CA2797444A1 - Solid oral dosage forms comprising tadalafil - Google Patents
Solid oral dosage forms comprising tadalafil Download PDFInfo
- Publication number
- CA2797444A1 CA2797444A1 CA2797444A CA2797444A CA2797444A1 CA 2797444 A1 CA2797444 A1 CA 2797444A1 CA 2797444 A CA2797444 A CA 2797444A CA 2797444 A CA2797444 A CA 2797444A CA 2797444 A1 CA2797444 A1 CA 2797444A1
- Authority
- CA
- Canada
- Prior art keywords
- dosage form
- tadalafil
- polyoxyethylene
- esters
- acetyl
- 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.)
- Abandoned
Links
- 229960000835 tadalafil Drugs 0.000 title claims abstract description 75
- 239000007787 solid Substances 0.000 title claims abstract description 25
- 239000006186 oral dosage form Substances 0.000 title claims abstract description 11
- IEHKWSGCTWLXFU-IIBYNOLFSA-N tadalafil Chemical compound C1=C2OCOC2=CC([C@@H]2C3=C([C]4C=CC=CC4=N3)C[C@H]3N2C(=O)CN(C3=O)C)=C1 IEHKWSGCTWLXFU-IIBYNOLFSA-N 0.000 title claims abstract 19
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000005063 solubilization Methods 0.000 claims abstract description 16
- 230000007928 solubilization Effects 0.000 claims abstract description 16
- 239000002552 dosage form Substances 0.000 claims description 50
- -1 tragacantha Polymers 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 22
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 18
- 239000008137 solubility enhancer Substances 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 17
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 9
- 239000004014 plasticizer Substances 0.000 claims description 9
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000012876 carrier material Substances 0.000 claims description 7
- 239000003086 colorant Substances 0.000 claims description 7
- 239000004615 ingredient Substances 0.000 claims description 7
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 7
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 7
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 235000010489 acacia gum Nutrition 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 235000003599 food sweetener Nutrition 0.000 claims description 5
- 239000003765 sweetening agent Substances 0.000 claims description 5
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 4
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 4
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 4
- 238000005266 casting Methods 0.000 claims description 4
- 239000000796 flavoring agent Substances 0.000 claims description 4
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 4
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 4
- 229940041616 menthol Drugs 0.000 claims description 4
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims description 4
- 229960002622 triacetin Drugs 0.000 claims description 4
- AMMPRZCMKXDUNE-UHFFFAOYSA-N trihexyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCCCCOC(=O)CC(O)(C(=O)OCCCCCC)CC(=O)OCCCCCC AMMPRZCMKXDUNE-UHFFFAOYSA-N 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- 229920000858 Cyclodextrin Polymers 0.000 claims description 3
- 229920002907 Guar gum Polymers 0.000 claims description 3
- 239000005639 Lauric acid Substances 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 3
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 claims description 3
- 229920002125 Sokalan® Polymers 0.000 claims description 3
- 239000001785 acacia senegal l. willd gum Substances 0.000 claims description 3
- 229960000686 benzalkonium chloride Drugs 0.000 claims description 3
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 3
- 229960001927 cetylpyridinium chloride Drugs 0.000 claims description 3
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 claims description 3
- 229940097362 cyclodextrins Drugs 0.000 claims description 3
- 229960000633 dextran sulfate Drugs 0.000 claims description 3
- 239000000665 guar gum Substances 0.000 claims description 3
