CH535259A - Verfahren zur Herstellung von Derivaten der 7-Aminocephalosporansäure - Google Patents

Verfahren zur Herstellung von Derivaten der 7-Aminocephalosporansäure

Info

Publication number: CH535259A
Authority: CH; Switzerland
Prior art keywords: formula; ethyl acetate; salts; radical; compounds
Prior art date: 1969-11-28

Application number

CH1773169A

Other languages

German (de)

English (en)

Inventor

Hans Dr Bickel

Rolf Dr Bosshardt

Johannes Dr Mueller

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.)

1969-11-28

Filing date

1969-11-28

Publication date

1973-03-31

Priority to BE759570D priority Critical patent/BE759570A/xx

1969-11-28 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1969-11-28 Priority to CH1912071A priority patent/CH535261A/de

1969-11-28 Priority to CH1773169A priority patent/CH535259A/de

1970-11-17 Priority to US00090470A priority patent/US3719673A/en

1970-11-18 Priority to ZA707786A priority patent/ZA707786B/xx

1970-11-20 Priority to DE2056983A priority patent/DE2056983B2/de

1970-11-24 Priority to FR7042091A priority patent/FR2073428B1/fr

1970-11-24 Priority to CA098,942A priority patent/CA972363A/en

1970-11-25 Priority to FI703172A priority patent/FI52094C/fi

1970-11-25 Priority to IE1514/70A priority patent/IE34762B1/xx

1970-11-26 Priority to SU1494601A priority patent/SU507245A3/ru

1970-11-26 Priority to SE7016021A priority patent/SE386902B/xx

1970-11-26 Priority to SU1766771A priority patent/SU449488A3/ru

1970-11-26 Priority to EG498/70A priority patent/EG10710A/xx

1970-11-26 Priority to ES385906A priority patent/ES385906A1/es

1970-11-26 Priority to OA54099A priority patent/OA03830A/xx

1970-11-27 Priority to AT1071970A priority patent/AT301756B/de

1970-11-27 Priority to PL1970144679A priority patent/PL81220B1/pl

1970-11-27 Priority to CS8019A priority patent/CS177055B2/cs

1970-11-27 Priority to CS7973A priority patent/CS177093B2/cs

1970-11-27 Priority to AT926671A priority patent/AT303970B/de

1970-11-27 Priority to GB5641370A priority patent/GB1336318A/en

1970-11-27 Priority to NL7017401A priority patent/NL7017401A/xx

1970-11-28 Priority to HUCI001055 priority patent/HU162758B/hu

1970-11-28 Priority to JP45104507A priority patent/JPS5017075B1/ja

1973-03-31 Publication of CH535259A publication Critical patent/CH535259A/de

1973-06-01 Priority to ES415467A priority patent/ES415467A1/es

Links

239000002253 acid Substances 0.000 title claims description 11
229910052799 carbon Inorganic materials 0.000 claims abstract description 18
125000005842 heteroatom Chemical group 0.000 claims abstract description 11
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 10
229930195733 hydrocarbon Natural products 0.000 claims abstract description 10
229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 213
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 129
239000000243 solution Substances 0.000 claims description 86
-1 α-p-chlorophenyl-α-cyanoacetylamino Chemical group 0.000 claims description 79
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 72
239000000203 mixture Substances 0.000 claims description 63
235000002639 sodium chloride Nutrition 0.000 claims description 59
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 48
239000000741 silica gel Substances 0.000 claims description 48
229910002027 silica gel Inorganic materials 0.000 claims description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
150000001875 compounds Chemical class 0.000 claims description 42
150000003839 salts Chemical class 0.000 claims description 39
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 38
238000003756 stirring Methods 0.000 claims description 37
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 32
238000000034 method Methods 0.000 claims description 29
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 28
239000012074 organic phase Substances 0.000 claims description 28
159000000000 sodium salts Chemical class 0.000 claims description 26
239000002244 precipitate Substances 0.000 claims description 25
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 19
229960000583 acetic acid Drugs 0.000 claims description 19
229910052708 sodium Inorganic materials 0.000 claims description 19
239000011734 sodium Substances 0.000 claims description 19
239000007864 aqueous solution Substances 0.000 claims description 18
229910052757 nitrogen Inorganic materials 0.000 claims description 18
239000012071 phase Substances 0.000 claims description 18
239000000872 buffer Substances 0.000 claims description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
239000012362 glacial acetic acid Substances 0.000 claims description 17
230000007935 neutral effect Effects 0.000 claims description 17
229920006395 saturated elastomer Polymers 0.000 claims description 17
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 16
238000001914 filtration Methods 0.000 claims description 16
239000008363 phosphate buffer Substances 0.000 claims description 16
239000011780 sodium chloride Substances 0.000 claims description 16
229910052938 sodium sulfate Inorganic materials 0.000 claims description 16
235000011152 sodium sulphate Nutrition 0.000 claims description 16
239000008346 aqueous phase Substances 0.000 claims description 15
239000007795 chemical reaction product Substances 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
239000002156 adsorbate Substances 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
239000000706 filtrate Substances 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 6
229910000396 dipotassium phosphate Inorganic materials 0.000 claims description 6
235000019797 dipotassium phosphate Nutrition 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
150000003573 thiols Chemical class 0.000 claims description 6
FPVUWZFFEGYCGB-UHFFFAOYSA-N 5-methyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CC1=NN=C(S)S1 FPVUWZFFEGYCGB-UHFFFAOYSA-N 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 claims description 5
150000002576 ketones Chemical class 0.000 claims description 5
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
125000006413 ring segment Chemical group 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 4
239000000284 extract Substances 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
FZDRVLJSDYQRPO-HWZXHQHMSA-N (6r)-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CC(C)S[C@@H]2CC(=O)N21 FZDRVLJSDYQRPO-HWZXHQHMSA-N 0.000 claims description 3
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 claims description 3
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 3
239000005695 Ammonium acetate Substances 0.000 claims description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
229940043376 ammonium acetate Drugs 0.000 claims description 3
235000019257 ammonium acetate Nutrition 0.000 claims description 3
150000001735 carboxylic acids Chemical class 0.000 claims description 3
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 claims description 3
238000000354 decomposition reaction Methods 0.000 claims description 3
238000002844 melting Methods 0.000 claims description 3
230000008018 melting Effects 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
ZMFZQRZVPPIXKL-FGYPVYOSSA-N CC1S[C@H](C(C2=O)NC(CC#N)=O)N2C(C(O)=O)=C1SC1=NN=NN1C Chemical compound CC1S[C@H](C(C2=O)NC(CC#N)=O)N2C(C(O)=O)=C1SC1=NN=NN1C ZMFZQRZVPPIXKL-FGYPVYOSSA-N 0.000 claims description 2
TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 claims description 2
238000004587 chromatography analysis Methods 0.000 claims description 2
239000012043 crude product Substances 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
230000007717 exclusion Effects 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
239000006188 syrup Substances 0.000 claims description 2
235000020357 syrup Nutrition 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
125000003831 tetrazolyl group Chemical group 0.000 claims 3
125000001113 thiadiazolyl group Chemical group 0.000 claims 3
125000001425 triazolyl group Chemical group 0.000 claims 3
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
241000588724 Escherichia coli Species 0.000 abstract description 3
241000607142 Salmonella Species 0.000 abstract description 3
241000894006 Bacteria Species 0.000 abstract description 2
241000588769 Proteus <enterobacteria> Species 0.000 abstract description 2
125000000623 heterocyclic group Chemical group 0.000 abstract description 2
125000004434 sulfur atom Chemical group 0.000 abstract 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
150000003254 radicals Chemical class 0.000 description 9
229910000029 sodium carbonate Inorganic materials 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000002211 ultraviolet spectrum Methods 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
229910052784 alkaline earth metal Inorganic materials 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
125000005843 halogen group Chemical group 0.000 description 5
125000001544 thienyl group Chemical group 0.000 description 5
XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000001118 alkylidene group Chemical group 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
239000003513 alkali Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
150000005840 aryl radicals Chemical group 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
239000007858 starting material Substances 0.000 description 3
SFFUEHODRAXXIA-UHFFFAOYSA-N 2,2,2-trifluoroacetonitrile Chemical compound FC(F)(F)C#N SFFUEHODRAXXIA-UHFFFAOYSA-N 0.000 description 2
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
OITVBHWDBZTXTE-ANXXIGAQSA-N CC1S[C@H](C(C2=O)NC(CC#N)=O)N2C(C(O)=O)=C1SC1=NN=C(C)S1 Chemical compound CC1S[C@H](C(C2=O)NC(CC#N)=O)N2C(C(O)=O)=C1SC1=NN=C(C)S1 OITVBHWDBZTXTE-ANXXIGAQSA-N 0.000 description 2
241000588747 Klebsiella pneumoniae Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000013078 crystal Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
244000005700 microbiome Species 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
YPXORIWMZWNGLK-PVSHWOEXSA-N (6R)-4-methyl-4-(1-methyltetrazol-5-yl)sulfanyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SC1(S[C@H]2N(C(=C1)C(=O)O)C(C2)=O)C YPXORIWMZWNGLK-PVSHWOEXSA-N 0.000 description 1
NQOYPRFYENFQCW-ANXXIGAQSA-N (6R)-7-[(2-cyanoacetyl)amino]-4-methyl-3-[(5-methyl-1H-1,2,4-triazol-3-yl)sulfanyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(#N)CC(=O)NC1[C@@H]2N(C(=C(C(S2)C)SC2=NC(=NN2)C)C(=O)O)C1=O NQOYPRFYENFQCW-ANXXIGAQSA-N 0.000 description 1
KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
ZWKNLRXFUTWSOY-QPJJXVBHSA-N (e)-3-phenylprop-2-enenitrile Chemical compound N#C\C=C\C1=CC=CC=C1 ZWKNLRXFUTWSOY-QPJJXVBHSA-N 0.000 description 1
125000004503 1,2,3-oxadiazol-5-yl group Chemical group O1N=NC=C1* 0.000 description 1
125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 1
125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 description 1
125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 1
125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 description 1
125000004510 1,3,4-oxadiazol-5-yl group Chemical group O1C=NN=C1* 0.000 description 1
125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
GRWKNBPOGBTZMN-UHFFFAOYSA-N 2-benzyl-3-phenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1CC(N)(CN)CC1=CC=CC=C1 GRWKNBPOGBTZMN-UHFFFAOYSA-N 0.000 description 1
VKIGAWAEXPTIOL-UHFFFAOYSA-N 2-hydroxyhexanenitrile Chemical compound CCCCC(O)C#N VKIGAWAEXPTIOL-UHFFFAOYSA-N 0.000 description 1
QPHZWABVAIGWHI-UHFFFAOYSA-N 3-methyl-2h-1,2,4-thiadiazole-5-thione Chemical compound CC1=NSC(S)=N1 QPHZWABVAIGWHI-UHFFFAOYSA-N 0.000 description 1
BMRPJOWYCLFENV-UHFFFAOYSA-N 3-oxopropanenitrile Chemical class O=[C]CC#N BMRPJOWYCLFENV-UHFFFAOYSA-N 0.000 description 1
JLAMDELLBBZOOX-UHFFFAOYSA-N 3h-1,3,4-thiadiazole-2-thione Chemical compound SC1=NN=CS1 JLAMDELLBBZOOX-UHFFFAOYSA-N 0.000 description 1
TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 1
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
OUZCWDMJTKYHCA-UHFFFAOYSA-N 5-methyl-1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound CC1=NNC(S)=N1 OUZCWDMJTKYHCA-UHFFFAOYSA-N 0.000 description 1
ZVGKPQCCKGLQPB-UHFFFAOYSA-N 5-methyl-3h-1,3,4-oxadiazole-2-thione Chemical compound CC1=NN=C(S)O1 ZVGKPQCCKGLQPB-UHFFFAOYSA-N 0.000 description 1
CFWGYKRJMYXYND-UHFFFAOYSA-N 5-methylsulfanyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CSC1=NN=C(S)S1 CFWGYKRJMYXYND-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
JWHHVVUQTDBZJY-FGYPVYOSSA-N CC1S[C@H](C(C2=O)NC(CC#N)=O)N2C(C(O)=O)=C1SC1=NN=C(SC)S1 Chemical compound CC1S[C@H](C(C2=O)NC(CC#N)=O)N2C(C(O)=O)=C1SC1=NN=C(SC)S1 JWHHVVUQTDBZJY-FGYPVYOSSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
101100295741 Gallus gallus COR4 gene Proteins 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
CZDSWGSBWBDBQV-UHFFFAOYSA-N acetic acid;pentan-1-amine Chemical compound CC(O)=O.CCCCCN CZDSWGSBWBDBQV-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000002070 alkenylidene group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
125000002820 allylidene group Chemical group [H]C(=[*])C([H])=C([H])[H] 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003674 animal food additive Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
239000002585 base Substances 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 1
229940117916 cinnamic aldehyde Drugs 0.000 description 1
KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
229940031098 ethanolamine Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000011630 iodine Substances 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
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 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
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000000843 powder 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
229960004919 procaine Drugs 0.000 description 1
239000000047 product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
- C07D501/36—Methylene radicals, substituted by sulfur atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1773169A 1969-11-28 1969-11-28 Verfahren zur Herstellung von Derivaten der 7-Aminocephalosporansäure CH535259A (de)

Priority Applications (26)

Application Number	Priority Date	Filing Date	Title
BE759570D BE759570A (fr)	1969-11-28		Derives de l'acide 7-cyanacetylamino-cephalosporanique et procede pour leur preparation
CH1912071A CH535261A (de)	1969-11-28	1969-11-28	Verfahren zur Herstellung von Derivaten der 7-Aminocephalosporansäure
CH1773169A CH535259A (de)	1969-11-28	1969-11-28	Verfahren zur Herstellung von Derivaten der 7-Aminocephalosporansäure
US00090470A US3719673A (en)	1969-11-28	1970-11-17	Derivatives of 7-aminocephalosporanic acid
ZA707786A ZA707786B (en)	1969-11-28	1970-11-18	New derivatives of 7-aminocephalosporanic acid
DE2056983A DE2056983B2 (de)	1969-11-28	1970-11-20	S-Heterocyclylthiomethyl-Cephalosporine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
FR7042091A FR2073428B1 (cs)	1969-11-28	1970-11-24
CA098,942A CA972363A (en)	1969-11-28	1970-11-24	Process for the manufacture of new derivatives of 7-amino-cephalosporanic acid
FI703172A FI52094C (fi)	1969-11-28	1970-11-25	Menetelmä uusien, antimikrobisesti tehokkaiden 7-asyyliamino-kef-3-em- 4-karbonihapon 3-asemassa substituoitujen johdannaisten valmistamiseks i.
IE1514/70A IE34762B1 (en)	1969-11-28	1970-11-25	Derivatives of 7-aminocephalosporanic acid
EG498/70A EG10710A (en)	1969-11-28	1970-11-26	Process for the manufacture of new derivatives of 7-aminocephalosporanic acid having a curative action & can be used as a preservative for food and as antiseptics
SE7016021A SE386902B (sv)	1969-11-28	1970-11-26	Forfarande for framstellning av nya cefalosporiner
SU1766771A SU449488A3 (ru)	1969-11-28	1970-11-26	Способ получени производных 7-аминоцефалоспорановой кислоты
SU1494601A SU507245A3 (ru)	1969-11-28	1970-11-26	Способ получени производных 7-ациламиноцефалоспорановой кислоты
ES385906A ES385906A1 (es)	1969-11-28	1970-11-26	Procedimiento para la obtencion de derivados del acido -7- amino cefaloesporanico.
OA54099A OA03830A (fr)	1969-11-28	1970-11-26	Procédé pour la préparation de composés acylaminogènes.
CS7973A CS177093B2 (cs)	1969-11-28	1970-11-27
PL1970144679A PL81220B1 (en)	1969-11-28	1970-11-27	Derivatives of 7-aminocephalosporanic acid[us3719673a]
CS8019A CS177055B2 (cs)	1969-11-28	1970-11-27
AT1071970A AT301756B (de)	1969-11-28	1970-11-27	Verfahren zur Herstellung neuer Derivate der 7-Amino-cephalosporansäure
AT926671A AT303970B (de)	1969-11-28	1970-11-27	Verfahren zur Herstellung neuer Derivate der 7-Amino-cephalo-sporansäure
GB5641370A GB1336318A (en)	1969-11-28	1970-11-27	Derivatives of 7-aminocephalosporanic acid
NL7017401A NL7017401A (cs)	1969-11-28	1970-11-27
HUCI001055 HU162758B (cs)	1969-11-28	1970-11-28
JP45104507A JPS5017075B1 (cs)	1969-11-28	1970-11-28
ES415467A ES415467A1 (es)	1969-11-28	1973-06-01	Procedimiento para la obtencion de derivados del acido 7- amino-cefalosporanico.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1773169A CH535259A (de)	1969-11-28	1969-11-28	Verfahren zur Herstellung von Derivaten der 7-Aminocephalosporansäure

Publications (1)

Publication Number	Publication Date
CH535259A true CH535259A (de)	1973-03-31

Family

ID=4427654

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1773169A CH535259A (de)	1969-11-28	1969-11-28	Verfahren zur Herstellung von Derivaten der 7-Aminocephalosporansäure
CH1912071A CH535261A (de)	1969-11-28	1969-11-28	Verfahren zur Herstellung von Derivaten der 7-Aminocephalosporansäure

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1912071A CH535261A (de)	1969-11-28	1969-11-28	Verfahren zur Herstellung von Derivaten der 7-Aminocephalosporansäure

Country Status (3)

Country	Link
CH (2)	CH535259A (cs)
CS (2)	CS177055B2 (cs)
ZA (1)	ZA707786B (cs)

1969
- 1969-11-28 CH CH1773169A patent/CH535259A/de not_active IP Right Cessation
- 1969-11-28 CH CH1912071A patent/CH535261A/de not_active IP Right Cessation
1970
- 1970-11-18 ZA ZA707786A patent/ZA707786B/xx unknown
- 1970-11-27 CS CS8019A patent/CS177055B2/cs unknown
- 1970-11-27 CS CS7973A patent/CS177093B2/cs unknown

Also Published As

Publication number	Publication date
ZA707786B (en)	1971-12-29
CS177093B2 (cs)	1977-07-29
CH535261A (de)	1973-03-31
CS177055B2 (cs)	1977-07-29

Legal Events

Date	Code	Title	Description
1980-07-31	PL	Patent ceased

Publication	Publication Date	Title
DE3037997A1 (de)	1982-05-13	(beta) -lactamantibiotika, verfahren zu deren herstellung sowie sie enthaltende mittel
DE1670625B2 (de)	1974-10-24	7-alpha-Aminobenzyl-3-methylcephalosporinanaloge und ihre Herstellung
EP0004956B1 (de)	1981-10-14	Beta-Lactamantibiotika, Verfahren zu ihrer Herstellung, Futterzusatzmittel, Arzneimittel sowie Verfahren zu deren Herstellung
DE2801644A1 (de)	1978-08-17	Heteromonocyclische und heterobicyclische derivate der ungesaettigten 7-acylamido-3-cephem-4-carbonsaeure, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische oder veterinaer- zubereitung
DE1670324A1 (de)	1970-10-29	Neue Derivate der 7-Amino-cephalosporansaeure
DE2056983A1 (de)	1971-06-09	Verfahren zur Herstellung von Acylamino verbindungen
DE3887691T2 (de)	1994-06-09	Cephalosporin-antibiotika.
CH626370A5 (en)	1981-11-13	Process for the preparation of the syn isomer or of a mixture of syn and anti isomers of 7beta-acylamidoceph-3-em-4-carboxylic acids with antibiotic activity
DE2732283A1 (de)	1979-01-25	Beta-lactam-verbindungen
DE2558869C2 (de)	1982-09-23	Cephalosporine
CH636879A5 (de)	1983-06-30	Verfahren zur herstellung 7-substituierter aminoacetamido-oxadethia-cephalosporine.
DE2715038A1 (de)	1977-11-24	Neue antibakterielle verbindungen
CH535259A (de)	1973-03-31	Verfahren zur Herstellung von Derivaten der 7-Aminocephalosporansäure
EP0098433B1 (de)	1987-12-02	Beta-Lactamantibiotika, Verfahren zu deren Herstellung sowie sie enthaltende Mittel
AT301756B (de)	1972-09-25	Verfahren zur Herstellung neuer Derivate der 7-Amino-cephalosporansäure
DE2655717A1 (de)	1977-06-30	Thiadiazolylderivate von 7-acylamido-3-cephem-4-carbonsaeure, verfahren zu deren herstellung und dieselben enthaltende pharmazeutische und veterinaermedizinische mittel
DE2645144C2 (de)	1986-11-27	Cephalosporine, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Mittel
EP0054970B1 (de)	1985-07-17	7-Beta-(Ketooximinoacylamido)-ceph-3-em-4-carbonsäurederivate, Verfahren zur Herstellung derselben und diese enthaltende Arzneimittel
DE2356704A1 (de)	1974-05-22	3-(heterocyclische-thiomethyl)-cephalosporinverbindungen und ihre pharmakologisch vertraeglichen salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
DE2454109A1 (de)	1975-05-15	Neue cephalosporinderivate, deren herstellung und diese enthaltende zusammensetzungen
DE2818985C2 (de)	1995-08-17	Halogenarylmalonamidooxacephalosporine und deren Verwendung bei der Bekämpfung bakterieller Infektionen
CH623327A5 (cs)	1981-05-29
CH556357A (de)	1974-11-29	Verfahren zur herstellung von derivaten der 7-aminocephalosporansaeure.
DE2632006A1 (de)	1977-02-10	7- eckige klammer auf alpha-amino- omega-(3,4-methylendioxyphenyl)acylamido eckige klammer zu cephalosporansaeurederivate
AT255646B (de)	1967-07-10	Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure