115956-12-2

Usage

Uses

Used in Pharmaceutical Industry:
(2alpha,6alpha,8alpha,9abeta)-Octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl-1H-indole-3-carboxylate is used as an active pharmaceutical ingredient for the prevention and treatment of postoperative nausea and vomiting. Its specific mechanism of action involves acting as a serotonin (5HT3) receptor antagonist, which helps to reduce the incidence and severity of these symptoms.
Used in Anticancer Applications:
In the field of oncology, (2alpha,6alpha,8alpha,9abeta)-Octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl-1H-indole-3-carboxylate is used as an anticancer agent. It modulates various oncological signaling pathways, potentially exerting inhibitory effects on tumor growth and progression. Additionally, it may demonstrate synergistic anticancer effects when combined with conventional chemotherapeutic drugs, enhancing chemo-sensitivity and efficacy in resistant cases.
Used in Drug Delivery Systems:
To improve the delivery, bioavailability, and therapeutic outcomes of (2alpha,6alpha,8alpha,9abeta)-Octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl-1H-indole-3-carboxylate, novel drug delivery systems have been developed. These systems employ various organic and metallic nanoparticles as carriers, aiming to enhance the compound's efficacy against cancer cells and other medical applications.
Chemical Properties:
(2alpha,6alpha,8alpha,9abeta)-Octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl-1H-indole-3-carboxylate is a white solid, indicating its potential for formulation into various dosage forms for pharmaceutical use.
Brand Name:
Anzemet (Sanofi Aventis) is a brand name under which (2alpha,6alpha,8alpha,9abeta)-Octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl-1H-indole-3-carboxylate may be marketed, specifically for the prevention of postoperative or chemotherapy-induced nausea.

InChI:InChI=1/C19H20N2O3/c22-17-10-21-13-5-12(17)6-14(21)8-15(7-13)24-19(23)18-16-4-2-1-3-11(16)9-20-18/h1-4,12-15H,5-10H2

Upstream product

• 771-50-6 1H-indole-3-carboxylic acid 
• 115956-07-5 endo-hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one 
• 143343-85-5 endo-5-hydroxy-8-azatricyclo[5.3.1.0³,⁸]-undecan-10-one 
• 115956-07-5 trans-hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one 
• 22980-09-2 indolyl-3-glyoxylyl chloride 
• 115956-07-5 endo-hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3-(4H)-one 
• 115956-07-5 endo-hexahydro-8-hydroxy-2.6-methano-2H-quinolizin-3(4H)-one 

Downstream Products

• 115956-13-3 dolasetron mesylate 
• 115956-13-3 dolasetron mesylate 
• 1184914-65-5 CH₄O₃S*C₁₉H₂₀N₂O₃ 
• 115956-13-3 endo-hexahydro-8-(3-indolylcarbonyloxy)-2,6-methano-2H-quinolizin-3(4H)-one mesylate 
• 115956-13-3 endo-hexahydro-8-(3-indolylcarbonyloxy)-2,6-methano-2H-quinolizin-3(4H)-one methanesulphonate monohydrate 

Relevant academic research and scientific papers

Dolasetron N-oxide, preparation method and application thereof

The invention relates to a dolasetron N-oxide with a structure shown in a formula (I) or a salt thereof, and a preparation method and application of the compound, wherein the compound has a relatively strong inhibition effect on kinases Lyn and MST1, and can be used as an antitumor drug.

Dolasetron oxide and preparation method and application thereof

The invention relates to dolasetron oxide with a structure shown as a formula (I) or salt thereof, and a preparation method and application of the dolasetron oxide, and the dolasetron oxide has a strong inhibition effect on kinase Lyn and MST1, and can be used as an antitumor drug.

Dolasetron mesylate crystal form and preparation method

The invention provides a dolasetron mesylate crystal form. The molecular structural formula is represented in the description. The crystal form is a white powdery crystal, molecular composition is C19H20N2O3.CH3SO3H.H2O, a reflection angle 2 theta of X-ray powder diffraction of the crystal form has characteristic peaks at 11.8 degrees, 12.1 degrees, 15.1 degrees, 15.4 degrees, 22.9 degrees, 26.6 degrees, 29.9 degrees and 30.1 degrees, and differential scanning calorimetry shows that three absorption peaks exist at 150 DEG C, 164 DEG C and 260 DEG C. According to the dolasetron mesylate crystalform, product purity is high, few single impurities are contained, and heat stability of the crystal form is good. The invention further provides a preparation method of the dolasetron mesylate crystal form.

INTERMEDIATE COMPOUNDS USEFUL TO PREPARE DOLASETRON

The present invention relates to intermediates useful in the synthesis of Dolasetron and synthetic precursors thereof, as well as to processes for obtaining them. In addition, it refers to the hydrochloric salt of Dolasetron and polymorphic forms of Dolasetron and precursors thereof.

Polymorphs of Dolasetron base and process for preparation thereof

The present invention provides polymorphic forms of dolasetron base and methods for their use and preparation.

Polymorphic Forms of Dolasetron Base and Processes of Preparing Dolasetron Base, Its Polymorphic Forms and Salt Thereof

The present disclosure relates to a process for the preparation of endo-hexahydro-8-(3-indolylcarbonyloxy)-2,6-methano-2H-quinolizin-3(4H)-one or Dolasetron base. It also discloses a process for the preparation of endo-hexahydro-8-(3-indolylcarbonyloxy)-2,6-methano-2H-quinolizin-3(4H)-one mesylate or Dolasetron mesylate. Further, the present disclosure relates to a process for producing Form I of Dolasetron base, and to the novel crystalline polymorphs, Form II, III, IV and V of Dolasetron base and industrial processes for producing them.

METHOD FOR OBTAINING A PHARMACEUTICALLY ACTIVE COMPOUND, SYNTHESIS INTERMEDIATES THEREOF AND METHODS FOR OBTAINING THEM

The present invention relates to a method for obtaining Dolasetron that comprises: a) Esterification of the alcohol of formula (IV) with indole-3-carboxylic acid (compound (III)) or a reactive derivative thereof, to give a compound of formula (V), followed by step b) which includes Dieckmann reaction of the intermediate (V), by reaction with a strong organic or inorganic base, to give the intermediate (VI), and step c) which comprises dealcoxycarbonylation of the intermediate (VI) to give Dolasetron base and, if desired, a pharmaceutically acceptable salt thereof, hydrates or solvates of the base of said salt. The invention also relates to the intermediates (V) and (VI), and methods for obtaining them. With the method of the present invention Dolasetron is obtained at industrial scale with good yields, with decreased use of reactants and solvents, while said method is also of greater atomic efficiency.

PRODUCTION OF DOLASETRON

The present invention provides an improved process for the preparation of Dolasetron salts, in particularly Dolasetron mesylate. % Also provided are intermediates for the process and methods of preparing the intermediates.

METHOD FOR PREPARING HEXAHYDRO-8-HYDROXY-2,6-METHANO-2H-CHINOLIZIN-3(4H)-ONE ESTERS

The invention concerns a method for preparing optionally substituted 3-indolcarboxylic acid esters, with hexahydro-8-hydroxy-2,6-methano-2H-chinolizin-3(4H)-one. The invention is characterized in that the optionally substituted 3-indolcarboxylic acid is c

USE OF 5-HT3 RECEPTOR ANTAGONISTS IN TREATING PANIC DISORDERS OR OBSESSIVE COMPULSIVE COMPULSIVE DISORDERS

5-HT 3 Receptor antagonists are useful in treating panic disorders or obsessive compulsive disorders.