330792-68-2

Usage

Uses

Used in Chemical Synthesis Industry:
Propanedinitrile, 2-[hydroxy(4-phenoxyphenyl)methylene]-, is utilized as a key intermediate in the synthesis of various complex organic compounds. Its unique structure facilitates multiple types of chemical reactions, making it a valuable building block for the creation of pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Pharmaceutical Development:
In the pharmaceutical industry, Propanedinitrile, 2-[hydroxy(4-phenoxyphenyl)methylene]-, serves as a precursor for the development of new drugs. Its chemical versatility allows for the design of molecules with specific therapeutic properties, potentially leading to the discovery of novel treatments for various diseases.
Used in Material Science:
Propanedinitrile, 2-[hydroxy(4-phenoxyphenyl)methylene]-, is employed in the development of advanced materials with tailored properties. Its incorporation into polymers and other materials can enhance their performance, leading to applications in coatings, adhesives, and composites with improved characteristics.
Used in Environmental Applications:
Propanedinitrile, 2-[hydroxy(4-phenoxyphenyl)Methylene]can be used in environmental remediation processes, where its chemical reactivity can be leveraged to neutralize or break down pollutants, contributing to cleaner and safer environmental conditions.

Upstream product

• 1623-95-6 4-phenoxybenzoyl chloride 
• 109-77-3 malononitrile 
• 2215-77-2 4-Phenoxybenzoic acid 
• 21218-94-0 methyl 4-phenoxybenzoate 
• 619-44-3 methyl 4-iodobenzoate 
• 108-95-2 phenol 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 330792-69-3 2-[(4-phenoxy-phenyl)-methoxy-methylene]-malononitrile 
• 330786-24-8 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 936563-87-0 1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one 
• 936563-86-9 tert-butyl 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate 
• 1609467-43-7 benzyl 3-[5-amino-4-cyano-3-(4-phenoxy-phenyl)-pyrazol-1-yl]-piperidine-1-carboxylate 
• 1609467-44-8 5-amino-3-(4-phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazole-4-carbonitrile 
• 1609467-45-9 5-amino-3-(4-phenoxyphenyl)-1-piperidin-3-yl-1H-pyrazole-4-carboxylic acid amide 
• 1609465-64-6 5-amino-1-(1-cyanopiperidin-3-yl)-3-(4-phenoxyphenyl)-1H-pyrazole carboxamide 
• 1609468-23-6 (S)-5-amino-3-(4-phenoxyphenyl)-1-piperidin-3-yl-1H-pyrazole-4-carboxylic acid amide 
• 1609467-02-8 1-[(3S)-1-acryloylpiperidin-3-yl]-5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide 
• 1558038-42-8 (R)-5-amino-3-(4-phenoxyphenyl)-1-piperidin-3-yl-1H-pyrazole-4-carboxylic acid amide 
• 1558036-85-3 1-[(3R)-1-acryloylpiperidin-3-yl]-5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide 
• 1609467-03-9 5-amino-1-{1-[(2E)-but-2-enoyl]piperidin-3-yl}-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide 
• 1609467-04-0 5-amino-1-{(3R)-1-[(2E)-4-hydroxybut-2-enoyl]piperidin-3-yl}-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide 

Relevant academic research and scientific papers

PROCESSES AND INTERMEDIATES FOR PREPARING A BTK INHIBITOR

Disclosed is a process for the preparation of certain intermediates, e.g. process for preparing a compound of formula (I) or a pharmaceutically acceptable salt thereof, in an enantioenriched form, which intermediate and processes are useful in the preparation of a BTK inhibitor, such as ibrutinib.

TREATMENT OF INDOLENT OR AGGRESSIVE B-CELL LYMPHOMAS USING A COMBINATION COMPRISING BTK INHIBITORS

Disclosed herein is a method for the prevention, delay of progression or treatment of indolent or aggressive B-cell lymphomas in an individual in need thereof, comprising administering a Btk inhibitor (in particularly (S)-7-(1-acryloylpiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carboxamide or a pharmaceutically acceptable salt thereof) in combination with an anti-PD-1 antibody. The potent and selective BTK inhibitor in combination with the anti-PD-1 antibody have a manageable toxicity profile in patients with indolent and aggressive lymphomas.

Therapeutic Combinations of a Proteasome Inhibitor and a BTK Inhibitor

Therapeutic combinations of a proteasome inhibitor and a Bruton's tyrosine kinase (BTK) inhibitor are described. In some embodiments, the invention provides pharmaceutical compositions comprising combinations of a proteasome inhibitor and a BTK inhibitor and methods of using the pharmaceutical compositions for treating a disease, in particular a cancer.

Catalytic Azido-Hydrazination of Alkenes Enabled by Visible Light: Mechanistic Studies and Synthetic Applications

A visible-light-enabled catalytic intermolecular azido-hydrazination method for unactivated alkenes is developed via an orderly radical addition sequence. This transformation features metal-free and redox-neutral conditions and is applicable to a wide range of alkenes with commercially available reagents. Mechanistic and kinetic studies reveal that the efficient generation of azide radical enabled by fluorenone under visible-light is critical to this methodology. The β-azido alkyl hydrazines prepared with this reaction can be conveniently derived to valuable synthetic building blocks, and one of the products has been successfully applied in the total synthesis of (±)-ibrutinib, which is used to treat B cell cancers. (Figure presented.).

USE OF A COMBINATION COMPRISING A BTK INHIBITOR FOR TREATING CANCERS

A method for the prevention, delay of progression or treatment of cancer in a subject, comprising administering to the subject in need thereof a Btk inhibitor, particularly, (S)-7-(1-acryloylpiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetra-hydropyrazolo[1,5-a]pyrimidine-3-carboxamide or a pharmaceutically acceptable salt thereof, in combination with an immune checkpoint inhibitor or a targeted therapy agent. A pharmaceutical combination comprising a Btk inhibitor, particularly, (S)-7-(1-acryloylpiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetra-hydropyrazolo[1,5-a]pyrimidine-3-carboxamide or a pharmaceutically acceptable salt thereof, in combination with an immune checkpoint inhibitor or a targeted therapy agent.

CRYSTALLINE FORM OF (S)-7-(1-ACRYLOYLPIPERIDIN-4-YL)-2-(4-PHENOXYPHENYL)-4,5,6,7-TETRAHYDROPYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXAMIDE, PREPARATION, AND USES THEREOF

The present invention relates to a crystalline form of (S)-7-(1-acryloylpiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetra-hydropyrazolo[1,5-a]pyrimidine-3-carboxamide for inhibiting Btk, methods of preparation thereof and pharmaceutical compositions, and use of the crystalline form above in the treatment of a disease, or in the manufacturing of a medicament for the treatment of a disease.

CRYSTALLINE FORMS OF (S) -7- (1- (BUT-2-YNOYL) PIPERIDIN-4-YL) -2- (4-PHENOXYPHENYL) -4, 5, 6, 7-TETRAHY DROPYRAZOLO [1, 5-A] PYRIMIDINE-3-CARBOXAMIDE, PREPARATION, AND USES THEREOF

The present invention relates to a crystalline form of (S) -7- (1- (but-2-ynoyl) piperidin-4-yl) -2- (4-phenoxyphenyl) -4, 5, 6, 7-tetrahydropyrazolo [1, 5-a] pyri midine-3-carboxamide for inhibiting Btk, methods of preparation thereof and pharmaceutical compositions, and use of the crystalline form above in the treatment of a disease, or in the manufacturing of a medicament for the treatment of a disease.

Methods of Using BTK Inhibitors to Treat Dermatoses

In certain embodiments, the invention includes therapeutic methods of using a BTK inhibitor to treat dermatoses, such as psoriasis, atopic dermatitis, contact dermatitis, scleroderma, and cutaneous lupus erythematosus. In other embodiments, the methods of the invention further comprise the step of administering a therapeutically effective dose of an anti-inflammatory agent.

Method for preparing ibrutinib

The invention discloses a method for preparing ibrutinib. The method includes the following steps of 1, preparation of IB-A, 2, preparation of IB-B, 3, preparation of IB-C, 4, preparation of IB-D, 5,preparation of IB-E, 6, preparation of IB-F, 7, preparation of IB-G, 8, preparation of IB-H, and 9, preparation of IB-J. The method has the advantages that the process is mature and stable, the quality of the product is stable, the production process is safe and reliable, and the ibrutinib is suitable for industrial production.

Ibrutinib intermediate and preparation method thereof

The invention discloses an ibrutinib intermediate and a preparation method thereof. The structure of the ibrutinib intermediate provided by the invention is shown as a formula I; the definition of R is shown as a specification and a claim. The ibrutinib intermediate can be used for preparing an ibrutinib key intermediate of 3-(4-phenoxyl phenyl)-1H-parazole[3,4-d]pyrimidine-4-amine; the preparation method comprises the steps of preparing an active intermediate of a compound shown as a formula II from a compound shown as a formula I under the effect of active nucleophilic reagents; cyclizing the compound shown as the formula II to obtain a compound 3-amino-5-(4-phenoxyl phenyl)-4-cyan-1H-parazole shown as a formula 4; performing ring closing on the compound shown as the formula 4 to obtainthe ibrutinib key intermediate. The method has the advantages that the raw materials are cheap and can be easily obtained; the use of dangerous reagents is not needed; the reaction conditions are mild; the operation is simple; the method is suitable for industrial production. (The formulas are shown in the description.).