EP4259065A1 - Dérivés de tétrahydrocannabinol à base de silicium et leurs compositions - Google Patents

Dérivés de tétrahydrocannabinol à base de silicium et leurs compositions

Info

Publication number
EP4259065A1
EP4259065A1 EP20835965.3A EP20835965A EP4259065A1 EP 4259065 A1 EP4259065 A1 EP 4259065A1 EP 20835965 A EP20835965 A EP 20835965A EP 4259065 A1 EP4259065 A1 EP 4259065A1
Authority
EP
European Patent Office
Prior art keywords
silicon
tetrahydrocannabinol
derivative according
group
formula
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.)
Pending
Application number
EP20835965.3A
Other languages
German (de)
English (en)
Inventor
Barry C. Arkles
Taewoo Min
Jonathan D. GOFF
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.)
Gelest Inc
Original Assignee
Gelest Inc
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
Application filed by Gelest Inc filed Critical Gelest Inc
Publication of EP4259065A1 publication Critical patent/EP4259065A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • 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
    • A61K31/695—Silicon compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions

Definitions

  • Tetrahydrocannabinol is a phytocannabinoid which is known to have antiinflammatory activity. It is the primary psychoactive cannabinoid and is known to bind to cannabinoid receptors (CB 1 and CB2) to reduce pain, inflammation, and hyperalgesia (see, for example, Citti et al, Sci. Rep. 9, 20335 (2019); Karsak et al, Science, 316,1494 (2007);
  • Tetrahydrocannabinol is the designated name for (6a7?,10a7?)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-67/-benzo[c]chromen-l-ol, shown below:
  • a silicon-based tetrahydrocannabinol derivative according to an embodiment of the disclosure contains a silicon-based functional group containing Si-O-Si bonds which is bound to a tetrahydrocannabinol molecule having Formula (I):
  • a topical or dermatological formulation according to an embodiment of the disclosure contains a base formulation and at least one silicon-based tetrahydrocannabinol derivative comprising at least one silicon-based functional group containing Si-O-Si bonds which is bound to a tetrahydrocannabinol molecule having Formula (I):
  • the disclosure relates to compositions containing derivatives of tetrahydrocannabinol (THC) containing a silicon-containing functional group which are beneficial for various applications, including the formulation of topical medicinal products and personal care products, and methods for their preparation.
  • THC tetrahydrocannabinol
  • the silicon-containing tetrahydrocannabinol derivatives described herein are unique hybrid organosilicon compounds formed by attaching tetrahydrocannabinol to a siloxane backbone, also described as a molecule comprising one silicon-based functional group containing Si-O-Si bonds which is bound to a tetrahydrocannabinol molecule.
  • cannabinoid acceptors of the compounds described herein has not yet been studied, they are expected to provide increased stability and solubility and to release the free tetrahydrocannabinol uniformly and over a prolonged period.
  • tetrahydrocannabinol and THC are intended to encompass all isomers of tetrahydrocannabinol, including those found naturally or developed synthetically.
  • Preferred embodiments of the compounds of the disclosure include trisiloxanyl derivatives of tetrahydrocannabinol in which a siloxane-based group is bound through the phenolic hydroxyl group of the tetrahydrocannabinol molecule, forming an Si-O-C bond.
  • the silicon-based tetrahydrocannabinol derivatives include a tetrahydrocannabinol molecule, such as shown in Formula (I), having a silicon-based group as a functional group. Most preferably, the silicon-based group is a siloxanyl group or a trialkoxysilane- containing group.
  • Preferred tetrahydrocannabinol derivatives described herein have a structure in accordance with Formula (I) above in which the phenolic hydroxyl group is bound to a siloxane moiety containing two or more silicon atoms, preferably three or more silicon atoms, most preferably about 3 to about 10 silicon atoms.
  • Tetrahydrocannabinol derivatives according to embodiments of the invention have general formula (A).
  • R may be, for example and without limitation, SiMe(OSiMe 3 )2, SiMe2(OSiMe2)4CH2CH2CH 2 CH3, SiMe 2 OSiMe3, and SiMe 2 OSiMe2C 6 H5, in which “Me” is a methyl group.
  • compounds having formula (A) that are within the scope of the disclosure are not limited to these substituents, and other silicon-containing functional groups having Si-O-Si bonds that are known in the art or to be developed would also be suitable for R.
  • Substituents containing a single silicon atom without an oxane (oxygen) bridge between two or more silicon atoms are not within the scope of the disclosure because such tetrahydrocannabinol derivatives fail to provide acceptable film-forming properties.
  • simple trialkylsilyl derivatives, as well as derivatives containing only alkyl, aryl, hydrogen, halogen, vinyl, allyl and/or alkoxy substituents on the silicon are not within the scope of the disclosure as these are not effective for the intended purpose.
  • Other compounds within the scope of the disclosure include polydimethylsiloxanes in which the tetrahydrocannabinol substitutes through the phenolic oxygen in place of a methyl group on a polydimethylsiloxane, such as Me3Si(OSiMe2)m(OSiMeTHC)nSiMe3, in which “THC” represents tetrahydrocannabinol, Me is a methyl group, and m and n are integers.
  • m is 1 to about 100 and n is 1 to about 10.
  • the silicon-based tetrahydrocannabinol derivatives according to embodiments of the disclosure include a wide variety of derivatized compounds, including most preferred compounds such as, for example, (tetrahydrocannabinoloxy)heptamethyltrisiloxane (formula (II)), tetrahydrocannabinoloxy-terminated polydimethylsiloxane (formula (III)), and tetrahydrocannabinoloxypropyl-terminated polydimethylsiloxane (formula (IV)), shown below, in which m and n are integers; preferably m is 1 to about 100 and n is 1 to about 10.
  • Compounds according to embodiments of the disclosure may contain a direct ether linkage between the silicon-containing functional group and the phenolic hydroxyl group of the tetrahydrocannabinol molecule (direct Si-0 bond) or may contain an alkyl group spacer between the phenolic hydroxyl group on tetrahydrocannabinol and the silicon-based functional group, such as compounds in which R in formula (A) is CfbSiNfeOSiMes or CfbSiNfeOSiNfeCeHs.
  • the spacer is not limited to CH2, and may also be a longer alkyl chain containing up to about 11 carbon atoms, such as (CH2)3, which, along with CH2, is also a preferred embodiment.
  • Compounds according to embodiments of the disclosure which contain an alkyl group spacer between the phenolic hydroxyl group on tetrahydrocannabinol and the silicon-based functional group may have general formula (B) below, in which R’ is a silicon-based group and x is an integer ranging from 1 to about 11, preferably 1 (methyl) to 3 (propyl). Most preferably, the silicon-based group is a siloxanyl group or a trialkoxysilane-containing group.
  • R’ may be, for example and without limitation, SiMe(OSiMe3)2, SiMe2(OSiMe2)4CH2CH2CH2CH3, SiMe2OSiMe3, or SiMe2OSiMe2CeH5, in which Me is methyl.
  • Direct Si-0 linkage of the tetrahydrocannabinol derivatives may result in diminished allergic inflammation by releasing free tetrahydrocannabinol over a prolonged period by slow hydrolysis.
  • the Si-0 bond on tetrahydrocannabinol derivatives is not stable when exposed to moisture, which results in slow decomposition of compounds to form free tetrahydrocannabinol and low molecular weight siloxanes.
  • the silane-based tetrahydrocannabinol derivatives are anticipated to be stable when stored in air and protected from moisture. They are anticipated to show bioactivity in medicinal applications either directly or by slow hydrolysis to form underivatized THC.
  • silicones and silicone derivatives are easily incorporated into topical or dermatological products, including anti-inflammatory and palliative formulations, due to their solubility in a range of polar compounds such as castor oil and a variety of cosmetic or dermatological vehicles. They may also act as co-solvents for silicones. Further, due to such solubility, these derivatives may be useful as compatibilizers for other bioactives, such as unmodified cannabidiol and tetrahydrocannabinol compounds, among other possible applications.
  • the tetrahydrocannabinol derivatives described herein may be prepared by various synthetic pathways.
  • the compounds may be prepared by reacting the hydroxyl group on the benzenoid ring of tetrahydrocannabinol with an allylic halide in a solvent to form an allyloxytetrahydrocannabinol intermediate, and then hydrosilylating the intermediate with a silane compound and catalyst to form a silicon-based tetrahydrocannabinol derivative with a spacer.
  • a direct Si-0 linkage on the hydroxyl group of tetrahydrocannabinol by reacting the hydroxyl group (C-OH) with a chlorine-containing siloxane compound (-Si-Cl) in the presence of a base acceptor, or by the dehydrogenative coupling of the hydroxyl group with a hydride- containing siloxane compound (-Si-H).
  • the silane compounds used in the reactions described above may be any of a wide variety of silicon-based compounds, and preferably include alkylsilanes, alkoxysilanes, alkylsiloxanes and alkoxysiloxanes and their derivatized or functionalized counterparts. In general, it is preferred to have two or more silicon atoms in the substitution in order to provide solubility and spreading characteristics suitable for topical creams and ointments.
  • Examples include, without limitation, bis(trimethylsiloxy)methylsilane, bis(trimethylsiloxy)ethylsilane, bis(trimethylsiloxy)propylsilane, bis(triethylsiloxy)methylsilane, bis(triethylsiloxy)ethylsilane, bis(triethylsiloxy)propylsilane, triethoxysilane, trimethoxysilane, tripropylsilane, bis(tripropylsiloxy)methylsilane, bis(tripropylsiloxy)ethylsilane, bis(tripropylsiloxy)propylsilane and similar compounds.
  • silane compounds herein are polymeric silicon-containing molecules having similar reactive capabilities as the silane monomeric structures noted above, such as polydimethylsiloxane, polydiethylsiloxane, poly dipropyl siloxane, polymethylethylsilane, polymethylpropylsiloxane, and other polyalkyl- or polyalkenyl-siloxanes as are known in the art or to be developed. Chain lengths may vary, but it is preferred that the molecular weight (Mn) of polymeric silane compounds used to form polymeric silicon-based derivative groups on tetrahydrocannabinol be from 100 to about 5000, and most preferably from about 500 to about 2000.
  • Mn molecular weight
  • the derivatives described herein may be produced using pure tetrahydrocannabinol.
  • the derivatives may be formed and provided as a component of phytocannabinoid and/or other phytochemical mixtures.
  • the tetrahydrocannabinol derivative of cannabis extracts may be formed without isolating the pure tetrahydrocannabinol component.
  • compositions according to the invention may contain one or more of the derivatives described herein and one or more phytochemicals extracted from cannabis.
  • the silicon-based tetrahydrocannabinols described herein may be used in various topical and dermatological compositions, including preferably those which have silicon compounds or silicone-based polymers in the base formulation because the derivatives facilitate compatibility and solubility in such compounds within formulations.
  • the disclosure is not limited to those compositions and may include any topical or dermatological composition in which the silicon-based tetrahydrocannabinol derivatives are useful.
  • the cosmetic and topical compositions of the present disclosure include a base formulation, which may be any suitable topical or dermatological base formulation as described above, and at least one silicon-based tetrahydrocannabinol derivative as described herein.
  • the silicon-based tetrahydrocannabinol derivatives include a tetrahydrocannabinol molecule or a commercial or natural derivative thereof and include a silicon-based functional group bonded to the tetrahydrocannabinol molecule (or the derivative thereof) through the oxygen atom of the benzenoid ring.
  • the silicon-based tetrahydrocannabinol derivative is present in an amount of about 0.01 percent by weight to about 20 percent by weight, preferably about 0.5 percent by weight to about 5 weight percent and most preferably about 0.5 to about 1.0 percent by weight based on the weight of the formulation.
  • reaction mixture is filtered through silica gel (40g) and washed with tetrahydrofuran (400g). The filtrate is concentrated in vacuo. The residue contains the product and unreacted tetrahydrocannabinol and is analyzed by NMR and FTIR.
  • Example 2 Synthesis of 1-butyl-l, 1,3, 3,5,5, 7,7,9,9-decamethyl-9-(((6aR,10aR)-6,6,9-trimethyl- 3 -pentyl-6a,7, 8, 10a-tetrahvdro-6H-benzol clchromen- 1 -yl)oxy)pentasiloxane (III)
  • reaction mixture is filtered through silica gel (40g) and washed with tetrahydrofuran (400g). The filtrate is concentrated in vacuo. The residue contains the product and unreacted tetrahydrocannabinol and is analyzed by NMR and FTIR.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne des dérivés de tétrahydrocannabinol à base de silicium et des procédés pour leur synthèse, les dérivés contenant une molécule de tétrahydrocannabinol et au moins un groupe à base de silicium contenant des liaisons Si-O-Si. Les dérivés sont utiles dans des compositions topiques et dermatologiques, ont des propriétés topiques bénéfiques potentielles, et améliorent la solubilité et la compatibilité dans des formulations topiques et dermatologiques contenant les matériaux à base de silicium.
EP20835965.3A 2020-12-10 2020-12-10 Dérivés de tétrahydrocannabinol à base de silicium et leurs compositions Pending EP4259065A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2020/064235 WO2022125095A1 (fr) 2020-12-10 2020-12-10 Dérivés de tétrahydrocannabinol à base de silicium et leurs compositions

Publications (1)

Publication Number Publication Date
EP4259065A1 true EP4259065A1 (fr) 2023-10-18

Family

ID=74125705

Family Applications (1)

Application Number Title Priority Date Filing Date
EP20835965.3A Pending EP4259065A1 (fr) 2020-12-10 2020-12-10 Dérivés de tétrahydrocannabinol à base de silicium et leurs compositions

Country Status (6)

Country Link
EP (1) EP4259065A1 (fr)
JP (1) JP2023554329A (fr)
KR (1) KR20230143137A (fr)
CN (1) CN116685595A (fr)
CA (1) CA3201704A1 (fr)
WO (1) WO2022125095A1 (fr)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2854896B1 (fr) * 2003-05-16 2007-08-17 Mayoly Spindler Lab Nouveaux tensioactifs, compositions les comprenant
EP2176208B1 (fr) * 2007-07-30 2015-01-21 Zynerba Pharmaceuticals, Inc. Promédicaments de cannabidiol, compositions comprenant les promédicaments de cannabidiol et leurs procédés d'utilisation
WO2018148785A1 (fr) * 2017-02-15 2018-08-23 Botanix Pharmaceuticals Ltd Formulations de cannabinoïdes pour le traitement de la dermatite et de maladies cutanées inflammatoires
WO2018148787A1 (fr) * 2017-02-15 2018-08-23 Botanix Pharmaceuticals Ltd Formulations de cannabinoïdes pour le traitement du psoriasis
WO2020214574A1 (fr) * 2019-04-15 2020-10-22 Trustees Of Boston University Synthèse à médiation par l'écoulement en une étape de cannabidiol (cbd) et de ses dérivés
CN112047973B (zh) * 2019-06-06 2022-11-18 上海科技大学 一种大麻素类化合物，其制备方法、组合物和用途

Also Published As

Publication number Publication date
WO2022125095A1 (fr) 2022-06-16
KR20230143137A (ko) 2023-10-11
CA3201704A1 (fr) 2022-06-16
JP2023554329A (ja) 2023-12-27
CN116685595A (zh) 2023-09-01

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