; CATECHOL METHYLTRANSFERASE INHIBITOR; ENTACAPONE; ENZYME INHIBITOR; GLUCURONIDE; LEVODOPA; METHYLTRANSFERASE INHIBITOR; N (6 OXO 1H PYRID 2 YL) N',N' DIPROPYLFORMAMIDINE; NEBICAPONE; NITECAPONE; O BETA DEXTRO GLUCURONIDE; PYROGALLOL; QUERCETIN; TOLCAPONE; TRANSFERASE INHIBITOR; TROPOLONE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AREA UNDER THE CURVE; BOOK; CLINICAL TRIAL; DOSE RESPONSE; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG DISTRIBUTION; DRUG DOSE INCREASE; DRUG HALF LIFE; DRUG MECHANISM; DRUG MEGADOSE; DRUG PENETRATION; DRUG POTENCY; DRUG RESEARCH; DRUG SCREENING; DRUG SOLUBILITY; DRUG STRUCTURE; HUMAN; LIPOPHILICITY; LIVER FAILURE; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; PARKINSON DISEASE; PARKINSONISM; PHYSIOLOGICAL PROCESS; PRIORITY JOURNAL; PROTEIN FUNCTION; PROTEIN STRUCTURE; STRUCTURE ACTIVITY RELATION;

EID: 78649390863     PISSN: 00747742     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-381326-8.00006-5     Document Type: Chapter

References (117)

1. Ahlmark, M., Bäckström, R., Luiro, A., Pystynen, J., and Tiainen, E. (2007). New pharmaceutical compounds. WO2007/010085 A2.
2. Alewood P.F., Johns R.B., Valerio R.M., Kemp B.E. A simple preparation of O-phospho-L-tyrosine. Synthesis 1983, 1:30.
3. Almeida L., Soares-da-Silva P. Pharmacokinetics and pharmacodynamics of BIA 3-202, a novel COMT inhibitor, during first administration to humans. Drugs in R&D 2003, 4:207-217.
4. Almeida L., Soares-da-Silva P. Pharmacokinetic and pharmacodynamic profiles of BIA 3-202, a novel catechol-O-methyltransferase (COMT) inhibitor, during multiple-dose administration to healthy subjects. J. Clin. Pharmacol. 2003, 43:1350-1360.
5. Archer S., Arnold A., Kullnig R.K., Wylie D. The enzymic methylation of pyrogallol. Arch. Biochem. Biophys. 1960, 87:153-154.
6. Axelrod J., LaRoche M.-J. Inhibitor of O-methylation of epinephrine and norepinephrine in vitro and in vivo. Science 1959, 130:800.
7. Axelrod J., Senoh S., Witkop B. O-Methylation of catecholamines in vivo. J. Biol. Chem. 1958, 233:697-701.
8. Axelrod J., Tomchick R. Enzymatic O-methylation of epinephrine and other catechols. J. Biol. Chem. 1958, 233:702-705.
9. Bäckström R., Honkanen E., Pippuri A., Kairisalo P., Pystynen J., Heinola K., Nissinen E., Linden I.B., Männist P.T., Kaakkola S., Pohto P. Synthesis of some novel potent and selective inhibitors of catechol-O-methyltransferase. J. Med. Chem. 1989, 32:841-846.
10. Bäckström, R., Pystynen, J., Lotta, T., Ovaska, M., and Taskinen, J. (2002). Derivatives of naphthalene with COMT inhibiting activity. WO2002/22551 A1.
11. Bäckström, R.J., Heinola, K.E., Honkanen, E.J., Kaakola, S.K., Kairisalo, P.J., Linden, I.-B.Y., Männistö, P.T., Nissinen, E.A.O., Pohto, P., Pipurri, A.K., and Pystynen, J.J. (1990). Pharmacologically active compounds, methods for the preparation thereof and compositions containing the same. US Patent 4,963,590.
12. Bäckström, R.J., Heinola, K.E., Honkanen, E.J., Kaakola, S.K., Kairisalo, P.J., Linden, I.-B.Y., Männistö, P.T., Nissinen, E.A.O., Pohto, P., Pipurri, A.K., and Pystynen, J.J. (1995). Pharmacologically active catechol derivatives. US Patent 5,446,194.
13. Bacq Z.M., Gosselin L., Dresse A., Renson J. Inhibition of O-methyltransferase by catechol and sensitization to epinephrine. Science 1959, 130:453-454.
