EP2013195A1 - Gem-difluorid-c-glycopeptidverbindungen, ihre herstellung und verwendung insbesondere zur konservierung biologischer materialien - Google Patents

Gem-difluorid-c-glycopeptidverbindungen, ihre herstellung und verwendung insbesondere zur konservierung biologischer materialien

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Publication number
EP2013195A1
EP2013195A1 EP07731371A EP07731371A EP2013195A1 EP 2013195 A1 EP2013195 A1 EP 2013195A1 EP 07731371 A EP07731371 A EP 07731371A EP 07731371 A EP07731371 A EP 07731371A EP 2013195 A1 EP2013195 A1 EP 2013195A1
Authority
EP
European Patent Office
Prior art keywords
och
compound
mmol
gem
nmr
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.)
Withdrawn
Application number
EP07731371A
Other languages
English (en)
French (fr)
Inventor
Géraldine CASTELOT DELIENCOURT-GODEFROY
Jean-Charles Quirion
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.)
Institut National des Sciences Appliquees de Rouen
Original Assignee
Institut National des Sciences Appliquees de Rouen
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 Institut National des Sciences Appliquees de Rouen filed Critical Institut National des Sciences Appliquees de Rouen
Publication of EP2013195A1 publication Critical patent/EP2013195A1/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
    • C07D309/10—Oxygen atoms
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • 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]
    • 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
    • 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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings 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
    • C07D307/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/524—Preservatives

Definitions

  • the invention relates to a process for the synthesis of gem-difluorinated C-glycopeptide compounds. It applies more particularly, but not exclusively, to the preparation of compounds or compositions that can be used in particular for the preservation of biological materials such as cells, tissues and organs at different temperatures, but also in the treatment of inflammation.
  • glycoproteins due to the presence of a saccharide bond (bond involving oxygen said to anomeric position), are fragile vis-à-vis several enzyme systems including glycosidase enzymes and are also sensitive to acid-base hydrolyses, which makes their synthesis more difficult.
  • the CF 2 group is particularly resistant to biochemical degradation processes and thus allows the synthesis of non-hydrolyzable structures.
  • the Applicant has developed gem-difluoroglycopeptides which have demonstrated a very high activity of preserving different cell lines at temperatures ranging from -196 ° C to + 37 ° C. Indeed, the structural changes made compared to native compounds and the observation of a true anti-apoptosis effect, that is to say no cell death, at physiological temperatures have led the Applicant to extend the spectrum of activity of the compounds. These compounds have been named AAGP for Anti Aging GlycoProteins.
  • Such compounds would be useful for many applications such as the preservation of cells, platelets, tissues and organs.
  • Preservation is more generally understood to include preservation at different temperatures including cryopreservation up to temperatures of -196 ° C.
  • compounds used as admixtures during storage and having good stability could be useful for preserving biological materials, particularly in the medical field: - to maintain whole human organs such as kidneys, hearts and livers to transplant without time constraint, - to preserve cells or delicate tissues with a minimum of damage and long enough to allow their possibly international distribution, to preserve blood platelets and different cells,
  • the object of the invention is to solve these disadvantages.
  • n is an integer from 3 to 4,
  • R represents a hydrogen atom, a linear or branched alkyl group, benzyl, acetyl, trimethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, R represents OR, NR "R"', N 3 , or a phthalimide,
  • R “and R” which may be identical or different, represent a hydrogen atom or a linear or branched alkyl, aryl, benzyl, benzoyl, acetyl, alkyloxycarbonyl, allyloxycarbonyl or benzyloxycarbonyl group,
  • R 1 represents a hydrogen atom or a linear or branched alkyl group, benzyl, alkylcarbamate, allylcarbamate, benzylcarbamate, acetyl, R 1 may also represent an amino acid, but in this case R 2 represents only OR,
  • R 2 represents an amino acid, but in this case R 1 represents a hydrogen atom or a linear or branched alkyl group, benzyl, alkylcarbamate, allylcarbamate, benzylcarbamate, acetyl, R 2 represents OR when R 1 represents an amino acid, R 3 represents a hydrogen atom or a free or protected alcohol function, as well as its derivatives in the base state, from addition to a mineral or organic acid, hydrate or solvate physiologically or pharmaceutically acceptable.
  • the linear or branched alkyl groups may be groups having 1 to 10 carbon atoms.
  • Said amino acid may be an alanine or a glycine or a proline.
  • physiologically acceptable is meant compatible with the skin, lips, scalp and / or hair.
  • the subject of the invention is also a medicinal product comprising, as active ingredient, at least one gem-difluorinated C-glycopeptide compound of formula I as defined above.
  • the present invention relates to the use of at least one gem-difluorinated C-glycopeptide compound of formula I as defined above for the preparation of medicaments for treating inflammation.
  • the invention also relates to the use of a gem-difluorinated C-glycopeptide compound of formula I for the preparation of compounds or compositions that can be used for preserving or cryopreserving biological materials such as fibroblasts.
  • compositions comprising at least one gem-difluorinated C-glycopeptide compound of formula I as defined above.
  • composition according to the invention may comprise a gem-difluorinated C-glycopeptide compound of formula I alone or as a mixture and in any proportion.
  • composition according to the invention may be intended for a cosmetic or pharmaceutical use, especially a dermatological one.
  • composition may be ingested, injected or applied to the skin, lips, scalp and / or hair.
  • composition according to the invention may be in any of the galenical forms normally used.
  • composition may comprise a medium and / or a physiologically or pharmaceutically acceptable carrier.
  • the active principles may be administered in unit dosage forms, in admixture with conventional pharmaceutically acceptable carriers.
  • suitable unit dosage forms include oral forms such as tablets, capsules, powders, granules and oral solutions or suspensions, topical administration forms, implants, subcutaneous dosage forms, cutaneous, intramuscular, intravenous, intranasal or intraocular and forms of rectal administration.
  • compositions thus obtained may also contain preservatives.
