Title:
METHOD FOR ISOLATING PHENOTHIAZINE DERIVATIVE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2024/018764
Kind Code:
A1
Abstract:
In the present invention, when converting the phenothiazine carbaldehyde derivative compound or phenothiazine acetyl derivative compound represented by general formula (b) (wherein, R1 is a monovalent aliphatic hydrocarbon group having 1-10 carbon atoms, and R2 is a hydrogen atom or methyl group) into the phenothiazine derivative compound represented by general formula (I) (wherein, R1 and R2 are the same as the above definitions) by a Wittig reaction, the phenothiazine derivative compound (I) is crystallized, by using ethanol, from a reaction mixture containing the phenothiazine derivative compound (I) after the Wittig reaction and triphenylphosphine oxide, thereby isolating the phenothiazine derivative compound.
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Inventors:
SAITO SATORU (JP)
Application Number:
PCT/JP2023/020476
Publication Date:
January 25, 2024
Filing Date:
June 01, 2023
Export Citation:
Assignee:
UNIMATEC CO LTD (JP)
International Classes:
C07D279/36
Other References:
QIU XIANPING, LU RAN: "Synthesis and Optical Properties of Monodisperse Phenothiazinevinylene‐Based Conjugated Oligomers", CHEMISTRYSELECT, WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 5, no. 39, 22 October 2020 (2020-10-22), DE , pages 12218 - 12223, XP093131774, ISSN: 2365-6549, DOI: 10.1002/slct.202003194
ZHANG TONG; HAN YANNING; LIANG MENG; BIAN WEIXIAO; ZHANG YAN; LI XIAOTING; ZHANG CHUNYU; XUE PENGCHONG: "Substituent effect on photophysical properties, crystal structures and mechanochromism of D-π-A phenothiazine derivatives", DYES AND PIGMENTS, ELSEVIER APPLIED SCIENCE PUBLISHERS BARKING, GB, vol. 171, 2 July 2019 (2019-07-02), GB , XP085790305, ISSN: 0143-7208, DOI: 10.1016/j.dyepig.2019.107692
XUE PENGCHONG, YAO BOQI, LIU XUHUI, SUN JIABAO, GONG PENG, ZHANG ZHENQI, QIAN CHONG, ZHANG YUAN, LU RAN: "Reversible mechanochromic luminescence of phenothiazine-based 10,10′-bianthracene derivatives with different lengths of alkyl chains", JOURNAL OF MATERIALS CHEMISTRY C, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 3, no. 5, 1 January 2015 (2015-01-01), GB , pages 1018 - 1025, XP093131783, ISSN: 2050-7526, DOI: 10.1039/C4TC02126F
QIU, X. LU, R. ZHOU, H. ZHANG, X. XU, T. LIU, X. ZHAO, Y.: "Synthesis of linear monodisperse vinylene-linked phenothiazine oligomers", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 48, no. 43, 26 September 2007 (2007-09-26), Amsterdam , NL , pages 7582 - 7585, XP022272143, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2007.09.002
ZHANG, X.H. ; CHOI, S.H. ; CHOI, D. ; AHN, K.H.: "Synthesis and photophysical properties of phenothiazine-labeled conjugated dendrimers", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 46, no. 32, 8 August 2005 (2005-08-08), Amsterdam , NL , pages 5273 - 5276, XP027862566, ISSN: 0040-4039
BATESKY DONALD C., GOLDFOGEL MATTHEW J., WEIX DANIEL J.: "Removal of Triphenylphosphine Oxide by Precipitation with Zinc Chloride in Polar Solvents", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 82, no. 19, 6 October 2017 (2017-10-06), pages 9931 - 9936, XP093131789, ISSN: 0022-3263, DOI: 10.1021/acs.joc.7b00459