- 235000010417 guar gum Nutrition 0.000 claims description 3
- 229960002154 guar gum Drugs 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- 229940033355 lauric acid Drugs 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- 150000002888 oleic acid derivatives Chemical class 0.000 claims description 3
- 239000003961 penetration enhancing agent Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 229920000136 polysorbate Polymers 0.000 claims description 3
- 229940068965 polysorbates Drugs 0.000 claims description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 3
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 3
- 229960004025 sodium salicylate Drugs 0.000 claims description 3
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims 6
- 239000000194 fatty acid Substances 0.000 claims 6
- 229930195729 fatty acid Natural products 0.000 claims 6
- 125000005456 glyceride group Chemical group 0.000 claims 6
- 239000002202 Polyethylene glycol Substances 0.000 claims 5
- 239000005977 Ethylene Substances 0.000 claims 3
- 229920002675 Polyoxyl Polymers 0.000 claims 3
- 229920001214 Polysorbate 60 Polymers 0.000 claims 3
- 229930182558 Sterol Natural products 0.000 claims 3
- 229920001400 block copolymer Polymers 0.000 claims 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- 125000005908 glyceryl ester group Chemical group 0.000 claims 3
- 239000008172 hydrogenated vegetable oil Substances 0.000 claims 3
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims 3
- 150000003432 sterols Chemical class 0.000 claims 3
- 235000003702 sterols Nutrition 0.000 claims 3
- 235000015112 vegetable and seed oil Nutrition 0.000 claims 3
- 239000008158 vegetable oil Substances 0.000 claims 3
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 claims 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims 2
- 229920000084 Gum arabic Polymers 0.000 claims 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims 2
- 239000004368 Modified starch Substances 0.000 claims 2
- 229920000881 Modified starch Polymers 0.000 claims 2
- 229920002807 Thiomer Polymers 0.000 claims 2
- 239000000205 acacia gum Substances 0.000 claims 2
- 230000003078 antioxidant effect Effects 0.000 claims 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims 2
- 229920001577 copolymer Polymers 0.000 claims 2
- 235000013355 food flavoring agent Nutrition 0.000 claims 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims 2
- 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 2
- 235000019426 modified starch Nutrition 0.000 claims 2
- 229920001206 natural gum Polymers 0.000 claims 2
- 235000010413 sodium alginate Nutrition 0.000 claims 2
- 239000000661 sodium alginate Substances 0.000 claims 2
- 229940005550 sodium alginate Drugs 0.000 claims 2
- 239000011363 dried mixture Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 4
- 238000010521 absorption reaction Methods 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000011159 matrix material Substances 0.000 abstract description 2
- 230000003381 solubilizing effect Effects 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- WOXKDUGGOYFFRN-IIBYNOLFSA-N tadalafil Chemical compound C1=C2OCOC2=CC([C@@H]2C3=C(C4=CC=CC=C4N3)C[C@H]3N2C(=O)CN(C3=O)C)=C1 WOXKDUGGOYFFRN-IIBYNOLFSA-N 0.000 description 56
- 229940079593 drug Drugs 0.000 description 13
- 239000003814 drug Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004376 Sucralose Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000003623 enhancer Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 3
- 235000019408 sucralose Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 208000010228 Erectile Dysfunction Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 210000003128 head Anatomy 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 201000001881 impotence Diseases 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000003232 mucoadhesive effect Effects 0.000 description 2
- 238000010951 particle size reduction Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008371 vanilla flavor Substances 0.000 description 2
- SERLAGPUMNYUCK-DCUALPFSSA-N 1-O-alpha-D-glucopyranosyl-D-mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SERLAGPUMNYUCK-DCUALPFSSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-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
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920006125 amorphous polymer Polymers 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 229920001531 copovidone Polymers 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000000905 isomalt Substances 0.000 description 1
- 235000010439 isomalt Nutrition 0.000 description 1
- HPIGCVXMBGOWTF-UHFFFAOYSA-N isomaltol Natural products CC(=O)C=1OC=CC=1O HPIGCVXMBGOWTF-UHFFFAOYSA-N 0.000 description 1
- 238000009685 knife-over-roll coating Methods 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229960000502 poloxamer Drugs 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000006068 taste-masking agent Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 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
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32796910P | 2010-04-26 | 2010-04-26 | |
| US61/327,969 | 2010-04-26 | ||
| US13/079,348 | 2011-04-04 | ||
| US13/079,348 US20110263606A1 (en) | 2010-04-26 | 2011-04-04 | Solid oral dosage forms comprising tadalafil |
| PCT/IB2011/000882 WO2011135426A1 (en) | 2010-04-26 | 2011-04-22 | Solid oral dosage forms comprising tadalafil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2797444A1 true CA2797444A1 (en) | 2011-11-03 |
Family
ID=44816306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2797444A Abandoned CA2797444A1 (en) | 2010-04-26 | 2011-04-22 | Solid oral dosage forms comprising tadalafil |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US20110263606A1 (enExample) |
| EP (1) | EP2563346A4 (enExample) |
| JP (1) | JP2013527164A (enExample) |
| CA (1) | CA2797444A1 (enExample) |
| WO (1) | WO2011135426A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110136815A1 (en) | 2009-12-08 | 2011-06-09 | Horst Zerbe | Solid oral film dosage forms and methods for making same |
| US10610528B2 (en) | 2009-12-08 | 2020-04-07 | Intelgenx Corp. | Solid oral film dosage forms and methods for making same |
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| GB2497933B (en) * | 2011-12-21 | 2014-12-24 | Londonpharma Ltd | Drug delivery technology |
| WO2013109221A1 (en) * | 2012-01-18 | 2013-07-25 | Mahmut Bilgic | New effervescent formulations comprising sweetener composition |
| WO2014092661A1 (en) * | 2012-01-18 | 2014-06-19 | Mahmut Bilgic | Particulate formulations of tadalafil in effervescent form |
| WO2014027975A2 (en) * | 2012-08-17 | 2014-02-20 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Novel orally administered pharmaceutical formulations |
| US20150231092A1 (en) * | 2012-08-17 | 2015-08-20 | Sanovell IIac Sanayi Ve Ticaret Anonim Sirketi | Novel effervescent sachet formulations of dapoxetine and a pde5 inhibitor |
| WO2014027981A2 (en) * | 2012-08-17 | 2014-02-20 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Effervescent tablet formulations of dapoxetine and a pde5 inhibitor |
| WO2014027980A1 (en) * | 2012-08-17 | 2014-02-20 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Oral film formulations comprising dapoxetine and tadalafil |
| CN105209025B (zh) * | 2013-04-11 | 2019-06-18 | 西梯茜生命工学股份有限公司 | 包括聚乙二醇类聚合物和/或乙烯基吡咯烷酮类聚合物作为分散稳定剂的含他达拉非游离碱的膜剂形式 |
| US11116769B2 (en) | 2013-04-11 | 2021-09-14 | Ctc Bio, Inc. | Tadalafil free base-containing film dosage form containing polyethylene glycol-based polymer and/or vinyl pyrrolidone-based polymer as dispersion stabilizer |
| KR102239291B1 (ko) * | 2013-06-28 | 2021-04-14 | 한미약품 주식회사 | 타다라필 또는 이의 약학적으로 허용가능한 염을 포함하는 저작정 제제 |
| CA2919442A1 (en) * | 2013-07-31 | 2015-02-05 | Intelgenx Corp. | Instantly wettable oral film dosage form without surfactant or polyalcohol |
| KR20150138671A (ko) * | 2014-06-02 | 2015-12-10 | 에스케이케미칼주식회사 | 타달라필을 함유하는 구강 붕해 필름 및 이의 제조방법 |
| PL3111929T3 (pl) * | 2014-06-24 | 2019-01-31 | Wooshin Labottach Co., Ltd. | Ulegający rozpadowi w jamie ustnej preparat w postaci błony zawierający tadalafil i sposób jego wytwarzania |
| KR101538985B1 (ko) * | 2014-09-02 | 2015-07-24 | 주식회사 서울제약 | 타다라필 구강붕해필름 및 이의 제조방법 |
| CZ2016570A3 (cs) * | 2016-09-15 | 2018-03-28 | Zentiva, K.S. | Stabilní kompozice ODF obsahující těžce rozpustné terapeutické činidlo |
| CZ2017781A3 (cs) * | 2017-12-05 | 2019-06-12 | Zentiva, K.S. | Těžko rozpustné terapeutická činidla,která patřící do BCS skupiny II nebo IV, suspendovaná v kapalné formulaci a/nebo v konečné nanovláknité struktuře |
| US20210137919A1 (en) * | 2018-02-07 | 2021-05-13 | Smawa Gmbh | Pharmaceutical formulations, method for producing a pharmaceutical formulation, and medicament comprising same |
| CN109157520B (zh) * | 2018-09-07 | 2021-04-02 | 苏州科技城医院 | 他达拉非片剂及其制备方法 |
| US10828254B2 (en) | 2018-09-28 | 2020-11-10 | Intelgenx Corp. | Oral film formulation for modulating absorption profile |
| US12303501B2 (en) | 2018-11-05 | 2025-05-20 | Intelgenx Corp. | Lipophilic active oral film formulation and method of making the same |
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|---|---|---|---|---|
| DE19646392A1 (de) * | 1996-11-11 | 1998-05-14 | Lohmann Therapie Syst Lts | Zubereitung zur Anwendung in der Mundhöhle mit einer an der Schleimhaut haftklebenden, Pharmazeutika oder Kosmetika zur dosierten Abgabe enthaltenden Schicht |
| MXPA00003997A (es) * | 1999-04-30 | 2002-03-08 | Lilly Icos Llc | Articulos de fabricacion. |
| MX2008000087A (es) * | 2005-06-23 | 2008-03-18 | Schering Corp | Formulaciones orales rapidamente absorbentes de inhibidores de la fosfodiesterasa 5. |
| UA90763C2 (ru) * | 2005-11-08 | 2010-05-25 | Пфайзер Лимитед | Производные пиразола, способ их получения, фармацевтический состав на их основе и их применение |
| US9532945B2 (en) * | 2006-04-04 | 2017-01-03 | Kg Acquisition Llc | Oral dosage forms including an antiplatelet agent and an enterically coated acid inhibitor |
| BRPI0621852A2 (pt) * | 2006-07-07 | 2011-12-20 | Teva Pharma | compostos sólidos consistindo de tadalafil e pelo menos um veìculo |
| US20090098211A1 (en) * | 2007-04-25 | 2009-04-16 | Ilan Zalit | Solid dosage forms |
| US20080292683A1 (en) * | 2007-05-24 | 2008-11-27 | Monosolrx, Llc. | Film shreds and delivery system incorporating same |
| DE102007028869A1 (de) * | 2007-06-22 | 2008-12-24 | Ratiopharm Gmbh | Verfahren zur Herstellung eines Arzneimittels enthaltend Tadalafil |
| US20090047330A1 (en) * | 2007-08-17 | 2009-02-19 | Ramesh Bangalore | Oral fast dissolving films for erectile dysfunction bioactive agents |
| EP2214478A1 (en) * | 2007-10-19 | 2010-08-11 | Innozen, Inc. | Composition for administering an active ingredient and method for making and using the same |
| KR101074271B1 (ko) * | 2009-06-25 | 2011-10-17 | (주)차바이오앤디오스텍 | 불쾌한 맛을 효과적으로 은폐한 경구용 속용 필름 |
-
2011
- 2011-04-04 US US13/079,348 patent/US20110263606A1/en not_active Abandoned
- 2011-04-22 WO PCT/IB2011/000882 patent/WO2011135426A1/en not_active Ceased
- 2011-04-22 JP JP2013506767A patent/JP2013527164A/ja active Pending
- 2011-04-22 CA CA2797444A patent/CA2797444A1/en not_active Abandoned
- 2011-04-22 EP EP11774495.3A patent/EP2563346A4/en not_active Withdrawn
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2017
- 2017-11-27 US US15/822,734 patent/US20180078549A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013527164A (ja) | 2013-06-27 |
| EP2563346A1 (en) | 2013-03-06 |
| WO2011135426A1 (en) | 2011-11-03 |
| US20110263606A1 (en) | 2011-10-27 |
| US20180078549A1 (en) | 2018-03-22 |
| EP2563346A4 (en) | 2013-10-23 |
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