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
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CZ
Czechia
Prior art keywords
general formula
aminooxylipids
butoxycarbonyl
construction
self
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 US16/336,844 priority patent/US11492327B2/en
Priority to CA3039404A priority patent/CA3039404C/en
Priority to PCT/CZ2017/050054 priority patent/WO2018082723A1/en
Priority to EP17832461.2A priority patent/EP3535238B1/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—Liposomes
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated 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
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
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
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
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

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

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

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