CN100384854C - Process for preparing ampicillin sodium - Google Patents
Process for preparing ampicillin sodium Download PDFInfo
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- CN100384854C CN100384854C CNB2004100088076A CN200410008807A CN100384854C CN 100384854 C CN100384854 C CN 100384854C CN B2004100088076 A CNB2004100088076 A CN B2004100088076A CN 200410008807 A CN200410008807 A CN 200410008807A CN 100384854 C CN100384854 C CN 100384854C
- Authority
- CN
- China
- Prior art keywords
- ampicillin
- preparing
- crystallization
- ritalin
- filtrate
- 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.)
- Expired - Lifetime
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- KLOHDWPABZXLGI-YWUHCJSESA-M ampicillin sodium Chemical compound [Na+].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 KLOHDWPABZXLGI-YWUHCJSESA-M 0.000 title claims abstract description 13
- 229960001931 ampicillin sodium Drugs 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title description 5
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin 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=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims abstract description 28
- 238000005406 washing Methods 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 229960003311 ampicillin trihydrate Drugs 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000002425 crystallisation Methods 0.000 claims description 19
- 229960000723 ampicillin Drugs 0.000 claims description 18
- 230000008025 crystallization Effects 0.000 claims description 17
- JUMYIBMBTDDLNG-OJERSXHUSA-N hydron;methyl (2r)-2-phenyl-2-[(2r)-piperidin-2-yl]acetate;chloride Chemical compound Cl.C([C@@H]1[C@H](C(=O)OC)C=2C=CC=CC=2)CCCN1 JUMYIBMBTDDLNG-OJERSXHUSA-N 0.000 claims description 16
- 229940099204 ritalin Drugs 0.000 claims description 16
- 239000000706 filtrate Substances 0.000 claims description 13
- 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 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 claims description 9
- 239000006210 lotion Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 6
- 238000011146 sterile filtration Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 101001031591 Mus musculus Heart- and neural crest derivatives-expressed protein 2 Proteins 0.000 claims description 2
- 238000011045 prefiltration Methods 0.000 claims description 2
- 230000004044 response Effects 0.000 claims description 2
- 230000001954 sterilising effect Effects 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000013078 crystal Substances 0.000 abstract description 2
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 abstract 3
- 229940043279 diisopropylamine Drugs 0.000 abstract 1
- FUGVTYHNTOTQMG-UHFFFAOYSA-M sodium;6-methylheptanoate Chemical compound [Na+].CC(C)CCCCC([O-])=O FUGVTYHNTOTQMG-UHFFFAOYSA-M 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 5
- 238000010189 synthetic method Methods 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005267 amalgamation Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000013068 control sample Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 2
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- QMWWAEFYIXXXQW-UHFFFAOYSA-M potassium;2-[(4-ethoxy-4-oxobut-2-en-2-yl)amino]-2-phenylacetate Chemical compound [K+].CCOC(=O)C=C(C)NC(C([O-])=O)C1=CC=CC=C1 QMWWAEFYIXXXQW-UHFFFAOYSA-M 0.000 description 2
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000012716 precipitator Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention discloses a new method for preparing ampicillin sodium. The method comprises the following steps: dissolving ampicillin trihydrate in anhydrous alcohol; making the solution react with diisopropylamine; purifying the reaction solution; making the reaction solution react with purified sodium isocaprylate; crystallizing the reaction solution in a crystallizing tank; filtering, washing and drying the obtained crystals to obtain a finished product of ampicillin sodium. The ampicillin sodium prepared by the present invention is superior to similar products in quality, and is completely in conformity with the quality requirements of PRC Codex (the 2000 edition).
Description
Technical field
The present invention relates to a kind of synthetic method of Western medicine, relate in particular to a kind of synthetic method of ampicillin.
Background technology
The Ampicillin Trihydrate is the semisynthetic penicillin of Britain BEECHAM company initiative, the synthetic method patent after existing up to now a lot of relevant Ampicillin synthetic methods and the improvement thereof.It is the same with principle in the disquisition of publishing in 1978 to produce the most frequently used method at present on a large scale, and its ultimate principle is as follows: amine was protected in the amino of D-(-) phenylglycocoll formed with the methyl aceto acetate reaction, production Dane salt.Except that desolvating and isolating Dane salt solid; be suspended from acetone or the methylene dichloride; under basic catalyst (as: N-methylmorpholine) effect, react with Vinyl chloroformate or trimethyl-acetyl chloride; form mixed acid anhydride; add 6-amino-penicillanic acid (6-APA) in the dichloromethane solvent of triethyl amine salt; the reaction back generates the protected Ampicillin of N-; add entry and hydrochloric acid under 0 ℃; the pH value is adjusted to 1.5～2.5; amine hydrolysis in making; remove dichloromethane layer, re-adjustment aqueous pH values to 5 (iso-electric point), the Ampicillin Trihydrate of three crystal water can be separated out.
