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
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CL
Chile
Prior art keywords
psychosis
treatment
pharmaceutical composition
phenylindan
trimethylpiperazine
Prior art date
Application number
CL2013003646A
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English (en)
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
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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
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    • 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
    • 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)

Abstract

COMPUESTO DE FÓRMULA Y, DONDE R 1 - R1° SON, DE MODO INDEPENDIENTE, HIDRÓGENO O DEUTERIO, EN DONDE AL MENOS UNO DE R1—R1° COMPRENDE AL MENOS EL 50% DE DEUTERIO O UNA DE SUS SALES POR ADICIÓN DE ÁCIDOS FARMACÉUTICAMENTE ACEPTABLES. COMPOSICIÓN FARMACÉUTICA, QUE COMPRENDE DICHO COMPUESTO Y UNO O VARIOS PORTADORES, DILUYENTES O EXCIPIENTES FARMACÉUTICAMENTE ACEPTABLES. USO DE DICHO COMPUESTO PARA EL TRATAMIENTO DE PSICOSIS, OTRAS ENFERMEDADES QUE INCLUYEN SÍNTOMAS PSICÓTICOS, TRASTORNOS PSICÓTICOS O ENFERMEDADES QUE SE PRESENTAN CON SÍNTOMAS PSICÓTICOS. COMPUESTO INTERMEDIARIO Y PROCESOS PARA LA PREPARACIÓN DE DICHO COMPUESTO.
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

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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)

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US (8) US8575174B2 (es)
EP (4) EP4215512A1 (es)
JP (1) JP5668177B2 (es)
KR (2) KR101879474B1 (es)
CN (1) CN103649019B (es)
AP (1) AP3310A (es)
AR (1) AR086987A1 (es)
AU (1) AU2012273657B2 (es)
BR (1) BR112013031702B1 (es)
CA (1) CA2837820C (es)
CL (1) CL2013003646A1 (es)
CO (1) CO6821965A2 (es)
CR (1) CR20130654A (es)
CY (2) CY1118158T1 (es)
DK (2) DK2720989T3 (es)
DO (1) DOP2013000305A (es)
EA (1) EA024651B1 (es)
EC (1) ECSP14013155A (es)
ES (3) ES2939477T3 (es)
GE (1) GEP201706655B (es)
GT (1) GT201300304A (es)
HK (1) HK1197228A1 (es)
HR (2) HRP20161348T1 (es)
HU (2) HUE044043T2 (es)
IL (1) IL229640B (es)
JO (1) JO3128B1 (es)
LT (2) LT3135656T (es)
MA (1) MA35268B1 (es)
MD (1) MD4538C1 (es)
ME (2) ME03375B (es)
MX (1) MX339552B (es)
MY (1) MY196998A (es)
PE (2) PE20141113A1 (es)
PL (2) PL2720989T3 (es)
PT (2) PT2720989T (es)
RS (2) RS58546B1 (es)
SI (2) SI3135656T1 (es)
SM (1) SMT201600383B (es)
TW (3) TWI614234B (es)
WO (1) WO2012176066A1 (es)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ME03375B (me) 2011-06-20 2020-01-20 H Lundbeck As Deuterizovani 1-piperazin0-3-fenil indani za tretiranje šizofrenije
AR094054A1 (es) * 2012-12-19 2015-07-08 H Lundbeck As 6-cloro-3-(fenil-d₅)-inden-1-ona y uso de la misma
US11214545B2 (en) 2017-09-07 2022-01-04 Otsuka Pharmaceutical Co., Ltd. Industrial process of mono-alkylating piperidine nitrogen in piperidine derivative with deuterated-lower-alkyl
WO2020089147A1 (en) 2018-10-29 2020-05-07 H. Lundbeck A/S Amorphous compounds of formula (i) and amorphous compounds of formula (i) salts
JP2022509965A (ja) 2018-12-03 2022-01-25 ハー・ルンドベック・アクチエゼルスカベット ４－（（１Ｒ，３Ｓ）－６－クロロ－３－フェニル－２，３－ジヒドロ－１Ｈ－インデン－１－イル）－１，２，２－トリメチルピペラジン及び４－（（１Ｒ，３Ｓ）－６－クロロ－３－（フェニル－ｄ５）－２，３－ジヒドロ－１Ｈ－インデン－１－イル）－２，２－ジメチル－１－（メチル－ｄ３）ピペラジンのプロドラッグ
JP2022515156A (ja) * 2018-12-21 2022-02-17 テラン バイオサイエンシズ， インコーポレイテッド ボリナンセリンの重水素化形態および誘導体
EP3939954A4 (en) * 2019-03-13 2023-01-04 Otsuka Pharmaceutical Co., Ltd. METHOD FOR INTRODUCING A DEUTERED LOWER ALKYL INTO AN AMINE FRACTION OF A COMPOUND CONTAINING A SECONDARY AMINE

Family Cites Families (30)

* 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
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
DE69535592T2 (de) * 1994-03-25 2008-06-12 Isotechnika, Inc., Edmonton Verbesserung der effektivität von arzneimitteln duren deuterierung
US6221335B1 (en) 1994-03-25 2001-04-24 Isotechnika, Inc. Method of using deuterated calcium channel blockers
UA81749C2 (uk) 2001-10-04 2008-02-11 Х. Луннбек А/С Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну
JP5043429B2 (ja) 2003-08-18 2012-10-10 ハー・ルンドベック・アクチエゼルスカベット トランス−４−（（１ｒ，３ｓ）−６−クロロ−３−フェニルインダン−１−イル）−１，２，２−トリメチルピペラジンのコハク酸塩およびマロン酸塩、および薬剤としての使用方法
EA200600443A1 (ru) * 2003-08-18 2006-08-25 Х. Лундбекк А/С Транс-1-(6-хлор-3-фенилиндан-1-ил)-3,3-диметилпиперазин
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
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
US7863274B2 (en) 2005-07-29 2011-01-04 Concert Pharmaceuticals Inc. Deuterium enriched analogues of tadalafil as PDE5 inhibitors
CN101273024A (zh) 2005-07-29 2008-09-24 康瑟特制药公司 新颖苯并[d][1,3]-二氧杂环戊烯衍生物
EP1954669B1 (en) 2005-12-01 2015-07-08 Auspex Pharmaceuticals, Inc. Substituted phenethylamines with serotoninergic and/or norepinephrinergic 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
WO2008128166A1 (en) 2007-04-13 2008-10-23 Concert Pharmaceuticals Inc. Deuterated derivatives of 4-(6-fluoro-1, 2-benzisoxazol-3-yl) piperidine compounds
US7528131B2 (en) 2007-04-19 2009-05-05 Concert Pharmaceuticals Inc. Substituted morpholinyl compounds
AU2008267048C1 (en) 2007-06-12 2013-01-17 Concert Pharmaceuticals, Inc. Azapeptide derivatives
US20090062303A1 (en) 2007-08-29 2009-03-05 Protia, Llc Deuterium-enriched ziprasidone
BRPI0912223A2 (pt) 2008-05-07 2015-10-06 Lundbeck & Co As H métodos para melhorar funcionamento cognitivo e para tratar uma doença, composto, uso do mesmo, e, composição farmacêutica.
EA201170512A1 (ru) 2008-10-03 2011-08-30 Х. Лундбекк А/С Композиция для перорального введения
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
US8658236B2 (en) * 2009-08-21 2014-02-25 Deuteria Beverages, Llc Alcoholic compositions having a lowered risk of acetaldehydemia
CN102020522A (zh) * 2009-09-21 2011-04-20 陈松源 氘代药物的制备方法和应用
US8278460B2 (en) 2009-10-15 2012-10-02 Concert Pharmaceuticals, Inc. Substituted 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
ME03375B (me) 2011-06-20 2020-01-20 H Lundbeck As Deuterizovani 1-piperazin0-3-fenil indani za tretiranje šizofrenije

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