CN101553487B - 取代的3-异丁基-9,10-二甲氧基-1,3,4,6,7,11b-六氢-2H-吡啶并[2,1-a]异喹啉-2-醇化合物和与其相关的方法 - Google Patents

取代的3-异丁基-9,10-二甲氧基-1,3,4,6,7,11b-六氢-2H-吡啶并[2,1-a]异喹啉-2-醇化合物和与其相关的方法 Download PDF

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CN101553487B
CN101553487B CN2007800395790A CN200780039579A CN101553487B CN 101553487 B CN101553487 B CN 101553487B CN 2007800395790 A CN2007800395790 A CN 2007800395790A CN 200780039579 A CN200780039579 A CN 200780039579A CN 101553487 B CN101553487 B CN 101553487B
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dimethoxy
pyrido
hexahydro
isobutyl
isoquinolin
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CN101553487A (zh
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凯尔·W·加诺
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Neurocrine Biosciences Inc
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    • 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

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
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  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CN2007800395790A 2006-11-08 2007-11-08 取代的3-异丁基-9,10-二甲氧基-1,3,4,6,7,11b-六氢-2H-吡啶并[2,1-a]异喹啉-2-醇化合物和与其相关的方法 Active CN101553487B (zh)

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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

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CN101553487B true CN101553487B (zh) 2012-06-13

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US (2) US8039627B2 (OSRAM)
EP (1) EP2081929B1 (OSRAM)
JP (1) JP5290185B2 (OSRAM)
KR (1) KR101500766B1 (OSRAM)
CN (1) CN101553487B (OSRAM)
AU (1) AU2007317242B2 (OSRAM)
BR (1) BRPI0718247B1 (OSRAM)
CA (1) CA2668689C (OSRAM)
DK (1) DK2081929T3 (OSRAM)
EA (1) EA018378B1 (OSRAM)
ES (1) ES2402220T3 (OSRAM)
IL (1) IL198250A0 (OSRAM)
MX (1) MX2009004910A (OSRAM)
PL (1) PL2081929T3 (OSRAM)
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Families Citing this family (71)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2007317242B2 (en) 2006-11-08 2013-08-01 Neurocrine Biosciences, Inc. 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
US8524733B2 (en) 2008-09-18 2013-09-03 Auspex Pharmaceuticals Benzoquinoline inhibitors of vesicular monoamine transporter 2
WO2011153157A2 (en) 2010-06-01 2011-12-08 Auspex Pharmaceutical, 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
IN2015DN01662A (OSRAM) 2012-09-18 2015-07-03 Auspex Pharmaceuticals Inc
US9550780B2 (en) 2012-09-18 2017-01-24 Auspex Pharmaceuticals, Inc. Formulations pharmacokinetics of deuterated benzoquinoline inhibitors of vesicular monoamine transporter 2
CA2899707A1 (en) * 2013-01-31 2014-08-07 Auspex Pharmaceuticals, Inc. Benzoquinolone inhibitors of vmat2
WO2015048370A1 (en) * 2013-09-27 2015-04-02 Auspex Pharmaceuticals, Inc. Benzoquinolone inhibitors of vmat2
AU2014357518A1 (en) * 2013-12-03 2016-06-09 Auspex Pharmaceuticals, Inc. Methods of manufacturing benzoquinoline compounds
MX2016009817A (es) 2014-01-27 2017-02-28 Auspex Pharmaceuticals Inc Inhibidores de benzoquinolina del transportador vesicular de monoaminas 2.
CN113368110A (zh) * 2014-02-07 2021-09-10 纽罗克里生物科学有限公司 包含抗精神病药物和vmat2抑制剂的药物组合物及其用途
US10166183B2 (en) 2014-02-07 2019-01-01 Auspex Pharmaceuticals, Inc. Pharmaceutical formulations
ME03654B (me) 2014-02-13 2020-07-20 Incyte Corp Ciklopropilamini kao lsd1 inhibitori
SI3936130T1 (sl) * 2014-05-06 2024-05-31 Neurocrine Biosciences, Inc., Režim odmerjanja valbenazina za zdravljenje hiperkinetičnih gibalnih motenj
WO2016127133A1 (en) * 2015-02-06 2016-08-11 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
JP6932641B2 (ja) 2015-03-06 2021-09-08 オースペックス ファーマシューティカルズ インコーポレイテッド 異常不随意運動障害の処置のための方法
AU2016243939B2 (en) 2015-04-03 2020-09-03 Incyte Holdings Corporation Heterocyclic compounds as LSD1 inhibitors
KR20240125709A (ko) * 2015-06-23 2024-08-19 뉴로크린 바이오사이언시즈 인코퍼레이티드 신경계 질환 또는 장애를 치료하기 위한 vmat2 억제제
KR102710120B1 (ko) 2015-08-12 2024-09-27 인사이트 홀딩스 코포레이션 Lsd1 저해제의 염
EP3359148A1 (en) 2015-10-09 2018-08-15 Teva Pharmaceuticals International GmbH Combination of deuterated levodopa with carbidopa and opicapone for the treatment of parkinson`s disease
ES2972600T3 (es) 2015-10-30 2024-06-13 Neurocrine Biosciences Inc Sales de diclorhidrato de valbenazina y polimorfos de las mismas
DK3394057T3 (da) 2015-12-23 2022-04-11 Neurocrine Biosciences Inc Syntetisk fremgangsmåde til fremstilling af (S)-(2R,3R,11BR)-3-isobutyl-9,10-dimethoxy-2,3,4,6,7,11B-hexahydro-1H-pyrido[2,1,-A]isoquinolin-2-yl 2-amino-3-methylbutanoat-di(4-methylbenzensulfonat)
WO2017182916A1 (en) * 2016-04-22 2017-10-26 Lupin Limited Novel process for preparation of tetrabenazine and deutetrabenazine
ES2811048T3 (es) * 2016-06-29 2021-03-10 Crystal Pharmaceutical Suzhou Co Ltd Formas cristalinas de NBI-98854, método de preparación para las mismas y uso de las mismas
EP3523300A1 (en) 2016-10-06 2019-08-14 Assia Chemical Industries Ltd. Solid state forms of valbenazine
TW202515564A (zh) 2016-12-02 2025-04-16 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
WO2018130345A1 (en) 2017-01-10 2018-07-19 Sandoz Ag Crystalline valbenazine free base
JP7199359B2 (ja) * 2017-01-27 2023-01-05 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
US10954235B2 (en) 2017-02-27 2021-03-23 Sandoz Ag Crystalline forms of valbenazine salts
WO2018164996A1 (en) 2017-03-06 2018-09-13 Neurocrine Biosciences, Inc. Dosing regimen for valbenazine
PE20191819A1 (es) 2017-03-15 2019-12-27 Auspex Pharmaceuticals Inc Analogos de deutetrabenazina, su preparacion y uso
GB201705303D0 (en) 2017-04-01 2017-05-17 Adeptio Pharmaceuticals Ltd Pharmaceutical compositions
GB201705306D0 (en) 2017-04-01 2017-05-17 Adeptio Pharmaceuticals Ltd Pharmaceutical compositions
GB201705302D0 (en) 2017-04-01 2017-05-17 Adeptio Pharmaceuticals Ltd Pharmaceutical compositions
WO2018178243A2 (en) * 2017-04-01 2018-10-04 Adeptio Pharmaceuticals Limited Pharmaceutical compositions
GB201705304D0 (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
BR112020005373A2 (pt) 2017-09-21 2020-09-24 Neurocrine Biosciences Inc. formulação de valbenazina em alta dosagem e composições, métodos e kits relacionados com valbenazina
KR20250070134A (ko) 2017-10-10 2025-05-20 뉴로크린 바이오사이언시즈 인코퍼레이티드 특정 vmat2 억제제의 투여 방법
SG11202003194YA (en) * 2017-10-10 2020-05-28 Neurocrine Biosciences Inc Methods for the administration of certain vmat2 inhibitors
EP3706748A4 (en) * 2017-11-08 2021-08-11 Foresee Pharmaceuticals Co., Ltd. ESTER OF DIHYDROTETRABENAZINE
US11384077B2 (en) 2017-11-22 2022-07-12 Assia Chemical Industries Ltd. Solid state form of Valbenazine
US11339158B2 (en) 2017-12-26 2022-05-24 Crystal Pharmaceutical (Suzhou) Co., Ltd. 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
TW202011963A (zh) * 2018-06-14 2020-04-01 美商紐羅克里生物科學有限公司 Vmat2抑制劑化合物、組合物及其相關方法
MA53239A (fr) 2018-08-15 2022-05-04 Neurocrine Biosciences Inc Procédés d'administration de certains inhibiteurs de vmat2
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
CN114302883B (zh) * 2019-08-12 2022-09-06 山东绿叶制药有限公司 Vmat2抑制剂及其制备方法和应用
US10940141B1 (en) 2019-08-23 2021-03-09 Neurocrine Biosciences, Inc. Methods for the administration of certain VMAT2 inhibitors
EP4028397A1 (en) 2019-09-13 2022-07-20 Neurocrine Biosciences, Inc. Processes for the synthesis of valbenazine
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
EP4606429A3 (en) 2021-03-22 2025-12-03 Neurocrine Biosciences, Inc. Vmat2 inhibitors and methods of use
JP2024516199A (ja) 2021-04-26 2024-04-12 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方法
WO2023278991A1 (en) 2021-06-30 2023-01-05 Neurocrine Biosciences, Inc. Valbenazine for use in the treatment of dyskinesia due to cerebral palsy
BR112023026691A2 (pt) 2021-06-30 2024-03-05 Neurocrine Biosciences Inc Valbenazina para uso no tratamento complementar de esquizofrenia
EP4489754A1 (en) 2022-03-07 2025-01-15 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
PE20251750A1 (es) 2022-09-21 2025-07-09 Neurocrine Biosciences Inc Inhibidores de hexahidro-2h-pirido[2,1-a]isoquinolina vmat2 y metodos de uso
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

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005077946A1 (en) * 2004-02-11 2005-08-25 Cambridge Laboratories (Ireland) Limited Dihydrotetrabenazines and pharmaceutical compositions containing them

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3209005A (en) * 1965-09-28 Hexahydro-llbh-benzo[a] quinolizines and processes therefor
US2843591A (en) * 1958-07-15 Method for preparing same
US2852518A (en) * 1957-05-23 1958-09-16 Parke Davis & Co Di-substituted quinoline compounds
WO1991016920A1 (en) 1990-05-07 1991-11-14 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
WO2006053067A2 (en) 2004-11-09 2006-05-18 Prestwick Pharmaceuticals, Inc. Combination of amantadine and a tetrabenazine compound for treating hyperkinetic disorders
CA2623794A1 (en) 2005-06-29 2007-01-11 The 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
PT1855677E (pt) 2005-08-06 2009-01-13 Cambridge Lab Ireland Ltd 3-11b-cis-di-hidrotetrabenazina para o tratamento da esquizofrenia e de outras psicoses
AU2007317242B2 (en) 2006-11-08 2013-08-01 Neurocrine Biosciences, Inc. 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

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005077946A1 (en) * 2004-02-11 2005-08-25 Cambridge Laboratories (Ireland) Limited Dihydrotetrabenazines and pharmaceutical compositions containing them

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Aranda,G. et al..Synthesis and biological activity of iodinated and photosensitive derivatives of tetrabenazine.《Eur. J. Med. Chem.》.1990,第25卷(第4期),369-374. *
Brossi,A. et al..Syntheseversuche in der Emetin-Reihe.《Helvetica Chimica Acta》.1958,第41卷(第4期),1793-1806. *
Kilbourn,M.R. et al..Absolute Configuration of (+)-a-Dihydrotetrabenazine, an Active Metabolite of Tetrabenazine.《Chirality》.1997,第9卷(第1期),59-62. *

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ES2402220T8 (es) 2021-12-23
PT2081929E (pt) 2013-04-15
AU2007317242A1 (en) 2008-05-15
CA2668689A1 (en) 2008-05-15
CA2668689C (en) 2015-12-29
MX2009004910A (es) 2009-07-24
EA200970461A1 (ru) 2009-12-30
JP5290185B2 (ja) 2013-09-18
BRPI0718247A2 (pt) 2014-01-07
KR101500766B9 (ko) 2024-09-25
KR101500766B1 (ko) 2015-03-16
EP2081929A1 (en) 2009-07-29
ES2402220T3 (es) 2013-04-29
BRPI0718247B1 (pt) 2021-09-21
EA018378B1 (ru) 2013-07-30
US20120077839A1 (en) 2012-03-29
IL198250A0 (en) 2009-12-24
DK2081929T3 (da) 2013-04-15
WO2008058261A1 (en) 2008-05-15
KR20090079257A (ko) 2009-07-21
AU2007317242B2 (en) 2013-08-01
US8039627B2 (en) 2011-10-18
US8357697B2 (en) 2013-01-22
EP2081929B1 (en) 2013-01-09
US20080167337A1 (en) 2008-07-10
JP2010509366A (ja) 2010-03-25
PL2081929T3 (pl) 2013-06-28
CN101553487A (zh) 2009-10-07

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Inventor after: Gano Kyle W.

Inventor after: Nichol Harriot

Inventor before: Gano Kyle W.