CA2237316C - Complex cationic lipids - Google Patents

Complex cationic lipids Download PDF

Info

Publication number
CA2237316C
CA2237316C CA2237316A CA2237316A CA2237316C CA 2237316 C CA2237316 C CA 2237316C CA 2237316 A CA2237316 A CA 2237316A CA 2237316 A CA2237316 A CA 2237316A CA 2237316 C CA2237316 C CA 2237316C
Authority
CA
Canada
Prior art keywords
groups
alkyl
compound according
group
dmrie
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
CA2237316A
Other languages
English (en)
French (fr)
Other versions
CA2237316A1 (en
Inventor
Carl J. Wheeler
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.)
Fresh Tracks Therapeutics Inc
Original Assignee
Vical Inc
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 Vical Inc filed Critical Vical Inc
Publication of CA2237316A1 publication Critical patent/CA2237316A1/en
Application granted granted Critical
Publication of CA2237316C publication Critical patent/CA2237316C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
    • C07K5/0825—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp and Glp-amino acid; Derivatives 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
    • A61K47/54—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C225/04—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
    • C07C225/06—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and acyclic
    • 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
    • C07C229/12—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 acyclic carbon skeletons
    • 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
    • C07C237/06—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 atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C07C275/14—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/30—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to nitro or nitroso groups
    • C07C279/32—N-nitroguanidines
    • C07C279/36—Substituted N-nitroguanidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/081—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dispersion Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2237316A 1995-11-30 1996-11-27 Complex cationic lipids Expired - Fee Related CA2237316C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US56575695A 1995-11-30 1995-11-30
US08/565,756 1995-11-30
PCT/US1996/019721 WO1997019675A2 (en) 1995-11-30 1996-11-27 Complex cationic lipids

Publications (2)

Publication Number Publication Date
CA2237316A1 CA2237316A1 (en) 1997-06-05
CA2237316C true CA2237316C (en) 2012-06-26

Family

ID=24259963

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2237316A Expired - Fee Related CA2237316C (en) 1995-11-30 1996-11-27 Complex cationic lipids

Country Status (5)

Country Link
US (2) US6670332B1 (enExample)
EP (1) EP0863749A2 (enExample)
JP (2) JP4430135B2 (enExample)
CA (1) CA2237316C (enExample)
WO (1) WO1997019675A2 (enExample)

