CH601314A5 - Antibacterial alkanoyloxymethyl cephalosporin esters - Google Patents
Antibacterial alkanoyloxymethyl cephalosporin estersInfo
- Publication number
- CH601314A5 CH601314A5 CH635475A CH635475A CH601314A5 CH 601314 A5 CH601314 A5 CH 601314A5 CH 635475 A CH635475 A CH 635475A CH 635475 A CH635475 A CH 635475A CH 601314 A5 CH601314 A5 CH 601314A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- tetrazol
- cephem
- ylthiomethyl
- carboxylic acid
- Prior art date
Links
- -1 alkanoyloxymethyl cephalosporin esters Chemical class 0.000 title claims abstract description 59
- 229940124587 cephalosporin Drugs 0.000 title claims abstract description 14
- 229930186147 Cephalosporin Natural products 0.000 title claims abstract description 9
- 230000000844 anti-bacterial effect Effects 0.000 title abstract 2
- 239000002253 acid Substances 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 29
- 238000005886 esterification reaction Methods 0.000 claims description 24
- 230000032050 esterification Effects 0.000 claims description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 150000001450 anions Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- NHYXMAKLBXBVEO-UHFFFAOYSA-N bromomethyl acetate Chemical compound CC(=O)OCBr NHYXMAKLBXBVEO-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Chemical group 0.000 claims description 5
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- RRJHESVQVSRQEX-MRXJRLSOSA-N (6R)-7-[[(2R)-2-formyloxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(=O)O[C@@H](C(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)O)C1=O)C1=CC=CC=C1 RRJHESVQVSRQEX-MRXJRLSOSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- OLVCFLKTBJRLHI-ZUZSALNQSA-N (6R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C([C@H](O)C1=CC=CC=C1)(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)O)C1=O OLVCFLKTBJRLHI-ZUZSALNQSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- JLAWNOKQPBBITM-JDQGPONISA-N CC(OCOC(C1=C(CSC2=NN=NN2C)CS[C@H](C2NC([C@@H](C3=CC=CC=C3)O)=O)N1C2=O)=O)=O Chemical compound CC(OCOC(C1=C(CSC2=NN=NN2C)CS[C@H](C2NC([C@@H](C3=CC=CC=C3)O)=O)N1C2=O)=O)=O JLAWNOKQPBBITM-JDQGPONISA-N 0.000 claims 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 239000002585 base Substances 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- SMJYMSAPPGLBAR-UHFFFAOYSA-N chloromethyl acetate Chemical compound CC(=O)OCCl SMJYMSAPPGLBAR-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000004970 halomethyl group Chemical group 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- ACBDNFPUXYGKPT-UHFFFAOYSA-N bromomethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCBr ACBDNFPUXYGKPT-UHFFFAOYSA-N 0.000 description 3
- 125000005997 bromomethyl group Chemical group 0.000 description 3
- 150000001780 cephalosporins Chemical class 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000005042 acyloxymethyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000006237 oxymethylenoxy group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 150000002960 penicillins Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000003335 steric effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- LJAJSQKLOBWCTG-MRVPVSSYSA-N (1-methyltetrazol-5-yl)sulfanylmethyl (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound CN1N=NN=C1SCOC(=O)C1=CCS[C@H]2N1C(C2)=O LJAJSQKLOBWCTG-MRVPVSSYSA-N 0.000 description 1
- CNAGMNMBHMQZPF-MKTAYPAQSA-N (6R)-3-(acetyloxymethyl)-7-[(2-hydroxy-2-phenylacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C(C(O)C1=CC=CC=C1)(=O)NC1[C@@H]2N(C(=C(CS2)COC(C)=O)C(=O)O)C1=O CNAGMNMBHMQZPF-MKTAYPAQSA-N 0.000 description 1
- PIXMOMPJMIAMLJ-FFFFSGIJSA-N (6R)-3-(acetyloxymethyl)-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N1(N=NN=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)COC(C)=O)C(=O)O)C1=O PIXMOMPJMIAMLJ-FFFFSGIJSA-N 0.000 description 1
- XGCZJDZFYNKVIK-SBXXRYSUSA-N (6R)-3-(methylsulfanylmethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CSCC=1CS[C@H]2N(C=1C(=O)O)C(C2NC(CC=1SC=CC=1)=O)=O XGCZJDZFYNKVIK-SBXXRYSUSA-N 0.000 description 1
- WJJYDNKVEGMTBM-FBMWCMRBSA-N (6r)-3-(acetyloxymethyl)-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)NC(=O)COC1=CC=CC=C1 WJJYDNKVEGMTBM-FBMWCMRBSA-N 0.000 description 1
- GOFCPYKUMJBHBH-FBMWCMRBSA-N (6r)-3-(acetyloxymethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)NC(=O)CC1=CC=CC=C1 GOFCPYKUMJBHBH-FBMWCMRBSA-N 0.000 description 1
- XIURVHNZVLADCM-WPZCJLIBSA-N (6r)-3-(acetyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)NC(=O)CC1=CC=CS1 XIURVHNZVLADCM-WPZCJLIBSA-N 0.000 description 1
- NGUGGZZGPVSQNS-FQNRMIAFSA-N (6r)-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)C(NC(=O)COC=3C=CC=CC=3)[C@H]2SC1 NGUGGZZGPVSQNS-FQNRMIAFSA-N 0.000 description 1
- FGYKFRAJEMTRRR-FQNRMIAFSA-N (6r)-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)C(NC(=O)CC=3C=CC=CC=3)[C@H]2SC1 FGYKFRAJEMTRRR-FQNRMIAFSA-N 0.000 description 1
- QNJVDZUXRBFPRA-SBXXRYSUSA-N (6r)-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)C(NC(=O)CC=3SC=CC=3)[C@H]2SC1 QNJVDZUXRBFPRA-SBXXRYSUSA-N 0.000 description 1
- RNVNQJDGAABCAO-QHDYGNBISA-N (6r)-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)C(NC(=O)CN3N=NN=C3)[C@H]2SC1 RNVNQJDGAABCAO-QHDYGNBISA-N 0.000 description 1
- IYNQZPTYTYFUPZ-FBMWCMRBSA-N (6r)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)C(NC(=O)COC=3C=CC=CC=3)[C@H]2SC1 IYNQZPTYTYFUPZ-FBMWCMRBSA-N 0.000 description 1
- JKSGJOGGZPWNTE-FBMWCMRBSA-N (6r)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)C(NC(=O)CC=3C=CC=CC=3)[C@H]2SC1 JKSGJOGGZPWNTE-FBMWCMRBSA-N 0.000 description 1
- MLYYVTUWGNIJIB-FFFFSGIJSA-N (6r)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)C(NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-FFFFSGIJSA-N 0.000 description 1
- CIPQGGYPCPIDBB-WPZCJLIBSA-N (6r)-3-methyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(O)=O)NC(=O)CC1=CC=CC=C1 CIPQGGYPCPIDBB-WPZCJLIBSA-N 0.000 description 1
- KCCXIEAFHKKZLW-JLOHTSLTSA-N (6r)-3-methyl-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(O)=O)NC(=O)CC1=CC=CS1 KCCXIEAFHKKZLW-JLOHTSLTSA-N 0.000 description 1
- OLVCFLKTBJRLHI-IJGSQOGDSA-N (6r)-7-[(2-hydroxy-2-phenylacetyl)amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)C(NC(=O)C(O)C=3C=CC=CC=3)[C@H]2SC1 OLVCFLKTBJRLHI-IJGSQOGDSA-N 0.000 description 1
- VDFFPBOAOLQAJV-MKTAYPAQSA-N (6r)-7-[(2-hydroxy-2-phenylacetyl)amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)C(NC(=O)C(O)C=3C=CC=CC=3)[C@H]2SC1 VDFFPBOAOLQAJV-MKTAYPAQSA-N 0.000 description 1
- BMYHQZVYLLQHKO-MBRGGSNBSA-N (6r)-7-[(2-hydroxy-2-phenylacetyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(O)=O)NC(=O)C(O)C1=CC=CC=C1 BMYHQZVYLLQHKO-MBRGGSNBSA-N 0.000 description 1
- XZWUXKVIZOHFTC-QHDYGNBISA-N (6r)-7-acetamido-3-(acetyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(COC(C)=O)=C(C(O)=O)N2C(=O)C(NC(=O)C)[C@H]21 XZWUXKVIZOHFTC-QHDYGNBISA-N 0.000 description 1
- VMZFBPKXDAYFCI-OMNKOJBGSA-N (6r)-7-acetamido-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)NC(=O)C)CC=1CSC1=NN=NN1C VMZFBPKXDAYFCI-OMNKOJBGSA-N 0.000 description 1
- LKKFYNULQQYBOV-IOJJLOCKSA-N (6r)-7-acetamido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)C(NC(=O)C)[C@H]21 LKKFYNULQQYBOV-IOJJLOCKSA-N 0.000 description 1
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- RBTFXTIDUUBYRK-LQRGHNGLSA-N CC(=O)OCOC(=O)C1=C(CS[C@H]2N1C(=O)C2NC(=O)[C@@H](C3=CC=CC=C3)OC=O)CSC4=NN=NN4C Chemical compound CC(=O)OCOC(=O)C1=C(CS[C@H]2N1C(=O)C2NC(=O)[C@@H](C3=CC=CC=C3)OC=O)CSC4=NN=NN4C RBTFXTIDUUBYRK-LQRGHNGLSA-N 0.000 description 1
- ULOVZMQVZXWKLO-LQRGHNGLSA-N CC(C)(C)C(=O)OCOC(=O)C1=C(CS[C@H]2N1C(=O)C2NC(=O)[C@@H](C3=CC=CC=C3)O)CSC4=NN=NN4C Chemical compound CC(C)(C)C(=O)OCOC(=O)C1=C(CS[C@H]2N1C(=O)C2NC(=O)[C@@H](C3=CC=CC=C3)O)CSC4=NN=NN4C ULOVZMQVZXWKLO-LQRGHNGLSA-N 0.000 description 1
- FFUGMQNACCIPMW-QHNQYTFYSA-N CC(C)(C)C(=O)OCOC(=O)C1=C(CS[C@H]2N1C(=O)C2NC(=O)[C@@H](C3=CC=CC=C3)OC=O)CSC4=NN=NN4C Chemical compound CC(C)(C)C(=O)OCOC(=O)C1=C(CS[C@H]2N1C(=O)C2NC(=O)[C@@H](C3=CC=CC=C3)OC=O)CSC4=NN=NN4C FFUGMQNACCIPMW-QHNQYTFYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- AIEFWPONAXOMOR-UHFFFAOYSA-N iodomethyl butanoate Chemical compound CCCC(=O)OCI AIEFWPONAXOMOR-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940083555 sodium cephalothin Drugs 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000005406 washing 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
- C07D501/36—Methylene radicals, substituted by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/471,528 US3933808A (en) | 1974-05-20 | 1974-05-20 | Cephalosporin esters |
| US471527A US3928333A (en) | 1974-05-20 | 1974-05-20 | Process for the preparation of 3 cephalosporin esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH601314A5 true CH601314A5 (en) | 1978-07-14 |
Family
ID=27043469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH635475A CH601314A5 (en) | 1974-05-20 | 1975-05-16 | Antibacterial alkanoyloxymethyl cephalosporin esters |
Country Status (13)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190897B (it) * | 1982-06-29 | 1988-02-24 | Opos Biochimica Srl | Procedimento per la preparazione dell'estere 1-etossicarbonilossietilico dell'acido 6-(d(-)-alfa aminoalfa fenilacetamido)-penicillanico |
| US4606865A (en) * | 1982-09-20 | 1986-08-19 | Astra Lakemedel Aktiebolag | Methods for the preparation of α-bromodiethylcarbonate |
-
1975
- 1975-05-16 CH CH635475A patent/CH601314A5/de not_active IP Right Cessation
- 1975-05-16 YU YU01255/75A patent/YU125575A/xx unknown
- 1975-05-17 PL PL1975180468A patent/PL103490B1/pl unknown
- 1975-05-19 CS CS753481A patent/CS196272B2/cs unknown
- 1975-05-19 SU SU752134779A patent/SU731899A3/ru active
- 1975-05-19 HU HUEI620A patent/HU170561B/hu unknown
- 1975-05-20 AT AT381675A patent/AT340589B/de not_active IP Right Cessation
- 1975-05-20 ES ES437809A patent/ES437809A1/es not_active Expired
- 1975-05-20 DK DK221875A patent/DK221875A/da unknown
- 1975-05-20 BG BG031234A patent/BG25228A3/xx unknown
- 1975-05-20 AR AR258878A patent/AR212321A1/es active
- 1975-05-20 SE SE7505741A patent/SE421701B/xx unknown
- 1975-05-20 DD DD186129A patent/DD120446A5/xx unknown
- 1975-05-20 BG BG030033A patent/BG25096A3/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG25228A3 (en) | 1978-08-10 |
| DD120446A5 (enrdf_load_stackoverflow) | 1976-06-12 |
| BG25096A3 (en) | 1978-07-12 |
| CS196272B2 (en) | 1980-03-31 |
| SU731899A3 (ru) | 1980-04-30 |
| DK221875A (da) | 1975-11-21 |
| PL103490B1 (pl) | 1979-06-30 |
| AR212321A1 (es) | 1978-06-30 |
| SE421701B (sv) | 1982-01-25 |
| ES437809A1 (es) | 1977-04-01 |
| YU125575A (en) | 1982-05-31 |
| ATA381675A (de) | 1977-04-15 |
| AT340589B (de) | 1977-12-27 |
| SE7505741L (sv) | 1975-11-21 |
| HU170561B (enrdf_load_stackoverflow) | 1977-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |