WO2015137838A1 - Hexose derivatives, preparation and uses thereof - Google Patents

Hexose derivatives, preparation and uses thereof Download PDF

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Publication number
WO2015137838A1
WO2015137838A1 PCT/PT2015/050001 PT2015050001W WO2015137838A1 WO 2015137838 A1 WO2015137838 A1 WO 2015137838A1 PT 2015050001 W PT2015050001 W PT 2015050001W WO 2015137838 A1 WO2015137838 A1 WO 2015137838A1
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WO
WIPO (PCT)
Prior art keywords
compound
salt
mmol
experiment
synthesis
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.)
Ceased
Application number
PCT/PT2015/050001
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English (en)
French (fr)
Inventor
Christopher DAVID MAYCOCK
Maria Rita Mendes Bordalo Ventura Centeno Lima
Eva CORREIA LOURENÇO
Maria Helena Dias Dos Santos
Ana Sofia DA CUNHA MIGUEL
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.)
EXTREMOCHEM LDA
Universidade de Lisboa
Universidade Nova de Lisboa
Original Assignee
EXTREMOCHEM LDA
Universidade de Lisboa
Universidade Nova de Lisboa
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
Priority to BR112016021231-2A priority Critical patent/BR112016021231B1/pt
Priority to CA2942635A priority patent/CA2942635C/en
Priority to CN201580014386.4A priority patent/CN106573952A/zh
Priority to CN202211044372.5A priority patent/CN115448964A/zh
Priority to MX2016011808A priority patent/MX386787B/es
Priority to JP2016575290A priority patent/JP7067867B2/ja
Priority to EP15724386.6A priority patent/EP3116886A1/en
Priority to SG11201607530XA priority patent/SG11201607530XA/en
Priority to US15/125,522 priority patent/US11708387B2/en
Application filed by EXTREMOCHEM LDA, Universidade de Lisboa, Universidade Nova de Lisboa filed Critical EXTREMOCHEM LDA
Priority to KR1020227017066A priority patent/KR102651029B1/ko
Priority to KR1020167028609A priority patent/KR102401853B1/ko
Priority to RU2016140337A priority patent/RU2731563C2/ru
Priority to KR1020247009385A priority patent/KR102828884B1/ko
Publication of WO2015137838A1 publication Critical patent/WO2015137838A1/en
Priority to IL247531A priority patent/IL247531B/en
Anticipated expiration legal-status Critical
Priority to US18/332,157 priority patent/US12590117B2/en
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/06—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing nitrogen as ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
    • C07K1/113—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides without change of the primary structure
    • C07K1/1136—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides without change of the primary structure by reversible modification of the secondary, tertiary or quarternary structure, e.g. using denaturating or stabilising agents
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/96—Stabilising an enzyme by forming an adduct or a composition; Forming enzyme conjugates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/22—Hormones
    • A61K38/28—Insulins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/43—Enzymes; Proenzymes; Derivatives thereof
    • A61K38/44—Oxidoreductases (1)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/43—Enzymes; Proenzymes; Derivatives thereof
    • A61K38/46—Hydrolases (3)
    • A61K38/465—Hydrolases (3) acting on ester bonds (3.1), e.g. lipases, ribonucleases
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/43—Enzymes; Proenzymes; Derivatives thereof
    • A61K38/46—Hydrolases (3)
    • A61K38/47—Hydrolases (3) acting on glycosyl compounds (3.2), e.g. cellulases, lactases

Definitions

  • FIG. 4 Stabilising effect of different lactate derivatives against thermal denaturation of malate dehydrogenase (MDH) , staphylococcal nuclease (SNase) and lysozyme.
  • MDH malate dehydrogenase
  • SNase staphylococcal nuclease
  • lysozyme lysozyme
  • FIG. 7 Stabilising effect of different galactosyl glycerate derivatives against thermal denaturation of malate dehydrogenase (MDH) , staphylococcal nuclease (SNase) and lysozyme.
  • MDH malate dehydrogenase
  • SNase staphylococcal nuclease
  • lysozyme lysozyme
  • FIG. 10 Dependence of lysozyme melting temperature on the concentration of solutes.
  • the compound of formula I is not a naturally occurring compound.
  • the compound when an asymmetric center is present in R 1 , the compound is the S enantiomer.
  • R z is N 3 .
  • R 3 is -H.
  • the compound i is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N
  • the compound is in the form of a pharmaceutically acceptable salt.
  • the invention also provides a method of stabilizing a biological material, comprising adding at least one compound of the invention, or a salt thereof, to a solution containing the biological material to form a stabilized solution.
  • the glycosylation reaction of donor 19 with acceptor 4 was performed according to the procedure described in experiment 2.
  • the glycosylation reaction of donor 19 with acceptor 7 was performed according to the procedure described in experiment 2.
  • the aqueous phase was extracted with CH 2 CI 2 and the combined organic phases were dried with MgS0 4 , filtered and concentrated under vacuum.
  • the aqueous phase was extracted with ⁇ 2 01 2 and the combined organic phases were dried with MgS0 4 , filtered and concentrated under vacuum.
  • the methanolysis of the acetate group of the galactoside 34 was performed according to the procedure described in experiment 26.
  • the methanolysis of the acetate group of the glucoside 136 was performed according to the procedure described in experiment 26.
  • the crude was purified by flash column chromatography on silica gel (40:60, EtOAc/Hex) affording the a (0.594 g, 82 %) and the ⁇ -alcohol (0.066 g, 9 %) as viscous colourless gums.
  • the methanolysis of the acetate group of the galactoside 139 was performed according to the procedure described in experiment 26.
  • the crude was purified by flash column chromatography on silica gel (50:50, EtOAc/Hex) affording the a (0.642 g, 57 %) and ⁇ - alcohol (0.176 g, 16%) as viscous colourless gums, and recovery of the starting material 139 (0.020 g, 16 %) and the product of the hydrolysis at the anomeric position (0.067 g, 8 %).
  • the methanolysis of the acetate group of the ⁇ -galactoside 141 (0.275 g, 0.33 mmol) was performed according to the procedure described in experiment 26.
  • the crude was purified by flash column chromatography on silica gel (40:60, EtOAc/Hex) affording the alcohol (0.243 g, 93 %) as a viscous colourless residue.
  • Example 2 Protein stabilizing effects of the compatible solutes of Example 1 in three model proteins

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Immunology (AREA)
  • Endocrinology (AREA)
  • Epidemiology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Emergency Medicine (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • Analytical Chemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Biomedical Technology (AREA)
  • Saccharide Compounds (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
PCT/PT2015/050001 2014-03-14 2015-03-13 Hexose derivatives, preparation and uses thereof Ceased WO2015137838A1 (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
US15/125,522 US11708387B2 (en) 2014-03-14 2015-03-13 Hexose derivatives, preparation and uses thereof
CN201580014386.4A CN106573952A (zh) 2014-03-14 2015-03-13 己糖衍生物及其制剂和用途
KR1020227017066A KR102651029B1 (ko) 2014-03-14 2015-03-13 헥소스 유도체, 그의 제제 및 용도
MX2016011808A MX386787B (es) 2014-03-14 2015-03-13 Derivados de hexosa, preparación y usos de los mismos.
JP2016575290A JP7067867B2 (ja) 2014-03-14 2015-03-13 ヘキソース誘導体、その製剤および使用
EP15724386.6A EP3116886A1 (en) 2014-03-14 2015-03-13 Hexose derivatives, preparation and uses thereof
SG11201607530XA SG11201607530XA (en) 2014-03-14 2015-03-13 Hexose derivatives, preparation and uses thereof
BR112016021231-2A BR112016021231B1 (pt) 2014-03-14 2015-03-13 Composto derivado de hexose, composição e método de estabilização de um material biológico
CN202211044372.5A CN115448964A (zh) 2014-03-14 2015-03-13 己糖衍生物及其制剂和用途
CA2942635A CA2942635C (en) 2014-03-14 2015-03-13 Hexose derivatives, preparation and uses thereof
KR1020167028609A KR102401853B1 (ko) 2014-03-14 2015-03-13 헥소스 유도체, 그의 제제 및 용도
RU2016140337A RU2731563C2 (ru) 2014-03-14 2015-03-13 Производные гексозы, их получение и применение
KR1020247009385A KR102828884B1 (ko) 2014-03-14 2015-03-13 헥소스 유도체, 그의 제제 및 용도
IL247531A IL247531B (en) 2014-03-14 2016-08-29 The history of ksuz, their preparation and uses
US18/332,157 US12590117B2 (en) 2014-03-14 2023-06-09 Hexose derivatives, preparation and uses thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201461953392P 2014-03-14 2014-03-14
US61/953,392 2014-03-14

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US15/125,522 A-371-Of-International US11708387B2 (en) 2014-03-14 2015-03-13 Hexose derivatives, preparation and uses thereof
US18/332,157 Continuation US12590117B2 (en) 2014-03-14 2023-06-09 Hexose derivatives, preparation and uses thereof

Publications (1)

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WO2015137838A1 true WO2015137838A1 (en) 2015-09-17

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PCT/PT2015/050001 Ceased WO2015137838A1 (en) 2014-03-14 2015-03-13 Hexose derivatives, preparation and uses thereof

Country Status (12)

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US (2) US11708387B2 (https=)
EP (1) EP3116886A1 (https=)
JP (2) JP7067867B2 (https=)
KR (3) KR102651029B1 (https=)
CN (2) CN106573952A (https=)
BR (1) BR112016021231B1 (https=)
CA (1) CA2942635C (https=)
IL (1) IL247531B (https=)
MX (1) MX386787B (https=)
RU (1) RU2731563C2 (https=)
SG (2) SG10201807891UA (https=)
WO (1) WO2015137838A1 (https=)

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FR3061013A1 (fr) * 2016-12-22 2018-06-29 Greenpharma Composition contenant le digeneaside, son procede d'obtention et son utilisation cosmetique, veterinaire ou nutraceutique
WO2019092504A1 (en) 2017-11-13 2019-05-16 Extremochem, Lda. Neutral glycosylated amides and dianionic glucuronidated acids as stabilizers for biological molecules

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KR102651029B1 (ko) * 2014-03-14 2024-03-25 파쿠우다지 지 씨엔씨아스 다 우니베르시다지 지 리스보아 헥소스 유도체, 그의 제제 및 용도
CN116251110B (zh) * 2022-11-18 2025-02-14 广东药科大学 β-D-吡喃葡萄糖基-乳酸及其衍生物在制备治疗代谢性疾病、炎症药物中的应用

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3061013A1 (fr) * 2016-12-22 2018-06-29 Greenpharma Composition contenant le digeneaside, son procede d'obtention et son utilisation cosmetique, veterinaire ou nutraceutique
WO2019092504A1 (en) 2017-11-13 2019-05-16 Extremochem, Lda. Neutral glycosylated amides and dianionic glucuronidated acids as stabilizers for biological molecules
US12098162B2 (en) 2017-11-13 2024-09-24 Extremochem, Lda Neutral glycosylated amides and dianionic glucuronidated acids as stabilizers for biological molecules

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