CA2141679C - New derivatives of neuraminic acid - Google Patents

New derivatives of neuraminic acid Download PDF

Info

Publication number: CA2141679C
Authority: CA; Canada
Prior art keywords: acid; group; carboxylic; derived; ethylglycoside
Prior art date: 1992-08-03
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.): Expired - Fee Related

Application number

CA002141679A

Other languages

English (en)

French (fr)

Other versions

CA2141679A1 (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

Fidia SpA

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.)

1992-08-03

Filing date

1993-08-03

Publication date

2000-09-19

1993-08-03 Application filed by Fidia SpA filed Critical Fidia SpA

1994-02-17 Publication of CA2141679A1 publication Critical patent/CA2141679A1/en

2000-09-19 Application granted granted Critical

2000-09-19 Publication of CA2141679C publication Critical patent/CA2141679C/en

2013-08-03 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

CERZMXAJYMMUDR-QBTAGHCHSA-N 5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid Chemical class N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO CERZMXAJYMMUDR-QBTAGHCHSA-N 0.000 title description 13
150000001408 amides Chemical class 0.000 claims abstract description 82
150000001875 compounds Chemical class 0.000 claims abstract description 62
-1 heterocyclic carboxylic acid Chemical class 0.000 claims abstract description 47
125000001931 aliphatic group Chemical group 0.000 claims abstract description 24
125000003118 aryl group Chemical group 0.000 claims abstract description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
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238000002560 therapeutic procedure Methods 0.000 claims abstract description 4
230000003818 metabolic dysfunction Effects 0.000 claims abstract description 3
BQINXKOTJQCISL-GRCPKETISA-N keto-neuraminic acid Chemical class OC(=O)C(=O)C[C@H](O)[C@@H](N)[C@@H](O)[C@H](O)[C@H](O)CO BQINXKOTJQCISL-GRCPKETISA-N 0.000 claims abstract 3
239000002253 acid Substances 0.000 claims description 75
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
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XKIXFVUBVFVZIA-AYAKNUJESA-N CCCCCCCCCCCCCCCC(=O)N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO XKIXFVUBVFVZIA-AYAKNUJESA-N 0.000 claims description 41
SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 claims description 34
SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 claims description 34
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QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 28
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CERZMXAJYMMUDR-UHFFFAOYSA-N neuraminic acid Natural products NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO CERZMXAJYMMUDR-UHFFFAOYSA-N 0.000 claims description 27
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HZNQSWJZTWOTKM-UHFFFAOYSA-N 2,3,4-trimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC)=C1OC HZNQSWJZTWOTKM-UHFFFAOYSA-N 0.000 claims description 3
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Classifications

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- 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
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- 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
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- 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

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Biotechnology (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biomedical Technology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurology (AREA)
Biophysics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Psychiatry (AREA)
Cardiology (AREA)
Hospice & Palliative Care (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Crystallography & Structural Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

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
ITPD920146A IT1260156B (it)	1992-08-03	1992-08-03	Derivati dell'acido neuraminico
ITPD92A000146		1992-08-03
PCT/US1993/007307 WO1994003469A1 (en)	1992-08-03	1993-08-03	New derivatives of neuraminic acid

Publications (2)

