RU2550133C2 - Фармацевтические составы, включающие производные нитрокатехола, и способы их получения - Google Patents
Фармацевтические составы, включающие производные нитрокатехола, и способы их получения Download PDFInfo
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- RU2550133C2 RU2550133C2 RU2011143619/15A RU2011143619A RU2550133C2 RU 2550133 C2 RU2550133 C2 RU 2550133C2 RU 2011143619/15 A RU2011143619/15 A RU 2011143619/15A RU 2011143619 A RU2011143619 A RU 2011143619A RU 2550133 C2 RU2550133 C2 RU 2550133C2
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16579409P | 2009-04-01 | 2009-04-01 | |
| US61/165,794 | 2009-04-01 | ||
| PCT/PT2010/000015 WO2010114405A2 (en) | 2009-04-01 | 2010-03-31 | Pharmaceutical formulations comprising nitrocatechol derivatives and methods of making the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2011143619A RU2011143619A (ru) | 2013-05-10 |
| RU2550133C2 true RU2550133C2 (ru) | 2015-05-10 |
Family
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Families Citing this family (23)
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| WO2007013830A1 (en) | 2005-07-26 | 2007-02-01 | Portela & Ca. S.A. | Nitrocatechol derivatives as comt inhibitors |
| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| DK2481410T3 (en) | 2007-01-31 | 2016-10-24 | Bial - Portela & Ca S A | Nitrocatecholderivater as COMT inhibitors administered in a specific dosage regimen |
| BRPI0908731A2 (pt) | 2008-03-17 | 2017-05-16 | Bial - Portela & C A S A | formas cristalinas de 5-[3-(2,5-dicloro-4,6-dimetil-1-óxi-piridina-3-il)[1,2,4]oxadiazol-5-il]-3-nitrobenzeno-1,2-diol |
| CN102448444B (zh) | 2009-04-01 | 2016-05-25 | 巴尔-波特拉及康邦亚股份有限公司 | 包括硝基儿茶酚衍生物的药物制剂及其制备方法 |
| US20140045900A1 (en) * | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| US9126988B2 (en) | 2011-12-13 | 2015-09-08 | Bial—Portela & Ca, S.A. | Intermediate for preparing a catechol-O-methyltransferase inhibitor |
| NO2699580T3 (enExample) | 2014-01-24 | 2018-02-24 | ||
| WO2016083863A1 (en) | 2014-11-28 | 2016-06-02 | Bial - Portela & Ca, S.A. | Medicaments for slowing parkinson's disease |
| EP3728241A4 (en) * | 2017-12-18 | 2021-02-24 | Unichem Laboratories Ltd | PROCESS FOR THE MANUFACTURING OF OPICAPON AND INTERMEDIATE PRODUCTS THEREOF |
| PT3758708T (pt) * | 2018-03-01 | 2025-02-13 | Astrazeneca Ab | Composições farmacêuticas compreendendo (2s)-{(1,s)-1-ciano-2-[4-(3-metil-2-oxo-2,3-di-hidro-1,3-benzoxazol-5-il)fenil]etil}-1,4-oxazepano-2-carboxamida |
| CA3106269A1 (en) | 2018-07-17 | 2020-01-23 | Insmed Incorporated | Certain (2s)-n-[(1s)-1-cyano-2-phenylethyl]-1,4-oxazepane-2-carboxamides for treating lupus nephritis |
| WO2020072884A1 (en) | 2018-10-05 | 2020-04-09 | Neurocrine Biosciences, Inc. | Methods for the administration of comt inhibitors |
| EP3860603A1 (en) | 2018-10-05 | 2021-08-11 | Neurocrine Biosciences, Inc. | Methods for the administration of comt inhibitors |
| JP2023517690A (ja) | 2020-03-13 | 2023-04-26 | ビアル－ポルテラ エ コンパニア，ソシエダッド アノニマ | 微粉化オピカポン |
| 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 |
| WO2022131944A1 (en) | 2020-12-17 | 2022-06-23 | 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 |
| GB202212082D0 (en) | 2022-08-18 | 2022-10-05 | Bial Portela & Ca Sa | Treatment regimens for parkinson's disease |
| JP2026503035A (ja) | 2023-01-06 | 2026-01-27 | インスメッド インコーポレイテッド | 新規な可逆性ｄｐｐ１阻害剤及びその用途 |
| CN121487727A (zh) | 2023-05-25 | 2026-02-06 | 巴尔-波特拉及康邦亚股份有限公司 | 用于早期特发性帕金森病的治疗方案 |
| WO2025162472A1 (en) | 2024-01-31 | 2025-08-07 | Insmed Incorporated | Linear dipeptidyl peptidase 1 inhibitors and uses thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1845097A1 (en) * | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1532178A (en) * | 1921-07-25 | 1925-04-07 | Louis A Godbold | Lubricator |
| IL31990A (en) * | 1968-04-26 | 1974-05-16 | Chinoin Gyogyszer Es Vegyeszet | Pyridyl 1,2,4-oxadiazole derivatives,process for the preparation thereof and pharmaceutical compositions containing same |
| US4085563A (en) * | 1977-01-31 | 1978-04-25 | Campbell Soup Company | Cookie dispensing apparatus |
| US4264573A (en) * | 1979-05-21 | 1981-04-28 | Rowell Laboratories, Inc. | Pharmaceutical formulation for slow release via controlled surface erosion |
| US4368668A (en) * | 1981-05-15 | 1983-01-18 | Veb Kombinat Polygraph "Werner Lamberz" Leipzig | Printing plate mounting arrangement |
| US5236952A (en) * | 1986-03-11 | 1993-08-17 | Hoffmann-La Roche Inc. | Catechol derivatives |
| YU213587A (en) * | 1986-11-28 | 1989-06-30 | Orion Yhtymae Oy | Process for obtaining new pharmacologic active cateholic derivatives |
| US6361794B1 (en) * | 1996-06-12 | 2002-03-26 | Basf Corporation | Method of making ibuprofen and narcotic analgesic composition |
| US6206110B1 (en) * | 1996-09-09 | 2001-03-27 | Smith International, Inc. | Protected lubricant reservoir with pressure control for sealed bearing earth boring drill bit |
| AU762245B2 (en) * | 1998-09-18 | 2003-06-19 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
| GB2344819A (en) * | 1998-12-18 | 2000-06-21 | Portela & Ca Sa | 2-Phenyl-1-(3,4-dihydroxy-5-nitrophenyl)-1-ethanones |
| US6660753B2 (en) * | 1999-08-19 | 2003-12-09 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| WO2002044209A2 (en) * | 2000-11-28 | 2002-06-06 | Zymogenetics, Inc. | Cytonkine receptor zcytor19 |
| US20040097555A1 (en) * | 2000-12-26 | 2004-05-20 | Shinegori Ohkawa | Concomitant drugs |
| DE60234812D1 (de) * | 2001-01-29 | 2010-02-04 | Shionogi & Co | Arzneipräparat, das als wirkstoff 5-methyl-1-phenyl-2-(1h)-pyridon enthält |
| US7041685B2 (en) * | 2001-06-08 | 2006-05-09 | Cytovia, Inc. | Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| JP2006516250A (ja) * | 2002-12-18 | 2006-06-29 | サイトビア インコーポレイティッド | カスパーゼ活性化剤およびアポトーシス誘導物質としての３，５−二置換−［１，２，４］−オキサジアゾールおよびそれらの誘導体ならびにそれらの使用 |
| WO2005006945A2 (en) * | 2003-07-03 | 2005-01-27 | The Salk Institute For Biological Studies | Methods for treating neural disorders and compounds useful therefor |
| ES2933479T3 (es) * | 2003-09-29 | 2023-02-09 | Novo Nordisk Healthcare Ag | Estabilidad mejorada de formulaciones de progestágenos |
| US7300406B2 (en) * | 2003-09-30 | 2007-11-27 | Carter Vandette B | Medical examination apparatus |
| GB0325956D0 (en) * | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
| EP1751133B1 (en) * | 2004-04-28 | 2010-04-14 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of rock and other protein kinases |
| EP1625849A1 (en) * | 2004-08-09 | 2006-02-15 | Liconsa, Liberacion Controlada de Sustancias Activas, S.A. | Pharmaceutical composition comprising drospirenone and ethynylestradiol |
| GB0510143D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds A1 |
| US20080051441A1 (en) * | 2004-12-28 | 2008-02-28 | Astrazeneca Ab | Aryl Sulphonamide Modulators |
