SU927118A3 - Способ получени производных цефалоспорина - Google Patents
Способ получени производных цефалоспорина Download PDFInfo
- Publication number
- SU927118A3 SU927118A3 SU802928400A SU2928400A SU927118A3 SU 927118 A3 SU927118 A3 SU 927118A3 SU 802928400 A SU802928400 A SU 802928400A SU 2928400 A SU2928400 A SU 2928400A SU 927118 A3 SU927118 A3 SU 927118A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- solution
- thia
- oxo
- bicyclo
- aza
- Prior art date
Links
- 229940124587 cephalosporin Drugs 0.000 title claims abstract description 7
- 229930186147 Cephalosporin Natural products 0.000 title claims abstract description 6
- 150000001780 cephalosporins Chemical class 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title description 7
- -1 cyanomethyl Chemical group 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 122
- 239000000243 solution Substances 0.000 claims description 66
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 32
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 28
- 239000012047 saturated solution Substances 0.000 claims description 23
- 238000001228 spectrum Methods 0.000 claims description 23
- 238000002329 infrared spectrum Methods 0.000 claims description 22
- 239000012074 organic phase Substances 0.000 claims description 22
- 239000011780 sodium chloride Substances 0.000 claims description 20
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 14
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 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 4
- 238000009835 boiling Methods 0.000 claims description 3
- 150000002081 enamines Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000006317 isomerization reaction Methods 0.000 claims description 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 2
- 235000010755 mineral Nutrition 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 5
- 229920002554 vinyl polymer Chemical group 0.000 abstract description 5
- 239000000543 intermediate Substances 0.000 abstract description 3
- 239000003242 anti bacterial agent Substances 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 230000001681 protective effect Effects 0.000 abstract 5
- ARYQWIKYCPXNBM-UHFFFAOYSA-N 2-(3-cyclooctylcycloocten-1-yl)acetaldehyde Chemical compound O=CCC1=CC(CCCCC1)C1CCCCCCC1 ARYQWIKYCPXNBM-UHFFFAOYSA-N 0.000 abstract 2
- BPFUBCUAUHXMDJ-UHFFFAOYSA-N 2-(3-cyclooctylcyclooctylidene)acetaldehyde Chemical group C1C(=CC=O)CCCCCC1C1CCCCCCC1 BPFUBCUAUHXMDJ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000012153 distilled water Substances 0.000 description 23
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 7
- HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- PBZUAIHRZUBBAJ-UHFFFAOYSA-N Hydroxyiminoacetic acid Natural products ON=CC(O)=O PBZUAIHRZUBBAJ-UHFFFAOYSA-N 0.000 description 2
- 241000717981 Meringis Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004071 soot Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- VSIMNRRKKQUGMF-UHFFFAOYSA-N 1,1-dimethoxy-n-methylmethanamine Chemical compound CNC(OC)OC VSIMNRRKKQUGMF-UHFFFAOYSA-N 0.000 description 1
- ATIJWZXWXNXVOY-UHFFFAOYSA-N 1-ethoxy-n,n,n',n'-tetramethylmethanediamine Chemical compound CCOC(N(C)C)N(C)C ATIJWZXWXNXVOY-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical class CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- PKPGSMOHYWOGJR-UHFFFAOYSA-N 2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid Chemical compound CON=C(C(O)=O)C1=CSC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 PKPGSMOHYWOGJR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001641404 Meringa Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- PVQATPQSBYNMGE-UHFFFAOYSA-N [benzhydryloxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)C1=CC=CC=C1 PVQATPQSBYNMGE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 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
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- XKXIQBVKMABYQJ-UHFFFAOYSA-M tert-butyl carbonate Chemical compound CC(C)(C)OC([O-])=O XKXIQBVKMABYQJ-UHFFFAOYSA-M 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members 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
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7913097A FR2457297A1 (fr) | 1979-05-23 | 1979-05-23 | Nouvelles vinyl-3 cephalosporines, et leur preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU927118A3 true SU927118A3 (ru) | 1982-05-07 |
Family
ID=9225763
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802928400A SU927118A3 (ru) | 1979-05-23 | 1980-05-21 | Способ получени производных цефалоспорина |
| SU802928399A SU965358A3 (ru) | 1979-05-23 | 1980-05-21 | Способ получени производных 3-оксивинилцефалоспорина |
| SU813229954A SU984411A3 (ru) | 1979-05-23 | 1981-01-19 | Способ получени производных 3-оксивинилцефалоспорина |
| SU813229054A SU988193A3 (ru) | 1979-05-23 | 1981-01-19 | Способ получени производных 3-оксивинилцефалоспорина |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802928399A SU965358A3 (ru) | 1979-05-23 | 1980-05-21 | Способ получени производных 3-оксивинилцефалоспорина |
| SU813229954A SU984411A3 (ru) | 1979-05-23 | 1981-01-19 | Способ получени производных 3-оксивинилцефалоспорина |
| SU813229054A SU988193A3 (ru) | 1979-05-23 | 1981-01-19 | Способ получени производных 3-оксивинилцефалоспорина |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US4365062A (enExample) |
| JP (2) | JPS55154978A (enExample) |
| AT (2) | AT370737B (enExample) |
| AU (2) | AU532884B2 (enExample) |
| BE (2) | BE883418A (enExample) |
| CA (2) | CA1148141A (enExample) |
| CH (2) | CH645380A5 (enExample) |
| CS (1) | CS235508B2 (enExample) |
| DD (2) | DD151064A5 (enExample) |
| DE (2) | DE3019445A1 (enExample) |
| DK (2) | DK222280A (enExample) |
| ES (4) | ES491688A0 (enExample) |
| FI (2) | FI801642A7 (enExample) |
| FR (1) | FR2457297A1 (enExample) |
| GB (2) | GB2051061B (enExample) |
| GR (2) | GR68436B (enExample) |
| HU (2) | HU184759B (enExample) |
| IE (2) | IE49813B1 (enExample) |
| IL (2) | IL60141A (enExample) |
| IT (2) | IT1140972B (enExample) |
| LU (2) | LU82476A1 (enExample) |
| NL (2) | NL8003010A (enExample) |
| NO (2) | NO801503L (enExample) |
| NZ (2) | NZ193800A (enExample) |
| PH (2) | PH15916A (enExample) |
| PL (3) | PL126671B1 (enExample) |
| PT (2) | PT71277A (enExample) |
| SE (2) | SE8003823L (enExample) |
| SU (4) | SU927118A3 (enExample) |
| YU (3) | YU136980A (enExample) |
| ZA (2) | ZA803035B (enExample) |
| ZW (1) | ZW12380A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2494276A2 (fr) * | 1980-11-20 | 1982-05-21 | Rhone Poulenc Ind | Nouvelles vinyl-3 cephalosporines, et leur preparation |
| FR2511372A1 (fr) * | 1981-08-17 | 1983-02-18 | Rhone Poulenc Sante | Nouveaux derives de la cephalosporine et leur preparation |
| FR2511376A1 (fr) * | 1981-08-17 | 1983-02-18 | Rhone Poulenc Sante | Nouveaux derives de la cephalosporine et leur prepration |
| FR2531712A1 (fr) * | 1982-08-13 | 1984-02-17 | Rhone Poulenc Sante | Nouveaux derives de la cephalosporine et leur preparation |
