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

Info

Publication number
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
Authority
CN
China
Prior art keywords
dimethoxy
pyrido
hexahydro
isobutyl
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
Application number
CN2007800395790A
Other languages
English (en)
Chinese (zh)
Other versions
CN101553487A (zh
Inventor
凯尔·W·加诺
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Neurocrine Biosciences Inc
Original Assignee
Neurocrine Biosciences Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=39110526&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CN101553487(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Neurocrine Biosciences Inc filed Critical Neurocrine Biosciences Inc
Publication of CN101553487A publication Critical patent/CN101553487A/zh
Application granted granted Critical
Publication of CN101553487B publication Critical patent/CN101553487B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

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)
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)

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
CN101553487A CN101553487A (zh) 2009-10-07
CN101553487B true CN101553487B (zh) 2012-06-13

Family

ID=39110526

Family Applications (1)

Application Number Title Priority Date Filing Date
CN2007800395790A Active CN101553487B (zh) 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

Country Status (16)

Country Link
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 (73)

* 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
EP3345905B1 (en) 2008-09-18 2021-09-01 Auspex Pharmaceuticals, Inc. Deuterated benzoquinolizine derivatives as 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
EP2897615A4 (en) 2012-09-18 2016-04-27 Auspex Pharmaceuticals Inc PHARMACOKINETIC FORMULATIONS OF DEUTERATED BENZOCHINOL INHIBITORS OF THE VESICLE 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
US20160068526A1 (en) 2013-01-31 2016-03-10 Auspex Pharmaceuticals, Inc. Benzoquinolone inhibitors of vmat2
WO2015048370A1 (en) * 2013-09-27 2015-04-02 Auspex Pharmaceuticals, Inc. Benzoquinolone inhibitors of vmat2
EP3424504A1 (en) * 2013-12-03 2019-01-09 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.
WO2015120110A2 (en) 2014-02-07 2015-08-13 Auspex Pharmaceuticals, Inc. Novel pharmaceutical formulations
WO2015120317A1 (en) 2014-02-07 2015-08-13 Neurocrine Biosciences, Inc. Pharmaceutical compositions comprising an antipsychotic drug and a vmat2 inhibitor and uses thereof
PE20161573A1 (es) 2014-02-13 2017-01-19 Incyte Corp Ciclopropilamina como inhibidor de la lsd1
KR20240011255A (ko) * 2014-05-06 2024-01-25 뉴로크린 바이오사이언시즈 인코퍼레이티드 과다운동성 운동 장애의 치료를 위한 vmat2 억제제
CN107438606B (zh) * 2015-02-06 2020-09-18 纽罗克里生物科学有限公司 [9,10-二甲氧基-3-(2-甲基丙基)-1h,2h,3h,4h,6h,7h,11bh-吡啶并-[2,1-a]异喹啉-2-基]甲醇及与其相关的化合物、组合物和方法
WO2016144901A1 (en) 2015-03-06 2016-09-15 Auspex Pharmaceuticals, Inc. Methods for the treatment of abnormal involuntary movement disorders
PE20180455A1 (es) 2015-04-03 2018-03-05 Incyte Corp Compuestos heterociclicos como inhibidores de lsd1
MX390795B (es) * 2015-06-23 2025-03-21 Neurocrine Biosciences Inc Inhibidores de transportador de monoamina vesicular tipo 2 (vmat2) para tratar enfermedades o trastornos neurologicos.
SG10202001219UA (en) 2015-08-12 2020-03-30 Incyte Corp Salts of an lsd1 inhibitor
WO2017060870A1 (en) 2015-10-09 2017-04-13 Hermann Russ Combination of deuterated levodopa with carbidopa and opicapone for the treatment of parkinson`s disease
CN115304596A (zh) * 2015-10-30 2022-11-08 纽罗克里生物科学有限公司 Valbenazine盐及其多晶形物
SI3394057T1 (sl) 2015-12-23 2022-06-30 Neurocrine Biosciences, Inc. Sintetičen postopek za pripravo (S)-(2R,3R,11bR)-3-izobutil-9,10-dimetoksi-2,3,4,6,7,11b-heksahidro-1H- pirido(2,1,-a)izokinolin-2-il 2-amino-3-metilbutanoat di(4-metilbenzensulfonata)
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
WO2018067945A1 (en) * 2016-10-06 2018-04-12 Assia Chemical Industries Ltd. Solid state forms of valbenazine
WO2018102673A1 (en) 2016-12-02 2018-06-07 Neurocrine Biosciences, Inc. Use of valbenazine for treating schizophrenia or schizoaffective disorder
WO2018130345A1 (en) 2017-01-10 2018-07-19 Sandoz Ag Crystalline valbenazine free base
MY199695A (en) * 2017-01-27 2023-11-18 Neurocrine Biosciences Inc Methods for the administration of certain vmat2 inhibitors
WO2018153632A1 (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
KR20230003308A (ko) 2017-03-15 2023-01-05 오스펙스 파마슈티칼스, 인코포레이티드 듀테트라베나진의 유사체, 이의 제조 및 용도
GB201705303D0 (en) * 2017-04-01 2017-05-17 Adeptio Pharmaceuticals Ltd Pharmaceutical compositions
CN110691596A (zh) * 2017-04-01 2020-01-14 阿德普蒂奥制药有限公司 药物组合物
GB201705305D0 (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
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
DK3684333T3 (da) 2017-09-21 2025-05-12 Neurocrine Biosciences Inc Valbenazin-formulering med høj dosis og sammensætninger, fremgangsmåder og kits relateret hertil
KR20250070134A (ko) 2017-10-10 2025-05-20 뉴로크린 바이오사이언시즈 인코퍼레이티드 특정 vmat2 억제제의 투여 방법
US20200230127A1 (en) 2017-10-10 2020-07-23 Neurocrine Biosciences, Inc. Methods for the Administration of Certain VMAT2 Inhibitors
RU2020114598A (ru) 2017-11-08 2021-12-09 Фореси Фармасьютикалс Ко., Лтд. Сложные эфиры дигидротетрабеназина
US11384077B2 (en) 2017-11-22 2022-07-12 Assia Chemical Industries Ltd. Solid state form of Valbenazine
JP7212958B2 (ja) 2017-12-26 2023-01-26 ▲蘇▼州科睿思制▲葯▼有限公司 バルベナジントシル酸塩の結晶形及びその製造方法並びに用途
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
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.
BR112021000019A2 (pt) 2018-08-15 2021-04-06 Neurocrine Biosciences Inc. Métodos para administração de certos inibidores 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
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
CN117736203A (zh) 2019-09-13 2024-03-22 纽罗克里生物科学有限公司 用于合成缬苯那嗪的方法
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
AR125188A1 (es) 2021-03-22 2023-06-21 Neurocrine Biosciences Inc Inhibidores del vmat2 y métodos de uso
WO2022232060A1 (en) 2021-04-26 2022-11-03 Neurocrine Biosciences, Inc. Processes for the synthesis of valbenazine
EP4362944A1 (en) 2021-06-30 2024-05-08 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.
IL315181A (en) 2022-03-07 2024-10-01 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
CN119907800A (zh) 2022-09-21 2025-04-29 纽罗克里生物科学有限公司 六氢-2H-吡啶并[2,1-a]异喹啉VMAT2抑制剂及其使用方法
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

