JPH0611699B2 - 固体薬剤調製物及びその製造法 - Google Patents
固体薬剤調製物及びその製造法Info
- Publication number
- JPH0611699B2 JPH0611699B2 JP63153676A JP15367688A JPH0611699B2 JP H0611699 B2 JPH0611699 B2 JP H0611699B2 JP 63153676 A JP63153676 A JP 63153676A JP 15367688 A JP15367688 A JP 15367688A JP H0611699 B2 JPH0611699 B2 JP H0611699B2
- Authority
- JP
- Japan
- Prior art keywords
- core
- group
- coating
- active compound
- coated
- 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.)
- Expired - Lifetime
Links
- 239000007787 solid Substances 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 13
- 229940079593 drug Drugs 0.000 title description 10
- 239000003814 drug Substances 0.000 title description 10
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 16
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000005923 long-lasting effect Effects 0.000 claims abstract description 7
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 62
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 62
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 61
- 239000011248 coating agent Substances 0.000 claims description 57
- 238000000576 coating method Methods 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 44
- 238000007906 compression Methods 0.000 claims description 40
- 230000006835 compression Effects 0.000 claims description 40
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 claims description 28
- 229960001597 nifedipine Drugs 0.000 claims description 28
- 239000002245 particle Substances 0.000 claims description 24
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 18
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 18
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 18
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 18
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 16
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 16
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 16
- 239000012730 sustained-release form Substances 0.000 claims description 15
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 12
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims description 12
- VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 claims description 11
- 229960000227 nisoldipine Drugs 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000010410 layer Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 7
- 238000013268 sustained release Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- UIAGMCDKSXEBJQ-IBGZPJMESA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-IBGZPJMESA-N 0.000 claims description 4
- 210000004051 gastric juice Anatomy 0.000 claims description 4
- 229920000609 methyl cellulose Polymers 0.000 claims description 4
- 239000001923 methylcellulose Substances 0.000 claims description 4
- 235000010981 methylcellulose Nutrition 0.000 claims description 4
- 229960000715 nimodipine Drugs 0.000 claims description 4
- 229920003169 water-soluble polymer Polymers 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000011247 coating layer Substances 0.000 claims description 3
- 229920001577 copolymer Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims 2
- -1 nitorendipine Chemical compound 0.000 claims 2
- RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 229920006184 cellulose methylcellulose Polymers 0.000 claims 1
- 238000000975 co-precipitation Methods 0.000 claims 1
- 229960003580 felodipine Drugs 0.000 claims 1
- 239000003906 humectant Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 description 87
- 239000008187 granular material Substances 0.000 description 80
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 80
- 239000000203 mixture Substances 0.000 description 47
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 41
- 239000008101 lactose Substances 0.000 description 41
- 235000019359 magnesium stearate Nutrition 0.000 description 40
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 26
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 24
- 239000007900 aqueous suspension Substances 0.000 description 23
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 22
- 229920002261 Corn starch Polymers 0.000 description 15
- 239000008120 corn starch Substances 0.000 description 15
- 238000005303 weighing Methods 0.000 description 15
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 13
- 239000002202 Polyethylene glycol Substances 0.000 description 13
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 13
- 239000008108 microcrystalline cellulose Substances 0.000 description 13
- 229940016286 microcrystalline cellulose Drugs 0.000 description 13
- 229920001223 polyethylene glycol Polymers 0.000 description 13
- 239000004408 titanium dioxide Substances 0.000 description 13
- 229960005425 nitrendipine Drugs 0.000 description 12
- PVHUJELLJLJGLN-INIZCTEOSA-N (S)-nitrendipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 PVHUJELLJLJGLN-INIZCTEOSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 11
- 239000008119 colloidal silica Substances 0.000 description 11
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- 238000007873 sieving Methods 0.000 description 8
- 239000013543 active substance Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000012530 fluid Substances 0.000 description 5
- 230000003204 osmotic effect Effects 0.000 description 5
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 5
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000005469 granulation Methods 0.000 description 4
- 230000003179 granulation Effects 0.000 description 4
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 4
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007932 molded tablet Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 229920003072 Plasdone™ povidone Polymers 0.000 description 2
- 239000004141 Sodium laurylsulphate Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000007888 film coating Substances 0.000 description 2
- 238000009501 film coating Methods 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000007939 sustained release tablet Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 102100026681 Chromobox protein homolog 8 Human genes 0.000 description 1
- 229920003114 HPC-L Polymers 0.000 description 1
- 101000910841 Homo sapiens Chromobox protein homolog 8 Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 241000022844 Praxis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000000280 densification Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000007907 direct compression Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229920003112 high viscosity grade hydroxypropyl cellulose Polymers 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229920003117 medium viscosity grade hydroxypropyl cellulose Polymers 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- PVHUJELLJLJGLN-UHFFFAOYSA-N nitrendipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 PVHUJELLJLJGLN-UHFFFAOYSA-N 0.000 description 1
- 238000003921 particle size analysis Methods 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 239000007916 tablet composition Substances 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
- A61K9/209—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat containing drug in at least two layers or in the core and in at least one outer layer
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3720757.1 | 1987-06-24 | ||
| DE19873720757 DE3720757A1 (de) | 1987-06-24 | 1987-06-24 | Dhp-manteltablette |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8321158A Division JP2955524B2 (ja) | 1987-06-24 | 1996-11-18 | 固体薬剤調製物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6422822A JPS6422822A (en) | 1989-01-25 |
| JPH0611699B2 true JPH0611699B2 (ja) | 1994-02-16 |
Family
ID=6330136
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63153676A Expired - Lifetime JPH0611699B2 (ja) | 1987-06-24 | 1988-06-23 | 固体薬剤調製物及びその製造法 |
| JP8321158A Expired - Lifetime JP2955524B2 (ja) | 1987-06-24 | 1996-11-18 | 固体薬剤調製物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8321158A Expired - Lifetime JP2955524B2 (ja) | 1987-06-24 | 1996-11-18 | 固体薬剤調製物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4892741A (en, 2012) |
| EP (1) | EP0299211B1 (en, 2012) |
| JP (2) | JPH0611699B2 (en, 2012) |
| AT (1) | ATE75142T1 (en, 2012) |
| CA (1) | CA1309951C (en, 2012) |
| DE (2) | DE3720757A1 (en, 2012) |
| ES (1) | ES2051800T3 (en, 2012) |
| GR (1) | GR3004448T3 (en, 2012) |
| IE (1) | IE60352B1 (en, 2012) |
| IL (1) | IL86827A (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0776660A2 (en) | 1995-11-28 | 1997-06-04 | Bayer Ag | Long-lasting release nifedipine preparation |
| WO2004082665A1 (ja) * | 2003-03-17 | 2004-09-30 | Takeda Pharmaceutical Company Limited | 放出制御組成物 |
| JP2004300149A (ja) * | 2003-03-17 | 2004-10-28 | Takeda Chem Ind Ltd | 放出制御組成物 |
Families Citing this family (92)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2618073B1 (fr) * | 1987-07-16 | 1990-09-07 | Pf Medicament | Comprimes de type a matrice hydrophile a base de salbutamol et leur procede de preparation |
