FI59601C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla 0-substituerade 7beta-amino-3-cefem-3-ol-4-karbonsyrafoereningar - Google Patents

Foerfarande foer framstaellning av farmakologiskt vaerdefulla 0-substituerade 7beta-amino-3-cefem-3-ol-4-karbonsyrafoereningar Download PDF

Info

Publication number: FI59601C
Authority: FI; Finland
Prior art keywords: carboxylic acid; cephem; formula; methoxy; compound
Prior art date: 1972-06-29

Application number

FI1750/73A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI59601B (fi

Inventor

Riccardo Scartazzini

Hans Bickel

Original Assignee

Ciba Geigy 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.)

1972-06-29

Filing date

1973-05-30

Publication date

1981-09-10

1972-06-29 Priority claimed from CH978872A external-priority patent/CH587268A5/de

1972-12-22 Priority claimed from CH1872272A external-priority patent/CH605987A5/de

1973-02-23 Priority claimed from CH265573A external-priority patent/CH605988A5/de

1973-05-30 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1981-05-29 Application granted granted Critical

1981-05-29 Publication of FI59601B publication Critical patent/FI59601B/fi

1981-09-10 Publication of FI59601C publication Critical patent/FI59601C/fi

Links

230000000144 pharmacologic effect Effects 0.000 title description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 186
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 170
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 85
-1 diphenylmethyl ester Chemical class 0.000 claims description 82
239000000203 mixture Substances 0.000 claims description 71
150000001875 compounds Chemical class 0.000 claims description 61
150000003839 salts Chemical class 0.000 claims description 43
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 21
238000000034 method Methods 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
239000000284 extract Substances 0.000 claims description 6
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
229910052938 sodium sulfate Inorganic materials 0.000 claims description 5
235000011152 sodium sulphate Nutrition 0.000 claims description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
150000008049 diazo compounds Chemical class 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
239000012074 organic phase Substances 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 111
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 81
239000000243 solution Substances 0.000 description 76
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 59
238000000862 absorption spectrum Methods 0.000 description 59
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 53
239000000741 silica gel Substances 0.000 description 50
229910002027 silica gel Inorganic materials 0.000 description 50
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 36
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 31
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
238000003756 stirring Methods 0.000 description 21
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 20
239000007858 starting material Substances 0.000 description 18
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 17
239000002244 precipitate Substances 0.000 description 17
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
239000012299 nitrogen atmosphere Substances 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 12
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 10
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
239000003153 chemical reaction reagent Substances 0.000 description 9
238000001816 cooling Methods 0.000 description 9
229910052740 iodine Inorganic materials 0.000 description 9
239000000047 product Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
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 8
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
239000011630 iodine Substances 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 7
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 7
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
125000003545 alkoxy group Chemical group 0.000 description 7
229910052804 chromium Inorganic materials 0.000 description 7
239000011651 chromium Substances 0.000 description 7
235000019253 formic acid Nutrition 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
239000000843 powder Substances 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
OGIIWTRTOXDWEH-UHFFFAOYSA-N [O].[O-][O+]=O Chemical compound [O].[O-][O+]=O OGIIWTRTOXDWEH-UHFFFAOYSA-N 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
125000004356 hydroxy functional group Chemical group O* 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
238000012360 testing method Methods 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
241000588724 Escherichia coli Species 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000012043 crude product Substances 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
229940126062 Compound A Drugs 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000002585 base Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
238000010828 elution Methods 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
125000000524 functional group Chemical group 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000002480 mineral oil Substances 0.000 description 4
235000010446 mineral oil Nutrition 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
239000011701 zinc Substances 0.000 description 4
PFJVIOBMBDFBCJ-UHFFFAOYSA-N (1z)-1-diazobutane Chemical compound CCCC=[N+]=[N-] PFJVIOBMBDFBCJ-UHFFFAOYSA-N 0.000 description 3
DNGJVDGPCGXBFF-UHFFFAOYSA-N 4-methyl-n-(methyldiazenyl)aniline Chemical compound CN=NNC1=CC=C(C)C=C1 DNGJVDGPCGXBFF-UHFFFAOYSA-N 0.000 description 3
241000894006 Bacteria Species 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
241000588748 Klebsiella Species 0.000 description 3
241000588770 Proteus mirabilis Species 0.000 description 3
ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
125000005002 aryl methyl group Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical class C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
150000002084 enol ethers Chemical class 0.000 description 3
150000002085 enols Chemical class 0.000 description 3
238000006266 etherification reaction Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
229910001385 heavy metal Inorganic materials 0.000 description 3
239000012535 impurity Substances 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
231100000053 low toxicity Toxicity 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000000155 melt Substances 0.000 description 3
MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 3
OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 3
230000011987 methylation Effects 0.000 description 3
238000007069 methylation reaction Methods 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
238000012746 preparative thin layer chromatography Methods 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
230000007017 scission Effects 0.000 description 3
238000006884 silylation reaction Methods 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
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 3
SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical class S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 description 2
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
244000063299 Bacillus subtilis Species 0.000 description 2
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
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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 2
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FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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229920002472 Starch Polymers 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000003463 adsorbent Substances 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229940106164 cephalexin Drugs 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
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229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000012336 iodinating agent Substances 0.000 description 1
230000026045 iodination Effects 0.000 description 1
238000006192 iodination reaction Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 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
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229960002523 mercuric chloride Drugs 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229910001511 metal iodide Inorganic materials 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000012022 methylating agents‎ Substances 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
238000004452 microanalysis Methods 0.000 description 1
244000005700 microbiome Species 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
BPOZIJBDYFHEJR-UHFFFAOYSA-N n-(ethyldiazenyl)-4-methylaniline Chemical compound CCN=NNC1=CC=C(C)C=C1 BPOZIJBDYFHEJR-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
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000007248 oxidative elimination reaction Methods 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000005797 stannylation reaction Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
150000004654 triazenes Chemical class 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
QDNCLIPKBNMUPP-UHFFFAOYSA-N trimethyloxidanium Chemical compound C[O+](C)C QDNCLIPKBNMUPP-UHFFFAOYSA-N 0.000 description 1
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 description 1
238000005866 tritylation reaction Methods 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
238000009736 wetting Methods 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
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/59—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3 with hetero atoms directly attached in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65613—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. cephalosporins and analogs
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Oncology (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Communicable Diseases (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

