EP2833874A1 - Capsule formulations comprising ceftibuten - Google Patents
Capsule formulations comprising ceftibutenInfo
- Publication number
- EP2833874A1 EP2833874A1 EP13724914.0A EP13724914A EP2833874A1 EP 2833874 A1 EP2833874 A1 EP 2833874A1 EP 13724914 A EP13724914 A EP 13724914A EP 2833874 A1 EP2833874 A1 EP 2833874A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formulation
- formulation according
- ceftibuten
- agent
- range
- 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.)
- Withdrawn
Links
- 229960004086 ceftibuten Drugs 0.000 title claims abstract description 46
- 239000007963 capsule composition Substances 0.000 title claims description 19
- UNJFKXSSGBWRBZ-BJCIPQKHSA-N ceftibuten Chemical compound S1C(N)=NC(C(=C\CC(O)=O)\C(=O)N[C@@H]2C(N3C(=CCS[C@@H]32)C(O)=O)=O)=C1 UNJFKXSSGBWRBZ-BJCIPQKHSA-N 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims abstract description 95
- 238000009472 formulation Methods 0.000 claims abstract description 68
- 239000002775 capsule Substances 0.000 claims abstract description 12
- 208000015181 infectious disease Diseases 0.000 claims abstract description 6
- 230000002485 urinary effect Effects 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 46
- SSWTVBYDDFPFAF-DKOGRLLHSA-N ceftibuten dihydrate Chemical compound O.O.S1C(N)=NC(C(=C\CC(O)=O)\C(=O)N[C@@H]2C(N3C(=CCS[C@@H]32)C(O)=O)=O)=C1 SSWTVBYDDFPFAF-DKOGRLLHSA-N 0.000 claims description 44
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 14
- 239000007884 disintegrant Substances 0.000 claims description 11
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 10
- 239000000314 lubricant Substances 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 7
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 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 6
- 150000004683 dihydrates Chemical group 0.000 claims description 6
- -1 glidant Substances 0.000 claims description 6
- 229920000609 methyl cellulose Polymers 0.000 claims description 6
- 239000001923 methylcellulose Substances 0.000 claims description 6
- 235000010981 methylcellulose Nutrition 0.000 claims description 6
- 206010006451 bronchitis Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 239000008187 granular material Substances 0.000 claims description 5
- 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 claims description 4
- 239000005995 Aluminium silicate Substances 0.000 claims description 4
- 229920002785 Croscarmellose sodium Polymers 0.000 claims description 4
- 108010010803 Gelatin Proteins 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 206010035664 Pneumonia Diseases 0.000 claims description 4
- 229920002472 Starch Polymers 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 235000012211 aluminium silicate Nutrition 0.000 claims description 4
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 claims description 4
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 4
- 229960001681 croscarmellose sodium Drugs 0.000 claims description 4
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 claims description 4
- 229920000159 gelatin Polymers 0.000 claims description 4
- 239000008273 gelatin Substances 0.000 claims description 4
- 235000019322 gelatine Nutrition 0.000 claims description 4
- 235000011852 gelatine desserts Nutrition 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 235000001055 magnesium Nutrition 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 4
- 229940069328 povidone Drugs 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 235000012239 silicon dioxide Nutrition 0.000 claims description 4
- 239000008107 starch Substances 0.000 claims description 4
- 235000019698 starch Nutrition 0.000 claims description 4
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims description 4
- 235000019731 tricalcium phosphate Nutrition 0.000 claims description 4
- 150000004684 trihydrates Chemical group 0.000 claims description 4
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 3
- 238000005469 granulation Methods 0.000 claims description 3
- 230000003179 granulation Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 208000020029 respiratory tract infectious disease Diseases 0.000 claims description 3
- 206010044008 tonsillitis Diseases 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 2
- 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
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 2
- 206010024971 Lower respiratory tract infections Diseases 0.000 claims description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 2
- 206010033078 Otitis media Diseases 0.000 claims description 2
- 239000008118 PEG 6000 Substances 0.000 claims description 2
- 201000007100 Pharyngitis Diseases 0.000 claims description 2
- 229920002584 Polyethylene Glycol 6000 Polymers 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 206010037597 Pyelonephritis acute Diseases 0.000 claims description 2
- 206010037601 Pyelonephritis chronic Diseases 0.000 claims description 2
- 206010046306 Upper respiratory tract infection Diseases 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 230000009798 acute exacerbation Effects 0.000 claims description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 2
- 235000013539 calcium stearate Nutrition 0.000 claims description 2
- 239000008116 calcium stearate Substances 0.000 claims description 2
- 229920003123 carboxymethyl cellulose sodium Polymers 0.000 claims description 2
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 claims description 2
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 235000010980 cellulose Nutrition 0.000 claims description 2
- 208000007451 chronic bronchitis Diseases 0.000 claims description 2
- 229940075614 colloidal silicon dioxide Drugs 0.000 claims description 2
- 229960000913 crospovidone Drugs 0.000 claims description 2
- 201000003146 cystitis Diseases 0.000 claims description 2
- 229940061607 dibasic sodium phosphate Drugs 0.000 claims description 2
- FSBVERYRVPGNGG-UHFFFAOYSA-N dimagnesium dioxido-bis[[oxido(oxo)silyl]oxy]silane hydrate Chemical compound O.[Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O FSBVERYRVPGNGG-UHFFFAOYSA-N 0.000 claims description 2
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 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
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 2
- 229940071676 hydroxypropylcellulose Drugs 0.000 claims description 2
- 229960003943 hypromellose Drugs 0.000 claims description 2
- 239000000391 magnesium silicate Substances 0.000 claims description 2
- 235000019792 magnesium silicate Nutrition 0.000 claims description 2
- 229910052919 magnesium silicate Inorganic materials 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- 229940091250 magnesium supplement Drugs 0.000 claims description 2
- 229960002900 methylcellulose Drugs 0.000 claims description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 2
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 2
- 229940045641 monobasic sodium phosphate Drugs 0.000 claims description 2
- 150000004682 monohydrates Chemical group 0.000 claims description 2
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 claims description 2
- 239000004223 monosodium glutamate Substances 0.000 claims description 2
- 235000013923 monosodium glutamate Nutrition 0.000 claims description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims description 2
- 235000019799 monosodium phosphate Nutrition 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 2
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 claims description 2
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 229940103091 potassium benzoate Drugs 0.000 claims description 2
- 235000010235 potassium benzoate Nutrition 0.000 claims description 2
- 239000004300 potassium benzoate Substances 0.000 claims description 2
- 239000001508 potassium citrate Substances 0.000 claims description 2
- 229960002635 potassium citrate Drugs 0.000 claims description 2
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 claims description 2
- 235000011082 potassium citrates Nutrition 0.000 claims description 2
- 229960001866 silicon dioxide Drugs 0.000 claims description 2
- 201000009890 sinusitis Diseases 0.000 claims description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 2
- 235000010234 sodium benzoate Nutrition 0.000 claims description 2
- 239000004299 sodium benzoate Substances 0.000 claims description 2
- 239000001509 sodium citrate Substances 0.000 claims description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 2
- 229940083608 sodium hydroxide Drugs 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 2
- 229940045902 sodium stearyl fumarate Drugs 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 235000012222 talc Nutrition 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims description 2
- 229940038773 trisodium citrate Drugs 0.000 claims description 2
- 235000019263 trisodium citrate Nutrition 0.000 claims description 2
- 208000000143 urethritis Diseases 0.000 claims description 2
- 238000007873 sieving Methods 0.000 claims 2
- 206010039587 Scarlet Fever Diseases 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 230000001050 lubricating effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 210000002345 respiratory system Anatomy 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007909 solid dosage form Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005550 wet granulation Methods 0.000 description 2
- YKMDNKRCCODWMG-UHFFFAOYSA-M 2,5-dinitrobenzoate Chemical compound [O-]C(=O)C1=CC([N+]([O-])=O)=CC=C1[N+]([O-])=O YKMDNKRCCODWMG-UHFFFAOYSA-M 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010014568 Empyema Diseases 0.000 description 1
- 208000004232 Enteritis Diseases 0.000 description 1
- 208000005577 Gastroenteritis Diseases 0.000 description 1
- 206010031252 Osteomyelitis Diseases 0.000 description 1
- 208000005141 Otitis Diseases 0.000 description 1
- 206010035742 Pneumonitis Diseases 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- 206010062255 Soft tissue infection Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 206010048038 Wound infection Diseases 0.000 description 1
- 206010000269 abscess Diseases 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229960001247 ceftibuten dihydrate Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 208000019258 ear infection Diseases 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 208000013223 septicemia Diseases 0.000 description 1
- PFMBRNMAXCVTIV-UHFFFAOYSA-K trisodium hydrogen carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.OC([O-])=O.OC([O-])=O PFMBRNMAXCVTIV-UHFFFAOYSA-K 0.000 description 1
- 231100000397 ulcer Toxicity 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
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
- A61K31/546—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine containing further heterocyclic rings, e.g. cephalothin
-
- 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
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
Definitions
- the present invention relates to pharmaceutical formulations comprising ceftibuten for use in treatment of upper and lower respiratory tract and urinary system infections. Said formulations are characterized in being in capsule form. Ceftibuten was first disclosed in the application numbered US 4634697.
- ceftibuten is indicated for infections such as abscesses caused by susceptible bacteria, bronchitis, dermatitis, otitis, empyema, enteritis, gastroenteritis, nasopharyngitis, osteomyelitis, pneumonia, pneumonitis, pustulosis, pyelonephritis, respiratory tract infections, rhinitis, septicemia, tonsillitis, ulcer, urinary system infections, wound and soft tissue infections.
- infections such as abscesses caused by susceptible bacteria, bronchitis, dermatitis, otitis, empyema, enteritis, gastroenteritis, nasopharyngitis, osteomyelitis, pneumonia, pneumonitis, pustulosis, pyelonephritis, respiratory tract infections, rhinitis, septicemia, tonsillitis, ulcer, urinary system infections, wound and soft tissue infections.
- Ceftibuten is present in 200 and 400 mg tablet forms on the market.
- ceftibuten is stabile in dihydrate and trihydrate forms. Furtermore, it is also disclosed in said patents that dihydrate and trihydrate forms of ceftibuten can be filled into hard gelatin capsules for oral administration.
- ceftibuten formulations are formulated in capsule form, low solubility of the capsules in gastro-intestinal liquid in body and difficulties of dissolution of ceftibuten decreases absorption of the medicine and leads to loss of effectiveness of the treatment. Therefore, there is still need for new approaches in order to develop ceftibuten formulations produced in capsule form which can disperse easily and fast in body, have high absorption and bioavailability during oral use.
- ceftibuten capsule forms which comprise a composition of at least two different pH agents having high water solubility as pH agent wherein the ratio of the first pH agent to the second pH agent composing this composition is in the range of 1 :5 to 5: 1 by weight disperse easily and fast in body and absorption and thus bioavailability of the drug is high.
- the present invention relates to capsule formulations comprising ceftibuten and is characterized in that said formulations comprise a composition of at least two different pH agents having high solubility in aqueous solutions and the ratio of the first pH agent to the second pH agent composing this composition is in the range of 1 :5 to 5:1 by weight.
- the ratio of the first pH agent to the second pH agent in the composition comprising at least two different pH agents is preferably in the range of 1 :3 to 5: 1 , more preferably in the range of 1 :2 to 4: 1 by weight.
- the first and the second pH agents composing the composition comprising at least two different pH agents having high solubility in aqueous solutions to be used in the formulations of the present invention can be selected from a group comprising tribasic calcium phosphate, monosodium glutamate, potassium citrate, trisodium citrate, sodium hydroxide, dibasic sodium phosphate, monobasic sodium phosphate, disodium hydrogen phosphate, sodium bicarbonate or combinations thereof.
- the first pH agent in the composition comprising at least two different pH agents having high solubility in aqueous solutions that shall be used in the formulations of the present invention can be disodium hydrogen phosphate.
- the second pH agent in the composition comprising at least two different pH agents having high solubility in aqueous solutions that shall be used in the formulations of the present invention can be sodium bicarbonate.
- the ratio of the two different pH agents disodium hydrogen phosphate and disodium sodium bicarbonate having high solubility in aqueous solutions to be used in the formulations of the present invention to each other can be in the range of 1 :5 to 5: 1 , preferably in the range of 1 :3 to 5 : 1 , more preferably in the range of 1 :2 to 4: 1 by weight.
- the present invention relates to capsule formulations comprising ceftibuten and another characteristic feature of said formulations is that the capsule formulations in which the ceftibuten formulation is filled is prepared from titanium dioxide, gelatin or a combination thereof.
- Solid dosage forms of the molecule ceftibuten having low water solubility present weak dispersibility and solubility characteristics and this results in decrease in absorption of the drug and thus effectiveness of the treatment.
- the inventors have observed that capsule formulations comprising ceftibuten present optimum dispersibility and solubility in the case that the ratio of ceftibuten to the pH agent composition comprising at least two different pH agents having high solubility in aqueous solutions is in the range of 1 : 1 to 15:1, preferably in the range of 3: 1 to 10:1.
- capsule formulations of the present invention comprise at least one pharmaceutically acceptable excipient in addition to ceftibuten and pH agent composition.
- the pharmaceutically acceptable excipients that can be used in the formulations of the present invention can be selected from a group comprising disintegrant, glidant, lubricant and binder.
- the disintegrant that can be used in the capsule formulations of the present invention comprising ceftibuten can be selected from a group comprising carboxymethyl cellulose calcium, carboxymethyl cellulose sodium, microcrystalline cellulose, silicon dioxide, croscarmellose sodium, crospovidone, hydroxypropyl cellulose, methylcellulose, povidone, magnesium aluminium silicate, starch.
- croscarmellose sodium can be used as the disintegrant in the capsule formulations of the present invention comprising ceftibuten.
- the glidant that can be used in the capsule formulations of the present invention comprising ceftibuten can be selected from a group comprising magnesium silicate, silicon dioxide, colloidal silicon dioxide, starch, talc, tribasic calcium phosphate or a combination thereof.
- the lubricant that can be used in the capsule formulations of the present invention comprising ceftibuten can be selected form a group comprising calcium stearate, magnesium stearate, sodium stearyl fumarate, polyethylene glycol, PEG 6000, polyvinyl alcohol, potassium benzoate, sodium benzoate.
- the binder that can be used in the capsule formulations of the present invention comprising ceftibuten can be selected from a group comprising ethyl cellulose, gelatin, hydroxyl ethyl cellulose, hydroxyl methyl cellulose, hydroxyl propyl cellulose, hypromellose, magnesium aluminium silicate, methyl cellulose, povidone.
- capsule formulations of the present invention comprising ceftibuten
- said formulations comprise ceftibuten in the range of 5-99%, preferably in the range of 10-95%, more preferably in the range of 30-90% by weight in proportion to total weight of the unit dose amount.
- ceftibuten in the form of its pharmaceutically acceptable solvates, monohydrate form, dihydrate form, trihydrate form, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms.
- ceftibuten in the capsule formulations of the present invention comprising ceftibuten, can preferably be in hydrate form, more preferably in dihydrate form.
- the formulations prepared according to the present invention can comprise 5-25% pH agent, 1-15% binder, 0.5-5% disintegrant, 0.01-0.5% glidant, 0.1-1.5% lubricant by weight in proportion to total weight of the unit dose amount.
- wet granulation method is used for preparation of the formulation of the present invention.
- ceftibuten is granulated with the granulation solution and the obtained granules are dried.
- the pH agent, disintegrant and glidant are added to the sieved granules and they are mixed together.
- the mixture is sieved again, lubricated adding the lubricant and then filled into capsules.
- the capsules are blistered and put into cartons.
- capsule formulations of the present invention comprising ceftibuten are used for production of a medicament effective in treatment of pharyngitis in children and/or adults; tonsillitis, sinusitis, red fever; upper respiratory tract infections such as otitis media in children, acute bronchitis, acute exacerbations of chronic bronchitis in adults; and lower respiratory tract infections such as pneumonia in patients suitable for oral treatment; urinary system infections such as acute and chronic pyelitis, cystopyelitis, cystitis, urethritis in adults and children.
- the examples below are given in order to explain the pharmaceutical compositions of the present invention and their preparation methods, yet the invention cannot be limited to these.
- the formulation given above is prepared by using wet granulation method. According to this, ceftibuten dihydrate is granulated with a granulation solution comprising binder. The obtained granules are dried, sieved and mixed with the pH agents, disintegrant and glidant. At the last phase, lubrication is applied with the lubricant and mixture is filled into capsules. Capsules are blistered and put into cartons.
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Abstract
The present invention relates to pharmaceutical formulations comprising ceftibuten for use in treatment of upper and lower respiratory tract and urinary system infections. Said formulations are characterized in being in capsule form.
Description
CAPSULE FORMULATIONS COMPRISING CEFTIBUTEN
The present invention relates to pharmaceutical formulations comprising ceftibuten for use in treatment of upper and lower respiratory tract and urinary system infections. Said formulations are characterized in being in capsule form. Ceftibuten was first disclosed in the application numbered US 4634697. It has been disclosed in said document that ceftibuten is indicated for infections such as abscesses caused by susceptible bacteria, bronchitis, dermatitis, otitis, empyema, enteritis, gastroenteritis, nasopharyngitis, osteomyelitis, pneumonia, pneumonitis, pustulosis, pyelonephritis, respiratory tract infections, rhinitis, septicemia, tonsillitis, ulcer, urinary system infections, wound and soft tissue infections.
Ceftibuten is present in 200 and 400 mg tablet forms on the market.
It is disclosed in the patents numbered US 4933443 and US 4812561 that ceftibuten is stabile in dihydrate and trihydrate forms. Furtermore, it is also disclosed in said patents that dihydrate and trihydrate forms of ceftibuten can be filled into hard gelatin capsules for oral administration.
However, low solubility of the molecule ceftibuten in aqueous solutions due to its hygroscopic nature leads to dispersibility and solubility problems during use of solid dosage forms of formulations comprising ceftibuten. In the case that ceftibuten formulations are formulated in capsule form, low solubility of the capsules in gastro-intestinal liquid in body and difficulties of dissolution of ceftibuten decreases absorption of the medicine and leads to loss of effectiveness of the treatment. Therefore, there is still need for new approaches in order to develop ceftibuten formulations produced in capsule form which can disperse easily and fast in body, have high absorption and bioavailability during oral use.
The inventors have surprisingly observed that ceftibuten capsule forms which comprise a composition of at least two different pH agents having high water solubility as pH agent wherein the ratio of the first pH agent to the second pH agent composing this composition is in the range of 1 :5 to 5: 1 by weight disperse easily and fast in body and absorption and thus bioavailability of the drug is high.
Description of the Invention
The present invention relates to capsule formulations comprising ceftibuten and is characterized in that said formulations comprise a composition of at least two different pH agents having high solubility in aqueous solutions and the ratio of the first pH agent to the second pH agent composing this composition is in the range of 1 :5 to 5:1 by weight.
Another characteristic of the formulations prepared according to the present invention is that the ratio of the first pH agent to the second pH agent in the composition comprising at least two different pH agents is preferably in the range of 1 :3 to 5: 1 , more preferably in the range of 1 :2 to 4: 1 by weight. The first and the second pH agents composing the composition comprising at least two different pH agents having high solubility in aqueous solutions to be used in the formulations of the present invention can be selected from a group comprising tribasic calcium phosphate, monosodium glutamate, potassium citrate, trisodium citrate, sodium hydroxide, dibasic sodium phosphate, monobasic sodium phosphate, disodium hydrogen phosphate, sodium bicarbonate or combinations thereof.
Preferably, the first pH agent in the composition comprising at least two different pH agents having high solubility in aqueous solutions that shall be used in the formulations of the present invention can be disodium hydrogen phosphate.
Preferably, the second pH agent in the composition comprising at least two different pH agents having high solubility in aqueous solutions that shall be used in the formulations of the present invention can be sodium bicarbonate.
The ratio of the two different pH agents disodium hydrogen phosphate and disodium sodium bicarbonate having high solubility in aqueous solutions to be used in the formulations of the present invention to each other can be in the range of 1 :5 to 5: 1 , preferably in the range of 1 :3 to 5 : 1 , more preferably in the range of 1 :2 to 4: 1 by weight.
The present invention relates to capsule formulations comprising ceftibuten and another characteristic feature of said formulations is that the capsule formulations in which the ceftibuten formulation is filled is prepared from titanium dioxide, gelatin or a combination thereof. Solid dosage forms of the molecule ceftibuten having low water solubility present weak dispersibility and solubility characteristics and this results in decrease in absorption of the drug and thus effectiveness of the treatment. The inventors have observed that capsule formulations comprising ceftibuten present optimum dispersibility and solubility in the case that the ratio of ceftibuten to the pH agent composition comprising at least two different pH agents having high solubility in aqueous solutions is in the range of 1 : 1 to 15:1, preferably in the range of 3: 1 to 10:1.
Another characteristic feature of the capsule formulations of the present invention is that said formulations comprise at least one pharmaceutically acceptable excipient in addition to ceftibuten and pH agent composition. The pharmaceutically acceptable excipients that can be used in the formulations of the present invention can be selected from a group comprising disintegrant, glidant, lubricant and binder.
The disintegrant that can be used in the capsule formulations of the present invention comprising ceftibuten can be selected from a group comprising carboxymethyl cellulose calcium, carboxymethyl cellulose sodium, microcrystalline cellulose, silicon dioxide, croscarmellose sodium, crospovidone, hydroxypropyl cellulose, methylcellulose, povidone, magnesium aluminium silicate, starch.
Preferably, croscarmellose sodium can be used as the disintegrant in the capsule formulations of the present invention comprising ceftibuten.
The glidant that can be used in the capsule formulations of the present invention comprising ceftibuten can be selected from a group comprising magnesium silicate, silicon dioxide, colloidal silicon dioxide, starch, talc, tribasic calcium phosphate or a combination thereof.
The lubricant that can be used in the capsule formulations of the present invention comprising ceftibuten can be selected form a group comprising calcium stearate, magnesium stearate, sodium stearyl fumarate, polyethylene glycol, PEG 6000, polyvinyl alcohol, potassium benzoate, sodium benzoate.
The binder that can be used in the capsule formulations of the present invention comprising ceftibuten can be selected from a group comprising ethyl cellulose, gelatin, hydroxyl ethyl cellulose, hydroxyl methyl cellulose, hydroxyl propyl cellulose, hypromellose, magnesium aluminium silicate, methyl cellulose, povidone. Another characteristic of the capsule formulations of the present invention comprising ceftibuten is that said formulations comprise ceftibuten in the range of 5-99%, preferably in the range of 10-95%, more preferably in the range of 30-90% by weight in proportion to total weight of the unit dose amount.
In the capsule formulations of the present invention comprising ceftibuten, ceftibuten can be in the form of its pharmaceutically acceptable solvates, monohydrate form, dihydrate form, trihydrate form, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms.
In the capsule formulations of the present invention comprising ceftibuten, ceftibuten can preferably be in hydrate form, more preferably in dihydrate form. The formulations prepared according to the present invention can comprise 5-25% pH agent, 1-15% binder, 0.5-5% disintegrant, 0.01-0.5% glidant, 0.1-1.5% lubricant by weight in proportion to total weight of the unit dose amount.
Preferably, wet granulation method is used for preparation of the formulation of the present invention. According to this method, ceftibuten is granulated with the granulation solution and the obtained granules are dried. The pH agent, disintegrant and glidant are added to the sieved granules and they are mixed together. The mixture is sieved again, lubricated adding the lubricant and then filled into capsules. The capsules are blistered and put into cartons.
Another characteristic feature of the capsule formulations of the present invention comprising ceftibuten is that they are used for production of a medicament effective in treatment of pharyngitis in children and/or adults; tonsillitis, sinusitis, red fever; upper respiratory tract infections such as otitis media in children, acute bronchitis, acute exacerbations of chronic bronchitis in adults; and lower respiratory tract infections such as pneumonia in patients suitable for oral treatment; urinary system infections such as acute and chronic pyelitis, cystopyelitis, cystitis, urethritis in adults and children.
The examples below are given in order to explain the pharmaceutical compositions of the present invention and their preparation methods, yet the invention cannot be limited to these.
EXAMPLE I. Capsule formulations comprising ceftibuten
The formulation given above is prepared by using wet granulation method. According to this, ceftibuten dihydrate is granulated with a granulation solution comprising binder. The obtained granules are dried, sieved and mixed with the pH agents, disintegrant and glidant. At the last phase, lubrication is applied with the lubricant and mixture is filled into capsules. Capsules are blistered and put into cartons.
Claims
1. Capsule formulations comprising ceftibuten, characterized in that said formulations comprise a composition comprising at least two different pH agents having high water solubility and the ratio of the first pH agent to the second pH agent composing this composition is in the range of 1 :5 to 5:1 by weight.
2. The formulation according to claim 1 , characterized in that the ratio of the first pH agent to the second pH agent composing the pH agent composition in said formulations is in the range of 1 :3 to 5: 1 by weight.
3. The formulation according to claim 2, characterized in that the ratio of the first pH agent to the second pH agent composing the pH agent composition in said formulations is in the range of 1 :2 to 4: 1 by weight.
4. The formulation according to claims 1-3, characterized in that the first and the second pH agents composing the pH agent composition in said formulations are selected from a group comprising tribasic calcium phosphate, monosodium glutamate, potassium citrate, trisodium citrate, sodium hydroxide, dibasic sodium phosphate, monobasic sodium phosphate, disodium hydrogen phosphate, sodium bicarbonate or combinations thereof.
5. The formulation according to claim 4, characterized in that disodium hydrogen phosphate is used as the first pH agent composing the pH agent composition in said formulation.
6. The formulation according to claim 4, characterized in that sodium bicarbonate is used as the second pH agent composing the pH agent composition in said formulation.
7. The formulation according to claims 1-6, characterized in that the ratio of the pH agents disodium hydrogen phosphate: sodium bicarbonate composing the pH composition to each other is in the range of 1 :5 to 5: 1 by weight.
8. The formulation according to claim 7, characterized in that the ratio of the pH agents disodium hydrogen phosphate: sodium bicarbonate composing the pH composition to each other is in the range of 1 :3 to 5:1 by weight.
9. The formulation according to claim 8, characterized in that the ratio of the pH agents disodium hydrogen phosphate: sodium bicarbonate composing the pH composition to each other is in the range of 1 :2 to 4: 1 by weight.
10. The formulation according to claims 1-9, characterized in that the ratio of ceftibuten-.pH agent composition is in the range of 1 : 1 to 15: 1 by weight.
1 1. The formulation according to claim 10, characterized in that the ratio of ceftibutenrpH agent composition is in the range of 3: 1 to 10: 1 by weight.
12. The formulation according to claims 1-1 1 , characterized in that said formulation comprises at least one pharmaceutically acceptable excipient in addition to ceftibuten and the pH agent composition.
13. The formulation according to claim 12, characterized in that the excipients that can be used in said formulation are selected from a group comprising disintegrant, glidant, lubricant and binder.
14. The formulation according to claim 13, characterized in that the disintegrant that can be used in said formulation is selected from a group comprising carboxymethyl cellulose calcium, carboxymethyl cellulose sodium, microcrystalline cellulose, silicon dioxide, croscarmellose sodium, crospovidone, hydroxypropyl cellulose, methylcellulose, povidone, magnesium aluminium silicate, starch or combinations thereof.
15. The formulation according to claim 14, characterized in that croscarmellose sodium is preferably used as the disintegrant that can be used in said formulation.
16. The formulation according to claim 13, characterized in that the glidant that can be used in said formulation is selected from a group comprising magnesium silicate, silicon dioxide, colloidal silicon dioxide, starch, talc, tribasic calcium phosphate or a combination thereof.
17. The formulation according to claim 13, characterized in that the lubricant that can be used in said formulation is selected from a group comprising calcium stearate, magnesium stearate, sodium stearyl fumarate, polyethylene glycol, PEG 6000, polyvinyl alcohol, potassium benzoate, sodium benzoate.
18. The formulation according to claim 13, characterized in that the binder that can be used in said formulation is selected from a group comprising ethyl cellulose, gelatin, hydroxyl ethyl cellulose, hydroxyl methyl cellulose, hydroxyl propyl cellulose, hypromellose, magnesium aluminium silicate, methyl cellulose, povidone.
19. The formulation according to any preceding claims, characterized in that the capsule formulation used in the capsule wherein ceftibuten formulation is filled is prepared from titanium dioxide, gelatin or a combination thereof.
