CN102351885B - Method for preparing cefuroxime-L-arginine hydrate - Google Patents

Method for preparing cefuroxime-L-arginine hydrate Download PDF

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CN102351885B
CN102351885B CN2011102395134A CN201110239513A CN102351885B CN 102351885 B CN102351885 B CN 102351885B CN 2011102395134 A CN2011102395134 A CN 2011102395134A CN 201110239513 A CN201110239513 A CN 201110239513A CN 102351885 B CN102351885 B CN 102351885B
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cephalofruxin
arginine
cefuroxime
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杨鹏博
宋珊珊
张超
何成光
刘竟飞
黄晓军
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NANCHANG LIJIAN PHARMACEUTICAL CO Ltd
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Abstract

The invention discloses a method for preparing a cefuroxime-L-arginine hydrate. The method comprises: dissolving cefuroxime in an L-arginine aqueous solution, with cefuroxime and the L-arginine added in proportion, then freeze-drying the solution or adding an organic solvent for recrystallization, thus finally obtaining a cefuroxime-L-arginine hydrate containing crystal water. The compound of the invention includes crystal water able to enhance cefuroxime stability. In the invention, the structural particularity of the compound is utilized to improve the disadvantages of easy discoloring and unstability in production, storage and usage of cefuroxime sodium, and the stability of cefuroxime is improved, so that medical products of high efficiency and stability can be prepared.

Description

Be used to prepare the method for cephalofruxin-L-l-arginine hydrate
Technical field
The present invention relates to field of medicaments, relate in particular to the method that is used to prepare the high cephalofruxin compound of a kind of stability, specifically is the method that is used to prepare cephalofruxin-L-l-arginine hydrate.
Background technology
Cephalofruxin is the second generation cephalosporin of wide spectrum, and its mechanism of action is through the combination bacterioprotein, thereby suppresses the synthetic of bacteria cell wall.Cephalofruxin has wider anti-microbial activity for pathogenic bacteria, and stable to many β-Nei Xiananmeis, and is especially stable to plasmid-mediated enzyme common in the enterobacteriaceae.Confirm in the treatment of animal in vitro tests and clinical infection that cephalofruxin has anti-microbial activity to aerobic gram positive organism such as streptococcus aureus (comprising that β-Nei Xiananmei produces bacterium), streptococcus pneumoniae, micrococcus scarlatinae and escherichia coli, hemophilus influenza (comprising beta-lactamase-producing), haemophilus parainfluenzae, Klebsiella Pneumoniae, moraxelle catarrhalis (comprising beta-lactamase-producing), NEISSERIA GONORRHOEAE aerobic gram-negative bacterias such as (comprising beta-lactamase-producing).In vitro tests shows that most of bacterial strain of enterococcus faecalis, methicillin-resistant staphylococcus aureus, difficile toxins and bacteroide fragilis is to the cephalofruxin resistance.Cephalofruxin is mainly used in treatment responsive microbial septicemia, skin and soft tissue infection, tonsillitis, respiratory system infection, meningitis, gonorrhoea, urinary tract infections, bone and the infection of joint etc.
The cephalofruxin bulk drug of domestic production at present is the sodium salt of cephalofruxin; Because Cefuroxime sodium is unstable; Variable color very easily takes place, have a strong impact on quality product, the storage of this product, transportation etc. have been brought certain difficulty; Usually adopt low temperature to store and control variable color, but improved storage, the transportation cost of this medicine greatly.
Therefore, prior art awaits to improve and development.
Summary of the invention
Deficiency in view of above-mentioned prior art; The object of the present invention is to provide the method that is used to prepare the high cephalofruxin compound of a kind of stability; Specifically be the method that is used to prepare cephalofruxin-L-l-arginine hydrate, be intended to solve easy to change in production, storage and use, the problem of unstable of existing cephalofruxin sodium salt.
Technical scheme of the present invention is following:
Be used to prepare the method for cephalofruxin-L-l-arginine hydrate, wherein, the preparation method of said cephalofruxin-L-l-arginine hydrate may further comprise the steps:
S100, cefuroxime acid is dissolved in the L-l-arginine aqueous solution;
S200, freeze-drying or adding organic solvent recrystallization.
The described method that is used to prepare cephalofruxin-L-l-arginine hydrate, wherein, said cephalofruxin-L-l-arginine hydrate contains the crystal water that strengthens cephalofruxin stability, and molecular formula is C 22H 30N 8O 10SnH 2O, n are greater than 0, and its chemical structural formula is following:
Figure 72318DEST_PATH_IMAGE001
。
The described method that is used to prepare cephalofruxin-L-l-arginine hydrate, wherein, among the said step S100, the arginic mol ratio of cefuroxime acid and L-is 5:1 ~ 1:5.
The described method that is used to prepare cephalofruxin-L-l-arginine hydrate, wherein, among the said step S100, the arginic mol ratio of cefuroxime acid and L-is 3:1 ~ 1:3.
The described method that is used to prepare cephalofruxin-L-l-arginine hydrate, wherein, said organic solvent is an acetone soln.
Beneficial effect: the method that is used to prepare cephalofruxin-L-l-arginine hydrate provided by the present invention; What preparation technology adopted is water system dissolving freeze-drying or recrystallization technology; Specifically be that cefuroxime acid is dissolved in the L-l-arginine aqueous solution; Cefuroxime acid and L-l-arginine add according to a certain percentage, and freeze-drying or add the organic solvent recrystallization then finally obtains containing the cephalofruxin-L-l-arginine hydrate of crystal water.Comprise a kind of crystal water that strengthens cephalofruxin stability in this compound structure.The present invention utilizes the singularity of this compound structure to improve shortcomings such as the cephalofruxin sodium salt is easy to change in production, storage and use, instability, has improved cephalofruxin stability, thereby has prepared efficient, stable medicament prodn.
Embodiment
