CN101798314A - High-purity cefmenoxime hydrochloride compound - Google Patents
High-purity cefmenoxime hydrochloride compound Download PDFInfo
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- CN101798314A CN101798314A CN 201010130555 CN201010130555A CN101798314A CN 101798314 A CN101798314 A CN 101798314A CN 201010130555 CN201010130555 CN 201010130555 CN 201010130555 A CN201010130555 A CN 201010130555A CN 101798314 A CN101798314 A CN 101798314A
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- cefmenoxime
- filtrate
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Links
- 229960003791 cefmenoxime Drugs 0.000 title claims abstract description 15
- -1 cefmenoxime hydrochloride compound Chemical class 0.000 title claims abstract description 10
- 238000000746 purification Methods 0.000 claims abstract description 15
- 238000000926 separation method Methods 0.000 claims abstract description 8
- MPTNDTIREFCQLK-UNVJPQNDSA-N cefmenoxime hydrochloride Chemical compound [H+].[Cl-].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=NN=NN1C.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=NN=NN1C MPTNDTIREFCQLK-UNVJPQNDSA-N 0.000 claims description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000000706 filtrate Substances 0.000 claims description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 8
- 238000005261 decarburization Methods 0.000 claims description 8
- 238000004237 preparative chromatography Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 235000017550 sodium carbonate Nutrition 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 238000010669 acid-base reaction Methods 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 6
- HJJDBAOLQAWBMH-YCRCPZNHSA-N cefmenoxime Chemical compound 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=NN=NN1C HJJDBAOLQAWBMH-YCRCPZNHSA-N 0.000 description 5
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 239000005864 Sulphur Substances 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
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000003570 biosynthesizing effect Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000013094 purity test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Abstract
The invention relates to a cefmenoxime hydrochloride compound, which is prepared through acid-base reaction, activated carbon adsorption, separation and purification of prepared chromatography so as to achieve the aim of purification and obtain the high-purity cefmenoxime hydrochloride compound finally. The invention optimizes the product quality, and guarantees safety of clinical medication.
Description
Technical field
The present invention relates to a kind of purification process of cefmenoxime hydrochloride compound, can obtain highly purified Cefmenoxime Hemihydrochloride, belong to medical technical field by method of the present invention.
Background technology
Cefmenoxime Hemihydrochloride, its chemical name is: (6R, 7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-methoxyimino kharophen]-3-[[1-methyl isophthalic acid H-tetrazolium-5-yl)-sulphur] methyl]-8-oxo-5-thia-1-azabicyclo [4.2.0] oct-2-ene-2-formate hydrochlorate (2: 1), molecular formula: C
16H
17N
9O
5S
31/2HCl, molecular weight: 529.79, structural formula is:
Cefmenoxime Hemihydrochloride is the third generation cephalosporin that Japanese Wu Tian company develops, and nineteen eighty-three is a kind of Broad spectrum antibiotics in Japanese Initial Public Offering, reaches germicidal action by the biosynthesizing that suppresses bacteria cell wall.
About the synthetic method of Cefmenoxime Hemihydrochloride, according to bibliographical information, mainly be raw material with 7-ACA, (1) 3 condensations, 7 condensations more earlier; (2) 7 condensations, 3 condensations more earlier.
At present, domestic each the preparation manufacturer of Cefmenoxime Hemihydrochloride relies on the imported raw material medicine, but its purity is relatively poor, color and luster is bad, and content is low, has influenced its quality of the pharmaceutical preparations, therefore, a kind of high purity, high-load Cefmenoxime Hemihydrochloride have certain social benefit and economic benefit.
Summary of the invention
The object of the present invention is to provide a kind of process for purification of cefmenoxime hydrochloride compound, by acid-base reaction, charcoal absorption and preparative chromatography separation and purification, reach the purpose of refining purifying, finally obtain highly purified cefmenoxime hydrochloride compound, optimize quality product, ensured safety of clinical administration.
The process for purification of cefmenoxime hydrochloride compound provided by the invention comprises the steps:
(1) the Cefmenoxime Hemihydrochloride crude product is soluble in water, slowly add alkali then, stirring reaction to pH value of solution is 6-10, wherein said alkali is sodium hydroxide, potassium hydroxide, yellow soda ash, sodium bicarbonate, salt of wormwood or saleratus, and preferred sodium hydroxide, yellow soda ash or sodium bicarbonate, most preferably sodium hydroxide, the gac that adds overall solution volume 0.01-0.05 (g/ml) then, 20-50 ℃ was stirred 0.5-1.5 hour, filtered decarburization, collected filtrate.
(2) adding hydrochloric acid reaction to pH value of solution value in the filtrate that upwards step obtains is 4-6, and preferred pH value is 4.5-5.5, adds organic solvent again, and stirring at room reaction 30-60 minute is filtered, and 45-50 ℃ of drying under reduced pressure obtains the purified Cefmenoxime Hemihydrochloride; Wherein organic solvent is selected from ethanol, acetone, Virahol or propyl carbinol.
Perhaps, (2 ') will go up the filtrate that obtains of step and utilize the preparative chromatography post to carry out separation and purification to obtain the purified Cefmenoxime Hemihydrochloride, wherein the moving phase used of chromatographic column accounts for the methylene dichloride of moving phase 30-50% or acetone and volume as volume and accounts for the hydrochloric acid soln of the pH of moving phase 50-70% as 1-2, and fixed phase stuffing is a silica gel; Flow velocity is 4.5-6.8ml/min; Column temperature: 20-25 ℃.Collect filtrate, drying under reduced pressure obtains the purified Cefmenoxime Hemihydrochloride.
As the present invention's one preferred embodiment, stirring reaction to pH value of solution value is 7-9 in the step (1).
As the present invention's one preferred embodiment, organic solvent is a Virahol in the step (2).
The process for purification of cefmenoxime hydrochloride compound provided by the invention, by acid-base reaction, charcoal absorption and preparative chromatography separation and purification have improved the purity of Cefmenoxime Hemihydrochloride greatly, have optimized the quality product of preparation, have ensured safety of clinical administration; Present method technology is simple, and cost is low, and the yield height is suitable for suitability for industrialized production.
Embodiment
Below further explain and describe content of the present invention by embodiment, but embodiment is not to be construed as limiting the scope of the invention.
Purity testing is undertaken by high performance liquid chromatography with reference to two appendix VD of Chinese Pharmacopoeia version in 2005.The filling of the preparative chromatography post that uses in the treating process is undertaken by ordinary method.Determine that by nucleus magnetic resonance and infrared spectra the resulting product in refining back is a Cefmenoxime Hemihydrochloride.
Making with extra care of embodiment 1 Cefmenoxime Hemihydrochloride
(1) 100g Cefmenoxime Hemihydrochloride crude product is dissolved in the 120ml water, slowly adds 5% sodium carbonate solution then, stirring reaction to pH value of solution is 7, adds the gac of 1.22g then, and stirring at room 30 minutes is filtered decarburization, collects filtrate.
(2) upwards going on foot hydrochloric acid reaction to the pH value of solution value that adds 0.1mol/L in the filtrate that obtains is 5.5, adds Virahol 1000ml again, stirring at room reaction 30 minutes, filter, 45 ℃ of drying under reduced pressure obtain purified Cefmenoxime Hemihydrochloride 91.4g, yield is 91.4%, and HPLC purity is 99.6%.
1H-NMR MHz (Bruker AV400mHz) (DMSO-d
6) δ: 9.63 (d, 1H, CONH), 6.73 (s, 1H, thiazole ring C
5-H), 5.77 (dd, 1H, C
7-H), 5.11 (d, 1H, C
6-H), 4.22 (q, 2H, C
3-CH
2), 3.93 (s, 3H ,-OCH
3), 3.84 (s, 3H ,-NCH
3), 3.72 (q, 2H, C
2-CH
2).
Making with extra care of embodiment 2 Cefmenoxime Hemihydrochlorides
(1) 100g Cefmenoxime Hemihydrochloride crude product is dissolved in the 150ml water, slowly adds 10% sodium hydrogen carbonate solution then, stirring reaction to pH value of solution is 8, adds the gac of 2.98g then, and stirring at room 20 minutes is filtered decarburization, collects filtrate.
(2) upwards going on foot hydrochloric acid reaction to the pH value of solution value that adds 1mol/L in the filtrate that obtains is 4.5, adds Virahol 150ml again, stirring at room reaction 60 minutes, filter, 50 ℃ of drying under reduced pressure obtain purified Cefmenoxime Hemihydrochloride 92.5g, yield is 92.5%, and HPLC purity is 99.5%.
1H-NMR MHz (Bruker AV400mHz) (DMSO-d
6) δ: 9.63 (d, 1H, CONH), 6.73 (s, 1H, thiazole ring C
5-H), 5.77 (dd, 1H, C
7-H), 5.11 (d, 1H, C
6-H), 4.22 (q, 2H, C
3-CH
2), 3.93 (s, 3H ,-OCH
3), 3.84 (s, 3H ,-NCH
3), 3.72 (q, 2H, C
2-CH
2).
Making with extra care of embodiment 3 Cefmenoxime Hemihydrochlorides
(1) 100g Cefmenoxime Hemihydrochloride crude product is dissolved in the 150ml water, slowly adds 8% sodium hydroxide solution then, stirring reaction to pH value of solution is 7.5, adds the gac of 2.56g then, and stirring at room 30 minutes is filtered decarburization, collects filtrate.
(2) upwards going on foot hydrochloric acid reaction to the pH value of solution value that adds 0.5mol/L in the filtrate that obtains is 5.0, adds Virahol 150ml again, stirring at room reaction 60 minutes, filter, 45 ℃ of drying under reduced pressure obtain purified Cefmenoxime Hemihydrochloride 91.8g, yield is 91.8%, and HPLC purity is 99.6%.
1H-NMR MHz (Bruker AV400mHz) (DMSO-d
6) δ: 9.63 (d, 1H, CONH), 6.73 (s, 1H, thiazole ring C
5-H), 5.77 (dd, 1H, C
7-H), 5.11 (d, 1H, C
6-H), 4.22 (q, 2H, C
3-CH
2), 3.93 (s, 3H ,-OCH
3), 3.84 (s, 3H ,-NCH
3), 3.72 (q, 2H, C
2-CH
2).
Making with extra care of embodiment 4 Cefmenoxime Hemihydrochlorides
(1) 100g Cefmenoxime Hemihydrochloride crude product is dissolved in the 150ml water, slowly adds 9% sodium hydroxide solution then, stirring reaction to pH value of solution is 9, adds the gac of 2.49 grams then, and 30 ℃ were stirred 40 minutes, filtered decarburization, collected filtrate.
(2 ') will go up the filtrate that obtains of step and utilize the preparative chromatography post to carry out separation and purification to obtain the purified Cefmenoxime Hemihydrochloride, wherein to account for the acetone of moving phase 40% and pH that volume accounts for moving phase 60% as volume be 1 hydrochloric acid soln to the moving phase used of chromatographic column, and fixed phase stuffing is a silica gel; Flow velocity is 4.8ml/min; Column temperature: 20 ℃.Collect filtrate, drying under reduced pressure obtains purified Cefmenoxime Hemihydrochloride 92.0g, and yield is 92.0%, and HPLC purity is 99.8%.
1H-NMR MHz (Bruker AV400mHz) (DMSO-d
6) δ: 9.63 (d, 1H, CONH), 6.73 (s, 1H, thiazole ring C
5-H), 5.77 (dd, 1H, C
7-H), 5.11 (d, 1H, C
6-H), 4.22 (q, 2H, C
3-CH
2), 3.93 (s, 3H ,-OCH
3), 3.84 (s, 3H ,-NCH
3), 3.72 (q, 2H, C
2-CH
2).
Making with extra care of embodiment 5 Cefmenoxime Hemihydrochlorides
(1) 100g Cefmenoxime Hemihydrochloride crude product is dissolved in the 180ml water, slowly adds 11% sodium carbonate solution then, stirring reaction to pH value of solution is 8, adds the gac of 2.48 grams then, and 25 ℃ were stirred 45 minutes, filtered decarburization, collected filtrate.
(2 ') will go up the filtrate that obtains of step and utilize the preparative chromatography post to carry out separation and purification to obtain the purified Cefmenoxime Hemihydrochloride, wherein to account for the acetone of moving phase 30% and pH that volume accounts for moving phase 70% as volume be 1 hydrochloric acid soln to the moving phase used of chromatographic column, and fixed phase stuffing is a silica gel; Flow velocity is 5.6ml/min; Column temperature: 25 ℃.Collect filtrate, drying under reduced pressure obtains purified Cefmenoxime Hemihydrochloride 92.4g, and yield is 92.4%, and HPLC purity is 99.8%.
1H-NMR MHz (Bruker AV400mHz) (DMSO-d
6) δ: 9.63 (d, 1H, CONH), 6.73 (s, 1H, thiazole ring C
5-H), 5.77 (dd, 1H, C
7-H), 5.11 (d, 1H, C
6-H), 4.22 (q, 2H, C
3-CH
2), 3.93 (s, 3H ,-OCH
3), 3.84 (s, 3H ,-NCH
3), 3.72 (q, 2H, C
2-CH
2).
Making with extra care of embodiment 6 Cefmenoxime Hemihydrochlorides
(1) 100g Cefmenoxime Hemihydrochloride crude product is dissolved in the 120ml water, slowly adds 12% sodium hydrogen carbonate solution then, stirring reaction to pH value of solution is 8, adds the gac of 2.46 grams then, and 35 ℃ were stirred 35 minutes, filtered decarburization, collected filtrate.
(2 ') will go up the filtrate that obtains of step and utilize the preparative chromatography post to carry out separation and purification to obtain the purified Cefmenoxime Hemihydrochloride, wherein to account for the acetone of moving phase 42% and pH that volume accounts for moving phase 58% as volume be 1 hydrochloric acid soln to the moving phase used of chromatographic column, and fixed phase stuffing is a silica gel; Flow velocity is 6.2ml/min; Column temperature: 25 ℃.Collect filtrate, drying under reduced pressure obtains purified Cefmenoxime Hemihydrochloride 92.2g, and yield is 92.2%, and HPLC purity is 99.8%.
1H-NMR MHz (Bruker AV400mHz) (DMSO-d
6) δ: 9.63 (d, 1H, CONH), 6.73 (s, 1H, thiazole ring C
5-H), 5.77 (dd, 1H, C
7-H), 5.11 (d, 1H, C
6-H), 4.22 (q, 2H, C
3-CH
2), 3.93 (s, 3H ,-OCH
3), 3.84 (s, 3H ,-NCH
3), 3.72 (q, 2H, C
2-CH
2).
Claims (3)
1. the cefmenoxime hydrochloride compound shown in the formula (I) comprises the steps:
(1) the Cefmenoxime Hemihydrochloride crude product is soluble in water, slowly add alkali then, stirring reaction to pH value of solution is 6-10, wherein said alkali is sodium hydroxide, potassium hydroxide, yellow soda ash, sodium bicarbonate, salt of wormwood or saleratus, and preferred sodium hydroxide, yellow soda ash or sodium bicarbonate, most preferably sodium hydroxide, the gac that adds overall solution volume 0.01-0.05 (g/ml) then, 20-50 ℃ was stirred 0.5-1.5 hour, filtered decarburization, collected filtrate.
(2) adding hydrochloric acid reaction to pH value of solution value in the filtrate that upwards step obtains is 4-6, and preferred pH value is 4.5-5.5, adds organic solvent again, and stirring at room reaction 30-60 minute is filtered, and 45-50 ℃ of drying under reduced pressure obtains the purified Cefmenoxime Hemihydrochloride; Wherein organic solvent is selected from ethanol, acetone, Virahol or propyl carbinol.
Perhaps, (2 ') will go up the filtrate that obtains of step and utilize the preparative chromatography post to carry out separation and purification to obtain the purified Cefmenoxime Hemihydrochloride, wherein the moving phase used of chromatographic column accounts for the methylene dichloride of moving phase 30-50% or acetone and volume as volume and accounts for the hydrochloric acid soln of the pH of moving phase 50-70% as 1-2, and fixed phase stuffing is a silica gel; Flow velocity is 4.5-6.8ml/min; Column temperature: 20-25 ℃.Collect filtrate, drying under reduced pressure obtains the purified Cefmenoxime Hemihydrochloride.
2. process for purification according to claim 1 is characterized in that stirring reaction to pH value of solution value is 7-9 in the step (1).
3. process for purification according to claim 1 is characterized in that organic solvent is a Virahol in the step (2).
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102329329A (en) * | 2011-07-15 | 2012-01-25 | 海南灵康制药有限公司 | Novel method for preparing cefmenoxime hydrochloride compound |
| CN102329313A (en) * | 2011-07-15 | 2012-01-25 | 海南灵康制药有限公司 | Azasetron hydrochloride compound and preparation method thereof |
| CN102408439A (en) * | 2011-10-20 | 2012-04-11 | 桂林澳林制药有限责任公司 | Cefmenoxime hydrochloride compound used for injection |
| CN102731531A (en) * | 2012-06-12 | 2012-10-17 | 浙江尖峰药业有限公司 | Cefmenoxime hydrochloride compound and synthesizing method thereof |
| CN102816174A (en) * | 2012-09-10 | 2012-12-12 | 天津市嵩锐医药科技有限公司 | Amorphous cefmenoxime hydrochloride compound |
| CN103145735A (en) * | 2013-03-21 | 2013-06-12 | 四川省惠达药业有限公司 | Cefmenoxime hydrochloride compound for injection and pharmaceutical composition thereof |
| CN103554136A (en) * | 2013-10-31 | 2014-02-05 | 哈药集团制药总厂 | Preparation method of cefmenoxine hydrochloride dry powder |
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| WO2013010296A1 (en) * | 2011-07-15 | 2013-01-24 | 海南灵康制药有限公司 | Novel method for preparing cefmenoxime hydrochloride compound |
| CN102329313A (en) * | 2011-07-15 | 2012-01-25 | 海南灵康制药有限公司 | Azasetron hydrochloride compound and preparation method thereof |
| CN102329329B (en) * | 2011-07-15 | 2012-09-05 | 海南灵康制药有限公司 | Novel method for preparing cefmenoxime hydrochloride compound |
| CN102329313B (en) * | 2011-07-15 | 2012-09-26 | 海南灵康制药有限公司 | Azasetron hydrochloride compound and preparation method thereof |
| CN102329329A (en) * | 2011-07-15 | 2012-01-25 | 海南灵康制药有限公司 | Novel method for preparing cefmenoxime hydrochloride compound |
| US8895728B2 (en) | 2011-07-15 | 2014-11-25 | Hainan Lingkang Pharmaceutical Co., Ltd. | Method for preparing cefmenoxime hydrochloride compound |
| CN102408439A (en) * | 2011-10-20 | 2012-04-11 | 桂林澳林制药有限责任公司 | Cefmenoxime hydrochloride compound used for injection |
| CN102408439B (en) * | 2011-10-20 | 2012-08-29 | 桂林澳林制药有限责任公司 | Cefmenoxime hydrochloride compound used for injection |
| CN102731531A (en) * | 2012-06-12 | 2012-10-17 | 浙江尖峰药业有限公司 | Cefmenoxime hydrochloride compound and synthesizing method thereof |
| CN102816174A (en) * | 2012-09-10 | 2012-12-12 | 天津市嵩锐医药科技有限公司 | Amorphous cefmenoxime hydrochloride compound |
| CN103145735A (en) * | 2013-03-21 | 2013-06-12 | 四川省惠达药业有限公司 | Cefmenoxime hydrochloride compound for injection and pharmaceutical composition thereof |
| CN103145735B (en) * | 2013-03-21 | 2014-02-26 | 四川省惠达药业有限公司 | Cefmenoxime hydrochloride compound for injection and pharmaceutical composition thereof |
| CN103554136A (en) * | 2013-10-31 | 2014-02-05 | 哈药集团制药总厂 | Preparation method of cefmenoxine hydrochloride dry powder |
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| CN101798314B (en) | 2012-06-27 |
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