14. Bader, T., Furegati, M., and Jungmann, O. (2008). Novel crystalline forms of entacapone and production thereof. US2008/0076825 A1.
15. Bailey K., Tan E.W. Synthesis and evaluation of bifunctional nitrocatechol inhibitors of pig liver catechol-O-methyltransferase. Bioorg. Med. Chem 2005, 13:5740-5749.
16. Belleau B., Burba J. Tropolones: a unique class of potent non-competitive inhibitors of S-adenosylmethionine-catechol methyltransferase. Biochim. Biophys. Acta 1961, 54:195-196.
17. Belleau B., Burba J. Occupancy of adrenergic receptors and inhibition of catechol-O-methyltransferase by tropolones. J. Med. Chem 1963, 6:755-759.
18. Bernauer, K., Borgulya, J., Bruderer, H., Da Prada, M., and Zürcher, G. (1993). Catechol derivatives. US Patent 5,236,952.
19. Bernauer, K., Borgulya, J., Bruderer, H., Da Prada, M., and Zürcher, G. (1995a). Catechol derivatives. US Patent 5,389,653.
20. Bernauer, K., Borgulya, J., Bruderer, H., Da Prada, M., and Zürcher, G. (1995b). Catechol derivatives. US Patent 5,476,875.
21. Bernauer, K., Borgulya, J., Bruderer, H., Da Prada, M., and Zürcher, G. (1997). Catechol derivatives. US Patent 5,633,371.
22. Bernauer, K., Borgulya, J., Bruderer, H., Da Prada, M., and Zürcher, G. (1998). Catechol derivatives. US Patent 5,705,703.
23. Bonifácio M.J., Archer M., Rodrigues M.L., Matias P.M., Learmonth D.A., Carrondo M.A., Soares-Da-Silva P. Kinetics and crystal structure of catechol-O-methyltransferase complex with co-substrate and a novel inhibitor with potential therapeutic application. Mol. Pharmacol. 2002, 62:795-805.
24. Bonifácio M.J., Vieira-Coelho M.A., Soares-da-Silva P. Kinetic inhibitory profile of BIA 3-202, a novel fast tight-binding, reversible and competitive catechol-O-methyltransferase inhibitor. Eur. J. Pharmacol 2003, 460:163-170.
25. Booth A.N., Masri M., Robbins D.J., Emerson O.H., Jones F.T., Deeds F. The metabolic fate of gallic acid and related compounds. J. Biol. Chem. 1959, 234:3014-3016.
26. Borchardt R.T. Catechol-O-methyltransferase. 4. In vitro inhibition by 3-hydroxy-4-pyrones, 3-hydroxy-2-pyridones and 3-hydroxy-4-pyridones. J. Med. Chem. 1973, 16:581-583.
27. Borchardt R.T. Catechol-O-methyltransferase. 2. In vitro inhibition by substituted 8-hydroxyquinolines. J. Med. Chem. 1973, 16:382-386.
28. Borges N. Tolcapone in Parkinson's disease: liver toxicity and clinical efficacy. Expert Opin. Drug Saf. 2005, 41:69-73.
29. Borgulya J., Bruderer H., Bernauer K., Zurcher G., Da Prada M. Catechol-O-methyltransferase-inhibiting pyrocatechol derivatives: synthesis and structure-activity studies. Helv Chim. Acta 1989, 72:952-968.
30. Borgulya J., Da Prada M., Dingemanse J., Scherschlicht R., Schäppl B., Zürcher G. Ro40-7592 (3,4-dihydroxy-4'-methyl-5-nitrobenzophenone), catecholamine-O-methyltransferase (COMT) inhibitor. Drugs Future 1991, 16:719-721.
31. Brevitt S.E., Tan E.W. Synthesis and in vitro evaluation of two progressive series of bifunctional polyhdroxybenzamide catechol-O-methyltransferase inhibitors. J. Med. Chem. 1997, 40:2035-2039.
32. Broch O.J. The in vivo effect of tropolone on noradrenaline metabolism and catechol-O-methyltransferase activity in the striatum of the rat. Acta Pharmacol. Toxicol. 1973, 33:417-428.