Families Citing this family (50)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6673776B1 (en) 1989-03-21 2004-01-06 Vical Incorporated Expression of exogenous polynucleotide sequences in a vertebrate, mammal, fish, bird or human
US5703055A (en) 1989-03-21 1997-12-30 Wisconsin Alumni Research Foundation Generation of antibodies through lipid mediated DNA delivery
US6867195B1 (en) 1989-03-21 2005-03-15 Vical Incorporated Lipid-mediated polynucleotide administration to reduce likelihood of subject's becoming infected
US6214804B1 (en) 1989-03-21 2001-04-10 Vical Incorporated Induction of a protective immune response in a mammal by injecting a DNA sequence
ATE162219T1 (de) 1989-11-16 1998-01-15 Univ Duke Transformation von tierischen hautzellen mit hilfe von partikeln
US6228844B1 (en) 1991-11-12 2001-05-08 Vical Incorporated Stimulating vascular growth by administration of DNA sequences encoding VEGF
US6706694B1 (en) 1990-03-21 2004-03-16 Vical Incorporated Expression of exogenous polynucleotide sequences in a vertebrate
US7105574B1 (en) 1999-03-26 2006-09-12 Vical Incorporated Adjuvant compositions and methods for enhancing immune responses to polynucleotide-based vaccines
US5641665A (en) * 1994-11-28 1997-06-24 Vical Incorporated Plasmids suitable for IL-2 expression
EP0863749A2 (en) * 1995-11-30 1998-09-16 Vical Incorporated Complex cationic lipids
DE69815707T2 (de) * 1997-11-20 2004-07-01 Vical, Inc., San Diego Behandlung von krebs durch verwendung von zytokin-exprimierender polynukleotiden und zusammensetzungen dafür
US6043390A (en) 1998-04-03 2000-03-28 The Regents Of The University Of California Pentaerythritol lipid derivatives and nucleic-acid complexes
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
US7078224B1 (en) * 1999-05-14 2006-07-18 Promega Corporation Cell concentration and lysate clearance using paramagnetic particles
ATE397942T1 (de) 1999-03-26 2008-07-15 Vical Inc Adjuvanszusammensetzungen zur erhöhung der immunantwort bezüglich polynukleotid-basierenden impfstoffen
EP1459766B1 (en) * 1999-03-26 2008-06-11 Vical Incorporated Adjuvant compositions for enhancing immune responses to polynucleotide-based vaccines
JP4723097B2 (ja) * 1999-05-28 2011-07-13 バイカル インコーポレイテッド サイトフェクチン二量体およびその使用方法
US6696424B1 (en) 1999-05-28 2004-02-24 Vical Incorporated Cytofectin dimers and methods of use thereof
CA2407074A1 (en) * 2000-04-21 2001-11-01 Jukka Hartikka Compositions and methods for in vivo delivery of polynucleotide-based therapeutics
US7935812B2 (en) * 2002-02-20 2011-05-03 Merck Sharp & Dohme Corp. RNA interference mediated inhibition of hepatitis C virus (HCV) expression using short interfering nucleic acid (siNA)
AU2003278776A1 (en) * 2002-09-10 2004-04-30 Vical Incorporated Codon-optimized polynucleotide-based vaccines against bacillus anthracis infection
AU2003293195A1 (en) * 2002-12-23 2004-07-29 Vical Incorporated Method for freeze-drying nucleic acid/block copolymer/cationic surfactant complexes
WO2004060363A1 (en) * 2002-12-23 2004-07-22 Vical Incorporated Method for producing sterile polynucleotide based medicaments
US8080642B2 (en) * 2003-05-16 2011-12-20 Vical Incorporated Severe acute respiratory syndrome DNA compositions and methods of use
AU2005248361B2 (en) * 2004-05-18 2010-03-11 Vical Incorporated Influenza virus vaccine composition and methods of use
AU2005252273B2 (en) 2004-06-07 2011-04-28 Arbutus Biopharma Corporation Lipid encapsulated interfering RNA
US20060134221A1 (en) * 2004-12-03 2006-06-22 Vical Incorporated Methods for producing block copolymer/amphiphilic particles
WO2007086883A2 (en) * 2005-02-14 2007-08-02 Sirna Therapeutics, Inc. Cationic lipids and formulated molecular compositions containing them
US7404969B2 (en) * 2005-02-14 2008-07-29 Sirna Therapeutics, Inc. Lipid nanoparticle based compositions and methods for the delivery of biologically active molecules
WO2007070381A2 (en) 2005-12-09 2007-06-21 Promega Corporation Nucleic acid purification with a binding matrix
JP2009528845A (ja) * 2006-03-08 2009-08-13 プロメガ・コーポレーション 低分子量ｒｎａの精製方法
US8193246B2 (en) 2006-12-19 2012-06-05 Marina Biotech, Inc. Lipids and lipid assemblies comprising transfection enhancer elements
US20100015218A1 (en) * 2007-02-16 2010-01-21 Vasant Jadhav Compositions and methods for potentiated activity of biologically active molecules
WO2008148057A2 (en) * 2007-05-23 2008-12-04 Vical Incorporated Cationic lipids compositions and methods for enhancing immune responses to vaccines
WO2009129395A1 (en) * 2008-04-16 2009-10-22 Abbott Laboratories Cationic lipids and uses thereof
US8569256B2 (en) 2009-07-01 2013-10-29 Protiva Biotherapeutics, Inc. Cationic lipids and methods for the delivery of therapeutic agents
US9018187B2 (en) 2009-07-01 2015-04-28 Protiva Biotherapeutics, Inc. Cationic lipids and methods for the delivery of therapeutic agents
US8222397B2 (en) 2009-08-28 2012-07-17 Promega Corporation Methods of optimal purification of nucleic acids and kit for use in performing such methods
US8039613B2 (en) 2009-08-28 2011-10-18 Promega Corporation Methods of purifying a nucleic acid and formulation and kit for use in performing such methods
EP2567952A4 (en) 2010-04-28 2015-11-25 Kyowa Hakko Kirin Co Ltd CATIONIC LIPID
US9408914B2 (en) 2010-04-28 2016-08-09 Kyowa Hakko Kirin Co., Ltd. Cationic lipid
US8956646B2 (en) 2010-08-14 2015-02-17 The Regents Of The University Of California Zwitterionic lipids
JP2013095755A (ja) 2011-11-02 2013-05-20 Kyowa Hakko Kirin Co Ltd カチオン性脂質
TW201330874A (zh) 2011-12-12 2013-08-01 Kyowa Hakko Kirin Co Ltd 含有陽離子性脂質之組合之脂質奈米粒子
TWI594767B (zh) 2011-12-12 2017-08-11 協和醱酵麒麟有限公司 含有陽離子性脂質之藥物傳遞系統用脂質奈米粒子
TW201726600A (zh) 2012-07-06 2017-08-01 協和醱酵麒麟有限公司 陽離子性脂質
US9913907B2 (en) 2012-07-16 2018-03-13 Kyowa Hakko Kirin Co., Ltd. RNAi pharmaceutical composition for suppressing expression of KRAS gene
WO2017111172A1 (ja) 2015-12-25 2017-06-29 協和発酵キリン株式会社 カチオン性脂質としての化合物
CA3089826A1 (en) * 2018-02-01 2019-08-08 Trustees Of Tufts College Lipid-like nanocomplexes and uses thereof
KR20240013087A (ko) 2021-05-24 2024-01-30 쑤저우 아보젠 바이오사이언시스 컴퍼니 리미티드 지질 화합물 및 지질 나노입자 조성물

Family Cites Families (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2368208A (en) 1940-12-16 1945-01-30 Emulsol Corp Chemical compounds and method of preparing same
US3265719A (en) 1959-12-28 1966-08-09 American Cyanamid Co Betaines
ZA8681B (en) 1985-01-07 1987-08-26 Syntex Inc 1,2-dialkoxy-omega-trialkylammonium cationic surfactants
US5049386A (en) 1985-01-07 1991-09-17 Syntex (U.S.A.) Inc. N-ω,(ω-1)-dialkyloxy)- and N-(ω,(ω-1)-dialkenyloxy)Alk-1-YL-N,N,N-tetrasubstituted ammonium lipids and uses therefor
DE3618517A1 (de) 1985-06-04 1986-12-04 Lion Corp., Tokio/Tokyo Emulgiermittel zur emulsionspolymerisation
US4864060A (en) 1987-08-31 1989-09-05 Witco Corporation Surface active compounds, methods for making same and uses thereof
US5068431A (en) 1987-08-31 1991-11-26 Witco Corporation Methods of making new surface active compounds
JP2801727B2 (ja) * 1990-03-06 1998-09-21 花王株式会社 低刺激性界面活性剤
US5279833A (en) 1990-04-04 1994-01-18 Yale University Liposomal transfection of nucleic acids into animal cells
US5264618A (en) 1990-04-19 1993-11-23 Vical, Inc. Cationic lipids for intracellular delivery of biologically active molecules
DE4013632A1 (de) 1990-04-27 1991-10-31 Max Planck Gesellschaft Liposomen mit positiver ueberschussladung
WO1991017424A1 (en) * 1990-05-03 1991-11-14 Vical, Inc. Intracellular delivery of biologically active substances by means of self-assembling lipid complexes
JPH0525106A (ja) 1991-07-22 1993-02-02 Kao Corp カルボキシベタイン誘導体及びこれを含有する化粧料
WO1993012240A1 (en) 1991-12-17 1993-06-24 The Regents Of The University Of California Gene therapy for cystic fibrosis transmembrane conductance regulator activity (cftr)
US5334761A (en) 1992-08-28 1994-08-02 Life Technologies, Inc. Cationic lipids
WO1995002698A1 (en) * 1993-07-12 1995-01-26 Life Technologies, Inc. Composition and methods for transfecting eukaryotic cells
NZ276975A (en) 1993-11-24 1998-04-27 Megabios Corp Guanidine based amphiphiles and their use in liposomes for delivering genetic material intracellularly
JPH09505593A (ja) 1993-11-24 1997-06-03 メガバイオス・コーポレイション ピペラジンの両親媒性誘導体
US5928944A (en) 1994-02-04 1999-07-27 The United States Of America As Represented By The Department Of Health And Human Services Method of adenoviral-medicated cell transfection
US6075012A (en) * 1994-02-11 2000-06-13 Life Technologies, Inc. Reagents for intracellular delivery of macromolecules
US5908635A (en) * 1994-08-05 1999-06-01 The United States Of America As Represented By The Department Of Health And Human Services Method for the liposomal delivery of nucleic acids
US5780009A (en) 1995-01-20 1998-07-14 Nexia Biotechnologies, Inc. Direct gene transfer into the ruminant mammary gland
US5739271A (en) 1995-06-07 1998-04-14 Gen-Probe Incorporated Thiocationic lipids
US5711964A (en) * 1995-06-07 1998-01-27 United States Of America Method for the intracellular delivery of biomolecules using liposomes containing cationic lipids and vitamin D
KR19990022597A (ko) 1995-06-07 1999-03-25 다니엘 엘. 캐시앙, 헨리 엘. 노르호프 티오양이온성 지질, 제약조성물 및 그 사용 방법
WO1996040961A1 (en) 1995-06-07 1996-12-19 Life Technologies, Inc. Peptide-enhanced cationic lipid transfections
US5869715A (en) * 1995-09-27 1999-02-09 The Reagents Of The University Of California Polyfunctional cationic cytofectins
AU7078396A (en) * 1995-09-27 1997-04-30 Regents Of The University Of California, The Polyfunctional cationic cytofectins, formulations and methods for generating active cytofectin:polynucleotide transfection complexes
EP0863749A2 (en) 1995-11-30 1998-09-16 Vical Incorporated Complex cationic lipids
AU2112697A (en) * 1996-02-09 1997-08-28 Pi-Wan Cheng Receptor ligand-facilitated delivery of biologically active molecules
JP3258900B2 (ja) 1996-03-22 2002-02-18 三洋電機株式会社 電気炊飯器
US5962429A (en) * 1996-11-22 1999-10-05 University Of Iowa Complexes of adenovirus with cationic molecules

