DE2011376C3 - - Google Patents
Info
- Publication number
- DE2011376C3 DE2011376C3 DE19702011376 DE2011376A DE2011376C3 DE 2011376 C3 DE2011376 C3 DE 2011376C3 DE 19702011376 DE19702011376 DE 19702011376 DE 2011376 A DE2011376 A DE 2011376A DE 2011376 C3 DE2011376 C3 DE 2011376C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- same
- pyridine
- oxide
- reaction
- 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.)
- Expired
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 57
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 24
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 2
- XJMFIMBSWLGRQW-UHFFFAOYSA-N P(O)(O)=O.ClCCl Chemical compound P(O)(O)=O.ClCCl XJMFIMBSWLGRQW-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
- -1 cyano, carboxy Chemical group 0.000 description 45
- 239000002253 acid Substances 0.000 description 41
- 235000019441 ethanol Nutrition 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- 150000003839 salts Chemical class 0.000 description 36
- 239000011780 sodium chloride Substances 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 28
- LKYXEULZVGJVTG-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH] LKYXEULZVGJVTG-UHFFFAOYSA-N 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- 239000000203 mixture Substances 0.000 description 23
- 239000002585 base Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 229940049954 Penicillin Drugs 0.000 description 17
- 229960000626 benzylpenicillin Drugs 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 235000011007 phosphoric acid Nutrition 0.000 description 16
- 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 14
- 239000003054 catalyst Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000004809 thin layer chromatography Methods 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 125000002252 acyl group Chemical group 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- IQTYUGSHUITLHX-UHFFFAOYSA-N P([O-])(O)=O.ClCCl.[NH+]1=CC=CC=C1 Chemical compound P([O-])(O)=O.ClCCl.[NH+]1=CC=CC=C1 IQTYUGSHUITLHX-UHFFFAOYSA-N 0.000 description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000002808 molecular sieve Substances 0.000 description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N Isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-Methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 150000001780 cephalosporins Chemical class 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- IXTGXVWLIBNABC-UHFFFAOYSA-N dichloromethylphosphonic acid Chemical compound OP(O)(=O)C(Cl)Cl IXTGXVWLIBNABC-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- YPWNNTBDMSIJIR-UHFFFAOYSA-N 14696-82-3 Chemical compound IN=[N+]=[N-] YPWNNTBDMSIJIR-UHFFFAOYSA-N 0.000 description 4
- JYZIHLWOWKMNNX-UHFFFAOYSA-N Benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- RBKMMJSQKNKNEV-RITPCOANSA-N Penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium monoxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- QHTOIDKCEPKVCM-ZCFIWIBFSA-N cepham Chemical compound S1CCCN2C(=O)C[C@H]21 QHTOIDKCEPKVCM-ZCFIWIBFSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000005712 crystallization Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 150000003009 phosphonic acids Chemical class 0.000 description 4
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-Nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N 8-Hydroxyquinoline Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N Benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
- 229960001701 Chloroform Drugs 0.000 description 3
- 230000002378 acidificating Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000003115 biocidal Effects 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-M caproate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229960003540 oxyquinoline Drugs 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000001603 reducing Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- IRLYGRLEBKCYPY-UHFFFAOYSA-N 2,5-dimethylbenzenesulfonic acid Chemical compound CC1=CC=C(C)C(S(O)(=O)=O)=C1 IRLYGRLEBKCYPY-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-Methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-Aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- ZVAYUUUQOCPZCZ-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)aniline Chemical compound CCOP(=O)(OCC)CC1=CC=C(N)C=C1 ZVAYUUUQOCPZCZ-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-Chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- JKTYGPATCNUWKN-UHFFFAOYSA-N 4-nitrobenzyl alcohol Chemical compound OCC1=CC=C([N+]([O-])=O)C=C1 JKTYGPATCNUWKN-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N Anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 229940064005 Antibiotic throat preparations Drugs 0.000 description 2
- 229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 description 2
- 229940042052 Antibiotics for systemic use Drugs 0.000 description 2
- 229940042786 Antitubercular Antibiotics Drugs 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N Bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N Diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- XPFVYQJUAUNWIW-UHFFFAOYSA-N Furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 2
- 229940093922 Gynecological Antibiotics Drugs 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- ZYDCYYCORHLHDQ-UHFFFAOYSA-N P([O-])([O-])=O.ClCCl.[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1 Chemical compound P([O-])([O-])=O.ClCCl.[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1 ZYDCYYCORHLHDQ-UHFFFAOYSA-N 0.000 description 2
- CKRZKMFTZCFYGB-UHFFFAOYSA-N Phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N Silver nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 229940024982 Topical Antifungal Antibiotics Drugs 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 2
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 238000005947 deacylation reaction Methods 0.000 description 2
- 238000006344 deformylation reaction Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 229940079866 intestinal antibiotics Drugs 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 2
- 229940005935 ophthalmologic Antibiotics Drugs 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000001681 protective Effects 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- MTNQLAKBYRCDTF-UHFFFAOYSA-N (2-nitrophenyl)phosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1[N+]([O-])=O MTNQLAKBYRCDTF-UHFFFAOYSA-N 0.000 description 1
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-Trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-Chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-Formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N 2-Pentanone Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- RSWBDNVBJPQFAN-UHFFFAOYSA-N 2-amino-6-hydroxybenzenesulfonic acid Chemical compound NC1=CC=CC(O)=C1S(O)(=O)=O RSWBDNVBJPQFAN-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 1
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-Methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- JRJGKUTZNBZHNK-UHFFFAOYSA-N 3-Phenylpropyl acetate Chemical compound CC(=O)OCCCC1=CC=CC=C1 JRJGKUTZNBZHNK-UHFFFAOYSA-N 0.000 description 1
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- XWCBTCLNKUWVJL-UHFFFAOYSA-N 4-methylpyridine;phosphoric acid Chemical compound OP(O)(O)=O.CC1=CC=NC=C1 XWCBTCLNKUWVJL-UHFFFAOYSA-N 0.000 description 1
