1553977-42-6

Basic information

• Product Name: Btk inhibitor 1 (R enantioMer hydrochloride)
• Synonyms: Btk inhibitor 1 (R enantioMer hydrochloride);3-(4-Phenoxyphenyl)-1-(3R)-3-piperidinyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine hydrochloride (1:1);Btk inhibitor 1 R enantiomer HCl
• CAS NO: 1553977-42-6
• Molecular Formula: C₂₂H₂₂N₆O*ClH
• Molecular Weight: 422.91062
• Mol File: 1553977-42-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Btk inhibitor 1 (R enantioMer hydrochloride)(CAS DataBase Reference)
• NIST Chemistry Reference: Btk inhibitor 1 (R enantioMer hydrochloride)(1553977-42-6)
• EPA Substance Registry System: Btk inhibitor 1 (R enantioMer hydrochloride)(1553977-42-6)

Safety Data

• Hazardous Substances Data: 1553977-42-6(Hazardous Substances Data)

Usage

General Description

Btk inhibitor 1 (R enantiomer hydrochloride) is a chemical compound that acts as an inhibitor of Bruton’s tyrosine kinase (Btk), an enzyme that plays a crucial role in the activation of immune cells. Btk inhibitor 1 (R enantioMer hydrochloride) specifically targets the R enantiomer form of the molecule and is commonly used in research and drug development for the treatment of various Btk-related diseases, including certain types of cancer and autoimmune disorders. By inhibiting Btk, this compound has the potential to suppress the activation of immune cells and reduce inflammation, making it a promising candidate for the development of novel therapeutic agents.

Upstream product

• 940890-90-4 (S)-3-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester 
• 83255-86-1 3-bromo-4-aminopyrazolo<3,4-d>pyrimidine 
• 51067-38-0 4-phenoxyphenylboronic acid 
• 1419223-01-0 tert-butyl (3R)-3-(4-amino-3-bromo-1H-pyrazolo [3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate 
• 1276110-38-3 (R)-3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylic acid tert-butyl ester 
• 143900-44-1 tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate 
• 2380-63-4 4-Aminopyrazolo<3,4-d>pyrimidin 
• 151266-23-8 4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine 
• 1022150-11-3 (3R)‐4‐amino‐3‐(4-phenoxyphenyl)‐1‐(1‐tert-butoxycarbonylpiperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine 
• 330786-24-8 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1022150-12-4 (R)-3-(4-phenoxyphenyl)-1-(piperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine-4-amine 
• 330792-69-3 2-[(4-phenoxy-phenyl)-methoxy-methylene]-malononitrile 
• 330792-68-2 2-[hydroxy-(4-phenoxy-phenyl)-methylene]-malononitrile 
• 1623-95-6 4-phenoxybenzoyl chloride 

Downstream Products

• 1553977-08-4 (R)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-2,3,3-d₃-1-one 
• 936563-87-0 ibrutinib 

Relevant articles and documents

Tumor-Cell-Specific Targeting of Ibrutinib: Introducing Electrostatic Antibody-Inhibitor Conjugates (AiCs)

Ibrutinib is an inhibitor of Bruton's tyrosine kinase that has been approved for the treatment of patients with chronic lymphocytic leukemia, mantle cell lymphoma and Waldenstrom's macroglobulinemia and is connected with toxicities. To minimize its toxicities, we linked ibrutinib to a cell-targeted, internalizing antibody. To this end, we synthesized a poly-anionic derivate, ibrutinib-Cy3.5, that retains full functionality. This anionic inhibitor is complexed by our anti-CD20-protamine targeting conjugate and free protamine, and thereby spontaneously assembles into an electrostatically stabilized vesicular nanocarrier. The complexation led to an accumulation of the drug driven by the CD20 antigen internalization to the intended cells and an amplification of its pharmacological effectivity. In vivo, we observed a significant enrichment of the drug in xenograft lymphoma tumors in immune-compromised mice and a significantly better response to lower doses compared to the original drug.

Refined preparing method of ibrutinib

The invention discloses a refined preparing method of ibrutinib. According to the method, a compound with a formula 1 is used as a raw material, and the compound with the formula 1 and a compound with a formula 2 are reacted in the presence of a mitsunobu reaction reagent to generate a compound with a formula 3, and a protecting group of the compound with the formula 3 is removed in the presence of acid to generate a compound with a formula 4; the compound with the formula 4 and a compound with a formula 5 are subjected to a Suzuki coupling reaction in the presence of alkali and a catalyst to generate a compound with a formula 6; the compound with the formula 6 and acryloyl chloride are reacted in the presence of alkali to generate ibrutinib. Finally column chromatography separation is conducted, macroporous adsorption resin is adopted as filler, the eluent is ethyl acetate or petroleum ether, and a high-purity material is obtained. According to the refined preparing method of ibrutinib, the yield is high in every step, the product is convenient to purify, the purity is high, and the industrialized production prospect is good.

PROCESS FOR THE PREPARATION OF IBRUTINIB AND NEW SYNTHESIS INTERMEDIATE

Subject-matter of the invention is a process for the preparation of ibrutinib and intermediate compound.