FR2464960A1 - Nouvelle forme non hygroscopique d'une cephalosporine sodique, son procede de preparation et son application en therapeutique - Google Patents
Nouvelle forme non hygroscopique d'une cephalosporine sodique, son procede de preparation et son application en therapeutique Download PDFInfo
- Publication number
- FR2464960A1 FR2464960A1 FR8019396A FR8019396A FR2464960A1 FR 2464960 A1 FR2464960 A1 FR 2464960A1 FR 8019396 A FR8019396 A FR 8019396A FR 8019396 A FR8019396 A FR 8019396A FR 2464960 A1 FR2464960 A1 FR 2464960A1
- Authority
- FR
- France
- Prior art keywords
- sodium salt
- fur
- solution
- acetoxymethyl
- water
- 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.)
- Granted
Links
- 229910052708 sodium Inorganic materials 0.000 title claims description 19
- 239000011734 sodium Substances 0.000 title claims description 19
- 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 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229930186147 Cephalosporin Natural products 0.000 title description 7
- 229940124587 cephalosporin Drugs 0.000 title description 7
- 150000001780 cephalosporins Chemical class 0.000 title description 7
- 230000001225 therapeutic effect Effects 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 69
- 159000000000 sodium salts Chemical class 0.000 claims description 62
- 239000000243 solution Substances 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 239000007924 injection Substances 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 13
- 238000002329 infrared spectrum Methods 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 238000005169 Debye-Scherrer Methods 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 238000002441 X-ray diffraction Methods 0.000 claims description 2
- 239000006286 aqueous extract Substances 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 abstract description 7
- 238000002425 crystallisation Methods 0.000 abstract description 4
- 230000008025 crystallization Effects 0.000 abstract description 4
- NOJNFULGOQGBKB-UHFFFAOYSA-M sodium;3-[3-tert-butylsulfanyl-1-[[4-(6-ethoxypyridin-3-yl)phenyl]methyl]-5-[(5-methylpyridin-2-yl)methoxy]indol-2-yl]-2,2-dimethylpropanoate Chemical compound [Na+].C1=NC(OCC)=CC=C1C(C=C1)=CC=C1CN1C2=CC=C(OCC=3N=CC(C)=CC=3)C=C2C(SC(C)(C)C)=C1CC(C)(C)C([O-])=O NOJNFULGOQGBKB-UHFFFAOYSA-M 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- 238000001914 filtration Methods 0.000 description 11
- 239000003981 vehicle Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 244000005700 microbiome Species 0.000 description 7
- -1 for example Chemical class 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical class [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229940063655 aluminum stearate Drugs 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229940049964 oleate Drugs 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 2
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 2
- 229940113124 polysorbate 60 Drugs 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- SOYANKPFXHJUCE-UHFFFAOYSA-N 1,4-dioxane-2-carbaldehyde Chemical compound O=CC1COCCO1 SOYANKPFXHJUCE-UHFFFAOYSA-N 0.000 description 1
- IQXJCCZJOIKIAD-UHFFFAOYSA-N 1-(2-methoxyethoxy)hexadecane Chemical compound CCCCCCCCCCCCCCCCOCCOC IQXJCCZJOIKIAD-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YQKXNEWHNMPIKL-UHFFFAOYSA-N Dioxamine Natural products C1=C2OCOC2=CC(C=CC(NCCC=2C=C3OCOC3=CC=2)=O)=C1 YQKXNEWHNMPIKL-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 241000588697 Enterobacter cloacae Species 0.000 description 1
- YXAGIRHBJJLWHW-UHFFFAOYSA-N Ethyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCC YXAGIRHBJJLWHW-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000192041 Micrococcus Species 0.000 description 1
- 241000219470 Mirabilis Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 241000607715 Serratia marcescens Species 0.000 description 1
- 241000607760 Shigella sonnei Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229940083916 aluminum distearate Drugs 0.000 description 1
- RDIVANOKKPKCTO-UHFFFAOYSA-K aluminum;octadecanoate;hydroxide Chemical compound [OH-].[Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O RDIVANOKKPKCTO-UHFFFAOYSA-K 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 description 1
- 229960001668 cefuroxime Drugs 0.000 description 1
- 239000007765 cera alba Substances 0.000 description 1
- 229950009789 cetomacrogol 1000 Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960002242 chlorocresol Drugs 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000001332 colony forming effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 229940075529 glyceryl stearate Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- CKQVRZJOMJRTOY-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CKQVRZJOMJRTOY-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229940115939 shigella sonnei Drugs 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- UDWXLZLRRVQONG-UHFFFAOYSA-M sodium hexanoate Chemical compound [Na+].CCCCCC([O-])=O UDWXLZLRRVQONG-UHFFFAOYSA-M 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7931379 | 1979-09-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2464960A1 true FR2464960A1 (fr) | 1981-03-20 |
| FR2464960B1 FR2464960B1 (enExample) | 1984-02-10 |
Family
ID=10507735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8019396A Granted FR2464960A1 (fr) | 1979-09-10 | 1980-09-09 | Nouvelle forme non hygroscopique d'une cephalosporine sodique, son procede de preparation et son application en therapeutique |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4341777A (enExample) |
| JP (1) | JPS5645486A (enExample) |
| AU (1) | AU6216080A (enExample) |
| BE (1) | BE885143A (enExample) |
| DE (1) | DE3033868A1 (enExample) |
| DK (1) | DK382580A (enExample) |
| FR (1) | FR2464960A1 (enExample) |
| GB (1) | GB2061922B (enExample) |
| IT (1) | IT1128177B (enExample) |
| NL (1) | NL8005072A (enExample) |
| NZ (1) | NZ194895A (enExample) |
| ZA (1) | ZA805556B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60120886A (ja) * | 1983-12-02 | 1985-06-28 | Takeda Chem Ind Ltd | セフェムカルボン酸のナトリウム塩の結晶 |
| US6930983B2 (en) * | 2000-03-15 | 2005-08-16 | Texas Instruments Incorporated | Integrated circuits, systems, apparatus, packets and processes utilizing path diversity for media over packet applications |
| US6911441B2 (en) | 2002-12-16 | 2005-06-28 | Akzo Nobel N.V. | Prolonged release pharmaceutical composition |
| EP3764485A1 (en) | 2019-07-12 | 2021-01-13 | Ratier-Figeac SAS | Brush assembly |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2241318A2 (enExample) * | 1973-08-21 | 1975-03-21 | Glaxo Lab Ltd | |
| GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
| FR2414509A1 (fr) * | 1978-01-17 | 1979-08-10 | Glaxo Group Ltd | Procede de cristallisation de cefuroxime sodique |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3974153A (en) * | 1971-05-14 | 1976-08-10 | Glaxo Laboratories Limited | 7-Hydrocarbonoxy imino-acetamido-3-carbamoyloxy methylceph-3-em-4 carboxylic acids |
| US3971778A (en) * | 1972-05-12 | 1976-07-27 | Glaxo Laboratories Limited | Cephalosporins having (α-etherified oximino)acylamido groups at the 7-position |
-
1980
- 1980-09-05 US US06/184,383 patent/US4341777A/en not_active Expired - Lifetime
- 1980-09-09 IT IT49634/80A patent/IT1128177B/it active
- 1980-09-09 DK DK382580A patent/DK382580A/da not_active Application Discontinuation
- 1980-09-09 DE DE19803033868 patent/DE3033868A1/de not_active Withdrawn
- 1980-09-09 NZ NZ194895A patent/NZ194895A/xx unknown
- 1980-09-09 ZA ZA00805556A patent/ZA805556B/xx unknown
- 1980-09-09 AU AU62160/80A patent/AU6216080A/en not_active Abandoned
- 1980-09-09 BE BE0/202033A patent/BE885143A/fr not_active IP Right Cessation
- 1980-09-09 GB GB8029059A patent/GB2061922B/en not_active Expired
- 1980-09-09 JP JP12523980A patent/JPS5645486A/ja active Pending
- 1980-09-09 FR FR8019396A patent/FR2464960A1/fr active Granted
- 1980-09-09 NL NL8005072A patent/NL8005072A/nl not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
| FR2241318A2 (enExample) * | 1973-08-21 | 1975-03-21 | Glaxo Lab Ltd | |
| FR2414509A1 (fr) * | 1978-01-17 | 1979-08-10 | Glaxo Group Ltd | Procede de cristallisation de cefuroxime sodique |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1128177B (it) | 1986-05-28 |
| FR2464960B1 (enExample) | 1984-02-10 |
| AU6216080A (en) | 1981-03-19 |
| US4341777A (en) | 1982-07-27 |
| NZ194895A (en) | 1983-07-15 |
| IT8049634A0 (it) | 1980-09-09 |
| DE3033868A1 (de) | 1981-04-02 |
| BE885143A (fr) | 1981-03-09 |
| DK382580A (da) | 1981-03-11 |
| NL8005072A (nl) | 1981-03-12 |
| JPS5645486A (en) | 1981-04-25 |
| GB2061922A (en) | 1981-05-20 |
| GB2061922B (en) | 1983-12-14 |
| ZA805556B (en) | 1982-04-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR0180798B1 (ko) | 결정성 페니실린 유도체, 그의 제법 및 용도 | |
| FR2466467A1 (fr) | Pentahydrate de cephalosporine, son procede de preparation et son application en therapeutique | |
| JPS62174018A (ja) | 細菌性感染症治療剤 | |
| JPS5944391A (ja) | 新規なセフロキシムエステル | |
| KR910004301B1 (ko) | 나트륨 세퓨록심의 제조방법 | |
| FR2528050A1 (fr) | Facteurs 1, 2, 3, 4 et 5 isoles purs de la teichomycine a2 utiles notamment comme medicaments antibiotiques et procede pour leur preparation | |
| FR2466469A1 (fr) | Bischlorhydrate de cephalosporine, son procede de preparation et ses applications, notamment en therapeutique | |
| BE487301A (enExample) | ||
| TW201309676A (zh) | 旋轉酶抑制劑（ｒ）－１－乙基－３－［５－［２－（１－羥基－１－甲基－乙基）嘧啶－５－基］－７－（四氫呋喃－２－基］－１ｈ－苯并咪唑－２－基］脲之固體形式 | |
| FR2610196A1 (fr) | Clavulanate de potassium, procedes de preparation, compositions pharmaceutiques le contenant et utilisation comme agents antibacteriens | |
| BE883390A (fr) | Derives de l'acide penicillanique utiles comme medicaments, compositions therapeutiques les contenant et procedes de leur preparation | |
| US5225427A (en) | 10-substituted ether derivatives of dihydroartemisinin, process for their preparation and their use as antiprotozoal agents | |
| FR2464960A1 (fr) | Nouvelle forme non hygroscopique d'une cephalosporine sodique, son procede de preparation et son application en therapeutique | |
| KR100416946B1 (ko) | 클라뷸란산염류 | |
| US6414142B1 (en) | Process for preparing potassium clavulanate | |
| IE44445B1 (en) | Pseudomonic acid amides | |
| FR2952M (enExample) | ||
| US20020004595A1 (en) | Process for preparing potassium clavulanate | |
| JP3796612B2 (ja) | 抗菌剤 | |
| DD213927A5 (de) | Verfahren zur herstellung von (3-benzothienyl)-glycylamidocephalosporin-derivaten | |
| FR2485540A1 (fr) | Nouveaux derives antibiotiques des cephalosporines, leur procede de preparation et les medicaments en contenant | |
| BE556491A (enExample) | ||
| KR810000005B1 (ko) | 6-메톡시-α-카르복시 페니실린류의 제조방법 | |
| JPH0240072B2 (enExample) | ||
| EP1998770B1 (fr) | Utilisation de la canthin-6-one et ses analogues dans le traitement des pathologies liees aux mycobacteries |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |