CH626625A5 - - Google Patents
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- CH626625A5 CH626625A5 CH484377A CH484377A CH626625A5 CH 626625 A5 CH626625 A5 CH 626625A5 CH 484377 A CH484377 A CH 484377A CH 484377 A CH484377 A CH 484377A CH 626625 A5 CH626625 A5 CH 626625A5
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- CH
- Switzerland
- Prior art keywords
- acid
- cephem
- group
- formula
- general formula
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- -1 halomethyl cephem compound Chemical class 0.000 claims description 122
- 238000000034 method Methods 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000007858 starting material Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 9
- QSBIAXINNCXXNV-SSDOTTSWSA-N (6r)-3-(hydroxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical class C1C(CO)=CS[C@@H]2CC(=O)N21 QSBIAXINNCXXNV-SSDOTTSWSA-N 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 150000001447 alkali salts Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical compound S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
- 229940106681 chloroacetic acid Drugs 0.000 claims description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229960005215 dichloroacetic acid Drugs 0.000 claims description 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 125000005103 alkyl silyl group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229940013688 formic acid Drugs 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000007273 lactonization reaction Methods 0.000 description 7
- 125000004442 acylamino group Chemical group 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- OLCDHLIQTOUMBO-SSDOTTSWSA-N (6r)-3-(hydroxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1CC(CO)=CN2C(=O)C[C@H]21 OLCDHLIQTOUMBO-SSDOTTSWSA-N 0.000 description 4
- MAFIPFSQYBWLAM-BAFYGKSASA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid Chemical compound OC(=O)C1C=CS[C@@H]2CC(=O)N12 MAFIPFSQYBWLAM-BAFYGKSASA-N 0.000 description 4
- 229930186147 Cephalosporin Natural products 0.000 description 4
- 229940124587 cephalosporin Drugs 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001780 cephalosporins Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 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 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 108090000371 Esterases Proteins 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- TZCYHGNGYPKDLP-KQJPBFKISA-N benzhydryl (6R)-3-(3-hydroxybutanoyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate Chemical compound S1C(=CC=C1)CC(=O)NC1[C@@H]2N(C(C(=CS2)COC(CC(C)O)=O)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O TZCYHGNGYPKDLP-KQJPBFKISA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RHLBGAGAUSNVLN-HWZXHQHMSA-N (6r)-3-hydroxy-4-methyl-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class C1=C(O)C(C)S[C@@H]2CC(=O)N21 RHLBGAGAUSNVLN-HWZXHQHMSA-N 0.000 description 1
- MXDKSPBDKGTHDW-NQPNHJOESA-N (6r)-4-(bromomethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class C1=CC(CBr)S[C@@H]2CC(=O)N21 MXDKSPBDKGTHDW-NQPNHJOESA-N 0.000 description 1
- NFNTZXPJBVMMEV-SSDOTTSWSA-N (6r)-4-(hydroxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical compound S1C(CO)=CCN2C(=O)C[C@H]21 NFNTZXPJBVMMEV-SSDOTTSWSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UEVPKMPAHXHIEF-SECBINFHSA-N [(6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl acetate Chemical group S1CC(COC(=O)C)=CN2C(=O)C[C@H]21 UEVPKMPAHXHIEF-SECBINFHSA-N 0.000 description 1
- FAGLETQHUJYDMO-SSDOTTSWSA-N [(6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl carbamate Chemical class S1CC(COC(=O)N)=CN2C(=O)C[C@H]21 FAGLETQHUJYDMO-SSDOTTSWSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- SYZLNPAPUUIUFB-QEMNHKJVSA-N benzhydryl (6R)-3-(4-hydroxybutanoyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate Chemical compound S1C(=CC=C1)CC(=O)NC1[C@@H]2N(C(C(=CS2)COC(CCCO)=O)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O SYZLNPAPUUIUFB-QEMNHKJVSA-N 0.000 description 1
