JP2015500335A5 - - Google Patents
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- JP2015500335A5 JP2015500335A5 JP2014547135A JP2014547135A JP2015500335A5 JP 2015500335 A5 JP2015500335 A5 JP 2015500335A5 JP 2014547135 A JP2014547135 A JP 2014547135A JP 2014547135 A JP2014547135 A JP 2014547135A JP 2015500335 A5 JP2015500335 A5 JP 2015500335A5
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- 150000001875 compounds Chemical class 0.000 claims 23
- 238000000034 method Methods 0.000 claims 22
- 238000006243 chemical reaction Methods 0.000 claims 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 238000010520 demethylation reaction Methods 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 230000017858 demethylation Effects 0.000 claims 2
- 235000019253 formic acid Nutrition 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- BVWTXUYLKBHMOX-UHFFFAOYSA-N methyl vanillate Chemical compound COC(=O)C1=CC=C(O)C(OC)=C1 BVWTXUYLKBHMOX-UHFFFAOYSA-N 0.000 claims 2
- 238000006396 nitration reaction Methods 0.000 claims 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- PPQJCISYYXZCAE-UHFFFAOYSA-N 1,10-phenanthroline;hydrate Chemical compound O.C1=CN=C2C3=NC=CC=C3C=CC2=C1 PPQJCISYYXZCAE-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 229940113088 dimethylacetamide Drugs 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 claims 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161570141P | 2011-12-13 | 2011-12-13 | |
| GBGB1121413.7A GB201121413D0 (en) | 2011-12-13 | 2011-12-13 | Chemical compounds and processes |
| US61/570,141 | 2011-12-13 | ||
| GB1121413.7 | 2011-12-13 | ||
| US201261593625P | 2012-02-01 | 2012-02-01 | |
| GBGB1201758.8A GB201201758D0 (en) | 2012-02-01 | 2012-02-01 | Chemical compounds and processes |
| GB1201758.8 | 2012-02-01 | ||
| US61/593,625 | 2012-02-01 | ||
| US201261718589P | 2012-10-25 | 2012-10-25 | |
| US61/718,589 | 2012-10-25 | ||
| PCT/PT2012/000048 WO2013089573A1 (en) | 2011-12-13 | 2012-12-12 | Chemical compound useful as intermediate for preparing a catechol-o-methyltransferase inhibitor |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017207738A Division JP6721558B2 (ja) | 2011-12-13 | 2017-10-27 | カテコール−ｏ−メチル転移酵素阻害剤を調製するための中間体として有用な化学的化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015500335A JP2015500335A (ja) | 2015-01-05 |
| JP2015500335A5 true JP2015500335A5 (enExample) | 2016-02-12 |
| JP6456143B2 JP6456143B2 (ja) | 2019-01-23 |
Family
ID=48612903
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014547135A Active JP6456143B2 (ja) | 2011-12-13 | 2012-12-12 | カテコール−ｏ−メチル転移酵素阻害剤を調製するための中間体として有用な化学的化合物 |
| JP2017207738A Active JP6721558B2 (ja) | 2011-12-13 | 2017-10-27 | カテコール−ｏ−メチル転移酵素阻害剤を調製するための中間体として有用な化学的化合物 |
| JP2019214566A Withdrawn JP2020059729A (ja) | 2011-12-13 | 2019-11-27 | カテコール−ｏ−メチル転移酵素阻害剤を調製するための中間体として有用な化学的化合物 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017207738A Active JP6721558B2 (ja) | 2011-12-13 | 2017-10-27 | カテコール−ｏ−メチル転移酵素阻害剤を調製するための中間体として有用な化学的化合物 |
| JP2019214566A Withdrawn JP2020059729A (ja) | 2011-12-13 | 2019-11-27 | カテコール−ｏ−メチル転移酵素阻害剤を調製するための中間体として有用な化学的化合物 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US9126988B2 (enExample) |
| EP (2) | EP2791134B1 (enExample) |
| JP (3) | JP6456143B2 (enExample) |
| BR (1) | BR112014014341A2 (enExample) |
| CA (2) | CA2858025C (enExample) |
| CY (1) | CY1122580T1 (enExample) |
| DK (1) | DK2791134T3 (enExample) |
| ES (2) | ES2758659T3 (enExample) |
| HR (1) | HRP20192133T8 (enExample) |
| HU (1) | HUE047856T2 (enExample) |
| PL (1) | PL2791134T3 (enExample) |
| PT (2) | PT2791134T (enExample) |