| US5032406A (en) * | 1989-02-21 | 1991-07-16 | Norwich Eaton Pharmaceuticals, Inc. | Dual-action tablet |
| FI93924C (fi) * | 1991-09-17 | 1995-06-26 | Martti Lauri Antero Marvola | Menetelmä säädellysti lääkeainetta vapauttavan valmisteen valmistamiseksi |
| DE69222006T2 (de) * | 1991-10-30 | 1998-01-22 | Glaxo Group Ltd | Mehrschichtzusammensetzungen enthaltend Histamin- oder Serotonin- Antagonisten |
| DE4201173C2 (de) * | 1992-01-17 | 1998-10-29 | Alfatec Pharma Gmbh | Akutarzneimittel in Form von Dihydropyridinderivaten enthaltenden Pellets und ihre Herstellung |
| DE4201179A1 (de) * | 1992-01-17 | 1993-07-22 | Alfatec Pharma Gmbh | Wirkstoff(e) enthaltendes granulat oder pellet mit einem geruest aus hydrophilen makromolekuelen und verfahren zu seiner herstellung |
| AU3949093A (en) * | 1992-03-31 | 1993-11-08 | Benzon Pharma A/S | A pharmaceutical formulation |
| US5455046A (en) * | 1993-09-09 | 1995-10-03 | Edward Mendell Co., Inc. | Sustained release heterodisperse hydrogel systems for insoluble drugs |
| US6726930B1 (en) * | 1993-09-09 | 2004-04-27 | Penwest Pharmaceuticals Co. | Sustained release heterodisperse hydrogel systems for insoluble drugs |
| US5662933A (en) * | 1993-09-09 | 1997-09-02 | Edward Mendell Co., Inc. | Controlled release formulation (albuterol) |
| US5773025A (en) | 1993-09-09 | 1998-06-30 | Edward Mendell Co., Inc. | Sustained release heterodisperse hydrogel systems--amorphous drugs |
| US6676967B1 (en) * | 1993-09-20 | 2004-01-13 | Kos Pharmaceuticals, Inc. | Methods for reducing flushing in individuals being treated with nicotinic acid for hyperlipidemia |
| US6129930A (en) | 1993-09-20 | 2000-10-10 | Bova; David J. | Methods and sustained release nicotinic acid compositions for treating hyperlipidemia at night |
| US6746691B2 (en) | 1993-09-20 | 2004-06-08 | Kos Pharmaceuticals, Inc. | Intermediate release nicotinic acid compositions for treating hyperlipidemia having unique biopharmaceutical characteristics |
| US6080428A (en) | 1993-09-20 | 2000-06-27 | Bova; David J. | Nicotinic acid compositions for treating hyperlipidemia and related methods therefor |
| US6818229B1 (en) | 1993-09-20 | 2004-11-16 | Kos Pharmaceuticals, Inc. | Intermediate release nicotinic acid compositions for treating hyperlipidemia |
| US20060263428A1 (en) * | 1993-09-20 | 2006-11-23 | Eugenio Cefali | Methods for treating hyperlipidemia with intermediate release nicotinic acid compositions having unique biopharmaceutical characteristics |
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-
1987
- 1987-06-24 DE DE19873720757 patent/DE3720757A1/de not_active Withdrawn
-
1988
- 1988-06-08 US US07/204,056 patent/US4892741A/en not_active Expired - Lifetime
- 1988-06-14 DE DE8888109420T patent/DE3870338D1/de not_active Expired - Lifetime
- 1988-06-14 EP EP88109420A patent/EP0299211B1/de not_active Expired - Lifetime
- 1988-06-14 AT AT88109420T patent/ATE75142T1/de not_active IP Right Cessation
- 1988-06-14 ES ES88109420T patent/ES2051800T3/es not_active Expired - Lifetime
- 1988-06-22 IL IL86827A patent/IL86827A/xx not_active IP Right Cessation
- 1988-06-22 CA CA000570069A patent/CA1309951C/en not_active Expired - Lifetime
- 1988-06-23 IE IE191688A patent/IE60352B1/en not_active IP Right Cessation
- 1988-06-23 JP JP63153676A patent/JPH0611699B2/ja not_active Expired - Lifetime
-
1992
- 1992-04-23 GR GR920400734T patent/GR3004448T3/el unknown
-
1996
- 1996-11-18 JP JP8321158A patent/JP2955524B2/ja not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0776660A2 (en) | 1995-11-28 | 1997-06-04 | Bayer Ag | Long-lasting release nifedipine preparation |
| WO2004082665A1 (ja) * | 2003-03-17 | 2004-09-30 | Takeda Pharmaceutical Company Limited | 放出制御組成物 |
| JP2004300149A (ja) * | 2003-03-17 | 2004-10-28 | Takeda Chem Ind Ltd | 放出制御組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2051800T3 (es) | 1994-07-01 |
| DE3720757A1 (de) | 1989-01-05 |
| IE881916L (en) | 1988-12-24 |
| US4892741A (en) | 1990-01-09 |
| IL86827A (en) | 1993-02-21 |
| GR3004448T3 (en, 2012) | 1993-03-31 |
| CA1309951C (en) | 1992-11-10 |
| JPS6422822A (en) | 1989-01-25 |
| DE3870338D1 (de) | 1992-05-27 |
| IE60352B1 (en) | 1994-06-29 |
| JP2955524B2 (ja) | 1999-10-04 |
| ATE75142T1 (de) | 1992-05-15 |
| JPH09183728A (ja) | 1997-07-15 |
| EP0299211B1 (de) | 1992-04-22 |
| EP0299211A1 (de) | 1989-01-18 |
| IL86827A0 (en) | 1988-11-30 |
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