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Carbamates as btk inhibitors

A technology of carbadithioformic acid and dithioformic acid, which is applied in the field of preparation of new carbamate compounds for the treatment or prevention of cancer, and can solve the problem of under-immunity, lack of antibodies, and B cell death And other issues

Active Publication Date: 2020-08-11
北京博远精准医疗科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It was first found that the function of BTK was related to human immune diseases. In X-linked agammaglobulinemia (XLA), it was found that the mutation of BTK would affect the expression of BTK protein, resulting in the immature death of B cells. The patient lacked antibodies and Mature peripheral B lymphocytes, immune system

Method used

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  • Carbamates as btk inhibitors
  • Carbamates as btk inhibitors
  • Carbamates as btk inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0063] Next, the present invention will be described in further detail through examples, but the present invention is not limited to these examples.

[0064] In an exemplary embodiment, the compound of the present invention is synthesized by the following method, wherein each substituent is as defined in the general formula (I).

preparation Embodiment 1

[0065] Preparation Example 1: 2-Chloro-5-fluoro-N-(3-nitrophenyl)pyrimidin-4-amine

[0066]

[0067] Dissolve 2,4-dichloro-5-fluoropyrimidine (2g, 12mmol) and m-nitroaniline (1.38g, 10mmol) in 20ml of isopropanol, then add DIEA (1.6ml, 10mmol), and heat at 90°C Reflux for 6 hours until a large number of yellow solids are formed, cool to room temperature, filter with suction, wash the solid with 95% ethanol and ether, and dry to obtain a light yellow flocculent solid (1.77g, yield 66%). 1 H NMR (400MHz, DMSO-d 6 )δ10.38(s,1H),8.72(t,J=2.1Hz,1H),8.41(d,J=3.3Hz,1H),8.14(dd,J=8.2,1.4Hz,1H),7.98– 7.89 (m, 1H), 7.65 (t, J=8.2Hz, 1H).

preparation Embodiment 2a

[0068] Preparative Example 2a: 1-(2-Chloroethoxy)-4-nitrobenzene

[0069]

[0070] Add p-nitrophenol (1.39g, 10mmol) and potassium carbonate (1.38g, 10mmol) to 25ml of acetonitrile, then dropwise add 1-bromo-2-chloroethane (2.5ml, 30mmol), and reflux overnight at 80°C. After the reaction, add water to dissolve potassium carbonate, extract with ethyl acetate, wash the organic phase with saturated sodium bicarbonate and brine, evaporate to dryness under reduced pressure to give a white solid (1.69g, yield 84%), the product is directly used without purification react in the next step.

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Abstract

The invention aims at providing a dithiocarbamate type compound used as a BTK (Bruton Tyrosine Kinase) inhibitor and a pharmaceutical composition thereof, a preparation method and application. The compound provided by the invention has a structure shown as a general formula (I). The formula (I) is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and relates to a novel compound, a method for preparing the compound, a pharmaceutical composition and a use thereof. Specifically, the invention relates to a novel carbamate compound as a BTK inhibitor, and the preparation of these compounds Use in medicines for the treatment or prevention of cancer. Background technique [0002] Lymphoma is a relatively common tumor in my country, ranking 11-13 in the cause of death from malignant tumors. Malignancies of B cell origin include chronic lymphocytic leukemia (CLL), acute lymphoblastic leukemia (ALL), small lymphocytic lymphoma (SLL), mantle cell lymphoma (MCL), follicular lymphoma (FL), Diffuse large B-cell lymphoma (DLBCL), multiple myeloma (MM) and Waldenstrom macroglobulinemia (WM), etc. Currently, chemotherapy is the main treatment for lymphoma, and commonly used drugs include cytotoxic drugs such as chlorambucil, cyclophosphamide...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/48C07D413/12C07D401/12C07D403/12A61K31/505A61K31/506A61K31/5377A61P35/02A61P35/00
CPCA61P35/00A61P35/02C07D239/48C07D401/12C07D403/12C07D413/12
Inventor 尹玉新翟峥
Owner 北京博远精准医疗科技有限公司