CA2668689C - Substituted 3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2h-pyrido[2,1-a]isoquinolin-2-ol compounds and methods relating thereto - Google Patents
Substituted 3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2h-pyrido[2,1-a]isoquinolin-2-ol compounds and methods relating thereto Download PDFInfo
- Publication number
- CA2668689C CA2668689C CA2668689A CA2668689A CA2668689C CA 2668689 C CA2668689 C CA 2668689C CA 2668689 A CA2668689 A CA 2668689A CA 2668689 A CA2668689 A CA 2668689A CA 2668689 C CA2668689 C CA 2668689C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- dimethoxy
- hexahydro
- pyrido
- isoquinolin
- 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.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86494406P | 2006-11-08 | 2006-11-08 | |
| US60/864,944 | 2006-11-08 | ||
| PCT/US2007/084176 WO2008058261A1 (en) | 2006-11-08 | 2007-11-08 | Substituted 3-isobutyl-9, 10-dimethoxy-1,3,4,6,7,11b-hexahydro-2h-pyrido[2,1-a] isoquinolin-2-ol compounds and methods relating thereto |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2668689A1 CA2668689A1 (en) | 2008-05-15 |
| CA2668689C true CA2668689C (en) | 2015-12-29 |
Family
ID=39110526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2668689A Active CA2668689C (en) | 2006-11-08 | 2007-11-08 | Substituted 3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2h-pyrido[2,1-a]isoquinolin-2-ol compounds and methods relating thereto |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US8039627B2 (https=) |
| EP (1) | EP2081929B1 (https=) |
| JP (1) | JP5290185B2 (https=) |
| KR (1) | KR101500766B1 (https=) |
| CN (1) | CN101553487B (https=) |
| AU (1) | AU2007317242B2 (https=) |
| BR (1) | BRPI0718247B1 (https=) |
| CA (1) | CA2668689C (https=) |
| DK (1) | DK2081929T3 (https=) |
| EA (1) | EA018378B1 (https=) |
| ES (1) | ES2402220T3 (https=) |
| IL (1) | IL198250A0 (https=) |
| MX (1) | MX2009004910A (https=) |
| PL (1) | PL2081929T3 (https=) |
| PT (1) | PT2081929E (https=) |
| WO (1) | WO2008058261A1 (https=) |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2081929T3 (pl) | 2006-11-08 | 2013-06-28 | Neurocrine Biosciences Inc | Podstawione związki 3-izobutylo-9,10-dimetoksy-1,3,4,6,7,11b-heksahydro-2H-pirydo[2,1-a]izochinolin-2-olowe i ich wytwarzania |
| WO2010044981A2 (en) | 2008-09-18 | 2010-04-22 | Auspex Pharmaceutical ,Inc. | Benzoquinoline inhibitors of vesicular monoamine transporter 2 |
| CA2801061A1 (en) * | 2010-06-01 | 2011-12-08 | Auspex Pharmaceuticals, Inc. | Benzoquinolone inhibitors of vmat2 |
| WO2012000308A1 (zh) * | 2010-06-29 | 2012-01-05 | 中国药科大学 | 丁苯那嗪的拆分方法 |
| US8351329B2 (en) * | 2010-09-14 | 2013-01-08 | Cisco Technology, Inc. | Universal load-balancing tunnel encapsulation |
| CN102285984B (zh) * | 2010-11-25 | 2012-10-10 | 江苏威凯尔医药科技有限公司 | (2R,3R,11bR)-二氢丁苯那嗪及相关化合物的制备方法 |
| WO2012081031A1 (en) * | 2010-12-15 | 2012-06-21 | Enaltec Labs Pvt. Ltd. | Process for preparing tetrabenazine |
| US9550780B2 (en) | 2012-09-18 | 2017-01-24 | Auspex Pharmaceuticals, Inc. | Formulations pharmacokinetics of deuterated benzoquinoline inhibitors of vesicular monoamine transporter 2 |
| CN104684555A (zh) | 2012-09-18 | 2015-06-03 | 奥斯拜客斯制药有限公司 | 囊泡单胺转运体2的氘化苯并喹啉抑制剂的制剂药代动力学 |
| EA202091397A1 (ru) * | 2013-01-31 | 2020-09-04 | Ауспекс Фармацетикалс, Инк. | Бензохинолоновые ингибиторы vmat2 |
| HK1221645A1 (zh) * | 2013-09-27 | 2017-06-09 | Auspex Pharmaceuticals, Inc. | Vmat2的苯并喹啉抑制剂 |
| EA201791466A1 (ru) * | 2013-12-03 | 2017-11-30 | Оспекс Фармасьютикалз, Инк. | Способы получения соединений бензохинолина |
| EA201691512A1 (ru) | 2014-01-27 | 2017-01-30 | Оспекс Фармасьютикалз, Инк. | Бензохинолиновые ингибиторы везикулярного переносчика моноамина 2 |
| US10166183B2 (en) | 2014-02-07 | 2019-01-01 | Auspex Pharmaceuticals, Inc. | Pharmaceutical formulations |
| NZ760790A (en) * | 2014-02-07 | 2022-11-25 | Neurocrine Biosciences Inc | Pharmaceutical compositions comprising an antipsychotic drug and a vmat2 inhibitor and uses thereof |
| SI3105218T1 (sl) | 2014-02-13 | 2019-11-29 | Incyte Corp | Ciklopropilamini kot inhibitorji LSD1 |
| WO2015171802A1 (en) * | 2014-05-06 | 2015-11-12 | Neurocrine Biosciences, Inc. | Vmat2 inhibitors for the treatment of hyperkinetic movement disorders |
| CA2974540C (en) * | 2015-02-06 | 2023-09-26 | Neurocrine Biosciences, Inc. | [9,10-dimethoxy-3-(2-methylpropyl)-1h,2h,3h,4h,6h,7h,11bh-pyrido-[2,1-a]isoquinolin-2-yl]methanol and compounds, compositions and methods relating thereto |
| HRP20221106T1 (hr) | 2015-03-06 | 2022-11-25 | Auspex Pharmaceuticals, Inc. | Postupci liječenja abnormalnih nevoljnih poremećaja pokreta |
| EP3277689B1 (en) | 2015-04-03 | 2019-09-04 | Incyte Corporation | Heterocyclic compounds as lsd1 inhibitors |
| EA036837B1 (ru) * | 2015-06-23 | 2020-12-25 | Нейрокрин Байосайенсиз, Инк. | Ингибиторы vmat2 для лечения неврологических заболеваний или расстройств |
| LT3334709T (lt) | 2015-08-12 | 2025-03-10 | Incyte Holdings Corporation | Lsd1 inhibitoriaus druskos |
| MX383906B (es) | 2015-10-09 | 2025-03-14 | Teva Pharmaceuticals Int Gmbh | Combinación de levodopa deuterado con carbidopa y opicapona para el tratamiento del mal de parkinson |
| MY193767A (en) * | 2015-10-30 | 2022-10-27 | Neurocrine Biosciences Inc | Valbenazine salts and polymorphs thereof |
| CN108925135B (zh) * | 2015-12-23 | 2025-09-19 | 纽罗克里生物科学有限公司 | 制备(S)-(2R,3R,11bR)-3-异丁基-9,10-二甲氧基-2,3,4,6,7,11b-六氢-1H-吡啶并[2,1-a]异喹啉-2-基2-氨基-3-甲基丁酸酯二(4-甲基苯磺酸盐)的合成方法 |
| US10479787B2 (en) | 2016-04-22 | 2019-11-19 | Lupin Limited | Process for preparation of tetrabenazine and deutetrabenazine |
| US10442800B2 (en) * | 2016-06-29 | 2019-10-15 | Crystal Pharmaceutical (Suzhou) Co., Ltd. | Crystal forms of NBI-98854, preparation method and use thereof |
| EP3523300A1 (en) | 2016-10-06 | 2019-08-14 | Assia Chemical Industries Ltd. | Solid state forms of valbenazine |
| TW202345829A (zh) | 2016-12-02 | 2023-12-01 | 美商紐羅克里生物科學有限公司 | 戊苯那嗪（valbenazine）於治療精神分裂症或情感性精神分裂症之用途 |
| EP3568394A1 (en) | 2017-01-10 | 2019-11-20 | Sandoz AG | Crystalline valbenazine free base |
