PE99298A1 - MODIFIED OLIGOSACCHARIDS - Google Patents
MODIFIED OLIGOSACCHARIDSInfo
- Publication number
- PE99298A1 PE99298A1 PE1997000688A PE00068897A PE99298A1 PE 99298 A1 PE99298 A1 PE 99298A1 PE 1997000688 A PE1997000688 A PE 1997000688A PE 00068897 A PE00068897 A PE 00068897A PE 99298 A1 PE99298 A1 PE 99298A1
- Authority
- PE
- Peru
- Prior art keywords
- glcnac
- compounds
- formula
- preferred
- tetrahidropirano
- Prior art date
Links
- -1 PREFERRED Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 abstract 2
- OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical compound CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 abstract 2
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 abstract 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 2
- 208000030090 Acute Disease Diseases 0.000 abstract 1
- 208000017667 Chronic Disease Diseases 0.000 abstract 1
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 abstract 1
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 abstract 1
- 230000001154 acute effect Effects 0.000 abstract 1
- PNNNRSAQSRJVSB-KCDKBNATSA-N aldehydo-L-fucose Chemical compound C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-KCDKBNATSA-N 0.000 abstract 1
- 230000001363 autoimmune Effects 0.000 abstract 1
- 230000001413 cellular effect Effects 0.000 abstract 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical class C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 1
- 229930182830 galactose Natural products 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 230000002757 inflammatory effect Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- BQINXKOTJQCISL-GRCPKETISA-N keto-neuraminic acid Chemical compound 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 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- CERZMXAJYMMUDR-UHFFFAOYSA-N neuraminic acid Natural products NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO CERZMXAJYMMUDR-UHFFFAOYSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7008—Compounds having an amino group directly attached to a carbon atom of the saccharide radical, e.g. D-galactosamine, ranimustine
-
- 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
- A61K31/702—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
SE REFIERE A COMPUESTOS DE FORMULA (I), EN DONDE: R1 ES UN METILO EN CONFIGURACION S SUSTITUIDO POR UN CARBOXI Y OTRO SUSTITUYENTE o -CH(R4)-COOR3; R2 ES H, ALQUILO C1-C12 o ARILO C6; R3 ES H o My, EN DONDE My es METAL MONO O DIVALENTE, DE PREFERENCIA, Na o K; R4 ES DE PREFERENCIA CH2-C6H5, (CH2)2-C6H5, CICLOHEXILO, METILO, ETILO o ISOPROPILO; "Z" ES UN RADICAL DE FORMULA (IIa), (IIb) o (IIc), EN DONDE: "X" ES CO, COO, CS, C(S)O, ENTRE OTROS; RT1 ES ALQUILO C1-C12, DE PREFERENCIA ES (CH2)8-COO-CH3, (CH2)8-COONa o CH3; RT2 ES CICLOALQUILO C3-C12, HETEROCICLOALQUILO C2-C11, ARILO C6-C10 o HETEROARILO C5-C9, DE PREFERENCIA ES -3,4-(OH)2-C6H3 o -3,4-(OCH3)2-C6H3; RB5 ES AMINO PRIMARIO o AMIDO; R5 ES DE PREFERENCIA CH2OH, CH3 o COONa. TAMBIEN SE REFIERE AL PROCEDIMIENTO DE PREPARACION DE LOS COMPUESTOS (I), DONDE LA GALACTOSA-(GlcNAc o TETRAHIDROPIRANO) o FUCOSA-(GlcNAc o TETRAHIDROPIRANO) ESTA ENLAZADO CON LA FUCOSA o GALACTOSA RESPECTIVAMENTE. LOS COMPUESTOS DE FORMULA (I) SON DERIVADOS DEL SIALIL LEWIS (LIGANDO NATURAL DE LA E-SELECTINA EN LA ADHESION CELULAR), EN DONDE SE REEMPLAZA EL RESIDUO DEL ACIDO NEURAMINICO Y GlcNAc NATURAL POR R1 Y "Z" RESPECTIVAMENTE, POR LO QUE ACTUARIAN INHIBIENDO EL ENLACE DE E-SELECTINA, SIENDO UTILES EN EL TRATAMIENTO DE ENFERMEDADES INFLAMATORIAS O AUTOINMUNES AGUDAS O CRONICAS, ENTRE OTRASREFERS TO COMPOUNDS OF FORMULA (I), WHERE: R1 IS A METHYL IN CONFIGURATION S REPLACED BY A CARBOXI AND ANOTHER SUBSTITUTE or -CH (R4) -COOR3; R2 IS H, C1-C12 ALKYL or C6 ARYL; R3 IS H or My, WHERE My is MONO OR DIVALENT METAL, PREFERRED, Na or K; R4 IS OF PREFERENCE CH2-C6H5, (CH2) 2-C6H5, CYCLOHEXYL, METHYL, ETHYL or ISOPROPYL; "Z" IS A RADICAL OF FORMULA (IIa), (IIb) or (IIc), WHERE: "X" IS CO, COO, CS, C (S) O, AMONG OTHERS; RT1 IS C1-C12 ALKYL, PREFERRED IS (CH2) 8-COO-CH3, (CH2) 8-COONa or CH3; RT2 IS C3-C12 CYCLLOALKYL, C2-C11 HETEROCICLOALKYL, C6-C10 ARYL or C5-C9 HETEROARYL, PREFERRED ES -3.4- (OH) 2-C6H3 or -3.4- (OCH3) 2-C6H3; RB5 IS PRIMARY AMINO or AMIDO; R5 IS OF PREFERENCE CH2OH, CH3 or COONa. IT ALSO REFERS TO THE PREPARATION PROCEDURE OF THE COMPOUNDS (I), WHERE THE GALACTOSE- (GlcNAc or TETRAHIDROPIRANO) or FUCOSA- (GlcNAc or TETRAHIDROPIRANO) IS LINKED TO THE RESPECTIVE FUCOSE OR GALACTOSE. THE COMPOUNDS OF FORMULA (I) ARE DERIVED FROM SIALIL LEWIS (NATURAL LINKAGE OF E-SELECTIN IN CELLULAR ACCESSION), WHERE THE RESIDUE OF THE NEURAMINIC ACID AND NATURAL GLcNAc IS REPLACED, WHEREAS ACTUALLY INHIBITING THE LINK OF E-SELECTIN, BEING USEFUL IN THE TREATMENT OF INFLAMMATORY OR AUTOIMMUNE ACUTE OR CHRONIC DISEASES, AMONG OTHERS
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96810527 | 1996-08-08 | ||
| EP96810526 | 1996-08-08 | ||
| EP96810636 | 1996-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE99298A1 true PE99298A1 (en) | 1999-01-21 |
Family
ID=27237868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE1997000688A PE99298A1 (en) | 1996-08-08 | 1997-08-07 | MODIFIED OLIGOSACCHARIDS |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0920437A1 (en) |
| JP (1) | JP2000516224A (en) |
| KR (1) | KR20000029862A (en) |
| CN (1) | CN1227563A (en) |
| AR (1) | AR008283A1 (en) |
| AU (1) | AU720381B2 (en) |
| BR (1) | BR9711117A (en) |
| CA (1) | CA2260854A1 (en) |
| CO (1) | CO4900075A1 (en) |
| CZ (1) | CZ39099A3 (en) |
| ID (1) | ID18010A (en) |
| IL (1) | IL127908A0 (en) |
| NO (1) | NO990497L (en) |
| NZ (1) | NZ334048A (en) |
| PE (1) | PE99298A1 (en) |
| PL (1) | PL331286A1 (en) |
| SK (1) | SK15699A3 (en) |
| TR (1) | TR199900245T2 (en) |
| WO (1) | WO1998006730A1 (en) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5888984A (en) * | 1994-05-12 | 1999-03-30 | Dermal Research Laboratories, Inc. | Pharmaceutical composition of complex carbohydrates and essential oils and methods of using the same |
| US8003782B1 (en) | 1999-02-01 | 2011-08-23 | Dermal Research Laboratories, Inc. | Pharmaceutical composition of complex carbohydrates and essential oils and methods of using the same |
| US7879824B2 (en) | 2001-07-31 | 2011-02-01 | Dermal Research Laboratories, Inc. | Methods of preventing or treating diseases and conditions using complex carbohydrates |
| US20040096396A1 (en) * | 2002-07-03 | 2004-05-20 | Glycomimetics, Inc. | Compositions and methods for diagnosis and therapy of medical conditions involving angiogenesis |
| MXPA05003844A (en) | 2002-10-11 | 2005-06-22 | Yamanouchi Europ Bv | Glucose-based compounds with affinity to p-selectin. |
| EP1763533B1 (en) | 2003-11-19 | 2008-01-09 | GlycoMimetics, Inc. | Specific antagonist for both e- and p-selectins |
| US20050187171A1 (en) * | 2003-11-19 | 2005-08-25 | Glycomimetics, Inc. | Glycomimetic antagonists for both E-and P-selectins |
| WO2006127906A1 (en) * | 2005-05-25 | 2006-11-30 | Glycomimetics, Inc. | Heterobifunctional compounds for selectin inhibition |
| WO2007021721A2 (en) | 2005-08-09 | 2007-02-22 | Glycomimetics, Inc. | Glycomimetic inhibitors of the pa-il lectin, pa-iil lectin or both the lectins from pseudomonas |
| SI2264043T1 (en) | 2005-09-02 | 2018-01-31 | Glycomimetics, Inc. | Heterobifunctional pan-selectin inhibitors |
| NZ598863A (en) * | 2007-02-09 | 2013-11-29 | Glycomimetics Inc | Methods of use of glycomimetics with replacements for hexoses and n-acetyl hexosamines |
| WO2009073911A1 (en) | 2007-12-10 | 2009-06-18 | Mater Medical Research Institute | Treatment and prophylaxis |
| US8895510B2 (en) | 2008-04-08 | 2014-11-25 | Glycomimetics, Inc. | Pan-selectin inhibitor with enhanced pharmacokinetic activity |
| WO2012037034A1 (en) | 2010-09-14 | 2012-03-22 | Glycomimetics, Inc. | E-selectin antagonists |
| SI2794626T1 (en) | 2011-12-22 | 2018-02-28 | Glycomimetics, Inc. | E-selectin antagonist compounds |
| SI2928476T1 (en) | 2012-12-07 | 2018-06-29 | Glycomimetics, Inc. | Compounds, compositions and methods using e-selectin antagonists for mobilization of hematopoietic cells |
| DK3227310T3 (en) | 2014-12-03 | 2019-09-30 | Glycomimetics Inc | HETEROBIFUNCTIONAL INHIBITORS OF E-SELECTINES AND CXCR4-CHEMOKIN RECEPTORS |
| CA3009836A1 (en) | 2016-01-22 | 2017-07-27 | Glycomimetics, Inc. | Glycomimetic inhibitors of pa-il and pa-iil lectins |
| US11291678B2 (en) | 2016-03-02 | 2022-04-05 | Glycomimetics, Inc | Methods for the treatment and/or prevention of cardiovascular disease by inhibition of E-selectin |
| US11433086B2 (en) | 2016-08-08 | 2022-09-06 | Glycomimetics, Inc. | Combination of T-cell checkpoint inhibitors with inhibitors of e-selectin or CXCR4, or with heterobifunctional inhibitors of both E-selectin and CXCR4 |
| CN117298287A (en) | 2016-10-07 | 2023-12-29 | 糖模拟物有限公司 | High potency multimeric E-selectin antagonists |
| JP7272956B2 (en) | 2017-03-15 | 2023-05-12 | グリコミメティクス， インコーポレイテッド | Galactopyranosyl-cyclohexyl derivatives as E-selectin antagonists |
| US11712446B2 (en) | 2017-11-30 | 2023-08-01 | Glycomimetics, Inc. | Methods of mobilizing marrow infiltrating lymphocytes and uses thereof |
| KR20200104889A (en) | 2017-12-29 | 2020-09-04 | 글리코미메틱스, 인크. | E-selectin and heterobifunctional inhibitors of galectin-3 |
| CN108299525B (en) * | 2018-01-05 | 2021-03-26 | 佛山科学技术学院 | Synthetic method of Lewis oligosaccharide-X |
| CN111867601A (en) | 2018-03-05 | 2020-10-30 | 糖模拟物有限公司 | Methods for the treatment of acute myeloid leukemia and related conditions |
| US11845771B2 (en) | 2018-12-27 | 2023-12-19 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectin and galectin-3 |
| CN109762032A (en) * | 2019-01-16 | 2019-05-17 | 天津科技大学 | A kind of sulfonated Lewis X trisaccharide and its synthesis method and application |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993023031A1 (en) * | 1992-05-08 | 1993-11-25 | The Biomembrane Institute | Multivalent mimetics and peptide mimetics for blocking carbohydrate-dependent cellular interaction and for eliciting anticarbohydrate t-cell response |
| EP0687684A4 (en) * | 1993-03-04 | 1998-03-04 | Kanto Ishi Pharma Co Ltd | Lewis-associated compound, process for producing the same, and anti-inflammatory |
| CA2162478A1 (en) * | 1993-05-14 | 1994-11-24 | Shawn A. Defrees | Sialyl lex analogues as inhibitors of cellular adhesion |
| EP0801071A4 (en) * | 1994-12-28 | 1999-01-13 | Sumitomo Pharma | LEWIS-X DERIVATIVES AND METHOD FOR THEIR PRODUCTION |
-
1997
- 1997-08-06 AR ARP970103580A patent/AR008283A1/en unknown
- 1997-08-06 CN CN97197077A patent/CN1227563A/en active Pending
- 1997-08-06 JP JP10509358A patent/JP2000516224A/en active Pending
- 1997-08-06 IL IL12790897A patent/IL127908A0/en unknown
- 1997-08-06 SK SK156-99A patent/SK15699A3/en unknown
- 1997-08-06 WO PCT/EP1997/004279 patent/WO1998006730A1/en not_active Ceased
- 1997-08-06 EP EP97941916A patent/EP0920437A1/en not_active Withdrawn
- 1997-08-06 CZ CZ99390A patent/CZ39099A3/en unknown
- 1997-08-06 PL PL97331286A patent/PL331286A1/en unknown
- 1997-08-06 NZ NZ334048A patent/NZ334048A/en unknown
- 1997-08-06 CA CA002260854A patent/CA2260854A1/en not_active Abandoned
- 1997-08-06 KR KR1019997001025A patent/KR20000029862A/en not_active Withdrawn
- 1997-08-06 BR BR9711117-1A patent/BR9711117A/en not_active Application Discontinuation
- 1997-08-06 TR TR1999/00245T patent/TR199900245T2/en unknown
- 1997-08-06 AU AU43788/97A patent/AU720381B2/en not_active Ceased
- 1997-08-07 PE PE1997000688A patent/PE99298A1/en not_active Application Discontinuation
- 1997-08-08 CO CO97045596A patent/CO4900075A1/en unknown
- 1997-08-08 ID IDP972766A patent/ID18010A/en unknown
-
1999
- 1999-02-03 NO NO990497A patent/NO990497L/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1998006730A1 (en) | 1998-02-19 |
| NZ334048A (en) | 2000-05-26 |
| KR20000029862A (en) | 2000-05-25 |
| JP2000516224A (en) | 2000-12-05 |
| BR9711117A (en) | 1999-09-08 |
| AU720381B2 (en) | 2000-06-01 |
| PL331286A1 (en) | 1999-07-05 |
| CN1227563A (en) | 1999-09-01 |
| CZ39099A3 (en) | 1999-05-12 |
| AU4378897A (en) | 1998-03-06 |
| CO4900075A1 (en) | 2000-03-27 |
| EP0920437A1 (en) | 1999-06-09 |
| SK15699A3 (en) | 1999-07-12 |
| IL127908A0 (en) | 1999-11-30 |
| NO990497L (en) | 1999-03-24 |
| ID18010A (en) | 1998-02-19 |
| TR199900245T2 (en) | 1999-05-21 |
| AR008283A1 (en) | 1999-12-29 |
| CA2260854A1 (en) | 1998-02-19 |
| NO990497D0 (en) | 1999-02-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration | ||
| FD | Application declared void or lapsed |