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
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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)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (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)
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
EP13195864.7 2013-12-05
EP13195864 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)

Publication Number Publication Date
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

Country Status (19)

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

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6454707B2 (ja) 2013-12-05 2019-01-16 エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft trans−8−クロロ−5−メチル−1−[4−(ピリジン−2−イルオキシ)−シクロヘキシル]−5,6−ジヒドロ−4H−2,3,5,10b−テトラアザ−ベンゾ[e]アズレン及びその結晶形態の合成
WO2017191117A1 (en) 2016-05-03 2017-11-09 Bayer Pharma Aktiengesellschaft V1a receptor antagonists for use in the treatment of renal diseases
BR112020004035A2 (pt) 2017-12-08 2020-09-01 F. Hoffmann-La Roche Ag formulação farmacêutica
WO2020139670A1 (en) 2018-12-27 2020-07-02 Teva Pharmaceuticals International Gmbh Solid state forms of balovaptan
WO2023059110A1 (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
KR100750028B1 (ko) * 2003-02-19 2007-08-16 화이자 인코포레이티드 치료에 유용한 트리아졸 화합물
GB0400700D0 (en) 2004-01-13 2004-02-18 Pfizer Ltd Compounds useful in therapy
CA2578370A1 (en) 2004-08-25 2006-03-02 Pfizer Inc. 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
RU2510397C2 (ru) * 2008-11-18 2014-03-27 Ф. Хоффманн-Ля Рош Аг Алкилциклогексиловые эфиры дигидротетраазабензоазуленов
BRPI0922303B1 (pt) 2008-11-28 2019-11-12 Hoffmann La Roche arilciclo-hexiléteres de di-hidrotetra-azabenzoazulenos, seu processo de preparação, composição farmacêutica que os compreende e uso
US8492376B2 (en) 2010-04-21 2013-07-23 Hoffmann-La Roche Inc. Heteroaryl-cyclohexyl-tetraazabenzo[e]azulenes
PE20160203A1 (es) 2013-08-19 2016-04-20 Hoffmann La Roche Antagonistas de via para tratar trastornos del sueno por cambio de fase
JP6454707B2 (ja) * 2013-12-05 2019-01-16 エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft trans−8−クロロ−5−メチル−1−[4−(ピリジン−2−イルオキシ)−シクロヘキシル]−5,6−ジヒドロ−4H−2,3,5,10b−テトラアザ−ベンゾ[e]アズレン及びその結晶形態の合成

Also Published As

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

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