WO2018104729A8 - Ketamine derivatives - Google Patents

Ketamine derivatives Download PDF

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Publication number
WO2018104729A8
WO2018104729A8 PCT/GB2017/053672 GB2017053672W WO2018104729A8 WO 2018104729 A8 WO2018104729 A8 WO 2018104729A8 GB 2017053672 W GB2017053672 W GB 2017053672W WO 2018104729 A8 WO2018104729 A8 WO 2018104729A8
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
present
provides
ketamine
ketamine derivatives
Prior art date
Application number
PCT/GB2017/053672
Other languages
French (fr)
Other versions
WO2018104729A1 (en
Inventor
Richard MYERSON
Jonathan Hull
Paul Blaney
Peter RANDS
Alan Armstrong
Original Assignee
Small Pharma Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from GBGB1620690.6A external-priority patent/GB201620690D0/en
Priority claimed from GBGB1712304.3A external-priority patent/GB201712304D0/en
Application filed by Small Pharma Ltd filed Critical Small Pharma Ltd
Publication of WO2018104729A1 publication Critical patent/WO2018104729A1/en
Publication of WO2018104729A8 publication Critical patent/WO2018104729A8/en

Links

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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/423—Oxazoles condensed with carbocyclic rings
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4525—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
    • 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
    • A61P25/24—Antidepressants

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pain & Pain Management (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention provides conformationally stabilized analogues of the ketamine metabolites 6-hydroxyketamine and 6-hydroxynorketamine with applications in the treatment of depression disorders and anxiety disorders. In particular the present invention provides a compound of Formula I, or a pharmaceutically acceptable salt thereof; wherein R1 is H or C1-C4 alkyl; R2 is H or C1-C4 alkyl; R3 is H or C1-C4 alkyl; R4 is H or C1- C4 alkyl; R5 is H or C1-C4 alkyl; R5 is H or C1-C4 alkyl; and R6 represents 0, 1, 2, 3, 4 or 5 haloatoms each independently selected from F, C1, Br,I, wherein when R2 is H, preferably at least one of R3, R4 and R5 is not H.
PCT/GB2017/053672 2016-12-05 2017-12-05 Ketamine derivatives WO2018104729A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB1620690.6 2016-12-05
GBGB1620690.6A GB201620690D0 (en) 2016-12-05 2016-12-05 Ketamine derivatives
GBGB1712304.3A GB201712304D0 (en) 2017-07-31 2017-07-31 Synthetic methods
GB1712304.3 2017-07-31

Publications (2)

Publication Number Publication Date
WO2018104729A1 WO2018104729A1 (en) 2018-06-14
WO2018104729A8 true WO2018104729A8 (en) 2018-12-20

Family

ID=60702834

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2017/053672 WO2018104729A1 (en) 2016-12-05 2017-12-05 Ketamine derivatives

Country Status (1)

Country Link
WO (1) WO2018104729A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110540509A (en) * 2019-05-24 2019-12-06 北京大学深圳研究生院 Long-acting compound

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110343050B (en) * 2018-04-04 2021-09-24 上海键合医药科技有限公司 Aromatic compound and preparation method and application thereof
WO2020237748A1 (en) * 2019-05-24 2020-12-03 北京大学深圳研究生院 Method for preparing long-acting compound
WO2020237747A1 (en) * 2019-05-24 2020-12-03 北京大学深圳研究生院 Applications of long-acting compound in preparing medicament
IL299108A (en) * 2020-06-17 2023-02-01 Spirify Pharma Inc Hydroxynorketamine analogues, compositions comprising same and methods of use thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6296985B2 (en) * 2011-10-14 2018-03-20 ザ ユナイテッド ステイツ オブ アメリカ， アズ リプレゼンテッド バイ ザ セクレタリー， デパートメント オブ ヘルス アンド ヒューマン サービシーズ Use of (2R, 6R) -hydroxynorketamine, (S) -dehydronorketamine and other (R, S) -ketamine stereoisomeric dehydro and hydroxylated metabolites in the treatment of depression and neuropathic pain
US11111210B2 (en) * 2015-11-18 2021-09-07 Spirify Pharma Inc. Phenyl cyclohexanone derivatives and methods of making and using them

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110540509A (en) * 2019-05-24 2019-12-06 北京大学深圳研究生院 Long-acting compound
CN110540509B (en) * 2019-05-24 2020-08-07 北京大学深圳研究生院 Long-acting compound

Also Published As

Publication number Publication date
WO2018104729A1 (en) 2018-06-14

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