CN110251467A - A kind of preparation method of amorphous state Cefditoren pivoxil Cephalosporins composition - Google Patents
A kind of preparation method of amorphous state Cefditoren pivoxil Cephalosporins composition Download PDFInfo
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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
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
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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
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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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
- C07D501/12—Separation; Purification
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cephalosporin Compounds (AREA)
Abstract
The present invention relates to pharmaceutical chemistry to synthesize field, provides a kind of new preparation process of amorphous state cefditoren composition.It is characterized in that crystalline state cefditoren is taken to be dissolved in the mixed organic solvents for being heated to certain temperature, a certain proportion of water-soluble high-molecular material is suspended in the mixed organic solvents, spray-dried device is dry, and amorphous state Cefditoren pivoxil Cephalosporins composition (wrapping up a certain proportion of water-soluble high-molecular material in inside) can be obtained.
Description
Technical field
The present invention relates to a kind of pharmaceutical chemistry to synthesize field, is related to Cefditoren pivoxil Cephalosporins, in particular to a kind of amorphous head
The preparation method of the appropriate logical sequence pivoxil composition of spore.
Background technique
Cefditoren pivoxil Cephalosporins (cefditoren pivoxil), is third generation oral cephalosporin class antibiotic, 1994
It is developed by Japanese Meiji Seika Kaisba company, it is especially right for treating gram-positive bacteria and the microbial infection of Gram-negative
Staphylococcus, the gram-positive bacteria of the streptococcus including streptococcus pneumonia, Escherichia coli, catarrh Blanc Chinese ball
The Gram-negative bacterias such as bacterium, Kleb, Proteus, haemophilus influenzae and Peptostreptococcus, acne third
The anaerobic bacterias such as acidfast bacilli, Bacteroides all show very strong antimicrbial power.Due to Cefditoren pivoxil Cephalosporins has a broad antifungal spectrum, thus
It is widely used in clinic, chemical structural formula are as follows:
Cefditoren pivoxil Cephalosporins exists with two kinds of crystal forms: crystalline state and amorphous state.Wherein crystalline state Cefditoren pivoxil Cephalosporins phase
Advantage for amorphous state is with high stability: including stability of crystal form and chemical stability under high wet heat condition.It is convenient
Storage and transport, therefore Cefditoren pivoxil Cephalosporins raw material on sale at present is that crystalline state form exists.
There are significant disadvantages compared with amorphous state for crystalline state Cefditoren pivoxil Cephalosporins: poorly water-soluble.Poorly water-soluble causes
Its solution rate, solubility are poor, so that dissolution generates large effect in vivo to it, therefore are unable to satisfy formulation requirements.And
Amorphous state Cefditoren pivoxil Cephalosporins has good water solubility, can satisfy formulation requirements, at present original triturate -- Japanese Mingzhi
What the Cefditoren pivoxil Cephalosporins granules/tablets listed in producing country, Zhi Guo Co., Ltd. were all made of is amorphous state cefoperon
Ester composition.
Therefore amorphous state need to be converted by crystalline state Cefditoren pivoxil Cephalosporins before preparation preparation and used, original is found at present
Grind technique used by MingZhi fruit Co., Ltd, Japan, company (Patent No. CN99802785.5) are as follows: crystalline state cefoperon
Ester and water-soluble high-molecular material are dissolved in acid flux material, are added dropwise in alkaline solution and acid flux material, solid are precipitated, collect and do
It is dry to obtain amorphous state Cefditoren pivoxil Cephalosporins composition (containing a certain proportion of water-soluble high-molecular material).The verified technique
Feasible poor, there are larger problems: 1, because this product stability is poor, being dissolved in aqueous solution related substance rapid development；2, water
As solvent seasoning difficulty, drying temperature is higher longer with drying time, and amorphous state Cefditoren pivoxil Cephalosporins composition high temperature is high
Stability of crystal form is poor under the conditions of wet, easily transits to lower state (crystalline state) by upper state (amorphous state), mixed crystal occurs, cause
Crystal form is impure, influences the preparation of subsequent preparation.
In summary problem, need to develop it is achievable, can industrialization, process stabilizing prepare amorphous state cefoperon
The preparation method of ester composition, to meet subsequent formulation samples preparation.
Summary of the invention
The present invention provides a kind of preparation methods of amorphous state Cefditoren pivoxil Cephalosporins composition for pharmaceutical preparation, protect
Its purity is demonstrate,proved, and its growth in relation to substance can be effectively controlled.Process stabilizing, easy industrialization.
In order to achieve the above technical purposes, the present invention is realized especially by following technical scheme:
A kind of preparation method of amorphous state Cefditoren pivoxil Cephalosporins composition, which is characterized in that take crystalline state cefoperon
Pivoxil dissolves in mixed organic solvents, and water-soluble high-molecular material is suspended in mixed organic solvents, spray-dried, obtains
Amorphous state Cefditoren pivoxil Cephalosporins composition.
The mixed organic solvents are acetone, ethyl acetate, ethyl alcohol, acetonitrile, methylene chloride, chloroform and N, N- bis-
Any two kinds of solvents and any two or more compositions in methylformamide.
The water-soluble high-molecular material is hydroxypropyl methylcellulose, hydroxypropyl cellulose, polyvinylpyrrolidone and first
It is any a kind of or any two or more in base cellulose.
The temperature of the dissolving crystallized state cefditoren is 30~50 DEG C.
The drying process with atomizing parameter: inlet air temperature is 50-80 DEG C, leaving air temp is 30-60 DEG C, atomization frequency is
30HZ-50HZ。
The dosage mass volume ratio of crystalline state cefditoren and organic solvent is 1:8~1:20G/ML.
Water-soluble high-molecular material and crystalline state cefditoren mass ratio are 1:40~1:200G/G.
The utility model has the advantages that
1, acid leach solution is replaced using organic solvent, it is related during aqueous solution that Cefditoren pivoxil Cephalosporins can be reduced
The growth of substance；2, dry using organic solvent since stability is very poor under the condition of high temperature and high humidity for amorphous state cefditoren
Dry process is easily removed compared with water as solvent, and same drying temperature can be reduced can shorten with drying time, avoid the occurrence of mixed crystal as a result,
Amorphous state very high purity is made；3, a certain proportion of water-soluble high-molecular material, which is added, can increase its stable crystal formation, and
It is precipitated again after dissolution in vivo and still ensures that exist with a certain proportion of amorphous state, enhance its bioavilability；4, using spray
Mist drying process, it is ensured that high molecular material is uniformly dispersed, and can reduce the related object that drying time effectively controls amorphous state
The growth of matter, process stabilizing and controllable；
Detailed description of the invention
Fig. 1 is the XRD spectrum that embodiment 1 measures.
Fig. 2 is the XRD spectrum that embodiment 2 measures
Fig. 3 is the XRD spectrum that embodiment 3 measures
Fig. 4 is the XRD spectrum that embodiment 4 measures
Fig. 5 is the XRD spectrum that embodiment 5 measures
Fig. 6 is the XRD spectrum that embodiment 6 measures
Fig. 7 is the XRD spectrum that comparative example 1 measures
Specific embodiment
Following embodiments are used to be further described the embodiment of claim, but are not limited to the present invention.
Embodiment 1
50g cefditoren is suspended in 500ml methylene chloride and acetone (volume ratio 1:1), is heated up 40 DEG C and is stirred
0.5g hydroxypropyl methylcellulose is added until being completely dissolved in 0.5h, and stirring 5min to hydroxypropyl methylcellulose is uniformly dispersed, and is spray-dried,
50-60 DEG C of inlet air temperature, atomization frequency 35HZ-40HZ, collect solid powder inspection XRD, map is such as by 30-35 DEG C of leaving air temp
Fig. 1 (salt free ligands angle), it was demonstrated that be amorphous.
Embodiment 2
20g cefditoren is suspended in 300ml chloroform, acetonitrile, in ethyl alcohol (2:1:1), and heat up 35 DEG C of stir abouts
0.5g hydroxypropyl methylcellulose is added until being completely dissolved in 0.5h-1h, and stirring 5min to hydroxypropyl methylcellulose is uniformly dispersed, spraying dry
Dry, 65-70 DEG C of inlet air temperature, atomization frequency 40-50HZ, collect solid powder inspection XRD, map is such as by 30-40 DEG C of leaving air temp
Fig. 2 (salt free ligands angle), it was demonstrated that be amorphous.
Embodiment 3
50g cefditoren is suspended in 500ml methylene chloride and acetone (volume ratio 1:1), is heated up 40 DEG C and is stirred
0.25g povidone k30 is added until being completely dissolved in 0.5h, and stirring 5min is uniformly dispersed to it, is spray-dried, inlet air temperature 50-
60 DEG C, atomization frequency 30HZ-40HZ, collect solid powder inspection XRD, map such as Fig. 3 (salt free ligands by 30-35 DEG C of leaving air temp
Angle), it was demonstrated that it is amorphous.
Embodiment 4
100g cefditoren is suspended in 2000ml ethyl acetate and acetone (volume ratio 1:2), and 40 DEG C of heating is stirred
0.5h is mixed, until being completely dissolved, 2g hydroxypropyl cellulose is added, stirring 10min is uniformly dispersed to it, is spray-dried, inlet air temperature
60-65 DEG C, atomization frequency 35HZ-40HZ, collect solid powder inspection XRD, map such as Fig. 4 (spread out by nothing by 30-35 DEG C of leaving air temp
Firing angle), it was demonstrated that it is amorphous.
