78281-61-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-3-benzoyl-alpha-(methylthio)benzeneacetamide is used as an impurity in the production of Nepafenac (N390080) for its anti-inflammatory and analgesic effects. 2-Amino-3-benzoyl-alpha-(methylthio)benzeneacetamide contributes to the overall efficacy of Nepafenac as a selective COX-2 inhibitor, helping to reduce inflammation and alleviate pain without causing the side effects typically associated with non-selective NSAIDs.
As an impurity in Nepafenac, 2-Amino-3-benzoyl-alpha-(methylthio)benzeneacetamide may also play a role in the drug's pharmacological activity, potentially enhancing its therapeutic effects or modifying its pharmacokinetic properties. However, it is essential to monitor and control the levels of this impurity to ensure the safety and efficacy of the final drug product.

InChI:InChI=1/C16H16N2O2S/c1-21-15(16(18)20)12-9-5-8-11(13(12)17)14(19)10-6-3-2-4-7-10/h2-9,15H,17H2,1H3,(H2,18,20)

Upstream product

• 22551-24-2 2-(methylthio)acetamide 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 

Downstream Products

• 78281-72-8 nepafenac 

Relevant academic research and scientific papers

Preparation method of high-purity nepafenac intermediate

The invention provides a preparation method of a high-purity nepafenac intermediate, which belongs to the technical field of medicine synthesis. The preparation method comprises the following steps of dissolving a chlorinating agent in an organic solvent,

Preparation method of nepafenac

The invention discloses a preparation method of nepafenac. The method comprises the following steps: 1, synthesizing 2-(methylthio) acetamide; 2, synthesizing alpha-methylthio (2-amino-3-benzoyl) phenylacetamide; 3, synthesizing the nepafenac. Compared with the prior art, the preparation method of the nepafenac has the advantages that raw materials are easy to buy, excessive chlorinated impurities of a side reaction are easily purified, the less energy is consumed by increasing reaction temperature, and the final product does not need to be subjected to octadecyl silane (ODS) reverse phase rapid chromatography.

PROCESS FOR THE PREPARATION OF NEPAFENAC

Described herein are processes for the preparation of nepafenac and related intermediates, particularly wherein 2-aminobenzophenone is treated with a 2-(alkylthio)acetamide in the presence of sulfuryl chloride to afford a 2-(2-amino-3-benzoylphenyl)-2-(alkylthio)acetamide, which upon reduction affords nepafenac. Described herein are also processes for the purification of nepafenac, particularly for the removal of structurally similar impurities.

Development and a practical synthesis of nepafenac intermediate via modified gassman reaction

Modification of nepafenac intermediate synthesis (5A) via Gassman specific ortho-substitution is reported. According to the process, 2-aminobenzophenone (1A) and 2-(methylthio)acetamide (2) were reacted in the convenient temperature conditions, in the presence of N-chlorophthalimide (3) or 1,3-dichloro-5,5- dimethylhydantoin (4), to activate the formation of azasulfonium salt and rearrangement thereof to pure 2-amino-3-benzoyl-α-(methylthio) phenylacetamide (5A). The procedure appears to be suitable for a reaction carried out in a large scale.

Process For Preparing A Benzoylbenzeneacetamide Derivative

Disclosed is a process for preparing anti-inflammatory compound nepafenac comprising preparing a compound of formula (V) wherein a N-halosuccinimide is used as the halogenating agent, followed by desulfurization using Raney Nickel. Also disclosed is a polymorphic form B of 2-amino-3-benzoyl-α-(methylthio)-benzeneacetamide (i.e., a compound of formula (V) wherein R is methyl

Antiinflammatory Agents. 4. Syntheses and Biological Evaluation of Potential Prodrugs of 2-Amino-3-benzoylbenzeneacetic Acid and 2-Amino-3-(4-chlorobenzoyl)benzeneacetic Acid

A series of potential prodrugs of 2-amino-3-benzoylbenzeneacetic acid (amfenac) and 2-amino-3-(4-chlorobenzoyl)benzeneacetic acid were synthesized and evaluated for their cyclooxygenase inhibiting properties, antiinflammatory potency, and gastrointestinal irritation liability.One compound, 2-amino-3-(4-chlorobenzoyl)benzeneacetamide, possessed a therapeutic index 1 order of magnitude greater than that of indomethacin.

Method of producing an inhibitory effect on blood platelet aggregation

Novel 2-amino-3-benzoyl-phenylacetamides are provided having the formula: STR1 wherein R represents hydrogen or lower alkyl, R1 and R2 represent hydrogen, lower alkyl, cycloalkyl, phenyl and phenyl substituted by lower alkyl, lower alkoxy, halogen, nitro and trifluoromethyl, and R1 and R2 when taken together with the adjacent nitrogen may form a heterocyclic residue; X represents hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl; Y represents hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, lower alkylthio, lower alkyloxythio or lower alkyldioxythio; Am is primary amino (--NH2), methylamino or dimethylamino, and n is 1 to 3 inclusive. The compounds exhibit anti-inflammatory, antipyretic, anti-blood platelet aggregation and analgetic pharmacological activities.