CA1086226A - Ion exchange resin prolonged release pharmaceutical preparations - Google Patents
Ion exchange resin prolonged release pharmaceutical preparationsInfo
- Publication number
- CA1086226A CA1086226A CA291,664A CA291664A CA1086226A CA 1086226 A CA1086226 A CA 1086226A CA 291664 A CA291664 A CA 291664A CA 1086226 A CA1086226 A CA 1086226A
- Authority
- CA
- Canada
- Prior art keywords
- complex
- drug
- resin
- coated
- coating
- 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
- 230000002035 prolonged effect Effects 0.000 title claims abstract description 16
- 239000000825 pharmaceutical preparation Substances 0.000 title claims abstract description 8
- 239000003456 ion exchange resin Substances 0.000 title claims description 11
- 229920003303 ion-exchange polymer Polymers 0.000 title claims description 11
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 title claims description 10
- 229920005989 resin Polymers 0.000 claims abstract description 103
- 239000011347 resin Substances 0.000 claims abstract description 103
- 229940079593 drug Drugs 0.000 claims abstract description 93
- 239000003814 drug Substances 0.000 claims abstract description 93
- 238000000576 coating method Methods 0.000 claims abstract description 64
- 239000011248 coating agent Substances 0.000 claims abstract description 62
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 25
- 230000004888 barrier function Effects 0.000 claims abstract description 16
- 238000009792 diffusion process Methods 0.000 claims abstract description 13
- 239000002245 particle Substances 0.000 claims description 64
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 claims description 56
- 229960000395 phenylpropanolamine Drugs 0.000 claims description 56
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 claims description 54
- 238000002360 preparation method Methods 0.000 claims description 31
- 239000001856 Ethyl cellulose Substances 0.000 claims description 25
- 229920001249 ethyl cellulose Polymers 0.000 claims description 25
- 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 24
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 24
- 239000002202 Polyethylene glycol Substances 0.000 claims description 19
- 229920001223 polyethylene glycol Polymers 0.000 claims description 19
- 229960001985 dextromethorphan Drugs 0.000 claims description 16
- MKXZASYAUGDDCJ-SZMVWBNQSA-N LSM-2525 Chemical compound C1CCC[C@H]2[C@@]3([H])N(C)CC[C@]21C1=CC(OC)=CC=C1C3 MKXZASYAUGDDCJ-SZMVWBNQSA-N 0.000 claims description 15
- 229920001429 chelating resin Polymers 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 238000004090 dissolution Methods 0.000 description 25
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 25
- 239000000203 mixture Substances 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 18
- 238000009472 formulation Methods 0.000 description 16
- 229960003562 phentermine Drugs 0.000 description 14
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 13
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 12
- 239000012530 fluid Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 238000002156 mixing Methods 0.000 description 10
- 239000011162 core material Substances 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000002775 capsule Substances 0.000 description 7
- 229960003908 pseudoephedrine Drugs 0.000 description 7
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 235000015112 vegetable and seed oil Nutrition 0.000 description 7
- 239000008158 vegetable oil Substances 0.000 description 7
- 229960002179 ephedrine Drugs 0.000 description 6
- 210000001035 gastrointestinal tract Anatomy 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 235000013311 vegetables Nutrition 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 230000036765 blood level Effects 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 241000282414 Homo sapiens Species 0.000 description 4
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 230000036470 plasma concentration Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 229960004126 codeine Drugs 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 235000020375 flavoured syrup Nutrition 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229960000264 phentermine resin Drugs 0.000 description 2
- -1 polyethylene Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 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 compound 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
- QWFMDSOYEQHWMF-UHFFFAOYSA-N 2,3-bis(ethenyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C=C)=C1C=C QWFMDSOYEQHWMF-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 241000282412 Homo Species 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
- 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 1
- 229930195725 Mannitol Natural products 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical compound CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 239000000150 Sympathomimetic Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 239000000850 decongestant Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 229950009195 phenylpropanol Drugs 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229940127230 sympathomimetic drug Drugs 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
- A61K47/585—Ion exchange resins, e.g. polystyrene sulfonic acid resin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74532576A | 1976-11-26 | 1976-11-26 | |
| US80010577A | 1977-05-24 | 1977-05-24 | |
