CN108785263B - Solid pharmaceutical composition of pramipexole or pharmaceutical salt thereof and preparation method thereof - Google Patents

Solid pharmaceutical composition of pramipexole or pharmaceutical salt thereof and preparation method thereof Download PDF

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CN108785263B
CN108785263B CN201810376240.XA CN201810376240A CN108785263B CN 108785263 B CN108785263 B CN 108785263B CN 201810376240 A CN201810376240 A CN 201810376240A CN 108785263 B CN108785263 B CN 108785263B
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pharmaceutical composition
solid pharmaceutical
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pramipexole
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陈爱玲
衡伟利
潘凯
刘凯
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Jiangsu Hengrui Medicine Co Ltd
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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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/428—Thiazoles condensed with carbocyclic rings
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2009—Inorganic compounds
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs

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Abstract

The invention relates to a solid pharmaceutical composition of pramipexole or a medicinal salt thereof and a preparation method thereof. Specifically, the solid pharmaceutical composition comprises pramipexole or a medicinal salt or a solvate thereof as an active ingredient, and also comprises a sustained-release matrix material, a calcium phosphate salt and other excipients. The solid pharmaceutical composition has good dissolution rate and stability, and still has good release behavior under the conditions of high temperature and high humidity.

Description

Solid pharmaceutical composition of pramipexole or pharmaceutical salt thereof and preparation method thereof
Technical Field
The invention belongs to the field of medicinal chemistry, and relates to a solid medicinal composition containing pramipexole or medicinal salt thereof and a preparation method thereof.
Background
Parkinson's disease is a common, slowly progressing degenerative disease of the nervous system occurring in the elderly. Clinically, resting tremor, muscular rigidity and dyskinesia are the main characteristics. With the aging process of the population, the prevalence rate of the disease is increased year by year. For a long time, drug replacement therapy mainly based on levodopa is the first choice for the treatment of parkinson's disease. However, long-term administration of levodopa by patients often results in decreased efficacy and fluctuations in response, such as "end-of-dose" and "switching", as well as motor complications, such as dyskinesia and dystonia.
Figure RE-GDA0001695549880000011
Pramipexole, chemical name (S) -2-amino-4, 5,6, 7-tetrahydro-6- (propylamino) benzothiazole, structure of which is shown above, is a non-ergot dopamine receptor agonist which can effectively activate dopamine D2 subgroup receptors, wherein the affinity to D3 receptor is higher than that of D2 or D4 receptor, and the pramipexole can be used for treating Parkinson' S disease, and compared with levodopa, the pramipexole used in early stage can delay the side effects and improve the life quality of patients. In 1997, pramipexole immediate release tablets from bliringer ingenhe
Figure RE-GDA0001695549880000012
On the market in the united states, for the treatment of parkinson's disease, the drug must be taken three times daily. In order to simplify the administration scheme, improve the compliance of patients and reduce the side effects caused by the fluctuation of blood concentration, the Boringer Vargham further develops a once-a-day sustained release tablet
Figure RE-GDA0001695549880000013
Figure RE-GDA0001695549880000014
And marketed in the united states in 2010.
CN101005830B discloses an extended release formulation of pramipexole and a method for preparing the same, the extended release formulation comprising at least two water swellable polymers other than pregelatinized starch, at least one of which is an anionic water swellable polymer and at least one neutral water swellable polymer other than pregelatinized starch. Wherein the anionic water-swelling polymer is a pH-related slow-release skeleton material, the content of the anionic water-swelling polymer is 0.25-25% of the total weight of the slow-release preparation, and the neutral water-swelling polymer of the non-pregelatinized starch is a pH-unrelated slow-release skeleton material, and the content of the neutral water-swelling polymer is 10-75%. The sustained release formulation achieves different release rates depending on or independent of pH by two different principles. The oral sustained release preparation can treat the symptoms of patients by being taken once a day, thereby improving the convenience and the compliance of the patients. However, the anionic water-swellable polymer with the weight described in the patent is taken as a pH value-related slow-release skeleton material, and the prepared preparation has poor stability, and the release behavior can be greatly changed after the preparation is placed under high-temperature or high-humidity conditions.
