CA1283405C - Crystalline hydrate of oral cephalosporin and its composition - Google Patents
Crystalline hydrate of oral cephalosporin and its compositionInfo
- Publication number
- CA1283405C CA1283405C CA000541183A CA541183A CA1283405C CA 1283405 C CA1283405 C CA 1283405C CA 000541183 A CA000541183 A CA 000541183A CA 541183 A CA541183 A CA 541183A CA 1283405 C CA1283405 C CA 1283405C
- Authority
- CA
- Canada
- Prior art keywords
- hydrate
- gelatin
- drying
- capsule
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 30
- 229940124588 oral cephalosporin Drugs 0.000 title abstract description 3
- 108010010803 Gelatin Proteins 0.000 claims abstract description 36
- 229920000159 gelatin Polymers 0.000 claims abstract description 36
- 239000008273 gelatin Substances 0.000 claims abstract description 36
- 235000019322 gelatine Nutrition 0.000 claims abstract description 36
- 235000011852 gelatine desserts Nutrition 0.000 claims abstract description 36
- 239000013078 crystal Substances 0.000 claims abstract description 23
- 239000007902 hard capsule Substances 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 58
- 239000002775 capsule Substances 0.000 claims description 36
- 239000000243 solution Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 32
- 238000001035 drying Methods 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000011260 aqueous acid Substances 0.000 claims description 8
- 150000004683 dihydrates Chemical group 0.000 claims description 8
- 239000001913 cellulose Substances 0.000 claims description 7
- 229920002678 cellulose Polymers 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- -1 liquid paraffin Chemical compound 0.000 claims description 7
- 150000004684 trihydrates Chemical group 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 235000011181 potassium carbonates Nutrition 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
- 238000002441 X-ray diffraction Methods 0.000 claims description 4
- 239000004067 bulking agent Substances 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
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 3
- 239000004203 carnauba wax Substances 0.000 claims description 3
- 235000013869 carnauba wax Nutrition 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000008101 lactose Substances 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 230000005070 ripening Effects 0.000 claims description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 229920002261 Corn starch Polymers 0.000 claims description 2
- 229930091371 Fructose Natural products 0.000 claims description 2
- 239000005715 Fructose Substances 0.000 claims description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 239000003957 anion exchange resin Substances 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- 229910021538 borax Inorganic materials 0.000 claims description 2
- 239000008120 corn starch Substances 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 235000010944 ethyl methyl cellulose Nutrition 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229940057995 liquid paraffin Drugs 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- 239000001923 methylcellulose Substances 0.000 claims description 2
- 229920003087 methylethyl cellulose Polymers 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 2
- 229920000053 polysorbate 80 Polymers 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- 229940086066 potassium hydrogencarbonate Drugs 0.000 claims description 2
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 2
- 229920001592 potato starch Polymers 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 2
- 239000004328 sodium tetraborate Substances 0.000 claims description 2
- 235000010339 sodium tetraborate Nutrition 0.000 claims description 2
- 239000008117 stearic acid Substances 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 1
- 239000008116 calcium stearate Substances 0.000 claims 1
- 235000013539 calcium stearate Nutrition 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims 1
- 235000010234 sodium benzoate Nutrition 0.000 claims 1
- 239000004299 sodium benzoate Substances 0.000 claims 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 14
- 239000000843 powder Substances 0.000 description 11
- 238000007789 sealing Methods 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 229960000443 hydrochloric acid Drugs 0.000 description 7
- 239000004408 titanium dioxide Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000011812 mixed powder Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- RAGZEDHHTPQLAI-UHFFFAOYSA-L disodium;2',4',5',7'-tetraiodo-3-oxospiro[2-benzofuran-1,9'-xanthene]-3',6'-diolate Chemical compound [Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(I)=C([O-])C(I)=C1OC1=C(I)C([O-])=C(I)C=C21 RAGZEDHHTPQLAI-UHFFFAOYSA-L 0.000 description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 238000007908 dry granulation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
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- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
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- 238000011835 investigation Methods 0.000 description 1
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- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61156954A JP2544113B2 (ja) | 1986-07-02 | 1986-07-02 | 安定なカプセル製剤 |
| JP156954/1986 | 1986-07-02 | ||
| JP21626086A JPH0717651B2 (ja) | 1986-09-12 | 1986-09-12 | 経口投与用セフアロスポリン水和物結晶 |
| JP216260/1986 | 1986-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1283405C true CA1283405C (en) | 1991-04-23 |
Family
ID=26484565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000541183A Expired - Lifetime CA1283405C (en) | 1986-07-02 | 1987-07-02 | Crystalline hydrate of oral cephalosporin and its composition |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US4812561A (OSRAM) |
| KR (1) | KR950005302B1 (OSRAM) |
| CN (1) | CN1015106B (OSRAM) |
| AR (1) | AR243893A1 (OSRAM) |
| AT (1) | AT392472B (OSRAM) |
| AU (1) | AU594167B2 (OSRAM) |
| BE (1) | BE1001691A4 (OSRAM) |
| CA (1) | CA1283405C (OSRAM) |
| CH (1) | CH672788A5 (OSRAM) |
| DE (1) | DE3721913A1 (OSRAM) |
| DK (1) | DK161080C (OSRAM) |
| ES (2) | ES2004952A6 (OSRAM) |
| FI (1) | FI89052C (OSRAM) |
| FR (1) | FR2601014B1 (OSRAM) |
| GB (1) | GB2192183B (OSRAM) |
| GR (1) | GR871014B (OSRAM) |
| HK (1) | HK47893A (OSRAM) |
| HU (1) | HU200777B (OSRAM) |
| IE (1) | IE59613B1 (OSRAM) |
| IL (1) | IL83059A (OSRAM) |
| IT (1) | IT1211469B (OSRAM) |
| NL (1) | NL193136C (OSRAM) |
| NO (1) | NO170889C (OSRAM) |
| NZ (1) | NZ220764A (OSRAM) |
| PL (1) | PL159180B1 (OSRAM) |
| RU (1) | RU1829932C (OSRAM) |
| SE (1) | SE466257B (OSRAM) |
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| US5089270A (en) * | 1990-05-15 | 1992-02-18 | L. Perrigo Company | Capsule-shaped tablet |
| US5599557A (en) * | 1992-04-30 | 1997-02-04 | Schering Corporation | Stable hydrated cephalosporin dry powder for oral suspension formulation |
| JP2002528575A (ja) * | 1998-10-27 | 2002-09-03 | イーストマン ケミカル カンパニー | オレフィンの重合方法、新規ポリエチレン並びにそれから製造されるフィルム及び物品 |
| US6565882B2 (en) * | 2000-02-24 | 2003-05-20 | Advancis Pharmaceutical Corp | Antibiotic composition with inhibitor |
| US6544555B2 (en) | 2000-02-24 | 2003-04-08 | Advancis Pharmaceutical Corp. | Antibiotic product, use and formulation thereof |
| AT412213B (de) * | 2000-05-30 | 2004-11-25 | Sandoz Ag | Verfahren zur trocknung von amoxicillin oder amoxicillin-hältigen, oralen, festen pharmazeutischen zusammensetzungen unter verwendung eines gases mit einer definierten gasfeuchte |
| US6541014B2 (en) * | 2000-10-13 | 2003-04-01 | Advancis Pharmaceutical Corp. | Antiviral product, use and formulation thereof |
| US20020068078A1 (en) * | 2000-10-13 | 2002-06-06 | Rudnic Edward M. | Antifungal product, use and formulation thereof |
| US20020197314A1 (en) * | 2001-02-23 | 2002-12-26 | Rudnic Edward M. | Anti-fungal composition |
| US7842791B2 (en) * | 2002-12-19 | 2010-11-30 | Nancy Jean Britten | Dispersible pharmaceutical compositions |
| EP1648415A4 (en) * | 2003-07-21 | 2011-11-16 | Middlebrook Pharmaceuticals Inc | ANTIBIOTIC PRODUCT, ITS USE AND FORMULATION |
| EP1648418A4 (en) * | 2003-07-21 | 2011-11-16 | Middlebrook Pharmaceuticals Inc | ANTIBIOTIC PRODUCT, ITS USE AND FORMULATION |
| CA2533292C (en) * | 2003-07-21 | 2013-12-31 | Advancis Pharmaceutical Corporation | Antibiotic product, use and formulation thereof |
| WO2005016311A1 (en) * | 2003-08-11 | 2005-02-24 | Advancis Pharmaceutical Corporation | Robust pellet |
| CA2535398C (en) * | 2003-08-12 | 2013-11-12 | Advancis Pharmaceuticals Corporation | Antibiotic product, use and formulation thereof |
| EP1658034A4 (en) * | 2003-08-29 | 2011-06-22 | Middlebrook Pharmaceuticals Inc | ANTIBIOTIC PRODUCT, ITS USE AND FORMULATION |
| WO2005027877A1 (en) * | 2003-09-15 | 2005-03-31 | Advancis Pharmaceutical Corporation | Antibiotic product, use and formulation thereof |
| AU2004308419B2 (en) * | 2003-12-24 | 2011-06-02 | Victory Pharma, Inc. | Enhanced absorption of modified release dosage forms |
| US8715727B2 (en) * | 2004-07-02 | 2014-05-06 | Shionogi Inc. | Tablet for pulsed delivery |
| US20110104109A1 (en) * | 2005-07-13 | 2011-05-05 | Frank Bennett | Tetracyclic indole derivatives and their use for treating or preventing viral infections |
| EP1948179A1 (en) | 2005-11-11 | 2008-07-30 | Boehringer Ingelheim International GmbH | Quinazoline derivatives for the treatment of cancer diseases |
| US8778924B2 (en) * | 2006-12-04 | 2014-07-15 | Shionogi Inc. | Modified release amoxicillin products |
| US8357394B2 (en) | 2005-12-08 | 2013-01-22 | Shionogi Inc. | Compositions and methods for improved efficacy of penicillin-type antibiotics |
| US8299052B2 (en) * | 2006-05-05 | 2012-10-30 | Shionogi Inc. | Pharmaceutical compositions and methods for improved bacterial eradication |
| AR062927A1 (es) * | 2006-10-11 | 2008-12-17 | Bayer Healthcare Ag | 4- [4-( [ [ 4- cloro-3-( trifluorometil) fenil) carbamoil] amino] -3- fluorofenoxi) -n- metilpiridin-2- carboxamida monohidratada |
| CA2674831A1 (en) | 2006-12-22 | 2008-11-13 | Schering Corporation | 5,6-ring annulated indole derivatives and methods of use thereof |
| MX2009006880A (es) | 2006-12-22 | 2009-07-03 | Schering Corp | Derivados indolicos con anillo unido en las posiciones 4,5 para tratar o prevenir infecciones virales por virus de la hepatitis c e infecciones virales relacionadas. |
| JP5211068B2 (ja) * | 2006-12-22 | 2013-06-12 | メルク・シャープ・アンド・ドーム・コーポレーション | Ｈｃｖおよび関連するウイルス疾患の治療または予防のための４，５−環インドール誘導体 |
| CA2697500A1 (en) | 2007-08-29 | 2009-03-12 | Schering Corporation | 2,3-substituted azaindole derivatives for treating viral infections |
| EP2197842B1 (en) * | 2007-08-29 | 2012-05-23 | Schering Corporation | 2, 3-substituted indole derivatives for treating viral infections |
| ES2447543T3 (es) * | 2007-08-29 | 2014-03-12 | Merck Sharp & Dohme Corp. | Derivados de indol sustituidos y métodos de utilización de los mismos |
| CA2705586A1 (en) * | 2007-11-16 | 2009-05-22 | Schering Corporation | 3-heterocyclic substituted indole derivatives and methods of use thereof |
| EP2222672B1 (en) * | 2007-11-16 | 2013-12-18 | Merck Sharp & Dohme Corp. | 3-aminosulfonyl substituted indole derivatives and methods of use thereof |
| WO2009152200A1 (en) * | 2008-06-13 | 2009-12-17 | Schering Corporation | Tricyclic indole derivatives and methods of use thereof |
| TW201020245A (en) | 2008-08-20 | 2010-06-01 | Schering Corp | Ethynyl-substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
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| WO2010022126A1 (en) | 2008-08-20 | 2010-02-25 | Schering Corporation | Azo-substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
| CA2734486A1 (en) | 2008-08-20 | 2010-02-25 | Southern Research Institute | Substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
| CA2763140A1 (en) | 2009-05-29 | 2010-12-02 | Schering Corporation | Antiviral compounds composed of three linked aryl moieties to treat diseases such as hepatitis c |
| PL2451445T3 (pl) | 2009-07-06 | 2019-09-30 | Boehringer Ingelheim International Gmbh | Sposób suszenia BIBW2992, jego soli i stałych preparatów farmaceutycznych zawierających tę substancję czynną |
| AU2010324871A1 (en) | 2009-11-25 | 2012-06-14 | Merck Sharp & Dohme Corp. | Fused tricyclic compounds and derivatives thereof useful for the treatment of viral diseases |
| CA2785488A1 (en) | 2009-12-22 | 2011-07-21 | Merck Sharp & Dohme Corp. | Fused tricyclic compounds and methods of use thereof for the treatment of viral diseases |
| US9433621B2 (en) | 2010-02-18 | 2016-09-06 | Merck Sharp & Dohme Corp. | Substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
| EP2545060B1 (en) | 2010-03-09 | 2015-11-25 | Merck Sharp & Dohme Corp. | Fused tricyclic silyl compounds and methods of use thereof for the treatment of viral diseases |
| WO2011139253A2 (en) | 2010-05-04 | 2011-11-10 | Mahmut Bilgic | Pharmaceutical compositions comprising ceftibuten |
| WO2012018534A2 (en) | 2010-07-26 | 2012-02-09 | Schering Corporation | Substituted biphenylene compounds and methods of use thereof for the treatment of viral diseases |
| EP2621279B1 (en) | 2010-09-29 | 2018-04-04 | Merck Sharp & Dohme Corp. | Fused tetracycle derivatives and methods of use thereof for the treatment of viral diseases |
| US9156872B2 (en) | 2011-04-13 | 2015-10-13 | Merck Sharp & Dohme Corp. | 2′-azido substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| EP2696681B1 (en) | 2011-04-13 | 2018-10-03 | Merck Sharp & Dohme Corp. | 2'-substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| WO2013033899A1 (en) | 2011-09-08 | 2013-03-14 | Merck Sharp & Dohme Corp. | Substituted benzofuran compounds and methods of use thereof for the treatment of viral diseases |
| WO2013033901A1 (en) | 2011-09-08 | 2013-03-14 | Merck Sharp & Dohme Corp. | Heterocyclic-substituted benzofuran derivatives and methods of use thereof for the treatment of viral diseases |
| WO2013033900A1 (en) | 2011-09-08 | 2013-03-14 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds and methods of use thereof for the treatment of viral diseases |
| WO2013039876A1 (en) | 2011-09-14 | 2013-03-21 | Merck Sharp & Dohme Corp. | Silyl-containing heterocyclic compounds and methods of use thereof for the treatment of viral diseases |
| WO2013151518A1 (en) * | 2012-04-04 | 2013-10-10 | Mahmut Bilgic | Capsule formulations comprising ceftibuten |
| EP2815743A1 (en) | 2013-06-21 | 2014-12-24 | Sanovel Ilac Sanayi ve Ticaret A.S. | Ceftibuten formulations |
| US10167298B2 (en) | 2013-10-30 | 2019-01-01 | Merck Sharp & Dohme Corp. | Pseudopolymorphs of an HCV NS5A inhibitor and uses thereof |
| US9242965B2 (en) | 2013-12-31 | 2016-01-26 | Boehringer Ingelheim International Gmbh | Process for the manufacture of (E)-4-N,N-dialkylamino crotonic acid in HX salt form and use thereof for synthesis of EGFR tyrosine kinase inhibitors |
| CN103948932B (zh) * | 2014-04-17 | 2016-03-16 | 海南日中天制药有限公司 | 一种头孢克肟组合物及其制备方法 |
| EP3031450A1 (en) | 2014-12-12 | 2016-06-15 | Sanovel Ilac Sanayi ve Ticaret A.S. | Ceftibuten capsule compositions |
| CA3022684A1 (en) | 2016-05-13 | 2017-11-16 | Aeromics, Inc. | Crystals |
| MY196909A (en) | 2016-06-30 | 2023-05-09 | Qpex Biopharma Inc | Boronic acid derivatives and therapeutic uses thereof |
| CN106397454B (zh) * | 2016-08-30 | 2018-08-24 | 山东罗欣药业集团股份有限公司 | 一种抗感染药物头孢布烯晶型化合物及其组合物 |
| CN106432270A (zh) * | 2016-09-21 | 2017-02-22 | 临沂草之美医药科技有限公司 | 一种制备治疗外科手术感染的药物头孢布烯晶体化合物的方法 |
| CN106397457A (zh) * | 2016-09-21 | 2017-02-15 | 临沂草之美医药科技有限公司 | 一种治疗外科手术感染的药物头孢布烯晶体化合物 |
| CN106432272A (zh) * | 2016-09-21 | 2017-02-22 | 临沂草之美医药科技有限公司 | 一种制备治疗外科手术感染的药物头孢布烯晶体化合物的方法 |
| CN106432271A (zh) * | 2016-09-21 | 2017-02-22 | 临沂草之美医药科技有限公司 | 一种治疗外科手术感染的药物头孢布烯晶体化合物 |
| US12552815B2 (en) | 2020-05-05 | 2026-02-17 | Qpex Biopharma, Inc. | Boronic acid derivatives and synthesis, polymorphic forms, and therapeutic uses thereof |
| US20240327426A1 (en) * | 2021-07-01 | 2024-10-03 | Qpex Biopharma, Inc. | Crystalline forms of ceftibuten |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3819620A (en) * | 1972-06-01 | 1974-06-25 | Squibb & Sons Inc | 7-(d-alpha-amino-1,4-cyclohexadien-1-ylacet-amido)desacetoxycephalosporanic acid dihydrate |
| JPS5726692A (en) * | 1980-07-22 | 1982-02-12 | Fujisawa Pharmaceut Co Ltd | Preparation of stable crystal of salt of ceftizoxime |
| DE3037997A1 (de) * | 1980-10-08 | 1982-05-13 | Bayer Ag | (beta) -lactamantibiotika, verfahren zu deren herstellung sowie sie enthaltende mittel |
| YU44680B (en) * | 1982-07-30 | 1990-12-31 | Glaxo Lab Ltd | Process for obtaining very pure amorphous form of cephuroxim axetile |
| AU575854B2 (en) * | 1983-10-04 | 1988-08-11 | Shionogi & Co., Ltd. | 7beta-(carboxyalkenamido) cephalosporins |
| AU580855B2 (en) * | 1985-03-29 | 1989-02-02 | Shionogi & Co., Ltd. | Alkeneamidocephalosporin esters |
-
1987
- 1987-06-19 NZ NZ220764A patent/NZ220764A/xx unknown
- 1987-06-26 NL NL8701507A patent/NL193136C/nl not_active IP Right Cessation
- 1987-06-26 GB GB8715064A patent/GB2192183B/en not_active Expired - Lifetime
- 1987-06-29 IE IE173887A patent/IE59613B1/en not_active IP Right Cessation
- 1987-06-29 GR GR871014A patent/GR871014B/el unknown
- 1987-06-30 NO NO872729A patent/NO170889C/no not_active IP Right Cessation
- 1987-06-30 DK DK336487A patent/DK161080C/da not_active IP Right Cessation
- 1987-06-30 SE SE8702705A patent/SE466257B/sv not_active IP Right Cessation
- 1987-07-01 FI FI872903A patent/FI89052C/fi not_active IP Right Cessation
- 1987-07-01 IL IL83059A patent/IL83059A/xx not_active IP Right Cessation
- 1987-07-01 IT IT8767566A patent/IT1211469B/it active Protection Beyond IP Right Term
- 1987-07-01 US US07/068,333 patent/US4812561A/en not_active Expired - Lifetime
- 1987-07-01 PL PL1987266567A patent/PL159180B1/pl unknown
- 1987-07-01 FR FR878709316A patent/FR2601014B1/fr not_active Expired - Lifetime
- 1987-07-01 AT AT1658/87A patent/AT392472B/de not_active IP Right Cessation
- 1987-07-01 HU HU872992A patent/HU200777B/hu unknown
- 1987-07-01 CH CH2482/87A patent/CH672788A5/de not_active IP Right Cessation
- 1987-07-02 AR AR87308050A patent/AR243893A1/es active
- 1987-07-02 CA CA000541183A patent/CA1283405C/en not_active Expired - Lifetime
- 1987-07-02 AU AU75040/87A patent/AU594167B2/en not_active Expired
- 1987-07-02 ES ES8702189A patent/ES2004952A6/es not_active Expired
- 1987-07-02 BE BE8700740A patent/BE1001691A4/fr not_active IP Right Cessation
- 1987-07-02 KR KR1019870007019A patent/KR950005302B1/ko not_active Expired - Lifetime
- 1987-07-02 CN CN87105009A patent/CN1015106B/zh not_active Expired
- 1987-07-02 DE DE19873721913 patent/DE3721913A1/de not_active Withdrawn
- 1987-11-02 ES ES8703123A patent/ES2008759A6/es not_active Expired
- 1987-12-30 RU SU874203950A patent/RU1829932C/ru active
-
1988
- 1988-11-21 US US07/275,093 patent/US4933443A/en not_active Expired - Lifetime
-
1993
- 1993-05-20 HK HK478/93A patent/HK47893A/xx not_active IP Right Cessation
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