WO2025023235A1 - 分岐型マルチ水酸基保護オリゴマー及びこれと結合されてなる連結体、並びに当該連結体が脱保護されてなる分岐型マルチ水酸基オリゴマー - Google Patents

分岐型マルチ水酸基保護オリゴマー及びこれと結合されてなる連結体、並びに当該連結体が脱保護されてなる分岐型マルチ水酸基オリゴマー Download PDF

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WO2025023235A1
WO2025023235A1 PCT/JP2024/026267 JP2024026267W WO2025023235A1 WO 2025023235 A1 WO2025023235 A1 WO 2025023235A1 JP 2024026267 W JP2024026267 W JP 2024026267W WO 2025023235 A1 WO2025023235 A1 WO 2025023235A1
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formula
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nmr
mhz
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French (fr)
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忠勝 萬代
悠生 妹尾
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Tomoike Bio Ltd
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Tomoike Bio Ltd
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Priority to JP2025535829A priority Critical patent/JP7784786B2/ja
Priority to CN202480061053.6A priority patent/CN121909184A/zh
Priority to KR1020267006192A priority patent/KR20260043131A/ko
Publication of WO2025023235A1 publication Critical patent/WO2025023235A1/ja
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Definitions

  • the present invention relates to a branched multi-hydroxyl protected oligomer, a linker bonded thereto, and a branched multi-hydroxyl oligomer obtained by deprotecting the linker.
  • Pterostilbene a type of polyphenol, and resveratrol are known to have antioxidant and anti-inflammatory effects, as well as to improve skin elasticity.
  • they are poorly water-soluble, and have problems with not mixing uniformly and precipitating over time.
  • Glycosylation in which sugar components are chemically linked to aglycones, is known as a method for improving the water solubility of poorly water-soluble compounds, but in order to achieve sufficient water solubility, it is necessary to combine multiple monosaccharides, and the hydroxyl groups of the monosaccharides also need to be protected, which can be costly.
  • multi-hydroxylation examples include polyethylene glycol (PEG), polyglycerol (PGL), and branched oligomer (BGL).
  • PEG polyethylene glycol
  • PGL polyglycerol
  • BGL branched oligomer
  • X is a general representation of a functional group that links to a poorly water-soluble target, and n is an integer equal to or greater than 1.
  • PEG is highly toxic in its monomers and dimers, and only oligomers with more than a few dozen can fully exhibit water solubility.
  • PGL has many uncontrollable asymmetric carbons, making it difficult to maintain reproducibility in the production, homogeneity, and quality assurance of the compound.
  • both PEG and PGL are produced by polymerization reactions, uneven molecular weight is also a problem.
  • the stereochemistry at the sugar linkage (anomeric position) is often uncontrollable and mixtures are produced.
  • BGL does not have asymmetric carbons, and a production method that can control the molecular weight has been established.
  • the arylmethyl group is not particularly limited as long as it has a structure in which an aryl group is bonded to a methyl group, and examples thereof include a benzyl group and a 4-methoxybenzyl group.
  • R a , R c and R d each represent at least one selected from the group consisting of a hydrogen atom and an alkyl group.
  • the above-mentioned protecting groups may further have a substituent, and such substituents include halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms; alkyl groups such as methyl groups, ethyl groups, and n-propyl groups; alkenyl groups such as vinyl groups, allyl groups, methylvinyl groups, and propenyl groups; alkynyl groups such as ethynyl groups, propynyl groups, and propargyl groups; aryl groups such as phenyl groups and naphthyl groups; alkoxy groups such as methoxy groups, ethoxy groups, propoxy groups, isopropoxy groups, and butoxy groups; alkylthio groups such as methylthio groups, ethylthio groups, propylthio groups, and butylthio groups; arylthio groups such as phenylthio groups and naphthy
  • the halogen atom in Xa is preferably a bromine atom, a chlorine atom, or an iodine atom.
  • the substituent X in the obtained branched multi-hydroxyl-protected oligomer is at least one selected from the group consisting of groups represented by formula (2), and it is possible to convert it to a desired substituent X by appropriately carrying out a tosylation reaction, a deallylation reaction, or the like.
  • X has the same meaning as in formula (1), Xa is a halogen atom, and R 1 is a group obtained by removing —OH from at least one alcohol R 1 —OH selected from the group consisting of the following formula (4)]
  • X has the same meaning as in formula (1), Xa is a halogen atom, and R 1 is a group obtained by removing —OH from at least one alcohol R 1 —OH selected from the group consisting of the following formula (4)]
