JP2014522413A5 - - Google Patents
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- JP2014522413A5 JP2014522413A5 JP2014514905A JP2014514905A JP2014522413A5 JP 2014522413 A5 JP2014522413 A5 JP 2014522413A5 JP 2014514905 A JP2014514905 A JP 2014514905A JP 2014514905 A JP2014514905 A JP 2014514905A JP 2014522413 A5 JP2014522413 A5 JP 2014522413A5
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- level
- less
- ppm
- item
- 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.)
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- 238000000034 method Methods 0.000 claims description 32
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 claims description 21
- 229960004419 dimethyl fumarate Drugs 0.000 claims description 21
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 7
- 239000001530 fumaric acid Substances 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- RAQPZQAQMHUKTB-TYYBGVCCSA-N (e)-but-2-enedioic acid;methanol Chemical compound OC.OC(=O)\C=C\C(O)=O RAQPZQAQMHUKTB-TYYBGVCCSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161494775P | 2011-06-08 | 2011-06-08 | |
| US61/494,775 | 2011-06-08 | ||
| PCT/US2012/041715 WO2012170923A1 (en) | 2011-06-08 | 2012-06-08 | Process for preparing high purity and crystalline dimethyl fumarate |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016111809A Division JP2016155868A (ja) | 2011-06-08 | 2016-06-03 | 高純度結晶性ジメチルフマラートの調製方法 |
| JP2018107557A Division JP2018162266A (ja) | 2011-06-08 | 2018-06-05 | 高純度結晶性ジメチルフマラートの調製方法 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2014522413A JP2014522413A (ja) | 2014-09-04 |
| JP2014522413A5 true JP2014522413A5 (enExample) | 2015-07-23 |
| JP6385273B2 JP6385273B2 (ja) | 2018-09-05 |
| JP6385273B6 JP6385273B6 (ja) | 2023-12-15 |
Family
ID=47296498
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014514905A Expired - Fee Related JP6385273B6 (ja) | 2011-06-08 | 2012-06-08 | 高純度結晶性ジメチルフマラートの調製方法 |
| JP2016111809A Pending JP2016155868A (ja) | 2011-06-08 | 2016-06-03 | 高純度結晶性ジメチルフマラートの調製方法 |
| JP2018107557A Pending JP2018162266A (ja) | 2011-06-08 | 2018-06-05 | 高純度結晶性ジメチルフマラートの調製方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016111809A Pending JP2016155868A (ja) | 2011-06-08 | 2016-06-03 | 高純度結晶性ジメチルフマラートの調製方法 |
| JP2018107557A Pending JP2018162266A (ja) | 2011-06-08 | 2018-06-05 | 高純度結晶性ジメチルフマラートの調製方法 |
Country Status (32)
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005023241A1 (en) | 2003-09-09 | 2005-03-17 | Fumapharm Ag | The use of fumaric acid derivatives for treating cardiac insufficiency, and asthma |
| DK1799196T3 (en) | 2004-10-08 | 2016-08-15 | Forward Pharma As | Controlled release pharmaceutical compositions comprising a fumaric acid ester |
| EP2334378B1 (en) | 2008-08-19 | 2014-04-09 | XenoPort, Inc. | Prodrugs of methyl hydrogen fumarate, pharmaceutical compositions thereof, and methods of use |
| US9422226B2 (en) | 2011-06-08 | 2016-08-23 | Biogen Ma Inc. | Process for preparing high purity and crystalline dimethyl fumarate |
| JP2015527372A (ja) | 2012-08-22 | 2015-09-17 | ゼノポート，インコーポレイティド | 副作用を低減させるモノメチルフマレートおよびそのプロドラッグの投与方法 |
| AU2013305684B2 (en) | 2012-08-22 | 2016-11-24 | Xenoport, Inc. | Oral dosage forms of methyl hydrogen fumarate and prodrugs thereof |
| AR094277A1 (es) | 2012-12-21 | 2015-07-22 | Biogen Idec Inc | Derivados de fumarato sustituidos con deuterio |
| US8669281B1 (en) | 2013-03-14 | 2014-03-11 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| PT2970101T (pt) | 2013-03-14 | 2018-10-04 | Alkermes Pharma Ireland Ltd | Pró-fármacos de fumaratos e seu uso no tratamento de várias doenças |
