CN113105455B - 晶型b阿维巴坦钠的制备方法 - Google Patents
晶型b阿维巴坦钠的制备方法 Download PDFInfo
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- CN113105455B CN113105455B CN202010026347.9A CN202010026347A CN113105455B CN 113105455 B CN113105455 B CN 113105455B CN 202010026347 A CN202010026347 A CN 202010026347A CN 113105455 B CN113105455 B CN 113105455B
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- Prior art keywords
- avibactam sodium
- crystal form
- avibactam
- preparation
- temperature
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- 229960001496 avibactam sodium Drugs 0.000 title claims abstract description 136
- RTCIKUMODPANKX-JBUOLDKXSA-M avibactam sodium Chemical compound [Na+].NC(=O)[C@@H]1CC[C@H]2N(OS([O-])(=O)=O)C(=O)N1C2 RTCIKUMODPANKX-JBUOLDKXSA-M 0.000 title claims abstract description 136
- 239000013078 crystal Substances 0.000 title claims abstract description 83
- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 93
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000002904 solvent Substances 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000002425 crystallisation Methods 0.000 claims abstract description 26
- 230000008025 crystallization Effects 0.000 claims abstract description 26
- 238000003756 stirring Methods 0.000 claims abstract description 23
- 238000010438 heat treatment Methods 0.000 claims abstract description 13
- 238000001816 cooling Methods 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 22
- 238000004090 dissolution Methods 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 6
- 239000003599 detergent Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 238000000967 suction filtration Methods 0.000 claims description 4
- 238000002441 X-ray diffraction Methods 0.000 description 17
- 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 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- 229960000484 ceftazidime Drugs 0.000 description 6
- NMVPEQXCMGEDNH-TZVUEUGBSA-N ceftazidime pentahydrate Chemical compound O.O.O.O.O.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 NMVPEQXCMGEDNH-TZVUEUGBSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 108090000204 Dipeptidase 1 Proteins 0.000 description 5
- 229960002379 avibactam Drugs 0.000 description 5
- NDCUAPJVLWFHHB-UHNVWZDZSA-N avibactam Chemical compound C1N2[C@H](C(N)=O)CC[C@@]1([H])N(OS(O)(=O)=O)C2=O NDCUAPJVLWFHHB-UHNVWZDZSA-N 0.000 description 5
- 102000006635 beta-lactamase Human genes 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000000634 powder X-ray diffraction Methods 0.000 description 5
- 238000001291 vacuum drying Methods 0.000 description 5
- 230000003321 amplification Effects 0.000 description 4
- 238000003199 nucleic acid amplification method Methods 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- 239000003781 beta lactamase inhibitor Substances 0.000 description 3
- 229940126813 beta-lactamase inhibitor Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000009776 industrial production Methods 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 3
- LVFGWOQWXQLVRO-XJDKXYGGSA-N (6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;[(2s,5r)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate Chemical compound NC(=O)[C@@H]1CC[C@H]2N(OS(O)(=O)=O)C(=O)N1C2.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)/C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 LVFGWOQWXQLVRO-XJDKXYGGSA-N 0.000 description 2
- 239000005660 Abamectin Substances 0.000 description 2
- 206010037596 Pyelonephritis Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- OJYGBLRPYBAHRT-UHFFFAOYSA-N alphachloralose Chemical compound O1C(C(Cl)(Cl)Cl)OC2C(O)C(C(O)CO)OC21 OJYGBLRPYBAHRT-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003952 β-lactams Chemical group 0.000 description 2
- XQDYOPKCGHWFBY-UHFFFAOYSA-N 1-cyclooctyl-1,3-diazocan-2-one Chemical class O=C1NCCCCCN1C1CCCCCCC1 XQDYOPKCGHWFBY-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical group C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 1
- -1 6-azabicyclo [3.2.1] oct-6-yl Chemical group 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- 206010023424 Kidney infection Diseases 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 229950008167 abamectin Drugs 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 1
- 229940091875 avycaz Drugs 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229940041011 carbapenems Drugs 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 229940125532 enzyme inhibitor Drugs 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 208000027096 gram-negative bacterial infections Diseases 0.000 description 1
- 229960004716 idoxuridine Drugs 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
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CN115677697A (zh) * | 2022-09-19 | 2023-02-03 | 瑞阳制药股份有限公司 | 粒度可调控且流动性好的b晶型阿维巴坦钠析晶方法 |
Citations (9)
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---|---|---|---|---|
CN102834395A (zh) * | 2009-10-09 | 2012-12-19 | 诺维塞尔公司 | 药物化合物的多晶型形式和假多晶型形式 |
CN107325096A (zh) * | 2016-04-29 | 2017-11-07 | 正大天晴药业集团股份有限公司 | 一种阿维巴坦单钠盐的新结晶 |
CN107417686A (zh) * | 2017-09-19 | 2017-12-01 | 北京化工大学 | 一种阿维巴坦钠的合成方法 |
CN107827886A (zh) * | 2017-11-23 | 2018-03-23 | 中山奕安泰医药科技有限公司 | 一种高纯度阿维巴坦的精制制备工艺 |
CN107880042A (zh) * | 2016-09-30 | 2018-04-06 | 上海复星星泰医药科技有限公司 | 阿维巴坦钠及其中间体化合物的制备方法 |
CN107922411A (zh) * | 2015-08-10 | 2018-04-17 | 桑多斯股份公司 | 阿维巴坦钠的晶型c |
CN107936017A (zh) * | 2018-01-12 | 2018-04-20 | 上海龙翔生物医药开发有限公司 | 一种通过结晶制备晶型a或晶型d阿维巴坦产品的方法 |
CN109641901A (zh) * | 2016-08-26 | 2019-04-16 | 桑多斯股份公司 | 阿维巴坦游离酸 |
CN110267956A (zh) * | 2017-02-08 | 2019-09-20 | 桑多斯股份公司 | 用于制备阿维巴坦钠结晶形式c的方法 |
-
2020
- 2020-01-10 CN CN202010026347.9A patent/CN113105455B/zh active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102834395A (zh) * | 2009-10-09 | 2012-12-19 | 诺维塞尔公司 | 药物化合物的多晶型形式和假多晶型形式 |
CN107922411A (zh) * | 2015-08-10 | 2018-04-17 | 桑多斯股份公司 | 阿维巴坦钠的晶型c |
CN107325096A (zh) * | 2016-04-29 | 2017-11-07 | 正大天晴药业集团股份有限公司 | 一种阿维巴坦单钠盐的新结晶 |
CN109641901A (zh) * | 2016-08-26 | 2019-04-16 | 桑多斯股份公司 | 阿维巴坦游离酸 |
CN107880042A (zh) * | 2016-09-30 | 2018-04-06 | 上海复星星泰医药科技有限公司 | 阿维巴坦钠及其中间体化合物的制备方法 |
CN110267956A (zh) * | 2017-02-08 | 2019-09-20 | 桑多斯股份公司 | 用于制备阿维巴坦钠结晶形式c的方法 |
CN107417686A (zh) * | 2017-09-19 | 2017-12-01 | 北京化工大学 | 一种阿维巴坦钠的合成方法 |
CN107827886A (zh) * | 2017-11-23 | 2018-03-23 | 中山奕安泰医药科技有限公司 | 一种高纯度阿维巴坦的精制制备工艺 |
CN107936017A (zh) * | 2018-01-12 | 2018-04-20 | 上海龙翔生物医药开发有限公司 | 一种通过结晶制备晶型a或晶型d阿维巴坦产品的方法 |
Non-Patent Citations (1)
Title |
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赵临襄主编.《化学制药工艺学》.中国医药科技出版社,2015,第104页. * |
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