JPS5833236B2 - ７−（ アルフア − チカンアミノアルカンアミド ）−３− チカン −３− セフエム −４− カルボンサンユウドウタイノ セイゾウホウ - Google Patents
７−（ アルフア − チカンアミノアルカンアミド ）−３− チカン −３− セフエム −４− カルボンサンユウドウタイノ セイゾウホウInfo
- Publication number
- JPS5833236B2 JPS5833236B2 JP3608074A JP3608074A JPS5833236B2 JP S5833236 B2 JPS5833236 B2 JP S5833236B2 JP 3608074 A JP3608074 A JP 3608074A JP 3608074 A JP3608074 A JP 3608074A JP S5833236 B2 JPS5833236 B2 JP S5833236B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- substituted
- solution
- acetyl
- 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
- -1 piperazinylthiocarbonylthio group Chemical class 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000000623 heterocyclic group Chemical class 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 124
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
- 239000000243 solution Substances 0.000 description 98
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 74
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
- 238000000862 absorption spectrum Methods 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- 238000000354 decomposition reaction Methods 0.000 description 41
- 238000003756 stirring Methods 0.000 description 37
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000000203 mixture Substances 0.000 description 29
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 28
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 25
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 238000001816 cooling Methods 0.000 description 17
- 239000012141 concentrate Substances 0.000 description 15
- 150000008064 anhydrides Chemical class 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Chemical class 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 8
- 239000008363 phosphate buffer Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- 239000004471 Glycine Substances 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000012264 purified product Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- NLZHNYNXJJFHRW-ZCFIWIBFSA-N (6r)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)C[C@H]21 NLZHNYNXJJFHRW-ZCFIWIBFSA-N 0.000 description 2
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 2
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- VFSVXTZQYLKGFK-CQSZACIVSA-N (2R)-2-[[2-(2,6-dichlorophenoxy)acetyl]amino]-2-phenylacetic acid Chemical compound N([C@@H](C(=O)O)C=1C=CC=CC=1)C(=O)COC1=C(Cl)C=CC=C1Cl VFSVXTZQYLKGFK-CQSZACIVSA-N 0.000 description 1
- ARUHGGCKUFXRBF-MRXNPFEDSA-N (2R)-2-[[2-(2-methoxyphenoxy)acetyl]amino]-2-phenylacetic acid Chemical compound COC1=CC=CC=C1OCC(=O)N[C@@H](C(O)=O)C1=CC=CC=C1 ARUHGGCKUFXRBF-MRXNPFEDSA-N 0.000 description 1
- PPUUIAQWBMSHOR-OAHLLOKOSA-N (2R)-2-[[2-(2-nitrophenoxy)acetyl]amino]-2-phenylacetic acid Chemical compound OC(=O)[C@H](NC(=O)COC1=C(C=CC=C1)[N+]([O-])=O)C1=CC=CC=C1 PPUUIAQWBMSHOR-OAHLLOKOSA-N 0.000 description 1
- CAYQJYBQQCYCEC-OAHLLOKOSA-N (2R)-2-[[2-(2-nitrophenyl)sulfanylacetyl]amino]-2-phenylacetic acid Chemical compound N([C@@H](C(=O)O)C=1C=CC=CC=1)C(=O)CSC1=CC=CC=C1[N+]([O-])=O CAYQJYBQQCYCEC-OAHLLOKOSA-N 0.000 description 1
