22316-55-8

Usage

Uses

Used in Pharmaceutical Applications:
8-Chloro-1-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione is used as an active metabolite for clobazam, a pharmaceutical drug with depressant properties. Its role in modulating GABAA receptors contributes to its therapeutic effects in treating various conditions.
Used in Research Applications:
8-Chloro-1-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione is used as an analytical reference material in research settings, particularly for studying the effects and mechanisms of benzodiazepines. It helps researchers understand the interactions between these compounds and GABAA receptors.
Used in Forensic Applications:
8-Chloro-1-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione is used as a certified reference material in forensic analysis. It is particularly useful in forensic toxicology and urine drug testing, where it helps in the identification and quantification of clobazam and its metabolites in biological samples.
Used in Drug Testing Applications:
8-Chloro-1-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione is utilized in drug testing to detect the presence of clobazam and its metabolites in urine, serum, and plasma samples. It aids in the diagnosis of substance abuse and monitoring of therapeutic drug levels in patients undergoing treatment with clobazam.

InChI:InChI=1/C15H11ClN2O2/c16-10-6-7-12-13(8-10)18(11-4-2-1-3-5-11)15(20)9-14(19)17-12/h1-8H,9H2,(H,17,19)

Upstream product

• 22316-46-7 N-carbethoxy acetyl N-phenyl 5-chloro o-phenylene diamine 
• 25781-92-4 5-chloro-2-nitro-N-phenylaniline 
• 22316-45-6 ethyl 2-(N-(5-chloro-2-nitrophenyl)-N-phenylamino)formylacetate 
• 603-33-8 triphenylbismuthane 
• 61911-86-2 7-chloro-1H-1,5-benzodiazepine-2,4(3H,5H)-dione 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 89-63-4 4-Chloro-2-nitroaniline 
• 62-53-3 aniline 
• 68406-47-3 4-chloro-N₂-phenylbenzene-1,2-diamine 
• 1663-67-8 malonoyl dichloride 
• 700-37-8 4-chloro-2-fluoro-nitrobenzene 
• 610-40-2 3,4-dinitro-chlorobenzene 
• 16695-14-0 Malonic acid monomethyl ester 
• 105-53-3 diethyl malonate 

Downstream Products

• 36985-45-2 8-chloro-4-(dimethylamino)-1,3-dihydro-1-phenyl-2H-1,5-benzodiazepin-2-one 
• 36985-42-9 7-chloro-2-methylamino-5-phenyl-4H-3,5-dihydro-1,5-benzodiazepin-4-one 
• 40114-80-5 8-chloro-1-phenyl-4-thioxo-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one 
• 1267634-92-3 C₁₉H₁₈ClN₃O₃ 
• 1267634-94-5 C₁₈H₁₆ClN₃O₃ 
• 1267634-97-8 C₂₂H₁₇ClN₄O₂ 
• 22316-47-8 clobazam 
• 1329991-47-0 C₂₀H₂₁ClN₄O 
• 1329990-25-1 C₁₇H₁₃ClN₄O 
• 1329990-87-5 C₁₇H₁₃ClN₄O 
• 1267635-28-8 C₁₈H₁₅ClN₄O 
• 1267634-98-9 C₂₀H₂₀ClN₃O₃ 
• 69754-68-3 7-chloro-3,5-dihydro-2-methoxy-5-phenyl-4H-1,5-benzodiazepin-4-one 
• 38224-97-4 3-(butylamino-methylene)-8-chloro-1-phenyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione 

Relevant academic research and scientific papers

Method for industrially producing clobazam

The invention discloses a method for industrially producing clobazam, and belongs to the technical field of medicine synthesis. According to the method, 5-chloro-2-nitrobenzidine is used as a raw material, and a clobazam bulk drug is prepared through processes of acylation, reduction ring closing, methylation and refining. According to the invention, the problems that reagents with high toxicity are used in the prior art, the pollution is serious, and potential safety hazards exist in the pressurized hydrogenation reaction are solved, the production cost is reduced, and the product quality and economic benefits are improved.

Preparation method of clobazam

The invention provides a preparation method of clobazam. The preparation method comprises the following steps: (1), using 2-nitro-5-chlorodiphenylamine and ethyl malonyl chloride as raw materials, performing a reflow reaction in an organic solvent, after the reaction, decompressing the organic solvent in the reaction system, then performing evaporation to dryness, and adding a refining solvent for refining treatment so as to obtain a compound as shown in a formula II; (2), performing zinc powder reduction on the compound as shown in the formula II, and performing ammonolysis cyclization so as to obtain a compound as shown in a formula III; (3) enabling the compound as shown in the formula III to react with methyl iodide in an alkaline alcohol solution so as to obtain the clobazam, wherein alkali is one or more of sodium hydroxide, lithium hydroxide and potassium hydroxide. The clobazam prepared by the method is few in impurities and high in purity.

A 1,5-benzodiazepine derivatives zhuo Tong method for the preparation of (by machine translation)

This invention relates to a kind of 1,5 the zhuo Tong[...] and method for preparing derivatives of nitrogen, characterized in that in order to replace the raw materials of dinitro compound is phthalic acid, with a substituted aniline reaction, the reaction with malonic acid monoester, then cyclization to obtain a target compound. The method step of this invention is simple, cheap material, easy to operate and achieve commercial, yield and purity are greatly improved. (by machine translation)

Method being suitable for industrially producing clobazam

The invention discloses a method of industrially producing clobazam and belongs to the technical field of medicine synthesis. With 5-chloro-2-nitrobenzidine as an initial raw material, the method includes the steps of reduction with a nano heavy metal granular catalyst, catalytic condensation with Lewis acid, methylation, and purification to prepare the clobazam that satisfies clinical medicinal requirement. The method solves the problems of heavy toxicity and serious pollution in the prior art, is beneficial to labor protection and reduces production cost, and improves product quality and economic benefit.

PROCESS FOR PREPARING CLOBAZAM USING NOVEL INTERMEDIATES

Processes for preparation of 7-chloro-1-methyl-5-phenyl-1,5-dihydro- benzo[b][1,4]diazepine-2,4-dione (Clobazam) are provided. The present invention also relates to the novel intermediates and its use in preparation of clobazam.

AN IMPROVED PROCESS FOR THE PREPARATION OF CLOBAZAM AND ITS INTERMEDIATE

The present invention provides an improved process for the preparation of 8-chloro-1-phenyl- 1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione (hereafter referred to as the compound (IV)), which is useful as a key intermediate for the synthesis of Clobazam (referred to as the compound (I)) 7-chloro-1-methyl-5-phenyl-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione. The process of the present invention further involves transformation of the compound (IV) into Clobazam (I), comprising (a) reacting the compound (II) (as described herein) with monoalkyl malonate in the presence of a coupling agent to obtain the compound (III) (as described herein); followed by the cyclization using a base; (b) reacting the compound-IV (as described herein) obtained from step (a) with methylating agent. The process of the present invention involves formation of novel intermediates methyl 3-((4- chloro-2-(phenylamino)phenyl)amino)-3-oxopropanoate (IlIa) and 3-((4-chloro-2- (phenylamino)phenyl)amino)-3-oxopropanoic acid (V).

DERIVATIVES OF 1-PHENYL-1,5-DIHYDRO-BENZO[B] [1.4]DIAZEPINE-2.4-DIONE AS INHIBITORS OF HIV REPLICATION

Compounds of formula (I) wherein m, R1, R2, R3, X and Y are defined herein, are useful as inhibitors of HIV replication.

Discovery of a 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione series of inhibitors of HIV-1 capsid assembly

The discovery of a 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione series of inhibitors of HIV-1 capsid assembly is described. Synthesis of analogs of the 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione hit established structure-activity relationships. Replacement of the enamine functionality of the hit series with either an imidazole or a pyrazole ring led to compounds that inhibited both capsid assembly and reverse transcriptase. Optimization of the bicyclic benzodiazepine scaffold to include a 3-phenyl substituent led to lead compound 48, a pure capsid assembly inhibitor with improved antiviral activity.

SYNTHESIS AND BIOLOGICAL EVALUATION OF 7-CHLORO-1-TRIDEUTERIOMETHYL-5-PHENYL-1H-1,5-BENZODIAZEPINE-2,4(3H,5H)-DIONE (CLOBAZAM-D3)

Clobazam-d3 has been prepared by treatment of norclobazam sodium salt with trideuteriomethyl iodide.Clobazam-d3 has a pharmacological profile rather similar to that of clobazam.It differs by its longer duration of anti-epileptic action.Keywords - anti-epiliptic action / clobazam-d3

1,5-Benzodiazepine-2,4-diones

This invention relates to substituted 1,5-benzodiazepines having the formula SPC1 Wherein R1 and R2 are hydrogen or substituents, R3 is hydrogen or substituents, R4 is methyl or aryl group, As well as the process of producing the same. The compounds of the invention are tranquillizing analgesic, antipyretic and anti-inflammatory agents.