JPS609516B2 - セフエム骨格の環化製法 - Google Patents
セフエム骨格の環化製法Info
- Publication number
- JPS609516B2 JPS609516B2 JP50028452A JP2845275A JPS609516B2 JP S609516 B2 JPS609516 B2 JP S609516B2 JP 50028452 A JP50028452 A JP 50028452A JP 2845275 A JP2845275 A JP 2845275A JP S609516 B2 JPS609516 B2 JP S609516B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- groups
- parts
- amino
- 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
- 238000007363 ring formation reaction Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000001118 alkylidene group Chemical class 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
- -1 aralkanoyl Chemical group 0.000 description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- 238000003756 stirring Methods 0.000 description 31
- 239000002904 solvent Substances 0.000 description 29
- 125000001424 substituent group Chemical group 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- 125000002252 acyl group Chemical group 0.000 description 19
- 229960000583 acetic acid Drugs 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 239000005457 ice water Substances 0.000 description 13
- 239000002994 raw material Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- QNXQLPUEZYZYFC-UHFFFAOYSA-N (4-nitrophenyl)methyl acetate Chemical compound CC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 QNXQLPUEZYZYFC-UHFFFAOYSA-N 0.000 description 11
- 125000003396 thiol group Chemical group [H]S* 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 125000003277 amino group Chemical group 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 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 8
- SVDWECPQUANQNC-UHFFFAOYSA-N 2-(azetidin-1-yl)acetic acid Chemical class OC(=O)CN1CCC1 SVDWECPQUANQNC-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 125000004354 sulfur functional group Chemical group 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000004423 acyloxy group Chemical group 0.000 description 6
- 125000001475 halogen functional group Chemical group 0.000 description 6
- 229960001866 silicon dioxide Drugs 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 125000004149 thio group Chemical group *S* 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000005035 acylthio group Chemical group 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 150000007522 mineralic acids Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000007524 organic acids Chemical group 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- XHAXVDWUMCHTCY-UHFFFAOYSA-N 2,2,2-trichloroethyl acetate Chemical compound CC(=O)OCC(Cl)(Cl)Cl XHAXVDWUMCHTCY-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003435 aroyl group Chemical group 0.000 description 3
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- QBKMWJRMLACRJD-UHFFFAOYSA-N benzhydryl acetate Chemical compound C=1C=CC=CC=1C(OC(=O)C)C1=CC=CC=C1 QBKMWJRMLACRJD-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000002743 phosphorus functional group Chemical group 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 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 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical group OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000005277 alkyl imino group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000005587 carbonate group Chemical group 0.000 description 2
- 150000001782 cephems Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- 125000005638 hydrazono group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 125000005499 phosphonyl group Chemical group 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 125000000464 thioxo group Chemical group S=* 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YBADLXQNJCMBKR-UHFFFAOYSA-N (4-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C([N+]([O-])=O)C=C1 YBADLXQNJCMBKR-UHFFFAOYSA-N 0.000 description 1
- WTZPXQAJILENBR-UUSAFJCLSA-N (4-nitrophenyl)methyl (6R)-3-hydroxy-7-[(2-hydroxyphenyl)methylideneamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(C=1C(O)=CC=CC=1)=NC1[C@@H]2N(C(=C(CS2)O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O WTZPXQAJILENBR-UUSAFJCLSA-N 0.000 description 1
- MSJBRVIZZHKNPL-BDPMCISCSA-N (4-nitrophenyl)methyl (6r)-3-hydroxy-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)O)C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)NC(=O)COC1=CC=CC=C1 MSJBRVIZZHKNPL-BDPMCISCSA-N 0.000 description 1
- YTCUEIOOUOMPAT-RXMQYKEDSA-N (6r)-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=C(O)CS[C@@H]2CC(=O)N12 YTCUEIOOUOMPAT-RXMQYKEDSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 241001609213 Carassius carassius Species 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- KFOMSQLCZUDRNJ-UHFFFAOYSA-N N(=[N+]=[N-])N=NN=NNNN Chemical compound N(=[N+]=[N-])N=NN=NNNN KFOMSQLCZUDRNJ-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000000676 alkoxyimino group Chemical group 0.000 description 1
- 125000005138 alkoxysulfonyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 125000004467 aryl imino group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001753 carvones Chemical class 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- QHTOIDKCEPKVCM-ZCFIWIBFSA-N cepham group Chemical group S1CCCN2[C@H]1CC2=O QHTOIDKCEPKVCM-ZCFIWIBFSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- UETQVDZZPKAQIC-UHFFFAOYSA-N chlorane Chemical compound Cl.Cl.Cl.Cl UETQVDZZPKAQIC-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (83)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP50028452A JPS609516B2 (ja) | 1975-03-07 | 1975-03-07 | セフエム骨格の環化製法 |
CA000245317A CA1136132A (en) | 1975-02-17 | 1976-02-09 | Cyclization to form cephem ring and intermediates therefor |
SE7601715A SE421691B (sv) | 1975-02-17 | 1976-02-16 | Nya azetidinforening till anvendning som mellanprodukter for framstellning av 3-cefemforeningar |
DK061976A DK156575C (da) | 1975-02-17 | 1976-02-16 | Fremgangsmaade til fremstilling af 3-hydroxy-3-cephem- eller 3-oxo-cepham-carboxylsyrederivater |
PT64806A PT64806B (en) | 1975-02-17 | 1976-02-16 | Process of cyclization to form cephem ring and intermediate products for same |
IL57541A IL57541A (en) | 1975-02-17 | 1976-02-16 | 7-oxo-alpha-4-thia-2,6-diazabicyclo(3,2,0)heptene derivatives,process for their preparation and their cyclization to form cephem compounds and pharmaceutical compositions comprising said cephem compounds |
IL49048A IL49048A (en) | 1975-02-17 | 1976-02-16 | Cyclization process to form a cephem ring and intermediates therefor |
GB6187/76A GB1548641A (en) | 1975-02-17 | 1976-02-17 | Cyclization to form a cephem ring and intermediates therefor |
RO7694586A RO75006A (ro) | 1975-02-17 | 1976-02-17 | Procedeu pentru prepararea unor mercaptoazetidinone |
NZ184637A NZ184637A (en) | 1975-02-17 | 1976-02-17 | Method of cleaving a thiazoline ring |
RO7684836A RO68460A (ro) | 1975-02-17 | 1976-02-17 | Procedeu pentru prepararea unor derivati de azetidinona |
US05/658,665 US4079181A (en) | 1975-02-17 | 1976-02-17 | Certain 7-oxo-4-thio-2,6-diazabicyclo-3,2,0-hept-2-ene compounds |
BG034108A BG25076A3 (en) | 1975-02-17 | 1976-02-17 | A method of obtaining mercapto-azetidine derivatives |
GB41074/78A GB1548643A (en) | 1975-02-17 | 1976-02-17 | Thiazoline ring cleavage |
BG034105A BG24949A3 (en) | 1975-02-17 | 1976-02-17 | A method of obtaining mercaptoazetidine derivatives |
MX890676U MX6599E (es) | 1975-03-07 | 1976-02-17 | Procedimiento para la preparacion de compuestos de mercaptoacetidina |
DD7600195997A DD127901A5 (de) | 1975-02-17 | 1976-02-17 | Verfahren zur herstellung von mercaptoazetidin-derivaten |
MX890576U MX6578E (es) | 1975-02-21 | 1976-02-17 | Procedimiento para preparar derivados de 4-mercaptoacetidinona |
DD191283A DD124986A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-02-17 | 1976-02-17 | |
NZ184638A NZ184638A (en) | 1975-02-17 | 1976-02-17 | Derivatives of 7-oxo-4-thia-2,6-diazobicylic-hept-2-enes |
NZ184639A NZ184639A (en) | 1975-02-17 | 1976-02-17 | Azetidinones, intermediates for cephem compounds |
CH191876A CH627160A5 (en) | 1975-02-17 | 1976-02-17 | Process for preparing halogenated azetidinone or thiazolinoazetidinone derivatives |
BG034107A BG27557A4 (en) | 1975-02-17 | 1976-02-17 | Method of obtaining of cephemic compounds |
PL1976212108A PL114624B1 (en) | 1975-03-07 | 1976-02-17 | Process for preparing novel cephem derivatives |
MX890776U MX6579E (es) | 1975-03-07 | 1976-02-17 | Procedimiento para la preparacion de un compuesto de 3-oxocefem |
BG034106A BG25216A3 (en) | 1975-02-17 | 1976-02-17 | A method of obtaining mercaptoazetidyne derivatives |
IE313/76A IE42479B1 (en) | 1975-02-17 | 1976-02-17 | Cyclization to form a cephem ring and intermediates therefor |
AR262283A AR225878A1 (es) | 1975-02-17 | 1976-02-17 | Nuevos derivados de 3-amino-2-azetidinon-1-((2-halo-acetil o 2-haloetiliden))-acetico,procedimiento para prepararlos y procedimiento para obtener compuestos 3-cefem a partir de dichos derivados |
DD7600195998A DD127902A5 (de) | 1975-02-17 | 1976-02-17 | Verfahren zur herstellung von mercaptoazetidin-derivaten |
NL7601613A NL190721C (nl) | 1975-02-17 | 1976-02-17 | Werkwijze voor het bereiden van 3-hydroxy-cephem derivaten. |
DD7600195993A DD127899A5 (de) | 1975-02-17 | 1976-02-17 | Verfahren zur herstellung von cephem-verbindungen |
ES445250A ES445250A1 (es) | 1975-02-17 | 1976-02-17 | Un procedimiento para halogenar productos intermedios para la obtencion de anillos de cefem. |
BE164401A BE838656A (fr) | 1975-02-17 | 1976-02-17 | Procede de cyclisation menant au cycle de cepheme et intermediaires pour son execution |
NZ184640A NZ184640A (en) | 1975-02-17 | 1976-02-17 | Derivatives of 7-oxo-4-thia-2,6-diazo-bicyclic-hept-2-enes |
RO7694587A RO74958A (ro) | 1975-02-17 | 1976-02-17 | Procedeu de preparare a unor cefalosporine |
MX76898U MX3818E (es) | 1975-02-17 | 1976-02-17 | Procedimiento para la preparacion de enaminas de compuestos hidroxi-3-cefem |
AU11181/76A AU508160B2 (en) | 1975-02-17 | 1976-02-17 | Cyclization |
NZ184641A NZ184641A (en) | 1975-02-17 | 1976-02-17 | Mercaptoazetidines, intermediates for cephem ring compounds |
DE19762606278 DE2606278A1 (de) | 1975-02-17 | 1976-02-17 | Azetidin-derivate und verfahren zu ihrer herstellung |
MX890376U MX6598E (es) | 1975-03-07 | 1976-02-17 | Procedimiento para la preparacaion de enaminas de compuestos 3-hidroxi-3-cefem |
FR7604318A FR2334669A1 (fr) | 1975-02-17 | 1976-02-17 | Procede de cyclisation pour former un noyau de cephem et nouveaux produits ainsi obtenus |
GR50078A GR60437B (en) | 1975-02-17 | 1976-02-17 | Process for cyclization to form cephem ring and intermediates therefor |
YU384/76A YU40272B (en) | 1975-02-17 | 1976-02-17 | Process for producing beta-lactamine compounds |
NZ180037A NZ180037A (en) | 1975-02-17 | 1976-02-17 | Derivetives of2-azetidinone and cyclisation to form cephemring |
GB41073/78A GB1548642A (en) | 1975-02-17 | 1976-02-17 | 2-oxo-azetidine acetic acids |
PL1976212107A PL114457B1 (en) | 1975-03-07 | 1976-02-17 | Process for preparing novel derivatives of mercaptoazetidine |
DD7600195995A DD127900A5 (de) | 1975-02-17 | 1976-02-17 | Verfahren zur herstellung von mercaptoazetidin-derivaten |
BG032385A BG24948A3 (en) | 1975-02-17 | 1976-02-17 | A method of obtaining beta-lactam compounds |
PH18164A PH18022A (en) | 1975-02-17 | 1976-03-03 | Cyclization to form cephem ring and intermediate thereof |
SU762331355A SU1187717A3 (ru) | 1975-03-07 | 1976-03-05 | "cпocoб пoлучehия 2-okco-aзetидиhobыx coeдиhehий" |
RO197694535A RO74936A (fr) | 1975-02-17 | 1976-07-17 | Procede pour la preparation des mercaptoazetidiones |
FR7701590A FR2334684A1 (fr) | 1975-03-07 | 1977-01-20 | Procede de cyclisation d'halocetones ou d'halogenols pour former un noyau de cephem et nouveaux produits ainsi obtenus |
FR7701587A FR2334686A1 (fr) | 1975-02-21 | 1977-01-20 | Procede de preparation de sulfonates d'enolesters, ainsi que d'enamines non halogenes et nouveaux produits ainsi obtenus |
SU772446154A SU795463A4 (ru) | 1975-03-07 | 1977-01-26 | Способ получени 2-оксо-3-ацилами-HO-4-МЕРКАпТОАзЕТидиНОВ |
SU772442946A SU791247A3 (ru) | 1975-03-07 | 1977-01-26 | Способ получени производных 3-окси-3-цефем-4-карбоновой кислоты или соответствующей 3-оксоцефам-4-карбоновой кислоты |
US05/856,806 US4160085A (en) | 1975-02-17 | 1977-12-01 | Cyclization to form cephem ring and intermediates therefor |
CS78970A CS207654B2 (cs) | 1975-03-07 | 1978-02-15 | Způsob přípravy derivátů 7-acylamino-3-hydroxy-3cefem-4-karboxylové kyseliny nebo jejich oxoforem |
AT417178A AT351044B (de) | 1975-03-07 | 1978-06-08 | Verfahren zur herstellung von neuen azetidin- derivaten |
AT417078A AT361120B (de) | 1975-03-07 | 1978-06-08 | Verfahren zur herstellung von azetidinderivaten |
IL56050A IL56050A0 (en) | 1975-02-17 | 1978-11-26 | Azetidinones |
IL56049A IL56049A0 (en) | 1975-02-17 | 1978-11-26 | Thiazoline ring cleavage |
IL57418A IL57418A0 (en) | 1975-02-17 | 1979-05-28 | 7-oxo-4-thia-2,6-diazabicyclo(3,2,0)heptene derivatives |
IL57541A IL57541A0 (en) | 1975-02-17 | 1979-06-11 | 7-oxo- -4-thia-2,6-diazabicyclo(3,2,0)heptene derivatives,process for their preparation and pharmaceutical compositons comprising the same |
SE7907811A SE444811B (sv) | 1975-02-17 | 1979-09-20 | Azetidinylforening for framstellning av 3-hydroxi-cefemforeningar och forfarande for dess framstellning |
SE7907813A SE434637B (sv) | 1975-02-17 | 1979-09-20 | Ozoniseringsforfarande for framstellning av alfa-(azetidinyl)-alfa-(hydroxietyliden)-ettiksyraforeningar |
SE7907812A SE434950B (sv) | 1975-02-17 | 1979-09-20 | Forfarande for framstellning av 3-hydroxi-cefalosporinforeningar |
CA000337974A CA1077936A (en) | 1975-02-17 | 1979-10-19 | Cyclization to form cephem ring and intermediates therefor |
CA000337973A CA1144924A (en) | 1975-02-17 | 1979-10-19 | Cyclization to form cephem ring and intermediates therefor |
CA000337975A CA1095026A (en) | 1975-02-17 | 1979-10-19 | Cyclization to form cephem ring and intermediates therefor |
CA000338132A CA1132547A (en) | 1975-02-17 | 1979-10-22 | Cyclization to form cephem ring and intermediates therefor |
CH75080A CH628030A5 (en) | 1975-02-17 | 1980-01-30 | Process for the preparation of an enamine compound |
CH74880A CH630074A5 (en) | 1975-02-17 | 1980-01-30 | Process for preparing an acetidinone compound |
CH75180A CH628031A5 (en) | 1975-02-17 | 1980-01-30 | Process for the preparation of azetidinone compounds |
CH74980A CH634579A5 (en) | 1975-02-17 | 1980-01-30 | Process for preparing cephem compounds |
US06/125,232 US4332722A (en) | 1975-02-17 | 1980-02-27 | Cyclization to form cephem ring and intermediates therefor |
US06/125,233 US4346218A (en) | 1975-02-17 | 1980-02-27 | Cyclization process to form cephem ring |
AT0286880A AT363598B (de) | 1975-03-07 | 1980-05-29 | Verfahren zur herstellung von azetidinderivaten |
US06/338,651 US4440683A (en) | 1975-02-17 | 1982-01-11 | Cyclization to form cephem ring and azetidinone intermediates therefor |
DK76882A DK76882A (da) | 1975-02-17 | 1982-02-22 | Mellemprodukter til dannelse af en sephemring og fremgangsmaader til fremstilling deraf |
YU1738/82A YU40411B (en) | 1975-02-17 | 1982-08-10 | Process for obtaining mrcapto azetidine compounds |
YU1742/82A YU40414B (en) | 1975-02-17 | 1982-08-10 | Process for obtaining new azetidinone derivatives |
YU1739/82A YU40412B (en) | 1975-02-17 | 1982-08-10 | Process for producing mercapto azetidine compounds |
YU1741/82A YU40413B (en) | 1975-02-17 | 1982-08-10 | Process for obtaining cephem compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP50028452A JPS609516B2 (ja) | 1975-03-07 | 1975-03-07 | セフエム骨格の環化製法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS51105088A JPS51105088A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-17 |
JPS609516B2 true JPS609516B2 (ja) | 1985-03-11 |
Family
ID=12249046
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50028452A Expired JPS609516B2 (ja) | 1975-02-17 | 1975-03-07 | セフエム骨格の環化製法 |
Country Status (5)
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4013651A (en) * | 1975-05-12 | 1977-03-22 | Eli Lilly And Company | 3-substituted amino-cephalosporins |
US4024152A (en) * | 1975-09-19 | 1977-05-17 | Eli Lilly And Company | 4-Dithio-3-imido-azetidin-2-ones |
CA1148938A (en) * | 1979-05-08 | 1983-06-28 | John R. Corfield | Preparation of cephalosporins and intermediates employed therein |
JP3195959B2 (ja) * | 1991-03-13 | 2001-08-06 | 大塚化学株式会社 | 3−ヒドロキシセフェム誘導体の製造法 |
-
1975
- 1975-03-07 JP JP50028452A patent/JPS609516B2/ja not_active Expired
-
1976
- 1976-02-17 PL PL1976212108A patent/PL114624B1/pl unknown
- 1976-02-17 PL PL1976212107A patent/PL114457B1/pl unknown
- 1976-03-05 SU SU762331355A patent/SU1187717A3/ru active
-
1977
- 1977-01-20 FR FR7701590A patent/FR2334684A1/fr active Granted
- 1977-01-26 SU SU772442946A patent/SU791247A3/ru active
-
1978
- 1978-06-08 AT AT417078A patent/AT361120B/de not_active IP Right Cessation
-
1980
- 1980-05-29 AT AT0286880A patent/AT363598B/de not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
JPS51105088A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-17 |
SU1187717A3 (ru) | 1985-10-23 |
ATA286880A (de) | 1981-01-15 |
SU791247A3 (ru) | 1980-12-23 |
PL114457B1 (en) | 1981-01-31 |
AT363598B (de) | 1981-08-10 |
FR2334684B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-03-28 |
FR2334684A1 (fr) | 1977-07-08 |
PL114624B1 (en) | 1981-02-28 |
ATA417078A (de) | 1980-07-15 |
AT361120B (de) | 1981-02-25 |
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