WO2002012258A1 - New immunoeffector compounds - Google Patents

New immunoeffector compounds Download PDF

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Publication number
WO2002012258A1
WO2002012258A1 PCT/US2001/024284 US0124284W WO0212258A1 WO 2002012258 A1 WO2002012258 A1 WO 2002012258A1 US 0124284 W US0124284 W US 0124284W WO 0212258 A1 WO0212258 A1 WO 0212258A1
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WO
WIPO (PCT)
Prior art keywords
group
compound
pharmaceutical composition
subscripts
configuration
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
PCT/US2001/024284
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English (en)
French (fr)
Inventor
David A. Johnson
Jory Baldridge
Greg Sowell
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.)
Corixa Corp
Original Assignee
Corixa Corp
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 Corixa Corp filed Critical Corixa Corp
Priority to CA2417806A priority Critical patent/CA2417806C/en
Priority to AU8100101A priority patent/AU8100101A/xx
Priority to AU2001281001A priority patent/AU2001281001B2/en
Priority to DE60118207T priority patent/DE60118207T2/de
Priority to EP01959445A priority patent/EP1311522B1/en
Priority to JP2002518232A priority patent/JP4843181B2/ja
Priority to US10/469,620 priority patent/US7129219B2/en
Publication of WO2002012258A1 publication Critical patent/WO2002012258A1/en
Anticipated expiration legal-status Critical
Priority to US11/519,275 priority patent/US7501399B2/en
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings

Definitions

  • Immune adjuvants are compounds which, when administered to an individual or tested in vitro, increase the immune response to an antigen in a subject to which the antigen is administered, or enhance certain activities of cells from the immune system.
  • a number of compounds exhibiting varying degrees of adjuvant activity have been prepared and tested (see, for example, Shimizu et al. 1985, Bulusu et al. 1992, Ikeda et al. 1993, Shimizu et al. 1994, Shimizu et al. 1995, Miyajima et al. 1996).
  • these and other prior adjuvant systems often display toxic properties, are unstable and/or have unacceptably low immunostimulatory effects.
  • alkylene by itself or as part of another substituent means a divalent radical derived from an alkane, as exemplified by -CH 2 CH 2 CH 2 CH -, and further includes those groups known as “heteroalkylenes.”
  • alkoxy alkylamino
  • alkylthio refer to those groups having an alkyl group attached to the remainder ofthe molecule through an oxygen, nitrogen or sulfur atom, respectively.
  • Examples of pharmaceutically acceptable acid addition salts include those derived from inorganic acids like hydrochloric, hydrobromic, nitric, carbonic, monohydrogencarbonic, phosphoric, monohydrogenphosphoric, dihydrogenphosphoric, sulfuric, monohy ⁇ rogensulfuric, hydriodic, or phosphorous acids and the like, as well as the salts derived from relatively nontoxic organic acids like acetic, propionic, isobutyric, oxalic, maleic, malonic, benzoic, succinic, suberic, fumaric, mandelic, phthalic, benzenesulfonic, p-tolylsulfonic, citric, tartaric, methanesulfonic, and the like.
  • inorganic acids like hydrochloric, hydrobromic, nitric, carbonic, monohydrogencarbonic, phosphoric, monohydrogenphosphoric, dihydrogenphosphoric, sulfuric, monohy ⁇ rogensulfuric, hydri
  • the present invention provides compounds which are in a prodrug form.
  • Prodrugs ofthe compounds described herein are those compounds that readily undergo chemical changes under physiological conditions to provide the compounds ofthe present invention.
  • prodrugs can be converted to the compounds ofthe present invention by chemical or biochemical methods in an ex vivo environment. For example, prodrugs can be slowly converted to the compounds ofthe present invention when placed in a transdermal patch reservoir with a suitable enzyme or chemical reagent.
  • Certain compounds ofthe present invention possess asymmetric carbon atoms (optical centers) or double bonds; the racemates, diastereomers, geometric isomers and individual isomers are all intended to be encompassed within the scope ofthe present invention.
  • the compounds of the present invention may also contain unnatural proportions of atomic isotopes at one or more ofthe atoms that constitute such compounds.
  • the compounds may be radiolabeled with radioactive isotopes, such as for example tritium ( 3 H), iodine-125 ( 125 I) or carbon-14 ( 14 C). All isotopic variations ofthe compounds ofthe present invention, whether radioactive or not, are intended to be encompassed within the scope ofthe present invention.
  • In vivo and ex vivo transfection of dendritic cells may generally be performed using any methods known in the art, such as those described in WO 97/24447, or the gene gun approach described by Mahvi et al., Immunology and cell Biology 75:456-460, 1997.
  • Antigen loading of dendritic cells may be achieved by incubating dendritic cells or progenitor cells with the antigen polypeptide, DNA (naked or within a plasmid vector) or RNA; or with antigen-expressing recombinant bacterium or viruses (e.g., vaccinia, fowlpox, adeno virus or lenti virus vectors).
  • RC-553 is able to enhance immunity to vaccine antigens.
  • RC-553 enhanced serum titers to two distinct vaccine antigens, influenza and hepatitis surface antigens.
  • MPL® immunostimulant the RC-553 mediated a shift in the antibody profile from a response dominated by the IgGl isotype to a response with high levels of IgG2a antibodies.
  • RC-553 is a good adjuvant for inducing CTL activity.
  • Example 7 Inducible Nitric Oxide Synthase (iNOS) stimulation by RC-553
  • iNOS Nitric Oxide Synthase
  • the murine macrophage cell line J774 can be primed by JJFN- ⁇ in vitro and is very responsive to subsequent LPS stimulation of iNOS upregulation as measured by a standard Greiss reagent ELISA assay procedure.
  • the assay utilizes J774 cells seeded at 1 x 10 6 /mL with 30 mL/flask and with IFN- ⁇ added at 100 units/mL for 16-24 hrs.
  • MPL® immunostimulant was found to have an ED 50 of about 2 ng/mL resulting in high levels of nitrite elaboration while RC-553 exhibited a nominal ED50 of about > 3000 (ng/ml).

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Diabetes (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Immunology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Dermatology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Cardiology (AREA)
  • Pain & Pain Management (AREA)
  • Neurology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Saccharide Compounds (AREA)
  • Medicinal Preparation (AREA)
PCT/US2001/024284 2000-08-04 2001-08-03 New immunoeffector compounds Ceased WO2002012258A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
CA2417806A CA2417806C (en) 2000-08-04 2001-08-03 New immunoeffector compounds
AU8100101A AU8100101A (en) 2000-08-04 2001-08-03 New immunoeffector compounds
AU2001281001A AU2001281001B2 (en) 2000-08-04 2001-08-03 New immunoeffector compounds
DE60118207T DE60118207T2 (de) 2000-08-04 2001-08-03 Neue immunoeffectorverbindungen
EP01959445A EP1311522B1 (en) 2000-08-04 2001-08-03 New immunoeffector compounds
JP2002518232A JP4843181B2 (ja) 2000-08-04 2001-08-03 免疫エフェクター化合物
US10/469,620 US7129219B2 (en) 2000-08-04 2001-08-03 Immunoeffector compounds
US11/519,275 US7501399B2 (en) 2000-08-04 2006-09-11 Immunoeffector compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US22305600P 2000-08-04 2000-08-04
US60/223,056 2000-08-04

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US10496620 A-371-Of-International 2001-08-03
US11/519,275 Division US7501399B2 (en) 2000-08-04 2006-09-11 Immunoeffector compounds

Publications (1)

Publication Number Publication Date
WO2002012258A1 true WO2002012258A1 (en) 2002-02-14

Family

ID=22834828

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/024284 Ceased WO2002012258A1 (en) 2000-08-04 2001-08-03 New immunoeffector compounds

Country Status (9)

Country Link
US (2) US7129219B2 (https=)
EP (1) EP1311522B1 (https=)
JP (1) JP4843181B2 (https=)
AT (1) ATE321063T1 (https=)
AU (2) AU8100101A (https=)
CA (1) CA2417806C (https=)
DE (1) DE60118207T2 (https=)
ES (1) ES2261453T3 (https=)
WO (1) WO2002012258A1 (https=)

Cited By (18)

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US6525028B1 (en) 2002-02-04 2003-02-25 Corixa Corporation Immunoeffector compounds
WO2003066065A1 (en) 2002-02-04 2003-08-14 Corixa Corporation Prophylactic and therapeutic treatment of infectious and other diseases with immunoeffector compounds
WO2004005308A2 (en) 2002-07-08 2004-01-15 Corixa Corporation Processes for the production of aminoalkyl glucosaminide phosphate and disaccharide immunoeffectors, and intermediates therefor
WO2004062599A2 (en) 2003-01-06 2004-07-29 Corixa Corporation Certain aminoalkyl glucosaminide phosphate compounds and their use
US6911434B2 (en) 2002-02-04 2005-06-28 Corixa Corporation Prophylactic and therapeutic treatment of infectious and other diseases with immunoeffector compounds
EP1482795A4 (en) * 2002-02-04 2006-08-09 Corixa Corp NEW IMMUNE EFFECTOR LINKS
WO2007071711A2 (en) 2005-12-22 2007-06-28 Glaxosmithkline Biologicals Sa Vaccine
WO2007116028A2 (en) 2006-04-07 2007-10-18 Glaxosmithkline Biologicals S.A. Conjugate vaccines
US7288640B2 (en) 2002-07-08 2007-10-30 Corixa Corporation Processes for the production of aminoalkyl glucosaminide phosphate and disaccharide immunoeffectors, and intermediates therefor
WO2009000826A1 (en) 2007-06-26 2008-12-31 Glaxosmithkline Biologicals S.A. Vaccine comprising streptococcus pneumoniae capsular polysaccharide conjugates
WO2012055981A1 (en) 2010-10-27 2012-05-03 Glaxosmithkline Biologicals S.A. Immunogenic compositions and methods for treating neurologic disorders
WO2013020723A1 (en) 2011-08-05 2013-02-14 Glaxosmithkline Biologicals S.A. Compositions and uses thereof for the treatment or prevention of alzheimer's disease
EP2940027A1 (en) 2004-07-08 2015-11-04 Corixa Corporation Certain aminoalkyl glucosaminide phosphate compounds and their use
US9827260B2 (en) 2013-03-15 2017-11-28 Glaxosmithkline Biologicals Sa Composition for buffered aminoalkyl glucosaminide phosphate compounds and its use for enhancing an immune response
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Cited By (34)

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US20070004914A1 (en) 2007-01-04
CA2417806C (en) 2011-05-10
EP1311522A4 (en) 2004-06-09
US7129219B2 (en) 2006-10-31
AU2001281001B2 (en) 2005-11-03
DE60118207T2 (de) 2006-11-09
DE60118207D1 (de) 2006-05-11
EP1311522A1 (en) 2003-05-21
JP4843181B2 (ja) 2011-12-21
AU8100101A (en) 2002-02-18
EP1311522B1 (en) 2006-03-22
JP2004505986A (ja) 2004-02-26
CA2417806A1 (en) 2002-02-14
ES2261453T3 (es) 2006-11-16
US7501399B2 (en) 2009-03-10
ATE321063T1 (de) 2006-04-15

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