JPS59219219A - 持続吸収性の薬剤組成物 - Google Patents
持続吸収性の薬剤組成物Info
- Publication number
- JPS59219219A JPS59219219A JP59068974A JP6897484A JPS59219219A JP S59219219 A JPS59219219 A JP S59219219A JP 59068974 A JP59068974 A JP 59068974A JP 6897484 A JP6897484 A JP 6897484A JP S59219219 A JPS59219219 A JP S59219219A
- Authority
- JP
- Japan
- Prior art keywords
- theophylline
- water
- absorption
- acid
- sustained
- 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.)
- Granted
Links
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- 229940079593 drug Drugs 0.000 title claims description 6
- 239000003814 drug Substances 0.000 title claims description 6
- 230000000717 retained effect Effects 0.000 title 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 212
- 229960000278 theophylline Drugs 0.000 claims description 106
- 239000008188 pellet Substances 0.000 claims description 69
- 238000010521 absorption reaction Methods 0.000 claims description 39
- 238000004090 dissolution Methods 0.000 claims description 29
- 230000002459 sustained effect Effects 0.000 claims description 28
- 229920003169 water-soluble polymer Polymers 0.000 claims description 22
- 229920003176 water-insoluble polymer Polymers 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 18
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 239000001856 Ethyl cellulose Substances 0.000 claims description 10
- 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 description 10
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- 238000005259 measurement Methods 0.000 claims description 9
- 229920001800 Shellac Polymers 0.000 claims description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 8
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- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 claims description 8
- 229940113147 shellac Drugs 0.000 claims description 8
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- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 7
- 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 7
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 6
- 239000012736 aqueous medium Substances 0.000 claims description 6
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- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 5
- 239000001630 malic acid Substances 0.000 claims description 5
- 235000011090 malic acid Nutrition 0.000 claims description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
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- 239000001913 cellulose Substances 0.000 claims description 3
- RFXQCUDAHXPYOF-UHFFFAOYSA-N diphyllin Natural products COc1cc2c(c3ccc4OCOc4c3)c5C(=O)OCc5c(O)c2cc1O RFXQCUDAHXPYOF-UHFFFAOYSA-N 0.000 claims description 3
- 229960002819 diprophylline Drugs 0.000 claims description 3
- KSCFJBIXMNOVSH-UHFFFAOYSA-N dyphylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CC(O)CO)C=N2 KSCFJBIXMNOVSH-UHFFFAOYSA-N 0.000 claims description 3
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- 239000002775 capsule Substances 0.000 claims description 2
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- 239000000243 solution Substances 0.000 description 60
- 239000000843 powder Substances 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 8
- 229920003134 Eudragit® polymer Polymers 0.000 description 7
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
- 239000012730 sustained-release form Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
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- 239000004014 plasticizer Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
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- 229960001948 caffeine Drugs 0.000 description 4
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- 235000010981 methylcellulose Nutrition 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- 206010014561 Emphysema Diseases 0.000 description 2
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- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
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- 238000002347 injection Methods 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
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- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- UOMBURBYNOYDKO-UHFFFAOYSA-N (-)-ophirin B Natural products O1C2CC(C)=CCCC(C)(OC(C)=O)C1C1C2C(C)=CC(OC(=O)C)C1C(C)(C)OC(C)=O UOMBURBYNOYDKO-UHFFFAOYSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical group CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- JTDTXGMXNXBGBZ-YVHUGQOKSA-N (2s)-1-[2-[[(2s)-1-[(2s)-2-[[(2s)-1-[(2s)-6-amino-2-[[(2s,3r)-2-amino-3-hydroxybutanoyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C[C@@H](O)[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@H](C(=O)NCC(=O)N2[C@@H](CCC2)C(O)=O)CCC1 JTDTXGMXNXBGBZ-YVHUGQOKSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241001057685 Kerriidae Species 0.000 description 1
- 101000878457 Macrocallista nimbosa FMRFamide Proteins 0.000 description 1
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- 240000007594 Oryza sativa Species 0.000 description 1
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- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229960003556 aminophylline Drugs 0.000 description 1
- FQPFAHBPWDRTLU-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=C1NC=N2.O=C1N(C)C(=O)N(C)C2=C1NC=N2 FQPFAHBPWDRTLU-UHFFFAOYSA-N 0.000 description 1
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- 239000011230 binding agent Substances 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- WLPACTAQECUARH-UHFFFAOYSA-L calcium;1,3-dimethyl-2-oxopurin-6-olate Chemical compound [Ca+2].CN1C(=O)N(C)C([O-])=C2N=CN=C21.CN1C(=O)N(C)C([O-])=C2N=CN=C21 WLPACTAQECUARH-UHFFFAOYSA-L 0.000 description 1
- HBGYWKVYHHULPL-UHFFFAOYSA-L calcium;1,3-dimethyl-7h-purine-2,6-dione;2-oxidobenzoate Chemical compound [Ca+2].[O-]C(=O)C1=CC=CC=C1[O-].O=C1N(C)C(=O)N(C)C2=C1NC=N2 HBGYWKVYHHULPL-UHFFFAOYSA-L 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- NHTGQOXRZFUGJX-UHFFFAOYSA-N chlorquinox Chemical compound N1=CC=NC2=C(Cl)C(Cl)=C(Cl)C(Cl)=C21 NHTGQOXRZFUGJX-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000004247 glycine and its sodium salt Substances 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 229960002050 hydrofluoric acid Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
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- 230000035987 intoxication Effects 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
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- 210000004185 liver Anatomy 0.000 description 1
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- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- UOMBURBYNOYDKO-ZHXAXXGGSA-N ophirin Chemical compound C([C@@H]1O2)\C(C)=C\CC[C@@](C)(OC(C)=O)[C@@H]2[C@H]2[C@@H]1C(C)=C[C@@H](OC(=O)C)[C@@H]2C(C)(C)OC(C)=O UOMBURBYNOYDKO-ZHXAXXGGSA-N 0.000 description 1
- GHLREYLPKHABCF-UHFFFAOYSA-N ophirin Natural products CC(=O)OC1=C(C)C2C3CC(=CCCC(C)(OC(=O)C)C(O3)C2C(C1)C(C)(C)OC(=O)C)C GHLREYLPKHABCF-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 229940029258 sodium glycinate Drugs 0.000 description 1
- WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical compound [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
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- 229960004559 theobromine Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
- A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core
Landscapes
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE789/83A IE55745B1 (en) | 1983-04-06 | 1983-04-06 | Sustained absorption pharmaceutical composition |
| IE789/83 | 1983-04-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59219219A true JPS59219219A (ja) | 1984-12-10 |
| JPH0466207B2 JPH0466207B2 (https=) | 1992-10-22 |
Family
ID=11018164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59068974A Granted JPS59219219A (ja) | 1983-04-06 | 1984-04-06 | 持続吸収性の薬剤組成物 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US4663150A (https=) |
| EP (1) | EP0122077B1 (https=) |
| JP (1) | JPS59219219A (https=) |
| AT (1) | ATE53176T1 (https=) |
| BE (1) | BE899293A (https=) |
| CH (1) | CH660688B (https=) |
| DE (1) | DE3482374D1 (https=) |
| IE (1) | IE55745B1 (https=) |
| PH (1) | PH18904A (https=) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS635021A (ja) * | 1986-06-20 | 1988-01-11 | エラン コ−ポレ−シヨン ピ− エル シ− | 吸収制御薬剤組成物 |
| JP2002524409A (ja) * | 1998-09-09 | 2002-08-06 | カーディアック ペースメーカーズ，インコーポレイティド | 徐方性ドラッグデリバリー |
| JP2002526401A (ja) * | 1998-10-02 | 2002-08-20 | レーム ゲゼルシヤフト ミツト ベシユレンクテル ハフツング ウント コンパニー コマンディートゲゼルシャフト | 制御された作用物質放出性を有する被覆された医薬品形 |
| JP2006096771A (ja) * | 1992-07-29 | 2006-04-13 | Gacell Lab Ab | 制御放出モルヒネ製剤 |
| JP2008534530A (ja) * | 2005-03-29 | 2008-08-28 | エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツング | 活性成分放出に関して調節作用を有する物質を有するペレットを含有している多粒子薬剤形 |
| JP2022502406A (ja) * | 2018-09-27 | 2022-01-11 | イニブサ ギネコロジア, エセ.ア.Inibsa Ginecologia, S.A. | コハク酸ドキシラミンと塩酸ピリドキシンとの改変放出型複合単位経口投薬形態物の調製方法 |
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|---|---|---|---|---|
| FR2470599A1 (fr) * | 1979-12-07 | 1981-06-12 | Panoz Donald | Perfectionnements apportes aux procedes de preparation de formes galeniques a action retard et a liberation programmee et formes galeniques de medicaments ainsi obtenus |
| IE55745B1 (en) * | 1983-04-06 | 1991-01-02 | Elan Corp Plc | Sustained absorption pharmaceutical composition |
| IE58246B1 (en) * | 1984-12-21 | 1993-08-11 | Byk Gulden Lomberg Chem Fab | Theophylline sustained release formulation |
| GB2170104A (en) * | 1985-01-30 | 1986-07-30 | Warner Lambert Co | Coated pharmaceutical dosage forms |
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| GB8628728D0 (en) * | 1986-12-02 | 1987-01-07 | Euro Celtique Sa | Spheroids |
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| CA1323833C (en) * | 1987-04-28 | 1993-11-02 | Yatindra M. Joshi | Pharmaceutical compositions in the form of beadlets and method |
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| IE64726B1 (en) | 1987-11-20 | 1995-08-23 | Elan Corp Plc | Pharmaceutical formulations for preventing drug tolerance |
| US5296236A (en) * | 1988-09-16 | 1994-03-22 | Recordati S.A., Chemical And Pharmaceutical Company | Controlled release therapeutic system for a liquid pharmaceutical formulations |
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| US5122384A (en) * | 1989-05-05 | 1992-06-16 | Kv Pharmaceutical Company | Oral once-per-day organic nitrate formulation which does not induce tolerance |
| DE3929864A1 (de) * | 1989-09-08 | 1991-03-14 | Nordmark Arzneimittel Gmbh | Verfahren zur herstellung von theophyllin-pellets |
| JPH0674206B2 (ja) * | 1989-12-28 | 1994-09-21 | 田辺製薬株式会社 | 放出制御型製剤およびその製法 |
| US5162110A (en) * | 1990-12-19 | 1992-11-10 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Binding theophylline to ion exchange resins |
| US5431922A (en) * | 1991-03-05 | 1995-07-11 | Bristol-Myers Squibb Company | Method for administration of buspirone |
| WO1992020326A1 (en) * | 1991-05-20 | 1992-11-26 | Marion Laboratories, Inc. | Multi-layered controlled release formulation |
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| US20060068018A1 (en) * | 1996-03-25 | 2006-03-30 | Wyeth | Extended release formulation |
| US20030215507A1 (en) * | 1996-03-25 | 2003-11-20 | Wyeth | Extended release formulation |
| US5766623A (en) * | 1996-03-25 | 1998-06-16 | State Of Oregon Acting By And Through The Oregon State Board Of Higher Education On Behalf Of Oregon State University | Compactable self-sealing drug delivery agents |
| FR2758461A1 (fr) * | 1997-01-17 | 1998-07-24 | Pharma Pass | Composition pharmaceutique presentant une biodisponibilite elevee et son procede de preparation |
| FR2758459B1 (fr) * | 1997-01-17 | 1999-05-07 | Pharma Pass | Composition pharmaceutique de fenofibrate presentant une biodisponibilite elevee et son procede de preparation |
| US6066339A (en) * | 1997-10-17 | 2000-05-23 | Elan Corporation, Plc | Oral morphine multiparticulate formulation |
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| CN101410094B (zh) * | 2006-01-27 | 2013-04-17 | 阿普塔利斯制药股份有限公司 | 包含弱碱性选择性5-羟色胺5-ht3阻断剂和有机酸的药物递送系统 |
| JP5661281B2 (ja) * | 2006-08-18 | 2015-01-28 | エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツングＥｖｏｎｉｋ Ｒｏｅｈｍ ＧｍｂＨ | 良好な水溶解性を有する作用物質のための作用物質の制御送達を有する医薬組成物 |
| US8133506B2 (en) * | 2008-03-12 | 2012-03-13 | Aptalis Pharmatech, Inc. | Drug delivery systems comprising weakly basic drugs and organic acids |
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| US8992898B2 (en) | 2010-04-17 | 2015-03-31 | Shannon Elizabeth Klingman | Antiperspirants and deodorants |
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| US10722473B2 (en) | 2018-11-19 | 2020-07-28 | Purdue Pharma L.P. | Methods and compositions particularly for treatment of attention deficit disorder |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56122311A (en) * | 1980-02-29 | 1981-09-25 | Eisai Co Ltd | Lasting theophylline pharmaceutical composition |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2853420A (en) * | 1956-01-25 | 1958-09-23 | Lowey Hans | Ethyl cellulose coatings for shaped medicinal preparations |
| US3081233A (en) * | 1960-08-08 | 1963-03-12 | Upjohn Co | Enteric-coated pilules |
| NL122039C (https=) * | 1960-10-20 | |||
| BE636568A (https=) * | 1961-01-31 | |||
| US3247066A (en) * | 1962-09-12 | 1966-04-19 | Parke Davis & Co | Controlled release dosage form containing water-swellable beadlet |
| NL297631A (https=) * | 1963-06-03 | |||
| US3949068A (en) * | 1964-02-20 | 1976-04-06 | University Of Alabama In Birmingham Medical And Educational Foundation | Pharmaceutical compositions |
| US3400185A (en) * | 1965-04-08 | 1968-09-03 | Bristol Myers Co | Agglomeration of smaller pharmaceutical particles into larger microspherules and enteic-coating thereof |
| DE2010416B2 (de) * | 1970-03-05 | 1979-03-29 | Hoechst Ag, 6000 Frankfurt | Oral anwendbare Arzneiform mit Retardwirkung |
| US4016254A (en) * | 1972-05-19 | 1977-04-05 | Beecham Group Limited | Pharmaceutical formulations |
| DE2336218C3 (de) * | 1973-07-17 | 1985-11-14 | Byk Gulden Lomberg Chemische Fabrik Gmbh, 7750 Konstanz | Orale Arzneiform |
| DE2343218C2 (de) * | 1973-08-28 | 1986-08-07 | Hoechst Ag, 6230 Frankfurt | Furosemid enthaltende Pellets |
| US3906087A (en) * | 1973-09-10 | 1975-09-16 | Union Corp | Sustained release of methantheline |
| US4085214A (en) * | 1976-10-18 | 1978-04-18 | Interx Research Corporation | Stable pro-drug forms of theophylline |
