WO1997028173B1 - Analogues d'epitopes de sialyle-lewisa et de sialyle-lewis?x¿ - Google Patents
Analogues d'epitopes de sialyle-lewisa et de sialyle-lewis?x¿Info
- Publication number
- WO1997028173B1 WO1997028173B1 PCT/EP1997/000222 EP9700222W WO9728173B1 WO 1997028173 B1 WO1997028173 B1 WO 1997028173B1 EP 9700222 W EP9700222 W EP 9700222W WO 9728173 B1 WO9728173 B1 WO 9728173B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- mono
- sialyl
- compound according
- alkylamino
- Prior art date
Links
- LAQPKDLYOBZWBT-NYLDSJSYSA-N (2s,4s,5r,6r)-5-acetamido-2-{[(2s,3r,4s,5s,6r)-2-{[(2r,3r,4r,5r)-5-acetamido-1,2-dihydroxy-6-oxo-4-{[(2s,3s,4r,5s,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1r,2r)-1,2,3-trihydrox Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]([C@@H](NC(C)=O)C=O)[C@@H]([C@H](O)CO)O[C@H]1[C@H](O)[C@@H](O[C@]2(O[C@H]([C@H](NC(C)=O)[C@@H](O)C2)[C@H](O)[C@H](O)CO)C(O)=O)[C@@H](O)[C@@H](CO)O1 LAQPKDLYOBZWBT-NYLDSJSYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 4
- -1 benzylamino, sulfhydryl Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000006725 C1-C10 alkenyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 abstract 1
- SHZGCJCMOBCMKK-PQMKYFCFSA-N L-Fucose Natural products C[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O SHZGCJCMOBCMKK-PQMKYFCFSA-N 0.000 abstract 1
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 abstract 1
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 abstract 1
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 abstract 1
- 125000003047 N-acetyl group Chemical group 0.000 abstract 1
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 abstract 1
- 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 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- 229950006780 n-acetylglucosamine Drugs 0.000 abstract 1
- 235000000346 sugar Nutrition 0.000 abstract 1
- 150000008163 sugars Chemical class 0.000 abstract 1
Abstract
Cette invention concerne des analogues d'épitopes de sialyle-Lewisa et de sialyle-Lewisx dans lesquels le groupe N-acétyle d'origine naturelle du monomère de N-acétylglucosamine est remplacé par différents substituants aliphatiques ou aromatiques et le L-fucose naturellement présent est remplacé par divers sucres qui sont ou non d'origine naturelle.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69737496T DE69737496D1 (de) | 1996-01-30 | 1997-01-17 | SIALYL-LEWISa UND SIALYL LEWISx EPITOP-ANALOGE |
| EP97901546A EP0886640B1 (fr) | 1996-01-30 | 1997-01-17 | ANALOGUES D'EPITOPES DE SIALYLE-LEWISa ET DE SIALYLE-LEWISx |
| AU15423/97A AU1542397A (en) | 1996-01-30 | 1997-01-17 | Sialyl-lewisa and sialyl-lewisx epitope analogues |
| US09/117,482 US6169077B1 (en) | 1996-01-30 | 1997-01-17 | Sialyl-Lewisa and sialyl-Lewisx epitope analogues |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH230/96 | 1996-01-30 | ||
| CH23096 | 1996-01-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1997028173A1 WO1997028173A1 (fr) | 1997-08-07 |
| WO1997028173B1 true WO1997028173B1 (fr) | 1997-09-18 |
Family
ID=4182259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1997/000222 WO1997028173A1 (fr) | 1996-01-30 | 1997-01-17 | Analogues d'epitopes de sialyle-lewisa et de sialyle-lewis?x¿ |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6169077B1 (fr) |
| EP (1) | EP0886640B1 (fr) |
| AT (1) | ATE357452T1 (fr) |
| AU (1) | AU1542397A (fr) |
| DE (1) | DE69737496D1 (fr) |
| WO (1) | WO1997028173A1 (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7060685B2 (en) | 2002-05-16 | 2006-06-13 | Glycomimetics, Inc. | Compounds and methods for inhibiting selectin-mediated function |
| US7361644B2 (en) | 2003-11-19 | 2008-04-22 | Glycomimetics, Inc. | Specific antagonist for both E- and P-selectins |
| US8921328B2 (en) | 2010-09-14 | 2014-12-30 | Glycomimetics, Inc. | E-selectin antagonists |
| US9534009B2 (en) | 2008-04-08 | 2017-01-03 | Glycomimetics, Inc. | Pan-selectin inhibitor with enhanced pharmacokinetic activity |
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|---|---|---|---|---|
| PT1001961E (pt) * | 1997-08-08 | 2005-04-29 | Aventis Pharma Gmbh | Derivados substituidos de tetra-hidropirano bem como processo para a sua preparacao |
| SE9904581D0 (sv) * | 1999-12-15 | 1999-12-15 | A & Science Invest Ab | A novel helicobacter pylori-binding substance and use thereof |
| US7481790B2 (en) * | 2000-12-27 | 2009-01-27 | Advanced Cardiovascular Systems, Inc. | Vessel enlargement by arteriogenic factor delivery |
| JP2006502986A (ja) * | 2002-07-03 | 2006-01-26 | グリコミメティクス， インコーポレイテッド | 新脈管形成に関与する医学的状態の診断および治療のための組成物および方法 |
| JP2006515306A (ja) * | 2002-12-20 | 2006-05-25 | グリコミメティクス， インコーポレイテッド | Ｐｓｅｕｄｏｍｏｎａｓ細菌感染の処置のためのオリゴ糖およびその結合体 |
| US20040219158A1 (en) * | 2003-05-02 | 2004-11-04 | Glycomimetics, Inc. | Compositions and methods for diagnosis and therapy of medical conditions involving infection with pseudomonas bacteria |
| WO2005054264A2 (fr) * | 2003-11-19 | 2005-06-16 | Glycomimetics, Inc. | Antagonistes glycomimetiques pour les selectines de type e et p |
| US8201377B2 (en) * | 2004-11-05 | 2012-06-19 | Faus Group, Inc. | Flooring system having multiple alignment points |
| WO2006127906A1 (fr) * | 2005-05-25 | 2006-11-30 | Glycomimetics, Inc. | Composes heterobifonctionnels pour l’inhibition de la selectine |
| CA2618638C (fr) * | 2005-08-09 | 2014-03-11 | Glycomimetics, Inc. | Inhibiteurs glycomimetiques de lectine pa-il ou de lectine pa-iil, ou lectines pa-il et pa-iil provenant de pseudomonas |
| CA2670130A1 (fr) * | 2005-09-02 | 2007-03-08 | Glycomimetics, Inc. | Inhibiteurs de pan-selectine heterobifonctionnels |
| US20090176717A1 (en) * | 2006-06-01 | 2009-07-09 | Glycomimetics, Inc. | Galactosides and thiodigalactosides as inhibitors of pa-il lectin from pseudomonas |
| US7964569B2 (en) | 2006-10-12 | 2011-06-21 | Glycomimetics, Inc. | Glycomimetic replacements for hexoses and N-acetyl hexosamines |
| WO2008100453A1 (fr) * | 2007-02-09 | 2008-08-21 | Glycomimetics, Inc. | Procédés d'utilisation de glycomimétiques avec des remplacements d'hexoses et d'hexosamines d'acétyle n |
| US8039442B2 (en) | 2007-07-18 | 2011-10-18 | Glycomimetics, Inc. | Compounds and methods for treatment of sickle cell disease or complications associated therewith |
| AU2009257536B2 (en) * | 2008-06-13 | 2015-07-02 | Glycomimetics, Inc. | Treatment of cancers of the blood using selected glycomimetic compounds |
| JP5726171B2 (ja) * | 2009-05-01 | 2015-05-27 | グリコミメティックス インコーポレイテッド | Ｅ−セレクチンおよびｃｘｃｒ４ケモカイン受容体のヘテロ二官能性阻害剤 |
| LT2794626T (lt) | 2011-12-22 | 2018-02-12 | Glycomimetics, Inc. | E selektino antagonisto junginiai |
| GB201214736D0 (en) | 2012-08-17 | 2012-10-03 | Isis Innovation | Inflammation imaging and therapy |
| HUE038423T2 (hu) | 2012-12-07 | 2018-10-29 | Glycomimetics Inc | E-szelektin antagonistákat felhasználó vegyületek, készítmények és eljárások vérképzõ sejtek mobilizációjára |
| HUE045542T2 (hu) | 2014-12-03 | 2019-12-30 | Glycomimetics Inc | E-szelektinek és CXCR4 kemokin receptorok heterobifunkcionális inhibitorai |
| JP2019502727A (ja) | 2016-01-22 | 2019-01-31 | グリコミメティクス， インコーポレイテッド | Ｐａ−ｉｌおよび／またはｐａ−ｉｉｌレクチンの糖模倣体阻害剤 |
| 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 |
| JP2019524791A (ja) | 2016-08-08 | 2019-09-05 | グリコミメティクス， インコーポレイテッド | Ｅ−セレクチンの阻害剤もしくはｃｘｃｒ４の阻害剤との、またはｅ−セレクチンおよびｃｘｃｒ４両方のヘテロ二機能性阻害剤とのｔ細胞チェックポイント阻害剤の組み合わせ |
| EP3522931A1 (fr) | 2016-10-07 | 2019-08-14 | GlycoMimetics, Inc. | Antagonistes de e-sélectine multimériques très puissants |
| WO2018169853A1 (fr) | 2017-03-15 | 2018-09-20 | Glycomimetics, Inc. | Dérivés de galactopyranosyle-cyclohexyle utilisés en tant qu'antagonistes d'e-sélectine |
| EP3717013A1 (fr) | 2017-11-30 | 2020-10-07 | GlycoMimetics, Inc. | Méthodes de mobilisation de lymphocytes infiltrant la moelle et leurs utilisations |
| CA3085356A1 (fr) | 2017-12-29 | 2019-07-04 | Glycomimetics, Inc. | Inhibiteurs heterobifonctionnels de e-selectine et de galectine -3 |
| BR112020018184A2 (pt) | 2018-03-05 | 2021-02-02 | Glycomimetics, Inc. | usos de compostos |
| WO2020139962A1 (fr) | 2018-12-27 | 2020-07-02 | Glycomimetics, Inc. | Inhibiteurs hétérobifonctionnels d'e-sélectine et de galectine-3 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4925796A (en) * | 1986-03-07 | 1990-05-15 | Massachusetts Institute Of Technology | Method for enhancing glycoprotein stability |
| SE9301677L (sv) | 1993-05-14 | 1994-11-18 | Kurt G I Nilsson | Syntesmetod |
| PL176272B1 (pl) * | 1993-05-14 | 1999-05-31 | Cytel Corp | Analogi sialilowe Le jako inhibitory adhezji komórkowej |
-
1997
- 1997-01-17 EP EP97901546A patent/EP0886640B1/fr not_active Expired - Lifetime
- 1997-01-17 WO PCT/EP1997/000222 patent/WO1997028173A1/fr active IP Right Grant
- 1997-01-17 AT AT97901546T patent/ATE357452T1/de not_active IP Right Cessation
- 1997-01-17 DE DE69737496T patent/DE69737496D1/de not_active Expired - Lifetime
- 1997-01-17 US US09/117,482 patent/US6169077B1/en not_active Expired - Lifetime
- 1997-01-17 AU AU15423/97A patent/AU1542397A/en not_active Abandoned
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7060685B2 (en) | 2002-05-16 | 2006-06-13 | Glycomimetics, Inc. | Compounds and methods for inhibiting selectin-mediated function |
| US7361644B2 (en) | 2003-11-19 | 2008-04-22 | Glycomimetics, Inc. | Specific antagonist for both E- and P-selectins |
| US9534009B2 (en) | 2008-04-08 | 2017-01-03 | Glycomimetics, Inc. | Pan-selectin inhibitor with enhanced pharmacokinetic activity |
| US8921328B2 (en) | 2010-09-14 | 2014-12-30 | Glycomimetics, Inc. | E-selectin antagonists |
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