Inventing and understanding catalytic, enantioselective reactions

Current Opinion in Drug Discovery and Development

Volumn 12, Issue 6, 2009, Pages 862-875

  Shibasaki, Masakatsu ^a   Kumagai, Naoya ^a   Mashiko, Tomoyuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aldose reductase inhibitor; Amination; Asymmetric catalysis; Diabetes mellitus; Diabetic complications; Dipeptidyl peptidase 4 inhibitor; DPP 4 inhibitor; Hydrogenation; Lanthanum; Ranirestat; Sitagliptin

Indexed keywords

ALDEHYDE REDUCTASE; DIPEPTIDYL PEPTIDASE IV; EPALRESTAT; KINEDAC; RANIRESTAT; SITAGLIPTIN; SUCCINIMIDE; UNCLASSIFIED DRUG; VILDAGLIPTIN;

AMINATION; ASYMMETRIC CATALYSIS; CLINICAL TRIAL; DIABETIC NEUROPATHY; DRUG BINDING; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HUMAN; HYDROGENATION; NON INSULIN DEPENDENT DIABETES MELLITUS; REVIEW; STOICHIOMETRY;

ALDEHYDE REDUCTASE; AMINATION; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; DIPEPTIDYL-PEPTIDASE IV INHIBITORS; ENZYME INHIBITORS; HYDROGENATION; HYPOGLYCEMIC AGENTS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PYRAZINES; SPIRO COMPOUNDS; STEREOISOMERISM; TRIAZOLES;

EID: 70350763865     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (49)

1. Núñez MC, García-Rubiño ME, Conejo-García A, Cruz-López O, Kimatrai M, Gallo MA, Espinosa A, Campos JM: Homochiral drugs: A demanding tendency of the pharmaceutical industry. Curr Med Chem (2009) 16(16):2064-2074.
2. Izake EL: Chiral discrimination and enantioselective analysis of drugs: An overview. J Pharm Sci (2007) 96(7):1659-1676.
3. Agranat I, Caner H, Caldwell J: Putting chirality to work: The strategy of chiral switches. Nat Rev Drug Discov (2002) 1(10):753-768.
4. Eichelbaum M, Testa B, Somogyi A (Eds): Stereochemical Aspects of Drug Action and Disposition. Springer-Verlag, Heidelberg, Germany 2002).
5. Blaser H-U, Pugin B, Spindler F, Thommen M: From a chiral switch to a ligand portfolio for asymmetric catalysis. Acc Chem Res (2007) 40(12):1240-1250.
6. Walsh PJ, Kozlowski MC (Eds): Fundamentals of Asymmetric Catalysis. University Science Books, Herndon, VA, USA (2008).
7. Mohr JT, Krout MR, Stoltz BM: Natural products as inspiration for the development of asymmetric catalysis. Nature (2008) 455(7211):323-332.
8. Ojima I (Ed): Catalytic Asymmetric Synthesis. Wiley & Sons Inc, New York, NY, USA (2000).
9. Jacobsen EN, Pfaltz A, Yamamoto H (Eds): Comprehensive Asymmetric Catalysis I-III, Supplements. Springer Verlag, Heidelberg, Germany (1999/2004).
10. Green Chemistry: US Environmental Protection Agency, Washington, DC, USA (2008). www.epa.gov/greenchemistry
11. Sheldon RA, Arends I, Hanefeld U (Eds): Green Chemistry and Catalysis. Wiley-VCH, Weinheim, Germany 2007).
12. International Diabetes Federation: Diabetes Atlas, 3rd Edition. IDF, Brussels, Belgium (2006). www.iotf.org/diabetes.asp
13. Nath D, Heemels M-T, Anson L: Obesity and diabetes. Nature (2006) 444(7121):839.
14. Mojosov S, Weir GC, Habener JF: Insulinotropin: Glucagon-like peptide I (7-37) co-encoded in the glucagon gene is a potent stimulator of insulin release in the perfused rat pancreas. J Clin Invest (1987) 79(2):616-619.
15. Vilsbøll T, Holst JJ: Incretins, insulin secretion and type 2 diabetes. Diabetologia (2004) 47(3):357-366.
16. Nauck MA, Homberger E, Siegel EG, Allen RC, Eaton RP, Ebert R, Creutzfeldt W: Incretin effects of increasing glucose loads in man calculated from venous insulin and C-peptide responses. J Clin Endocrinol Metab (1986) 63(2):492-498.
17. Idris I, Donnelly R: Dipeptidyl peptidase IV inhibitors: A major new class of oral antidiabetic drug. Diabetes Obes Metab (2007) 9(2):153-165.
18. von Geldern TW, Trevillyan JM: "The next big thing" in diabetes: Clinical progress on DPP-IV inhibitors. Drug Dev Res (2006) 67(8):627-642.
19. Weber AE: Dipeptidyl peptidase IV inhibitors for the treatment of diabetes. J Med Chem (2004) 47(17):4135-4141.
20. Thornberry NA, Weber AE: Discovery of JANUVIATM (sitagliptin), a selective dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. Curr Top Med Chem (2007) 7(6):557-568.
21. Drucker D, Easley C, Kirkpatrick P: Fresh from the pipeline-Sitagliptin. Nat Rev Drug Discov (2007) 6(2):109-110.
22. Ammirati MJ, Andrews KM, Boyer DD, Brodeur AM, Danley DE, Doran SD, Hulin B, Liu S, McPherson RK, Orena SJ, Parker JC et al: (3,3-Difuoro-pyrrolidin-1- yl)-[(2S,4S)-4-(4-pyrimidin-2-yl-piperazin-1-yl)-pyrrolidin-2-yl]-methanone: A potent, selective orally active dipeptidyl peptidase IV inhibitor. Bioorg Med Chem Lett (2009) 19(7):1991-1995.
23. Merck & Co Inc: SEC Filing: Merck & Co 10-K. Form 10-K (2009): February
24. Kim D, Wang L, Beconi M, Eiermann GJ, Fisher MH, He H, Hickey GJ, Kowalchick JE, Leiting B, Lyons K, Marsilio F et al: (2R)-4-oxo-4[3- (trifluoromethyl)-5,6-dihydro[1,2,4] triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5- trifluorophenyl) butan-2-amine: A potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. J Med Chem (2005) 48(1):141-151.
25. Schöllkopf U, Groth U, Deng C: Enantioselective syntheses of (R)-amino acids using l-valine as chiral agent. Angew Chem Int Ed (1981) 20(9):798-799.
26. Trost BM: The atom economy-A search for synthetic effciency. Science (1991) 254(5037):1471-1477.
27. Wender PA, Verma VA, Paxton TJ, Pillow TH: Function-oriented synthesis, step economy, and drug design. Acc Chem Res (2008) 41(1):40-49.
28. Hansen K, Balsells J, Dreher S, Hsiao Y, Kubryk M, Palucki M, Rivera N, Steinhuebel D, Armstrong JD 3rd, Askin D, Grabowski EJJ: First generation process for the preparation of the DPP-IV inhibitor sitagliptin. Org Process Res Dev (2005) 9(5):634-639.
29. Noyori R, Ohkuma T, Kitamura M, Takaya H, Sayo N, Kumobayashi H, Akutagawa S: Asymmetric hydrogenation of ?-keto carboxylic esters. A practical, purely chemical access to ?-hydroxy esters in high enantiomeric purity. J Am Chem Soc (1987) 109(19): 5856-5858.
30. Noyori R: Asymmetric Catalysis in Organic Synthesis. Wiley & Sons Inc, New York, NY, USA (1994).
31. Hansen KB, Hsiao Y, Xu F, Rivera N, Clausen A, Kubryk M, Krska S, Rosner T, Simmons B, Balsells J, Ikemoto N et al: Highly effcient asymmetric synthesis of sitagliptin. J Am Chem Soc (2009) 131(25):8798-8804.
32. Young IS, Baran PS: Protecting-group-free synthesis as an opportunity for invention. Nat Chem (2009) 1(1):193-205.
33. Hsiao Y, Rivera NR, Rosner T, Krska SW, Njolito E, Wang F, Sun Y, Armstrong JD 3rd, Grabowski EJ, Tillyer RD, Spindler F et al: Highly effcient synthesis of ?-amino acid derivatives via asymmetric hydrogenation of unprotected enamines. J Am Chem Soc (2004) 126(32):9918-9919.
34. Xu F, Armstrong JD 3rd, Zhou GX, Simmons B, Hughes D, Ge Z, Grabowski EJ: Mechanistic evidence for an ?-oxoketene pathway in the formation of ?-ketoamides/esters via Meldrum's acid adducts. J Am Chem Soc (2004) 126(40):13002-13009.
35. Clausen AM, Dziadul B, Cappuccio KL, Kaba M, Starbuck C, Hsiao Y, Dowling TM: Identifcation of ammonium chloride as an effective promoter of the asymmetric hydrogenation of a ?-enamine amide. Org Process Res Dev (2006) 10(4):723-726.
36. Giannoukakis N: Drug evaluation: Ranirestat-An aldose reductase inhibitor for the potential treatment of diabetic complications. Curr Opin Invest Drugs (2006) 7(10):916-923.
37. Yabe-Nishimura C: Aldose reductase in glucose toxicity: A potential target for the prevention of diabetic complications. Pharmacol Rev (1998) 50(1):21-33.
38. Oka M, Kato N: Aldose reductase inhibitors. J Enzym Inhib (2001) 16(6):465-473.
39. Negoro T, Murata M, Ueda S, Fujitani B, Ono Y, Kuromiya A, Suzuki K, Matsumoto J-I: Novel, highly potent aldose reductase inhibitors: (R)-(-)-2-(4-bromo-2-fuorobenzyl)-1,2,3,4-tetrahydropyrrolo[1,2-a] pyrazine-4-spiro-3'-pyrrolidine-1,2',3,5'-tetrone (AS-3201) and its congeners. J Med Chem (1998) 41(21):4118-4129.
40. Ramirez MA, Borja NL: Epalrestat: An aldose reductase inhibitor for the treatment of diabetic neuropathy. Pharmacotherapy (2008) 28(5):646-655.
41. Kurono M, Fujii A, Murata M, Fujitani B, Negoro T: Stereospecifc recognition of a spirosuccinimide type aldose reductase inhibitor (AS-3201) by plasma proteins: A signifcant role of specifc binding by serum albumin in the improved potence and stability. Biochem Pharmacol (2006) 71(3):338-353.
42. Riant O, Hannedouche J: Asymmetric catalysis for the construction of quaternary carbon centers: Nucleophilic addition on ketones and ketimines. Org Biomol Chem (2007) 5(6):873-888.
43. Watanabe T, Kawabata T: Asymmetric Dieckmann condensation via memory of chirality: Synthesis of the key intermediate for AS-3201, an aldose reductase inhibitor. Heterocycles (2008) 76(2):1593-1606.
44. Cativiela C, Ordóñez M: Recent progress on the stereoselective synthesis of cyclic quaternary ?-amino acids. Tetrahedron Asymmetry (2009) 20(1):1-63.
45. Nair V, Biju AT, Mathew SC, Babu BP: Carbon-nitrogen bond-forming reactions of dialkyl azodicarboxylate: A promising synthetic strategy. Chem Asian J (2008) 3(5):810-820.
46. Mashiko T, Hara K, Tanaka D, Fujiwara Y, Kumagai N, Shibasaki M: En route to an effcient asymmetric synthesis of AS-3201. J Am Chem Soc (2007) 129(37):11342-11343.
47. He R, Wang X, Hashimoto T, Maruoka K: Binaphthyl-modifed quaternary phosphonium salts as chiral phase-transfer catalysis: Asymmetric amination of ?-keto esters. Angew Chem Int Ed (2008) 47(49):9466-9468.
48. Mashiko T, Kumagai N, Shibasaki M: An improved lanthanum catalyst system for asymmetric amination: Toward a practical asymmetric synthesis of AS-3201 (ranirestat). Org Lett (2008) 10(13):2725-2728. doi: 10.1021/ja9052653
49. Mashiko T, Kumagai N, Shibasaki M: Managing highly coordinative substrates in asymmetric catalysis: A catalytic asymmetric amination with a lanthanum-based ternary catalyst. J Am Chem Soc (2009) doi: 10.1021/ja9052653.