RU2018121633A - Фенфлураминовые композиции и способы их получения - Google Patents
Фенфлураминовые композиции и способы их получения Download PDFInfo
- Publication number
- 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
- Authority
- RU
- Russia
- Prior art keywords
- fenfluramine
- composition
- trifluoromethyl
- phenyl
- less
- Prior art date
Links
- 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
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- 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
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Child & Adolescent Psychology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2020128323A Division RU2020128323A (ru) | 2015-12-22 | 2016-12-20 | Фенфлураминовые композиции и способы их получения |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2018121633A true RU2018121633A (ru) | 2020-01-23 |
| RU2018121633A3 RU2018121633A3 (ru) | 2020-03-20 |
| RU2731179C2 RU2731179C2 (ru) | 2020-08-31 |
Family
ID=59065032
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2018121633A RU2731179C2 (ru) | 2015-12-22 | 2016-12-20 | Фенфлураминовые композиции и способы их получения |
| RU2020128323A RU2020128323A (ru) | 2015-12-22 | 2016-12-20 | Фенфлураминовые композиции и способы их получения |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2020128323A RU2020128323A (ru) | 2015-12-22 | 2016-12-20 | Фенфлураминовые композиции и способы их получения |
Country Status (25)
| Country | Link |
|---|---|
| US (4) | US10351509B2 (ru) |
| EP (3) | EP3393655B1 (ru) |
| JP (3) | JP6893213B2 (ru) |
| KR (1) | KR102688278B1 (ru) |
| CN (2) | CN113499330B (ru) |
| AU (3) | AU2016379346B2 (ru) |
| BR (1) | BR112018011777A2 (ru) |
| CA (1) | CA3007286A1 (ru) |
| DK (3) | DK4293009T3 (ru) |
| ES (3) | ES3024232T3 (ru) |
| FI (2) | FI4293009T3 (ru) |
| HR (3) | HRP20210267T1 (ru) |
| HU (2) | HUE053114T2 (ru) |
| IL (3) | IL286391B (ru) |
| LT (3) | LT4293009T (ru) |
| MX (2) | MX391077B (ru) |
| PL (3) | PL3393655T3 (ru) |
| PT (3) | PT3393655T (ru) |
| RS (1) | RS61506B1 (ru) |
| RU (2) | RU2731179C2 (ru) |
| SA (1) | SA518391868B1 (ru) |
| SG (2) | SG11201804811WA (ru) |
| SI (3) | SI3393655T1 (ru) |
| WO (1) | WO2017112702A1 (ru) |
| ZA (1) | ZA201803583B (ru) |
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 |
| CA3007673A1 (en) | 2015-12-22 | 2017-06-29 | Zogenix International Limited | Metabolism resistant fenfluramine analogs and methods of using the same |
| EP3393655B1 (en) | 2015-12-22 | 2020-12-09 | Zogenix International Limited | Fenfluramine compositions and methods of preparing the same |
| EP4201427A1 (en) | 2016-08-24 | 2023-06-28 | Zogenix International Limited | Formulation for inhibiting formation of 5-ht 2b agonists and methods of using same |
| 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 |
| US10682317B2 (en) * | 2017-09-26 | 2020-06-16 | Zogenix International Limited | Ketogenic diet compatible fenfluramine formulation |
| JP2021526507A (ja) | 2018-05-11 | 2021-10-07 | ゾゲニクス インターナショナル リミテッド | 発作により誘発される突然死を処置するための組成物および方法 |
| WO2019241005A1 (en) | 2018-06-14 | 2019-12-19 | Zogenix International Limited | Compositions and methods for treating respiratory depression with fenfluramine |
| EP3883555A1 (en) | 2018-11-19 | 2021-09-29 | Zogenix International Limited | Methods of treating rett syndrome using fenfluramine |
| WO2020112460A1 (en) * | 2018-11-30 | 2020-06-04 | Zogenix International Limited | A method of treating refractory epilepsy syndromes using fenfluramine enantiomers |
| EP4031114A1 (en) | 2019-09-17 | 2022-07-27 | Zogenix International Limited | Methods of treating epileptic patients with fenfluramine |
| WO2021117057A1 (en) * | 2019-12-10 | 2021-06-17 | Maithri Drugs Pvt Ltd | Polymorph of n-ethyl-1-(3-(trifluoromethyl)phenyl)propan-2-amine hydrochloride and process for preparation thereof |
| US11612574B2 (en) | 2020-07-17 | 2023-03-28 | Zogenix International Limited | Method of treating patients infected with severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) |
| US20240343675A1 (en) * | 2021-08-19 | 2024-10-17 | Biophore India Pharmaceuticals Pvt. Ltd. | An improved process for the preparation of n-ethyl- a -methyl-3-(trifluoromethyl) phenethylamine hydrochloride |
Family Cites Families (149)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR104F (ru) | 1960-11-05 | |||
| US3117160A (en) | 1961-07-27 | 1964-01-07 | Pfizer & Co C | Aralkylamines |
| US3198834A (en) | 1964-07-27 | 1965-08-03 | Snc Science Union Et Compagnie | Optical isomers of trifluoromethylated phenethylamines |
| GB1254332A (en) | 1969-02-27 | 1971-11-17 | Science Union & Cie | Amino acids and their derivatives and processes for preparing them |
| DE2143204C3 (de) | 1971-08-28 | 1979-09-27 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | N-Fluoralkyl-phenylisopropylamin-Derivate und deren Salze, Verfahren zu deren Herstellung und Arzneimittel auf deren Basis |
| DE2150399A1 (de) | 1971-10-09 | 1973-04-12 | Hoechst Ag | Neue oxime |
| GB1413078A (en) | 1973-07-27 | 1975-11-05 | Beecham Group Ltd | Process for the production of plus-norfenfluramine and plus-fenfluramine and salts thereof |
| GB1413070A (en) | 1973-07-27 | 1975-11-05 | Beecham Group Ltd | Process for the production of - norfenfluramine and - fenfluramine and salts thereof |
| JPS54144347A (en) * | 1978-05-02 | 1979-11-10 | Nikken Kagaku Kk | 3-(2-fluoro-4-biphenylyl)-2-butanone |
| US4452815A (en) | 1980-06-16 | 1984-06-05 | Massachusetts Institute Of Technology | Method of utilizing d,l-fenfluramine for modifying feeding behavior |
| US4309445A (en) | 1980-06-16 | 1982-01-05 | Massachusetts Institute Of Technology | d-Fenfluramine for modifying feeding behavior |
| KR870001541B1 (ko) * | 1985-06-14 | 1987-09-02 | 미쯔이도야쯔 가가꾸 가부시기 가이샤 | 에폭시수지 경화용 아미노벤질아민 조성물 |
| US4721823A (en) * | 1986-09-19 | 1988-01-26 | Pennzoil Products Company | Lubricants comprising novel cyclopentanes, cyclopentadienes, cyclopentenes, and mixtures thereof and methods of manufacture |
| DE3717434C1 (de) | 1987-05-23 | 1988-09-15 | Degussa | Verfahren zur Herstellung von m-Trifluormethylphenylacetonitril |
| KR890003368A (ko) * | 1987-08-06 | 1989-04-14 | 원본미기재 | 특정의 치환된 페닐알킬아미노(및 아미노산) 유도체 및 기타 세로토닌농도 저하제로 오심 및 구토를 치료하는 방법 |
| US4857533A (en) | 1988-12-15 | 1989-08-15 | Baker Cummins Pharmaceuticals, Inc. | Method of treatment for autoimmune diseases |
| HU204497B (en) | 1989-10-09 | 1992-01-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing phenfluramine |
| IT1238686B (it) * | 1990-02-09 | 1993-09-01 | Lab Mag Spa | Procedimento per la preparazione di levo e destro fenfluramina |
| FR2684552B1 (fr) | 1991-12-06 | 1995-04-28 | Adir | Utilisation de la d-fenfluramine et de derives de la fenfluramine dans le traitement de l'hypertension chez des sujets insulino-resistants. |
| US5985880A (en) | 1996-06-05 | 1999-11-16 | Delta Pharmaceuticals | Compositions and methods for reducing respiratory depression and attendant side effects of mu opioid compounds |
| DE69422044T2 (de) | 1993-08-06 | 2000-05-31 | Pharmacia & Upjohn Co., Kalamazoo | 2-aminoindane als selektive dopamin-d3-liganden |
| US5834477A (en) | 1993-12-08 | 1998-11-10 | The United States Of America As Represented By The Secretary Of The Army | Opiate analgesic formulation with improved safety |
| US5412102A (en) | 1994-05-27 | 1995-05-02 | Syntex (U.S.A.) Inc. | Processes for preparing 1-butyl-2-[2'-(2H-tetrazol-5-yl) biphenyl-4-ylmethyl]-1H-indole-3-carboxylic acid |
| ATE199829T1 (de) * | 1994-06-03 | 2001-04-15 | Thejmde Trust | Meta substituierte arylalkylamine und therapeutische und diagnostische verwendung davon |
| IT1298349B1 (it) * | 1996-05-29 | 2000-01-05 | Alfa Chem Ital | Processo per la produzione di 1 - (3-trifluorometil) fenil-propan- 2-one intermedio nella sintesi della fenfluramina |
| IT1292885B1 (it) * | 1997-04-28 | 1999-02-11 | Alfa Chem Ital | Processo per la produzione degli isomeri (r) ed (s)- alfa -metil-3- (trifluorometil)benzene-etanamina. |
| EP0920864A1 (en) | 1997-12-03 | 1999-06-09 | Pfizer Products Inc. | Combination therapy including a specific beta-3 agonist and an anorectic agent |
| US20020098175A1 (en) | 1998-06-16 | 2002-07-25 | Zohoungbogbo Mathias C. | Dietetic food composition and dietetic method using such composition |
| US6045501A (en) | 1998-08-28 | 2000-04-04 | Celgene Corporation | Methods for delivering a drug to a patient while preventing the exposure of a foetus or other contraindicated individual to the drug |
| ES2193777T3 (es) | 1998-12-23 | 2003-11-01 | Orphan Medical Inc | Disoluciones estables e inalterables microbiologicamente de sal de gamma-hidroxibutirato para el tratamiento de la narcolepsia. |
| US20080103179A1 (en) | 2006-10-27 | 2008-05-01 | Tam Peter Y | Combination Therapy |
| US7124031B1 (en) | 2000-05-11 | 2006-10-17 | Medco Health Solutions, Inc. | System for monitoring regulation of pharmaceuticals from data structure of medical and labortory records |
| AU2001275095A1 (en) | 2000-07-17 | 2002-01-30 | Opt-E-Scrip, Inc. | Single-patient drug trials used with accumulated database |
| US6315720B1 (en) | 2000-10-23 | 2001-11-13 | Celgene Corporation | Methods for delivering a drug to a patient while avoiding the occurrence of an adverse side effect known or suspected of being caused by the drug |
| US7585493B2 (en) * | 2001-05-24 | 2009-09-08 | Alexza Pharmaceuticals, Inc. | Thin-film drug delivery article and method of use |
| CA2446904A1 (en) * | 2001-05-24 | 2003-04-03 | Alexza Molecular Delivery Corporation | Delivery of drug esters through an inhalation route |
| DE60235234D1 (de) | 2001-06-22 | 2010-03-18 | Univ Catholique Louvain | Hydrogelkugeln oder kapseln als künstliches medium zur eiablage von insekten und zucht von endoparasitoiden |
| MXPA04001026A (es) | 2001-07-31 | 2005-06-20 | Wyeth Corp | Formulacion de sucralosa para disimular sabores desagradables. |
| AUPR732601A0 (en) * | 2001-08-28 | 2001-09-20 | Polychip Pharmaceuticals Pty Ltd | Methods for the synthesis of amines such as ephedrine and inter mediates |
| RU2317104C2 (ru) * | 2001-09-24 | 2008-02-20 | Импиэриэл Инноувейшнс Лимитид | Способ модификации пищевого поведения и применение pyy или его агониста в качестве средства для модификации пищевого поведения |
| AU2002332054B2 (en) | 2001-09-24 | 2007-11-08 | Imperial Innovations Limited | Modification of feeding behavior |
| US6599901B1 (en) | 2001-11-19 | 2003-07-29 | Hoffman-La Roche Inc. | Pyridone substituted benzothiazole derivatives |
| US7101572B2 (en) | 2001-12-07 | 2006-09-05 | Unilab Pharmatech, Ltd. | Taste masked aqueous liquid pharmaceutical composition |
| WO2003077847A2 (en) | 2002-03-12 | 2003-09-25 | Merck & Co., Inc. | Substituted amides |
| WO2003082191A2 (en) | 2002-03-28 | 2003-10-09 | Merck & Co., Inc. | Substituted 2,3-diphenyl pyridines |
| EP1537076A1 (en) * | 2002-09-05 | 2005-06-08 | Novo Nordisk A/S | Novel vinyl carboxylic acid derivatives and their therapeutical use |
| US7668730B2 (en) | 2002-12-17 | 2010-02-23 | JPI Commercial, LLC. | Sensitive drug distribution system and method |
| WO2005004865A1 (en) | 2003-07-08 | 2005-01-20 | Georg-August-Universität Göttingen | Use of 5-ht4(a)-serotonin receptor agonists |
| GB0410266D0 (en) | 2004-05-07 | 2004-06-09 | Ketocytonyx Inc | Treatment of apoptosis |
| US20050260610A1 (en) | 2004-05-20 | 2005-11-24 | Kurtz Richard E | Method for diagnosing and prescribing a regimen of therapy for human health risk |
| RU2007106863A (ru) * | 2004-08-26 | 2008-08-27 | Пфайзер Инк. (US) | Энантиоселективное биопреобразование для получения промежуточных соединений ингибитора белка тирозинкиназы |
| US9820658B2 (en) | 2006-06-30 | 2017-11-21 | Bao Q. Tran | Systems and methods for providing interoperability among healthcare devices |
| CN100567252C (zh) * | 2004-10-11 | 2009-12-09 | 俞锋 | 盐酸芬氟拉明原料药和片剂及其制备方法 |
| CN101193588A (zh) | 2005-03-21 | 2008-06-04 | 海尔思-斯玛特有限公司 | 连续血压监测的系统 |
| MX2007014713A (es) | 2005-05-25 | 2008-02-14 | Janssen Pharmaceutica Nv | Formulacion pediatrica de topiramato. |
| EP1904630A4 (en) | 2005-06-16 | 2009-10-21 | Bionomics Ltd | METHODS OF TREATING AND DIAGNOSING EPILEPSY BY DETECTING MUTATIONS OF THE SCN1A GENE |
| GB0515090D0 (en) | 2005-07-22 | 2005-08-31 | Birmingham Res & Dev Ltd | Novel epilepsy treatment |
| EP1937255A4 (en) | 2005-09-14 | 2013-06-26 | Univ Witwatersrand Jhb | PHARMACEUTICAL COMPOSITION |
| WO2007034476A2 (en) | 2005-09-19 | 2007-03-29 | Biolert Ltd | A device and method for detecting an epileptic event |
| CA2911569C (en) | 2005-11-29 | 2019-11-26 | Children's Hospital Medical Center | Optimization and individualization of medication selection and dosing |
| US7592461B2 (en) | 2005-12-21 | 2009-09-22 | Bristol-Myers Squibb Company | Indane modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
| EP1971394A4 (en) | 2005-12-28 | 2009-04-01 | Neurovista Corp | METHOD AND SYSTEMS FOR PROPOSING A TREATMENT FOR A PATIENT TO CHECK EPILEPSIA AND OTHER NEUROLOGICAL DISEASES |
| RU2008135692A (ru) | 2006-02-06 | 2010-03-20 | Новартис АГ (CH) | Комбинация органический х-соединений |
| AR061311A1 (es) * | 2006-06-08 | 2008-08-20 | Medichem Sa | Procesos para preparar clorhidrato de cinacalcet y formas polimorficas del mismo |
| DE102006030113B4 (de) | 2006-06-28 | 2009-02-12 | Chemische Fabrik Budenheim Kg | Graphitfreier Hochtemperatur-Schmierstoff |
| EP2061471A4 (en) | 2006-08-31 | 2012-02-01 | Univ Alberta | PROCESS FOR INHIBITING RESTRICTED DEPRESSION WITH POSITIVE ALLOSTER AMPA RECEPTOR MODULATORS |
| US20080183498A1 (en) | 2007-01-31 | 2008-07-31 | Quintiles Transnational Corp., Inc. | Methods and systems for site startup |
| US20100130607A1 (en) | 2007-02-08 | 2010-05-27 | Ralf Gold | Neuroprotection in demyelinating diseases |
| JP2010520162A (ja) * | 2007-02-28 | 2010-06-10 | スミスクライン ビーチャム コーポレーション | ステアロイル−ＣｏＡデサチュラーゼ阻害剤であるチアジアゾール誘導体 |
| GB2456183A (en) | 2008-01-04 | 2009-07-08 | Gw Pharma Ltd | Anti-psychotic composition comprising cannabinoids and anti-psychotic medicament |
| CA2749273C (en) | 2008-01-09 | 2018-09-04 | Charleston Laboratories, Inc. | Pharmaceutical oral dosage form comprising a triptan and an antiemetic |
| MX2011001384A (es) | 2008-08-06 | 2011-09-27 | Gosforth Ct Holdings Pty Ltd | Composiciones y metodos para tratar trastornos psiquiatricos. |
| WO2010020585A1 (en) | 2008-08-18 | 2010-02-25 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Serotonin reuptake inhibitors for the treatment of rett syndrome |
| LT2735338T (lt) | 2008-09-05 | 2019-04-10 | Grünenthal GmbH | 3-(3-dimetilamino-1-etil-2-metil-propil)-fenolio ir pregabalino arba gabapentino farmacinis derinys |
| US8664442B2 (en) * | 2008-09-09 | 2014-03-04 | Chemtura Corporation | Anti-oxidants |
| US8386274B1 (en) | 2008-09-17 | 2013-02-26 | Mckesson Financial Holdings Limited | Systems and methods for a prescription safety network utilizing eligibility verification transactions |
| UA103906C2 (ru) | 2008-10-09 | 2013-12-10 | Ацьєнде Кіміке Ріуніте Анджеліні Франческо А.Чі.Р.А.Ф. С.П.А. | Жидкая фармацевтическая композиция, которая содержит парацетамол |
| EP2355818A4 (en) | 2008-10-10 | 2012-04-11 | Us Of America As Represented By The Secretary Of The Army On Behalf Of Walter Reed Army Inst Of Res | METHOD AND COMPOSITIONS FOR TREATING THE STATUS EPILEPTICUS AND STATUS EPILEPTICUS CAUSING ATTACHMENTS |
| TWI424832B (zh) | 2008-12-15 | 2014-02-01 | Proteus Digital Health Inc | 與身體有關的接收器及其方法 |
| US20120065999A1 (en) | 2009-03-09 | 2012-03-15 | Celgene Corporation | Device for Delivering a Drug to a Patient While Restricting Access to the Drug by Patients for Whom the Drug May Be Contraindicated and Methods for Use Thereof |
| WO2010121022A1 (en) | 2009-04-15 | 2010-10-21 | Research Triangle Institute | Monoamine reuptake inhibitors |
| US20100324936A1 (en) | 2009-04-22 | 2010-12-23 | Suresh-Kumar Venkata Vishnubhatla | Pharmacy management and administration with bedside real-time medical event data collection |
| US9453027B2 (en) | 2009-07-27 | 2016-09-27 | Daljit Singh Dhanoa | Deuterium-enriched pyridinonecarboxamides and derivatives |
| WO2011085181A1 (en) | 2010-01-08 | 2011-07-14 | Eurand, Inc. | Taste masked topiramate composition and an orally disintegrating tablet comprising the same |
| DK2545522T3 (en) | 2010-03-09 | 2017-10-16 | Perceptimed Inc | Drug verification and dispensing |
| WO2011119227A2 (en) | 2010-03-25 | 2011-09-29 | Columbia Northwest Pharmaceuticals, Llc | Compositions for the treatment of central nervous system disorders including depression employing novel drug combination therapy to reduce suicidality in patients |
| JP2011221623A (ja) | 2010-04-06 | 2011-11-04 | Kakimori Suri | 在宅診療支援システム及び方法 |
| AU2011255276B2 (en) | 2010-05-21 | 2016-09-22 | Research Triangle Institute | Phenylmorpholines and analogues thereof |
| EP2399513B1 (en) | 2010-06-23 | 2017-01-04 | Qatar University Qstp-B | System for non-invasive automated monitoring, detection, analysis, characterisation, prediction or prevention of seizures and movement disorder symptoms |
| US20140162942A1 (en) | 2010-07-30 | 2014-06-12 | Anima Ghosal | Inhibition of cyp3a drug metabolism |
| CN103189053A (zh) | 2010-09-01 | 2013-07-03 | 艾尼纳制药公司 | 用于体重控制的5-ht2c激动剂的调节释放剂型 |
| US20120270848A1 (en) | 2010-10-22 | 2012-10-25 | Galleon Pharmaceuticals, Inc. | Novel Compositions and Therapeutic Methods Using Same |
| KR20130097211A (ko) | 2010-10-26 | 2013-09-02 | 알파마 파머슈티컬스 엘엘씨 | 오피오이드 과다투여에 의해 유도된 호흡 저하를 약화시키기 위한 제제 및 방법 |
| RU103209U1 (ru) | 2010-10-29 | 2011-03-27 | Общество С Ограниченной Ответственностью "Правовое Сопровождение Бизнеса" | Клиническая информационная система |
| GB2487712B (en) | 2011-01-04 | 2015-10-28 | Otsuka Pharma Co Ltd | Use of the phytocannabinoid cannabidiol (CBD) in combination with a standard anti-epileptic drug (SAED) in the treatment of epilepsy |
| US8748418B2 (en) * | 2011-03-18 | 2014-06-10 | Hoffmann-La Roche Inc. | 1,4-oxazepines as BACE1 and/or BACE2 inhibitors |
| JP5693325B2 (ja) | 2011-03-29 | 2015-04-01 | 小林クリエイト株式会社 | 健診結果出力システム及び健診結果出力プログラム |
| TWI542596B (zh) * | 2011-05-09 | 2016-07-21 | 健生藥品公司 | （２ｓ,３ｒ,４ｒ,５ｓ,６ｒ）－２－（３－（（５－（４－氟苯基）噻吩－２－基）甲基）－４－甲基苯基）－６－（羥甲基）四氫－２ｈ－哌喃－３,４,５－三醇之ｌ－脯胺酸及檸檬酸共晶體 |
| GB201111712D0 (en) | 2011-07-08 | 2011-08-24 | Gosforth Ct Holdings Pty Ltd | Pharmaceutical compositions |
| US20140348966A1 (en) | 2011-12-22 | 2014-11-27 | Onesmo B. Balemba | Garcinia buchananii baker compounds, compositions and related methods |
| WO2013122897A1 (en) | 2012-02-13 | 2013-08-22 | Amgen Inc. | Dihydrobenzoxazine and tetrahydroquinoxaline sodium channel inhibitors |
| US20130218586A1 (en) | 2012-02-21 | 2013-08-22 | Frederic J. Huser | Methods and elements for identifying the appropriate patient populations who can safely use prescription chronic care drugs that are switched to an over-the-counter regulatory status |
| JP6075973B2 (ja) | 2012-06-04 | 2017-02-08 | 富士通株式会社 | 健康状態判定装置およびその作動方法 |
| CA2891342A1 (en) | 2012-11-15 | 2014-05-22 | Galleon Pharmaceuticals, Inc. | Novel orally bioavailable breathing control modulating compounds, and methods of using same |
| WO2014106825A2 (en) | 2013-01-06 | 2014-07-10 | Jonathan Rabinowitz | Methods and devices for identifying improper medical reporting |
| US9549909B2 (en) | 2013-05-03 | 2017-01-24 | The Katholieke Universiteit Leuven | Method for the treatment of dravet syndrome |
| CN103342648A (zh) * | 2013-07-22 | 2013-10-09 | 北京科莱博医药开发有限责任公司 | 瑞替加滨中间体的制备方法和瑞替加滨的制备方法 |
| RS61038B1 (sr) | 2013-08-19 | 2020-12-31 | Univ California | Jedinjenja i metodi za lečenje epileptičnog poremećaja |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| WO2015077057A1 (en) | 2013-11-20 | 2015-05-28 | Texas Southern University | Methionine aminopeptidase inhibitors for treating infectious diseases |
| CN103886415A (zh) | 2014-03-25 | 2014-06-25 | 北京蝶禾谊安信息技术有限公司 | 药品管理方法和装置 |
| WO2015187988A1 (en) * | 2014-06-04 | 2015-12-10 | Intellimedix | Composition and methods of treating epilepsy and/or epilepsy-related disorders |
| GB2530001B (en) | 2014-06-17 | 2019-01-16 | Gw Pharma Ltd | Use of cannabidiol in the reduction of convulsive seizure frequency in treatment-resistant epilepsy |
| RU2704749C2 (ru) | 2014-09-29 | 2019-10-30 | Зодженикс Интернэшнл Лимитед | Система управления для управления распределением лекарственных продуктов |
| EP4059522A1 (en) | 2015-02-06 | 2022-09-21 | Marinus Pharmaceuticals, Inc. | Intravenous ganaxolone formulations and their use in treating status epilepticus and other seizure disorders |
| AU2016222804C1 (en) | 2015-02-25 | 2021-10-14 | The Regents Of The University Of California | 5HT agonists for treating disorders |
| US10292996B2 (en) | 2015-03-26 | 2019-05-21 | The Trustees Of Columbia University In The City Of New York | Deoxyribonucleoside monophospate bypass therapy for mitochondrial DNA depletion syndrome |
| JP6668045B2 (ja) | 2015-05-15 | 2020-03-18 | ゾゲニクス インターナショナル リミテッド | ドラベ症候群を処置するための選択的５−ｈｔ受容体アゴニストおよびアンタゴニスト |
| KR20250048602A (ko) | 2015-06-17 | 2025-04-09 | 더 트러스티스 오브 컬럼비아 유니버시티 인 더 시티 오브 뉴욕 | 미토콘드리아 dna 고갈 증후군을 포함하는 불균형 뉴클레오타이드 풀에 의해 야기된 질환에 대한 데옥시뉴클레오타이드 요법 |
| US10294228B2 (en) | 2015-06-30 | 2019-05-21 | Neurad Ltd. | Breathing control modulating compounds, and methods of making and using same |
| EP3324975B1 (en) | 2015-07-22 | 2022-05-18 | John Hsu | Composition comprising a therapeutic agent and a respiratory stimulant and methods for the use thereof |
| BR112018002046A2 (pt) | 2015-08-24 | 2018-09-18 | Zogenix International Ltd | métodos de tratamento da síndrome de lennox-gastaut usando fenfluramina |
| US20220193082A1 (en) | 2015-09-14 | 2022-06-23 | Zogenix International Limited | Combination treatment of specific forms of epilepsy |
| US20170071949A1 (en) | 2015-09-14 | 2017-03-16 | Zogenix International Limited | Combination treatment of specific forms of epilepsy |
| EP3170807B1 (en) | 2015-11-23 | 2019-12-11 | Frau Pharma S.r.l. | New method for synthesis of fenfluramine |
| EP3393655B1 (en) | 2015-12-22 | 2020-12-09 | Zogenix International Limited | Fenfluramine compositions and methods of preparing the same |
| CA3007673A1 (en) | 2015-12-22 | 2017-06-29 | Zogenix International Limited | Metabolism resistant fenfluramine analogs and methods of using the same |
| JP6753418B2 (ja) | 2016-01-14 | 2020-09-09 | Ａｇｃ株式会社 | フッ素樹脂含有溶液、フッ素樹脂含有溶液の製造方法、塗料組成物および塗装物品 |
| EP4201427A1 (en) | 2016-08-24 | 2023-06-28 | Zogenix International Limited | Formulation for inhibiting formation of 5-ht 2b agonists and methods of using same |
| US20190083425A1 (en) | 2016-08-24 | 2019-03-21 | Zogenix International Limited | Formulation for inhibiting formation of 5-ht2b agonists and methods of using same |
| US20180092864A1 (en) | 2016-09-30 | 2018-04-05 | Zogenix International Limited | Compositions and methods for treating seizure disorders |
| AU2018265353A1 (en) | 2017-05-09 | 2019-11-21 | Zogenix International Limited | Methods of treating Doose syndrome using fenfluramine |
| US20190247333A1 (en) | 2017-09-26 | 2019-08-15 | Zogenix International Limited | Method of reduction in convulsive seizure frequency |
| US20190091179A1 (en) | 2017-09-26 | 2019-03-28 | Zogenix International Limited | Congnitive function with fenfluramine |
| 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 |
| US20190125697A1 (en) | 2017-09-26 | 2019-05-02 | Zogenix International Limited | Method of reduction in convulsive seizure frequency |
| US11352882B2 (en) | 2018-03-12 | 2022-06-07 | Cameron International Corporation | Plug assembly for a mineral extraction system |
| JP7769355B2 (ja) | 2018-04-18 | 2025-11-13 | ザ・トラスティーズ・オブ・コロンビア・ユニバーシティ・イン・ザ・シティ・オブ・ニューヨーク | ミトコンドリアｄｎａ枯渇症候群を含む不均衡ヌクレオチドプールに起因する疾患の遺伝子治療 |
| JP2021526507A (ja) | 2018-05-11 | 2021-10-07 | ゾゲニクス インターナショナル リミテッド | 発作により誘発される突然死を処置するための組成物および方法 |
| WO2019241005A1 (en) | 2018-06-14 | 2019-12-19 | Zogenix International Limited | Compositions and methods for treating respiratory depression with fenfluramine |
| US20210113495A1 (en) | 2018-07-10 | 2021-04-22 | Zogenix International Limited | Method of treating epilepsy or epileptic encephalopathy with fenfluramine in patients without pulmonary hypertension |
| AU2019310600A1 (en) | 2018-07-27 | 2021-02-11 | Xenon Pharmaceuticals Inc. | Method for treating epilepsy |
| EP3883555A1 (en) | 2018-11-19 | 2021-09-29 | Zogenix International Limited | Methods of treating rett syndrome using fenfluramine |
| WO2020112460A1 (en) | 2018-11-30 | 2020-06-04 | Zogenix International Limited | A method of treating refractory epilepsy syndromes using fenfluramine enantiomers |
| 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 |
| US20210299064A1 (en) | 2020-02-05 | 2021-09-30 | Zogenix International Limited | Method of treating patients with lennox-gastaut syndrome |
| US11612574B2 (en) | 2020-07-17 | 2023-03-28 | Zogenix International Limited | Method of treating patients infected with severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) |
| US20220096514A1 (en) | 2020-09-29 | 2022-03-31 | Zogenix International Limited | Methods of treating thymidine kinase 2 deficiency by administering deoxycytidine and deoxythymidine |
-
2016
- 2016-12-20 EP EP16879990.6A patent/EP3393655B1/en active Active
- 2016-12-20 ES ES20210227T patent/ES3024232T3/es active Active
- 2016-12-20 LT LTEP23207021.9T patent/LT4293009T/lt unknown
- 2016-12-20 DK DK23207021.9T patent/DK4293009T3/da active
- 2016-12-20 ES ES23207021T patent/ES3040587T3/es active Active
- 2016-12-20 PT PT168799906T patent/PT3393655T/pt unknown
- 2016-12-20 SI SI201631057T patent/SI3393655T1/sl unknown
- 2016-12-20 WO PCT/US2016/067856 patent/WO2017112702A1/en not_active Ceased
- 2016-12-20 DK DK20210227.3T patent/DK3800177T3/da active
- 2016-12-20 LT LTEP20210227.3T patent/LT3800177T/lt unknown
- 2016-12-20 SI SI201631916T patent/SI4293009T1/sl unknown
- 2016-12-20 EP EP23207021.9A patent/EP4293009B8/en active Active
- 2016-12-20 US US15/385,525 patent/US10351509B2/en active Active
- 2016-12-20 EP EP20210227.3A patent/EP3800177B1/en active Active
- 2016-12-20 FI FIEP23207021.9T patent/FI4293009T3/fi active
- 2016-12-20 RS RS20210237A patent/RS61506B1/sr unknown
- 2016-12-20 LT LTEP16879990.6T patent/LT3393655T/lt unknown
- 2016-12-20 PL PL16879990T patent/PL3393655T3/pl unknown
- 2016-12-20 HR HRP20210267TT patent/HRP20210267T1/hr unknown
- 2016-12-20 SI SI201631896T patent/SI3800177T1/sl unknown
- 2016-12-20 DK DK16879990.6T patent/DK3393655T3/da active
- 2016-12-20 PT PT232070219T patent/PT4293009T/pt unknown
- 2016-12-20 PL PL20210227.3T patent/PL3800177T3/pl unknown
- 2016-12-20 MX MX2021000482A patent/MX391077B/es unknown
- 2016-12-20 HR HRP20250898TT patent/HRP20250898T1/hr unknown
- 2016-12-20 HR HRP20250432TT patent/HRP20250432T1/hr unknown
- 2016-12-20 CN CN202110608226.XA patent/CN113499330B/zh active Active
- 2016-12-20 AU AU2016379346A patent/AU2016379346B2/en active Active