Also Published As

Publication number Publication date
JP2008247906A (ja) 2008-10-16
JP2000502061A (ja) 2000-02-22
WO1997019675A2 (en) 1997-06-05
WO1997019675A3 (en) 1997-10-02
EP0863749A2 (en) 1998-09-16
JP4430135B2 (ja) 2010-03-10
US8541628B2 (en) 2013-09-24
JP4965489B2 (ja) 2012-07-04
US20040171572A1 (en) 2004-09-02
US6670332B1 (en) 2003-12-30
CA2237316A1 (en) 1997-06-05

Similar Documents

Publication Publication Date Title
CA2237316C (en) Complex cationic lipids
US6022874A (en) Piperazine based cytofectins
EP1019365B1 (en) Novel compositions for the delivery of negatively charged molecules
EP0902780B1 (en) Quaternary cytofectins
CA2079814C (en) Cationic lipids for intracellular delivery of biologically active molecules
US6656498B1 (en) Cationic liposomes for gene transfer
AU738083B2 (en) Cationic amphiphile/ DNA complexes
US20030073640A1 (en) Novel compositions for the delivery of negatively charged molecules
EP0730404A4 (en) IMIDAZOLINIUM AMPHIPHILIC DERIVATIVES
US6489495B2 (en) Cationic amphiphiles for liposomal gene transfer
EP1187807B1 (en) Bipolar lipids and their use for the delivery of bioactive substances
HK1029578B (en) Novel compositions for the delivery of negatively charged molecules
EP1724254A2 (en) Novel compositions for the delivery of negatively charged molecules
AU5718099A (en) Cationic amphiphiles and plasmids for intracellular delivery of therapeutic molecules

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20151127