JP5511390B2 - ヘキソースおよびｎ−アセチルヘキソサミンの置換体を有する糖模倣体の使用方法 - Google Patents
ヘキソースおよびｎ−アセチルヘキソサミンの置換体を有する糖模倣体の使用方法 Download PDFInfo
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- JP5511390B2 JP5511390B2 JP2009549133A JP2009549133A JP5511390B2 JP 5511390 B2 JP5511390 B2 JP 5511390B2 JP 2009549133 A JP2009549133 A JP 2009549133A JP 2009549133 A JP2009549133 A JP 2009549133A JP 5511390 B2 JP5511390 B2 JP 5511390B2
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- Prior art keywords
- alkanyl
- aryl
- alkynyl
- alkenyl
- heteroaryl
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- 238000000034 method Methods 0.000 title description 122
- OVRNDRQMDRJTHS-BKJPEWSUSA-N N-acetyl-D-hexosamine Chemical group CC(=O)NC1C(O)O[C@H](CO)C(O)C1O OVRNDRQMDRJTHS-BKJPEWSUSA-N 0.000 title 1
- 150000002402 hexoses Chemical group 0.000 title 1
- 238000006467 substitution reaction Methods 0.000 title 1
- 125000003342 alkenyl group Chemical group 0.000 claims description 310
- 125000003118 aryl group Chemical group 0.000 claims description 299
- 150000001875 compounds Chemical class 0.000 claims description 274
- 125000001072 heteroaryl group Chemical group 0.000 claims description 267
- 125000004650 C1-C8 alkynyl group Chemical group 0.000 claims description 177
- 229910052739 hydrogen Inorganic materials 0.000 claims description 171
- 229910052799 carbon Inorganic materials 0.000 claims description 158
- 125000000304 alkynyl group Chemical group 0.000 claims description 134
- 150000003839 salts Chemical group 0.000 claims description 97
- 239000000203 mixture Substances 0.000 claims description 94
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- 239000002202 Polyethylene glycol Substances 0.000 claims description 59
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- 229910052731 fluorine Inorganic materials 0.000 claims description 36
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 175
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 35
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- 235000019439 ethyl acetate Nutrition 0.000 description 32
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 31
- 238000004440 column chromatography Methods 0.000 description 30
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 28
- 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 description 27
- 229910052736 halogen Inorganic materials 0.000 description 27
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- -1 and Me Chemical group 0.000 description 26
- 238000003756 stirring Methods 0.000 description 26
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 25
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 24
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- 150000001934 cyclohexanes Chemical class 0.000 description 21
- 241000699670 Mus sp. Species 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 17
- 239000012267 brine Substances 0.000 description 17
- 239000012043 crude product Substances 0.000 description 17
- 150000002772 monosaccharides Chemical class 0.000 description 17
- 229920006395 saturated elastomer Polymers 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
- 238000012360 testing method Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 229910052786 argon Inorganic materials 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 13
- 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 description 13
- 238000010586 diagram Methods 0.000 description 13
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 208000009329 Graft vs Host Disease Diseases 0.000 description 12
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- 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 description 11
- 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 description 11
- SRBFZHDQGSBBOR-OWMBCFKOSA-N L-ribopyranose Chemical compound O[C@H]1COC(O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-OWMBCFKOSA-N 0.000 description 11
- XXFXTBNFFMQVKJ-UHFFFAOYSA-N [diphenyl(trityloxy)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XXFXTBNFFMQVKJ-UHFFFAOYSA-N 0.000 description 11
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- A61K31/7032—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a polyol, i.e. compounds having two or more free or esterified hydroxy groups, including the hydroxy group involved in the glycosidic linkage, e.g. monoglucosyldiacylglycerides, lactobionic acid, gangliosides
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90039807P | 2007-02-09 | 2007-02-09 | |
| US60/900,398 | 2007-02-09 | ||
| US93277907P | 2007-05-31 | 2007-05-31 | |
| US60/932,779 | 2007-05-31 | ||
| PCT/US2008/001762 WO2008100453A1 (en) | 2007-02-09 | 2008-02-07 | Methods of use of glycomimetics with replacements for hexoses and n-acetyl hexosamines |
Publications (3)
| Publication Number | Publication Date |
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| JP2010518094A JP2010518094A (ja) | 2010-05-27 |
| JP2010518094A5 JP2010518094A5 (enExample) | 2012-03-15 |
| JP5511390B2 true JP5511390B2 (ja) | 2014-06-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2009549133A Active JP5511390B2 (ja) | 2007-02-09 | 2008-02-07 | ヘキソースおよびｎ−アセチルヘキソサミンの置換体を有する糖模倣体の使用方法 |
Country Status (7)
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| CA (1) | CA2677747A1 (enExample) |
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| WO (1) | WO2008100453A1 (enExample) |
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| CN102076865B (zh) | 2008-05-02 | 2016-03-16 | 西雅图基因公司 | 用于制造核心岩藻糖基化降低的抗体和抗体衍生物的方法和组合物 |
| WO2009152245A1 (en) * | 2008-06-13 | 2009-12-17 | Glycomimetics, Inc. | Treatment of cancers of the blood using selected glycomimetic compounds |
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| 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 |
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| US11712446B2 (en) | 2017-11-30 | 2023-08-01 | Glycomimetics, Inc. | Methods of mobilizing marrow infiltrating lymphocytes and uses thereof |
| BR112020013198A2 (pt) | 2017-12-29 | 2020-12-01 | Glycomimetics, Inc. | inibidores heterobifuncionais de e-selectina e galectina-3 |
| KR20200128025A (ko) | 2018-03-05 | 2020-11-11 | 글리코미메틱스, 인크. | 급성 골수성 백혈병 및 관련 병태의 치료 방법 |
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2008
- 2008-02-07 WO PCT/US2008/001762 patent/WO2008100453A1/en not_active Ceased
- 2008-02-07 AU AU2008216794A patent/AU2008216794A1/en not_active Abandoned
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- 2008-02-07 US US12/069,436 patent/US8026222B2/en active Active
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2011
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| EP2457573A1 (en) | 2012-05-30 |
| US20120202762A1 (en) | 2012-08-09 |
| US8026222B2 (en) | 2011-09-27 |
| AU2008216794A1 (en) | 2008-08-21 |
| NZ598863A (en) | 2013-11-29 |
| US20080200406A1 (en) | 2008-08-21 |
| EP2117561A1 (en) | 2009-11-18 |
| WO2008100453A1 (en) | 2008-08-21 |
| CA2677747A1 (en) | 2008-08-21 |
| JP2010518094A (ja) | 2010-05-27 |
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