  • X has the same meaning as in formula (1), Xb is a halogen atom, and R 1 -OH is at least one selected from the group consisting of alcohols represented by formula (4):
  • the obtained branched multi-hydroxyl-protected oligomer can be bonded to a target compound.
  • a conjugate can be obtained by reacting it with the hydroxyl group of the target compound, pterostilbene, as shown in the following reaction formula (IV).
  • a conjugate formed by bonding a branched multi-hydroxyl-protected oligomer to a target compound is a preferred embodiment.
  • a poorly water-soluble compound is preferred as the target compound, and a polyphenol compound having a hydroxyl group, such as pterostilbene or resveratrol, is preferred as the poorly water-soluble compound.
  • the branched multi-hydroxyl-protected oligomer to be bonded to the target compound may be a deprotected branched multi-hydroxyl-protected oligomer, but from the viewpoint of efficient reaction, it is a preferred embodiment to obtain a linker bonded to the target compound and then deprotect the linker.
  • a known method is used for the deprotection.
  • the protecting groups in the linker are deprotected to generate a large number of hydroxyl groups.
  • the branched multi-hydroxyl-protected oligomer of the present invention has a very high effect of improving the water solubility of the target compound, which is a poorly water-soluble compound. Therefore, a water solubility improver consisting of a branched multi-hydroxyl-protected oligomer is a preferred embodiment.
  • A1 (1-methyl-2,6,7-trioxabicyclo[2.2.2]octan-4-yl)methanol is a known compound whose preparation is described in T. Jeffrey Dunn, William L. Neumann, Milorad M. Rogic, and Steven R. Woulfe J. Org. Chem., 1990, 55, 6368-6373.
  • A2 (2s,5s)-2-methyl-1,3-dioxan-5-ol can be obtained by the known method of WO2020/255741A1.
  • A3 (2,2-dimethyl-1,3-dioxolan-4-yl)methanol can be obtained from TCI (Tokyo Chemical Industry Co., Ltd.).
  • A22 1,3-bis((2,2-dimethyl-1,3-dioxan-5-yl)oxy)propan-2-ol can be synthesized by the known method described in Nemoto, Hisao; Kamiya, Masaki; Nakamoto, Aki; Katagiri, Ayato; Yoshitomi, Kohsuke; Kawamura, Tomoyuki; Hattori, Hatsuhiko. Chem. Lett. 2010, 39, 856-857.
  • A23 1,3-bis((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)propan-2-ol is commercially available from Synnovator Product.
  • 1,3-dibromo-2-(bromomethyl)-2-((methoxymethoxy)methyl)propane can be produced in 80% yield by the equilibrium reaction of acetal exchange between 3-bromo-2,2-bis(bromomethyl)propan-1-ol and 20 equivalents of dimethoxymethane in the absence of a solvent and under acid catalysis for 12 hours.
  • Ion-exchanged water 50-80 mL was poured into the suspension at room temperature, and the mixture was extracted with ethyl acetate (200-300 mL). The resulting organic layer was washed with ion-exchanged water (50-80 mL, 2-3 times), and then concentrated under reduced pressure.
  • the target compound H117 was obtained by using H116 as R 4 —OH in Synthesis Example 5. The crude product of H117 was used as it was in the next reaction.
  • the target compound H127' was obtained by using H124 as R 4 -OH in Synthesis Example 5. The crude product of H127' was used as it was in the next reaction.
  • the target compound H127 was obtained by using H126 as R 4 —OH in Synthesis Example 5. The crude product of H127 was used as it was in the next reaction.
  • the target compound H137 was obtained by using H136 as R 4 —OH in Synthesis Example 5. The crude product of H137 was used as it was in the next reaction.
  • Example 19 Water solubility evaluation
  • the deprotected pterostilbene conjugates obtained in the examples were evaluated for water solubility by the following method. The results are shown in Figures 1 and 2.
  • the numbers in the ellipses for each compound represent the degree of water solubility in molar ratios when the water solubility of F1 (pterostilbene) (21 mg (0.0819 mmol) dissolved in 1 L) is taken as 1.0.
  • the water solubility of F1 (pterostilbene) was determined by the value described in Sarah J. Bethune et al., Cryst. Growth Des. 2011, 11, 2817-2823.
  • the water solubility of F1 glycoside (pterostilbene monoglycoside) was determined by the value described in Jose L. Gonzalez-Alfonso et al., Molecules 2018, 23, 1271.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/JP2024/026267 2023-07-26 2024-07-23 分岐型マルチ水酸基保護オリゴマー及びこれと結合されてなる連結体、並びに当該連結体が脱保護されてなる分岐型マルチ水酸基オリゴマー Pending WO2025023235A1 (ja)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2025535829A JP7784786B2 (ja) 2023-07-26 2024-07-23 分岐型マルチ水酸基保護オリゴマー及びこれと結合されてなる連結体、並びに当該連結体が脱保護されてなる分岐型マルチ水酸基オリゴマー
CN202480061053.6A CN121909184A (zh) 2023-07-26 2024-07-23 分支型多羟基保护低聚物和与其结合而成的连接体、以及该连接体脱保护而成的分支型多羟基低聚物
KR1020267006192A KR20260043131A (ko) 2023-07-26 2024-07-23 분기형 멀티 수산기 보호 올리고머, 이와 결합되어 이루어지는 연결체 및 상기 연결체가 탈보호되어 이루어지는 분기형 멀티 수산기 올리고머