FI1750/73A 1972-06-29 1973-05-30 Foerfarande foer framstaellning av farmakologiskt vaerdefulla 0-substituerade 7beta-amino-3-cefem-3-ol-4-karbonsyrafoereningar FI59601C (fi)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
CH978872A CH587268A5 (en)	1972-06-29	1972-06-29	Substd carboxylic acid derivs - broad spectrum antibiotics and inters
CH978872		1972-06-29
CH1219572		1972-08-17
CH1219572		1972-08-17
CH1872272A CH605987A5 (en)	1972-12-22	1972-12-22	Substd carboxylic acid derivs
CH1872272		1972-12-22
CH265573		1973-02-23
CH265573A CH605988A5 (en)	1973-02-23	1973-02-23	Substd 7-beta-amino ceph-3-em-3-ol 4-carboxylic acids

Publications (2)

Publication Number	Publication Date
FI59601B FI59601B (fi)	1981-05-29
FI59601C true FI59601C (fi)	1981-09-10

Family

ID=27428472

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
FI1750/73A FI59601C (fi)	1972-06-29	1973-05-30	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 0-substituerade 7beta-amino-3-cefem-3-ol-4-karbonsyrafoereningar
FI1752/73A FI60870C (fi)	1972-06-29	1973-05-30	Foerfarande foer framstaellning av farmakologiskt vaerdefulla o-substituerade 7beta-amino-3-cefem-3-ol-4-karbonsyrafoereningar
FI1751/73A FI59602C (fi)	1972-06-29	1973-05-30	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 0-substituerade 7beta-amino-3-cefem-3-ol-4-karbonsyrafoereningar

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
FI1752/73A FI60870C (fi)	1972-06-29	1973-05-30	Foerfarande foer framstaellning av farmakologiskt vaerdefulla o-substituerade 7beta-amino-3-cefem-3-ol-4-karbonsyrafoereningar
FI1751/73A FI59602C (fi)	1972-06-29	1973-05-30	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 0-substituerade 7beta-amino-3-cefem-3-ol-4-karbonsyrafoereningar

Country Status (26)

Country	Link
US (2)	US4405778A (ro)
JP (3)	JPS5933598B2 (ro)
AR (6)	AR206201A1 (ro)
AT (5)	AT356810B (ro)
BE (1)	BE801597A (ro)
BG (1)	BG24954A3 (ro)
CA (1)	CA1110230A (ro)
DD (3)	DD107470A5 (ro)
DE (1)	DE2331133C2 (ro)
DK (1)	DK153324B (ro)
FI (3)	FI59601C (ro)
FR (1)	FR2190418B1 (ro)
GB (1)	GB1435111A (ro)
HK (1)	HK73778A (ro)
HU (3)	HU168017B (ro)
IE (1)	IE37767B1 (ro)
IL (1)	IL42506A (ro)
LU (3)	LU67891A1 (ro)
MY (1)	MY7900008A (ro)
NL (3)	NL7309136A (ro)
NO (3)	NO145241C (ro)
PH (1)	PH18567A (ro)
PL (1)	PL91608B1 (ro)
RO (4)	RO64226A (ro)
SE (5)	SE417099B (ro)
YU (8)	YU39909B (ro)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
YU36970B (en) *	1973-02-23	1984-08-31	Lilly Co Eli	Process for obtaining 7-(amino)-acylamido-3-halocephalosporins
US4301278A (en) *	1974-02-26	1981-11-17	Ciba-Geigy Corporation	Process for the manufacture of enol derivatives
AU498131B2 (en) *	1974-02-26	1979-02-15	Ciba-Geigy Ag	Production of cephems by cyclization
US3928334A (en) *	1974-06-06	1975-12-23	Bristol Myers Co	Process for the production of cefamandole
US4045435A (en) *	1974-10-09	1977-08-30	Eli Lilly And Company	Preparation of cephalosporin ethers
AT342197B (de) *	1975-02-20	1978-03-28	Ciba Geigy Ag	Neues verfahren zur herstellung von 3-cephemverbindungen
US4147864A (en) *	1975-02-20	1979-04-03	Ciba-Geigy Corporation	Process for the manufacture of 7β-amino-3-cephem-3-ol-4 carboxylic acid compounds
CH622802A5 (ro) *	1975-08-20	1981-04-30	Ciba Geigy Ag
PH17188A (en) *	1977-03-14	1984-06-14	Fujisawa Pharmaceutical Co	New cephem and cepham compounds and their pharmaceutical compositions and method of use
US4604386A (en) *	1984-07-09	1986-08-05	Eli Lilly And Company	3-(alkynylalkyloxy) cephalosporins
GR861118B (en)	1985-04-30	1986-08-18	Lilly Co Eli	7-substituted bicyclic pyrazolidinones
EP0280240B1 (en) *	1987-02-27	1994-09-14	Banyu Pharmaceutical Co., Ltd.	Cephalosporin derivatives, process for their preparation and antibacterial agents
JP2676763B2 (ja) *	1987-02-27	1997-11-17	萬有製薬株式会社	セファロスポリン誘導体
JPS63255800A (ja) *	1987-04-14	1988-10-24	礒井　誠二郎	警報装置
AU618029B2 (en) *	1987-11-02	1991-12-12	Imperial Chemical Industries Plc	Polypeptide compounds
GB8813356D0 (en) *	1988-06-06	1988-07-13	Ici Plc	Polypeptide compounds
DK0521827T3 (da)	1991-07-03	1996-11-11	Ciba Geigy Ag	Farmakologisk virksomme hydrazinderivater og fremgangsmåde til deres fremstilling
GB9115203D0 (en) *	1991-07-15	1991-08-28	Biochemie Gmbh	Improvements in or relating to beta lactam production
MXPA01009808A (es) *	1999-04-01	2002-04-24	Dsm Nv	Aglomerados por cristalizacion.
US6627556B1 (en)	2002-04-24	2003-09-30	Lsi Logic Corporation	Method of chemically altering a silicon surface and associated electrical devices
CN102268023B (zh) *	2011-08-15	2013-04-17	南京丰融化学技术有限公司	头孢类衍生物cxd的晶型
CN115160097B (zh) *	2022-07-22	2024-05-28	温州大学	一种硫代乙酸还原n-o键合成酰胺的方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1308822A (en) *	1970-04-14	1973-03-07	Beecham Group Ltd	4-isopropylidene-3-oxocephams
GB1348985A (en) *	1970-06-16	1974-03-27	Merck & Co Inc	Esters of cephalosporin compounds
IL37879A (en) *	1970-10-27	1974-12-31	Ciba Geigy Ag	3-unsubstituted cephalosporin derivatives,process for their manufacture and compositions containing them
US3704297A (en) *	1971-03-05	1972-11-28	American Home Prod	7 - (1,4 - cyclohexadienylacylamido)cephalosporanic acids and related compounds
US3741962A (en) *	1971-05-21	1973-06-26	Squibb & Sons Inc	Alpha-thioureidocephalosporanic acid compounds
US3846417A (en) *	1972-06-23	1974-11-05	Squibb & Sons Inc	1,4-cyclohexadienyl imidazolidinyl cephalosporanic acids and derivatives thereof
US3917588A (en) *	1972-11-28	1975-11-04	Lilly Co Eli	{60 -Aminoacyl cephalosporin ethers
US3917587A (en) *	1972-11-28	1975-11-04	Lilly Co Eli	Cephalosporin ethers
US3907786A (en) *	1973-09-04	1975-09-23	Bristol Myers Co	7-{8 {60 -(2-aminomethyl-1,4-cyclohexadienyl)acetamido{9 -3-heterocyclic-thiomethyl-3-cephem-4-carboxylic acids and salts

1973
- 1973-01-01 AR AR248828A patent/AR206201A1/es active
- 1973-05-30 FI FI1750/73A patent/FI59601C/fi active
- 1973-05-30 FI FI1752/73A patent/FI60870C/fi active
- 1973-05-30 FI FI1751/73A patent/FI59602C/fi active
- 1973-06-07 IE IE914/73A patent/IE37767B1/xx unknown
- 1973-06-12 SE SE7308234A patent/SE417099B/xx unknown
- 1973-06-12 SE SE7308235A patent/SE417430B/xx unknown
- 1973-06-12 SE SE7308237A patent/SE7308237L/sv unknown
- 1973-06-12 SE SE7308233A patent/SE417429B/sv unknown
- 1973-06-14 RO RO7375138A patent/RO64226A/ro unknown
- 1973-06-14 RO RO7384759A patent/RO73345A/ro unknown
- 1973-06-14 RO RO7386374A patent/RO64419A/ro unknown
- 1973-06-14 RO RO7300860064A patent/RO63761A/ro unknown
- 1973-06-15 IL IL42506A patent/IL42506A/xx unknown
- 1973-06-19 DE DE2331133A patent/DE2331133C2/de not_active Expired
- 1973-06-26 FR FR7323235A patent/FR2190418B1/fr not_active Expired
- 1973-06-27 GB GB3053773A patent/GB1435111A/en not_active Expired
- 1973-06-27 LU LU67891A patent/LU67891A1/xx unknown
- 1973-06-27 BG BG024001A patent/BG24954A3/xx unknown
- 1973-06-27 LU LU67888A patent/LU67888A1/xx unknown
- 1973-06-27 LU LU67887A patent/LU67887A1/xx unknown
- 1973-06-28 DD DD171905A patent/DD107470A5/xx unknown
- 1973-06-28 DD DD171906A patent/DD106187A5/xx unknown
- 1973-06-28 DD DD171903A patent/DD106184A5/xx unknown
- 1973-06-28 AT AT569573A patent/AT356810B/de not_active IP Right Cessation
- 1973-06-28 AT AT57675*A patent/ATA57675A/de unknown
- 1973-06-28 HU HUCI1392A patent/HU168017B/hu unknown
- 1973-06-28 AT AT57675*7A patent/AT329762B/de not_active IP Right Cessation
- 1973-06-28 HU HUCI1393A patent/HU167726B/hu unknown
- 1973-06-28 PH PH14784A patent/PH18567A/en unknown
- 1973-06-28 NO NO2682/73A patent/NO145241C/no unknown
- 1973-06-28 NO NO2683/73A patent/NO145242C/no unknown
- 1973-06-28 CA CA175,100A patent/CA1110230A/en not_active Expired
- 1973-06-28 NO NO2681/73A patent/NO145240C/no unknown
- 1973-06-28 AT AT569673A patent/AT329745B/de not_active IP Right Cessation
- 1973-06-28 BE BE132845A patent/BE801597A/xx not_active IP Right Cessation
- 1973-06-28 DK DK358873AA patent/DK153324B/da not_active Application Discontinuation
- 1973-06-28 HU HUCI1391A patent/HU169032B/hu unknown
- 1973-06-28 AT AT569473A patent/AT356809B/de not_active IP Right Cessation
- 1973-06-29 PL PL1973163719A patent/PL91608B1/pl unknown
- 1973-06-29 JP JP48074354A patent/JPS5933598B2/ja not_active Expired
- 1973-06-29 AR AR248827A patent/AR212317A1/es active
- 1973-06-29 NL NL7309136A patent/NL7309136A/xx unknown
- 1973-06-29 YU YU1792/73A patent/YU39909B/xx unknown
- 1973-06-29 YU YU1795/73A patent/YU39911B/xx unknown
- 1973-06-29 JP JP48074355A patent/JPS5933599B2/ja not_active Expired
- 1973-06-29 JP JP48074353A patent/JPS5934716B2/ja not_active Expired
- 1973-06-29 YU YU1793/73A patent/YU39910B/xx unknown
- 1973-06-29 NL NL7309137A patent/NL7309137A/xx not_active Application Discontinuation
- 1973-06-29 AR AR248826A patent/AR212576A1/es active
- 1973-06-29 NL NL7309139A patent/NL7309139A/xx not_active Application Discontinuation
1975
- 1975-09-30 AR AR264921A patent/AR212028A1/es active
1976
- 1976-02-13 US US05/657,904 patent/US4405778A/en not_active Expired - Lifetime
- 1976-02-13 US US05/657,908 patent/US4073902A/en not_active Expired - Lifetime
- 1976-09-30 AR AR264920A patent/AR211870A1/es active
- 1976-09-30 AR AR264922A patent/AR211871A1/es active
- 1976-10-29 SE SE7612053A patent/SE435289B/xx not_active IP Right Cessation
1978
- 1978-12-14 HK HK737/78A patent/HK73778A/xx unknown
1979
- 1979-12-30 MY MY8/79A patent/MY7900008A/xx unknown
1980
- 1980-11-03 YU YU02807/80A patent/YU280780A/xx unknown
- 1980-11-06 YU YU02842/80A patent/YU284280A/xx unknown
1981
- 1981-09-16 YU YU02237/81A patent/YU223781A/xx unknown
- 1981-09-16 YU YU02236/81A patent/YU223681A/xx unknown
- 1981-09-16 YU YU02238/81A patent/YU223881A/xx unknown

Also Published As

Publication number	Publication date
AU5738673A (en)	1975-01-09
NO145241C (no)	1982-02-10
SE417099B (sv)	1981-02-23
YU39910B (en)	1985-06-30
JPS5933598B2 (ja)	1984-08-16
DK153324B (da)	1988-07-04
YU179273A (en)	1982-06-30
SE417430B (sv)	1981-03-16
BG24954A3 (en)	1978-06-15
NO145240C (no)	1982-02-10
IE37767B1 (en)	1977-10-12
SE7308237L (ro)	1974-01-08
AR206201A1 (es)	1976-07-07
RO73345A (ro)	1982-09-09
IE37767L (en)	1973-12-29
AT329745B (de)	1976-05-25
NL7309136A (ro)	1974-01-02
HK73778A (en)	1978-12-22
JPS5934716B2 (ja)	1984-08-24
MY7900008A (en)	1979-12-31
SE7308233L (ro)	1973-12-31
AR211871A1 (es)	1978-03-31
NO145242B (no)	1981-11-02
NO145240B (no)	1981-11-02
RO63761A (fr)	1978-12-15
PH18567A (en)	1985-08-12
US4073902A (en)	1978-02-14
JPS5933599B2 (ja)	1984-08-16
FI60870C (fi)	1982-04-13
LU67887A1 (ro)	1975-04-11
BE801597A (fr)	1973-12-28
FI59602C (fi)	1981-09-10
FI59601B (fi)	1981-05-29
PL91608B1 (en)	1977-03-31
SE7612053L (sv)	1976-10-29
ATA57675A (de)	1975-08-15
YU284280A (en)	1983-01-21
DD106187A5 (ro)	1974-06-05
ATA569573A (de)	1975-06-15
JPS4949987A (ro)	1974-05-15
RO64419A (fr)	1979-07-15
SE7308234L (sv)	1973-12-31
YU179573A (en)	1982-06-30
YU280780A (en)	1983-02-28
US4405778A (en)	1983-09-20
AR212576A1 (es)	1978-08-15
DD107470A5 (ro)	1974-08-05
DD106184A5 (ro)	1974-06-05
FR2190418A1 (ro)	1974-02-01
NL7309139A (ro)	1974-01-02
AT329762B (de)	1976-05-25
FI59602B (fi)	1981-05-29
NL7309137A (ro)	1974-01-02
ATA569673A (de)	1975-08-15
YU179373A (en)	1982-06-30
JPS4949988A (ro)	1974-05-15
FR2190418B1 (ro)	1977-07-15
AR211870A1 (es)	1978-03-31
DE2331133A1 (de)	1974-01-17
SE435289B (sv)	1984-09-17
JPS4949986A (ro)	1974-05-15
IL42506A0 (en)	1973-08-29
AT356809B (de)	1980-05-27
RO64226A (fr)	1979-05-15
YU223881A (en)	1983-06-30
HU169032B (ro)	1976-09-28
YU223681A (en)	1983-06-30
LU67888A1 (ro)	1975-04-11
YU223781A (en)	1983-06-30
YU39911B (en)	1985-06-30
AR212028A1 (es)	1978-04-28
FI60870B (fi)	1981-12-31
IL42506A (en)	1976-09-30
LU67891A1 (ro)	1975-04-11
GB1435111A (en)	1976-05-12
SE417429B (sv)	1981-03-16
DE2331133C2 (de)	1984-04-12
YU39909B (en)	1985-06-30
ATA569473A (de)	1975-04-15
AT356810B (de)	1980-05-27
NO145242C (no)	1982-02-10
CA1110230A (en)	1981-10-06
HU168017B (ro)	1976-02-28
SE7308235L (ro)	1973-12-31
HU167726B (ro)	1975-12-25
NO145241B (no)	1981-11-02
AR212317A1 (es)	1978-06-30

Publication	Publication Date	Title
FI59601C (fi)	1981-09-10	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 0-substituerade 7beta-amino-3-cefem-3-ol-4-karbonsyrafoereningar
JPS5946955B2 (ja)	1984-11-15	抗生物質の新規中間体の製造方法
SU1407400A3 (ru)	1988-06-30	Способ получени замещенных винилцефалоспоринов
US4226866A (en)	1980-10-07	Novel antibiotic analogues of cephalosporins
JPS625919B2 (ro)	1987-02-07
JPS5934714B2 (ja)	1984-08-24	７β−アミノ−セフアム−３−オル−４−カルボン酸化合物または相当する３−θ−エステルの製法
IE56401B1 (en)	1991-07-17	Fluoromethylthiooxacephalosporins
US4181733A (en)	1980-01-01	Carboxyl derivatives of thienamycin
CA1041084A (en)	1978-10-24	PROCESS FOR THE MANUFACTURE OF 7.beta.-AMINO-3-CEPHEM-4-CARBOXYLIC ACID COMPOUNDS
FI66619B (fi)	1984-07-31	Foerfarande foer framstaellning av farceutiskt anvaendbara 7beta-(d-2-amino-2-(laogalkylsulfonylaminofenyl)-asetylamino)-3-r-3-cefem-4-karboxylsyror
CH587268A5 (en)	1977-04-29	Substd carboxylic acid derivs - broad spectrum antibiotics and inters
US4325951A (en)	1982-04-20	1-Oxadethiacephalosporin derivatives and antibacterial use thereof
US4078067A (en)	1978-03-07	3-(.beta.-Aminoethylidene)-7-oxo-4-oxaazabicyclo[3.2.0]heptane-2-carboxylic acid and derivatives thereof
US4957912A (en)	1990-09-18	7 acylamidocarbacephem antibacterial agents
US3971780A (en)	1976-07-27	Thio-β-lactam cephalosporins
CA1128930A (en)	1982-08-03	Cephalosporin compounds
CS216935B2 (en)	1982-12-31	Method of maling the derivatives of the 7-beta-aminothiazolylactamido-3-cefem-4-carboxyle acid
FI59803C (fi)	1981-10-12	Foerfarande foer framstaellning av terapeutiskt anvaendbara penicillansyraderivater
FI64941C (fi)	1984-02-10	0-substituerade 7beta-amino-3-cefem-3-ol-4-karboxylsyrafoereningar
US4078068A (en)	1978-03-07	3-(β-Aminoethylidene)-6-(α-hydroxyethyl)-7-oxo-4-oxaazabicyclo[3.]heptane-2-carboxylic acid and derivatives thereof
IE44352B1 (en)	1981-11-04	Chephalosporin derivatives
US3796711A (en)	1974-03-12	Process for preparing cephalosporin intermediates
US4171435A (en)	1979-10-16	[(Thioalkyl)thioacetyl)]cephalosporin derivatives
AT353971B (de)	1979-12-10	Verfahren zur herstellung von neuen, eine niederalkylsulfonylaminogruppe enthaltenden cephalosporinen
EP0098615B1 (en)	1988-01-07	1-oxadethiacephalosporin compound and antibacterial agent containing the same