654655-80-8

Usage

Uses

Used in Pharmaceutical Industry:
Bedaquiline (Mixture of DiastereoMers) is used as an antituberculosis agent for its ability to inhibit mycobacterial growth, offering a new treatment option for drug-resistant tuberculosis cases and improving patient outcomes.

Upstream product

• 654655-69-3 3-benzyl-6-bromo-2-methoxyquinoline 
• 10320-49-7 3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone 
• 941-98-0 1'-naphthacetophenone 
• 654653-93-7 rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol 
• 106-40-1 4-bromo-aniline 
• 316146-27-7 N-(4-bromophenyl)-3-phenylpropanamide 
• 654655-68-2 3-benzyl-6-bromo-2-chloro-quinoline 
• 66-77-3 1-naphthaldehyde 
• 2631-61-0 3-dimethylamino-1-(naphthalen-2-yl)propan-1-one hydrochloride 
• 924632-90-6 (±)-3-bromo-3-(bromo(phenyl)methyl)-2-methoxyquinoline 
• 1189178-87-7 6-bromo-3-[chloro(phenyl)methyl]-2-methoxyquinoline 

Downstream Products

• 654655-69-3 3-benzyl-6-bromo-2-methoxyquinoline 
• 10320-49-7 3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone 
• 843663-66-1 bedaquiline 
• 845533-86-0 [4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium 3-carboxyprop-2-enoate 
• 916800-77-6 C₃₃H₃₂N₂O₃ 
• 2752-87-6 3-(dimethylamino)-1-(naphthalen-2-yl)propan-1-one 
• 1032468-55-5 C₃₂H₂₉BrN₂O 

Relevant academic research and scientific papers

PROCESS FOR PREPARING (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-butan-2-ol AND PHARMACEUTICALLY ACCEPTABLE SALT

The present invention relates to a process for the preparation of bedaquiline ((1R, 2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-butan-2-ol) or a pharmaceutically acceptable salt thereof, the process comprising: isolating (1R, 2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-butan-2-ol. The method can achieve large-scale preparation, so that the preparation method is an economical preparation method and has high yield.

Preparation method of bedaquiline and intermediate thereof

The invention discloses a preparation method of a bedaquiline racemate and a key intermediate compound used in the preparation method. According to the method for preparing the bedaquiline racemate, the ultra-low temperature reaction in the prior art is changed, and the ultra-low temperature reaction which is difficult to realize in the prior art is carried out at the conventional temperature, sothat large-scale industrialization becomes possible. Besides, the method provided by the invention greatly improves the conversion rate of the reaction substrate, improves the reaction yield, makes the product more easily crystallized and purified, and reduces the production cost at the same time.

Preparation method of bedaquiline

The invention provides a method for preparing bedaquiline shown as a formula IV (See the specification). The method comprises the step of reacting a compound II with a compound III. According to the method disclosed by the invention, the ultralow-temperat

For preparing beda quinoline intermediate and its preparation method and application

The invention discloses an intermediate for preparing bedaquiline and a preparation method therefor. The intermediate disclosed by the invention has the advantages that the intermediate avoids hydrogenation and enolization of an alpha-site in the intermediate, reduces occurrence of side reactions, and increases the conversion rate of raw materials and the total yield of reaction, and is suitable for large-scale industrial production. The intermediate for preparing bedaquiline is characterized by being a compound with a structural formula (9) or an optical isomer thereof: FORMULA is shown in the description.

Beda quinoline preparation method

The invention discloses a preparation method for bedaquiline. The preparation method comprises the following steps: enabling a compound (9) to be reacted with a reducing agent in a solvent; and then collecting racemate of bedaquiline from a reaction product. The preparation method has the advantages that the compound (9) is a novel compound which has not been reported in literature; the racemate of bedaquiline is prepared from a compound (8) and the compound (9); the obtained product is greatly increased in yield (greater than 47%) which is remarkably greater than the yield (26%) in the original patent; and the obtained racemate of bedaquiline is high in purity, stable and controllable in quality, and beneficial for subsequent resolution reaction, and has relatively great positive effects and relatively high practical application value. The reaction formula is shown as follows: a FORMULA as shown in the description.

A beda quinoline multiples of the synthetic route and method

The invention relates to a new synthesis route and method of a bedaquiline racemate, and belongs to the medical technical field. The method comprises the steps: (1) carrying out a reaction of a starting material 3-bromobenzyl-6-bromo-2-methoxyquinoline (I

A highly efficient way to recycle inactive stereoisomers of Bedaquiline into two previous intermediates via base-catalyzed Csp3Csp3 bond cleavage

Abstract Bedaquiline is a new medicine for pulmonary multi-drug resistant tuberculosis (MDR-TB), which is a pure enantiomer with two chiral centers. The current industrial preparation process requires the separation of active Bedaquiline from a mixture of four isomers. Obviously, direct dispose of the other three undesired stereoisomers will cause significant waste and increase the unnecessary cost of production. Here, we developed an efficient, facile and scalable process for recycling the inactive stereoisomers of Bedaquiline. All these inactive stereoisomers could be recycled by their conversion to two important intermediates in the Bedaquiline synthesis via a base-catalyzed Csp3Csp3 bond cleavage of a benzyl alcohol intermediate. And the precise conditions and mechanism of the base-catalyzed cleavage reaction were discussed.

QUINOLINE DERIVATIVES FOR THE TREATMENT OF LATENT TUBERCULOSIS

Use of a compound of formula (Ia) or (Ib) for the manufacture of a medicament for the 5 treatment of latent tuberculosis, wherein the compound of formula (Ia) or (Ib) is a pharmaceutically acceptable salt, a quaternary amine, a N-oxide, a tautomeric form or a stereochemically isomeric form thereof wherein R1 is hydrogen, halo, haloalkyl, cyano, hydroxy, Ar, Het, alkyl, alkyloxy, alkylthio, alkyloxyalkyl, alkylthioalkyl, Ar-alkyl or di(Ar)alkyl; p is 1, 2, 3 or 4; R2 is hydrogen, hydroxy, mercapto, alkyloxy, alkyloxyalkyloxy, alkylthio, mono or di(alkyl)amino or a radical of formula (II); R3 is alkyl, Ar, Ar-alkyl, Het or Het-alkyl; q is zero, 1, 2, 3 or 4; R4 and R5 each independently are hydrogen, alkyl or benzyl; or R4 and R5 may be taken together including the N to which they are attached; R6 is hydrogen, halo, haloalkyl, hydroxy, Ar, alkyl, alkyloxy, alkylthio, alkyloxyalkyl, alkylthioalkyl, Ar-alkyl or di(Ar)alkyl ; or two vicinal R6 radicals may be taken together to form a bivalent radical -CH=CH-CH=CH-; r is 1, 2, 3, 4 or 5 ; R7 is hydrogen, alkyl, Ar or Het; R8 is hydrogen or alkyl; R9 is oxo; or R8 and R9 together form the radical =N-CH=CH-.