SK286631B6 - Žltá prášková kompozícia na orálne podávanie a spôsob jej prípravy - Google Patents
Žltá prášková kompozícia na orálne podávanie a spôsob jej prípravy Download PDFInfo
- Publication number
- SK286631B6 SK286631B6 SK1026-2000A SK10262000A SK286631B6 SK 286631 B6 SK286631 B6 SK 286631B6 SK 10262000 A SK10262000 A SK 10262000A SK 286631 B6 SK286631 B6 SK 286631B6
- Authority
- SK
- Slovakia
- Prior art keywords
- aqueous solution
- cefditoren pivoxil
- additive
- particles
- precipitate
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 97
- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 6
- AFZFFLVORLEPPO-UVYJNCLZSA-N cefditoren pivoxil Chemical compound S([C@@H]1[C@@H](C(N1C=1C(=O)OCOC(=O)C(C)(C)C)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1\C=C/C=1SC=NC=1C AFZFFLVORLEPPO-UVYJNCLZSA-N 0.000 claims abstract description 279
- 229960002142 cefditoren pivoxil Drugs 0.000 claims abstract description 266
- 239000007864 aqueous solution Substances 0.000 claims abstract description 198
- 239000000654 additive Substances 0.000 claims abstract description 146
- 230000000996 additive effect Effects 0.000 claims abstract description 142
- 239000002244 precipitate Substances 0.000 claims abstract description 129
- 239000002245 particle Substances 0.000 claims abstract description 120
- 239000008240 homogeneous mixture Substances 0.000 claims abstract description 77
- 239000000243 solution Substances 0.000 claims abstract description 58
- 239000002253 acid Substances 0.000 claims abstract description 29
- 238000001035 drying Methods 0.000 claims abstract description 12
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 6
- 229950009297 pivoxil Drugs 0.000 claims abstract description 6
- 230000002378 acidificating effect Effects 0.000 claims description 113
- 239000000843 powder Substances 0.000 claims description 97
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 86
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 86
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 86
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 86
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 79
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 79
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 79
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 64
- 238000006386 neutralization reaction Methods 0.000 claims description 60
- 239000000126 substance Substances 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- 229920000609 methyl cellulose Polymers 0.000 claims description 42
- 235000010981 methylcellulose Nutrition 0.000 claims description 42
- 239000001923 methylcellulose Substances 0.000 claims description 42
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 37
- 239000011541 reaction mixture Substances 0.000 claims description 37
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 32
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 32
- 239000007787 solid Substances 0.000 claims description 29
- 238000005406 washing Methods 0.000 claims description 26
- -1 alginic acid ester Chemical class 0.000 claims description 25
- 239000002344 surface layer Substances 0.000 claims description 24
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 20
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 20
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 20
- 229920002678 cellulose Polymers 0.000 claims description 17
- 239000001913 cellulose Substances 0.000 claims description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 16
- 238000000862 absorption spectrum Methods 0.000 claims description 15
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 239000000908 ammonium hydroxide Substances 0.000 claims description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 11
- 238000010521 absorption reaction Methods 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 8
- 229960004069 cefditoren Drugs 0.000 claims description 8
- 238000000975 co-precipitation Methods 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims description 8
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 239000003929 acidic solution Substances 0.000 claims description 7
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 7
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 7
- 229920001451 polypropylene glycol Polymers 0.000 claims description 7
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 6
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 6
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 6
- 235000010418 carrageenan Nutrition 0.000 claims description 6
- 239000000679 carrageenan Substances 0.000 claims description 6
- 229920001525 carrageenan Polymers 0.000 claims description 6
- 229940113118 carrageenan Drugs 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 235000010443 alginic acid Nutrition 0.000 claims description 4
- 239000000783 alginic acid Substances 0.000 claims description 4
- 229920000615 alginic acid Polymers 0.000 claims description 4
- 229960001126 alginic acid Drugs 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 238000005119 centrifugation Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000011736 potassium bicarbonate Substances 0.000 claims description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 235000011181 potassium carbonates Nutrition 0.000 claims description 3
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 235000017550 sodium carbonate Nutrition 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 8
- 239000010419 fine particle Substances 0.000 description 103
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 27
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 24
- 238000002441 X-ray diffraction Methods 0.000 description 17
- 150000007529 inorganic bases Chemical class 0.000 description 12
- 238000010191 image analysis Methods 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 3
- 238000010936 aqueous wash Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 235000015424 sodium Nutrition 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 2
- 150000004781 alginic acids Chemical class 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- QMHIMXFNBOYPND-UHFFFAOYSA-N 4-methylthiazole Chemical compound CC1=CSC=N1 QMHIMXFNBOYPND-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 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 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic 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; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic 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; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Inorganic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP192098 | 1998-01-07 | ||
| PCT/JP1999/000020 WO1999034832A1 (en) | 1998-01-07 | 1999-01-07 | Crystallographically stable amorphous cephalosporin compositions and process for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK10262000A3 SK10262000A3 (sk) | 2001-01-18 |
| SK286631B6 true SK286631B6 (sk) | 2009-02-05 |
Family
ID=11515039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1026-2000A SK286631B6 (sk) | 1998-01-07 | 1999-01-07 | Žltá prášková kompozícia na orálne podávanie a spôsob jej prípravy |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US6342493B1 (cs) |
| EP (1) | EP1051978B1 (cs) |
| JP (1) | JP3413406B2 (cs) |
| KR (1) | KR100435315B1 (cs) |
| CN (1) | CN1151845C (cs) |
| AU (1) | AU736555B2 (cs) |
| BR (1) | BRPI9907084B8 (cs) |
| CA (1) | CA2316841C (cs) |
| CZ (1) | CZ302082B6 (cs) |
| EA (1) | EA002881B1 (cs) |
| ES (1) | ES2393972T3 (cs) |
| HU (1) | HU230295B1 (cs) |
| ID (1) | ID25469A (cs) |
| IL (2) | IL137004A0 (cs) |
| NZ (1) | NZ505871A (cs) |
| PL (1) | PL194097B1 (cs) |
| PT (1) | PT1051978E (cs) |
| SK (1) | SK286631B6 (cs) |
| TR (1) | TR200001903T2 (cs) |
| TW (1) | TW587946B (cs) |
| UA (1) | UA70311C2 (cs) |
| WO (1) | WO1999034832A1 (cs) |
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| TR200001903T2 (tr) * | 1998-01-07 | 2000-11-21 | Meiji Seika Kaisha, Ltd. | Kristalografik açıdan kararlı, şekilsiz sefalosporin bileşimleri ve bunların üretilmesine ilişkin işlem. |
| HK1049656A1 (zh) | 1999-10-08 | 2003-05-23 | Smithkline Beecham Corporation | Fab i抑制剂 |
| DK1560584T3 (da) | 2001-04-06 | 2009-05-18 | Affinium Pharm Inc | Fab I inhibitorer |
| PT1389462E (pt) * | 2001-04-26 | 2012-06-19 | Meiji Seika Pharma Co Ltd | Composição de cefditoreno pivoxil amorfo e processo para o produzir |
| AU2003235962A1 (en) | 2002-10-02 | 2004-04-23 | Meiji Seika Kaisha, Ltd. | Antibacterial medicinal composition of enhanced oral absorptivity |
| ES2518316T3 (es) | 2002-12-06 | 2014-11-05 | Debiopharm International Sa | Compuestos heterocíclicos, métodos de fabricación de los mismos y su uso en terapia |
| CA2519429C (en) * | 2003-03-17 | 2013-08-06 | Affinium Pharmaceuticals, Inc. | Pharmaceutical compositions comprising inhibitors of fab i and further antibiotics |
| WO2004113451A1 (ja) * | 2003-06-20 | 2004-12-29 | Meiji Seika Kaisha, Ltd. | 難溶性物質と水溶性高分子との共沈物およびその製造方法 |
| EP1671635B1 (en) * | 2003-10-08 | 2012-01-04 | Meiji Seika Pharma Co., Ltd. | Noncrystalline antibacterial composition containing cefditoren pivoxil |
| JP2007510709A (ja) * | 2003-11-07 | 2007-04-26 | ランバクシー ラボラトリーズ リミテッド | 高純度３−（２−置換ビニル）セファロスポリンの製法 |
| JP2005162696A (ja) * | 2003-12-04 | 2005-06-23 | Nichiko Pharmaceutical Co Ltd | 溶出性に優れたセフジトレンピボキシル製剤 |
| WO2005082330A2 (en) * | 2004-02-19 | 2005-09-09 | Ranbaxy Laboratories Limited | Co-precipitated amorphous cefditoren pivoxil and dosage forms comprising the same |
| SI1828167T1 (sl) | 2004-06-04 | 2014-12-31 | Debiopharm International Sa Forum "Apres-Demain" | Akrilamidni derivati kot anitibiotična sredstva |
| US20080069879A1 (en) * | 2006-05-02 | 2008-03-20 | Ravishekhar Bhiwgade | Stable solid dosage form containing amorphous cefditoren pivoxil and process for preparation thereof |
| CA2658506C (en) | 2006-07-20 | 2016-01-26 | Affinium Pharmaceuticals, Inc. | Acrylamide derivatives as fab 1 inhibitors |
| WO2008057058A1 (en) * | 2006-11-10 | 2008-05-15 | Nobel Ilac Sanayii Ve Ticaret As | Oral pharmaceutical compositions |
| EP2125802A4 (en) | 2007-02-16 | 2014-08-20 | Debiopharm Int Sa | SALTS, PRODRUGS AND POLYMORPHES OF FAB I INHIBITORS |
| CN101560216B (zh) * | 2009-05-27 | 2011-06-15 | 上海交通大学 | 头孢妥仑酯的制备方法 |
| WO2012010938A2 (en) * | 2010-07-23 | 2012-01-26 | Lupin Limited | Pharmaceutical compositions of cefditoren pivoxil |
| US20130217708A1 (en) | 2010-09-30 | 2013-08-22 | Toyama Chemical Co., Ltd. | Meglumine salt of 6-fluoro-3-hydroxy-2-pyrazine carboxamide |
| PH12013500604A1 (en) | 2010-09-30 | 2013-05-06 | Toyama Chemical Co Ltd | Sodium salt of 6-fluoro-3-hydroxy-2-pyrazine carboxamide |
| LT2861608T (lt) | 2012-06-19 | 2019-07-10 | Debiopharm International Sa | (e)-n-metil-n-((3-metilbenzofuran-2-il)metil)-3-(7-okso-5,6,7,8-tetrahidro-1,8-nafthidrin-3-il)akrilamido provaisto dariniai |
| IN2013MU02828A (cs) * | 2013-08-29 | 2015-07-03 | Cadila Healthcare Ltd | |
| EP3244879A1 (en) | 2015-01-16 | 2017-11-22 | Ögün, Yusuf Toktamis | Cefditoren pivoxil compositions with improved stability and production methods thereof |
| WO2017144717A1 (en) | 2016-02-26 | 2017-08-31 | Debiopharm International S.A. | Medicament for treatment of diabetic foot infections |
| CN109053768A (zh) * | 2018-08-07 | 2018-12-21 | 中国医药集团总公司四川抗菌素工业研究所 | 一种无定型头孢妥仑酯的制备方法 |
| CA3129508A1 (en) | 2019-02-14 | 2020-08-20 | Debiopharm International S.A. | Solid formulations of afabicin with histidine |
| UA129222C2 (uk) | 2019-06-14 | 2025-02-12 | Дебіофарм Інтернешнл С.А. | Лікарський засіб і його застосування для лікування бактеріальних інфекцій, пов'язаних з біоплівкою |
| CN110251467A (zh) * | 2019-06-26 | 2019-09-20 | 北京济美堂医药研究有限公司 | 一种无定形态头孢妥仑匹酯组合物的制备方法 |
| CN112190539B (zh) * | 2020-11-10 | 2021-11-02 | 深圳立健药业有限公司 | 一种头孢妥仑匹酯组合物及其应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0678234B2 (ja) * | 1988-04-19 | 1994-10-05 | 明治製菓株式会社 | 経口投与用抗菌組成物 |
| JPH05306227A (ja) * | 1992-04-27 | 1993-11-19 | Lion Corp | 徐放性口腔内疾患治療剤 |
| JP2576927B2 (ja) * | 1992-05-15 | 1997-01-29 | ファイザー製薬株式会社 | 細粒核 |
| JPH06316517A (ja) * | 1993-02-22 | 1994-11-15 | Grelan Pharmaceut Co Ltd | 放出制御製剤 |
| JPH0717866A (ja) * | 1993-06-16 | 1995-01-20 | Meiji Seika Kaisha Ltd | 医薬組成物 |
| AU4314196A (en) | 1994-12-21 | 1996-07-10 | Yamanouchi Pharmaceutical Co., Ltd. | Solid composition with improved solubility and absorbability |
| AR004014A1 (es) * | 1995-10-13 | 1998-09-30 | Meiji Seika Kaisha | Una composicion antibacteriana de cefditoren pivoxilo para administracion oral y metodo para obtener dicha composicion |
| EP0904060B1 (en) | 1996-05-20 | 2003-12-10 | Janssen Pharmaceutica N.V. | Antifungal compositions with improved bioavailability |
| BR9712072A (pt) * | 1996-09-20 | 1999-08-24 | Meiji Seika Kaisha | Subst-ncia cristalina de defditoren pivoxil e a produ-Æo da mesma |
| TR200001903T2 (tr) * | 1998-01-07 | 2000-11-21 | Meiji Seika Kaisha, Ltd. | Kristalografik açıdan kararlı, şekilsiz sefalosporin bileşimleri ve bunların üretilmesine ilişkin işlem. |
-
1999
- 1999-01-07 TR TR2000/01903T patent/TR200001903T2/xx unknown
- 1999-01-07 PT PT99900136T patent/PT1051978E/pt unknown
- 1999-01-07 JP JP2000527279A patent/JP3413406B2/ja not_active Expired - Lifetime
- 1999-01-07 CN CNB998027855A patent/CN1151845C/zh not_active Expired - Lifetime
- 1999-01-07 HU HU0101272A patent/HU230295B1/hu unknown
- 1999-01-07 CA CA002316841A patent/CA2316841C/en not_active Expired - Lifetime
- 1999-01-07 BR BRPI9907084A patent/BRPI9907084B8/pt not_active IP Right Cessation
- 1999-01-07 EA EA200000742A patent/EA002881B1/ru not_active IP Right Cessation
- 1999-01-07 KR KR10-2000-7007546A patent/KR100435315B1/ko not_active Expired - Lifetime
- 1999-01-07 WO PCT/JP1999/000020 patent/WO1999034832A1/ja not_active Ceased
- 1999-01-07 US US09/582,937 patent/US6342493B1/en not_active Expired - Lifetime
- 1999-01-07 ES ES99900136T patent/ES2393972T3/es not_active Expired - Lifetime
- 1999-01-07 PL PL99341589A patent/PL194097B1/pl unknown
- 1999-01-07 AU AU17845/99A patent/AU736555B2/en not_active Ceased
- 1999-01-07 CZ CZ20002542A patent/CZ302082B6/cs not_active IP Right Cessation
- 1999-01-07 IL IL13700499A patent/IL137004A0/xx unknown
- 1999-01-07 SK SK1026-2000A patent/SK286631B6/sk not_active IP Right Cessation
- 1999-01-07 EP EP99900136A patent/EP1051978B1/en not_active Expired - Lifetime
- 1999-01-07 NZ NZ505871A patent/NZ505871A/xx not_active IP Right Cessation
- 1999-01-07 ID IDW20001303A patent/ID25469A/id unknown
- 1999-06-28 TW TW088110903A patent/TW587946B/zh not_active IP Right Cessation
- 1999-07-01 UA UA2000084638A patent/UA70311C2/uk unknown
-
2000
- 2000-06-26 IL IL137004A patent/IL137004A/en not_active IP Right Cessation
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2001
- 2001-11-26 US US09/991,694 patent/US6486149B2/en not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TC4A | Change of owner's name |
Owner name: MEIJI SEIKA PHARMA CO., LTD, CHUO-KU, TOKYO, JP Effective date: 20120309 |
|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20150107 |