29975-16-4

Usage

Uses

Used in Pharmaceutical Industry:
Estazolam is used as a tranquilizer for its anxiolytic, anticonvulsant, hypnotic, sedative, and skeletal muscle relaxant properties. It is commonly prescribed to treat short-term insomnia.
Used as a Controlled Substance:
Estazolam is classified as a controlled substance due to its potential for dependence and abuse. It is important to follow medical guidelines and prescriptions when using this medication to ensure safe and effective treatment.

Pharmacology

Estazolam is classed as a "triazolo" benzodiazepine drug.Estazolam exerts its therapeutic effects via its benzodiazepines receptor agonist properties.Estazolam at high doses decreases histamine turnover via its action at the benzodiazepine-GABA receptor complex in mouse brains.

Adverse reactions

Common adverse reactions such as drowsiness, drowsiness, dizziness, fatigue, unsteady gait, etc., increasing the dose may occasionally cause adverse reactions such as headache, ataxia, motor dysfunction, slurred speech, respiratory depression, tremor, etc.?Long-term use can lead to memory loss Adverse reactions such as decline, weight gain, cognitive impairment, loss of libido, etc. In addition, long-term use of estazolam can cause down-regulation of benzodiazepine receptors in the central nervous system, which can lead to tolerance and dependence, and sudden withdrawal can cause Headache, insomnia, depression, nervousness, restlessness, irritability, anxiety, tremor, tachycardia and other withdrawal symptoms, namely drug addiction, are the most serious adverse reactions of long-term use of estazolam.

Originator

Eurodin,Takeda,Japan,1975

Manufacturing Process

A mixture of 5.74 grams (0.020 mol) of 7-chloro-1,3-dihydro-5-phenyl-2H- 1,4-benzodiazepine-2-thione, 3.6 grams (0.060 mol) of formic acid hydrazide and 200 ml of 1-butanol was refluxed for 3.75 hours with a slow stream of nitrogen bubbling through the mixture. The mixture was concentrated, the residue was suspended in water and the suspension was filtered. The filter cake consisted principally of unchanged starting material. The filtrate was concentrated, ethyl acetate and Skellysolve B hexanes being added during the concentration, giving crude product (2.54 grams), MP 220.5° to 225°C. Recrystallization of this material from ethyl acetate-Skellysolve B hexanes gave 8-chloro-6-phenyl-4H-s-triazolo[4,3-a] [1,4]benzodiazepine, MP 228° to 229°C.

Therapeutic Function

Hypnotic, Sedative

InChI:InChI=1/C16H11ClN4/c17-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)18-9-15-20-19-10-21(14)15/h1-8,10H,9H2

Upstream product

• 55514-31-3 2-methylimidazolium chloride 
• 122-51-0 orthoformic acid triethyl ester 
• 7564-07-0 2-amino-7-chloro-5-phenyl-3H-1,4-benzodiazepine 
• 693-98-1 2-methylimidazole 
• 6313-33-3 formamidine hydrochloride 
• 18091-89-9 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine 

Downstream Products

• 71616-85-8 8-chloro-1,4-bis-(dimethylamino-methyl)-6-phenyl-benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine 
• 37115-32-5 adinazolam 
• 121899-04-5 4-<(dimethylamino)methyl>-8-chloro-6-phenyl-4H-s-triazolo<4,3-a><1,4>-benzodiazepine hydrochloride 
• 39667-62-4 1-bromo-8-chloro-6-phenyl-1H-s-triazolo<4,3-a><1,4>benzodiazepine 
• 118790-80-0 [2-(3-Aminomethyl-[1,2,4]triazol-4-yl)-5-chloro-phenyl]-phenyl-methanone 
• 56910-08-8 8-chloro-1-(4-methylpiperazino)-6-phenyl-4H-s-triazolo<4,3-a>-1,4-benzodiazepine 
• 88701-67-1 8-chloro-1-<4-(2-methoxyethyl)piperazino>-6-phenyl-4H-s-triazolo<4,3-a>-1,4-benzodiazepine 
• 37115-43-8 8-chloro-1-hydroxymethyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine 

Relevant academic research and scientific papers

5-chloro-2-(3-chloromethyl-S-triazolyl)benzophenone chloroacetate as well as crystal form and preparation method thereof

The invention discloses 5-chloro-2-(3-chloromethyl-S-triazolyl) benzophenone chloroacetate as well as a crystal form and a preparation method thereof. The preparation method comprises the following steps: dissolving 5-chloro-2-((N-chloracetyl-N-chloracetylhydrazinemethyl)amino)benzophenone in a solvent, adding chloroacetic acid, stirring and heating the mixed liquid to carry out rearrangement reaction, cooling and crystallizing the reaction product after the reaction is finished, carrying out solid-liquid separation, and drying the substance to obtain a chloroacetate crystal form of 5-chloro-2-(3-chloromethyl-S-triazolyl)benzophenone, namely a crystal form A. According to the invention, based on the of the 5-chloro-2-(3-chloromethyl-S-triazolyl) benzophenone chloroacetate, the requirementfor subsequent synthesis of eszolam can be met, chloroacetic acid is used for rearrangement and salification in the preparation process, and complex solvent conversion aftertreatment operation is avoided.

Benzodiazepine derivatives

Benzodiazepine derivatives of the general formula STR1 where R1 is hydrogen or a hydrocarbon residue of 1-8 carbon atoms, R2 is hydrogen or lower alkyl and rings A and B are unsubstituted or substituted by nitro, trifluoromethyl, halogen, lower alkyl or lower alkoxy, the nitrogen atom in the 5-position being unsubstituted or substituted by an oxygen atom, useful as muscle relaxants, anticonvulsants, sedatives and tranquilizing agents, and processes for production thereof. Also provided are novel intermediates of the general formula STR2 where R2 has the above meaning, rings A and B are unsubstituted or substituted as above and the nitrogen atom in the 4-position is unsubstituted or substituted by an oxygen atom.

6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines

6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula (IV): SPC1 wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, phenyl, benzyl and -COOR' in which R' is alkyl of 1 to 4 carbon atoms, inclusive; wherein R1 is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; and wherein R2, R3, R4 and R5 are selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkanoylamino and dialkylamino in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive, are produced by condensing a 1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione of the formula (I): SPC2 wherein R1, R2, R3, R4 and R5 are defined as above, with an organic acid hydrazide of the formula: EQU1 wherein R is defined as above. The new products of formula IV including their pharmacologically acceptable acid addition salts are useful as sedatives, tranquilizers and muscle relaxants in mammals and birds.

Animal feed and process

An animal feed comprising a compound of the group consisting of 6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula: STR1 WHEREIN R is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, phenyl, benzyl and -COOR' in which R' is alkyl of 1 to 4 carbon atoms, inclusive; wherein R1 is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; and wherein R2, R3, R4 and R5 are selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkanoylamino and dialkylamino in which the carbon chain moieties are of 1 to 3 carbon atom, inclusive and their pharmacologically acceptable acid addition salts in combination with a nutrient feed. A process for obtaining increased productivity in meat producing, milk producing, and egg laying animals by feeding the aforementioned compounds in combination with nutrient feeds.