KR101879474B1 - 정신 분열증의 치료를 위한 중수소화 1-피페라지노-3-페닐 인단 - Google Patents

정신 분열증의 치료를 위한 중수소화 1-피페라지노-3-페닐 인단 Download PDF

Info

Publication number
KR101879474B1
KR101879474B1 KR1020137033717A KR20137033717A KR101879474B1 KR 101879474 B1 KR101879474 B1 KR 101879474B1 KR 1020137033717 A KR1020137033717 A KR 1020137033717A KR 20137033717 A KR20137033717 A KR 20137033717A KR 101879474 B1 KR101879474 B1 KR 101879474B1
Authority
KR
South Korea
Prior art keywords
compound
deuterium
delete delete
phenyl
chloro
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
KR1020137033717A
Other languages
English (en)
Korean (ko)
Other versions
KR20140041567A (ko
Inventor
모르텐 요르겐센
페테르 혼가르 안데르센
클라우스 기에르비 옌센
메테 그라우룬드 베네가르
라시나 바돌로
미켈 포그 야콥센
Original Assignee
하. 룬드벡 아크티에셀스카브
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 하. 룬드벡 아크티에셀스카브 filed Critical 하. 룬드벡 아크티에셀스카브
Publication of KR20140041567A publication Critical patent/KR20140041567A/ko
Application granted granted Critical
Publication of KR101879474B1 publication Critical patent/KR101879474B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic 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
    • C07D295/04Heterocyclic 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
    • C07D295/06Heterocyclic 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
    • C07D295/073Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • 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
    • A61K31/4523Non 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • 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
    • A61K31/4523Non 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/496Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/554Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002Heterocyclic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation 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
    • C07C45/67Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D241/00Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05Isotopically modified compounds, e.g. labelled

Landscapes

  • 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)
KR1020137033717A 2011-06-20 2012-06-19 정신 분열증의 치료를 위한 중수소화 1-피페라지노-3-페닐 인단 Active KR101879474B1 (ko)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201161498651P 2011-06-20 2011-06-20
US61/498,651 2011-06-20
US201161537103P 2011-09-21 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

Related Child Applications (1)

Application Number Title Priority Date Filing Date
KR1020187018343A Division KR101939546B1 (ko) 2011-06-20 2012-06-19 정신 분열증의 치료를 위한 중수소화 1-피페라지노-3-페닐 인단

Publications (2)

Publication Number Publication Date
KR20140041567A KR20140041567A (ko) 2014-04-04
KR101879474B1 true KR101879474B1 (ko) 2018-07-17

Family

ID=46682855

Family Applications (2)

Application Number Title Priority Date Filing Date
KR1020137033717A Active KR101879474B1 (ko) 2011-06-20 2012-06-19 정신 분열증의 치료를 위한 중수소화 1-피페라지노-3-페닐 인단
KR1020187018343A Active KR101939546B1 (ko) 2011-06-20 2012-06-19 정신 분열증의 치료를 위한 중수소화 1-피페라지노-3-페닐 인단

Family Applications After (1)

Application Number Title Priority Date Filing Date
KR1020187018343A Active KR101939546B1 (ko) 2011-06-20 2012-06-19 정신 분열증의 치료를 위한 중수소화 1-피페라지노-3-페닐 인단

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

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
WO2005016901A1 (en) * 2003-08-18 2005-02-24 H. Lundbeck A/S Trans-1(6-chloro-3-phenylindan-1-yl)-3,3-dimethylpiperazine

Family Cites Families (46)

* 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
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
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

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
WO2005016901A1 (en) * 2003-08-18 2005-02-24 H. Lundbeck A/S Trans-1(6-chloro-3-phenylindan-1-yl)-3,3-dimethylpiperazine

Also Published As

Publication number Publication date
CY1121514T1 (el) 2020-05-29
PL3135656T3 (pl) 2019-07-31
KR101939546B1 (ko) 2019-01-16
SI2720989T1 (sl) 2016-11-30
US20160068497A1 (en) 2016-03-10
US10501427B2 (en) 2019-12-10
EP3508468B1 (en) 2023-01-18
PT3135656T (pt) 2019-05-03
EP4215512A1 (en) 2023-07-26
EP2720989B1 (en) 2016-08-10
ES2719145T3 (es) 2019-07-08
ES2939477T3 (es) 2023-04-24
GT201300304A (es) 2015-01-16
DK3135656T3 (en) 2019-04-23
TW201722895A (zh) 2017-07-01
JP2014520140A (ja) 2014-08-21
SMT201900179T1 (it) 2019-05-10
LT3135656T (lt) 2019-04-25
HUE030883T2 (en) 2017-06-28
HRP20190593T1 (hr) 2019-05-17
DK2720989T3 (en) 2016-11-28
GEP201706655B (en) 2017-04-25
TWI659741B (zh) 2019-05-21
LT2720989T (lt) 2016-11-25
HUE044043T2 (hu) 2019-09-30
EA024651B1 (ru) 2016-10-31
MD4538C1 (ro) 2018-07-31
MX2013014849A (es) 2014-03-31
EP2720989A1 (en) 2014-04-23
EP3508468A1 (en) 2019-07-10
ME03375B (me) 2020-01-20
ES2601213T3 (es) 2017-02-14
US8575174B2 (en) 2013-11-05
SMT201600383B (it) 2017-01-10
CN103649019A (zh) 2014-03-19
TWI614234B (zh) 2018-02-11
MX339552B (es) 2016-05-31
US9012453B2 (en) 2015-04-21
MA35268B1 (fr) 2014-07-03
TW201311248A (zh) 2013-03-16
TWI627956B (zh) 2018-07-01
DOP2013000305A (es) 2014-02-28
US20220119362A1 (en) 2022-04-21
US12116355B2 (en) 2024-10-15
US20130281436A1 (en) 2013-10-24
RS55304B1 (sr) 2017-03-31
PE20141113A1 (es) 2014-09-25
ECSP14013155A (es) 2014-02-28
KR20180075717A (ko) 2018-07-04
US20190031631A1 (en) 2019-01-31
ME02513B (me) 2017-02-20
US20200131143A1 (en) 2020-04-30
JO3128B1 (ar) 2017-09-20
AP3310A (en) 2015-06-30
HK1197228A1 (zh) 2015-01-09
AU2012273657A1 (en) 2013-12-12
US9216961B2 (en) 2015-12-22
TW201902481A (zh) 2019-01-16
JP5668177B2 (ja) 2015-02-12
CA2837820C (en) 2019-02-19
EP3135656A1 (en) 2017-03-01
RS58546B1 (sr) 2019-05-31
US9617231B2 (en) 2017-04-11
AP2013007338A0 (en) 2013-12-31
BR112013031702A2 (pt) 2016-12-13
MY196998A (en) 2023-05-17
AU2012273657B2 (en) 2016-07-21
KR20140041567A (ko) 2014-04-04
NZ618222A (en) 2015-03-27
PT2720989T (pt) 2016-11-07
HRP20161348T1 (hr) 2016-12-02
SI3135656T1 (sl) 2019-05-31
MD4538B1 (ro) 2017-12-31
CN103649019B (zh) 2015-09-16
EP3135656B1 (en) 2019-02-27
AR086987A1 (es) 2014-02-05
PH12013502598A1 (en) 2014-02-10
US20120322811A1 (en) 2012-12-20
US20170158650A1 (en) 2017-06-08
MD20140004A2 (en) 2014-05-31
US20250250244A1 (en) 2025-08-07
CO6821965A2 (es) 2013-12-31
EA201490045A1 (ru) 2014-07-30
CR20130654A (es) 2014-03-24
WO2012176066A1 (en) 2012-12-27
CY1118158T1 (el) 2017-06-28
IL229640B (en) 2018-02-28
IL229640A0 (en) 2014-01-30
PL2720989T3 (pl) 2017-05-31
CL2013003646A1 (es) 2014-07-04
PE20150928A1 (es) 2015-06-26
CA2837820A1 (en) 2012-12-27
US10118907B2 (en) 2018-11-06
US11059798B2 (en) 2021-07-13
BR112013031702B1 (pt) 2021-11-03
US20150307458A1 (en) 2015-10-29

Similar Documents

Publication Publication Date Title
KR101879474B1 (ko) 정신 분열증의 치료를 위한 중수소화 1-피페라지노-3-페닐 인단
HK40003441A (en) Deuterated 1-piperazino-3-phenyl indanes for treatment of schizophrenia
HK40003441B (en) Deuterated 1-piperazino-3-phenyl indanes for treatment of schizophrenia
HK1235050A1 (en) Deuterated 1-piperazino-3-phenyl indanes for treatment of schizophrenia
HK1235050B (en) Deuterated 1-piperazino-3-phenyl indanes for treatment of schizophrenia
HK1197228B (en) Deuterated 1-piperazino-3-phenyl indanes for treatment of schizophrenia
OA16797A (en) Deuterated 1-Piperazino-3-Phenyl-Indanes for treatment of Schizophrenia.

Legal Events

Date Code Title Description
PA0105 International application

Patent event date: 20131218

Patent event code: PA01051R01D

Comment text: International Patent Application

PG1501 Laying open of application
A201 Request for examination
A302 Request for accelerated examination
PA0201 Request for examination

Patent event code: PA02012R01D

Patent event date: 20170616

Comment text: Request for Examination of Application

PA0302 Request for accelerated examination

Patent event date: 20170616

Patent event code: PA03022R01D

Comment text: Request for Accelerated Examination

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

Comment text: Notification of reason for refusal

Patent event date: 20171012

Patent event code: PE09021S01D

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

Comment text: Notification of reason for refusal

Patent event date: 20180205

Patent event code: PE09021S01D

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

Patent event code: PE07011S01D

Comment text: Decision to Grant Registration

Patent event date: 20180418

A107 Divisional application of patent
PA0104 Divisional application for international application

Comment text: Divisional Application for International Patent

Patent event code: PA01041R01D

Patent event date: 20180627

GRNT Written decision to grant
PR0701 Registration of establishment

Comment text: Registration of Establishment

Patent event date: 20180711

Patent event code: PR07011E01D

PR1002 Payment of registration fee

Payment date: 20180711

End annual number: 3

Start annual number: 1

PG1601 Publication of registration
FPAY Annual fee payment

Payment date: 20210617

Year of fee payment: 4

PR1001 Payment of annual fee

Payment date: 20210617

Start annual number: 4

End annual number: 4

FPAY Annual fee payment

Payment date: 20220526

Year of fee payment: 5

PR1001 Payment of annual fee

Payment date: 20220526

Start annual number: 5

End annual number: 5