CA2141679A1 - New Derivatives of Neuraminic Acid - Google Patents

New Derivatives of Neuraminic Acid

Info

Publication number
CA2141679A1
CA2141679A1 CA 2141679 CA2141679A CA2141679A1 CA 2141679 A1 CA2141679 A1 CA 2141679A1 CA 2141679 CA2141679 CA 2141679 CA 2141679 A CA2141679 A CA 2141679A CA 2141679 A1 CA2141679 A1 CA 2141679A1
Authority
CA
Canada
Prior art keywords
neuraminic acid
new derivatives
amides
derivatives
diseases
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.)
Granted
Application number
CA 2141679
Other languages
French (fr)
Other versions
CA2141679C (en
Inventor
Aurelio Romeo
Gunter Kirschner
Hari Manev
Martino Trimarco
Gino Toffano
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.)
Fidia SpA
Original Assignee
Aurelio Romeo
Gunter Kirschner
Hari Manev
Martino Trimarco
Gino Toffano
Fidia S.P.A.
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 Aurelio Romeo, Gunter Kirschner, Hari Manev, Martino Trimarco, Gino Toffano, Fidia S.P.A. filed Critical Aurelio Romeo
Publication of CA2141679A1 publication Critical patent/CA2141679A1/en
Application granted granted Critical
Publication of CA2141679C publication Critical patent/CA2141679C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C07H13/06—Fatty acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/10—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to heterocyclic rings
    • 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
    • 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
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
    • C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Abstract

Provided are new derivatives of neuraminic acid of formula (I), where Ac represents an aryl residue of an aliphatic, araliphatic aromatic, alicyclic, or heterocyclic carboxylic acid, including carboxylic amides, their 2-hydrocarbyl-glycosides, and their peracylated derivatives at the hydroxy groups of both these series of amides.
These compounds are therapeutically useful in providing a protective effect against the neurotoxicity induced by excitatory amino acids, and can therefore be used in therapies of the central nervous system following cerebral degenerations or lesions, metabolic dysfunctions, aging, and toxic-infective and chronic neurodegenerative diseases such as Alzheimer's, Parkinson's, and Huntington's diseases.
CA002141679A 1992-08-03 1993-08-03 New derivatives of neuraminic acid Expired - Fee Related CA2141679C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
ITPD92A000146 1992-08-03
ITPD920146A IT1260156B (en) 1992-08-03 1992-08-03 NEURAMINIC ACID DERIVATIVES
PCT/US1993/007307 WO1994003469A1 (en) 1992-08-03 1993-08-03 New derivatives of neuraminic acid

Publications (2)

Publication Number Publication Date
CA2141679A1 true CA2141679A1 (en) 1994-02-17
CA2141679C CA2141679C (en) 2000-09-19

Family

ID=11390038

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002141679A Expired - Fee Related CA2141679C (en) 1992-08-03 1993-08-03 New derivatives of neuraminic acid

Country Status (6)

Country Link
EP (1) EP0652887A1 (en)
JP (1) JPH08502953A (en)
AU (1) AU4801493A (en)
CA (1) CA2141679C (en)
IT (1) IT1260156B (en)
WO (1) WO1994003469A1 (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5783564A (en) * 1993-12-24 1998-07-21 Mitsubishi Chemical Corporation Sialic acid derivatives
TW479061B (en) * 1993-12-24 2002-03-11 Mitsubishi Chem Corp Sialic acid derivatives
IT1271624B (en) * 1994-03-21 1997-06-04 Lifegroup Spa GLUCOSIDIC DERIVATIVES OF N-ACYL ALCHYLAMINES CAPABLE OF EXERCISING EFFECT OR NEUROPROTECTIVE USABLE IN ACUTE AND CHRONIC PATHOLOGIES OF THE CENTRAL NERVOUS SYSTEM RELATED TO EXCITOTOXICITY
US5849709A (en) * 1995-05-10 1998-12-15 Glycomed Incorporated Saccharopeptides and derivatives thereof
DE69616554T2 (en) 1995-06-23 2002-07-11 Mitsubishi Chem Corp SIALIC DERIVATIVES
US5824662A (en) * 1996-09-27 1998-10-20 Guilford Pharmaceuticals Inc. Treatment of global and focal ischemia using naaladase inhibitors
HUP0001062A3 (en) 1996-09-27 2001-09-28 Guilford Pharmaceuticals Inc B Pharmaceutical compositions of phosphinic acid derivatives having naaladase inhibitor acivity
WO1999052931A1 (en) 1998-04-10 1999-10-21 Mitsubishi Chemical Corporation Solid dispersion containing sialic acid derivative
WO2002094302A1 (en) * 2001-05-23 2002-11-28 Gil-Ja Jhon Compositions comprising extract of ganoderma lucidum, oleamide and its structural analogue as an effective component for preventing or treating dementia
JP4005115B1 (en) * 2007-02-08 2007-11-07 日本臓器製薬株式会社 Pain disease treatment
JP5327839B2 (en) * 2008-06-09 2013-10-30 国立大学法人埼玉大学 Method for producing sialic acid derivative and its use as an influenza virus inhibitor
JP5298390B2 (en) * 2009-11-19 2013-09-25 学校法人福岡大学 Fluorosylated sialic acid derivative and analysis method thereof
TWI599354B (en) 2016-08-10 2017-09-21 國立臺灣師範大學 Use of tetrahydropyranol derivatives for manufacturing pharmaceutical composition of tau-associated diseases

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3014027A (en) * 1956-01-20 1961-12-19 Ciba Pharm Prod Inc N-acylamino compounds
IL41409A (en) * 1972-02-04 1977-04-29 Richter Gedeon Vegyeszet Lysergic acid amides and process for their preparation
JPS60231690A (en) * 1984-05-01 1985-11-18 Kanto Ishi Pharma Co Ltd N-substituted neuraminic acid derivative and its preparation
NL194729C (en) * 1986-10-13 2003-01-07 Novartis Ag Process for the preparation of peptide alcohols via solid phase.
JPH03151398A (en) * 1989-11-06 1991-06-27 Mect Corp Sialic acid-bonded physiologically active peptide and production thereof

Also Published As

Publication number Publication date
WO1994003469A1 (en) 1994-02-17
AU4801493A (en) 1994-03-03
ITPD920146A1 (en) 1994-02-03
EP0652887A1 (en) 1995-05-17
JPH08502953A (en) 1996-04-02
ITPD920146A0 (en) 1992-08-03
CA2141679C (en) 2000-09-19
IT1260156B (en) 1996-03-28

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