| WO2018140092A1 (en) | 2017-01-27 | 2018-08-02 | Obrien Christopher F | Methods for the administration of certain vmat2 inhibitors |
| CA3054238A1 (en) | 2017-02-27 | 2018-08-30 | Sandoz Ag | Crystalline forms of valbenazine salts |
| WO2018164996A1 (en) | 2017-03-06 | 2018-09-13 | Neurocrine Biosciences, Inc. | Dosing regimen for valbenazine |
| UA127052C2 (uk) | 2017-03-15 | 2023-03-29 | Оспекс Фармасьютікалс, Інк. | Аналоги деутетрабеназину, їхнє отримання та застосування |
| GB201705302D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| JP7250692B2 (ja) * | 2017-04-01 | 2023-04-03 | アデプティオ ファーマシューティカルズ リミテッド | 運動障害の治療における使用のためのジヒドロテトラベナジン |
| GB201705306D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201705304D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201705303D0 (en) * | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201705305D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| JOP20190239A1 (ar) | 2017-04-19 | 2019-10-09 | Neurocrine Biosciences Inc | مركبات مثبطة لـ vmat2 وتركيبات منها |
| WO2018200605A1 (en) | 2017-04-26 | 2018-11-01 | Neurocrine Biosciences, Inc. | Use of valbenazine for treating levodopa-induced dyskinesia |
| ES3024958T3 (en) | 2017-09-21 | 2025-06-05 | Neurocrine Biosciences Inc | High dosage valbenazine formulation and compositions, methods, and kits related thereto |
| JP2021502959A (ja) | 2017-10-10 | 2021-02-04 | ニューロクライン バイオサイエンシーズ，インコーポレイテッド | 特定のｖｍａｔ２インヒビターを投与するための方法 |
| KR20250070134A (ko) | 2017-10-10 | 2025-05-20 | 뉴로크린 바이오사이언시즈 인코퍼레이티드 | 특정 vmat2 억제제의 투여 방법 |
| CA3081709A1 (en) * | 2017-11-08 | 2019-05-16 | Yuhua Li | Esters of dihydrotetrabenazine |
| EP3713938A1 (en) | 2017-11-22 | 2020-09-30 | Assia Chemical Industries Ltd | Solid state form of valbenazine |
| CA3086611C (en) | 2017-12-26 | 2023-07-25 | Crystal Pharmaceutical (Suzhou) Co., Ltd. | A crystalline form of valbenazine ditosylate, processes for preparation thereof and use thereof |
| CN110092785A (zh) * | 2018-01-31 | 2019-08-06 | 广东东阳光药业有限公司 | 一种丁苯那嗪的动态拆分方法 |
| GB201808464D0 (en) | 2018-05-23 | 2018-07-11 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compounds for use in treating huntington's disease |
| MX2020013004A (es) * | 2018-06-14 | 2021-02-17 | Neurocrine Biosciences Inc | Compuestos inhibidores del transportador de monoamina 2 (vmat2), composiciones, y metodos relacionados con los mismos. |
| SG11202100303QA (en) | 2018-08-15 | 2021-02-25 | Neurocrine Biosciences Inc | Methods for the administration of certain vmat2 inhibitors |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
| EP3860599B1 (en) | 2018-10-04 | 2024-05-15 | Adeptio Pharmaceuticals Limited | (+)-alpha-dihydrotetrabenazine dosage regimen for treating movement disorders |
| CA3065236A1 (en) | 2018-12-27 | 2020-06-27 | Apotex Inc. | Novel crystalline form of valbenazine dibesylate |
| WO2020213014A1 (en) | 2019-04-19 | 2020-10-22 | Mylan Laboratories Limited | An improved process for the preparation of valbenazine and its salts |