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-APA Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N Anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- BIBDCOCSEPMDQL-TYZXPVIJSA-M C1(=CC=CC=C1)CC(=O)NC1S[C@H]2N(C(=C1)C(=O)[O-])C(C2)=O Chemical compound C1(=CC=CC=C1)CC(=O)NC1S[C@H]2N(C(=C1)C(=O)[O-])C(C2)=O BIBDCOCSEPMDQL-TYZXPVIJSA-M 0.000 description 1
- RFAGAGYCSREFDN-UHFFFAOYSA-N CI.P(O)(O)=O Chemical compound CI.P(O)(O)=O RFAGAGYCSREFDN-UHFFFAOYSA-N 0.000 description 1
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- QILSFLSDHQAZET-UHFFFAOYSA-N Diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 1
- TWBYWOBDOCUKOW-UHFFFAOYSA-N Isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
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- NHQDETIJWKXCTC-UHFFFAOYSA-N Meta-Chloroperoxybenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N N-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- OIKOWAZRUFZSIA-UHFFFAOYSA-N N1=CC=CC=C1.BrC1=CC=CC=C1 Chemical compound N1=CC=CC=C1.BrC1=CC=CC=C1 OIKOWAZRUFZSIA-UHFFFAOYSA-N 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N Nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N O-Anisidine Chemical group COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- AELXREXQYKNSPY-UHFFFAOYSA-N P(O)(O)=O.[N+](=O)([O-])C1=CC=CC=C1 Chemical compound P(O)(O)=O.[N+](=O)([O-])C1=CC=CC=C1 AELXREXQYKNSPY-UHFFFAOYSA-N 0.000 description 1
- YVXVKEMPSICOEJ-UHFFFAOYSA-N P([O-])(O)=O.ClCCl.C1=[NH+]C=CC2=CC=CC=C12 Chemical compound P([O-])(O)=O.ClCCl.C1=[NH+]C=CC2=CC=CC=C12 YVXVKEMPSICOEJ-UHFFFAOYSA-N 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N Phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N Phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N Propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N Pyrophosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N Quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 1
- 241001481789 Rupicapra Species 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N Sec-Butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N THP Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- IKFIAYNBJNQVLS-UHFFFAOYSA-N [S].C1CSCN1 Chemical compound [S].C1CSCN1 IKFIAYNBJNQVLS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- JGDITNMASUZKPW-UHFFFAOYSA-K aluminium trichloride hexahydrate Chemical compound O.O.O.O.O.O.Cl[Al](Cl)Cl JGDITNMASUZKPW-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000005002 aryl methyl group Chemical group 0.000 description 1
- 238000011001 backwashing Methods 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- MOFCYHDQWIZKMY-UHFFFAOYSA-N chloromethylphosphonic acid Chemical compound OP(O)(=O)CCl MOFCYHDQWIZKMY-UHFFFAOYSA-N 0.000 description 1
- UZEDIBTVIIJELN-UHFFFAOYSA-N chromium(2+) Chemical compound [Cr+2] UZEDIBTVIIJELN-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- WNJHCCYBBGRYAE-UHFFFAOYSA-N dichloromethylphosphonic acid;pyridine Chemical compound C1=CC=NC=C1.OP(O)(=O)C(Cl)Cl WNJHCCYBBGRYAE-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 201000009910 diseases by infectious agent Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- RIMIDGSPFGJFCN-UHFFFAOYSA-N hydroxymethyl benzoate Chemical compound OCOC(=O)C1=CC=CC=C1 RIMIDGSPFGJFCN-UHFFFAOYSA-N 0.000 description 1
- GJAPDVNULBELLQ-UHFFFAOYSA-N iodomethane;phosphoric acid Chemical compound IC.OP(O)(O)=O GJAPDVNULBELLQ-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- BLTAPEIEHGWKKN-UHFFFAOYSA-N methanesulfonate;pyridin-1-ium Chemical compound CS(O)(=O)=O.C1=CC=NC=C1 BLTAPEIEHGWKKN-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 230000001717 pathogenic Effects 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- NJRWNWYFPOFDFN-UHFFFAOYSA-L phosphonate(2-) Chemical compound [O-][P]([O-])=O NJRWNWYFPOFDFN-UHFFFAOYSA-L 0.000 description 1
- HOJLDGRYURJOJS-UHFFFAOYSA-N phosphoric acid;pyridine Chemical compound OP(O)(O)=O.C1=CC=NC=C1 HOJLDGRYURJOJS-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000000607 poisoning Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- MZKUGCOENXBMFR-UHFFFAOYSA-N pyridin-1-ium;phosphate Chemical compound [O-]P([O-])([O-])=O.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 MZKUGCOENXBMFR-UHFFFAOYSA-N 0.000 description 1
- PTMBWNZJOQBTBK-UHFFFAOYSA-N pyridin-4-ylmethanol Chemical compound OCC1=CC=NC=C1 PTMBWNZJOQBTBK-UHFFFAOYSA-N 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 1
- NRTYMEPCRDJMPZ-UHFFFAOYSA-N pyridine;2,2,2-trifluoroacetic acid Chemical compound C1=CC=NC=C1.OC(=O)C(F)(F)F NRTYMEPCRDJMPZ-UHFFFAOYSA-N 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910001961 silver nitrate 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
- 239000011343 solid material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atoms Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- NWEPJDPAVFDLBY-UHFFFAOYSA-N trichloromethylphosphonic acid Chemical compound OP(O)(=O)C(Cl)(Cl)Cl NWEPJDPAVFDLBY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 238000005429 turbidity Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1286669 | 1969-03-11 | ||
| GB1286669 | 1969-03-11 | ||
| GB4662269 | 1969-09-22 | ||
| GB4662269 | 1969-09-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2011376A1 DE2011376A1 (de) | 1970-10-08 |
| DE2011376B2 DE2011376B2 (de) | 1975-08-28 |
| DE2011376C3 true DE2011376C3 (sv) | 1976-04-08 |
Family
ID=26249323
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2011376A Granted DE2011376B2 (de) | 1969-03-11 | 1970-03-10 | Verfahren zur Herstellung von 7beta-Acylamido-S-methylceph-S-em^-carbonsäureestern |
| DE2065236A Expired DE2065236C3 (de) | 1969-03-11 | 1970-03-10 | Phosphonsäuresalze, ihre Herstellung und Verwendung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2065236A Expired DE2065236C3 (de) | 1969-03-11 | 1970-03-10 | Phosphonsäuresalze, ihre Herstellung und Verwendung |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3725399A (sv) |
| JP (1) | JPS50838B1 (sv) |
| AT (1) | AT306919B (sv) |
| BE (1) | BE747119A (sv) |
| CH (2) | CH547310A (sv) |
| DE (2) | DE2011376B2 (sv) |
| DK (1) | DK136480B (sv) |
| ES (1) | ES377330A1 (sv) |
| FR (1) | FR2037858A5 (sv) |
| HU (2) | HU167757B (sv) |
| IE (1) | IE34580B1 (sv) |
| IL (1) | IL34045A (sv) |
| NL (1) | NL159389B (sv) |
| NO (1) | NO138629C (sv) |
| PL (1) | PL80548B1 (sv) |
| SE (1) | SE404527B (sv) |
| SU (1) | SU383303A3 (sv) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU35448B (en) * | 1970-02-18 | 1981-02-28 | Koninkl Gist Spiritus | Process for obtaining 7-substituted amino-deacetoxy cephalosporanic acids |
| US3843637A (en) * | 1971-05-11 | 1974-10-22 | Bristol Myers Co | Process for rearranging 6-acylamidopenicillanic acid-1-oxides to 7-acyla mido-3-methyl-ceph-3-em-4-carboxylic acids |
| DE2265798C2 (de) * | 1971-06-24 | 1985-09-26 | Fujisawa Pharmaceutical Co., Ltd., Osaka | Verfahren zur Herstellung von Oxoazetidin-Derivaten |
| US4003894A (en) * | 1971-08-17 | 1977-01-18 | Gist-Brocades N.V. | Preparation of 7-substituted amino-desacetoxycephalosporanic acid compounds |
| JPS536158B2 (sv) * | 1972-03-23 | 1978-03-04 | ||
| US3944545A (en) * | 1972-05-10 | 1976-03-16 | Eli Lilly And Company | Process for preparing desacetoxycephalosporins |
| DE2230372A1 (de) * | 1972-06-21 | 1973-01-11 | Fujisawa Pharmaceutical Co | Verfahren zur herstellung von oxidierten penam-derivaten |
| GB1431174A (en) * | 1972-06-30 | 1976-04-07 | Clin Midy | Process for the conversion of a penicillin s-oxide into a corresponding desacetoxycephalosporin |
| JPS4943999A (sv) * | 1972-09-01 | 1974-04-25 | ||
| GB1451459A (en) * | 1972-10-20 | 1976-10-06 | Fujisawa Pharamceutical Co Ltd | Process for preparing 3-alkyl-3-cephem-4-carboxylic acids and intermediates thereof |
| JPS4970989A (sv) * | 1972-11-15 | 1974-07-09 | ||
| GB1442785A (en) * | 1972-12-09 | 1976-07-14 | Nikken Chemicals Co Ltd | Desacetoxy ceaphalosporanic acids |
| GB1465893A (en) * | 1973-02-09 | 1977-03-02 | Gist Brocades Nv | I-carboxypropenyl-4-iminothio-azetidine-2-one derivatives methods for their preparation and use |
| DE2309599A1 (de) * | 1973-02-26 | 1974-09-05 | Bayer Ag | Verfahren zur herstellung von 7-acylamino-desacetoxy-cephalosporansaeurederivaten |
| US3932398A (en) * | 1973-04-19 | 1976-01-13 | American Home Products Corporation | 3-Halo-cepham derivatives |
| US4010156A (en) * | 1973-04-19 | 1977-03-01 | American Home Products Corporation | Process for the rearrangement of penicillins to cephalosporins and intermediate compounds thereof |
| JPS5084591A (sv) * | 1973-11-29 | 1975-07-08 | ||
| US3932392A (en) * | 1974-01-14 | 1976-01-13 | Bristol-Myers Company | Process for the preparation of 7-aminocephalosporanic acids |
| US3953440A (en) * | 1974-12-13 | 1976-04-27 | Eli Lilly And Company | Deacetoxycephalosporins via penicillin sulfoxide rearrangement |
| IT1063088B (it) * | 1976-06-01 | 1985-02-11 | Dobfar Spa | Derivati azetidinonici e procedimento per la preparazione di cefalosporine |
| EP0012106A1 (de) * | 1978-10-26 | 1980-06-11 | Ciba-Geigy Ag | Ammoniumsalze der Methylphosphonsäure, ihre Herstellung, ihre Verwendung als Zusätze für Hydraulikflüssigkeiten und Hydraulikflüssigkeiten, die sie enthalten |
| US5593992A (en) * | 1993-07-16 | 1997-01-14 | Smithkline Beecham Corporation | Compounds |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275626A (en) | 1962-07-31 | 1966-09-27 | Lilly Co Eli | Penicillin conversion via sulfoxide |
| US3280131A (en) | 1964-02-10 | 1966-10-18 | Millmaster Onyx Corp | Quaternary ammonium salts of organophosphorus acids |
-
1970
- 1970-03-10 FR FR7008450A patent/FR2037858A5/fr not_active Expired
- 1970-03-10 IE IE317/70A patent/IE34580B1/xx unknown
- 1970-03-10 HU HUGA1143A patent/HU167757B/hu unknown
- 1970-03-10 ES ES377330A patent/ES377330A1/es not_active Expired
- 1970-03-10 DE DE2011376A patent/DE2011376B2/de active Granted
- 1970-03-10 SU SU701411634A patent/SU383303A3/ru active
- 1970-03-10 IL IL34045A patent/IL34045A/xx unknown
- 1970-03-10 NO NO841/70A patent/NO138629C/no unknown
- 1970-03-10 HU HUGA1000A patent/HU168215B/hu unknown
- 1970-03-10 CH CH355470A patent/CH547310A/xx not_active IP Right Cessation
- 1970-03-10 DE DE2065236A patent/DE2065236C3/de not_active Expired
- 1970-03-10 CH CH1596673A patent/CH565809A5/xx not_active IP Right Cessation
- 1970-03-10 SE SE7003186A patent/SE404527B/sv unknown
- 1970-03-10 US US00018283A patent/US3725399A/en not_active Expired - Lifetime
- 1970-03-10 DK DK117470AA patent/DK136480B/da unknown
- 1970-03-10 BE BE747119D patent/BE747119A/xx not_active IP Right Cessation
- 1970-03-10 NL NL7003358.A patent/NL159389B/xx not_active IP Right Cessation
- 1970-03-10 AT AT225170A patent/AT306919B/de not_active IP Right Cessation
- 1970-03-10 PL PL1970139316A patent/PL80548B1/pl unknown
-
1972
- 1972-05-10 JP JP47045559A patent/JPS50838B1/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275626A (en) | 1962-07-31 | 1966-09-27 | Lilly Co Eli | Penicillin conversion via sulfoxide |
| US3280131A (en) | 1964-02-10 | 1966-10-18 | Millmaster Onyx Corp | Quaternary ammonium salts of organophosphorus acids |
Non-Patent Citations (7)
| Title |
|---|
| CA, Vol. 44, 1950, 8321a |
| CA, Vol. 49, 1955, 10835l |
| CA, Vol. 52, 1958, 17092h |
| CA, Vol. 54, 1960, 17426d |
| Houben - Weyl: Methoden der org. Chemie, Vol. XII, 1, 1963, S. 383-384 |
| J.org.Chem., Vol. 18, 1953, S. 362-366 |
| Wazer, van: Phosphorus and its Compounds 1966,, Bd . 1, S. 360, 385 |
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