CN102276582A - Lomefloxacin aspartate compound - Google Patents
Lomefloxacin aspartate compound Download PDFInfo
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- CN102276582A CN102276582A CN2011102279595A CN201110227959A CN102276582A CN 102276582 A CN102276582 A CN 102276582A CN 2011102279595 A CN2011102279595 A CN 2011102279595A CN 201110227959 A CN201110227959 A CN 201110227959A CN 102276582 A CN102276582 A CN 102276582A
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Abstract
The invention relates to a crystal form of lomefloxacin aspartate and a preparation method thereof, and relates to a medicinal composition of lomefloxacin aspartate containing the crystal form and application of the crystal form to the preparation of medicaments for treating general infections such as human or animal respiratory tract infection, urogenital infection, gastrointestinal tract bacterial infection, infection of enterocoelia, biliary tract, typhoid fever and the like, bone and joint infection, skin soft tissue infection, ichorrhemia and the like which are caused by grampositive or gramnegative bacterial sensitive bacteria and other infections such as paranasal sinusitis, tympanitis, blepharitis and the like.
Description
Technical field
Pharmaceutical composition, preparation method and this crystal formation that the present invention relates to contain lomefloxacin aspartate crystal formation is used for making the application of the hypochondriacal medicine of treatment.
Background technology
Infectious diseases is a modal clinically class disease, relates to clinical nearly all training, also is one of modal reason that causes death.According to the World Health Organization's 1997 annual reports, the number of suffering from infectious diseases death is up to 33.3% of all kinds of reason death toll summations.In China, because vast people in the countryside and still also very backward medical health protection system, the principal disease of harm people ' s health is still by the various microbial infectious diseases that cause a disease, and also is to cause to disable and main causes of death.Anti-infective is human powerful mean of struggling with infectious diseases, its quantity maximum, most species, with fastest developing speed, and the market requirement of this respect medicine is always very vigorous.According to statistics, the sales volume of anti-infection drug accounts for about 15% of world's medicine sales volume, is only second to painstaking effort tubing medicine.In China, anti-infective accounts for the market share of whole medicine sale about 14%, ranks first in all medicine types.
Fluoroquinolones (fluoroquinolone) is the antibacterials that develop rapidly in the last few years, has strong and other antimicrobial drug commonly used of has a broad antifungal spectrum, antimicrbial power and does not have many characteristics such as cross resistance.30.4 hundred million dollars of its world's sales volumes in 1997.At present, the appearance of a lot of new fluoroquinolones and structural modification thing, the limited compound of the early stage application of this class is developed into have suitable broad spectrum antibiotic activity, the medicine of good pharmacokinetic property, thereby more and more be subjected to the concern and the attention of countries in the world, become and competitively produce exploitation and the kind of using.
International academic community is divided into four-stage with the research and development of quinolones: the fs is the early stage of development, time is the seventies in 20th century, main products has Nalidixic Acid, pipemidic acid etc., these products only have moderate anti-Gram-negative bacteria activity, and pharmacokinetics and security are undesirable, now belong to superseded kind substantially.From subordinate phase, quinolone enters fast-developing period, the chemically modified fluoroquinolone that after its main ring 6 or 8 add fluorine atom, is otherwise known as, and representative products has norfloxicin, Ofloxacine USP 23, Ciprofloxacin.Coming out one after another of fluoroquinolone series products, make academia brand-new evaluation arranged and obtained clinical application widely the quinolone product, obtain consistent favorable comment, its comprehensive clinical efficacy is with Gram-negative bacteria, surpass penicillin family, reached the effect of first and second cynnematin in generation.Wherein the anti-microbial activity of Ciprofloxacin is the strongest, account in the world first of this work-in-process sales volume, nineteen ninety, sales volume was above 800,000,000 dollars, occupy second of all antibiotics, 1989-1995 is sure to occupy the 4th of U.S.'s prescription drug continuously, it is predicted that Ciprofloxacin will keep being in great demand in a few years from now on, a year volume of trade will reach 1,500,000,000 dollars.Phase III has been the new listing product since entering the nineties in 20th century, compare with old fluoroquinolone compounds, antimicrobial spectrum on the pharmacodynamics expands anti-Gram-negative and negative bacterium to, pathogenic bacterium in chlamydozoan, mycoplasma and the cell, anti-microbial activity also improves greatly, pharmacokinetics and security simultaneously also had very big improvement, and comprehensive clinical efficacy reaches new level, and academia generally acknowledges the effect that has reached fully above third generation cephalosporin.
