CA2931016C - 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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CA2931016C
CA2931016C CA2931016A CA2931016A CA2931016C CA 2931016 C CA2931016 C CA 2931016C CA 2931016 A CA2931016 A CA 2931016A CA 2931016 A CA2931016 A CA 2931016A CA 2931016 C CA2931016 C CA 2931016C
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compound
formula
certain embodiment
relates
reacting
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French (fr)
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CA2931016A1 (en
Inventor
Benno Rothenhaeusler
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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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)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (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)
CA2931016A 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 CA2931016C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3142754A 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

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP13195864 2013-12-05
EP13195864.7 2013-12-05
PCT/EP2014/076041 WO2015082370A1 (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 crytalline forms thereof

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA3142754A Division 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

Publications (2)

Publication Number Publication Date
CA2931016A1 CA2931016A1 (en) 2015-06-11
CA2931016C true CA2931016C (en) 2022-11-01

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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
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

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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

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US (3) US10246460B2 (enExample)
EP (1) EP3077396B1 (enExample)
JP (1) JP6454707B2 (enExample)
KR (3) KR102384630B1 (enExample)
CN (1) CN105793263B (enExample)
AR (1) AR098592A1 (enExample)
AU (2) AU2014359409A1 (enExample)
CA (2) CA2931016C (enExample)
ES (1) ES2875411T3 (enExample)
HR (1) HRP20210966T1 (enExample)
IL (2) IL245450A0 (enExample)
MX (1) MX372971B (enExample)
MY (1) MY175464A (enExample)
NZ (1) NZ720340A (enExample)
PL (1) PL3077396T3 (enExample)
SG (1) SG11201604502SA (enExample)
SI (1) SI3077396T1 (enExample)
WO (1) WO2015082370A1 (enExample)
ZA (1) ZA201603304B (enExample)

Families Citing this family (5)

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Publication number Priority date Publication date Assignee Title
KR102384630B1 (ko) * 2013-12-05 2022-04-11 에프. 호프만-라 로슈 아게 트랜스-8-클로로-5-메틸-1-[4-(피리딘-2-일옥시)-사이클로헥실]-5,6-다이하이드로-4H-2,3,5,10b-테트라아자-벤조[e]아줄렌 및 그의 결정 형태의 합성
WO2017191117A1 (en) 2016-05-03 2017-11-09 Bayer Pharma Aktiengesellschaft V1a receptor antagonists for use in the treatment of renal diseases
JP7308193B2 (ja) 2017-12-08 2023-07-13 エフ. ホフマン-ラ ロシュ アーゲー 医薬組成物
WO2020139670A1 (en) 2018-12-27 2020-07-02 Teva Pharmaceuticals International Gmbh Solid state forms of balovaptan
KR20230049576A (ko) 2021-10-06 2023-04-13 주식회사 엘지에너지솔루션 배터리 모듈

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
GB0303852D0 (en) 2003-02-19 2003-03-26 Pfizer Ltd Triazole compounds useful in therapy
DE602004003914T2 (de) * 2003-02-19 2007-05-31 Pfizer Inc. Für die therapie geeignete triazolverbindungen
GB0400700D0 (en) 2004-01-13 2004-02-18 Pfizer Ltd Compounds useful in therapy
JP2008510789A (ja) 2004-08-25 2008-04-10 ファイザー・インク トリアゾロベンゾジアゼピン及びバゾプレシンアンタゴニストとしてのそれらの使用
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
DK2358714T3 (da) * 2008-11-18 2012-08-20 Hoffmann La Roche Alkylcyclohexylethere af dihydrotetraazabenzoazulener
KR101359742B1 (ko) * 2008-11-28 2014-02-06 에프. 호프만-라 로슈 아게 수용체 길항제를 통해 바소프레신으로 사용되는 다이하이드로테트라아자벤조아줄렌의 아릴사이클로헥실에테르
US8492376B2 (en) 2010-04-21 2013-07-23 Hoffmann-La Roche Inc. Heteroaryl-cyclohexyl-tetraazabenzo[e]azulenes
EP3035939B1 (en) 2013-08-19 2020-03-25 F. Hoffmann-La Roche AG V1a antagonists to treat phase shift sleep disorders
KR102384630B1 (ko) 2013-12-05 2022-04-11 에프. 호프만-라 로슈 아게 트랜스-8-클로로-5-메틸-1-[4-(피리딘-2-일옥시)-사이클로헥실]-5,6-다이하이드로-4H-2,3,5,10b-테트라아자-벤조[e]아줄렌 및 그의 결정 형태의 합성

Also Published As

Publication number Publication date
KR20210132745A (ko) 2021-11-04
KR20160093709A (ko) 2016-08-08
NZ759478A (en) 2021-06-25
NZ720340A (en) 2020-03-27
JP6454707B2 (ja) 2019-01-16
US20210284648A1 (en) 2021-09-16
IL264891B (en) 2021-02-28
AR098592A1 (es) 2016-06-01
EP3077396A1 (en) 2016-10-12
US11040977B2 (en) 2021-06-22
WO2015082370A1 (en) 2015-06-11
SG11201604502SA (en) 2016-07-28
US12459947B2 (en) 2025-11-04
AU2014359409A1 (en) 2016-05-19
MY175464A (en) 2020-06-29
SI3077396T1 (sl) 2021-08-31
KR102384630B1 (ko) 2022-04-11
CN105793263B (zh) 2019-08-23
US20160280712A1 (en) 2016-09-29
KR102384629B1 (ko) 2022-04-11
ES2875411T3 (es) 2021-11-10
RU2018135601A3 (enExample) 2022-05-05
CA2931016A1 (en) 2015-06-11
EP3077396B1 (en) 2021-04-21
IL245450A0 (en) 2016-06-30
PL3077396T3 (pl) 2021-10-04
KR102384608B1 (ko) 2022-04-08
MX372971B (es) 2020-03-27
CA3142754C (en) 2024-01-02
KR20210134985A (ko) 2021-11-11
AU2019201183B2 (en) 2021-03-04
US20190194210A1 (en) 2019-06-27
JP2016539168A (ja) 2016-12-15
ZA201603304B (en) 2022-05-25
HK1223918A1 (zh) 2017-08-11
HRP20210966T1 (hr) 2021-09-17
US10246460B2 (en) 2019-04-02
AU2019201183A1 (en) 2019-03-14
RU2018135601A (ru) 2018-11-22
CN105793263A (zh) 2016-07-20
MX2016006558A (es) 2016-08-03
CA3142754A1 (en) 2015-06-11

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