CA1308708C - Cephalosporins - Google Patents
CephalosporinsInfo
- Publication number
- CA1308708C CA1308708C CA000276067A CA276067A CA1308708C CA 1308708 C CA1308708 C CA 1308708C CA 000276067 A CA000276067 A CA 000276067A CA 276067 A CA276067 A CA 276067A CA 1308708 C CA1308708 C CA 1308708C
- Authority
- CA
- Canada
- Prior art keywords
- syn
- salt
- aminothiazol
- cephem
- ester
- 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
- 229930186147 Cephalosporin Natural products 0.000 title claims abstract description 22
- 229940124587 cephalosporin Drugs 0.000 title claims abstract description 22
- 150000001780 cephalosporins Chemical class 0.000 title claims description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 186
- 150000001875 compounds Chemical class 0.000 claims abstract description 183
- 150000002148 esters Chemical class 0.000 claims abstract description 150
- 125000003277 amino group Chemical group 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 7
- -1 carbamoyloxy Chemical group 0.000 claims description 259
- 238000000034 method Methods 0.000 claims description 129
- 125000006239 protecting group Chemical group 0.000 claims description 78
- 238000004519 manufacturing process Methods 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 125000002252 acyl group Chemical group 0.000 claims description 22
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000004423 acyloxy group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 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 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 9
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 8
- NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 claims description 7
- 125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 7
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- ZJIANJKJAAXAOC-HWZXHQHMSA-N (6r)-7-amino-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(COC(N)=O)=C(C(O)=O)N2C(=O)C(N)[C@H]21 ZJIANJKJAAXAOC-HWZXHQHMSA-N 0.000 claims description 5
- XUTQHTOXGKVJPN-XCGJVMPOSA-N (6r)-7-amino-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)C(N)[C@H]2SC1 XUTQHTOXGKVJPN-XCGJVMPOSA-N 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- GRQHDWCAMMHHNK-QHDYGNBISA-N (6r)-7-amino-8-oxo-3-(3-oxobutanoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(COC(=O)CC(=O)C)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 GRQHDWCAMMHHNK-QHDYGNBISA-N 0.000 claims description 2
- PAEXAIBDCHBNDC-UHFFFAOYSA-N 2-pyridin-4-ylacetic acid Chemical compound OC(=O)CC1=CC=NC=C1 PAEXAIBDCHBNDC-UHFFFAOYSA-N 0.000 claims description 2
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical group BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 claims description 2
- PWRBCZZQRRPXAB-UHFFFAOYSA-N 3-chloropyridine Chemical group ClC1=CC=CN=C1 PWRBCZZQRRPXAB-UHFFFAOYSA-N 0.000 claims description 2
- XDELKSRGBLWMBA-UHFFFAOYSA-N 3-iodopyridine Chemical group IC1=CC=CN=C1 XDELKSRGBLWMBA-UHFFFAOYSA-N 0.000 claims description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-O 4-methylpyridin-1-ium Chemical group CC1=CC=[NH+]C=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-O 0.000 claims description 2
- 125000005042 acyloxymethyl group Chemical group 0.000 claims description 2
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- RXYWJVBHDBOSNT-UHFFFAOYSA-N n-(hydroxymethyl)pyridine-4-carboxamide Chemical group OCNC(=O)C1=CC=NC=C1 RXYWJVBHDBOSNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- VFQXVTODMYMSMJ-UHFFFAOYSA-O pyridin-1-ium-4-carboxamide Chemical group NC(=O)C1=CC=[NH+]C=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-O 0.000 claims description 2
- PTMBWNZJOQBTBK-UHFFFAOYSA-N pyridin-4-ylmethanol Chemical compound OCC1=CC=NC=C1 PTMBWNZJOQBTBK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 229950010765 pivalate Drugs 0.000 claims 16
- 125000005633 phthalidyl group Chemical group 0.000 claims 12
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- LLCOQBODWBFTDD-UHFFFAOYSA-N 1h-triazol-1-ium-4-thiolate Chemical compound SC1=CNN=N1 LLCOQBODWBFTDD-UHFFFAOYSA-N 0.000 claims 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 4
- MLOZJRLUNNFSGD-IOJJLOCKSA-N (6r)-7-amino-8-oxo-3-(2h-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1CSC=1C=NNN=1 MLOZJRLUNNFSGD-IOJJLOCKSA-N 0.000 claims 3
- XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 claims 2
- UJBXVTJYSIDCIE-UHFFFAOYSA-N 2-[(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)sulfanyl]acetic acid Chemical compound OC(=O)CSC1=NNC(=S)S1 UJBXVTJYSIDCIE-UHFFFAOYSA-N 0.000 claims 2
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 claims 2
- NLDLXEAUMGUSPX-UHFFFAOYSA-N (5-sulfanylidene-2h-tetrazol-1-yl)methanesulfonic acid Chemical compound OS(=O)(=O)CN1N=NN=C1S NLDLXEAUMGUSPX-UHFFFAOYSA-N 0.000 claims 1
- RENYKLOVWMQOCD-OMNKOJBGSA-N (6R)-7-amino-3-[(1-methylimidazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC1[C@@H]2N(C(=C(CS2)CSC=2N(C=CN=2)C)C(=O)O)C1=O RENYKLOVWMQOCD-OMNKOJBGSA-N 0.000 claims 1
- FODVAYZBHAKEJN-HWZXHQHMSA-N (6r)-4-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CC(COC(=O)N)S[C@@H]2CC(=O)N21 FODVAYZBHAKEJN-HWZXHQHMSA-N 0.000 claims 1
- RGCSNQVGNVIUNF-OMNKOJBGSA-N (6r)-7-amino-3-[(4,5-dimethyl-1,2,4-triazol-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)C(N)[C@H]2SC1 RGCSNQVGNVIUNF-OMNKOJBGSA-N 0.000 claims 1
- NHGDIVKLXRLQQK-HWZXHQHMSA-N (6r)-7-amino-3-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1CSC1=NN=C(N)S1 NHGDIVKLXRLQQK-HWZXHQHMSA-N 0.000 claims 1
- FAKMUWSCVNYPHG-IOJJLOCKSA-N (6r)-7-amino-3-[(5-methyl-1,3,4-oxadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound O1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)C(N)[C@H]2SC1 FAKMUWSCVNYPHG-IOJJLOCKSA-N 0.000 claims 1
- HJSGHKMSDOLGJJ-IOJJLOCKSA-N (6r)-7-amino-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)C(N)[C@H]2SC1 HJSGHKMSDOLGJJ-IOJJLOCKSA-N 0.000 claims 1
- MDGYFLVHPNJXOI-IOJJLOCKSA-N (6r)-7-amino-3-[[1-(2-amino-2-oxoethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1CSC1=NN=NN1CC(N)=O MDGYFLVHPNJXOI-IOJJLOCKSA-N 0.000 claims 1
- KWWQYVGEBIIDFO-IOJJLOCKSA-N (6r)-7-amino-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1CSC1=NN=NN1CC(O)=O KWWQYVGEBIIDFO-IOJJLOCKSA-N 0.000 claims 1
- MFMIAOGDSQDUIH-XCGJVMPOSA-N (6r)-7-amino-8-oxo-3-(1h-1,2,4-triazol-5-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1CSC1=NC=NN1 MFMIAOGDSQDUIH-XCGJVMPOSA-N 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 claims 1
- GVVFXDASYCRTOC-UHFFFAOYSA-N 2-(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)acetamide Chemical compound NC(=O)CC1=NN=C(S)S1 GVVFXDASYCRTOC-UHFFFAOYSA-N 0.000 claims 1
- MYTWYPWDKHLWED-UHFFFAOYSA-N 2-(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)acetic acid Chemical compound OC(=O)CC1=NN=C(S)S1 MYTWYPWDKHLWED-UHFFFAOYSA-N 0.000 claims 1
- UOTQEHLQKASWQO-UHFFFAOYSA-N 2-(5-sulfanylidene-2h-tetrazol-1-yl)acetic acid Chemical compound OC(=O)CN1N=NN=C1S UOTQEHLQKASWQO-UHFFFAOYSA-N 0.000 claims 1
- ITQTTZVARXURQS-UHFFFAOYSA-O 3-methylpyridin-1-ium Chemical group CC1=CC=C[NH+]=C1 ITQTTZVARXURQS-UHFFFAOYSA-O 0.000 claims 1
- OQQHBSKUYSDTHT-UHFFFAOYSA-N 4,5-dimethyl-1H-1,2,4-triazole-5-thiol Chemical compound CN1C(NN=C1)(S)C OQQHBSKUYSDTHT-UHFFFAOYSA-N 0.000 claims 1
- KKHBRTFQIYIHEI-UHFFFAOYSA-N 4,5-dimethyl-3h-1,3-thiazole-2-thione Chemical compound CC=1N=C(S)SC=1C KKHBRTFQIYIHEI-UHFFFAOYSA-N 0.000 claims 1
- IIYVNMXPYWIJBL-UHFFFAOYSA-N 4-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=NC=C1 IIYVNMXPYWIJBL-UHFFFAOYSA-N 0.000 claims 1
- URCMHOZVBVATRJ-UHFFFAOYSA-N 5-[(dimethylamino)methyl]-3h-1,3,4-thiadiazole-2-thione Chemical compound CN(C)CC1=NN=C(S)S1 URCMHOZVBVATRJ-UHFFFAOYSA-N 0.000 claims 1
- GDGIVSREGUOIJZ-UHFFFAOYSA-N 5-amino-3h-1,3,4-thiadiazole-2-thione Chemical compound NC1=NN=C(S)S1 GDGIVSREGUOIJZ-UHFFFAOYSA-N 0.000 claims 1
- ZVGKPQCCKGLQPB-UHFFFAOYSA-N 5-methyl-3h-1,3,4-oxadiazole-2-thione Chemical compound CC1=NN=C(S)O1 ZVGKPQCCKGLQPB-UHFFFAOYSA-N 0.000 claims 1
- FPVUWZFFEGYCGB-UHFFFAOYSA-N 5-methyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CC1=NN=C(S)S1 FPVUWZFFEGYCGB-UHFFFAOYSA-N 0.000 claims 1
- 206010011703 Cyanosis Diseases 0.000 claims 1
- 125000004848 alkoxyethyl group Chemical group 0.000 claims 1
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims 1
- NOHWTPLPUJCKLF-UHFFFAOYSA-N methyl n-(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)carbamate Chemical compound COC(=O)NC1=NN=C(S)S1 NOHWTPLPUJCKLF-UHFFFAOYSA-N 0.000 claims 1
- BIAGWQYHUNVQCD-UHFFFAOYSA-N n-cyanopyridine-4-carboxamide Chemical compound N#CNC(=O)C1=CC=NC=C1 BIAGWQYHUNVQCD-UHFFFAOYSA-N 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 abstract description 16
- 241000588777 Providencia rettgeri Species 0.000 abstract description 7
- 241000894006 Bacteria Species 0.000 abstract description 6
- 241000588724 Escherichia coli Species 0.000 abstract description 5
- 241000588919 Citrobacter freundii Species 0.000 abstract description 4
- 241000607715 Serratia marcescens Species 0.000 abstract description 4
- 241000588697 Enterobacter cloacae Species 0.000 abstract description 3
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 258
- 239000000203 mixture Substances 0.000 description 127
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 110
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 96
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 93
- 229940093499 ethyl acetate Drugs 0.000 description 86
- 235000019439 ethyl acetate Nutrition 0.000 description 86
- 239000000047 product Substances 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 59
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 55
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 52
- 238000001816 cooling Methods 0.000 description 50
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 48
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 48
- 239000002904 solvent Substances 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 43
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 36
- 239000011734 sodium Substances 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
- 239000007864 aqueous solution Substances 0.000 description 34
- 239000011541 reaction mixture Substances 0.000 description 33
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 32
- 239000010410 layer Substances 0.000 description 32
- 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 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 29
- 238000001914 filtration Methods 0.000 description 29
- 229910052708 sodium Inorganic materials 0.000 description 29
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 28
- 239000000843 powder Substances 0.000 description 28
- 239000013078 crystal Substances 0.000 description 27
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 27
- 235000017557 sodium bicarbonate Nutrition 0.000 description 26
- 239000002244 precipitate Substances 0.000 description 25
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- HASOOENYFDJEAK-UHFFFAOYSA-N ethyl 2-methoxyimino-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=NOC HASOOENYFDJEAK-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- HQOQSFITXGQQDM-SSDOTTSWSA-N methyl (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound COC(=O)C1=CCS[C@@H]2CC(=O)N12 HQOQSFITXGQQDM-SSDOTTSWSA-N 0.000 description 1
- VYMCJSNANDEONB-UHFFFAOYSA-N methyl N-(pyridine-4-carbonyl)carbamate Chemical compound COC(=O)NC(=O)C1=CC=NC=C1 VYMCJSNANDEONB-UHFFFAOYSA-N 0.000 description 1
- 125000006405 methylpyridazinyl group Chemical group 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 235000014786 phosphorus Nutrition 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- MYMGMVJBMZEJFP-GILAUPEISA-M sodium;(6r)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].C1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)C([O-])=O)NC(=O)CC1=CSC(N)=N1 MYMGMVJBMZEJFP-GILAUPEISA-M 0.000 description 1
- MKPLRAFOAAEKEG-UHFFFAOYSA-M sodium;oxolane;acetate Chemical compound [Na+].CC([O-])=O.C1CCOC1 MKPLRAFOAAEKEG-UHFFFAOYSA-M 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP42885/1976 | 1976-04-14 | ||
| JP4288576A JPS52125188A (en) | 1976-04-14 | 1976-04-14 | Cephalosporin derivatives and their preparation |
| JP51108102A JPS597717B2 (ja) | 1976-09-08 | 1976-09-08 | セフアロスポリン誘導体およびその製造法 |
| JP108102/1976 | 1976-09-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1308708C true CA1308708C (en) | 1992-10-13 |
Family
ID=26382633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000276067A Expired - Lifetime CA1308708C (en) | 1976-04-14 | 1977-04-13 | Cephalosporins |
Country Status (23)
| Country | Link |
|---|---|
| US (4) | US4520194A (en, 2012) |
| AT (1) | AT351164B (en, 2012) |
| AU (1) | AU508449B2 (en, 2012) |
| BG (1) | BG60438B2 (en, 2012) |
| CA (1) | CA1308708C (en, 2012) |
| CH (4) | CH629499A5 (en, 2012) |
| DE (2) | DE2760484C2 (en, 2012) |
| DK (1) | DK158671C (en, 2012) |
| ES (1) | ES457751A1 (en, 2012) |
| FI (1) | FI66618C (en, 2012) |
| FR (1) | FR2348218A1 (en, 2012) |
| GB (1) | GB1581854A (en, 2012) |
| GR (1) | GR63088B (en, 2012) |
| HK (1) | HK27684A (en, 2012) |
| HU (1) | HU182052B (en, 2012) |
| MX (1) | MX4879E (en, 2012) |
| MY (1) | MY8500265A (en, 2012) |
| NL (1) | NL7704057A (en, 2012) |
| NO (1) | NO771285L (en, 2012) |
| PH (2) | PH23284A (en, 2012) |
| PT (1) | PT66435B (en, 2012) |
| SE (2) | SE464580B (en, 2012) |
| SG (1) | SG76183G (en, 2012) |
Families Citing this family (111)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4668783A (en) * | 1974-12-19 | 1987-05-26 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido cephalosporin compounds |
| US4376203A (en) * | 1976-01-23 | 1983-03-08 | Roussell Uclaf | Novel 3-acetoxymethyl-7-(iminoacetamido)-cephalosporanic acid derivatives |
| DE2760123C2 (de) * | 1976-01-23 | 1986-04-30 | Roussel-Uclaf, Paris | 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
| IE44888B1 (en) * | 1976-03-09 | 1982-05-05 | Fujisawa Pharmaceutical Co | 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation theroef |
| FR2345153A1 (fr) * | 1976-03-25 | 1977-10-21 | Roussel Uclaf | Nouvelles alcoyloximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| BE878433A (fr) * | 1978-08-31 | 1980-02-25 | Fujisawa Pharmaceutical Co | Procede de preparation de derives d'acide 3-cephem-4-carboxylique 3,7-disubstitue, nouveaux produits ainsi obtenus et leur utilisation pour leur activite antibacterienne |
| BE878514A (fr) * | 1978-09-04 | 1980-02-29 | Fujisawa Pharmaceutical Co | Procede de preparation de composes d'acide 3-cephem-4-carboxylique a disubstitution en positions 3 et 7, nouveaux produits ainsi obtenus et leur utilisation pour leur activite antibacterienne |
| US4431643A (en) * | 1976-04-12 | 1984-02-14 | Fujisawa Pharmaceutical Co., Ltd. | Syn-isomer of 3-substituted-7-[2-cyclopentyloxyimino-2-(2-aminothiazol-4-yl)-acetamido]-3 |
| FR2367756B1 (fr) * | 1976-04-12 | 1985-07-05 | Fujisawa Pharmaceutical Co | Derives 2-alcoxyamino-2-(amino-1,3-thiazolyl) acetiques et leur utilisation |
| DK162391C (da) * | 1976-04-12 | 1992-03-09 | Fujisawa Pharmaceutical Co | Analogifremgangsmaade til fremstilling af syn-isomerer af 3,7-disubstituerede 3-cephem-4-carboxylsyreforbindelser |
| FR2381053A1 (fr) * | 1977-02-18 | 1978-09-15 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-thiadiazolyl thiomethyl 7-aminothiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| JPS53103493A (en) | 1977-02-18 | 1978-09-08 | Takeda Chem Ind Ltd | Cephalosporin derivatives and process for their preparation |
| DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
| DE2857696C2 (de) * | 1977-07-23 | 1984-08-30 | Toyama Chemical Co. Ltd., Tokio / Tokyo | Cephalosporine |
| FR2410655A1 (fr) * | 1977-12-05 | 1979-06-29 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-substitue 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| US4200745A (en) * | 1977-12-20 | 1980-04-29 | Eli Lilly And Company | 7[2-(2-Aminothiazol-4-yl)-2-alkoxyimino]acetamido 3[4-alkyl-5-oxo-6-hydroxy-3,4 dihydro 1,2,4-triazin 3-yl]thio methyl cephalosporins |
| JPS5498795A (en) * | 1978-01-13 | 1979-08-03 | Takeda Chem Ind Ltd | Cephalosporin derivative and its preparation |
| FR2387235A1 (fr) * | 1978-01-23 | 1978-11-10 | Fujisawa Pharmaceutical Co | Procede de preparation de composes d'acide 3,7-disubstitue-3-cephem-4-carboxylique et nouveaux produits ainsi obtenus, ayant une forte activite antibacterienne |
| FR2422668A1 (fr) * | 1978-04-14 | 1979-11-09 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-azidomethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| MC1259A1 (fr) | 1978-05-30 | 1980-01-14 | Hoffmann La Roche | Derives acyles |
| CH641468A5 (de) | 1978-05-30 | 1984-02-29 | Hoffmann La Roche | Cephemderivate. |
| JPS54160392A (en) * | 1978-06-02 | 1979-12-19 | Takeda Chem Ind Ltd | Cephalosporin derivative and its preparation |
| US4341775A (en) * | 1978-09-11 | 1982-07-27 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| DE2945248A1 (de) * | 1978-11-13 | 1980-05-22 | Fujisawa Pharmaceutical Co | Cephem-verbindungen, verfahren zu ihrer herstellung und sie enthaltende antibakterielle pharmazeutische mittel |
| FR2448543A1 (fr) * | 1979-02-09 | 1980-09-05 | Roussel Uclaf | Nouvelles oximes o-substituees par un radical comportant un ammonium quaternaire et derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| US4331666A (en) * | 1979-05-11 | 1982-05-25 | Farmitalia Carlo Erba S.P.A. | 3-[(8-Carboxy-6-tetrazolo[1,5-b]pyridazinyl)-thiomethyl]-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-3-cephem-4-carboxylic acid |
| EP0021688B1 (en) * | 1979-06-07 | 1983-07-13 | Yamanouchi Pharmaceutical Co., Ltd. | 7-(thiazolylpropionamido) cephalosporins, their preparation, and pharmaceutical compositions containing them |
| US4252951A (en) | 1979-10-09 | 1981-02-24 | Eli Lilly And Company | Isolation of syn-7-(2-amino-4-thiazolyl)-(methoxyimino)acetamido-3-acetoxymethyl-3-cephem-4-carboxylic acid |
| US4420477A (en) * | 1979-11-30 | 1983-12-13 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| EP0076528B1 (fr) * | 1980-02-18 | 1990-05-23 | Roussel-Uclaf | Nouvelles oximes dérivées de l'acide 3-alkyloxy ou 3-alkylthiométhyl 7-amino thiazolylacétamido céphalosporanique et leur préparation |
| FR2476087A1 (fr) * | 1980-02-18 | 1981-08-21 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkyl-thiomethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| CH642957A5 (de) | 1980-02-18 | 1984-05-15 | Lonza Ag | Verfahren zur herstellung von (2-aminothiazol-4-yl)-essigsaeure-hydrochlorid. |
| DE3006888A1 (de) * | 1980-02-23 | 1981-09-10 | Hoechst Ag, 6000 Frankfurt | Cephalosporinderivate und verfahren zu ihrer herstellung |
| CA1154009A (en) * | 1980-03-25 | 1983-09-20 | Roland Reiner | Cephalosporin derivatives |
| IL63207A (en) * | 1980-07-24 | 1985-09-29 | Lonza Ag | Process for the preparation of 2-(2-aminothiazole-4-yl)-2-(syn)-methoxyiminoacetic acid esters |
| US4399132A (en) * | 1980-08-11 | 1983-08-16 | American Cyanamid Company | 7-Beta-[alpha-syn-methoxyimino-alpha-(2-aminothiazol-4-yl)-acetamido]-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-3-cephem-4-carboxylic acid and C1 -C6 alkyl derivatives thereof |
| US4443444A (en) * | 1980-08-11 | 1984-04-17 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| EP0046964B1 (en) * | 1980-08-29 | 1986-08-20 | Fujisawa Pharmaceutical Co., Ltd. | New cephem compounds and processes for preparation thereof |
| NZ198350A (en) * | 1980-09-25 | 1985-02-28 | Toyama Chemical Co Ltd | Cephalosporins and intermediates;pharmaceutical compositions |
| US4486425A (en) * | 1980-09-30 | 1984-12-04 | Sankyo Company Limited | 7-[2-(2-Aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylates |
| JPS5759894A (en) * | 1980-09-30 | 1982-04-10 | Sankyo Co Ltd | Cephalosporin for oral administration |
| US4367228A (en) * | 1980-10-29 | 1983-01-04 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compound and composition |
| US4431642A (en) * | 1980-12-01 | 1984-02-14 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| US4427677A (en) * | 1980-12-31 | 1984-01-24 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| FR2499995A1 (fr) * | 1981-02-13 | 1982-08-20 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkylthiomethyl 7-amino thiazolylacetamido cephalosporanique, leur preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus. |
| US4336253A (en) * | 1981-03-11 | 1982-06-22 | Eli Lilly And Company | Cephalosporin antibiotics |
| DE3118732A1 (de) * | 1981-05-12 | 1982-12-02 | Hoechst Ag, 6000 Frankfurt | Cephalosporinderivate und verfahren zu ihrer herstellung |
| FR2508458A1 (fr) * | 1981-06-29 | 1982-12-31 | Sandoz Sa | Nouveaux derives de l'acide cephalosporanique, leur preparation et leur application comme medicaments |
| US4577014A (en) * | 1981-09-08 | 1986-03-18 | Eli Lilly And Company | Thieno and furopyridinium-substituted cephalosporins |
| US4406898A (en) * | 1981-09-08 | 1983-09-27 | Eli Lilly And Company | Oxazole and oxadiazole cephalosporins |
| PL238158A1 (en) * | 1981-09-08 | 1984-11-19 | Lilly Co Eli | Method of obtaining new cephalosporin derivatives |
| US4396620A (en) * | 1981-09-08 | 1983-08-02 | Eli Lilly And Company | Cephalosporin quinolinium betaines |
| JPS5859991A (ja) * | 1981-09-14 | 1983-04-09 | Fujisawa Pharmaceut Co Ltd | 新規セフェム化合物 |
| EP0075110A3 (de) * | 1981-09-23 | 1984-12-12 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Cephalosporinderivate, Verfahren zu deren Herstellung und Zwischenprodukte dafür sowie entsprechende pharmazeutische Präparate |
| EP0075104A3 (de) * | 1981-09-23 | 1984-11-28 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Cephalosporinderivate, Verfahren zu deren Herstellung und Zwischenprodukte dafür sowie entsprechende pharmazeutische Präparate |
| EP0075095A3 (de) * | 1981-09-23 | 1984-10-17 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Cephalosporinderivate, Verfahren zu deren Herstellung und Zwischenprodukte dafür sowie entsprechende pharmazeutische Präparate |
| US4388316A (en) * | 1981-10-02 | 1983-06-14 | Eli Lilly And Company | Amino-substituted oxazole, oxadiazole and isoxazole-substituted cephalosporins |
| US4402955A (en) * | 1981-10-02 | 1983-09-06 | Eli Lilly And Company | Dioximino cephalosporin antibiotics |
| US4450270A (en) * | 1981-10-02 | 1984-05-22 | Eli Lilly And Company | Dioximino cephalosporin antibiotics |
| US4401668A (en) * | 1981-10-02 | 1983-08-30 | Eli Lilly And Company | Pyrazinium substituted cephalosporins |
| US4400503A (en) * | 1981-10-30 | 1983-08-23 | Eli Lilly And Company | Purification of syn-7-[[(2-amino-4-thiazolyl)(methoxyimino) acetyl]amino]-3-methyl-3-cephem-4-carboxylic acid |
| US4594417A (en) * | 1981-10-30 | 1986-06-10 | Eli Lilly Company | Crystalline antibiotic salt |
| US4576938A (en) * | 1981-12-08 | 1986-03-18 | Tanabe Seiyaku Co., Ltd. | Cephalosporin compound and process for preparing the same |
| US4501739A (en) * | 1982-01-19 | 1985-02-26 | Eli Lilly And Company | Thieno and furopyridinium-substituted cephalosporins |
| CA1213882A (en) * | 1982-03-04 | 1986-11-12 | Jun Okumura | Cephalosporins |
| US4406899A (en) * | 1982-03-04 | 1983-09-27 | Bristol-Myers Company | Cephalosporins |
| US4457929A (en) * | 1982-03-29 | 1984-07-03 | Bristol-Myers Company | 3-Quaternary ammonium methyl)-substituted cephalosporin derivatives |
| US4500526A (en) * | 1982-06-28 | 1985-02-19 | Bristol-Myers Company | Cephalosporin derivatives |
| ATE30724T1 (de) * | 1982-06-28 | 1987-11-15 | Bristol Myers Co | Cephalosporinderivate, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen die sie enthalten. |
| LU84887A1 (fr) * | 1982-06-30 | 1984-03-07 | Glaxo Group Ltd | Antibiotiques de la nature des cephalosporines et leur procede de preparation |
| US4616081A (en) * | 1982-07-07 | 1986-10-07 | Asahi Kasei Kogyo Kabushiki Kaisha | Cephalosporin compounds |
| IE55406B1 (en) * | 1982-08-07 | 1990-09-12 | Tanabe Seiyaku Co | Novel cephalosporin compounds and preparation thereof |
| DE3247614A1 (de) * | 1982-12-23 | 1984-07-05 | Hoechst Ag, 6230 Frankfurt | Cephalosporinderivate und verfahren zu ihrer herstellung |
| US4681877A (en) * | 1982-12-24 | 1987-07-21 | Kureha Kagaku Kogyo Kabushiki Kaisha | Pivaloyloxymethyl 7-β-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-(2-amino-1,3-thiadiazolyl-5-thiomethyl)-3-cepheme-4-carboxylate and pharmaceutical composition containing the same |
| US4525473A (en) * | 1983-03-30 | 1985-06-25 | Bristol-Myers Company | Cephalosporins |
| EP0132501A3 (en) * | 1983-03-31 | 1985-09-18 | Ajinomoto Co., Inc. | Cephalosporin derivatives, their preparation and pharmaceutical compositions |
| FR2546520B1 (fr) * | 1983-05-27 | 1985-08-30 | Sanofi Sa | Nouveaux composes antibiotiques derives des cephalosporines |
| GB8413152D0 (en) * | 1983-06-03 | 1984-06-27 | Ici Pharma | Cephalosporin derivatives |
| JPS60178891A (ja) * | 1984-02-24 | 1985-09-12 | Kureha Chem Ind Co Ltd | セファロスポリン誘導体及び該誘導体を含有する医薬 |
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| US5872249A (en) * | 1995-09-01 | 1999-02-16 | Korea Institute Of Science And Technology | 3-ammoniopropenyl cephalosporin compounds as antibacterial agents and process for preparing the same |
| IT1286494B1 (it) * | 1996-11-19 | 1998-07-15 | Hichem Pharma S P A | Procedimento per la preparazione di derivati cefalosporanici |
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| CN111072515B (zh) * | 2019-12-25 | 2023-02-28 | 普洛药业股份有限公司 | 一种连续合成氨噻肟酸中间体的方法 |
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|---|---|---|---|---|
| CA996929A (en) * | 1971-04-05 | 1976-09-14 | Kohzi Nakano | Acyloxyalkyl ester derivatives of penicillin |
| US4033950A (en) * | 1971-05-14 | 1977-07-05 | Glaxo Laboratories Limited | 3-Hydroxymethyl-7β-(2-alkoxy-or benzyloxyimino-2-arylacetamido)ceph-3-em-4-carboxylic acids and salts thereof |
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| GB1425933A (en) * | 1972-03-13 | 1976-02-25 | Astra Laekemedel Ab | Cephalosporins |
| US4092476A (en) * | 1974-02-21 | 1978-05-30 | Beecham Group Limited | Phthalidyl esters of 7-[(α amino, 2 substituted acetamido)-3-(heterocyclic-thio methyl)]cephalosporins |
| CH606001A5 (en, 2012) * | 1974-05-13 | 1978-10-13 | Ciba Geigy Ag | |
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| FR2346014A1 (fr) * | 1976-01-23 | 1977-10-28 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| SE440655B (sv) * | 1976-01-23 | 1985-08-12 | Roussel Uclaf | Sett att framstella nya oximderivat av 7-amino-tiazolyl-acetamido-cefalosporansyra |
| US4202893A (en) * | 1976-03-25 | 1980-05-13 | Roussel Uclaf | Alkyloximes of 7-amino-thiazolyl-acetamido-cephalosporanic acids |
| FR2345153A1 (fr) * | 1976-03-25 | 1977-10-21 | Roussel Uclaf | Nouvelles alcoyloximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
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| US4066762A (en) * | 1976-07-12 | 1978-01-03 | Smithkline Corporation | Derivatives of 7-(2-substituted-2-hydroxyiminoacetamido)-3-(1-substituted tetrazol-5-ylthiomethyl-3-cephem-4-carboxylic acid |
-
1977
- 1977-04-06 DE DE2760484A patent/DE2760484C2/de not_active Expired - Lifetime
- 1977-04-06 DE DE19772715385 patent/DE2715385A1/de active Granted
- 1977-04-06 GR GR53169A patent/GR63088B/el unknown
- 1977-04-12 PH PH19652A patent/PH23284A/en unknown
- 1977-04-13 NL NL7704057A patent/NL7704057A/xx active Search and Examination
- 1977-04-13 NO NO771285A patent/NO771285L/no unknown
- 1977-04-13 DK DK164177A patent/DK158671C/da not_active IP Right Cessation
- 1977-04-13 ES ES457751A patent/ES457751A1/es not_active Expired
- 1977-04-13 CA CA000276067A patent/CA1308708C/en not_active Expired - Lifetime
- 1977-04-13 PT PT66435A patent/PT66435B/pt unknown
- 1977-04-13 AU AU24219/77A patent/AU508449B2/en not_active Expired
- 1977-04-13 AT AT256577A patent/AT351164B/de not_active IP Right Cessation
- 1977-04-13 FR FR7711134A patent/FR2348218A1/fr active Granted
- 1977-04-13 HU HU77TA1437A patent/HU182052B/hu unknown
- 1977-04-13 SE SE7704233A patent/SE464580B/xx not_active IP Right Cessation
- 1977-04-14 CH CH465477A patent/CH629499A5/de not_active IP Right Cessation
- 1977-04-14 MX MX775637U patent/MX4879E/es unknown
- 1977-04-14 GB GB15527/77A patent/GB1581854A/en not_active Expired
- 1977-04-14 FI FI771176A patent/FI66618C/fi not_active IP Right Cessation
- 1977-04-14 CH CH3959/82A patent/CH650503A5/de not_active IP Right Cessation
-
1978
- 1978-07-06 US US05/922,423 patent/US4520194A/en not_active Expired - Lifetime
-
1979
- 1979-08-08 US US06/064,743 patent/US4278671A/en not_active Expired - Lifetime
-
1981
- 1981-07-30 CH CH495581A patent/CH630635A5/de not_active IP Right Cessation
- 1981-07-30 CH CH495681A patent/CH630632A5/de not_active IP Right Cessation
-
1982
- 1982-09-29 US US06/428,032 patent/US4510138A/en not_active Expired - Lifetime
-
1983
- 1983-12-02 SG SG761/83A patent/SG76183G/en unknown
- 1983-12-05 SE SE8306702A patent/SE453086B/sv not_active IP Right Cessation
-
1984
- 1984-01-20 PH PH30133A patent/PH22747A/en unknown
- 1984-03-22 HK HK276/84A patent/HK27684A/xx unknown
- 1984-10-04 US US06/657,778 patent/US4680390A/en not_active Expired - Lifetime
-
1985
- 1985-12-30 MY MY265/85A patent/MY8500265A/xx unknown
-
1994
- 1994-02-11 BG BG098462A patent/BG60438B2/bg unknown
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