CA1336687C - Mode de preparation de comprimes contenant de l'ibuprofene, de l'acetaminophere et de la cafeine, les produits ainsi obtenue et leurs applications - Google Patents
Mode de preparation de comprimes contenant de l'ibuprofene, de l'acetaminophere et de la cafeine, les produits ainsi obtenue et leurs applicationsInfo
- Publication number
- CA1336687C CA1336687C CA000609161A CA609161A CA1336687C CA 1336687 C CA1336687 C CA 1336687C CA 000609161 A CA000609161 A CA 000609161A CA 609161 A CA609161 A CA 609161A CA 1336687 C CA1336687 C CA 1336687C
- Authority
- CA
- Canada
- Prior art keywords
- caffeine
- tablets
- tablet
- ibuprofen
- apap
- 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 - Fee Related
Links
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 title claims abstract description 126
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 title claims abstract description 87
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 229960001680 ibuprofen Drugs 0.000 title claims abstract description 71
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 229960001948 caffeine Drugs 0.000 title claims abstract description 63
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 22
- 230000008569 process Effects 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 238000005550 wet granulation Methods 0.000 claims abstract description 16
- 229960005489 paracetamol Drugs 0.000 claims abstract description 14
- 206010037660 Pyrexia Diseases 0.000 claims abstract description 4
- 230000004054 inflammatory process Effects 0.000 claims abstract description 4
- 238000005469 granulation Methods 0.000 claims description 52
- 230000003179 granulation Effects 0.000 claims description 52
- 239000004480 active ingredient Substances 0.000 claims description 30
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 14
- 239000007888 film coating Substances 0.000 claims description 7
- 238000009501 film coating Methods 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 4
- 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 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 3
- 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 3
- 239000001856 Ethyl cellulose Substances 0.000 claims description 2
- 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 2
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 claims description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 2
- 229920001249 ethyl cellulose Polymers 0.000 claims description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 abstract description 13
- 208000029618 autoimmune pulmonary alveolar proteinosis Diseases 0.000 abstract 1
- 239000003826 tablet Substances 0.000 description 120
- 238000004090 dissolution Methods 0.000 description 28
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 21
- 229960001138 acetylsalicylic acid Drugs 0.000 description 19
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 18
- 239000002245 particle Substances 0.000 description 17
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 13
- 230000000202 analgesic effect Effects 0.000 description 12
- 238000007907 direct compression Methods 0.000 description 12
- 229920002472 Starch Polymers 0.000 description 11
- 235000021355 Stearic acid Nutrition 0.000 description 11
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 11
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 11
- 239000008107 starch Substances 0.000 description 11
- 235000019698 starch Nutrition 0.000 description 11
- 229940032147 starch Drugs 0.000 description 11
- 239000008117 stearic acid Substances 0.000 description 11
- 229940069328 povidone Drugs 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 229920002261 Corn starch Polymers 0.000 description 9
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 239000008120 corn starch Substances 0.000 description 9
- 229940016286 microcrystalline cellulose Drugs 0.000 description 9
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 9
- 239000008108 microcrystalline cellulose Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 229960000913 crospovidone Drugs 0.000 description 5
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 5
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 229920001213 Polysorbate 20 Polymers 0.000 description 4
- LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 4
- 239000002518 antifoaming agent Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 4
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical group O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000000889 atomisation Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000007908 dry granulation Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000007941 film coated tablet Substances 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- -1 polymethylsiloxane Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- 206010061218 Inflammation Diseases 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229940124827 caffeine tablet Drugs 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 229960001681 croscarmellose sodium Drugs 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- AMTWCFIAVKBGOD-UHFFFAOYSA-N dioxosilane;methoxy-dimethyl-trimethylsilyloxysilane Chemical group O=[Si]=O.CO[Si](C)(C)O[Si](C)(C)C AMTWCFIAVKBGOD-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 229940085392 excedrin Drugs 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 239000000820 nonprescription drug Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229940068977 polysorbate 20 Drugs 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229940083037 simethicone Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229950006451 sorbitan laurate Drugs 0.000 description 1
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000004408 titanium dioxide 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
- A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000609161A CA1336687C (fr) | 1989-08-23 | 1989-08-23 | Mode de preparation de comprimes contenant de l'ibuprofene, de l'acetaminophere et de la cafeine, les produits ainsi obtenue et leurs applications |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000609161A CA1336687C (fr) | 1989-08-23 | 1989-08-23 | Mode de preparation de comprimes contenant de l'ibuprofene, de l'acetaminophere et de la cafeine, les produits ainsi obtenue et leurs applications |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1336687C true CA1336687C (fr) | 1995-08-15 |
Family
ID=4140485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000609161A Expired - Fee Related CA1336687C (fr) | 1989-08-23 | 1989-08-23 | Mode de preparation de comprimes contenant de l'ibuprofene, de l'acetaminophere et de la cafeine, les produits ainsi obtenue et leurs applications |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1336687C (fr) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006004449A3 (fr) * | 2004-07-07 | 2006-03-02 | Aft Pharmaceuticals Ltd | Composition combinee |
| US7320985B2 (en) | 1997-02-04 | 2008-01-22 | Senju Pharmaceutical Co., Ltd. | Method for stabilizing arylcarboxylic acid, stabilizer thereof and aqueous solution containing stabilized arylcarboxylic acid |
| WO2010044681A1 (fr) * | 2008-10-14 | 2010-04-22 | Aft Pharmaceuticals Limited | Produit médicamenteux et traitement associé |
| US8580856B2 (en) | 2006-10-20 | 2013-11-12 | Ncneil-Ppc, Inc. | Acetaminophen/ibuprofen combinations and method for their use |
| WO2016030091A1 (fr) * | 2014-08-28 | 2016-03-03 | Boehringer Ingelheim International Gmbh | Comprimés pelliculés pour le traitement de la douleur aiguë |
| EP3185861A1 (fr) * | 2014-08-28 | 2017-07-05 | Sanofi-Aventis Deutschland GmbH | Composition pharmaceutique pour le traitement de la douleur aiguë des dents ou des mâchoires |
| US11197830B2 (en) | 2019-02-27 | 2021-12-14 | Aft Pharmaceuticals Limited | Pharmaceutical composition containing acetaminophen and ibuprofen |
-
1989
- 1989-08-23 CA CA000609161A patent/CA1336687C/fr not_active Expired - Fee Related
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7320985B2 (en) | 1997-02-04 | 2008-01-22 | Senju Pharmaceutical Co., Ltd. | Method for stabilizing arylcarboxylic acid, stabilizer thereof and aqueous solution containing stabilized arylcarboxylic acid |
| RU2455983C1 (ru) * | 2004-07-07 | 2012-07-20 | АФТ Фармасьютикалз Лимитед | Комбинированная композиция |
| GB2431346A (en) * | 2004-07-07 | 2007-04-25 | Aft Pharmaceuticals Ltd | A combination composition |
| AU2005260243B2 (en) * | 2004-07-07 | 2009-10-29 | Aft Pharmaceuticals Limited | A combination composition |
| GB2431346B (en) * | 2004-07-07 | 2010-01-27 | Aft Pharmaceuticals Ltd | A combination composition comprising paracetamol and ibuprofen |
| US10532036B2 (en) | 2004-07-07 | 2020-01-14 | Aft Pharmaceuticals Limited | Combination composition |
| WO2006004449A3 (fr) * | 2004-07-07 | 2006-03-02 | Aft Pharmaceuticals Ltd | Composition combinee |
| US8580856B2 (en) | 2006-10-20 | 2013-11-12 | Ncneil-Ppc, Inc. | Acetaminophen/ibuprofen combinations and method for their use |
| US8580855B2 (en) * | 2006-10-20 | 2013-11-12 | Mcneil-Ppc, Inc. | Acetaminophen / ibuprofen combinations and method for their use |
| GB2476418B (en) * | 2008-10-14 | 2013-04-24 | Aft Pharmaceuticals Ltd | A medicinal product and treatment |
| RU2487707C2 (ru) * | 2008-10-14 | 2013-07-20 | АФТ Фармасьютикалз Лимитед | Применение парацетамола и ибупрофена в лечении |
| GB2476418A (en) * | 2008-10-14 | 2011-06-22 | Aft Pharmaceuticals Ltd | A medicinal product and treatment |
| WO2010044681A1 (fr) * | 2008-10-14 | 2010-04-22 | Aft Pharmaceuticals Limited | Produit médicamenteux et traitement associé |
| CN107106502A (zh) * | 2014-08-28 | 2017-08-29 | 赛诺菲-安万特德国有限公司 | 用于治疗急性疼痛的薄膜包衣片 |
| EP3185861A1 (fr) * | 2014-08-28 | 2017-07-05 | Sanofi-Aventis Deutschland GmbH | Composition pharmaceutique pour le traitement de la douleur aiguë des dents ou des mâchoires |
| WO2016030091A1 (fr) * | 2014-08-28 | 2016-03-03 | Boehringer Ingelheim International Gmbh | Comprimés pelliculés pour le traitement de la douleur aiguë |
| AU2015309175B2 (en) * | 2014-08-28 | 2020-09-03 | Sanofi-Aventis Deutschland Gmbh | Film coated tablet for the treatment of acute pain |
| US11197830B2 (en) | 2019-02-27 | 2021-12-14 | Aft Pharmaceuticals Limited | Pharmaceutical composition containing acetaminophen and ibuprofen |
| US11534407B2 (en) | 2019-02-27 | 2022-12-27 | Aft Pharmaceuticals Limited | Pharmaceutical compostion containing acetominophen and ibuprofen |
| US11872317B2 (en) | 2019-02-27 | 2024-01-16 | Aft Pharmaceuticals Limited | Pharmaceutical composition containing acetominophen and ibuprofen |
| US12194151B2 (en) | 2019-02-27 | 2025-01-14 | Aft Pharmaceuticals Limited | Pharmaceutical compostion containing acetominophen and ibuprofen |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |