118307-04-3

Usage

Uses

Used in Organic Synthesis:
5-Chloroacetyl-6-chloro-1,3-dihydro-2H-indole-2-one is used as a synthetic building block for the creation of more complex organic molecules. Its chemical properties make it a versatile compound that can be utilized in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Chloroacetyl-6-chloro-1,3-dihydro-2H-indole-2-one is used as an intermediate in the synthesis of various drugs. Its unique structure allows for the development of novel therapeutic agents with potential applications in treating a wide range of diseases and medical conditions.
Used in Agrochemical Industry:
5-Chloroacetyl-6-chloro-1,3-dihydro-2H-indole-2-one is also used in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its incorporation into these products can lead to improved efficacy and selectivity, ultimately contributing to more sustainable agricultural practices.
Used in Dye and Pigment Industry:
In the dye and pigment industry, 5-Chloroacetyl-6-chloro-1,3-dihydro-2H-indole-2-one is used as a starting material for the production of various dyes and pigments. Its light brown solid form can be transformed into a range of colors, making it a valuable component in the creation of new and improved dyes and pigments for various applications.
Used in Research and Development:
5-Chloroacetyl-6-chloro-1,3-dihydro-2H-indole-2-one is also utilized in research and development settings, where it serves as a key compound for exploring new chemical reactions and understanding the underlying mechanisms of organic synthesis. Its use in this context can lead to the discovery of new synthetic pathways and the development of innovative applications across various industries.

InChI:InChI=1/C10H7Cl2NO2/c11-4-9(14)6-1-5-2-10(15)13-8(5)3-7(6)12/h1,3H,2,4H2,(H,13,15)

Upstream product

• 147124-32-1 dimethyl (4-chloro-2-nitrophenyl)malonate 
• 89-61-2 2,5-dichloronitrobenzene 
• 79-04-9 chloroacetyl chloride 
• 56341-37-8 6-chloro-2-oxindole 

Downstream Products

• 884305-08-2 5-(2-(4-(1,2-benzisothiazole-3-yl)-1-piperazinyl)-1-hydroxyethyl)-6-chloro-1,3-dihydro-2H-indole-2-one 
• 884305-07-1 5-(2-(4-(1,2-benzisothiazole-3-yl)-1-piperazinyl)-1-oxoethyl)-6-chloro-1,3-dihydro-2H-indole-2-one 
• 122883-93-6 ziprazidone 
• 1156390-49-6 6-chloro-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid 
• 118289-55-7 6-chloro-5-(2-chloroethyl)-2-oxindole 
• 884305-06-0 6-chloro-5-(2-chloro-1-hydroxyethyl) indolin-2-one 

Relevant academic research and scientific papers

Impurity in ziprasidone hydrochloride and preparation method of impurity

The invention provides an impurity in ziprasidone hydrochloride. The impurity has a structure as shown in formula 1. According to the present invention, the impurity with the specific structure is obtained based on incomplete reaction during the ziprasidone hydrochloride preparation process, and the impurity is introduced and transferred to a final product, and the corresponding impurity preparation steps are provided so as to provide the corresponding technical support for the ziprasidone hydrochloride preparation. The synthesis method provided by the invention is simple in process, high in controllability and mild in condition, can be used for quality standard establishment and quality control links such as ziprasidone hydrochloride process research and development, production and the like, and provides technical support for ziprasidone hydrochloride medication safety. The method can be used for quality research such as qualitative and quantitative analysis of impurities in ziprasidone hydrochloride synthesis, so that improvement of the quality of ziprasidone hydrochloride is facilitated, and great guiding significance is provided for reducing the medication risk of ziprasidone hydrochloride.

Discovery of indolin-2-one derivatives as potent PAK4 inhibitors: Structure-activity relationship analysis, biological evaluation and molecular docking study

Utilizing a pharmacophore hybridization approach, a novel series of substituted indolin-2-one derivatives were designed, synthesized and evaluated for their in vitro biological activities against p21-activated kinase 4. Compounds 11b, 12d and 12g exhibited the most potent inhibitory activity against PAK4 (IC50?=?22?nM, 16?nM and 27?nM, respectively). Among them, compound 12g showed the highest antiproliferative activity against A549 cells (IC50?=?0.83?μM). Apoptosis analysis in A549 cells suggested that compound 12g delayed cell cycle progression by arresting cells in the G2/M phase of the cell cycle, retarding cell growth. Further investigation demonstrated that compound 12g strongly inhibited migration and invasion of A549 cells. Western blot analysis indicated that compound 12g potently inhibited the PAK4/LIMK1/cofilin signalling pathways. Finally, the binding mode between compound 12g with PAK4 was proposed by molecular docking. A preliminary ADME profile of the compound 12g was also drawn on the basis of QikProp predictions.

A SHORT PROCESS FOR THE PREPARATION OF ZIPRASIDONE AND INTERMEDIATES THEREOF

A process for the preparation of oxindole derivative (Ziprasidone hydrochloride) of formula (I) comprising reacting compound of formula (II) with metal or metal compound mineral acid to give compound of formula (III) in a single step which is converted into compound of formula IV which is a key intermediate for the preparation of compound of compound of formula (I).

Improved process for the preparation of 6-chloro-5-(2-chloroethyl)oxindole

The current process for ziprasidone involves preparation and isolation of the key intermediate 6-chloro-5-(2-chloroethyl)oxindole. An improved process for the synthesis of this intermediate is reported here. The new process involves use of a novel Lewis acid-mediated selective deoxygenation of the precursor ketone with tetramethyldisiloxane. The new method affords the desired compound in a one-pot process obviating the need for isolation of the potentially hazardous precursor ketone. This process was successfully scaled up to multikilo scale.

Ziprasidone process

A process for preparing ziprasidone having low levels of keto ziprasidone and hydroxy ziprasidone impurities.

Process for the preparation of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1piperazinyl) ethyl)-6-chloro-1, 3-dihydro-2h-indol-2-one hydrochloride (ziprasidone hydrochloride) and its intermediate

The present invention relates to improved processes for the preparation of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl) ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one and its hydrochloride, which is known as Ziprasidone hydrochloride of Formula (I) and 5-(2-Chloro acetyl)-6-chloro oxindole of Formula (IV), which is an intermediate for the preparation of 5-(2-chloro ethyl)-6-chloro oxindole of Formula (V). Ziprasidone hydrochloride of Formula (I) of the present invention is depicted by the following structure.

A PROCESS FOR THE PREPARATION OF OXINDOLE DERIVATIVES

A process for the preparation of oxindole derivative of formula (I) comprising reacting compound of formula (II) with dialkyl malonate, COOR1-COOR1, in the presence of a mild base to give compound of formula (III); and wherein R is selected from hydrogen, linear, branched or cyclic alkyl, aryl, substituted aryl, heteroaryl, haloalkyl like CF3, alkoxy, haloalkoxy, thioalkyl and halogen.; R1 is selected from linear, branched and cyclic alkyl (C1 to C4 groups); and X is selected from chloro, bromo, fluoro and iodo groups;further converting compound of formula (III) to compound of formula (I).

METHOD OF TREATING GLAUCOMA AND ISCHEMIC RETINOPATHY

A method for treating glaucoma and ischemic retinopathy in a mammal, comprising administering to said mammal a therapeutically effective amount of a compound of the formula or a pharmaceutically acceptable acid addition salt thereof, wherein n, X, Y and A

Method of treating psychiatric conditions

A method for treating a psychiatic condition or disorder selected from anxiety disorders such as panic disorder, posttraumatic stress disorder and phobias, psychotic episodes of anxiety, anxiety associated with psychosis, psychotic mood disorders such as severe major depressive disorder and mood disorders associated with psychotic disorders such as acute mania or depression associated with bipolar disorder, schizophrenia, behavioral manifestations of mental retardation, conduct disorder or autistic disorder, dementias such as dementias of the Alzheimer's type, and dyskinesias such as drug induced and neurodegeneration based dyskinesias in a mammal, including a human, comprising administering to said mammal a pharmaceutically effective amount of a compound of the formula or a pharmaceutically acceptable acid addition salt thereof, wherein n, X, Y and Ar are as defined above.

Method of treating tourette's syndrome and obsessive compulsive disorder

A method for treating Tourette's syndrome, obsessive compulsive disorder, chronic motor or vocal tic disorder in a mammal, including a human, comprising administering to said mammal an effective amount of a compound of the formula STR1 or a pharmaceutically acceptable acid addition salt thereof, wherein n, X, Y and Ar are as defined above.