The present invention provides a kind of method that is used to prepare cephalofruxin-L-l-arginine hydrate, and is clearer, clear and definite for making the object of the invention, technical scheme and effect, below to further explain of the present invention.Should be appreciated that specific embodiment described herein only in order to explanation the present invention, and be not used in qualification the present invention.
The cephalofruxin that the present invention carried-L-l-arginine hydrate comprises a kind of crystal water that strengthens cephalofruxin stability in this compound structure.Cephalofruxin-L-l-arginine hydrate can comprise n crystal water, and wherein n is greater than 0, and molecular formula is C 22H 30N 8O 10SnH 2O, its chemical structural formula is following:
。
The present invention utilizes the singularity of this compound structure to improve shortcomings such as the cephalofruxin sodium salt is easy to change in production, storage and use, instability, has improved cephalofruxin stability, thereby has prepared efficient, stable medicament prodn.
The said method that is used to prepare cephalofruxin-L-l-arginine hydrate; What its preparation technology adopted is water system dissolving freeze-drying or recrystallization technology; Specifically be that cefuroxime acid is dissolved in the L-l-arginine aqueous solution; Cefuroxime acid and L-l-arginine add according to a certain percentage, and freeze-drying or add the organic solvent recrystallization then finally obtains containing the cephalofruxin-L-l-arginine hydrate of crystal water.Said organic solvent can be recrystallization organic solvent commonly used.The quantity of crystal water depends on cefuroxime acid and L-l-arginine reaction ratio in the compound, and the arginic mol ratio of cefuroxime acid and L-is generally 5:1 ~ 1:5, is preferably 3:1 ~ 1:3.The present invention focuses on the stability how solution strengthens cephalofruxin; Discover that crystal water in the compound can strengthen the stability of this compound; Also there are certain relation in the quantity and the medicine stability of crystal water simultaneously, so the arginic reaction ratio of cefuroxime acid and L-is most important.The quantity that draws crystal water in the compound through a series of structural identification methods such as ultimate analysis, Ka Er-Fei Xiushi method, HPLC is 1 ~ 4, is preferably 2 ~ 3 through a large amount of contrast experiment's proofs again.
When containing 1 crystal water in cephalofruxin-L-l-arginine hydrate, molecular formula is C 22H 30N 8O 10SH 2O, molecular weight are 616.60, and its chemical structural formula is following:
Figure 224131DEST_PATH_IMAGE002
。
When containing 2 crystal water in cephalofruxin-L-l-arginine hydrate, molecular formula is C 22H 30N 8O 10S2H 2O, molecular weight are 634.62, and its chemical structural formula is following:
Figure 219769DEST_PATH_IMAGE003
。
When containing 3 crystal water in cephalofruxin-L-l-arginine hydrate, molecular formula is C 22H 30N 8O 10S3H 2O, molecular weight are 652.63, and its chemical structural formula is following:
Figure 888648DEST_PATH_IMAGE004
.
When containing 4 crystal water in cephalofruxin-L-l-arginine hydrate, molecular formula is C 22H 30N 8O 10S4H 2O, molecular weight are 670.64, and its chemical structural formula is following:
Figure 209908DEST_PATH_IMAGE005
。
Simultaneously, with The compounds of this invention and in the market the cephalofruxin preparation of sodium be the high temperature contrast experiment, prove that further The compounds of this invention stability is superior to the commercially available prod.
Said cephalofruxin-L-l-arginine hydrate is white to little yellow crystalline powder, and with the form administration that deep intramuscularly, intravenous injection or quiet notes instil, single dose comprises cephalofruxin 750mg to 3000mg.Adult's usual amounts is a 0.75g～1.5g, is administered once 5～10 days courses of treatment in per 8 hours.Child dose, the infant more than 3 months, every day, per kilogram of body weight 50～100mg divided 3～4 administrations.
Further specify the present invention with instance below, said instance should not be construed as limiting the invention.
Instance 1
Technology: cefuroxime acid is dissolved in the L-l-arginine aqueous solution, and the arginic mol ratio of cefuroxime acid and L-is 5:1, adds recrystallization in the acetone soln then, finally obtains containing the medical compounds of crystal water.
Detect:
1, ultimate analysis (C 22H 30N 8O 10SH 2O): C 42.81%; H 5.21%; N 18.13%; S 5.15%.(theory: C 42.85%; H 5.23%; N 18.17%; S 5.20%)
2, Shi Yong Ka Er-Fei Xiushi method records that moisture is 2.8 ~ 3.5% (theories: 2.9%) in this material; The thermogravimetric analysis result is indicated as the characteristic of monohydrate.
3, content analysis (HPLC method): containing cephalofruxin is 75.1%; Yield is 65.2%.