| US745,325 | 1985-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1086226A true CA1086226A (en) | 1980-09-23 |
Family
ID=27114439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA291,664A Expired CA1086226A (en) | 1976-11-26 | 1977-11-24 | Ion exchange resin prolonged release pharmaceutical preparations |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS609697B2 (cg-RX-API-DMAC7.html) |
| AR (1) | AR218047A1 (cg-RX-API-DMAC7.html) |
| AT (1) | AT359197B (cg-RX-API-DMAC7.html) |
| AU (1) | AU511080B2 (cg-RX-API-DMAC7.html) |
| BE (1) | BE861141A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1086226A (cg-RX-API-DMAC7.html) |
| CH (1) | CH639560A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2752728C2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK150534C (cg-RX-API-DMAC7.html) |
| FI (1) | FI65910C (cg-RX-API-DMAC7.html) |
| FR (1) | FR2373288A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1544761A (cg-RX-API-DMAC7.html) |
| GR (1) | GR61724B (cg-RX-API-DMAC7.html) |
| IE (1) | IE45998B1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL53462A (cg-RX-API-DMAC7.html) |
| LU (1) | LU78584A1 (cg-RX-API-DMAC7.html) |
| NL (1) | NL182283C (cg-RX-API-DMAC7.html) |
| NO (1) | NO147626C (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ185772A (cg-RX-API-DMAC7.html) |
| PT (1) | PT67323B (cg-RX-API-DMAC7.html) |
| SE (1) | SE426781B (cg-RX-API-DMAC7.html) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2929456A1 (de) | 1979-07-20 | 1981-02-05 | Lentia Gmbh | Zusammensetzung mit verlaengerter broncholytischer und tokolytischer wirksamkeit, ein verfahren zu deren herstellung und broncholytisch und tokolytisch wirkendes mittel |
| CA1236023A (en) * | 1984-07-18 | 1988-05-03 | Yegnaswami Raghunathan | Controlled release pharmaceutical preparations |
| US4692462A (en) * | 1985-03-18 | 1987-09-08 | Menley & James Laboratories, Ltd. | Compositions and method of controlling transdermal penetration of topical and systemic agents |
| US5612059A (en) * | 1988-08-30 | 1997-03-18 | Pfizer Inc. | Use of asymmetric membranes in delivery devices |
| US5188825A (en) * | 1989-12-28 | 1993-02-23 | Iles Martin C | Freeze-dried dosage forms and methods for preparing the same |
| US5876752A (en) * | 1990-08-07 | 1999-03-02 | Pfizer Inc. | Use of interfacially-polymerized membranes in delivery devices |
| US5436011A (en) * | 1993-04-16 | 1995-07-25 | Bristol-Myers Squibb Company | Solid pharmaceutical dosage form and a method for reducing abrasion |
| US20130230587A1 (en) * | 2010-11-10 | 2013-09-05 | Rubicon Research Private Limited | Sustained release compositions |
| FR3059903B1 (fr) * | 2016-12-08 | 2019-03-22 | Salsarulo Pharma | Medicament oral comprenant un laxatif osmotique incorpore dans une matrice a base de matieres grasses vegetales |
| EP3694555A4 (en) | 2017-10-09 | 2021-07-07 | Rhodes Pharmaceuticals L.P. | RESINATE-BASED PHARMACEUTICAL COMPOSITIONS AND THEIR MANUFACTURING AND USE PROCESSES |
| WO2020234842A1 (en) * | 2019-05-23 | 2020-11-26 | G.D Societa' Per Azioni | Filling unit to fill a container, in particular a cartridge, with a liquid product of the pharmaceutical industry |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE550150A (cg-RX-API-DMAC7.html) * | 1955-08-08 | |||
| GB843118A (en) * | 1957-02-13 | 1960-08-04 | Ici Ltd | Pharmaceutical compositions containing piperidine derivatives |
| US3158538A (en) * | 1961-02-23 | 1964-11-24 | White Lab Inc | Antidiarrheal compositions and method of using |
| GB982150A (en) * | 1961-09-29 | 1965-02-03 | Glaxo Group Ltd | Therapeutic resin complexes |
| US3594470A (en) * | 1968-02-19 | 1971-07-20 | Abbott Lab | Chewable tablets including coated particles of pseudoephedrine-weak cation exchange resin |
| GB1218102A (en) * | 1968-03-15 | 1971-01-06 | Philips Nv | Improvements in medicaments comprising drug/ion-exchange resin compounds |
| 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 |
| DE2343218C2 (de) * | 1973-08-28 | 1986-08-07 | Hoechst Ag, 6230 Frankfurt | Furosemid enthaltende Pellets |
-
1977
- 1977-11-24 BE BE182882A patent/BE861141A/xx not_active IP Right Cessation
- 1977-11-24 NZ NZ185772A patent/NZ185772A/xx unknown
- 1977-11-24 JP JP52140093A patent/JPS609697B2/ja not_active Expired
- 1977-11-24 IL IL53462A patent/IL53462A/xx unknown
- 1977-11-24 FI FI773568A patent/FI65910C/fi not_active IP Right Cessation
- 1977-11-24 CA CA291,664A patent/CA1086226A/en not_active Expired
- 1977-11-24 GR GR54861A patent/GR61724B/el unknown
- 1977-11-24 GB GB48997/77A patent/GB1544761A/en not_active Expired
- 1977-11-25 AU AU30986/77A patent/AU511080B2/en not_active Expired
- 1977-11-25 LU LU78584A patent/LU78584A1/xx unknown
- 1977-11-25 AT AT848077A patent/AT359197B/de not_active IP Right Cessation
- 1977-11-25 NL NLAANVRAGE7712996,A patent/NL182283C/xx not_active IP Right Cessation
- 1977-11-25 CH CH1450177A patent/CH639560A5/de not_active IP Right Cessation
- 1977-11-25 NO NO774051A patent/NO147626C/no unknown
- 1977-11-25 FR FR7735611A patent/FR2373288A1/fr active Granted
- 1977-11-25 DE DE2752728A patent/DE2752728C2/de not_active Expired
- 1977-11-25 SE SE7713370A patent/SE426781B/sv not_active IP Right Cessation
- 1977-11-25 DK DK523277A patent/DK150534C/da not_active IP Right Cessation
- 1977-11-25 PT PT67323A patent/PT67323B/pt unknown
- 1977-11-25 IE IE2391/77A patent/IE45998B1/en not_active IP Right Cessation
- 1977-11-25 AR AR270132A patent/AR218047A1/es active
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