DE3019445A1 - Neue 3-vinyl-cephalosporine und verfahren zu deren herstellung - Google Patents
Neue 3-vinyl-cephalosporine und verfahren zu deren herstellungInfo
- Publication number
- DE3019445A1 DE3019445A1 DE19803019445 DE3019445A DE3019445A1 DE 3019445 A1 DE3019445 A1 DE 3019445A1 DE 19803019445 DE19803019445 DE 19803019445 DE 3019445 A DE3019445 A DE 3019445A DE 3019445 A1 DE3019445 A1 DE 3019445A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- general formula
- oxo
- oct
- thia
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 130
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- -1 cyanomethyl radical Chemical class 0.000 claims description 608
- 239000000203 mixture Substances 0.000 claims description 355
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 claims description 175
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 173
- 150000001875 compounds Chemical class 0.000 claims description 171
- 150000003254 radicals Chemical class 0.000 claims description 122
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 69
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 51
- 125000006239 protecting group Chemical group 0.000 claims description 50
- 239000002253 acid Substances 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 229940124587 cephalosporin Drugs 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 19
- 229930186147 Cephalosporin Natural products 0.000 claims description 18
- 150000001780 cephalosporins Chemical class 0.000 claims description 16
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 229920002554 vinyl polymer Polymers 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 150000003462 sulfoxides Chemical class 0.000 claims description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 12
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 150000001412 amines Chemical group 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 7
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- RZSIFLMFZCYCID-UHFFFAOYSA-N bicyclo[4.2.0]oct-4-ene Chemical compound C1=CCCC2CCC21 RZSIFLMFZCYCID-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000005462 imide group Chemical group 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- OHSJPLSEQNCRLW-UHFFFAOYSA-N triphenylmethyl radical Chemical compound C1=CC=CC=C1[C](C=1C=CC=CC=1)C1=CC=CC=C1 OHSJPLSEQNCRLW-UHFFFAOYSA-N 0.000 claims description 4
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 3
- 125000006502 nitrobenzyl group Chemical group 0.000 claims description 3
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 434
- 239000000243 solution Substances 0.000 description 385
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 306
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 159
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 149
- 229940093499 ethyl acetate Drugs 0.000 description 145
- 235000019439 ethyl acetate Nutrition 0.000 description 142
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 134
- 238000002329 infrared spectrum Methods 0.000 description 133
- 238000001228 spectrum Methods 0.000 description 123
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 121
- 238000005481 NMR spectroscopy Methods 0.000 description 119
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 118
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 108
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 104
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 102
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 87
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 81
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 79
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 75
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 72
- 229910052938 sodium sulfate Inorganic materials 0.000 description 72
- 235000011152 sodium sulphate Nutrition 0.000 description 72
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 70
- 239000000047 product Substances 0.000 description 69
- 239000007787 solid Substances 0.000 description 66
- 239000002904 solvent Substances 0.000 description 64
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 63
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 59
- 235000019253 formic acid Nutrition 0.000 description 52
- 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 51
- 239000000843 powder Substances 0.000 description 51
- 229910002027 silica gel Inorganic materials 0.000 description 50
- 239000000741 silica gel Substances 0.000 description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- 239000012153 distilled water Substances 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 48
- 239000000377 silicon dioxide Substances 0.000 description 48
- 238000003756 stirring Methods 0.000 description 47
- 235000012239 silicon dioxide Nutrition 0.000 description 45
- 229910052757 nitrogen Inorganic materials 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 39
- 235000019341 magnesium sulphate Nutrition 0.000 description 39
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 39
- 239000000499 gel Substances 0.000 description 38
- 239000012074 organic phase Substances 0.000 description 38
- 235000017557 sodium bicarbonate Nutrition 0.000 description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 37
- 238000001035 drying Methods 0.000 description 35
- 238000010898 silica gel chromatography Methods 0.000 description 34
- 238000001914 filtration Methods 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
- 238000010992 reflux Methods 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 27
- 229920006395 saturated elastomer Polymers 0.000 description 27
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 25
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 25
- 229940113088 dimethylacetamide Drugs 0.000 description 24
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- 230000009471 action Effects 0.000 description 22
- 230000009467 reduction Effects 0.000 description 20
- 239000011780 sodium chloride Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
- 239000003480 eluent Substances 0.000 description 17
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 17
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 16
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 16
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 16
- 239000008346 aqueous phase Substances 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- 239000003513 alkali Substances 0.000 description 13
- 125000003282 alkyl amino group Chemical group 0.000 description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 13
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 13
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 12
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 11
- 159000000000 sodium salts Chemical class 0.000 description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 125000004442 acylamino group Chemical group 0.000 description 10
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 10
- 150000002923 oximes Chemical class 0.000 description 10
- 150000003573 thiols Chemical class 0.000 description 10
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- 239000003610 charcoal Substances 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 235000008504 concentrate Nutrition 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Chemical class 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- YCTDZYMMFQCTEO-FNORWQNLSA-N (E)-3-octene Chemical class CCCC\C=C\CC YCTDZYMMFQCTEO-FNORWQNLSA-N 0.000 description 7
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 7
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- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- JROJIDFJTHBZBD-UHFFFAOYSA-N n,n-dimethoxypropan-2-amine Chemical compound CON(OC)C(C)C JROJIDFJTHBZBD-UHFFFAOYSA-N 0.000 description 1