33. Burke T.R., Barchi J.J., George C., Wolf G., Schoelson S.E., Yan X. Conformationally restrained phosphotyrosyl mimetics designed as monomeric Src homology 2 domain inhibitors. J. Med. Chem. 1995, 38:1386-1396.
34. Chen D., Wang C.Y., Lambert J.D., Ai N., Welsh W.J., Yang C.S. Inhibition of human liver catechol-O-methyltransferase by tea catechins and their metabolites: structure-activity relationship and molecular modeling studies. Biochem. Pharmacol. 2005, 69:1523-1531.
35. Crout J.R., Creveling C.R., Udenfriend S. Norepinephrine metabolism in rat brain and heart. J. Pharmacol. Exp. Ther. 1961, 132:269-277.
36. Despande, P.B., Luthra, P.K., Pandey, A.K., and Darmesh, D.R. (2006). Process for the preparation of (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide (entacapone). US2006/0258877 A1.
37. Ding Y.-S., Sugano Y., Koomen D., Aggarwal D. Synthesis of [18F]-Ro41-0960, a potent catechol-O-methyltransferase inhibitor, for PET studies. J. Labelled Comp. Radiopharm. 1997, 39:303-318.
38. Ferreira J., Rosa M.M., Coelho M., Cunha L., Januario C., Machado C., Morgadinho A., Ticmeanu M., Mitu C.-E., Novac M. A double-blind, randomised, placebo- and entacapone-controlled study to investigate the effect of nebicapone (BIA 3-202) on the levodopa pharmacokinetics, COMT activity and motor response in Parkinson disease patients. Mov. Disord. 2006, 21(Suppl. 15):S644-S645.
39. Giles R.E., Miller J.W. The catechol-O-methyltransferase activity and endogenous catecholamine content of various tissues in the rat and the effect of administration of U-0521 (3,4-dihydroxy-2-methylpropiophenone). J. Pharmacol. Exp. Ther. 1967, 158:189-194.
40. Gugler R., Dengler H.J. Inhibition of liver catechol-O-methyltransferase by flavanoids. Naunyn Schmiedebergs Arch. Exp. Pathol. Pharmakol. 1973, 201:353-361.
41. Guldberg H.C., Marsden C.A. Catechol-O-methyltransferase:pharmacological aspects and physiological role. Pharmacol. Rev. 1975, 27:135-206.
42. Haasio K., Koponen A., Pentilla K.E., Nissinen E. Effects of entacapone and tolcapone on mitochondrial membrane potential. Eur. J. Pharmacol 2002, 453:21-26.
43. Jorga K., Fotteler B., Heizmann P., Gasser R. Metabolism and excretion of tolcapone, a novel inhibitor of catechol-O-methyltransferase. Br. J. Clin. Pharmacol. 1999, 48:513-520.
44. Jorga K.M., Fotteler B., Heizmann P., Zürcher G. Pharmacokinetics and pharmacodynamics after oral and intravenous administration of tolcapone, a novel adjunct to Parkinson's disease therapy. Eur. J. Clin. Pharmacol. 1998, 54:443-447.
45. Kaakkola S., Wurtman R.J. Effects of COMT inhibitors on striatal dopamine metabolism: a microdialysis study. Brain Res. 1992, 587:241-249.
46. Kahn K., Bruice T.C. Transition-state and ground-state structures and their interaction with the active-site residues in catechol-O-methyl transferase. J. Am. Chem. Soc. 2000, 122:46-51.
47. Keränen T., Gordin A., Karlsson M., Korpela K., Pentikäinen P.J., Rita H., Schultz E., Seppäl L., Wikberg T. Inhibition of soluble catechol-O-methyltransferase and single-dose pharmacokinetics after oral and intravenous administration of entacapone. Eur. J. Clin. Pharmacol 1994, 46:151-157..
48. Korlipara L.P., Cooper J.M., Schapira A.H. Differences in toxicity of the catechol-O-methyltransferase inhibitors, tolcapone and entacapone to cultured human neuroblastoma cells. Neuropharmacology 2004, 46:562-569.
49. Kuhn B., Kollman P.A. QM-FE and molecular dynamics calculations on catechol-O-methyltransferase: free energy of activation in the enzyme and in aqueous solution and regioselectivity of the enzyme-catalyzed reaction. J. Am. Chem. Soc. 2000, 122:2586-2596.
