1645-32-5

Usage

Uses

Used in Pharmaceutical Industry:
N-desmethylquazepam is used as a metabolite of quazepam for its contribution to the sedative and anxiolytic effects of the parent drug. Its longer half-life compared to quazepam may influence the duration of action and the potential for side effects and drug interactions. This makes it an important compound to consider in the development and assessment of benzodiazepine medications and their metabolites for therapeutic use.

InChI:InChI=1/C15H10ClFN2S/c16-9-5-6-13-11(7-9)15(18-8-14(20)19-13)10-3-1-2-4-12(10)17/h1-7H,8H2,(H,19,20)

Upstream product

• 784-38-3 2-amino-5-chloro-2'-fluorobenzophenone 
• 393-52-2 2-Fluorobenzoyl chloride 
• 1584-62-9 2?(2?bromoacetamido)?5?chloro?2'?fluorobenzophenone 
• 2886-65-9 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-1,4-benzodiazepin-2(2H)-one 
• 2836-40-0 2-(2-chloroacetyl)amino-4-chloro-2'-fluorobenzophenone 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 67974-53-2 2-(2-dimethylaminoethylthio)-5-(2-fluorophenyl)-7-chloro-3H-1,4-benzodiazepine 
• 39256-30-9 2-(methylthio)-5-(o-fluorophenyl)-7-chloro-3H-1,4-benzodiazepine 
• 59467-61-7 [7-chloro-5-(2-fluoro-phenyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-ylidene]-methyl-amine 
• 59467-61-7 7-chloro-5-(2-fluorophenyl)-3H-1,4-benzodiazepine-2-methylamine 
• 28910-91-0 flualprazolam 
• 819793-80-1 8?chloro?6?(2?fluorophenyl)?1?methyl?3?(4?toluenesulfonyl)?4H?imidazo[1,5?a][1,4]benzodiazepine 

Relevant academic research and scientific papers

Synthesis of?some?new substituted triazolo [4,3-a][1,4] benzodiazepine derivatives as?potent anticonvulsants

Novel 8-chloro-6-(2-fluorophenyl)-1-(aryl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepines (5a-f) were prepared by treating 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-thione with various aromatic acid hydrazides. The newly prepared compounds were characterized by spectral analysis. Compounds were tested for anticonvulsant activity. Four of the tested compounds such as 5a, 5d, 5e and 5f exhibited excellent anticonvulsant activity in comparison with standard drug, diazepam.

Preparation method of flualprazolam

The invention discloses a preparation method of flualprazolam, and relates to the technical field of medicine synthesis. The preparation method of the flualprazolam comprises the following steps: by taking phosphorus pentasulfide as a vulcanizing reagent, vulcanizing carbonyl groups of 7-chloro-1,3-dihydro-5-(2-fluorophenyl)-3H-1,4-benzodiazepine-2-one to obtain an intermediate; and adding the intermediate and acethydrazide into an organic solvent, and reacting to obtain flualprazolam. The synthesis method provided by the invention only needs two steps and is simple to operate, so the reactiontime is greatly shortened, the reaction cost is reduced, and the reaction efficiency is improved; and the reaction process conditions are mild, and the reagent toxicity is low, so the synthesis process is safe and environment-friendly.

Preparation method of 7-chloro-5-(2-fluorophenyl)-3H-1, 4-benzodiazepin-2-methylamine

The invention provides a preparation method of 7-chloro-5-(2-fluorophenyl)-3H-1, 4-benzodiazepin-2-methylamine, which comprises the following steps: (1) reacting 7-chloro-5-(2-fluorophenyl)-1, 3-dihydro-2H-1, 4-benzodiazepin-2-one with phosphorus pentasulfide to obtain 7-chloro-5-(2-fluorophenyl)-1, 3-dihydro-2H-1, 4-benzodiazepin-2-thione, and (2) enabling the 7-chloro-5-(2-fluorophenyl)-1, 3-dihydro-2H-1, 4-benzodiazepin-2-thione to react with a methylamine alcohol solution, so as to prepare the 7-chloro-5-(2-fluorophenyl)-3H-1, 4-benzodiazepin-2-methylamine. The preparation method providedby the invention is low in cost, mild in condition, safe in production, high in yield, stable and reliable in product quality, simple and convenient to operate and more suitable for industrial production.

SHORT-ACTING BENZODIAZEPINE DERIVATIVES, PREPARATION METHOD THEREFOR, AND USE THEREOF

The present invention relates to a benzodiazepine derivative of Formula I as a short-acting anesthetic, a pharmaceutical composition comprising the same, a kit comprising the same, a preparation method thereof, an method of anesthesia using the same and use thereof in the manufacture of an anesthetic medicament.

PERIPHERALLY RESTRICTED GABA POSITIVE ALLOSTERIC MODULATORS FOR THE TREATMENT OF IRRITABLE BOWEL SYNDROME AND OTHER AILMENTS OF THE PERIPHERAL NERVOUS SYSTEM

The present invention provides compounds and compositions which are positive allosteric modulators of GABA-A receptors that selectively target the peripheral nervous system and organs of the body, and which do not pass through the blood-brain barrier. The compounds and compositions of the present invention are useful for treatment of diseases or disorders which are mediated by GABA-A neuronal activity, such as, for example, visceral pain, gut motility, irritable bowel syndrome, functional abdominal pain, functional idiopathic diarrhea, inflammatory bowel diseases, drug induced pain, bile salt malabsorption, lactase or other carbohydrate intolerance.

Pyrazolobenzodiazepines: Part I. Synthesis and SAR of a potent class of kinase inhibitors

A novel series of pyrazolobenzodiazepines 3 has been identified as potent inhibitors of cyclin-dependent kinase 2 (CDK2). Their synthesis and structure-activity relationships (SAR) are described. Representative compounds from this class reversibly inhibit CDK2 activity in vitro, and block cell cycle progression in human tumor cell lines. Further exploration has revealed that this class of compounds inhibits several kinases that play critical roles in cancer cell growth and division as well as tumor angiogenesis. Together, these properties suggest a compelling basis for their use as antitumor agents.

Reactions of 1,4-benzodiazepinic N-nitrosoamidines with tosylmethyl isocyanide: A novel synthesis of midazolam

Reaction of 1,4-benzodiazepinic N-nitrosoamidines, used as synthetic equivalents of imidoyl chlorides, with the monoanion of tosylmethyl isocyanide is described. The process gives entry to 3-(4-tosyl)imidazo[1,5-a][1,4] benzodiazepines, compounds which have not been described yet in the literature. These systems can be derivatized to the corresponding trisubstituted 1,4-benzodiazepines by alkylation or acylation of the imidazole ring. These new heterocyclic derivatives are potentially useful in the field of medicinal chemistry. In addition, midazolam 3, the anesthetic properties of which are well established, can be easily prepared in one step by desulfonylation of compound 7a.

Synthesis and spectral properties of 2-[(o- and p-substituted)aminophenyl]-3H-5-[(o- and p-substituted)phenyl]-7-chloro-1,4-benzodiazepines

A series of twelve new 2-[(o- and p-substituted)aminophenyl]-3H-5-[(o- and p-substituted)phenyl]-7-chloro-1,4-benzodiazepines, which have possible pharmacological properties has been obtained. The synthesis was carried out following six steps. The structure of all products was corroborated by ir, 1H nmr, 13C nmr and ms. In addition for the compound 2-(o-chloroaminophenyl)-3H-5-(o-fluorophenyl)-7-chloro-1,4-benzodiazepine 7, its structure was confirmed by X-ray diffraction.

2-(2-Alkynylamino)-3H-1,4-benzodiazepines

Novel 6-substituted 4H-imidazo[1,2-a][1,4]benzodiazepines, the intermediate 5-substituted-2-(2-alkynylamino)-3H-1,4-benzodiazepines, pharmacologically acceptable acid addition salts thereof, and processes for their production. The compounds of this invention and the pharmacologically acceptable acid addition salts thereof are central nervous system depressants. They are useful as sedatives, hypnotics, tranquilizers, muscle relaxants and anticonvulsants, and also as feed additives for increasing growth rate and feed efficiency of livestock and poultry, milk production in the mammalian species and egg production in avian species.