| US10689380B1 (en) | 2019-07-30 | 2020-06-23 | Farmhispania S.A. | Crystalline forms of valbenazine ditosylate |
| US12565495B2 (en) * | 2019-08-12 | 2026-03-03 | Luye Innomind Pharma Shijiazhuang Co., Ltd. | VMAT2 inhibitor and preparation method therefor and application thereof |
| US10940141B1 (en) | 2019-08-23 | 2021-03-09 | Neurocrine Biosciences, Inc. | Methods for the administration of certain VMAT2 inhibitors |
| JP2022547990A (ja) | 2019-09-13 | 2022-11-16 | ニューロクライン バイオサイエンシーズ，インコーポレイテッド | バルベナジンの合成のための方法 |
| CN110698397A (zh) * | 2019-10-28 | 2020-01-17 | 南京红杉生物科技有限公司 | 丁苯那嗪中间体及其合成方法、应用和合成用中间产物 |
| PT4168409T (pt) | 2021-03-22 | 2025-06-12 | Neurocrine Biosciences Inc | Inibidores de vmat2 e métodos de utilização |
| US20240239791A1 (en) | 2021-04-26 | 2024-07-18 | Neurocrine Biosciences, Inc. | Processes for the synthesis of valbenazine |
| BR112023026691A2 (pt) | 2021-06-30 | 2024-03-05 | Neurocrine Biosciences Inc | Valbenazina para uso no tratamento complementar de esquizofrenia |
| MX2023014977A (es) | 2021-06-30 | 2024-02-09 | Neurocrine Biosciences Inc | Valbenazina para usarse en el tratamiento de discinesia debido a paralisis cerebral. |
| WO2023172849A1 (en) | 2022-03-07 | 2023-09-14 | Neurocrine Biosciences, Inc. | Valbenazine, a vmat2 inhibitor, as a free base a tosylate or ditosylate salt, for use in the treatment of chorea associated with huntington's disease |
| TW202421131A (zh) | 2022-09-21 | 2024-06-01 | 美商紐羅克里生物科學有限公司 | Vmat2抑制劑及其使用方法 |
| WO2025038959A1 (en) | 2023-08-17 | 2025-02-20 | Neurocrine Biosciences, Inc. | Methods for the administration of certain vmat2 inhibitors |
| WO2025038938A1 (en) | 2023-08-17 | 2025-02-20 | Neurocrine Biosciences, Inc. | Valbenazine for use in the treatment of huntington's chorea |
| WO2025096823A1 (en) | 2023-11-01 | 2025-05-08 | Neurocrine Biosciences, Inc. | Improvement, maintenance or reduction of decline of motor function associated with huntington disease using valbenazine |
| WO2025188830A1 (en) | 2024-03-06 | 2025-09-12 | Neurocrine Biosciences, Inc. | Methods for the administration of certain vmat2 inhibitors |
| WO2025199234A1 (en) | 2024-03-20 | 2025-09-25 | Neurocrine Biosciences, Inc. | Vmat2 inhibitors and methods of use |
| WO2026050236A1 (en) | 2024-08-27 | 2026-03-05 | Neurocrine Biosciences, Inc. | Muscarinic receptor agonist in combination with a vesicular monoamine transporter 2 inhibitor, for use in the treatment of a neurological or psychiatric disorder |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2843591A (en) * | 1958-07-15 | Method for preparing same | ||
| US3209005A (en) * | 1965-09-28 | Hexahydro-llbh-benzo[a] quinolizines and processes therefor | ||
| US2852518A (en) * | 1957-05-23 | 1958-09-16 | Parke Davis & Co | Di-substituted quinoline compounds |
| AU7872491A (en) | 1990-05-07 | 1991-11-27 | Vical, Inc. | Lipid prodrugs of salicylate and nonsteroidal anti-inflammatory drugs |
| US6610841B1 (en) | 1997-12-18 | 2003-08-26 | Gilead Sciences, Inc. | Nucleotide-based prodrugs |
| US7045543B2 (en) * | 2001-11-05 | 2006-05-16 | Enzrel Inc. | Covalent conjugates of biologically-active compounds with amino acids and amino acid derivatives for targeting to physiologically-protected sites |
| GB2410947B (en) * | 2004-02-11 | 2008-09-17 | Cambridge Lab Ltd | Pharmaceutical compounds |
| WO2006053067A2 (en) | 2004-11-09 | 2006-05-18 | Prestwick Pharmaceuticals, Inc. | Combination of amantadine and a tetrabenazine compound for treating hyperkinetic disorders |
| WO2007005283A2 (en) | 2005-06-29 | 2007-01-11 | Trustees Of Columbia University In The City Of New York | Use of dtbz for imaging endocrine pancreas and beta cell mass in type 1 diabetes |
| GB0514501D0 (en) | 2005-07-14 | 2005-08-24 | Cambridge Lab Ireland Ltd | Pharmaceutical compounds |
| GB0516168D0 (en) | 2005-08-05 | 2005-09-14 | Cambridge Lab Ireland Ltd | Pharmaceutical compounds |
| EP1855677B1 (en) | 2005-08-06 | 2008-12-03 | Cambridge Laboratories (Ireland) Limited | 3,11b cis dihydrotetrabanezine for the treatment of schizophrenia and other psychoses |
| PL2081929T3 (pl) | 2006-11-08 | 2013-06-28 | Neurocrine Biosciences Inc | Podstawione związki 3-izobutylo-9,10-dimetoksy-1,3,4,6,7,11b-heksahydro-2H-pirydo[2,1-a]izochinolin-2-olowe i ich wytwarzania |
-
2007
- 2007-11-08 PL PL07864160T patent/PL2081929T3/pl unknown
- 2007-11-08 DK DK07864160.2T patent/DK2081929T3/da active
- 2007-11-08 WO PCT/US2007/084176 patent/WO2008058261A1/en not_active Ceased
- 2007-11-08 CA CA2668689A patent/CA2668689C/en active Active
- 2007-11-08 MX MX2009004910A patent/MX2009004910A/es active IP Right Grant
- 2007-11-08 ES ES07864160T patent/ES2402220T3/es active Active
- 2007-11-08 EA EA200970461A patent/EA018378B1/ru unknown
- 2007-11-08 CN CN2007800395790A patent/CN101553487B/zh active Active
- 2007-11-08 EP EP07864160A patent/EP2081929B1/en active Active
- 2007-11-08 AU AU2007317242A patent/AU2007317242B2/en active Active
- 2007-11-08 BR BRPI0718247-3A patent/BRPI0718247B1/pt active IP Right Grant
- 2007-11-08 PT PT78641602T patent/PT2081929E/pt unknown
- 2007-11-08 JP JP2009536493A patent/JP5290185B2/ja active Active
- 2007-11-08 KR KR1020097011731A patent/KR101500766B1/ko active Active
- 2007-11-08 US US11/937,445 patent/US8039627B2/en active Active
-
2009
- 2009-04-21 IL IL198250A patent/IL198250A0/en active IP Right Grant
-
2011
- 2011-09-20 US US13/237,709 patent/US8357697B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007317242B2 (en) | 2013-08-01 |
| ES2402220T3 (es) | 2013-04-29 |
| KR101500766B1 (ko) | 2015-03-16 |
| US8039627B2 (en) | 2011-10-18 |
| EP2081929B1 (en) | 2013-01-09 |
| IL198250A0 (en) | 2009-12-24 |
| US8357697B2 (en) | 2013-01-22 |
| KR101500766B9 (ko) | 2024-09-25 |
| CA2668689A1 (en) | 2008-05-15 |
| PT2081929E (pt) | 2013-04-15 |
| JP2010509366A (ja) | 2010-03-25 |
| CN101553487A (zh) | 2009-10-07 |
| DK2081929T3 (da) | 2013-04-15 |
| AU2007317242A1 (en) | 2008-05-15 |
| EP2081929A1 (en) | 2009-07-29 |
| PL2081929T3 (pl) | 2013-06-28 |
| MX2009004910A (es) | 2009-07-24 |
| CN101553487B (zh) | 2012-06-13 |
| EA200970461A1 (ru) | 2009-12-30 |
| WO2008058261A1 (en) | 2008-05-15 |
| ES2402220T8 (es) | 2021-12-23 |
| BRPI0718247A2 (pt) | 2014-01-07 |
| US20120077839A1 (en) | 2012-03-29 |
| KR20090079257A (ko) | 2009-07-21 |
| BRPI0718247B1 (pt) | 2021-09-21 |
| US20080167337A1 (en) | 2008-07-10 |
| EA018378B1 (ru) | 2013-07-30 |
| JP5290185B2 (ja) | 2013-09-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2668689C (en) | Substituted 3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2h-pyrido[2,1-a]isoquinolin-2-ol compounds and methods relating thereto | |
| EP3652167A1 (en) | Spiroheptanyl hydantoins as rock inhibitors | |
| CA3163933A1 (en) | Antagonists of the muscarinic acetylcholine receptor m4 | |
| EP1154988B1 (en) | Mevinolin derivatives | |
| US10501466B2 (en) | WDR5 inhibitors and modulators | |
| CA3103120A1 (en) | Chemical compounds | |
| BR112018013955B1 (pt) | Compostos ligantes de dopamina d3 de 6,7,8,9-tetra-hidro-5h-pirido [2,3- d] azepina, composição farmacêutica que os compreende e uso dos mesmos | |
| FI113769B (fi) | Neurosuojaavia kromaaniyhdisteitä | |
| EP3867244B1 (en) | 4-pyrazin-2-ylmethyl-morpholine derivatives and the use thereof as medicament | |
| EP3720855B1 (en) | Imidazopyridine derivatives and the use thereof as medicament | |
| CN118302418A (zh) | 一种芳杂环类化合物及其应用 | |
| CN111356677B (zh) | 四氢异喹啉类衍生物及其制备方法和用途 | |
| EP3980401B1 (en) | Purine derivatives, as nr2b negative modulators and the use thereof as medicament, in particular for treating depressive disorders | |
| EP3866854B1 (en) | 4-pyridinylmethyl-morpholine derivatives and the use thereof as medicament | |
| EP3867245B1 (en) | 4-pyrimidin-5-ylmethyl-morpholine derivatives and the use thereof as medicament | |
| Xi et al. | Drug metabolism-based design, synthesis, and bioactivities of 1-(2, 6-dimethylphenoxy)-2-(3, 4-dimethoxyphenylethylamino) propane hydrochloride (DDPH) analogs as α1-adrenoceptors antagonists | |
| EA052032B1 (ru) | Новые соединения в качестве двойных ингибиторов андрогенового рецептора и фосфодиэстеразы | |
| KR20260056261A (ko) | Pde 7 조절제 화합물 | |
| IL324923A (en) | Asymmetric phenylalkylamines | |
| CN121532384A (zh) | 嘧啶化合物及其作为usp1抑制剂的用途 | |
| CN119912454A (zh) | 抗肿瘤化合物及其制备方法和用途 | |
| WO2020246487A1 (ja) | ジスピロジケトピペラジン構造を有する化合物 | |
| HK40033047A (en) | Imidazopyridine derivatives and the use thereof as medicament | |
| HK40059626A (en) | 4-pyrazin-2-ylmethyl-morpholine derivatives and the use thereof as medicament | |
| HK40059626B (en) | 4-pyrazin-2-ylmethyl-morpholine derivatives and the use thereof as medicament |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MPN | Maintenance fee for patent paid |
Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 17TH ANNIV.) - STANDARD Year of fee payment: 17 |
|
| U00 | Fee paid |
Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED Effective date: 20241101 |
|
| U11 | Full renewal or maintenance fee paid |
Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT Effective date: 20241101 |