CA1121343A - Procede de preparation d'une forme cristalline du sel de sodium d'un derive oximine de l'acide 7-amino thiazolyl acetamido cephalosporanique - Google Patents
Procede de preparation d'une forme cristalline du sel de sodium d'un derive oximine de l'acide 7-amino thiazolyl acetamido cephalosporaniqueInfo
- Publication number
- CA1121343A CA1121343A CA000309454A CA309454A CA1121343A CA 1121343 A CA1121343 A CA 1121343A CA 000309454 A CA000309454 A CA 000309454A CA 309454 A CA309454 A CA 309454A CA 1121343 A CA1121343 A CA 1121343A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- solvate
- sodium salt
- formula
- hydrate
- 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
Links
- 159000000000 sodium salts Chemical class 0.000 title claims abstract description 61
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000002253 acid Substances 0.000 claims abstract description 83
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 66
- 239000012453 solvate Substances 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 150000007524 organic acids Chemical class 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 238000011065 in-situ storage Methods 0.000 claims abstract description 4
- 150000004677 hydrates Chemical class 0.000 claims abstract 3
- 150000001450 anions Chemical class 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 55
- 229910001868 water Inorganic materials 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 20
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 16
- 239000001632 sodium acetate Substances 0.000 claims description 12
- 235000017281 sodium acetate Nutrition 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 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 9
- BLSRNVDCHVKXSO-UHFFFAOYSA-M sodium;2-ethylbutanoate Chemical compound [Na+].CCC(CC)C([O-])=O BLSRNVDCHVKXSO-UHFFFAOYSA-M 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 5
- GTBXAGPZKPTPEJ-UHFFFAOYSA-N CC[Na].CCCCCC(O)=O Chemical compound CC[Na].CCCCCC(O)=O GTBXAGPZKPTPEJ-UHFFFAOYSA-N 0.000 claims description 2
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 241000894006 Bacteria Species 0.000 abstract description 7
- 230000003115 biocidal effect Effects 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 31
- -1 2-amino 4-thiazolyl Chemical group 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 14
- 239000013078 crystal Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 206010001497 Agitation Diseases 0.000 description 7
- 238000013019 agitation Methods 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 229960004592 isopropanol Drugs 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 241000588767 Proteus vulgaris Species 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 229940007042 proteus vulgaris Drugs 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 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
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- 241000588747 Klebsiella pneumoniae Species 0.000 description 2
- 241000588769 Proteus <enterobacteria> Species 0.000 description 2
- 241000588770 Proteus mirabilis Species 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- 241000708948 Solva Species 0.000 description 2
- 241000295644 Staphylococcaceae Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 241000534944 Thia Species 0.000 description 2
- 125000001931 aliphatic group Chemical class 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- UDTVQXNZIKQKOI-BAFYGKSASA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-4-carboxylic acid Chemical compound C1=CC(C(=O)O)S[C@@H]2CC(=O)N21 UDTVQXNZIKQKOI-BAFYGKSASA-N 0.000 description 1
- LAOROLNDGSJOEB-UHFFFAOYSA-N 3-(2-chlorophenothiazin-10-yl)-n,n-dimethylpropan-1-amine;4-(dimethylamino)-1,5-dimethyl-2-phenylpyrazol-3-one;n-(4-ethoxyphenyl)acetamide;1,3,7-trimethylpurine-2,6-dione Chemical compound CCOC1=CC=C(NC(C)=O)C=C1.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1.C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 LAOROLNDGSJOEB-UHFFFAOYSA-N 0.000 description 1
- SOQIQLVMDDDNHO-UHFFFAOYSA-N 3h-1,2-thiazol-2-amine Chemical compound NN1CC=CS1 SOQIQLVMDDDNHO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 201000004813 Bronchopneumonia Diseases 0.000 description 1
- 241001214176 Capros Species 0.000 description 1
- 206010007882 Cellulitis Diseases 0.000 description 1
- 102000001327 Chemokine CCL5 Human genes 0.000 description 1
- 108010055166 Chemokine CCL5 Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000283715 Damaliscus lunatus Species 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- 201000000297 Erysipelas Diseases 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 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 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 241000219470 Mirabilis Species 0.000 description 1
- 101100001347 Mus musculus Akt1s1 gene Proteins 0.000 description 1
- 241000282322 Panthera Species 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 229930182555 Penicillin Natural products 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
- 208000006311 Pyoderma Diseases 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 206010039740 Screaming Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- 101150110390 Slc10a6 gene Proteins 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 208000033809 Suppuration Diseases 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 241000218220 Ulmaceae Species 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940059720 apra Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000240602 cacao Species 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000004674 formic acids Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940090044 injection Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 101150111342 nol9 gene Proteins 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 208000013223 septicemia Diseases 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tert-butyl alcohol Substances CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
-
- 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
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7725142A FR2400519A1 (fr) | 1977-08-17 | 1977-08-17 | Forme cristalline du sel de sodium d'un derive oximine de l'acide 7-amino-thiazolyl acetamido cephalosporanique, son procede de preparation et son application comme medicament |
| FR7725142 | 1977-08-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1121343A true CA1121343A (fr) | 1982-04-06 |
Family
ID=9194564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000309454A Expired CA1121343A (fr) | 1977-08-17 | 1978-08-16 | Procede de preparation d'une forme cristalline du sel de sodium d'un derive oximine de l'acide 7-amino thiazolyl acetamido cephalosporanique |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US4224371A (en, 2012) |
| EP (1) | EP0001024B1 (en, 2012) |
| JP (1) | JPS5441890A (en, 2012) |
| AT (2) | AT366049B (en, 2012) |
| AU (1) | AU520898B2 (en, 2012) |
| BG (2) | BG33888A3 (en, 2012) |
| CA (1) | CA1121343A (en, 2012) |
| CS (2) | CS207646B2 (en, 2012) |
| DD (1) | DD137588A5 (en, 2012) |
| DE (1) | DE2860358D1 (en, 2012) |
| DK (2) | DK152213C (en, 2012) |
| EG (1) | EG13520A (en, 2012) |
| ES (1) | ES472381A1 (en, 2012) |
| FI (1) | FI65433C (en, 2012) |
| FR (1) | FR2400519A1 (en, 2012) |
| GE (2) | GEP19960475B (en, 2012) |
| GR (1) | GR73661B (en, 2012) |
| HR (1) | HRP931395B1 (en, 2012) |
| HU (1) | HU181497B (en, 2012) |
| IE (1) | IE47230B1 (en, 2012) |
| IL (1) | IL55186A (en, 2012) |
| IT (1) | IT1107961B (en, 2012) |
| MD (2) | MD247C2 (en, 2012) |
| MX (2) | MX155976A (en, 2012) |
| NO (1) | NO156168C (en, 2012) |
| NZ (1) | NZ188163A (en, 2012) |
| OA (1) | OA06016A (en, 2012) |
| PL (1) | PL126619B1 (en, 2012) |
| PT (1) | PT68431A (en, 2012) |
| RO (1) | RO79999A (en, 2012) |
| SI (1) | SI7811917A8 (en, 2012) |
| SU (2) | SU799666A3 (en, 2012) |
| YU (1) | YU42166B (en, 2012) |
| ZA (1) | ZA784187B (en, 2012) |
Families Citing this family (17)
| 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 |
| DE150507T1 (de) * | 1983-12-29 | 1987-02-26 | Mochida Pharmaceutical Co., Ltd., Tokio/Tokyo | Cephalosporinverbindungen, verfahren zu ihrer herstellung und pharmazeutishe praeparate. |
| JPS60142987A (ja) * | 1983-12-29 | 1985-07-29 | Mochida Pharmaceut Co Ltd | セフアロスポリン誘導体 |
| US4840945A (en) * | 1985-04-01 | 1989-06-20 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
| EP0233255B1 (en) * | 1985-08-12 | 1996-05-29 | The Upjohn Company | Conversion of cephalosporin hydrohalide salt to alkali metal salt |
| JPS63132893A (ja) * | 1986-11-25 | 1988-06-04 | Mochida Pharmaceut Co Ltd | 新規セフアロスポリン誘導体、その製法およびそれらを有効成分とする抗菌剤 |
| US4880798A (en) * | 1986-11-25 | 1989-11-14 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
| RU2021274C1 (ru) | 1991-05-17 | 1994-10-15 | Польска Акадэмия Наук Институт Хэмии Органичнэй | Способ получения аминотиазолильных производных цефалоспорина |
| US5318781A (en) * | 1993-04-06 | 1994-06-07 | Hoffmann-La Roche Inc. | Absorption enhancement of antibiotics |
