SU544376A3 - Способ получени производных цефалоспорина или их солей в виде смеси диастереоизомеров или отдельных диастереоизомеров - Google Patents
Способ получени производных цефалоспорина или их солей в виде смеси диастереоизомеров или отдельных диастереоизомеровInfo
- Publication number
- SU544376A3 SU544376A3 SU2105526A SU2105526A SU544376A3 SU 544376 A3 SU544376 A3 SU 544376A3 SU 2105526 A SU2105526 A SU 2105526A SU 2105526 A SU2105526 A SU 2105526A SU 544376 A3 SU544376 A3 SU 544376A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- weight
- parts
- oxo
- sodium
- chlorocarbonyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 17
- 229930186147 Cephalosporin Natural products 0.000 title claims description 15
- 229940124587 cephalosporin Drugs 0.000 title claims description 15
- 150000001780 cephalosporins Chemical class 0.000 title claims description 11
- 150000003839 salts Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- -1 for example Substances 0.000 claims description 22
- 229910052708 sodium Inorganic materials 0.000 claims description 16
- 239000011734 sodium Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 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 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000000872 buffer Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 238000002329 infrared spectrum Methods 0.000 claims 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 11
- 239000000243 solution Substances 0.000 claims 11
- 229950004030 cefaloglycin Drugs 0.000 claims 7
- 150000004683 dihydrates Chemical class 0.000 claims 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 239000003153 chemical reaction reagent Substances 0.000 claims 6
- 159000000000 sodium salts Chemical class 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 claims 5
- 235000019439 ethyl acetate Nutrition 0.000 claims 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims 5
- 239000002244 precipitate Substances 0.000 claims 5
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 claims 5
- 150000007513 acids Chemical class 0.000 claims 4
- 238000003756 stirring Methods 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- AVGYWQBCYZHHPN-CYJZLJNKSA-N cephalexin monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 AVGYWQBCYZHHPN-CYJZLJNKSA-N 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- PSGBEZYOQCOMKH-UHFFFAOYSA-N 2-oxo-3-phenylimidazolidine-1-carbonyl chloride Chemical compound O=C1N(C(=O)Cl)CCN1C1=CC=CC=C1 PSGBEZYOQCOMKH-UHFFFAOYSA-N 0.000 claims 2
- OIOGFDPKEOSFCZ-UHFFFAOYSA-N 3-methyl-2-oxoimidazolidine-1-carbonyl chloride Chemical compound CN1CCN(C(Cl)=O)C1=O OIOGFDPKEOSFCZ-UHFFFAOYSA-N 0.000 claims 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
- 230000003115 biocidal effect Effects 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 229940106164 cephalexin Drugs 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 150000003951 lactams Chemical class 0.000 claims 2
- OHLUUHNLEMFGTQ-DYCDLGHISA-N n-deuterio-n-methylacetamide Chemical compound [2H]N(C)C(C)=O OHLUUHNLEMFGTQ-DYCDLGHISA-N 0.000 claims 2
- 230000020477 pH reduction Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- 238000001228 spectrum Methods 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
- JTPZTKBRUCILQD-UHFFFAOYSA-N 1-methylimidazolidin-2-one Chemical compound CN1CCNC1=O JTPZTKBRUCILQD-UHFFFAOYSA-N 0.000 claims 1
- LTIKXHNURBSILH-UHFFFAOYSA-N 2-oxo-3-sulfamoylimidazolidine-1-carbonyl chloride Chemical compound NS(=O)(=O)N1CCN(C(Cl)=O)C1=O LTIKXHNURBSILH-UHFFFAOYSA-N 0.000 claims 1
- VOVWRNNUBILFJT-UHFFFAOYSA-N 3-benzoyl-2-oxoimidazolidine-1-carbonyl chloride Chemical compound O=C1N(C(=O)Cl)CCN1C(=O)C1=CC=CC=C1 VOVWRNNUBILFJT-UHFFFAOYSA-N 0.000 claims 1
- ZWTPALHHEULAPI-UHFFFAOYSA-N 3-methylsulfonyl-2-oxoimidazolidine-1-carbonyl chloride Chemical compound CS(=O)(=O)N1CCN(C(Cl)=O)C1=O ZWTPALHHEULAPI-UHFFFAOYSA-N 0.000 claims 1
