127199-06-8

Basic information

• Product Name: DU 6858
• Synonyms: 7-[(7R)-7-Amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1S,2R)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid;DU 6858;SitafloxacinisomerⅡ(RSR);3-Quinolinecarboxylic acid, 7-[(7R)-7-aMino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1S,2R)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-;7-[(7R)-7-Amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1S,2R)-2-fluorocyclopropyl]-1;7-[(7R)-7-amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1S,2R)-2-fluoro-cyclopropyl]-1,4-dihydro-4-oxo-Quinolin-3-carboxylic acid;Sitafloxacin Isomer Impurity 2
• CAS NO: 127199-06-8
• Molecular Formula: C19H18ClF2N3O3
• Molecular Weight: 409.818
• Mol File: 127199-06-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 1.63
• CAS DataBase Reference: DU 6858(CAS DataBase Reference)
• NIST Chemistry Reference: DU 6858(127199-06-8)
• EPA Substance Registry System: DU 6858(127199-06-8)

Safety Data

• Hazardous Substances Data: 127199-06-8(Hazardous Substances Data)

Usage

General Description

DU 6858, also known as desmethylclozapine, is a potential antipsychotic drug with antagonist activity at serotonin 5-HT2A and dopamine D2 receptors, as well as partial agonist activity at 5-HT1A receptors. It has been shown to have significant efficacy in treating schizophrenia and other psychotic disorders, with a favorable side effect profile compared to other antipsychotic drugs. Additionally, DU 6858 has been investigated for its potential use in treating bipolar disorder and dementia-related psychosis. Preclinical studies have also suggested that it may have promising antidepressant effects. Overall, DU 6858 shows significant promise as a potential treatment for a range of psychiatric disorders, with the potential for improved efficacy and reduced side effects compared to currently available medications.

Upstream product

• 180506-32-5 (R)-5-Benzyl-7-hydroxy-5-aza-spiro[2.4]heptan-4-one 
• 144282-35-9 5-benzyl-7(S)-amino-5-azaspiro[2,4]heptane 
• 1432056-70-6 5-benzyl-7(S)-tert-butoxycarbonylamino-5-azaspiro[2,4]heptane 
• 129306-05-4 ethyl 1-(2-bromoacetyl)cyclopropanecarboxylate 
• 127199-24-0 8-Chloro-6,7-difluoro-1-((1S,2R)-2-fluoro-cyclopropyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 127199-43-3 7(R)-<(tert-butoxycarbonyl)amino>-5-<1(R)-phenylethyl>-5-azaspiro<2.4>heptane 
• 127199-39-7 7-(R)-amino-5-<1(R)-phenylethyl>-4-oxo-5-azaspiro<2.4>heptane 
• 127199-44-4 7(R)-<(tert-butoxycarbonyl)amino>-5-azaspiro<2.4>heptane 
• 127199-40-0 7-(R)-amino-5-<1(R)-phenylethyl>-5-azaspiro<2.4>heptane 
• 127199-25-1 8-chloro-6,7-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 
• 127199-42-2 7(S)-<(tert-butoxycarbonyl)amino>-5-<1(R)-phenylethyl>-5-azaspiro<2.4>heptane 
• 127199-38-6 7-(S)-amino-5-<1(R)-phenylethyl>-4-oxo-5-azaspiro<2.4>heptane 
• 127199-45-5 (7S)-5-azaspiro[2.4]heptan-7-ylcarbamic acid tert-butyl ester 
• 127199-41-1 7-(S)-amino-5-<1(R)-phenylethyl>-5-azaspiro<2.4>heptane 

Relevant articles and documents

Preparation method of sitafloxacin hydrate

The invention discloses a preparation method of sitafloxacin hydrate. The method comprises the following steps: taking ethyl 4-bromoacetoacetate used as a raw material, enabling ethyl 4-bromoacetoacetate to be fully reacted with 1,2-dibromoethane and preparing the obtained product into a compound II in the presence of carbonyl reduction enzyme; taking the compound II, enabling the compound II to carry out cyclization reaction with benzylamine in a solvent in the presence of cesium carbonate, enabling the obtained product to be reacted with DPPA and preparing a compound IV; reducing nitrine group of the compound IV to prepare a compound V; connecting primary amine group of the compound V with a BOC protection group to obtain a compound VI; reducing the compound VI through Pd/C, enabling theobtained product to be reacted with 8-chlorine-6,7-difluoro-1-[(1R,2s)-2-fluorocyclopropyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester to prepare a compound VIII; and carrying out deprotection of the compound VIII to obtain sitafloxacin hydrate. The sitafloxacin hydrate is few in preparation steps, simple in post-treatment and relatively high in yield.

A Sitafloxacine intermediate, Sitafloxacine preparation method and Sitafloxacine pharmaceutical composition

The invention discloses a sitafloxacin intermediate, a preparation method of sitafloxacin and a sitafloxacin pharmaceutical composition. The preparation method can be used for solving the problems of low yield, troublesome aftertreatment, poor safety and higher cost in the existing sitafloxacin preparation. The preparation method disclosed by the invention is simple in process, easily available in raw materials, lower in cost, the solvent after reaction is easy to treat, high yield and quite suitable for large-scale industrial production. The sitafloxacin pharmaceutical composition obtained by virtue of the preparation method provided by the invention can be used for further improving the product dissolution effect, improving the in-vivo bioavailability of the sitafloxacin and enhancing the exertion of medical effect.

Synthesis and characterization of sitafloxacin

The convenient protocol for the synthesis of sitafloxacin is described. Reaction of ethyl 3-(3-choloro-2,4,5-trifluorophenyl)-3-oxopropanoate with triethylorthoformate and (1R,2S)-(-)-cis-1,2 fluorine cyclopropane amino-p-toluene sulfonic acid salt by condensation under sodium hydrogen condition. The reaction mixture take place hydrolysis of ester in hydrochloric acid solution. Subsequence reacted with (S)-N[(oxoboryl) methylene] -5-azaspiro[2,4]heptan-7-amine by condensation. In the end taken off the protection group gives sitafloxacin and total conversion about 52-65%. The structure of sitafloxacin was characterized by 1H NMR, 13C NMR, IR, MS and elemental analysis.