Process research for multikilogram production of etamicastat: A novel dopamine β-hydroxylase inhibitor

Organic Process Research and Development

Volumn 16, Issue 4, 2012, Pages 704-709

  Beliaev, Alexandre ^a   Wahnon, Jorge ^a   Russo, Domenico ^a  

^a DEPARTMENT OF RESEARCH AND DEVELOPMENT   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC HYDROGENATION; HYDROXYLASES; SYNTHETIC APPROACH; SYNTHETIC STRATEGIES;

HYDROGENATION;

EID: 84860185974     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op300012d     Document Type: Article

References (30)

1. Beliaev, A.; Ferreira, H.; Learmonth, D. L.; Soares-da-Silva, P. Dopamine β-monooxygenase: mechanism, substrates and inhibitors Curr. Enzyme Inhib. 2009, 5, 27
2. Rocha, J. F.; Vaz-da-Silva, M.; Nunes, T.; Igreja, B.; Loureiro, A. I.; Bonifácio, M. J.; Wright, L. C.; Falcão, A.; Almeida, L.; Soares-da-Silva, P. Single-Dose Tolerability, Pharmacokinetics, and Pharmacodynamics of Etamicastat (BIA 5-453), a New Dopamine β-Hydroxylase Inhibitor, in Healthy Subjects J. Clin. Pharmacol. 2011, 10.1177/ 0091270010390805
3. Beliaev, A.; Learmonth, D. A.; Soares-da-Silva, P. Synthesis and biological evaluation of novel, peripherally selective chromanyl imidazolethione-based inhibitors of dopamine β-hydroxylase J. Med. Chem. 2006, 49, 1191
4. Cherney, R. L.; Wang, L. Efficient Mitsunobu Reactions with N -Phenylfluorenyl or N -Trityl Serine Esters J. Org. Chem. 1996, 61, 2544
5. McClure, D. E.; Arison, B. H.; Jones, J. H.; Baldwin, J. J. Chiral α-Amino Ketones from the Friedel-Crafts Reaction of Protected Amino Acids J. Org. Chem. 1981, 46, 2431
6. Martinez, G. R.; Gooding, O. W.; Repke, D. B.; Teitelbaum, P. J.; Walker, K. A. M.; Whiting, R. L. Benzocycloalkylazolethione derivatives. U.S. Patent 5,538,988, 1996.
7. Shiba, T.; Akiyama, H.; Umeda, I.; Okada, S.; Wakamiya, T. Synthesis and stereochemistry of hypusine, a new amino acid in bovine brain Bull. Chem. Soc. Jpn. 1982, 55, 899
8. Sarda, N.; Grouiller, A.; Pacheco, H. Nouvelle synthese de l'amino-3-chromanne. Synthese et configuration absolue de ses enantiomeres Tetrahedron Lett. 1976, 271
9. Norlander, E. J.; Njoroge, F. G.; Payne, M. J.; Warman, D. N -(Trifluoroacetyl)-α-amino Acid Chlorides As Chiral Reagents for Friedel-Crafts Synthesis J. Org. Chem. 1985, 50, 3481
10. Norlander, E. J.; Payne, M. J.; Njoroge, F. G.; Balk, M. A.; Laikos, G. D.; Vishvanath, V. M. Friedel-Crafts acylation with N -(Trifluoroacetyl)- α-amino Acid Chlorides. Application to the Preparation of β-Arylalkylamines and 3-Substituted 1,2,3,4-Tetrahydroisoquinolines J. Org. Chem. 1984, 49, 4107
11. Yato, M.; Homma, K.; Ishida, A. New silane reduction of aromatic ketones mediated by titanium tetrachloride: a synthesis of γ- and δ-aryl substituted amino acids Heterocycles 1998, 49, 233
12. Perry, P. J.; Pavlidis, V. H.; Coutts, I. G. C. The rapid reduction of α,α-diaryl alcohols to the corresponding alkanes using iodotrimethylsilane Synth. Commun. 1996, 26, 101
