JP7156759B2 - ケイ素ベースのカンナビジオール誘導体及びその組成物 - Google Patents
ケイ素ベースのカンナビジオール誘導体及びその組成物 Download PDFInfo
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- JP7156759B2 JP7156759B2 JP2020571843A JP2020571843A JP7156759B2 JP 7156759 B2 JP7156759 B2 JP 7156759B2 JP 2020571843 A JP2020571843 A JP 2020571843A JP 2020571843 A JP2020571843 A JP 2020571843A JP 7156759 B2 JP7156759 B2 JP 7156759B2
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- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- IXEXMSWSWDRVIF-UHFFFAOYSA-N triethyl-[silyl(triethylsilyloxy)methoxy]silane Chemical compound CC[Si](CC)(CC)OC([SiH3])O[Si](CC)(CC)CC IXEXMSWSWDRVIF-UHFFFAOYSA-N 0.000 description 1
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- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
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- PBADBUWJLFERAM-UHFFFAOYSA-N tripropyl-[silyl(tripropylsilyloxy)methoxy]silane Chemical compound CCC[Si](CCC)(CCC)OC([SiH3])O[Si](CCC)(CCC)CCC PBADBUWJLFERAM-UHFFFAOYSA-N 0.000 description 1
- ZHOVAWFVVBWEGQ-UHFFFAOYSA-N tripropylsilane Chemical compound CCC[SiH](CCC)CCC ZHOVAWFVVBWEGQ-UHFFFAOYSA-N 0.000 description 1
- ICWQKCGSIHTZNI-UHFFFAOYSA-N tris(16-methylheptadecyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCCCCCCCCCC(C)C)CC(=O)OCCCCCCCCCCCCCCCC(C)C ICWQKCGSIHTZNI-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- 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
-
- 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
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/08—Dihydroxy benzenes; Alkylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/305—Compounds having groups having acetal carbon atoms as rings members or bound to carbon atoms of rings other than six-membered aromatic rings
-
- 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
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Silicon Polymers (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
[0002]本出願は、2019年10月25日に出願された同時係属中の米国特許仮出願第62/925,945号の優先権を主張するものであり、その開示は、参照により本明細書に組み込まれる。
[0003]カンナビジオールは、抗炎症活性を有すると考えられている植物性カンナビノイドである。カンナビジオールは、生物学的作用を呈するが、一方で神経精神薬理学的効果をほとんど又は全く呈さない、構造的に関連する化合物のファミリーの1つのメンバーである(D.L.Boggs Neuropsychopharmacology;43(1):142~154;2018)。カンナビジオールは、以下に示す2-[(1R,6R)-3-メチル-6-(1-メチルエテニル)-2-シクロヘキセン-1-イル]-5-ペンチル-1,3-ベンゼンジオールの指定名である:
[0005]本開示の実施形態に従うケイ素ベースのカンナビジオール誘導体は、式(I):
を有するカンナビジオール分子と結合されている、Si-O-Si結合を含有する少なくとも1つのケイ素ベースの官能基を含む。
を有するカンナビジオール分子と結合されている、Si-O-Si結合を含有する少なくとも1つのケイ素ベースの官能基を含む少なくとも1つのケイ素ベースのカンナビジオール誘導体とを含む。
[0007]本開示は、局所用医薬品及びパーソナルケア製品への製剤化を含む種々の用途に有用なカンナビジオール(CBD)のシリコーン可溶性誘導体を含有する組成物、並びに該組成物の調製のための方法に関する。本明細書において記述されているカンナビジオールのケイ素ベースの誘導体は、カンナビジオールをシロキサン骨格に結合させることによって形成される独自のハイブリッド有機ケイ素化合物であり、カンナビジオール分子と結合されている、Si-O-Si結合を含有する少なくとも1つのケイ素ベースの官能基を含む分子としても記述されている。カンナビジオール置換基は、シロキサン骨格に皮膚処置特性を付加し、一方、シロキサン成分は、カンナビジオールの皮膚軟化性スリップ(emolliency slip)及び皮膚感触を改善する。この独自の構造は、有機ケイ素変性カンナビノイド化合物が、鉱物及び植物性ワックスを含む若干数の化粧用ビヒクル、並びに非誘導体化カンナビノイドにおいて、可溶化剤として挙動することを可能にする。このことは、非誘導体化カンナビノイド化合物の局所用製剤の溶解性の欠如及び不良な展延性が、所望の組成及び活性の均一な薄膜を塗布することへの障害となることから、重要である。本明細書において記述されている組成製品は、経表皮活性を呈しても呈さなくてもよいが、カンナビノイドの均一な分布のためのビヒクルとして作用する該組成製品の能力は、より低いレベル及びより均一な経皮活性を可能にすることによって、エンドカンナビノイド受容体に関連する非変性カンナビノイドの薬理活性を向上させる可能性を有する。
実施例1:2-[(1R,6R)-3-メチル-6-(1-メチル-2-(ビス(トリメチルシロキシ)メチルシリル)エチル)-2-シクロヘキセン-1-イル]-5-ペンチル-1,3-ベンゼンジオールの合成
[0033]ビス(トリメチルシロキシ)メチルシラン(21.36g、0.10mol)及びカルステッド触媒(キシレン中2%Pt濃度、1mL)を反応器に投入した。トルエン(21.89g)中のカンナビジオール(25.16g、0.08mol)の溶液を、ポット温度を30℃未満に保ちながら、30分間かけて滴下添加した。得られた反応混合物を室温で2時間撹拌し、次いで、シリカゲル(80g)に通して濾過し、トルエン(800g)で洗浄した。濾液を真空中で濃縮した。残留物は、橙色油としての生成物(32.0g、74%)であった。分析データ:25℃におけるR.I. 1.488;1H NMR(400MHz,CDCl3)δ6.23(bs,2H)、6.00(bs,1H)、5.52(s,1H)、4.63(bs,1H)、3.81(dd,J=6.0,2.4Hz,1H),2.47~2.41(m,2H)、2.23~2.05(m,1H)、1.76~1.73(m,3H)、1.62~1.55(m,6H)、1.38~1.25(m,6H)、0.90~0.82(m,6H)、0.146(dd,J=14.0,12.4Hz,1H)、0.08(s,9H)、0.07(s,9H)、0.00(s,3H);FTIR(cm-1):3435、2956、2929、2873、2858、1628、1582、1514、1443、1377、1251、1218、1039、1025;GC-MS m/z:536(M)、521(M-Me)、446(M-OSiMe3)。
[0034]1-ブチル-1,1,3,3,5,5,7,7,9,9-デカメチルペンタシロキサン(34.89g、0.08mol)及びカルステッド触媒(キシレン中2%Pt濃度、1mL)を反応器に投入した。トルエン(17.78g)中のカンナビジオール(20.44g、0.07mol)の溶液を、ポット温度を50℃未満に保ちながら、30分間かけて滴下添加した。得られた反応混合物を40℃で3~5時間加熱し、シリカゲル(50g)に通して濾過し、トルエン(400g)で洗浄した。濾液を真空中で濃縮した。残留物は、所望の生成物(III)及び副産物(V)(比率9:1、46.7g)を粘性橙色液体として含有していた。分析データ:25℃におけるR.I. 1.462;d:1.019g/mL;1H NMR(400MHz,CDCl3)δ6.26(bs,1H)、6.15(bs,1H)、6.01(bs,1H)、5.52(s,1H)、5.12(bs,1H)、3.84~3.81(m,1H)、2.46~2.41(m,2H)、2.15~2.06(m,1H)、1.76~1.55(m,9H)、1.35~1.25(m,12H)、0.9~0.87(m,12H)、0.56~0.52(m,3H)、0.12~0.03(m,32H);FTIR(cm-1):3451、2958、2926、1628、1583、1444、1257、1219、1022。
[0035]ナトリウム(0.77g、0.03mol)及びテトラヒドロフラン(13.42g)を反応器に投入した。テトラヒドロフラン(37.98g)中のカンナビジオール(5.03g、0.02mol)の溶液を、ポット温度を70℃未満に保ちながら、30分間かけて滴下添加した。得られた反応混合物を、すべてのナトリウムが消費されるまで、室温で撹拌した。ビス(トリメチルシロキシ)メチルシラン(14.24g、0.06mol)を70℃で10分間かけて滴下添加し、次いで、反応混合物を110~120℃で10時間加熱した。反応混合物をシリカゲル(40g)に通して濾過し、テトラヒドロフラン(400g)で洗浄した。濾液を真空中で濃縮し、次いで、残留物をフラッシュオーバー蒸留(flash-over distillation)によって精製した。留出物は、生成物及び未反応のカンナビジオール(9:1混合物、8.4g)を透明な粘性液体として含有していた。分析データ:25℃におけるR.I. 1.453;d=1.001g/mL;FTIR(cm-1):3458、2958、2927、2857、1622、1574、1436、1376、1251、1037。
[0036]式(I)を有するカンナビジオール単離物(CBD)並びに上記の実施例1、2及び3で記述した通りの3つのシリル化CBD誘導体を、若干数の最も一般的な油及びシリコーンへの溶解性について室温で評価し、データを以下の表1にまとめる(「S」=可溶性、「I」=不溶性)。CBD単離物はすべての油に可溶性であり、すべてのシリコーン及び水に不溶性であったと結論付けることができる。CBD誘導体は水に不溶性であり、油及びシリコーンの両方に可溶性であった(実施例1の誘導体については加熱が必要とされた)。実施例2の誘導体は、ヒマシ油に部分的にのみ可溶性であった(部分加熱しながらでも)。故に、ケイ素含有基の存在は、試験したすべてのシリコーンにおいてCBDの溶解性を増大させた。
[0037]実施例3において調製された5gのトリシロキサニル-カンナビジオール生成物(IV)及び5gのn-プロピルヘプタメチルトリシロキサン(Gelestから市販されている)を20mlのバイアルに添加することによって、溶液を調製した。試料1は、一片のシリコーンエラストマー(1.5cm×2.5cm、0.35g、Gelestから市販されている)を、溶液を含有する20mlのバイアルに挿入し、バイアルを、蓋を閉めて30分間静置して、溶液をエラストマーに吸収させることによって、調製した。試料2(対照)は、同一のシリコーンエラストマー片であり、このエラストマーを、ヘンプシードオイルを含有する20mlのバイアルに挿入し、蓋を閉めて30分間静置して、ヘンプオイルをエラストマーに吸収させた。
Claims (18)
- 請求項1に記載のケイ素ベースのカンナビジオール誘導体を製造するための方法であって、カンナビジオールのイソプロペニル基をヒドロシリル化して、前記ケイ素ベースのカンナビジオール誘導体を形成するステップを含む、方法。
- 請求項1に記載のケイ素ベースのカンナビジオール誘導体を製造するための方法であって、カンナビジオールをハロゲン化アリルと溶媒中で反応させて、アリルオキシカンナビジオール中間体を形成するステップと、前記アリルオキシカンナビジオール中間体をシラン化合物及び触媒と反応させて、前記ケイ素ベースのカンナビジオール誘導体を形成するステップとを含む、方法。
- 請求項1に記載のケイ素ベースのカンナビジオール誘導体を製造するための方法であって、塩素含有シロキサン化合物を、ヒドロキシル基と、塩基受容体の存在下で反応させることにより、カンナビジオール分子にシリル化アルキルエーテルを形成するステップを含む、方法。
- 請求項1に記載のケイ素ベースのカンナビジオール誘導体を製造するための方法であって、水素化物含有シロキサンの脱水素カップリングにより、カンナビジオール分子にシリル化アルキルエーテルを形成するステップを含む、方法。
- 請求項1に記載のケイ素ベースのカンナビジオール誘導体を製造するための方法であって、中間体アルカリ金属アルコキシドを形成すること及びそれに続く、ケイ素-水素化物又はケイ素-塩素含有化合物との反応により、カンナビジオール分子にシリル化アルキルエーテルを形成するステップを含む、方法。
- 請求項1に記載のケイ素ベースのカンナビジオール誘導体と、ヘンプオイルから抽出された少なくとも1種の植物性化学物質とを含む、組成物。
- 請求項1に記載のケイ素ベースのカンナビジオール誘導体と、シロキサンとを含む、組成物であって、前記組成物が薄膜に展延し、前記薄膜が水分との反応時にカンナビジオールを形成する、組成物。
- 請求項17に記載の組成物が注入された、シリコーンエラストマー又は流体。
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