- ZZNMRBGELWVJND-UHFFFAOYSA-N 3-phenyl-1h-imidazol-2-one Chemical compound O=C1NC=CN1C1=CC=CC=C1 ZZNMRBGELWVJND-UHFFFAOYSA-N 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-YYWVXINBSA-N N,N-dimethylformamide-d7 Chemical compound [2H]C(=O)N(C([2H])([2H])[2H])C([2H])([2H])[2H] ZMXDDKWLCZADIW-YYWVXINBSA-N 0.000 claims 1
- 229930182555 Penicillin Natural products 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 229920013678 Strux Polymers 0.000 claims 1
- 239000008351 acetate buffer Substances 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 238000004458 analytical method Methods 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 230000008033 biological extinction Effects 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000007979 citrate buffer Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 238000001962 electrophoresis Methods 0.000 claims 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 1
- 235000019341 magnesium sulphate Nutrition 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 235000010755 mineral Nutrition 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000004682 monohydrates Chemical class 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 239000012188 paraffin wax Substances 0.000 claims 1
- 150000002960 penicillins Chemical class 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 239000008363 phosphate buffer Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 239000001488 sodium phosphate Substances 0.000 claims 1
- 229910000162 sodium phosphate Inorganic materials 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000002585 base Substances 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-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
- 241000228143 Penicillium Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000001540 azides Chemical group 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical class [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229960000603 cefalotin Drugs 0.000 description 1
- VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 1
- 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
- 238000007796 conventional method Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
- 229950010879 phenamine Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2407715A DE2407715C2 (de) | 1974-02-18 | 1974-02-18 | Cephalosporine, Verfahren zu ihrer Herstellung sowie Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU544376A3 true SU544376A3 (ru) | 1977-01-25 |
Family
ID=5907728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2105526A SU544376A3 (ru) | 1974-02-18 | 1975-02-14 | Способ получени производных цефалоспорина или их солей в виде смеси диастереоизомеров или отдельных диастереоизомеров |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS50116489A (en, 2012) |
| AR (1) | AR207586A1 (en, 2012) |
| AT (1) | AT334533B (en, 2012) |
| BE (1) | BE825623A (en, 2012) |
| BG (1) | BG26394A3 (en, 2012) |
| DD (1) | DD118649A5 (en, 2012) |
| DE (1) | DE2407715C2 (en, 2012) |
| DK (1) | DK57275A (en, 2012) |
| EG (1) | EG11586A (en, 2012) |
| ES (1) | ES434797A1 (en, 2012) |
| FI (1) | FI750417A7 (en, 2012) |
| FR (1) | FR2261010B1 (en, 2012) |
| GB (1) | GB1476905A (en, 2012) |
| HU (1) | HU168594B (en, 2012) |
| IL (1) | IL46631A0 (en, 2012) |
| LU (1) | LU71860A1 (en, 2012) |
| NL (1) | NL7501914A (en, 2012) |
| NO (1) | NO750351L (en, 2012) |
| PL (1) | PL98594B1 (en, 2012) |
| RO (1) | RO66018A (en, 2012) |
| SE (1) | SE7501719L (en, 2012) |
| SU (1) | SU544376A3 (en, 2012) |
| ZA (1) | ZA75965B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2525541C2 (de) * | 1975-06-07 | 1984-01-12 | Bayer Ag, 5090 Leverkusen | β-Lactam-Antibiotica, Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel |
| DE2528079A1 (de) * | 1975-06-24 | 1977-01-20 | Bayer Ag | Penicilline, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| IL49846A (en) * | 1975-06-24 | 1979-07-25 | Bayer Ag | Penicillin and cephalosporin compounds containing an imidazolidinone ring substituted by a carbocycle or heterocycletheir preparation and pharmaceutical compositions comprising them |