| US5574154A (en) * | 1994-09-29 | 1996-11-12 | Alnejma Bulk Pharmaceutical Co. A.B.P.C. | Process for the preparation of cephalosporanic compounds |
| GB9423459D0 (en) * | 1994-11-21 | 1995-01-11 | Biochemie Gmbh | Silylation process |
| AT402928B (de) * | 1994-12-23 | 1997-09-25 | Biochemie Gmbh | Neues verfahren zur herstellung von cefotaxim |
| AU690482B2 (en) * | 1996-03-18 | 1998-04-23 | Ranbaxy Laboratories Limited | Process for producing cephalosporin antibiotics |
| GB9717629D0 (en) * | 1997-08-21 | 1997-10-22 | Johnson Matthey Plc | Removal of residual organic solvents |
| WO2001092254A1 (fr) * | 2000-05-30 | 2001-12-06 | Fujisawa Pharmaceutical Co., Ltd. | Procede permettant de remplacer des solvants contenus dans des cristaux de type clathrates |
| WO2004063203A1 (en) * | 2003-01-10 | 2004-07-29 | Orchid Chemicals & Pharmaceuticals Ltd | Process for the preparation of cefotaxime sodium |
| CN100361995C (zh) * | 2004-10-27 | 2008-01-16 | 山东瑞阳制药有限公司 | 注射级无菌头孢噻肟钠的一步法制备工艺 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3970651A (en) * | 1974-01-07 | 1976-07-20 | Bristol-Myers Company | Crystalline cephalosporin derivative |
| US3985747A (en) * | 1974-05-24 | 1976-10-12 | Bristol-Myers Company | Crystalline sesquihydrate of 7-[D-α-amino-α-(p-hydroxyphenyl)acetamido]-3-(1,2,3-triazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid |
| DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| US4006138A (en) * | 1975-04-11 | 1977-02-01 | Eli Lilly And Company | Crystalline form of sodium O-formylcefamandole |
| DE2760123C2 (de) * | 1976-01-23 | 1986-04-30 | Roussel-Uclaf, Paris | 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
| SE440655B (sv) * | 1976-01-23 | 1985-08-12 | Roussel Uclaf | Sett att framstella nya oximderivat av 7-amino-tiazolyl-acetamido-cefalosporansyra |
-
1977
- 1977-08-17 FR FR7725142A patent/FR2400519A1/fr active Granted
-
1978
- 1978-07-20 IL IL55186A patent/IL55186A/xx active IP Right Grant
- 1978-07-22 OA OA56566A patent/OA06016A/xx unknown
- 1978-07-24 ZA ZA00784187A patent/ZA784187B/xx unknown
- 1978-08-02 DD DD78207090A patent/DD137588A5/xx unknown
- 1978-08-03 EP EP78400072A patent/EP0001024B1/fr not_active Expired
- 1978-08-03 AT AT0563578A patent/AT366049B/de not_active IP Right Cessation
- 1978-08-03 DE DE7878400072T patent/DE2860358D1/de not_active Expired
- 1978-08-04 ES ES472381A patent/ES472381A1/es not_active Expired
- 1978-08-08 CS CS785183A patent/CS207646B2/cs unknown
- 1978-08-08 IT IT50648/78A patent/IT1107961B/it active Protection Beyond IP Right Term
- 1978-08-09 SU SU782645701A patent/SU799666A3/ru active
- 1978-08-10 SI SI7811917A patent/SI7811917A8/sl unknown
- 1978-08-10 YU YU1917/78A patent/YU42166B/xx unknown
- 1978-08-10 US US05/932,437 patent/US4224371A/en not_active Expired - Lifetime
- 1978-08-11 MX MX7926A patent/MX155976A/es unknown
- 1978-08-11 MX MX787309U patent/MX5448E/es unknown
- 1978-08-11 GR GR56985A patent/GR73661B/el unknown
- 1978-08-15 BG BG042035A patent/BG33888A3/xx unknown
- 1978-08-15 BG BG040671A patent/BG33887A3/xx unknown
- 1978-08-16 NZ NZ188163A patent/NZ188163A/xx unknown
- 1978-08-16 RO RO78101982A patent/RO79999A/ro unknown
- 1978-08-16 NO NO782782A patent/NO156168C/no unknown
- 1978-08-16 DK DK361078A patent/DK152213C/da not_active IP Right Cessation
- 1978-08-16 PT PT68431A patent/PT68431A/pt unknown
- 1978-08-16 CA CA000309454A patent/CA1121343A/fr not_active Expired
- 1978-08-16 EG EG510/78A patent/EG13520A/xx active
- 1978-08-16 FI FI782494A patent/FI65433C/fi not_active IP Right Cessation
- 1978-08-16 AU AU38965/78A patent/AU520898B2/en not_active Expired
- 1978-08-16 PL PL1978209080A patent/PL126619B1/pl unknown
- 1978-08-16 HU HU78RO993A patent/HU181497B/hu unknown
- 1978-08-17 IE IE1669/78A patent/IE47230B1/en not_active IP Right Cessation
- 1978-08-17 JP JP9958078A patent/JPS5441890A/ja active Granted
-
1979
- 1979-06-27 CS CS794439A patent/CS207647B2/cs unknown
-
1980
- 1980-01-31 AT AT0052280A patent/AT366050B/de not_active IP Right Cessation
- 1980-03-12 SU SU802891755A patent/SU852175A3/ru active
-
1986
- 1986-04-09 DK DK159786A patent/DK163514C/da not_active IP Right Cessation
-
1993
- 1993-07-31 GE GEAP19931371A patent/GEP19960475B/en unknown
- 1993-07-31 GE GEAP19931355A patent/GEP19960476B/en unknown
- 1993-11-11 HR HRP-1917/78A patent/HRP931395B1/xx not_active IP Right Cessation
-
1994
- 1994-09-08 MD MD94-0275A patent/MD247C2/ro unknown
- 1994-09-08 MD MD94-0267A patent/MD225C2/ro unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |