158147-48-9

Upstream product

• 158147-47-8 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethyl)quinoline-3-carboxylic acid ethyl ester 
• 158147-45-6 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-3-ethoxycarbonylquinoline-2-acetic acid ethyl ester 
• 153394-55-9 2-amino-4,5,3',4'-tetramethoxybenzophenone 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 

Downstream Products

• 173253-20-8 ethyl 2-[2-(N,N-diethylamino)ethyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate 

Relevant academic research and scientific papers

Pharmaceutical composition containing quinoline or quinazoline derivatives

The present invention provides a pharmaceutical composition for inhibiting bone resorption or for preventing or treating osteoporosis which comprises a quinoline or quinazoine derivative as an active ingredient.

Pharmaceutical composition containing quinoline or quinazoline derivatives and derivatives therefor

This invention provides an anti-inflammatory agent, particularly an agent for treating arthritis, containing a quinoline or quinazoline derivative or a salt thereof STR1 wherein Y is a nitrogen atom or C--G in which G is an optionally esterified carboxyl group;R 1 and R 2 are each independently a hydrogen atom, optionally substituted hydrocarbon group or optionally substituted heterocyclic group, or R 1 and R 2 are linked together to form a saturated ring;each of the ring A and ring B may optionally be substituted;n is an integer of 1 to 4; andk is 0 or 1.This invention also provides a novel quinoline or quinazoline derivative having anti-inflammatory activity.

Studies on disease-modifying antirheumatic drugs: Synthesis of novel quinoline and quinazoline derivatives and their anti-inflammatory effect

In the course of our study aimed at developing new types of DMARDs (disease-modifying antirheumatic drugs), we found that quinoline derivative 1a had a potent anti-inflammatory effect in an adjuvant arthritis (AA) rat model, starting from the potent bone resorption inhibitors justicidins as the lead compounds. Further modification of 1a was performed, and various quinoline and quinazoline derivatives having a heteroaryl moiety on the alkyl side chain at the 2-position of the skeleton were prepared. These compounds were evaluated for antiinflammatory effects using the AA rat model. Most of these compounds, especially those having an imidazole or a triazole moiety on the 2-alkyl chain, exhibited a potent effect. Among the compounds synthesized, ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-(1,2,4-triazol-1- yl-methyl)quinoline-3-carboxylate (12d), having an ED50 value of 2.6 mg/kg/day (anti-inflammatory effect in an AA rat model, po), was selected as a candidate for further investigation. In vitro, 12d inhibited mitogen- induced proliferation at 10-7-10-5 M but not prostaglandin E2 production at 10-5 M. Moreover, 12d preferentially inhibited the IFN-γ production by Th1-type clones over the IL-4 production by Th2-type clones. This preferential suppression of Th1 cytokine production is considered the essential immunomodulating action of 12d for the present. Synthesis and structure-activity relationships for this novel series of quinoline and quinazoline derivatives are detailed.

Quinoline or quinazoline derivatives, their production and use

A compound represented by the general formula: STR1 wherein Y represents a nitrogen atom or C--G (G represents a carboxyl group which may be esterified); ring R is a nitrogen-containing unsaturated heterocyclic group which may be substituted or unsubstituted; each of rings A and B may have a substituent; n represents an integer from 1 to 4; k represents the integer 0 or 1, or a salt thereof, which serves well as an anti-inflammatory agent, particularly a therapeutic agent for arthritis.