CA2979853C - Deuterated analogs of etifoxine, their derivatives and uses therof - Google Patents

Deuterated analogs of etifoxine, their derivatives and uses therof Download PDF

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Publication number
CA2979853C
CA2979853C CA2979853A CA2979853A CA2979853C CA 2979853 C CA2979853 C CA 2979853C CA 2979853 A CA2979853 A CA 2979853A CA 2979853 A CA2979853 A CA 2979853A CA 2979853 C CA2979853 C CA 2979853C
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CA
Canada
Prior art keywords
compound
chloro
pharmaceutically acceptable
amine
etifoxine
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
CA2979853A
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English (en)
French (fr)
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CA2979853A1 (en
Inventor
Olivier Dasse
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.)
Gaba Inc
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Gaba Inc
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Publication date
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Publication of CA2979853A1 publication Critical patent/CA2979853A1/en
Application granted granted Critical
Publication of CA2979853C publication Critical patent/CA2979853C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • 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
    • A61K31/01—Hydrocarbons
    • A61K31/015—Hydrocarbons carbocyclic
    • 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
    • A61K31/02—Halogenated hydrocarbons
    • A61K31/025—Halogenated hydrocarbons carbocyclic
    • A61K31/03—Halogenated hydrocarbons carbocyclic aromatic
    • 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
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/536—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines ortho- or peri-condensed with carbocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
    • C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Rheumatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Immunology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Medicinal Preparation (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
CA2979853A 2015-03-20 2016-03-18 Deuterated analogs of etifoxine, their derivatives and uses therof Active CA2979853C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562135979P 2015-03-20 2015-03-20
US62/135,979 2015-03-20
PCT/US2016/023231 WO2016154039A1 (en) 2015-03-20 2016-03-18 Deuterated analogs of etifoxine, their derivatives and uses therof

Publications (2)

Publication Number Publication Date
CA2979853A1 CA2979853A1 (en) 2016-09-29
CA2979853C true CA2979853C (en) 2021-05-11

Family

ID=56977741

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2979853A Active CA2979853C (en) 2015-03-20 2016-03-18 Deuterated analogs of etifoxine, their derivatives and uses therof

Country Status (21)

Country Link
US (4) US10080755B2 (enExample)
EP (1) EP3347006B1 (enExample)
JP (3) JP6762507B2 (enExample)
KR (1) KR102290766B1 (enExample)
CN (1) CN107530323B (enExample)
AU (2) AU2016235495B2 (enExample)
BR (1) BR112017020081B1 (enExample)
CA (1) CA2979853C (enExample)
DK (1) DK3347006T3 (enExample)
ES (1) ES2928396T3 (enExample)
HR (1) HRP20221240T1 (enExample)
HU (1) HUE060240T2 (enExample)
IL (2) IL270627B2 (enExample)
LT (1) LT3347006T (enExample)
MX (1) MX383647B (enExample)
PL (1) PL3347006T3 (enExample)
PT (1) PT3347006T (enExample)
RS (1) RS63654B1 (enExample)
SI (1) SI3347006T1 (enExample)
SM (1) SMT202200407T1 (enExample)
WO (1) WO2016154039A1 (enExample)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3347006B1 (en) * 2015-03-20 2022-07-27 GABA Therapeutics Inc. Deuterated analogs of etifoxine, their derivatives and uses therof
US10420773B2 (en) * 2017-09-26 2019-09-24 Ovid Therapeutics Inc. Methods of treating developmental disorders and/or seizure disorders with etifoxine
JP2021519276A (ja) * 2018-03-23 2021-08-10 コンサート ファーマシューティカルズ インコーポレイテッド Ｄ−β−ヒドロキシ酪酸の重水素化類似体およびその使用
EP3781264A4 (en) * 2018-05-18 2021-06-16 Ovid Therapeutics Inc. METHODS FOR TREATING A HYPERACTIVITY DISORDER WITH ATTENTION DEFICIT
CN112125862A (zh) * 2019-06-25 2020-12-25 上海安谱实验科技股份有限公司 一种稳定同位素标记的阿特拉津-d5及其合成方法
WO2021097427A1 (en) 2019-11-15 2021-05-20 Karuna Therapeutics, Inc. Xanomeline derivatives and methods for treating neurological disorders
US20240383942A1 (en) * 2021-09-14 2024-11-21 Nanjing Minova Pharmaceutical Co., Ltd. Water-soluble allopregnanolone derivative, and preparation method therefor and use thereof
WO2023218251A1 (en) * 2022-05-10 2023-11-16 Clearsynth Labs Limied Novel deuterium-enriched nefazodone analogues and method for preparing thereof
CN120390643A (zh) * 2022-10-24 2025-07-29 加巴疗法股份有限公司 艾替伏辛的氘代类似物及施用而没有代谢自身诱导的方法
AU2024366024B2 (en) * 2023-10-23 2026-07-09 Glomesh Intl Pty Ltd A module for mounting items

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1670772C3 (de) 1966-11-24 1978-04-20 Hoechst Ag, 6000 Frankfurt 4H-3,1-Benzoxazin-Derivate, deren Salze und pharmazeutische Präparate
FR2888748B1 (fr) 2005-07-19 2007-10-12 Biocodex Composes neuroprotecteurs et compositions pharmaceutiques les comprenant
US20080039453A1 (en) * 2006-03-20 2008-02-14 David Putman Enantiomerically pure R-etifoxine, pharmaceutical compositions thereof and methods of their use
CA2646007A1 (en) * 2006-03-20 2007-09-27 Xytis Inc. Enantiomerically pure s-etifoxine, pharmaceutical compositions thereof and methods of their use
JP2011001308A (ja) * 2009-06-19 2011-01-06 Research Foundation Itsuu Laboratory 重水素化カルボスチリル化合物
AU2011274496B2 (en) * 2010-07-09 2016-03-10 Teva Pharmaceutical Industries Ltd. Deuterated N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide, salts and uses thereof
EP2730559A4 (en) * 2011-07-05 2015-03-04 Kemphys Ltd DEUTERATED PHENYLPROPIONIC ACID DERIVATIVE
FR3016881B1 (fr) 2014-01-29 2016-03-04 Biocodex Traitement des degenerescences et des lesions photo-induites de la retine
EP3347006B1 (en) * 2015-03-20 2022-07-27 GABA Therapeutics Inc. Deuterated analogs of etifoxine, their derivatives and uses therof

Also Published As

Publication number Publication date
CN107530323B (zh) 2021-05-04
JP2023009114A (ja) 2023-01-19
JP2018508592A (ja) 2018-03-29
KR20170137085A (ko) 2017-12-12
JP6762507B2 (ja) 2020-09-30
EP3347006A4 (en) 2019-04-24
BR112017020081B1 (pt) 2021-11-30
WO2016154039A1 (en) 2016-09-29
HUE060240T2 (hu) 2023-02-28
SMT202200407T1 (it) 2022-11-18
IL254567B (en) 2020-03-31
KR102290766B1 (ko) 2021-08-19
US11672805B2 (en) 2023-06-13
MX383647B (es) 2025-03-14
EP3347006A1 (en) 2018-07-18
EP3347006B1 (en) 2022-07-27
LT3347006T (lt) 2022-10-25
AU2016235495B2 (en) 2020-05-14
US10080755B2 (en) 2018-09-25
PL3347006T3 (pl) 2022-11-14
JP7376668B2 (ja) 2023-11-08
US10736901B2 (en) 2020-08-11
US20200405726A1 (en) 2020-12-31
US20180064717A1 (en) 2018-03-08
RS63654B1 (sr) 2022-11-30
IL270627A (enExample) 2019-12-31
CA2979853A1 (en) 2016-09-29
AU2020201728A1 (en) 2020-03-26
DK3347006T3 (da) 2022-10-17
IL254567A0 (en) 2017-11-30
IL270627B (en) 2022-11-01
BR112017020081A2 (pt) 2018-06-05
MX2017011978A (es) 2018-02-09
AU2016235495A1 (en) 2017-10-05
AU2020201728B2 (en) 2021-12-23
US12433896B2 (en) 2025-10-07
IL270627B2 (en) 2023-03-01
ES2928396T3 (es) 2022-11-17
JP2021001174A (ja) 2021-01-07
PT3347006T (pt) 2022-10-17
CN107530323A (zh) 2018-01-02
HRP20221240T1 (hr) 2022-12-09
SI3347006T1 (sl) 2022-11-30
US20230263805A1 (en) 2023-08-24
US20190015419A1 (en) 2019-01-17

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