- 2016-12-20 HU HUE16879990A patent/HUE053114T2/hu unknown
- 2016-12-20 KR KR1020187020707A patent/KR102688278B1/ko active Active
- 2016-12-20 SG SG11201804811WA patent/SG11201804811WA/en unknown
- 2016-12-20 CA CA3007286A patent/CA3007286A1/en active Pending
- 2016-12-20 MX MX2018007088A patent/MX381004B/es unknown
- 2016-12-20 RU RU2018121633A patent/RU2731179C2/ru active
- 2016-12-20 PT PT202102273T patent/PT3800177T/pt unknown
- 2016-12-20 ES ES16879990T patent/ES2861774T3/es active Active
- 2016-12-20 BR BR112018011777A patent/BR112018011777A2/pt not_active Application Discontinuation
- 2016-12-20 FI FIEP20210227.3T patent/FI3800177T3/fi active
- 2016-12-20 JP JP2018532740A patent/JP6893213B2/ja active Active
- 2016-12-20 HU HUE20210227A patent/HUE071191T2/hu unknown
- 2016-12-20 CN CN201680075127.7A patent/CN108883399B/zh active Active
- 2016-12-20 SG SG10202005916QA patent/SG10202005916QA/en unknown
- 2016-12-20 PL PL23207021.9T patent/PL4293009T3/pl unknown
- 2016-12-20 IL IL286391A patent/IL286391B/en unknown
- 2016-12-20 RU RU2020128323A patent/RU2020128323A/ru not_active Application Discontinuation
-
2018
- 2018-01-31 US US15/884,742 patent/US10351510B2/en active Active
- 2018-05-30 ZA ZA2018/03583A patent/ZA201803583B/en unknown
- 2018-05-30 IL IL259703A patent/IL259703B/en active IP Right Grant
- 2018-06-23 SA SA518391868A patent/SA518391868B1/ar unknown
-
2019
- 2019-06-04 US US16/431,391 patent/US10947183B2/en active Active
-
2020
- 2020-12-02 JP JP2020199969A patent/JP7412320B2/ja active Active
-
2021
- 2021-01-27 US US17/159,367 patent/US11634377B2/en active Active
- 2021-03-02 AU AU2021201339A patent/AU2021201339B2/en active Active
- 2021-03-09 IL IL281368A patent/IL281368B/en unknown
- 2021-04-27 AU AU2021202576A patent/AU2021202576B2/en active Active
-
2022
- 2022-06-07 JP JP2022091999A patent/JP7394919B2/ja active Active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2018121633A (ru) | Фенфлураминовые композиции и способы их получения | |
| DE602007013242D1 (de) | Herstellung von essigsäure | |
| KR102236806B1 (ko) | 거울상 이성질체 농후화된 3-아미노피페리딘의 제조 방법 | |
| KR20110137336A (ko) | 시나칼세트 및 그의 염의 제조방법, 및 상기 제조방법에 사용되는 중간체 | |
| AR078179A1 (es) | Procedimiento de sintesis de la ivabradina y de sus sales de adicion a un acido farmaceuticamente aceptable | |
| US10370329B2 (en) | Process for the enantiomeric resolution of apremilast intermediates | |
| JP2009531353A5 (ru) | ||
| JP5999600B2 (ja) | 光学活性テトラヒドロフラン−２−カルボン酸の製造方法 | |
| US9932321B2 (en) | Process for the preparation of piperidine compounds | |
| WO2014118606A2 (en) | A novel process for the preparation of silodosin | |
| KR20120084306A (ko) | 2-(1-페닐에틸)아이소인돌린-1-온 화합물의 제조 방법 | |
| JP2014520796A5 (ru) | ||
| WO2011161255A4 (en) | Processes for the resolution of nitrogen substituted (s) - 5 -alkoxy- 2 -aminotetralin derivatives | |
| KR102587339B1 (ko) | N-[4-(1-아미노-에틸)-2,6-다이플루오로-페닐]-메테인설폰아마이드의 거울상 이성질체들의 라세미화 방법 | |
| CN101613292B (zh) | (s)-3-(1-二甲氨基乙基)苯酚的制备方法 | |
| KR101842425B1 (ko) | 시탈로프람 및 에스시탈로프람의 신규 제조방법 | |
| MA35806B1 (fr) | Nouveau procede de synthese du 3-(2-bromo-4,5-dimethoxyphenil) propanenitrile, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable | |
| US10125074B2 (en) | 5-substituted-5-hydroxy-5-aryl-3-oxo-pentanoate derivatives and their enantiopure forms | |
| JPWO2010013510A1 (ja) | 光学活性化合物の製造方法 | |
| US20100312010A1 (en) | Process for the Preparation of (S)-Pregabalin | |
| KR20160061542A (ko) | 새로운 루리코나졸 이성체 분리 방법 | |
| WO2013001511A1 (en) | Novel salt intermediates for the synthesis of bazedoxifene acetate and process thereof | |
| KR102134179B1 (ko) | 카보네이트를 이용한 시탈로프람 및 에스시탈로프람의 새로운 제조 방법 | |
| CN114436965A (zh) | 一种盐酸右美托咪定降解杂质的制备方法 | |
| AR089325A1 (es) | Procedimiento de sintesis de la ivabradina y de sus sales de adicion a un acido farmaceuticamente aceptable |