CN113214121A - Glibenclamide-arginine co-amorphous - Google Patents
Glibenclamide-arginine co-amorphous Download PDFInfo
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
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- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
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- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/59—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of rings other than six-membered aromatic rings
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- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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Abstract
The present disclosure relates to glibenclamide-arginine co-amorphous forms. Particularly, the disclosure relates to a co-amorphous substance of glibenclamide and arginine, which can greatly improve the solubility of glibenclamide, has good stability, and is suitable for industrial production and industrial application.
Description
Technical Field
The disclosure relates to the field of medicines, in particular to a glibenclamide and arginine co-amorphous substance, which improves the solubility of glibenclamide, has good stability and is suitable for industrial production and application.
Background
Glyburide (Glyburide) is a second generation of sulfonylurea oral hypoglycemic drug with the chemical name of N- [2- [4- [ [ [ (cyclohexylamino) carbonyl ] amino ] sulfonyl ] phenyl ] ethyl ] -2-methoxy-5-chlorobenzamide, and has the advantages of small dosage, small toxic and side effects, strong hypoglycemic effect and the like. However, glibenclamide has low water solubility (the solubility in water at 25 ℃ is 0.1mg/mL and is insoluble according to the definition of Chinese pharmacopoeia), is highly lipophilic (LogP is 4.5), belongs to a typical BCSII medicament, and has extremely low bioavailability so as to limit the clinical application of the glibenclamide.
The present disclosure provides a co-amorphous substance of glibenclamide and arginine, which can improve the solubility of glibenclamide to a great extent, has good stability, and is suitable for industrial production and industrial application.
Disclosure of Invention
The present disclosure provides a glibenclamide-arginine co-amorphous form.
In some embodiments, the glyburide-arginine co-amorphous comprises glyburide and arginine in a molar ratio selected from 1:3.1 to 8.5.
The present disclosure provides a glibenclamide-arginine co-amorphous form, which is formed by combining glibenclamide and arginine according to a molar ratio of 1: 3.1-8.5.
In some embodiments, the glibenclamide-arginine co-amorphous form is formed by combining glibenclamide and arginine in a molar ratio of 1:3.1 to 1:4.1, 1:3.5 to 1:4.5, 1:4.1 to 1:5.1, 1:4.5 to 1:5.5, 1:5.1 to 1:6.1, 1:5.5 to 1:6.5, 1:6.1 to 1:7.1, 1:6.5 to 1:7.5, 1:7.1 to 1:8.1, or 1:7.5 to 5: 8.5.
In some embodiments, the glibenclamide-arginine co-amorphous form is formed by combining glibenclamide and arginine in a molar ratio of 1:5.5, 1:5.6, 1:5.7, 1:5.8, 1:5.9, 1:6, 1:6.1, 1:6.2, 1:6.3, 1:6.4, or 1: 6.5.
In some embodiments, the molar ratio of glyburide to arginine in the glyburide-arginine co-amorphous is selected from 1:3.1 to 1:4.1, 1:3.5 to 1:4.5, 1:4.1 to 1:5.1, 1:4.5 to 1:5.5, 1:5.1 to 1:6.1, 1:5.5 to 1:6.5, 1:6.1 to 1:7.1, 1:6.5 to 1:7.5, 1:7.1 to 1:8.1, or 1:7.5 to 5: 8.5.
In some embodiments, the molar ratio of glyburide to arginine in the glyburide-arginine co-amorphous is selected from 1:5.5, 1:5.6, 1:5.7, 1:5.8, 1:5.9, 1:6, 1:6.1, 1:6.2, 1:6.3, 1:6.4, or 1: 6.5.
In some embodiments, the molar ratio of glibenclamide to arginine in the solution after the glibenclamide-arginine co-amorphous dissolution is 1: 3.1-8.5.
In some embodiments, the molar ratio of glyburide to arginine in the solution after glyburide-arginine co-amorphous dissolution is selected from 1:3.1 to 1:4.1, 1:3.5 to 1:4.5, 1:4.1 to 1:5.1, 1:4.5 to 1:5.5, 1:5.1 to 1:6.1, 1:5.5 to 1:6.5, 1:6.1 to 1:7.1, 1:6.5 to 1:7.5, 1:7.1 to 1:8.1, or 1:7.5 to 5: 8.5.
In some embodiments, the molar ratio of glyburide to arginine in the solution after glyburide-arginine co-amorphous dissolution is selected from 1:5.5, 1:5.6, 1:5.7, 1:5.8, 1:5.9, 1:6, 1:6.1, 1:6.2, 1:6.3, 1:6.4, or 1: 6.5.
The glibenclamide-arginine co-amorphous form disclosed by the disclosure is characterized in that a powder X-ray diffraction pattern of the glibenclamide-arginine co-amorphous form has no sharp diffraction peak.
The glibenclamide-arginine co-amorphous disclosed by the disclosure is characterized by an infrared absorption spectrum of 1637, 1550, 1404, 1319, 1275, 1239, 1178, 1123, 1083, 1081, 910, 867, 810, 661, 611, 545cm-1Has characteristic peaks.
The glibenclamide-arginine co-amorphous disclosed by the disclosure is characterized in that the infrared absorption spectrum of the glibenclamide-arginine co-amorphous is 3351, 1637, 1550, 1404, 1319, 1275, 1239, 1178, 1123, 1083, 1081, 910, 867, 810, 661, 611, 545cm-1Has characteristic peaks.
The glibenclamide-arginine co-amorphous form disclosed by the disclosure is characterized in that an infrared absorption spectrum is shown in figure 4.
The glibenclamide-arginine co-amorphous substance is characterized by having an infrared absorption spectrum of 3354, 1637, 1550, 1404,1319、1275、1239、1178、1123、1083、1081、910、867、810、661、611、545cm-1Has characteristic peaks.
The glibenclamide-arginine co-amorphous form disclosed by the disclosure is characterized in that an infrared absorption spectrum is shown in figure 5.
The glibenclamide-arginine co-amorphous form disclosed by the disclosure is characterized in that the Tg of the glibenclamide-arginine co-amorphous form is-105.24 ℃.
The glibenclamide-arginine co-amorphous substance disclosed by the disclosure is characterized by a Raman spectrum of 83.74, 262.48, 367.32, 686.06 and 1153.58cm-1Without a characteristic peak.
The glibenclamide-arginine co-amorphous form of the present disclosure is characterized by a Raman spectrum with a characteristic peak at 1125.63.
The glibenclamide-arginine co-amorphous form of the present disclosure is characterized by a Raman spectrum as shown in the spectral curves of batch 1, batch 2 or batch 3 (i.e., top-to-bottom curves 3, 4 and 5) in fig. 6.
The disclosure also provides a preparation method of the glibenclamide-arginine co-amorphous form, which is characterized in that a solvent evaporation method or a grinding method is adopted.
The preparation method of the glibenclamide-arginine co-amorphous is characterized in that a solvent evaporation method is selected from a solution drying method or a freeze drying method.
The glibenclamide-arginine co-amorphous preparation method comprises the following steps: weighing certain mass of glibenclamide and arginine, adding certain volume of water, stirring for a period of time at room temperature, filtering a membrane, and drying supernatant to obtain the glibenclamide-arginine co-amorphous form disclosed by the invention, wherein the mass of the glibenclamide and the arginine added into the water is larger than the solubility of the glibenclamide and the arginine.
The present disclosure also provides a pharmaceutical composition comprising the glibenclamide-arginine co-amorphous form, optionally comprising one or more pharmaceutically acceptable carriers and/or diluents.
The present disclosure also provides a pharmaceutical composition prepared from the glibenclamide-arginine co-amorphous form.
In some embodiments, the pharmaceutical composition further comprises one or more pharmaceutically acceptable carriers and/or diluents.
