AU705549B2 - Phosphonic acid-based cationic lipids - Google Patents

Phosphonic acid-based cationic lipids Download PDF

Info

Publication number
AU705549B2
AU705549B2 AU63287/96A AU6328796A AU705549B2 AU 705549 B2 AU705549 B2 AU 705549B2 AU 63287/96 A AU63287/96 A AU 63287/96A AU 6328796 A AU6328796 A AU 6328796A AU 705549 B2 AU705549 B2 AU 705549B2
Authority
AU
Australia
Prior art keywords
moiety
carbon atoms
lipid
group
alkyl
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.)
Ceased
Application number
AU63287/96A
Other languages
English (en)
Other versions
AU6328796A (en
Inventor
Bob Dale Brown
Brian Patrick Dwyer
Alexander V. Lebedev
David Aaron Schwartz
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.)
Promega Biosciences Inc
Original Assignee
Genta 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 Genta Inc filed Critical Genta Inc
Publication of AU6328796A publication Critical patent/AU6328796A/en
Application granted granted Critical
Publication of AU705549B2 publication Critical patent/AU705549B2/en
Assigned to PROMEGA BIOSCIENCES, INC. reassignment PROMEGA BIOSCIENCES, INC. Alteration of Name(s) in Register under S187 Assignors: GENTA INCORPORATED
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4075—Esters with hydroxyalkyl compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
    • 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
    • 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
    • A61K47/548—Phosphates or phosphonates, e.g. bone-seeking
    • 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
    • C07J—STEROIDS
    • C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00

Landscapes

  • 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)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biophysics (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Steroid Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Detergent Compositions (AREA)
AU63287/96A 1995-06-07 1996-06-05 Phosphonic acid-based cationic lipids Ceased AU705549B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US48471695A 1995-06-07 1995-06-07
US08/484716 1995-06-07
PCT/US1996/009478 WO1996040725A1 (en) 1995-06-07 1996-06-05 Phosphonic acid-based cationic lipids

Publications (2)

Publication Number Publication Date
AU6328796A AU6328796A (en) 1996-12-30
AU705549B2 true AU705549B2 (en) 1999-05-27

Family

ID=23925304

Family Applications (1)

Application Number Title Priority Date Filing Date
AU63287/96A Ceased AU705549B2 (en) 1995-06-07 1996-06-05 Phosphonic acid-based cationic lipids

Country Status (6)

Country Link
US (2) US5958901A (https=)
EP (1) EP0840744A4 (https=)
JP (1) JPH11507815A (https=)
AU (1) AU705549B2 (https=)
CA (1) CA2223179A1 (https=)
WO (1) WO1996040725A1 (https=)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0840744A4 (en) * 1995-06-07 1999-03-10 Genta Inc CATIONIC LIPIDS BASED ON PHOSPHONIC ACID
EP1724254A3 (en) * 1997-07-23 2012-01-04 Sirna Therapeutics, Inc. Novel compositions for the delivery of negatively charged molecules
US20030073640A1 (en) * 1997-07-23 2003-04-17 Ribozyme Pharmaceuticals, Inc. Novel compositions for the delivery of negatively charged molecules
CA2299429C (en) 1997-08-13 2010-04-20 Biontex Laboratories Gmbh New lipopolyamines,their preparation and the use thereof
US7915238B2 (en) * 1999-02-01 2011-03-29 Eisai R & D Management Co., Ltd. Immunomodulatory compounds and methods of use thereof
US6835721B2 (en) * 1999-02-01 2004-12-28 Eisai Co., Ltd. Immunomodulatory compounds and methods of use thereof
US6551600B2 (en) * 1999-02-01 2003-04-22 Eisai Co., Ltd. Immunological adjuvant compounds compositions and methods of use thereof
US20040006242A1 (en) 1999-02-01 2004-01-08 Hawkins Lynn D. Immunomodulatory compounds and method of use thereof
AU1925501A (en) * 1999-11-24 2001-06-04 University Of Oregon Complexes of alkylphosphonic acids
CA2395636A1 (en) * 1999-12-30 2001-07-12 Novartis Ag Novel colloid synthetic vectors for gene therapy
US6800728B2 (en) 2000-03-22 2004-10-05 Solulink Biosciences, Inc. Hydrazine-based and carbonyl-based bifunctional crosslinking reagents
US6686461B1 (en) 2000-03-22 2004-02-03 Solulink Bioscience, Inc. Triphosphate oligonucleotide modification reagents and uses thereof
US7102024B1 (en) 2000-08-01 2006-09-05 Schwartz David A Functional biopolymer modification reagents and uses thereof
JP2002071941A (ja) * 2000-08-25 2002-03-12 Kureha Chem Ind Co Ltd 光学材料
DE10117043A1 (de) * 2001-04-05 2002-11-07 Gerhard Puetz Verfahren zur Eliminierung von potentiell toxischen und/oder schädlichen Stoffen
AU2002348163A1 (en) * 2001-11-02 2003-05-19 Intradigm Corporation Therapeutic methods for nucleic acid delivery vehicles
EP1519714B1 (en) 2002-06-28 2010-10-20 Protiva Biotherapeutics Inc. Method and apparatus for producing liposomes
EP1664316B1 (en) 2003-09-15 2012-08-29 Protiva Biotherapeutics Inc. Polyethyleneglycol-modified lipid compounds and uses thereof
US7158353B2 (en) * 2003-11-06 2007-01-02 Seagate Technology Llc Magnetoresistive sensor having specular sidewall layers
CA2569664C (en) 2004-06-07 2013-07-16 Protiva Biotherapeutics, Inc. Lipid encapsulated interfering rna
CA2587411A1 (en) * 2004-11-17 2006-05-26 Protiva Biotherapeutics, Inc. Sirna silencing of apolipoprotein b
US20070292418A1 (en) * 2005-04-26 2007-12-20 Eisai Co., Ltd. Compositions and methods for immunotherapy
CN103285392A (zh) 2005-04-26 2013-09-11 卫材R&D管理株式会社 用于癌症免疫疗法的组合物和其用途
US20070087045A1 (en) * 2005-10-14 2007-04-19 Industrial Technology Research Institute Lipid carrier and method of preparing the same
CN101346393B (zh) 2005-11-02 2015-07-22 普洛体维生物治疗公司 修饰的siRNA分子及其应用
ES2535419T3 (es) * 2007-12-27 2015-05-11 Protiva Biotherapeutics Inc. Silenciamiento de expresión de quinasa tipo polo usando ARN interferente
WO2009086558A1 (en) * 2008-01-02 2009-07-09 Tekmira Pharmaceuticals Corporation Improved compositions and methods for the delivery of nucleic acids
CA2721333C (en) 2008-04-15 2020-12-01 Protiva Biotherapeutics, Inc. Novel lipid formulations for nucleic acid delivery
CA2740000C (en) 2008-10-09 2017-12-12 Tekmira Pharmaceuticals Corporation Improved amino lipids and methods for the delivery of nucleic acids
US9023820B2 (en) 2009-01-26 2015-05-05 Protiva Biotherapeutics, Inc. Compositions and methods for silencing apolipoprotein C-III expression
US20100240883A1 (en) * 2009-03-18 2010-09-23 Nian Wu Lipid-drug conjugates for drug delivery
WO2011000107A1 (en) 2009-07-01 2011-01-06 Protiva Biotherapeutics, Inc. Novel lipid formulations for delivery of therapeutic agents to solid tumors
US9018187B2 (en) 2009-07-01 2015-04-28 Protiva Biotherapeutics, Inc. Cationic lipids and methods for the delivery of therapeutic agents
US8569256B2 (en) 2009-07-01 2013-10-29 Protiva Biotherapeutics, Inc. Cationic lipids and methods for the delivery of therapeutic agents
US8716464B2 (en) 2009-07-20 2014-05-06 Thomas W. Geisbert Compositions and methods for silencing Ebola virus gene expression
US8455455B1 (en) 2010-03-31 2013-06-04 Protiva Biotherapeutics, Inc. Compositions and methods for silencing genes involved in hemorrhagic fever
US9006417B2 (en) 2010-06-30 2015-04-14 Protiva Biotherapeutics, Inc. Non-liposomal systems for nucleic acid delivery
US8466122B2 (en) 2010-09-17 2013-06-18 Protiva Biotherapeutics, Inc. Trialkyl cationic lipids and methods of use thereof
US9035039B2 (en) 2011-12-22 2015-05-19 Protiva Biotherapeutics, Inc. Compositions and methods for silencing SMAD4
EP2912045A4 (en) * 2012-10-29 2016-07-13 Molecular Transfer Inc POLYCATION METHYL PHOSPHOLIPIDES FOR IMPROVED RELEASE OF NUCLEIC ACIDS IN EUKARYOTIC CELLS
JP5914418B2 (ja) 2013-06-26 2016-05-11 富士フイルム株式会社 脂質粒子、核酸送達キャリア、核酸送達キャリア製造用組成物、脂質粒子の製造方法及び遺伝子導入方法
EP4295895A3 (en) 2017-05-11 2024-03-27 Tc1 Llc Thermal interconnect for implantable blood pump
CA3101484A1 (en) * 2018-05-30 2019-12-05 Translate Bio, Inc. Phosphoester cationic lipids
WO2022115645A1 (en) 2020-11-25 2022-06-02 Akagera Medicines, Inc. Lipid nanoparticles for delivery of nucleic acids, and related methods of use
CA3256897A1 (en) 2022-05-25 2023-11-30 Akagera Medicines, Inc. Lipid nanoparticles for the administration of nucleic acids and their methods of use

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4680290A (en) * 1983-08-25 1987-07-14 Hoffmann-La Roche Inc. Steroids for the treatment of hypercholesterolemia
US5215972A (en) * 1989-11-22 1993-06-01 Hoffmann-La Roche Inc. Steroids

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4897355A (en) * 1985-01-07 1990-01-30 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
EP0467954B1 (en) * 1989-03-31 1996-05-01 The Regents Of The University Of California Preparation of liposome and lipid complex compositions
FR2645866B1 (fr) * 1989-04-17 1991-07-05 Centre Nat Rech Scient Nouvelles lipopolyamines, leur preparation et leur emploi
US5264618A (en) * 1990-04-19 1993-11-23 Vical, Inc. Cationic lipids for intracellular delivery of biologically active molecules
US5283185A (en) * 1991-08-28 1994-02-01 University Of Tennessee Research Corporation Method for delivering nucleic acids into cells
US5334761A (en) * 1992-08-28 1994-08-02 Life Technologies, Inc. Cationic lipids
US5420328A (en) * 1992-09-11 1995-05-30 Affymax Technologies, N.V. Methods for the synthesis of phosphonate esters
KR100283601B1 (ko) * 1993-02-19 2001-03-02 아만 히데아키 글리세롤 유도체, 디바이스 및 의약 조성물
US5651981A (en) * 1994-03-29 1997-07-29 Northwestern University Cationic phospholipids for transfection
WO1996040726A1 (en) * 1995-06-07 1996-12-19 Genta Incorporated Novel carbamate-based cationic lipids
EP0840744A4 (en) * 1995-06-07 1999-03-10 Genta Inc CATIONIC LIPIDS BASED ON PHOSPHONIC ACID

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4680290A (en) * 1983-08-25 1987-07-14 Hoffmann-La Roche Inc. Steroids for the treatment of hypercholesterolemia
US5215972A (en) * 1989-11-22 1993-06-01 Hoffmann-La Roche Inc. Steroids

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NUCLEOSIDES & NUCLEOTIDES, 13(9) 1994 P1843-53 BALOGOPALA ET *

Also Published As

Publication number Publication date
WO1996040725A1 (en) 1996-12-19
US5958901A (en) 1999-09-28
CA2223179A1 (en) 1996-12-19
EP0840744A1 (en) 1998-05-13
JPH11507815A (ja) 1999-07-13
AU6328796A (en) 1996-12-30
US6172049B1 (en) 2001-01-09
EP0840744A4 (en) 1999-03-10

Similar Documents

Publication Publication Date Title
AU705549B2 (en) Phosphonic acid-based cationic lipids
AU701106B2 (en) Novel carbamate-based cationic lipids
US6020526A (en) Amide-based cationic lipids
US6034135A (en) Dimeric cationic lipids
WO1996040726A9 (en) Novel carbamate-based cationic lipids
US6638529B2 (en) Amide-based cationic lipids
US5877220A (en) Amide-based oligomeric cationic lipids
WO1997003939A9 (en) Novel amide-based cationic lipids
US6503945B2 (en) Cationic amphiphiles containing N-hydroxyalkyl group for intracellular delivery of biologically active molecules
WO1998039358A9 (en) Oligomeric cationic lipids
JP4467084B2 (ja) 核酸を細胞に導入するための化合物、その製法及びその使用
US5906922A (en) Delivery of nucleic acids
JP2002530364A (ja) 両親媒性ポリアミン化合物
JP4990153B2 (ja) ジアルキレントリアミンのアミドおよびペプチド誘導体、ならびにトランスフェクション剤としてのそれらの使用
MXPA99010489A (en) Compounds, preparation and use for transferring nucleic acids into cells

Legal Events

Date Code Title Description
PC Assignment registered

Owner name: PROMEGA BIOSCIENCES, INC.

Free format text: FORMER OWNER WAS: GENTA INCORPORATED