JP7186460B2 - ２－［（１ｒ，６ｒ）－６－イソプロペニル－３－メチルシクロヘキサ－２－エン－１－イル］－５－ペンチルベンゼン－１，３－ジオールの共結晶 - Google Patents

２－［（１ｒ，６ｒ）－６－イソプロペニル－３－メチルシクロヘキサ－２－エン－１－イル］－５－ペンチルベンゼン－１，３－ジオールの共結晶 Download PDF

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JP7186460B2
JP7186460B2 JP2020506341A JP2020506341A JP7186460B2 JP 7186460 B2 JP7186460 B2 JP 7186460B2 JP 2020506341 A JP2020506341 A JP 2020506341A JP 2020506341 A JP2020506341 A JP 2020506341A JP 7186460 B2 JP7186460 B2 JP 7186460B2
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crystal
isopropenyl
diol
methylcyclohex
pentylbenzene
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JP2020529450A5 (enExample
JP2020529450A (ja
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クリスチャン コメリー，アレキサンダー
テッソン，ニコラス
ゴンザレス，カルメン ヒメネス
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エナンティア，エセ．エレ．
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds 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
    • C07C39/17—Compounds 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
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds 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
    • C07C229/04—Compounds 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
    • C07C229/06—Compounds 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
    • C07C229/10—Compounds 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
    • C07C229/12—Compounds 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds 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
    • C07C229/04—Compounds 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
    • C07C229/22—Compounds 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/23—Compounds 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic 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
    • C07D207/04—Heterocyclic 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
    • C07D207/10—Heterocyclic 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; 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
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems 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)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (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)
JP2020506341A 2017-08-07 2018-08-06 ２－［（１ｒ，６ｒ）－６－イソプロペニル－３－メチルシクロヘキサ－２－エン－１－イル］－５－ペンチルベンゼン－１，３－ジオールの共結晶 Active JP7186460B2 (ja)

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

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JP2020529450A JP2020529450A (ja) 2020-10-08
JP2020529450A5 JP2020529450A5 (enExample) 2021-08-19
JP7186460B2 true JP7186460B2 (ja) 2022-12-09

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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
AU2018383598B2 (en) 2017-12-11 2024-03-07 Artelo Biosciences, Inc. New solid forms of cannabidiol and uses thereof
US20230381134A1 (en) * 2020-01-03 2023-11-30 Purisys, Llc Cocrystals of cannabinoids
US20230183202A1 (en) * 2020-05-19 2023-06-15 Ebers Tech Inc. Tetrahydrococannabinolic 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

Citations (6)

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WO2004026802A1 (en) 2002-09-23 2004-04-01 Gw Pharma Limited Method of preparing cannabidiol from plant material
WO2010126501A1 (en) 2009-04-29 2010-11-04 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
JP2011256175A (ja) 2003-12-09 2011-12-22 Medcrystalforms Llc 活性剤との混合相共結晶の調製方法
WO2012116349A2 (en) 2011-02-26 2012-08-30 Amplio Pharma, Llc Novel cocrystals of ezetimibe
JP2021505674A (ja) 2017-12-11 2021-02-18 アーテロ バイオサイエンシズ，インコーポレイテッド カンナビジオールの新しい固体形態およびその使用

Family Cites Families (6)

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Publication number Priority date Publication date Assignee Title
TWI366460B (en) 2005-06-16 2012-06-21 Euro Celtique Sa Cannabinoid active pharmaceutical ingredient for improved dosage forms
AU2006297300B2 (en) 2005-09-29 2012-05-10 Albany Molecular Research, Inc. Process for production of delta-9-tetrahydrocannabinol
ES2534900T3 (es) 2007-07-30 2015-04-30 Zynerba Pharmaceuticals, Inc. Profármacos de cannabidiol, composiciones que comprenden los profármacos de cannabidiol y métodos de uso de 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
EP2842933B1 (de) 2013-09-03 2015-07-29 Symrise AG Mischungen cannabinoider Verbindungen, deren Herstellung und Verwendung
US10226442B2 (en) * 2017-07-10 2019-03-12 Syneurx International (Taiwan) Corp. Lithium salts of N-substituted glycine compounds and uses thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004026802A1 (en) 2002-09-23 2004-04-01 Gw Pharma Limited Method of preparing cannabidiol from plant material
JP2011256175A (ja) 2003-12-09 2011-12-22 Medcrystalforms Llc 活性剤との混合相共結晶の調製方法
WO2010126501A1 (en) 2009-04-29 2010-11-04 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
JP2021505674A (ja) 2017-12-11 2021-02-18 アーテロ バイオサイエンシズ，インコーポレイテッド カンナビジオールの新しい固体形態およびその使用

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He, Hongyan et al.，Modulating the Dissolution and Mechanical Properties of Resveratrol by Cocrystallization，Crystal Growth & Design，2017年，(2017 ), 17(7), 3989-3996
He, Hongyan et al.，Zwitterionic Cocrystals of Flavonoids and Proline: Solid-State Characterization, Pharmaceutical Properties, and Pharmacokinetic Performance，Crystal Growth & Design，2016年，(2016), 16(4), 2348-2356
Pharm Tech Japan，2009年，Vol. 25, No.12，p.155-66
Qiao, Ning et al.，Pharmaceutical cocrystals: An overview，International Journal of Pharmaceutics，2011年，(2011), 419(1-2), 1-11
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CN111183127A (zh) 2020-05-19
US11168047B2 (en) 2021-11-09
WO2019030158A1 (en) 2019-02-14
EP3665145A1 (en) 2020-06-17
US20200369586A1 (en) 2020-11-26
CN111183127B (zh) 2023-02-21
JP2020529450A (ja) 2020-10-08
CA3107566A1 (en) 2019-02-14

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