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
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
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
EP2698170A1 (en) 2005-06-29 2014-02-19 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
EP1855677B1 (en) 2005-08-06 2008-12-03 Cambridge Laboratories (Ireland) Limited 3,11b cis dihydrotetrabanezine 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

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. *

Also Published As

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

Similar Documents

Publication Publication Date Title
CN101553487B (zh) 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
AU2013296627C9 (en) Deuterated ibrutinib
JP2025081429A (ja) （ｓ）－７－（１－アクリロイルピペリジン－４－イル）－２－（４－フェノキシフェニル）－４，５，６，７－テトラ－ヒドロピラゾロ［１，５－ａ］ピリミジン－３－カルボキサミドの結晶形、その調製、及びその使用
US20150071918A1 (en) Peptides for the treatment of cancer
US20090156671A1 (en) Deuterium-enriched oxybutynin
EP1638934B1 (en) 3-aminopyrrolidines as inhibitors of monoamine uptake
EP1120416A1 (en) Pyrido[2.3-b][1,4]benzodiazepinones as M2 receptor ligand for the treatment of neurological disorders
US6825193B2 (en) Citric acid salt of a therapeutic compound and pharmaceutical compositions thereof
US20240327372A1 (en) Preparation of phenethylamines and cathinones and stereoisomers thereof and precursors thereof
EP3980401B1 (en) Purine derivatives, as nr2b negative modulators and the use thereof as medicament, in particular for treating depressive disorders
RU2840772C1 (ru) Замещенные пиперидиновые соединения и их применение
WO2018023009A1 (en) Deuterated lurasidone
US20090062331A1 (en) Deuterium-enriched maraviroc
HK40129633A (zh) 苯乙胺和卡西酮及其立体异构体与其前体的制备
EP1501793A1 (en) Tamsulosin derivative
CN121532384A (zh) 嘧啶化合物及其作为usp1抑制剂的用途
IL324923A (en) Asymmetric phenylalkylamines
US20220306637A1 (en) Imidazopyrazine Derivatives and the Use Thereof as Medicament
Muth Design, Synthesis, and Biological Evaluation of Novel Polyamine Transport System Probes and Their Application to Human Cancers
US20220064122A1 (en) Analogs of Dextromethorphan with Balanced Receptor Activities
CN104520272A (zh) 新型多奈哌齐衍生物

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CB03 Change of inventor or designer information
CB03 Change of inventor or designer information

Inventor after: Gano Kyle W.

Inventor after: Nichol Harriot

Inventor before: Gano Kyle W.