WO2007139886A2 - Duloxetine hydrochloride delayed release formulations - Google Patents
Duloxetine hydrochloride delayed release formulations Download PDFInfo
- Publication number
- WO2007139886A2 WO2007139886A2 PCT/US2007/012387 US2007012387W WO2007139886A2 WO 2007139886 A2 WO2007139886 A2 WO 2007139886A2 US 2007012387 W US2007012387 W US 2007012387W WO 2007139886 A2 WO2007139886 A2 WO 2007139886A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formulation
- layer
- talc
- percent
- enteric
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 152
- 238000009472 formulation Methods 0.000 title claims abstract description 111
- 229960002496 duloxetine hydrochloride Drugs 0.000 title claims abstract description 79
- JFTURWWGPMTABQ-UHFFFAOYSA-N n,n-dimethyl-3-naphthalen-1-yloxy-3-thiophen-2-ylpropan-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1OC(CCN(C)C)C1=CC=CS1 JFTURWWGPMTABQ-UHFFFAOYSA-N 0.000 title claims abstract description 79
- 230000003111 delayed effect Effects 0.000 title claims abstract description 39
- 239000010410 layer Substances 0.000 claims abstract description 174
- 229940079593 drug Drugs 0.000 claims abstract description 78
- 239000003814 drug Substances 0.000 claims abstract description 78
- 239000012055 enteric layer Substances 0.000 claims abstract description 59
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims abstract description 27
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims abstract description 23
- 229940117841 methacrylic acid copolymer Drugs 0.000 claims abstract description 18
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000000454 talc Substances 0.000 claims description 73
- 229910052623 talc Inorganic materials 0.000 claims description 73
- 229940033134 talc Drugs 0.000 claims description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 72
- 239000000725 suspension Substances 0.000 claims description 60
- 239000008188 pellet Substances 0.000 claims description 54
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 51
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 47
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 47
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 46
- 229960003943 hypromellose Drugs 0.000 claims description 46
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 37
- 229940075614 colloidal silicon dioxide Drugs 0.000 claims description 35
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 33
- 229930006000 Sucrose Natural products 0.000 claims description 33
- 239000005720 sucrose Substances 0.000 claims description 33
- 239000011248 coating agent Substances 0.000 claims description 30
- 239000002775 capsule Substances 0.000 claims description 28
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 23
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 23
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 23
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 22
- 239000004408 titanium dioxide Substances 0.000 claims description 22
- 229940069328 povidone Drugs 0.000 claims description 20
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims description 19
- 238000000576 coating method Methods 0.000 claims description 19
- 239000001069 triethyl citrate Substances 0.000 claims description 19
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 claims description 19
- 235000013769 triethyl citrate Nutrition 0.000 claims description 19
- 229960004793 sucrose Drugs 0.000 claims description 16
- 229960005196 titanium dioxide Drugs 0.000 claims description 15
- -1 glidants Substances 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- 229940032961 iron sucrose Drugs 0.000 claims description 7
- 239000002562 thickening agent Substances 0.000 claims description 7
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 6
- 239000002552 dosage form Substances 0.000 claims description 6
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 6
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 6
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 5
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 4
- 230000000181 anti-adherent effect Effects 0.000 claims description 4
- 239000003911 antiadherent Substances 0.000 claims description 4
- 229960005191 ferric oxide Drugs 0.000 claims description 4
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 4
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 4
- 235000012222 talc Nutrition 0.000 claims description 4
- 239000002216 antistatic agent Substances 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 208000020401 Depressive disease Diseases 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims 2
- 229920000609 methyl cellulose Polymers 0.000 claims 1
- 239000001923 methylcellulose Substances 0.000 claims 1
- 235000010981 methylcellulose Nutrition 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 235000012239 silicon dioxide Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 description 60
- 239000012530 fluid Substances 0.000 description 44
- 239000008213 purified water Substances 0.000 description 36
- 239000007921 spray Substances 0.000 description 22
- ZUAAPNNKRHMPKG-UHFFFAOYSA-N acetic acid;butanedioic acid;methanol;propane-1,2-diol Chemical compound OC.CC(O)=O.CC(O)CO.OC(=O)CCC(O)=O ZUAAPNNKRHMPKG-UHFFFAOYSA-N 0.000 description 10
- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 8
- 210000002784 stomach Anatomy 0.000 description 8
- 229920003134 Eudragit® polymer Polymers 0.000 description 7
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000009505 enteric coating Methods 0.000 description 6
- 239000002702 enteric coating Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 5
- 229940029644 cymbalta Drugs 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 210000000813 small intestine Anatomy 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 229960002866 duloxetine Drugs 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- CZMRCDWAGMRECN-MPZPMKCMSA-N (2r,4s,5s)-2-[(2s,4r,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound OC1[C@@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1C(O)[C@@H](O)[C@H](O)C(CO)O1 CZMRCDWAGMRECN-MPZPMKCMSA-N 0.000 description 2
- GMHDOCXPDYDKOR-KRWDZBQOSA-N (3s)-n-methyl-3-naphthalen-1-yloxy-3-thiophen-3-ylpropan-1-amine Chemical compound C=1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)C=CSC=1 GMHDOCXPDYDKOR-KRWDZBQOSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 235000013980 iron oxide Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 2
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000010215 titanium dioxide Nutrition 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 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 description 1
- 239000005414 inactive ingredient Substances 0.000 description 1
- KHLVKKOJDHCJMG-QDBORUFSSA-L indigo carmine Chemical compound [Na+].[Na+].N/1C2=CC=C(S([O-])(=O)=O)C=C2C(=O)C\1=C1/NC2=CC=C(S(=O)(=O)[O-])C=C2C1=O KHLVKKOJDHCJMG-QDBORUFSSA-L 0.000 description 1
- 239000004179 indigotine Substances 0.000 description 1
- 235000012738 indigotine Nutrition 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 description 1
- 229940127221 norepinephrine reuptake inhibitor Drugs 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
- A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core
-
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5026—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- 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
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
- A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
- A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
- A61K9/5047—Cellulose ethers containing no ester groups, e.g. hydroxypropyl methylcellulose
Definitions
- the invention encompasses duloxetine hydrochloride delayed release formulations and methods for their manufacture.
