CN104193767A - Cefamandole nafate superfine powder preparation and preparation method thereof - Google Patents
Cefamandole nafate superfine powder preparation and preparation method thereof Download PDFInfo
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- CN104193767A CN104193767A CN201410385066.7A CN201410385066A CN104193767A CN 104193767 A CN104193767 A CN 104193767A CN 201410385066 A CN201410385066 A CN 201410385066A CN 104193767 A CN104193767 A CN 104193767A
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- sodium
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- superfine powder
- compound
- formylcefamole
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- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 239000000843 powder Substances 0.000 title claims abstract description 23
- 229960002440 cefamandole nafate Drugs 0.000 title abstract 3
- RRJHESVQVSRQEX-SUYBPPKGSA-N O-formylcefamandole Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](OC=O)C=3C=CC=CC=3)[C@H]2SC1 RRJHESVQVSRQEX-SUYBPPKGSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 7
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 claims abstract description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 235000019253 formic acid Nutrition 0.000 claims abstract description 4
- 239000002245 particle Substances 0.000 claims abstract description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 4
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 4
- 159000000000 sodium salts Chemical class 0.000 claims abstract description 4
- 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 27
- 239000011734 sodium Substances 0.000 claims description 27
- 229910052708 sodium Inorganic materials 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- ICZOIXFFVKYXOM-YCLOEFEOSA-M cefamandole nafate Chemical compound [Na+].CN1N=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)[C@H](OC=O)C=3C=CC=CC=3)[C@H]2SC1 ICZOIXFFVKYXOM-YCLOEFEOSA-M 0.000 claims description 9
- AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000012046 mixed solvent Substances 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical group Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 3
- 238000012856 packing Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000010923 batch production Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- XUTQHTOXGKVJPN-XCGJVMPOSA-N (6r)-7-amino-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)C(N)[C@H]2SC1 XUTQHTOXGKVJPN-XCGJVMPOSA-N 0.000 abstract 1
- -1 compound cefamandole nafate Chemical class 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000000227 grinding Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229930186147 Cephalosporin Natural products 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 150000001780 cephalosporins Chemical class 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N Amide-Phenylacetic acid Natural products NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000003445 biliary tract Anatomy 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical group CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 206010034674 peritonitis Diseases 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 208000013223 septicemia Diseases 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 210000002229 urogenital system Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
The invention discloses a method for preparing a cefamandole nafate superfine powder preparation. The method comprises the following steps: (1) reacting benzoyl acetic acid with thionyl chloride, and removing the thionyl chloride after the reaction is ended; (2) dissolving the obtained product in dichloromethane, adding 7-amino-3-[(1-methyl-1H-tetrazole-5-yl) thiomethyl]-3-cephem-4-carboxylic acid into the above solution, thereby obtaining a compound (I) after the reaction; (3) dissolving the compound (I) into tetrahydrofuran, adding sodium borohydride into the above solution, thereby obtaining a compound (II) after the reaction; (4) reacting the compound (II) with formic acid, thereby obtaining a compound cefamandole nafate; (5) preparing a sodium salt; and (6) drying, and grinding the sodium salt into superfine powder by using airflow, wherein the particle diameter of the superfine powder is 0.5-3 microns. According to the method, the structure is simple, the raw materials are cheap, and batch production is promoted.
Description
Technical field
The present invention relates to a kind of preparation method of Sodium O-formylcefamole superfine powder preparation.
Background technology
Sodium O-formylcefamole belongs to second generation cephalosporin class microbiotic, this product is the second generation cephalosporin class microbiotic of being succeeded in developing by U.S. Lilly company at first, the site infections such as respiratory tract, genito-urinary system, skin and soft tissue, bone and the joint of clinical application due to the responsive gram-negative bacteria, pharynx otorhinolaryngology and peritonitis, septicemia etc.Biliary tract and intestinal tract infections are had to good therapeutic effect.
Sodium O-formylcefamole was applied to clinical in 1978, commodity are called Mandol, chemistry 7-D-(2-methanoyl phenylacetamide)-3-[(1-methyl isophthalic acid H-tetrazolium-5 base by name) thiomethyl]-3-cephem-4-carboxylic acid sodium salt, molecular weight is 512.50, its structural formula is suc as formula shown in I:
Formula 1
The synthetic method of Sodium O-formylcefamole of the prior art all can effectively be prepared Sodium O-formylcefamole, but the purity of target product is not high, colour-difference, and content is low.The reasons such as while method complicated operation, post-processed are loaded down with trivial details are being subject to larger restriction in large production.
Summary of the invention
Due to the above-mentioned shortcoming of prior art, the present invention proposes a kind of Sodium O-formylcefamole superfine powder preparation and preparation method thereof, and it can effectively solve the above-mentioned shortcoming of prior art.
The present invention is by the following technical solutions:
A kind of preparation method of Sodium O-formylcefamole superfine powder preparation:
(1), benzoyl acetic acid is reacted with thionyl chloride, reaction after finishing is removed thionyl chloride;
(2), the product obtaining in step (1) is dissolved in methylene dichloride, and then add wherein 7-amino-3-[(1-methyl isophthalic acid H-tetrazolium-5-yl) thiomethyl]-3-cephem-4-carboxylic acid, after reaction, obtain compound (I), compound (I) structure is as follows:
；
(3), compound (I) is dissolved in tetrahydrofuran (THF), then, wherein to entering sodium borohydride, obtain compound (II) after reaction, the structure of compound (II) is as follows:
；
(4), compound (II) is reacted with formic acid esterification and obtains compound Mandokef;
(5), Mandokef is made to sodium salt;
(6), with comminution by gas stream, become superfine powder after Sodium O-formylcefamole is dry, reclaim, packing, the particle diameter of superfine powder is 0.5 ~ 3 μ m.
In step (1), the condition of reaction is stirring at room.
Comminution by gas stream in described step (6) adopts multi-stage crushing method, and gas velocity is 350 ~ 450m/s.
In described step (2), the condition of reaction is stirring at room, and the product obtaining in step (1) and 7-amino-3-[(1-methyl isophthalic acid H-tetrazolium-5-yl) thiomethyl] mol ratio of-3-cephem-4-carboxylic acid is 1:1.5.
The product obtaining in step (2), by the mixed solvent recrystallization of ethanol and methylene dichloride, is obtained to the monocrystalline of compound (I).
In step (4), esterification solvent used is ethyl acetate, and catalyzer is 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride.
The ethanol that the product obtaining in described step (2) is 10:11 by volume ratio and the mixed solvent recrystallization of methylene dichloride.
A kind of preparation that contains Sodium O-formylcefamole superfine powder prepared by above-mentioned preparation method.
The present invention has the following advantages: present method is simple in structure, and raw material is cheap, is beneficial to batch production.
embodiment:
Below in conjunction with embodiment, describe the present invention in detail.Should be understood that these embodiments are only not used in and limit the scope of the invention for the present invention is described.In addition should be understood that those skilled in the art can make various changes or modifications the present invention after having read the content of the present invention's instruction, these equivalent form of values fall within the application's appended claims limited range equally.
Embodiment 1:
The benzoyl acetic acid of 1mol is dissolved in the thionyl chloride of 5 mL, stirring at room reaction, after reaction finishes removes thionyl chloride evaporation; The product obtaining is dissolved in methylene dichloride, and then adds wherein 7-amino-3-[(1-methyl isophthalic acid H-tetrazolium-5-yl of 1.5mol) thiomethyl]-3-cephem-4-carboxylic acid, after reaction, obtain compound (I); Compound (I) is dissolved in tetrahydrofuran (THF), then under condition of ice bath wherein to entering sodium borohydride, after reaction, obtain compound (II), in the mixed solvent that is 10:11 in ethanol and methylene chloride volume ratio by compound (II) heating for dissolving, the crystal of cooling precipitation compounds (II); Compound (II) is dissolved in ethyl acetate, then add wherein 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride of catalytic amount and the formic acid of 1.5mol, reflux 12h, reaction obtains compound Mandokef, and the product that reaction is obtained is purified and obtained the Mandokef of sterling by column chromatography; Then Mandokef is dissolved in the ethanol and acetone of 5 mL 1:1, then add wherein sodium acetate, stirring at room reaction is to there being crystallization, filtering product, and with ethanol and the washing with acetone filter cake of 1:1, product vacuum-drying under 40 degree, obtains Sodium O-formylcefamole 315g, the Sodium O-formylcefamole obtaining is adopted to multi-stage crushing method by comminution by gas stream, and gas velocity is that 350 ~ 450m/s prepares the superfine powder that particle diameter is 0.5 ~ 3 μ m.
Embodiment 2
By the sample preparing in embodiment 1, add water and make the solution that contains Sodium O-formylcefamole 20 μ g in every 1mL, according to spectrophotometry (Chinese Pharmacopoeia 2005 version two), measure, result has maximum absorption at the wavelength place of 269nm, and result meets the ultraviolet spectrum characteristic of Sodium O-formylcefamole.
Embodiment 3
Adopt the chromatographic column that weighting agent is octadecylsilane chemically bonded silica, acetonitrile-10% triethylamine (with phosphorus acid for adjusting pH value to 2.5) of take is (20:80) moving phase, detection wavelength is 254nm, the Sodium O-formylcefamole preparing in embodiment 1 is added to water and make the solution that every 1 mL contains Sodium O-formylcefamole 0.5mg, as test sample, the Sodium O-formylcefamole of getting listing is made the solution of same concentrations, then injecting chromatograph, record retention time, result shows that retention time is consistent.
Result of implementation shows, the sample in embodiment 1 is measured and shown that it is consistent with the reference substance of Sodium O-formylcefamole through HPLC.
Embodiment 4
The Mandokef superfine powder preparing in embodiment 1 is made to preparation.
Should be understood that these embodiments are only not used in and limit the scope of the invention for the present invention is described.In addition should be understood that those skilled in the art can make various changes or modifications formula of the present invention after having read the content of the present invention's instruction, these equivalent form of values fall within the application's appended claims limited range equally.
Claims (8)
1. a preparation method for Sodium O-formylcefamole superfine powder preparation, is characterized in that:
(1), benzoyl acetic acid is reacted with thionyl chloride, reaction after finishing is removed thionyl chloride;
(2), the product obtaining in step (1) is dissolved in methylene dichloride, and then add wherein 7-amino-3-[(1-methyl isophthalic acid H-tetrazolium-5-yl) thiomethyl]-3-cephem-4-carboxylic acid, after reaction, obtain compound (I), compound (I) structure is as follows:
；
(3), compound (I) is dissolved in tetrahydrofuran (THF), then, wherein to entering sodium borohydride, obtain compound (II) after reaction, the structure of compound (II) is as follows:
；
(4), compound (II) is reacted with formic acid esterification and obtains compound Mandokef;
(5), Mandokef is made to sodium salt;
(6), with comminution by gas stream, become superfine powder after Sodium O-formylcefamole is dry, reclaim, packing, the particle diameter of superfine powder is 0.5 ~ 3 μ m.
2. the preparation method of Sodium O-formylcefamole superfine powder preparation according to claim 1, is characterized in that: in step (1), the condition of reaction is stirring at room.
3. the preparation method of Sodium O-formylcefamole superfine powder preparation according to claim 2, is characterized in that: the comminution by gas stream in described step (6) adopts multi-stage crushing method, and gas velocity is 350 ~ 450m/s.
4. the preparation method of Sodium O-formylcefamole superfine powder preparation according to claim 3, it is characterized in that: in described step (2), the condition of reaction is stirring at room, and the product obtaining in step (1) and 7-amino-3-[(1-methyl isophthalic acid H-tetrazolium-5-yl) thiomethyl] mol ratio of-3-cephem-4-carboxylic acid is 1:1.5.
5. the preparation method of Sodium O-formylcefamole superfine powder preparation according to claim 4, is characterized in that: the product obtaining in step (2), by the mixed solvent recrystallization of ethanol and methylene dichloride, is obtained to the monocrystalline of compound (I).
6. the preparation method of Sodium O-formylcefamole superfine powder preparation according to claim 5, it is characterized in that: in step (4), esterification solvent used is ethyl acetate, and catalyzer is 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride.
7. the preparation method of Sodium O-formylcefamole superfine powder preparation according to claim 6, is characterized in that: the ethanol that the product obtaining in described step (2) is 10:11 by volume ratio and the mixed solvent recrystallization of methylene dichloride.
8. a preparation that contains the Sodium O-formylcefamole superfine powder that as claimed in any of claims 1 to 7 in one of claims prepared by preparation method.
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| CN104193767B CN104193767B (en) | 2016-07-06 |
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|---|---|---|---|---|
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| US3928334A (en) * | 1974-06-06 | 1975-12-23 | Bristol Myers Co | Process for the production of cefamandole |
| JPS5390285A (en) * | 1977-01-17 | 1978-08-08 | Sankyo Co Ltd | Preparation of cephalosporin derivs. |
| EP0029202B1 (en) * | 1979-11-16 | 1983-04-13 | Asahi Kasei Kogyo Kabushiki Kaisha | Novel tetrazole-5-thiol esters and process for preparing cefamandole using same |
| CN101108856A (en) * | 2007-07-27 | 2008-01-23 | 苏州中联化学制药有限公司 | Method for synthesizing antibiotic cefamandole nafate |
| CN101475580A (en) * | 2009-01-21 | 2009-07-08 | 海南美大制药有限公司 | Cefamandole nafate compounds and synthesizing method thereof |
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| WO2013057197A1 (en) * | 2011-10-20 | 2013-04-25 | Dsm Sinochem Pharmaceuticals Netherlands B.V. | Process for the formylation of cefamandole |
| WO2013057196A1 (en) * | 2011-10-20 | 2013-04-25 | Dsm Sinochem Pharmaceuticals Netherlands B.V. | Process for the preparation of cefamandole nafate |
-
2014
- 2014-08-07 CN CN201410385066.7A patent/CN104193767B/en active Active
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641021A (en) * | 1969-04-18 | 1972-02-08 | Lilly Co Eli | 3 7-(ring-substituted) cephalosporin compounds |
| US3928334A (en) * | 1974-06-06 | 1975-12-23 | Bristol Myers Co | Process for the production of cefamandole |
| JPS5390285A (en) * | 1977-01-17 | 1978-08-08 | Sankyo Co Ltd | Preparation of cephalosporin derivs. |
| EP0029202B1 (en) * | 1979-11-16 | 1983-04-13 | Asahi Kasei Kogyo Kabushiki Kaisha | Novel tetrazole-5-thiol esters and process for preparing cefamandole using same |
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