| RS (1) | RS59666B1 (enExample) |
| SI (1) | SI2791134T1 (enExample) |
| WO (1) | WO2013089573A1 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0613859B8 (pt) | 2005-07-26 | 2021-05-25 | Bial Portela & Ca Sa | inibidores da comt, seus usos, e composição farmacêutica |
| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| SI2481410T1 (sl) | 2007-01-31 | 2017-01-31 | Bial - Portela & Ca., S.A. | Derivati nitrokatehola kot COMT inhibitorji, ki se dajejo s specifičnim dozirnim režimom |
| TW200942531A (en) | 2008-03-17 | 2009-10-16 | Bial Portela & Companhia S A | Crystal forms of a nitrocatechol |
| RU2701731C2 (ru) | 2009-04-01 | 2019-10-01 | Биал-Портела Энд Ка, С.А. | Фармацевтические препараты, содержащие производные нитрокатехина, и способы их получения |
| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| EP2791134B1 (en) * | 2011-12-13 | 2019-09-25 | BIAL - Portela & Cª S.A. | Chemical compound useful as intermediate for preparing a catechol-o-methyltransferase inhibitor |
| JP2018500300A (ja) | 2014-11-28 | 2018-01-11 | ノヴィファーマ，エス．アー． | パーキンソン病を遅延させるための医薬 |
| GB2563858A (en) * | 2017-06-27 | 2019-01-02 | Azad Pharmaceutical Ingredients Ag | New route of synthesis for opicapone |
| WO2019123066A1 (en) * | 2017-12-18 | 2019-06-27 | Unichem Laboratories Ltd | Process for the preparation of opicapone and intermediates thereof |
| US12097193B2 (en) | 2018-10-05 | 2024-09-24 | Bial—Portela & Ca, S.A. | Methods for the administration of COMT inhibitors |
| EP3860602A1 (en) * | 2018-10-05 | 2021-08-11 | Neurocrine Biosciences, Inc. | Methods for the administration of comt inhibitors |
| CN109529881A (zh) * | 2018-11-12 | 2019-03-29 | 刘晓菊 | 一种治疗帕金森药物用中间体5-硝基香草酸的制备方法 |
| BR112022017401A2 (pt) | 2020-03-13 | 2022-10-18 | Bial Portela & Ca Sa | Opicapona micronizada |
| TW202200138A (zh) * | 2020-05-26 | 2022-01-01 | 日商小野藥品工業股份有限公司 | 包含奧匹卡朋（ｏｐｉｃａｐｏｎｅ）之錠劑 |
| GB202011709D0 (en) | 2020-07-28 | 2020-09-09 | Bial Portela & Ca Sa | Solid dispersion of opicapone |
| GB202016425D0 (en) | 2020-10-16 | 2020-12-02 | Bial Portela & Ca Sa | Treatment regimens for parkinson's disease |
| CN112375014A (zh) * | 2020-12-17 | 2021-02-19 | 重庆柳江医药科技有限公司 | 一种奥匹卡朋工艺杂质及制备方法和用途 |
| EP4262798A1 (en) | 2020-12-17 | 2023-10-25 | Bial-Portela & CA, S.A. | Treatment regimens for early idiopathic parkinson's disease |
| US20240300930A1 (en) * | 2021-02-26 | 2024-09-12 | Msn Laboratories Private Limited, R&D Center | Novel process for the preparation of 2,5-dichloro-3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-4,6-dimethylpyridine-1-oxide |
| CN113292489B (zh) * | 2021-06-16 | 2022-08-30 | 泓博智源(开原)药业有限公司 | 二氯代二烷基烟腈的制备方法 |
| GB202204798D0 (en) | 2022-04-01 | 2022-05-18 | Bial Portela & Ca Sa | Prodrugs of opicapone |
| GB202212082D0 (en) | 2022-08-18 | 2022-10-05 | Bial Portela & Ca Sa | Treatment regimens for parkinson's disease |
| GB202219669D0 (en) | 2022-12-23 | 2023-02-08 | Bial Portela & Ca Sa | Processes and intermediates for synthesising opicapone |
| AU2023449890A1 (en) | 2023-05-25 | 2025-11-27 | Bial-Portela & Ca., S.A. | Treatment regimens for early idiopathic parkinson's disease |
| WO2024260874A1 (en) * | 2023-06-19 | 2024-12-26 | Medichem, S.A. | Process for preparing opicapone |
| WO2025012643A1 (en) | 2023-07-11 | 2025-01-16 | Tay Therapeutics Limited | Compounds comprising a naphthyridine or pyridopyrimidine core as ptc read-through agents |
| CN119775271A (zh) * | 2024-12-31 | 2025-04-08 | 南京海纳医药科技股份有限公司 | 一种奥吡卡朋粗品的精制方法 |
| CN120081837A (zh) * | 2025-02-14 | 2025-06-03 | 江苏天士力帝益药业有限公司 | 一种低单杂高纯度的奥匹卡朋中间体05的制备方法 |