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JP2023121964 2023-07-26
JP2023-121964 2023-07-26

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US3261686A (en) * 1963-04-23 1966-07-19 Du Pont Photopolymerizable compositions and elements
JP2009527581A (ja) * 2006-02-21 2009-07-30 ネクター セラピューティックス エイエル，コーポレイション 分割型の分解性重合体とそれから生成される複合体
US20110286956A1 (en) * 2008-11-03 2011-11-24 Beijing Jenkem Technology Co. Ltd. Novel multi-arm polyethylene glycol, preparation method and uses thereof
JP2011530597A (ja) * 2008-08-11 2011-12-22 ネクター セラピューティックス マルチアームポリマーアルカノエートコンジュゲート
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WO2020255741A1 (ja) 2019-06-17 2020-12-24 有限会社ケミカル電子 親水性金属表面処理剤
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JP2022014977A (ja) 2020-07-08 2022-01-21 東ソー・ファインケム株式会社 含フッ素化合物並びにその重合体及び表面改質剤組成物

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US7696359B2 (en) 2003-09-03 2010-04-13 Kyowa Hakko Kirin Co., Ltd. Compound modified with glycerol derivative
MX2007010402A (es) * 2005-04-20 2008-01-22 Dendritic Nanotechnologies Inc Polimeros dendriticos con amplificacion mejorada y funcionalidad interior.
KR20150125727A (ko) * 2008-01-23 2015-11-09 세키스이가가쿠 고교가부시키가이샤 합판 유리용 중간막, 및 합판 유리
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WO2020255741A1 (ja) 2019-06-17 2020-12-24 有限会社ケミカル電子 親水性金属表面処理剤
JP2022014977A (ja) 2020-07-08 2022-01-21 東ソー・ファインケム株式会社 含フッ素化合物並びにその重合体及び表面改質剤組成物

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JP7784786B2 (ja) 2025-12-12
CN121909184A (zh) 2026-04-21
KR20260043131A (ko) 2026-03-31

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