CA3142754C - Synthesis of trans-8-chloro-5-methyl- 1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof - Google Patents

Synthesis of trans-8-chloro-5-methyl- 1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof Download PDF

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CA3142754C
CA3142754C CA3142754A CA3142754A CA3142754C CA 3142754 C CA3142754 C CA 3142754C CA 3142754 A CA3142754 A CA 3142754A CA 3142754 A CA3142754 A CA 3142754A CA 3142754 C CA3142754 C CA 3142754C
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compound
formula
certain embodiment
relates
mmol
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French (fr)
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CA3142754A1 (en
Inventor
Benno Rothenhaeulsler
Rene Trussardi
Fabienne Hoffmann-Emery
Urs Schwitter
Jean-Michel Adam
Olaf Grassmann
Thomas Hartung
Frederic Ran
Ralph Diodone
Christophe Pfleger
Bjoern Bartels
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F Hoffmann La Roche AG
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems
    • 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
    • A61K31/55131,4-Benzodiazepines, e.g. diazepam or clozapine
    • A61K31/55171,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D243/00Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/141,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13Crystalline forms, e.g. polymorphs

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
CA3142754A 2013-12-05 2014-12-01 Synthesis of trans-8-chloro-5-methyl- 1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof Active CA3142754C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP13195864 2013-12-05
EP13195864.7 2013-12-05
CA2931016A CA2931016C (en) 2013-12-05 2014-12-01 Synthesis of trans-8-chloro-5-methyl-1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof

Related Parent Applications (1)

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CA2931016A Division CA2931016C (en) 2013-12-05 2014-12-01 Synthesis of trans-8-chloro-5-methyl-1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof

Publications (2)

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CA3142754A1 CA3142754A1 (en) 2015-06-11
CA3142754C true CA3142754C (en) 2024-01-02

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CA3142754A Active CA3142754C (en) 2013-12-05 2014-12-01 Synthesis of trans-8-chloro-5-methyl- 1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof
CA2931016A Active CA2931016C (en) 2013-12-05 2014-12-01 Synthesis of trans-8-chloro-5-methyl-1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof

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CA2931016A Active CA2931016C (en) 2013-12-05 2014-12-01 Synthesis of trans-8-chloro-5-methyl-1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof

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US (3) US10246460B2 (OSRAM)
EP (1) EP3077396B1 (OSRAM)
JP (1) JP6454707B2 (OSRAM)
KR (3) KR102384629B1 (OSRAM)
CN (1) CN105793263B (OSRAM)
AR (1) AR098592A1 (OSRAM)
AU (2) AU2014359409A1 (OSRAM)
CA (2) CA3142754C (OSRAM)
ES (1) ES2875411T3 (OSRAM)
HR (1) HRP20210966T1 (OSRAM)
IL (2) IL245450A0 (OSRAM)
MX (1) MX372971B (OSRAM)
MY (1) MY175464A (OSRAM)
NZ (1) NZ720340A (OSRAM)
PL (1) PL3077396T3 (OSRAM)
SG (1) SG11201604502SA (OSRAM)
SI (1) SI3077396T1 (OSRAM)
WO (1) WO2015082370A1 (OSRAM)
ZA (1) ZA201603304B (OSRAM)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HRP20210966T1 (hr) 2013-12-05 2021-09-17 F. Hoffmann - La Roche Ag Sinteza trans-8-kloro-5-metil-1-[4-(piridin-2-iloksi)-cikloheksil]-5,6-dihidro-4h-2,3,5,10b-tetraaza­benzo[e]azulena i njegovih kristalnih oblika
WO2017191117A1 (en) 2016-05-03 2017-11-09 Bayer Pharma Aktiengesellschaft V1a receptor antagonists for use in the treatment of renal diseases
TWI816718B (zh) 2017-12-08 2023-10-01 瑞士商赫孚孟拉羅股份公司 醫藥調配物
WO2020139670A1 (en) 2018-12-27 2020-07-02 Teva Pharmaceuticals International Gmbh Solid state forms of balovaptan
US20240154207A1 (en) 2021-10-06 2024-05-09 Lg Energy Solution, Ltd. Battery module

