RU2018121633A - Фенфлураминовые композиции и способы их получения - Google Patents
Фенфлураминовые композиции и способы их получения Download PDFInfo
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- RU2018121633A RU2018121633A RU2018121633A RU2018121633A RU2018121633A RU 2018121633 A RU2018121633 A RU 2018121633A RU 2018121633 A RU2018121633 A RU 2018121633A RU 2018121633 A RU2018121633 A RU 2018121633A RU 2018121633 A RU2018121633 A RU 2018121633A
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- Prior art keywords
- fenfluramine
- composition
- trifluoromethyl
- phenyl
- less
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- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 title claims 31
- 229960001582 fenfluramine Drugs 0.000 title claims 30
- 239000000203 mixture Substances 0.000 title claims 26
- 238000000034 method Methods 0.000 title claims 20
- 150000003839 salts Chemical class 0.000 claims 12
- BLXXCCIBGGBDHI-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]acetic acid Chemical group OC(=O)CC1=CC=CC(C(F)(F)F)=C1 BLXXCCIBGGBDHI-UHFFFAOYSA-N 0.000 claims 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 6
- JPHQCDCEBDRIOL-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]propan-2-one Chemical group CC(=O)CC1=CC=CC(C(F)(F)F)=C1 JPHQCDCEBDRIOL-UHFFFAOYSA-N 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- -1 Trifluoromethyl-phenyl Chemical group 0.000 claims 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 4
- 239000006227 byproduct Substances 0.000 claims 4
- 238000011084 recovery Methods 0.000 claims 4
- JOIYKSLWXLFGGR-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]acetonitrile Chemical compound FC(F)(F)C1=CC=CC(CC#N)=C1 JOIYKSLWXLFGGR-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000008186 active pharmaceutical agent Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- TYOCDHCKTWANIR-UHFFFAOYSA-N 2-[2-(trifluoromethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1C(F)(F)F TYOCDHCKTWANIR-UHFFFAOYSA-N 0.000 claims 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
- ZDVRPKUWYQVVDX-UHFFFAOYSA-N 2-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C=O ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/28—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with other reducing agents
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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
- A61K31/12—Ketones
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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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
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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
- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
- C07C49/233—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
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- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
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- Animal Behavior & Ethology (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
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- Child & Adolescent Psychology (AREA)
- Obesity (AREA)
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- Diabetes (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Claims (41)
1. Способ получения фенфлураминового активного фармацевтического ингредиента, данный способ включает:
(a) гидролиз 2-(3-(трифторметил)фенил)ацетонитрильной композиции, чтобы получить композицию 2-(3-(трифторметил)фенил)уксусной кислоты;
(b) реакционное взаимодействие композиции 2-(3-(трифторметил)фенил)уксусной кислоты с уксусным ангидридом и катализатором, чтобы получить композицию 1-(3-(трифторметил)фенил)пропан-2-она; и
(c) восстановительное аминирование композиции 1-(3-(трифторметил)фенил)пропан-2-она этиламином при применении борогидридного восстановителя, чтобы получить фенфлураминовую композицию.
2. Способ по п. 1, где 2-(3-(трифторметил)фенил)ацетонитрильная композиция содержит по меньшей мере 0,2 масс.% трифторметил-фенильных региоизомеров.
3. Способ по п. 1, где 2-(3-(трифторметил)фенил)ацетонитрильную композицию получают из трифторметилбензола.
4. Способ по п. 1, дополнительно включающий, перед стадией (b), очистку композиции 2-(3-(трифторметил)фенил)уксусной кислоты, чтобы получить композицию, по существу не содержащую один или несколько трифторметил-фенильных региоизомеров и по существу не содержащую трифторметилбензальдегид и бензальдегид.
5. Способ по п. 4, где очистка включает кристаллизацию 2-(3-(трифторметил)фенил)уксусной кислоты из композиции.
6. Способ по п. 1, где стадия (b) включает очистку композиции 1-(3-(трифторметил)фенил)пропан-2-она кетоновым бисульфитным аддуктом.
7. Способ по п. 1, где стадия (b) включает селективное реакционное взаимодействие 2-(3-(трифторметил)фенил)уксусной кислоты в присутствии непрореагировавшей 2-(2-(трифторметил)фенил)уксусной кислоты.
8. Способ по п. 1, где стадия (b) дополнительно включает удаление непрореагировавшего региоизомера 2-(2-(трифторметил)фенил)уксусной кислоты из композиции 1-(3-(трифторметил)фенил)пропан-2-она.
9. Способ по п. 1, где фенфлураминовая композиция является исходной неочищенной и по существу не включает:
трифторметил-фенильные региоизомеры фенфлурамина или их соли;
металлические катализаторы;
растворители Класса I (ICH Q3C); и
спиртовый побочный продукт восстановления.
10. Способ по п. 1, где фенфлураминовая композиция является исходной неочищенной и содержит менее чем 1 масс.% суммарно трифторметил-фенильных региоизомеров фенфлурамина или их солей.
11. Способ по п. 1, где фенфлураминовая композиция является исходной неочищенной и имеет менее чем 10 масс.% спиртового побочного продукта восстановления.
12. Способ по п. 1, дополнительно включающий кристаллизацию фенфлурамина или его соли из фенфлураминовой композиции.
13. Способ по п. 1, где стадию (b) выполняют при условиях, которые включают приведение композиции 2-(3-(трифторметил)фенил)уксусной кислоты в контактирование с примерно 0,5 эквивалента 1-метилимидазола и примерно 5 эквивалентами или более уксусного ангидрида, в необязательном растворителе.
14. Способ по п. 1, где стадию (c) выполняют при условиях, которые включают контактирование композиции 1-(3-(трифторметил)фенил)пропан-2-она с раствором 70 масс.% этиламина в воде и примерно 2,25 эквивалента или более триацетоксиборогидрида в метаноле в качестве растворителя.
15. Способ по п. 1, где фенфлураминовая композиция имеет следующий профиль:
по меньшей мере 80 масс.% фенфлурамина или его соли;
менее чем 1 масс.% 2-фенфлурамина или его соли;
менее чем 1 масс.% 4-фенфлурамина или его соли; и
менее чем 10 масс.% спиртового побочного продукта восстановления фенфлурамина.
16. Способ по п. 1, дополнительно включающий:
преобразование фенфлурамина в фенфлураминовой композиции в фармацевтически приемлемую соль фенфлурамина;
кристаллизацию фармацевтически приемлемой соли фенфлурамина из фенфлураминовой композиции; где фармацевтически приемлемая соль фенфлурамина имеет следующий профиль чистоты:
по меньшей мере 90% или более фармацевтически приемлемой соли фенфлурамина;
менее чем 1 масс.% 2-фенфлурамина;
менее чем 5 масс.% 4-фенфлурамина; и
менее чем 5 масс.% спиртового побочного продукта восстановления фенфлурамина.
17. Способ по п. 1, дополнительно включающий очистку свободного основания фенфлурамина из фенфлураминовой композиции.
18. Способ по п. 1, дополнительно включающий выполнение хирального разделения рацемической фенфлураминовой композиции, чтобы получить нерацемическую фенфлураминовую композицию, содержащую доминирующий стереоизомер фенфлурамина.
19. Фенфлураминовый активный фармацевтический ингредиент, содержащий фармацевтически приемлемую соль фенфлурамина и имеющий менее чем 0,2 масс.% суммарно трифторметильных региоизомеров.
