60695-25-2Relevant academic research and scientific papers
Bulky amine analogues of ketoprofen: Potent antiinflammatory agents
Schlegel,Zenitz,Fellows,Laskowski,Behn,Phillips,Botton,Speight
, p. 1682 - 1690 (2007/10/02)
Replacement of the carboxyl group of 2-(3-benzoylphenyl)propionic acid (Ketoprofen) with various bulky amines has produced a series of highly active antiinflammatory agents that have reduced intestinal ulcerogenicity and have better therapeutic ratios in the 21-day adjuvant arthritis assay on rats than currently marketed nonsteroidal antiinflammatory drugs. Activity is maintained on reduction of these 2-(3-benzoylphenyl)propyl bulky amines to the corresponding alcohols or methylene analogues, on conversion of the ketone function to a primary amine or oxime, and on introduction of a 4-halo substituent (Cl or F) on the terminal aromatic ring. Removal of the α-CH3 group greatly reduces the antiinflammatory activity of the series. These compounds have been synthesized by the reductive amination of 2-(3-bromophenyl)propionaldehyde with the respective amine followed by lithiation of this product and condensation with the appropriate benzonitrile.
4-[[3-[α-Aminobenzyl]phenyl]methyl]morpholine and 4-[-[3-benzoylphenyl]ethyl]morpholine
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, (2008/06/13)
N-{2, 3- and 4-[R1 -(phenyl)-C(=X)]-phenyl-lower-alkyl}amines, useful as anti-inflammatory agents, are prepared either by reduction of 2-, 3- or 4-[R1 -(phenyl)-CO]-phenyl-lower-alkanoylamines, which are also useful as anti-inflammatory agents; by benzoylating a phenyl-lower-alkylamine; by reaction of a 2-, 3- or 4-lithiophenyl-lower-alkylamine with a R1 -(phenyl)-carboxaldehyde, a R1 -(phenyl)-lower-alkyl ketone or a R1 -(phenyl)-carbonitrile; by reaction of a 2-, 3- or 4-[R1 -(phenyl)-CO]-phenyl-lower-alkyl tosylate with an appropriate amine; or by transformations involving manipulations of a carbonyl or carbinol group.
Intermediates for preparing anti-inflammatory phenyl-lower-alkylamines
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, (2008/06/13)
N-{3- and 4-[R1 -(phenyl)-C(=X)]-phenyl-lower-alkyl}amines, useful as anti-inflammatory agents, are prepared either by reduction of 3- or 4-[R1 -(phenyl)-CO]-phenyl-lower-alkanoylamines, which are also useful as anti-inflammatory agents; by benzoylating a phenyl-lower-alkylamine; by reaction of a 3- or 4-lithiophenyl-lower-alkylamine with a R1 -(phenyl)-carboxaldehyde, a R1 -(phenyl)-lower-alkyl ketone or a R1 -(phenyl)-carbonitrile or by transformations involving manipulations of a carbonyl or carbinol group.
Anti-inflammatory phenyl-lower-alkylamines
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, (2008/06/13)
N-{3-[R1 -(phenyl)-C(=X)]-phenyl-lower-alkyl}amines having anti-inflammatory utility are prepared either by reduction of a 3-[R1 -(phenyl)-CO]-phenyl-lower-alkanoylamine; by benzoylating a phenyl-lower-alkylamine; by reaction of a 3-lithiophenyl-lower-alkylamine with a R1 -(phenyl)-carboxaldehyde, a R1 -(phenyl)lower-alkyl ketone or a R1 -(phenyl)-carbonitrile or by transformations involving manipulations of a carbonyl or carbinol group.
