ME02509B - Proces za proizvodnju metansulfonatnih soli ralfinamida ili njihovih r-enantiomera - Google Patents
Proces za proizvodnju metansulfonatnih soli ralfinamida ili njihovih r-enantiomeraInfo
- Publication number
- ME02509B ME02509B MEP-2016-169A MEP16916A ME02509B ME 02509 B ME02509 B ME 02509B ME P16916 A MEP16916 A ME P16916A ME 02509 B ME02509 B ME 02509B
- Authority
- ME
- Montenegro
- Prior art keywords
- salt
- water
- mixture
- ralfinamide
- crystalline
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 27
- BHJIBOFHEFDSAU-LBPRGKRZSA-N ralfinamide Chemical compound C1=CC(CN[C@@H](C)C(N)=O)=CC=C1OCC1=CC=CC=C1F BHJIBOFHEFDSAU-LBPRGKRZSA-N 0.000 claims abstract 28
- 150000003839 salts Chemical class 0.000 claims abstract 28
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract 27
- 239000002904 solvent Substances 0.000 claims abstract 21
- 150000001875 compounds Chemical class 0.000 claims abstract 13
- 230000001738 genotoxic effect Effects 0.000 claims abstract 13
- 239000012535 impurity Substances 0.000 claims abstract 13
- 239000002243 precursor Substances 0.000 claims abstract 13
- 238000000746 purification Methods 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 36
- 239000000203 mixture Substances 0.000 claims 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 30
- 238000002425 crystallisation Methods 0.000 claims 18
- 230000008025 crystallization Effects 0.000 claims 18
- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 claims 14
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 14
- 125000004432 carbon atom Chemical group C* 0.000 claims 13
- 231100000024 genotoxic Toxicity 0.000 claims 12
- 238000010438 heat treatment Methods 0.000 claims 12
- 239000007787 solid Substances 0.000 claims 11
- 229940098779 methanesulfonic acid Drugs 0.000 claims 8
- 239000000243 solution Substances 0.000 claims 8
- 239000013078 crystal Substances 0.000 claims 7
- 239000012458 free base Substances 0.000 claims 7
- 239000013557 residual solvent Substances 0.000 claims 7
- 238000002441 X-ray diffraction Methods 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 238000010899 nucleation Methods 0.000 claims 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 238000001816 cooling Methods 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- -1 compound (S)-2-[4-(2-fluorobenzyloxy)benzylamino]propanamide salt Chemical class 0.000 claims 2
- 230000007812 deficiency Effects 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 claims 1
- 238000003109 Karl Fischer titration Methods 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000000295 complement effect Effects 0.000 claims 1
- 238000005384 cross polarization magic-angle spinning Methods 0.000 claims 1
- 238000012926 crystallographic analysis Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- SWWHCQCMVCPLEQ-UHFFFAOYSA-N propan-2-yl methanesulfonate Chemical compound CC(C)OS(C)(=O)=O SWWHCQCMVCPLEQ-UHFFFAOYSA-N 0.000 claims 1
- 238000001757 thermogravimetry curve Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 abstract 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/04—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Psychology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10161207 | 2010-04-27 | ||
| EP11714958.3A EP2563355B1 (en) | 2010-04-27 | 2011-04-06 | Process for the production of ralfinamide methanesulfonate salts or their R-enantiomers |
| PCT/EP2011/055309 WO2011134763A1 (en) | 2010-04-27 | 2011-04-06 | Process for the production of ralfinamide methanesulfonate salts or their r-enantiomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ME02509B true ME02509B (me) | 2017-02-20 |
Family
ID=42634917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2016-169A ME02509B (me) | 2010-04-27 | 2011-04-06 | Proces za proizvodnju metansulfonatnih soli ralfinamida ili njihovih r-enantiomera |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US9505708B2 (enExample) |
| EP (1) | EP2563355B1 (enExample) |
| JP (3) | JP5808392B2 (enExample) |
| KR (1) | KR101851118B1 (enExample) |
| CN (2) | CN105037188B (enExample) |
| AR (1) | AR085171A1 (enExample) |
| AU (1) | AU2011246707B2 (enExample) |
| BR (1) | BR112012027623B1 (enExample) |
| CA (1) | CA2794389C (enExample) |
| CY (1) | CY1117879T1 (enExample) |
| DK (1) | DK2563355T3 (enExample) |
| EA (1) | EA021389B1 (enExample) |
| ES (1) | ES2590128T3 (enExample) |
| HR (1) | HRP20161077T1 (enExample) |
| HU (1) | HUE030504T2 (enExample) |
| IL (1) | IL222532A (enExample) |
| LT (1) | LT2563355T (enExample) |
| ME (1) | ME02509B (enExample) |
| MX (1) | MX342697B (enExample) |
| NZ (2) | NZ602648A (enExample) |
| PL (1) | PL2563355T3 (enExample) |
| PT (1) | PT2563355T (enExample) |
| RS (1) | RS55084B1 (enExample) |
| SI (1) | SI2563355T1 (enExample) |
| SM (1) | SMT201600266B (enExample) |
| TW (1) | TWI492919B (enExample) |
| WO (1) | WO2011134763A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2563355T3 (pl) * | 2010-04-27 | 2016-12-30 | Sposób wytwarzania soli stanowiących metanosulfoniany ralfinamidu lub jego enancjomerów R | |
| CN103804341B (zh) * | 2012-11-13 | 2018-04-10 | 中国人民解放军军事医学科学院毒物药物研究所 | 酰胺衍生物及其医药用途 |
| CN104761531B (zh) * | 2014-01-03 | 2017-12-01 | 中国人民解放军军事医学科学院毒物药物研究所 | 镇痛活性化合物及其医药用途 |
| CN104292128A (zh) * | 2014-07-01 | 2015-01-21 | 南京正科制药有限公司 | 一种沙芬酰胺晶型a |
| CN115368310B (zh) * | 2021-05-18 | 2025-06-27 | 奥库菲尔医药公司 | 合成甲磺酸酚妥拉明的方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL94466A (en) | 1989-05-25 | 1995-01-24 | Erba Carlo Spa | Pharmaceutical preparations containing the history of A-amino carboxamide N-phenylalkyl are converted into such new compounds and their preparation |
| GB9515412D0 (en) * | 1995-07-27 | 1995-09-27 | Pharmacia Spa | 2-(4-substituted)-benzylamino-2-methyl-propanamide derivatives |
| GB9727523D0 (en) | 1997-12-31 | 1998-02-25 | Pharmacia & Upjohn Spa | Alpha-aminoamide derivatives useful as analgesic agents |
| DE60209152T2 (de) | 2001-09-03 | 2006-08-03 | Newron Pharmaceuticals S.P.A. | Pharmazeutische zusammensetzung, umfassend gabapentin oder ein analogon davon und ein alpha-aminoamid |
| EP1438956A1 (en) | 2003-01-16 | 2004-07-21 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful as antimigraine agents |
| JP2006515326A (ja) * | 2003-01-30 | 2006-05-25 | ダイノジェン ファーマシューティカルズ， インコーポレイテッド | 胃腸管障害を処置するためのナトリウムチャネルモジュレーターの使用 |
| AR044007A1 (es) | 2003-04-11 | 2005-08-24 | Newron Pharmaceuticals Inc | Metodos para el tratamiento de la enfermedad de parkinson |
| WO2005018627A1 (en) | 2003-08-25 | 2005-03-03 | Newron Pharmaceuticals, Spa | Alpha-aminoamide derivatives useful as anti-inflammatory agents |
| EP1557166A1 (en) | 2004-01-21 | 2005-07-27 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful in the treatment of lower urinary tract disorders |
| EP1588704A1 (en) | 2004-04-22 | 2005-10-26 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful in the treatment of restless legs syndrome and addictive disorders |
