AR119319A1 - Procesos e intermediario para la preparación a gran escala de hemisuccinato de 2,4,6-trifluoro-n-[6-(1-metil-piperidina-4-carbonil)-piridin-2-il]-benzamida y preparación de acetato de 2,4,6-trifluoro-n-[6-(1-metil-piperidina-4-carbonil)-piridin-2-il]-benzamida - Google Patents
Procesos e intermediario para la preparación a gran escala de hemisuccinato de 2,4,6-trifluoro-n-[6-(1-metil-piperidina-4-carbonil)-piridin-2-il]-benzamida y preparación de acetato de 2,4,6-trifluoro-n-[6-(1-metil-piperidina-4-carbonil)-piridin-2-il]-benzamidaInfo
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- AR119319A1 AR119319A1 ARP200101854A ARP200101854A AR119319A1 AR 119319 A1 AR119319 A1 AR 119319A1 AR P200101854 A ARP200101854 A AR P200101854A AR P200101854 A ARP200101854 A AR P200101854A AR 119319 A1 AR119319 A1 AR 119319A1
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- methyl
- treatment
- pyridyl
- subsequent
- methylpiperidine
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/08—Acetic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/10—Succinic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicinal Preparation (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Reivindicación 1: Un proceso para preparar un compuesto de la fórmula (1) que comprende las siguientes etapas: i.) tratamiento de ácido piperidina-4-carboxílico en condiciones de aminación reductora que comprende formaldehído y ácido fórmico en agua con tratamiento posterior con HCl acuoso seguido de destilación de agua y adición de acetonitrilo, con dilución / destilación repetida hasta que el contenido de agua no sea superior a 0,2% mediante análisis de Karl-Fischer, para obtener clorhidrato de ácido 1-metilpiperidina-4-carboxílico sólido; ii.) tratamiento de clorhidrato de ácido 1-metilpiperidina-4-carboxílico con un agente de cloración, tal como cloruro de tionilo en clorobenceno para obtener cloruro de ácido 1-metilpiperidina-4-carboxílico; iii.) tratamiento de cloruro de ácido 1-metilpiperidina-4-carboxílico con N,N-dietilamina en clorobenceno que contiene trietilamina con el posterior lavado de base y el posterior tratamiento con HCl acuoso en isopropanol para obtener clorhidrato de N,N-dietil-1-metil-piperidina-4-carboxamida hidrato sólido; iv.) tratamiento del clorhidrato de N,N-dietil-1-metil-piperidina-4-carboxamida hidrato con una base mineral, tal como NaOH acuoso en un solvente no polar, tal como metil-ter-butil éter con el posterior lavado con agua, separación de fases y destilación del solvente orgánico hasta que el contenido de agua no sea superior a 0,1% en peso mediante análisis de Karl Fischer para obtener N,N-dietil-1-metil-piperidina-4-carboxamida; v.) tratamiento posterior de N,N-dietil-1-metil-piperidina-4-carboxamida con (6-bromo-2-piridil)litio en un solvente orgánico no polar, tal como metilter-butil éter con la posterior extracción de la mezcla resultante con agua y un solvente orgánico adecuado, tal como n-butanol, separación de fases y destilación repetida del solvente orgánico hasta que el contenido de agua no sea más de 0,2% en peso mediante análisis de Karl-Fischer, para obtener (6-bromo-2-piridil)-(1-metil-4-piperidil)metanona; vi.) tratamiento de (6-bromo-2-piridil)-(1-metil-4-piperidil)metanona con HBr acuoso y la posterior extracción con n-butanol seguido de destilación repetida del solvente orgánico hasta que el contenido de agua no sea superior a 0,3% mediante análisis de Karl-Fischer, para obtener bromhidrato de (6-bromo-2-piridil)-(1-metil-4-piperidil)metanona sólido; vii.) tratamiento de bromhidrato de (6-bromo-2-piridil-1-metil-4-piperidil)metanona con una solución de NH₃ en etilenglicol en presencia de catalizador Cu₂O a alrededor de 80ºC durante alrededor de 2 h, con posteriores lavados con agua, NaCl acuoso saturado y 20% de NaOH acuoso y la posterior extracción con un solvente aprótico no polar, tal como metil-ter-butil éter, separación de fases y tratamiento de la fase orgánica con 5% en peso de carbón; viii.) filtración de la mezcla anterior, dilución con un solvente alcohólico polar adecuado, tal como isopropanol, y destilación repetida del solvente orgánico hasta que el contenido de agua no sea superior a 0,2% mediante análisis de Karl-Fischer, con el posterior tratamiento del residuo resultante con isopropanol, agua y 20% en peso de HCl, en donde la concentración de agua de la suspensión resultante es de al menos 2%, filtración de la suspensión resultante y secado al vacío a 40ºC durante 16 - 24 h para obtener diclorhidrato de (6-amino-2-piridil)-(1-metil-4-piperidil)metanona dihidrato sólido; ix.) tratamiento