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| JP4738419B2 (ja) | 2005-11-30 | 2011-08-03 | 富士フイルムＲｉファーマ株式会社 | アミロイドの凝集及び／又は沈着に起因する疾患の診断薬及び治療薬 |
| GB0606774D0 (en) | 2006-04-03 | 2006-05-10 | Novartis Ag | Organic compounds |
| EP1845097A1 (en) * | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| PE20080906A1 (es) | 2006-08-17 | 2008-07-05 | Kemia Inc | Derivados heteroarilo como inhibidores de citocina |
| US8486979B2 (en) | 2006-12-12 | 2013-07-16 | Abbvie Inc. | 1,2,4 oxadiazole compounds and methods of use thereof |
| US20080167286A1 (en) | 2006-12-12 | 2008-07-10 | Abbott Laboratories | Pharmaceutical compositions and their methods of use |
| SI2481410T1 (sl) | 2007-01-31 | 2017-01-31 | Bial - Portela & Ca., S.A. | Derivati nitrokatehola kot COMT inhibitorji, ki se dajejo s specifičnim dozirnim režimom |
| JP5718053B2 (ja) | 2007-08-27 | 2015-05-13 | ヘリコン・セラピューティクス・インコーポレーテッド | 治療用イソオキサゾール化合物 |
| KR20100126452A (ko) | 2008-02-28 | 2010-12-01 | 바이알 - 포르텔라 앤드 씨에이 에스에이 | 난용성 약물용 약학적 조성물 |
| TW200942531A (en) * | 2008-03-17 | 2009-10-16 | Bial Portela & Companhia S A | Crystal forms of a nitrocatechol |
| AR072846A1 (es) | 2008-07-29 | 2010-09-22 | Bial Portela & Ca Sa | RÉGIMEN DE ADMINISTRACIoN DE NITROCATECOLES PARA LA PREVENCIoN O TRATAMIENTO DE TRASTORNOS ASOCIADOS AL SISTEMA NERVIOSO CENTRAL. |
| RU2701731C2 (ru) | 2009-04-01 | 2019-10-01 | Биал-Портела Энд Ка, С.А. | Фармацевтические препараты, содержащие производные нитрокатехина, и способы их получения |
| US20100256194A1 (en) | 2009-04-01 | 2010-10-07 | Bial - Portela & Ca, S.A. | Pharmaceutical formulations comprising nitrocatechol derivatives and methods of making the same |
| CN102781424B (zh) | 2010-03-04 | 2016-03-30 | 奥赖恩公司 | 左旋多巴、卡比多巴和恩他卡朋用于治疗帕金森病的应用 |
| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| EP2791134B1 (en) * | 2011-12-13 | 2019-09-25 | BIAL - Portela & Cª S.A. | Chemical compound useful as intermediate for preparing a catechol-o-methyltransferase inhibitor |
-
2012
- 2012-12-12 EP EP12806720.4A patent/EP2791134B1/en active Active
- 2012-12-12 PT PT128067204T patent/PT2791134T/pt unknown
- 2012-12-12 WO PCT/PT2012/000048 patent/WO2013089573A1/en not_active Ceased
- 2012-12-12 RS RS20191562A patent/RS59666B1/sr unknown
- 2012-12-12 HU HUE12806720A patent/HUE047856T2/hu unknown
- 2012-12-12 HR HRP20192133TT patent/HRP20192133T8/hr unknown
- 2012-12-12 US US14/365,265 patent/US9126988B2/en active Active
- 2012-12-12 JP JP2014547135A patent/JP6456143B2/ja active Active
- 2012-12-12 PT PT191947563T patent/PT3604299T/pt unknown
- 2012-12-12 BR BR112014014341A patent/BR112014014341A2/pt not_active Application Discontinuation
- 2012-12-12 PL PL12806720T patent/PL2791134T3/pl unknown
- 2012-12-12 ES ES12806720T patent/ES2758659T3/es active Active
- 2012-12-12 ES ES19194756T patent/ES2960805T3/es active Active
- 2012-12-12 CA CA2858025A patent/CA2858025C/en active Active
- 2012-12-12 SI SI201231703T patent/SI2791134T1/sl unknown
- 2012-12-12 CA CA3088684A patent/CA3088684C/en active Active
- 2012-12-12 EP EP19194756.3A patent/EP3604299B1/en active Active
- 2012-12-12 DK DK12806720T patent/DK2791134T3/da active
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2015
- 2015-07-31 US US14/814,603 patent/US9630955B2/en active Active
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2017
- 2017-10-27 JP JP2017207738A patent/JP6721558B2/ja active Active
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2019
- 2019-11-27 JP JP2019214566A patent/JP2020059729A/ja not_active Withdrawn
- 2019-11-27 CY CY20191101241T patent/CY1122580T1/el unknown
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