CA2299429C - New lipopolyamines,their preparation and the use thereof - Google Patents

New lipopolyamines,their preparation and the use thereof Download PDF

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Publication number
CA2299429C
CA2299429C CA2299429A CA2299429A CA2299429C CA 2299429 C CA2299429 C CA 2299429C CA 2299429 A CA2299429 A CA 2299429A CA 2299429 A CA2299429 A CA 2299429A CA 2299429 C CA2299429 C CA 2299429C
Authority
CA
Canada
Prior art keywords
case
compounds
dna
salts
octadecyl
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.)
Expired - Fee Related
Application number
CA2299429A
Other languages
English (en)
French (fr)
Other versions
CA2299429A1 (en
Inventor
Roland Klosel
Stephan Konig
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.)
Biontex Laboratories GmbH
Original Assignee
Biontex Laboratories GmbH
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 claimed from DE19834683A external-priority patent/DE19834683A1/de
Application filed by Biontex Laboratories GmbH filed Critical Biontex Laboratories GmbH
Publication of CA2299429A1 publication Critical patent/CA2299429A1/en
Application granted granted Critical
Publication of CA2299429C publication Critical patent/CA2299429C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • 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
    • A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
    • 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
    • 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
    • A61K48/00—Medicinal preparations containing genetic material which is inserted into cells of the living body to treat genetic diseases; Gene therapy
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/14—Amines containing amino groups bound to at least two aminoalkyl groups, e.g. diethylenetriamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/42—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having etherified hydroxy groups and at least two amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
    • 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
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/87—Introduction of foreign genetic material using processes not otherwise provided for, e.g. co-transformation
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/902—Specified use of nanostructure
    • Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
    • Y10S977/915—Therapeutic or pharmaceutical composition

Landscapes

  • 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)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biophysics (AREA)
  • Biotechnology (AREA)
  • Biomedical Technology (AREA)
  • Wood Science & Technology (AREA)
  • General Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • Physics & Mathematics (AREA)
  • Plant Pathology (AREA)
  • Dispersion Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicinal Preparation (AREA)
  • Detergent Compositions (AREA)
  • Peptides Or Proteins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
CA2299429A 1997-08-13 1998-08-13 New lipopolyamines,their preparation and the use thereof Expired - Fee Related CA2299429C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE19735125.5 1997-08-13
DE19735125 1997-08-13
DE19834683A DE19834683A1 (de) 1997-08-13 1998-07-31 Neue Lipopolyamine, deren Darstellung und Anwendung
DE19834683.2 1998-07-31
PCT/EP1998/005156 WO1999008997A1 (de) 1997-08-13 1998-08-13 Neue lipopolyamine, deren darstellung und anwendung

Publications (2)

Publication Number Publication Date
CA2299429A1 CA2299429A1 (en) 1999-02-25
CA2299429C true CA2299429C (en) 2010-04-20

Family

ID=26039111

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2299429A Expired - Fee Related CA2299429C (en) 1997-08-13 1998-08-13 New lipopolyamines,their preparation and the use thereof

Country Status (8)

Country Link
US (1) US6281371B1 (enExample)
EP (1) EP1003711B1 (enExample)
JP (1) JP4504559B2 (enExample)
AT (1) ATE208369T1 (enExample)
AU (1) AU745958B2 (enExample)
CA (1) CA2299429C (enExample)
ES (1) ES2167939T3 (enExample)
WO (1) WO1999008997A1 (enExample)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002511446A (ja) 1998-04-08 2002-04-16 セルテック・セラピューティクス・リミテッド 脂 質
US6852334B1 (en) * 1999-04-20 2005-02-08 The University Of British Columbia Cationic peg-lipids and methods of use
AU4421200A (en) * 1999-04-26 2000-11-10 Celltech R & D Limited Bipolar lipids and their use for the delivery of bioactive substances
US20030054007A1 (en) * 1999-12-17 2003-03-20 Felgner Philip L. Intracellular protein delivery compositions and methods of use
US7189705B2 (en) 2000-04-20 2007-03-13 The University Of British Columbia Methods of enhancing SPLP-mediated transfection using endosomal membrane destabilizers
US7294511B2 (en) * 2001-03-22 2007-11-13 Chromos Molecular Systems, Inc. Methods for delivering nucleic acid molecules into cells and assessment thereof
US7001925B1 (en) 2002-09-27 2006-02-21 University Of Central Florida Research Foundation, Inc. Compounds and method for enhancing the efficacy of anti-cancer drugs
US7906122B2 (en) * 2003-06-18 2011-03-15 Yissum Research Development Company Of The Hebrew University Of Jersusalem Sphingoid polyalkylamine conjugates for Hepatitis B virus vaccination
US8242089B2 (en) * 2003-06-18 2012-08-14 Yissum Research Development Company Of The Hebrew University Of Jerusalem Sphingolipids polyalkylamine conjugates for use in transfection
US20110045001A1 (en) * 2008-03-28 2011-02-24 Biontex Laboratories Gmbh Transfection results of non-viral gene delivery systems by influencing of the innate immune system
WO2013016058A1 (en) * 2011-07-22 2013-01-31 Merck Sharp & Dohme Corp. Novel bis-nitrogen containing cationic lipids for oligonucleotide delivery
EP3218012A1 (en) 2014-11-10 2017-09-20 ethris GmbH Induction of osteogenesis by delivering bmp encoding rna
CA3129912A1 (en) 2019-02-14 2020-08-20 Ethris Gmbh Treatment of ciliopathies
FI4240396T3 (fi) 2020-11-04 2025-03-31 Ethris Gmbh IFN-lambda-mRNA virusinfektioiden hoitamiseksi
WO2024121160A1 (en) 2022-12-05 2024-06-13 Ethris Gmbh Regulator(s) of energy homeostasis-encoding rna molecule(s) with increased translation efficiency

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1963189A1 (de) 1969-12-17 1971-06-24 Bayer Ag Verfahren zur Herstellung von flammfesten,Urethangruppen aufweisenden Schaumstoffen
US4339767A (en) 1980-05-05 1982-07-13 International Business Machines Corporation High performance PNP and NPN transistor structure
DE69034168T3 (de) 1989-03-21 2013-04-11 Vical, Inc. Expression von exogenen Polynukleotidsequenzen in Wirbeltieren
FR2645866B1 (fr) * 1989-04-17 1991-07-05 Centre Nat Rech Scient Nouvelles lipopolyamines, leur preparation et leur emploi
US5538722A (en) 1989-06-13 1996-07-23 Stanford University Isolation, growth, differentiation and genetic engineering of human muscle cells
US5264618A (en) 1990-04-19 1993-11-23 Vical, Inc. Cationic lipids for intracellular delivery of biologically active molecules
IL103059A0 (en) 1991-09-30 1993-02-21 Boehringer Ingelheim Int Conjugates for introducing nucleic acid into higher eucaryotic cells
DE4139001A1 (de) * 1991-11-27 1993-06-03 Boehringer Mannheim Gmbh Verfahren zur einschleusung von nukleinsaeuren in zellen
US5972600A (en) 1992-04-03 1999-10-26 The Regents Of The University Of California Separation of active complexes
US5334761A (en) * 1992-08-28 1994-08-02 Life Technologies, Inc. Cationic lipids
GB9218762D0 (en) 1992-09-04 1992-10-21 Exxon Chemical Patents Inc Esters
CA2158655A1 (en) 1993-03-19 1994-09-29 Max L. Birnstiel Process for preparing cancer vaccines
US5777153A (en) 1994-07-08 1998-07-07 Gilead Sciences, Inc. Cationic lipids
US5650096A (en) * 1994-12-09 1997-07-22 Genzyme Corporation Cationic amphiphiles for intracellular delivery of therapeutic molecules
US5939401A (en) 1994-12-09 1999-08-17 Genzyme Corporation Cationic amphiphile compositions for intracellular delivery of therapeutic molecules
US6071890A (en) 1994-12-09 2000-06-06 Genzyme Corporation Organ-specific targeting of cationic amphiphile/DNA complexes for gene therapy
AU705549B2 (en) 1995-06-07 1999-05-27 Promega Biosciences, Inc. Phosphonic acid-based cationic lipids
AU701106B2 (en) 1995-06-07 1999-01-21 Promega Biosciences, Inc. Novel carbamate-based cationic lipids
WO1996040265A1 (en) 1995-06-07 1996-12-19 The Regents Of The University Of California Stabilization of polynucleotide complexes
US5811406A (en) 1995-06-07 1998-09-22 Regents Of The University Of California Dry powder formulations of polynucleotide complexes
DE19521412A1 (de) 1995-06-14 1996-12-19 Boehringer Mannheim Gmbh Neue kationische und polykationische Amphiphile, diese enthaltende Reagenzien und deren Verwendung
JPH11510489A (ja) * 1995-07-21 1999-09-14 ジンタ・インコーポレイテッド 新規アミド基本カチオン性脂質
DE19607686A1 (de) 1996-02-29 1997-09-04 Chemicon Lab Gmbh Neue metabolisierbare Lipopolyamine, deren Darstellung und Anwendung
US5747509A (en) 1996-06-03 1998-05-05 Schering Aktiengesellschaft Method for lowering plasma levels of lipoprotein(a)

Also Published As

Publication number Publication date
AU9342198A (en) 1999-03-08
ES2167939T3 (es) 2002-05-16
EP1003711B1 (de) 2001-11-07
CA2299429A1 (en) 1999-02-25
JP4504559B2 (ja) 2010-07-14
JP2001515060A (ja) 2001-09-18
AU745958B2 (en) 2002-04-11
ATE208369T1 (de) 2001-11-15
WO1999008997A1 (de) 1999-02-25
EP1003711A1 (de) 2000-05-31
US6281371B1 (en) 2001-08-28

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