50. Lautala P., Ulmanen I., Taskinen J. Molecular mechanisms controlling the rate and specificity of catechol-O-methylation by human soluble catechol-O-methyltransferase. Mol. Pharmacol. 2001, 59:393-402.
51. Learmonth D.A., Bonifácio M.J., Soares-da-Silva P. Synthesis and biological evaluation of a novel series of "ortho-nitrated" inhibitors of catechol-O-methyltransferase. J. Med. Chem. 2005, 48:8070-8078.
52. Learmonth, D.A., Kiss, L.E., Palma, P.N., Ferreira, H., and Soares-da-Silva, P. (2007). Nitrocatechol derivatives as COMT inhibitors. WO2007/013830 A1.
53. Learmonth D.A., Palma P.N., Vieira-Coelho M.A., Soares-da-Silva P. Synthesis, biological evaluation, and molecular modeling Studies of a novel, peripherally selective inhibitor of catechol-O-methyltransferase. J. Med. Chem 2004, 47:6207-6217.
54. Learmonth D.A., Vieira-Coelho M.A., Benes J., Alves P.C., Borges N., Freitas A.P., Soares-da-Silva P. Synthesis of 1-(3,4-dihydroxy-5-nitrophenyl)-2-phenyl-ethanone and derivatives as potent and long-acting peripheral inhibitors of catechol-O-methyltransferase. J. Med. Chem. 2002, 45:685-695.
55. Lee C.-P., de Vrueh R.L.A., Smith P.L. Selection of developmentcandidates based on in vitro permeability measurements. Adv. Drug Deliv. Rev. 1997, 23:47-62.
56. Leppänen J., Huuskonen J., Nevalainen T., Gynther J., Taipale H., Järvinen T. Design and synthesis of a novel L-dopa-entacapone codrug. J. Med. Chem. 2002, 45:1379-1382.
57. Leppänen J., Huuskonen J., Savolainen J., Nevalainen T., Taipale H., Vepsäläinen J., Gynther J., Järvinen T. Synthesis of a water-soluble prodrug of entacapone. Biorg. Med. Chem. Lett. 2000, 10:1967-1969.
58. Leppänen J., Savolainen J., Nevalainen T., Forsberg M., Huuskonen J., Taipale H., Gynther J., Männist P.T., Järvinen T. Synthesis and in-vitro/in-vivo evaluation of orally administered entacapone prodrugs. J. Pharm. Pharmacol. 2001, 53:1489-1498.
59. Lerner C., Masjost B., Ruf A., Gramlich V., Jakob-Roetne R., Zürcher G., Borroni E., Diederich F. Bisubstrate inhibitors for the enzyme catechol-O-methyltransferase (COMT): influence of inhibitor preorganisation and linker length between the two substrate moieties on binding affinity. Org. Biomol. Chem. 2003, 1:42-49.
60. Lerner C., Ruf A., Gramlich V., Masjost B., Zürcher G., Jakob-Roetne R., Borroni E., Diederich F. X-ray crystal structure of a bisubstrate inhibitor bound to enzyme catechol-O-methyltransferase: a dramatic effect of inhibitor preorganization on binding affinity. Angew. Chem. Int. Ed. 2001, 40:4040-4042.
61. Lotta T., Taskinen J., Bäckström R., Nissinen E. PLS modelling of structure-activity relationships of catechol-O-methyltransferase inhibitors. J. Comput. Aided Mol. Des. 1992, 6:253-272.
62. Lotta T., Vidgren J., Tilgmann C., Ulmanen I., Melen K., Julkunen I., Taskinen J. Kinetics of human soluble and membrane-bound catechol-O-methyltransferase: a revised mechanism and description of the thermolabile variant of the enzyme. Biochemistry 1995, 34:4202-4210.
63. Loureiro A.I., Bonifácio M.J., Fernandes-Lopes C., Almeida L., Wright L.C., Soares-Da-Silva P. Human metabolism of nebicapone (BIA 3-202), a novel catechol-O-methyltransferase inhibitor: characterization of in vitro glucuronidation. Drug Metab. Dispos. 2006, 34(11):1856-1862.
64. Lutz W.B., Creveling C.R., Daly J.W., Witkop B., Goldberg L.I. Sulfur analogues of dopamine and norepinephrine. Inhibition of catechol-O-methyltransferase. J. Med. Chem 1972, 15:795-802.
