CA2502285A1 - Molecules de cardiolipine et procedes pour leur synthese - Google Patents

Molecules de cardiolipine et procedes pour leur synthese Download PDF

Info

Publication number
CA2502285A1
CA2502285A1 CA002502285A CA2502285A CA2502285A1 CA 2502285 A1 CA2502285 A1 CA 2502285A1 CA 002502285 A CA002502285 A CA 002502285A CA 2502285 A CA2502285 A CA 2502285A CA 2502285 A1 CA2502285 A1 CA 2502285A1
Authority
CA
Canada
Prior art keywords
cardiolipin
composition
acid
liposome
mmol
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.)
Abandoned
Application number
CA002502285A
Other languages
English (en)
Inventor
Moghis U. Ahmad
Murali K. Ukkalam
Imran Ahmad
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.)
Neopharm Inc
Original Assignee
Individual
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 PCT/US2003/013917 external-priority patent/WO2004062569A2/fr
Priority claimed from PCT/US2003/016412 external-priority patent/WO2003099830A2/fr
Application filed by Individual filed Critical Individual
Publication of CA2502285A1 publication Critical patent/CA2502285A1/fr
Abandoned 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/10—Phosphatides, e.g. lecithin
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A61K31/52—Purines, e.g. adenine
    • A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
    • 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
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • 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
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • A61K31/7072—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
    • 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
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers with substantial amounts of non-phosphatidyl, i.e. non-acylglycerophosphate, surfactants as bilayer-forming substances, e.g. cationic lipids

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Dispersion Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)

Abstract

La présente invention concerne de nouvelles voies de la synthèse de la cardiolipine avec différents acides gras et/ou chaînes alkyle de longueur de chaîne variable, avec ou sans insaturation, et plus particulièrement une cardiolipine à chaîne courte. Pour ce procédé, on prend un 1,2-O-sn-diacyle/1,2-O-sn-dialkyle glycérol ou un glycérol 2-<I>O</I>-protégé, et on le fait réagir avec un réactif au phosphoramidite ou un triester de phosphate de façon à produire une cardiolipine protégée que l'on déprotège pour obtenir la cardiolipine à chaîne courte. Ces logiques de réaction se prêtent à l'obtention de nouvelles variantes de cardiolipine. La cardiolipine ainsi obtenue peut s'incorporer à des liposomes pouvant également inclure des agents actifs tels que des médicaments hydrophobes ou hydrophiles. De tels liposomes conviennent pour le traitement de maladies ou pour des essais de diagnostic ou d'analyse. Les liposomes peuvent également comporter des ligands permettant de cibler un type de cellule particulier ou un tissu spécifique.
CA002502285A 2002-10-16 2003-09-05 Molecules de cardiolipine et procedes pour leur synthese Abandoned CA2502285A1 (fr)

Applications Claiming Priority (13)

Application Number Priority Date Filing Date Title
US41927702P 2002-10-16 2002-10-16
US60/419,277 2002-10-16
US42928502P 2002-11-26 2002-11-26
US60/429,285 2002-11-26
US43865903P 2003-01-07 2003-01-07
US60/438,659 2003-01-07
US46733103P 2003-05-02 2003-05-02
US60/467,331 2003-05-02
USPCT/US03/13917 2003-05-04
PCT/US2003/013917 WO2004062569A2 (fr) 2003-01-07 2003-05-04 Compositions de cardiolipine, leurs procedes de preparation et d'utilisation
USPCT/US03/16412 2003-05-23
PCT/US2003/016412 WO2003099830A2 (fr) 2002-05-24 2003-05-23 Compositions de cardiolipine, leurs procedes de preparation et d'utilisation
PCT/US2003/027806 WO2004039817A1 (fr) 2002-10-16 2003-09-05 Molecules de cardiolipine et procedes pour leur synthese

Publications (1)

Publication Number Publication Date
CA2502285A1 true CA2502285A1 (fr) 2004-05-13

Family

ID=32234368

Family Applications (2)

Application Number Title Priority Date Filing Date
CA002502285A Abandoned CA2502285A1 (fr) 2002-10-16 2003-09-05 Molecules de cardiolipine et procedes pour leur synthese
CA002501990A Abandoned CA2501990A1 (fr) 2002-10-16 2003-10-16 Analogues de cardiolipine cationiques et utilisation de ceux-ci

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA002501990A Abandoned CA2501990A1 (fr) 2002-10-16 2003-10-16 Analogues de cardiolipine cationiques et utilisation de ceux-ci

Country Status (7)

Country Link
EP (2) EP1556392A1 (fr)
JP (2) JP2006510733A (fr)
AU (2) AU2003268478A1 (fr)
CA (2) CA2502285A1 (fr)
EA (2) EA200500659A1 (fr)
HK (1) HK1080087A1 (fr)
WO (2) WO2004039817A1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8815599B2 (en) 2004-06-01 2014-08-26 Pronai Therapeutics, Inc. Methods and compositions for the inhibition of gene expression
US20080286351A1 (en) * 2004-06-29 2008-11-20 Ahmad Moghis U Pegylated Cardiolipin Analogs, Methods of Synthesis, and Uses Thereof
EP1819715A4 (fr) * 2004-11-08 2010-02-17 Neopharm Inc Synthese de produits analogues de la cardiolipine et leurs applications
WO2006113679A2 (fr) 2005-04-15 2006-10-26 Board Of Regents, The University Of Texas System Administration d'arnsi par compositions lipidiques neutres
WO2007014150A2 (fr) * 2005-07-22 2007-02-01 Neopharm, Inc. Procede d'administration de liposomes contenant des oligonucleotides
JP5122474B2 (ja) 2005-12-01 2013-01-16 プロネイ・セラピューティクス・インコーポレイテッド 両性リポソーム製剤
WO2007065017A2 (fr) * 2005-12-01 2007-06-07 Pronai Therapeutics, Inc. Systeme d'administration de liposomes cationiques a oligonucleotides
JP2009527576A (ja) * 2006-02-24 2009-07-30 ネオフアーム・インコーポレイテツド カルジオリピン調製の方法および工程
HUE052571T2 (hu) * 2008-09-27 2021-05-28 Jina Pharmaceuticals Inc Lipid alapú gyógyszerészeti készítmények helyi alkalmazáshoz
KR101778169B1 (ko) * 2012-04-11 2017-09-13 리폭센 테크놀로지즈 리미티드 미엘린염기성단백질의 올리고펩티드 단편을 함유하는 리포솜, 의약조성물 및 다발성경화증의 치료법

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2113606A (en) * 1934-05-24 1938-04-12 Alba Pharmaceutical Company In Quaternary ammonium compounds
US6461637B1 (en) * 2000-09-01 2002-10-08 Neopharm, Inc. Method of administering liposomal encapsulated taxane
WO2000027795A1 (fr) * 1998-11-12 2000-05-18 Invitrogen Corporation Reactifs de transfection
EP1183231B1 (fr) * 1999-05-28 2004-11-24 Vical Incorporated Dimeres de cytofectine et procedes d'utilisation associes

Also Published As

Publication number Publication date
CA2501990A1 (fr) 2004-04-29
AU2003277445A1 (en) 2004-05-04
WO2004039817A1 (fr) 2004-05-13
EA200500661A1 (ru) 2005-10-27
JP2006510733A (ja) 2006-03-30
WO2004039817A9 (fr) 2004-07-22
JP2006503112A (ja) 2006-01-26
AU2003268478A1 (en) 2004-05-25
WO2004035523A1 (fr) 2004-04-29
EA200500659A1 (ru) 2005-10-27
EP1556392A1 (fr) 2005-07-27
HK1080087A1 (zh) 2006-04-21
EP1558562A1 (fr) 2005-08-03
WO2004035523B1 (fr) 2004-08-26

Similar Documents

Publication Publication Date Title
US20050266068A1 (en) Cardiolipin molecules and methods of synthesis
US20050181037A1 (en) Cardiolipin compositions their methods of preparation and use
US20050277611A1 (en) Cationic cardiolipin analoges and its use thereof
Eibl Phospholipids as functional constituents of biomembranes
US9637515B2 (en) Guggulphospholipid methods and compositions
US20080286351A1 (en) Pegylated Cardiolipin Analogs, Methods of Synthesis, and Uses Thereof
JPH08504439A (ja) リポソーム組込みのためのホスホノ酸の脂質誘導体および使用方法
CN1360611A (zh) 中性脂质聚合物以及含中性脂质聚合物的脂质体组合物
CA2502285A1 (fr) Molecules de cardiolipine et procedes pour leur synthese
US20080300418A1 (en) Synthesis of Cardiolipin Analogues and Uses Thereof
US6344576B1 (en) Phospholipid-analogous compounds
AU754862B2 (en) Use of bisphosphonates for the prevention and treatment of infectious processes
CN1714095A (zh) 心磷脂分子及合成方法
WO2007100808A2 (fr) Procédés servant à préparer de la cardiolipine
WO2004062569A2 (fr) Compositions de cardiolipine, leurs procedes de preparation et d&#39;utilisation
WO2004060899A1 (fr) Derives de phospholipides et procedes de leur production
CN1714094A (zh) 心磷脂组合物及它们制备的方法和应用
JP2003522203A (ja) 天然に存在しない核酸組成物、核酸を細胞中にトランスフェクションするのに有用な処方物の調製のためのそれらの使用、および応用
WO2024019770A1 (fr) Procédés de fabrication de lipides ionisables et de nanoparticules lipidiques pour l&#39;administration d&#39;arnm

Legal Events

Date Code Title Description
FZDE Dead