| DD146547A5 (de) * | 1978-07-15 | 1981-02-18 | Boehringer Sohn Ingelheim | Arzneimittel-retardform mit unloeslichen poroesen diffusionshuellen |
| US4173626A (en) * | 1978-12-11 | 1979-11-06 | Merck & Co., Inc. | Sustained release indomethacin |
| US4309406A (en) * | 1979-07-10 | 1982-01-05 | American Home Products Corporation | Sustained release pharmaceutical compositions |
| US4248858A (en) * | 1979-08-09 | 1981-02-03 | American Home Products Corporation | Sustained release pharmaceutical compositions |
| DE3000979A1 (de) * | 1980-01-12 | 1981-07-23 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue dipyridamol-retardformen und verfahren zu ihrer herstellung |
| NZ196349A (en) * | 1980-03-07 | 1984-08-24 | Interx Research Corp | Enhancement of absorption rate of orally administered polar bioactive agents |
| DE3127237A1 (de) * | 1981-07-10 | 1983-01-20 | Hoechst Ag, 6000 Frankfurt | Magenvertraegliche arzneiformen von xanthinderivaten und verfahren zu ihrer herstellung |
| DE3278491D1 (en) * | 1981-07-15 | 1988-06-23 | Key Pharma | Sustained release theophyline |
| IT1153487B (it) * | 1982-04-15 | 1987-01-14 | Prophin Lab Spa | Prodotti farmaceutici in forma-ritardo e procedimento per ottenerli |
| US4415547A (en) * | 1982-06-14 | 1983-11-15 | Sterling Drug Inc. | Sustained-release pharmaceutical tablet and process for preparation thereof |
| IE55745B1 (en) * | 1983-04-06 | 1991-01-02 | Elan Corp Plc | Sustained absorption pharmaceutical composition |
| US4710384A (en) * | 1986-07-28 | 1987-12-01 | Avner Rotman | Sustained release tablets made from microcapsules |
-
1983
- 1983-04-06 IE IE789/83A patent/IE55745B1/en not_active IP Right Cessation
-
1984
- 1984-03-22 EP EP84301954A patent/EP0122077B1/en not_active Expired - Lifetime
- 1984-03-22 DE DE8484301954T patent/DE3482374D1/de not_active Expired - Fee Related
- 1984-03-22 AT AT84301954T patent/ATE53176T1/de active
- 1984-03-30 BE BE0/212666A patent/BE899293A/fr not_active IP Right Cessation
- 1984-04-04 CH CH170584A patent/CH660688B/fr unknown
- 1984-04-05 PH PH30501A patent/PH18904A/en unknown
- 1984-04-06 JP JP59068974A patent/JPS59219219A/ja active Granted
-
1986
- 1986-05-21 US US06/870,293 patent/US4663150A/en not_active Expired - Lifetime
-
1987
- 1987-01-16 US US07/003,736 patent/US4820521A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56122311A (en) * | 1980-02-29 | 1981-09-25 | Eisai Co Ltd | Lasting theophylline pharmaceutical composition |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS635021A (ja) * | 1986-06-20 | 1988-01-11 | エラン コ−ポレ−シヨン ピ− エル シ− | 吸収制御薬剤組成物 |
| JP2006096771A (ja) * | 1992-07-29 | 2006-04-13 | Gacell Lab Ab | 制御放出モルヒネ製剤 |
| JP2002524409A (ja) * | 1998-09-09 | 2002-08-06 | カーディアック ペースメーカーズ，インコーポレイティド | 徐方性ドラッグデリバリー |
| JP2002526401A (ja) * | 1998-10-02 | 2002-08-20 | レーム ゲゼルシヤフト ミツト ベシユレンクテル ハフツング ウント コンパニー コマンディートゲゼルシャフト | 制御された作用物質放出性を有する被覆された医薬品形 |
| JP2008534530A (ja) * | 2005-03-29 | 2008-08-28 | エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツング | 活性成分放出に関して調節作用を有する物質を有するペレットを含有している多粒子薬剤形 |
| JP2022502406A (ja) * | 2018-09-27 | 2022-01-11 | イニブサ ギネコロジア, エセ.ア.Inibsa Ginecologia, S.A. | コハク酸ドキシラミンと塩酸ピリドキシンとの改変放出型複合単位経口投薬形態物の調製方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE53176T1 (de) | 1990-06-15 |
| JPH0466207B2 (https=) | 1992-10-22 |
| DE3482374D1 (de) | 1990-07-05 |
| EP0122077B1 (en) | 1990-05-30 |
| US4663150A (en) | 1987-05-05 |
| US4820521A (en) | 1989-04-11 |
| CH660688B (https=) | 1987-06-15 |
| IE55745B1 (en) | 1991-01-02 |
| EP0122077A3 (en) | 1985-09-11 |
| PH18904A (en) | 1985-10-30 |
| EP0122077A2 (en) | 1984-10-17 |
| BE899293A (fr) | 1984-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |