869893-91-4

Upstream product

• 85070-47-9 1-(bromomethyl)-3-chloro-2-fluorobenzene 
• 7440-66-6 zinc 

Downstream Products

• 882535-05-9 1-((2S)-1-tert-buthyldimethylsilyloxy-3-methylbutan-2-yl)-6-(3-chloro-2-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 
• 697762-66-6 6-(3-chloro-2-fluorobenzyl)-7-fluoro-1-[1-(S)-tert-butyldimethylsilyloxymethyl-2-methylprop-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 
• 880870-42-8 C₁₂H₈ClF₂N 
• 880870-14-4 C₁₃H₁₀Cl₂FNO 
• 880870-54-2 C₂₂H₃₁ClFNO₃Si 
• 880870-63-3 C₂₃H₂₈ClFN₂O₄ 
• 880870-06-4 C₂₇H₃₉ClFNO₃Si 
• 880870-34-8 C₁₁H₇Cl₂FN₂ 
• 949465-78-5 methyl 5-(3-chloro-2-fluorobenzyl)-2,4-dimethoxybenzoate 
• 949465-76-3 5-(3-chloro-2-fluorobenzyl)-2-fluoro-4-methoxybenzoic acid methyl ester 
• 1171823-54-3 8-[(S)-1-(tert-butyldimethylsilyloxy)-3-methylbutan-2-yl]-3-(3-chloro-2-fluoro-benzyl)-5-oxo-5,8-dihydropyrido[2.3-c]pyridazine-6-carboxylic acid ethyl ester 
• 1171823-58-7 1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-6-(3-chloro-2-fluoro-benzyl)-4-oxo-1,4-dihydro-[1.5]naphthyridine-3-carboxylic acid ethyl ester 
• 1171823-61-2 1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-7-chloro-6-(3-chloro-2-fluoro-benzyl)-4-oxo-1,4-dihydro-[1.5]naphthyridine-3-carboxylic acid ethyl ester 
• 1171823-27-0 1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-6-(3-chloro-2-fluoro-benzyl)-7-methoxy-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

An Improved Synthesis of Elvitegravir

An improved process for the active pharmaceutical ingredient of a new HIV integrase inhibitor elvitegravir (1) has been developed. It starts from commercially available 2,4-dimethoxyacetophenone, which is selectively halogenated into the position 5. The 5-halo acetophenones are condensed with dialkyl carbonates to give the corresponding benzoylacetates. Their treatment with N,N-dimethylformamide dimethyl acetal followed by (S)-valinol then provided the corresponding intermediate benzoyl acrylates. Cyclization to the required 1,4-dihydroquinolin-4-oxo derivatives by aromatic nucleophilic substitution of the 2-methoxy group was achieved by treatment with N,O-bis(trimethylsilyl)-acetamide, which also protected the OH group as the trimethylsilyl derivative. Finally, the Negishi coupling with 2-fluoro-3-chlorobenzylzinc bromide and the following hydrolysis provided elvitegravir (1). The preferred variant, the seven-step procedure starting from 2,4-dimethoxyacetophenone, provides elvitegravir in 29.3% yield.

PROCESS AND INTERMEDIATES FOR PREPARING INTEGRASE INHIBITORS

The invention provides synthetic processes and synthetic intermediates that can be used to prepare 4-oxoquinolone compounds having useful integrase inhibiting properties.

NOVEL COMPOSITIONS AND METHODS OF USE

Described herein are novel enzyme inhibitors. In some embodiments the enzyme inhibitors are integrase inhibitors, particularly HIV integrase inhibitors. Also described herein are compositions containing them and methods of using them. Thus, the compounds and compositions described herein are useful for the in vitro and in vivo inhibition of HIV integrase as a method of treating or preventing HIV, AIDS or related disorders.

PROCESS FOR PRODUCTION OF 4-OXOQUINOLINE COMPOUND

The present invention provides a compound useful as a synthetic intermediate for an anti-HIV agent having an integrase inhibitory activity, a production method thereof, and a production method of an anti-HIV agent using the synthetic intermediate. Specifi

DEUTERATED 4 -OXOQUINOLINE DERIVATIVES FOR THE TREATMENT OF HIV INFECTION

This invention relates to novel compounds that are 4-oxoquinoline derivatives and pharmaceutically acceptable salts thereof. More specifically, this invention relates to novel 4-oxoquinoline derivatives that are derivatives of elvitegravir. This invention

METHOD FOR PRODUCING 4-OXOQUINOLINE COMPOUND

The present invention provides a compound useful as a synthetic intermediate for an anti-HIV agent having an integrase inhibitory activity, and a production method thereof, and a production method of an anti-HIV agent using the synthetic intermediate. Spe

Quinolizinone compound and use thereof as HIV integrase inhibitor

A pharmaceutical agent having an anti-HIV action, particularly, a pharmaceutical agent having an integrase inhibitory action, is provided. The present invention relates to a quinolizinone compound represented by the following formula [I] wherein each symbol is as defined in the specification, a pharmaceutically acceptable salt thereof, and an anti-HIV agent containing same as an active ingredient. The compound of the present invention has an HIV integrase inhibitory action and is useful as an anti-HIV agent for the prophylaxis or therapy of AIDS. Moreover, by a combined use with other anti-HIV agents such as protease inhibitors, reverse transcriptase inhibitors and the like, the compounds can become a more effective anti-HIV agent. Since the compound has a high inhibitory activity specific for integrases, the compound can provide a safe pharmaceutical agent for human with a fewer side effects.

STABLE CRYSTAL OF 4-OXOQUINOLINE COMPOUND

The present invention provides a crystal of 6-(3-chloro-2-fluorobenzyl)-1-[(S)-1-hydroxymethyl-2-methylpropyl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, which shows a particular powder X-ray diffraction pattern of a characteristic diffractio

NOVEL 4-OXOQUINOLINE COMPOUND AND USE THEREOF AS HIV INTEGRASE INHIBITOR

Provision of a compound having an anti-HIV activity, particularly an integrase inhibitory activity.A 4-oxoquinoline compound represented by the following formula [I] or a pharmaceutically acceptable salt thereof: wherein each symbol is as defined in the specification.The present invention also relates to a pharmaceutical composition containing the 4-oxoquinoline compound or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier; an integrase inhibitor, an antiviral agent, anti-HIV agent and the like, which contains the 4-oxoquinoline compound or a pharmaceutically acceptable salt thereof as an active ingredient; an anti-HIV composition containing the 4-oxoquinoline compound or a pharmaceutically acceptable salt thereof, and one or more other kinds of anti-HIV activity substances as active ingredients; an anti-HIV agent containing the 4-oxoquinoline compound or a pharmaceutically acceptable salt thereof as an active ingredient, which is used for a multiple drug therapy with other anti-HIV agent(s), and the like.

4-OXOQUINOLINE COMPOUNDS AND UTILIZATION THEREOF AS HIV INTEGRASE INHIBITORS

An anti-HIV agent containing, as an active ingredient, a 4-oxoquinoline compound represented by the following formula [I] wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof. The compound of the present invention has HIV integrase inhibitory action and is useful as an anti-HIV agent for the prophylaxis or therapy of AIDS. Moreover, by a combined use with other anti-HIV agents such as protease inhibitors, reverse transcriptase inhibitors and the like, the compound can become a more effective anti-HIV agent. Since the compound has high inhibitory activity specific for integrases, it can provide a safe pharmaceutical agent with a fewer side effects for human.