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1197242A (en) * 1983-03-02 1985-11-26 Jean A. Gauthier Pyrimido¬1,2-a|pyrrolo¬2,1-c|¬1, 4|benzodiazepine-3-carboxylic acid derivatives
DE602004003914T2 (de) * 2003-02-19 2007-05-31 Pfizer Inc. Für die therapie geeignete triazolverbindungen
GB0303852D0 (en) 2003-02-19 2003-03-26 Pfizer Ltd Triazole compounds useful in therapy
GB0400700D0 (en) 2004-01-13 2004-02-18 Pfizer Ltd Compounds useful in therapy
WO2006021882A1 (en) 2004-08-25 2006-03-02 Pfizer Limited Triazolobenzodiazepines and their use as vasopressin antagonists
US7601715B2 (en) * 2005-06-22 2009-10-13 Bristol-Myers Squibb Company Process for preparing triazole substituted azaindoleoxoacetic piperazine derivatives and novel salt forms produced therein
KR101385433B1 (ko) * 2008-11-18 2014-04-14 에프. 호프만-라 로슈 아게 다이하이드로테트라아자벤조아줄렌의 알킬사이클로헥실에터
DK2370441T3 (da) * 2008-11-28 2013-10-21 Hoffmann La Roche Arylcyclohexylethere af dihydrotetraazabenzoazulener til anvendelse som vasopressin v1a-receptorantagonister
US8492376B2 (en) 2010-04-21 2013-07-23 Hoffmann-La Roche Inc. Heteroaryl-cyclohexyl-tetraazabenzo[e]azulenes
CN105492010B (zh) 2013-08-19 2020-01-03 豪夫迈·罗氏有限公司 用于治疗相移睡眠障碍的V1a拮抗剂
HRP20210966T1 (hr) * 2013-12-05 2021-09-17 F. Hoffmann - La Roche Ag Sinteza trans-8-kloro-5-metil-1-[4-(piridin-2-iloksi)-cikloheksil]-5,6-dihidro-4h-2,3,5,10b-tetraaza­benzo[e]azulena i njegovih kristalnih oblika

Also Published As

Publication number Publication date
EP3077396A1 (en) 2016-10-12
NZ720340A (en) 2020-03-27
MX372971B (es) 2020-03-27
SG11201604502SA (en) 2016-07-28
MY175464A (en) 2020-06-29
US20190194210A1 (en) 2019-06-27
RU2018135601A3 (OSRAM) 2022-05-05
CA2931016A1 (en) 2015-06-11
IL264891B (en) 2021-02-28
MX2016006558A (es) 2016-08-03
KR102384630B1 (ko) 2022-04-11
CA3142754A1 (en) 2015-06-11
KR20210134985A (ko) 2021-11-11
NZ759478A (en) 2021-06-25
ES2875411T3 (es) 2021-11-10
US12459947B2 (en) 2025-11-04
US20160280712A1 (en) 2016-09-29
ZA201603304B (en) 2022-05-25
US10246460B2 (en) 2019-04-02
US20210284648A1 (en) 2021-09-16
RU2018135601A (ru) 2018-11-22
AU2019201183B2 (en) 2021-03-04
CN105793263A (zh) 2016-07-20
KR20160093709A (ko) 2016-08-08
KR102384629B1 (ko) 2022-04-11
US11040977B2 (en) 2021-06-22
AU2019201183A1 (en) 2019-03-14
JP6454707B2 (ja) 2019-01-16
HRP20210966T1 (hr) 2021-09-17
KR20210132745A (ko) 2021-11-04
WO2015082370A1 (en) 2015-06-11
AR098592A1 (es) 2016-06-01
CN105793263B (zh) 2019-08-23
JP2016539168A (ja) 2016-12-15
CA2931016C (en) 2022-11-01
IL245450A0 (en) 2016-06-30
HK1223918A1 (zh) 2017-08-11
AU2014359409A1 (en) 2016-05-19
PL3077396T3 (pl) 2021-10-04
EP3077396B1 (en) 2021-04-21
KR102384608B1 (ko) 2022-04-08
SI3077396T1 (sl) 2021-08-31

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