DE2309599A1 - Verfahren zur herstellung von 7-acylamino-desacetoxy-cephalosporansaeurederivaten - Google Patents
Verfahren zur herstellung von 7-acylamino-desacetoxy-cephalosporansaeurederivatenInfo
- Publication number
- DE2309599A1 DE2309599A1 DE19732309599 DE2309599A DE2309599A1 DE 2309599 A1 DE2309599 A1 DE 2309599A1 DE 19732309599 DE19732309599 DE 19732309599 DE 2309599 A DE2309599 A DE 2309599A DE 2309599 A1 DE2309599 A1 DE 2309599A1
- Authority
- DE
- Germany
- Prior art keywords
- ester
- penicillin
- toluene
- sulfoxide
- silver
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title description 6
- -1 Butoxy, 2-thenyl Chemical group 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910001385 heavy metal Inorganic materials 0.000 claims description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052753 mercury Inorganic materials 0.000 claims description 4
- 150000002960 penicillins Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 239000004332 silver Substances 0.000 claims description 4
- 229910052716 thallium Inorganic materials 0.000 claims description 4
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 4
- 239000011135 tin Substances 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000011133 lead Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 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 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- ZGDWHDKHJKZZIQ-UHFFFAOYSA-N cobalt nickel Chemical compound [Co].[Ni].[Ni].[Ni] ZGDWHDKHJKZZIQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- HEPLMSKRHVKCAQ-UHFFFAOYSA-N lead nickel Chemical compound [Ni].[Pb] HEPLMSKRHVKCAQ-UHFFFAOYSA-N 0.000 claims 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 12
- 229940113088 dimethylacetamide Drugs 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- PUIOJZLIOUHNEV-CYBMUJFWSA-N (4-nitrophenyl)methyl (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [N+](=O)([O-])C1=CC=C(COC(=O)C2=CCS[C@H]3N2C(C3)=O)C=C1 PUIOJZLIOUHNEV-CYBMUJFWSA-N 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- RYKLZUPYJFFNRR-UHFFFAOYSA-N 3-hydroxypiperidin-2-one Chemical compound OC1CCCNC1=O RYKLZUPYJFFNRR-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- JALQQBGHJJURDQ-UHFFFAOYSA-L bis(methylsulfonyloxy)tin Chemical compound [Sn+2].CS([O-])(=O)=O.CS([O-])(=O)=O JALQQBGHJJURDQ-UHFFFAOYSA-L 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- DNPOVSLJNLLGMA-SJUANORRSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenoxyacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)COC1=CC=CC=C1 DNPOVSLJNLLGMA-SJUANORRSA-N 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 3
- 229930186147 Cephalosporin Natural products 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229930182555 Penicillin Natural products 0.000 description 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229940124587 cephalosporin Drugs 0.000 description 3
- 150000001780 cephalosporins Chemical class 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- UQJXHLBZULXQBV-CQSZACIVSA-N (4-methoxyphenyl)methyl (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1=CC(OC)=CC=C1COC(=O)C1=CCS[C@H]2N1C(=O)C2 UQJXHLBZULXQBV-CQSZACIVSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- FJOLTQXXWSRAIX-UHFFFAOYSA-K silver phosphate Chemical compound [Ag+].[Ag+].[Ag+].[O-]P([O-])([O-])=O FJOLTQXXWSRAIX-UHFFFAOYSA-K 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- FKJSFKCZZIXQIP-UHFFFAOYSA-N 2-bromo-1-(4-bromophenyl)ethanone Chemical compound BrCC(=O)C1=CC=C(Br)C=C1 FKJSFKCZZIXQIP-UHFFFAOYSA-N 0.000 description 1
- FLAYZKKEOIAALB-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C=C1 FLAYZKKEOIAALB-UHFFFAOYSA-N 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OIQLTUNIABSAFN-CQSZACIVSA-N [2-(4-bromophenyl)-2-oxoethyl] (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound BrC1=CC=C(C(COC(=O)C2=CCS[C@H]3N2C(C3)=O)=O)C=C1 OIQLTUNIABSAFN-CQSZACIVSA-N 0.000 description 1
- SGSYXTJBPMJUFP-CQSZACIVSA-N [2-(4-chlorophenyl)-2-oxoethyl] (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound ClC1=CC=C(C(COC(=O)C2=CCS[C@H]3N2C(C3)=O)=O)C=C1 SGSYXTJBPMJUFP-CQSZACIVSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000007854 aminals Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- SDFNZYMSEOUVIF-UHFFFAOYSA-N copper;methanesulfonic acid Chemical compound [Cu].CS(O)(=O)=O SDFNZYMSEOUVIF-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UTELLXMIACXNPY-MRVPVSSYSA-N cyanomethyl (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(#N)COC(=O)C1=CCS[C@H]2N1C(C2)=O UTELLXMIACXNPY-MRVPVSSYSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- FQQRAQNLVACMPX-UHFFFAOYSA-L mercury(2+);methanesulfonate Chemical compound [Hg+2].CS([O-])(=O)=O.CS([O-])(=O)=O FQQRAQNLVACMPX-UHFFFAOYSA-L 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229940019931 silver phosphate Drugs 0.000 description 1
- 229910000161 silver phosphate Inorganic materials 0.000 description 1
- JUDUFOKGIZUSFP-UHFFFAOYSA-M silver;4-methylbenzenesulfonate Chemical compound [Ag+].CC1=CC=C(S([O-])(=O)=O)C=C1 JUDUFOKGIZUSFP-UHFFFAOYSA-M 0.000 description 1
- GVFLIEBOPZQLON-UHFFFAOYSA-M silver;fluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)CF GVFLIEBOPZQLON-UHFFFAOYSA-M 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XWVKTOHUMPLABF-UHFFFAOYSA-N thallium(3+) Chemical compound [Tl+3] XWVKTOHUMPLABF-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000012749 thinning agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732309599 DE2309599A1 (de) | 1973-02-26 | 1973-02-26 | Verfahren zur herstellung von 7-acylamino-desacetoxy-cephalosporansaeurederivaten |
| US05/442,810 US3997533A (en) | 1973-02-26 | 1974-02-14 | Process for the preparation of 7-acylamino-desacetoxycephalosporanic derivatives |
| CA192,962A CA1032156A (en) | 1973-02-26 | 1974-02-19 | Process for the preparation of 7-acylaminodesace-toxycephalosporanic acid derivatives |
| RO7400077746A RO63497A (fr) | 1973-02-26 | 1974-02-19 | Procede pour la preparation des derives d'acide 7-acylamino dezacetoxyceposporanique |
| DD176699A DD113549A5 (enExample) | 1973-02-26 | 1974-02-20 | |
| LU69477A LU69477A1 (enExample) | 1973-02-26 | 1974-02-22 | |
| JP49020658A JPS49117489A (enExample) | 1973-02-26 | 1974-02-22 | |
| IL44265A IL44265A (en) | 1973-02-26 | 1974-02-22 | The preparation of 7-acylamino-desacetoxycephalosporanic acid derivatives from penicillin sulfoxides |
| CH255274A CH591498A5 (enExample) | 1973-02-26 | 1974-02-22 | |
| AU65909/74A AU476881B2 (en) | 1973-02-26 | 1974-02-22 | Process for the preparation of 7-acylamino-desacetoxycephalosporanic acid derivatives |
| EG51/74A EG11155A (en) | 1973-02-26 | 1974-02-23 | Process for the preparation of 7-acylaminodesaceto xycephalosporanic acid derivatives |
| ES423619A ES423619A1 (es) | 1973-02-26 | 1974-02-25 | Procedimiento para la produccion de derivados de acido 7- acilamino-desacetoxi-cefalosoporanico. |
| PL1974169070A PL88748B1 (enExample) | 1973-02-26 | 1974-02-25 | |
| BE141341A BE811521A (fr) | 1973-02-26 | 1974-02-25 | Procede de preparation de derives d'acides 7-acylamino-desacetoxy cephalosporaniques |
| NL7402533A NL7402533A (enExample) | 1973-02-26 | 1974-02-25 | |
| ZA00741210A ZA741210B (en) | 1973-02-26 | 1974-02-25 | Process for the preparation of 7-acylaminodesacetoxycephalosporanic acid derivatives |
| GB842174A GB1420573A (en) | 1973-02-26 | 1974-02-25 | Process for the preparation of 7-acylamino-desacetoxy cephalosporanic acid deri''tives |
| FR7406499A FR2219167B1 (enExample) | 1973-02-26 | 1974-02-26 | |
| HUBA3036A HU168588B (enExample) | 1973-02-26 | 1974-02-26 | |
| AT155474A AT330350B (de) | 1973-02-26 | 1974-02-26 | Verfahren zur herstellung von 7-acylamino- desacetoxy-cephalosporansaure- derivaten |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732309599 DE2309599A1 (de) | 1973-02-26 | 1973-02-26 | Verfahren zur herstellung von 7-acylamino-desacetoxy-cephalosporansaeurederivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2309599A1 true DE2309599A1 (de) | 1974-09-05 |
Family
ID=5873158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732309599 Pending DE2309599A1 (de) | 1973-02-26 | 1973-02-26 | Verfahren zur herstellung von 7-acylamino-desacetoxy-cephalosporansaeurederivaten |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3997533A (enExample) |
| JP (1) | JPS49117489A (enExample) |
| AT (1) | AT330350B (enExample) |
| AU (1) | AU476881B2 (enExample) |
| BE (1) | BE811521A (enExample) |
| CA (1) | CA1032156A (enExample) |
| CH (1) | CH591498A5 (enExample) |
| DD (1) | DD113549A5 (enExample) |
| DE (1) | DE2309599A1 (enExample) |
| EG (1) | EG11155A (enExample) |
| ES (1) | ES423619A1 (enExample) |
| FR (1) | FR2219167B1 (enExample) |
| GB (1) | GB1420573A (enExample) |
| HU (1) | HU168588B (enExample) |
| IL (1) | IL44265A (enExample) |
| LU (1) | LU69477A1 (enExample) |
| NL (1) | NL7402533A (enExample) |
| PL (1) | PL88748B1 (enExample) |
| RO (1) | RO63497A (enExample) |
| ZA (1) | ZA741210B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4164586A (en) * | 1974-07-19 | 1979-08-14 | Hoffmann-La Roche Inc. | Therapeutic agent for improving cardiovascular function |
| US4096329A (en) * | 1976-03-05 | 1978-06-20 | E. R. Squibb & Sons, Inc. | 7-Cyanoalkylureido 3 heterocylic thio methyl cephalosporins |
| US4128723A (en) * | 1977-02-02 | 1978-12-05 | E. R. Squibb & Sons, Inc. | Cyanoalkylureido cephalosporins |
| US4096330A (en) * | 1977-04-21 | 1978-06-20 | E. R. Squibb & Sons, Inc. | 7β-[[[(2-Cyanomethyl)amino]-1,2-dioxoethyl]amino]acyl cephalosporins |
| US4310459A (en) * | 1978-04-03 | 1982-01-12 | Bristol-Myers Company | Process for producing carbamoyl substituted penams and carbamoyl substituted cephams from penicillin sulfoxide esters |
| US4322347A (en) * | 1978-04-03 | 1982-03-30 | Bristol-Myers Company | 2-Carbamoyloxymethyl-penicillin derivatives |
| US4518773A (en) * | 1978-04-03 | 1985-05-21 | Bristol-Myers Company | "3-Carbamoyloxy cephalosporins" |
| US4426520A (en) | 1978-04-03 | 1984-01-17 | Bristol-Myers Company | 3-Carbamoyloxy-cepham-4-carboxylic acid derivatives |
| US4168266A (en) * | 1978-05-30 | 1979-09-18 | E. R. Squibb & Sons, Inc. | 6-[[[(2-Cyanomethyl)amino]-1,2-dioxoethyl]-amino]acyl penicillins |
| US4174399A (en) * | 1978-07-10 | 1979-11-13 | Syntex (Usa) Inc. | Treatment of lactic acidosis in ruminants |
| US4374982A (en) * | 1979-11-07 | 1983-02-22 | Bristol-Myers Company | Cepham compounds |
| CN103058932B (zh) * | 2013-02-01 | 2015-10-07 | 京博农化科技股份有限公司 | N-(2-苯并咪唑基)-氨基甲酸甲酯的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES377330A1 (es) * | 1969-03-11 | 1972-06-16 | Glaxo Lab Ltd | Procedimiento para preparar esteres de acido 7 beta-acila- mido-3-metilcef3-em-4-carboxilico. |
| US3853861A (en) * | 1969-03-18 | 1974-12-10 | Lilly Co Eli | Cephalexin intermediate |
| GB1312233A (en) * | 1969-12-05 | 1973-04-04 | Glaxo Lab Ltd | Cephalosporin compounds |
| US3852281A (en) * | 1970-02-18 | 1974-12-03 | Koninklijke Gist Spiritus | Process for the preparation of 7-substituted amino-desacetoxycephalosporanic acid compounds |
| US3799924A (en) * | 1970-12-18 | 1974-03-26 | Lilly Co Eli | Ester cleavage process |
| DE2064107A1 (de) * | 1970-12-28 | 1972-07-06 | Farbwerke Hoechst AG vormals Meister Lucius & Brüning, 6000 Frankfurt | Verfahren zur Herstellung von Cephem-4-carbonsäureestern |
| GB1431174A (en) * | 1972-06-30 | 1976-04-07 | Clin Midy | Process for the conversion of a penicillin s-oxide into a corresponding desacetoxycephalosporin |
-
1973
- 1973-02-26 DE DE19732309599 patent/DE2309599A1/de active Pending
-
1974
- 1974-02-14 US US05/442,810 patent/US3997533A/en not_active Expired - Lifetime
- 1974-02-19 CA CA192,962A patent/CA1032156A/en not_active Expired
- 1974-02-19 RO RO7400077746A patent/RO63497A/ro unknown
- 1974-02-20 DD DD176699A patent/DD113549A5/xx unknown
- 1974-02-22 JP JP49020658A patent/JPS49117489A/ja active Pending
- 1974-02-22 IL IL44265A patent/IL44265A/en unknown
- 1974-02-22 AU AU65909/74A patent/AU476881B2/en not_active Expired
- 1974-02-22 CH CH255274A patent/CH591498A5/xx not_active IP Right Cessation
- 1974-02-22 LU LU69477A patent/LU69477A1/xx unknown
- 1974-02-23 EG EG51/74A patent/EG11155A/xx active
- 1974-02-25 NL NL7402533A patent/NL7402533A/xx unknown
- 1974-02-25 ES ES423619A patent/ES423619A1/es not_active Expired
- 1974-02-25 GB GB842174A patent/GB1420573A/en not_active Expired
- 1974-02-25 BE BE141341A patent/BE811521A/xx unknown
- 1974-02-25 PL PL1974169070A patent/PL88748B1/pl unknown
- 1974-02-25 ZA ZA00741210A patent/ZA741210B/xx unknown
- 1974-02-26 FR FR7406499A patent/FR2219167B1/fr not_active Expired
- 1974-02-26 HU HUBA3036A patent/HU168588B/hu unknown
- 1974-02-26 AT AT155474A patent/AT330350B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU476881B2 (en) | 1976-10-07 |
| CA1032156A (en) | 1978-05-30 |
| FR2219167A1 (enExample) | 1974-09-20 |
| LU69477A1 (enExample) | 1974-09-25 |
| JPS49117489A (enExample) | 1974-11-09 |
| PL88748B1 (enExample) | 1976-09-30 |
| RO63497A (fr) | 1978-10-15 |
| AT330350B (de) | 1976-06-25 |
| AU6590974A (en) | 1975-08-28 |
| EG11155A (en) | 1977-05-31 |
| IL44265A (en) | 1976-10-31 |
| ZA741210B (en) | 1975-01-29 |
| BE811521A (fr) | 1974-08-26 |
| ES423619A1 (es) | 1976-05-01 |
| HU168588B (enExample) | 1976-06-28 |
| FR2219167B1 (enExample) | 1977-09-23 |
| USB442810I5 (enExample) | 1976-02-24 |
| IL44265A0 (en) | 1974-05-16 |
| US3997533A (en) | 1976-12-14 |
| GB1420573A (en) | 1976-01-07 |
| ATA155474A (de) | 1975-09-15 |
| CH591498A5 (enExample) | 1977-09-30 |
| NL7402533A (enExample) | 1974-08-28 |
| DD113549A5 (enExample) | 1975-06-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2309599A1 (de) | Verfahren zur herstellung von 7-acylamino-desacetoxy-cephalosporansaeurederivaten | |
| EP0731086B1 (de) | Verfahren zur Herstellung aromatischer Nitrile | |
| AT349029B (de) | Verfahren zur herstellung von neuen 1,2- dithiolderivaten | |
| DE2735454A1 (de) | Verfahren zur herstellung von 3-chlorcephemverbindungen | |
| DE1770822C3 (de) | Verfahren zur Herstellung von Estern der 7-Aminodesacetoxycephalosporansäure | |
| DE2320040A1 (de) | Verfahren zur herstellung von 7acylamino-desacetoxy-cephalosporansaeureester | |
| DE2225149A1 (de) | Neue Oxofurylesterdenvate von Penicillin und Cephalosporin | |
| DE2412598C2 (de) | Verfahren zur Herstellung von 7-Alkoxycephalosporinen bzw. 6-Alkoxypenicillinen | |
| DD149668A5 (de) | Verfahren zur herstellung von penicillinsulfoxiden | |
| EP0583672B1 (de) | Verfahren zur Herstellung von 2-Aryl-ethan-sulfonsäuren | |
| DE2429166A1 (de) | Verfahren zur selektiven spaltung der amidsaeurefunktion eines 7-(amidsaeure)cephalosporins | |
| DE2246203C3 (de) | Verfahren zur Herstellung von Steroid-21-alkoholen | |
| CH637973A5 (de) | Verfahren zur herstellung von steroiden. | |
| EP0342532B1 (de) | Verfahren zur Herstellung von 4-Chlor-2-methyl-5-nitro-phenol | |
| DE2332718A1 (de) | Verfahren zur umwandlung von penicillinverbindungen in desacetoxycephalosporinverbindungen | |
| DE2460477A1 (de) | Verbessertes verfahren zur herstellung von 6-alkoxy-substituierten penicillinen | |
| DE2209891C3 (de) | 9,10-Dihydro-thieno[3.2-b][f][4H]benzazepine sowie Verfahren zu deren Herstellung | |
| DE3833521C2 (enExample) | ||
| CH618702A5 (enExample) | ||
| DE2234836C3 (de) | Verfahren zur Herstellung und Isolierung von Äthylauraminsalzen | |
| DE1643463B2 (de) | Verfahren zur Herstellung von l-(p-Chlorbenzoyl)-2-methyl-3-indoiylessigsäuren | |
| LU86853A1 (de) | Neue 8-beziehungsweise 1,8-substituierte ergolenderivate und verfahren zu ihrer herstellung | |
| AT317219B (de) | Verfahren zur Herstellung neuer 4-Phenyl-2(1H)-chinazolinone | |
| AT274800B (de) | Verfahren zur Herstellung von Indolderivaten | |
| AT266115B (de) | Verfahren zur Herstellung von neuen aliphatischen α-(3-Indolyl)-carbonsäuren und ihren Salzen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |