Title:
METHOD FOR EVALUATING DEGREE OF PURITY OF PHARMACEUTICAL SUBSTANCE CONTAINED IN COMPOSITE BODY, AND METHOD FOR PRODUCING COMPOSITE BODY
Document Type and Number:
WIPO Patent Application WO/2022/025228
Kind Code:
A1
Abstract:
Disclosed is a method that can evaluate the degree of purity of an active pharmaceutical substance contained in a composite body. Also disclosed is a method for producing a composite body in which the degree of purity of an active pharmaceutical substance itself is 95.0% or higher. The method for evaluating purity comprises: a reaction step for reacting, in a polar solvent, a nitrogen-containing nucleophilic agent, such as hydroxylamine, with a composite body in the presence of a protonic acid; and an evaluation step for evaluating, using rapid liquid chromatography, the degree of purity of a reaction mixture obtained in the reaction step. The method for producing a composite body comprises a reaction step for obtaining a composite body by reacting, in a polar solvent, N-(2-hydroxypropyl)methacrylamide polymer with an anthracycline pharmaceutical substance, in the presence of a protonic acid and at 10°C or lower.
Inventors:
OKANO TSUBASA (JP)
UJIIE SATOSHI (JP)
UJIIE SATOSHI (JP)
Application Number:
PCT/JP2021/028274
Publication Date:
February 03, 2022
Filing Date:
July 30, 2021
Export Citation:
Assignee:
TORAY INDUSTRIES (JP)
BIODYNAMIC RES FOUNDATION (JP)
BIODYNAMIC RES FOUNDATION (JP)
International Classes:
C08F20/56; A61K47/58; G01N30/06; G01N30/88
Domestic Patent References:
| WO2017191843A1 | 2017-11-09 | |||
| WO2020105701A1 | 2020-05-28 | |||
| WO2008047948A1 | 2008-04-24 | |||
| WO2017191843A1 | 2017-11-09 |
Foreign References:
| JP5904602B2 | 2016-04-13 |
Other References:
ETRYCH TOMáš; TSUKIGAWA KENJI; NAKAMURA HIDEAKI; CHYTIL PETR; FANG JUN; ULBRICH KAREL; OTAGIRI MASAKI; MAEDA HIROSHI: "Comparison of the pharmacological and biological properties of HPMA copolymer-pirarubicin conjugates: A single-chain copolymer conjugate and its biodegradable tandem-diblock copolymer conjugate", EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, ELSEVIER AMSTERDAM, NL, vol. 106, 18 May 2017 (2017-05-18), NL , pages 10 - 19, XP085124698, ISSN: 0928-0987, DOI: 10.1016/j.ejps.2017.05.031
NAKAMURA HIDEAKI, KOZIOLOVÁ EVA, CHYTIL PETR, TSUKIGAWA KENJI, FANG JUN, HARATAKE MAMORU, ULBRICH KAREL, ETRYCH TOMÁŠ, MAEDA HIROS: "Pronounced Cellular Uptake of Pirarubicin versus That of Other Anthracyclines: Comparison of HPMA Copolymer Conjugates of Pirarubicin and Doxorubicin", MOLECULAR PHARMACEUTICS, AMERICAN CHEMICAL SOCIETY, US, vol. 13, no. 12, 5 December 2016 (2016-12-05), US , pages 4106 - 4115, XP055890336, ISSN: 1543-8384, DOI: 10.1021/acs.molpharmaceut.6b00697
CONFIGLIACCHI E., G RAZZANO, V RIZZO, A VIGEVANI: "HPLC methods for the determination of bound and free doxorubicin, and of bound and free galactosamine, in methacrylamide polymer-drug conjugates", JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, ELSEVIER B.V., AMSTERDAM, NL, vol. 15, 31 October 1996 (1996-10-31), AMSTERDAM, NL , pages 123 - 129, XP055890340, ISSN: 0731-7085, DOI: 10.1016/0731-7085(96)01825-0
FRAIER D., E FRIGERIO, E PIANEZZOLA, M STROLIN BENEDETTI, J CASSIDY, P VASEY: "A sensitive procedure for the quantitation of free and N-(2-hydroxypropyl)methacrylamide polymer-bound doxorubicin (PK1) and some of its metabolites, 13- dihydrodoxorubicin, 13-dihydrodoxorubicinone and doxorubicinone, in human plasma and urine by reversed-phase HPLC with fluorimetric detection", JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, ELSEVIER B.V., AMSTERDAM, NL, vol. 13, no. 4/5, 30 April 1995 (1995-04-30), AMSTERDAM, NL , pages 625 - 633, XP055890341, ISSN: 0731-7085, DOI: 10.1016/0731-7085(95)01301-z
NAKAMURA HIDEAKI: " Development of Tumor-targeting Antitumor Agents Based on Polymer Effect", THE PHARMACEUTICAL SOCIETY OF JAPAN, vol. 140, no. 10, 1 October 2020 (2020-10-01), pages 1243 - 1249, XP055890344, DOI: 10.1248/yakushi.20-00158
ETRYCH ET AL., EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 106, 2017, pages 10 - 19
FRAIER ET AL., JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, vol. 13, 1995, pages 625 - 633
SUMIE YOSHIOKA: "Stability of Medicines", 1995, NANKODO CO., LTD., pages: 142
NAKAMURA HIDEAKI, KOZIOLOVÁ EVA, CHYTIL PETR, TSUKIGAWA KENJI, FANG JUN, HARATAKE MAMORU, ULBRICH KAREL, ETRYCH TOMÁŠ, MAEDA HIROS: "Pronounced Cellular Uptake of Pirarubicin versus That of Other Anthracyclines: Comparison of HPMA Copolymer Conjugates of Pirarubicin and Doxorubicin", MOLECULAR PHARMACEUTICS, AMERICAN CHEMICAL SOCIETY, US, vol. 13, no. 12, 5 December 2016 (2016-12-05), US , pages 4106 - 4115, XP055890336, ISSN: 1543-8384, DOI: 10.1021/acs.molpharmaceut.6b00697
CONFIGLIACCHI E., G RAZZANO, V RIZZO, A VIGEVANI: "HPLC methods for the determination of bound and free doxorubicin, and of bound and free galactosamine, in methacrylamide polymer-drug conjugates", JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, ELSEVIER B.V., AMSTERDAM, NL, vol. 15, 31 October 1996 (1996-10-31), AMSTERDAM, NL , pages 123 - 129, XP055890340, ISSN: 0731-7085, DOI: 10.1016/0731-7085(96)01825-0
FRAIER D., E FRIGERIO, E PIANEZZOLA, M STROLIN BENEDETTI, J CASSIDY, P VASEY: "A sensitive procedure for the quantitation of free and N-(2-hydroxypropyl)methacrylamide polymer-bound doxorubicin (PK1) and some of its metabolites, 13- dihydrodoxorubicin, 13-dihydrodoxorubicinone and doxorubicinone, in human plasma and urine by reversed-phase HPLC with fluorimetric detection", JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, ELSEVIER B.V., AMSTERDAM, NL, vol. 13, no. 4/5, 30 April 1995 (1995-04-30), AMSTERDAM, NL , pages 625 - 633, XP055890341, ISSN: 0731-7085, DOI: 10.1016/0731-7085(95)01301-z
NAKAMURA HIDEAKI: " Development of Tumor-targeting Antitumor Agents Based on Polymer Effect", THE PHARMACEUTICAL SOCIETY OF JAPAN, vol. 140, no. 10, 1 October 2020 (2020-10-01), pages 1243 - 1249, XP055890344, DOI: 10.1248/yakushi.20-00158
ETRYCH ET AL., EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 106, 2017, pages 10 - 19
FRAIER ET AL., JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, vol. 13, 1995, pages 625 - 633
SUMIE YOSHIOKA: "Stability of Medicines", 1995, NANKODO CO., LTD., pages: 142
Attorney, Agent or Firm:
TANIGAWA AND PARTNERS, PATENT FIRM (JP)
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