JP2010506832A5 - - Google Patents
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- JP2010506832A5 JP2010506832A5 JP2009532370A JP2009532370A JP2010506832A5 JP 2010506832 A5 JP2010506832 A5 JP 2010506832A5 JP 2009532370 A JP2009532370 A JP 2009532370A JP 2009532370 A JP2009532370 A JP 2009532370A JP 2010506832 A5 JP2010506832 A5 JP 2010506832A5
- Authority
- JP
- Japan
- Prior art keywords
- alkanyl
- aryl
- alkynyl
- alkenyl
- heteroaryl
- 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.)
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- 125000003118 aryl group Chemical group 0.000 claims description 72
- 125000003342 alkenyl group Chemical group 0.000 claims description 70
- 125000004650 C1-C8 alkynyl group Chemical group 0.000 claims description 67
- 125000001072 heteroaryl group Chemical group 0.000 claims description 65
- 150000001875 compounds Chemical class 0.000 claims description 55
- 229910052799 carbon Inorganic materials 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 33
- 150000004820 halides Chemical class 0.000 claims description 27
- -1 OMe Halide Chemical class 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical class CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 claims description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 4
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 3
- 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 claims description 3
- 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 claims description 3
- WQZGKKKJIJFFOK-DHVFOXMCSA-N L-galactose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-DHVFOXMCSA-N 0.000 claims description 3
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims description 3
- SRBFZHDQGSBBOR-OWMBCFKOSA-N L-ribopyranose Chemical compound O[C@H]1COC(O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-OWMBCFKOSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 3
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims description 2
- OVRNDRQMDRJTHS-KEWYIRBNSA-N N-acetyl-D-galactosamine Chemical class CC(=O)N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-KEWYIRBNSA-N 0.000 claims description 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 claims description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 2
- 150000001336 alkenes Chemical group 0.000 claims description 2
- 150000001345 alkine derivatives Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 229930182830 galactose Natural products 0.000 claims description 2
- 150000002256 galaktoses Chemical class 0.000 claims description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 102000015689 E-Selectin Human genes 0.000 claims 1
- 108010024212 E-Selectin Proteins 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 34
- 229920001542 oligosaccharide Polymers 0.000 description 13
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 12
- 150000001934 cyclohexanes Chemical class 0.000 description 11
- 150000002482 oligosaccharides Chemical class 0.000 description 11
- 238000000034 method Methods 0.000 description 6
- 0 COC(*)(CN)O* Chemical compound COC(*)(CN)O* 0.000 description 4
- MSWZFWKMSRAUBD-UHFFFAOYSA-N 2-Amino-2-Deoxy-Hexose Chemical compound NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N c1cc2cccnc2cc1 Chemical compound c1cc2cccnc2cc1 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 150000002402 hexoses Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- POTIYWUALSJREP-UHFFFAOYSA-N C(CC1)CC2C1NCCC2 Chemical compound C(CC1)CC2C1NCCC2 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N C1CCNCC1 Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- CWYAKYNWAFWQET-LCYDCBTBSA-N CC(CC(C)C1OC(C(C2[NH+]3[O-])O)OC(C)C2C3O)CC1OC(C1OC(c2ccccc2)=O)OC2C=[O]C2C1O[C@@H](CC1CCCCC1)C(NO)=O Chemical compound CC(CC(C)C1OC(C(C2[NH+]3[O-])O)OC(C)C2C3O)CC1OC(C1OC(c2ccccc2)=O)OC2C=[O]C2C1O[C@@H](CC1CCCCC1)C(NO)=O CWYAKYNWAFWQET-LCYDCBTBSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N c1c[o]c2c1cccc2 Chemical compound c1c[o]c2c1cccc2 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 150000002243 furanoses Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001483 monosaccharide substituent group Chemical group 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003214 pyranose derivatives Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85146706P | 2006-10-12 | 2006-10-12 | |
| US60/851,467 | 2006-10-12 | ||
| PCT/US2007/021541 WO2008060378A2 (en) | 2006-10-12 | 2007-10-09 | Glycomimetic replacements for hexoses and n-acetyl hexosamines |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013126449A Division JP2013189471A (ja) | 2006-10-12 | 2013-06-17 | ヘキソースおよびｎ−アセチルヘキソサミンの糖模倣体置換 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010506832A JP2010506832A (ja) | 2010-03-04 |
| JP2010506832A5 true JP2010506832A5 (cg-RX-API-DMAC7.html) | 2010-04-22 |
| JP5298020B2 JP5298020B2 (ja) | 2013-09-25 |
Family
ID=39402172
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009532370A Active JP5298020B2 (ja) | 2006-10-12 | 2007-10-09 | ヘキソースおよびｎ−アセチルヘキソサミンの糖模倣体置換 |
| JP2013126449A Withdrawn JP2013189471A (ja) | 2006-10-12 | 2013-06-17 | ヘキソースおよびｎ−アセチルヘキソサミンの糖模倣体置換 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013126449A Withdrawn JP2013189471A (ja) | 2006-10-12 | 2013-06-17 | ヘキソースおよびｎ−アセチルヘキソサミンの糖模倣体置換 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US7964569B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2074132B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP5298020B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2666103C (cg-RX-API-DMAC7.html) |
| WO (1) | WO2008060378A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (20)
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| US9486497B2 (en) | 2007-12-10 | 2016-11-08 | The University Of Queensland | Treatment of immunocompromised conditions |
| US8410066B2 (en) | 2009-05-01 | 2013-04-02 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectins and CXCR4 chemokine receptors |
| WO2011040574A1 (ja) * | 2009-09-30 | 2011-04-07 | 国立大学法人京都大学 | アゼチジニルメトキシピリジン誘導体の製造方法及びその使用 |
| WO2012037034A1 (en) * | 2010-09-14 | 2012-03-22 | Glycomimetics, Inc. | E-selectin antagonists |
| WO2012061662A1 (en) | 2010-11-03 | 2012-05-10 | Glycomimetics, Inc. | Glycomimetic-peptidomimetic inhibitors of e-selectins and cxcr4 chemokine receptors |
| WO2013096926A1 (en) | 2011-12-22 | 2013-06-27 | Glycomimetics, Inc. | E-selectin antagonist compounds, compositions, and methods of use |
| ES2668045T3 (es) | 2012-12-07 | 2018-05-16 | Glycomimetics, Inc. | Compuestos, composiciones y métodos que usan antagonistas de la E-selectina para la movilización de las células hematopoyéticas |
| WO2014149837A1 (en) * | 2013-03-15 | 2014-09-25 | Glycomimetics, Inc. | Compounds and methods to enhance the oral availability of glycomimetics |
| US20160333043A1 (en) * | 2014-01-17 | 2016-11-17 | Glycomimetics, Inc. | E-Selectin Antagonists Modified By Macrocycle Formation to the Galactose |
| US10519181B2 (en) | 2014-12-03 | 2019-12-31 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectins and CXCR4 chemokine receptors |
| EP3405473A1 (en) * | 2016-01-22 | 2018-11-28 | 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 |
| EP3522931A1 (en) * | 2016-10-07 | 2019-08-14 | GlycoMimetics, Inc. | Highly potent multimeric e-selectin antagonists |
| JP7272956B2 (ja) * | 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 | Ｅ－セレクチンアンタゴニストとしてのガラクトピラノシル－シクロヘキシル誘導体 |
| EP3717013A1 (en) | 2017-11-30 | 2020-10-07 | GlycoMimetics, Inc. | Methods of mobilizing marrow infiltrating lymphocytes and uses thereof |
| CA3085356A1 (en) | 2017-12-29 | 2019-07-04 | Glycomimetics, Inc. | Heterobifunctional inhibitors of e-selectin and galectin-3 |
| AU2019230013A1 (en) | 2018-03-05 | 2020-09-10 | Glycomimetics, Inc. | Methods for treating acute myeloid leukemia and related conditions |
| WO2020139962A1 (en) | 2018-12-27 | 2020-07-02 | Glycomimetics, Inc. | Heterobifunctional inhibitors of e-selectin and galectin-3 |
| AU2020263266A1 (en) | 2019-04-24 | 2021-12-16 | Glycomimetics, Inc. | Galactose-linked multimeric glycomimetic inhibitors of E-selectins, galectin-3, and/or CXCR4 chemokine receptors |
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-
2007
- 2007-10-09 JP JP2009532370A patent/JP5298020B2/ja active Active
- 2007-10-09 CA CA2666103A patent/CA2666103C/en active Active
- 2007-10-09 US US11/973,891 patent/US7964569B2/en active Active
- 2007-10-09 EP EP07867214.4A patent/EP2074132B1/en active Active
- 2007-10-09 WO PCT/US2007/021541 patent/WO2008060378A2/en not_active Ceased
-
2011
- 2011-04-25 US US13/093,611 patent/US20110257380A1/en not_active Abandoned
-
2013
- 2013-06-17 JP JP2013126449A patent/JP2013189471A/ja not_active Withdrawn
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