Embodiment 5
30g cefditoren is suspended in 600ml ethyl acetate and acetone (volume ratio 1:2), is heated up 50 DEG C and is stirred
0.6g hydroxypropyl cellulose is added until being completely dissolved in 10min, and stirring 10min is uniformly dispersed to it, is spray-dried, inlet air temperature
60-65 DEG C, atomization frequency 35HZ-40HZ, collect solid powder inspection XRD, map such as Fig. 5 (spread out by nothing by 40-45 DEG C of leaving air temp
Firing angle), it was demonstrated that it is amorphous.
Embodiment 6
50g cefditoren is suspended in 400mlN, and dinethylformamide heats up with acetone (volume ratio 1:3)
1g methylcellulose is added until being completely dissolved in 30 DEG C of stirring 0.5h, and stirring 10min is uniformly dispersed to it, is spray-dried, air inlet
60-80 DEG C of temperature, atomization frequency 40HZ-50HZ, collect solid powder inspection XRD, map such as Fig. 6 by 50-60 DEG C of leaving air temp
(salt free ligands angle), it was demonstrated that be amorphous.
Comparative example 1
Suitable 1mol/L hydrochloric acid, 1mol/L ammonia spirit is respectively configured, weighs 0.5g hydroxypropyl cellulose in stirring bar
It is dissolved under part in the 1M hydrochloric acid of 350ml to complete clarification, weighs and above-mentioned acidity is added under the appropriate logical sequence ester stirring condition of 50g crystalline cephem
Solvent is added under agitation with above-mentioned acid solution in 1mol/L ammonium hydroxide, solid is analysed in N-process to complete clarification
Out, titration end-point pH6.5-7.0 is collected using filter paper and filtered on buchner funnel and solid is precipitated, depressurized in being dried under reduced pressure case
Under the conditions of 40-50 DEG C, it is dried to obtain solid powder, inspection XRD, map such as Fig. 7 (there are the part angles of diffraction).
Comparative example 1 and embodiment 1-6 map compare, and there are the part angles of diffraction in comparative example map, show non-high-purity
The amorphous state of degree, there are partially crystallizable states.Verified is amorphous state cefditoren, and crystal form is steady under the condition of high temperature and high humidity
Qualitative very poor, using water as solvent, drying temperature is higher longer with drying time, will lead to drying process partial material crystal form
Crystalline state is switched to by amorphous state, obtains mixed crystal cefditoren.
Embodiment 1-6 prepares the equal salt free ligands angle of sample XRD spectrum, show use present invention determine that technique obtain high-purity
Amorphous state cefoperon rouge, and process stabilizing.
Claims (7)
1. a kind of preparation method of amorphous state Cefditoren pivoxil Cephalosporins composition, which is characterized in that take crystalline state cefoperon
Ester dissolves in mixed organic solvents, and water-soluble high-molecular material is suspended in mixed organic solvents, spray-dried, obtains nothing
Shape state Cefditoren pivoxil Cephalosporins composition.
2. a kind of preparation method of amorphous state cefditoren composition according to claim 1, which is characterized in that institute
The mixed organic solvents stated are acetone, ethyl acetate, ethyl alcohol, acetonitrile, methylene chloride, chloroform and N,N-dimethylformamide
In any two kinds of solvents and any two or more compositions.
3. a kind of preparation method of amorphous state cefditoren according to claim 1, which is characterized in that the water
Soluble macromolecular material be in hydroxypropyl methylcellulose, hydroxypropyl cellulose, polyvinylpyrrolidone and methylcellulose it is any it
It is a kind of or any two or more.
4. a kind of preparation method of amorphous cefditoren according to claim 1, which is characterized in that the dissolution
The temperature of crystalline state cefditoren is 30~50 DEG C.
5. a kind of preparation method of amorphous cefditoren according to claim 1, which is characterized in that described spraying dry
Drying process parameter: inlet air temperature is 50-80 DEG C, leaving air temp is 30-60 DEG C, atomization frequency is 30HZ-50HZ.
6. a kind of preparation method of amorphous cefditoren according to claim 1, which is characterized in that crystalline state cephalo
The dosage mass volume ratio of appropriate logical sequence ester and organic solvent is 1:8~1:20g/ml.
7. a kind of preparation method of amorphous cefditoren according to claim 1, which is characterized in that water-soluble high score
Sub- material and crystalline state cefditoren mass ratio are 1:40~1:200g/g.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112190539A (en) * | 2020-11-10 | 2021-01-08 | 深圳立健药业有限公司 | Cefditoren pivoxil composition and application thereof |
| CN114306246A (en) * | 2020-09-29 | 2022-04-12 | 北京济美堂医药研究有限公司 | Preparation method of cefditoren pivoxil granules |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114306246A (en) * | 2020-09-29 | 2022-04-12 | 北京济美堂医药研究有限公司 | Preparation method of cefditoren pivoxil granules |
| CN112190539A (en) * | 2020-11-10 | 2021-01-08 | 深圳立健药业有限公司 | Cefditoren pivoxil composition and application thereof |
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