The production method of ampicillin sodium salt has two kinds, and a kind of is that Ampicillin Trihydrate three water acid compounds are suspended from the water, adds sodium hydroxide solution and makes its dissolving, isolates sodium salt by freeze-drying or spray drying process.This method exists the defective of aspects such as product content is low, content of degradation products is high, product easily produces allergy; Another kind method is the precipitator method, is about to be dissolved with the solvent of Sodium isooctanoate such as amine organic solvent that ritalin is added to Ampicillin as in two butanols.It is strong that this method exists used dibutylamine solvent toxic side effect, is unfavorable for the deficiency of aspects such as workman's labour protection.
Summary of the invention
The object of the invention provides a kind of quality product height, the method for preparing ampicillin sodium salt that aftertreatment is simple, safe.
The present invention seeks to realize by following approach:
The preparation method of ampicillin sodium salt comprises the following steps:
1) purifying of Sodium isooctanoate: the Sodium isooctanoate of 16.5～20.5 weight parts is dissolved in the ritalin of 68.9～12.5 weight parts, gained solution is filtered, the place that solution passes through during with the ritalin washing and filtering, merging filtrate and washing lotion place the sterilisable chamber high level tank to preserve standby down in 0～5 ℃ amalgamation liquid;
2) Ampicillin Trihydrate three water acid are dissolved in the dehydrated alcohol, add two Isopropylamines then and react, after reaction is finished, solution is cooled to 0～5 ℃, adds gac, filter, filtrate is placed the sterilisable chamber crystallizer, and this crystallizer places under the high level tank, preserves standby down in 0～7 ℃;
3) crystallization: join step 2) in the crystallizer while the Sodium isooctanoate solution of step 1) sterilisable chamber high level tank stirred, after question response is finished, with reaction solution crystallization in crystallizer, crystallization condition is: temperature-2～2 ℃, stirred under 80～120 rev/mins stirring velocity 60～90 minutes;
4) it is standby ritalin to be placed on the sterilisable chamber high level tank through sterile filtration;
5) crystallisate of gained in the step 3) is filtered, use the ritalin wash crystallization thing 2～3 times in the step 4) again, filtrate and washing lotion reclaim, and the pure crystallisate after the washing is drying to obtain ampicillin sodium salt.
Among the above-mentioned preparation method, wherein the described filter type of step 1) is for to carry out in prefilter and sterilizing filter.Preferred 4 ℃ of the storage temperature of amalgamation liquid in the sterilisable chamber high level tank.
Step 2) the Ampicillin Trihydrate three water acid with 30 weight parts in are dissolved in the dehydrated alcohol of 8.4～57.8 weight parts, and then the two Isopropylamines that add 19～22 weight parts react.After reaction is finished, add gac when preferably it being cooled to 3 ℃ again; Described filter type is that de-carbon filters and sterile filtration; Filtrate and washing lotion place the sterilisable chamber crystallizer to preserve standby down in 2 ℃.
In the crystallisation process of step 3), the crystallization optimum condition is: 0 ℃ of temperature, and stirring velocity: 100 rev/mins, churning time: 80 minutes.
In the step 5) with preferred 2 times of the number of times of ritalin wash crystallization powder.
All raw materials for production all can be bought from market and obtain, and its specification separately is as follows:
Described Ampicillin Trihydrate three water acid outward appearance is white in color or the off-white color crystalline powder, content 〉=96% (pressing anhydride calculates), moisture content: 12%～15%.
Described pair of Isopropylamine outward appearance is achromaticity and clarification liquid, content 〉=99%, moisture≤0.5%.
Described ritalin outward appearance is a colourless transparent liquid, content 〉=95%, moisture≤0.3%.
The content of described dehydrated alcohol 〉=99.7%, moisture＜0.3%.
Embodiment
The preparation of embodiment ampicillin sodium salt
The 18.5kg Sodium isooctanoate is dissolved in the 56.5kg ritalin, gained solution is filtered, the place that solution passes through during with the ritalin washing and filtering, merging filtrate and washing lotion place the sterilisable chamber high level tank to preserve standby down in 4 ℃ amalgamation liquid.The three water acid of 30kg Ampicillin Trihydrate are dissolved in the mixing solutions of the two Isopropylamines of 45.522kg dehydrated alcohol and 21.381kg, treat dissolving fully after, it is cooled to 2 ℃, add gac, at first de-carbon filters, filtrate is collected in sterile filtration again; Washings is collected in the place that reaction solution passes through during with the dehydrated alcohol washing and filtering; Merging filtrate and washings place the sterilisable chamber crystallisation chamber to preserve standby down in 4 ℃ the liquid after merging.
Sodium isooctanoate solution in the sterilisable chamber high level tank is joined in the crystallizer while stirring, beginning crystallization production in crystallizer, crystallization condition is: 0 ℃ of temperature, stirred 80 minutes under 100 rev/mins stirring velocity; It is standby that the 10L ritalin is placed on the sterilisable chamber high level tank through sterile filtration; The crystallization that generates in the crystallizer is filtered, the ritalin wash crystallization powder in the usefulness sterilisable chamber high level tank 2 times, filtrate and washing lotion reclaim, and the crystallisate after the washing is drying to obtain ampicillin sodium salt.
Test the quality simultaneous test of the ampicillin sodium salt of routine the present invention's preparation
1, for test agent: the ampicillin sodium salt that the embodiment of the invention is prepared
2, control sample: ampicillin for inj sodium, lot number: 021123
3, test method and result:
According to the every requirement under 2000 editions ampicillin items of Chinese Pharmacopoeia, trial-product and control sample are carried out complete check.
Every test-results sees Table 1.
The ampicillin of table 1 the present invention preparation and the quality simultaneous test of prior art products
The result: the quality simultaneous test shows that the quality of the ampicillin that the present invention is prepared is better than control sample, meets the specification of quality of Pharmacopoeia of People's Republic of China 2000 editions fully.
Claims (9)
1. the preparation method of an ampicillin may further comprise the steps:
1) purifying of Sodium isooctanoate: the Sodium isooctanoate of 16.5～20.5 weight parts is dissolved in the ritalin of 68.9～12.5 weight parts, above-mentioned solution is filtered, the place that solution passes through during with the ritalin washing and filtering, filtrate and washing lotion are merged, place the sterilisable chamber high level tank to preserve standby down the liquid after merging in 0～5 ℃;
2) Ampicillin Trihydrate three water acid are thrown in the dehydrated alcohol, and then the two Isopropylamines of adding react, after reaction is finished, mixing solutions is cooled to 0～5 ℃, add gac, mixing solutions is filtered, and the place that filtrate is passed through during with the dehydrated alcohol washing and filtering, filtrate and washing lotion are merged, place the sterilisable chamber crystallizer to preserve standby down at 0～7 ℃;
3) crystallization: join step 2) in the crystallizer while the Sodium isooctanoate solution in the step 1) sterilisable chamber high level tank stirred, after question response was finished, with reaction solution crystallization in crystallizer, crystallization condition was: temperature-2～2 ℃, rotating speed: 80～120 rev/mins, churning time: 60～90 minutes;
4) it is standby ritalin to be placed on the sterilisable chamber high level tank through sterile filtration;
5) crystallization of the formation in the step 3) is filtered, the ritalin wash crystallization thing in the usefulness step 4) 2～3 times, filtrate and washing lotion are recyclable, and the pure crystallisate after the washing is drying to obtain ampicillin sodium salt.
2. the method for preparing ampicillin according to claim 1, wherein step 2) in the Ampicillin Trihydrate three water acid of 30 weight parts are dissolved in the dehydrated alcohol of 8.4～57.8 weight parts, and then the two Isopropylamines that add 19～22 weight parts react.
3. the method for preparing ampicillin according to claim 1, wherein the filter type in the step 1) is for to carry out in prefilter and sterilizing filter.
4. the method for preparing ampicillin according to claim 1, the liquid after wherein step 1) will merge place the sterilisable chamber high level tank to preserve standby down in 4 ℃.
5. the method for preparing ampicillin according to claim 1, wherein step 2) in solution to be mixed add activated carbon when being cooled to 3 ℃ again.
6. the method for preparing ampicillin according to claim 1, wherein step 2) in filter type be that de-carbon filters and sterile filtration.
7. the method for preparing ampicillin according to claim 1, wherein step 2) in filtrate and washing lotion after merging be 4 ℃ at the storage temperature of sterilisable chamber crystallizer.
8. the method for preparing ampicillin according to claim 1, wherein the crystallization condition in the step 3) is: 0 ℃ of temperature, stirring velocity: 100 rev/mins, churning time: 80 minutes.
