- Preparation method of lasmiditan
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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.
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Paragraph 0091-0093
(2021/07/01)
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- 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
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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).
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- PROCESS FOR PREPARATION OF LASMIDITAN
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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.
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- Preparation method of 5-HT1F agonist compound
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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.
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- CRYSTALLINE FORM OF RECEPTOR AGONIST, AND MANUFACTURING METHOD AND PHARMACEUTICAL COMPOSITION THEREOF
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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
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Paragraph 0252-0253
(2019/08/22)
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- COMPOSITIONS AND METHODS OF SYNTHESIS OF PYRIDINOYLPIPERIDINE 5-HT1F AGONISTS
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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
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Page/Page column 27-28
(2011/10/13)
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- PYRIDINOYLPIPERIDINES AS 5-HT1F AGONISTS
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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.
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Page/Page column 35
(2008/06/13)
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