Publication Number	Publication Date
CA2141679A1 CA2141679A1 (en)	1994-02-17
CA2141679C true 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 (it)
JP (1)	JPH08502953A (it)
AU (1)	AU4801493A (it)
CA (1)	CA2141679C (it)
IT (1)	IT1260156B (it)
WO (1)	WO1994003469A1 (it)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW479061B (en) *	1993-12-24	2002-03-11	Mitsubishi Chem Corp	Sialic acid derivatives
US5783564A (en) *	1993-12-24	1998-07-21	Mitsubishi Chemical Corporation	Sialic acid derivatives
IT1271624B (it) *	1994-03-21	1997-06-04	Lifegroup Spa	Derivati glucosidici di n-acil alchilamine capaci di esercitare effetto o neuroprotettivo utilizzabili nelle patologie acute e croniche del sistema nervoso centrale correlate ad eccitotossicita'
US5849709A (en) *	1995-05-10	1998-12-15	Glycomed Incorporated	Saccharopeptides and derivatives thereof
WO1997000885A1 (fr)	1995-06-23	1997-01-09	Mitsubishi Chemical Corporation	Derives d'acide sialique
US5824662A (en) *	1996-09-27	1998-10-20	Guilford Pharmaceuticals Inc.	Treatment of global and focal ischemia using naaladase inhibitors
CA2264043A1 (en)	1996-09-27	1998-04-02	Guilford Pharmaceuticals Inc.	Naaladase compositions and methods for treating glutamate abnormality and effecting neuronal activity in animals
US6444649B1 (en)	1998-04-10	2002-09-03	Mitsubishi Chemical Corporation	Solid dispersion containing sialic acid derivative
CN1523994A (zh) *	2001-05-23	2004-08-25	钱吉子	一种用于预防和/或治疗痴呆的以灵芝提取物、十八碳烯酰胺及其衍生物作为有效成分的组合物
JP4005115B1 (ja) *	2007-02-08	2007-11-07	日本臓器製薬株式会社	疼痛疾患治療剤
JP5327839B2 (ja) *	2008-06-09	2013-10-30	国立大学法人埼玉大学	シアル酸誘導体の製造方法とインフルエンザウィルス阻害剤としての利用
JP5298390B2 (ja) *	2009-11-19	2013-09-25	学校法人福岡大学	フルオラス化シアル酸誘導体およびその分析方法
TWI599354B (zh)	2016-08-10	2017-09-21	國立臺灣師範大學	四氫吡喃醇衍生化合物用於製備Tau蛋白病變類疾病之醫藥組成物上之用途

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 (ja) *	1984-05-01	1985-11-18	Kanto Ishi Pharma Co Ltd	Ｎ―置換ノイラミン酸誘導体
NL194729C (nl) *	1986-10-13	2003-01-07	Novartis Ag	Werkwijze voor de bereiding van peptidealcoholen via vaste fase.
JPH03151398A (ja) *	1989-11-06	1991-06-27	Mect Corp	シアル酸結合生理活性ペプチド及びその製造方法

1992
- 1992-08-03 IT ITPD920146A patent/IT1260156B/it active IP Right Grant
1993
- 1993-08-03 AU AU48014/93A patent/AU4801493A/en not_active Abandoned
- 1993-08-03 WO PCT/US1993/007307 patent/WO1994003469A1/en not_active Ceased
- 1993-08-03 JP JP6505524A patent/JPH08502953A/ja active Pending
- 1993-08-03 EP EP93918621A patent/EP0652887A1/en not_active Withdrawn
- 1993-08-03 CA CA002141679A patent/CA2141679C/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2141679A1 (en)	1994-02-17
AU4801493A (en)	1994-03-03
WO1994003469A1 (en)	1994-02-17
ITPD920146A0 (it)	1992-08-03
IT1260156B (it)	1996-03-28
ITPD920146A1 (it)	1994-02-03
EP0652887A1 (en)	1995-05-17
JPH08502953A (ja)	1996-04-02

Legal Events

Date	Code	Title	Description
1995-02-09	EEER	Examination request
2002-08-05	MKLA	Lapsed

Publication	Publication Date	Title
CA2141679C (en)	2000-09-19	New derivatives of neuraminic acid
US5424294A (en)	1995-06-13	Modified gangliosides and the functional derivatives thereof
EP0373038B1 (en)	1997-03-05	New lysosphingolipid derivatives
EP0599908B1 (en)	1997-03-12	New ganglioside derivatives
US5677285A (en)	1997-10-14	Derivatives of neuraminic acid
EP0373039B1 (en)	1994-04-06	New lysoganglioside derivatives
DE69031448T2 (de)	1998-02-26	Halbsynthetische Gangliosidanaloge
Bulusu et al.	1992	Acyclic analogs of lipid A: synthesis and biological activities.
PT88568B (pt)	1992-11-30	Processo para a preparacao de derivados de sacaridos
DE69033027T2 (de)	1999-11-25	Di-lysogangliosidderivate
US6407072B1 (en)	2002-06-18	Lysoganglioside derivatives
US5795869A (en)	1998-08-18	Sulfated lyso-ganglioside derivatives
US5849717A (en)	1998-12-15	O-sulfated gangliosides and lyso-ganglioside derivatives
DE3879622T2 (de)	1993-09-30	Aminopimelinsäure-Derivate, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel.
EP0688331B1 (en)	2001-06-13	New sulfated lyso-ganglioside derivatives
CZ130398A3 (cs)	1999-11-17	Lipofilní analogy N-acetyl-normuramoyl-L-alfa-aminobutanoyl-D-isoglutaminu s imunostimulační aktivitou