- FOFRQNUHFXUGMU-NUVVQUMISA-N benzhydryl (6R)-3-[(4-hydroxy-3-methylhexanoyl)oxymethyl]-8-oxo-7-[(2-phenylethanethioyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate Chemical compound C1(=CC=CC=C1)CC(=S)NC1[C@@H]2N(C(C(=CS2)COC(CC(C(CC)O)C)=O)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O FOFRQNUHFXUGMU-NUVVQUMISA-N 0.000 description 1
- FEVAYOIKJROVDI-ZWAGFTRDSA-N benzhydryl (6r)-3-(bromomethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)CBr)C(=O)OC(C=1C=CC=CC=1)C=1C=CC=CC=1)NC(=O)CC1=CC=CS1 FEVAYOIKJROVDI-ZWAGFTRDSA-N 0.000 description 1
- GOLTVERXHUZLIL-QGPIEZSZSA-N benzhydryl (6r)-3-(hydroxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate Chemical compound C1([C@H]2SC=C(C(N2C1=O)C(=O)OC(C=1C=CC=CC=1)C=1C=CC=CC=1)CO)NC(=O)CC1=CC=CS1 GOLTVERXHUZLIL-QGPIEZSZSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical group 0.000 description 1
- 125000006244 carboxylic acid protecting group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001782 cephems Chemical class 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000000422 delta-lactone group Chemical group 0.000 description 1
- NNQIJOYQWYKBOW-UHFFFAOYSA-N desacetoxycephalosphorin G Natural products S1CC(C)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C12 NNQIJOYQWYKBOW-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000000457 gamma-lactone group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- QGQPUSJDLQOCIN-UHFFFAOYSA-M lithium;4-hydroxy-3-methylbutanoate Chemical compound [Li+].OCC(C)CC([O-])=O QGQPUSJDLQOCIN-UHFFFAOYSA-M 0.000 description 1
- OEUDJWOBYRGRHQ-UHFFFAOYSA-M lithium;4-hydroxypentanoate Chemical compound [Li+].CC(O)CCC([O-])=O OEUDJWOBYRGRHQ-UHFFFAOYSA-M 0.000 description 1
- VLKFHPNOUILXDR-UHFFFAOYSA-M lithium;5-hydroxy-4-methylheptanoate Chemical compound [Li+].CCC(O)C(C)CCC([O-])=O VLKFHPNOUILXDR-UHFFFAOYSA-M 0.000 description 1
- UQCUDUALRXFSMO-UHFFFAOYSA-M lithium;5-hydroxypentanoate Chemical compound [Li+].OCCCCC([O-])=O UQCUDUALRXFSMO-UHFFFAOYSA-M 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- URMOIQPAWQIYLI-NQPNHJOESA-N methyl (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate Chemical compound COC(=O)C1C=CS[C@H]2N1C(C2)=O URMOIQPAWQIYLI-NQPNHJOESA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- XRDQAKWNVVTFQN-BGNXCDLCSA-N phenacyl (6r)-7-acetamido-3-[(3-ethyl-4-hydroxyhexanoyl)oxymethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate Chemical compound CC(=O)NC([C@H]1SC=C2COC(=O)CC(CC)C(O)CC)C(=O)N1C2C(=O)OCC(=O)C1=CC=CC=C1 XRDQAKWNVVTFQN-BGNXCDLCSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- GVLQIMPIIXUTDM-UHFFFAOYSA-M potassium;3-(hydroxymethyl)pentanoate Chemical compound [K+].CCC(CO)CC([O-])=O GVLQIMPIIXUTDM-UHFFFAOYSA-M 0.000 description 1
- TXSIWDVUJVMMKM-UHFFFAOYSA-M potassium;4-hydroxybutanoate Chemical compound [K+].OCCCC([O-])=O TXSIWDVUJVMMKM-UHFFFAOYSA-M 0.000 description 1
- RDMYSPKAXVSWHV-UHFFFAOYSA-M potassium;4-hydroxyhexanoate Chemical compound [K+].CCC(O)CCC([O-])=O RDMYSPKAXVSWHV-UHFFFAOYSA-M 0.000 description 1
- STKGREVDBZERKZ-UHFFFAOYSA-M potassium;5-hydroxy-4-methylpentanoate Chemical compound [K+].OCC(C)CCC([O-])=O STKGREVDBZERKZ-UHFFFAOYSA-M 0.000 description 1
- KHFFSBFZEDPRLL-UHFFFAOYSA-M potassium;5-hydroxyheptanoate Chemical compound [K+].CCC(O)CCCC([O-])=O KHFFSBFZEDPRLL-UHFFFAOYSA-M 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JFPPNYXGWQBUDC-UHFFFAOYSA-M sodium;3-ethyl-4-hydroxyhexanoate Chemical compound [Na+].CCC(O)C(CC)CC([O-])=O JFPPNYXGWQBUDC-UHFFFAOYSA-M 0.000 description 1
- GXOOPGFBZZUVAY-UHFFFAOYSA-M sodium;4-ethyl-5-hydroxyheptanoate Chemical compound [Na+].CCC(O)C(CC)CCC([O-])=O GXOOPGFBZZUVAY-UHFFFAOYSA-M 0.000 description 1
- ALFDZXABELUALH-UHFFFAOYSA-M sodium;4-hydroxy-3-methylhexanoate Chemical compound [Na+].CCC(O)C(C)CC([O-])=O ALFDZXABELUALH-UHFFFAOYSA-M 0.000 description 1
- ZCDPXBDALNLGCH-UHFFFAOYSA-M sodium;4-hydroxy-3-methylpentanoate Chemical compound [Na+].CC(O)C(C)CC([O-])=O ZCDPXBDALNLGCH-UHFFFAOYSA-M 0.000 description 1
- BBVZNMRMCITBJG-UHFFFAOYSA-M sodium;5-hydroxy-4-methylhexanoate Chemical compound [Na+].CC(O)C(C)CCC([O-])=O BBVZNMRMCITBJG-UHFFFAOYSA-M 0.000 description 1
- WIBUBADCTYEVQP-UHFFFAOYSA-M sodium;5-hydroxyhexanoate Chemical compound [Na+].CC(O)CCCC([O-])=O WIBUBADCTYEVQP-UHFFFAOYSA-M 0.000 description 1
- ZJDDLWNQIJLIQU-UHFFFAOYSA-M sodium;5-hydroxypentanoate Chemical compound [Na+].OCCCCC([O-])=O ZJDDLWNQIJLIQU-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WQPLMXOSQCQQSN-AFMYVXGZSA-N tert-butyl (6r)-3-(4-hydroxybutanoyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(C(=CS2)COC(=O)CCCO)C(=O)OC(C)(C)C)NC(=O)CC1=CC=CS1 WQPLMXOSQCQQSN-AFMYVXGZSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene 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
- C07D501/02—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
-
- 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
- C07D501/60—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 3 and 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/678,086 US4038275A (en) | 1976-04-19 | 1976-04-19 | Process for preparation of 3-hydroxymethylcephems |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626625A5 true CH626625A5 (ja) | 1981-11-30 |
Family
ID=24721325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH484377A CH626625A5 (ja) | 1976-04-19 | 1977-04-19 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4038275A (ja) |
| JP (1) | JPS52128392A (ja) |
| BE (1) | BE853684A (ja) |
| CA (1) | CA1084905A (ja) |
| CH (1) | CH626625A5 (ja) |
| DE (1) | DE2716814A1 (ja) |
| ES (1) | ES457708A1 (ja) |
| FR (1) | FR2348928A1 (ja) |
| GB (1) | GB1574524A (ja) |
| IE (1) | IE44867B1 (ja) |
| IL (1) | IL51653A (ja) |
| NL (1) | NL7704284A (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1571989A (en) * | 1976-10-08 | 1980-07-23 | Glaxo Lab Ltd | Manufacture of 3-hydroxymethyl cephalosporin compounds |
| CN103570745A (zh) * | 2013-10-10 | 2014-02-12 | 哈药集团制药总厂 | 一种盐酸头孢替安内酯的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3948906A (en) * | 1967-08-21 | 1976-04-06 | Glaxo Laboratories Limited | Cephalosporin compounds |
| DE1906194C3 (de) * | 1968-02-07 | 1980-11-13 | Eli Lilly And Co., Indianapolis, Id (V.St.A.) | 3-Brommethyl-A2 -cephalosporine und Verfahren zu ihrer Herstellung |
| US3950329A (en) * | 1972-12-11 | 1976-04-13 | E. I. Du Pont De Nemours And Company | Fluorinated cephalosporins |
-
1976
- 1976-04-19 US US05/678,086 patent/US4038275A/en not_active Expired - Lifetime
-
1977
- 1977-03-11 IE IE537/77A patent/IE44867B1/en unknown
- 1977-03-14 IL IL51653A patent/IL51653A/xx unknown
- 1977-03-18 CA CA274,243A patent/CA1084905A/en not_active Expired
- 1977-04-11 ES ES457708A patent/ES457708A1/es not_active Expired
- 1977-04-13 GB GB15264/77A patent/GB1574524A/en not_active Expired
- 1977-04-14 JP JP4342777A patent/JPS52128392A/ja active Pending
- 1977-04-15 BE BE1008079A patent/BE853684A/xx not_active IP Right Cessation
- 1977-04-15 DE DE19772716814 patent/DE2716814A1/de active Granted
- 1977-04-19 NL NL7704284A patent/NL7704284A/xx not_active Application Discontinuation
- 1977-04-19 FR FR7711771A patent/FR2348928A1/fr active Granted
- 1977-04-19 CH CH484377A patent/CH626625A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2348928B1 (ja) | 1980-02-08 |
| IE44867B1 (en) | 1982-04-21 |
| FR2348928A1 (fr) | 1977-11-18 |
| DE2716814C2 (ja) | 1987-11-26 |
| NL7704284A (nl) | 1977-10-21 |
| US4038275A (en) | 1977-07-26 |
| IL51653A0 (en) | 1977-05-31 |
| ES457708A1 (es) | 1978-02-16 |
| BE853684A (fr) | 1977-10-17 |
| DE2716814A1 (de) | 1977-10-27 |
| CA1084905A (en) | 1980-09-02 |
| IE44867L (en) | 1977-10-19 |
| JPS52128392A (en) | 1977-10-27 |
| GB1574524A (en) | 1980-09-10 |
| IL51653A (en) | 1980-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |