WO1999029706A3 - DISALICYLATE ANALOG BASED SIALYL LEWISx MIMETICS - Google Patents

DISALICYLATE ANALOG BASED SIALYL LEWISx MIMETICS Download PDF

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Publication number
WO1999029706A3
WO1999029706A3 PCT/US1998/025788 US9825788W WO9929706A3 WO 1999029706 A3 WO1999029706 A3 WO 1999029706A3 US 9825788 W US9825788 W US 9825788W WO 9929706 A3 WO9929706 A3 WO 9929706A3
Authority
WO
WIPO (PCT)
Prior art keywords
selectin
disalicylate
mimetics
compounds
distance
Prior art date
Application number
PCT/US1998/025788
Other languages
French (fr)
Other versions
WO1999029706A2 (en
Inventor
Mark B Anderson
Daniel E Levy
Kevin R Holme
Original Assignee
Glycomed Inc
Sankyo Co
Mark B Anderson
Daniel E Levy
Kevin R Holme
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 Glycomed Inc, Sankyo Co, Mark B Anderson, Daniel E Levy, Kevin R Holme filed Critical Glycomed Inc
Priority to AU19036/99A priority Critical patent/AU1903699A/en
Publication of WO1999029706A2 publication Critical patent/WO1999029706A2/en
Publication of WO1999029706A3 publication Critical patent/WO1999029706A3/en

Links

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
    • C07H15/18—Acyclic radicals, substituted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/105—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C66/00—Quinone carboxylic acids
    • C07C66/02—Anthraquinone carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention discloses medicaments that are selectin-ligand structural mimetics that bind to certain selectins wherein the mimetics may lack the sialic acid and/or fucose of the natural selecting ligand, sialyl Lewisx (sLex), but have a structure capable of mimicking the structural features necessary for selectin recognition. In particular, the invention compounds mimic the key structural features of the oligosaccharides responsible for selectin-mediated cell adhesion. These features consist of the charge-distance-coordination relationship between the carboxylic acid functionality of sialic acid at a distance of 8-12 angstroms of the L-fucose moiety. The invention compounds are disalicylate, its analogs, and disalicylate-based C-glycoside compounds. The present invention also discloses methods of treating selectin-mediated disorders comprising administering the compounds disclosed.
PCT/US1998/025788 1997-12-08 1998-12-04 DISALICYLATE ANALOG BASED SIALYL LEWISx MIMETICS WO1999029706A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU19036/99A AU1903699A (en) 1997-12-08 1998-12-04 Disalicylate analog based sialyl lewisx mimetics

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US6787797P 1997-12-08 1997-12-08
US60/067,877 1997-12-08

Publications (2)

Publication Number Publication Date
WO1999029706A2 WO1999029706A2 (en) 1999-06-17
WO1999029706A3 true WO1999029706A3 (en) 1999-08-12

Family

ID=22079008

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/025788 WO1999029706A2 (en) 1997-12-08 1998-12-04 DISALICYLATE ANALOG BASED SIALYL LEWISx MIMETICS

Country Status (2)

Country Link
AU (1) AU1903699A (en)
WO (1) WO1999029706A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1577289A1 (en) 2004-03-18 2005-09-21 Revotar Biopharmaceuticals AG Non-glycosylated/-glycosidic/-peptidic small molecule selectin inhibitors for the treament of inflammatory disorders
EP1764095A1 (en) 2005-09-20 2007-03-21 Revotar Biopharmaceuticals AG Novel nitrocatechol derivatives having selectin ligand activity
EP1764093A1 (en) 2005-09-20 2007-03-21 Revotar Biopharmaceuticals AG Novel aromatic compounds and their use in medical applications
EP1764096A1 (en) 2005-09-20 2007-03-21 Revotar Biopharmaceuticals AG Novel phloroglucinol derivatives having selectin ligand activity
US11013750B2 (en) 2017-01-20 2021-05-25 Aurin Biotech Inc. Methods for treating and preventing nociceptive pain
JPWO2020158931A1 (en) * 2019-01-31 2021-12-02 三菱瓦斯化学株式会社 Compounds, resins, compositions, resist pattern forming methods, circuit pattern forming methods and resin purification methods

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991015200A2 (en) * 1990-04-03 1991-10-17 Radopath Limited Use of trinitrobenzenes or carminic acid in the treatment of cancer or viral diseases
WO1992001664A1 (en) * 1990-07-17 1992-02-06 European Colour Plc Synthesis of carminic acid and principal intermediates
DE4122210A1 (en) * 1991-07-04 1993-01-14 Deutsches Krebsforsch Conjugate comprising antitumoural cpd. and protein in native form - which is stable and accumulates at high levels in the tumour
WO1994018189A1 (en) * 1993-02-08 1994-08-18 Glycomed Incorporated Anthraquinone and anthracene derivatives as inhibitors of the cell-adhesion molecules of the immune system
WO1997001335A1 (en) * 1995-06-29 1997-01-16 Texas Biotechnology Corporation Di- and trivalent small molecule selectin inhibitors
WO1997030984A1 (en) * 1996-02-21 1997-08-28 Glycomed Incorporated Sialyl lewisx mimetics containing phenyl backbones
WO1998031697A1 (en) * 1997-01-15 1998-07-23 Sankyo Company, Limited Aryl c-glycoside compounds and sulfated esters thereof

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991015200A2 (en) * 1990-04-03 1991-10-17 Radopath Limited Use of trinitrobenzenes or carminic acid in the treatment of cancer or viral diseases
WO1992001664A1 (en) * 1990-07-17 1992-02-06 European Colour Plc Synthesis of carminic acid and principal intermediates
DE4122210A1 (en) * 1991-07-04 1993-01-14 Deutsches Krebsforsch Conjugate comprising antitumoural cpd. and protein in native form - which is stable and accumulates at high levels in the tumour
WO1994018189A1 (en) * 1993-02-08 1994-08-18 Glycomed Incorporated Anthraquinone and anthracene derivatives as inhibitors of the cell-adhesion molecules of the immune system
WO1997001335A1 (en) * 1995-06-29 1997-01-16 Texas Biotechnology Corporation Di- and trivalent small molecule selectin inhibitors
WO1997030984A1 (en) * 1996-02-21 1997-08-28 Glycomed Incorporated Sialyl lewisx mimetics containing phenyl backbones
WO1998031697A1 (en) * 1997-01-15 1998-07-23 Sankyo Company, Limited Aryl c-glycoside compounds and sulfated esters thereof

Also Published As

Publication number Publication date
AU1903699A (en) 1999-06-28
WO1999029706A2 (en) 1999-06-17

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