20. Фенфлураминовый активный фармацевтический ингредиент по п. 19, имеющий следующий профиль:
по меньшей мере 90% или по массе фармацевтически приемлемой соли фенфлурамина;
менее чем 0,2 масс.% 2-фенфлурамина;
менее чем 0,2 масс.% 4-фенфлурамина; и
менее чем 1 масс.% фенфлураминового спирта.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562271172P | 2015-12-22 | 2015-12-22 | |
| US62/271,172 | 2015-12-22 | ||
| PCT/US2016/067856 WO2017112702A1 (en) | 2015-12-22 | 2016-12-20 | Fenfluramine compositions and methods of preparing the same |
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| RU2020128323A Division RU2020128323A (ru) | 2015-12-22 | 2016-12-20 | Фенфлураминовые композиции и способы их получения |
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| RU2018121633A true RU2018121633A (ru) | 2020-01-23 |
| RU2018121633A3 RU2018121633A3 (ru) | 2020-03-20 |
| RU2731179C2 RU2731179C2 (ru) | 2020-08-31 |
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| RU2018121633A RU2731179C2 (ru) | 2015-12-22 | 2016-12-20 | Фенфлураминовые композиции и способы их получения |
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| US (4) | US10351509B2 (ru) |
| EP (3) | EP3393655B1 (ru) |
| JP (3) | JP6893213B2 (ru) |
| KR (1) | KR102688278B1 (ru) |
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| AU (3) | AU2016379346B2 (ru) |
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| SG (2) | SG11201804811WA (ru) |
| SI (3) | SI4293009T1 (ru) |
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Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9549909B2 (en) | 2013-05-03 | 2017-01-24 | The Katholieke Universiteit Leuven | Method for the treatment of dravet syndrome |
| PT3393655T (pt) * | 2015-12-22 | 2021-02-23 | Zogenix International Ltd | Composições de fenfluramina e métodos de preparação das mesmas |
| WO2017112701A1 (en) | 2015-12-22 | 2017-06-29 | Zogenix International Limited | Metabolism resistant fenfluramine analogs and methods of using the same |
| ES3029536T3 (en) | 2016-08-24 | 2025-06-24 | Zogenix International Ltd | Formulation comprising fenfluramine and cannabidiol and its use in the treatment of seizures |
| US10682317B2 (en) | 2017-09-26 | 2020-06-16 | Zogenix International Limited | Ketogenic diet compatible fenfluramine formulation |
| WO2019067413A1 (en) | 2017-09-26 | 2019-04-04 | Zogenix International Limited | USE OF A FENFLURAMINE FORMULATION TO REDUCE THE NUMBER AND FREQUENCIES OF CONVULSIVE CRISES IN PATIENT POPULATIONS |
| WO2019216919A1 (en) | 2018-05-11 | 2019-11-14 | Zogenix International Limited | Compositions and methods for treating seizure-induced sudden death |
| US10517841B1 (en) | 2018-06-14 | 2019-12-31 | Zogenix International Limited | Compositions and methods for treating respiratory depression with fenfluramine |
| WO2020105005A1 (en) | 2018-11-19 | 2020-05-28 | Zogenix International Limited | Methods of treating rett syndrome using fenfluramine |
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| CN112312929A (zh) | 2018-04-18 | 2021-02-02 | 纽约市哥伦比亚大学理事会 | 用于包括线粒体dna耗竭综合征在内的由不平衡的核苷酸库引起的疾病的基因疗法 |
| WO2019216919A1 (en) | 2018-05-11 | 2019-11-14 | Zogenix International Limited | Compositions and methods for treating seizure-induced sudden death |
| US10517841B1 (en) | 2018-06-14 | 2019-12-31 | Zogenix International Limited | Compositions and methods for treating respiratory depression with fenfluramine |
| EP3820459A1 (en) | 2018-07-10 | 2021-05-19 | Zogenix International Limited | Fenfluramine for use for treating epilepsy or epileptic encephalopathy in patients without pulmonary hypertension |
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| WO2020105005A1 (en) | 2018-11-19 | 2020-05-28 | Zogenix International Limited | Methods of treating rett syndrome using fenfluramine |
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| JP2022521446A (ja) | 2019-02-25 | 2022-04-07 | ゾゲニクス インターナショナル リミテッド | 発作制御を改善するための製剤 |
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| US20220096514A1 (en) | 2020-09-29 | 2022-03-31 | Zogenix International Limited | Methods of treating thymidine kinase 2 deficiency by administering deoxycytidine and deoxythymidine |
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