CN101005831B discloses pramipexole extended release tablets comprising at least one pregelatinized starch, one anionic polymer and a third water swellable polymer and a process for their preparation. The content of the anionic water-swellable polymer in the preparation is 0.25-25% of the total weight, and the release behavior is changed after the preparation is placed under the conditions of high humidity and high temperature. This instability poses risks to the patient during the administration process and increases the requirements for packaging and storage of the drug, making commercial production of the formulation difficult.
The invention aims to overcome the defects of the prior art and provide a pramipexole solid pharmaceutical composition with good dissolution rate and stability. Furthermore, the invention optimizes the content of the anionic water-swelling polymer by optimizing the type of the sustained-release framework material, improves the release performance and stability of the sustained-release preparation, and unexpectedly discovers that the stability of the preparation under the conditions of high temperature and high humidity can be obviously improved by adding a certain amount of calcium phosphate salt into the preparation, thereby reducing the requirements on packaging and storage, being more suitable for the commercial production of the preparation, and ensuring the safety of patients in the medication process.
Disclosure of Invention
The invention aims to provide a pramipexole solid pharmaceutical composition which can still keep good release behavior that the average release ratio in 2 hours is within the range of 12-32%, the average release ratio in 9 hours is within the range of 42-62% and the average release ratio in 24 hours is not less than 70% in a phosphate buffer solution with the pH value of 6.8 when the pramipexole solid pharmaceutical composition is placed under the high-temperature and high-humidity condition, so that the risk that the release effect of the pharmaceutical composition is changed due to the influence of the environment in the use process is reduced, the medication safety and stability are improved, and the requirements of commercial production and storage conditions of pharmaceutical preparations are reduced.
The invention provides a solid pharmaceutical composition, which contains an active ingredient of pramipexole or medicinal salt or solvate thereof, calcium phosphate salt and a sustained-release skeleton material.
In some embodiments, the active ingredient of the solid pharmaceutical composition is pramipexole or a pharmaceutically acceptable salt or solvate of a salt thereof selected from the group consisting of hydrochloride, sulfate, hydrobromide, citrate, hydroiodide, phosphate, nitrate, benzoate, methanesulfonate, benzenesulfonate, 2-hydroxyethanesulfonate, p-toluenesulfonate, acetate, propionate, oxalate, malonate, succinate, glutarate, adipate, tartrate, maleate, fumarate, malate and mandelate, preferably in the form of the hydrochloride, more preferably the dihydrochloride, most preferably in the form of the dihydrochloride monohydrate.
Further, the active ingredient is contained in an amount of 0.05 to 10%, preferably 0.05 to 7%, more preferably 0.05 to 5%, most preferably 0.05 to 3% by weight of the pharmaceutical composition.
The "calcium phosphate salt" of the present invention refers to a salt selected from Phosphate (PO) with calcium ion as metal ion4 3－) Monohydrogen phosphate (HPO)4 2－) And dihydrogen phosphate radical (H)2PO4 －) The anion of (2) as an acid ion, and may further include organic solvent compounds and hydrates thereof.
In some embodiments, the calcium phosphate salt of the present invention is selected from anhydrous calcium hydrogen phosphate, calcium hydrogen phosphate dihydrate, and calcium phosphate, preferably anhydrous calcium hydrogen phosphate and calcium hydrogen phosphate dihydrate, and most preferably calcium hydrogen phosphate dihydrate.
Further, the calcium phosphate salt is present in an amount of 1.0-30%, preferably 2.0-20%, more preferably 2.0-10%, most preferably 2.0-5.0% by weight of the pharmaceutical composition.
In some embodiments, the sustained release matrix material of the present invention comprises at least two water swellable polymers, one of which is an anionic polymer selected from the group consisting of: acrylic acid polymers, methacrylic acid copolymers, alginates, carrageenan, gum arabic, xanthan gum, chitosan, sodium carboxymethylcellulose, calcium carboxymethylcellulose, preferably alginate; the other is a neutral polymer selected from: alkylcelluloses, hydroxyalkylcelluloses, hydroxyalkylalkylcelluloses, hydroxyalkylcellulose esters, disaccharides, oligosaccharides and polysaccharides, polyvinyl alcohols, polyvinylpyrrolidone, copolymers of polyvinylpyrrolidone with vinyl acetate, combinations of polyvinyl alcohol and polyvinylpyrrolidone, polyalkylene oxides, preferably polyoxyethylene or polyvinyl alcohol.
In some embodiments, the anionic polymer of the present invention is present in an amount of 25 to 80%, preferably 30 to 60%, more preferably 30 to 50%, most preferably 30 to 40% by weight of the pharmaceutical composition.
In some embodiments, the neutral polymer of the present invention is present in an amount of 10 to 80%, preferably 20 to 60%, more preferably 30 to 60%, most preferably 40 to 60% by weight of the pharmaceutical composition.
In some embodiments, the slow release matrix material of the present invention comprises one or more of sodium alginate and polyoxyethylene or polyvinyl alcohol.
In one embodiment, the slow release matrix material comprises sodium alginate and polyoxyethylene.
In another embodiment, the slow release matrix material comprises sodium alginate and polyvinyl alcohol.
Further, the sodium alginate has a viscosity of about 100 to 1000 mPa-s, preferably 200 to 800 mPa-s, more preferably 300 to 600 mPa-s, most preferably 400 to 600 mPa-s in a 1% by weight solution at 20 ℃.
Further, the molecular weight of the polyoxyethylene is in the range of about 900,000 daltons to 7,000,000 daltons, preferably 1,000,000 daltons to 7,000,000 daltons, more preferably 4,000,000 daltons to 7,000,000 daltons, and most preferably 5,000,000 daltons to 7,000,000 daltons.
Further, the molecular weight of the polyvinyl alcohol ranges from about 10,000 daltons to 3,000,000 daltons, preferably from 20,000 daltons to 2,000,000 daltons, more preferably from 30,000 daltons to 1,000,000 daltons, and most preferably from 30,000 daltons to 500,000 daltons.
In some embodiments, the formulations of the present invention may optionally further comprise additional excipients, i.e., pharmaceutically acceptable agents, in order to improve the manufacturability, compactibility, appearance, and taste of the formulation. Such pharmaceutical agents include, for example, diluents or fillers, glidants, binders, granulating agents, anti-caking agents, lubricants, fragrances, coloring preservatives. Other conventional excipients known in the art may also be included.
The solid pharmaceutical compositions provided herein may also include one or more lubricants to aid tableting. The lubricant can be selected from pulvis Talci, magnesium stearate, zinc stearate, glyceryl behenate, sodium lauryl sulfate, hydrogenated vegetable oil, colloidal silica, etc., preferably magnesium stearate.
Further, the content of the lubricant is 0.5-2% by weight of the pharmaceutical composition.
The dosage numerical range of the active ingredients or other types of pharmaceutical excipients is calculated by the weight of the tablet core without the coating agent according to the weight of the pharmaceutical composition.
In an embodiment of the invention, the solid pharmaceutical composition consists of:
Figure BDA0001639825280000031
in one embodiment, the sustained release formulation consists of:
Figure BDA0001639825280000032
in another embodiment, the sustained release formulation consists of:
Figure BDA0001639825280000041
another object of the present invention is to provide a method for preparing the above solid pharmaceutical composition, which is a direct powder compression method.
In some embodiments, when prepared by direct compression of a powder, the active ingredient, calcium phosphate salt, sustained release matrix material, and other excipients may be mixed together and compressed into tablets.
Drawings
Figure 1 shows the release profile of the tablets of examples 1 to 6 starting in phosphate buffer at ph 6.8.
FIG. 2 shows the release profile of the tablets of example 2 in pH6.8 phosphate buffer initially and after standing at a temperature of 60 ℃.
FIG. 3 shows the release profile of the tablets of comparative example 2 in pH6.8 phosphate buffer, initially and after standing at a temperature of 60 ℃.
FIG. 4 shows the release profile of the tablets of comparative example 7 in pH6.8 phosphate buffer, initially and after standing at a temperature of 60 ℃.
FIG. 5 shows the release profile of the tablets of example 2 in phosphate buffer pH6.8 starting with a temperature of 25 ℃ and after standing at 92.5% RH.
FIG. 6 shows the release profile of the tablets of comparative example 2 in phosphate buffer pH6.8 at the start and after standing at 25 ℃ and 92.5% RH.
FIG. 7 shows the release profile of the tablets of comparative example 4 in phosphate buffer pH6.8 starting with a temperature of 25 ℃ and after being left at 92.5% RH.
FIG. 8 shows the release profile of the tablets of comparative example 5 in phosphate buffer pH6.8 at the start and after standing at 25 ℃ and RH 92.5%.
FIG. 9 shows the release profile of the tablets of comparative example 6 in phosphate buffer pH6.8 starting with a temperature of 25 ℃ and after being left at 92.5% RH.
FIG. 10 shows the release profile of the tablets of comparative example 7 in a phosphate buffer pH6.8 at the start and after standing at 25 ℃ and 92.5% RH.
FIG. 11 shows the release profile of the tablets of comparative example 8 in a phosphate buffer pH6.8 at the start and after standing at 25 ℃ and 92.5% RH.
Detailed Description
The present invention will be explained in more detail with reference to examples, which are provided only for illustrating the technical solutions of the present invention and the spirit and scope of the present invention are not limited thereto.
Examples 1 to 3:
pramipexole dihydrochloride, sodium alginate, polyoxyethylene, calcium hydrophosphate and magnesium stearate are mixed by a rotary mixer according to the proportion in the table 1 and then directly tabletted.
TABLE 1
Figure BDA0001639825280000051
Examples 4 to 6:
pramipexole dihydrochloride, sodium alginate, polyvinyl alcohol, calcium hydrophosphate and magnesium stearate are mixed by a rotary mixer according to the proportion in the table 2 and then directly tabletted.
TABLE 2
Figure BDA0001639825280000052
Comparative examples 1 to 3:
pramipexole dihydrochloride, hydroxypropyl methylcellulose, corn starch, carbomer 941, colloidal silicon dioxide and magnesium stearate are mixed by a rotary total mixer according to the proportion in the table 3 and then directly tabletted.
TABLE 3
Figure BDA0001639825280000053
Figure BDA0001639825280000061
Comparative examples 4 to 6:
the materials were weighed according to the recipe in table 4, mixed using a rotary master mixer and then directly tabletted.
TABLE 4
Figure BDA0001639825280000062
Comparative examples 7 to 8
Pramipexole dihydrochloride, sodium alginate, polyoxyethylene and magnesium stearate are mixed by a rotary mixer according to the proportion in the table 5 and then directly tabletted.
TABLE 5
Figure BDA0001639825280000063
Figure BDA0001639825280000071
Experimental examples 1 to 6: initial dissolution test of tablets
According to the first method of 0931, the four general rules of the Chinese pharmacopoeia 2015 edition, a phosphate buffer solution with pH6.8 is used as a dissolution medium, and dissolution tests are carried out at 37 +/-0.5 ℃. The results show that: the sustained-release preparations of examples 1 to 6 all had good release behavior at the beginning, and the average release rate was 12 to 32% at 2 hours, 42 to 62% at 9 hours, and not less than 70% at 24 hours. The release profile is shown in figure 1.
Stability study at 60 deg.C
The naked tablets of example 2, comparative example 2 and comparative example 7 were placed in an oven at 60 ℃ for 1 week and 3 weeks, and then the release profile after the sample was placed was measured by using a phosphate buffer solution of ph6.8 as an elution medium according to the first method of 0931, the four-part rule of chinese pharmacopoeia 2015 edition. The results show that: comparative example 2 the release was significantly reduced after 1 week and 3 weeks in an oven at 60 ℃. Comparative example 7 the release was slightly reduced after 1 week and 3 weeks in an oven at 60 ℃.
Example 2 after being placed in an oven at 60 ℃ for 1 week and 3 weeks, the release rate was not significantly changed from the initial release rate, and still had good release behavior, the 2-hour average release rate was in the range of 12-32%, the 9-hour average release rate was in the range of 42-62%, and the 24-hour average release rate was not less than 70%. The release profiles are shown in fig. 2 to 4.
Stability study at 25 ℃ and RH 92.5%
The exposed tablets of example 2, comparative example 2 and comparative examples 4 to 8 were left to stand at 25 ℃ and RH 92.5% for 1 week and 3 weeks, and then the release profile of the sample after the standing was measured by using a phosphate buffer solution of ph6.8 as an elution medium according to the first method of 0931, the four-part general rule of chinese pharmacopoeia 2015 edition. The results show that: comparative example 2 and comparative examples 4 to 6, the release was significantly increased after being left in an oven at 60 ℃ for 1 week and 3 weeks. In comparative examples 7 and 8, the release rate was slightly increased after the test piece was left in an oven at 60 ℃ for 1 week and 3 weeks.
Example 2 after being placed at 25 ℃ and RH 92.5% for 1 week and 3 weeks, the release rate was not significantly changed from the initial value, and the release rate was still good, the 2-hour average release rate was in the range of 12-32%, the 9-hour average release rate was in the range of 42-62%, and the 24-hour average release rate was not less than 70%. The results show that the solid pharmaceutical composition provided by the invention is stable under high humidity conditions, and the addition of calcium phosphate salt in the formula is also beneficial to the stability of the solid pharmaceutical composition under high humidity conditions. The release profiles are shown in fig. 5 to 11.

Claims (11)

1. A solid pharmaceutical composition comprises the following components in percentage by weight:
Figure FDA0002953421410000011
2. a solid pharmaceutical composition comprises the following components in percentage by weight:
Figure FDA0002953421410000012
3. a solid pharmaceutical composition according to any one of claims 1-2, characterized in that the mean release rate is in the range of 12-32% for 2 hours at 37 ± 0.5 ℃ in phosphate buffer ph 6.8.
4. A solid pharmaceutical composition according to claim 3, characterized in that the mean release rate in phosphate buffer at ph6.8 at 37 ± 0.5 ℃ for 9 hours is in the range of 42-62%.
5. The solid pharmaceutical composition according to claim 3, wherein the average release rate in phosphate buffer at pH6.8 at 37 ± 0.5 ℃ for 24 hours is not less than 70%.
6. The solid pharmaceutical composition according to claim 4, wherein the average release rate in phosphate buffer at pH6.8 at 37 ± 0.5 ℃ for 24 hours is not less than 70%.
7. A process for the preparation of a solid pharmaceutical composition according to any one of claims 1-2, 4-6, which process is a powder direct compression process.
8. A process for preparing the solid pharmaceutical composition of claim 3, which is a powder direct compression process.
9. Use of the solid pharmaceutical composition of any one of claims 1-2, 4-6, 8 in the manufacture of a medicament for the treatment of parkinson's disease.
10. Use of the solid pharmaceutical composition of claim 3 in the manufacture of a medicament for the treatment of parkinson's disease.
11. Use of the solid pharmaceutical composition of claim 7 in the manufacture of a medicament for the treatment of parkinson's disease.
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