AU2009305255B2 - Process for the preparation of rufinamide - Google Patents
Process for the preparation of rufinamide Download PDFInfo
- Publication number
- AU2009305255B2 AU2009305255B2 AU2009305255A AU2009305255A AU2009305255B2 AU 2009305255 B2 AU2009305255 B2 AU 2009305255B2 AU 2009305255 A AU2009305255 A AU 2009305255A AU 2009305255 A AU2009305255 A AU 2009305255A AU 2009305255 B2 AU2009305255 B2 AU 2009305255B2
- Authority
- AU
- Australia
- Prior art keywords
- formula
- azide
- rufinamide
- methyl
- process according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 55
- POGQSBRIGCQNEG-UHFFFAOYSA-N rufinamide Chemical compound N1=NC(C(=O)N)=CN1CC1=C(F)C=CC=C1F POGQSBRIGCQNEG-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 229960003014 rufinamide Drugs 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 37
- JSZUBPHMRHROHZ-UHFFFAOYSA-N 2-(azidomethyl)-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1CN=[N+]=[N-] JSZUBPHMRHROHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001540 azides Chemical class 0.000 claims abstract description 13
- IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 12
- 150000001805 chlorine compounds Chemical group 0.000 claims abstract description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical group [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 16
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 238000002955 isolation Methods 0.000 claims description 10
- XVEURJOWGBWEPY-UHFFFAOYSA-N methyl 1-[(2,6-difluorophenyl)methyl]triazole-4-carboxylate Chemical compound N1=NC(C(=O)OC)=CN1CC1=C(F)C=CC=C1F XVEURJOWGBWEPY-UHFFFAOYSA-N 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- -1 alkali metal azide Chemical class 0.000 claims description 6
- 238000005580 one pot reaction Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001649 bromium compounds Chemical group 0.000 claims description 2
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 claims description 2
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical group C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 claims description 2
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical group C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims 1
- BSKYMXVRPQKKNE-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-5-methyltriazole-4-carboxylic acid Chemical compound CC1=C(C(O)=O)N=NN1CC1=C(F)C=CC=C1F BSKYMXVRPQKKNE-UHFFFAOYSA-N 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 description 20
- 235000011114 ammonium hydroxide Nutrition 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 206010015037 epilepsy Diseases 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 125000005103 alkyl silyl group Chemical group 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- LSXJPJGBWSZHTM-UHFFFAOYSA-N 2-(bromomethyl)-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1CBr LSXJPJGBWSZHTM-UHFFFAOYSA-N 0.000 description 2
- MJXRENZUAQXZGJ-UHFFFAOYSA-N 2-(chloromethyl)-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1CCl MJXRENZUAQXZGJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- CPGRMGOILBSUQC-UHFFFAOYSA-N phosphoryl azide Chemical compound [N-]=[N+]=NP(=O)(N=[N+]=[N-])N=[N+]=[N-] CPGRMGOILBSUQC-UHFFFAOYSA-N 0.000 description 2
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- GTODOEDLCNTSLG-UHFFFAOYSA-N 2h-triazole-4-carboxylic acid Chemical compound OC(=O)C1=CNN=N1 GTODOEDLCNTSLG-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 229910007991 Si-N Inorganic materials 0.000 description 1
- 229910006294 Si—N Inorganic materials 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4192—1,2,3-Triazoles
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2190/MUM/2008 | 2008-10-13 | ||
| IN2190MU2008 | 2008-10-13 | ||
| PCT/GB2009/002419 WO2010043849A1 (en) | 2008-10-13 | 2009-10-09 | Process for the preparation of rufinamide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU2009305255A1 AU2009305255A1 (en) | 2010-04-22 |
| AU2009305255A8 AU2009305255A8 (en) | 2011-08-25 |
| AU2009305255B2 true AU2009305255B2 (en) | 2014-02-06 |
Family
ID=41786401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009305255A Ceased AU2009305255B2 (en) | 2008-10-13 | 2009-10-09 | Process for the preparation of rufinamide |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8183269B2 (enExample) |
| EP (1) | EP2334653A1 (enExample) |
| JP (2) | JP2012505191A (enExample) |
| KR (1) | KR20110067022A (enExample) |
| AU (1) | AU2009305255B2 (enExample) |
| CA (1) | CA2736703A1 (enExample) |
| NZ (1) | NZ591725A (enExample) |
| WO (1) | WO2010043849A1 (enExample) |
| ZA (1) | ZA201101836B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ591725A (en) | 2008-10-13 | 2012-09-28 | Cipla Ltd | PROCESS FOR THE PREPARATION OF RUFINAMIDE which is also known as 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide |
| WO2011135105A1 (en) | 2010-04-30 | 2011-11-03 | Laboratorios Lesvi, S.L. | Improved process for preparing rufinamide intermediate |
| JP6108112B2 (ja) * | 2010-08-25 | 2017-04-05 | ラオ ダヴルリ，ラマモハン | 改良されたルフィナミド調製プロセス |
| WO2012032540A1 (en) | 2010-09-06 | 2012-03-15 | Indoco Remedies Limited | Process for preparation of fluorinated triazole compound |
| CN102219752B (zh) * | 2011-04-21 | 2013-04-10 | 华润赛科药业有限责任公司 | 一种1-(2,6-二氟苄基)-1h-1,2,3-三唑-4-甲酰胺的晶型d |
| US20140357871A1 (en) | 2012-01-10 | 2014-12-04 | Lupin Limited | Process for preparation of rufinamide |
| CN103539750A (zh) * | 2012-07-09 | 2014-01-29 | 旭和（天津）医药科技有限公司 | 一种合成卢非酰胺的工艺 |
| WO2014072992A1 (en) | 2012-11-12 | 2014-05-15 | Aarti Industries Limited | A process for preparing triazole compounds |
| WO2014120994A1 (en) * | 2013-01-31 | 2014-08-07 | The Johns Hopkins University | Rufinamide and derivatives and their use in modulating the gating process of human voltage-gated sodium channels |
| WO2014121383A1 (en) * | 2013-02-11 | 2014-08-14 | Apotex Technologies Inc. | A process for the preparation of rufinamide and intermediates thereof |
| KR20190081386A (ko) | 2017-12-29 | 2019-07-09 | 강원대학교산학협력단 | 루핀아마이드를 유효성분으로 함유하는 허혈성 뇌혈관 질환 예방용 조성물 |
| CN109438374B (zh) * | 2018-10-10 | 2020-10-30 | 凯莱英医药集团（天津）股份有限公司 | 卢非酰胺的连续化合成方法 |
| US20230026724A1 (en) * | 2019-10-11 | 2023-01-26 | Chengdu Mfs Pharma. Co., Ltd. | Substituted nitrogen heterocyclic compound and anesthetic effect thereof |
| CN114106211A (zh) * | 2021-08-31 | 2022-03-01 | 海南医学院 | 一种云南鸡油菌多糖及其分离纯化方法 |
| CN116854644B (zh) * | 2023-07-06 | 2025-10-21 | 浙江大学 | 5-氨基-1-烷基-1h-1,2,3-三氮唑-4-甲酰胺类化合物及其制备和应用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4789680A (en) * | 1982-12-23 | 1988-12-06 | Ciba-Geigy Corporation | Aralkyltriazole compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK283990B6 (sk) | 1996-07-11 | 2004-07-07 | Novartis Ag | Spôsob prípravy 1-substituovaných 4-kyano-1,2,3-triazolov, 4-kyano-1-(2,6-difluórbenzyl)-1H-1,2,3-triazol |
| TW403740B (en) * | 1997-06-10 | 2000-09-01 | Novartis Ag | Novel crystal modifications of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide |
| NZ591725A (en) | 2008-10-13 | 2012-09-28 | Cipla Ltd | PROCESS FOR THE PREPARATION OF RUFINAMIDE which is also known as 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide |
-
2009
- 2009-10-09 NZ NZ591725A patent/NZ591725A/xx not_active IP Right Cessation
- 2009-10-09 JP JP2011530559A patent/JP2012505191A/ja active Pending
- 2009-10-09 US US13/063,440 patent/US8183269B2/en not_active Expired - Fee Related
- 2009-10-09 AU AU2009305255A patent/AU2009305255B2/en not_active Ceased
- 2009-10-09 WO PCT/GB2009/002419 patent/WO2010043849A1/en not_active Ceased
- 2009-10-09 CA CA2736703A patent/CA2736703A1/en not_active Abandoned
- 2009-10-13 KR KR1020117006738A patent/KR20110067022A/ko not_active Ceased
- 2009-10-13 EP EP09744712A patent/EP2334653A1/en not_active Withdrawn
-
2011
- 2011-03-10 ZA ZA2011/01836A patent/ZA201101836B/en unknown
-
2014
- 2014-11-28 JP JP2014240724A patent/JP2015096515A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4789680A (en) * | 1982-12-23 | 1988-12-06 | Ciba-Geigy Corporation | Aralkyltriazole compounds |
Non-Patent Citations (2)
| Title |
|---|
| SULTAN T. ABU-ORABI ET AL.: "Effect of solvant and reaction time on the products of the 1,3-dipolar cycloaddition of substituted benzyl azides with di-tert-butyl acetylenedicarboxylate" GAZZETTA CHIMICA ITALIANA, vol. 122, 1992, pages 29-32 * |
| WANG J ET AL "Synthesis and anticonvulsant activity of 1-substituted benzyl-N-substituted-1,2,3-triazole-4-formamides", Progress in Natural Science, vol. 16, No. 9, September 2006, pages 925-929 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US8183269B2 (en) | 2012-05-22 |
| ZA201101836B (en) | 2011-10-26 |
| JP2012505191A (ja) | 2012-03-01 |
| JP2015096515A (ja) | 2015-05-21 |
| AU2009305255A8 (en) | 2011-08-25 |
| KR20110067022A (ko) | 2011-06-20 |
| AU2009305255A1 (en) | 2010-04-22 |
| CA2736703A1 (en) | 2010-04-22 |
| NZ591725A (en) | 2012-09-28 |
| WO2010043849A8 (en) | 2011-06-30 |
| US20110207938A1 (en) | 2011-08-25 |
| EP2334653A1 (en) | 2011-06-22 |
| WO2010043849A1 (en) | 2010-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TH | Corrigenda |
Free format text: IN VOL 25, NO 13, PAGE(S) 1557 UNDER THE HEADING PCT APPLICATIONS THAT HAVE ENTERED THE NATIONAL PHASE - NAME INDEX UNDER THE NAME CIPLA LIMITED, APPLICATION NO. 2009305255, UNDER INID (22) CORRECT THE DATE TO READ 09 OCTOBER 2009 |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |