PREPARATION METHOD FOR R-TYPE KETOROLAC AND USE THEREOF

WIPO Patent Application WO/2024/041629

A1

The present invention provides a preparation method for R-type ketorolac and use thereof, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: step 1, preparing ketorolac; and step 2, splitting R-configuration ketorolac, wherein the splitting is chiral amine splitting or enzyme splitting. In the present application, glacial acetic acid is used as a reaction solvent, and the glacial acetic acid is not only environment-friendly, but also can be removed easily, so that the conversion of a raw material SM1 can be significantly improved, thereby improving the yield and purity of ketorolac. The highest yield of the obtained ketorolac can reach 70% or above, and the purity thereof reaches 99% or above. Chiral amine or enzyme is used to carry out chiral splitting on ketorolac, so that high-purity and high-yield R-type ketorolac can be obtained, and the obtained R-type ketorolac can prevent chemotherapy drug resistance and improve the chemotherapy curative effect and the cure rate.

JPH07267932	5-AMINO-1H-PYRAZOLE COMPOUND
WO/2021/165818	PROCESS AND INTERMEDIATES FOR THE PREPARATION OF 2-FLUORO-N-METHYL-4-[7-QUINOLIN-6-YL-METHYL)-IMIDAZO[1,2-B][1,2,4]TRIAZIN-2YL]BENZAMIDE
WO/2009/094157	DIHYDRO- 1H- PYRROLO [1,2-A] INDOL-1-YL CARBOXYLIC DERIVATIVES WHICH ACT AS S1P1 AGONISTS

ZHANG LINGBING (CN)
ZHANG DONGXU (CN)

PCT/CN2023/114864

February 29, 2024

August 25, 2023

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YINUOKE MEDICINE SCIENCE ANG TECH COMPANY LTD (CN)

C07D487/04; A61P35/00; C12P17/18; C12P41/00

CN114031621A	2022-02-11
US5955504A	1999-09-21
CN115181105A	2022-10-14

GUZMáN A, YUSTE F, TOSCANO R A, YOUNG J M, VAN HORN A R, MUCHOWSKI J M: "Absolute configuration of (-)-5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-alpha]pyrrole-1-carboxylic acid, the active enantiomer of ketorolac.", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 29, no. 4, 1 April 1986 (1986-04-01), US , pages 589 - 591, XP002720053, ISSN: 0022-2623, DOI: 10.1021/jm00154a027
KIM, Y.H. CHEONG, C.S. LEE, S.H. KIM, K.S.: "Enzymatic kinetic resolution of ketorolac", TETRAHEDRON ASYMMETRY, PERGAMON PRESS LTD, OXFORD, GB, vol. 12, no. 13, 30 July 2001 (2001-07-30), OXFORD, GB , pages 1865 - 1869, XP004318057, ISSN: 0957-4166, DOI: 10.1016/S0957-4166(01)00332-9

BEIJING FINELAND IP FIRM (CN)

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