116002-70-1

Basic information

• Product Name: ONDANSETRON
• Synonyms: AKOS NCG1-0013;9-METHYL-3-[(2-METHYLIMIDAZOL-1-YL)METHYL]-2,3-DIHYDRO-1H-CARBAZOL-4-ONE;Ondansetron HCl 2H2O;OndansetronHclDihydrateUspXxiv;OndansetronBase;Ondansetron Hcl 103639-04 / Base;Ondansetron (base and/or unspecified salts);OMEPRAZOLESODIUM
• CAS NO: 116002-70-1
• Molecular Formula: C₁₈H₁₉N₃O
• Molecular Weight: 293.36
• EINECS: 1308068-626-2
• Mol File: 116002-70-1.mol

Chemical Properties

• Appearance: /
• Refractive Index: 1.691
• CAS DataBase Reference: ONDANSETRON(CAS DataBase Reference)
• NIST Chemistry Reference: ONDANSETRON(116002-70-1)
• EPA Substance Registry System: ONDANSETRON(116002-70-1)

Safety Data

• Hazardous Substances Data: 116002-70-1(Hazardous Substances Data)

Usage

Brand name

Zofran (GlaxoSmithKline).

InChI:InChI=1/C17H18N4O/c1-12-18-8-10-20(12)11-21-9-7-15-16(17(21)22)13-5-3-4-6-14(13)19(15)2/h3-6,8,10H,7,9,11H2,1-2H3

Upstream product

• 693-98-1 2-methylimidazole 
• 99614-64-9 9-methyl-3-methylene-1,2,3,9-tetrahydro-4H-carbazol-4-one 
• 27387-31-1 9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one 
• 1630-73-5 N-ethyloxazolidine 
• 20073-50-1 2-(oxazolidin-3-yl)ethanol 
• 51200-87-4 4,4-dimethyl-oxazolidine 
• 108-74-7 1,3,5-trimethyl-1,3,5-triazacyclohexane 
• 51-80-9 bis-(dimethylamino)methane 
• 880-09-1 di(N-piperidinyl)methane 
• 60498-72-8 N-(trimethylsilyl)-2-methylimidazole 
• 123-91-1 1,4-dioxane 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 132659-89-3 3-[(dimethylamine)methyl]-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one hydrochloride 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 99614-14-9 1,2,3,9-Tetrahydro-3-[(2-methyl-1H-imidazolyl-1-yl)methyl]-4H-carbazol-4-one 
• 126671-71-4 8-Hydroxyondansetron 
• 99614-01-4 Ondansetron hydrochloride 

Relevant articles and documents

An efficient process of ondansetron synthesis

An efficient and practical two-step synthesis of ondansetron (1) was accomplished from readily available N-methyltetrahydrocarbazolone (2) via direct Mannich a-methylenation and alumina catalyzed Michael addition resulting in a 70% overall yield.

C(sp2)-H Bond Multiple Functionalization in Air for Construction of Tetrahydrocarbazoles with Continuous Quaternary Carbons and Polycyclic Diversification

The C(sp2)-H function of indole ketone with diazo compound via a rhodium(II)-catalyzed intramolecular electrophilic trapping reaction under mild conditions in air was demonstrated. The established methodology provided a highly efficient approach for direct synthesis of mutisubstituted tetrahydrocarbazoles with continuous quaternary carbons. The resulting products facilitate further modification to conveniently construct tetrahydrocarbazoles with additional fused heterocyclic rings. By phenotypic screening, several products exhibit good anticancer bioctivities in osteosarcoma cell lines.

IMIDAZOLYL MODULATORS OF 5-HT3 RECEPTORS

The present invention relates to new imidazolyl modulators of 5-HT3 receptors, pharmaceutical compositions thereof, and methods of use thereof.

Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one and ondansetron therefrom

The present invention provides a rapid, high-yielding process for preparing 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one from 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one without using a secondary amine as a catalyst, and without using glacial acetic acid as a solvent. The present invention further provides a rapid, high-yielding process for preparing ondansetron from 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one without using alumina as a catalyst.

