CN104059086A - 一种阿莫西林晶体及其制备方法 - Google Patents
一种阿莫西林晶体及其制备方法 Download PDFInfo
- Publication number
- CN104059086A CN104059086A CN201410274773.9A CN201410274773A CN104059086A CN 104059086 A CN104059086 A CN 104059086A CN 201410274773 A CN201410274773 A CN 201410274773A CN 104059086 A CN104059086 A CN 104059086A
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- CN
- China
- Prior art keywords
- organic solvent
- amoxycilline trihydrate
- crystal
- preparation
- stirring
- 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.)
- Granted
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 title abstract description 6
- 229960003022 amoxicillin Drugs 0.000 title abstract description 6
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 title abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000706 filtrate Substances 0.000 claims abstract description 8
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 6
- 229910017488 Cu K Inorganic materials 0.000 claims abstract description 4
- 229910017541 Cu-K Inorganic materials 0.000 claims abstract description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000012065 filter cake Substances 0.000 claims abstract description 4
- 150000004684 trihydrates Chemical class 0.000 claims description 43
- 238000005352 clarification Methods 0.000 claims description 6
- 230000008030 elimination Effects 0.000 claims description 6
- 238000003379 elimination reaction Methods 0.000 claims description 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 238000001291 vacuum drying Methods 0.000 claims description 6
- 230000005260 alpha ray Effects 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000003814 drug Substances 0.000 abstract description 9
- 229940079593 drug Drugs 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 3
- 239000000843 powder Substances 0.000 abstract description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 2
- 238000001914 filtration Methods 0.000 abstract 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 210000003445 biliary tract Anatomy 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002485 urinary effect Effects 0.000 description 2
- 241000588832 Bordetella pertussis Species 0.000 description 1
- 241000589562 Brucella Species 0.000 description 1
- 108090000204 Dipeptidase 1 Proteins 0.000 description 1
- 241000588653 Neisseria Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 description 1
- RXDALBZNGVATNY-CWLIKTDRSA-N ampicillin trihydrate Chemical class O.O.O.C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 RXDALBZNGVATNY-CWLIKTDRSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 102000006635 beta-lactamase Human genes 0.000 description 1
- 235000019636 bitter flavor Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002389 essential drug Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
- C07D499/68—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with aromatic rings as additional substituents on the carbon chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/04—Preparation
- C07D499/18—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201410274773.9A CN104059086B (zh) | 2014-06-19 | 2014-06-19 | 一种阿莫西林晶体及其制备方法 |
Applications Claiming Priority (1)
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---|---|---|---|
CN201410274773.9A CN104059086B (zh) | 2014-06-19 | 2014-06-19 | 一种阿莫西林晶体及其制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN104059086A true CN104059086A (zh) | 2014-09-24 |
CN104059086B CN104059086B (zh) | 2016-04-13 |
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CN201410274773.9A Active CN104059086B (zh) | 2014-06-19 | 2014-06-19 | 一种阿莫西林晶体及其制备方法 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105061468A (zh) * | 2015-09-23 | 2015-11-18 | 河北远征药业有限公司 | 一种阿莫西林缓释晶体的制备方法 |
CN109867687A (zh) * | 2017-12-05 | 2019-06-11 | 上海朝瑞化工有限公司 | 一种高水溶性阿莫西林及其制备方法 |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB678508A (en) * | 1948-01-02 | 1952-09-03 | Merck & Co Inc | Preparation of crystalline benzylpenicillinic acid-diisopropyl etherate |
GB1532672A (en) * | 1976-07-20 | 1978-11-15 | Bristol Myers Co | Process for the preparation of amoxicillin trihydrate |
CN1298408A (zh) * | 1998-04-29 | 2001-06-06 | Dsm有限公司 | 结晶β-内酰胺抗生素的方法 |
CN101845053A (zh) * | 2010-03-09 | 2010-09-29 | 河北科技大学 | 一种分离提纯阿莫西林三水化合物的方法 |
CN102260278A (zh) * | 2003-03-21 | 2011-11-30 | 帝斯曼知识产权资产管理有限公司 | 三水羟氨苄青霉素结晶粉末 |
CN102660621A (zh) * | 2012-05-04 | 2012-09-12 | 联邦制药(内蒙古)有限公司 | 一种改进的酶法制备阿莫西林的方法 |
CN102718778A (zh) * | 2012-07-02 | 2012-10-10 | 天津市嘉凡生物科技有限公司 | 阿莫西林a晶型 |
CN102731528A (zh) * | 2012-07-02 | 2012-10-17 | 天津市嘉凡生物科技有限公司 | 阿莫西林c晶型 |
CN103012430A (zh) * | 2013-01-16 | 2013-04-03 | 湖北济生医药有限公司 | 美洛西林钠化合物及其药物组合物 |
CN103145733A (zh) * | 2013-03-20 | 2013-06-12 | 四川省惠达药业有限公司 | 一种阿莫西林化合物及该化合物和克拉维酸钾的药物组合物 |
CN103833774A (zh) * | 2014-03-21 | 2014-06-04 | 山东新时代药业有限公司 | 一种从克拉维酸钾混粉中回收有效成分的方法 |
-
2014
- 2014-06-19 CN CN201410274773.9A patent/CN104059086B/zh active Active
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB678508A (en) * | 1948-01-02 | 1952-09-03 | Merck & Co Inc | Preparation of crystalline benzylpenicillinic acid-diisopropyl etherate |
GB1532672A (en) * | 1976-07-20 | 1978-11-15 | Bristol Myers Co | Process for the preparation of amoxicillin trihydrate |
CN1298408A (zh) * | 1998-04-29 | 2001-06-06 | Dsm有限公司 | 结晶β-内酰胺抗生素的方法 |
CN102260278A (zh) * | 2003-03-21 | 2011-11-30 | 帝斯曼知识产权资产管理有限公司 | 三水羟氨苄青霉素结晶粉末 |
CN101845053A (zh) * | 2010-03-09 | 2010-09-29 | 河北科技大学 | 一种分离提纯阿莫西林三水化合物的方法 |
CN102660621A (zh) * | 2012-05-04 | 2012-09-12 | 联邦制药(内蒙古)有限公司 | 一种改进的酶法制备阿莫西林的方法 |
CN102718778A (zh) * | 2012-07-02 | 2012-10-10 | 天津市嘉凡生物科技有限公司 | 阿莫西林a晶型 |
CN102731528A (zh) * | 2012-07-02 | 2012-10-17 | 天津市嘉凡生物科技有限公司 | 阿莫西林c晶型 |
CN103012430A (zh) * | 2013-01-16 | 2013-04-03 | 湖北济生医药有限公司 | 美洛西林钠化合物及其药物组合物 |
CN103145733A (zh) * | 2013-03-20 | 2013-06-12 | 四川省惠达药业有限公司 | 一种阿莫西林化合物及该化合物和克拉维酸钾的药物组合物 |
CN103833774A (zh) * | 2014-03-21 | 2014-06-04 | 山东新时代药业有限公司 | 一种从克拉维酸钾混粉中回收有效成分的方法 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105061468A (zh) * | 2015-09-23 | 2015-11-18 | 河北远征药业有限公司 | 一种阿莫西林缓释晶体的制备方法 |
CN105061468B (zh) * | 2015-09-23 | 2018-07-06 | 河北远征药业有限公司 | 一种阿莫西林缓释晶体的制备方法 |
CN109867687A (zh) * | 2017-12-05 | 2019-06-11 | 上海朝瑞化工有限公司 | 一种高水溶性阿莫西林及其制备方法 |
CN109867687B (zh) * | 2017-12-05 | 2021-08-17 | 上海朝瑞化工有限公司 | 一种高水溶性阿莫西林及其制备方法 |
Also Published As
Publication number | Publication date |
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CN104059086B (zh) | 2016-04-13 |
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GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Amoxicillin crystal and preparation method thereof Effective date of registration: 20211224 Granted publication date: 20160413 Pledgee: China Construction Bank Corporation Zhengzhou Railway Sub Branch Pledgor: HENAN SOAR VETERINARY PHARMACEUTICAL Co.,Ltd. Registration number: Y2021980016170 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20160413 Pledgee: China Construction Bank Corporation Zhengzhou Railway Sub Branch Pledgor: HENAN SOAR VETERINARY PHARMACEUTICAL Co.,Ltd.|HENAN MUXIANG BIOTECHNOLOGY Co.,Ltd. Registration number: Y2021980016170 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A type of amoxicillin crystal and its preparation method Granted publication date: 20160413 Pledgee: China Construction Bank Corporation Zhengzhou Railway Sub Branch Pledgor: HENAN SOAR VETERINARY PHARMACEUTICAL Co.,Ltd.|HENAN MUXIANG BIOTECHNOLOGY Co.,Ltd. Registration number: Y2024980004821 |