CS247081B2 - Production method of cefemderivatives - Google Patents

Production method of cefemderivatives Download PDF

Info

Publication number: CS247081B2
Authority: CS; Czechoslovakia
Prior art keywords: group; formula; carbon atoms; alkyl; optionally
Prior art date: 1983-05-07

Application number

CS843303A

Other languages

Czech (cs)

English (en)

Inventor

Wilfried Schwab

Walter Duerckheimer

Reiner Kirrstetter

Rudolf Lattrell

Original Assignee

Hoechst Ag

Priority date (The priority date 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 date listed.)

1983-05-07

Filing date

1984-05-04

Publication date

1986-11-13

1984-05-04 Application filed by Hoechst Ag filed Critical Hoechst Ag

1986-11-13 Publication of CS247081B2 publication Critical patent/CS247081B2/cs

Links

238000004519 manufacturing process Methods 0.000 title 1
-1 decamethylene ring Chemical group 0.000 claims description 39
150000001875 compounds Chemical class 0.000 claims description 33
125000004432 carbon atom Chemical group C* 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 7
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000003302 alkenyloxy group Chemical group 0.000 claims description 3
125000005133 alkynyloxy group Chemical group 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
IDIOJRGTRFRIJL-UHFFFAOYSA-N iodosilane Chemical compound I[SiH3] IDIOJRGTRFRIJL-UHFFFAOYSA-N 0.000 claims description 3
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 3
125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
239000000243 solution Substances 0.000 description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 9
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
238000007792 addition Methods 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
150000001735 carboxylic acids Chemical class 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
KRNSYSYRLQDHDK-UHFFFAOYSA-N 6,7-dihydro-5h-cyclopenta[b]pyridine Chemical compound C1=CN=C2CCCC2=C1 KRNSYSYRLQDHDK-UHFFFAOYSA-N 0.000 description 4
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 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical group 0.000 description 4
239000007858 starting material Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 3
PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000013078 crystal Substances 0.000 description 3
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
125000005394 methallyl group Chemical group 0.000 description 3
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
150000007970 thio esters Chemical class 0.000 description 2
239000005051 trimethylchlorosilane Substances 0.000 description 2
125000006593 (C2-C3) alkynyl group Chemical group 0.000 description 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
MASDFXZJIDNRTR-UHFFFAOYSA-N 1,3-bis(trimethylsilyl)urea Chemical compound C[Si](C)(C)NC(=O)N[Si](C)(C)C MASDFXZJIDNRTR-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
RZYHXKLKJRGJGP-UHFFFAOYSA-N 2,2,2-trifluoro-n,n-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)N([Si](C)(C)C)C(=O)C(F)(F)F RZYHXKLKJRGJGP-UHFFFAOYSA-N 0.000 description 1
NDVMCQUOSYOQMZ-UHFFFAOYSA-N 2,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)C(C(N)=O)[Si](C)(C)C NDVMCQUOSYOQMZ-UHFFFAOYSA-N 0.000 description 1
UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
BFJMHTOBRRZELQ-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-c]pyridine Chemical compound N1=CC=C2C(I)=NNC2=C1 BFJMHTOBRRZELQ-UHFFFAOYSA-N 0.000 description 1
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
TZCYLJGNWDVJRA-UHFFFAOYSA-N 6-chloro-1-hydroxybenzotriazole Chemical compound C1=C(Cl)C=C2N(O)N=NC2=C1 TZCYLJGNWDVJRA-UHFFFAOYSA-N 0.000 description 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
150000001782 cephems Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
RCFDIXKVOHJQPP-UHFFFAOYSA-N furo[2,3-b]pyridine Chemical compound C1=CN=C2OC=CC2=C1 RCFDIXKVOHJQPP-UHFFFAOYSA-N 0.000 description 1
YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 description 1
WJDMEHCIRPKRRQ-UHFFFAOYSA-N furo[3,2-c]pyridine Chemical compound N1=CC=C2OC=CC2=C1 WJDMEHCIRPKRRQ-UHFFFAOYSA-N 0.000 description 1
LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
NEXSMEBSBIABKL-UHFFFAOYSA-N hexamethyldisilane Chemical compound C[Si](C)(C)[Si](C)(C)C NEXSMEBSBIABKL-UHFFFAOYSA-N 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000005649 metathesis reaction Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 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
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
SMZMHUCIDGHERP-UHFFFAOYSA-N thieno[2,3-b]pyridine Chemical compound C1=CN=C2SC=CC2=C1 SMZMHUCIDGHERP-UHFFFAOYSA-N 0.000 description 1
GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical compound C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 description 1
DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical compound N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 description 1
FKNKKPFULFAZLX-UHFFFAOYSA-N thieno[3,4-b]pyridine Chemical compound N1=CC=CC2=CSC=C21 FKNKKPFULFAZLX-UHFFFAOYSA-N 0.000 description 1
QXWYLVQTEJWMKW-UHFFFAOYSA-N thieno[3,4-c]pyridine Chemical compound C1=NC=CC2=CSC=C21 QXWYLVQTEJWMKW-UHFFFAOYSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- 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
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CS843303A 1983-05-07 1984-05-04 Production method of cefemderivatives CS247081B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19833316798 DE3316798A1 (de)	1983-05-07	1983-05-07	Verfahren zur herstellung von cephemverbindungen

Publications (1)

Publication Number	Publication Date
CS247081B2 true CS247081B2 (en)	1986-11-13

Family

ID=6198462

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS843303A CS247081B2 (en)	1983-05-07	1984-05-04	Production method of cefemderivatives

Country Status (24)

Country	Link
US (1)	US4667028A (sv)
EP (1)	EP0124889A3 (sv)
JP (1)	JPS6034972A (sv)
KR (1)	KR910004332B1 (sv)
AU (1)	AU575825B2 (sv)
CA (1)	CA1224457A (sv)
CS (1)	CS247081B2 (sv)
DD (1)	DD251133A5 (sv)
DE (1)	DE3316798A1 (sv)
DK (1)	DK166282C (sv)
ES (1)	ES8502445A1 (sv)
FI (1)	FI82055C (sv)
HU (1)	HU191683B (sv)
IL (1)	IL71771A (sv)
MA (1)	MA20110A1 (sv)
MT (1)	MTP947B (sv)
MX (1)	MX168599B (sv)
NO (1)	NO841792L (sv)
NZ (1)	NZ208064A (sv)
OA (1)	OA07766A (sv)
PH (1)	PH19554A (sv)
PT (1)	PT78544B (sv)
YU (1)	YU45965B (sv)
ZA (1)	ZA843343B (sv)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS60169486A (ja) *	1984-02-10	1985-09-02	Yamanouchi Pharmaceut Co Ltd	７−アミノ−３−置換メチル−３−セフエム−４−カルボン酸およびその低級アルキルシリル誘導体の製造法
IL74822A (en) *	1984-04-17	1989-06-30	Daiichi Seiyaku Co	Cephalosporin derivatives and salts thereof and their preparation
US4788185A (en) *	1984-04-23	1988-11-29	Takeda Chemical Industries, Ltd.	Cephalosporin compounds
DE3588208D1 (de) *	1984-11-23	1999-04-08	Biochemie Gmbh	Cephalosporinderivative
ATE89826T1 (de) *	1985-03-01	1993-06-15	Takeda Chemical Industries Ltd	Antibakterielle verbindungen, ihre herstellung und verwendung.
US4703118A (en) *	1985-04-08	1987-10-27	Eli Lilly And Company	Synthesis of 3-iodomethyl cephalosporins
GB8519606D0 (en) *	1985-08-05	1985-09-11	Fujisawa Pharmaceutical Co	3 7-d substituted-3-cephem compounds
US4714760A (en) *	1985-08-20	1987-12-22	Bristol-Myers Company	Cephalosporin intermediates
US4749522A (en) *	1985-10-31	1988-06-07	Angio-Medical Corporation	Supercritical fluid extraction of animal derived materials
DE3542644A1 (de) *	1985-12-03	1987-06-04	Hoechst Ag	Verfahren zur herstellung von cefodizim
CA1296012C (en) *	1986-03-19	1992-02-18	Susumu Nakagawa	6,7-dihydroxy-isoquinoline derivatives
US4868294A (en) *	1986-07-11	1989-09-19	Bristol-Myers Company	Process for preparing cephalosporin intermediates
DE3706020A1 (de) *	1987-02-25	1988-09-08	Hoechst Ag	Kristallisierte cephem-saeureadditionssalze und verfahren zu ihrer herstellung
TWI335332B (en) *	2001-10-12	2011-01-01	Theravance Inc	Cross-linked vancomycin-cephalosporin antibiotics
CN102002058B (zh) *	2010-11-05	2012-04-04	山东鲁抗立科药物化学有限公司	硫酸头孢喹肟的合成方法
RS66326B1 (sr)	2011-09-09	2025-01-31	Merck Sharp & Dohme Llc	Ceftolozan/tazobaktam za lečenje intrapulmonalnih infekcija
US8809314B1 (en)	2012-09-07	2014-08-19	Cubist Pharmacueticals, Inc.	Cephalosporin compound
US8476425B1 (en)	2012-09-27	2013-07-02	Cubist Pharmaceuticals, Inc.	Tazobactam arginine compositions
US9872906B2 (en)	2013-03-15	2018-01-23	Merck Sharp & Dohme Corp.	Ceftolozane antibiotic compositions
US20140274990A1 (en)	2013-03-15	2014-09-18	Cubist Pharmaceuticals, Inc.	Ceftolozane pharmaceutical compositions
NZ700372A (en)	2013-03-15	2016-01-29	Merck Sharp & Dohme	Ceftolozane antibiotic compositions
US10376496B2 (en)	2013-09-09	2019-08-13	Merck, Sharp & Dohme Corp.	Treating infections with ceftolozane/tazobactam in subjects having impaired renal function
US20150094293A1 (en)	2013-09-27	2015-04-02	Calixa Therapeutics, Inc.	Solid forms of ceftolozane
CN103601738A (zh) *	2013-12-04	2014-02-26	哈药集团制药总厂	一种头孢匹罗氢碘酸盐的制备方法
CN105646543B (zh) *	2016-03-17	2018-03-27	天津大学	一种头孢喹肟晶体及其制备方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR229883A1 (es) *	1978-05-26	1983-12-30	Glaxo Group Ltd	Procedimiento para la preparacion de antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)-acetamido)-3-(1-piridinometil)-cef-3-em-4-carboxilato
US4266049A (en) *	1980-02-20	1981-05-05	Eli Lilly And Company	Process for 3-iodomethyl cephalosporins
US4367228A (en) *	1980-10-29	1983-01-04	Fujisawa Pharmaceutical Co., Ltd.	Cephem compound and composition
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
ATE31535T1 (de) *	1981-07-17	1988-01-15	Glaxo Group Ltd	Cephalosporinverbindungen.
ZA826538B (en) *	1981-09-08	1984-04-25	Lilly Co Eli	Thieno and furopyridinium-substituted cephalosporin derivatives
US4396620A (en) *	1981-09-08	1983-08-02	Eli Lilly And Company	Cephalosporin quinolinium betaines
US4396619A (en) *	1981-09-08	1983-08-02	Eli Lilly And Company	Cephalosporin betaines
US4402955A (en) *	1981-10-02	1983-09-06	Eli Lilly And Company	Dioximino cephalosporin antibiotics

1983
- 1983-05-07 DE DE19833316798 patent/DE3316798A1/de not_active Withdrawn
1984
- 1984-04-27 YU YU76684A patent/YU45965B/sh unknown
- 1984-05-02 HU HU841704A patent/HU191683B/hu not_active IP Right Cessation
- 1984-05-03 MA MA20331A patent/MA20110A1/fr unknown
- 1984-05-03 FI FI841764A patent/FI82055C/sv not_active IP Right Cessation
- 1984-05-03 MT MT947A patent/MTP947B/xx unknown
- 1984-05-04 KR KR1019840002447A patent/KR910004332B1/ko not_active Application Discontinuation
- 1984-05-04 MX MX007999A patent/MX168599B/es unknown
- 1984-05-04 DK DK224284A patent/DK166282C/da active
- 1984-05-04 NO NO841792A patent/NO841792L/no unknown
- 1984-05-04 CS CS843303A patent/CS247081B2/cs unknown
- 1984-05-04 AU AU27705/84A patent/AU575825B2/en not_active Ceased
- 1984-05-04 DD DD84262706A patent/DD251133A5/de not_active IP Right Cessation
- 1984-05-04 US US06/607,403 patent/US4667028A/en not_active Expired - Fee Related
- 1984-05-04 ES ES532183A patent/ES8502445A1/es not_active Expired
- 1984-05-04 PT PT78544A patent/PT78544B/pt unknown
- 1984-05-04 CA CA000453602A patent/CA1224457A/en not_active Expired
- 1984-05-04 NZ NZ208064A patent/NZ208064A/en unknown
- 1984-05-04 EP EP84105025A patent/EP0124889A3/de not_active Withdrawn
- 1984-05-04 ZA ZA843343A patent/ZA843343B/xx unknown
- 1984-05-06 IL IL71771A patent/IL71771A/xx unknown
- 1984-05-07 PH PH30651A patent/PH19554A/en unknown
- 1984-05-07 OA OA58291A patent/OA07766A/xx unknown
- 1984-05-07 JP JP59090842A patent/JPS6034972A/ja active Pending

Also Published As

Publication number	Publication date
MX168599B (es)	1993-06-01
JPS6034972A (ja)	1985-02-22
MA20110A1 (fr)	1984-12-31
MTP947B (en)	1985-01-17
PT78544B (de)	1986-07-17
CA1224457A (en)	1987-07-21
KR910004332B1 (ko)	1991-06-26
HU191683B (en)	1987-03-30
DE3316798A1 (de)	1984-11-08
EP0124889A3 (de)	1985-11-27
FI82055C (sv)	1991-01-10
FI841764A0 (fi)	1984-05-03
IL71771A (en)	1988-06-30
ES532183A0 (es)	1985-01-01
DK166282C (da)	1993-08-23
OA07766A (fr)	1985-08-30
EP0124889A2 (de)	1984-11-14
YU76684A (en)	1986-10-31
HUT34506A (en)	1985-03-28
ES8502445A1 (es)	1985-01-01
AU575825B2 (en)	1988-08-11
NZ208064A (en)	1987-07-31
FI841764A (fi)	1984-11-08
PH19554A (en)	1986-05-21
DK224284D0 (da)	1984-05-04
DD251133A5 (de)	1987-11-04
IL71771A0 (en)	1984-09-30
AU2770584A (en)	1984-11-08
ZA843343B (en)	1984-12-24
YU45965B (sh)	1992-12-21
FI82055B (fi)	1990-09-28
DK224284A (da)	1984-11-08
US4667028A (en)	1987-05-19
NO841792L (no)	1984-11-08
PT78544A (de)	1984-06-01
DK166282B (da)	1993-03-29
KR840009116A (ko)	1984-12-24

Publication	Publication Date	Title
CS247081B2 (en)	1986-11-13	Production method of cefemderivatives
KR880001541B1 (ko)	1988-08-20	세팔로스포린 유도체의 제조방법
US7452990B2 (en)	2008-11-18	Intermediates for synthesis of cephalosporins and process for preparation of such intermediates
EP0175610A2 (en)	1986-03-26	New cephalosporin compounds and the production thereof
JP2004520336A (ja)	2004-07-08	新規チアゾリル酢酸チオエステル誘導体およびそれらのセファロスポリン化合物製造のための使用
US4714760A (en)	1987-12-22	Cephalosporin intermediates
CS248714B2 (en)	1987-02-12	Production method of new 7-(2 syn-oxomino-(5 amino-1,2,4-thiadiazol-3-y)cefeme derivatives
CS247080B2 (en)	1986-11-13	Production method of cefemderivatives
EP0175814B1 (en)	1990-05-23	Process for preparing cephem derivatives
WO2002083634A2 (en)	2002-10-24	Process for the preparation of cefpodoxime acid
JPS59130294A (ja)	1984-07-26	セフアロスポリン誘導体類およびその製造法
EP0628561B1 (en)	1997-09-03	Process for preparing cephalosporin compounds from reactive organic acid derivatives
KR100249581B1 (ko)	2000-04-01	7-알파-아미노아실-세팔로스포린의 제조방법
JPS6097983A (ja)	1985-05-31	セフアロスポリン誘導体、その製法および医薬組成物
GB1582960A (en)	1981-01-21	Chemical synthesis of -lactam derivatives
KR930007260B1 (ko)	1993-08-04	세팔로스포린 유도체의 제조방법
KR0129567B1 (ko)	1998-04-09	반응성 유기산 유도체로부터 세팔로스포린 화합물의 제조방법
JPH06247973A (ja)	1994-09-06	３−ビニルセファロスポリンの製造法
KR970005893B1 (ko)	1997-04-21	반응성 유기산 유도체로부터 세팔로스포린 화합물의 제조방법
EP0148004A2 (en)	1985-07-10	Cephalosporin antibiotics
PL179324B1 (pl)	2000-08-31	Nowa reaktywna tiofosforanowa pochodna kwasu tia(dia) zolooctowegoi sposób jej otrzymywania PL
AU2002307885A1 (en)	2002-10-28	Process for the preparation of cefpodoxime acid