TAMBOLI YASINALLI, KASHID BHARAT B., YADAV RAM PRASAD, RAFEEQ MOHAMMAD, YEOLE RAVINDRA, MERWADE ARVIND Y.: "Triphenylphosphine Oxide Removal from Reactions: The Role of Solvent and Temperature", ACS OMEGA, ACS PUBLICATIONS, US, vol. 6, no. 21, 1 June 2021 (2021-06-01), US , pages 13940 - 13945, XP093131790, ISSN: 2470-1343, DOI: 10.1021/acsomega.1c01996
PIETER D. DE KONING, DOUGLAS MCANDREW, ROBERT MOORE, IAN B. MOSES, DAVID C. BOYLES, KYLE KISSICK, COREY L. STANCHINA, TIMOTHY CUTH: "Fit-for-Purpose Development of the Enabling Route to Crizotinib (PF-02341066)", ORGANIC PROCESS RESEARCH & DEVELOPMENT, AMERICAN CHEMICAL SOCIETY, vol. 15, no. 5, 16 September 2011 (2011-09-16), pages 1018 - 1026, XP055078841, ISSN: 10836160, DOI: 10.1021/op200131n
ZHANG TONG; HAN YANNING; LIANG MENG; BIAN WEIXIAO; ZHANG YAN; LI XIAOTING; ZHANG CHUNYU; XUE PENGCHONG: "Substituent effect on photophysical properties, crystal structures and mechanochromism of D-π-A phenothiazine derivatives", DYES AND PIGMENTS, ELSEVIER APPLIED SCIENCE PUBLISHERS BARKING, GB, vol. 171, 2 July 2019 (2019-07-02), GB , XP085790305, ISSN: 0143-7208, DOI: 10.1016/j.dyepig.2019.107692
XUE PENGCHONG, YAO BOQI, LIU XUHUI, SUN JIABAO, GONG PENG, ZHANG ZHENQI, QIAN CHONG, ZHANG YUAN, LU RAN: "Reversible mechanochromic luminescence of phenothiazine-based 10,10′-bianthracene derivatives with different lengths of alkyl chains", JOURNAL OF MATERIALS CHEMISTRY C, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 3, no. 5, 1 January 2015 (2015-01-01), GB , pages 1018 - 1025, XP093131783, ISSN: 2050-7526, DOI: 10.1039/C4TC02126F
QIU, X. LU, R. ZHOU, H. ZHANG, X. XU, T. LIU, X. ZHAO, Y.: "Synthesis of linear monodisperse vinylene-linked phenothiazine oligomers", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 48, no. 43, 26 September 2007 (2007-09-26), Amsterdam , NL , pages 7582 - 7585, XP022272143, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2007.09.002
ZHANG, X.H. ; CHOI, S.H. ; CHOI, D. ; AHN, K.H.: "Synthesis and photophysical properties of phenothiazine-labeled conjugated dendrimers", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 46, no. 32, 8 August 2005 (2005-08-08), Amsterdam , NL , pages 5273 - 5276, XP027862566, ISSN: 0040-4039
BATESKY DONALD C., GOLDFOGEL MATTHEW J., WEIX DANIEL J.: "Removal of Triphenylphosphine Oxide by Precipitation with Zinc Chloride in Polar Solvents", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 82, no. 19, 6 October 2017 (2017-10-06), pages 9931 - 9936, XP093131789, ISSN: 0022-3263, DOI: 10.1021/acs.joc.7b00459
TAMBOLI YASINALLI, KASHID BHARAT B., YADAV RAM PRASAD, RAFEEQ MOHAMMAD, YEOLE RAVINDRA, MERWADE ARVIND Y.: "Triphenylphosphine Oxide Removal from Reactions: The Role of Solvent and Temperature", ACS OMEGA, ACS PUBLICATIONS, US, vol. 6, no. 21, 1 June 2021 (2021-06-01), US , pages 13940 - 13945, XP093131790, ISSN: 2470-1343, DOI: 10.1021/acsomega.1c01996
PIETER D. DE KONING, DOUGLAS MCANDREW, ROBERT MOORE, IAN B. MOSES, DAVID C. BOYLES, KYLE KISSICK, COREY L. STANCHINA, TIMOTHY CUTH: "Fit-for-Purpose Development of the Enabling Route to Crizotinib (PF-02341066)", ORGANIC PROCESS RESEARCH & DEVELOPMENT, AMERICAN CHEMICAL SOCIETY, vol. 15, no. 5, 16 September 2011 (2011-09-16), pages 1018 - 1026, XP055078841, ISSN: 10836160, DOI: 10.1021/op200131n
Attorney, Agent or Firm:
YOSHIDA Kazuko (JP)
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