CZ307452B6 - Aminooxylipidy pro konstrukci samoskladných liposomálních systémů umožňujících jejich následnou modifikaci biologicky funkčními molekulami - Google Patents

Aminooxylipidy pro konstrukci samoskladných liposomálních systémů umožňujících jejich následnou modifikaci biologicky funkčními molekulami

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Publication number
CZ307452B6
CZ307452B6 CZ2016-685A CZ2016685A CZ307452B6 CZ 307452 B6 CZ307452 B6 CZ 307452B6 CZ 2016685 A CZ2016685 A CZ 2016685A CZ 307452 B6 CZ307452 B6 CZ 307452B6
Authority
CZ
Czechia
Prior art keywords
general formula
aminooxylipids
butoxycarbonyl
construction
assembly
Prior art date
Application number
CZ2016-685A
Other languages
English (en)
Other versions
CZ2016685A3 (cs
Inventor
Miroslav Ledvina
Roman Effenberg
Jaroslav Turánek
Elissa Bartheldyová
Ladislav DroĹľ
Original Assignee
Vysoká škola chemicko-technologická v Praze
VÝZKUMNÝ ÚSTAV VETERINÁRNÍHO LÉKAŘSTVÍ, v.v.i.
Apigenex S.R.O.
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 Vysoká škola chemicko-technologická v Praze, VÝZKUMNÝ ÚSTAV VETERINÁRNÍHO LÉKAŘSTVÍ, v.v.i., Apigenex S.R.O. filed Critical Vysoká škola chemicko-technologická v Praze
Priority to CZ2016-685A priority Critical patent/CZ307452B6/cs
Priority to EP17832461.2A priority patent/EP3535238B1/en
Priority to US16/336,844 priority patent/US11492327B2/en
Priority to PCT/CZ2017/050054 priority patent/WO2018082723A1/en
Priority to CA3039404A priority patent/CA3039404C/en
Publication of CZ2016685A3 publication Critical patent/CZ2016685A3/cs
Publication of CZ307452B6 publication Critical patent/CZ307452B6/cs

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
    • C07C239/08—Hydroxylamino compounds or their ethers or esters
    • C07C239/20—Hydroxylamino compounds or their ethers or esters having oxygen atoms of hydroxylamino groups etherified
    • 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
    • A61K47/543—Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine
    • 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
    • A61K47/56—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 macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/61—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 macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
    • 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
    • A61K47/68—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 antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6835—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 antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site
    • 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
    • A61K47/69—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6905—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion
    • A61K47/6911—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion the form being a liposome
    • 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
    • A61K47/69—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6905—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion
    • A61K47/6911—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion the form being a liposome
    • A61K47/6913—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion the form being a liposome the liposome being modified on its surface by an antibody
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Immunology (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicinal Preparation (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Nové aminooxylipidy obecného vzorce I, kde n= 5 až 30 a X je polymethylenová spojka obecného vzorce II, kde n= 2 až 10, nebo polyethylenglykolová spojka obecného vzorce III, kde n= 1 až 14. Způsob přípravy aminooxylipidů obecného vzorce I, vyznačující se tím, že acylacíbutoxykarbonyl-polymethylendiaminu, či-butoxykarbonyl-polyethyleglykoldiaminu symetricky v poloze C(2) větvenou mastnou kyselinou obecného vzorce IV, v přítomnosti kondenzačního činidla nebo od kyseliny I odvozeným acylchloridem obecného vzorce V, se připraví-Boc-aminolipidy obecného vzorce VI. Ty se převedou na aminolipidy obecného vzorce VII. Jejich kondenzací s kyselinou-butoxykarbonylaminooxyoctovou v přítomnosti kondenzačního činidla se získajíBoc-aminooxylipidy obecného vzorce VIII, které debocylací poskytnou aminooxylipidy obecného vzorce I. Acylchloridy obecného vzorce V se připraví reakcí kyselin obecného vzorce IV s oxalylchloridem v přítomnosti katalytického množství-dimethylformamidu v organickém aprotickém rozpouštědle. Použití netoxických aminooxylipidů obecného vzorce I pro konstrukci netoxických samoskladných liposomálních nosičů léčiv prezentujících aminooxyskupiny a takzvaná "postliposomální" modifikace těchto nosičů biologicky funkčními molekulami za použití oximové ligační techniky.
CZ2016-685A 2016-11-03 2016-11-03 Aminooxylipidy pro konstrukci samoskladných liposomálních systémů umožňujících jejich následnou modifikaci biologicky funkčními molekulami CZ307452B6 (cs)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CZ2016-685A CZ307452B6 (cs) 2016-11-03 2016-11-03 Aminooxylipidy pro konstrukci samoskladných liposomálních systémů umožňujících jejich následnou modifikaci biologicky funkčními molekulami
EP17832461.2A EP3535238B1 (en) 2016-11-03 2017-11-02 Aminooxylipids for the construction of self-assembling liposomal systems enabling their subsequent modification by biologically functional molecules
US16/336,844 US11492327B2 (en) 2016-11-03 2017-11-02 Aminooxylipids for the construction of self-assembling liposomal systems enabling their subsequent modification by biologically functional molecules
PCT/CZ2017/050054 WO2018082723A1 (en) 2016-11-03 2017-11-02 Aminooxylipids for the construction of self-assembling liposomal systems enabling their subsequent modification by biologically functional molecules
CA3039404A CA3039404C (en) 2016-11-03 2017-11-02 Aminooxylipids for construction of self-assembling liposomal systems enabling their subsequent modification by biologically functional molecules

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CZ2016-685A CZ307452B6 (cs) 2016-11-03 2016-11-03 Aminooxylipidy pro konstrukci samoskladných liposomálních systémů umožňujících jejich následnou modifikaci biologicky funkčními molekulami

Publications (2)

Publication Number Publication Date
CZ2016685A3 CZ2016685A3 (cs) 2018-05-16
CZ307452B6 true CZ307452B6 (cs) 2018-09-05

Family

ID=61007406

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CZ2016-685A CZ307452B6 (cs) 2016-11-03 2016-11-03 Aminooxylipidy pro konstrukci samoskladných liposomálních systémů umožňujících jejich následnou modifikaci biologicky funkčními molekulami

Country Status (5)

Country Link
US (1) US11492327B2 (cs)
EP (1) EP3535238B1 (cs)
CA (1) CA3039404C (cs)
CZ (1) CZ307452B6 (cs)
WO (1) WO2018082723A1 (cs)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002048170A1 (en) * 2000-12-12 2002-06-20 Mitsubishi Chemical Corporation Lipids comprising an aminoxy group
WO2006016097A2 (en) * 2004-08-13 2006-02-16 Ic Vec Limited Vector comprising polymer modified sirna liposomes
US20120220668A1 (en) * 2011-02-24 2012-08-30 Dennis Bong Membrane stabilizing compositions and methods
WO2013104346A1 (en) * 2012-01-13 2013-07-18 Ustav Organicke Chemie A Biochemie Av Cr, V.V.I. Lipopolyamines of spermine type for construction of liposomal transfection systems
US20130302891A1 (en) * 2012-05-10 2013-11-14 Muhammad Naveed Yousaf Compositions and methods for promoting liposomal and cellular adhesion
WO2013181697A1 (en) * 2012-06-05 2013-12-12 The University Of Melbourne Bicyclo[6.1.0]non-4-yne compounds suitable for use as linkers in biological applications
WO2014197991A1 (en) * 2013-06-12 2014-12-18 Muhammad Yousaf Compounds for promoting liposomal and cellular adhesion and compositions and methods of use thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050287202A1 (en) 2000-12-12 2005-12-29 Miller Andrew D Compound

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002048170A1 (en) * 2000-12-12 2002-06-20 Mitsubishi Chemical Corporation Lipids comprising an aminoxy group
WO2006016097A2 (en) * 2004-08-13 2006-02-16 Ic Vec Limited Vector comprising polymer modified sirna liposomes
US20120220668A1 (en) * 2011-02-24 2012-08-30 Dennis Bong Membrane stabilizing compositions and methods
WO2013104346A1 (en) * 2012-01-13 2013-07-18 Ustav Organicke Chemie A Biochemie Av Cr, V.V.I. Lipopolyamines of spermine type for construction of liposomal transfection systems
US20130302891A1 (en) * 2012-05-10 2013-11-14 Muhammad Naveed Yousaf Compositions and methods for promoting liposomal and cellular adhesion
WO2013181697A1 (en) * 2012-06-05 2013-12-12 The University Of Melbourne Bicyclo[6.1.0]non-4-yne compounds suitable for use as linkers in biological applications
WO2014197991A1 (en) * 2013-06-12 2014-12-18 Muhammad Yousaf Compounds for promoting liposomal and cellular adhesion and compositions and methods of use thereof

Also Published As

Publication number Publication date
EP3535238B1 (en) 2021-04-21
CA3039404A1 (en) 2018-05-11
US11492327B2 (en) 2022-11-08
EP3535238A1 (en) 2019-09-11
CZ2016685A3 (cs) 2018-05-16
WO2018082723A1 (en) 2018-05-11
US20210292275A1 (en) 2021-09-23
CA3039404C (en) 2021-09-07

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