Title:
POLYPEPTIDE SYNTHESIS USING DIKETOPIPERAZINE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2024/075813
Kind Code:
A1
Abstract:
Provided are: a novel diketopiperazine compound for rapid and easy synthesis of various polypeptides; and a method for manufacturing the same. The diketopiperazine compound is represented by general formula (1). (In the formula, R1, R2, R3, R4, and R5 are each independently a hydrogen atom, a substituted or unsubstituted hydrocarbon group, or a substituted or unsubstituted heterocyclic group. R1 and R2, R1 and R5, R2 and R5, and/or R3 and R4 are each optionally bonded to form a ring. PGE represents an electron-withdrawing protective group.)
Inventors:
YAMAMOTO HISASHI (JP)
MITSUDA MASARU (JP)
HATTORI TOMOHIRO (JP)
MITSUDA MASARU (JP)
HATTORI TOMOHIRO (JP)
Application Number:
PCT/JP2023/036352
Publication Date:
April 11, 2024
Filing Date:
October 05, 2023
Export Citation:
Assignee:
CHUBU UNIV EDUCATIONAL FOUNDATION (JP)
International Classes:
C07D241/08; C07K1/00; C07K5/10; C07K7/06
Domestic Patent References:
| WO2017025031A1 | 2017-02-16 | |||
| WO2004048345A2 | 2004-06-10 | |||
| WO2004098602A1 | 2004-11-18 |
Foreign References:
| CN112778183A | 2021-05-11 | |||
| JP2011530559A | 2011-12-22 | |||
| JP2012504576A | 2012-02-23 |
Other References:
HABASHITA HIROMU, KOKUBO MASAYA, HAMANO SHIN-ICHI, HAMANAKA NOBUYUKI, TODA MASAAKI, SHIBAYAMA SHIRO, TADA HIDEAKI, SAGAWA KENJI, F: "Design, Synthesis, and Biological Evaluation of the Combinatorial Library with a New Spirodiketopiperazine Scaffold. Discovery of Novel Potent and Selective Low-Molecular-Weight CCR5 Antagonists", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 49, no. 14, 1 July 2006 (2006-07-01), US , pages 4140 - 4152, XP093044169, ISSN: 0022-2623, DOI: 10.1021/jm060051s
DANIEL FARRAN: "Regioselective and sequential reactivity of activated 2,5‐diketopiperazines", JOURNAL OF PEPTIDE SIENCE, JOHN WILEY & SONS, INC., HOBOKEN, USA, vol. 15, no. 7, 1 July 2009 (2009-07-01), Hoboken, USA, pages 474 - 478, XP093157443, ISSN: 1075-2617, DOI: 10.1002/psc.1139
JUAN F SANZ-CERVERA: "Synthesis and evaluation of microtubule assembly inhibition and cytotoxicity of prenylated derivatives of cyclo-l-Trp-l-Pro", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 8, no. 10, 1 October 2000 (2000-10-01), AMSTERDAM, NL, pages 2407 - 2415, XP093157444, ISSN: 0968-0896, DOI: 10.1016/S0968-0896(00)00171-1
HONG‐QIAO LAN; JIAN‐LIANG YE; AI‐E WANG; YUAN‐PING RUAN; PEI‐QIANG HUANG: "A Flexible Asymmetric Approach to Methyl 5‐Alkyltetramates and Its Application in the Synthesis of Cytotoxic Marine Natural Product Belamide A", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 17, no. 3, 19 November 2010 (2010-11-19), DE, pages 958 - 968, XP071833391, ISSN: 0947-6539, DOI: 10.1002/chem.201002063
MARIO ORDÓÑEZ; FERNANDO TORRES‐HERNÁNDEZ; JOSÉ LUIS VIVEROS‐CEBALLOS: "Highly Diastereoselective Synthesis of Cyclic α‐Aminophosphonic and α‐Aminophosphinic Acids from Glycyl‐l‐Proline 2,5‐Diketopiperazine", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2019, no. 44, 18 November 2019 (2019-11-18), DE , pages 7378 - 7383, XP072122938, ISSN: 1434-193X, DOI: 10.1002/ejoc.201901439
ANNA‐LENA LEISTNER: "Fluorinated Azobenzenes Switchable with Red Light", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 27, no. 31, 1 June 2021 (2021-06-01), DE, pages 8094 - 8099//S1-S161, XP093157446, ISSN: 0947-6539, DOI: 10.1002/chem.202005486
MAKOTO OBA: "Substituent-dependent asymmetric synthesis of L-threo-and ~-erythro-[2,3-2H~]phenylalanine from chiral (2)-dehydrophenylalanine", CHEMICAL COMMUNICATIONS, 1 January 1996 (1996-01-01), pages 1875 - 1876, XP093157451
KOCIENSKI, P. ; DIXON, N.J. ; WADMAN, S.: "A stereoselective synthesis of tri-substituted alkenes. The nickel-catalysed coupling of Grignard reagents with 6-alkyl-3,4-dihydro-2H-pyrans.", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 29, no. 19, 1 January 1988 (1988-01-01), Amsterdam , NL , pages 2353 - 2356, XP022581031, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)86058-X
MURRAY. GOODMAN: "Peptide Synthesis via Amino Acid Active Esters. II.1 Some Abnormal Reactions during Peptide Synthesis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 84, no. 7, 5 April 1962 (1962-04-05), pages 1279 - 1283, XP093157456, ISSN: 0002-7863, DOI: 10.1021/ja00866a044
MARIELL PETTERSSON, MARIA QUANT, JAEKI MIN, LUIGI ICONARU, RICHARD W. KRIWACKI, M. BRETT WADDELL, R. KIPLIN GUY, KRISTINA LUTHMAN,: "Design, Synthesis and Evaluation of 2,5-Diketopiperazines as Inhibitors of the MDM2-p53 Interaction", PLOS ONE, vol. 10, no. 10, pages e0137867, XP055629438, DOI: 10.1371/journal.pone.0137867
VEERMAN J J N,ET AL: "Synthesis of 2,6-bridged piperazine-3-ones by N-acyliminium ion chemistry.", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 68, no. 11, 30 May 2003 (2003-05-30), pages 4486 - 4494, XP002279630, ISSN: 0022-3263, DOI: 10.1021/jo0342572
N. GOSH: "Reaction of Benzil with substituted Urea in Presence of Alkali", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, INDIAN CHEMICAL SOCIETY, IN, vol. 25, no. 11, 1 January 1948 (1948-01-01), IN , pages 515 - 518, XP009553848, ISSN: 0019-4522
DANIEL FARRAN: "Regioselective and sequential reactivity of activated 2,5‐diketopiperazines", JOURNAL OF PEPTIDE SIENCE, JOHN WILEY & SONS, INC., HOBOKEN, USA, vol. 15, no. 7, 1 July 2009 (2009-07-01), Hoboken, USA, pages 474 - 478, XP093157443, ISSN: 1075-2617, DOI: 10.1002/psc.1139
JUAN F SANZ-CERVERA: "Synthesis and evaluation of microtubule assembly inhibition and cytotoxicity of prenylated derivatives of cyclo-l-Trp-l-Pro", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 8, no. 10, 1 October 2000 (2000-10-01), AMSTERDAM, NL, pages 2407 - 2415, XP093157444, ISSN: 0968-0896, DOI: 10.1016/S0968-0896(00)00171-1
HONG‐QIAO LAN; JIAN‐LIANG YE; AI‐E WANG; YUAN‐PING RUAN; PEI‐QIANG HUANG: "A Flexible Asymmetric Approach to Methyl 5‐Alkyltetramates and Its Application in the Synthesis of Cytotoxic Marine Natural Product Belamide A", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 17, no. 3, 19 November 2010 (2010-11-19), DE, pages 958 - 968, XP071833391, ISSN: 0947-6539, DOI: 10.1002/chem.201002063
MARIO ORDÓÑEZ; FERNANDO TORRES‐HERNÁNDEZ; JOSÉ LUIS VIVEROS‐CEBALLOS: "Highly Diastereoselective Synthesis of Cyclic α‐Aminophosphonic and α‐Aminophosphinic Acids from Glycyl‐l‐Proline 2,5‐Diketopiperazine", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2019, no. 44, 18 November 2019 (2019-11-18), DE , pages 7378 - 7383, XP072122938, ISSN: 1434-193X, DOI: 10.1002/ejoc.201901439
ANNA‐LENA LEISTNER: "Fluorinated Azobenzenes Switchable with Red Light", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 27, no. 31, 1 June 2021 (2021-06-01), DE, pages 8094 - 8099//S1-S161, XP093157446, ISSN: 0947-6539, DOI: 10.1002/chem.202005486
MAKOTO OBA: "Substituent-dependent asymmetric synthesis of L-threo-and ~-erythro-[2,3-2H~]phenylalanine from chiral (2)-dehydrophenylalanine", CHEMICAL COMMUNICATIONS, 1 January 1996 (1996-01-01), pages 1875 - 1876, XP093157451
KOCIENSKI, P. ; DIXON, N.J. ; WADMAN, S.: "A stereoselective synthesis of tri-substituted alkenes. The nickel-catalysed coupling of Grignard reagents with 6-alkyl-3,4-dihydro-2H-pyrans.", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 29, no. 19, 1 January 1988 (1988-01-01), Amsterdam , NL , pages 2353 - 2356, XP022581031, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)86058-X
MURRAY. GOODMAN: "Peptide Synthesis via Amino Acid Active Esters. II.1 Some Abnormal Reactions during Peptide Synthesis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 84, no. 7, 5 April 1962 (1962-04-05), pages 1279 - 1283, XP093157456, ISSN: 0002-7863, DOI: 10.1021/ja00866a044
MARIELL PETTERSSON, MARIA QUANT, JAEKI MIN, LUIGI ICONARU, RICHARD W. KRIWACKI, M. BRETT WADDELL, R. KIPLIN GUY, KRISTINA LUTHMAN,: "Design, Synthesis and Evaluation of 2,5-Diketopiperazines as Inhibitors of the MDM2-p53 Interaction", PLOS ONE, vol. 10, no. 10, pages e0137867, XP055629438, DOI: 10.1371/journal.pone.0137867
VEERMAN J J N,ET AL: "Synthesis of 2,6-bridged piperazine-3-ones by N-acyliminium ion chemistry.", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 68, no. 11, 30 May 2003 (2003-05-30), pages 4486 - 4494, XP002279630, ISSN: 0022-3263, DOI: 10.1021/jo0342572
N. GOSH: "Reaction of Benzil with substituted Urea in Presence of Alkali", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, INDIAN CHEMICAL SOCIETY, IN, vol. 25, no. 11, 1 January 1948 (1948-01-01), IN , pages 515 - 518, XP009553848, ISSN: 0019-4522
Attorney, Agent or Firm:
AOKI, Atsushi et al. (JP)
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