4, with this sample 60 ℃ of condition held of high temperature 10 days, respectively at 5 days, 10 days sampling test sample colors and solution colour, sample was white in color when the result showed 5 days, solution and yellow No. 3 color solution colors quite (=Y3); Sample is off-white color to little yellow in the time of 10 days, solution and yellow No. 5 color solution colors quite (=Y5).
Instance 2
Technology: cefuroxime acid is dissolved in the L-l-arginine aqueous solution, and the arginic mol ratio of cefuroxime acid and L-is 4:1, adds recrystallization in the acetone soln then, finally obtains containing the medical compounds of crystal water.
Detect:
1, ultimate analysis (C 22H 30N 8O 10SH 2O): C 42.83%; H 5.22%; N 18.13%; S 5.17%.(theory: C 42.85%; H5.23%; N 18.17%; S 5.20%)
2, Shi Yong Ka Er-Fei Xiushi method records that moisture is 2.8 ~ 3.5% (theories: 2.9%) in this material; The thermogravimetric analysis result is indicated as the characteristic of monohydrate.
3, content analysis: (HPLC method) contains cephalofruxin is 75.6%; Yield is 72.3%.
4, with this sample 60 ℃ of condition held of high temperature 10 days, respectively at 5 days, 10 days sampling test sample colors and solution colour, sample was white in color when the result showed 5 days, solution and yellow No. 3 color solution colors quite (=Y3); Sample is off-white color to little yellow in the time of 10 days, solution and yellow No. 5 color solution colors quite (=Y5).
Instance 3
Technology: cefuroxime acid is dissolved in the L-l-arginine aqueous solution, and the arginic mol ratio of cefuroxime acid and L-is 3:1, adds recrystallization in the acetone soln then, finally obtains containing the medical compounds of crystal water.
Detect:
1, ultimate analysis (C 22H 30N 8O 10S2H 2O): C 41.54%; H 5.20%; N 17.67%; S 5.03%.(theory: C 41.64%; H 5.40%; N 17.66%; S 5.05%)
2, Shi Yong Ka Er-Fei Xiushi method records that moisture is 5.5 ~ 6.0% (theories: 5.7%) in this material; The thermogravimetric analysis result is indicated as the characteristic of duohydrate.
3, content analysis: (HPLC method) contains cephalofruxin is 73.6%; Yield is 86.8%.
4, with this sample 60 ℃ of condition held of high temperature 10 days, respectively at 5 days, 10 days sampling test sample colors and solution colour, sample was white in color when the result showed 5 days, solution and yellow No. 2 color solution colors quite (=Y2); Sample is off-white color in the time of 10 days, solution and yellow No. 3 color solution colors quite (=Y3).
Instance 4
Technology: cefuroxime acid is dissolved in the L-l-arginine aqueous solution, and the arginic mol ratio of cefuroxime acid and L-is 2:1, adds recrystallization in the acetone soln then, finally obtains containing the medical compounds of crystal water.
Detect:
1, ultimate analysis (C 22H 30N 8O 10S2H 2O): C 41.58%; H 5.24%; N 17.66%; S 5.03%.(theory: C 41.64%; H 5.40%; N 17.66%; S 5.05%)
2, Shi Yong Ka Er-Fei Xiushi method records that moisture is 5.5 ~ 6.0% (theories: 5.7%) in this material; The thermogravimetric analysis result is indicated as the characteristic of duohydrate.
3, content analysis: (HPLC method) contains cephalofruxin is 73.9%; Yield is 90.1%.
4, with this sample 60 ℃ of condition held of high temperature 10 days, respectively at 5 days, 10 days sampling test sample colors and solution colour, sample was white in color when the result showed 5 days, solution and yellow No. 2 color solution colors quite (=Y2); Sample is off-white color in the time of 10 days, solution and yellow No. 3 color solution colors quite (=Y3).
Instance 5
Technology: cefuroxime acid is dissolved in the L-l-arginine aqueous solution, and the arginic mol ratio of cefuroxime acid and L-is 1:1, and freeze-drying then finally obtains containing the medical compounds of crystal water.
Detect:
1, ultimate analysis (C 22H 30N 8O 10S2H 2O): C 41.58%; H 5.22%; N 17.67%; S 5.04%.(theory: C 41.64%; H 5.40%; N 17.66%; S 5.05%)
2, Shi Yong Ka Er-Fei Xiushi method records that moisture is 5.5 ~ 6.0% (theories: 5.7%) in this material; The thermogravimetric analysis result is indicated as the characteristic of duohydrate.
3, content analysis: (HPLC method) contains cephalofruxin is 74.1%; Yield is 99.9%.
4, with this sample 60 ℃ of condition held of high temperature 10 days, respectively at 5 days, 10 days sampling test sample colors and solution colour, sample was white in color when the result showed 5 days, solution and yellow No. 2 color solution colors quite (=Y2); Sample is off-white color in the time of 10 days, solution and yellow No. 3 color solution colors quite (=Y3).
Instance 6
Technology: cefuroxime acid is dissolved in the L-l-arginine aqueous solution, and the arginic mol ratio of cefuroxime acid and L-is 1:2, adds recrystallization in the acetone soln then, finally obtains containing the medical compounds of crystal water.