| DE2528077A1 (de) * | 1975-06-24 | 1977-01-20 | Bayer Ag | Beta-lactamantibiotika, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| FR2362146A1 (fr) * | 1976-08-17 | 1978-03-17 | Fujisawa Pharmaceutical Co | Procede de preparation de composes d'acide 7-(n-substitue-2-phenylglycinamido)-3-substitue-3-cephem-4-carboxylique et nouveaux produits ainsi obtenus, a activite antibacterienne |
| DE2658906A1 (de) * | 1976-12-24 | 1978-07-06 | Bayer Ag | Beta-lactam-antibiotika, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| JPS545974A (en) * | 1977-06-16 | 1979-01-17 | Ajinomoto Co Inc | Imidazoledicaroboxylic acid derivatives |
| DE2810083A1 (de) | 1978-03-08 | 1979-09-20 | Bayer Ag | Beta-lactam-verbindungen |
| EP0015240A1 (de) * | 1979-02-16 | 1980-09-03 | Ciba-Geigy Ag | Azacyclyl (thio) ureidoacetyl-Verbindungen und Verfahren zu ihrer Herstellung |
| US4464366A (en) * | 1979-12-19 | 1984-08-07 | Ciba Geigy Corporation | Cephem compounds having a terminal aminocarboxylic acid grouping and containing an azacyclyl(thio)ureido group |
| CN114552015B (zh) * | 2022-02-25 | 2024-04-05 | 珠海市赛纬电子材料股份有限公司 | 电解液添加剂、锂离子电池电解液及锂离子电池 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641021A (en) * | 1969-04-18 | 1972-02-08 | Lilly Co Eli | 3 7-(ring-substituted) cephalosporin compounds |
| DE2104580C3 (de) * | 1971-02-01 | 1981-04-02 | Bayer Ag, 5090 Leverkusen | Acylureidopenicilline |
| BE786271A (fr) * | 1971-07-17 | 1973-01-15 | Takeda Chemical Industries Ltd | Cephalosporines |
| BE790440A (en, 2012) * | 1971-10-23 | 1973-04-24 | Bayer Ag |
-
1974
- 1974-02-18 DE DE2407715A patent/DE2407715C2/de not_active Expired
-
1975
- 1975-01-01 AR AR257669A patent/AR207586A1/es active
- 1975-02-04 NO NO750351A patent/NO750351L/no unknown
- 1975-02-12 BG BG028956A patent/BG26394A3/xx unknown
- 1975-02-14 IL IL7546631A patent/IL46631A0/xx unknown
- 1975-02-14 FI FI750417A patent/FI750417A7/fi not_active Application Discontinuation
- 1975-02-14 SU SU2105526A patent/SU544376A3/ru active
- 1975-02-15 EG EG64/75A patent/EG11586A/xx active
- 1975-02-15 PL PL1975178088A patent/PL98594B1/pl unknown
- 1975-02-17 JP JP50018955A patent/JPS50116489A/ja active Pending
- 1975-02-17 GB GB658675A patent/GB1476905A/en not_active Expired
- 1975-02-17 ES ES434797A patent/ES434797A1/es not_active Expired
- 1975-02-17 LU LU71860A patent/LU71860A1/xx unknown
- 1975-02-17 DK DK57275*#A patent/DK57275A/da unknown
- 1975-02-17 ZA ZA00750965A patent/ZA75965B/xx unknown
- 1975-02-17 DD DD184251A patent/DD118649A5/xx unknown
- 1975-02-17 SE SE7501719A patent/SE7501719L/xx unknown
- 1975-02-17 BE BE153428A patent/BE825623A/xx unknown
- 1975-02-18 HU HUBA3208A patent/HU168594B/hu unknown
- 1975-02-18 NL NL7501914A patent/NL7501914A/xx not_active Application Discontinuation
- 1975-02-18 FR FR7505043A patent/FR2261010B1/fr not_active Expired
- 1975-02-18 AT AT118975A patent/AT334533B/de not_active IP Right Cessation
- 1975-02-18 RO RO197581437A patent/RO66018A/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK57275A (en, 2012) | 1975-10-20 |
| DD118649A5 (en, 2012) | 1976-03-12 |
| BG26394A3 (bg) | 1979-03-15 |
| AR207586A1 (es) | 1976-10-15 |
| IL46631A0 (en) | 1975-04-25 |
| PL98594B1 (pl) | 1978-05-31 |
| GB1476905A (en) | 1977-06-16 |
| SE7501719L (en, 2012) | 1975-08-19 |
| NL7501914A (nl) | 1975-08-20 |
| ZA75965B (en) | 1976-01-28 |
| JPS50116489A (en, 2012) | 1975-09-11 |
| DE2407715A1 (de) | 1975-09-04 |
| ATA118975A (de) | 1976-05-15 |
| FI750417A7 (en, 2012) | 1975-08-19 |
| AU7820875A (en) | 1976-08-19 |
| LU71860A1 (en, 2012) | 1975-12-09 |
| DE2407715C2 (de) | 1982-12-02 |
| AT334533B (de) | 1976-01-25 |
| FR2261010A1 (en, 2012) | 1975-09-12 |
| RO66018A (fr) | 1980-01-15 |
| BE825623A (fr) | 1975-08-18 |
| HU168594B (en, 2012) | 1976-06-28 |
| ES434797A1 (es) | 1977-02-01 |
| EG11586A (en) | 1978-06-30 |
| FR2261010B1 (en, 2012) | 1980-01-11 |
| NO750351L (en, 2012) | 1975-08-19 |
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