CN102924434A - 一种右旋雷贝拉唑钠单水合物晶型及其制备方法 - Google Patents
一种右旋雷贝拉唑钠单水合物晶型及其制备方法 Download PDFInfo
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- CN102924434A CN102924434A CN201210398888XA CN201210398888A CN102924434A CN 102924434 A CN102924434 A CN 102924434A CN 201210398888X A CN201210398888X A CN 201210398888XA CN 201210398888 A CN201210398888 A CN 201210398888A CN 102924434 A CN102924434 A CN 102924434A
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- Prior art keywords
- dextral
- monohydrate crystal
- crystal formation
- rabeprazole sodium
- sodium monohydrate
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- 239000013078 crystal Substances 0.000 title claims abstract description 67
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 229960000646 dexrabeprazole Drugs 0.000 title abstract 5
- YREYEVIYCVEVJK-RUZDIDTESA-N dexrabeprazole Chemical compound COCCCOC1=CC=NC(C[S@@](=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-RUZDIDTESA-N 0.000 title abstract 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 9
- 238000010521 absorption reaction Methods 0.000 claims abstract description 5
- 238000004455 differential thermal analysis Methods 0.000 claims abstract description 3
- 230000005855 radiation Effects 0.000 claims abstract description 3
- 238000001228 spectrum Methods 0.000 claims abstract description 3
- 229960001778 rabeprazole sodium Drugs 0.000 claims description 62
- 230000015572 biosynthetic process Effects 0.000 claims description 36
- 239000007787 solid Substances 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 20
- 229960004157 rabeprazole Drugs 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 10
- 239000000706 filtrate Substances 0.000 claims description 10
- 238000001291 vacuum drying Methods 0.000 claims description 10
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 6
- 150000004682 monohydrates Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000000967 suction filtration Methods 0.000 claims description 5
- 239000012065 filter cake Substances 0.000 claims description 4
- 238000002329 infrared spectrum Methods 0.000 claims description 4
- 208000025865 Ulcer Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- 230000036269 ulceration Effects 0.000 claims description 3
- 229910017488 Cu K Inorganic materials 0.000 claims description 2
- 229910017541 Cu-K Inorganic materials 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 abstract description 3
- 238000005755 formation reaction Methods 0.000 description 24
- KRCQSTCYZUOBHN-UHFFFAOYSA-N rabeprazole sodium Chemical compound [Na+].COCCCOC1=CC=NC(CS(=O)C=2[N-]C3=CC=CC=C3N=2)=C1C KRCQSTCYZUOBHN-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229960004756 ethanol Drugs 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000005070 sampling Methods 0.000 description 5
- ZGDLVKWIZHHWIR-UHFFFAOYSA-N 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]morpholine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(N2CCOCC2)N=C1 ZGDLVKWIZHHWIR-UHFFFAOYSA-N 0.000 description 4
- 238000005352 clarification Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 description 3
- 241000590002 Helicobacter pylori Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
- 229940037467 helicobacter pylori Drugs 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
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- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102100021022 Gastrin Human genes 0.000 description 1
- 108010052343 Gastrins Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 201000008629 Zollinger-Ellison syndrome Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 201000000052 gastrinoma Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 229960000381 omeprazole Drugs 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229940126409 proton pump inhibitor Drugs 0.000 description 1
- 239000000612 proton pump inhibitor Substances 0.000 description 1
- 102220305863 rs1015663503 Human genes 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
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Claims (7)
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103113350A (zh) * | 2013-02-27 | 2013-05-22 | 安徽省新星药物开发有限责任公司 | R-雷贝拉唑钠水合物的新晶型及制备方法和应用 |
CN104311540A (zh) * | 2014-10-22 | 2015-01-28 | 湖南明瑞制药有限公司 | 一种右旋雷贝拉唑钠的合成方法 |
CN104693180A (zh) * | 2015-03-02 | 2015-06-10 | 湖南如虹制药有限公司 | 一种雷贝拉唑钠单水合物晶型及其制备方法 |
CN104725358A (zh) * | 2013-12-23 | 2015-06-24 | 江苏神龙药业有限公司 | 一种右旋雷贝拉唑钠水合物的新晶型及其制备方法 |
CN104910135A (zh) * | 2014-03-11 | 2015-09-16 | 南京柯菲平盛辉制药有限公司 | 右旋雷贝拉唑钠新晶型的制备方法 |
CN106632306A (zh) * | 2016-12-26 | 2017-05-10 | 珠海润都制药股份有限公司 | 无定型右旋雷贝拉唑钠及其制备方法 |
WO2018233678A1 (zh) * | 2017-06-23 | 2018-12-27 | 江苏奥赛康药业股份有限公司 | 右旋雷贝拉唑钠化合物及其药物组合物 |
Citations (3)
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CN101250183A (zh) * | 2008-04-03 | 2008-08-27 | 北京润德康医药技术有限公司 | 一种雷贝拉唑的光学异构体及其制备方法、医药用途 |
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2012
- 2012-10-18 CN CN201210398888.XA patent/CN102924434B/zh active Active
Patent Citations (3)
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WO2008152462A1 (en) * | 2007-06-15 | 2008-12-18 | Emcure Pharmaceuticals Limited | A process of sulfoxidation of biologically active compounds |
CN101250183A (zh) * | 2008-04-03 | 2008-08-27 | 北京润德康医药技术有限公司 | 一种雷贝拉唑的光学异构体及其制备方法、医药用途 |
CN101343266A (zh) * | 2008-06-23 | 2009-01-14 | 陕西新安医药科技有限公司 | 光学纯雷贝拉唑的制备方法 |
Non-Patent Citations (2)
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RAJENDRA D. MAHALE ET AL: "Davis Oxaziridine-mediated asymmetric synthesis of proton pump inhibitors using DBU salt of prochiral sulfide", 《ORGANIC PROCESS RESEARCH & DEVELOPMENT》 * |
SHIGEHARU NOCHI ET AL: "Preparation and absolute configurations of optical isomers of sodium 2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]-1H-benzimidazole(E3810)", 《CHEM. PHARM. BULL.》 * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103113350A (zh) * | 2013-02-27 | 2013-05-22 | 安徽省新星药物开发有限责任公司 | R-雷贝拉唑钠水合物的新晶型及制备方法和应用 |
CN104725358A (zh) * | 2013-12-23 | 2015-06-24 | 江苏神龙药业有限公司 | 一种右旋雷贝拉唑钠水合物的新晶型及其制备方法 |
CN104725358B (zh) * | 2013-12-23 | 2018-12-21 | 江苏神龙药业股份有限公司 | 一种右旋雷贝拉唑钠水合物的晶型及其制备方法 |
CN104910135A (zh) * | 2014-03-11 | 2015-09-16 | 南京柯菲平盛辉制药有限公司 | 右旋雷贝拉唑钠新晶型的制备方法 |
CN104311540A (zh) * | 2014-10-22 | 2015-01-28 | 湖南明瑞制药有限公司 | 一种右旋雷贝拉唑钠的合成方法 |
CN104693180A (zh) * | 2015-03-02 | 2015-06-10 | 湖南如虹制药有限公司 | 一种雷贝拉唑钠单水合物晶型及其制备方法 |
CN106632306A (zh) * | 2016-12-26 | 2017-05-10 | 珠海润都制药股份有限公司 | 无定型右旋雷贝拉唑钠及其制备方法 |
CN106632306B (zh) * | 2016-12-26 | 2019-11-15 | 珠海润都制药股份有限公司 | 无定型右旋雷贝拉唑钠及其制备方法 |
WO2018233678A1 (zh) * | 2017-06-23 | 2018-12-27 | 江苏奥赛康药业股份有限公司 | 右旋雷贝拉唑钠化合物及其药物组合物 |
US11078184B2 (en) | 2017-06-23 | 2021-08-03 | Jiangsu Aosaikang Pharmaceutical Co., Ltd. | Dexrabeprazole sodium compound and pharmaceutical composition thereof |
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Address after: 226221 Binjiang Fine Chemical Industrial Park, Nantong, Jiangsu, China, Qidong Patentee after: JIANGSU CHENGXIN PHARMACEUTICAL Co.,Ltd. Address before: 226221 Binjiang Fine Chemical Industrial Park, Nantong, Jiangsu, China, Qidong Patentee before: JIANGSU CHENGXIN PHARMACEUTICAL Co.,Ltd. |
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Commission number: 4W107950 Conclusion of examination: Claims 1-4 and 7 of invention patent 201210398888. X are declared invalid, and the patent shall continue to be valid on the basis of claims 5-6. Decision date of declaring invalidation: 20190301 Decision number of declaring invalidation: 39147 Denomination of invention: Dexrabeprazole sodium monohydrate crystal form and preparation method thereof Granted publication date: 20140618 Patentee: JIANGSU CHENGXIN PHARMACEUTICAL Co.,Ltd. |
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