CN100335485C - 注射级无菌头孢曲松钠的一步法制备工艺 - Google Patents
注射级无菌头孢曲松钠的一步法制备工艺 Download PDFInfo
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- CN100335485C CN100335485C CNB2005101182366A CN200510118236A CN100335485C CN 100335485 C CN100335485 C CN 100335485C CN B2005101182366 A CNB2005101182366 A CN B2005101182366A CN 200510118236 A CN200510118236 A CN 200510118236A CN 100335485 C CN100335485 C CN 100335485C
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- CN
- China
- Prior art keywords
- ceftriaxone sodium
- aseptic
- solvent
- preparation process
- sodium
- 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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- 229960000479 ceftriaxone sodium Drugs 0.000 title claims abstract description 41
- FDRNWTJTHBSPMW-GNXCPKRQSA-L disodium;(6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-methyl-6-oxido-5-oxo-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].[Na+].S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)/C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C([O-])=NN1C FDRNWTJTHBSPMW-GNXCPKRQSA-L 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 238000002347 injection Methods 0.000 title claims abstract description 17
- 239000007924 injection Substances 0.000 title claims abstract description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000003756 stirring Methods 0.000 claims abstract description 20
- 238000002425 crystallisation Methods 0.000 claims abstract description 19
- 230000008025 crystallization Effects 0.000 claims abstract description 19
- 239000012046 mixed solvent Substances 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 150000002148 esters Chemical class 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 13
- 239000000243 solution Substances 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000013078 crystal Substances 0.000 claims abstract description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 7
- 150000001412 amines Chemical class 0.000 claims abstract description 7
- 238000005406 washing Methods 0.000 claims abstract description 7
- 239000000843 powder Substances 0.000 claims abstract description 5
- 238000000605 extraction Methods 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 12
- 229960004756 ethanol Drugs 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 11
- 238000005352 clarification Methods 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 6
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 claims description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 5
- 239000001632 sodium acetate Substances 0.000 claims description 5
- 235000017281 sodium acetate Nutrition 0.000 claims description 5
- 229940043279 diisopropylamine Drugs 0.000 claims description 4
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 3
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000000247 postprecipitation Methods 0.000 claims description 2
- 238000011146 sterile filtration Methods 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 abstract description 12
- 238000004519 manufacturing process Methods 0.000 abstract description 11
- 238000001035 drying Methods 0.000 abstract description 7
- 238000001914 filtration Methods 0.000 abstract description 6
- 239000006184 cosolvent Substances 0.000 abstract 2
- 239000005456 alcohol based solvent Substances 0.000 abstract 1
- 230000032798 delamination Effects 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000004278 EU approved seasoning Substances 0.000 description 5
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 235000011194 food seasoning agent Nutrition 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 5
- 229960004249 sodium acetate Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 206010056519 Abdominal infection Diseases 0.000 description 1
- 206010051548 Burn infection Diseases 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 206010018612 Gonorrhoea Diseases 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 206010067268 Post procedural infection Diseases 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- -1 Sodium isooctanoates Chemical class 0.000 description 1
- 206010062255 Soft tissue infection Diseases 0.000 description 1
- 206010048038 Wound infection Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000000013 bile duct Anatomy 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 206010034674 peritonitis Diseases 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 208000013223 septicemia Diseases 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2005101182366A CN100335485C (zh) | 2004-10-27 | 2005-10-21 | 注射级无菌头孢曲松钠的一步法制备工艺 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200410155401.0 | 2004-10-27 | ||
CN 200410155401 CN1634933A (zh) | 2004-10-27 | 2004-10-27 | 头孢曲松钠的制备工艺 |
CNB2005101182366A CN100335485C (zh) | 2004-10-27 | 2005-10-21 | 注射级无菌头孢曲松钠的一步法制备工艺 |
Publications (2)
Publication Number | Publication Date |
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CN1765902A CN1765902A (zh) | 2006-05-03 |
CN100335485C true CN100335485C (zh) | 2007-09-05 |
Family
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Family Applications (1)
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CNB2005101182366A Active CN100335485C (zh) | 2004-10-27 | 2005-10-21 | 注射级无菌头孢曲松钠的一步法制备工艺 |
Country Status (1)
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CN (1) | CN100335485C (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102875574A (zh) * | 2012-08-31 | 2013-01-16 | 石药集团中诺药业(石家庄)有限公司 | 头孢曲松钠晶型及其制备方法 |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011012965A1 (en) * | 2009-07-27 | 2011-02-03 | Nectar Lifesciences Ltd. | Improved process for preparation of ceftriaxone disodium hemiheptahydrate |
CN104031067B (zh) * | 2014-05-21 | 2016-06-01 | 丽珠医药集团股份有限公司 | 一种头孢曲松钠粗品的精制方法 |
CN104876948A (zh) * | 2015-05-28 | 2015-09-02 | 华北制药河北华民药业有限责任公司 | 一种头孢曲松钠的制备方法 |
CN106008554A (zh) * | 2016-05-23 | 2016-10-12 | 河南康达制药有限公司 | 一种头孢曲松钠无菌粉的制备方法及产品 |
CN106366099B (zh) * | 2016-08-22 | 2018-08-31 | 山东罗欣药业集团恒欣药业有限公司 | 一种抗感染药物头孢曲松钠晶体化合物及其制备方法 |
CN110396101B (zh) * | 2018-12-03 | 2021-01-22 | 广东金城金素制药有限公司 | 曲索芬头孢曲松钠药物制剂治疗细菌性内膜炎的新适应症 |
CN112679524B (zh) * | 2020-12-24 | 2022-07-01 | 华北制药河北华民药业有限责任公司 | 一种头孢曲松钠的制备方法 |
-
2005
- 2005-10-21 CN CNB2005101182366A patent/CN100335485C/zh active Active
Non-Patent Citations (1)
Title |
---|
法合成头孢曲松钠 覃宁等,广东药学,第13卷第5期 2003 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102875574A (zh) * | 2012-08-31 | 2013-01-16 | 石药集团中诺药业(石家庄)有限公司 | 头孢曲松钠晶型及其制备方法 |
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Publication number | Publication date |
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CN1765902A (zh) | 2006-05-03 |
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GR01 | Patent grant | ||
C56 | Change in the name or address of the patentee |
Owner name: RUIYANG PHARMACY CO., LTD. Free format text: FORMER NAME OR ADDRESS: SHANGDONG RUIYANG PHARMACEUTICAL CO., LTD. |
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CP03 | Change of name, title or address |
Address after: No. 6 Erlang mountain road, Yiyuan County, Zibo, Shandong Patentee after: Reyoung Pharmaceutical Co., Ltd. Address before: No. 6 Erlang mountain road, Yiyuan County, Zibo, Shandong Patentee before: Shandong Ruiyang Pharmaceutical Co., Ltd. |
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PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: One-step preparation process of aseptic ceftriaxone sodium for injection Effective date of registration: 20161027 Granted publication date: 20070905 Pledgee: Agricultural Bank of China, Limited by Share Ltd, Yiyuan county subbranch Pledgor: Reyoung Pharmaceutical Co., Ltd. Registration number: 2016990000912 |
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CP01 | Change in the name or title of a patent holder |
Address after: 256100 No. 6 Erlang Road, Yiyuan County, Zibo, Shandong Patentee after: Ruiyang Pharmaceutical Co., Ltd Address before: 256100 No. 6 Erlang Road, Yiyuan County, Zibo, Shandong Patentee before: REYOUNG PHARMACEUTICAL Co.,Ltd. |
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PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20201228 Granted publication date: 20070905 Pledgee: Agricultural Bank of China Limited by Share Ltd. Yiyuan county subbranch Pledgor: REYOUNG PHARMACEUTICAL Co.,Ltd. Registration number: 2016990000912 |
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