CN109111428A - A kind of dextral-rabeprazole sodium compound and its pharmaceutical composition - Google Patents
A kind of dextral-rabeprazole sodium compound and its pharmaceutical composition Download PDFInfo
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- CN109111428A CN109111428A CN201710485939.5A CN201710485939A CN109111428A CN 109111428 A CN109111428 A CN 109111428A CN 201710485939 A CN201710485939 A CN 201710485939A CN 109111428 A CN109111428 A CN 109111428A
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- dextral
- rabeprazole sodium
- sodium compound
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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Abstract
The present invention provides a kind of C crystal forms of dextral-rabeprazole sodium compound, it uses Cu target emanation, and the X-ray powder diffraction collection indicated with 2 θ angles has characteristic peak at about 6.22 ± 0.2,12.14 ± 0.2,12.46 ± 0.2,15.82 ± 0.2,18.90 ± 0.2,22.38 ± 0.2,26.56 ± 0.2,28.06 ± 0.2 degree.The crystal form is anhydrous crystal forms, and moisture content is low and is not easy the moisture absorption, and stability is good, is suitble to prepare dextral-rabeprazole preparation of sodium.
Description
Technical field
The invention belongs to field of medicaments, and in particular to a kind of novel crystal forms of dextral-rabeprazole sodium compound and its preparation side
Method, and the pharmaceutical composition containing the dextral-rabeprazole sodium compound.
Background technique
Dextral-rabeprazole sodium (Dexrabeprazole sodium, Formulas I), chemical name R- (+) -2- { [4- (3- methoxyl group
Propoxyl group) -3- picoline -2- base] methanesulfinyl -1H- benzimidazole sodium salt, by EMCURE pharmaceuticals of India first
Exploitation, in September, 2007 India list, for treat gastric ulcer, duodenal ulcer, marginal ulcer, reflux esophagitis,
Zhuo-Chinese mugwort (Zollinger-Ellison) syndrome (gastrinoma) active duodenal ulcer, benign active gastric ulcer,
H. pylori can be eradicated with antibiotic appropriate combination with the aggressivity of clinical symptoms or ulcerative stomach-esophageal reflux card
The duodenal ulcer of the bacterium positive.
CN104910135A discloses a kind of amorphous form of dextral-rabeprazole sodium, but amorphous form stability
Difference is not suitable for preparing solid pharmaceutical preparation.CN102924434A discloses a kind of monohydrate crystal form of dextral-rabeprazole sodium, is mesh
A kind of preceding disclosed relatively stable crystal form.CN102260244A discloses a kind of Rabeprazole sodium crystal, but wherein refers to ee
Value can not determine raceme or left or right rotation enantiomer, and the method according to specification, which repeats experiment, to be obtained
Solid.Furthermore without other crystal forms of discovery dextral-rabeprazole sodium.In order to improve the quality of dextral-rabeprazole preparation of sodium, into
The advantage drug crystal forms of one step research and development dextral-rabeprazole sodium are of great significance.
Summary of the invention
The purpose of the present invention is to provide a kind of crystal form of dextral-rabeprazole sodium compound shown in formula (I), the crystal forms
With excellent stability, particularly suitable for pharmaceutical preparation is prepared.
The present invention the following technical schemes are provided:
The C crystal form of one kind dextral-rabeprazole sodium compound as shown in formula (I) uses Cu target emanation, with 2 θ angles
X-ray powder diffraction (XRPD) map of expression about 6.22 ± 0.2,12.14 ± 0.2,12.46 ± 0.2,15.82 ± 0.2,
There is characteristic peak at 18.90 ± 0.2,22.38 ± 0.2,26.56 ± 0.2,28.06 ± 0.2 degree.The wherein maximum peak of relative intensity
It is about 6.22 ± 0.2 degree of characteristic peak.
Further, the X-ray powder diffraction collection about 6.22 ± 0.2,12.14 ± 0.2,12.46 ± 0.2,
13.10±0.2、15.82±0.2、17.34±0.2、17.70±0.2、18.90±0.2、20.18±0.2、20.74±0.2、
21.60±0.2、22.08±0.2、22.38±0.2、23.42±0.2、26.56±0.2、28.06±0.2、30.80±0.2
There is characteristic peak at degree.
Further, there is the C crystal form of the dextral-rabeprazole sodium compound XRPD substantially as shown in Figure 1 to scheme.Its
In 2 angles the θ error that allows to have ± 0.2 degree.
Differential scanning calorimetry (DSC) map of the B crystal form of the dextral-rabeprazole sodium compound is put at about 234 DEG C
Thermal spike.The wherein error that the temperature allows to have ± 5 DEG C.
There is the C crystal form of the dextral-rabeprazole sodium compound DSC substantially as shown in Figure 2 to scheme.
There is the C crystal form of the dextral-rabeprazole sodium compound TGA substantially as shown in Figure 3 to scheme.
There is the C crystal form of the dextral-rabeprazole sodium compound IR substantially as shown in Figure 4 to scheme.
The present invention also provides a kind of methods for preparing the C crystal form of dextral-rabeprazole sodium compound shown in formula (I), including
Step:
1) dextral-rabeprazole sodium is dissolved in methanol or ethyl alcohol, is concentrated to dryness, repeated aforementioned operation at least 1 time；
2) acetonitrile is added to the resulting residue of step 1), stirring is concentrated to dryness；
3) solvent toluene is added to the resulting residue of step 2) or dimethylbenzene, stirring and crystallizing obtains C crystal form.
In a preferred embodiment, dextral-rabeprazole sodium is dissolved in methanol in the step 1).
In a preferred embodiment, the dissolution of the step 1) and the number of repetition of concentration operation are preferably 1-6 times, more
It is preferred that 2-5 times, such as 3-4 times.
In a preferred embodiment, the stirring and crystallizing of step 3) carries out under inert gas protection, such as nitrogen.
In a preferred embodiment, the ratio of dextral-rabeprazole sodium and organic solvent can be 1g:(1- in step 1)
20) ml, such as 1g:(3-10) ml.
In a preferred embodiment, the ratio of acetonitrile can be 1g:(1-20 in dextral-rabeprazole sodium and step 2))
Ml, such as 1g:(3-10) ml.
In a preferred embodiment, the ratio of solvent can be 1g:(5-30 in dextral-rabeprazole sodium and step 3))
ml。
The present invention also provides a kind of pharmaceutical compositions, dextral-rabeprazole sodium compound and medicine containing above-mentioned crystal form
Acceptable carrier on.Any dosage form, preferably oral preparation, such as enteric coated tablet, glue can be made in described pharmaceutical composition
Capsule etc. or ejection preparation, such as freeze drying powder injection.
The present invention also provides above-mentioned dextral-rabeprazole sodium compound or its pharmaceutical composition in preparation for treating or pre-
Purposes in anti-gastrointestinal disease.For example, gastric ulcer, duodenal ulcer, marginal ulcer, reflux esophagitis, Zhuo-Chinese mugwort
(Zollinger-Ellison) syndrome (gastrinoma) active duodenal ulcer, benign active gastric ulcer, with facing
The aggressivity or ulcerative stomach-esophageal reflux card of bed symptom can eradicate the helicobacter pylori positive with antibiotic appropriate combination
Duodenal ulcer.
Dextral-rabeprazole sodium crystal of the invention is anhydrous crystal forms, and moisture content is low and is not easy the moisture absorption, is had excellent
Stability, suitable for preparing pharmaceutical preparation.
Detailed description of the invention
Fig. 1 is the XRPD figure of the C crystal form of dextral-rabeprazole sodium compound.
Fig. 2 is the DSC figure of the C crystal form of dextral-rabeprazole sodium compound.
Fig. 3 is the TGA figure of the C crystal form of dextral-rabeprazole sodium compound.
Fig. 4 is the IR figure of the C crystal form of dextral-rabeprazole sodium compound.
Fig. 5 is the XRPD figure of the A crystal form of dextral-rabeprazole sodium compound.
Fig. 6 is the XRPD figure of the amorphous state of dextral-rabeprazole sodium compound.
Fig. 7 is XRPD figure of the different crystal forms of dextral-rabeprazole sodium compound under grinding/hot conditions.
Fig. 8 is XRPD figure of the different crystal forms of dextral-rabeprazole sodium compound in suspension solution.
Specific embodiment
Below by way of specific embodiment, the present invention will be described in detail, it will be appreciated by those skilled in the art that following implementations
Example is only purpose of explanation, without limiting the scope of the invention in any way.Unless otherwise instructed, the behaviour in embodiment
It is routine operation as step.Room temperature can be 15-35 DEG C, and the crystallization time can be 3 hours to 4 days.
Test method:
XRPD tests (Fig. 1, Institute of Analysis of Nanjing Normal University): instrument model D/max 2500VL/PC, target type:
Cu (60kV, 100mA), scanning range: 3 ° -40 ° (2theta value), scanning step: 0.02, scanning speed: 5；
DSC test: instrument model: Perkin Elmer DSC 8500, temperature range: 50-300 DEG C, sweep speed: 10
DEG C/min, nitrogen flow rate: 50ml/min
TGA test: instrument model: Netzsch TG 209F3, temperature range: 25-700 DEG C, sweep speed: 20 DEG C/
Min, purge gass: 25ml/min protects gas: 15ml/min
IR test: instrument model: Thermo company NICOLET is5 infrared chromatograph, scanning times: 32, resolution ratio:
4.000, sampling gain: 1.0, sound speed: 0.4747, diaphragm: 100.00, detector DTGS KBr, beam splitter: KBr, light
Source: infrared light supply
XRPD tests (Fig. 5-8, Nanjing University's modern analysis center): instrument model: Thermo company X ' TRA type X diffraction
Instrument, target type: Cu (40kV, 40mA), scanning range: 2 ° -40 ° (2theta value), scanning step: 0.02, scanning speed: 5；
Water of hydroscopicity point measurement: 25 ± 1 DEG C of thermostatic driers (putting ammonium chloride saturated solution in bottom)
Related substance chromatographic condition:
Chromatographic column: with octadecylsilane chemically bonded silica be filler (Agilent ZORBAX Extend C18,250 ×
4.6mm,5μm)；
Mobile phase A: 0.025mol/L phosphate solution (0.025mol/L dipotassium hydrogen phosphate solution with phosphorus acid for adjusting pH value extremely
7.2)-acetonitrile (95:5)；Mobile phase B: methanol；Mobile phase C: acetonitrile；
According to the form below carries out linear gradient elution:
| Time (min) | A (%) | B (%) | C (%) |
| 0 | 65 | 30 | 5 |
| 15 | 65 | 30 | 5 |
| 45 | 15 | 55 | 30 |
| 50 | 15 | 55 | 30 |
| 52 | 65 | 30 | 5 |
| 60 | 65 | 30 | 5 |
Detection wavelength: 280nm, 220nm (are used for impurity H)
Flow velocity: 1.0ml/min
Column temperature: 25 DEG C
Sample volume: 5 μ l
Dilution: 0.1mol/L dipotassium hydrogen phosphate solution 2mol/L potassium hydroxide solution adjusts pH to 11.3- methanol
(45:55)
Laevoisomer detects chromatographic condition:
Chromatographic column: Chiralpack AGP chiral chromatographic column (150mm × 4.0mm, 5 μm)
Mobile phase: 0.01mol/L phosphate solution (0.01mol/L dipotassium hydrogen phosphate solution phosphorus acid for adjusting pH to 6.8,
Up to)-acetonitrile (90:10)
Dilution: 0.05mol/L sodium hydroxide solution-methanol (40:60)
Detection wavelength: 290nm
Flow velocity: 0.8ml/min
Column temperature: 30 DEG C
Sample volume: 10 μ l
Embodiment 1: the preparation of the C crystal form of dextral-rabeprazole sodium
Dextral-rabeprazole sodium 10g is taken, 50ml methanol stirring and dissolving is added, is concentrated to dryness in 45 DEG C, show bubble,
It repeats above-mentioned concentration step 5 times, about 20-35 DEG C stirred crystallization 18-24h of acetonitrile 50ml is added in residue, by T=45 DEG C of reaction solution
It is concentrated under reduced pressure, toluene 150ml is added to residue, under nitrogen protection for 24 hours in 35 DEG C of stirred crystallizations, filtering, filter cake toluene
50ml elution drain, 40 DEG C be dried under reduced pressure for 24 hours white solid 9.5g.Related substance HPLC:99.92%, single miscellaneous 0.028%,
Moisture KF 0.11%；Isomers HPLC:100%.
XRPD map is as shown in Figure 1.DSC map is as shown in Figure 2.TGA map is as shown in Figure 3.IR map is as shown in Figure 4.
The XRPD spectrum data of the C crystal form of 1. dextral-rabeprazole sodium of table
Embodiment 2: the preparation of the C crystal form of dextral-rabeprazole sodium
Dextral-rabeprazole sodium 20g is taken, 100ml methanol stirring and dissolving is added, is concentrated to dryness in 45 DEG C, is in foam
Shape repeats above-mentioned concentration step 4 times, and about 25 DEG C of stirred crystallization 20h of acetonitrile 100ml are added in residue, and 45 DEG C of reaction solution are depressurized
Toluene 300ml is added to residue in concentration, and under nitrogen protection for 24 hours in 35 DEG C of stirred crystallizations, filtering, filter cake toluene 90ml drenches
Wash and drain, 40 DEG C be dried under reduced pressure for 24 hours white solid 18.9g.It tests map and embodiment 1 is almost the same.
The polymorphous physicochemical property research of 3 dextral-rabeprazole sodium of embodiment
Dextral-rabeprazole sodium crystal is prepared according to the method for CN102924434A specification embodiment 1, is denoted as A crystal form.
XRPD map is as shown in figure 5, with consistent disclosed in this application.
Dextral-rabeprazole 100g is dissolved in 300ml methylene chloride, divides and goes upper aqueous layer, organic layer is slowly added into different
Propyl ether 2L, be stirred at room temperature 1h filtering, filter cake isopropyl ether 500ml is eluted, is drained, 35 DEG C be dried under reduced pressure 12h and obtain dextrorotation Lei Beila
Azoles sodium solid 63.5g is amorphous state.XRPD map is as shown in Figure 6.
Above-mentioned dextral-rabeprazole sodium amorphous state, A crystal form, C crystal form is separately sampled, physicochemical property is detected, is as a result seen
Table 2.
The polymorphous physicochemical property research of 2. dextral-rabeprazole sodium of table
Test result is shown: the appearance character of three kinds of samples is off-white powder shape；It is in water soluble；Without fixed
Form fusing point is lower, and melting range is longer, is in thermodynamic instability state, remaining two kinds of crystal form fusing point is higher, and C crystal form
Fusing point is apparently higher than A crystal form.Draw moist investigation result to have been surprisingly found that, C crystal form low in hygroscopicity is in A crystal form, and since its is extremely low
Initial moisture (almost anhydrous crystal form C), making it have in storage process can keep for a long time potential compared with low moisture content
Advantage.Especially in such as storing process of oral tablet, capsule, low moisture content and resistance to water soak are usually able to ascend original
Supplementary material degradation side reaction of the product because of the excessively high generation of hygroscopic moisture is effectively reduced in the chemical stability of material and auxiliary material.It keeps away simultaneously
Exempt from product because moisture is excessive, disintegrating agent contact wetting early period and reduce intracorporal disintegrating property.
The 4 polymorphous stability study of dextral-rabeprazole sodium of embodiment
The test of 4.1 influence factors
Dextral-rabeprazole sodium A crystal form, each 100mg of C crystal form are taken, is placed under different condition, was sampled in 0,10,20,30 day
Observe crystal form detection character and related substance.The results are shown in Table 3.
The 3. polymorphous stability study of dextral-rabeprazole sodium of table
Test result shows that C crystal form is suitable with A stability of crystal form under illumination condition；C crystal form under the conditions of high temperature and humidity
Stability is better than A crystal form.
4.2 hot test
It takes and is placed under different condition shown in dextral-rabeprazole sodium A crystal form, C crystal form according to the form below 4, sampling carries out XRPD inspection
It surveys, investigates crystal form variation.XRPD fitted figure is as shown in Figure 7.
The stability study of 4. dextral-rabeprazole sodium polymorphic of table under the high temperature conditions
It can be seen that crystal form C from the result of Fig. 7 and keep stable at high temperature, will not occur to turn crystalline substance；A crystal form is at high temperature
It is unstable, it is easy to happen and turns crystalline substance, the characteristic peak of crystal form C occur, judge to be changed into C crystal form under its hot conditions；A crystal form is being ground
When be converted into part unformed shape.Therefore C crystal form is stable crystal form, is suitble to prepare solid pharmaceutical preparation, such as oral tablet, capsule
Deng.
4.3 suspension blance tests
Unformed shape, A crystal form and C crystal form sample are respectively taken 1g to mix, in 35 DEG C and nitrogen atmosphere condition by according to the form below group
Lower and 10ml stirring solvent, sampling carry out XRPD detection, and map is as shown in Figure 8.Experimental condition and result are as shown in table 5 below.
The polymorphous suspension balance of 5. dextral-rabeprazole sodium of table
| Group | Initial sample mixture | Suspension solvent | It is suspended in time (day) | Product form |
| G-1 | C crystal form+unformed | Acetonitrile | 2 | C crystal form |
| G-2 | A crystal form+C crystal form | Acetonitrile | 2 | C crystal form |
| G-3 | A crystal form+unformed | Acetonitrile | 2 | C crystal form |
The results show that the stability of dextral-rabeprazole sodium C crystal form is better than amorphous state and A crystal form, it is most stable of crystalline substance
Type.