| WO2014160633A1 (en) | 2013-03-24 | 2014-10-02 | Xenoport, Inc. | Pharmaceutical compositions of dimethyl fumarate |
| CN104098471A (zh) * | 2013-04-03 | 2014-10-15 | 南京卡文迪许生物工程技术有限公司 | 富马酸二甲酯多晶型物及其制备方法和药物组合物 |
| WO2014197860A1 (en) | 2013-06-07 | 2014-12-11 | Xenoport, Inc. | Method of making monomethyl fumarate |
| US9421182B2 (en) | 2013-06-21 | 2016-08-23 | Xenoport, Inc. | Cocrystals of dimethyl fumarate |
| EP3041467A1 (en) | 2013-09-06 | 2016-07-13 | XenoPort, Inc. | Crystalline forms of (n,n-diethylcarbamoyl)methyl methyl (2e)but-2-ene-1,4-dioate, methods of synthesis and use |
| IN2013MU03070A (enExample) * | 2013-09-25 | 2015-07-17 | Glenmark Pharmaceuticals Ltd | |
| IN2014CH00308A (enExample) * | 2014-01-24 | 2015-07-31 | Shilpa Medicare Ltd | |
| EP3110793B1 (en) | 2014-02-24 | 2019-08-21 | Alkermes Pharma Ireland Limited | Sulfonamide and sulfinamide prodrugs of fumarates and their use in treating various diseases |
| US9326947B1 (en) | 2014-02-28 | 2016-05-03 | Banner Life Sciences Llc | Controlled release fumarate esters |
| US9636318B2 (en) | 2015-08-31 | 2017-05-02 | Banner Life Sciences Llc | Fumarate ester dosage forms |
| US10098863B2 (en) | 2014-02-28 | 2018-10-16 | Banner Life Sciences Llc | Fumarate esters |
| WO2015130998A1 (en) | 2014-02-28 | 2015-09-03 | Banner Life Sciences Llc | Controlled release enteric soft capsules of fumarate esters |
| WO2015140811A2 (en) * | 2014-03-17 | 2015-09-24 | Biophore India Pharmaceuticals Pvt. Ltd. | An improved process for the synthesis of dimethyl fumarate |
| US9999672B2 (en) | 2014-03-24 | 2018-06-19 | Xenoport, Inc. | Pharmaceutical compositions of fumaric acid esters |
| EP3164378A1 (en) * | 2014-07-03 | 2017-05-10 | Synthon B.V. | Process for making microcrystalline dimethyl fumarate |
| CN104151165B (zh) * | 2014-08-11 | 2016-08-24 | 广东东阳光药业有限公司 | 制备富马酸二甲酯的方法 |
| CN104761453A (zh) * | 2015-04-22 | 2015-07-08 | 河南中帅医药科技股份有限公司 | 一种富马酸二甲酯晶型及其制备方法 |
| CA2987895A1 (en) * | 2015-06-01 | 2016-12-08 | Sun Pharmaceutical Industries Ltd. | Pharmaceutical compositions of dimethyl fumarate |
| MX387092B (es) * | 2015-06-17 | 2025-03-19 | Biogen Ma Inc | Particulas de dimetilfumarato y composiciones farmaceuticas de estas. |
| CN106316841A (zh) * | 2015-06-30 | 2017-01-11 | 深圳翰宇药业股份有限公司 | 一种富马酸二甲酯的制备方法 |
| WO2017013672A1 (en) * | 2015-07-23 | 2017-01-26 | Natco Pharma Ltd | Process for the preparation of pharmaceutical grade dimethyl fumarate |
| US10011663B2 (en) | 2016-02-04 | 2018-07-03 | Eastman Chemical Company | Vulcanizing composition containing cyclododecasulfur and improved cyclododecasulfur compound |
| RU2616605C1 (ru) * | 2016-04-07 | 2017-04-18 | Олег Ростиславович Михайлов | Кристаллическая бета - модификация (Е)-диметилбутендиоата, способ её получения и фармацевтическая композиция на её основе |
| CN107285320A (zh) * | 2017-08-02 | 2017-10-24 | 内蒙古新福地科技有限公司 | 一种氟硅酸钠的结晶方法及装置 |
| CN111201235B (zh) * | 2017-10-10 | 2023-02-10 | 辉瑞公司 | 劳拉替尼游离碱水合物的结晶形式 |
| US11903918B2 (en) | 2020-01-10 | 2024-02-20 | Banner Life Sciences Llc | Fumarate ester dosage forms with enhanced gastrointestinal tolerability |
| KR102271575B1 (ko) * | 2020-09-16 | 2021-07-01 | 김갑용 | 염의 이온교환법을 이용한 친환경 고효율 에스터화반응 기반의 에스터화합물 제조방법 및 이의 화합물 |
| JP6865489B1 (ja) * | 2020-10-20 | 2021-04-28 | 株式会社エス・ディー・エス バイオテック | ２，３，５，６−テトラクロロ−１，４−ベンゼンジカルボン酸ジメチルの製造方法 |
| CN117550970A (zh) * | 2023-10-30 | 2024-02-13 | 寿光金远东变性淀粉有限公司 | 一种高纯度衣康酸二甲酯的生产方法 |
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