Synthesis of diketopiperazines

Details Synthesis of diketopiperazines Synthesis of diketopiperazines

2006-03-27

2010-06-08

Wilson, James O (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C544S370000, C544S385000

Reexamination Certificate

active

07732605

ABSTRACT:
Disclosed herein are methods for synthesizing diketopiperazines with enantiomeric excess by inducing cyclization of an α-keto acid with an acid catalyst.

REFERENCES:
patent: 5891877 (1999-04-01), Brocchini et al.
patent: 6358957 (2002-03-01), Fukumoto et al.
patent: 6972289 (2005-12-01), Kanzaki et al.
patent: 2004/0102454 (2004-05-01), Hayashi et al.
patent: 2006/0167010 (2006-07-01), Hayashi et al.
patent: 2006/0217553 (2006-09-01), Hayashi et al.
patent: 0 655 060 (1998-01-01), None
patent: WO 99/38844 (1999-08-01), None
patent: WO 2004/054498 (2004-07-01), None
Siwicka, et al., Diastereodivergent Synthesis of 2,5-diketopiperazine Derivatives of B-carboline and Isoquinoline from L-amino Acids, Tetrahedron: Asymmetry 16, 975-993 (2005).
Akerlund et al., “Diketopiperazine-Based Polymers from Common Amino Acids,” Journal of Applied Polymer Science (2000), 78 (12), 2213-2218.
Goldfarb et al., “Synthesis of β-2-thienylalanine” Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, pp. 98-100 (1958), as abstracted by CAPLUS.
Hayashi, et al., “Total Synthesis of Anti-microtubule Diketopiperazine Derivatives: Phenylahistin and Aurantiamine,”J. Org. Chem.2000, 65: 8402-8405.
Kanoh et al., “Synthesis and Biological Activities of Phenylahistin Derivatives,” Bioorganic & Medicinal Chemistry, 7: 1451-1457 (1999).
Kopple et al., “A Convenient Synthesis of 2,5-Piperazinediones1a,”The Journal of Organic Chemistry, 33: 862-864 (1967).
Niemann et al., “The Synthesis of the Three Isomeric dl-β-Pyridylalanines” Journal of the American Chemical Society, vol. 64(7), pp. 1678-1682 (1942).
Nitecki et al., “A Simple Route to Sterically Pure Diketopiperazines1,”The Journal of Organic Chemistry, 33: 864-866 (1968).
Saito et al., Synthesis of novel octahydro-1, 5-imino-3-benzazocin-4, 7, 10-trione derivatives having a methyl group at the C-2 position as ABC ring models of saframycins.Chemical&Pharmaceutical Bulletin(1997), 45(7), 1120-1129.
Siwicka, et al., “Diastereodivergent synthesis of 2,5-diketopiperazine derivatives of β-carboline and isoquinoline from L-amino acids,” Tetrahedron:Asymmetry16 (2005) 975-993.
Zawadzka, et al., “Diastereoselective Synthesis of 1-Benzyltetrahydroisoquinoline Derivatives from Amino Acids by 1,4 Chirality Transfer,”Eur. J. Org. Chem.2003, 2443-2453.
International Search Report for International Appln. No. PCT/US2006/011206, mailed Dec. 6, 2006.

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