CN104045656A - Cefoxitin sodium superfine-powder preparation and preparation method thereof - Google Patents
Cefoxitin sodium superfine-powder preparation and preparation method thereof Download PDFInfo
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- CN104045656A CN104045656A CN201410247645.5A CN201410247645A CN104045656A CN 104045656 A CN104045656 A CN 104045656A CN 201410247645 A CN201410247645 A CN 201410247645A CN 104045656 A CN104045656 A CN 104045656A
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- 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
- C07D501/57—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with a further substituent in position 7, e.g. cephamycines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine
- A61K31/546—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, cefaclor, or cephalexine containing further heterocyclic rings, e.g. cephalothin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
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- 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
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Abstract
The invention discloses a preparation method of cefoxitin sodium superfine-powder preparations. The method comprises the following steps: 1, at room temperature, adding 7-alpha-methoxy-3-deacetyl cefalotin benzathine to acetone; 2, pouring reaction liquid obtained after reaction into ionized water, stirring the obtained mixture to carry out a hydrolysis reaction at 0-25 DEG C; 3, adding ethyl acetate to the obtained hydrolysis liquid; 4, adding activated carbon into an organic phase, stirring for 40 minutes, filtering the obtained product; 5, dissolving sodium iso-octoate into an ethanol solution; and 6, crushing dried cefoxitin sodium into superfine powder by using an air flow. The invention also discloses a cefoxitin sodium superfine-powder preparation which comprises special cefoxitin sodium superfine powder. According to the preparation method, the purity of cefoxitin sodium is greatly improved, so that the cefoxitin sodium has the advantages of high purity, less impurities, small particles, large specific surface area, good solubility, good activity and the like.
Description
Technical field
The invention provides a kind of cefoxitin sodium superfine powder preparation and preparation method thereof, belong to medical technical field.
Background technology
Cefoxitin sodium; chemical name is assorted nitrogen dicyclo (4.2.0) oct-2-ene-2-formic acid sodium salt of 3-carbamyl yloxymethyl-7-methoxyl group-8-oxo-7-(2-thiophene acetamido)-5-sulphur-1-; English name Cefoxitin, molecular formula is C
16h
16n
3naO
7s
2, molecular weight: 449.43, chemical structural formula is as follows:
Cefoxitin sodium is cephamycin-type microbiotic, system is the cephamycin C (CephamycinC) being produced by streptomycete Streptomyceslactamdurans, through the semi-synthetic class microbiotic making, its parent nucleus is similar to cynnematin, is put in second generation cephalosporin class.Cefoxitin sodium to the antibacterial ability of gram positive organism a little less than, strong to gram-negative bacteria effect, be clinically mainly used in the infection such as respiratory tract infection, endocarditis, peritonitis, pyelonephritis, urinary tract infections, septicemia and bone, joint, skin and soft tissue due to sensitive organism.
Disclose at present both at home and abroad the method for some cefoxitin preparation of sodium, but the cefoxitin preparation of sodium that these methods are made has that to imitate composition purity not high, and the problem such as the side effect causing is thus obvious.Therefore, there is at present the demand for preparation cefoxitin sodium formulation preparation method.
In December, 1999, " extraordinary superfine powder technology of preparing " obtains first-class National Scientific and Technological Progress Award, prize-winning unit: Institutes Of Technology Of Nanjing (Li Fengsheng), certificate number: 30-1-003-01.On January 2nd, 2014, Institutes Of Technology Of Nanjing exclusively assigns in Chang Dian pharmaceuticals about " application of extraordinary superfine powder technology of preparing in pharmaceutical preparation ", and corresponding product is carried out to formulation development and industrialization.
Summary of the invention
The object of the present invention is to provide extraordinary superfine powder preparation of a kind of cefoxitin sodium and preparation method thereof, this method significantly improves the purity of cefoxitin sodium, makes cefoxitin sodium have the advantages such as purity is high, impurity is few, particle is little, specific surface area is large, solvability is good, activity is good.
For addressing the above problem; the extraordinary superfine powder preparation of cefoxitin sodium of the present invention; with acetone and 7-α-methoxyl group-3-deacetyled cefoxitin benzathine; after chlorosulfonylation reaction; make cefoxitin acid finished product through hydrolysis, extraction, decolouring, contraction; then the ethanolic soln of sodium salt is added in the organic solvent that is dissolved with cefoxitin acid, obtain the extraordinary superfine powder of cefoxitin sodium finally by super-dry, air flow super.
For solving above technical problem, the preparation method of the extraordinary superfine powder of cefoxitin sodium provided by the invention, comprises the steps:
Step 1 under room temperature, adds 7-α-methoxyl group-3-deacetyled cefoxitin benzathine in acetone, adds chlorine sulphonyl second cyanate after being cooled to-70 ~-80 DEG C;
Step 2, pours the reaction solution after above-mentioned end in ionized water into, and reaction is hydrolyzed under 0 ~ 25 DEG C of temperature stirs;
Step 3 adds ethyl acetate in said hydrolyzed liquid, stirs after 15 minutes and filters, and filtrate is collected organic phase after leaving standstill phase-splitting;
Step 4 adds gac in above-mentioned organic phase, stirs after 40 minutes and filters, above-mentioned filtrate decompression is concentrated, separate out and stop concentrating when being concentrated into crystal, while being then warming up to 35 ~ 50 DEG C, in concentrated solution, add methylene dichloride, stir after 40 minutes filter to cefoxitin acid wet product;
Step 5, Sodium isooctanoate is dissolved in ethanolic soln, cefoxitin acid wet product is added in ethyl acetate and ethanol, add activated carbon decolorizing 25 minutes, suction filtration, washing with alcohol, under room temperature and low rate mixing, adds salts solution in acid solution, after crystallization, stir 2 hours, suction filtration, washing with alcohol three times, vacuum-drying, obtains cefoxitin sodium finished product;
Step 6, becomes superfine powder by dry cefoxitin sodium with comminution by gas stream, reclaims packaging.
As improvement of the present invention; in this step 1, the ratio of weight and number of 7-α-methoxyl group-3-deacetyled cefoxitin benzathine and acetone is 1:12, and the ratio of weight and number of 7-α-methoxyl group-3-deacetyled cefoxitin benzathine and Sulfuryl chloride isocyanate is 1.5: 1.
As improvement of the present invention, the reaction in this step 1 finishes while proceeding to 7-α-methoxyl group-3-deacetyled cefoxitin benzathine≤1.5%.
As improvement of the present invention, the reaction in described step 2 finishes while proceeding to midbody derivant≤1.5%.
As improvement of the present invention, the ratio of weight and number of the 7-α-methoxyl group-3-deacetyled cefoxitin benzathine in ethyl acetate and step 1 in described step 3 is 16:1.
As improvement of the present invention, in the methylene dichloride in described step 4 and step 1-ratio of weight and number of α-methoxyl group-3-deacetyled cefoxitin benzathine is 15:32.
As improvement of the present invention, the drying mode in described step 5 is that vacuum-drying comprises the following steps: normal pressure filters, and filter cake is put into the vacuum-drying that 40 DEG C is 0.09MPa with vacuum tightness and is dried 12 hours mutually after repeatedly washing with deionized water.
As improvement of the present invention, the comminution by gas stream in described step 6 adopts multi-stage crushing method, and gas velocity is 350 ~ 450m/s, and the particle diameter of superfine powder is 0.5 ~ 3 μ m.
The present invention also discloses a kind of cefoxitin sodium superfine powder preparation, and it comprises the extraordinary superfine powder of cefoxitin sodium.
The present invention has the following advantages: the present invention significantly improves the purity of cefoxitin sodium, makes cefoxitin sodium have the advantages such as purity is high, impurity is few, particle is little, specific surface area is large, solvability is good, activity is good.
Embodiment
Below in conjunction with embodiment, the present invention is further described in detail, the embodiment providing is only in order to illustrate the present invention, instead of in order to limit the scope of the invention.
The present invention discloses a kind of cefoxitin sodium superfine powder preparation, and it comprises the extraordinary superfine powder of cefoxitin sodium.
embodiment 1
7-α-methoxyl group-3-deacetyled cefoxitin benzathine 120g is added in 1.44L acetone, after being cooled to-70 DEG C ~-80 DEG C, add chlorine sulphonyl second cyanate 80g, while waiting reaction to proceed to 7-α-methoxyl group-3-deacetyled cefoxitin benzathine≤1.5%, finish; Gained reaction solution is poured in deionized water, the reaction that is hydrolyzed under 0 ~ 25 DEG C of temperature stirs adds 1.92L ethyl acetate in hydrolyzed solution, stirs filtration after 15 minutes, filtrate is collected organic phase after leaving standstill phase-splitting, in above-mentioned organic phase, add gac, stir after 40 minutes and filter, above-mentioned filtrate decompression is concentrated, when having crystal to separate out, inspissated juice stops concentrating, then be warming up to 40 DEG C, in concentrated solution, add methylene dichloride, stir filter after 40 minutes and extremely obtain cefoxitin acid wet product simultaneously.
Sodium isooctanoate is dissolved in ethanolic soln, cefoxitin acid wet product is added in ethyl acetate and ethanol, add activated carbon decolorizing 25 minutes, suction filtration, washing with alcohol, under room temperature and low rate mixing, salts solution is added in acid solution, after crystallization, stir 2 hours, suction filtration, washing with alcohol three times; Then adopt boulton process, normal pressure filters, and filter cake is put into the vacuum-drying that 40 DEG C is 0.09MPa with vacuum tightness and is dried 12 hours mutually after repeatedly washing with deionized water, obtain cefoxitin.
Analyze through HPLC, the purity of piperacillin sodium and tazobactam sodium powder mix is 98.9%, and number of effective theoretical plates is 2048.
Finally adopt comminution by gas stream, gas velocity is 350m/s, and the particle diameter of superfine powder is 1 ~ 3 μ m, reclaims packaging, the extraordinary superfine powder preparation of acquisition cefoxitin sodium.
embodiment 2
7-α-methoxyl group-3-deacetyled cefoxitin benzathine 120g is added in 1.44L acetone, after being cooled to-70 DEG C ~-80 DEG C, add chlorine sulphonyl second cyanate 80g, while waiting reaction to proceed to 7-α-methoxyl group-3-deacetyled cefoxitin benzathine≤1.5%, finish; Gained reaction solution is poured in deionized water, the reaction that is hydrolyzed under 0 ~ 25 DEG C of temperature stirs adds 1.92L ethyl acetate in hydrolyzed solution, stirs filtration after 15 minutes, filtrate is collected organic phase after leaving standstill phase-splitting, in above-mentioned organic phase, add gac, stir after 40 minutes and filter, above-mentioned filtrate decompression is concentrated, when having crystal to separate out, inspissated juice stops concentrating, then be warming up to 40 DEG C, in concentrated solution, add methylene dichloride, stir filter after 40 minutes and extremely obtain cefoxitin acid wet product simultaneously.
Sodium isooctanoate is dissolved in ethanolic soln, cefoxitin acid wet product is added in ethyl acetate and ethanol, add activated carbon decolorizing 25 minutes, suction filtration, washing with alcohol, under room temperature and low rate mixing, salts solution is added in acid solution, after crystallization, stir 2 hours, suction filtration, washing with alcohol three times; Then adopt boulton process, normal pressure filters, and filter cake is put into the vacuum-drying that 40 DEG C is 0.09MPa with vacuum tightness and is dried 12 hours mutually after repeatedly washing with deionized water, obtain cefoxitin.
Analyze through HPLC, the purity of piperacillin sodium and tazobactam sodium powder mix is 99.9%, and number of effective theoretical plates is 2048.
Finally adopt comminution by gas stream, gas velocity is 450m/s, and the particle diameter of superfine powder is 0.5 ~ 3 μ m, reclaims packaging, the extraordinary superfine powder preparation of acquisition cefoxitin sodium.
When the particle diameter of the superfine powder of cefoxitin sodium is 0.5～3 μ m, can be that cefoxitin sodium has good solvability; In the time that particle diameter is less than 0.5 μ m, solvability no longer increases along with diminishing of particle diameter, thereby it is very cost-effective that the particle diameter of the superfine powder of cefoxitin sodium adopts 0.5～3 μ m.
Adopt high velocity air method to spray grinding mode and prepare superfine powder, production process is simple and easy to control, and in the time that gas velocity is greater than 450m/s, particle diameter no longer diminishes along with the increase of speed, quoted passage, it is rationally effectively that comminution by gas stream adopts the speed of 350～450m/s.
embodiment 3 – safety testings (hypersensitive test)
20 of extracting waste cavys, body weight 280g ~ 350g, each class of male and female.Be divided into 4 groups, 5 of Meizus, i.e. cefoxitin sodium for injection (100mg/mL), Protalbinic acid liquid positive group (30mg/mL), physiological saline control group.
Every group of first corresponding solution 0.5mL of abdominal injection respectively the next day, totally 3 times, then above-mentioned each treated animal is equally divided into two groups again, one group obtains 14d after first administration, respectively auricular vein injection injection for cefoxitin sodium, Protalbinic acid liquid and physiological saline 2mL/, attack, observe the transformation reactions of the rear animal of injection, by the classification of transformation reactions progression standards of grading.Attack with method in injecting rear 21d first, and observe for the 2nd group.As transformation reactions progression, classification exceedes 2 grades, judges that transformation reactions is positive.
Result shows, cavy is 14d and 21d after injecting first, cefoxitin sodium for injection group and physiological saline control group, and transformation reactions progression is below 2, the positive control disorderly average transformation reactions progression of the single group of pendulum is 4, shows that cefoxitin sodium for injection can not cause cavy transformation reactions.
Claims (9)
1. a preparation method for cefoxitin sodium superfine powder preparation, is characterized in that: the method comprises the steps:
Step 1 under room temperature, adds 7-α-methoxyl group-3-deacetyled cefoxitin benzathine in acetone, adds chlorine sulphonyl second cyanate after being cooled to-70 ~-80 DEG C;
Step 2, pours the reaction solution after above-mentioned end in ionized water into, and reaction is hydrolyzed under 0 ~ 25 DEG C of temperature stirs;
Step 3 adds ethyl acetate in said hydrolyzed liquid, stirs after 15 minutes and filters, and filtrate is collected organic phase after leaving standstill phase-splitting;
Step 4 adds gac in above-mentioned organic phase, stirs after 40 minutes and filters, above-mentioned filtrate decompression is concentrated, separate out and stop concentrating when being concentrated into crystal, while being then warming up to 35 ~ 50 DEG C, in concentrated solution, add methylene dichloride, stir after 40 minutes filter to cefoxitin acid wet product;
Step 5, Sodium isooctanoate is dissolved in ethanolic soln, cefoxitin acid wet product is added in ethyl acetate and ethanol, add activated carbon decolorizing 25 minutes, suction filtration, washing with alcohol, under room temperature and low rate mixing, adds salts solution in acid solution, after crystallization, stir 2 hours, suction filtration, washing with alcohol three times, vacuum-drying, obtains cefoxitin sodium finished product;
Step 6, becomes superfine powder by dry cefoxitin sodium with comminution by gas stream, reclaims packaging.
2. the preparation method of the extraordinary superfine powder preparation of a kind of cefoxitin according to claim 1; it is characterized in that: in described step 1, the ratio of weight and number of 7-α-methoxyl group-3-deacetyled cefoxitin benzathine and acetone is 1:12, the ratio of weight and number of 7-α-methoxyl group-3-deacetyled cefoxitin benzathine and Sulfuryl chloride isocyanate is 1.5: 1.
3. the preparation method of a kind of cefoxitin sodium superfine powder preparation according to claim 2, is characterized in that: the reaction in described step 1 finishes while proceeding to 7-α-methoxyl group-3-deacetyled cefoxitin benzathine≤1.5%.
4. the preparation method of a kind of cefoxitin sodium superfine powder preparation according to claim 3, is characterized in that: the reaction in described step 2 finishes while proceeding to midbody derivant≤1.5%.
5. the preparation method of a kind of cefoxitin sodium superfine powder preparation according to claim 4, is characterized in that: the ratio of weight and number of the 7-α-methoxyl group-3-deacetyled cefoxitin benzathine in ethyl acetate and step 1 in described step 3 is 16:1.
6. the preparation method of a kind of cefoxitin sodium superfine powder preparation according to claim 5, is characterized in that: the ratio of weight and number of the 7-α-methoxyl group-3-deacetyled cefoxitin benzathine in methylene dichloride and step 1 in described step 4 is 15:32.
7. the preparation method of a kind of cefoxitin sodium superfine powder preparation according to claim 6, it is characterized in that: the drying mode in described step 5 is boulton process, comprise the following steps: normal pressure filters, filter cake is put into the vacuum-drying that 40 DEG C is 0.09MPa with vacuum tightness and is dried 12 hours mutually after repeatedly washing with deionized water.
8. a kind of preparation method of cefoxitin sodium superfine powder preparation according to claim 7, 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, and the particle diameter of superfine powder is 0.5 ~ 3 μ m.
9. a cefoxitin sodium superfine powder preparation, is characterized in that: it comprises the extraordinary superfine powder of cefoxitin sodium.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104402908A (en) * | 2014-10-23 | 2015-03-11 | 胡梨芳 | Cefoxitin sodium compound entity and composition and uses thereof |
| CN104447800A (en) * | 2014-11-21 | 2015-03-25 | 辽宁天华化工有限责任公司 | Synthesis technology of cefoxitin acid |
| CN104650115A (en) * | 2015-01-22 | 2015-05-27 | 杭州长典医药科技有限公司 | Cefoperazone sodium, special superfine compound powder preparation thereof and preparation method of special superfine compound powder preparation |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104402908A (en) * | 2014-10-23 | 2015-03-11 | 胡梨芳 | Cefoxitin sodium compound entity and composition and uses thereof |
| CN104447800A (en) * | 2014-11-21 | 2015-03-25 | 辽宁天华化工有限责任公司 | Synthesis technology of cefoxitin acid |
| CN104650115A (en) * | 2015-01-22 | 2015-05-27 | 杭州长典医药科技有限公司 | Cefoperazone sodium, special superfine compound powder preparation thereof and preparation method of special superfine compound powder preparation |
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Inventor after: Fu Miaoqing Inventor after: Li Fengsheng Inventor after: Chen Yudong Inventor before: Fu Miaoqing Inventor before: Li Fengsheng Inventor before: Chen Zongdong |
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Application publication date: 20140917 |