del diclorhidrato de (6-amino-2-piridil)-(1-metil-4-piperidil)metanona dihidrato en clorobenceno con 6% en peso/peso de NaOH en agua a alrededor de 54ºC durante alrededor de 30 min., con la posterior separación de fases y destilación al vacío de la solución acuosa para obtener (6-amino-2-piridil)-(1-metil-4-piperidil)metanona; x.) tratamiento posterior de (6-amino-2-piridil)-(1-metil-4-piperidil)metanona con cloruro de ácido 2,4,6-trifluorobenzoico en clorobenceno a alrededor de 100ºC durante alrededor de 4 h, con el posterior enfriamiento, carga con acetonitrilo y calentamiento de la suspensión resultante hasta 80ºC durante alrededor de 1 hora, y la posterior recolección del sólido resultante mediante filtración, para obtener clorhidrato de 2,4,6-trifluoro-N-[6-(1-metilpiperidina-4-carbonil)-2-piridil]benzamida; xi.) tratamiento de clorhidrato de 2,4,6-trifluoro-N-[6-(1-metilpiperidin-4-carbonil)-2-piridil]benzamida con solución acuosa saturada de Na₂CO₃ en metil-ter-butilo éter; xii.) tratamiento de la mezcla de la etapa xi anterior con SiO₂ con la posterior filtración, tratamiento con carbón, filtración y evaporación, dilución con etanol y destilación hasta que el contenido de agua no sea superior a 1% mediante análisis de Karl-Fischer, para obtener 2,4,6-trifluoro-N-[6-(1-metilpiperidina-4-carbonil)-2-piridil]benzamida; xiii.) tratamiento de 2,4,6-trifluoro-N-[6-(1-metilpiperidina-4-carbonil)-2-piridil]benzamida en etanol con una solución de 0,5 equivalentes de ácido succínico en etanol a alrededor de 55ºC durante no menos de 3 h a RT, y la posterior recolección del sólido mediante filtración, para obtener hemisuccinato de 2,4,6-trifluoro-N-[6-(1-metilpiperidina-4-carbonil)-2-piridil]benzamida sólido. Reivindicación 13: Un compuesto de la fórmula (2). Reivindicación 14: Una forma cristalina del compuesto de acuerdo con la reivindicación 13.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962871965P | 2019-07-09 | 2019-07-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR119319A1 true AR119319A1 (es) | 2021-12-09 |
Family
ID=71948732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP200101854A AR119319A1 (es) | 2019-07-09 | 2020-06-30 | Procesos e intermediario para la preparación a gran escala de hemisuccinato de 2,4,6-trifluoro-n-[6-(1-metil-piperidina-4-carbonil)-piridin-2-il]-benzamida y preparación de acetato de 2,4,6-trifluoro-n-[6-(1-metil-piperidina-4-carbonil)-piridin-2-il]-benzamida |
Country Status (36)
| Country | Link |
|---|---|
| US (5) | US20230137090A1 (es) |
| EP (2) | EP4410784A3 (es) |
| JP (3) | JP7301209B2 (es) |
| KR (3) | KR20220019772A (es) |
| CN (2) | CN120441536A (es) |
| AR (1) | AR119319A1 (es) |
| AU (2) | AU2020310852B2 (es) |
| BR (1) | BR112021026219A2 (es) |
| CA (2) | CA3146129C (es) |
| CL (2) | CL2022000018A1 (es) |
| CO (1) | CO2022000062A2 (es) |
| CR (1) | CR20220005A (es) |
| DK (1) | DK3996713T3 (es) |
| DO (1) | DOP2024000099A (es) |
| EC (1) | ECSP22001538A (es) |
| ES (1) | ES3006888T3 (es) |
| FI (1) | FI3996713T3 (es) |
| HR (1) | HRP20250049T1 (es) |
| HU (1) | HUE070451T2 (es) |
| IL (2) | IL289226B2 (es) |
| JO (1) | JOP20220002A1 (es) |
| LT (1) | LT3996713T (es) |
| MA (1) | MA56350B1 (es) |
| MD (1) | MD3996713T2 (es) |
| MX (2) | MX2022000372A (es) |
| MY (1) | MY201447A (es) |
| PE (1) | PE20220811A1 (es) |
| PH (1) | PH12022550031A1 (es) |
| PL (1) | PL3996713T3 (es) |
| PT (1) | PT3996713T (es) |
| RS (1) | RS66403B1 (es) |
| SA (1) | SA522431304B1 (es) |
| SI (1) | SI3996713T1 (es) |
| TW (2) | TWI776175B (es) |
| WO (1) | WO2021007155A1 (es) |
| ZA (2) | ZA202110805B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102753171A (zh) | 2009-04-02 | 2012-10-24 | 科鲁西德制药公司 | 2,4,6-三氟-n-[6-(1-甲基-哌啶-4-羰基)-吡啶-2-基]-苯甲酰胺的组合物 |
| TWI776175B (zh) * | 2019-07-09 | 2022-09-01 | 美商美國禮來大藥廠 | 大規模製備2,4,6-三氟-n-[6-(1-甲基-哌啶-4-羰基)-吡啶-2-基]-苯甲醯胺半琥珀酸鹽的方法及中間體，以及2,4,6-三氟-n-[6-(1-甲基-哌啶-4-羰基)-吡啶-2-基]-苯甲醯胺醋酸鹽之製備 |
| KR20240004942A (ko) | 2021-05-07 | 2024-01-11 | 일라이 릴리 앤드 캄파니 | 2,4,6-트리플루오로-n-[6-(1-메틸-피페리딘-4-카르보닐)-피리딘-2-일]-벤즈아미드헤미숙시네이트의 맛 차폐된 조성물 및 그를 포함하는 경구 붕해 정제 |
| CN115594665A (zh) * | 2021-07-08 | 2023-01-13 | 北京万全德众医药生物技术有限公司（Cn） | 拉司米地坦的新制备方法 |
| IT202100023861A1 (it) * | 2021-09-16 | 2023-03-16 | Procos Spa | Processo per la preparazione di (6-alopiridin-2-il)(1-metilpiperidin-4-il)metanone |
| CN113866318B (zh) * | 2021-10-21 | 2023-07-04 | 佛山奕安赛医药科技有限公司 | 一种(6-氨基吡啶-2-基)(1-甲基哌啶-4-基)甲酮双盐酸盐的检测方法 |
| WO2023152081A1 (en) * | 2022-02-09 | 2023-08-17 | Inke, S.A. | Process for preparing pyridinoylpiperidines 5-ht1f agonists and salts thereof |
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