CL2013003646A1 - Compuestos derivados de trans-1-(3s.1r)-6-cloro-3-fenilindan-1-il)-1,2,2-trimetilpiperazina deuterados, con actividad en los receptores 5ht2, d1 y d2; proceso de preparacion; compuesto intermediario; composicion y combinacion farmaceutica; y su uso para el tratamiento de la psicosis, entre otros. - Google Patents

Compuestos derivados de trans-1-(3s.1r)-6-cloro-3-fenilindan-1-il)-1,2,2-trimetilpiperazina deuterados, con actividad en los receptores 5ht2, d1 y d2; proceso de preparacion; compuesto intermediario; composicion y combinacion farmaceutica; y su uso para el tratamiento de la psicosis, entre otros.

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Publication number
CL2013003646A1
CL2013003646A1 CL2013003646A CL2013003646A CL2013003646A1 CL 2013003646 A1 CL2013003646 A1 CL 2013003646A1 CL 2013003646 A CL2013003646 A CL 2013003646A CL 2013003646 A CL2013003646 A CL 2013003646A CL 2013003646 A1 CL2013003646 A1 CL 2013003646A1
Authority
CL
Chile
Prior art keywords
psychosis
treatment
pharmaceutical composition
phenylindan
trimethylpiperazine
Prior art date
Application number
CL2013003646A
Other languages
English (en)
Spanish (es)
Inventor
Morten Jorgensen
Peter Hongaard Andersen
Mette Graulund Hvenegaard
Klaus Gjervig Jensen
Mikkel Fog Jacobsen
Lassina Badolo
Original Assignee
H Lundbeck As
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
Application filed by H Lundbeck As filed Critical H Lundbeck As
Publication of CL2013003646A1 publication Critical patent/CL2013003646A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
    • C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/451—Non condensed piperidines, e.g. piperocaine having a carbocyclic group directly attached to the heterocyclic ring, e.g. glutethimide, meperidine, loperamide, phencyclidine, piminodine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CL2013003646A 2011-06-20 2013-12-19 Compuestos derivados de trans-1-(3s.1r)-6-cloro-3-fenilindan-1-il)-1,2,2-trimetilpiperazina deuterados, con actividad en los receptores 5ht2, d1 y d2; proceso de preparacion; compuesto intermediario; composicion y combinacion farmaceutica; y su uso para el tratamiento de la psicosis, entre otros. CL2013003646A1 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161498651P 2011-06-20 2011-06-20
US201161537103P 2011-09-21 2011-09-21

Publications (1)

Publication Number Publication Date
CL2013003646A1 true CL2013003646A1 (es) 2014-07-04

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CL2013003646A CL2013003646A1 (es) 2011-06-20 2013-12-19 Compuestos derivados de trans-1-(3s.1r)-6-cloro-3-fenilindan-1-il)-1,2,2-trimetilpiperazina deuterados, con actividad en los receptores 5ht2, d1 y d2; proceso de preparacion; compuesto intermediario; composicion y combinacion farmaceutica; y su uso para el tratamiento de la psicosis, entre otros.

Country Status (40)

Country Link
US (9) US8575174B2 (https=)
EP (4) EP4215512A1 (https=)
JP (1) JP5668177B2 (https=)
KR (2) KR101879474B1 (https=)
CN (1) CN103649019B (https=)
AP (1) AP3310A (https=)
AR (1) AR086987A1 (https=)
AU (1) AU2012273657B2 (https=)
BR (1) BR112013031702B1 (https=)
CA (1) CA2837820C (https=)
CL (1) CL2013003646A1 (https=)
CO (1) CO6821965A2 (https=)
CR (1) CR20130654A (https=)
CY (2) CY1118158T1 (https=)
DK (2) DK2720989T3 (https=)
DO (1) DOP2013000305A (https=)
EA (1) EA024651B1 (https=)
EC (1) ECSP14013155A (https=)
ES (3) ES2719145T3 (https=)
GE (1) GEP201706655B (https=)
GT (1) GT201300304A (https=)
HR (2) HRP20161348T1 (https=)
HU (2) HUE044043T2 (https=)
IL (1) IL229640B (https=)
JO (1) JO3128B1 (https=)
LT (2) LT2720989T (https=)
MA (1) MA35268B1 (https=)
MD (1) MD4538C1 (https=)
ME (2) ME02513B (https=)
MX (1) MX339552B (https=)
MY (1) MY196998A (https=)
PE (2) PE20141113A1 (https=)
PH (1) PH12013502598A1 (https=)
PL (2) PL3135656T3 (https=)
PT (2) PT3135656T (https=)
RS (2) RS58546B1 (https=)
SI (2) SI2720989T1 (https=)
SM (2) SMT201900179T1 (https=)
TW (3) TWI614234B (https=)
WO (1) WO2012176066A1 (https=)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK2720989T3 (en) * 2011-06-20 2016-11-28 H Lundbeck As Deuterated 1-piperazino-3-phenyl-indanes used to treat schizophrenia
AR094054A1 (es) * 2012-12-19 2015-07-08 H Lundbeck As 6-cloro-3-(fenil-d₅)-inden-1-ona y uso de la misma
JP7266022B2 (ja) 2017-09-07 2023-04-27 大塚製薬株式会社 ピペリジン誘導体のピペリジン窒素を重水素低級アルキルでモノアルキル化する工業的製造方法
WO2020089147A1 (en) 2018-10-29 2020-05-07 H. Lundbeck A/S Amorphous compounds of formula (i) and amorphous compounds of formula (i) salts
WO2020114853A1 (en) 2018-12-03 2020-06-11 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-((1/r,3s)-6-chloro-3-(phenyl-d5)-2,3-dihydro-1h-inden-1-yl)-2,2-dimethy-1-(methyl-d3)piperazine
SG11202106692UA (en) * 2018-12-21 2021-07-29 Concert Pharmaceuticals Inc Deuterated forms and derivatives of volinanserin
ES3040728T3 (en) * 2019-03-13 2025-11-04 Otsuka Pharma Co Ltd Method for introducing deuterated lower alkyl into amine moiety of compound containing secondary amine
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

