CN114699504B - Preparation method of lisinopril sustained-release tablet - Google Patents
Preparation method of lisinopril sustained-release tablet Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/05—Dipeptides
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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
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
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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
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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
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
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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
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
A preparation method of lisinopril sustained-release tablets belongs to the field of pharmaceutical preparations, and comprises 4 steps of preparing a raw medicine emulsion, preparing raw medicine powder, preparing medicine-carrying granules and tabletting; according to the invention, through a spray drying process, lisinopril is coated by hydroxypropyl-beta-cyclodextrin, hydroxypropyl methylcellulose acetate succinate and polylactic acid, so that the release time of lisinopril is effectively prolonged, and the slow release effect is greatly improved; stearic acid and hydrogenated castor oil are used as framework materials, and the stearic acid and the hydrogenated castor oil are combined with the bonding effect of the cellulose acetate phthalate and the starch sodium octenylsuccinate, so that the raw lisinopril powder is uniformly dispersed in the framework materials under the emulsification and dispersion effects of the glyceryl monostearate and the triethyl citrate, and the lisinopril tablet with good slow release effect is finally prepared.
Description
Technical Field
The invention relates to a preparation method of lisinopril sustained-release tablets, and belongs to the field of pharmaceutical preparations.
Background
Lisinopril is a lysine derivative of enalaprilat, belongs to a third-generation angiotensin converting enzyme inhibitor, can inhibit the activity of angiotensin converting enzyme, reduces the concentrations of angiotensin II and aldosterone, increases the activity of plasma renin, causes peripheral vasodilation and vascular resistance to decrease, thereby generating a blood pressure reduction effect, and is mainly suitable for treating essential hypertension.
The onset of hypertension has the characteristic of circadian rhythm, the blood pressure of a human body shows rhythm change within 24 hours, the blood pressure rapidly rises to a peak value within hours after waking in the early morning, and drops to a valley value from midnight to early morning, and the morning peak phenomenon is one of two important characteristics of the blood pressure. The knowledge of the rhythm change rule of the human blood pressure has important guiding significance for clinically treating hypertension. Therefore, the ideal antihypertensive drug has better compliance, and can stably reduce blood pressure within 24 hours, remarkably reduce the early morning blood pressure of hypertensive, ensure that the safety of the antihypertensive drug exceeds the high-incidence time of cardiovascular and cerebrovascular events, and effectively protect the functions of target organs such as heart, brain, kidney and the like. The proper medicine is selected according to the blood pressure rhythm change of a human body and the medicine action is consistent with the rhythm of the disease in reasonable administration time, thereby achieving the purposes of optimal treatment effect and reducing the adverse reaction of the medicine.
Chinese patent CN107281461A discloses a lisinopril sustained-release tablet and a preparation method thereof, wherein the lisinopril sustained-release tablet consists of a tablet core containing lisinopril and a coating layer coated outside the tablet core, the coating layer is made of a water-insoluble coating material, and the tablet core comprises the following substances in parts by weight: 5-10 parts of lisinopril and 40-70 parts of porous carbon material. The lisinopril sustained-release tablet obtained in the patent is difficult to keep a good sustained-release effect within 24 hours.
The preparation method of the lisinopril sustained-release tablet disclosed in Chinese patent CN105055358A comprises 1-4% of lisinopril, 54-66% of a framework material, 18-24% of pregelatinized starch, 14.2-17.6% of microcrystalline cellulose and 0.4-0.8% of magnesium stearate; the matrix material is carbomer. The lisinopril sustained-release tablet obtained in the patent has the advantages of fast drug release and difficulty in keeping the steady drug release concentration within the whole period of 24 hours.
As can be seen from the above, the prior lisinopril sustained-release tablet still has poor sustained-release effect and is difficult to ensure the stability of the drug release speed within 24 hours.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a preparation method of lisinopril sustained-release tablets, which realizes the following purposes: the lisinopril sustained-release tablet which has good sustained-release effect and can release drug stably within 24 hours is prepared.
In order to realize the purpose, the invention adopts the following technical scheme:
a preparation method of lisinopril sustained-release tablets comprises 4 steps of preparing a raw medicine emulsion, preparing raw medicine powder, preparing medicine-carrying granules and tabletting.
The following is a further improvement of the above technical solution:
step 1, preparation of original medicine emulsion
Mixing lisinopril, vitamin E polyethylene glycol succinate, hydroxypropyl-beta-cyclodextrin and deionized water, and stirring to dissolve completely to obtain a raw water phase; dissolving hydroxypropyl methyl cellulose acetate succinate and polylactic acid in dichloromethane to obtain an oil phase, slowly adding the oil phase into a raw medicine water phase at a shearing rate of 35000-55000 r/min, and shearing and dispersing for 30-50 minutes to obtain a raw medicine emulsion;
the mass ratio of lisinopril, vitamin E polyethylene glycol succinate, hydroxypropyl-beta-cyclodextrin and deionized water in the raw water phase is 5-15: 1-8: 2-4.5: 90-130;
the mass ratio of hydroxypropyl methyl cellulose acetate succinate, polylactic acid and dichloromethane in the oil phase is 1-6: 4-10: 50-90;
the molecular weight of the polylactic acid is 11000-18000 g/mol;
the mass ratio of the oil phase to the original water phase in the original emulsion is 1-4: 10.
Step 2, preparation of raw medicine powder
Carrying out spray granulation on the original medicine emulsion, controlling the air inlet temperature to be 110-145 ℃ and the atomization pressure to be 80-120 kPa to obtain powder with the particle size of 20-60 microns, and drying the powder at the temperature of 75-90 ℃ for 1.5-4 hours to obtain original medicine powder.
Step 3, preparation of drug-loaded granules
Mixing stearic acid and hydrogenated castor oil, heating to 80-95 ℃, melting into liquid, slowly adding raw medicine powder into the liquid at a stirring speed of 5000-8000 rpm, then sequentially adding magnesium stearate, triethyl citrate, glyceryl monostearate, sodium starch octenyl succinate and cellulose acetate phthalate, continuously stirring for 2-4 hours after the addition is finished, cooling to room temperature to obtain a block solid, placing the block solid at-40 to-15 ℃, freezing for 2-6 hours, and then crushing into medicine-carrying granules with the particle size of 50-90 micrometers at-13 to-5 ℃;
the mass ratio of stearic acid, hydrogenated castor oil, raw drug powder, magnesium stearate, triethyl citrate, starch sodium octenyl succinate, cellulose acetate phthalate and glyceryl monostearate is 5-10: 13-20: 25-35: 1-5: 5-10: 2-8: 1-5: 6-12.
Step 4, tabletting
And pressing the drug-loaded granules into tablets to obtain lisinopril tablets with the hardness of 9-10.5 Kg.
Compared with the prior art, the invention has the following beneficial effects:
1. the lisinopril sustained-release tablet prepared by the invention has good sustained-release effect and can release drug stably within 24 hours, the average cumulative release amount of lisinopril in water for 1 hour, 5 hours, 9 hours, 13 hours, 17 hours, 21 hours and 25 hours is respectively 4.3-5.2%, 9.4-10.9%, 22.9-23.6%, 34.5-36.1%, 52.7-54.9%, 78.2-79.5% and 88.1-90.9%, the average cumulative release amount of lisinopril in 1 hour, 5 hours, 9 hours, 13 hours, 17 hours, 21 hours and 25 hours in the artificial gastric juice is respectively 8.6-10.6%, 13.1-15.2%, 28.9-32.7%, 45.9-47.9%, 68.3-71.6%, 85.9-88.9% and 97.4-99.4%, the average cumulative release amount of lisinopril in 1 hour, 5 hours, 9 hours, 13 hours, 17 hours, 21 hours and 25 hours in the artificial intestinal juice is respectively 7.2-8.1%, 11.9-13.5%, 24.8-28.6%, 41.3-42.8%, 58.3-60.7%, 80.3-83.7% and 94.5-98.2%;
2. according to the invention, through a spray drying process, lisinopril is coated by hydroxypropyl-beta-cyclodextrin, hydroxypropyl methylcellulose acetate succinate and polylactic acid, so that the release time of lisinopril is effectively prolonged, and the slow release effect is greatly improved;
3. according to the preparation method, stearic acid and hydrogenated castor oil are used as framework materials, and the bonding effect of cellulose acetate phthalate and starch sodium octenylsuccinate is combined, so that the raw lisinopril powder is uniformly dispersed in the framework materials under the emulsification and dispersion effects of glyceryl monostearate and triethyl citrate, and the lisinopril tablet with a good slow release effect is finally prepared.
Detailed Description
The following description of the preferred embodiments of the present invention is provided for the purpose of illustration and description, and is in no way intended to limit the invention.