In addition, the pharmaceutical compositions of the present invention may be administered to a patient or subject in need of such treatment by any suitable mode of administration, for example, oral, parenteral, rectal, pulmonary or topical administration. When used for oral administration, the pharmaceutical composition can be prepared into oral preparations, for example, oral solid preparations such as tablets, capsules, pills, granules and the like; or oral liquid preparations such as oral solution, oral suspension, syrup, etc. When formulated into oral preparations, the pharmaceutical preparations may further contain suitable fillers, binders, disintegrants, lubricants and the like. When used for parenteral administration, the pharmaceutical preparation can be prepared into injections, including injection solutions, sterile powders for injection, and concentrated solutions for injection. When prepared into injections, the pharmaceutical composition may be manufactured by a conventional method in the existing pharmaceutical field. When preparing injection, the pharmaceutical preparation can be added with no additive, or added with proper additive according to the nature of the medicine. When used for rectal administration, the pharmaceutical preparation may be formulated into suppositories and the like. For pulmonary administration, the pharmaceutical formulation may be formulated as an inhalant or a spray.
The disclosure also provides the use of the glibenclamide-arginine co-amorphous form in the preparation of a medicament for treating diabetes.
The glibenclamide-arginine co-amorphous provided by the invention has the advantage that the solubility of glibenclamide in water is remarkably improved and is 0.7-5.83 mg/ml.
The glibenclamide-arginine co-amorphous form disclosed by the invention is placed for 3 months, 6 months, 9 months, 12 months, 18 months or 24 months under the conditions of 40 ℃ and 75 +/-5% of relative humidity, and no crystal transformation occurs in the co-amorphous form, so that the glibenclamide-arginine co-amorphous form is good in stability, is suitable for production and storage of medicines, and has the potential of being developed into a pharmaceutical preparation.
The glibenclamide-arginine co-amorphous form of the present disclosure can be prepared using water as a solvent, using a solvent evaporation method. The preparation method avoids the use of organic solvent in the preparation process, and is more green and environment-friendly.
In some embodiments, the milling process does not comprise freeze milling. The glibenclamide-arginine co-amorphous form disclosed by the invention is suitable for industrial production without adopting a preparation method of freeze grinding, and is more favorable for application of the co-amorphous form in the pharmaceutical industry.
The Tg described in this disclosure allows for errors within ± 2 ℃.
The peak position of the infrared absorption spectrum disclosed by the disclosure allows the existence of +/-2 cm-1Although it is 1637cm, for example-1Has characteristic peaks, but actually comprises 1635-1639 cm-1In the case of characteristic peaks.
The molar ratio of glyburide to arginine described in the present disclosure allows for a 5% error, for example a co-amorphous molar ratio of 1:6 may encompass co-amorphous molar ratios in the range of 19:120 to 21: 120.
"optional" means that the subsequently described event or circumstance may, but need not, occur, and that the description includes instances where the event or circumstance occurs or does not. For example, "optionally comprising one or more pharmaceutically acceptable carriers and/or diluents" means that the pharmaceutically acceptable carrier and/or diluent may, but need not, be present.
Detailed Description
The present disclosure is further described below with reference to examples, but these examples do not limit the scope of the present disclosure.
The invention relates to an instrument and a method for collecting data, which comprises the following steps:
XRPD was X-ray powder diffraction detection: the measurement is carried out by using a BRUKER D8 type X-ray diffractometer, and the specific information is acquired: cu anode (40kV, 40mA), Cu-Ka ray
The scanning mode is as follows: q/2q, scanning range: 5-48 degrees.
DSC is differential scanning calorimetry: the measurement adopts a METTLER TOLEDO DSC 3+ differential scanning calorimeter, the temperature rise rate is10 ℃/min, the specific temperature range refers to a corresponding map (mostly 25-300 or 25-350 ℃), and the nitrogen purging speed is 50 mL/min.
DVS is dynamic moisture adsorption: the detection adopts SMS DVS Advantage, the humidity change is 50% -95% -0% -95% -50% at 25 ℃, the step is 10% (the last step is 5%) (the specific range of the humidity is based on the corresponding map, and the method listed in most application methods) and the judgment standard is that dM/dT is not more than 0.002.
IR spectrum: thermo Nicolet iS10 was used. The test method comprises the following steps: and preparing a sample tablet and a KBr blank tablet, and detecting to obtain an infrared spectrogram.
Drawings
FIG. 1: glibenclamide-arginine co-amorphous (1:6) XRPD patterns
FIG. 2 is a drawing: glibenclamide-arginine co-amorphous (1:6) DSC profile
FIG. 3: glibenclamide-arginine co-amorphous (1:6) DVS profiles
FIG. 4 is a drawing: glibenclamide-arginine co-amorphous (1:6) IR spectrum
FIG. 5: glibenclamide-arginine co-amorphous (1:6) IR spectrum
FIG. 6: glibenclamide-arginine co-amorphous (1:6) Raman spectra
FIG. 7: glibenclamide-arginine co-amorphous (1:1) IR spectrum
Example 1: preparation of glibenclamide-arginine co-amorphous form (1:6)
Experiment 1:
weighing 100mg of glibenclamide (crystal form A) and 36mg of arginine, adding 10mL of water, stirring overnight at room temperature, passing through a 0.45um membrane, measuring that the glibenclamide content in the supernatant is 1.76mg/mL and the arginine content is 3.50mg/mL, and simultaneously drying the supernatant at 60 ℃ to obtain a solid, wherein the Tg result shows-105.24 ℃. The XRPD pattern is shown in figure 1, the DSC pattern is shown in figure 2, the DVS pattern is shown in figure 3, the IR pattern is shown in figure 4, and the Raman pattern is shown in figure 6.
The solubility of the obtained co-amorphous substance having a molar ratio of glibenclamide to arginine of 1:6 was measured, and the results are shown in table 1.
TABLE 1 Glibenclamide-arginine amorphous (1:6) solubility study
Experiment 2:
weighing 500mg of glibenclamide and 720mg of arginine, adding 200ml of water, stirring overnight at room temperature, filtering with a 0.45um filter membrane, and drying the supernatant at 60 ℃ to obtain a solid. The IR spectrum is shown in figure 5, and the Raman spectrum is shown in figure 6.
Experiment 3:
the solid obtained in experiment 2 was weighed at 5mg, dissolved in 3ml of water, and lyophilized in a lyophilizer to obtain a sample. The Raman spectrum is shown in fig. 6.
FIG. 6 shows Raman spectra of glibenclamide amorphous form, arginine amorphous form, experiment 1 sample, experiment 3 sample, and experiment 2 sample from top to bottom.
Example 2: preparation of glibenclamide-arginine co-amorphous form (1:3)
Weighing 8mg of glibenclamide and 8mg of arginine, adding 10mL of water, obtaining a supersaturated solution at 60 ℃, passing through a 0.45um membrane, measuring that the glibenclamide content in a supernatant is 0.8mg/mL and the arginine content is 0.8mg/mL, and simultaneously drying the supernatant at 60 ℃ to obtain a solid, wherein an XRPD (X-ray diffraction pattern) of the solid shows that the solid is amorphous.
The solubility of the obtained co-amorphous substance having a molar ratio of glibenclamide to arginine of 1:3 was measured, and the results are shown in table 2.
TABLE 2 Glibenclamide-arginine co-amorphous (1:3) solubility study
Example 3: preparation of glibenclamide-arginine co-amorphous form (1:1)
500mg of glibenclamide and 180mg of arginine (molar ratio is 1:1) are weighed, 100ml of trichloromethane and 55ml of methanol-water (10:1) are added to be mixed, dissolved and clarified, rotary evaporation is carried out for 30min under the condition of 60 ℃/50mbar, and the solid sample is determined by XRPD (X-ray diffraction) results, so that the solid is amorphous. The Tg result showed 105.97 ℃. The IR spectrum is shown in FIG. 7.
Claims (11)
1. The glibenclamide-arginine co-amorphous is characterized in that a powder X-ray diffraction pattern of the glibenclamide-arginine co-amorphous has no sharp diffraction peak.
2. The glibenclamide-arginine co-amorphous form of claim 1 characterized by an infrared absorption spectrum at 1637, 1550, 1404, 1319, 1275, 1239, 1178, 1123, 1083, 1081, 910, 867, 810, 661, 611, 545cm-1Has characteristic peaks.
3. The glibenclamide-arginine co-amorphous form according to claim 1, characterized by a Tg of-105.24 ℃.
4. The glibenclamide-arginine co-amorphous form of claim 1 characterized by a Raman spectrum at 83.74, 262.48, 367.32, 686.06, 1153.58cm-1Without a characteristic peak.
5. The glibenclamide-arginine co-amorphous form of claim 1 characterized by a Raman spectrum with a characteristic peak at 1125.63.
6. The glibenclamide-arginine co-amorphous form according to claim 1, wherein the molar ratio of glibenclamide to arginine is 1:3.1 to 8.5.
7. A method for preparing glibenclamide-arginine co-amorphous form according to claim 1, characterized in that it uses solvent evaporation or milling.
8. The method according to claim 7, wherein the solvent used in the evaporation of the solvent is water.
9. A pharmaceutical composition comprising the glibenclamide-arginine co-amorphous form of claim 1, optionally with one or more pharmaceutically acceptable carriers and/or diluents.
10. A pharmaceutical composition prepared from the glibenclamide-arginine co-amorphous form of claim 1.
11. Use of the glibenclamide-arginine co-amorphous form of claim 1 or the pharmaceutical composition of claim 9 or 10 for the preparation of a medicament for the treatment of diabetes.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD249186A1 (en) * | 1986-05-26 | 1987-09-02 | Univ Halle Wittenberg | METHOD OF MANUFACTURING A NEW GLIBENCLAMID MEDICAMENT WITH HIGHER BIODEGRADABILITY |
| CN1660057A (en) * | 2004-12-29 | 2005-08-31 | 王召 | Solid dispersion and preoral combination of glibenclamide and preparation method |
| CN104415042A (en) * | 2013-08-30 | 2015-03-18 | 天津药物研究院 | Co-amorphous system and preparation method thereof |
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- 2021-01-21 CN CN202110080554.7A patent/CN113214121A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD249186A1 (en) * | 1986-05-26 | 1987-09-02 | Univ Halle Wittenberg | METHOD OF MANUFACTURING A NEW GLIBENCLAMID MEDICAMENT WITH HIGHER BIODEGRADABILITY |
| CN1660057A (en) * | 2004-12-29 | 2005-08-31 | 王召 | Solid dispersion and preoral combination of glibenclamide and preparation method |
| CN104415042A (en) * | 2013-08-30 | 2015-03-18 | 天津药物研究院 | Co-amorphous system and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| HENRI SORMUNEN等: "The effect of co-amorphization of glibenclamide on its dissolution properties and permeability through an MDCKII-MDR1 cell layer", 《INTERNATIONAL JOURNAL OF PHARMACEUTICS》 * |
| MARIKA RUPONEN等: "Permeability of glibenclamide through a PAMPA membrane: The effffect of co-amorphization", 《EUROPEAN JOURNAL OF PHARMACEUTICS AND BIOPHARMACEUTICS》 * |
| SACHIN KUMAR SINGH等: "Formulation of ternary complexes of glyburide with hydroxypropyl-β-cyclodextrin and other solubilizing agents and their effect on release behavior of glyburide in aqueous and buffered media at different agitation speeds", 《DRUG DEVELOPMENT AND INDUSTRIAL PHARMACY》 * |
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Application publication date: 20210806 |