GB1116670A - Process for the manufacture of pharmaceutical preparations in bead form - Google Patents
Process for the manufacture of pharmaceutical preparations in bead formInfo
- Publication number
- GB1116670A GB1116670A GB25691/65A GB2569165A GB1116670A GB 1116670 A GB1116670 A GB 1116670A GB 25691/65 A GB25691/65 A GB 25691/65A GB 2569165 A GB2569165 A GB 2569165A GB 1116670 A GB1116670 A GB 1116670A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- mixture
- medicament
- bead
- methyl methacrylate
- 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
Links
- 239000011324 bead Substances 0.000 title abstract 7
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 239000000825 pharmaceutical preparation Substances 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 abstract 10
- 239000003814 drug Substances 0.000 abstract 7
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 6
- 239000000178 monomer Substances 0.000 abstract 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- 235000011389 fruit/vegetable juice Nutrition 0.000 abstract 4
- 230000000968 intestinal effect Effects 0.000 abstract 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 4
- 210000002784 stomach Anatomy 0.000 abstract 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 3
- 238000006116 polymerization reaction Methods 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 abstract 3
- 229940117958 vinyl acetate Drugs 0.000 abstract 3
- -1 1-cyclohexenyl Chemical group 0.000 abstract 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 2
- 239000002612 dispersion medium Substances 0.000 abstract 2
- 239000003792 electrolyte Substances 0.000 abstract 2
- 239000000945 filler Substances 0.000 abstract 2
- 239000001530 fumaric acid Substances 0.000 abstract 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 abstract 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 abstract 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000004094 surface-active agent Substances 0.000 abstract 2
- 238000010557 suspension polymerization reaction Methods 0.000 abstract 2
- 230000008961 swelling Effects 0.000 abstract 2
- 229920003002 synthetic resin Polymers 0.000 abstract 2
- 239000000057 synthetic resin Substances 0.000 abstract 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 1
- ZAWQXWZJKKICSZ-UHFFFAOYSA-N 3,3-dimethyl-2-methylidenebutanamide Chemical compound CC(C)(C)C(=C)C(N)=O ZAWQXWZJKKICSZ-UHFFFAOYSA-N 0.000 abstract 1
- AUYLLSDPDMYNTF-UHFFFAOYSA-N 4-amino-N-[6-methoxy-2-(methoxymethyl)pyrimidin-4-yl]benzenesulfonamide Chemical compound NC1=CC=C(C=C1)S(=O)(=O)NC1=CC(=NC(=N1)COC)OC AUYLLSDPDMYNTF-UHFFFAOYSA-N 0.000 abstract 1
- 229930008281 A03AD01 - Papaverine Natural products 0.000 abstract 1
- GNOGSFBXBWBTIG-UHFFFAOYSA-N Acetrizoic acid Chemical compound CC(=O)NC1=C(I)C=C(I)C(C(O)=O)=C1I GNOGSFBXBWBTIG-UHFFFAOYSA-N 0.000 abstract 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- JMBQKKAJIKAWKF-UHFFFAOYSA-N Glutethimide Chemical compound C=1C=CC=CC=1C1(CC)CCC(=O)NC1=O JMBQKKAJIKAWKF-UHFFFAOYSA-N 0.000 abstract 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000002671 adjuvant Substances 0.000 abstract 1
- 229940125717 barbiturate Drugs 0.000 abstract 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 150000001869 cobalt compounds Chemical class 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 229960000890 hydrocortisone Drugs 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 239000006194 liquid suspension Substances 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 239000011572 manganese Substances 0.000 abstract 1
- 239000002609 medium Substances 0.000 abstract 1
- 229960001789 papaverine Drugs 0.000 abstract 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61J—CONTAINERS SPECIALLY ADAPTED FOR MEDICAL OR PHARMACEUTICAL PURPOSES; DEVICES OR METHODS SPECIALLY ADAPTED FOR BRINGING PHARMACEUTICAL PRODUCTS INTO PARTICULAR PHYSICAL OR ADMINISTERING FORMS; DEVICES FOR ADMINISTERING FOOD OR MEDICINES ORALLY; BABY COMFORTERS; DEVICES FOR RECEIVING SPITTLE
- A61J3/00—Devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61J—CONTAINERS SPECIALLY ADAPTED FOR MEDICAL OR PHARMACEUTICAL PURPOSES; DEVICES OR METHODS SPECIALLY ADAPTED FOR BRINGING PHARMACEUTICAL PRODUCTS INTO PARTICULAR PHYSICAL OR ADMINISTERING FORMS; DEVICES FOR ADMINISTERING FOOD OR MEDICINES ORALLY; BABY COMFORTERS; DEVICES FOR RECEIVING SPITTLE
- A61J3/00—Devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms
- A61J3/06—Devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms into the form of pills, lozenges or dragees
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
Abstract
A process for the manufacture of a pharmaceutical preparation in bead form comprises subjecting a mixture of a synthetic monomer and an organic medicament to bead polymerization, the mixture being capable when polymerized of yielding a physiologically tolerable polymeric material that is capable of being dissolved in or swollen by stomach and/or intestinal juices. Preferred monomers comprise methyl methacrylate and mixtures of methacrylic acid and methyl methacrylate, methacrylic acid and divinylbenzene with or without methyl methacrylate, acrylic acid and methyl acrylate, vinyl acetate and crotonic acid, styrene and acrylic acid and/or maleic anhydride, vinyl methyl ether and maleic anhydride and/or fumaric acid and/or itaconic acid. The polymerization mixture may contain conventional fillers, swelling agents, electrolytes, and surface active agents. The medicament may be coated in wax or fat, and synthetic resins that are insoluble in and not swollen by the stomach and/or intestinal juices may be included in the polymerization mixture. Bead polymerization may be effected by dispersing the synthetic monomer-medicament mixture in a dispersion medium with which it is immiscible, e.g. water, in such a manner that beads having the desired degree of fineness are obtained, polymerization being carried out at room temperature or above generally with the aid of a catalyst, e.g. benzoyl peroxide, t-butyl hydroperoxide or azodiisobutyronitrile, and, optionally, an accelerator, e.g. a tertiary amine, an iron, manganese or cobalt compound, a sulphinic acid or a sulphite, and a dispersing agent, e.g. sodium polyacrylate or polyethylene glycol. A preformed polymer may also be present, e.g. a vinylacetate/crotonic acid copolymer or an ethyl acrylate/t-butyl-acrylamide/acrylic acid copolymer.ALSO:A process for the manufacture of a pharmaceutical preparation in bead form comprises subjecting a mixture of a synthetic monomer and an organic medicament to bead polymerisation, the mixture being capable when polymerised of yielding a physiologically tolerable polymeric material that is capable of being dissolved in or swollen by stomach and/or intestinal juices. Preferred monomers comprise methyl methacrylate and mixtures of methacrylic acid and methyl methacrylate, methyl methacrylate and divinyl benzene, acrylic acid and methyl acrylate, vinyl acetate and crotonic acid, styrene and acrylic acid and/or maleic anhydride, vinyl methyl ether and maleic acid anhydride and/or fumaric acid and/or itaconic acid. Exemplified medicaments comprise 5 - (1-cyclohexenyl) - 5 - ethyl calcium barbiturate, acetyl para - phenetidine, 2 - ethyl - 2 - phenylglutarimide, papaverine, 4 - dimethylamino - 1 - phenyl - 2, 3 - dimethyl pyrozolone - 5, hydrocortisone, N - [6 - methoxy - 2 (methoxy - methyl) - 4 - pyrimidinyl] - sulphanilamide, and the sodium salt of 3 - acetylamino - 2,4,6 - triiodobenzoic acid. The preparations may contain conventional fillers, swelling agents, electrolytes, and surface active agents. The medicament may be coated in wax or fat, and synthetic resins that are insoluble in and not swollen by the stomach and/or intestinal juices may be included in the preparations. Bead polymerisation may be effected by dispersing the medicament - synthetic monomer mixture in a dispersion medium with which it is imiscible in such a manner that beads having the desired degree of fineness are obtained, polymerisation being carried out at room temperature or above generally with the aid of a catalyst and an accelerator. The preparations may be used in the form of granules, in capsules, in a liquid suspension medium, or in tablet form together with suitable adjuvants.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH806264A CH468192A (en) | 1964-06-19 | 1964-06-19 | Process for the manufacture of medicaments in pearl form |
| CH705065 | 1965-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1116670A true GB1116670A (en) | 1968-06-12 |
Family
ID=25700654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25691/65A Expired GB1116670A (en) | 1964-06-19 | 1965-06-17 | Process for the manufacture of pharmaceutical preparations in bead form |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3390050A (en) |
| BE (1) | BE665607A (en) |
| CH (1) | CH468192A (en) |
| DE (1) | DE1467843A1 (en) |
| FR (1) | FR1468716A (en) |
| GB (1) | GB1116670A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2125869C1 (en) * | 1993-05-15 | 1999-02-10 | Сосьете Де Консей Де Решерш Э Д' Аппликасьон Сьянтифик | Dry method for preparing particles based on active principles, dry particles prepared by this method, and pharmaceutical compositions containing such particles |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA935092A (en) * | 1968-09-03 | 1973-10-09 | S. Banker Gilbert | Molecular drug entrapment process and compositions |
| CA927282A (en) * | 1968-09-03 | 1973-05-29 | S. Banker Gilbert | Entrapment compositions and processes |
| USRE28316E (en) * | 1968-09-03 | 1975-01-21 | Entrapment compositions and processes | |
| AT319191B (en) * | 1969-08-01 | 1974-12-10 | Bush Boake Allen Ltd | Double-walled water-insoluble microcapsules for the delivery of flavoring substances |
| FR2407720A1 (en) * | 1977-11-08 | 1979-06-01 | Lipha Lyonnaise Indle Pharmace | Oral sustained-action capsule formulations - of drug and excipient which swells in contact with digestive juices |
| US4539199A (en) * | 1981-01-14 | 1985-09-03 | Egyt Gyogyszervegyeszeti Gyar | Sustained release pharmaceutical compositions |
| ES259491Y (en) * | 1981-07-15 | 1982-07-01 | GARDENING | |
| EP0076158B1 (en) * | 1981-09-30 | 1989-10-25 | National Research Development Corporation | Compositions comprising encapsulated particles |
| US4764380A (en) * | 1982-03-22 | 1988-08-16 | Alza Corporation | Drug delivery system comprising a volume increasing matrix containing a plurality of tiny pills |
| US4642233A (en) * | 1982-03-22 | 1987-02-10 | Alza Corporation | Gastrointestinal drug delivery system comprising a hydrogel reservoir containing a plurality of tiny pills |
| US4659558A (en) * | 1982-03-22 | 1987-04-21 | Alza Corporation | Oral delivery system comprising a plurality of tiny pills for delivering drug in the stomach and intestine |
| US4649043A (en) * | 1982-03-22 | 1987-03-10 | Alza Corporation | Drug delivery system for delivering a plurality of tiny pills in the gastrointestinal tract |
| JPS5965009A (en) * | 1982-10-05 | 1984-04-13 | Chisso Corp | Prolonged release type vasodilator |
| DE3314003A1 (en) * | 1983-04-18 | 1984-10-18 | Boehringer Ingelheim KG, 6507 Ingelheim | DIVISIBLE TABLET WITH DELAYED ACTIVE SUBSTANCE RELEASE AND METHOD FOR THE PRODUCTION THEREOF |
| US4548990A (en) * | 1983-08-15 | 1985-10-22 | Ciba-Geigy Corporation | Crosslinked, porous polymers for controlled drug delivery |
| US4795436A (en) * | 1983-11-14 | 1989-01-03 | Bio-Mimetics, Inc. | Bioadhesive composition and method of treatment therewith |
| US4983392A (en) * | 1983-11-14 | 1991-01-08 | Bio-Mimetics, Inc. | Bioadhesive compositions and methods of treatment therewith |
| GB8331546D0 (en) * | 1983-11-25 | 1984-01-04 | Exxon Research Engineering Co | Polymeric compositions |
| EP0143608B1 (en) * | 1983-11-25 | 1992-07-22 | Ciba Specialty Chemicals Water Treatments Limited | Manufacture and use of polymeric beads |
| US4624848A (en) * | 1984-05-10 | 1986-11-25 | Ciba-Geigy Corporation | Active agent containing hydrogel devices wherein the active agent concentration profile contains a sigmoidal concentration gradient for improved constant release, their manufacture and use |
| US4749576A (en) * | 1984-05-10 | 1988-06-07 | Ciba-Geigy Corporation | Active agent containing hydrogel devices wherein the active agent concentration profile contains a sigmoidal concentration gradient for improved constant release, their manufacture and use |
| DE3524337A1 (en) * | 1985-07-08 | 1987-01-08 | Roehm Gmbh | MEDICINAL PACKAGING |
| US4690825A (en) * | 1985-10-04 | 1987-09-01 | Advanced Polymer Systems, Inc. | Method for delivering an active ingredient by controlled time release utilizing a novel delivery vehicle which can be prepared by a process utilizing the active ingredient as a porogen |
| US5246714A (en) * | 1985-10-11 | 1993-09-21 | Aktiebolaget Hassle | Drug preparation |
| US5198226A (en) * | 1986-01-30 | 1993-03-30 | Syntex (U.S.A.) Inc. | Long acting nicardipine hydrochloride formulation |
| US4940556A (en) * | 1986-01-30 | 1990-07-10 | Syntex (U.S.A.) Inc. | Method of preparing long acting formulation |
| DE3608721A1 (en) * | 1986-03-15 | 1987-09-17 | Hoelter Heinz | Method for improving the service life of chemisorption compositions |
| NZ220599A (en) * | 1986-06-16 | 1990-10-26 | Merck & Co Inc | Controlled release oral dosage formulation of carbidopa and levodopa |
| US4851232A (en) * | 1987-02-13 | 1989-07-25 | Alza Corporation | Drug delivery system with means for obtaining desirable in vivo release rate pattern |
| US5030454A (en) * | 1987-10-26 | 1991-07-09 | Alza Corporation | Method for delivering drug in tiny pills in liquid carrier |
| US4961932A (en) * | 1987-10-26 | 1990-10-09 | Alza Corporation | Plurality of tiny pills in liquid dosage form |
| US4853229A (en) * | 1987-10-26 | 1989-08-01 | Alza Corporation | Method for adminstering tiny pills |
| US5055300A (en) * | 1988-06-17 | 1991-10-08 | Basic Bio Systems, Inc. | Time release protein |
| US5023080A (en) * | 1988-06-17 | 1991-06-11 | Basic Bio Systems, Inc. | Time release protein |
| US5079005A (en) * | 1988-06-17 | 1992-01-07 | Gupta Kashmiri L | Time release protein |
| US5154927A (en) * | 1989-01-19 | 1992-10-13 | Wm. Wrigley Jr. Company | Gum composition containing dispersed porous beads containing active chewing gum ingredients and method |
| US5139787A (en) * | 1989-01-19 | 1992-08-18 | Wm. Wrigley Jr. Company | Gum composition containing dispersed porous beads containing active chewing gum ingredients and method |
| US4963369A (en) * | 1989-01-19 | 1990-10-16 | Wm. Wrigley Jr. Co. | Gum composition containing dispersed porous beads containing active chewing gum ingredients and method |
| US5064698A (en) * | 1989-02-16 | 1991-11-12 | Wm. Wrigley, Jr. Company | Food packaging improvements |
| US5126174A (en) * | 1989-02-16 | 1992-06-30 | Wm. Wrigley Jr. Company | Food packaging improvements |
| US5007790A (en) * | 1989-04-11 | 1991-04-16 | Depomed Systems, Inc. | Sustained-release oral drug dosage form |
| ES2050096T3 (en) | 1989-10-31 | 1995-01-16 | Columbia Lab Inc | HUMIDIFYING COMPOSITION OF THE VAGINAL TISSUE. |
| DE4029591C2 (en) * | 1990-09-19 | 1995-01-26 | Stockhausen Chem Fab Gmbh | Process for the preparation of polymer-based absorption material with the addition of water-soluble substances and use of this absorption material for the absorption and / or subsequent release of water or aqueous solutions |
| US5154938A (en) * | 1990-12-20 | 1992-10-13 | Wm. Wrigley Jr. Company | Gum composition having dispersed porous beads containing plasticizers |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2846057A (en) * | 1954-02-09 | 1958-08-05 | Polin Herbert Spencer | Devices for dosage control |
| US2810716A (en) * | 1954-06-28 | 1957-10-22 | White Lab Inc | Batchwise copolymerization technique |
| US3092553A (en) * | 1959-01-30 | 1963-06-04 | Jr Carl E Fisher | Pharmaceutical preparations and method and apparatus for making same |
| US3162573A (en) * | 1959-10-14 | 1964-12-22 | Plants Products Corp | Internal treatment of animals with resin biocidal compositions |
| US3074795A (en) * | 1959-11-12 | 1963-01-22 | Pfizer & Co C | Production of bacitracin adsorbate and process of administration to animals for promoting growth |
| US3121043A (en) * | 1960-05-11 | 1964-02-11 | Scient Associates Inc | Sustained release pharmaceutical preparation and methods for making same |
| US3158538A (en) * | 1961-02-23 | 1964-11-24 | White Lab Inc | Antidiarrheal compositions and method of using |
| US3202577A (en) * | 1962-05-25 | 1965-08-24 | White Lab Inc | Process of treating diarrhea with resins |
| US3247066A (en) * | 1962-09-12 | 1966-04-19 | Parke Davis & Co | Controlled release dosage form containing water-swellable beadlet |
| US3328256A (en) * | 1963-05-27 | 1967-06-27 | William E Gaunt | Spherical beads and their production |
-
1964
- 1964-06-19 CH CH806264A patent/CH468192A/en unknown
-
1965
- 1965-06-08 US US462450A patent/US3390050A/en not_active Expired - Lifetime
- 1965-06-12 DE DE19651467843 patent/DE1467843A1/en active Pending
- 1965-06-17 GB GB25691/65A patent/GB1116670A/en not_active Expired
- 1965-06-17 FR FR21168A patent/FR1468716A/en not_active Expired
- 1965-06-18 BE BE665607A patent/BE665607A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2125869C1 (en) * | 1993-05-15 | 1999-02-10 | Сосьете Де Консей Де Решерш Э Д' Аппликасьон Сьянтифик | Dry method for preparing particles based on active principles, dry particles prepared by this method, and pharmaceutical compositions containing such particles |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1467843A1 (en) | 1968-12-12 |
| US3390050A (en) | 1968-06-25 |
| FR1468716A (en) | 1967-02-10 |
| CH468192A (en) | 1969-02-15 |
| BE665607A (en) | 1965-12-20 |
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