94015-53-9

Upstream product

• 1203556-33-5 2-[4-(4-chlorophenyl)cyclohexyl]-3-(2-pyridin-2-ylthio)-naphthalene-1,4-dione 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 95233-37-7 trans-4-(p-chlorophenyl)cyclohexane carboxylic acid 
• 7473-18-9 2-ethoxy-1,4-naphthoquinone 
• 1409957-21-6 cis/trans-1a-(4-(4-chlorophenyl)cyclohexyl)naphtho[2,3-b]oxyrene-2,7(1aH,7aH)-dione 
• 1346600-43-8 trans-4-(4-chlorophenyl)cyclohexyl-1-carboxylic acid 
• 130-15-4 [1,4]naphthoquinone 
• 129719-64-8 2-[4-(4-chlorophenyl)-cyclohexyl]-3-chloro-1,4-naphthoquinone 

Downstream Products

• 95233-18-4 atovaquone 
• 137732-39-9 cis-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione 

Relevant academic research and scientific papers

Atovaquone synthesis technology

The invention discloses an atovaquone synthesis technology. The atovaquone synthesis technology comprises that in the presence of a silver nitrate catalyst, 2-ethoxy-1, 4-naphthoquinone and 4-(4-chlorophenyl)cyclohexyl-1-formic acid as raw materials are dissolved in an acetonitrile solvent, then the solution is added into a reactor and is heated along with stirring until reflux so that the reaction system undergoes a reaction, wherein in reflux, an ammonium persulfate aqueous solution is dropwisely added into the reaction system and the mole amount of the ammonium persulfate is 3-5 times that of 2-ethoxy-1, 4-naphthoquinone, after the reaction, the product is cooled and forms crystals, the crystals are filtered and are dissolved through trichloromethane, the solution is filtered, the filtrate is collected and is subjected to reduced pressure distillation so that trichloromethane is removed, and the solution is subjected to acetonitrile recrystallization so that atovaquone yellow acicular crystals are obtained. The atovaquone synthesis technology only needs one step, saves a synthesis cost, has a high yield and can produce high-purity atovaquone.

NOVEL METHOD FOR PREPARATION OF ATOVAQUONE

Provided is a process of preparation of 2-[trans,-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy- 1,4-naphthoquinone, i.e. Atovaquone [I] which is cost effective, green, and eco-friendly process, without separation of any diastereomers or geometric isomers of intermediates obtained during the reactions. Also provided is separation of 'cis' and 'trans ' isomer of intermediates VI, VII and VIII through selective crystallization in an appropriate solvent. A method for converting 2-[cis,-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone to 2-[trans-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy-l,4-naphthoquinone in presence of Lewis/ Bronsted acid is also provided. A process for preparation of compound 2-(4-(4- chlorophenyl)- 1 -hydroxy cyclohexyl)-3,4-dihydronaphthalen- 1 (2H)-one [IV] comprising condensation of (1,2-dihydronaphthalen-4-yloxy)trimethylsilane [II] with 4-(4- chlorophenyl)cyclohexanone [III] in presence of Lewis acid in organic solvent. The invention also encompasses a highly efficient and atomeconomic process for synthesis of compound [III] i.e. 4-(4-chlorophenyl)cyclohexanone as well as a process for synthesis of 2-[cis-4-(4'- chlorophenyl)cyclohexyl]-3-hydroxy-l,4-naphthoquinone. Further provided is a process for isomerization of cis- Atovaquone i.e. 2-[cis-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy-l,4- naphthoquinone to tnms-Atovaquone i.e. 2-[trans-4-(4'-chlorophenyl)cyclohexyl]-3- hydroxy- 1,4-naphthoquinone in presence of Lewis acid.

Process for the preparation of trans-2,3-disubstituted naphthoquinones

The invention concerns a new process for the preparation of naphthoquinones, in particular an improved process for the preparation of 2,3-disubstituted 1,4-naphthoquinones, in the trans configuration.

NEW PROCESS FOR PREPARATION OF ATOVAQUONE AND NOVEL INTERMEDIATES THEREOF

Disclosed herein is a novel process for preparation of atovaquone. The process includes reacting 1,4-naphthoquinone with trans-4-(4-chlorophenyl) cyclohexane carboxylic acid followed by halogenation to obtain a dihalo-compound. Further, dehydrohalogenatio

A PROCESS FOR PREPARING ATOVAQUONE AND ASSOCIATE INTERMEDIATES

The invention provides novel intermediates of atovaquone and use thereof for the preparation of atovaquone

PROCESS FOR PREPARATION OF ATOVAQUONE AND THE CONVERSION OF CIS-ISOMER TO TRANS- ISOMER

Substantially pure atovaquone and parocess for the preparation thereof is disclosed.

NOVEL POLYMORPHS OF ATOVAQUONE AND PROCESS OF PREPARATION THEREOF

Novel crystalline forms of anti Pneumocystis carinii compound (2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4--naphthoquinone) commonly known as Atovaquone and methods for producing the same is disclosed herein. This also provides pharmaceutical compositions comprising the said polymorphs of Atovaquone and method of treating Pneumocystis carinii pneumonia, the method comprising administering to a warm blooded animal an effective amount of a product-by-process composition of matter comprising polymorphic forms of Atovaquone.

Method for treating animals infected with Babesia spp.

The present invention relates to pharmaceutical compositions for the treatment and/or prophylaxis of protozoal infections caused by Kinetoplastida, Apicomplexa, Anaerobic protozoa and Mircosporidia comprising 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone or a physiologically acceptable salt or other functional derivative thereof as active ingredient and to a method of treating or preventing siad protozoal infections in an animal which comprises administering to said animal an effective amount of siad compound.

Use of 2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-1,4-Naphthoquinone for the treatment of cancer

The present invention relates to the use of 2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone or a physiologically acceptable salt or other physiologically functional derivative thereof for the manufacture of a medicament for the treatment of tumours in animals, to pharmaceutical compositions for the treatment of tumours in animals, to pharmaceutical compositions for the treatment of tumours, comprising said compound as active ingredient and to a method of treating tumours in an animal which comprises administering to said animal an effective amount of said compound.

Medicaments for the treatment of toxoplasmosis

The present invention relates to the use of 2-[4-(4-chlorophenyl) cyclohexyl]-3-hydroxy-1,4-naphthoquinone or a physiologically acceptable salt or other physiologically funtional derivative thereof for the manufacture of a medicament for the treatment and/or prophylaxis of toxoplasmosis in animals, to pharmaceutical compositions for the treatment and/or prophylaxis of toxoplasmosis, comprising said compound as active ingredient and to a method of treating or preventing toxoplasmosis in an animal which comprises administering to said animal an effective amount of said compound.