Family Cites Families (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE50867B1 (en) * 1980-02-29 1986-08-06 Kefalas As Indane derivatives
GB8427125D0 (en) 1984-10-26 1984-12-05 Lundbeck & Co As H Organic compounds
ATE60571T1 (de) 1984-12-04 1991-02-15 Sandoz Ag Inden-analoga von mevalonolakton und ihre derivate.
DK286990D0 (da) 1990-12-04 1990-12-04 Lundbeck & Co As H Indanderivater
DK55192D0 (da) * 1992-04-28 1992-04-28 Lundbeck & Co As H 1-piperazino-1,2-dihydroindenderivater
ES2293638T3 (es) 1994-03-25 2008-03-16 Isotechnika, Inc. Mejora de la eficacia de farmacos por deuteracion.
US6221335B1 (en) 1994-03-25 2001-04-24 Isotechnika, Inc. Method of using deuterated calcium channel blockers
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
PL1658277T3 (pl) 2003-08-18 2012-10-31 H Lundbeck As Sól bursztynianowa i malonianowa trans-4-((1R,3S)-6-chloro-3-fenyloindan-1-ylo)-1,2,2-tri-metylopiperazyny i zastosowanie jako lek
MEP2408A (xx) * 2003-08-18 2010-02-10 Lundbeck & Co As H Trans-1-(6-hloro-3 fenilindan-1-1l)-3,3-dimetilpiperazin
RU2366654C2 (ru) 2004-06-08 2009-09-10 ЭнЭсЭйБи, ФИЛИАЛ АФ НЕУРОСЕРЧ СВИДЕН АБ, СВЕРИЙЕ Новые дизамещенные фенилпиперидины/пиперазины в качестве модуляторов допаминовой нейротрансмиссии
ES2346452T3 (es) 2004-06-08 2010-10-15 Nsab, Filial Af Neurosearch Sweden Ab, Sverige Nuevas fenilpiperidinas/piperazinas disustituidas utilizadas como moduladores de la neurotransmision de la dopamina.
WO2006086985A1 (en) 2005-02-16 2006-08-24 H. Lundbeck A/S Tartrate and malate salts of trans-1-((1r,3s)-6-chloro-3-phenylindan-1-yl)-3,3-dimethylpiperazine
TWI376373B (en) 2005-02-16 2012-11-11 Lundbeck & Co As H Crystalline base of a pharmaceutical compound
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
KR101380190B1 (ko) 2005-07-29 2014-04-11 콘서트 파마슈티컬즈, 인크. 벤조 〔ｄ〕〔１,３〕―디옥솔 유도체
US7863274B2 (en) 2005-07-29 2011-01-04 Concert Pharmaceuticals Inc. Deuterium enriched analogues of tadalafil as PDE5 inhibitors
PT1954669E (pt) 2005-12-01 2015-10-23 Auspex Pharmaceuticals Inc Feniletilaminas substituídas com actividade serotoninérgica e/ou norepinefrinérgica
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
AU2008242703B2 (en) 2007-04-19 2011-08-18 Concert Pharmaceuticals Inc. Deuterated morpholinyl compounds
EP1997479A1 (en) 2007-05-31 2008-12-03 Helm AG Stabilized amorphous candesartan cilexetil compositions for oral administration
EP2116532B1 (en) 2007-06-12 2011-12-07 Concert Pharmaceuticals, Inc. Azapeptide derivatives as HIV protease inhibitors
US20090062303A1 (en) 2007-08-29 2009-03-05 Protia, Llc Deuterium-enriched ziprasidone
CN102065861B (zh) 2008-05-07 2013-10-16 H.隆德贝克有限公司 反式-4-((1r，3s)-6-氯-3-苯基茚满-1-基)-1，2，2-三甲基哌嗪用于改善认知的用途
CN102170884A (zh) 2008-10-03 2011-08-31 H.隆德贝克有限公司 口服制剂
JP2012506904A (ja) 2008-10-28 2012-03-22 エージェンシー フォー サイエンス，テクノロジー アンド リサーチ 難水溶性成分のためのメソ多孔性材料賦形剤
US20120071554A1 (en) 2008-10-28 2012-03-22 Liu Julie F 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
EP2639216B1 (en) 2010-11-09 2018-07-11 Kaneka Corporation Halogenated indenones and method for producing optically active indanones or optically active indanols by using same
US20130331575A1 (en) 2011-01-07 2013-12-12 Robert Dancer Method for resolution 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
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
DK2720989T3 (en) * 2011-06-20 2016-11-28 H Lundbeck As Deuterated 1-piperazino-3-phenyl-indanes used to treat schizophrenia
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

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