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 PDF

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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
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compound
dimethoxy
hexahydro
pyrido
isoquinolin
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French (fr)
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CA2668689A1 (en
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Kyle W. Gano
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Neurocrine Biosciences Inc
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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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • 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)
CA2668689A 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 Active CA2668689C (en)

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

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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)

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US (2) US8039627B2 (enExample)
EP (1) EP2081929B1 (enExample)
JP (1) JP5290185B2 (enExample)
KR (1) KR101500766B1 (enExample)
CN (1) CN101553487B (enExample)
AU (1) AU2007317242B2 (enExample)
BR (1) BRPI0718247B1 (enExample)
CA (1) CA2668689C (enExample)
DK (1) DK2081929T3 (enExample)
EA (1) EA018378B1 (enExample)
ES (1) ES2402220T3 (enExample)
IL (1) IL198250A0 (enExample)
MX (1) MX2009004910A (enExample)
PL (1) PL2081929T3 (enExample)
PT (1) PT2081929E (enExample)
WO (1) WO2008058261A1 (enExample)

Families Citing this family (72)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2081929B1 (en) 2006-11-08 2013-01-09 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
SI3061760T1 (en) 2008-09-18 2018-04-30 Auspex Pharmaceuticals, Inc. Deuterated benzoquinolizine derivatives as inhibitors of vesicular monoamine transporter 2
EP2576552A4 (en) * 2010-06-01 2013-11-13 Aupex 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
EP4345100A3 (en) 2012-09-18 2024-04-10 Auspex Pharmaceuticals, Inc. Formulations pharmacokinetics of deuterated benzoquinoline inhibitors of vesicular monoamine transporter 2
US9550780B2 (en) 2012-09-18 2017-01-24 Auspex Pharmaceuticals, Inc. Formulations pharmacokinetics of deuterated benzoquinoline inhibitors of vesicular monoamine transporter 2
EP2951178A4 (en) 2013-01-31 2016-07-06 Auspex Pharmaceuticals Inc VMAT2 INHIBITORS OF BENZOQUINOLONE TYPE
HK1221645A1 (zh) * 2013-09-27 2017-06-09 Auspex Pharmaceuticals, Inc. Vmat2的苯并喹啉抑制剂
CN105873589B (zh) 2013-12-03 2019-11-01 奥斯拜客斯制药有限公司 制造苯并喹啉化合物的方法
CA2936823A1 (en) * 2014-01-27 2015-07-30 Auspex Pharmaceuticals, Inc. Benzoquinoline inhibitors of vesicular monoamine transporter 2
WO2015120110A2 (en) 2014-02-07 2015-08-13 Auspex Pharmaceuticals, Inc. Novel pharmaceutical formulations
JP6718376B2 (ja) 2014-02-07 2020-07-08 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 抗精神病薬物およびｖｍａｔ２阻害剤を含む医薬組成物およびその使用
SI3105218T1 (sl) 2014-02-13 2019-11-29 Incyte Corp Ciklopropilamini kot inhibitorji LSD1
KR20200133003A (ko) * 2014-05-06 2020-11-25 뉴로크린 바이오사이언시즈 인코퍼레이티드 과다운동성 운동 장애의 치료를 위한 vmat2 억제제
MX375718B (es) * 2015-02-06 2025-03-06 Neurocrine Biosciences Inc [9,10-dimetoxi-3-(2-metilpropil)-1h,2h,3h,4h,6h,7h,11bh-pirido-[2,1-a]isoquinolin-2-il]metanol y compuestos, composiciones y metodos relacionados con los mismos.
DK3265085T3 (da) 2015-03-06 2022-10-03 Auspex Pharmaceuticals Inc Fremgangsmåder til behandling af forstyrrelser med abnorme ufrivillige bevægelser
US9944647B2 (en) 2015-04-03 2018-04-17 Incyte Corporation Heterocyclic compounds as LSD1 inhibitors
WO2016210180A2 (en) * 2015-06-23 2016-12-29 Neurocrine Biosciences, Inc. Vmat2 inhibitors for treating neurological diseases or disorders
SI3334709T1 (sl) 2015-08-12 2025-03-31 Incyte Holdings Corporation Soli zaviralca lsd1
AR106313A1 (es) 2015-10-09 2018-01-03 Teva Pharmaceuticals Int Gmbh Combinación de levodopa deuterada con carbidopa y opicapona para el tratamiento de enfermedad de parkinson
TN2018000121A1 (en) 2015-10-30 2019-10-04 Neurocrine Biosciences Inc Valbenazine salts and polymorphs thereof
LT3394057T (lt) 2015-12-23 2022-06-27 Neurocrine Biosciences, Inc. Sintezės būdas, skirtas pagaminti (s)-(2r,3r,11br)-3-izobutil-9,10-dimetoksi-2,3,4,6,7,11b-heksahidro-1h-pirido[2,1-a]izochinolin-2-ilo 2-amino-3-metilbutanoato di(4-metilbenzensulfonatą)
WO2017182916A1 (en) * 2016-04-22 2017-10-26 Lupin Limited Novel 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
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
WO2018140092A1 (en) * 2017-01-27 2018-08-02 Obrien Christopher F Methods for the administration of certain vmat2 inhibitors
JP2020508337A (ja) 2017-02-27 2020-03-19 サンド・アクチエンゲゼルシヤフト バルベナジン塩の結晶形態
WO2018164996A1 (en) 2017-03-06 2018-09-13 Neurocrine Biosciences, Inc. Dosing regimen for valbenazine
JP7608050B2 (ja) 2017-03-15 2025-01-06 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 デューテトラベナジンの類似体、その調製及び使用
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
GB201705305D0 (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
GB201705303D0 (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
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
US20200276184A1 (en) 2017-09-21 2020-09-03 Neurocrine Biosciences, Inc. High Dosage Valbenazine Formulation and Compositions, Methods, and Kits Related Thereto
EA202090932A1 (ru) 2017-10-10 2021-05-20 Нейрокрин Байосайенсиз, Инк Способы введения некоторых vmat2-ингибиторов
KR20250070134A (ko) 2017-10-10 2025-05-20 뉴로크린 바이오사이언시즈 인코퍼레이티드 특정 vmat2 억제제의 투여 방법
JP2021503009A (ja) * 2017-11-08 2021-02-04 フォアシー ファーマシューティカルズ シーオー．，リミテッド ジヒドロテトラベナジンのエステル
US11384077B2 (en) 2017-11-22 2022-07-12 Assia Chemical Industries Ltd. Solid state form of Valbenazine
CN110621674B (zh) 2017-12-26 2022-03-29 苏州科睿思制药有限公司 一种Valbenazine二对甲苯磺酸盐的晶型及其制备方法和用途
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
AU2019287524A1 (en) * 2018-06-14 2020-12-24 Neurocrine Biosciences, Inc. VMAT2 inhibitor compounds, compositions, and methods relating thereto
JP2021528481A (ja) 2018-08-15 2021-10-21 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阻害剤を投与するための方法
US10968200B2 (en) 2018-08-31 2021-04-06 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
US20220340562A1 (en) * 2019-08-12 2022-10-27 Shandong Luye Pharmaceutical 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
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
CN117062815A (zh) 2021-03-22 2023-11-14 纽罗克里生物科学有限公司 Vmat2抑制剂及使用方法
US20240239791A1 (en) 2021-04-26 2024-07-18 Neurocrine Biosciences, Inc. Processes for the synthesis of valbenazine
US20240342159A1 (en) 2021-06-30 2024-10-17 Neurocrine Biosciences, Inc. Valbenazine for use in the add-on treatment of schizophrenia
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
IL319670A (en) 2022-09-21 2025-05-01 Neurocrine Biosciences Inc VMAT2 inhibitors based on hexahydro-2H-pyridyl-1,2-[A]isoquinoline and methods of use
WO2025038959A1 (en) 2023-08-17 2025-02-20 Neurocrine Biosciences, Inc. Methods for the administration of certain vmat2 inhibitors
TW202521119A (zh) 2023-08-17 2025-06-01 美商紐羅克里生物科學有限公司 用於投與特定vmat2抑制劑之方法
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

Family Cites Families (13)

* 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
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
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
NZ566011A (en) 2005-08-06 2011-01-28 Biovail Lab Internat Barbados Srl 3, 11b cis dihydrotetrabenazine for the treatment of schizophrenia and other psychoses
EP2081929B1 (en) 2006-11-08 2013-01-09 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

Also Published As

Publication number Publication date
KR101500766B1 (ko) 2015-03-16
ES2402220T8 (es) 2021-12-23
US20080167337A1 (en) 2008-07-10
US8039627B2 (en) 2011-10-18
WO2008058261A1 (en) 2008-05-15
KR20090079257A (ko) 2009-07-21
BRPI0718247B1 (pt) 2021-09-21
DK2081929T3 (da) 2013-04-15
EP2081929B1 (en) 2013-01-09
CA2668689A1 (en) 2008-05-15
JP2010509366A (ja) 2010-03-25
KR101500766B9 (ko) 2024-09-25
EP2081929A1 (en) 2009-07-29
CN101553487B (zh) 2012-06-13
EA200970461A1 (ru) 2009-12-30
CN101553487A (zh) 2009-10-07
IL198250A0 (en) 2009-12-24
PT2081929E (pt) 2013-04-15
MX2009004910A (es) 2009-07-24
JP5290185B2 (ja) 2013-09-18
US20120077839A1 (en) 2012-03-29
PL2081929T3 (pl) 2013-06-28
EA018378B1 (ru) 2013-07-30
AU2007317242A1 (en) 2008-05-15
US8357697B2 (en) 2013-01-22
AU2007317242B2 (en) 2013-08-01
BRPI0718247A2 (pt) 2014-01-07
ES2402220T3 (es) 2013-04-29

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