IL30546A - Cephalosporin compounds for use as antibacterial agents and a process for their production - Google Patents

Cephalosporin compounds for use as antibacterial agents and a process for their production

Info

Publication number: IL30546A
Authority: IL; Israel
Prior art keywords: acid; water; mole; formula; product
Prior art date: 1967-08-18

Application number

IL30546A

Other languages

English (en)

Other versions

IL30546A0 (en

Original Assignee

Bristol Myers Co

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.)

1967-08-18

Filing date

1968-08-13

Publication date

1972-02-29

1968-08-13 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1968-10-24 Publication of IL30546A0 publication Critical patent/IL30546A0/xx

1972-02-29 Publication of IL30546A publication Critical patent/IL30546A/en

Links

238000000034 method Methods 0.000 title claims description 19
-1 Cephalosporin compounds Chemical class 0.000 title description 10
229930186147 Cephalosporin Natural products 0.000 title description 5
229940124587 cephalosporin Drugs 0.000 title description 5
238000004519 manufacturing process Methods 0.000 title description 2
239000003242 anti bacterial agent Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 16
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
231100000252 nontoxic Toxicity 0.000 claims description 6
230000003000 nontoxic effect Effects 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 4
150000008065 acid anhydrides Chemical class 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
239000000047 product Substances 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
239000002253 acid Substances 0.000 description 28
239000000243 solution Substances 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
239000007787 solid Substances 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
238000001914 filtration Methods 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000002024 ethyl acetate extract Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229940086542 triethylamine Drugs 0.000 description 5
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 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
229960003424 phenylacetic acid Drugs 0.000 description 4
239000003279 phenylacetic acid Substances 0.000 description 4
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000010933 acylation Effects 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
150000001780 cephalosporins Chemical class 0.000 description 3
229960001701 chloroform Drugs 0.000 description 3
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000395 magnesium oxide Substances 0.000 description 3
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
229940043265 methyl isobutyl ketone Drugs 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000012071 phase Substances 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
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
CFGDUGSIBUXRMR-UHFFFAOYSA-N 1,2-dihydropyrrol-2-ide Chemical compound C=1C=[C-]NC=1 CFGDUGSIBUXRMR-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
241000193998 Streptococcus pneumoniae Species 0.000 description 2
241000193996 Streptococcus pyogenes Species 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 2
238000010792 warming Methods 0.000 description 2
FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 description 1
WKVZMKDXJFCMMD-UVWUDEKDSA-L (5ar,8ar,9r)-5-[[(2r,4ar,6r,7r,8r,8as)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one;azanide;n,3-bis(2-chloroethyl)-2-ox Chemical compound [NH2-].[NH2-].Cl[Pt+2]Cl.ClCCNP1(=O)OCCCN1CCCl.COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3C(O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 WKVZMKDXJFCMMD-UVWUDEKDSA-L 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-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
VPHBBPORANRKLD-UHFFFAOYSA-N 2-(4-acetamidophenyl)-2-aminoacetic acid Chemical compound CC(=O)NC1=CC=C(C(N)C(O)=O)C=C1 VPHBBPORANRKLD-UHFFFAOYSA-N 0.000 description 1
RJMYTHGQVJWWJO-UHFFFAOYSA-N 2-azaniumyl-2-(3-nitrophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=CC([N+]([O-])=O)=C1 RJMYTHGQVJWWJO-UHFFFAOYSA-N 0.000 description 1
WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 1
JYJIMEQNTHFXMT-UHFFFAOYSA-N 2-nitro-2-phenylacetic acid Chemical compound OC(=O)C([N+]([O-])=O)C1=CC=CC=C1 JYJIMEQNTHFXMT-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
VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical group [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
241000588747 Klebsiella pneumoniae Species 0.000 description 1
XNPOFXIBHOVFFH-UHFFFAOYSA-N N-cyclohexyl-N'-(2-(4-morpholinyl)ethyl)carbodiimide Chemical compound C1CCCCC1N=C=NCCN1CCOCC1 XNPOFXIBHOVFFH-UHFFFAOYSA-N 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
238000007605 air drying Methods 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
239000012964 benzotriazole Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
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 description 1
238000006243 chemical reaction Methods 0.000 description 1
235000019628 coolness Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 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
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002401 inhibitory effect Effects 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
150000003932 ketenimines Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000004682 monohydrates Chemical class 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
230000000802 nitrating effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000012258 stirred mixture Substances 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
150000007970 thio esters Chemical class 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005292 vacuum distillation 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
- C07D501/14—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
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/32—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by an araliphatic carboxylic acid, which is substituted on the aliphatic radical by hetero atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cephalosporin Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Peptides Or Proteins (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IL30546A 1967-08-18 1968-08-13 Cephalosporin compounds for use as antibacterial agents and a process for their production IL30546A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US66152067A	1967-08-18	1967-08-18

Publications (2)

Publication Number	Publication Date
IL30546A0 IL30546A0 (en)	1968-10-24
IL30546A true IL30546A (en)	1972-02-29

Family

ID=24653945

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL30546A IL30546A (en)	1967-08-18	1968-08-13	Cephalosporin compounds for use as antibacterial agents and a process for their production

Country Status (8)

Country	Link
US (1)	US3464985A (de)
BE (1)	BE719594A (de)
CH (1)	CH505854A (de)
DE (1)	DE1795151C3 (de)
FR (2)	FR7996M (de)
GB (4)	GB1247714A (de)
IL (1)	IL30546A (de)
NL (1)	NL154740B (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3714146A (en) *	1970-10-05	1973-01-30	Bristol Myers Co	Novel syntheses of cephalexin and intermediates therefor
US4007173A (en) *	1973-05-07	1977-02-08	Smithkline Corporation	α-amino-α-(ureidophenyl)acetamidocephalosporins
US4022895A (en) *	1973-08-01	1977-05-10	Smithkline Corporation	Substituted phenylglycylcephalosporins
US4018921A (en) *	1973-08-01	1977-04-19	Smithkline Corporation	Substituted phenylglycylcephalosporins
US3931160A (en) *	1974-05-15	1976-01-06	Smithkline Corporation	α-Amino-α-(acylamidophenyl)acetamidocephalosporins
US4092480A (en) *	1975-12-15	1978-05-30	Smithkline Corporation	Intermediates for preparing substituted phenylglycylcephalosporins
DE2836613A1 (de) *	1978-08-22	1980-03-13	Bayer Ag	Alpha -aminophenylessigsaeurederivate
WO2016063246A1 (en) *	2014-10-22	2016-04-28	Sun Pharmaceutical Industries Limited	Crystalline form r of tedizolid phosphate

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3311621A (en) *	1966-04-07	1967-03-28	Bristol Myers Co	Derivatives of cephalosporanic acid

1967
- 1967-08-18 US US661520A patent/US3464985A/en not_active Expired - Lifetime
1968
- 1968-08-13 IL IL30546A patent/IL30546A/en unknown
- 1968-08-16 BE BE719594D patent/BE719594A/xx unknown
- 1968-08-16 NL NL686811676A patent/NL154740B/xx unknown
- 1968-08-16 DE DE1795151A patent/DE1795151C3/de not_active Expired
- 1968-08-19 GB GB03808/71D patent/GB1247714A/en not_active Expired
- 1968-08-19 CH CH1257968A patent/CH505854A/de not_active IP Right Cessation
- 1968-08-19 GB GB39617/68A patent/GB1247711A/en not_active Expired
- 1968-08-19 GB GB03807/71A patent/GB1247713A/en not_active Expired
- 1968-08-19 GB GB5020/71A patent/GB1247712A/en not_active Expired
- 1968-11-15 FR FR173954A patent/FR7996M/fr not_active Expired
1969
- 1969-08-16 FR FR1603727D patent/FR1603727A/fr not_active Expired

Also Published As

Publication number	Publication date
IL30546A0 (en)	1968-10-24
GB1247711A (en)	1971-09-29
NL6811676A (de)	1969-02-20
DE1795151A1 (de)	1972-03-23
NL154740B (nl)	1977-10-17
GB1247712A (en)	1971-09-29
GB1247713A (en)	1971-09-29
DE1795151C3 (de)	1975-04-24
DE1795151B2 (de)	1974-08-29
FR1603727A (de)	1971-05-24
GB1247714A (en)	1971-09-29
CH505854A (de)	1971-04-15
BE719594A (de)	1969-02-17
US3464985A (en)	1969-09-02
FR7996M (de)	1970-06-08

Publication	Publication Date	Title
DK144763B (da)	1982-06-01	Analogifremgangsmaade til fremstilling af cephalosporinderivater
JPS62174018A (ja)	1987-07-30	細菌性感染症治療剤
SU1480763A3 (ru)	1989-05-15	Способ получени производных 1-сульфо-2-оксоазетидинона или их солей, или сложных эфиров
US3687949A (en)	1972-08-29	Synthetic cephalosporins
JPS6237037B2 (de)	1987-08-10
IE45015B1 (en)	1982-06-02	New oxime derivatives of 7-aminothiazolylacetamido-cephalosporanic acid, processes for preparing them and pharmaceutical compositions incorporating them
US4012382A (en)	1977-03-15	α-Amino and α-formyl-α-(p-acyloxyphenyl)acetamidocephalosporanic acid derivatives
JPH0246565B2 (de)	1990-10-16
IL30546A (en)	1972-02-29	Cephalosporin compounds for use as antibacterial agents and a process for their production
SU447886A1 (ru)	1974-10-25	Способ получени защищенной 4,6-0-алкилиден- - -глюкопиранозы
SU845789A3 (ru)	1981-07-07	Способ получени -7- -(4-окси-6-метил-НиКОТиНАМидО)- -(4-ОКСифЕНил)АцЕТАМидО -3- (1-МЕТилТЕТРАзОл-5-ил)ТиОМЕТил-3-цЕфЕМ-4-КАРбО-НОВОй КиСлОТы
SE444683B (sv)	1986-04-28	Syn-isomerer av 3-substituerade 7-amino-tiazolyl-acetamido-cefalosporansyraforeningar och farmaceutiska kompositioner till anvendning mot gram-positiva och gram-negativa bakterier
JPS6337116B2 (de)	1988-07-22
US3527793A (en)	1970-09-08	Phenylglycine derivatives
HU181961B (en)	1983-11-28	Process for producing new oxime derivatives of 3-thiadiazolythio-methyl-7-aminothiazolylacetamido-ceph-3-eme-4-carboxylic acids
GB1584398A (en)	1981-02-11	Oxime derivatives of 3-carbamoyloxymethyl-7-amino-thiazolyl-acetamido-ceph-3-em-4-carboxylic acid processes for preparing them and pharmaceutical compositions containing them
US3910899A (en)	1975-10-07	7-(2-Aminomethylphenyl-acetamido)-3-{8 2-(5-hydroxymethyl-1,3,4-thiadiazolyl)-thiomethyl{9 -3-cephem-4-carboxylic acid
JPS5919114B2 (ja)	1984-05-02	セフアロスポリンの製造法
US4415567A (en)	1983-11-15	7α-Methoxycephalosporin derivatives, and antibacterial drugs containing the same
US4182863A (en)	1980-01-08	7-Amino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid
USRE29164E (en)	1977-03-29	7-Amino-cephalosporanic and decephalosporanic acid derivatives
US4285939A (en)	1981-08-25	Cephalosporin derivatives, and antibacterial drugs containing the derivatives
US2966484A (en)	1960-12-27	Chemical compounds
US3049551A (en)	1962-08-14	Novobiocin intermediate and process therefor
US3296250A (en)	1967-01-03	4-thiazolylmethylpenicillins