- REPVNSJSTLRQEQ-UHFFFAOYSA-N n,n-dimethylacetamide;n,n-dimethylformamide Chemical compound CN(C)C=O.CN(C)C(C)=O REPVNSJSTLRQEQ-UHFFFAOYSA-N 0.000 description 1
- HYGXISCUUFVGQW-UHFFFAOYSA-N n,n-dimethylformamide;1,4-dioxane Chemical compound CN(C)C=O.C1COCCO1 HYGXISCUUFVGQW-UHFFFAOYSA-N 0.000 description 1
- CZFNISFYDPIDNM-UHFFFAOYSA-N n,n-dimethylformamide;oxolane Chemical compound CN(C)C=O.C1CCOC1 CZFNISFYDPIDNM-UHFFFAOYSA-N 0.000 description 1
- RUUZGIXULFRUFD-UHFFFAOYSA-N n-[2-(aminocarbamothioylamino)ethyl]acetamide Chemical compound CC(=O)NCCNC(=S)NN RUUZGIXULFRUFD-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- ZAAGIQBAUWRDFA-UHFFFAOYSA-N s-(5-methyl-1,3,4-thiadiazol-2-yl) 2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]ethanethioate Chemical compound C=1SC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C(=NOC)C(=O)SC1=NN=C(C)S1 ZAAGIQBAUWRDFA-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000003420 transacetalization reaction Methods 0.000 description 1
- 238000005891 transamination reaction Methods 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with 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
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- 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
- 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
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7913097A FR2457297A1 (fr) | 1979-05-23 | 1979-05-23 | Nouvelles vinyl-3 cephalosporines, et leur preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3019445A1 true DE3019445A1 (de) | 1980-12-04 |
Family
ID=9225763
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803019445 Withdrawn DE3019445A1 (de) | 1979-05-23 | 1980-05-21 | Neue 3-vinyl-cephalosporine und verfahren zu deren herstellung |
| DE19803019430 Withdrawn DE3019430A1 (de) | 1979-05-23 | 1980-05-21 | Neue cephalosporine und ihre herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803019430 Withdrawn DE3019430A1 (de) | 1979-05-23 | 1980-05-21 | Neue cephalosporine und ihre herstellung |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US4365062A (enExample) |
| JP (2) | JPS55154978A (enExample) |
| AT (2) | AT370737B (enExample) |
| AU (2) | AU532884B2 (enExample) |
| BE (2) | BE883418A (enExample) |
| CA (2) | CA1148141A (enExample) |
| CH (2) | CH645380A5 (enExample) |
| CS (1) | CS235508B2 (enExample) |
| DD (2) | DD151064A5 (enExample) |
| DE (2) | DE3019445A1 (enExample) |
| DK (2) | DK222280A (enExample) |
| ES (4) | ES491688A0 (enExample) |
| FI (2) | FI801642A7 (enExample) |
| FR (1) | FR2457297A1 (enExample) |
| GB (2) | GB2051061B (enExample) |
| GR (2) | GR68436B (enExample) |
| HU (2) | HU184759B (enExample) |
| IE (2) | IE49813B1 (enExample) |
| IL (2) | IL60141A (enExample) |
| IT (2) | IT1140972B (enExample) |
| LU (2) | LU82476A1 (enExample) |
| NL (2) | NL8003010A (enExample) |
| NO (2) | NO801503L (enExample) |
| NZ (2) | NZ193800A (enExample) |
| PH (2) | PH15916A (enExample) |
| PL (3) | PL126671B1 (enExample) |
| PT (2) | PT71277A (enExample) |
| SE (2) | SE8003823L (enExample) |
| SU (4) | SU927118A3 (enExample) |
| YU (3) | YU136980A (enExample) |
| ZA (2) | ZA803035B (enExample) |
| ZW (1) | ZW12380A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4520022A (en) * | 1983-01-28 | 1985-05-28 | Bristol-Myers Company | Substituted vinyl cephalosporins |
| US4591641A (en) * | 1983-01-28 | 1986-05-27 | Bristol-Myers Company | Substituted vinyl cephalosporins |
| WO2003072582A1 (en) * | 2002-02-28 | 2003-09-04 | Lg Life Sciences Ltd. | Novel cephalosporin compounds and process for preparing the same |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2494276A2 (fr) * | 1980-11-20 | 1982-05-21 | Rhone Poulenc Ind | Nouvelles vinyl-3 cephalosporines, et leur preparation |
| FR2511372A1 (fr) * | 1981-08-17 | 1983-02-18 | Rhone Poulenc Sante | Nouveaux derives de la cephalosporine et leur preparation |
| FR2511376A1 (fr) * | 1981-08-17 | 1983-02-18 | Rhone Poulenc Sante | Nouveaux derives de la cephalosporine et leur prepration |
| FR2531712A1 (fr) * | 1982-08-13 | 1984-02-17 | Rhone Poulenc Sante | Nouveaux derives de la cephalosporine et leur preparation |
| US4609730A (en) * | 1982-11-22 | 1986-09-02 | Fujisawa Pharmaceutical Co., Ltd. | 7-[substituted imino-2-(2-aminothiazol-4-yl)-acetamido]-3(2,2-dihalovinyl or ethynyl)-3-cephem-4-carboxylic acid (syn isomers), having antimicrobial activities |
| JPS604883U (ja) * | 1983-06-24 | 1985-01-14 | 松下冷機株式会社 | 冷蔵庫等の冷却装置 |
| US4708955A (en) * | 1985-06-24 | 1987-11-24 | Bristol-Myers Company | 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof |
| US4874856A (en) * | 1985-06-24 | 1989-10-17 | Bristol-Myers Company | 3-(substituted)propenyl-7-(aminothiazolylacetamido) ceph-3-em-4-carboxylic acids and esters thereof |
| MY127641A (en) * | 1995-10-12 | 2006-12-29 | Essential Therapeutics Inc | Cephalosporin antibiotics |
| US6025352A (en) * | 1997-09-29 | 2000-02-15 | Microcide Pharmaceuticals, Inc. | Cephalosporin antibiotics |
| US6030965A (en) * | 1997-09-30 | 2000-02-29 | Microcide Pharmaceuticals, Inc. | Cephalosporin antibiotics |
| JP5733856B2 (ja) | 2007-10-09 | 2015-06-10 | ソファーミア，インコーポレイテッド | 広帯域β−ラクタマーゼ阻害薬 |
| CA2905240A1 (en) | 2013-03-12 | 2014-10-09 | Gladius Pharmaceuticals Coproration | Derivatized 3-styryl-cephalosporins |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3769277A (en) * | 1970-01-23 | 1973-10-30 | Glaxo Lab Ltd | Preparation of delta3-4 carboxy cephalosporins having a 3-vinyl or substituted 3-vinyl group |
| US3823139A (en) * | 1970-03-26 | 1974-07-09 | Glaxo Lab Ltd | Cephalosporins having a ypsilon-carbonyl group at position-3 |
| US3674784A (en) * | 1970-07-27 | 1972-07-04 | Lilly Co Eli | 3-formyl cephalosporin sulfoxides |
| US4065620A (en) * | 1971-06-14 | 1977-12-27 | Eli Lilly And Company | 3-(Substituted) vinyl cephalosporins |
| US4144393A (en) * | 1973-12-21 | 1979-03-13 | Glaxo Laboratories Limited | 3-Acetoxymethyl cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyiminoarylacetamido group |
| DE2637176A1 (de) | 1975-08-22 | 1977-03-03 | Ciba Geigy Ag | Carbonylmethylderivate |
| JPS5285185A (en) * | 1976-01-05 | 1977-07-15 | Teijin Ltd | Preparation of 7-acylaminocephalosporanic acids |
| JPS5289694A (en) * | 1976-01-23 | 1977-07-27 | Asahi Chem Ind Co Ltd | Novel cephalosporins |
| US4094978A (en) * | 1976-07-29 | 1978-06-13 | Syntex (U.S.A.) Inc. | 3-propenyl derivatives of cephalosporin, compositions and their use |
| US4255423A (en) * | 1977-07-27 | 1981-03-10 | Merck & Co., Inc. | Cephalosporin compounds |
| EP0015240A1 (de) * | 1979-02-16 | 1980-09-03 | Ciba-Geigy Ag | Azacyclyl (thio) ureidoacetyl-Verbindungen und Verfahren zu ihrer Herstellung |
-
1979
- 1979-05-23 FR FR7913097A patent/FR2457297A1/fr active Granted
-
1980
- 1980-05-21 BE BE0/200709A patent/BE883418A/fr not_active IP Right Cessation
- 1980-05-21 US US06/152,153 patent/US4365062A/en not_active Expired - Lifetime
- 1980-05-21 CS CS803544A patent/CS235508B2/cs unknown
- 1980-05-21 YU YU01369/80A patent/YU136980A/xx unknown
- 1980-05-21 LU LU82476A patent/LU82476A1/fr unknown
- 1980-05-21 CA CA000352346A patent/CA1148141A/fr not_active Expired
- 1980-05-21 FI FI801642A patent/FI801642A7/fi not_active Application Discontinuation
- 1980-05-21 BE BE0/200708A patent/BE883417A/fr not_active IP Right Cessation
- 1980-05-21 DK DK222280A patent/DK222280A/da not_active Application Discontinuation
- 1980-05-21 AT AT0271180A patent/AT370737B/de not_active IP Right Cessation
- 1980-05-21 DK DK223180A patent/DK223180A/da not_active Application Discontinuation
- 1980-05-21 HU HU801279A patent/HU184759B/hu unknown
- 1980-05-21 CH CH399180A patent/CH645380A5/fr not_active IP Right Cessation
- 1980-05-21 US US06/152,084 patent/US4307230A/en not_active Expired - Lifetime
- 1980-05-21 GB GB8016726A patent/GB2051061B/en not_active Expired
- 1980-05-21 SU SU802928400A patent/SU927118A3/ru active
- 1980-05-21 YU YU01370/80A patent/YU137080A/xx unknown
- 1980-05-21 DD DD80221267A patent/DD151064A5/de unknown
- 1980-05-21 AT AT0271080A patent/AT368509B/de not_active IP Right Cessation
- 1980-05-21 CH CH3990/80A patent/CH650000A5/fr not_active IP Right Cessation
- 1980-05-21 DE DE19803019445 patent/DE3019445A1/de not_active Withdrawn
- 1980-05-21 NZ NZ193800A patent/NZ193800A/xx unknown
- 1980-05-21 GR GR62017A patent/GR68436B/el unknown
- 1980-05-21 PL PL1980229959A patent/PL126671B1/pl unknown
- 1980-05-21 IT IT22241/80A patent/IT1140972B/it active
- 1980-05-21 IT IT22242/80A patent/IT1140973B/it active
- 1980-05-21 GB GB8016725A patent/GB2052488B/en not_active Expired
- 1980-05-21 PT PT71277A patent/PT71277A/pt unknown
- 1980-05-21 ES ES491688A patent/ES491688A0/es active Granted
- 1980-05-21 ZA ZA00803035A patent/ZA803035B/xx unknown
- 1980-05-21 IE IE1060/80A patent/IE49813B1/en unknown
- 1980-05-21 DE DE19803019430 patent/DE3019430A1/de not_active Withdrawn
- 1980-05-21 GR GR62016A patent/GR68428B/el unknown
- 1980-05-21 AU AU58593/80A patent/AU532884B2/en not_active Ceased
- 1980-05-21 ES ES491689A patent/ES491689A0/es active Granted
- 1980-05-21 NZ NZ193801A patent/NZ193801A/xx unknown
- 1980-05-21 SE SE8003823A patent/SE8003823L/xx not_active Application Discontinuation
- 1980-05-21 IE IE1059/80A patent/IE49812B1/en unknown
- 1980-05-21 PT PT71278A patent/PT71278A/pt unknown
- 1980-05-21 HU HU801280A patent/HU183143B/hu unknown
- 1980-05-21 PL PL1980224390A patent/PL126491B1/pl unknown
- 1980-05-21 AU AU58594/80A patent/AU537785B2/en not_active Ceased
- 1980-05-21 CA CA000352335A patent/CA1149375A/fr not_active Expired
- 1980-05-21 FI FI801643A patent/FI801643A7/fi not_active Application Discontinuation
- 1980-05-21 NO NO801503A patent/NO801503L/no unknown
- 1980-05-21 PL PL1980224392A patent/PL122638B1/pl unknown
- 1980-05-21 DD DD80221268A patent/DD151169A5/de unknown
- 1980-05-21 SE SE8003822A patent/SE8003822L/xx not_active Application Discontinuation
- 1980-05-21 SU SU802928399A patent/SU965358A3/ru active
- 1980-05-21 LU LU82478A patent/LU82478A1/fr unknown
- 1980-05-21 NO NO801504A patent/NO801504L/no unknown
- 1980-05-21 ZW ZW123/80A patent/ZW12380A1/xx unknown
- 1980-05-21 ZA ZA00803036A patent/ZA803036B/xx unknown
- 1980-05-22 PH PH24057A patent/PH15916A/en unknown
- 1980-05-22 IL IL60141A patent/IL60141A/xx unknown
- 1980-05-22 IL IL60140A patent/IL60140A/xx unknown
- 1980-05-22 PH PH24058A patent/PH17310A/en unknown
- 1980-05-23 JP JP6800680A patent/JPS55154978A/ja active Pending
- 1980-05-23 NL NL8003010A patent/NL8003010A/nl not_active Application Discontinuation
- 1980-05-23 JP JP6800780A patent/JPS55154979A/ja active Pending
- 1980-05-23 NL NL8003024A patent/NL8003024A/nl not_active Application Discontinuation
- 1980-09-22 ES ES495237A patent/ES495237A0/es active Granted
- 1980-09-22 ES ES495236A patent/ES8106533A1/es not_active Expired
-
1981
- 1981-01-19 SU SU813229954A patent/SU984411A3/ru active
- 1981-01-19 SU SU813229054A patent/SU988193A3/ru active
-
1983
- 1983-03-09 YU YU00561/83A patent/YU56183A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4520022A (en) * | 1983-01-28 | 1985-05-28 | Bristol-Myers Company | Substituted vinyl cephalosporins |
| US4591641A (en) * | 1983-01-28 | 1986-05-27 | Bristol-Myers Company | Substituted vinyl cephalosporins |
| WO2003072582A1 (en) * | 2002-02-28 | 2003-09-04 | Lg Life Sciences Ltd. | Novel cephalosporin compounds and process for preparing the same |
Also Published As
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Legal Events
| Date | Code | Title | Description |
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| 8141 | Disposal/no request for examination |