26638-66-4

Basic information

• Product Name: 3,11-Dichloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepine 5,5-dioxide
• Synonyms: 3,11-DICHLORO-6,11-DIHYDRO-5,5-DIOXO-11-HYDROXY-6-METHYLDIBENZO[C,F][1,2]THIAZEPINE;3,11-dichloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepine 5,5-dioxide;Dibenzo[c,f][1,2]thiazepine,3,11-dichloro-6,11-dihydro-6-methyl-,5,5-dioxide;3,11-DICHLORO-6,11-6-METHYLDIBENZO[C,F][1,2]THIAZEPINE5,5-DIOXIDE;5,8-DICHLORO-10-DIOXO-11-METHYL-DIBENZO[C,F][1,2]THIAZEPINE;DIBENZO[C,F][1,2]THIAZEPINE,3,11-DICHLORO-6,11-DIHYDRO-6-METHYL-,5,5-DIOXIDE (8CI,9CI);3-Chloro-6,11-dihydro-6-methyl-11-chlorodibenzo[c,f][1,2]thiazepine 5,5-dioxide;3,11-Dichloro-6,11-dihydro-6-methyl-5,5-dioxodibenzo[c,f][1,2]thiazepine
• CAS NO: 26638-66-4
• Molecular Formula: C₁₄H₁₁Cl₂NO₂S
• Molecular Weight: 328.21
• EINECS: 247-866-8
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 26638-66-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 445.3 °C at 760mmHg
• Flash Point: 223.1 °C
• Appearance: White to light yellow crystalline powder
• Density: 1.54 g/cm³
• Vapor Pressure: 3.99E-08mmHg at 25°C
• Refractive Index: 1.686
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly)
• PKA: -4.11±0.40(Predicted)
• CAS DataBase Reference: 3,11-Dichloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepine 5,5-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,11-Dichloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepine 5,5-dioxide(26638-66-4)
• EPA Substance Registry System: 3,11-Dichloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepine 5,5-dioxide(26638-66-4)

Safety Data

• Hazardous Substances Data: 26638-66-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Intermediate in the preparation of Tianeptine and respective metabolites

InChI:InChI=1/C14H11Cl2NO2S/c1-17-12-5-3-2-4-10(12)14(16)11-7-6-9(15)8-13(11)20(17,18)19/h2-8,14H,1H3

Upstream product

• 26638-53-9 8-chloro-10,10-dioxo-11-methyl-5,11-dihydrodibenzo<1,2>thiazepin-5-one 
• 26723-60-4 5-hydroxy-8-chloro-10,10-dioxo-11-methyl-5,11-dihydrodibenzo<1,2>thiazepine 

Downstream Products

• 1231718-21-0 7-(((11RS)-3-chloro-6-methyl-6,11-dihydro-dibenzo[c,f][1,2]thiazepin-11-yl)amino)heptanenitrile S,S-dioxide 
• 66981-77-9 ethyl 7-((3-chloro-6-methyl-5,5-dioxido-6,11-dihydrodibenzo[c,f][1,2]thiazepin-11-yl)amino)heptanoate 
• 191172-75-5 tianeptine 

Relevant articles and documents

A process for preparing 3,11-Dichloro-6-methyl -6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide

The present invention relates to a method for preparing 3,11-dichloro-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide. More particularly, the present invention relates to a method for preparing high-purity 3,11-dichloro-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide at a high yield under safe atmosphere through a quantitative reaction without introduction of an excessive amount of hydrogen chloride gas from the outside by substituting the hydroxyl group of 3-chloro-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine-11-ol 5,5-dioxide as a starting material with a chloride group by means of hydrogen chloride gas generated in situ under the environment of acetyl chloride and the same equivalent of alcohol.

New Triazine Derivatives as Potent Modulators of Multidrug Resistance

A series of 70 triazine derivatives have been synthesized and tested for their capacity to modulate multidrug resistance (MDR) in DC-3F/AD and KB-A1 tumor cells in vitro, in comparison with verapamil (VRP), a calcium channel antagonist currently used in therapy as an antihypertensive drug, which also shows MDR modulating activity.Among the 12 selected compounds, 16 (S9788) showed high MDR reversing properties in vitro (300- and 6-fold VRP at 5μM in DC-3F/AD and KB-A1 cells, respectively) and induced a strong accumulation of adriamycin.The relationship between the increase of ADR accumulation and the fold reversal induced by these compounds and their lack of effects on the sensitive DC-3F cells suggest that they act mainly by inhibiting the P-glycoprotein (Pgp) catalyzed efflux of cytotoxic agents, as already described for a majority of MDR modulators.In vivo, in association with the antitumor drug vincristine (0.25 mg/kg), 16 (100 mg/kg) increased the T/C by 39percent in mice bearing the resistant tumor cell line P388/VCR.According to these interesting properties, 16 was selected for a clinical development because it is more bioavailable than 34, even though it was less active.