20. The formulation according to any preceding claims, characterized in that said formulation comprises ceftibuten in the range of 5-99%.
21. The formulation according to claim 20, characterized in that said formulation comprises ceftibuten in the range of 10-95%.
22. The formulation according to claim 21, characterized in that said formulation comprises ceftibuten in the range of 30-90%.
23. The formulation according to any preceding claims, characterized in that ceftibuten comprised in said formulation is selected from a group comprising its pharmaceutically acceptable solvates, monohydrate form, dihydrate form, trihydrate form, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms.
24. The formulation according to claim 23, characterized in that ceftibuten in said formulation is in hydrate form.
25. The formulation according to claim 24, characterized in that ceftibuten in said formulation is in dihydrate form.
26. The formulation according to claim 24, characterized in that said formulation comprises 5-25% pH agent, 1-15% binder, 0.5-5% disintegrant, 0.01 -0.5% glidant, 0.1-1.5% lubricant by weight in proportion to total weight of unit dose amount.
27. A method for production of a formulation according to any preceding claims, characterized in that said method comprises the steps of granulating ceftibuten with the granulation solution, drying and sieving the obtained granules, adding pH agent, disintegrant and glidant to the granules and mixing them together, sieving the mixture again and lubricating it adding the lubricant, then filling the mixture into capsules.
28. The formulation according to any preceding claims, characterized in that said formulation is used for production of a medicament effective in treatment of pharyngitis in children and/or adults; tonsillitis, sinusitis, scarlet fever; upper respiratory tract infections such as otitis media in children, acute bronchitis, acute exacerbations of chronic bronchitis in adults; and lower respiratory tract infections such as pneumonia in patients suitable for oral treatment; urinary system infections such as acute and chronic pyelitis, cystopyelitis, cystitis, urethritis in adults and children.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TR201203836 | 2012-04-04 | ||
| PCT/TR2013/000109 WO2013151518A1 (en) | 2012-04-04 | 2013-04-03 | Capsule formulations comprising ceftibuten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2833874A1 true EP2833874A1 (en) | 2015-02-11 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP13724914.0A Withdrawn EP2833874A1 (en) | 2012-04-04 | 2013-04-03 | Capsule formulations comprising ceftibuten |
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| WO (1) | WO2013151518A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106432271A (en) * | 2016-09-21 | 2017-02-22 | 临沂草之美医药科技有限公司 | Pharmaceutical ceftibuten crystal compound for treating surgical infection |
| CN106397457A (en) * | 2016-09-21 | 2017-02-15 | 临沂草之美医药科技有限公司 | Drug ceftibuten crystal compound for treating surgical operation infection |
| CN106432270A (en) * | 2016-09-21 | 2017-02-22 | 临沂草之美医药科技有限公司 | Method for preparing medicine ceftibuten crystal compound for treating surgical infection |
| CN106432272A (en) * | 2016-09-21 | 2017-02-22 | 临沂草之美医药科技有限公司 | Method for preparing drug ceftibuten crystal compound for treating surgical operation infection |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU575854B2 (en) | 1983-10-04 | 1988-08-11 | Shionogi & Co., Ltd. | 7beta-(carboxyalkenamido) cephalosporins |
| NZ220764A (en) | 1986-07-02 | 1989-09-27 | Shionogi & Co | Crystalline form of 7beta((z)-2-(2-aminothiazol-4-yl)-4- carboxybut-2-enoylamino)-3-cephem-4-carboxylic acid and pharmaceutical compositions |
| FR2878159B1 (en) * | 2004-11-24 | 2008-10-17 | Flamel Technologies Sa | ORAL MEDICATION WITH MODIFIED RELEASE OF AT LEAST ONE ACTIVE PRINCIPLE IN MULTIMICROCAPSULAR FORM |
| JP2011516607A (en) * | 2008-04-15 | 2011-05-26 | サーコード コーポレイション | Delivery of LFA-1 antagonists to the gastrointestinal system |
-
2013
- 2013-04-03 WO PCT/TR2013/000109 patent/WO2013151518A1/en not_active Ceased
- 2013-04-03 EP EP13724914.0A patent/EP2833874A1/en not_active Withdrawn
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| See references of WO2013151518A1 * |
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