Preparation method of novel tinib medicine

A technology of tinib and drugs, applied in the field of medicine, can solve problems such as obvious side effects

Inactive Publication Date: 2021-03-26
天津羲泽润科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the effect of imatinib is remarkable, it also has obvious side effects. The main side effects include: neutropenia, thrombocytopenia, anemia, headache, indigestion, edema, weight gain, nausea, vomiting, muscle cramps, muscle Bone pain, diarrhea, rash, fatigue, and abdominal pain

Method used

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  • Preparation method of novel tinib medicine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add 27.7g (0.1mol, 1.0eq) N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2- Aminopyrimidine (1), 35.1g (0.11mol, 1.1eq) BOC-L-nitroarginine (2) and 250mL dimethylformamide (DMF), cooled to 10-20°C in an ice-water bath while stirring. Then add 45.5g (0.11mol, 1.1eq) of HCTU and 15.5g (0.12mol, 1.2eq) of DIPEA, and keep the reaction for 3 hours. The temperature was naturally raised to room temperature, and the reaction was continued for 2 h until the reaction of N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-aminopyrimidine (1) was completed. Add 500 mL of water to the reaction flask to quench the reaction, adjust the pH value to 9-10 with ammonia water, and precipitate a solid. After stirring for 1 hour, filter with suction, and rinse the obtained solid with 100 mL of water to obtain a crude product. Add the crude product into 200mL of ethyl acetate, heat to reflux to dissolve, cool down to 20-25°C with a water bath, stir and crystallize for 1 hour, filter with suction, and dry i...

Embodiment 2

[0020] Add 27.7g (0.1mol, 1.0eq) N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2- Aminopyrimidine (1), 38.3g (0.12mol, 1.2eq) BOC-L-nitroarginine (2) and 250mL dimethylformamide (DMF), cooled to 10-20°C in an ice-water bath while stirring. Then add 49.6g (0.12mol, 1.2eq) of HCTU and 18.1g (0.14mol, 1.4eq) of DIPE, and keep the reaction for 3 hours. The temperature was naturally raised to room temperature, and the reaction was continued for 2 h until the reaction of N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-aminopyrimidine (1) was completed. Add 500 mL of water to the reaction flask to quench the reaction, adjust the pH value to 9-10 with ammonia water, and precipitate a solid. After stirring for 1 hour, filter with suction, and rinse the obtained solid with 100 mL of water to obtain a crude product. Add the crude product into 200mL ethyl acetate, heat to reflux to dissolve, cool down to 20-25°C with a water bath, stir and crystallize for 1 hour, filter with suction, and dry in a ...

Embodiment 3

[0024] Add 27.7g (0.1mol, 1.0eq) N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2- Aminopyrimidine (1), 31.9g (0.1mol, 1.0eq) BOC-L-nitroarginine (2) and 250mL dimethylformamide (DMF), cooled to 10-20°C in an ice-water bath while stirring. Then add 45.5g (0.1mol, 1.1eq) HCTU and 15.5g (0.1mol, 1.2eq) DIPE, and keep the reaction for 3 hours. The temperature was naturally raised to room temperature, and the reaction was continued for 2 h until the reaction of N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-aminopyrimidine (1) was completed. Add 500 mL of water to the reaction flask to quench the reaction, adjust the pH value to 9-10 with ammonia water, and precipitate a solid. After stirring for 1 hour, filter with suction, and rinse the obtained solid with 100 mL of water to obtain a crude product. Add the crude product to 200mL ethyl acetate, heat to reflux to dissolve, cool down to 20-25°C with a water bath, stir and crystallize for 1 hour, filter with suction, and dry in a blast oven ...

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Abstract

The invention provides a preparation method of a novel tinib medicine, wherein the preparation method comprises the steps: by using N-(5-amino-2-methyl phenyl)-4-(3-pyridyl)-2-aminopyrimidine (imatinib amine) and BOC-L-nitroarginine as raw materials, carrying out condensation, palladium catalytic hydrogenation reduction and Boc removal from methanesulfonic acid to form a salt, recrystallizing andrefining to obtain the high-purity novel tinib medicine.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a preparation method of a novel tinib drug. Background technique [0002] Imatinib is an oral drug for the treatment of adult patients with Philadelphia chromosome (Ber-Abl) positive chronic myelogenous leukemia (CML) in the blast phase, accelerated phase and chronic phase after failure of interferon therapy. CML is a disease of hematopoietic stem cells caused by abnormalities in the DNA of stem cells in the bone marrow. Abnormal DNA produces abnormal proteins that interfere with the normal production of white blood cells in the bone marrow, eventually leading to a dramatic increase in the number of white blood cells. CML is divided into three stages: chronic phase, accelerated phase, and crisis phase. The average survival time of patients in the crisis phase is only 2-3 months. Imatinib is also effective in the treatment of gastrointestinal stromal tumors, with an effective rat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07B2200/07C07D401/04
Inventor 马军礼
Owner 天津羲泽润科技有限公司
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