AU2010289802C1 - Synthesis of a neurostimulative piperazine - Google Patents

Synthesis of a neurostimulative piperazine Download PDF

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Publication number
AU2010289802C1
AU2010289802C1 AU2010289802A AU2010289802A AU2010289802C1 AU 2010289802 C1 AU2010289802 C1 AU 2010289802C1 AU 2010289802 A AU2010289802 A AU 2010289802A AU 2010289802 A AU2010289802 A AU 2010289802A AU 2010289802 C1 AU2010289802 C1 AU 2010289802C1
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AU
Australia
Prior art keywords
formula
compound
reaction
ambient temperature
alkyl
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
AU2010289802A
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English (en)
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AU2010289802B2 (en
AU2010289802A1 (en
Inventor
Olga Lapina
Ying Li
Syed Mahmood
Mark Mclaws
Bingidimi I. Mobele
Jonathan Salsbury
Sripathy Venkatraman
Kellie Vercoe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Palisade Bio Inc
Original Assignee
Neuralstem Inc
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Publication date
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Application filed by Neuralstem Inc filed Critical Neuralstem Inc
Publication of AU2010289802A1 publication Critical patent/AU2010289802A1/en
Publication of AU2010289802B2 publication Critical patent/AU2010289802B2/en
Application granted granted Critical
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • 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
    • A61P25/28—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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Neurosurgery (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Hydrogenated Pyridines (AREA)
AU2010289802A 2009-08-24 2010-08-24 Synthesis of a neurostimulative piperazine Active AU2010289802C1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US23647709P 2009-08-24 2009-08-24
US61/236,477 2009-08-24
PCT/US2010/046537 WO2011028548A1 (en) 2009-08-24 2010-08-24 Synthesis of a neurostimulative piperazine

Publications (3)

Publication Number Publication Date
AU2010289802A1 AU2010289802A1 (en) 2012-04-12
AU2010289802B2 AU2010289802B2 (en) 2014-10-02
AU2010289802C1 true AU2010289802C1 (en) 2015-04-16

Family

ID=43649584

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2010289802A Active AU2010289802C1 (en) 2009-08-24 2010-08-24 Synthesis of a neurostimulative piperazine

Country Status (22)

Country Link
US (2) US9278933B2 (enExample)
EP (1) EP2470182B1 (enExample)
JP (1) JP5727482B2 (enExample)
KR (1) KR101701362B1 (enExample)
CN (2) CN105693601A (enExample)
AU (1) AU2010289802C1 (enExample)
BR (1) BR112012004161B1 (enExample)
CA (1) CA2772080C (enExample)
CL (1) CL2012000493A1 (enExample)
DK (1) DK2470182T3 (enExample)
ES (1) ES2475721T3 (enExample)
HR (1) HRP20140621T1 (enExample)
IL (1) IL218298A (enExample)
IN (1) IN2012DN02370A (enExample)
MX (1) MX2012002335A (enExample)
NZ (1) NZ598891A (enExample)
PL (1) PL2470182T3 (enExample)
PT (1) PT2470182E (enExample)
RU (1) RU2567390C2 (enExample)
SG (1) SG178867A1 (enExample)
SI (1) SI2470182T1 (enExample)
WO (1) WO2011028548A1 (enExample)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN2012DN02370A (enExample) * 2009-08-24 2015-08-21 Neuralstem Inc
WO2018048927A1 (en) * 2016-09-12 2018-03-15 Neuralstem, Inc. Amelioration of neural deficits associated with diabetes
US20180104240A1 (en) * 2016-10-18 2018-04-19 Neuralstem, Inc. Amelioration of radiation-induced cognitive dysfunction
US10042957B2 (en) 2017-01-12 2018-08-07 Innovationdock, Inc. Devices and methods for implementing dynamic collaborative workflow systems
WO2018148733A1 (en) * 2017-02-13 2018-08-16 Neuralstem, Inc. Amelioration of certain deficiencies due to stroke
CN117377664A (zh) * 2020-12-23 2024-01-09 贝勒医学院 孤儿核受体tlx的小分子调节剂
JP2024520722A (ja) 2021-06-03 2024-05-24 オルト・ニューロサイエンス・インコーポレイテッド 不良な認知を有するうつ病患者の治療方法及びベンジルピペラジン－アミノピリジン剤の恩恵を受ける他の患者の選択
US12208096B2 (en) 2022-12-05 2025-01-28 Alto Neuroscience, Inc. Effective treatment of depression in patients having impaired learning and/or memory or certain EEG characteristics with a benzylpiperazine-aminopyridine agent
AU2023391488A1 (en) 2022-12-05 2025-05-22 Alto Neuroscience, Inc. Effective treatment of depression in patients having impaired learning and/or memory or certain eeg characteristics with a benzylpiperazine-aminopyridine agent
US12233059B2 (en) 2022-12-05 2025-02-25 Alto Neuroscience, Inc. Effective treatment of depression in patients having impaired learning and/or memory or certain EEG characteristics with a benzylpiperazine-aminopyridine agent

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060040956A1 (en) * 2001-01-12 2006-02-23 Guoqing Chen Substituted alkylamine derivatives and methods of use
US20090005363A1 (en) * 2005-12-20 2009-01-01 Ralf Glatthar Organic Compounds
US7560553B1 (en) * 2003-08-08 2009-07-14 Neuralstem, Inc. Use of fuse nicotinamides to promote neurogenesis

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU175075B (hu) * 1977-06-30 1980-05-28 Egyt Gyogyszervegyeszeti Gyar Sposob poluchenija piperazidov piridin-karbonovoj kisloty
JPS54122283A (en) * 1978-03-13 1979-09-21 Sumitomo Chem Co Ltd Novel quinazoline derivative and its preparation
DE60330323D1 (de) * 2002-03-29 2010-01-14 Schering Corp Stereoselektive alkylierung von chirale 2-methyl-4-geschützte piperazinen
GB0222493D0 (en) * 2002-09-27 2002-11-06 Glaxo Group Ltd Compounds
BRPI0414209B8 (pt) * 2003-09-09 2021-05-25 Hoffmann La Roche derivados de 1-(2-amino-benzol)-piperazina, seus processos de preparação e seu uso, e medicamento
EP1828165B1 (en) 2004-10-29 2013-03-20 Msd K.K. Novel aminopyridine derivatives having aurora a selective inhibitory action
US7754724B2 (en) * 2005-06-30 2010-07-13 Dow Agrosciences Llc N-substituted piperazines
IN2012DN02370A (enExample) * 2009-08-24 2015-08-21 Neuralstem Inc

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060040956A1 (en) * 2001-01-12 2006-02-23 Guoqing Chen Substituted alkylamine derivatives and methods of use
US7560553B1 (en) * 2003-08-08 2009-07-14 Neuralstem, Inc. Use of fuse nicotinamides to promote neurogenesis
US20090005363A1 (en) * 2005-12-20 2009-01-01 Ralf Glatthar Organic Compounds

Also Published As

Publication number Publication date
RU2012111227A (ru) 2013-10-10
HK1172844A1 (en) 2013-05-03
US9278933B2 (en) 2016-03-08
JP2013502462A (ja) 2013-01-24
BR112012004161A2 (pt) 2016-03-29
AU2010289802B2 (en) 2014-10-02
IL218298A0 (en) 2012-04-30
EP2470182A4 (en) 2013-04-24
EP2470182B1 (en) 2014-06-04
PL2470182T3 (pl) 2015-05-29
BR112012004161B1 (pt) 2020-04-07
MX2012002335A (es) 2012-07-04
US20160090358A1 (en) 2016-03-31
IL218298A (en) 2017-03-30
CL2012000493A1 (es) 2012-09-28
US20130005974A1 (en) 2013-01-03
EP2470182A1 (en) 2012-07-04
CN102711764A (zh) 2012-10-03
AU2010289802A1 (en) 2012-04-12
KR20120054642A (ko) 2012-05-30
NZ598891A (en) 2014-05-30
DK2470182T3 (da) 2014-07-21
HRP20140621T1 (hr) 2014-11-21
ES2475721T3 (es) 2014-07-11
JP5727482B2 (ja) 2015-06-03
SI2470182T1 (sl) 2014-10-30
WO2011028548A1 (en) 2011-03-10
US9481649B2 (en) 2016-11-01
CN105693601A (zh) 2016-06-22
SG178867A1 (en) 2012-04-27
IN2012DN02370A (enExample) 2015-08-21
CA2772080A1 (en) 2011-03-10
KR101701362B1 (ko) 2017-02-01
CA2772080C (en) 2017-05-30
PT2470182E (pt) 2014-07-24
RU2567390C2 (ru) 2015-11-10

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