CN102942601A - 一种磺达肝癸钠的中间体的制备方法 - Google Patents
一种磺达肝癸钠的中间体的制备方法 Download PDFInfo
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- CN102942601A CN102942601A CN2012105021096A CN201210502109A CN102942601A CN 102942601 A CN102942601 A CN 102942601A CN 2012105021096 A CN2012105021096 A CN 2012105021096A CN 201210502109 A CN201210502109 A CN 201210502109A CN 102942601 A CN102942601 A CN 102942601A
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- XEKSTYNIJLDDAZ-JASSWCPGSA-F fondaparinux sodium Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].O[C@@H]1[C@@H](NS([O-])(=O)=O)[C@@H](OC)O[C@H](COS([O-])(=O)=O)[C@H]1O[C@H]1[C@H](OS([O-])(=O)=O)[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](OS([O-])(=O)=O)[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O[C@@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](COS([O-])(=O)=O)O4)NS([O-])(=O)=O)[C@H](O3)C(O)=O)O)[C@@H](COS([O-])(=O)=O)O2)NS([O-])(=O)=O)[C@H](C(O)=O)O1 XEKSTYNIJLDDAZ-JASSWCPGSA-F 0.000 title claims abstract description 25
- 229960003661 fondaparinux sodium Drugs 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 83
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 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 claims abstract description 5
- 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 abstract description 5
- 229950006780 n-acetylglucosamine Drugs 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 66
- 239000000243 solution Substances 0.000 claims description 41
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 230000035484 reaction time Effects 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 8
- 230000007935 neutral effect Effects 0.000 claims description 8
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 239000012044 organic layer Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 7
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 6
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 6
- 229940073608 benzyl chloride Drugs 0.000 claims description 6
- HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000010410 layer Substances 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 3
- 239000003444 phase transfer catalyst Substances 0.000 claims description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- 239000003637 basic solution Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 238000004821 distillation Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 239000004019 antithrombin Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 6
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical class OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 3
- 235000010262 sodium metabisulphite Nutrition 0.000 description 3
- -1 Acetonitrile Benzaldehyde dimethyl acetal Chemical compound 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 229940001584 sodium metabisulfite Drugs 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000003582 thrombocytopenic effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 0 *CC1=CCCC*1 Chemical compound *CC1=CCCC*1 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 230000010100 anticoagulation Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
反应温度 | 反应时间 | 收率 | |
1 | 50℃ | 10h | 71% |
2 | 60℃ | 40h | 80% |
3 | 70℃ | 70h | 78% |
化合物D1 | 乙腈 | 苯甲醛二甲缩醛 | 对甲苯磺酸 | 反应温度 | 反应时间 | 收率 | |
1 | 16g | 240ml | 24ml | 5.7g | 80℃ | 4h | 85% |
2 | 16g | 240ml | 24ml | 28.5g | 100℃ | 6h | 91% |
3 | 16g | 240ml | 24ml | 57g | 120℃ | 7h | 88% |
反应温度 | 反应时间 | 收率 | |
1 | 60℃ | 20h | 59% |
2 | 70℃ | 45h | 70% |
3 | 80℃ | 70h | 63% |
化合物D3 | 三氟甲磺酸酐 | 反应温度 | 反应时间 | 收率 | |
1 | 9.5g | 19.1g | 0℃ | 6h | 81% |
2 | 9.5g | 23.2g | 15℃ | 18h | 90% |
3 | 9.5g | 76.4g | 30℃ | 30h | 92% |
化合物D4 | 苄基氯 | 甲苯 | N-甲基吡咯烷酮 | 反应温度 | 反应时间 | 收率 | |
1 | 20g | 4.1g | 180ml | 20ml | 0℃ | 5h | 90% |
2 | 20g | 9.9g | 180ml | 20ml | 25℃ | 8h | 97% |
3 | 20g | 24.7g | 180ml | 20ml | 50℃ | 10h | 98% |
化合物D5 | 樟脑磺酸 | 反应温度 | 反应时间 | |
1 | 24.5g | 0.8g | 10℃ | 16h |
2 | 24.5g | 1.6g | 50℃ | 38h |
3 | 24.5g | 3.2g | 80℃ | 60h |
化合物D6 | 苯甲酰氯 | 反应温度 | 反应时间 | 收率 | |
1 | 31g | 7g | 10℃ | 16h | 83% |
2 | 31g | 14g | 50℃ | 38h | 92% |
3 | 31g | 28g | 80℃ | 60h | 94% |
Claims (10)
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103588825A (zh) * | 2013-11-14 | 2014-02-19 | 大连九信生物化工科技有限公司 | 一种苯甲醛二甲缩醛保护d-氨基葡萄糖衍生物的方法 |
CN103601765A (zh) * | 2013-09-02 | 2014-02-26 | 上海艾康睿医药科技有限公司 | 磺达肝癸钠及其中间体、以及制备方法 |
CN105622678A (zh) * | 2014-11-05 | 2016-06-01 | 海门慧聚药业有限公司 | 新工艺制备磺达肝癸钠中间体的双糖片段 |
CN106588644A (zh) * | 2016-11-16 | 2017-04-26 | 杭州师范大学 | 一种羧酸酯类化合物的合成方法 |
CN109111491A (zh) * | 2018-10-29 | 2019-01-01 | 雅本化学股份有限公司 | 一种磺达肝癸钠的制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1558911A (zh) * | 2001-09-07 | 2004-12-29 | 合成肝素五糖 | |
WO2011014793A2 (en) * | 2009-07-31 | 2011-02-03 | Reliable Biopharmaceutical Corporation | Process for preparing fondaparinux sodium and intermediates useful in the synthesis thereof |
CN102775450A (zh) * | 2012-07-03 | 2012-11-14 | 华东师范大学 | 一种1,6-脱水-2-叠氮-2-脱氧-β-D-吡喃葡萄糖的制备方法 |
-
2012
- 2012-11-30 CN CN201210502109.6A patent/CN102942601B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1558911A (zh) * | 2001-09-07 | 2004-12-29 | 合成肝素五糖 | |
WO2011014793A2 (en) * | 2009-07-31 | 2011-02-03 | Reliable Biopharmaceutical Corporation | Process for preparing fondaparinux sodium and intermediates useful in the synthesis thereof |
CN102775450A (zh) * | 2012-07-03 | 2012-11-14 | 华东师范大学 | 一种1,6-脱水-2-叠氮-2-脱氧-β-D-吡喃葡萄糖的制备方法 |
Non-Patent Citations (1)
Title |
---|
NAVNEET GOYAL,等: "Synthesis and characterization of D-glucosamine-derived low molecular weight gelators", 《TETRAHEDRON》 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103601765A (zh) * | 2013-09-02 | 2014-02-26 | 上海艾康睿医药科技有限公司 | 磺达肝癸钠及其中间体、以及制备方法 |
CN103601765B (zh) * | 2013-09-02 | 2017-01-04 | 上海艾康睿医药科技有限公司 | 磺达肝癸钠及其中间体、以及制备方法 |
CN103588825A (zh) * | 2013-11-14 | 2014-02-19 | 大连九信生物化工科技有限公司 | 一种苯甲醛二甲缩醛保护d-氨基葡萄糖衍生物的方法 |
CN103588825B (zh) * | 2013-11-14 | 2016-06-22 | 大连九信生物化工科技有限公司 | 一种苯甲醛二甲缩醛保护d-氨基葡萄糖衍生物的方法 |
CN105622678A (zh) * | 2014-11-05 | 2016-06-01 | 海门慧聚药业有限公司 | 新工艺制备磺达肝癸钠中间体的双糖片段 |
CN106588644A (zh) * | 2016-11-16 | 2017-04-26 | 杭州师范大学 | 一种羧酸酯类化合物的合成方法 |
CN106588644B (zh) * | 2016-11-16 | 2019-03-29 | 杭州师范大学 | 一种羧酸酯类化合物的合成方法 |
CN109111491A (zh) * | 2018-10-29 | 2019-01-01 | 雅本化学股份有限公司 | 一种磺达肝癸钠的制备方法 |
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Address after: 210008, E, 18 floor, international finance center, 1 Hankou Road, Gulou District, Jiangsu, Nanjing Applicant after: Cai Jin Applicant after: Chen Xuejun Address before: 210037, Hubin garden, No. 399, Middle Road, Gulou District, Jiangsu, Nanjing, 1-2-502 Applicant before: Cai Jin Applicant before: Chen Xuejun |
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Inventor after: Cai Jin Inventor after: Chen Xuejun Inventor after: Zhang Qiu Inventor before: Cai Jin Inventor before: Chen Xuejun |
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Free format text: CORRECT: ADDRESS; FROM: 210008 NANJING, JIANGSU PROVINCE TO: 225300 TAIZHOU, JIANGSU PROVINCE |
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Effective date of registration: 20130423 Address after: 225300 G15 building, China Pharmaceutical City, 1 drug city road, Jiangsu, Taizhou Applicant after: Curegen (Jiangsu) Pharmaceuticals Inc. Address before: 210008, E, 18 floor, international finance center, 1 Hankou Road, Gulou District, Jiangsu, Nanjing Applicant before: Cai Jin Applicant before: Chen Xuejun |
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