IL229640B - Deuterium-containing 1-piperazino-3-phenylindanes for the treatment of schizophrenia - Google Patents

Deuterium-containing 1-piperazino-3-phenylindanes for the treatment of schizophrenia

Info

Publication number
IL229640B
IL229640B IL229640A IL22964013A IL229640B IL 229640 B IL229640 B IL 229640B IL 229640 A IL229640 A IL 229640A IL 22964013 A IL22964013 A IL 22964013A IL 229640 B IL229640 B IL 229640B
Authority
IL
Israel
Prior art keywords
piperazino
deuterated
schizophrenia
treatment
indanes
Prior art date
Application number
IL229640A
Other languages
English (en)
Hebrew (he)
Other versions
IL229640A0 (en
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 IL229640A0 publication Critical patent/IL229640A0/en
Publication of IL229640B publication Critical patent/IL229640B/en

Links

Classifications

    • 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
    • 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
    • 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
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicinal Preparation (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
IL229640A 2011-06-20 2013-11-26 Deuterium-containing 1-piperazino-3-phenylindanes for the treatment of schizophrenia IL229640B (en)

Applications Claiming Priority (3)

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

Publications (2)

Publication Number Publication Date
IL229640A0 IL229640A0 (en) 2014-01-30
IL229640B true IL229640B (en) 2018-02-28

Family

ID=46682855

Family Applications (1)

Application Number Title Priority Date Filing Date
IL229640A IL229640B (en) 2011-06-20 2013-11-26 Deuterium-containing 1-piperazino-3-phenylindanes for the treatment of schizophrenia

Country Status (40)

Country Link
US (9) US8575174B2 (enExample)
EP (4) EP3508468B1 (enExample)
JP (1) JP5668177B2 (enExample)
KR (2) KR101879474B1 (enExample)
CN (1) CN103649019B (enExample)
AP (1) AP3310A (enExample)
AR (1) AR086987A1 (enExample)
AU (1) AU2012273657B2 (enExample)
BR (1) BR112013031702B1 (enExample)
CA (1) CA2837820C (enExample)
CL (1) CL2013003646A1 (enExample)
CO (1) CO6821965A2 (enExample)
CR (1) CR20130654A (enExample)
CY (2) CY1118158T1 (enExample)
DK (2) DK2720989T3 (enExample)
DO (1) DOP2013000305A (enExample)
EA (1) EA024651B1 (enExample)
EC (1) ECSP14013155A (enExample)
ES (3) ES2719145T3 (enExample)
GE (1) GEP201706655B (enExample)
GT (1) GT201300304A (enExample)
HR (2) HRP20161348T1 (enExample)
HU (2) HUE044043T2 (enExample)
IL (1) IL229640B (enExample)
JO (1) JO3128B1 (enExample)
LT (2) LT2720989T (enExample)
MA (1) MA35268B1 (enExample)
MD (1) MD4538C1 (enExample)
ME (2) ME03375B (enExample)
MX (1) MX339552B (enExample)
MY (1) MY196998A (enExample)
PE (2) PE20150928A1 (enExample)
PH (1) PH12013502598A1 (enExample)
PL (2) PL3135656T3 (enExample)
PT (2) PT3135656T (enExample)
RS (2) RS55304B1 (enExample)
SI (2) SI3135656T1 (enExample)
SM (2) SMT201900179T1 (enExample)
TW (3) TWI614234B (enExample)
WO (1) WO2012176066A1 (enExample)

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

Family Cites Families (48)

* 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
DK55192D0 (da) 1992-04-28 1992-04-28 Lundbeck & Co As H 1-piperazino-1,2-dihydroindenderivater
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
TWI388550B (zh) * 2003-08-18 2013-03-11 Lundbeck & Co As H 反-４-（（１ｒ，３ｓ）-６-氯-３-苯基二氫茚-１-基）-１，２，２-三甲基哌之琥珀酸氫鹽和丙二酸氫鹽及其作為醫藥品之用途
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

Also Published As

Publication number Publication date
AU2012273657B2 (en) 2016-07-21
LT3135656T (lt) 2019-04-25
PH12013502598A1 (en) 2014-02-10
US10501427B2 (en) 2019-12-10
HRP20161348T1 (hr) 2016-12-02
KR101939546B1 (ko) 2019-01-16
US11059798B2 (en) 2021-07-13
BR112013031702B1 (pt) 2021-11-03
US9216961B2 (en) 2015-12-22
US10118907B2 (en) 2018-11-06
TW201902481A (zh) 2019-01-16
SMT201600383B (it) 2017-01-10
EP2720989A1 (en) 2014-04-23
US20120322811A1 (en) 2012-12-20
AP3310A (en) 2015-06-30
JP2014520140A (ja) 2014-08-21
US20170158650A1 (en) 2017-06-08
GEP201706655B (en) 2017-04-25
DOP2013000305A (es) 2014-02-28
SI2720989T1 (sl) 2016-11-30
US20250250244A1 (en) 2025-08-07
HRP20190593T1 (hr) 2019-05-17
MY196998A (en) 2023-05-17
MD20140004A2 (en) 2014-05-31
TW201722895A (zh) 2017-07-01
ES2939477T3 (es) 2023-04-24
US20130281436A1 (en) 2013-10-24
TWI659741B (zh) 2019-05-21
SMT201900179T1 (it) 2019-05-10
AU2012273657A1 (en) 2013-12-12
HK1197228A1 (zh) 2015-01-09
CA2837820A1 (en) 2012-12-27
US20220119362A1 (en) 2022-04-21
CY1121514T1 (el) 2020-05-29
BR112013031702A2 (pt) 2016-12-13
DK3135656T3 (en) 2019-04-23
NZ618222A (en) 2015-03-27
DK2720989T3 (en) 2016-11-28
AP2013007338A0 (en) 2013-12-31
MX2013014849A (es) 2014-03-31
KR101879474B1 (ko) 2018-07-17
WO2012176066A1 (en) 2012-12-27
KR20140041567A (ko) 2014-04-04
RS58546B1 (sr) 2019-05-31
ME02513B (me) 2017-02-20
MD4538C1 (ro) 2018-07-31
CL2013003646A1 (es) 2014-07-04
HUE030883T2 (en) 2017-06-28
MA35268B1 (fr) 2014-07-03
TW201311248A (zh) 2013-03-16
US9617231B2 (en) 2017-04-11
US20150307458A1 (en) 2015-10-29
EP3135656B1 (en) 2019-02-27
EP3135656A1 (en) 2017-03-01
CR20130654A (es) 2014-03-24
RS55304B1 (sr) 2017-03-31
CN103649019B (zh) 2015-09-16
GT201300304A (es) 2015-01-16
CO6821965A2 (es) 2013-12-31
ES2601213T3 (es) 2017-02-14
PE20141113A1 (es) 2014-09-25
ES2719145T3 (es) 2019-07-08
SI3135656T1 (sl) 2019-05-31
US8575174B2 (en) 2013-11-05
PL2720989T3 (pl) 2017-05-31
EP3508468B1 (en) 2023-01-18
CY1118158T1 (el) 2017-06-28
ECSP14013155A (es) 2014-02-28
TWI627956B (zh) 2018-07-01
MD4538B1 (ro) 2017-12-31
US12116355B2 (en) 2024-10-15
CN103649019A (zh) 2014-03-19
MX339552B (es) 2016-05-31
CA2837820C (en) 2019-02-19
PL3135656T3 (pl) 2019-07-31
IL229640A0 (en) 2014-01-30
JP5668177B2 (ja) 2015-02-12
US20190031631A1 (en) 2019-01-31
US20160068497A1 (en) 2016-03-10
PT2720989T (pt) 2016-11-07
PT3135656T (pt) 2019-05-03
EA201490045A1 (ru) 2014-07-30
ME03375B (me) 2020-01-20
EP4215512A1 (en) 2023-07-26
US20200131143A1 (en) 2020-04-30
PE20150928A1 (es) 2015-06-26
HUE044043T2 (hu) 2019-09-30
AR086987A1 (es) 2014-02-05
US9012453B2 (en) 2015-04-21
KR20180075717A (ko) 2018-07-04
TWI614234B (zh) 2018-02-11
LT2720989T (lt) 2016-11-25
EP2720989B1 (en) 2016-08-10
JO3128B1 (ar) 2017-09-20
EP3508468A1 (en) 2019-07-10
EA024651B1 (ru) 2016-10-31

Similar Documents

Publication Publication Date Title
EP2717855A4 (en) PROCESSING METHODS
HRP20190593T1 (hr) Deuterirani 1-piperazino-3-fenil indani za liječenje shizofrenije
HUE047354T2 (hu) Ivacaftor deuterizált származékai
PL3235812T3 (pl) Deuterowane pochodne iwakaftoru
GB201110095D0 (en) Method of treatment
EP2773754A4 (en) Methods of Treatment
GB201106960D0 (en) Treatment of waste
EP2685823A4 (en) CANCER TREATMENT
EP2709665A4 (en) TREATMENT OF PSORIASIS
ZA201309613B (en) Deuterated 1-piperazino-3-phenyl indanes for treatment of schizophrenia
EP2791324A4 (en) PROCESSING METHOD
GB201118065D0 (en) Treatment of movement disorders
GB201109737D0 (en) Methods of treatment
GB201110602D0 (en) Methods of treatment
ZA201404348B (en) Treatment of seborrhoea
GB201121044D0 (en) Treatment of solutions
GB201111530D0 (en) Method of treatment
GB201109509D0 (en) Method of treatment
GB201109266D0 (en) Method of treatment
GB201103044D0 (en) Method of treatment
GB201118269D0 (en) Treatment of cardiovascular disease
GB201107988D0 (en) Treatment of cardiovascular disease

Legal Events

Date Code Title Description
FF Patent granted
KB Patent renewed