CN103462930B - A kind of ganciclovir capsule preparations and preparation method thereof - Google Patents
A kind of ganciclovir capsule preparations and preparation method thereof Download PDFInfo
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- CN103462930B CN103462930B CN201310400117.4A CN201310400117A CN103462930B CN 103462930 B CN103462930 B CN 103462930B CN 201310400117 A CN201310400117 A CN 201310400117A CN 103462930 B CN103462930 B CN 103462930B
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- ganciclovir
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- IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 title claims abstract description 68
- 229960002963 ganciclovir Drugs 0.000 title claims abstract description 68
- 238000002360 preparation method Methods 0.000 title claims abstract description 41
- 239000002775 capsule Substances 0.000 title claims abstract description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000003756 stirring Methods 0.000 claims abstract description 22
- 238000010792 warming Methods 0.000 claims abstract description 22
- 239000001856 Ethyl cellulose Substances 0.000 claims abstract description 21
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229920001249 ethyl cellulose Polymers 0.000 claims abstract description 21
- 235000019325 ethyl cellulose Nutrition 0.000 claims abstract description 21
- 239000006187 pill Substances 0.000 claims abstract description 20
- 229940057995 liquid paraffin Drugs 0.000 claims abstract description 14
- 239000004094 surface-active agent Substances 0.000 claims abstract description 13
- 230000003292 diminished effect Effects 0.000 claims abstract description 11
- 238000001914 filtration Methods 0.000 claims abstract description 11
- NWGKJDSIEKMTRX-MDZDMXLPSA-N Sorbitan oleate Chemical group CCCCCCCC\C=C\CCCCCCCC(=O)OCC(O)C1OCC(O)C1O NWGKJDSIEKMTRX-MDZDMXLPSA-N 0.000 claims description 9
- PRXRUNOAOLTIEF-WUOFIQDXSA-N sorbitan trioleate Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C\CCCCCCCC)C1OCC(O)C1OC(=O)CCCCCCC\C=C\CCCCCCCC PRXRUNOAOLTIEF-WUOFIQDXSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 abstract description 10
- 239000000463 material Substances 0.000 abstract description 2
- 238000009472 formulation Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 229940079593 drug Drugs 0.000 description 4
- 239000003094 microcapsule Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 206010048843 Cytomegalovirus chorioretinitis Diseases 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 208000001763 cytomegalovirus retinitis Diseases 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
- 229960003444 immunosuppressant agent Drugs 0.000 description 2
- 230000001861 immunosuppressant effect Effects 0.000 description 2
- 239000003018 immunosuppressive agent Substances 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 206010011831 Cytomegalovirus infection Diseases 0.000 description 1
- 108010080379 Fibrin Tissue Adhesive Proteins 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061598 Immunodeficiency Diseases 0.000 description 1
- 208000029462 Immunodeficiency disease Diseases 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- -1 common granulation Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 230000007813 immunodeficiency Effects 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention discloses a kind of ganciclovir capsule preparations, comprise capsule shells and content, described content is ganciclovir slow-release micro-pill, described ganciclovir slow-release micro-pill is prepared from as follows: ganciclovir, ethyl cellulose and Hydroxypropylcelliloxe are dissolved in ethanol, be added in the liquid paraffin containing surfactant under stirring condition, be warming up to 38-42 DEG C gradually, insulated and stirred 4-8h, be warming up to 68-72 DEG C, stir 0.5-2h, filtration under diminished pressure, obtains ganciclovir slow-release micro-pill.Invention formulation not only drastically reduce the area the consumption of slow-release material, and eliminates the prominent of medicine and release phenomenon.
Description
Technical field
The invention belongs to medical art, in particular to a kind of antiviral drugs preparation, particularly relate to a kind of ganciclovir capsule preparations and preparation method thereof.
Background technology
Ganciclovir (famcictovir, FCV) be second filial generation open nucleoside class antiviral agents, chemistry 9-(1 by name, 3-dihydroxy-2-third oxygen methyl) guanine, the cytomegalovirus infection of clinical prevention and treatment immunodeficiency patient, as HIV sufferers, accept the tumor patient of chemotherapy, use the organ transplant patients of immunosuppressant.In normal renal function situation: the maintaining treatment of CMV retinitis: after inductive treatment, maintenance dose is recommended to be each 1000mg, one day 3 times, with food with taking.Also can when non-sleep each serving 500mg, every 3 hours 1 time, every day 6 times, with food with taking.If CMV retinitis has development during maintaining treatment, then inductive treatment should be re-started.The prevention of late stage HIV infection patient CMV disease: preventive dose is each 1000mg, one day 3 times, with food with taking.The prevention of organ transplant recipients CMV disease: preventive dose is each 1000mg, one day 3 times, with food with taking.Drug treatment was determined according to immunosuppressant time and degree.In order to reduce medicining times, improving the interdependence of patient medication, reducing the generation of untoward reaction, developing ganciclovir slow releasing capsule.
The existing technology preparing ganciclovir capsule is all carry ganciclovir by Fibrin Glue, or uses emulsification-evaporation method to prepare ganciclovir medical resin slow-releasing microcapsule, and cause supplementary product kind many, consumption is large, is unfavorable for reducing production cost.
Summary of the invention
In view of the deficiencies in the prior art, the object of the present invention is to provide a kind of supplementary product kind and the less ganciclovir capsule preparations of consumption and preparation method thereof.
In order to realize object of the present invention, inventor is studied by lot of experiments, creatively by ethyl cellulose and Hydroxypropylcelliloxe coupling, intra-liquid desiccation method is utilized to be prepared into ganciclovir slow-release micro-pill, achieve beyond thought effect, not only drastically reduce the area the consumption of slow-release material, and eliminate the prominent of medicine and release phenomenon, and finally obtain following technical scheme:
A kind of ganciclovir capsule preparations, comprise capsule shells and content, described content is ganciclovir slow-release micro-pill, and described ganciclovir slow-release micro-pill is prepared from as follows: ganciclovir, ethyl cellulose and Hydroxypropylcelliloxe are dissolved in ethanol, be added in the liquid paraffin containing surfactant under stirring condition, be warming up to 38-42 DEG C gradually, insulated and stirred 4-8h, is warming up to 68-72 DEG C, stirs 0.5-2h, filtration under diminished pressure, obtains ganciclovir slow-release micro-pill.
Preferably, above-mentioned ganciclovir capsule preparations, the weight ratio of wherein said ganciclovir, ethyl cellulose and Hydroxypropylcelliloxe is 1:0.2-2:0.04-0.6.
Further preferably, above-mentioned ganciclovir capsule preparations, the weight ratio of wherein said ganciclovir, ethyl cellulose and Hydroxypropylcelliloxe is 1:0.6-1.2:0.1-0.3.
Again further preferably, above-mentioned ganciclovir capsule preparations, the weight ratio of wherein said ganciclovir, ethyl cellulose and Hydroxypropylcelliloxe is 1:1:0.2.
The ganciclovir capsule preparations that the present invention is above-mentioned, wherein said surfactant is sorbester p17 and/or sorbester p37; Described surfactant is preferably sorbester p37.
In addition, above-mentioned ganciclovir capsule preparations, the content of wherein said surfactant in liquid paraffin is at 0.2-2%(v/v).
Second object of the present invention is the preparation method providing a kind of above-mentioned ganciclovir capsule preparations, the method comprises the steps: ganciclovir, ethyl cellulose and Hydroxypropylcelliloxe to dissolve in ethanol, be added in the liquid paraffin containing surfactant under stirring condition, be warming up to 38-42 DEG C gradually, insulated and stirred 4-8h, is warming up to 68-72 DEG C, stirs 0.5-2h, filtration under diminished pressure, obtains ganciclovir slow-release micro-pill; Using described slow-release micro-pill as Contents Fill capsule shells, obtain ganciclovir capsule.
In the preparation method of above-mentioned ganciclovir capsule preparations, described surfactant is preferably sorbester p17 and/or sorbester p37.
In the preparation method of above-mentioned ganciclovir capsule preparations, the content of wherein said surfactant in liquid paraffin is at 0.2-2%(v/v).
Compared with prior art, ganciclovir capsule preparations that the present invention relates to and preparation method thereof tool has the following advantages and progress significantly: (1) supplementary product kind is few, consumption is few, and production cost is low; (2) technique is simple, meets large production requirement; (3) release of medicine solves zero-order release.
Detailed description of the invention
Following examples further describe preparation process of the present invention and beneficial effect, embodiment is only for the object of illustration, do not limit the scope of the invention, the simultaneously apparent change made according to the present invention of those of ordinary skill in the art and modification are also contained within the scope of the invention.
Embodiment 1
Preparation technology:
Recipe quantity takes ganciclovir, ethyl cellulose and Hydroxypropylcelliloxe, add in ethanol, be stirred to dissolve, be added to containing 0.5%(v/v under stirring condition) in the liquid paraffin of sorbester p17, be warming up to 40 DEG C gradually, insulated and stirred 6h, be warming up to 70 DEG C, stir 1h, filtration under diminished pressure, obtain ganciclovir slow-release micro-pill, capsule charge shell.
Embodiment 2
Preparation technology:
Recipe quantity takes ganciclovir, ethyl cellulose and Hydroxypropylcelliloxe, add in ethanol, be stirred to dissolve, be added to containing 2%(v/v under stirring condition) in the liquid paraffin of sorbester p17, be warming up to 40 DEG C gradually, insulated and stirred 6h, be warming up to 70 DEG C, stir 1h, filtration under diminished pressure, obtain ganciclovir slow-release micro-pill, capsule charge shell.
Embodiment 3
Preparation technology:
Recipe quantity takes ganciclovir, ethyl cellulose and Hydroxypropylcelliloxe, add in ethanol, be stirred to dissolve, be added to containing 0.5%(v/v under stirring condition) in the liquid paraffin of sorbester p17, be warming up to 40 DEG C gradually, insulated and stirred 6h, be warming up to 70 DEG C, stir 1h, filtration under diminished pressure, obtain ganciclovir slow-release micro-pill, capsule charge shell.
Comparative example 1
Preparation technology:
Recipe quantity takes ganciclovir, ethyl cellulose and low-viscosity hydroxypropylcelluloand, add in ethanol, be stirred to dissolve, be added to containing 0.5%(v/v under stirring condition) in the liquid paraffin of sorbester p17, be warming up to 40 DEG C gradually, insulated and stirred 6h, be warming up to 70 DEG C, stir 1h, filtration under diminished pressure, obtain ganciclovir slow-release micro-pill, capsule charge shell.
Comparative example 2
Ganciclovir 250g
Ethyl cellulose 250g
Hydroxypropylcelliloxe (H model) 50g
Appropriate amount of ethanol
Preparation technology:
Recipe quantity took the ganciclovir of 100 mesh sieves, ethyl cellulose and Hydroxypropylcelliloxe, added ethanol in proper amount and granulated, dry, crossed 20 mesh sieves, capsule charge shell.
Comparative example 3
Preparation technology:
Recipe quantity takes ganciclovir, especially strange RSPO, Hydroxypropylcelliloxe, add in ethanol, be stirred to dissolve, be added to containing 0.5%(v/v under stirring condition) in the liquid paraffin of sorbester p17, be warming up to 40 DEG C gradually, insulated and stirred 6h, be warming up to 70 DEG C, stir 1h, filtration under diminished pressure, obtain ganciclovir slow-release micro-pill, capsule charge shell.
Comparative example 4
Preparation technology:
Recipe quantity takes ganciclovir, ethyl cellulose, Hydroxypropylcelliloxe, add in ethanol, be stirred to dissolve, be added under stirring condition in liquid paraffin, be warming up to 40 DEG C gradually, insulated and stirred 6h, be warming up to 70 DEG C, stir 1h, filtration under diminished pressure, obtain ganciclovir slow-release micro-pill, capsule charge shell.
Embodiment 4 drug release determination is tested
The ganciclovir capsule prepared of Example 1-3 and comparative example 1-4 respectively, measure according to Chinese Pharmacopoeia version in 2010 two annex XD first methods, adopt the device of dissolution method first method, with 0.1mol/L hydrochloric acid 750ml for solvent, rotating speed is 100 turns per minute, operate in accordance with the law, through 1.5 hours, get solution 10ml, filter, as need testing solution 1, 0.1mol/L hydrochloric acid 10ml is supplemented in time in process container, and in 0.1mol/L hydrochloric acid, add the 0.2mol/L sodium radio-phosphate,P-32 solution 250ml (using 2mol/L hydrochloric acid solution or 2mol/L sodium hydroxide solution adjust ph 6.8 ± 0.05 if desired) of 37 DEG C simultaneously,
In 3 hours with within 8 hours, get solution 10ml respectively, filter, and in time in process container, supplement pH6.8 buffer (0.1mol/L hydrochloric acid: 0.2mol/L sodium phosphate is 3: 1) 10ml.Precision measures 3,8 hours sampling subsequent filtrate 5.0ml, puts in 25ml measuring bottle, is diluted to scale, as need testing solution with above-mentioned pH6.8 buffer.Separately get ganciclovir reference substance 25mg respectively, accurately weighed, be diluted to every ml containing the solution product solution in contrast of 25 μ g with 0.1mol/L hydrochloric acid and pH6.8 buffer solution respectively.Get three groups of need testing solutions of above-mentioned two kinds of solvents and the reference substance solution of above-mentioned two kinds of solvents, according to spectrophotography (Chinese Pharmacopoeia version in 2010 two annex IVA), measure trap at 305nm wavelength place, calculate the burst size of every capsules at different time respectively.
| Sample | 1.5h release (%) | 3h release (%) | 8h release (%) |
| Embodiment 1 | 24.5 | 64.4 | 100.1 |
| Embodiment 2 | 14.5 | 32.7 | 76.6 |
| Embodiment 3 | 21.2 | 51.2 | 96.6 |
| Comparative example 1 | 65.6 | 97.7 | 100.4 |
| Comparative example 2 | 40.7 | 87.4 | 98.1 |
| Comparative example 3 | 23.6 | 86.3 | 99.3 |
| Comparative example 4 | 62.2 | 86.1 | 99.6 |
Can be found out by the test data in above table, preparation prepared by embodiment of the present invention 1-3 has good slow release effect; And comparative example 1 replaces Hydroxypropylcelliloxe by low-viscosity hydroxypropylcelluloand, during drug release determination, low-viscosity hydroxypropylcelluloand is dissolved rapidly, and form cavity, medicine discharges rapidly; Comparative example 2 does not prepare microcapsule, common granulation, and medicine is not wrapped up encystation by ethyl cellulose, therefore discharges fast; Comparative example 3 uses especially strange RSPO to replace ethyl cellulose, although 1.5h release better in hydrochloric acid, discharges rapidly in pH6.8 buffer; Comparative example 4 does not add sorbester p17, and the encapsulation ratio preparing microcapsule is little, and most of medicine is attached to microcapsule surface, therefore early stage, release was very fast.
Claims (7)
1. a ganciclovir capsule preparations, comprise capsule shells and content, it is characterized in that: described content is ganciclovir slow-release micro-pill, described ganciclovir slow-release micro-pill is prepared from as follows: by ganciclovir, ethyl cellulose and Hydroxypropylcelliloxe dissolve in ethanol, be added in the liquid paraffin containing surfactant under stirring condition, be warming up to 38-42 DEG C gradually, insulated and stirred 4-8h, be warming up to 68-72 DEG C, stir 0.5-2h, filtration under diminished pressure, obtain ganciclovir slow-release micro-pill, described ganciclovir, the weight ratio of ethyl cellulose and Hydroxypropylcelliloxe is 1:0.2-2:0.04-0.6.
2. ganciclovir capsule preparations according to claim 1, is characterized in that: the weight ratio of described ganciclovir, ethyl cellulose and Hydroxypropylcelliloxe is 1:0.6-1.2:0.1-0.3.
3. ganciclovir capsule preparations according to claim 1, is characterized in that: the weight ratio of described ganciclovir, ethyl cellulose and Hydroxypropylcelliloxe is 1:1:0.2.
4. the ganciclovir capsule preparations according to any one of claim 1-3, is characterized in that: described surfactant is sorbester p17 and/or sorbester p37.
5. the ganciclovir capsule preparations according to any one of claim 1-3, is characterized in that: described surfactant is sorbester p37.
6. the ganciclovir capsule preparations according to any one of claim 1-3, is characterized in that: the content of described surfactant in liquid paraffin is at 0.2-2% (v/v).
7. the preparation method of the ganciclovir capsule preparations according to any one of claim 1-3, it is characterized in that comprising the steps: ganciclovir, ethyl cellulose and Hydroxypropylcelliloxe to dissolve in ethanol, be added in the liquid paraffin containing surfactant under stirring condition, be warming up to 38-42 DEG C gradually, insulated and stirred 4-8h, is warming up to 68-72 DEG C, stirs 0.5-2h, filtration under diminished pressure, obtains ganciclovir slow-release micro-pill; Using described slow-release micro-pill as Contents Fill capsule shells, obtain ganciclovir capsule.
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Address after: 223100 Renmin Road, Hongze County, Jiangsu, Huaian Patentee after: Nanjing Zhengkuan Pharmaceutical Science and Technology Co., Ltd. Address before: 211200 Lishui Economic Development Zone, Jiangsu, Nanjing No. 1 Shandong Road Patentee before: Nanjing Zhengkuan Pharmaceutical Science and Technology Co., Ltd. |
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| C56 | Change in the name or address of the patentee | ||
| CP02 | Change in the address of a patent holder |
Address after: 211200 Lishui Economic Development Zone, Jiangsu, Nanjing No. 1 Shandong Road Patentee after: Nanjing Zhengkuan Pharmaceutical Science and Technology Co., Ltd. Address before: 223100 Renmin Road, Hongze County, Jiangsu, Huaian Patentee before: Nanjing Zhengkuan Pharmaceutical Science and Technology Co., Ltd. |
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Effective date of registration: 20181101 Address after: 201112 C263 1, No. 1628, Su Zhao Road, Minhang District, Shanghai. Patentee after: Shanghai Yuanshi five Pharmaceutical Technology Co., Ltd. Address before: 211200 1 Shandong Road, Lishui Economic Development Zone, Nanjing, Jiangsu. Patentee before: Nanjing Zhengkuan Pharmaceutical Science and Technology Co., Ltd. |
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| CP01 | Change in the name or title of a patent holder | ||
| CP01 | Change in the name or title of a patent holder |
Address after: Room C263, Building 1628 Suzhao Road, Minhang District, Shanghai 201112 Patentee after: Shanghai Orola Pharmaceutical Technology Co., Ltd. Address before: Room C263, Building 1628 Suzhao Road, Minhang District, Shanghai 201112 Patentee before: Shanghai Yuanshi five Pharmaceutical Technology Co., Ltd. |