65. Manikumar G., Jin C., Rehder K.S. Convenient synthesis oftolcapone, a selective catechol-O-methyltransferase inhibitor. Synth. Commun. 2008, 38:810-815.
66. Mantegazza, S., Allegrini, P., and Razzetti, G. (2008). Process for the preparation ofentacapone. US2008/0146829 A1.
67. Masjost B., Ballmer P., Borroni E., Zürcher G., Winkler F.K., Jakob-Roetne R., Diederich F. Structure-based design, synthesis and in vitro evaluation of bisubstrate inhibitors for catechol-O-methyltransferase (COMT). Chem. Eur. J. 2000, 6:971-982.
68. Maître L. Effects of long-term administration of pyrogallol on tissue catecholamine levels, monoamine oxidase and catechol-O-methyltransferase activities in the rat. Biochem. Pharmacol. 1966, 15:1935-1945.
69. Männistö P.T., Kaakola S. Rationale for selective COMT inhibitors as adjuncts in the drug treatment of Parkinson's disease. Pharmacol. Toxicol. 1990, 66:317-323.
70. Männist P.T., Tuomainen T., Tuomainen R.K. Different in vivo properties of three new inhibitors of catechol-O-methyltransferase in the rat. Br. J. Pharmacol. 1992, 105:569-574.
71. Mukarram, S.M., Khan, R.A., Yadav, R.P., and Shaikh, Z.G. (2008). Stable polymorphs of (E)-N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide. US2008/0004343.
72. Nicolau, F.E., Ponce, A.M., Garcia, G.R., Benet-Buchholz, J., and Sola, L.C. (2008). New crystalline form of entacapone and process for its preparation. WO2008/058992 A1.
73. Nicolau, F.E., Ponce, A.M., Garcia, G.R., Benet-Buchholz, J., and Sola, L.C. (2009). Process for preparing entacapone substantially free of Z-isomer, synthesis intermediates thereof and a new crystalline form. US2009/0326062 A1.
74. Nissinen E., Kaheinen P., Pentilla K.E., Kaivola K., Linden I.B. Entacapone, a novel catechol-O-methyltransferase inhibitor for Parkinson's disease, does not impair mitochondrial energy production. Eur. J. Pharmacol. 1997, 340:287-294.
75. Nissinen E., Linden I.B., Schultz E., Kaakkola S., Männist P.T., Pohto P. Inhibition of catechol-O-methyltransferase activity by two novel disubstituted catechols in the rat. Eur. J. Pharmacol 1988, 153:263-269.
76. Nissinen E., Linden I.B., Schultz E., Pohto P. Biochemical and pharmacological properties of a peripherally acting catechol-O-methyltransferase inhibitor entacapone. Naunyn Schmiedebergs Arch. Pharmacol. 1992, 346:262-266.
77. Novaroli L., Doulakas G.B., Reist M., Rolando B., Fruttero R., Gasco A., Carrupt P.-A. The lipophilicity behaviour of three catechol-O-methyltransferase (COMT) inhibitors and simple analogues. Helv. Chim. Acta 2006, 89:144-152.
78. Olanow C.W. Tolcapone and hepatotoxic effects. Arch. Neurol. 2000, 57:263-267.
79. Palma P.N., Bonifácio M.J., Loureiro A.I., Wright L.C., Learmonth D.A., Soares-da- Silva P. Molecular modeling and metabolic studies of the interaction of catechol-O- methyltransferase and a new nitrocatechol inhibitor. Drug Metab. Dispos. 2003, 31(3):250-258.
80. Palma P.N., Rodrigues M.L., Archer M., Bonifácio M.J., Loureiro A.I., Learmonth D.A., Carrondo M.A., Soares-da-Silva P. Comparative study of ortho-and meta-nitrated inhibitors of catechol-O-methyltransferase. Interactions with the active site and regioselectivity of O-methylation. Mol. Pharmacol. 2006, 70:143-153.
81. Paulini R., Lerner C., Jakob-Roetne R., Zürcher G., Borroni E., Diederich F. Bisubstrate inhibitors of the enzyme catechol-O-methyltransferase (COMT): efficient inhibition despite the lack of a nitro group. Chem. Biochem. 2004, 5:1270-1274.
82. Pérez R.A., Fernández-Alvarez E., Nieto O., Piedrafita F.J. Dihydroxynitrobenzaldehydes and hydroxymethoxynitrobenzaldehydes: synthesis and biological activity as catechol-O-methyltransferase inhibitors. J. Med. Chem. 1992, 35:4584-4588.
83. Pérez R.A., Fernández-Alvarez E., Nieto O., Piedrafita F.J. Inhibition of catechol-O-methyltransferase by 1-vinyl derivatives of nitrocatechols and nitroguaiacols. Kinetics of the irreversible inhibition by 3-(3-hydroxy-4-methoxy-5-nitro benzylidene)-2,4-pentanedione. Biochem. Pharmacol. 1993, 45:1973-1981.
84. Pérez R.A., Fernández-Alvarez E., Nieto O., Piedrafita F.J. Kinetics of the reversible tight-binding inhibition of pig liver catechol-O-methyltransferase by [2-(3,4-dihydroxy-2-nitrophenyl)vinyl]phenyl ketone. J. Enzyme Inhib. 1994, 8:123-131.
85. Pippuri, A.K., Honkanen, E.J., and Haarala, J.V. (1992). Stable polymorphic form of (E)-N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide and the process for its preparation. US Patent 5,135,950.
86. Prous J., Rabasseda X., Castañer J. Entacapone. Drugs Future 1994, 19:641-645.
87. Pystynen, J., Ovaska, M., Vidgren, J., Lotta, T., and Yliperttula-ikonen, M. (2002). Coumarin derivatives with COMT inhibiting activity. WO2002/02548 A1.
88. Ramakrishnan, A., Bathani, G., and Taduri, S. (2009). An improved process for preparation of (2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)N,N-diethyl-2-propenamide polymorphic Form A. WO2009/084031 A2.
89. Reches A., Fahn S. Catechol-O-methyltransferase and Parkinson's disease. Adv. Neurol. 1984, 40:171-179.
90. Rice P.J., Abraham S.T., Huang N.Y., Doman R.J. Extraneuronal uptake inhibitor U-0521 decreases contractile responses in rat vas deferens. Gen. Pharmacol. 1997, 29:437-439.
91. Rivas E., de Ceballos M.L., Nieto O., Fontenla J.A. In vivo effects of new inhibitors of catechol-O-methyltransferase. Br. J. Pharmacol. 1999, 126:1667-1673.
92. Rodrigues M.L., Archer M., Bonifácio M.J., Soares-da-Silva P., Carrondo M.A. Crystallization and preliminary crystallographic characterization of catechol-O-methyltransferase in complex with its co-substrate and an inhibitor. Acta Crystallogr. 2001, D57(6):906-908.
93. Rodrigues M.L., Bonifácio M.J., Soares-da-Silva P., Carrondo M.A., Archer M. Crystallization and preliminary X-ray diffraction studies of a catechol-O- methyltransferase/inhibitor complex. Acta Crystallogr. F 2005, 61(1):118-120.
94. Ross S.B., Haljasmaa Ø. Catechol-O-methyltransferase inhibitors. In vivo inhibition in mice. Acta. Pharmacol. Toxicol. 1964, 21:215-225.
95. Sanmarti, M.B., Rocabert, J.G., Nicolau, F.E., and Ponce, A.M. (2008). Process for the preparation of entacapone and intermediates thereof. WO2008/119793 A1.
96. Savolainen J., Forsberg M., Taipale H., Männist P.T., Järvinen K., Gynther J., Jarho P., Järvinen T. Effects of aqueous solubility and dissolution characteristics on oral bioavailability of entacapone. Drug. Dev. Res. 2000, 49:238-244.
97. Savolainen J., Leppänen J., Forsberg M., Taipale H., Nevalainen T., Huuskonen J., Gynther J., Männist P.T., Järvinen T. Synthesis and in vitro/in vivo evaluation of novel oral N-alkyl and N,N-dialkyl-carbamate esters of entacapone. Life Sci. 2000, 67:205-206.
98. Semec, D.S., Marinkovic, M., Siljkovic, Z., and Horvat, M. (2007). New forms of active pharmaceutical ingredient. WO2007/135406 A2.
99. Sharpless N.S., McCann D.S. Dopa and 3-O-methyldopa in the cerebrospinal fluid of parkinsonism patients during treatment with oral L-dopa. Clin. Chim. Acta 1971, 31:155-169.
100. Sigurdsson S.T., Seeger B., Kutzke U., Eckstein F.A. A mild and simple method for the preparation of isocyanates from aliphatic amines using trichloromethyl chloroformate. Synthesis of an isocyanate containing an activated disulfide. J. Org. Chem. 1996, 61:3883-3884.
101. Silveira P., Vaz-Da-Silva M., Almeida L., Maia J., Falcão A., Loureiro A., Torrão L., Machado R., Wright L., Soares-da-Silva P. Pharmacokinetic-pharmacodynamic interaction between BIA 3-202, a novel COMT inhibitor, and levodopa/benserazide. Eur. J. Clin. Pharmacol. 2003, 59:603-609.
102. Sipila J., Taskinen J. CoMFA modeling of human catechol-O-methyltransferase enzyme kinetics. J. Chem. Inf. Comput. Sci. 2004, 44:97-104.
103. Smith K.S., Smith P.L., Heady T.N., Trugman J.M., Harman W.D., MacDonald T.L. In vitro metabolism of tolcapone to reactive intermediates: relevance to tolcapone liver toxicity. Chem. Res. Toxicol. 2003, 16:123-128.
104. Tarur, V.T., Sathe, D.G., Bhise, N.B., Naidu, A.V., Aher, U.P., and Patil, S.S. (2008). Process for the preparation of highly pure (E)- N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide (entacapone). US2008/0319226 A1.
105. Taskinen J., Vidgren J., Ovaska M., Bäckström R., Pippuri A., Nissinen E. QSAR and binding model for inhibition of rat liver catechol-O-methyltransferase by 1,5-substituted-3,4-dihydroxybenzenes. Quant. Struct. Act. Relat. 1989, 8:210-213.
106. Venkateswarlu, J., Reddy, A.V., Rajendiran, C., and Samjuddin, M.M. (2007).Methods for the preparation of entacapone. US2007/0060767 A1.
107. Vidgren J., Svensson L.A., Liljas A. Crystal structure of catechol-O-methyltransferase. Nature 1994, 368:354-358.
108. Vidgren J., Tilgmann C., Lundström K., Liljas A. Crystallisation and preliminary X-ray investigation of a recombinant form of catechol-O-methyltransferase. Proteins 1991, 11:233-236.
109. Waldmeier P.C., Baumann P.A., Feldtrauer J.J., Hauser K., Bittiger H., Bischoff S., von Sprecher G. CGP 28014, a new inhibitor of cerebral catechol-O-methylation with a non-catechol structure. Naunyn Schmiedebergs Arch. Pharmacol. 1990, 342:305-311.
110. Waldmeier P.C., De Herdt P., Maître L. Effects of the COMTinhibitor, CGP 28014, on plasma homovanillic acid and O-methylation of exogenous L-dopa in the rat. J. Neural Transm. Suppl. 1990, 32:381-386.
111. Wikberg T., Vuorela A., Ottoila P., Taskinen J. Identification of major metabolites of the catechol-O-methyltransferase inhibitor entacapone in rats and humans. Drug Metab. Dispos. 1993, 21:81-92.
112. Woodard R.W., Tsai M.D., Floss H.G., Crooks P.A., Coward J.K. Stereochemical course of the transmethylation catalyzed by catechol-O-methyltransferase. J. Biol. Chem. 1980, 255:9124-9127.
113. Yadav, R.P., Shaikh, Z.G., and Mukarram, S.M. (2008). Processes for the preparation of a stable polymorphic form of entacapone. WO2008/053304 A2.
114. Zheng Y.J., Bruice T.C. A theoretical examination of the factors controlling the catalytic efficiency of a transmethylation enzyme-catechol-O-methyltransferase. J. Am. Chem. Soc. 1997, 119:8137-8145.
115. Zhu B.T., Patel U.K., Cai M.X.X., Conney A.H. O-Methylation of tea polyphenols catalyzed by human placental cytosolic catechol-O-methyltransferase. Drug Metab. Dispos. 2000, 28:1024-1030.
116. Zürcher G., Colzi A., Da Prada M. Inhibition of COMT in rat brain and extracellular tissues. J. Neural Transm. Suppl. 1990, 32:375-380.
117. Zürcher G., Dingemanse J., Da Prada M. Potent COMT inhibition by Ro40-7592 in the periphery and in the brain: preclinical and clinical findings. Adv. Neurol 1993, 60:641-647.