676326-36-6

Basic information

• Product Name: Methyl 1-acetyl-2-oxoindoline-6-carboxylate
• Synonyms: Methyl 1-acetyl-2-oxoindoline-6-carboxylate;1-Acetyl-2,3-dihydro-2-oxo-1H-indole-6-carboxylic acid methyl ester;1-acetyl-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester
• CAS NO: 676326-36-6
• Molecular Formula: C₁₂H₁₁NO₄
• Molecular Weight: 233
• Mol File: 676326-36-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 489.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.330
• PKA: -1.94±0.20(Predicted)
• CAS DataBase Reference: Methyl 1-acetyl-2-oxoindoline-6-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 1-acetyl-2-oxoindoline-6-carboxylate(676326-36-6)
• EPA Substance Registry System: Methyl 1-acetyl-2-oxoindoline-6-carboxylate(676326-36-6)

Safety Data

• Hazardous Substances Data: 676326-36-6(Hazardous Substances Data)

Usage

Uses

Methyl 1-Acetyl-2-oxoindoline-6-carboxylate is a reagent used in the preparation of Nintedanib (N478290), an angiokinase inhibitor and is used in the treatment of idiopathic pulmonary fibrosis. Also inhibits the process blood vessel formation which may be used to assist in cancer therapy.

Upstream product

• 108-24-7 acetic anhydride 
• 14192-26-8 2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester 

Downstream Products

• 1168152-06-4 (E)-1-acetyl-3-(ethoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester 
• 1168152-07-5 (E)-1-acetyl-3-(methoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester 
• 656247-17-5 nintedanib 
• 894783-71-2 BIBF 1202 
• 1987887-92-2 methyl (Z)-3-(((4-(methylamino)phenyl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate 
• 1175365-43-1 methyl 1-acetyl-3-[ethoxy(phenyl)methylidene]-2-oxo-2,3-dihydro-7H-indole-6-carboxylate 
• 656247-18-6 methyl (3Z)-3-[({4-[N-methyl-2-(4-methylpiperazin-1-yl)acetamido]phenyl}amino)(phenyl)methylidene]-2-oxo-2,3-dihydro-1H-indole-6-carboxylate ethanesulfonate salt 
• 1253768-90-9 (Z)-1-acetyl-3-(hydroxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester 
• 1027407-75-5 (Z)-1-acetyl-3-(ethoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester 

Relevant articles and documents

Harnessing affinity-based protein profiling to reveal a novel target of nintedanib

Nintedanib (BIBF1120), a triple angiokinase inhibitor, was first approved for idiopathic pulmonary fibrosis (IPF) therapy and is also efficacious for lung carcinoma, and interstitial lung diseases, far beyond its inhibition of VEGFR/PDGFR/FGFR. We identified tripeptidyl-peptidase 1 (TPP1) as one of the direct targets of nintedanib employing the affinity-based protein profiling (AfBPP) technique. This may be a new mechanism for nintedanib's role different from tyrosine kinase inhibition.

Method for preparing nintedanib ethanesulfonate

The invention discloses a method for preparing nintedanib ethanesulfonate. The method comprises the following steps: carrying out acylation reaction on 2-oxoindole-6-methyl formate and acetic anhydride to obtain 1-acetyl-2-oxoindoline -6-methyl formate; condensing with trimethyl orthobenzoate to generate 1-acetyl-3-(methoxyphenyl methylene)-2-oxoindoline-6-methyl formate, and finally reacting withN-(4-aminophenyl)-N, 4-dimethyl-1-piperazinecarboxamide; under the condition of not separating a main product, adding an alkali for deprotection to generate nintedanib, and finally salifying with ethanesulfonic acid to generate the nintedanib ethanesulfonate. The method has the advantages of mild reaction conditions, simple process operation and high yield, can obtain the nintedanib ethanesulfonate with the purity of 100% without refining, and is suitable for industrial production.

ANTIBODY-ALK5 INHIBITOR CONJUGATES AND THEIR USES

The present disclosure relates to antibody-drug conjugates comprising ALK5 inhibitors and their uses.