CN103649019B - 用于治疗精神分裂症的氘化的1-哌嗪子基-3-苯基-茚满 - Google Patents

用于治疗精神分裂症的氘化的1-哌嗪子基-3-苯基-茚满 Download PDF

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CN103649019B
CN103649019B CN201280029731.8A CN201280029731A CN103649019B CN 103649019 B CN103649019 B CN 103649019B CN 201280029731 A CN201280029731 A CN 201280029731A CN 103649019 B CN103649019 B CN 103649019B
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compound
deuterium
phenyl
chloro
atom
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CN103649019A (zh
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M.乔根森
P.H.安德森
K.G.詹森
M.G.赫维內加尔德
L.巴多洛
M.F.贾科布森
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H Lundbeck AS
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    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445Non condensed piperidines, e.g. piperocaine
    • A61K31/451Non condensed piperidines, e.g. piperocaine having a carbocyclic group directly attached to the heterocyclic ring, e.g. glutethimide, meperidine, loperamide, phencyclidine, piminodine
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    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445Non condensed piperidines, e.g. piperocaine
    • A61K31/4523Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445Non condensed piperidines, e.g. piperocaine
    • A61K31/4523Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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    • A61K31/496Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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    • A61K31/55Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
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CN201280029731.8A 2011-06-20 2012-06-19 用于治疗精神分裂症的氘化的1-哌嗪子基-3-苯基-茚满 Active CN103649019B (zh)

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Application Number Priority Date Filing Date Title
US201161498651P 2011-06-20 2011-06-20
US61/498651 2011-06-20
US61/498,651 2011-06-20
US201161537103P 2011-09-21 2011-09-21
US61/537103 2011-09-21
US61/537,103 2011-09-21
PCT/IB2012/001386 WO2012176066A1 (en) 2011-06-20 2012-06-19 Deuterated 1-piperazino-3-phenyl indanes for treatment of schizophrenia

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CN103649019A CN103649019A (zh) 2014-03-19
CN103649019B true CN103649019B (zh) 2015-09-16

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Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2719145T3 (es) 2011-06-20 2019-07-08 H Lundbeck As 1-Piperazino-3-fenil-indanos deuterados para el tratamiento de la esquizofrenia
AR094054A1 (es) * 2012-12-19 2015-07-08 H Lundbeck As 6-cloro-3-(fenil-d₅)-inden-1-ona y uso de la misma
PT3679018T (pt) 2017-09-07 2022-04-05 Otsuka Pharma Co Ltd Processo industrial de monoalquilação de um nitrogénio de piperidina em derivados de piperidina com alquilo deuterado
EP3873885A1 (en) * 2018-10-29 2021-09-08 H. Lundbeck A/S Amorphous compounds of formula (i) and amorphous compounds of formula (i) salts
US11535600B2 (en) 2018-12-03 2022-12-27 H. Lundbeck A/S Prodrugs of 4-((1R,3S)-6-chloro-3-phenyl-2,3-dihydro-1H-inden-1-yl)-1,2,2-trimethylpiperazine and 4-((1R,3S)-6-chloro-3-(phenyl-d5)-2,3-dihydro-1H-inden-1-yl)-2,2-dimethyl-1-(methyl-d3)piperazine
EA202191731A1 (ru) * 2018-12-21 2021-10-28 Консерт Фармасьютикалз, Инк. Дейтерированные формы и производные волинансерина
CN113518771A (zh) * 2019-03-13 2021-10-19 大塚制药株式会社 向含有仲胺的化合物的胺部分导入氘代低级烷基的方法
CN117164518A (zh) * 2022-05-26 2023-12-05 四川大学 一种制备氘代咪唑类化合物的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993022293A1 (en) * 1992-04-28 1993-11-11 H. Lundbeck A/S 1-piperazino-1,2-dihydroindene derivatives
CN101935305A (zh) * 2003-08-18 2011-01-05 H.隆德贝克有限公司 反式-4-((1r,3s)-6-氯-3-苯基茚满-1-基)-1,2,2-三甲基哌嗪及其盐的制备方法及所用中间体

Family Cites Families (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ196284A (en) 1980-02-29 1983-12-16 Kefalas As 1-piperazino-3-phenylindane derivatives:pharmaceutical compositions
GB8427125D0 (en) 1984-10-26 1984-12-05 Lundbeck & Co As H Organic compounds
HU198005B (en) 1984-12-04 1989-07-28 Sandoz Ag Process for producing mevqlolakton, derivatives, its indene-analogues and pharmaceutical compositions containing them
DK286990D0 (da) 1990-12-04 1990-12-04 Lundbeck & Co As H Indanderivater
US6221335B1 (en) 1994-03-25 2001-04-24 Isotechnika, Inc. Method of using deuterated calcium channel blockers
JP3696884B2 (ja) 1994-03-25 2005-09-21 アイソテクニカ、インコーポレーテッド ジュウテリウム化による薬物の効能の増強
WO1999015524A1 (en) 1997-09-23 1999-04-01 Fujisawa Pharmaceutical Co., Ltd. Thiazole derivatives
US6350786B1 (en) 1998-09-22 2002-02-26 Hoffmann-La Roche Inc. Stable complexes of poorly soluble compounds in ionic polymers
SE9904850D0 (sv) 1999-12-30 1999-12-30 Pharmacia & Upjohn Ab Novel process and intermediates
UA81749C2 (uk) 2001-10-04 2008-02-11 Х. Луннбек А/С Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну
CA2536073A1 (en) 2003-08-18 2005-02-24 H. Lundbeck A/S Trans-1(6-chloro-3-phenylindan-1-yl)-3,3-dimethylpiperazine
RU2366654C2 (ru) 2004-06-08 2009-09-10 ЭнЭсЭйБи, ФИЛИАЛ АФ НЕУРОСЕРЧ СВИДЕН АБ, СВЕРИЙЕ Новые дизамещенные фенилпиперидины/пиперазины в качестве модуляторов допаминовой нейротрансмиссии
AU2005251909A1 (en) 2004-06-08 2005-12-22 Nsab, Filial Af Neurosearch Sweden Ab, Sverige New disubstituted phenylpiperidines as modulators of dopamine and serotonin neurotransmission
JP2008530039A (ja) 2005-02-16 2008-08-07 ハー・ルンドベック・アクチエゼルスカベット トランス−1−((1r,3s)−6−クロロ−3−フェニルインダン−1−イル)−3,3−ジメチルピペラジンの酒石酸塩およびリンゴ酸塩
TWI453198B (zh) 2005-02-16 2014-09-21 Lundbeck & Co As H 製造反式-1-((1r,3s)-6-氯基-3-苯基茚滿-1-基) -3 , 3 -二甲基六氫吡與其鹽類之方法及製造4-((1r , 3s)-6 -氯基-3-苯基茚滿-1-基 )-1,2,2-三甲基六氫吡與其鹽類之方法
TWI376373B (en) 2005-02-16 2012-11-11 Lundbeck & Co As H Crystalline base of a pharmaceutical compound
JP5301991B2 (ja) 2005-07-29 2013-09-25 コンサート ファーマシューティカルズ インコーポレイテッド 新規なベンゾ[d][1,3]−ジオキソール誘導体
US7863274B2 (en) 2005-07-29 2011-01-04 Concert Pharmaceuticals Inc. Deuterium enriched analogues of tadalafil as PDE5 inhibitors
HUE027865T2 (en) 2005-12-01 2016-11-28 Auspex Pharmaceuticals Inc Substituted phenyl ethylamines with serotonergic and / or norepinephrine activity
JP4986462B2 (ja) 2006-01-27 2012-07-25 シャープ株式会社 太陽電池ストリングおよびその製造方法、ならびに、その太陽電池ストリングを用いる太陽電池モジュール
TW200819426A (en) 2006-08-31 2008-05-01 Lundbeck & Co As H Novel indane compounds
WO2008086158A1 (en) 2007-01-04 2008-07-17 Smithkline Beecham Corporation Benzodihydroquinazoline as pi3 kinase inhibitors
US8198305B2 (en) 2007-04-13 2012-06-12 Concert Pharmaceuticals Inc. 1,2-benzisoxazol-3-yl compounds
WO2008131259A1 (en) 2007-04-19 2008-10-30 Concert Pharmaceuticals Inc. Deuterated morpholinyl compounds
EP1997479A1 (en) 2007-05-31 2008-12-03 Helm AG Stabilized amorphous candesartan cilexetil compositions for oral administration
SI2003120T1 (sl) 2007-06-12 2010-03-31 Concert Pharmaceuticals Inc Azapeptidni derivati kot inhibitorji hiv proteaze
US20090062303A1 (en) 2007-08-29 2009-03-05 Protia, Llc Deuterium-enriched ziprasidone
JP2011519873A (ja) 2008-05-07 2011-07-14 ハー・ルンドベック・アクチエゼルスカベット 認知欠損を治療する方法
CA2732613A1 (en) 2008-10-03 2010-04-08 H. Lundbeck A/S Oral formulation
EP2349336B1 (en) 2008-10-28 2017-11-22 Agency For Science, Technology And Research Mesoporous material excipients for poorly aqueous soluble ingredients
EP2362865A2 (en) 2008-10-28 2011-09-07 Concert Pharmaceuticals Inc. Deuterated 2-propylpentanoic acid compounds
US8263601B2 (en) 2009-02-27 2012-09-11 Concert Pharmaceuticals, Inc. Deuterium substituted xanthine derivatives
TW201102370A (en) 2009-07-07 2011-01-16 Lundbeck & Co As H Manufacture of 4-((1R,3S)-6-chloro-3-phenyl-indan-1-yl)-1,2,2-trimethyl-piperazine and 1-((1R,3S)-6-chloro-3-phenyl-indan-1-yl)-3,3-dimethyl piperazine
US8557994B2 (en) 2009-07-27 2013-10-15 Daljit Singh Dhanoa Deuterium-enriched pyridinonecarboxamides and derivatives
US8658236B2 (en) * 2009-08-21 2014-02-25 Deuteria Beverages, Llc Alcoholic compositions having a lowered risk of acetaldehydemia
KR101149529B1 (ko) 2009-09-11 2012-05-25 한국화학연구원 인덴온 유도체 및 이를 포함하는 약학적 조성물
CN102020522A (zh) * 2009-09-21 2011-04-20 陈松源 氘代药物的制备方法和应用
WO2011047315A1 (en) 2009-10-15 2011-04-21 Concert Pharmaceuticals, Inc. Subsitituted benzimidazoles
WO2011059080A1 (ja) * 2009-11-16 2011-05-19 第一三共株式会社 同位体置換されたジアミン誘導体
EP2521711B1 (en) 2010-01-07 2017-08-16 Alkermes Pharma Ireland Limited Quaternary ammonium salt prodrugs
CN103209949B (zh) 2010-11-09 2016-08-10 株式会社钟化 卤化茚酮类及使用其的光学活性茚满酮类或光学活性茚满醇类的制造方法
CN103429577A (zh) 2011-01-07 2013-12-04 H.隆德贝克有限公司 4-((1r,3s)-6-氯-3-苯基-茚满-1-基)-1,2,2-三甲基哌嗪和1-((1r,3s)-6-氯-3-苯基-茚满-1-基)-3,3-二甲基哌嗪的拆分方法
WO2012137225A1 (en) 2011-04-08 2012-10-11 Sphaera Pharma Pvt. Ltd Substituted methylformyl reagents and method of using same to modify physicochemical and/or pharmacokinetic properties of compounds
ES2719145T3 (es) 2011-06-20 2019-07-08 H Lundbeck As 1-Piperazino-3-fenil-indanos deuterados para el tratamiento de la esquizofrenia
AU2013326850B2 (en) 2012-10-04 2017-09-21 Inhibikase Therapeutics, Inc. Novel compounds, their preparation and their uses
AR094054A1 (es) 2012-12-19 2015-07-08 H Lundbeck As 6-cloro-3-(fenil-d₅)-inden-1-ona y uso de la misma

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993022293A1 (en) * 1992-04-28 1993-11-11 H. Lundbeck A/S 1-piperazino-1,2-dihydroindene derivatives
CN101935305A (zh) * 2003-08-18 2011-01-05 H.隆德贝克有限公司 反式-4-((1r,3s)-6-氯-3-苯基茚满-1-基)-1,2,2-三甲基哌嗪及其盐的制备方法及所用中间体

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