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Preparing method of compound FK506-A

A technology of FK506-A, 1. FK506-A is applied in the field of preparation of macrolide compound FK506-A compound, can solve the problems of unstable products of FK506FK506 and the like, achieves simple operation, improved reaction efficiency and low cost. Effect

Active Publication Date: 2015-04-22
NCPC NEW DRUG RES & DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] In the current research, FK506-A is considered to be an unstable product of FK506, so few people have conducted in-depth discussions and studies on it

Method used

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  • Preparing method of compound FK506-A
  • Preparing method of compound FK506-A
  • Preparing method of compound FK506-A

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] a. Put 10g of FK506 into an evaporating dish and heat at 120°C for 15 minutes to obtain the crude product of FK506-A;

[0035] b. Add ethyl acetate to the FK506-A crude product, add 19g of 300-400 mesh silica gel after dissolving, stir evenly and then dry to obtain a dry sample;

[0036] c. Add the dry sample to a chromatographic column equipped with 80g of 300-400 mesh silica gel, add ether for elution, use HPLC to detect the concentration of FK506-A in the eluate, and collect and determine the purity of FK506-A ≥ 75 % of the eluate, concentrated to dryness at 30°C under reduced pressure to obtain 1.6g of solid, to each gram of solid, add 15ml of crystallization solvent consisting of acetone and water with a volume ratio of 4:1, heat to dissolve, then slowly cool down to crystallize After the crystals were no longer precipitated, suction filtered, and the filter cake was washed twice with the above crystallization solvent, and the filter cake was vacuum-dried at 60 ° C...

Embodiment 2

[0041] a. Put 10g of FK506 into an evaporating dish and heat at 130°C for 5 minutes to obtain the crude product of FK506-A;

[0042] b. Add ethanol to the FK506-A crude product, add 25g of 160-230 mesh silica gel after dissolving, stir evenly and then dry to obtain a dry sample;

[0043] c. Add the dry sample to a chromatographic column equipped with 150g of 160-230 mesh silica gel, add a mixture of isopropyl ether and acetone with a volume ratio of 8:1 to elute, and collect and test the purity of FK506-A ≥ 75 by HPLC. % of the eluate was concentrated to dryness at 60°C under reduced pressure to obtain 2.1 g of solid, and 5 ml of ether was added to each gram of solid. After heating and dissolving, the temperature was slowly cooled to crystallize. After the crystals were no longer precipitated, filter and wash with ether After the cake was caked once, the filter cake was vacuum-dried at 30°C to obtain 1.9 g of pure FK506-A, and the purity of FK506-A in the obtained FK506-A pure...

Embodiment 3

[0045] a. Put 10g of FK506 into an evaporating dish and heat at 110°C for 25 minutes to obtain the crude product of FK506-A;

[0046] b. Add acetone to the FK506-A crude product, add 10g of 100-200 mesh silica gel after dissolving, stir evenly and dry to obtain a dry sample;

[0047]c. Add the dry sample to a chromatographic column equipped with 120g of 100-200 mesh silica gel, add a mixture of n-hexane and acetone with a volume ratio of 10:1 to elute, collect and test the purity of FK506-A ≥ 75% by HPLC The eluate was concentrated to dryness at 50°C under reduced pressure to obtain 1.8 g of solids. To each gram of solids, 13 milliliters of crystallization solvents consisting of n-hexane and acetone with a volume ratio of 10:1 were added. After dissolving, the temperature was slowly cooled to crystallize. After the crystals are no longer precipitated, filter, wash the filter cake once with the above crystallization solvent, and dry the filter cake under vacuum at 40°C to obtai...

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Abstract

The invention provides a preparing method of a compound FK506-A, which includes the following steps: a) heating FK506 for 2 to 25 minutes under 110 to 150 degrees C, so as to obtain a FK506-A crude product; b) adding organic solvent into the FK506-A crude product, adding silica gel after dissolving, and drying after uniformly stirring, so as to obtain a dry sample; and c) adding the dry sample into a chromatographic column filled with silica gel and eluting by adding eluting solvent, and collecting the eluent with the FK506-A purity determined by HPLC to be no less than 75% and concentrating to be dry solid, so as to obtain FK506-A pure product by crystallizing the solid. The preparing method of compound FK506-A has the advantages that the operation is simple, and the industrial production is easy.

Description

technical field [0001] The invention belongs to the technical field of biochemistry, and in particular relates to a preparation method of a macrolide compound FK506-A compound. technical background [0002] FK506 (Tacrolimus) is a macrolide compound produced by Streptomyces tsukubaensis, which is currently used to prepare immunosuppressive drugs. The molecular formula of this compound is C 44 h 69 NO 12 , with a molecular weight of 804.02, and a 23-membered ring structure in its molecule, its structural formula is as follows: [0003] [0004] According to literature reports, FK506 is unstable and can undergo isomerization reaction to produce isomers (Tetrahedron Letters, Vol31, No.45, pp6477-6480, 1990). The isomer with the structure shown in formula (1) was named FK506-A compound. [0005] [0006] Formula 1) [0007] In the current research, FK506-A is considered to be an unstable product of FK506, so few people have conducted in-depth discussions and studies ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/18
Inventor 任风芝段宝玲张雪霞陈书红李丽红刘进怀郑智慧成晓迅张艳立李晓露李宁王海燕孟雅娟
Owner NCPC NEW DRUG RES & DEV
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