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A kind of synthetic method of Kebomei

A technology that can produce and compound compounds, applied in the field of medicine and chemical industry, can solve the problems of difficult industrial production, harsh reaction conditions, expensive starting materials, etc., and achieve the effects of short production cycle, simple operation and low cost.

Active Publication Date: 2022-03-15
SHENZHEN KEXING PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] Patent CN108017583A is a preparation method of Kebomei, which is an improvement on the original patent WO2014014834A1, but the starting materials selected are relatively expensive
[0021] In summary, the existing synthetic method of Kebomei has the problems that the starting material reagents used are relatively expensive, and the methyl group is introduced through the intermediate isoquinolinone, the reaction conditions are harsh, the cost is high, and it is difficult to industrialize production.

Method used

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  • A kind of synthetic method of Kebomei

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] The preparation of embodiment 1 compound B

[0101] Add 136.5ml of acetic acid and compound A (27.3g, 0.1mol) to the reaction flask, slowly add acetic anhydride (61.2g, 0.6mol) under stirring, and then heat up to 65--70°C for 2-3 hours. The solvent was distilled off under reduced pressure, 300 ml of 80% ethanol aqueous solution was added, stirred, filtered, and dried to obtain 35.3 g of solid compound B with a yield of 99.0% and a purity of 95.6%.

Embodiment 2

[0102] The preparation of embodiment 2 compound C

[0103] Add 357.0ml of anhydrous ethyl alcohol and compound B (35.7g) to the reaction flask, add concentrated sulfuric acid (1ml), raise the temperature to 70-78°C for 2-3 hours, after completion, evaporate the solvent under reduced pressure, add 500ml of water / 200ml of ethyl acetate After ester extraction and liquid separation, the organic layer was concentrated to dryness under reduced pressure to obtain 37.0 g of compound C with a yield of 96.2% and a purity of 92.9%.

[0104] MS:[M+1]=386.1

[0105] 1 H NMR(400MHz,DMSO)δ8.50(s,1H)7.03-7.55(m,10H),5.15(d,1H),4.15(q,2H),2.23(s,3H),1.92(s,3H ), 1.25(t,3H).

Embodiment 3

[0106] The preparation of embodiment 3 compound D

[0107] Add 154.0ml of acetonitrile and compound C (38.5g) to the reaction flask, add phosphorus oxychloride (76.5g), raise the temperature to 78-80°C for 2-3 hours, after completion, evaporate the solvent under reduced pressure, add 500ml of water / 200ml of acetic acid Ethyl ester extraction, liquid separation, and the organic phase was concentrated to dryness under reduced pressure to obtain 31.2 g of compound D with a yield of 85.0% and a purity of 97.7%.

[0108] MS:[M+1]=368.1

[0109] 1 H NMR(400MHz,DMSO)δ7.02-7.58(m,8H),6.55(d,1H),4.11(q,2H),2.34(s,3H),2.20(s,3H),1.22(t, 3H).

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Abstract

The present invention provides a kind of synthesis method of Kebomei, 2-amino-3-hydroxyl-3-(4-phenoxyphenyl)propionic acid is protected by acetic anhydride, esterified, cyclized, oxidized aromatic ring, hydrolyzed, The step of glycine condensation can obtain Kebomei; the materials used in this synthesis method are simple and easy to obtain, the reaction operation is simple and convenient, the reaction conditions are mild, the product has high purity, the production cycle is short, and the cost is low, which is suitable for large-scale industrial production.

Description

technical field [0001] The present invention relates to the field of medicine and chemical industry, in particular to the synthesis method of Kebomei. Background technique [0002] Roxadustat is a small molecule inhibitor developed by FibroGen in the United States for regulating the stability or activity of hypoxia-inducible factor HIF. HIF (Hypoxia Inducible Factor) is a specific transcription factor that is very sensitive to cellular hypoxia and plays a key role in the homeostasis of oxygen in organisms. [0003] Kebomei, as a new type of oral hypoxia-inducible factor prolyl hydroxylase inhibitors (HIF-PHIs), has a good effect in the treatment of anemia patients with kidney disease. These drugs can stimulate the body to produce an effect similar to that in the plateau area, prompting the body to produce more red blood cells to transport the oxygen needed by the body, thereby improving the red blood cells in the blood associated with anemia in patients with end-stage renal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/26
CPCC07D217/26
Inventor 柏江涛马鸿杰赵彦轻
Owner SHENZHEN KEXING PHARM CO LTD
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