- KUKRGTKBYFASJR-MRXNPFEDSA-N (2R)-2-[[2-(3-methoxyphenoxy)acetyl]amino]-2-phenylacetic acid Chemical compound COC1=CC=CC(OCC(=O)N[C@@H](C(O)=O)C=2C=CC=CC=2)=C1 KUKRGTKBYFASJR-MRXNPFEDSA-N 0.000 description 1
- PXMVSZFTGOKXPT-OAHLLOKOSA-N (2R)-2-[[2-(4-chloro-2-nitrophenoxy)acetyl]amino]-2-phenylacetic acid Chemical compound N([C@@H](C(=O)O)C=1C=CC=CC=1)C(=O)COC1=CC=C(Cl)C=C1[N+]([O-])=O PXMVSZFTGOKXPT-OAHLLOKOSA-N 0.000 description 1
- TXTKUFTWDKNCQW-OAHLLOKOSA-N (2R)-2-[[2-(4-chloro-2-nitrophenyl)acetyl]amino]-2-phenylacetic acid Chemical compound N([C@@H](C(=O)O)C=1C=CC=CC=1)C(=O)CC1=CC=C(Cl)C=C1[N+]([O-])=O TXTKUFTWDKNCQW-OAHLLOKOSA-N 0.000 description 1
- BRTLWCOOTPDIEE-ZETCQYMHSA-N (2s)-2-[[2-(2-nitrophenoxy)acetyl]amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)COC1=CC=CC=C1[N+]([O-])=O BRTLWCOOTPDIEE-ZETCQYMHSA-N 0.000 description 1
- SMFGDZSYSGJFNG-LBPRGKRZSA-N (2s)-3-methyl-2-[[2-(2-nitrophenoxy)acetyl]amino]butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)COC1=CC=CC=C1[N+]([O-])=O SMFGDZSYSGJFNG-LBPRGKRZSA-N 0.000 description 1
- ZIIHHGBQMAAERK-ZCFIWIBFSA-N (6R)-3-(azidomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N(=[N+]=[N-])CC=1CS[C@H]2N(C=1C(=O)O)C(C2)=O ZIIHHGBQMAAERK-ZCFIWIBFSA-N 0.000 description 1
- UOWHFCPGNQOIGP-MRVPVSSYSA-N (6R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound Cc1nnc(SCC2=C(N3[C@@H](CC3=O)SC2)C(O)=O)s1 UOWHFCPGNQOIGP-MRVPVSSYSA-N 0.000 description 1
- ASGIQPRGHDBJBR-XCGJVMPOSA-N (6r)-4-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1C=C(C(O)=O)N2C(=O)C[C@H]2S1 ASGIQPRGHDBJBR-XCGJVMPOSA-N 0.000 description 1
- XUTQHTOXGKVJPN-XCGJVMPOSA-N (6r)-7-amino-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)C(N)[C@H]2SC1 XUTQHTOXGKVJPN-XCGJVMPOSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- AMOYMEBHYUTMKJ-UHFFFAOYSA-N 2-(2-phenylethoxy)ethylbenzene Chemical compound C=1C=CC=CC=1CCOCCC1=CC=CC=C1 AMOYMEBHYUTMKJ-UHFFFAOYSA-N 0.000 description 1
- XQVPYHNCQLHGTE-UHFFFAOYSA-N 2-[[2-(2-chlorophenoxy)acetyl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NC(=O)COC1=CC=CC=C1Cl XQVPYHNCQLHGTE-UHFFFAOYSA-N 0.000 description 1
- KXLMIPVBJNAAFQ-UHFFFAOYSA-N 2-[[2-(2-nitrophenoxy)acetyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)COC1=CC=CC=C1[N+]([O-])=O KXLMIPVBJNAAFQ-UHFFFAOYSA-N 0.000 description 1
- GXDWABGQWLAEFP-UHFFFAOYSA-N 2-[[2-(2-nitrophenyl)acetyl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NC(=O)CC1=CC=CC=C1[N+]([O-])=O GXDWABGQWLAEFP-UHFFFAOYSA-N 0.000 description 1
- ZWAFCNAZKRYSOY-UHFFFAOYSA-N 2-[[2-(3-nitrophenoxy)acetyl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NC(=O)COC1=CC=CC([N+]([O-])=O)=C1 ZWAFCNAZKRYSOY-UHFFFAOYSA-N 0.000 description 1
- KCVDVLCMMNNTGD-UHFFFAOYSA-N 2-[[2-(4-chlorophenoxy)acetyl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NC(=O)COC1=CC=C(Cl)C=C1 KCVDVLCMMNNTGD-UHFFFAOYSA-N 0.000 description 1
- ZVVPFBXPJJAUFN-UHFFFAOYSA-N 2-[[2-(4-nitrophenoxy)acetyl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NC(=O)COC1=CC=C([N+]([O-])=O)C=C1 ZVVPFBXPJJAUFN-UHFFFAOYSA-N 0.000 description 1