Detect:
1, ultimate analysis (C 22H 30N 8O 10S2H 2O): C 41.50%; H 5.32%; N 17.71%; S 5.03%.(theory: C 41.64%; H 5.40%; N 17.66%; S 5.05%)
2, Shi Yong Ka Er-Fei Xiushi method records that moisture is 5.5 ~ 6.0% (theories: 5.7%) in this material; The thermogravimetric analysis result is indicated as the characteristic of duohydrate.
3, content analysis: (HPLC method) contains cephalofruxin is 74.0%; Yield is 91.4%.
4, with this sample 60 ℃ of condition held of high temperature 10 days, respectively at 5 days, 10 days sampling test sample colors and solution colour, sample was white in color when the result showed 5 days, solution and yellow No. 2 color solution colors quite (=Y2); Sample is off-white color in the time of 10 days, solution and yellow No. 3 color solution colors quite (=Y3).
Instance 7
Technology: cefuroxime acid is dissolved in the L-l-arginine aqueous solution, and the arginic mol ratio of cefuroxime acid and L-is 1:3, adds recrystallization in the acetone soln then, finally obtains containing the medical compounds of crystal water.
Detect:
1, ultimate analysis (C 22H 30N 8O 10S3H 2O): C 40.43%; H 5.49%; N 17.21%; S 4.92%.(theory: C 40.49%; H 5.56%; N 17.17%; S 4.91%)
2, Shi Yong Ka Er-Fei Xiushi method records that moisture is 8.0 ~ 8.8% (theories: 8.3%) in this material; The thermogravimetric analysis result is indicated as the characteristic of trihydrate.
3, content analysis: (HPLC method) contains cephalofruxin is 72.1%; Yield is 91.7%.
4, with this sample 60 ℃ of condition held of high temperature 10 days, respectively at 5 days, 10 days sampling test sample colors and solution colour, sample was white in color when the result showed 5 days, solution and yellow No. 2 color solution colors quite (=Y2); Sample is off-white color in the time of 10 days, solution and yellow No. 4 color solution colors quite (=Y4).
Instance 8
Technology: cefuroxime acid is dissolved in the L-l-arginine aqueous solution, and the arginic mol ratio of cefuroxime acid and L-is 1:4, adds recrystallization in the acetone soln then, finally obtains containing the medical compounds of crystal water.
Detect:
1, ultimate analysis (C 22H 30N 8O 10S3H 2O): C 40.41%; H 5.54%; N 17.18%; S 4.89%.(theory: C 40.49%; H 5.56%; N 17.17%; S 4.91%)
2, Shi Yong Ka Er-Fei Xiushi method records that moisture is 8.0 ~ 8.8% (theories: 8.3%) in this material; The thermogravimetric analysis result is indicated as the characteristic of trihydrate.
3, content analysis: (HPLC method) contains cephalofruxin is 71.9%; Yield is 81.9%.
4, with this sample 60 ℃ of condition held of high temperature 10 days, respectively at 5 days, 10 days sampling test sample colors and solution colour, sample was white in color when the result showed 5 days, solution and yellow No. 2 color solution colors quite (=Y2); Sample is off-white color in the time of 10 days, solution and yellow No. 4 color solution colors quite (=Y4).
Instance 9
Technology: cefuroxime acid is dissolved in the L-l-arginine aqueous solution, and the arginic mol ratio of cefuroxime acid and L-is 1:5, adds recrystallization in the acetone soln then, finally obtains containing the medical compounds of crystal water.
Detect:
1, ultimate analysis (C 22H 30N 8O 10S4H 2O): C 39.42%; H 5.65%; N 16.78%; S 4.75%.(theory: C 39.40%; H 5.71%; N 16.71%; S 4.78%)
2, Shi Yong Ka Er-Fei Xiushi method records that moisture is 10.3 ~ 10.9% (theories: 10.7%) in this material; The thermogravimetric analysis result is indicated as the characteristic of tetrahydrate.
3, content analysis: (HPLC method) contains cephalofruxin is 70.6%; Yield is 72.7%.
4, with this sample 60 ℃ of condition held of high temperature 10 days, respectively at 5 days, 10 days sampling test sample colors and solution colour, sample was white in color when the result showed 5 days, solution and yellow No. 3 color solution colors quite (=Y3); Sample is off-white color to little yellow in the time of 10 days, solution and yellow No. 6 color solution colors quite (=Y6).
Instance 10
The contrast experiment: simultaneously 60 ℃ of condition held of high temperature 10 days, respectively at 5 days, 10 days sampling test sample colors and solution colour, the result shows with each hydrate and commercially available Cefuroxime sodium:
Figure 265369DEST_PATH_IMAGE006
Result from table can find out that cephalofruxin of the present invention-L-l-arginine hydrate is better, not easy to change than the stability of commercially available Cefuroxime sodium.
Should be understood that application of the present invention is not limited to above-mentioned giving an example, concerning those of ordinary skills, can improve or conversion that all these improvement and conversion all should belong to the protection domain of accompanying claims of the present invention according to above-mentioned explanation.