| US20060257473A1 (en) * | 2005-05-11 | 2006-11-16 | Porranee Puranajoti | Extended release tablet |
| ES2371774T3 (es) * | 2005-06-03 | 2012-01-10 | Abbott Laboratories | Derivados de ciclobutilamina. |
| JP2007024970A (ja) * | 2005-07-12 | 2007-02-01 | Miyakawa:Kk | 液晶表示装置の開口効率を上昇させるための樹脂レンズ製造法及びその製造装置 |
| WO2007013830A1 (en) * | 2005-07-26 | 2007-02-01 | Portela & Ca. S.A. | Nitrocatechol derivatives as comt inhibitors |
| US20070048384A1 (en) * | 2005-08-26 | 2007-03-01 | Joerg Rosenberg | Pharmaceutical compositions |
| JP2008162955A (ja) * | 2006-12-28 | 2008-07-17 | Chugai Pharmaceut Co Ltd | バリン含有高密度顆粒剤 |
| DK2481410T3 (en) * | 2007-01-31 | 2016-10-24 | Bial - Portela & Ca S A | Nitrocatecholderivater as COMT inhibitors administered in a specific dosage regimen |
| AR065802A1 (es) * | 2007-03-22 | 2009-07-01 | Schering Corp | Formulaciones de comprimidos que contienen sales de 8- [( 1- ( 3,5- bis- (trifluorometil) fenil) -etoxi ) - metil) -8- fenil -1, 7- diaza- spiro [ 4,5] decan -2- ona y comprimidos elaborados a partir de estas |
| BRPI0908731A2 (pt) * | 2008-03-17 | 2017-05-16 | Bial - Portela & C A S A | formas cristalinas de 5-[3-(2,5-dicloro-4,6-dimetil-1-óxi-piridina-3-il)[1,2,4]oxadiazol-5-il]-3-nitrobenzeno-1,2-diol |
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2010
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- 2010-03-31 ES ES10714386T patent/ES2915698T3/es active Active
- 2010-03-31 CN CN201080022455.3A patent/CN102438595B/zh active Active
- 2010-03-31 PL PL10714386.9T patent/PL2413913T3/pl unknown
- 2010-03-31 JP JP2012503351A patent/JP5864410B2/ja active Active
- 2010-03-31 WO PCT/PT2010/000015 patent/WO2010114405A2/en not_active Ceased
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2015
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2018
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2020
- 2020-12-15 US US17/122,013 patent/US20210315824A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1845097A1 (en) * | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
Also Published As
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| CA2757418C (en) | 2021-06-15 |
| US20100256194A1 (en) | 2010-10-07 |
| EP2413913A2 (en) | 2012-02-08 |
| JP5864410B2 (ja) | 2016-02-17 |
| AU2010231962B2 (en) | 2015-05-21 |
| WO2010114405A3 (en) | 2011-01-06 |
| US20190008774A1 (en) | 2019-01-10 |
| CA2757418A1 (en) | 2010-10-07 |
| MX361618B (es) | 2018-12-13 |
| PT2413913T (pt) | 2022-06-09 |
| DK2413913T3 (da) | 2022-06-13 |
| PL2413913T3 (pl) | 2022-09-26 |
| EP2413913B1 (en) | 2022-05-18 |
| CN102438595B (zh) | 2016-04-27 |
| KR20120008040A (ko) | 2012-01-25 |
| BRPI1016132A2 (pt) | 2016-04-19 |
| JP6336420B2 (ja) | 2018-06-06 |
| MX2011010311A (es) | 2012-03-07 |
| ES2915698T3 (es) | 2022-06-24 |
| JP2016020369A (ja) | 2016-02-04 |
| BRPI1016132B1 (pt) | 2020-11-24 |
| US20210315824A1 (en) | 2021-10-14 |
| JP2012522764A (ja) | 2012-09-27 |
| KR101824257B1 (ko) | 2018-01-31 |
| CN102438595A (zh) | 2012-05-02 |
| WO2010114405A2 (en) | 2010-10-07 |
| BRPI1016132B8 (pt) | 2021-05-25 |
| AU2010231962A1 (en) | 2011-11-17 |
| CN105816456A (zh) | 2016-08-03 |
| RU2011143619A (ru) | 2013-05-10 |
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| MM4A | The patent is invalid due to non-payment of fees |
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Effective date: 20171211 |