CN114425040A - Preparation method of montelukast sodium granules - Google Patents
Preparation method of montelukast sodium granules Download PDFInfo
- Publication number
- CN114425040A CN114425040A CN202210160823.5A CN202210160823A CN114425040A CN 114425040 A CN114425040 A CN 114425040A CN 202210160823 A CN202210160823 A CN 202210160823A CN 114425040 A CN114425040 A CN 114425040A
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- CN
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- Prior art keywords
- montelukast sodium
- mannitol
- granules
- preparing
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229960001951 montelukast sodium Drugs 0.000 title claims abstract description 31
- LBFBRXGCXUHRJY-HKHDRNBDSA-M montelukast sodium Chemical compound [Na+].CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC([O-])=O)CC1 LBFBRXGCXUHRJY-HKHDRNBDSA-M 0.000 title claims abstract description 31
- 239000008187 granular material Substances 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims abstract description 17
- 229930195725 Mannitol Natural products 0.000 claims abstract description 17
- 239000000594 mannitol Substances 0.000 claims abstract description 17
- 235000010355 mannitol Nutrition 0.000 claims abstract description 17
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims abstract description 16
- 239000000853 adhesive Substances 0.000 claims abstract description 13
- 230000001070 adhesive effect Effects 0.000 claims abstract description 13
- 239000000463 material Substances 0.000 claims abstract description 13
- 238000002156 mixing Methods 0.000 claims abstract description 11
- 238000005507 spraying Methods 0.000 claims abstract description 11
- 239000007788 liquid Substances 0.000 claims abstract description 10
- 238000000576 coating method Methods 0.000 claims abstract description 9
- 239000000243 solution Substances 0.000 claims abstract description 9
- 239000011248 coating agent Substances 0.000 claims abstract description 8
- 235000019359 magnesium stearate Nutrition 0.000 claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- 238000007873 sieving Methods 0.000 claims abstract description 7
- 238000007599 discharging Methods 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract description 4
- 239000002245 particle Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 3
- 238000012216 screening Methods 0.000 claims description 3
- 229920003115 HPC-SL Polymers 0.000 claims description 2
- 229920003116 HPC-SSL Polymers 0.000 claims description 2
- 238000000889 atomisation Methods 0.000 claims description 2
- 239000008213 purified water Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims 3
- 239000000843 powder Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
- 230000007547 defect Effects 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 5
- 208000006673 asthma Diseases 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 description 2
- 208000036284 Rhinitis seasonal Diseases 0.000 description 2
- 201000010105 allergic rhinitis Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 208000024695 exercise-induced bronchoconstriction Diseases 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 229960005127 montelukast Drugs 0.000 description 2
- 208000017022 seasonal allergic rhinitis Diseases 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 208000033309 Analgesic asthma syndrome Diseases 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 208000024744 aspirin-induced respiratory disease Diseases 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000003199 leukotriene receptor blocking agent Substances 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
- A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1682—Processes
- A61K9/1694—Processes resulting in granules or microspheres of the matrix type containing more than 5% of excipient
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
Abstract
The invention belongs to the field of pharmaceutical preparations, and particularly relates to a preparation method of montelukast sodium granules, which comprises the following steps: sieving mannitol, adding into a fluidized bed, starting top spraying and atomizing when the material reaches a certain temperature, supplying liquid, top spraying and coating an adhesive solution on the surface of the mannitol to form granules, top spraying and coating a montelukast sodium aqueous solution on the surfaces of the granules at a certain speed, drying, sieving with a 24-mesh sieve, placing in a mixer, adding magnesium stearate, mixing, and discharging to obtain montelukast sodium granules. The invention overcomes the defects of the prior art, has good stability and low production cost, and is suitable for industrial production.
Description
Technical Field
The invention relates to the field of pharmaceutical preparations, and in particular relates to a preparation method of montelukast sodium granules.
Background
Montelukast sodium is a leukotriene receptor antagonist and is used for preventing and treating asthma, exercise-induced bronchoconstriction, seasonal allergic rhinitis, etc. The variety is developed by research and development of Merck Sharp & Dohme Corp in the United states, is sold as Singulair, is suitable for prevention and long-term treatment of asthma in children over 1 year old, and comprises prevention of asthma symptoms in daytime and nighttime, treatment of aspirin-sensitive asthma patients and prevention of exercise-induced bronchoconstriction, and is also suitable for children 2 to 5 years old to relieve symptoms caused by seasonal allergic rhinitis.
CN100591329C is prepared by granular mannitol, the granular mannitol has higher price, which leads to the increase of production cost, and the reappearance of patent technology shows that the preparation has poorer stability and the related substance sulfoxide has faster growth trend under the acceleration condition; CN104546851B and CN105193743B improve the stability of the main drug by adding stabilizers in the prescription and the like, but various types of stabilizers have gastrointestinal hidden troubles; the prescription disclosed in CN103860480A adds acrylic resin as coating material, and the coating process is complex and the production cost is high; in addition, the prior art mostly uses imported auxiliary materials and is expensive.
The invention provides a novel preparation method of montelukast sodium granules, and the prepared product has high stability, saves the purchase and production process cost of raw and auxiliary materials, and improves the economic benefit on the basis of meeting the clinical requirement.
Disclosure of Invention
The invention provides a preparation method of montelukast sodium particles, aiming at solving the problems of poor stability, high preparation cost and the like of montelukast sodium particles. The technical scheme adopted by the invention is as follows:
a preparation method of montelukast sodium granules comprises the following steps:
s1 pretreatment: sieving mannitol in a prescription amount, and removing lumps for later use;
preparing an S2 adhesive and a bulk drug solution: preparing clear aqueous solution defoaming for later use by using the adhesive and the raw material medicaments in the prescription amount according to specific concentrations respectively;
s3 granulating: adding the mannitol obtained in the step S1 into a fluidized bed, setting parameters such as air inlet temperature, air volume and the like, starting top spraying and supplying liquid when the material temperature of the fluidized bed reaches a certain temperature, and top spraying the adhesive solution on the surface of the mannitol to form particles;
s4 medicine application: top-spraying and coating the montelukast sodium aqueous solution on the surface of the granules obtained after the step S3 according to a specific rate, and drying until the water content is less than or equal to 0.5 percent after the coating is finished;
s5 screening: sieving the dried granules with a 24-mesh sieve;
s6 mixing: and (4) adding the granules obtained in the step S5 into a mixer, converting the dosage of magnesium stearate according to the prescription proportion and yield, adding the magnesium stearate into the mixer, mixing for a corresponding time, and discharging to obtain the montelukast sodium granular preparation.
Further, the adhesive is hydroxypropyl cellulose, and the type is HPC-SL or HPC-SSL.
Further, the concentration of the bulk drug solution is 4% -10%, and the concentration of the adhesive is 4% -10%; the solvent is purified water.
Further, in the step S3, the liquid supply rotating speed is 10g/min-20g/min, and the atomization pressure is 2kg/cm2-3kg/cm2。
Further, the temperature of the material temperature in the step S3 reaching the equilibrium state is 25-45 ℃.
Further, the mixing time in the step S6 is 5min-8 min.
Advantageous effects
The montelukast sodium particles prepared by the invention have good particle stability under the condition of not adding a stabilizer.
The invention saves a large amount of cost from the aspects of raw and auxiliary materials and production process, and improves economic benefit.
Detailed Description
The present invention is embodied by the following examples, which are intended to illustrate the invention but are not to be construed as limiting the scope thereof.
Example 1:
1. formulation formula
| Raw and auxiliary materials | mg/bag | The proportion of the prescription is% |
| Montelukast sodium | 4.16 | 0.832 |
| Mannitol | 484.19 | 96.83 |
| Hydroxypropyl cellulose | 10.40 | 2.08 |
| Magnesium stearate SH-YM-M | 1.25 | 0.25 |
| Total up to | 500 | 100 |
Remarking:
4.16mg of montelukast sodium corresponds to 4mg of montelukast;
the actual charge was 4.16mg batch/content/(1-moisture), calculated as 100% above 100%.
2. Preparation process
S1 pretreatment: sieving mannitol with 24 mesh sieve to remove agglomeration for use;
preparing an S2 adhesive and a bulk drug solution: preparing a clear aqueous solution with the adhesive and the raw material medicines according to the prescription amount and the concentration of 10% for defoaming for later use;
s3 granulating: adding mannitol obtained in step S1 into fluidized bedThe inlet air temperature is 60 ℃, and the air volume is 30kg/m3When the material temperature of the fluidized bed reaches 35 ℃, the top is opened to atomize 3kg/cm2Top spraying the adhesive solution on the surface of the mannitol to form particles at a liquid supply speed of 15 g/min;
s4 medicine application: top-spraying and coating the montelukast sodium aqueous solution on the surface of the granules obtained in the step S3 according to the speed obtained in the step S3, and drying until the moisture is less than or equal to 0.5%;
s5 screening: all the dried particles pass through a 24-mesh sieve;
s6 mixing: adding the granules obtained in the step S5 into a mixer, converting the dosage of magnesium stearate according to the prescription proportion and the yield, adding the magnesium stearate into the mixer, mixing for 5min, and discharging to obtain the montelukast sodium granular preparation;
and (S7) subpackaging the granules: and (5) adding the granules obtained in the step (S6) into a full-automatic granule packaging machine, and subpackaging according to 0.5 g/bag to obtain the granules.
Example 2:
the prescription composition is unchanged, the concentration of the raw material medicine in the step S2 is prepared according to the concentration of 4 percent on the basis of the example 1, and the rest process steps are all consistent with the example 1;
example 3:
the prescription composition is unchanged, the adhesive concentration in the step S2 is prepared according to the concentration of 4 percent on the basis of the example 1, and the rest process steps are consistent with the example 1;
example 4:
the prescription composition is unchanged, the liquid supply rotating speed in the step S3 is set to be 10g/min on the basis of the embodiment 1, and the rest process steps are consistent with those in the embodiment 1;
example 5:
the prescription composition is unchanged, the liquid supply rotating speed in the step S3 is set to be 20g/min on the basis of the embodiment 1, and the rest process steps are consistent with those in the embodiment 1;
example 6:
the prescription composition is unchanged, the liquid supply rotating speed and the air inlet temperature in the step S3 are adjusted on the basis of the embodiment 1 to ensure that the material temperature in the fluidized bed is 25 +/-2 ℃, and the rest process steps are consistent with those in the embodiment 1;
example 7:
the prescription composition is unchanged, the liquid supply rotating speed and the air inlet temperature in the step S3 are adjusted on the basis of the embodiment 1 to ensure that the material temperature in the fluidized bed is 45 +/-2 ℃, and the rest process steps are consistent with those in the embodiment 1;
example 8:
the prescription composition is unchanged, the mixing time of the step S6 is adjusted to be 5min on the basis of the example 1, and the rest process steps are all consistent with the example 1;
example 9:
the prescription composition is unchanged, the mixing time of the step S6 is adjusted to be 8min on the basis of the example 1, and the rest process steps are all consistent with the example 1;
comparative example (original patent CN 100591329C):
the prescription was reproduced according to the protocol disclosed in the original patent CN100591329C, the diluent mannitol was 200SD and the source was Rogat, France.
3. Test results
The formulation samples, the comparative samples and the RLD samples of the original developers of example 3 and example 4 were respectively placed under accelerated (40 ℃, 75% RH) and long-term (25 ℃, 60% RH) test conditions to examine the changes of the related substances, and the test results are shown in Table 1:
table 1 stability test results of montelukast sodium granules
Remarking: total impurities are calculated after subtracting methylstyrene.
The results show that: compared with the sulfoxide impurity of comparative example, the sulfoxide impurity has a faster growth trend, and the growth trend is accelerated for 6 months, so that the montelukast sodium particles prepared in the examples 3 and 4 have an overrun risk, and through accelerated tests and long-term test investigation, the growth trend of the related substance during the stability period is lower than that of a reference preparation, and compared with 0 month, the growth trend is not obviously different for 6 months, so that the growth trend is within a qualified range, and the quality requirement is met. Therefore, the preparation method of the montelukast sodium granules has good technical effects, provides a new technical scheme for the preparation of the montelukast sodium granules, and can better meet clinical requirements.
The above-described embodiments are intended to be merely illustrative of the technical concepts and advantages of the present invention, and the present invention may be further modified in various forms, as will be apparent to those skilled in the art, and the above-described embodiments are merely exemplary of the scope of the present invention, and other modifications and embodiments are intended to be included within the scope of the appended claims.
Claims (7)
1. A preparation method of montelukast sodium particles is characterized by comprising the following steps:
s1 pretreatment: sieving mannitol in a prescription amount, and removing lumps for later use;
preparing an S2 adhesive and a bulk drug solution: preparing clear aqueous solution defoaming for later use by using the adhesive and the raw material medicaments in the prescription amount according to specific concentrations respectively;
s3 granulating: adding the mannitol obtained in the step S1 into a fluidized bed, setting parameters such as air inlet temperature, air volume and the like, starting top spraying and supplying liquid when the material temperature of the fluidized bed reaches a certain temperature, and top spraying the adhesive solution on the surface of the mannitol to form particles;
s4 medicine application: top-spraying and coating the montelukast sodium aqueous solution on the surface of the granules obtained after the step S3 according to a specific rate, and drying until the water content is less than or equal to 0.5 percent after the coating is finished;
s5 screening: sieving the dried granules with a 24-mesh sieve;
s6 mixing: and (4) adding the granules obtained in the step S5 into a mixer, converting the dosage of magnesium stearate according to the prescription proportion and yield, adding the magnesium stearate into the mixer, mixing for a corresponding time, and discharging to obtain the montelukast sodium granular preparation.
2. The method for preparing montelukast sodium granules according to claim 1, wherein the mannitol is mannitol in the form of common fine powder.
3. The method for preparing montelukast sodium particles according to claim 1, wherein the binder is hydroxypropylcellulose, and the type of the binder is HPC-SL or HPC-SSL.
4. The preparation method of montelukast sodium particles according to claim 1, wherein the concentration of the raw material solution is 4% -10%, and the concentration of the binder is 4% -10%; the solvent is purified water.
5. The method for preparing montelukast sodium particles according to claim 1, wherein the liquid supply speed in the step S3 is 10g/min-20g/min, and the atomization pressure is 2kg/cm2-3kg/cm2。
6. The method for preparing montelukast sodium particles according to claim 1, wherein the temperature of the material at equilibrium in the step S3 is 25 ℃ to 45 ℃.
7. The method for preparing montelukast sodium particles according to claim 1, wherein the mixing time in the step S6 is 5min to 8 min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210160823.5A CN114425040A (en) | 2022-02-24 | 2022-02-24 | Preparation method of montelukast sodium granules |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210160823.5A CN114425040A (en) | 2022-02-24 | 2022-02-24 | Preparation method of montelukast sodium granules |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114425040A true CN114425040A (en) | 2022-05-03 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210160823.5A Pending CN114425040A (en) | 2022-02-24 | 2022-02-24 | Preparation method of montelukast sodium granules |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1575163A (en) * | 2001-10-26 | 2005-02-02 | 麦克弗罗斯特(加拿大)公司 | Granule formulation |
| WO2009153305A2 (en) * | 2008-06-19 | 2009-12-23 | Sandoz Ag | Pharmaceutical compositions of montelukast sodium |
-
2022
- 2022-02-24 CN CN202210160823.5A patent/CN114425040A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1575163A (en) * | 2001-10-26 | 2005-02-02 | 麦克弗罗斯特(加拿大)公司 | Granule formulation |
| WO2009153305A2 (en) * | 2008-06-19 | 2009-12-23 | Sandoz Ag | Pharmaceutical compositions of montelukast sodium |
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Application publication date: 20220503 |