Title:
PREPARATION METHOD FOR BILIVERDIN OR DERIVATIVE THEREOF
Document Type and Number:
WIPO Patent Application WO/2022/134260
Kind Code:
A1
Abstract:
A preparation method for biliverdin or a derivative thereof. Biliverdin or the derivative thereof is prepared from a compound represented by formula 2. Formula II represents a single bond or a double bond. Formula II at the positions represented by A and B are independently selected from one of a single bond and a double bond, respectively. When formula II represents a single bond, R1 or R2 linked to the single bond is selected from one of p-toluenesulfonyl, p-toluenesulfinyl, phenylsulfonyl, and phenylsulfinyl, and when formula II represents a double bond, R1 or R2 linked to the double bond is hydrogen. The preparation method for biliverdin or the derivative thereof is simple in process, does not require a column chromatography method, is high in yield and low in cost, is suitable for industrial production, reduces the by-product generated in synthesis of biliverdin dimethyl ester or biliverdin, and improves the product purity.
More Like This:
Inventors:
CHEN FAPU (CN)
SHI YUXIN (CN)
CHEN FAKAI (CN)
SHI YUXIN (CN)
CHEN FAKAI (CN)
Application Number:
PCT/CN2021/073781
Publication Date:
June 30, 2022
Filing Date:
January 26, 2021
Export Citation:
Assignee:
POSEIDON PHARMACEUTICAL CO LTD (CN)
WUHAN DAPENG PHARMACEUTICAL CO LTD (CN)
WUHAN DAPENG PHARMACEUTICAL CO LTD (CN)
International Classes:
C07D207/44; A61K31/409
Foreign References:
| CN109535057A | 2019-03-29 | |||
| CN201811311801A |
Other References:
MORA MARÍA E, BARI SARA E, AWRUCH JOSEFINA, DELFINO JOSÉ M: "On how the conformation of biliverdins influences their reduction to bilirubins: A biological and molecular modeling study", BIOORGANIC, ELSEVIER, AMSTERDAM, NL, vol. 11, no. 21, 1 October 2003 (2003-10-01), AMSTERDAM, NL, pages 4661 - 4672, XP055945532, ISSN: 0968-0896, DOI: 10.1016/S0968-0896(03)00479-6
TAKEDA SHUZO, ET AL.: "An Efficient Method for the Conversion of 2-Bromo-5-tosylpyrroles to the Corresponding 5-Tosylpyrrolinones as the D-Ring of Phycocyanobilin Derivatives", CHEMISTRY LETTERS, vol. 30, no. 6, 30 June 2001 (2001-06-30), pages 590 - 591, XP055945972, DOI: 10.1246/cl.2001.590
HAMMAM MOSTAFA A. S., NAKAMURA HIROSHI, HIRATA YUKARI, KHAWN HTOI, MURATA YASUE, KINOSHITA HIDEKI, INOMATA KATSUHIKO: "Syntheses of Biliverdin Derivatives Sterically Locked at the CD-Ring Components", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOCIETY OF JAPAN,NIPPON KAGAKUKAI, JP, vol. 79, no. 10, 1 October 2006 (2006-10-01), JP , pages 1561 - 1572, XP055945542, ISSN: 0009-2673, DOI: 10.1246/bcsj.79.1561
KAKIUCHI TAKASHI, KINOSHITA HIDEKI, INOMATA KATSUHIKO: "Total Synthesis of (±)-Phytochromobilin Starting from Two Pyrrole Derivatives", SYNLETT, GEORG THIEME VERLAG, DE, vol. 1999, no. Sup. 1, 1 June 1999 (1999-06-01), DE , pages 901 - 904, XP055945973, ISSN: 0936-5214, DOI: 10.1055/s-1999-3105
K. M. SMITHR. K. PANDEY, TETRAHEDRON, vol. 40, 1984, pages 1749 - 1754
E. D. STURROCKJ. R. BULLBR.E. KIRSCH, J. LABELED COMPD. RAD., 1994, pages 263 - 274
CHEM LETT., vol. 6, 2001, pages 590 - 591
BULL. CHEM. SOC. JPN., vol. 67, 1994, pages 3088 - 3093
J. ORG. CHEM., vol. 85, 2020, pages 13015 - 13028
ANGEW. CHEM. INT. ED., vol. 37, no. 13-14, 1998, pages 1843 - 1846
MONATSHR CHEM., vol. 120, 1989, pages 575 - 580
TAKEDA SHUZO, ET AL.: "An Efficient Method for the Conversion of 2-Bromo-5-tosylpyrroles to the Corresponding 5-Tosylpyrrolinones as the D-Ring of Phycocyanobilin Derivatives", CHEMISTRY LETTERS, vol. 30, no. 6, 30 June 2001 (2001-06-30), pages 590 - 591, XP055945972, DOI: 10.1246/cl.2001.590
HAMMAM MOSTAFA A. S., NAKAMURA HIROSHI, HIRATA YUKARI, KHAWN HTOI, MURATA YASUE, KINOSHITA HIDEKI, INOMATA KATSUHIKO: "Syntheses of Biliverdin Derivatives Sterically Locked at the CD-Ring Components", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOCIETY OF JAPAN,NIPPON KAGAKUKAI, JP, vol. 79, no. 10, 1 October 2006 (2006-10-01), JP , pages 1561 - 1572, XP055945542, ISSN: 0009-2673, DOI: 10.1246/bcsj.79.1561
KAKIUCHI TAKASHI, KINOSHITA HIDEKI, INOMATA KATSUHIKO: "Total Synthesis of (±)-Phytochromobilin Starting from Two Pyrrole Derivatives", SYNLETT, GEORG THIEME VERLAG, DE, vol. 1999, no. Sup. 1, 1 June 1999 (1999-06-01), DE , pages 901 - 904, XP055945973, ISSN: 0936-5214, DOI: 10.1055/s-1999-3105
K. M. SMITHR. K. PANDEY, TETRAHEDRON, vol. 40, 1984, pages 1749 - 1754
E. D. STURROCKJ. R. BULLBR.E. KIRSCH, J. LABELED COMPD. RAD., 1994, pages 263 - 274
CHEM LETT., vol. 6, 2001, pages 590 - 591
BULL. CHEM. SOC. JPN., vol. 67, 1994, pages 3088 - 3093
J. ORG. CHEM., vol. 85, 2020, pages 13015 - 13028
ANGEW. CHEM. INT. ED., vol. 37, no. 13-14, 1998, pages 1843 - 1846
MONATSHR CHEM., vol. 120, 1989, pages 575 - 580
Attorney, Agent or Firm:
WUHAN KEHAO INTELLECTUAL PROPERTY ATTORNEYS(SPECIAL GENERAL PARTNERSHIP) (CN)
Download PDF:
Previous Patent: PYRROLINONE COMPOUND AND SYNTHESIS METHOD THEREFOR
Next Patent: BILIVERDIN COMPOUND, AND PREPARATION METHOD THEREFOR AND USE THEREOF
Next Patent: BILIVERDIN COMPOUND, AND PREPARATION METHOD THEREFOR AND USE THEREOF