| RU2391973C2 (ru) * | 2004-09-10 | 2010-06-20 | Ньюрон Фармасьютикалс С.П.А. | Применение (галобензилокси)бензиламино-пропанамидов для производства лекарственных средств, действующих как селективные модуляторы натриевых и/или кальциевых каналов |
| EP1870097A1 (en) | 2006-06-15 | 2007-12-26 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful in the treatment of cognitive disorders |
| RS55464B1 (sr) * | 2006-06-19 | 2017-04-28 | Newron Pharm Spa | 2-[4-(3- i 2 fluorbenziloksi) benzilamino] propanamidi visokog stepena čistoće za upotrebu kao lekovi i farmaceutski preparati koji ih sadrže |
| JP5315674B2 (ja) * | 2007-11-19 | 2013-10-16 | セントラル硝子株式会社 | 非水電池用電解液及びこれを用いた非水電池 |
| JP5460613B2 (ja) * | 2007-12-11 | 2014-04-02 | ニユーロン・フアーマシユーテイカルズ・エツセ・ピー・アー | 高純度を有する２−［４−（３−または２−フルオロベンジルオキシ）ベンジルアミノ］プロパンアミドの製造方法 |
| KR101500962B1 (ko) | 2007-12-19 | 2015-03-10 | 뉴론 파마슈티칼즈 에스. 피. 에이. | 정신 장애의 치료에 유용한 알파아미노아미드 유도체 |
| WO2009109334A1 (en) | 2008-03-07 | 2009-09-11 | Newron Pharmaceuticals S.P.A. | (s)-(+)-2-[4-fluorbenzyloxy)benzylamino]propanamide for use in the treatment of mixed or combined pain |
| PL2563355T3 (pl) * | 2010-04-27 | 2016-12-30 | Sposób wytwarzania soli stanowiących metanosulfoniany ralfinamidu lub jego enancjomerów R |
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2011
- 2011-04-06 PL PL11714958.3T patent/PL2563355T3/pl unknown
- 2011-04-06 NZ NZ602648A patent/NZ602648A/en unknown
- 2011-04-06 BR BR112012027623-9A patent/BR112012027623B1/pt active IP Right Grant
- 2011-04-06 EP EP11714958.3A patent/EP2563355B1/en active Active
- 2011-04-06 RS RS20160665A patent/RS55084B1/sr unknown
- 2011-04-06 MX MX2012012093A patent/MX342697B/es active IP Right Grant
- 2011-04-06 PT PT117149583T patent/PT2563355T/pt unknown
- 2011-04-06 SI SI201130927A patent/SI2563355T1/sl unknown
- 2011-04-06 ME MEP-2016-169A patent/ME02509B/me unknown
- 2011-04-06 JP JP2013506566A patent/JP5808392B2/ja active Active
- 2011-04-06 CN CN201510387405.XA patent/CN105037188B/zh active Active
- 2011-04-06 LT LTEP11714958.3T patent/LT2563355T/lt unknown
- 2011-04-06 NZ NZ700221A patent/NZ700221A/en unknown
- 2011-04-06 HU HUE11714958A patent/HUE030504T2/en unknown
- 2011-04-06 US US13/643,716 patent/US9505708B2/en active Active
- 2011-04-06 CA CA2794389A patent/CA2794389C/en active Active
- 2011-04-06 KR KR1020127030931A patent/KR101851118B1/ko active Active
- 2011-04-06 WO PCT/EP2011/055309 patent/WO2011134763A1/en not_active Ceased
- 2011-04-06 EA EA201291116A patent/EA021389B1/ru unknown
- 2011-04-06 CN CN201180020748.2A patent/CN102858330B/zh active Active
- 2011-04-06 AU AU2011246707A patent/AU2011246707B2/en active Active
- 2011-04-06 HR HRP20161077TT patent/HRP20161077T1/hr unknown
- 2011-04-06 DK DK11714958.3T patent/DK2563355T3/en active
- 2011-04-06 ES ES11714958.3T patent/ES2590128T3/es active Active
- 2011-04-18 TW TW100113339A patent/TWI492919B/zh active
- 2011-04-25 AR ARP110101401A patent/AR085171A1/es not_active Application Discontinuation
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2012
- 2012-10-18 IL IL222532A patent/IL222532A/en active IP Right Grant
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2015
- 2015-05-22 JP JP2015104930A patent/JP6345154B2/ja active Active
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2016
- 2016-08-05 SM SM201600266T patent/SMT201600266B/it unknown
- 2016-08-10 CY CY20161100786T patent/CY1117879T1/el unknown
- 2016-10-12 US US15/291,202 patent/US9856207B2/en active Active
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