9. the method for preparing ampicillin according to claim 1 is wherein used ritalin wash crystallization thing 2 times in the step 5).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100088076A CN100384854C (en) | 2004-03-12 | 2004-03-12 | Process for preparing ampicillin sodium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100088076A CN100384854C (en) | 2004-03-12 | 2004-03-12 | Process for preparing ampicillin sodium |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1666990A CN1666990A (en) | 2005-09-14 |
| CN100384854C true CN100384854C (en) | 2008-04-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100088076A Expired - Lifetime CN100384854C (en) | 2004-03-12 | 2004-03-12 | Process for preparing ampicillin sodium |
Country Status (1)
| Country | Link |
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| CN (1) | CN100384854C (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102971328A (en) * | 2010-06-16 | 2013-03-13 | 瓦尔德曼化学科技股份有限公司 | Improved process for preparing amoxicillin sodium |
| CN103467493B (en) * | 2013-10-16 | 2016-01-20 | 华北制药集团先泰药业有限公司 | The preparation method of ampicillin anhydrous |
| CN103880863B (en) * | 2014-03-27 | 2015-10-28 | 哈药集团制药总厂 | A kind of preparation method of ampicillin |
| CN104151324B (en) * | 2014-09-03 | 2016-08-24 | 齐鲁天和惠世制药有限公司 | A kind of solvent crystallization prepares the method for ampicillin |
| CN104644629A (en) * | 2015-01-27 | 2015-05-27 | 华北制药股份有限公司 | Ampicillin sodium sulbactam sodium preparation for injection and preparation method thereof |
| CN104945418A (en) * | 2015-05-28 | 2015-09-30 | 浙江长典医药有限公司 | Children ampicillin sodium compound entity and pharmaceutical preparation thereof |
| CN105384755A (en) * | 2015-11-13 | 2016-03-09 | 山东鲁抗医药股份有限公司 | Refining method for improving purity of ampicillin sodium |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3669957A (en) * | 1970-04-24 | 1972-06-13 | American Home Prod | Process for the preparation of sodium ampicillin |
| JPS5077524A (en) * | 1973-11-20 | 1975-06-24 |
-
2004
- 2004-03-12 CN CNB2004100088076A patent/CN100384854C/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3669957A (en) * | 1970-04-24 | 1972-06-13 | American Home Prod | Process for the preparation of sodium ampicillin |
| JPS5077524A (en) * | 1973-11-20 | 1975-06-24 |
Non-Patent Citations (2)
| Title |
|---|
| 氨苄青毒素钠的制备方法. 王太岭.中国药学杂志，第27卷第5期. 1992 |
| 氨苄青毒素钠的制备方法. 王太岭.中国药学杂志，第27卷第5期. 1992 * |
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| Publication number | Publication date |
|---|---|
| CN1666990A (en) | 2005-09-14 |
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Effective date of registration: 20090710 Address after: 24, Jianguo Road, Zhangjiakou, Hebei, Hebei Province, Limited by Share Ltd research and Development Department Patentee after: HEBEI XINZHANG PHARMACEUTICAL Co.,Ltd. Address before: No. 24 Jianguo Road, Hebei, Zhangjiakou Patentee before: Hebei Zhangyao Co.,Ltd. |
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Owner name: CHENGDU BRILLIANT PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: HEBEI XINZHANG PHARMACEUTICAL CO., LTD. Effective date: 20131105 |
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Free format text: CORRECT: ADDRESS; FROM: 075000 ZHANGJIAKOU, HEBEI PROVINCE TO: 610041 CHENGDU, SICHUAN PROVINCE |
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Effective date of registration: 20131105 Address after: 15 No. 610041 Sichuan city in Chengdu Province, Sichuan Province, Chengdu high tech Zone Gaopeng Avenue Patentee after: CHENGDU BRILLIANT PHARMACEUTICAL Co.,Ltd. Address before: 075000 research and development department, Hebei Zhang medicine Limited by Share Ltd, 24 Jianguo Road, Hebei, Zhangjiakou Patentee before: HEBEI XINZHANG PHARMACEUTICAL Co.,Ltd. |
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Address after: 15 No. 610041 Sichuan city in Chengdu Province, Sichuan Province, Chengdu high tech Zone Gaopeng Avenue Patentee after: Chengdu Beite Pharmaceutical Co.,Ltd. Address before: 15 No. 610041 Sichuan city in Chengdu Province, Sichuan Province, Chengdu high tech Zone Gaopeng Avenue Patentee before: CHENGDU BRILLIANT PHARMACEUTICAL Co.,Ltd. |
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Granted publication date: 20080430 |