13. Pettit, G. R.; Piatak, D. M. Steroids and Related Natural Products. XI. Reduction of Esters to Ethers J. Org. Chem. 1962, 27, 2127
14. Cain, G. A.; Holler, E. R. Extended scope of in situ iodotrimethysilane mediated selective reduction of benzylic alcohols Chem. Commun. 2001, 1168
15. Learmonth, D. A.; Beliaev, A. Process for preparing chroman derivatives. PCT Int. Appl. WO/2008/143540A1, 2008.
16. Broadbelt, B.; Beliaev, A.; Learmonth, D. A. Process. PCT Int. Appl. WO/2009/064210A2, 2009.
17. Learmonth, D. A.; Zanotti-Gerosa, A.; Grasa, G. A.; Beliaev, A. Process. PCT Int. Appl. WO/2008/071951A2, 2008.
18. Beliaev, A.; Learmonth, D. A.; Almena Perea, J. J.; Geiß, G.; Hitzel, P.; Kadyrov, R. Catalytic process for asymmetric hydrogenation. PCT Int. Appl. WO/2009/113891A1, 2009.
19. Beliaev, A.; Learmonth, D. A.; Li, W. Process. PCT Int. Appl. WO/2009/116883A2, 2009.
20. Beliaev, A.; Learmonth, D. A. Process. PCT Int. Appl. WO/2009/136803A2, 2009.
21. Muratake, H.; Natsume, M. Palladium-catalyzed intramolecular α-arylation of aliphatic ketones Tetrahedron Lett. 1997, 38, 7581
22. Finger, G. C.; Gortatowski, M. J.; Shiley, R. H.; White, R. H. Aromatic Fluorine Compounds. VIII. Plant Growth Regulators and Intermediates J. Am. Chem. Soc. 1959, 81, 94
23. Fang, Y.; Li, C. O -Arylation versus C -Arylation: Copper-Catalyzed Intramolecular Coupling of Aryl Bromides with 1,3-Dicarbonyls J. Org. Chem. 2006, 71, 6427
24. Dupau, P.; Hay, A.-E.; Alameda Angulo, C.; Dixneuf, P. H.; Bruneau, C. Direct preparation of N-(alk-1-en-1-yl)carbamates from cyclic ketones and unsubstituted carbamates Collect. Czech. Chem. Commun. 2002, 67, 235
25. Macor, J. E.; Cornelius, L. A. M.; Roberge, J. Y. Direct displacement of -OH by nucleophiles in hydroxymethylimidazoles Tetrahedron Lett. 2000, 41, 2777
26. Soares-da-Silva, P.; Beliaev, A.; Learmonth, D. A. Process for the preparation of (R)-5-(2-aminoethyl)-1-(6,8-aminochroman-3-yl)-1,3- dihydroimidazole-2-thione and pharmaceutically acceptable salts thereof, and for making intermediates useful in the formation of said compound. PCT Int. Appl. WO/2008/094055A1, 2008.
27. Hashimoto, M.; Eda, Y.; Osanai, Y.; Iwai, T.; Aoki, S. A novel decarboxylation of α-amino acids. A facile method of decarboxylation by the use of 2-cyclohexen-1-one as a catalyst Chem. Lett. 1986, 6, 893
28. Soares-da-Silva, P.; Beliaev, A.; Learmonth, D. A. Process for the preparation of (R)-5-(2-aminoethyl)-1-(6,8-aminochroman-3-yl)-1,3- dihydroimidazole-2-thione. PCT Int. Appl. WO/2008/094056A1, 2008.
29. Gaudry, M.; Marquet, A. Enolisation des cetones dissymetriques. III. Acces facile aux bromomethylcetones par bromation en presence de methanol Tetrahedron 1970, 26, 5611
30. Osby, J. O.; Martin, M. J.; Ganem, B. An exceptionally mild deprotection of phthalimides Tetrahedron Lett. 1984, 25, 2093