CA3107566A1 - A cocrystal of 2-[(1r,6r)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol - Google Patents

A cocrystal of 2-[(1r,6r)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol Download PDF

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Publication number
CA3107566A1
CA3107566A1 CA3107566A CA3107566A CA3107566A1 CA 3107566 A1 CA3107566 A1 CA 3107566A1 CA 3107566 A CA3107566 A CA 3107566A CA 3107566 A CA3107566 A CA 3107566A CA 3107566 A1 CA3107566 A1 CA 3107566A1
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Prior art keywords
cocrystal
cbd
methylcyclohex
diol
theta
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Pending
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CA3107566A
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English (en)
French (fr)
Inventor
Alexander Christian Comely
Nicolas Tesson
Carmen Jimenez Gonzalez
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Enantia SL
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Enantia SL
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Publication of CA3107566A1 publication Critical patent/CA3107566A1/en
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/17Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/84Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/08Antiepileptics; Anticonvulsants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/12Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/22Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/23Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/30Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Rheumatology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA3107566A 2017-08-07 2018-08-06 A cocrystal of 2-[(1r,6r)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol Pending CA3107566A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP17382555 2017-08-07
EP17382555.5 2017-08-07
PCT/EP2018/071238 WO2019030158A1 (en) 2017-08-07 2018-08-06 CO-CRYSTAL OF 2 - [(1R, 6R) -6-ISOPROPENYL-3-METHYLCYCLOHEX-2-EN-1-YL] -5-PENTYLBENZENE-1,3-DIOL

Publications (1)

Publication Number Publication Date
CA3107566A1 true CA3107566A1 (en) 2019-02-14

Family

ID=59677166

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3107566A Pending CA3107566A1 (en) 2017-08-07 2018-08-06 A cocrystal of 2-[(1r,6r)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol

Country Status (6)

Country Link
US (1) US11168047B2 (enExample)
EP (1) EP3665145A1 (enExample)
JP (1) JP7186460B2 (enExample)
CN (1) CN111183127B (enExample)
CA (1) CA3107566A1 (enExample)
WO (1) WO2019030158A1 (enExample)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190177258A1 (en) * 2017-12-11 2019-06-13 Artelo Biosciences, Inc. New solid forms of cannabidiol and uses thereof
WO2021138610A1 (en) * 2020-01-03 2021-07-08 Purisys Llc Cocrystals of cannabinoids
CA3179478A1 (en) * 2020-05-19 2021-11-25 Joanne Holland Tetrahydrocannabinolic acid cocrystals
CN111792982B (zh) * 2020-07-10 2024-05-14 云南农业大学 一种易于溶解的块状cbd晶型i及其制备方法
CN113004126B (zh) * 2021-03-05 2022-03-22 中国科学院上海药物研究所 羟基酪醇甜菜碱共晶,其制备方法及组合物

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2393182B (en) 2002-09-23 2007-03-14 Gw Pharma Ltd Method of preparing cannabidiol from plant material
JP2007516259A (ja) 2003-12-09 2007-06-21 メッドクリスタルフォームズ、エルエルシー 活性剤との混合相共結晶の調製方法
TWI366460B (en) 2005-06-16 2012-06-21 Euro Celtique Sa Cannabinoid active pharmaceutical ingredient for improved dosage forms
CN101316832A (zh) 2005-09-29 2008-12-03 Amr科技公司 δ-9-四氢大麻酚的生成方法
MX2010001242A (es) 2007-07-30 2010-07-02 Alltranz Inc Profarmacos de canabidiol, composiciones que comprenden profarmacos de canabidiol y metodos para utilizar los mismos.
EP2123626A1 (en) 2008-05-21 2009-11-25 Laboratorios del Dr. Esteve S.A. Co-crystals of duloxetine and co-crystal formers for the treatment of pain
AU2009345154A1 (en) 2009-04-29 2011-12-22 University Of Kentucky Research Foundation Cannabinoid-containing compositions and methods for their use
WO2011049191A1 (ja) 2009-10-23 2011-04-28 アステラス製薬株式会社 経口投与用医薬組成物
WO2012116349A2 (en) 2011-02-26 2012-08-30 Amplio Pharma, Llc Novel cocrystals of ezetimibe
ES2547354T3 (es) 2013-09-03 2015-10-05 Symrise Ag Mezclas de compuestos cannabinoides, su preparación y uso
US10226442B2 (en) * 2017-07-10 2019-03-12 Syneurx International (Taiwan) Corp. Lithium salts of N-substituted glycine compounds and uses thereof
US20190177258A1 (en) 2017-12-11 2019-06-13 Artelo Biosciences, Inc. New solid forms of cannabidiol and uses thereof

Also Published As

Publication number Publication date
WO2019030158A1 (en) 2019-02-14
CN111183127B (zh) 2023-02-21
US20200369586A1 (en) 2020-11-26
US11168047B2 (en) 2021-11-09
JP7186460B2 (ja) 2022-12-09
JP2020529450A (ja) 2020-10-08
EP3665145A1 (en) 2020-06-17
CN111183127A (zh) 2020-05-19

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