NZ334048A - Mimetics of natural carbohydrate epitotes as ligands for E and P Selectin - Google Patents
Mimetics of natural carbohydrate epitotes as ligands for E and P SelectinInfo
- Publication number
- NZ334048A NZ334048A NZ334048A NZ33404897A NZ334048A NZ 334048 A NZ334048 A NZ 334048A NZ 334048 A NZ334048 A NZ 334048A NZ 33404897 A NZ33404897 A NZ 33404897A NZ 334048 A NZ334048 A NZ 334048A
- Authority
- NZ
- New Zealand
- Prior art keywords
- 11aralkyl
- 12alkyl
- 10aryl
- 6alkylene
- replaced
- Prior art date
Links
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- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen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
Abstract
Derivatives of sialyl-Lewis X and A, in which the natural neuraminic acid residue is replaced by an S-configured methyl substituted with one carboxyl residue and one other substituent, and the natural N-acetylglucosamine monomer are replaced by a variety of different aliphatic and aromatic substituents or N-acetylglucosamine residue is replaced by tetrahydropyran derivative. This appears to increase the binding properties in which to prevent the interaction between P and E selectins and their receptors on the leukocyte membrane and which prevent the initial cellular adhesion process. This would decrease situations that the recruitment of leukocytes by adhesion to the endothelial cells is abnormal and in excess resulting in tissue damage instead of repair. This is the case in disorders such as cardiogenic shock, myocardial infarct, thrombosis, rheumatism, psoriasis, arthritis, dermatitis, acute respiratory distress syndrome, metastatic cancer and transplantation. The formula (IA)-(IC) wherein; X is -C(O)-, -S(O)2-, -C(O)Q, wherein Q is NH, O, S, S-C1-6alkylene, NH-C1-6alkylene or O-C1-6alkylene; R1 is an S-configured methyl substituted with a carboxy and one other substituent; R2 is H, C1-12alkyl or C6aryl; RT1 is C1-12alkyl, C2-12alkenyl, C1-12alkoxy, C3-12cycloalkyl, C2-11heterocycloalkyl, C2-11heterocycloalkenyl, C6-10aryl, C6-10aryloxy, C5-9heteroaryl, C6-10heteroaryloxy, C7-11aralkyl, C7-11aralkyloxy,C6-10heteroarakyl, C8-11aralkenyl or C7-10heteroaralkenyl; RT2 is C3-12cycloalkyl, C2-11heterocycloalkyl, C2-11heterocycloalkenyl, C6-10aryl, C6-10aryloxy, C5-9heteroaryl, C6-10heteroaryloxy, C7-11aralkyl, C7-11aralkyloxy,C6-10heteroarakyl, C8-11aralkenyl or C7-10heteroaralkenyl; RB5 is NH2, primary or secondary amino or amido; R3 is H or My R4 is C1-12alkyl, C2-12alkenyl, C3-12cycloalkyl, C3-12cycloalkenyl, C2-11heterocycloalkyl, C2-11heterocycloalkenyl, C6-10aryl, C5-9heteroaryl, C7-11aralkyl, C6-10heteroarakyl, C8-11aralkenyl or C7-10heteroaralkenyl; R5 is X`-RT1C, C(O)NRTC2RT3C, C(O)RT4C or C(O)ORT5C, wherein X` is C1-4alkylene; RT1C to RT5C are common hydrocarbon substituents; When y is 1 M is a monovalent metal or when y is 1/2 M is divalent metal.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96810527 | 1996-08-08 | ||
| EP96810526 | 1996-08-08 | ||
| EP96810636 | 1996-09-26 | ||
| PCT/EP1997/004279 WO1998006730A1 (en) | 1996-08-08 | 1997-08-06 | Modified oligosaccharides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ334048A true NZ334048A (en) | 2000-05-26 |
Family
ID=27237868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ334048A NZ334048A (en) | 1996-08-08 | 1997-08-06 | Mimetics of natural carbohydrate epitotes as ligands for E and P Selectin |
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 (26)
| 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 |
| CA2361268C (en) | 1999-02-01 | 2014-06-10 | Dermal Research Laboratories, Inc. | A 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 |
| WO2004004636A2 (en) * | 2002-07-03 | 2004-01-15 | Glycomimetics, Inc. | Compositions and methods for diagnosis and therapy of medical conditions involving angiogenesis |
| US7304039B2 (en) | 2002-10-11 | 2007-12-04 | Astellas Pharma Europe B.V. | Glucose-based compounds with affinity to P-selectin |
| US20050187171A1 (en) * | 2003-11-19 | 2005-08-25 | Glycomimetics, Inc. | Glycomimetic antagonists for both E-and P-selectins |
| US20090036386A1 (en) * | 2005-05-25 | 2009-02-05 | Glycomimetics, Inc | Heterobifunctional compounds for selectin inhibition |
| PL2264043T3 (en) | 2005-09-02 | 2018-04-30 | 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 |
| WO2009126556A1 (en) | 2008-04-08 | 2009-10-15 | Glycomimetics, Inc. | Pan-selectin inhibitor with enhanced pharmacokinetic activity |
| WO2012037034A1 (en) | 2010-09-14 | 2012-03-22 | Glycomimetics, Inc. | E-selectin antagonists |
| PL2794626T6 (en) | 2011-12-22 | 2020-11-02 | Glycomimetics, Inc. | E-selectin antagonist compounds |
| PL2928476T3 (en) | 2012-12-07 | 2018-07-31 | Glycomimetics, Inc. | Compounds, compositions and methods using e-selectin antagonists for mobilization of hematopoietic cells |
| AU2015355136B2 (en) | 2014-12-03 | 2020-06-25 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectins and CXCR4 chemokine 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 |
| WO2018031445A1 (en) | 2016-08-08 | 2018-02-15 | 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 |
| BR112019006642A2 (en) | 2016-10-07 | 2019-07-02 | Glycomimetics Inc | highly potent 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 |
| JP7275131B2 (en) | 2017-11-30 | 2023-05-17 | グリコミメティクス， インコーポレイテッド | Methods of mobilizing bone marrow-infiltrating lymphocytes and uses thereof |
| JP7304863B2 (en) | 2017-12-29 | 2023-07-07 | グリコミメティクス， インコーポレイテッド | Heterobifunctional inhibitors of E-selectin and galectin-3 |
| CN108299525B (en) * | 2018-01-05 | 2021-03-26 | 佛山科学技术学院 | Method for synthesizing Lewis oligose-X |
| JP7455064B2 (en) | 2018-03-05 | 2024-03-25 | グリコミメティクス， インコーポレイテッド | Methods of treating 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 synthetic 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 |
| US5763413A (en) * | 1993-03-04 | 1998-06-09 | Mect Corporation | Lewis-associated compound, process for producing the same, and anti-inflammatory |
| JPH08510729A (en) * | 1993-05-14 | 1996-11-12 | サイテル コーポレイション | Sialyl Le <ab> x analogues as inhibitors of cell adhesion |
| WO1996020204A1 (en) * | 1994-12-28 | 1996-07-04 | Sumitomo Pharmaceuticals Company, Limited | Lewis x derivative and process for producing the same |
-
1997
- 1997-08-06 BR BR9711117-1A patent/BR9711117A/en not_active Application Discontinuation
- 1997-08-06 EP EP97941916A patent/EP0920437A1/en not_active Withdrawn
- 1997-08-06 CA CA002260854A patent/CA2260854A1/en not_active Abandoned
- 1997-08-06 CN CN97197077A patent/CN1227563A/en active Pending
- 1997-08-06 KR KR1019997001025A patent/KR20000029862A/en not_active Application Discontinuation
- 1997-08-06 TR TR1999/00245T patent/TR199900245T2/en unknown
- 1997-08-06 WO PCT/EP1997/004279 patent/WO1998006730A1/en not_active Application Discontinuation
- 1997-08-06 NZ NZ334048A patent/NZ334048A/en unknown
- 1997-08-06 AR ARP970103580A patent/AR008283A1/en unknown
- 1997-08-06 JP JP10509358A patent/JP2000516224A/en active Pending
- 1997-08-06 PL PL97331286A patent/PL331286A1/en unknown
- 1997-08-06 AU AU43788/97A patent/AU720381B2/en not_active Ceased
- 1997-08-06 CZ CZ99390A patent/CZ39099A3/en unknown
- 1997-08-06 SK SK156-99A patent/SK15699A3/en unknown
- 1997-08-06 IL IL12790897A patent/IL127908A0/en unknown
- 1997-08-07 PE PE1997000688A patent/PE99298A1/en not_active Application Discontinuation
- 1997-08-08 ID IDP972766A patent/ID18010A/en unknown
- 1997-08-08 CO CO97045596A patent/CO4900075A1/en unknown
-
1999
- 1999-02-03 NO NO990497A patent/NO990497L/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU4378897A (en) | 1998-03-06 |
| AR008283A1 (en) | 1999-12-29 |
| NO990497D0 (en) | 1999-02-03 |
| TR199900245T2 (en) | 1999-05-21 |
| CN1227563A (en) | 1999-09-01 |
| BR9711117A (en) | 1999-09-08 |
| NO990497L (en) | 1999-03-24 |
| IL127908A0 (en) | 1999-11-30 |
| EP0920437A1 (en) | 1999-06-09 |
| WO1998006730A1 (en) | 1998-02-19 |
| AU720381B2 (en) | 2000-06-01 |
| PE99298A1 (en) | 1999-01-21 |
| CO4900075A1 (en) | 2000-03-27 |
| JP2000516224A (en) | 2000-12-05 |
| CA2260854A1 (en) | 1998-02-19 |
| CZ39099A3 (en) | 1999-05-12 |
| KR20000029862A (en) | 2000-05-25 |
| ID18010A (en) | 1998-02-19 |
| SK15699A3 (en) | 1999-07-12 |
| PL331286A1 (en) | 1999-07-05 |
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