A ONE-POT PROCESS FOR THE PREPARATION OF ANTIEMETIC AGENT, 1,2,3,9-TETRAHYDRO-9-METHYL-3[(2-METHYL)-1H-IMIDAZOLE-1-YL)METHYL]-4H-CARBAZOL-4-O

A one-pot industrial process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazole-1-yl)methyl]-4H-carbazol-4-one of Formula-(I) from 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one of Formula-(IV) involves reaction of Formula (IV) with HNR1R2 salt and paraformaldehyde, where R1,R2 are independently alkyl groups or together forms a cyclic alkyl group, in a solvent system of acetic acid and hydrocarbon solvent to form a crude mixture of intermediate compounds of Formula (III) and (VIII), which is converted to ondansetron (Formula (I)) without isolation by reaction with 2-methyimidazole in a suitable solvent system in the same pot.

PROCESS FOR PREPARING 1,2,3,9-TETRAHYDRO-9-METHYL-3-[(2-METHYL-1H-IMIDAZOLE-1-YL)METHYL]-4H-CARBAZOL-4-ONE OR ITS SALT

The present invention provides an improved process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one or its salt, which is useful as an anti-vomiting agent, in a high yield under a mild condition, so as to be favorably applied to a large-scale mass production thereof.

PROCESS FOR PREPARING 1,2,3,9-TETRAHYDRO-9-METHYL-3-[(2-METHYL-1H-IMIDAZOLE-1-YL)METHYL]-4H-CARBAZOL-4-ONE OR ITS SALT

1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]- 4H-carbazol-4-one or its salt is prepared in high yield by reacting a compound of formula 2 with a compound of formula 3 and a compound of formula 4 in the presence of an acid, an alkylsilylhalide compound or an acylhalide compound, in an solvent, and thus, such an inventive process can be favorably applied to a large-scale mass production thereof.

NEW POLYMORPHIC FORMS OF ONDANSETRON, PROCESSES FOR PREPARING THEM, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THEIR USE AS ANTIEMETICS

This invention relates to new polymorphs of (±)1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-il)methyl]-4H-carbazol-4-one, known under the INN of ondansetron, to processes for preparing said polymorphs, to pharmaceutical compositions containing them and to their use in the treatment and prophylaxis of nausea and vomiting. The invention provides new stable polymorphic forms of ondansetron and processes for manufacturing them at an industrial scale.

ONDANSETRON FORMS AND PROCESSES OF MAKING THE SAME

The invention relates to a solid crystalline ondansetron having at least one of the following characteristics: a melting endotherm peak greater than or equal to 240°C; a trace amount of a base or residue thereof comprising an alkali metal, an amine, an ammonium or an ion thereof; or a water content of 1.3 to 1.5 wt%, and to a composition comprising same and a pharmaceutically acceptable excipient, and to a process, which comprises: neutralizing an acid addition salt of ondansetron to liberate ondansetron free base; and precipitating said ondansetron free base from a liquid media, and to a process, which comprises dissolving ondansetron free base in a solvent and precipitating said dissolved ondansetron free base to form ondansetron having a melting endotherm peak of greater than or equal to 240°C measured on DSC at 5°C/min.

NOVEL PROCESS FOR THE PREPARATION OF IMIDAZOLYL COMPOUNDS

The present invention relates to a method for the preparation of an imidazolyl compound of the general formula (I), wherein: Ra and Rb each separately are (C1-C6)alkyl, (C1-C6)alkoxyalkyl, optionally substituted aryl or heteroaryl; or wherein Ra and Rb together form a further homocyclic or heterocyclic system comprising one or more rings; Ra’ and Rb’ each are hydrogen or together form a carbon-carbon double bond, said carbon-carbon double bond optionally being part of an aromatic system; Rc is hydrogen, (C1-C6)alkyl, (C1-C6)alkoxy, (C1,-C6)alkoxyalkyl or halogen; Rd is hydrogen or (C1-C4)aIkyl; Re is hydrogen or (C1-C4)aIkyl; m is 1 or 2; and R1, is hydrogen or (C1-C4)aIkyl; as well as its acid addition salt;characterized in that a compound of the general formula (II) is reacted with a compound of the formula (III), wherein: R is a hydrogen, a (C1-C4)alkyl group optionally substituted with a hydroxygroup or an optionally substituted aryl group, R', R", R'" and R"" each individually are a hydrogen or a (C1-C4)aIkyl group; followed by a reaction with a compound of the formula (IV), wherein R1, Rd and Re have the meanings defined above; and optionally followed by a reaction with a suitable acid. De method according to the present invention is especially useful for the preparation of ondansetron and cilansetron.