Example 1: preparation method of lisinopril sustained-release tablet
The method comprises the following steps:
1. preparation of technical emulsion
Mixing lisinopril, vitamin E polyethylene glycol succinate, hydroxypropyl-beta-cyclodextrin and deionized water, and stirring to dissolve completely to obtain a raw water phase; dissolving hydroxypropyl methyl cellulose acetate succinate and polylactic acid in dichloromethane to obtain an oil phase, slowly adding the oil phase into a raw medicine water phase at the shearing rate of 45000 r/min, and shearing and dispersing for 40 minutes to obtain a raw medicine emulsion;
the mass ratio of lisinopril, vitamin E polyethylene glycol succinate, hydroxypropyl-beta-cyclodextrin and deionized water in the aqueous phase of the raw medicine is 10:5:3: 110;
the mass ratio of hydroxypropyl methyl cellulose acetate succinate, polylactic acid and dichloromethane in the oil phase is 3:7: 75;
the molecular weight of the polylactic acid is 16000 g/mol;
the mass ratio of the oil phase to the aqueous phase in the original medicine emulsion is 2: 10.
2. Preparation of bulk drug powder
Spray granulating the original medicine emulsion, controlling the air inlet temperature at 130 deg.C and the atomization pressure at 100kPa to obtain powder with particle size of 40 μm, and drying the powder at 85 deg.C for 3 hr to obtain original medicine powder.
3. Preparation of drug-loaded pellets
Mixing stearic acid and hydrogenated castor oil, heating to 85 ℃, melting into liquid, slowly adding original medicine powder into the liquid at the stirring speed of 7000 rpm, then sequentially adding magnesium stearate, triethyl citrate, glyceryl monostearate, sodium starch octenyl succinate and cellulose acetate phthalate, continuously stirring for 3 hours after the addition is finished, cooling to room temperature to obtain a block solid, freezing the block solid at the temperature of minus 30 ℃ for 4 hours, and then crushing the block solid at the temperature of minus 10 ℃ into medicine-carrying granules with the particle size of 80 microns;
the mass ratio of stearic acid to hydrogenated castor oil to raw medicine powder to magnesium stearate to triethyl citrate to starch sodium octenyl succinate to cellulose acetate phthalate to glyceryl monostearate is 8:18:30:4:8:5:3: 10.
4. Tabletting
The drug-loaded pellets were compressed into tablets to obtain lisinopril tablets having a hardness of 9.5 Kg.
Example 2: preparation method of lisinopril sustained-release tablet
The method comprises the following steps:
1. preparation of technical emulsion
Mixing lisinopril, vitamin E polyethylene glycol succinate, hydroxypropyl-beta-cyclodextrin and deionized water, and stirring to dissolve completely to obtain a raw water phase; dissolving hydroxypropyl methyl cellulose acetate succinate and polylactic acid in dichloromethane to obtain an oil phase, slowly adding the oil phase into a raw medicine water phase at the shearing rate of 35000 r/min, and shearing and dispersing for 30 min to obtain a raw medicine emulsion;
the mass ratio of lisinopril, vitamin E polyethylene glycol succinate, hydroxypropyl-beta-cyclodextrin and deionized water in the aqueous phase of the raw medicine is 5:1:2: 90;
the mass ratio of hydroxypropyl methyl cellulose acetate succinate, polylactic acid and dichloromethane in the oil phase is 1:4: 50;
the molecular weight of the polylactic acid is 11000 g/mol;
the mass ratio of the oil phase to the aqueous phase in the original medicine emulsion is 1: 10.
2. Preparation of bulk drug powder
Spray granulating the original medicine emulsion, controlling the air inlet temperature at 110 ℃ and the atomization pressure at 80kPa to obtain powder with the particle size of 20 microns, and drying the powder at 75 ℃ for 1.5 hours to obtain original medicine powder.
3. Preparation of drug-loaded pellets
Mixing stearic acid and hydrogenated castor oil, heating to 80 ℃, melting into liquid, slowly adding original medicine powder into the liquid at the stirring speed of 5000 r/min, then sequentially adding magnesium stearate, triethyl citrate, glyceryl monostearate, sodium starch octenyl succinate and cellulose acetate phthalate, continuously stirring for 2 hours after the addition is finished, cooling to room temperature to obtain a block solid, freezing the block solid at the temperature of minus 40 ℃ for 2 hours, and then crushing the block solid at the temperature of minus 13 ℃ into medicine-carrying granules with the grain size of 50 microns;
the mass ratio of stearic acid to hydrogenated castor oil to raw medicine powder to magnesium stearate to triethyl citrate to starch sodium octenyl succinate to cellulose acetate phthalate to glyceryl monostearate is 5:13:25:1:5:2:1: 6.
4. Tablet press
And pressing the drug-loaded granules into tablets to obtain lisinopril tablets with the hardness of 9 Kg.
Example 3: preparation method of lisinopril sustained-release tablet
The method comprises the following steps:
1. preparation of technical emulsion
Mixing lisinopril, vitamin E polyethylene glycol succinate, hydroxypropyl-beta-cyclodextrin and deionized water, and stirring to dissolve completely to obtain a raw water phase; dissolving hydroxypropyl methyl cellulose acetate succinate and polylactic acid in dichloromethane to obtain an oil phase, slowly adding the oil phase into a raw medicine water phase at a shear rate of 55000 r/min, and shearing and dispersing for 50 minutes to obtain a raw medicine emulsion;
the mass ratio of lisinopril, vitamin E polyethylene glycol succinate, hydroxypropyl-beta-cyclodextrin and deionized water in the aqueous phase of the raw medicine is 15:8:4.5: 130;
the mass ratio of hydroxypropyl methyl cellulose acetate succinate, polylactic acid and dichloromethane in the oil phase is 6:10: 90;
the molecular weight of the polylactic acid is 18000 g/mol;
the mass ratio of the oil phase to the aqueous phase in the original drug emulsion is 4: 10.
2. Preparation of bulk drug powder
Spray granulating the original medicine emulsion, controlling the air inlet temperature at 145 ℃ and the atomization pressure at 120kPa to obtain powder with the particle size of 60 microns, and drying the powder at 90 ℃ for 4 hours to obtain original medicine powder.
3. Preparation of drug-loaded pellets
Mixing stearic acid and hydrogenated castor oil, heating to 95 ℃, melting into liquid, slowly adding original medicine powder into the liquid at a stirring speed of 8000 rpm, then sequentially adding magnesium stearate, triethyl citrate, glyceryl monostearate, sodium starch octenyl succinate and cellulose acetate phthalate, continuously stirring for 2-4 hours after the addition is finished, cooling to room temperature to obtain a block solid, freezing the block solid at-15 ℃ for 6 hours, and then crushing the block solid at-5 ℃ into medicine-carrying granules with the particle size of 90 micrometers;
the mass ratio of the stearic acid to the hydrogenated castor oil to the technical powder to the magnesium stearate to the triethyl citrate to the starch sodium octenyl succinate to the cellulose acetate phthalate to the glyceryl monostearate is 10:20:35:5:10:8:5: 12.
4. Tabletting
The drug-loaded pellets were compressed into tablets to obtain lisinopril tablets having a hardness of 10.5 Kg.
Comparative example 1: example 1 based on the above, two steps of preparing a drug emulsion and preparing a drug powder were not performed
Based on example 1, step 1 and step 2 were not performed;
in step 3, 30 parts of raw drug powder is replaced by 30 parts of lisinopril powder with the particle size of 40 microns on the basis of the example 1, and the other operations are the same as the example 1;
step 4 was performed as in example 1.
Comparative example 2: example 1 replacement of sodium starch octenyl succinate and cellulose acetate phthalate with hydroxypropylmethylcellulose
Steps 1 and 2 were the same as in example 1;
in step 3, 5 parts of starch sodium octenyl succinate and 3 parts of cellulose acetate phthalate are replaced by 8 parts of hydroxypropyl methylcellulose based on example 1, and the other operations are the same as example 1;
step 4 was performed as in example 1.
Release test
The lisinopril tablets obtained in examples 1, 2 and 3 and comparative examples 1 and 2 were tested for release according to the method specified in the chinese pharmacopoeia 2010, and the results are shown in the following table:
Claims (2)
1. a preparation method of lisinopril sustained-release tablets is characterized by comprising the following steps: comprises 4 steps of preparing original medicine emulsion, preparing original medicine powder, preparing medicine-carrying granules and tabletting;
the preparation method of the raw medicine emulsion comprises the steps of mixing lisinopril, vitamin E polyethylene glycol succinate, hydroxypropyl-beta-cyclodextrin and deionized water, and stirring and dissolving completely to obtain a raw medicine water phase; dissolving hydroxypropyl methyl cellulose acetate succinate and polylactic acid in dichloromethane to obtain an oil phase, slowly adding the oil phase into a raw medicine water phase at a shearing rate of 35000-55000 r/min, and shearing and dispersing for 30-50 minutes to obtain a raw medicine emulsion;
the mass ratio of lisinopril, vitamin E polyethylene glycol succinate, hydroxypropyl-beta-cyclodextrin and deionized water in the raw water phase is 5-15: 1-8: 2-4.5: 90-130;
the mass ratio of hydroxypropyl methyl cellulose acetate succinate, polylactic acid and dichloromethane in the oil phase is 1-6: 4-10: 50-90;
the molecular weight of the polylactic acid is 11000-18000 g/mol;
the mass ratio of the oil phase to the original water phase in the original emulsion is 1-4: 10;
the preparation method of the original drug powder comprises the steps of carrying out spray granulation on original drug emulsion, controlling the air inlet temperature to be 110-145 ℃, the atomization pressure to be 80-120 kPa, obtaining powder with the particle size of 20-60 microns, and drying the powder at the temperature of 75-90 ℃ for 1.5-4 hours to obtain original drug powder;
the preparation method of the drug-loaded granules comprises the steps of mixing stearic acid and hydrogenated castor oil, heating the mixture to 80-95 ℃, melting the mixture into liquid, slowly adding technical powder into the mixture at a stirring speed of 5000-8000 rpm, then sequentially adding magnesium stearate, triethyl citrate, glyceryl monostearate, sodium starch octenyl succinate and cellulose acetate phthalate, continuously stirring the mixture for 2-4 hours after the addition is finished, cooling the mixture to room temperature to obtain blocky solid, freezing the blocky solid at-40 to-15 ℃ for 2-6 hours, and then crushing the blocky solid at-13 to-5 ℃ into the drug-loaded granules with the particle size of 50-90 micrometers;
the weight ratio of stearic acid, hydrogenated castor oil, crude drug powder, magnesium stearate, triethyl citrate, starch sodium octenylsuccinate, cellulose acetate phthalate and glyceryl monostearate is 5-10: 13-20: 25-35: 1-5: 5-10: 2-8: 1-5: 6-12.
2. The method for preparing lisinopril sustained-release tablets according to claim 1, which is characterized in that:
and the tabletting is carried out, wherein the drug-loaded granules are pressed into tablets to obtain lisinopril tablets with the hardness of 9-10.5 Kg.
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| CN107281461A (en) * | 2017-06-13 | 2017-10-24 | 江苏黄河药业股份有限公司 | A kind of lisinopril sustained release tablets and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007036952A2 (en) * | 2005-07-01 | 2007-04-05 | Rubicon Research Pvt Ltd. | Novel sustained release dosage form |
| FR2891459B1 (en) * | 2005-09-30 | 2007-12-28 | Flamel Technologies Sa | MICROPARTICLES WITH MODIFIED RELEASE OF AT LEAST ONE ACTIVE INGREDIENT AND ORAL GALENIC FORM COMPRISING THE SAME |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2003113120A (en) * | 2001-08-03 | 2003-04-18 | Takeda Chem Ind Ltd | Sustained release medicine |
| CN1895230A (en) * | 2005-07-11 | 2007-01-17 | 刘凤鸣 | Lisinopril drop balls and production thereof |
| EP2387991A1 (en) * | 2006-02-01 | 2011-11-23 | Adventrx Pharmaceuticals, Inc. | Vitamin E succinate stabilized pharmaceutical compositions, methods for the preparation and the use thereof |
| CN103006612A (en) * | 2012-12-28 | 2013-04-03 | 台州职业技术学院 | Lisinopril controlled-release tablet and preparation method thereof |
| CN105055358A (en) * | 2015-07-31 | 2015-11-18 | 洛阳君山制药有限公司 | Preparation of lisinopril sustained-release tablets |
| CN107029208A (en) * | 2017-06-13 | 2017-08-11 | 江苏黄河药业股份有限公司 | It is a kind of to treat lisinopril compound preparation of angiocardiopathy and preparation method thereof |
| CN107281461A (en) * | 2017-06-13 | 2017-10-24 | 江苏黄河药业股份有限公司 | A kind of lisinopril sustained release tablets and preparation method thereof |
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