In recent years, microorganism causes very big concern to its chemical sproof growth.In the past few years, the research of new fluoroquinolone medicine is that target: ⑴ strengthens antipneumococcic activity to improve microbiological property; ⑵ strengthen the activity of resisting gram-positive coccus; ⑶ strengthen antistaphylococcic activity, particularly methicillin-resistant staphylococcus aureus (MRSA); ⑷ strengthen the activity of anaerobe resistant; ⑸ strengthen the activity of anti-anti-Ciprofloxacin and Ofloxacine USP 23; ⑹ strengthen the activity of anti-Gram-negative bacteria; ⑺ reduce the resistance occurrence rate.The medicine of Chu Xianing is tending towards satisfying above-mentioned requirements in some aspects subsequently.
On kind, the quinolone product that has gone on the market has tens kinds, is one of exploitation most active fields in the anti-infectives.Along with pharmaceutical chemical development, people can infer certain medicine voltinism matter that many side chains may have now, thereby can be by the developing direction of computer optimization structure and selected medicine, its development trend might surpass Beta-lactam medicine, become the principal item of the anti-infectives of 21 century.The eighties in 20th century, the kind of listing reached 11 kinds, and they are norfloxicin, enoxacin, Pefloxacin, Ofloxacine USP 23, Ciprofloxacin, lomefloxacin, sieve Flucloxacillin, fleroxacin, Tosulfloxacin, levofloxacin, Sparfloxacin etc.
Lomefloxacin (Lomefloxacin) is developed by HDK drugmaker and Shionogi company are common, and the product of being produced by U.S. Searle company (commodity be called Maxaquin) goes on the market.
Fluoroquinolones has characteristics such as has a broad antifungal spectrum, antimicrbial power are strong, better tolerance, and it is clinical that oral preparations is widely used in, and its injection can improve Plasma Concentration, heightens the effect of a treatment the broadened application scope.It is a kind of ideal parenterai administration approach.But because fluoroquinolones poorly water-soluble, generally increase the solvability of medicine in water with its salify, to reach the required concentration of injection with organic acid (as lactic acid, aspartic acid, gluconic acid etc.) that adapts to Human Physiology or mineral acid (example hydrochloric acid etc.).Lomefoxacin Aapartate has better solvability and stability than lomefloxacin hydrochloride.The Lomefoxacin Aapartate injection liquid directly injects human body by the mode of having an injection or infusing, and the peak reaching time of blood concentration of lomefloxacin is shortened, and is beneficial to particularly critical illness patient medication and see curative effect as early as possible of patient.
Popular name: Lomefoxacin Aapartate;
English name: Lomefloxacin Aspartate;
Chemical name: 1-ethyl-6,8-two fluoro-1,4-dihydro-7-(3-methyl isophthalic acid-piperazinyl)-4-oxo-3-quinoline carboxylic acid aspartate;
Structural formula: C
17H
19F
2N
3O
3C
4H
7NO
4
Molecular weight: 484.46;
Application number be CN03140207.0 disclosure of the Invention a kind of Lomefoxacin Aapartate pulvis and preparation technology's method thereof, it is characterized in that: described pulvis comprises Lomefoxacin Aapartate and vehicle, this vehicle is water miscible carbohydrate, has aldehyde, ketone, the alcohol of n hydroxyl; Carbon number m=3 ~ 8 of described aldehyde, ketone, alcohol, and n=(m-2), (m-1) or m.The invention provides a kind of formulation physico-chemical property stablizes, can reduce the preparation link in the clinical application, the Lomefoxacin Aapartate pulvis of being convenient to storage/transportation and a kind of corresponding processing method for preparing described Lomefoxacin Aapartate pulvis.
Application number is that the invention of CN200710166627.4 relates to a kind of aspartic acid laumosaren hydrate and preparation and purposes.(its molecular formula is C17H19F2N3O3C4H7NO4nH2O to aspartic acid laumosaren hydrate of the present invention, n=0.5 ~ 2.5), aspartic acid laumosaren hydrate of the present invention is a fluoroquinolone antibacterial agent, be used to be applicable to respiratory tract infection to the human or animal due to Gram-positive or the negative bacteria sensitive organism, urogenital infections, the gi tract infectation of bacteria, the abdominal cavity, biliary tract, infection such as typhoid fever, the bone and the infection of joint, skin soft-tissue infection, systemic infections such as septicemia, other infection are as nasal sinusitis, otitis media, blepharitises etc., its advantage are the stable existence of energy, be convenient to store and transportation, can conveniently be used for the preparation of pharmaceutical preparation.
The Lomefoxacin Aapartate injection liquid that prior art is produced all has very strict requirement to the requirement of storage, lucifuge, all has inconvenience in use, preservation and transportation.
The inventor finds that also there is heteromorphism in the lomefloxacin aspartate, has found other three kinds of crystal formations in research process, be different from disclosed the sort of crystal formation in the above-mentioned patent, surprised is that wherein a kind of crystal formation is different from other two kinds of crystal formations, has excellent characteristic, this crystal formation solubleness is big, this is of crucial importance to medicine performance curative effect, also has the purity height, good stability, on industrial production, have superiority, be fit to preparation technical process and standing storage.
Summary of the invention
One object of the present invention discloses a kind of new crystal of lomefloxacin aspartate.
Another object of the present invention discloses the preparation method of lomefloxacin aspartate new crystal.
Another purpose of the present invention discloses the pharmaceutical composition that comprises lomefloxacin aspartate new crystal.
Now content of the present invention is specifically described in conjunction with purpose of the present invention.
The invention provides a kind of new crystal of lomefloxacin aspartate, this crystal form X ray powder diffraction charateristic avsorption band (2 θ) and D value are as follows, and error is ± 0.2, sees accompanying drawing 1.
| Peak number | Diffraction angle (2 θ) | The D value | I/I 0 |
| 1 | 4.380 | 20.1574 | 4 |
| 2 | 5.000 | 17.6591 | 100 |
| 3 | 10.000 | 8.8380 | 37 |
| 4 | 11.780 | 7.5062 | 2 |
| 5 | 12.540 | 7.0530 | 1 |
| 6 | 15.020 | 5.8935 | 28 |
| 7 | 15.300 | 5.7863 | 8 |
| 8 | 16.280 | 5.4401 | 1 |
| 9 | 18.440 | 4.8075 | 3 |
| 10 | 18.920 | 4.6866 | 3 |
| 11 | 19.200 | 4.6189 | 8 |
| 12 | 19.560 | 4.5347 | 32 |
| 13 | 21.160 | 4.1952 | 5 |
| 14 | 22.780 | 3.9004 | 3 |
| 15 | 23.500 | 3.7825 | 5 |
| 16 | 24.440 | 3.6391 | 2 |
| 17 | 24.700 | 3.6014 | 2 |
| 18 | 25.260 | 3.5228 | 3 |
| 19 | 26.280 | 3.3884 | 2 |
| 20 | 26.720 | 3.3336 | 4 |
| 21 | 28.140 | 3.1685 | 2 |
| 22 | 28.460 | 3.1336 | 2 |
| 23 | 28.980 | 3.0785 | 2 |
| 24 | 30.360 | 2.9417 | 4 |
| 25 | 30.960 | 2.8860 | 2 |
| 26 | 35.060 | 2.5573 | 1 |
| 27 | 36.500 | 2.4597 | 2 |
| 28 | 37.560 | 2.3927 | 1 |
| 29 | 39.780 | 2.2641 | 1 |
| 30 | 40.940 | 2.2026 | 2 |
| 31 | 46.220 | 1.9625 | 2 |
| 32 | 46.800 | 1.9395 | 1 |
| 33 | 47.660 | 1.9065 | 1 |
The mensuration of 2 θ values is used light source among the present invention, and precision is ± 0.2 °, therefore represents above-mentioned value of getting to allow certain reasonably limit of error, and its limit of error is ± 0.2 °.
Fusing point test: measure fusing point according to Pharmacopoeia of People's Republic of China (2010 editions, two ones) appendix VI C first method, the fusing point that records is 262-265 ℃.
Another object of the present invention discloses the preparation method of lomefloxacin aspartate new crystal, by lomefloxacin being dissolved in 5-10 times of dimethyl formamides, feeds exsiccant hydrogenchloride, or adds the Aspartic Acid ether and obtain to PH1-3.Above-mentioned aprotic solvent has dimethyl formamide, dimethyl sulfoxide (DMSO), tetrahydrofuran (THF).
And, in the tetrahydrofuran (THF), add acidic alcohol respectively in the non-protonic solvent dimethyl sulfoxide (DMSO), and then obtain other 2 kinds of crystal formations respectively, be designated as 1 type, 2 types.
Above-mentioned three kinds of crystal formations, surprisingly, wherein a kind of crystal formation, lomefloxacin aspartate new crystal just disclosed by the invention has excellent characteristic, and this crystal formation solubleness is big, and this is of crucial importance to medicine performance curative effect, also has the purity height, good stability has superiority on industrial production, be fit to preparation technical process and standing storage.
Another purpose of the present invention provides the pharmaceutical composition that comprises lomefloxacin aspartate new crystal.Preparation of pharmaceutical compositions of the present invention is as follows: use standard and conventional technology; make acceptable solid or injection on The compounds of this invention and the technology of pharmaceutics; and make it at random to combine with acceptable auxiliary and vehicle on the technology of pharmaceutics and be prepared into particulate or microballoon, solid dosage comprises tablet, discrete particles, capsule, slow releasing tablet, sustained release pellet or the like.Solid carrier can be at least a material, and it can serve as thinner, flavouring agent, solubilizing agent, lubricant, suspension agent, tackiness agent, disintegrating agent and coating agent.Inert solid carrier comprises trimagnesium phosphate, Magnesium Stearate, smoothers sugar, lactose, pectin, propylene glycol, Polysorbate 80, dextrin, starch, gelatin, cellulose substances for example methylcellulose gum, Microcrystalline Cellulose, low melt point paraffin, polyoxyethylene glycol, N.F,USP MANNITOL, theobroma oil etc.
The amount of the active ingredient that contains in pharmaceutical composition and the unit dosage form (The compounds of this invention) can be according to patient's the state of an illness, specific being applied of situation of diagnosis, the amount of used compound or concentration are regulated in the scope of a broad, and the weight range of active compound is 1%～40%(weight of composition).
Stability test
The result: from 0-10 days, outward appearance, X powder diffraction, infrared absorption spectrum, thermogram spectrum did not all change the lomefloxacin aspartate, and stable crystal form is described, do not have the trichite of commentaries on classics and give birth to, and still keep original crystal formation under high light, high temperature, super-humid conditions; Related substance, content do not change in addition, illustrate that the new crystal chemical stability is good, are fit to the manufacturing and the standing storage of pharmaceutical preparation.
Solubility experiment
According to people such as Liu Kefei, Shenyang Pharmaceutical University's journal, 2010,27(11): 853, adopt classical null readings to measure the IV type, X III type, 1 type, 2 types, crystal formation dissolubility data of the present invention is represented with ug/ml.
Figure of description:
The X-ray diffractogram of lomefloxacin aspartate new crystal;
Embodiment:
The present invention is described further below in conjunction with embodiment, makes this area professional and technical personnel better understand the present invention.Embodiment only is indicative, means that never it limits the scope of the invention by any way.
Used Lomefoxacin Aapartate among the present invention, according to document Journal of Medicinal Chemistry, 2008,47 (19): 4684-4692, the method that provides is synthetic, purity 98.4% (HPLC normalization method).Chemical structure is proved conclusively through ultimate analysis, proves that chemical structure is correct.
Embodiment 1
In the 1000ml reaction flask of stirring, thermometer, condenser is housed, add 30 gram lomefloxacin and 180ml dimethyl formamides, start stirring, heat to 50 ℃-55 ℃, filter, filtrate is chilled to 5 ℃-10 ℃, adds the Aspartic Acid ether to PH1-3, be chilled to 0 ℃-5 ℃ then, insulated and stirred 13 hours.The crystallization of separating out is filtered, divide equally three washings with the 50ml anhydrous diethyl ether, indoor placement 1 hour, move in the vacuum drying oven then, room temperature vacuum-drying 3 hours, get 26.1 gram lomefloxacin aspartate white crystalline powders, fusing point is 262-265 ℃, purity 99.91% (HPLC normalization method).
The X-ray diffractogram of this crystalline powder is seen Fig. 1.Instrument model and condition determination: Japanese D/max 2500 type diffractometers of science; CuKa 40Kv 100mA; 2 θ sweep limit: 0-50
°
Embodiment 2
The granule that contains lomefloxacin aspartate new crystal
Prescription: lomefloxacin aspartate 100 grams of new crystal, lactose 650 grams, Microcrystalline Cellulose 30 grams, polyvinylpolypyrrolidone 68 grams, 80 gram PEG-4000, Vltra tears 110 grams, distilled water is an amount of, makes 1000 bags.
The lomefloxacin aspartate of technology: PEG-4000 and new crystal is pulverized jointly, crosses 80 mesh sieves, with behind other material mixing with being packed as granule after distilled water system softwood, granulation, the cryodrying.
Embodiment 3
The capsule that contains lomefloxacin aspartate new crystal
Prescription: lomefloxacin aspartate 100 grams of new crystal, propylene glycol 16ml, starch 120 grams, Magnesium Stearate 26 grams, colloidal silica 35 grams are made 1000.
Technology: lomefloxacin aspartate, starch, Magnesium Stearate, the colloidal silica of new crystal is wetting with 15% aqueous solution of propylene glycol, the granulation of sieving behind the mixing, 60 ℃ of dryings, whole grain, filled capsules.
Embodiment 4
The tablet that contains lomefloxacin aspartate new crystal
Prescription: lomefloxacin aspartate 100 grams of new crystal, Microcrystalline Cellulose 30 grams, lactose 160 grams, 16 gram PEG-4000, Magnesium Stearate 12 grams, 25 gram 30 POVIDONE K 30 BP/USPs 30, croscarmellose sodium 40 grams, talcum powder 10 grams, distilled water is an amount of, makes 1000.
The lomefloxacin aspartate of technology: PEG-4000 and new crystal is pulverized jointly, crosses 80 mesh sieves, with behind other material mixing with distilled water system softwood, 16 mesh sieve system particles are put in the loft drier in 40-45 ℃ of drying, the whole grain of 16 mesh sieves, Magnesium Stearate adds mixing in the dried particle, compressing tablet.
Embodiment 5
The injection that contains lomefloxacin aspartate new crystal
Lomefoxacin Aapartate 100g(is in lomefloxacin)
Water for injection adds to 2L
The preparation method: get recipe quantity water for injection 80%, temperature adds the recipe quantity Lomefoxacin Aapartate at 70-80 ℃, is stirred to dissolving fully; In above-mentioned solution, add Medicinal Charcoal, stir; Suction filtration replenishes water for injection to full dose, mixes; Record initial pH value,, regulate pH value scope at 3.0-5.0 with 4% sodium hydroxide solution and 10% CYSTEAMINE HCL acid solution according to initial pH value; Smart filter; Can; Sterilization; The lamp inspection; Warehouse-in; Get product.
Claims (6)
1.
Lomefoxacin Aapartate compound shown in the formula (I),
(I)
It is characterized in that: in measuring as the characteristic X-ray powder with the CuKa ray, its collection of illustrative plates has following 2 θ diffraction angle and D value,
The error of 2 θ diffraction angle is 0.2.
2. the described crystal formation of claim 1, it is characterized in that: the fusing point of described crystal formation is 262-265 ℃.
3. the preparation method of the described Lomefoxacin Aapartate crystal formation of claim 1 by Lomefoxacin Aapartate is dissolved in the aprotic solvent, adds the Aspartic Acid ether and obtains to PH1-3.
4. the described preparation method of claim 3, it is characterized in that comprising the following steps: by Lomefoxacin Aapartate being dissolved in 5-10 times of dimethyl formamides, start stirring, heat to 50 ℃-55 ℃, filter, filtrate is chilled to 5 ℃-10 ℃, adds the Aspartic Acid ether to PH1-3, be chilled to 0 ℃-5 ℃ then, insulated and stirred 12-15 hours.The crystallization of separating out is filtered, divide equally three washings with the 50ml anhydrous diethyl ether, indoor placement 1 hour moves in the vacuum drying oven then, and room temperature vacuum-drying 3 hours obtains the Lomefoxacin Aapartate white crystalline powder.
5. one kind contains the Lomefoxacin Aapartate of the described crystal formation of claim 1 and the Lomefoxacin Aapartate composition that one or more pharmaceutically acceptable carriers are formed.
6. right requires 5 described compositions, it is characterized in that said composition is used to prepare injection.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104352456A (en) * | 2014-11-21 | 2015-02-18 | 重庆方通动物药业有限公司 | Lomefloxacin hydrochloride powder-injection and preparation method thereof |
| CN105777711A (en) * | 2016-04-07 | 2016-07-20 | 常州大学 | Medicine eutectic of lomefloxacin and 5F-isophthalic acid and preparation method thereof |
| CN105949173A (en) * | 2016-05-26 | 2016-09-21 | 河南精康制药有限公司 | Preparation method of lomefloxacin aspartate |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1488349A (en) * | 2003-08-19 | 2004-04-14 | 洋浦华海医药物资有限公司 | Aspartic acid lomefloxacin powder and preparing method thereof |
| CN101029043A (en) * | 2006-12-05 | 2007-09-05 | 刘力 | Aspartic acid laumosaren hydrate, its production and use |
| CN101157684A (en) * | 2006-12-05 | 2008-04-09 | 刘力 | Aspartic acid lomefloxacin hydrate and preparation and uses thereof |
-
2011
- 2011-08-10 CN CN2011102279595A patent/CN102276582A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1488349A (en) * | 2003-08-19 | 2004-04-14 | 洋浦华海医药物资有限公司 | Aspartic acid lomefloxacin powder and preparing method thereof |
| CN101029043A (en) * | 2006-12-05 | 2007-09-05 | 刘力 | Aspartic acid laumosaren hydrate, its production and use |
| CN101157684A (en) * | 2006-12-05 | 2008-04-09 | 刘力 | Aspartic acid lomefloxacin hydrate and preparation and uses thereof |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104352456A (en) * | 2014-11-21 | 2015-02-18 | 重庆方通动物药业有限公司 | Lomefloxacin hydrochloride powder-injection and preparation method thereof |
| CN105777711A (en) * | 2016-04-07 | 2016-07-20 | 常州大学 | Medicine eutectic of lomefloxacin and 5F-isophthalic acid and preparation method thereof |
| CN105949173A (en) * | 2016-05-26 | 2016-09-21 | 河南精康制药有限公司 | Preparation method of lomefloxacin aspartate |
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Application publication date: 20111214 |