313368-91-1

Basic information

• Product Name: ITI-722
• Synonyms: ITI-722;Lumateperone
• CAS NO: 313368-91-1
• Molecular Formula: C₂₄H₂₈FN₃O
• Molecular Weight: 393.4970232
• Product Categories: API
• Mol File: 313368-91-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 556.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.26±0.1 g/cm3(Predicted)
• PKA: 9.10±0.20(Predicted)
• CAS DataBase Reference: ITI-722(CAS DataBase Reference)
• NIST Chemistry Reference: ITI-722(313368-91-1)
• EPA Substance Registry System: ITI-722(313368-91-1)

Safety Data

• Hazardous Substances Data: 313368-91-1(Hazardous Substances Data)

Usage

Description

Lumateperone is a novel antipsychotic agent with a unique mechanism of action with high 5-hydroxytryptamine 2A(5-HT2A) blocking activity. A Phase 2 study in treatment of insomnia revealed strong evidence of efficacy, with no impairment of next-day cognition.

Uses

Lumateperone was a drug developed for the treatment of schizophrenia. May have applications in bipolar depression.

Upstream product

• 1059630-08-8 (4aS,9bR)-ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate 
• 2098497-32-4 (4aS,9bR)-ethyl 6-bromo-5-(2-(methylamino)-2-oxoethyl)-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate 
• 313369-25-4 (6bR,10aS)-ethyl 2,3,6b,9,10,10a-hexahydro-3-methyl-2-oxo-1H-pyrido[3‘,4’:4,5]-pyrrolo[1,2,3-de]quinoxaline-8-carboxylate 
• 313369-26-5 (6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3‘,4’:4,5]-pyrrolo[1,2,3-de]quinoxaline-8-carboxylate 
• 1059630-07-7 [4aS,9bR]-6-bromo-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole 
• 439928-25-3 6-bromo-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 
• 352-13-6 4-flourophenylmagnesium bromide 
• 3874-54-2 4-(4-fluorophenyl)-4-oxo-n-butyl chloride 
• 313368-85-3 (6bR,10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido-[3’,4’:4,5]-pyrrolo[1,2,3-de]quinoxaline 

Downstream Products

• 1187020-80-9 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone toluenesulfonic acid salt 

Relevant articles and documents

Preparation method and intermediate of rumepirone

The invention provides a preparation method and intermediate of rumepirone. The preparation method comprises the following steps: taking a 6-bromine-2, 3, 4, 5-tetrahydro-1H-pyrido [4, 3-b] indole compound 1 as an initial raw material to obtain a compound 2, then carrying out Boc protection to obtain a compound 3, and then reacting the compound 3 with 2-chloro-N-methyl acetamide to obtain a compound 4; carrying out intramolecular Ullmann coupling reaction cyclization to obtain a compound 5; reducing the compound 5 by using borane to obtain a compound 6, then removing Boc protection and performing salifying to obtain a mepiquat key intermediate compound 7, or performing reducing and deprotecting by using a one-pot method and performing salifying to obtain an intermediate compound 7; enabling an intermediate compound 7 and a compound 8 to be subjected to reductive amination condensation to obtain a compound 9, and finally enabling the compound 9 to react with a 4-fluorophenyl Grignard reagent to obtain a rumepirone product compound 10, wherein the reaction route is shown in the specification.

ORGANIC COMPOUND

The invention relates to a particular substituted heterocycle fused gamma-carboline, in free, or pharmaceutically acceptable salt, and/or substantially pure form as described herein, pharmaceutical compositions thereof, and methods of use in the treatment of diseases involving the 5-HT2A receptor, the serotonin transporter (SERT), and/or pathways involving the dopamine D1 and D2 receptor signaling system.

METHOD FOR THE MANUFACTURE OF LUMATEPERONE AND ITS SALTS

Method for the production of formula (I) lumateperone or its acid addition salts so that the enantiomer compound with stereochemistry 6bR, 10aS is separated form the cis racemate using resolution and the formula (II) stereoisomer is alkylated with 4-halo-4'-fluoro butyrophenone (X = I, Br, CI) to produce the formula (I) lumateperone, or optionally its acid addition salt. The object of the invention also relates to the amorphous form of the morphologically uniform p-toluenesulfonic acid salt of lumateperone and to the naphthalene-2-sulfonic acid salt of lumateperone, to the 1 :2 stoichiometry salt of lumateperone formed with naphthalene-2-sulfonic acid.