439239-90-4

Basic information

• Product Name: LasMiditan
• Synonyms: LasMiditan;2,4,6-trifluoro-N-(6-(1-Methylpiperidine-4-carbonyl)pyridin-2-yl)benzaMide;2,4,6-Trifluoro-N-[6-[(1-methyl-4-piperidinyl)carbonyl]-2-pyridinyl]benzamide;COL 144;LY573144;LasMiditan (COL-144;Benzamide, 2,4,6-trifluoro-N-[6-[(1-methyl-4-piperidinyl)carbonyl]-2-pyridinyl]-;2,4-difluoro-N-(6-(1-methylpiperidine-4-carbonyl)pyridin-2-yl)benzamide
• CAS NO: 439239-90-4
• Molecular Formula: C₁₉H₁₈F₃N₃O₂
• Molecular Weight: 377.3603296
• Product Categories: API
• Mol File: 439239-90-4.mol

Chemical Properties

• Melting Point: 255℃
• Boiling Point: 433.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.351
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 9.91±0.70(Predicted)
• CAS DataBase Reference: LasMiditan(CAS DataBase Reference)
• NIST Chemistry Reference: LasMiditan(439239-90-4)
• EPA Substance Registry System: LasMiditan(439239-90-4)

Safety Data

• Hazardous Substances Data: 439239-90-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Lasmiditan is used as a pharmaceutical agent for the treatment of migraine headaches. It targets the serotonin (5-HT) receptor subtype 5-HT1F, providing relief from the symptoms associated with migraines.
Used in Research and Forensic Applications:
Lasmiditan is utilized as a research compound, aiding in the study of serotonin receptor subtype 5-HT1F and its role in migraine headaches. Additionally, it is employed in forensic applications, possibly for the analysis of its presence in biological samples or for the investigation of its potential misuse.
Used in Preventive Dentistry:
Lasmiditan is used as a preventive agent for periodontal disease and tooth loss. Although the specific mechanism of action in this context is not provided in the materials, it is likely that its agonistic effect on the 5-HT1F receptor may contribute to the prevention or management of these dental conditions.

Upstream product

• 613678-03-8 (6-aminopyridin-2-yl)(1-methylpiperidin-4-yl)methanone 
• 79538-29-7 2,4,6-trifluorobenzoyl chloride 
• 613677-28-4 2,4,6-trifluoro-N-(6-(1-methylpiperidine-4-carbonyl)pyridine-2-yl)benzamide hydrochloride 
• 1060801-23-1 2-amino-6-ethanoylpyridine 
• 5570-77-4 4-chloro-1-methylpiperidine 
• 41776-24-3 1-methylpiperidine-4-carboxylic acid chloride 
• 215950-19-9 1-methyl-piperidine-4-carboxylic acid methoxy-methyl-amide 
• 626-05-1 2,6-Dibromopyridine 
• 68947-43-3 1-methylpiperidine-4-carboxylic acid 
• 19798-81-3 2-Amino-6-bromopyridine 

Downstream Products

• 439239-92-6 2,4,6-trifluoro-N- [6-(1-methylpiperidine-4-carbonyl)-2-pyridyl]benzamide hemisuccinate 
• 613677-28-4 2,4,6-trifluoro-N-[6-(1-methylpiperidin-4-ylcarbonyl)-pyridin-2-yl]benzamide hydrochloride 
• 439239-92-6 2,4,6-trifluoro-N-[6-(1-methylpiperidine-4-carbonyl)pyridin-2-yl]benzamide hemisuccinate 

Relevant articles and documents

2,2-DIMETHYL-N-[6-(1-METHYL-PIPERIDIN-4-CARBONYL)-PYRIDIN-2-YL]-PROPIONAMIDE, METHOD FOR PREPARING (6-AMINO-PYRIDIN-2-YL)-(1-METHYL-PIPERIDIN-4-YL)-METHANONE USING SAID COMPOUND, AND USE OF SAID COMPOUND IN THE PREPARATION OF LASMIDITAN

The present invention relates to a new intermediate, (2,2-dimethyl-N-[6-(1-methyl-piperidin-4-carbonyl)-pyridin-2-yl]-propanamide) useful in the synthesis of lasmiditan, to a method for obtaining same, to the use of said intermediate for preparing lasmiditan, to a method for preparing lasmiditan making use of said intermediate, and to a method for preparing an intermediate ((6-amino-pyridin-2-yl)-(1-methyl-piperidin-4-yl)-methanone) from (2,2-dimethyl-N-[6-(1-methyl-piperidin-4-carbonyl)-pyridin-2-yl]-propanamide).

Preparation method of lasmiditan

The invention provides a preparation method of lasmiditan. Specifically, 2-bromo-6-aminopyridine is taken as a raw material and subjected to a condensation reaction with 2, 4, 6-trifluorobenzoyl chloride, and then the reaction product reacts with 1-methyl-4-ethyl piperidinecarboxylate to prepare the lasmiditan. The preparation method has the advantages of simple and safe synthesis route and operation, easily available raw materials, simple post-treatment and high yield, and is suitable for industrial production.

PROCESS FOR PREPARATION OF LASMIDITAN

The present invention relates to a process for the preparation of lasmiditan, a compound of formula I, or pharmaceutically acceptable salts thereof, the process comprising reacting a compound of formula IX with N-methoxymethylamine or salt thereof to obtain a compound of formula VII; reacting the compound of formula VII with a compound of formula XIV to obtain lasmiditan or salts thereof.

CRYSTALLINE FORM OF RECEPTOR AGONIST, AND MANUFACTURING METHOD AND PHARMACEUTICAL COMPOSITION THEREOF

The present invention relates to the crystalline forms of a 5-HT1F receptor agonist 2,4,6-trifluoro-N-[6-[(1-methyl-piperidine-4-yl)carbonyl]pyridin-2-yl]-benzene formamide (lasmiditan) and its hydrochloride. The crystalline forms of the presen

Preparation method of 5-HT1F agonist compound

The invention relates to a preparation method of a 5-HT1F agonist compound. The preparation method of the 5-HT1F agonist compound comprises the steps that 2,3-butanedione and 2-halogenated acrylonitrile are subjected to 1,4-addition reaction to obtain 2-halogenated-5,6-dioxo n-heptanoic nitrile, then the 2-halogenated-5,6-dioxo n-heptanoic nitrile and ammonia are subjected to pyridine cyclizationand amino protection to obtain 2-disubstituted methylamino-6-acetyl pyridine, then 2-disubstituted methylamino-6-(1-methyl piperidine-4-base)formyl group piperidine is prepared through hydroxyethylation, sulfonic acid esterification and methylamine condensation reaction, and then the 5-HT1F agonist compound Lasmiditan is obtained through deprotection reaction and 2,4,6-trifluoro-benzoyl chloride amidation. The raw materials of the preparation method of the 5-HT1F agonist compound are easy to get, ultralow temperature reaction is avoided, the operation is simple and convenient, the cost is low,and industrial production of Lasmiditan is easy.

COMPOSITIONS AND METHODS OF SYNTHESIS OF PYRIDINOYLPIPERIDINE 5-HT1F AGONISTS

The present invention provides a novel polymorph of the hemisuccinate salt of 2,4,6-trifluoro-N-[6-(1-methyl-piperidine-4-carbonyl)-pyridin-2-yl]-benzamide (Form A) characterized by a unique X-ray diffraction pattern and Differential Scanning Calorimetry

PYRIDINOYLPIPERIDINES AS 5-HT1F AGONISTS

The present invention relates to compounds of formula I:or pharmaceutically acceptable acid addition salts thereof, where;R1 is C1-C6 alkyl, substituted C1-C6 alkyl, C3-C7 cycloalkyl, substituted C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3 alkyl, substituted C3-C7 cycloalkyl-C1-C3 alkyl, phenyl, substituted phenyl, heterocycle, or substituted heterocycle;R2 is hydrogen, C1-C3 alkyl, C3-C6 cycloalkyl-C1-C3 alkyl, or a group of formula II II;R3 is hydrogen or C1-C3 alkyl; R4 is hydrogen, halo, or C1-C3 alkyl;R5 is hydrogen or C1-C3 alkyl; R6 is hydrogen or C1-C6 alkyl; and n is an integer from 1 to 6 inclusively. The compounds of the present invention are useful for activating 5-HT1F receptors, inhibiting neuronal protein extravasation, and for the treatment or prevention of migraine in a mammal. The present invention also relates to a process for the synthesis of intermediates in the synthesis of compounds of Formula I.