- WQELDIQOHGAHEM-UHFFFAOYSA-N 2-acetamidoacetamide Chemical compound CC(=O)NCC(N)=O WQELDIQOHGAHEM-UHFFFAOYSA-N 0.000 description 1
- AVZBOAGCVKEESJ-UHFFFAOYSA-O 2-ethyl-1,2-benzoxazol-2-ium-7-ol Chemical class C1=CC(O)=C2O[N+](CC)=CC2=C1 AVZBOAGCVKEESJ-UHFFFAOYSA-O 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- YNNIOBNUNOYVLD-UHFFFAOYSA-N 2-phenyl-2-[(2-phenylacetyl)amino]acetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NC(=O)CC1=CC=CC=C1 YNNIOBNUNOYVLD-UHFFFAOYSA-N 0.000 description 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HDFFVHSMHLDSLO-UHFFFAOYSA-N Dibenzyl phosphate Chemical compound C=1C=CC=CC=1COP(=O)(O)OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-N 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-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
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JVHPKYBRJQNPAT-UHFFFAOYSA-N n-cyclohexyl-2,2-diphenylethenimine Chemical compound C1CCCCC1N=C=C(C=1C=CC=CC=1)C1=CC=CC=C1 JVHPKYBRJQNPAT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Landscapes
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3608074A JPS5833236B2 (ja) | 1974-03-28 | 1974-03-28 | ７−（ アルフア − チカンアミノアルカンアミド ）−３− チカン −３− セフエム −４− カルボンサンユウドウタイノ セイゾウホウ |
| DE19752512284 DE2512284A1 (de) | 1974-03-28 | 1975-03-20 | Cephalosporansaeurederivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel |
| GB12273/75A GB1488591A (en) | 1974-03-28 | 1975-03-24 | Cephalosporanic acid derivatives and the preparation thereof |
| FR7509298A FR2265390B1 (enrdf_load_stackoverflow) | 1974-03-28 | 1975-03-25 | |
| US05/563,116 US4039536A (en) | 1974-03-28 | 1975-03-28 | 7-(α-SUBSTITUTED GLYCINAMIDO)-3-SUBSTITUTED METHYL-3-CEPHEM-4-CARBOXYLIC ACIDS AND THEIR DERIVATIVES |
| US05/796,663 US4178445A (en) | 1974-03-28 | 1977-05-13 | 7-(α-Substituted glycinamido)-3-substituted methyl-3-cephem-4-carboxylic acids and their derivatives |
| US06/053,095 US4252952A (en) | 1974-03-28 | 1979-06-28 | 7-(α-Substituted glycinamido)-3-substituted methyl-3-cephem-4-carboxylic acids and their derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3608074A JPS5833236B2 (ja) | 1974-03-28 | 1974-03-28 | ７−（ アルフア − チカンアミノアルカンアミド ）−３− チカン −３− セフエム −４− カルボンサンユウドウタイノ セイゾウホウ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50129588A JPS50129588A (enrdf_load_stackoverflow) | 1975-10-13 |
| JPS5833236B2 true JPS5833236B2 (ja) | 1983-07-18 |
Family
ID=12459749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3608074A Expired JPS5833236B2 (ja) | 1974-03-28 | 1974-03-28 | ７−（ アルフア − チカンアミノアルカンアミド ）−３− チカン −３− セフエム −４− カルボンサンユウドウタイノ セイゾウホウ |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5833236B2 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5331691A (en) * | 1976-09-06 | 1978-03-25 | Fujisawa Pharmaceut Co Ltd | N-(n-substituted phenylglycine amido)cephalosporanic acid derivatives |
-
1974
- 1974-03-28 JP JP3608074A patent/JPS5833236B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50129588A (enrdf_load_stackoverflow) | 1975-10-13 |
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