  • compositions may be added in these compositions.
  • amount of compound according to the invention and other possible active principles in such compositions may vary according to the applications, the age and the weight of the patient or the user if appropriate.
  • composition according to the invention may comprise a medium and / or a physiologically acceptable carrier.
  • composition may be in any galenical form normally used for topical application, especially in the form of an aqueous, hydroalcoholic or oily solution, an oil-in-water or water-in-oil or multiple emulsion. , an aqueous or oily gel, an anhydrous liquid, pasty or solid product, an oil dispersion in an aqueous phase using spherules that may be micro / nanocapsules or micro / nanoparticles, dispersions vesicles of ionic and / or nonionic type.
  • This composition may be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, a mousse . It may also be in solid form and, for example, in the form of a stick.
  • It can be used as a care product, as a cleaning product, as a makeup product.
  • composition according to the invention may also be a composition for hair care, and in particular a shampoo, a treatment lotion, a cream or a styling gel.
  • composition may also contain adjuvants usual in the cosmetic or dermatological fields.
  • adjuvants usual in the cosmetic or dermatological fields.
  • the amounts of the various adjuvants are those conventionally used in the fields under consideration.
  • adjuvants may be introduced into an aqueous phase, an oily phase, in vesicles and / or in micro / nanoparticles. It is understood that these adjuvants and their concentration should be such that they do not modify the desired property for the composition according to the invention.
  • the invention also relates to a cosmetic treatment method for protecting the skin, the lips and / or the hair, the scalp against oxidative stress and / or the UV of applying to the skin, the lips and / or the skin.
  • hair, the scalp a composition comprising at least one physiologically acceptable medium and at least one gem-difluorinated C-glycopeptide compound of formula I as defined above or one of its derivatives in the form of base, of addition salt a mineral or organic acid, hydrate or solvate physiologically or pharmaceutically acceptable.
  • Figure 1 is a reaction equation for obtaining compound 2;
  • Figure 2 is a reaction equation for obtaining compound 3;
  • Figure 3 is a reaction equation for obtaining compound 4;
  • Figure 4 is a reaction equation for obtaining compound 5;
  • Figure 5 is a reaction equation for obtaining compound 6;
  • Figure 6 is a reaction equation for obtaining compound 9;
  • Figure 7 is a reaction equation for obtaining compound 10;
  • Figure 8 is a reaction equation for obtaining compound H;
  • Fig. 9 is a reaction equation for obtaining compound 12;
  • Fig. 10 is a reaction equation for obtaining compound 14;
  • Figure 11 is a reaction equation for obtaining compound 15;
  • Fig. 12 is a reaction equation for obtaining compound 16;
  • Fig. 13 is a reaction equation for obtaining compound 19;
  • Fig. 14 is a reaction equation for obtaining compound 20;
  • Fig. 15 is a reaction equation for obtaining compound 21;
  • Fig. 16 is a reaction equation for obtaining compound 22;
  • Figure 17 is a reaction equation for obtaining compound 24;
  • Fig. 18 is a reaction equation for obtaining compound 25;
  • Fig. 19 is a reaction equation for obtaining compound 26;
  • Figure 20 is a reaction equation for obtaining compound 28;
  • Fig. 21 is a reaction equation for obtaining compound 29;
  • Fig. 22 is a reaction equation for obtaining compound 30;
  • Fig. 23 is a reaction equation for obtaining compound 32;
  • Fig. 24 is a reaction equation for obtaining compound 33;
  • Fig. 25 is a reaction equation for obtaining compound 34
  • Fig. 26 is a reaction equation for obtaining compound 35;
  • Figure 27 is a reaction equation for obtaining compound 36
  • Figure 28 is a reaction equation to obtain compound 37;
  • Figure 29 is a reaction equation to obtain compound 38
  • Fig. 30 is a reaction equation for obtaining compound 39;
  • Figure 31 is a reaction equation for obtaining compound 4_1;
  • Fig. 32 is a reaction equation for obtaining compound 42
  • Fig. 33 is a reaction equation for obtaining compound 43;
  • Figure 34 is a reaction equation for obtaining compound 44
  • Figure 35 is a representation of the effects of compound ⁇ ⁇ on adult UV-treated skin fibroblasts
  • Figure 36 is a representation of the effects of compound H on adult skin fibroblasts at -3 ° C;
  • Figures 37, 38 and 39 are representations of the effects of the various derivatives on the survival of HELA cells subjected to UVC.
  • the mass spectra were obtained on a Micromass TOF-SPEC, E 20 kV, ⁇ -cyano spectrophotometer.
  • Maldi and JEOL AX500 ionization 3 kV, Canon FAB JEOL, Xe, 4 kV, current limit 10 ⁇ A, GIy-NBA 50:50 for FAB ionization.
  • the separations by column chromatography are carried out under slight pressure using silica chromatography techniques Kieselgel 60 (230-400 Mesh, Merck).
  • the monitoring is provided by thin layer chromatography (TLC) with Kieselgel 60F-254-0.25mm plates.
  • TLC thin layer chromatography
  • the ratio of the migration distance of a compound on a given support to the migration distance of an eluent is called the frontal ratio (Rf).
  • the medium is hydrolyzed with water.
  • the aqueous phase is then extracted three times with ether.
  • the organic phases are then combined, washed several times with water, dried over magnesium sulfate, filtered and evaporated.
  • the product thus obtained is purified by chromatography on a silica column eluting with a cyclohexane / ethyl acetate mixture in proportions of nine to one. After concentrating the collected fractions, the product 2 is in the form of white crystals with a weight yield of 95%.
  • the mixture is extracted four times with 100 mL of toluene.
  • the organic phases are combined and then washed with 100 ml of water, 100 ml of a saturated solution of sodium hydrogencarbonate NaHCO 3 and finally with 100 ml of water.
  • the organic phase is then dried over magnesium sulfate, filtered and concentrated.
  • the product thus obtained is purified by chromatography on a silica column with cyclohexane / ethyl acetate as eluent in proportions of 8.5 to 1.5. After concentrating the collected fractions, the product 3 is in the form of white crystals with a weight yield of 75%.
  • the product is then purified by chromatography on a silica column eluting with cyclohexane / ethyl acetate in proportions of eight to two. After concentrating the collected fractions, the lactone 4 is in the form of a colorless oil with a weight yield of 82%.
  • aqueous and organic phases are separated and the aqueous phase is extracted twice more with dichloromethane.
  • the organic phases are combined, dried over magnesium sulfate, filtered and concentrated.
  • the product is then purified by chromatography on a silica column eluting with cyclohexane / ethyl acetate in proportions of eight to two. After concentrating the collected fractions, the product is in the form of white crystals with a weight yield of 82%.
  • Compound 6 is obtained in the form of a white oil with a quantitative yield.
  • the mixture is then purified by chromatography on a silica column with cyclohexane / ethyl acetate as eluent. After concentrating the collected fractions, the product is in the form of a white solid with a weight yield of 83%.
  • AIa 54.9 (N, H Lys); 67.4 and 67.6 (2OCH 2 Ph); 68.7 (C6); 71, 2 (C5); 73.5 and 73.8 (2OCH 2 Ph); 74.4 (C4); 75.0 (OCH 2 Ph; C2); 75.8 (OCH 2 Ph); 80.9
  • a flask containing the starting material (150 mg, 0.133 mmol) in a mixture of tetrahydrofuran THF (3 ml) and 1N HCl (2 ml) in the presence of a Pd / C palladium on charcoal spatula tip is placed under a hydrogen atmosphere. The mixture is left stirring overnight and then filtered through a Millipore® filter. The mixture is then concentrated to obtain the product ⁇ . in the form of an orange-yellow solid with a yield of 92%.
  • NMR 13 C (D 2 O, 75.5 MHz) 16.2 (CH 3 ); 21.5 (CH 2 ); 28.0 (CH 2 ); 30.7 (CH 2 ); 39.3 (CH 2 N); 49.1 (CH); 53.2 (NCH); 61 (C ( P), 62.6 (C6), 67.0 (C6), 68.9 (C6), 70.6 (C3P), 70.9 (C5), 72.5 (C6), C21), 73.9 (C3), 75.5 (C2), 80.2 (C4), 169.9 and 176.3 (CO).
  • the product is concentrated and then purified on a silica column (eluent cyclohexane / ethyl acetate 9.3 / 0.7) to recover the expected product 36 in the form of a colorless oil.
  • Compound 37 is obtained as a white oil in quantitative yield.
  • the mixture is then purified by chromatography on a silica column with cyclohexane / ethyl acetate as eluent. After concentrating the collected fractions, the product 38 is in the form of a white solid with a weight yield of 53%.
  • NMR 13 C (D 2 O, 75.5 MHz) 16.3 (CH 3 ); 21.5 (CH 2 ); 27.9 (CH 2 ); 30.8 (CH 2 ); 39.4 (CH 2 N); 49.1 (CH (Lys)); 53.2 (NCH (Ala)); 61.3 (C (T), 66.1 (C?) 69.0 (C1)), 74.0 (C1 ou or C1)), 77.3 (t, 24Hz, Cl), 79.6 (C1 ou); C3I or C6) 164.8 (d, 26Hz, CO), 169.9 and 176.3 (2O).
  • the organic phase is collected, dried over magnesium sulfate, filtered and concentrated.
  • the mixture is then purified by chromatography on a silica column with cyclohexane / ethyl acetate as eluent. After concentrating the collected fractions, the product 43 is in the form of a white solid with a weight yield of 43%.
  • the aim is to test the preservative activity of the ⁇ _ AAGP compounds at low temperatures.
  • the cells are thus incubated at -3 ° C. in the presence of compound AAGP ⁇ _.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Genetics & Genomics (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Rheumatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pain & Pain Management (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
EP07731371A 2006-05-03 2007-04-26 Gem-difluorid-c-glycopeptidverbindungen, ihre herstellung und verwendung insbesondere zur konservierung biologischer materialien Withdrawn EP2013195A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0603952A FR2900656A1 (fr) 2006-05-03 2006-05-03 Composes c-glycopeptides gem-difluores, leur preparation et leur utilisation notamment pour la preservation de materiaux biologiques
PCT/FR2007/000716 WO2007125203A1 (fr) 2006-05-03 2007-04-26 Composes c-glycopeptides gem-difluores, leur preparation et leur utilisation notamment pour la preservation de materiaux biologiques.

Publications (1)

Publication Number Publication Date
EP2013195A1 true EP2013195A1 (de) 2009-01-14

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Family Applications (1)

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EP07731371A Withdrawn EP2013195A1 (de) 2006-05-03 2007-04-26 Gem-difluorid-c-glycopeptidverbindungen, ihre herstellung und verwendung insbesondere zur konservierung biologischer materialien

Country Status (6)

Country Link
US (1) US20090311203A1 (de)
EP (1) EP2013195A1 (de)
BR (1) BRPI0711156A2 (de)
CA (1) CA2649993A1 (de)
FR (1) FR2900656A1 (de)
WO (1) WO2007125203A1 (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012016935A1 (en) 2010-08-02 2012-02-09 Centrum Für Angewandte Nanotechnologie (Can) Gmbh Seven carbon (c-7) sugars derivatives and their use
EP2655353B9 (de) * 2010-12-22 2015-08-05 Tfchem Glyco-cf2-serinderivate und glyco-cf2-threoninderivate
WO2013021018A1 (en) 2011-08-08 2013-02-14 Tfchem Gem-difluorinated c-isopropylgalactoside derivates
CA2942731C (en) * 2014-03-17 2022-11-22 Tfchem Glycopeptide derivatives for the preservation and protection of biological materials and microorganisms
EP3152297A4 (de) * 2014-06-04 2018-01-31 Protokinetix, Inc. Verwendung von anti-aging-glycopeptiden zur verbesserung der pankreaszellengesundheit, des überlebens und transplantationsergebnisses
CA3011449A1 (en) 2016-01-27 2017-08-03 Protokinetix Inc. Use of anti-aging glycoprotein for enhancing survival of neurosensory precursor cells
EP3573621B9 (de) 2017-01-30 2021-08-25 TFChem Glycopeptidderivate zur verwendung bei der behandlung und/oder vorbeugung und/oder abschwächung von fibroseerkrankungen
WO2019239425A1 (en) * 2018-06-11 2019-12-19 Aarti Industries Limited Improved process for preparation of 2,3,4,6-tetra-o-benzyl-d-galactose
WO2021009367A1 (en) * 2019-07-17 2021-01-21 Tfchem Glycopeptides increasing lipid synthesis
JP2024504135A (ja) 2021-01-20 2024-01-30 テーエフケム 環状糖アミノ酸誘導体

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2842810B1 (fr) * 2002-07-25 2006-01-27 Inst Nat Sciences Appliq Nouveaux composes gem difluores, leur procedes de preparation et leurs applications.
FR2878851B1 (fr) * 2004-12-02 2007-02-09 Inst Nat Sciences Appliq Composes c-glycopeptides gem-difluores, leur preparation et leur utilisation en cryochirurgie et/ou cryopreservation

Non-Patent Citations (1)

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Title
See references of WO2007125203A1 *

Also Published As

Publication number Publication date
BRPI0711156A2 (pt) 2011-08-23
CA2649993A1 (fr) 2007-11-08
FR2900656A1 (fr) 2007-11-09
US20090311203A1 (en) 2009-12-17
WO2007125203A1 (fr) 2007-11-08

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