Claims (2)

1. be used to prepare the method for cephalofruxin-L-l-arginine hydrate, it is characterized in that, the preparation method of said cephalofruxin-L-l-arginine hydrate may further comprise the steps:
S100, cefuroxime acid is dissolved in the L-l-arginine aqueous solution;
S200, freeze-drying or adding organic solvent recrystallization;
Among the said step S100, the arginic mol ratio of cefuroxime acid and L-is 5:1 ~ 1:5;
Said organic solvent is an acetone soln;
Said cephalofruxin-L-l-arginine hydrate contains the crystal water that strengthens cephalofruxin stability, and molecular formula is C 22H 30N 8O 10SnH 2O, n are 1 ~ 4 integer, and its chemical structural formula is following:
Figure FDA00001614953300011
2. the method that is used to prepare cephalofruxin-L-l-arginine hydrate according to claim 1 is characterized in that among the said step S100, the arginic mol ratio of cefuroxime acid and L-is 3:1 ~ 1:3.
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2072675A (en) * 1980-04-01 1981-10-07 Dobfar Spa Cephapirin salts
GB2073192A (en) * 1980-04-01 1981-10-14 Dobfar Spa Cefadroxil Salts
EP0189941A2 (en) * 1985-02-01 1986-08-06 Bristol-Myers Squibb Company Antibiotic compositions
EP0587121A1 (en) * 1992-09-08 1994-03-16 Bristol-Myers Squibb Company Crystalline dihydrate of a cephalosporin dihydrochloride salt and injectable compositions thereof
CN101007811A (en) * 2007-01-16 2007-08-01 陈文展 Organic amine salt of cephalosporin compound and its preparation method
CN101653443A (en) * 2009-08-18 2010-02-24 长沙京天生物医药科技有限公司 Composition of amino-cephalosporanic acid and arginine

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2072675A (en) * 1980-04-01 1981-10-07 Dobfar Spa Cephapirin salts
GB2073192A (en) * 1980-04-01 1981-10-14 Dobfar Spa Cefadroxil Salts
EP0189941A2 (en) * 1985-02-01 1986-08-06 Bristol-Myers Squibb Company Antibiotic compositions
EP0587121A1 (en) * 1992-09-08 1994-03-16 Bristol-Myers Squibb Company Crystalline dihydrate of a cephalosporin dihydrochloride salt and injectable compositions thereof
CN101007811A (en) * 2007-01-16 2007-08-01 陈文展 Organic amine salt of cephalosporin compound and its preparation method
CN101653443A (en) * 2009-08-18 2010-02-24 长沙京天生物医药科技有限公司 Composition of amino-cephalosporanic acid and arginine

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Address after: No. 22, Longtan Road, Nanchang economic and Technological Development Zone, Jiangxi Province, Jiangxi

Patentee after: Nanchang Lijian Pharmaceutical Co., Ltd.

Address before: 518109 Guangdong city of Shenzhen province Baoan District Longhua with rich industrial park road

Patentee before: Shenzhen Lijian Pharmaceutical Co., Ltd.

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