- the '276 patent discloses that the HPMCAS should be neutralized, for example, with ammonia to facilitate its dissolution.
- the '276 patent also discloses that duloxetine was found to react with many enteric coatings to form a slowly soluble or insoluble coating. This may lead to a disadvantageous drug-releasing profile and/or low bioavailability.
- the '276 patent also discloses that the enteric pharmaceutical formulations are manufactured in such a way that the product passes unchanged through the stomach of the patient, and dissolves and releases the active ingredient quickly when it leaves the stomach and enters the small intestine.
- the invention encompasses a duloxetine hydrochloride delayed release formulation comprising: (a) an inert core; (b) a drug layer comprising duloxetine hydrochloride; (c) a separating layer; (d) an enteric layer comprising at least one of a methacrylic acid copolymer and hydroxypropyl methyl cellulose phthalate; and, optionally, (e) a finish layer.
- the resulting solution is sprayed, while mixing, onto the sugar spheres in the fluid bed dryer through a 1 mm nozzle at an atomizing air pressure of 2.5 bar over a period of 240 minutes.
- the inlet air temperature is 60 0 C
- the outlet air temperature is 48°C
- the flap is 100 rrrVhr
- the spray rate is 5 to 10 g/min.
- the coated sugar spheres are then dried in the fluid bed dryer for an additional 5 minutes at 40 0 C to form drug-coated pellets.
- the inlet air temperature is 60 0 C
- the outlet air temperature is 45 0 C 5
- the flap is 80 m 3 /hr
- the spray rate is 10 g/min.
- Hypromellose, colloidal silicon dioxide and titanium dioxide are mixed in purified water in a mixer for 30 minutes to form a solution.
- Talc is mixed in purified water in a homogenizer for 30 minutes. The mixture of talc and water is then added to the solution in the mixer, and mixed for 15 minutes.
- the resulting suspension was sieved, and then sprayed onto the drug-coated pellets in the fluid bed dryer.
- the suspension was sprayed through a 1.2 mm nozzle at an atomizing air pressure of 2.5 bar over a period of 90 minutes.
- the inlet air temperature was 60 0 C
- the outlet air temperature was 45°C
- the flap was 80 m 3 /hr
- the spray rate was 10 g/min.
- EUDRAGIT ® L3OD55 methacrylic acid copolymer dispersion and triethyl citrate were mixed in a mixer for 15 minutes to form a 25-30 percent solution of film coating.
- Talc was mixed in purified water in a homogenizer for 30 minutes, and the resulting mixture of talc and water was added to the solution in the mixer. The resulting mixture was mixed for 15 minutes.
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (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)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009512149A JP2009538315A (en) | 2006-05-22 | 2007-05-22 | Duloxetine hydrochloride delayed release formulation |
CA002651716A CA2651716A1 (en) | 2006-05-22 | 2007-05-22 | Duloxetine hydrochloride delayed release formulations |
MX2008014758A MX2008014758A (en) | 2006-05-22 | 2007-05-22 | Duloxetine hydrochloride delayed release formulations. |
EP07795287A EP1919467A2 (en) | 2006-05-22 | 2007-05-22 | Duloxetine hydrochloride delayed release formulations |
BRPI0711606-3A BRPI0711606A2 (en) | 2006-05-22 | 2007-05-22 | delayed release duloxetine hydrochloride formulations |
IL194877A IL194877A0 (en) | 2006-05-22 | 2008-10-23 | Duloxetine hydrochloride delayed release formulations |
NO20085332A NO20085332L (en) | 2006-05-22 | 2008-12-19 | Delayed release duloxetine hydrogen chloride formulations |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US80284906P | 2006-05-22 | 2006-05-22 | |
US60/802,849 | 2006-05-22 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2007139886A2 true WO2007139886A2 (en) | 2007-12-06 |
WO2007139886A3 WO2007139886A3 (en) | 2008-03-13 |
Family
ID=38779216
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2007/012387 WO2007139886A2 (en) | 2006-05-22 | 2007-05-22 | Duloxetine hydrochloride delayed release formulations |
Country Status (12)
Country | Link |
---|---|
US (1) | US20070292511A1 (en) |
EP (1) | EP1919467A2 (en) |
JP (1) | JP2009538315A (en) |
KR (1) | KR20090005237A (en) |
CN (1) | CN101448493A (en) |
BR (1) | BRPI0711606A2 (en) |
CA (1) | CA2651716A1 (en) |
IL (1) | IL194877A0 (en) |
MX (1) | MX2008014758A (en) |
NO (1) | NO20085332L (en) |
RU (1) | RU2008148547A (en) |
WO (1) | WO2007139886A2 (en) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008020286A2 (en) * | 2006-08-14 | 2008-02-21 | Torrent Pharmaceuticals Limited | Pharmaceutical compositions of duloxetine |
WO2009004649A2 (en) * | 2007-05-21 | 2009-01-08 | Sun Pharmaceutical Industries Limited | Enteric coated pharmaceutical compositions |
WO2009066181A2 (en) * | 2007-07-09 | 2009-05-28 | Combino Pharm, S.L. | Oral delayed-release duloxentine hydrochloride pellets |
EP2133072A1 (en) | 2008-06-13 | 2009-12-16 | KRKA, D.D., Novo Mesto | Gastro-resistant pharmaceutical oral compositions comprising duloxetine or its pharmaceutically acceptable derivatives |
WO2009150238A2 (en) * | 2008-06-13 | 2009-12-17 | Krka, D.D. Novo Mesto | Gastro-resistant pharmaceutical oral compositions comprising duloxetine or its pharmaceutically acceptable derivatives |
WO2010078878A1 (en) * | 2009-01-12 | 2010-07-15 | Synthon B.V. | Duloxetine formulations |
DE102009033621A1 (en) | 2009-07-17 | 2011-01-20 | Add Technologies Ltd. | Separating layers for pharmaceutical preparations for preventing interactions between drugs and pharmaceutical-technological excipients |
US20110070299A1 (en) * | 2008-01-25 | 2011-03-24 | Alphapharm Pty Ltd. | Delayed release pharmaceutical composition of duloxetine |
EP2377525A1 (en) | 2010-03-26 | 2011-10-19 | Laboratorios del Dr. Esteve S.A. | Duloxetine enteric pellets |
ES2376095A1 (en) * | 2008-10-02 | 2012-03-09 | Laboratorios Del Dr. Esteve, S.A. | Duloxetine enteric pellets |
WO2015025261A1 (en) | 2013-08-21 | 2015-02-26 | Adamed Sp. Z O.O. | Duloxetine enteric coated tablet |
EP3335697A1 (en) * | 2016-12-14 | 2018-06-20 | Sun Pharmaceutical Industries Limited | Duloxetine sprinkles |
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JP2008543929A (en) * | 2005-06-20 | 2008-12-04 | カディラ・ヘルスケア・リミテッド | Duloxetine controlled release dosage formulation |
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2007
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- 2007-05-22 CA CA002651716A patent/CA2651716A1/en not_active Abandoned
- 2007-05-22 US US11/805,395 patent/US20070292511A1/en not_active Abandoned
- 2007-05-22 CN CNA200780018648XA patent/CN101448493A/en active Pending
- 2007-05-22 BR BRPI0711606-3A patent/BRPI0711606A2/en not_active IP Right Cessation
- 2007-05-22 RU RU2008148547/15A patent/RU2008148547A/en not_active Application Discontinuation
- 2007-05-22 JP JP2009512149A patent/JP2009538315A/en active Pending
- 2007-05-22 EP EP07795287A patent/EP1919467A2/en not_active Withdrawn
- 2007-05-22 MX MX2008014758A patent/MX2008014758A/en not_active Application Discontinuation
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2008
- 2008-10-23 IL IL194877A patent/IL194877A0/en unknown
- 2008-12-19 NO NO20085332A patent/NO20085332L/en not_active Application Discontinuation
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Also Published As
Publication number | Publication date |
---|---|
NO20085332L (en) | 2008-12-19 |
EP1919467A2 (en) | 2008-05-14 |
CN101448493A (en) | 2009-06-03 |
KR20090005237A (en) | 2009-01-12 |
IL194877A0 (en) | 2009-08-03 |
BRPI0711606A2 (en) | 2012-02-14 |
WO2007139886A3 (en) | 2008-03-13 |
US20070292511A1 (en) | 2007-12-20 |
RU2008148547A (en) | 2010-06-27 |
MX2008014758A (en) | 2009-01-19 |
CA2651716A1 (en) | 2007-12-06 |
JP2009538315A (en) | 2009-11-05 |
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