| US4609730A (en) * | 1982-11-22 | 1986-09-02 | Fujisawa Pharmaceutical Co., Ltd. | 7-[substituted imino-2-(2-aminothiazol-4-yl)-acetamido]-3(2,2-dihalovinyl or ethynyl)-3-cephem-4-carboxylic acid (syn isomers), having antimicrobial activities |
| US4520022A (en) * | 1983-01-28 | 1985-05-28 | Bristol-Myers Company | Substituted vinyl cephalosporins |
| ZM884A1 (en) * | 1983-01-28 | 1984-10-22 | Bristol Myers Co | Substituted vinyl cephalosporins |
| JPS604883U (ja) * | 1983-06-24 | 1985-01-14 | 松下冷機株式会社 | 冷蔵庫等の冷却装置 |
| US4708955A (en) * | 1985-06-24 | 1987-11-24 | Bristol-Myers Company | 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof |
| US4874856A (en) * | 1985-06-24 | 1989-10-17 | Bristol-Myers Company | 3-(substituted)propenyl-7-(aminothiazolylacetamido) ceph-3-em-4-carboxylic acids and esters thereof |
| MY127641A (en) * | 1995-10-12 | 2006-12-29 | Essential Therapeutics Inc | Cephalosporin antibiotics |
| US6025352A (en) * | 1997-09-29 | 2000-02-15 | Microcide Pharmaceuticals, Inc. | Cephalosporin antibiotics |
| US6030965A (en) * | 1997-09-30 | 2000-02-29 | Microcide Pharmaceuticals, Inc. | Cephalosporin antibiotics |
| WO2003072582A1 (en) * | 2002-02-28 | 2003-09-04 | Lg Life Sciences Ltd. | Novel cephalosporin compounds and process for preparing the same |
| JP5733856B2 (ja) | 2007-10-09 | 2015-06-10 | ソファーミア，インコーポレイテッド | 広帯域β−ラクタマーゼ阻害薬 |
| CA2905240A1 (en) | 2013-03-12 | 2014-10-09 | Gladius Pharmaceuticals Coproration | Derivatized 3-styryl-cephalosporins |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3769277A (en) * | 1970-01-23 | 1973-10-30 | Glaxo Lab Ltd | Preparation of delta3-4 carboxy cephalosporins having a 3-vinyl or substituted 3-vinyl group |
| US3823139A (en) * | 1970-03-26 | 1974-07-09 | Glaxo Lab Ltd | Cephalosporins having a ypsilon-carbonyl group at position-3 |
| US3674784A (en) * | 1970-07-27 | 1972-07-04 | Lilly Co Eli | 3-formyl cephalosporin sulfoxides |
| US4065620A (en) * | 1971-06-14 | 1977-12-27 | Eli Lilly And Company | 3-(Substituted) vinyl cephalosporins |
| US4144393A (en) * | 1973-12-21 | 1979-03-13 | Glaxo Laboratories Limited | 3-Acetoxymethyl cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyiminoarylacetamido group |
| DE2637176A1 (de) | 1975-08-22 | 1977-03-03 | Ciba Geigy Ag | Carbonylmethylderivate |
| JPS5285185A (en) * | 1976-01-05 | 1977-07-15 | Teijin Ltd | Preparation of 7-acylaminocephalosporanic acids |
| JPS5289694A (en) * | 1976-01-23 | 1977-07-27 | Asahi Chem Ind Co Ltd | Novel cephalosporins |
| US4094978A (en) * | 1976-07-29 | 1978-06-13 | Syntex (U.S.A.) Inc. | 3-propenyl derivatives of cephalosporin, compositions and their use |
| US4255423A (en) * | 1977-07-27 | 1981-03-10 | Merck & Co., Inc. | Cephalosporin compounds |
| EP0015240A1 (de) * | 1979-02-16 | 1980-09-03 | Ciba-Geigy Ag | Azacyclyl (thio) ureidoacetyl-Verbindungen und Verfahren zu ihrer Herstellung |
-
1979
- 1979-05-23 FR FR7913097A patent/FR2457297A1/fr active Granted
-
1980
- 1980-05-21 BE BE0/200709A patent/BE883418A/fr not_active IP Right Cessation
- 1980-05-21 US US06/152,153 patent/US4365062A/en not_active Expired - Lifetime
- 1980-05-21 CS CS803544A patent/CS235508B2/cs unknown
- 1980-05-21 YU YU01369/80A patent/YU136980A/xx unknown
- 1980-05-21 LU LU82476A patent/LU82476A1/fr unknown
- 1980-05-21 CA CA000352346A patent/CA1148141A/fr not_active Expired
- 1980-05-21 FI FI801642A patent/FI801642A7/fi not_active Application Discontinuation
- 1980-05-21 BE BE0/200708A patent/BE883417A/fr not_active IP Right Cessation
- 1980-05-21 DK DK222280A patent/DK222280A/da not_active Application Discontinuation
- 1980-05-21 AT AT0271180A patent/AT370737B/de not_active IP Right Cessation
- 1980-05-21 DK DK223180A patent/DK223180A/da not_active Application Discontinuation
- 1980-05-21 HU HU801279A patent/HU184759B/hu unknown
- 1980-05-21 CH CH399180A patent/CH645380A5/fr not_active IP Right Cessation
- 1980-05-21 US US06/152,084 patent/US4307230A/en not_active Expired - Lifetime
- 1980-05-21 GB GB8016726A patent/GB2051061B/en not_active Expired
- 1980-05-21 SU SU802928400A patent/SU927118A3/ru active
- 1980-05-21 YU YU01370/80A patent/YU137080A/xx unknown
- 1980-05-21 DD DD80221267A patent/DD151064A5/de unknown
- 1980-05-21 AT AT0271080A patent/AT368509B/de not_active IP Right Cessation
- 1980-05-21 CH CH3990/80A patent/CH650000A5/fr not_active IP Right Cessation
- 1980-05-21 DE DE19803019445 patent/DE3019445A1/de not_active Withdrawn
- 1980-05-21 NZ NZ193800A patent/NZ193800A/xx unknown
- 1980-05-21 GR GR62017A patent/GR68436B/el unknown
- 1980-05-21 PL PL1980229959A patent/PL126671B1/pl unknown
- 1980-05-21 IT IT22241/80A patent/IT1140972B/it active
- 1980-05-21 IT IT22242/80A patent/IT1140973B/it active
- 1980-05-21 GB GB8016725A patent/GB2052488B/en not_active Expired
- 1980-05-21 PT PT71277A patent/PT71277A/pt unknown
- 1980-05-21 ES ES491688A patent/ES491688A0/es active Granted
- 1980-05-21 ZA ZA00803035A patent/ZA803035B/xx unknown
- 1980-05-21 IE IE1060/80A patent/IE49813B1/en unknown
- 1980-05-21 DE DE19803019430 patent/DE3019430A1/de not_active Withdrawn
- 1980-05-21 GR GR62016A patent/GR68428B/el unknown
- 1980-05-21 AU AU58593/80A patent/AU532884B2/en not_active Ceased
- 1980-05-21 ES ES491689A patent/ES491689A0/es active Granted
- 1980-05-21 NZ NZ193801A patent/NZ193801A/xx unknown
- 1980-05-21 SE SE8003823A patent/SE8003823L/xx not_active Application Discontinuation
- 1980-05-21 IE IE1059/80A patent/IE49812B1/en unknown
- 1980-05-21 PT PT71278A patent/PT71278A/pt unknown
- 1980-05-21 HU HU801280A patent/HU183143B/hu unknown
- 1980-05-21 PL PL1980224390A patent/PL126491B1/pl unknown
- 1980-05-21 AU AU58594/80A patent/AU537785B2/en not_active Ceased
- 1980-05-21 CA CA000352335A patent/CA1149375A/fr not_active Expired
- 1980-05-21 FI FI801643A patent/FI801643A7/fi not_active Application Discontinuation
- 1980-05-21 NO NO801503A patent/NO801503L/no unknown
- 1980-05-21 PL PL1980224392A patent/PL122638B1/pl unknown
- 1980-05-21 DD DD80221268A patent/DD151169A5/de unknown
- 1980-05-21 SE SE8003822A patent/SE8003822L/xx not_active Application Discontinuation
- 1980-05-21 SU SU802928399A patent/SU965358A3/ru active
- 1980-05-21 LU LU82478A patent/LU82478A1/fr unknown
- 1980-05-21 NO NO801504A patent/NO801504L/no unknown
- 1980-05-21 ZW ZW123/80A patent/ZW12380A1/xx unknown
- 1980-05-21 ZA ZA00803036A patent/ZA803036B/xx unknown
- 1980-05-22 PH PH24057A patent/PH15916A/en unknown
- 1980-05-22 IL IL60141A patent/IL60141A/xx unknown
- 1980-05-22 IL IL60140A patent/IL60140A/xx unknown
- 1980-05-22 PH PH24058A patent/PH17310A/en unknown
- 1980-05-23 JP JP6800680A patent/JPS55154978A/ja active Pending
- 1980-05-23 NL NL8003010A patent/NL8003010A/nl not_active Application Discontinuation
- 1980-05-23 JP JP6800780A patent/JPS55154979A/ja active Pending
- 1980-05-23 NL NL8003024A patent/NL8003024A/nl not_active Application Discontinuation
- 1980-09-22 ES ES495237A patent/ES495237A0/es active Granted
- 1980-09-22 ES ES495236A patent/ES8106533A1/es not_active Expired
-
1981
- 1981-01-19 SU SU813229954A patent/SU984411A3/ru active
- 1981-01-19 SU SU813229054A patent/SU988193A3/ru active
-
1983
- 1983-03-09 YU YU00561/83A patent/YU56183A/xx unknown
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