Title:
ARGININE DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2023/033016
Kind Code:
A1
Abstract:
Provided are: a guanidyl-protected arginine compound which, when used in a liquid-phase peptide synthesis reaction, renders satisfactory liquid-liquid separation possible; and a peptide synthesis method in which the guanidyl-protected arginine compound is used. The present invention relates to an arginine derivative represented by formula (1), (2), or (3) or a salt thereof. (In the formulae, R1 and R2 are the same or different and each represent a hydrogen atom or a C1-C4 alkyl group, A represents a hydrogen atom or an amino-protecting group, R3 and R4 each represent a hydrogen atom or a Boc group, with the proviso that at least one of them is a Boc group, R5 and R6 each represent a hydrogen atom or a Boc group, with the proviso that at least one of theme is a Boc group, R7 and R8 each represent a hydrogen atom or a Boc group, with the proviso that at least one of them is a Boc group, and n represents an integer of 1-6 (with the proviso that the case where n is 3, R1 and R2 are each a hydrogen atom or a methyl group, and R3 to R8 are Boc groups is excluded).)
Inventors:
YANO SHINYA (JP)
MATSUMOTO SUGURU (JP)
MATSUMOTO SUGURU (JP)
Application Number:
PCT/JP2022/032699
Publication Date:
March 09, 2023
Filing Date:
August 31, 2022
Export Citation:
Assignee:
SEKISUI MEDICAL CO LTD (JP)
International Classes:
C07C279/24; C07K1/02; C07C279/14; C07F7/18
Domestic Patent References:
| WO2019118878A1 | 2019-06-20 |
Foreign References:
| JP2017526620A | 2017-09-14 | |||
| JP2002516342A | 2002-06-04 | |||
| JPS5962556A | 1984-04-10 |
Other References:
GAZDIK MICHELLE; JARMAN KATE E.; O’NEILL MATTHEW T.; HODDER ANTHONY N.; LOWES KYM N.; JOUSSET SABROUX HELENE; COWMAN ALAN F.: "Exploration of the P3region of PEXEL peptidomimetics leads to a potent inhibitor of thePlasmodiumprotease, plasmepsin V", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 24, no. 9, 16 March 2016 (2016-03-16), AMSTERDAM, NL, pages 1993 - 2010, XP029500706, ISSN: 0968-0896, DOI: 10.1016/j.bmc.2016.03.027
SARA TOMMASI, CHIARA ZANATO, REY CARABEO, ARDUINO MANGONI, SERGIO DALL’ANGELO, MATTEO ZANDA: "An Efficient Route to N-Monosubstituted Guanidino-Lactams", SYNTHESIS, GEORG THIEME VERLAG, STUTTGART, DE., vol. 47, no. 19, 17 September 2015 (2015-09-17), STUTTGART, DE. , pages 3067 - 3078, XP055483066, ISSN: 0039-7881, DOI: 10.1055/s-0034-1378845
CHEMICAL SOCIETY OF JAPAN: "NEW LECTURES ON EXPERIMENTAL CHEMISTRY", 1 January 2005, MARUZEN, TOKYO, , JP , ISBN: 4-621-07315-X, article CHEMICAL SOCIETY OF JAPAN: "Passage; Lecture on Experimental Chemistry 5th Edition Synthesis of 16 Organic Chemicals IV—Carboxylic Acids, Amino Acids, Peptides", pages: 243 - 246, XP009544042
DAISUKE TAKAHASHI; TATSUJI INOMATA; TATSUYA FUKUI: "AJIPHASE®: A Highly Efficient Synthetic Method for One‐Pot Peptide Elongation in the Solution Phase by an Fmoc Strategy", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 56, no. 27, 7 June 2017 (2017-06-07), Hoboken, USA, pages 7803 - 7807, XP072088667, ISSN: 1433-7851, DOI: 10.1002/anie.201702931
SARA TOMMASI, CHIARA ZANATO, REY CARABEO, ARDUINO MANGONI, SERGIO DALL’ANGELO, MATTEO ZANDA: "An Efficient Route to N-Monosubstituted Guanidino-Lactams", SYNTHESIS, GEORG THIEME VERLAG, STUTTGART, DE., vol. 47, no. 19, 17 September 2015 (2015-09-17), STUTTGART, DE. , pages 3067 - 3078, XP055483066, ISSN: 0039-7881, DOI: 10.1055/s-0034-1378845
CHEMICAL SOCIETY OF JAPAN: "NEW LECTURES ON EXPERIMENTAL CHEMISTRY", 1 January 2005, MARUZEN, TOKYO, , JP , ISBN: 4-621-07315-X, article CHEMICAL SOCIETY OF JAPAN: "Passage; Lecture on Experimental Chemistry 5th Edition Synthesis of 16 Organic Chemicals IV—Carboxylic Acids, Amino Acids, Peptides", pages: 243 - 246, XP009544042
DAISUKE TAKAHASHI; TATSUJI INOMATA; TATSUYA FUKUI: "AJIPHASE®: A Highly Efficient Synthetic Method for One‐Pot Peptide Elongation in the Solution Phase by an Fmoc Strategy", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 56, no. 27, 7 June 2017 (2017-06-07), Hoboken, USA, pages 7803 - 7807, XP072088667, ISSN: 1433-7851, DOI: 10.1002/anie.201702931
Attorney, Agent or Firm:
ARUGA PATENT OFFICE (JP)
Download PDF:
Previous Patent: METHOD FOR PRODUCING FMOC-PROTECTED AMINO GROUP-CONTAINING COMPOUND
Next Patent: METHOD FOR PRODUCING GANIRELIX OR SALT THEREOF
Next Patent: METHOD FOR PRODUCING GANIRELIX OR SALT THEREOF