635702-60-2

Usage

InChI:InChI=1/C9H11N3.ClH/c1-6-8-4-3-7(10)5-9(8)11-12(6)2;/h3-5H,10H2,1-2H3;1H

Upstream product

• 20191-74-6 2-ethyl-5-nitroaniline 
• 635702-59-9 3-methyl-6-nitro-1H-indazole sulfate 
• 6494-19-5 3-methyl-6-nitro-1H-indazole 
• 444731-73-1 2,3?dimethyl?6?nitro?2H?indazole 

Downstream Products

• 444731-74-2 N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine 
• 1226499-98-4 N2,N4-bis(2,3-dimethyl-2H-indazol-6-yl)-pyrimidine-2,4-diamine 

Relevant academic research and scientific papers

Method for preparing 2, 3-dimethyl-2H-indazole-6-benzylamine hydrochloride

The invention discloses a method for preparing 2, 3-dimethyl-2H-indazole-6-benzylamine hydrochloride. The method comprises the steps of reacting a glacial acetic acid solution of tert-butyl nitrite and a glacial acetic acid solution of 5-nitro-2-ethylaniline in a first microreactor to generate 3-methyl-6-nitro-1H-indazole; reacting a homogeneous solution formed by mixing the 3-methyl-6-nitro-1H-indazole and a dimethyl sulfoxide solution of methyl iodide and a dimethyl sulfoxide solution of sodium ethoxide in a second microreactor to generate 2,3-dimethyl-6-nitro-2H-indazole; then reacting withmixed liquor formed by stirring a concentrated hydrochloric acid solution of stannous chloride and ethyl alcohol in a third microreactor to generate the 2, 3-dimethyl-2H-indazole-6-benzylamine hydrochloride. The method provided by the invention has the advantages of less side reaction, high yield, simplification of a complicated multi-step synthesis process, low toxicity and pollution, low production cost, good product quality, environment friendliness, energy saving and high efficiency, and is suitable for industrialized application.

Pyrimidineamines as angiogenesis modulators

Pyrimidine derivatives, which are useful as VEGFR2 inhibitors are described herein. The described invention also includes methods of making such pyrimidine derivatives as well as methods of using the same in the treatment of hyperproliferative diseases.

Treatment Method

The present invention is directed to methods of treating an ocular neovascular disorder in a mammal by administration of pyrimidine derivatives, benzodiazepinyl derivatives and pharmaceutical compositions containing the same. The invention encompasses methods of treating an ocular neovascular disorder by administration of 5-[[4-[(2,3-Dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl]amino]-2-methylbenzenesulfonamide, (S)-3-oxo-8-[3-(pyridin-2-ylamino)-1-propyloxy]-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetic acid or salts or solvates thereof. Combination therapies for the treatment of ocular neovascular disorders are also encompassed.

Discovery of 5-[[4-[(2,3-dimethyl-2H-indazol-6-yl)methylamino]-2- pyrimidinyl]amino]-2-methyl-benzenesulfonamide (pazopanib), a novel and potent vascular endothelial growth factor receptor inhibitor

Inhibition of the vascular endothelial growth factor (VEGF) signaling pathway has emerged as one of the most promising new approaches for cancer therapy. We describe herein the key steps starting from an initial screening hit leading to the discovery of pazopanib, N4-(2,3-dimethyl-2H-indazol- 6-yl)-N4-methyl-N2-(4-methyl-3-sulfonamidophenyl)-2,4- pyrimidinediamine, a potent pan-VEGF receptor (VEGFR) inhibitor under clinical development for renal-cell cancer and other solid tumors.

CANCER TREATMENT METHOD

The present invention relates to a method of treating cancer in a mammal by administration of pyrimidine derivatives and quinazoline derivatives. In particular, the method relates to a method of treating cancer by administration of 5-[[4-[(2,3-dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl]amino]-2-methylbenzenesulfonamide or salts or solvates thereof, and N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methane sulphonyl)ethyl]amino}methyl)-2-furyl]-4-quinazolinamine, or salts or solvates thereof.

CANCER TREATMENT METHOD

The present invention relates to a method of treating cancer in a mammal by administration of pyrimidine derivatives. In particular, the method relates to a method of treating cancer by administration of 5-[[4-[(2,3-Dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl]amino]-2-methylbenzenesulfonamide or a salt or solvate thereof.

PYRIMIDIN DERIVATIVES FOR THE TREATMENT OF MULTIPLE MYELOMA

The present invention relates to a method of treating cancer in a mammal by administration of pyrimidine derivatives and pharmaceutical compositions containing the same. In particular, the method relates to a method of treating multiple myeloma by administration of 5-[[4-[(2,3-Dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl]amino]-2-methylbenzenesulfonamide or salts or solvates thereof.

CANCER TREATMENT METHOD

A method of treating cancer is described including administration of a pyrimidine derivative and a quinazoline derivative as well as a pharmaceutical composition including the same.

CHEMICAL PROCESS

A process for the preparation of pyrimidine derivatives, which are useful as VEGFR2 inhibitors is described herein. The described invention also includes pyrimidine derivatives as well as methods of using the same in the treatment of hyperproliferative diseases.