- Preparation method of nepafenac
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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.
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Paragraph 0039; 0047; 0054; 0055
(2017/09/01)
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- PROCESS FOR THE PREPARATION OF NEPAFENAC
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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.
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Page/Page column 14
(2015/01/16)
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- Development and a practical synthesis of nepafenac intermediate via modified gassman reaction
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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.
- Cybulski, Marcin,Formela, Adam,Mucha, Mariola,Klos, Karolina,Roszczynski, Jacek,Winiarski, Jerzy
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p. 461 - 464,4
(2020/08/24)
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- Process For Preparing A Benzoylbenzeneacetamide Derivative
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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
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Page/Page column 5-6
(2009/12/27)
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- FLUOROQUINOLONE DERIVATIVES FOR OPHTHALMIC APPLICATIONS
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The present invention relates to fluoroquinolone derivatives having enhanced ocular penetration characteristics and/or antimicrobial activity, and to compositions comprising such derivatives. The derivatives and compositions are particularly well suited for treating ophthalmic bacterial infections. The present invention more particularly relates to the discovery that a 2-methyl substitution on a diazabicyclo group attached to a fluoroquinolone ring system produces improved permeability characteristics, and that a 5-amino substitution on a fluoroquinolone ring system results in improved anti-microbial activity.
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- Topically administrable compositions containing 3-benzoylphenylacetic acid derivatives for treatment of ophthalmic inflammatory disorders
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Novel ester and amide derivatives of 3-benzoylphenylacetic acid are disclosed. The use of these novel derivatives and certain known derivatives in topically administrable compositions for the treatment of ophthalmic inflammatory disorders is also disclosed.
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- Antiinflammatory Agents. 4. Syntheses and Biological Evaluation of Potential Prodrugs of 2-Amino-3-benzoylbenzeneacetic Acid and 2-Amino-3-(4-chlorobenzoyl)benzeneacetic Acid
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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.
- Walsh, David A.,Moran, H. Wayne,Shamblee, Dwight A.,Welstead, William J.,Nolan, Joseph C.,et al.
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p. 2296 - 2304
(2007/10/02)
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- Method of producing an inhibitory effect on blood platelet aggregation
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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.
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