e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Antiallergy agents. 1. Substituted 1, 8-naphthyridin-2 (1H)-ones as inhibitors of SRS-A release

…, JJ Kaminski, WC Tom, JF Lee, SC Wong…

Index: Sherlock, Margaret H.; Kaminski, James J.; Tom, Wing C.; Lee, Joe F.; Wong, Shing-Chun; et al. Journal of Medicinal Chemistry, 1988 , vol. 31, # 11 p. 2108 - 2121

Full Text: HTML

Citation Number: 68

Abstract

Scheme I). The required nicotinic acids and esters described in Table I, and the substituted amines described in the experimental section were either commercially available or their method of preparation has been described previo~ sly.~*-~~ The substituted pyridines (3) and congeners described in Table I1 were prepared by the procedures described by Kermack and Weatherhead24 or Nantka-N amir~ ky,~~ respectively. Following the ...

2-Chloronicotinic acid Structure

2-Chloronicotin...

Benzylamine Structure

~93%

2-(benzylamino)nicotinic acid Structure

2-(benzylamino)...

Ethanoic anhydride Structure

Ethanoic anhydride

1-phenyl-4-prop-2-enoxy-1,8-naphthyridin-2-one Structure

1-phenyl-4-prop...

~50%

1-Phenyl-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one Structure

1-Phenyl-3-(2-p...

Cyclohexaneacetic acid,ethyl ester Structure

Cyclohexaneacet...

CHEMPACIFIC 39976 Structure

CHEMPACIFIC 39976

~28%

3-cyclohexyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-cyclohexyl-4-...

Methyl 2-chloronicotinate Structure

Methyl 2-chloro...

~%

3-cyclohexyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-cyclohexyl-4-...

Structure

~%

3-cyclohexyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-cyclohexyl-4-...

2-Chloronicotinic acid Structure

2-Chloronicotin...

4-Butylaniline Structure

~97%

Butanixin Structure

Ethyl hexanoate Structure

Ethyl hexanoate

methyl 3-anilinopyrazine-2-carboxylate Structure

methyl 3-anilin...

~65%

7-butyl-8-hydroxy-5-phenylpyrido[2,3-b]pyrazin-6-one Structure

7-butyl-8-hydro...

Methyl 2-chloronicotinate Structure

Methyl 2-chloro...

~%

4-hydroxy-1-phenyl-3-(4-phenylbutyl)-1,8-naphthyridin-2-one Structure

4-hydroxy-1-phe...

Structure

~%

4-hydroxy-1-phenyl-3-(4-phenylbutyl)-1,8-naphthyridin-2-one Structure

4-hydroxy-1-phe...

Ethyl hexanoate Structure

Ethyl hexanoate

methyl 2-((2,6-dimethylphenyl)amino)nicotinate Structure

methyl 2-((2,6-...

~61%

3-butyl-1-(2,6-dimethylphenyl)-4-hydroxy-1,8-naphthyridin-2-one Structure

3-butyl-1-(2,6-...

2-Chloronicotinic acid Structure

2-Chloronicotin...

~%

3-butyl-1-(2,6-dimethylphenyl)-4-hydroxy-1,8-naphthyridin-2-one Structure

3-butyl-1-(2,6-...

2-(2,6-dimethylanilino)pyridine-3-carboxylic acid Structure

2-(2,6-dimethyl...

~%

3-butyl-1-(2,6-dimethylphenyl)-4-hydroxy-1,8-naphthyridin-2-one Structure

3-butyl-1-(2,6-...

2,6-xylidine Structure

~%

3-butyl-1-(2,6-dimethylphenyl)-4-hydroxy-1,8-naphthyridin-2-one Structure

3-butyl-1-(2,6-...

cyanomethyl 2-(3-methylthiophenylamino)nicotinate Structure

cyanomethyl 2-(...

~96%

methyl 2-(3-methylsulfanylanilino)pyridine-3-carboxylate Structure

methyl 2-(3-met...

2-Chloronicotinic acid Structure

2-Chloronicotin...

~%

methyl 2-(3-methylsulfanylanilino)pyridine-3-carboxylate Structure

methyl 2-(3-met...

3-(Methylmercapto)aniline Structure

3-(Methylmercap...

~%

methyl 2-(3-methylsulfanylanilino)pyridine-3-carboxylate Structure

methyl 2-(3-met...

2-(3-Methylsulfanyl-phenylamino)-nicotinic acid Structure

2-(3-Methylsulf...

~%

methyl 2-(3-methylsulfanylanilino)pyridine-3-carboxylate Structure

methyl 2-(3-met...

Methyl 2-chloronicotinate Structure

Methyl 2-chloro...

Structure

~92%

CHEMPACIFIC 39976 Structure

CHEMPACIFIC 39976

2-Chloronicotinic acid Structure

2-Chloronicotin...

1,1-Dimethylethylenediamine Structure

1,1-Dimethyleth...

~58%

2-{[2-(Dimethylamino)ethyl]amino}nicotinic acid Structure

2-{[2-(Dimethyl...

2-Chloronicotinic acid Structure

2-Chloronicotin...

5-Aminoindan Structure

~77%

2-(5-indanamino)-3-pyridine carboxylic acid Structure

2-(5-indanamino...

N/A Structure

~54%

4-hydroxy-3-(3-hydroxybutyl)-1-phenyl-1,8-naphthyridin-2-one Structure

4-hydroxy-3-(3-...

Ethyl 4-oxopentanoate Structure

Ethyl 4-oxopent...

~%

4-hydroxy-3-(3-hydroxybutyl)-1-phenyl-1,8-naphthyridin-2-one Structure

4-hydroxy-3-(3-...

ethyl 5,5-(ethylenedioxy)levulinate Structure

ethyl 5,5-(ethy...

~%

4-hydroxy-3-(3-hydroxybutyl)-1-phenyl-1,8-naphthyridin-2-one Structure

4-hydroxy-3-(3-...

1-phenyl-3-[3,3-(ethylenedioxy)butyl]-4-hydroxy-1,8-naphthyridin-2(1H)-one Structure

1-phenyl-3-[3,3...

~%

4-hydroxy-3-(3-hydroxybutyl)-1-phenyl-1,8-naphthyridin-2-one Structure

4-hydroxy-3-(3-...

1-Phenyl-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one Structure

1-Phenyl-3-(2-p...

~90%

3-allyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one Structure

3-allyl-4-hydro...

3-butyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

~24%

3-butyl-1-phenyl-4-prop-2-ynoxy-1,8-naphthyridin-2-one Structure

3-butyl-1-pheny...

Methyl 2-chloronicotinate Structure

Methyl 2-chloro...

~%

3-butyl-1-phenyl-4-prop-2-ynoxy-1,8-naphthyridin-2-one Structure

3-butyl-1-pheny...

CHEMPACIFIC 39976 Structure

CHEMPACIFIC 39976

~%

3-butyl-1-phenyl-4-prop-2-ynoxy-1,8-naphthyridin-2-one Structure

3-butyl-1-pheny...

Structure

~%

3-butyl-1-phenyl-4-prop-2-ynoxy-1,8-naphthyridin-2-one Structure

3-butyl-1-pheny...

methyl 2-(N-phenylhexanamido)nicotinate Structure

methyl 2-(N-phe...

~%

3-butyl-1-phenyl-4-prop-2-ynoxy-1,8-naphthyridin-2-one Structure

3-butyl-1-pheny...

3-butyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

~60%

3-butyl-4-ethoxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-ethox...

Methyl 2-chloronicotinate Structure

Methyl 2-chloro...

~%

3-butyl-4-ethoxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-ethox...

CHEMPACIFIC 39976 Structure

CHEMPACIFIC 39976

~%

3-butyl-4-ethoxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-ethox...

Structure

~%

3-butyl-4-ethoxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-ethox...

methyl 2-(N-phenylhexanamido)nicotinate Structure

methyl 2-(N-phe...

~%

3-butyl-4-ethoxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-ethox...

Ethyl hexanoate Structure

Ethyl hexanoate

methyl 2-((4-(methylthio)phenyl)amino)nicotinate Structure

methyl 2-((4-(m...

~80%

3-butyl-4-hydroxy-1-(4-methylsulfanylphenyl)-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

2-Chloronicotinic acid Structure

2-Chloronicotin...

~%

3-butyl-4-hydroxy-1-(4-methylsulfanylphenyl)-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

2-(4-Methylsulfanyl-phenylamino)-nicotinic acid Structure

2-(4-Methylsulf...

~%

3-butyl-4-hydroxy-1-(4-methylsulfanylphenyl)-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

4-(Methylmercapto)aniline Structure

4-(Methylmercap...

~%

3-butyl-4-hydroxy-1-(4-methylsulfanylphenyl)-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

2-Chloronicotinic acid Structure

2-Chloronicotin...

3-anisidine Structure

~90%

2-(3-Methoxy-phenylamino)-nicotinic acid Structure

2-(3-Methoxy-ph...

3-butyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

2-Bromoethanol Structure

~41%

3-butyl-4-(2-hydroxyethoxy)-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-(2-hy...

Methyl 2-chloronicotinate Structure

Methyl 2-chloro...

~%

3-butyl-4-(2-hydroxyethoxy)-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-(2-hy...

CHEMPACIFIC 39976 Structure

CHEMPACIFIC 39976

~%

3-butyl-4-(2-hydroxyethoxy)-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-(2-hy...

Structure

~%

3-butyl-4-(2-hydroxyethoxy)-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-(2-hy...

methyl 2-(N-phenylhexanamido)nicotinate Structure

methyl 2-(N-phe...

~%

3-butyl-4-(2-hydroxyethoxy)-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-(2-hy...

Ethyl hexanoate Structure

Ethyl hexanoate

methyl 2-(3-methylsulfanylanilino)pyridine-3-carboxylate Structure

methyl 2-(3-met...

~87%

3-butyl-4-hydroxy-1-(3-methylsulfanylphenyl)-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

2-Chloronicotinic acid Structure

2-Chloronicotin...

~%

3-butyl-4-hydroxy-1-(3-methylsulfanylphenyl)-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

3-(Methylmercapto)aniline Structure

3-(Methylmercap...

~%

3-butyl-4-hydroxy-1-(3-methylsulfanylphenyl)-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

2-(3-Methylsulfanyl-phenylamino)-nicotinic acid Structure

2-(3-Methylsulf...

~%

3-butyl-4-hydroxy-1-(3-methylsulfanylphenyl)-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

cyanomethyl 2-(3-methylthiophenylamino)nicotinate Structure

cyanomethyl 2-(...

~%

3-butyl-4-hydroxy-1-(3-methylsulfanylphenyl)-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

2-Chloronicotinic acid Structure

2-Chloronicotin...

4-Fluoroaniline Structure

4-Fluoroaniline

~90%

2-(4-Fluoro-phenylamino)-nicotinic acid Structure

2-(4-Fluoro-phe...

allyl bromide Structure

3-butyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

~26%

3-butyl-1-phenyl-4-prop-2-enoxy-1,8-naphthyridin-2-one Structure

3-butyl-1-pheny...

Methyl 2-chloronicotinate Structure

Methyl 2-chloro...

~%

3-butyl-1-phenyl-4-prop-2-enoxy-1,8-naphthyridin-2-one Structure

3-butyl-1-pheny...

CHEMPACIFIC 39976 Structure

CHEMPACIFIC 39976

~%

3-butyl-1-phenyl-4-prop-2-enoxy-1,8-naphthyridin-2-one Structure

3-butyl-1-pheny...

Structure

~%

3-butyl-1-phenyl-4-prop-2-enoxy-1,8-naphthyridin-2-one Structure

3-butyl-1-pheny...

methyl 2-(N-phenylhexanamido)nicotinate Structure

methyl 2-(N-phe...

~%

3-butyl-1-phenyl-4-prop-2-enoxy-1,8-naphthyridin-2-one Structure

3-butyl-1-pheny...

2-(N-acetylanilino)-3-carbomethoxypyridine Structure

2-(N-acetylanil...

~93%

4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

4-hydroxy-1-phe...

CHEMPACIFIC 39976 Structure

CHEMPACIFIC 39976

~%

4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

4-hydroxy-1-phe...

Methyl 2-chloronicotinate Structure

Methyl 2-chloro...

~%

4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

4-hydroxy-1-phe...

Structure

~%

4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

4-hydroxy-1-phe...

3-butyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

3-Bromopropan-1-ol Structure

3-Bromopropan-1-ol

~88%

3-butyl-4-(3-hydroxypropoxy)-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-(3-hy...

Methyl 2-chloronicotinate Structure

Methyl 2-chloro...

~%

3-butyl-4-(3-hydroxypropoxy)-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-(3-hy...

CHEMPACIFIC 39976 Structure

CHEMPACIFIC 39976

~%

3-butyl-4-(3-hydroxypropoxy)-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-(3-hy...

Structure

~%

3-butyl-4-(3-hydroxypropoxy)-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-(3-hy...

methyl 2-(N-phenylhexanamido)nicotinate Structure

methyl 2-(N-phe...

~%

3-butyl-4-(3-hydroxypropoxy)-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-(3-hy...

4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

4-hydroxy-1-phe...

allyl bromide Structure

~46%

1-phenyl-4-prop-2-enoxy-1,8-naphthyridin-2-one Structure

1-phenyl-4-prop...

Methyl 2-chloronicotinate Structure

Methyl 2-chloro...

~%

1-phenyl-4-prop-2-enoxy-1,8-naphthyridin-2-one Structure

1-phenyl-4-prop...

CHEMPACIFIC 39976 Structure

CHEMPACIFIC 39976

~%

1-phenyl-4-prop-2-enoxy-1,8-naphthyridin-2-one Structure

1-phenyl-4-prop...

Structure

~%

1-phenyl-4-prop-2-enoxy-1,8-naphthyridin-2-one Structure

1-phenyl-4-prop...

2-(N-acetylanilino)-3-carbomethoxypyridine Structure

2-(N-acetylanil...

~%

1-phenyl-4-prop-2-enoxy-1,8-naphthyridin-2-one Structure

1-phenyl-4-prop...

ethyl cyclohexanepropionate Structure

ethyl cyclohexa...

CHEMPACIFIC 39976 Structure

CHEMPACIFIC 39976

~76%

3-(cyclohexylmethyl)-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-(cyclohexylme...

Methyl 2-chloronicotinate Structure

Methyl 2-chloro...

~%

3-(cyclohexylmethyl)-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-(cyclohexylme...

Structure

~%

3-(cyclohexylmethyl)-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-(cyclohexylme...

2-(3-ethoxycarbonylpropyl)pyridine Structure

2-(3-ethoxycarb...

CHEMPACIFIC 39976 Structure

CHEMPACIFIC 39976

~86%

4-hydroxy-1-phenyl-3-(2-pyridin-2-ylethyl)-1,8-naphthyridin-2-one Structure

4-hydroxy-1-phe...

Methyl 2-chloronicotinate Structure

Methyl 2-chloro...

~%

4-hydroxy-1-phenyl-3-(2-pyridin-2-ylethyl)-1,8-naphthyridin-2-one Structure

4-hydroxy-1-phe...

Structure

~%

4-hydroxy-1-phenyl-3-(2-pyridin-2-ylethyl)-1,8-naphthyridin-2-one Structure

4-hydroxy-1-phe...

Ethyl hexanoate Structure

Ethyl hexanoate

CHEMPACIFIC 39976 Structure

CHEMPACIFIC 39976

~82%

3-butyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

Methyl 2-chloronicotinate Structure

Methyl 2-chloro...

~%

3-butyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

Structure

~%

3-butyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

methyl 2-(N-phenylhexanamido)nicotinate Structure

methyl 2-(N-phe...

~%

3-butyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...

CHEMPACIFIC 39976 Structure

CHEMPACIFIC 39976

~%

3-butyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2-one Structure

3-butyl-4-hydro...