Claims (10)
1. a kind of dextral-rabeprazole sodium compound as shown in formula (I),
It is characterized in that, the dextral-rabeprazole sodium compound is C crystal form, Cu target emanation is used, is indicated with 2 θ angles
XRPD map 6.22 ± 0.2,12.14 ± 0.2,12.46 ± 0.2,15.82 ± 0.2,18.90 ± 0.2,22.38 ± 0.2,
There is characteristic peak at 26.56 ± 0.2,28.06 ± 0.2 degree.
2. dextral-rabeprazole sodium compound as described in claim 1, which is characterized in that the XRPD map 6.22 ±
0.2、12.14±0.2、12.46±0.2、13.10±0.2、15.82±0.2、17.34±0.2、17.70±0.2、18.90±
0.2、20.18±0.2、20.74±0.2、21.60±0.2、22.08±0.2、22.38±0.2、23.42±0.2、26.56±
0.2, there is characteristic peak at 28.06 ± 0.2,30.80 ± 0.2 degree.
3. dextral-rabeprazole sodium compound as described in claim 1, which is characterized in that the dextral-rabeprazole sodium is closed
Object has XRPD map substantially as shown in Figure 1.
4. dextral-rabeprazole sodium compound as described in claim 1, which is characterized in that the dextral-rabeprazole sodium is closed
The DSC map of object has exothermic peak at about 234 DEG C ± 5 DEG C.
5. dextral-rabeprazole sodium compound as described in claim 1, which is characterized in that the dextral-rabeprazole sodium is closed
Object has DSC map substantially as shown in Figure 2.
6. dextral-rabeprazole sodium compound as described in claim 1, which is characterized in that the dextral-rabeprazole sodium is closed
Object has TGA map substantially as shown in Figure 3.
7. a kind of method for preparing dextral-rabeprazole sodium compound described in claim 1, comprising steps of
1) dextral-rabeprazole sodium is dissolved in methanol or ethyl alcohol, is concentrated to dryness, repetitive operation the step at least 1 time；
2) acetonitrile is added to the resulting residue of step 1), stirring is concentrated to dryness；
3) solvent toluene or dimethylbenzene are added to the resulting residue of step 2), stirring and crystallizing to get.
8. the method for claim 7, including following characteristics a)-c) one or more:
A) wherein step 1) dextral-rabeprazole sodium is dissolved in methanol；
B) wherein the repetitive operation number of step 1) is preferably 1-6 times；
C) wherein the stirring and crystallizing of step 3) carries out under inert gas protection.
9. a kind of pharmaceutical composition includes dextral-rabeprazole sodium compound as claimed in any one of claims 1 to 6 and drug
Acceptable carrier on.
10. pharmaceutical composition as claimed in claim 9 is in preparation for treating or preventing the purposes in gastrointestinal disease, it is preferable that
The disease is selected from gastric ulcer, duodenal ulcer, marginal ulcer, reflux esophagitis, zes (gastrinoma)
Active duodenal ulcer, benign active gastric ulcer, the aggressivity with clinical symptoms or ulcerative stomach-esophageal reflux
Card can eradicate the duodenal ulcer of the helicobacter pylori positive with antibiotic appropriate combination.
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| CN201710485939.5A CN109111428A (en) | 2017-06-23 | 2017-06-23 | A kind of dextral-rabeprazole sodium compound and its pharmaceutical composition |
| US16/624,740 US11078184B2 (en) | 2017-06-23 | 2018-06-22 | Dexrabeprazole sodium compound and pharmaceutical composition thereof |
| PCT/CN2018/092347 WO2018233678A1 (en) | 2017-06-23 | 2018-06-22 | Dexrabeprazole sodium compound and pharmaceutical composition thereof |
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Cited By (3)
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|---|---|---|---|---|
| CN111024844A (en) * | 2019-12-18 | 2020-04-17 | 湖北省宏源药业科技股份有限公司 | Method for detecting related impurities of azithromycin capsules |
| CN111423412A (en) * | 2020-04-10 | 2020-07-17 | 江苏海悦康医药科技有限公司 | Crystalline form of d-rabeprazole sodium anhydride |
| CN113009029A (en) * | 2021-03-01 | 2021-06-22 | 丽珠集团丽珠制药厂 | Method for determining related substances of rabeprazole sodium enteric-coated preparation |
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