JPS6238357B2 - - Google Patents

Info

Publication number: JPS6238357B2
Authority: JP; Japan
Prior art keywords: ester; acid; salt; salts; esters
Prior art date: 1979-11-19
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

Application number

JP19117582A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5896092A (ja

Inventor

Takao Takatani

Hisashi Takasugi

Takashi Masugi

Hideaki Yamanaka

Koji Kawabata

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Fujisawa Pharmaceutical Co Ltd

Original Assignee

Fujisawa Pharmaceutical Co Ltd

Priority date (The priority date 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 date listed.)

1979-11-19

Filing date

1982-10-29

Publication date

1987-08-17

1982-10-29 Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd

1983-06-07 Publication of JPS5896092A publication Critical patent/JPS5896092A/ja

1987-08-17 Publication of JPS6238357B2 publication Critical patent/JPS6238357B2/ja

Status Granted legal-status Critical Current

Links

150000003839 salts Chemical class 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
125000004849 alkoxymethyl group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
-1 alkali metal salts Chemical class 0.000 description 91
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 11
239000000243 solution Substances 0.000 description 11
125000005907 alkyl ester group Chemical group 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 8
150000002148 esters Chemical group 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
VMHPUGMXEREVFV-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)acetamide Chemical compound NC(=O)CC1=CSC(N)=N1 VMHPUGMXEREVFV-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
150000003016 phosphoric acids Chemical class 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Chemical compound CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000003222 pyridines Chemical class 0.000 description 2
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-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
125000004455 (C1-C3) alkylthio group Chemical group 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
RSBOSGZHKSGSOB-UHFFFAOYSA-N 1-chloro-4-(4-chlorobut-3-enoxy)but-1-ene Chemical compound ClC=CCCOCCC=CCl RSBOSGZHKSGSOB-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
SNUSZUYTMHKCPM-UHFFFAOYSA-N 1-hydroxypyridin-2-one Chemical compound ON1C=CC=CC1=O SNUSZUYTMHKCPM-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
OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
ODXCMWLJDMOSSL-UHFFFAOYSA-N 2-ethyl-1,2-benzoxazol-2-ium Chemical class C1=CC=C2O[N+](CC)=CC2=C1 ODXCMWLJDMOSSL-UHFFFAOYSA-N 0.000 description 1
CRPFKUKPDCBUIX-UHFFFAOYSA-N 2-ethyl-5-phenyl-1,2-oxazol-2-ium-3-sulfonate Chemical compound [O-]S(=O)(=O)C1=[N+](CC)OC(C=2C=CC=CC=2)=C1 CRPFKUKPDCBUIX-UHFFFAOYSA-N 0.000 description 1
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 1
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-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
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 1
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
IGIJSFNBEUBMGB-UHFFFAOYSA-N 4-(cyclohexyliminomethylideneamino)-n,n-diethylcyclohexan-1-amine Chemical compound C1CC(N(CC)CC)CCC1N=C=NC1CCCCC1 IGIJSFNBEUBMGB-UHFFFAOYSA-N 0.000 description 1
KXVSPXCGTNISAP-UHFFFAOYSA-N 4-bromo-3-oxobutanoyl bromide Chemical compound BrCC(=O)CC(Br)=O KXVSPXCGTNISAP-UHFFFAOYSA-N 0.000 description 1
TZCYLJGNWDVJRA-UHFFFAOYSA-N 6-chloro-1-hydroxybenzotriazole Chemical compound C1=C(Cl)C=C2N(O)N=NC2=C1 TZCYLJGNWDVJRA-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229930186147 Cephalosporin Natural products 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
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-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
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
XNPOFXIBHOVFFH-UHFFFAOYSA-N N-cyclohexyl-N'-(2-(4-morpholinyl)ethyl)carbodiimide Chemical compound C1CCCCC1N=C=NCCN1CCOCC1 XNPOFXIBHOVFFH-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical group 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
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
229920000388 Polyphosphate Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
125000005910 alkyl carbonate group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
229940009098 aspartate Drugs 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 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
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000001805 chlorine compounds 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
238000001816 cooling Methods 0.000 description 1
125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
150000002019 disulfides Chemical class 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
150000002169 ethanolamines Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
WMYNMYVRWWCRPS-UHFFFAOYSA-N ethynoxyethane Chemical group CCOC#C WMYNMYVRWWCRPS-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
239000010410 layer Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
238000000034 method Methods 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical class C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 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
239000003960 organic solvent Substances 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 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
229940100595 phenylacetaldehyde Drugs 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000001205 polyphosphate Substances 0.000 description 1
235000011176 polyphosphates Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003892 tartrate salts Chemical class 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
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
229920001567 vinyl ester resin Polymers 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)
Thiazole And Isothizaole Compounds (AREA)
Pyridine Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP19117582A 1979-11-19 1982-10-29 ７−アシルアミノ−３−置換セフアロスポラン酸誘導体およびその製造法 Granted JPS5896092A (ja)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB7939985		1979-11-19
GB8004335		1980-04-21
GB8012991		1980-04-21
GB7939985		1980-04-21

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
JP16399080A Division JPS5686188A (en)	1979-11-19	1980-11-19	7-acylamino-3-substituted cephalosporanic acid derivative and its preparation

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP22640283A Division JPS59144788A (ja)	1979-11-19	1983-11-29	７−アシルアミノ−３−置換セフアロスポラン酸誘導体およびその製法

Publications (2)

Publication Number	Publication Date
JPS5896092A JPS5896092A (ja)	1983-06-07
JPS6238357B2 true JPS6238357B2 (fi)	1987-08-17

Family

ID=10509300

Family Applications (12)

Application Number	Title	Priority Date	Filing Date
JP16399080A Pending JPS5686188A (en)	1979-11-19	1980-11-19	7-acylamino-3-substituted cephalosporanic acid derivative and its preparation
JP16398980A Granted JPS5686187A (en)	1979-11-19	1980-11-19	7-acylamino-3-vinylcephalosporanic acid derivative and its preparation
JP19117582A Granted JPS5896092A (ja)	1979-11-19	1982-10-29	７−アシルアミノ−３−置換セフアロスポラン酸誘導体およびその製造法
JP22640283A Granted JPS59144788A (ja)	1979-11-19	1983-11-29	７−アシルアミノ−３−置換セフアロスポラン酸誘導体およびその製法
JP27813884A Pending JPS60185787A (ja)	1979-11-19	1984-12-29	７−アシルアミノ−３−置換セフアロスポラン酸誘導体およびその製造方法
JP62044400A Granted JPS62277391A (ja)	1979-11-19	1987-02-26	７−アシルアミノ−３−ビニルセフアロスポラン酸誘導体およびその製法
JP62290251A Granted JPS63152370A (ja)	1979-11-19	1987-11-17	新規カルボン酸
JP29024887A Granted JPS63152387A (ja)	1979-11-19	1987-11-17	７−アシルアミノ−３−ビニル　セファロスポラン酸誘導体
JP29025087A Granted JPS63152385A (ja)	1979-11-19	1987-11-17	新規な７−置換−３−ビニルセファロスポラン酸
JP62290252A Granted JPS63152371A (ja)	1979-11-19	1987-11-17	アミノチアゾール誘導体
JP62290253A Granted JPS63146863A (ja)	1979-11-19	1987-11-17	カルボン酸類
JP29024987A Granted JPS63152388A (ja)	1979-11-19	1987-11-17	新規なセフェム化合物

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
JP16399080A Pending JPS5686188A (en)	1979-11-19	1980-11-19	7-acylamino-3-substituted cephalosporanic acid derivative and its preparation
JP16398980A Granted JPS5686187A (en)	1979-11-19	1980-11-19	7-acylamino-3-vinylcephalosporanic acid derivative and its preparation

Family Applications After (9)

Application Number	Title	Priority Date	Filing Date
JP22640283A Granted JPS59144788A (ja)	1979-11-19	1983-11-29	７−アシルアミノ−３−置換セフアロスポラン酸誘導体およびその製法
JP27813884A Pending JPS60185787A (ja)	1979-11-19	1984-12-29	７−アシルアミノ−３−置換セフアロスポラン酸誘導体およびその製造方法
JP62044400A Granted JPS62277391A (ja)	1979-11-19	1987-02-26	７−アシルアミノ−３−ビニルセフアロスポラン酸誘導体およびその製法
JP62290251A Granted JPS63152370A (ja)	1979-11-19	1987-11-17	新規カルボン酸
JP29024887A Granted JPS63152387A (ja)	1979-11-19	1987-11-17	７−アシルアミノ−３−ビニル　セファロスポラン酸誘導体
JP29025087A Granted JPS63152385A (ja)	1979-11-19	1987-11-17	新規な７−置換−３−ビニルセファロスポラン酸
JP62290252A Granted JPS63152371A (ja)	1979-11-19	1987-11-17	アミノチアゾール誘導体
JP62290253A Granted JPS63146863A (ja)	1979-11-19	1987-11-17	カルボン酸類
JP29024987A Granted JPS63152388A (ja)	1979-11-19	1987-11-17	新規なセフェム化合物

Country Status (2)

Country	Link
JP (12)	JPS5686188A (fi)
ZA (1)	ZA806977B (fi)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4464369A (en) *	1977-03-14	1984-08-07	Fujisawa Pharmaceutical Co., Ltd.	7-Acylamino-3-cephem-4-carboxylic acid derivatives and pharmaceutical compositions
ZA806977B (en) *	1979-11-19	1981-10-28	Fujisawa Pharmaceutical Co	7-acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof
FR2476087A1 (fr) *	1980-02-18	1981-08-21	Roussel Uclaf	Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkyl-thiomethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments
EP0046964B1 (en) *	1980-08-29	1986-08-20	Fujisawa Pharmaceutical Co., Ltd.	New cephem compounds and processes for preparation thereof
JPS6052754B2 (ja) *	1981-01-29	1985-11-21	山之内製薬株式会社	７−アミノ−３−ハロゲノメチル−△↑３−セフェム−４−カルボン酸類およびその製法
JPS58135894A (ja) *	1982-01-22	1983-08-12	Fujisawa Pharmaceut Co Ltd	７―置換ブチルアミド―３―ビニルセファロスポラン酸誘導体
JPS5921695A (ja) *	1982-07-29	1984-02-03	Dai Ichi Seiyaku Co Ltd	セフアロスポリン誘導体
DK162718C (da) *	1982-09-30	1992-05-11	Fujisawa Pharmaceutical Co	Analogifremgangsmaade til fremstilling af 7-substitueret-3-vinyl-3-cephemforbindelser
ZA836918B (en) *	1982-09-30	1984-05-30	Fujisawa Pharmaceutical Co	7-substituted-3-vinyl-3-cephem compounds and processes for the production of the same
JPS58159496A (ja) *	1983-03-02	1983-09-21	Kyoto Yakuhin Kogyo Kk	セフエム系化合物
JPS59210092A (ja) *	1983-05-13	1984-11-28	Dai Ichi Seiyaku Co Ltd	セフアロスポリン誘導体
GB8318846D0 (en) *	1983-07-12	1983-08-10	Fujisawa Pharmaceutical Co	Prophylactic/therapeutic agent against fish diseases
GB8329030D0 (en) *	1983-10-31	1983-11-30	Fujisawa Pharmaceutical Co	Cephem compounds
CA1296012C (en)	1986-03-19	1992-02-18	Susumu Nakagawa	6,7-dihydroxy-isoquinoline derivatives
US4822786A (en) *	1986-07-01	1989-04-18	Kaken Pharmaceutical Co., Ltd.	Cephalosporin compounds, and antibacterial agents
JP4157177B2 (ja) *	1997-06-04	2008-09-24	大塚化学ホールディングス株式会社	３−アルケニルセフェム化合物の製造法
AT406773B (de) *	1998-04-02	2000-08-25	Biochemie Gmbh	Neues salz von 7-(2-(aminothiazol-4yl)-2-
ITMI20022076A1 (it) *	2002-10-01	2004-04-02	Antibioticos Spa	Sali di intermedi del cefdinir.
US7980324B2 (en)	2006-02-03	2011-07-19	Black & Decker Inc.	Housing and gearbox for drill or driver
JP4779741B2 (ja) *	2006-03-22	2011-09-28	株式会社日立製作所	ヒートポンプシステム，ヒートポンプシステムの軸封方法，ヒートポンプシステムの改造方法
UY34585A (es) *	2012-01-24	2013-09-02	Aicuris Gmbh & Co Kg	Compuestos b-lactámicos sustituidos con amidina, su preparación y uso
KR101485316B1 (ko) *	2014-04-16	2015-01-22	(주)에이치티씨	플렛 케이블용 컨넥터 핀 자동 압착장치

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE789817A (fr) *	1971-10-07	1973-04-06	Glaxo Lab Ltd	Perfectionnements aux composes de cephalosporine
GB1325846A (en) *	1972-02-23	1973-08-08	Lilly Co Eli	Process for the preparation of a 3-thiomethyl cephalosporin
DE2209019A1 (de) *	1972-02-25	1973-08-30	Lilly Co Eli	Verfahren zur herstellung von 3-thiomethylcephalosporinverbindungen
JPS5729474B2 (fi) *	1974-01-14	1982-06-23
DE2710902A1 (de) *	1977-03-12	1978-09-21	Hoechst Ag	Cephemderivate und verfahren zu ihrer herstellung
DE2714880A1 (de) *	1977-04-02	1978-10-26	Hoechst Ag	Cephemderivate und verfahren zu ihrer herstellung
US4200745A (en) *	1977-12-20	1980-04-29	Eli Lilly And Company	7[2-(2-Aminothiazol-4-yl)-2-alkoxyimino]acetamido 3[4-alkyl-5-oxo-6-hydroxy-3,4 dihydro 1,2,4-triazin 3-yl]thio methyl cephalosporins
FR2432521A1 (fr) *	1978-03-31	1980-02-29	Roussel Uclaf	Nouvelles oximes o-substituees derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments
HU184631B (en) *	1978-05-26	1984-09-28	Glaxo Group Ltd	Process for preparing cef-3-em-4-carboxylic acid derivatives with antiaiotic activity
GB1604723A (en) *	1978-05-26	1981-12-16	Glaxo Operations Ltd	7-(2-aminothiazol-4-yl)-2-oxyimino-acetamido)-cephem derivatives
JPS5559196A (en) *	1978-10-27	1980-05-02	Glaxo Group Ltd	Cephalosporin compound
BE879666A (fr) *	1978-10-27	1980-04-28	Glaxo Group Ltd	Nouvelles cephalosporines, leur preparation et compositions les contenant
ZA796130B (en) *	1978-11-15	1981-06-24	Glaxo Group Ltd	Cephalosporin antibiotics
BE880068A (fr) *	1978-11-17	1980-05-16	Glaxo Group Ltd	Nouvelles cephalosporines et leur preparation
BE881870A (fr) *	1979-02-23	1980-08-22	Glaxo Group Ltd	Nouvelles cephalosporines qui exercent une activite contre des organismes gram-negatifs
JPS55124790A (en) *	1979-03-19	1980-09-26	Sankyo Co Ltd	Cephem compound, its preparation and antimicrobials consisting the same mainly
NL160860B (nl) *	1979-03-22		American Cyanamid Co	Werkwijze voor het bereiden van een vulcaniseerbaar mengsel.
ZA806977B (en) *	1979-11-19	1981-10-28	Fujisawa Pharmaceutical Co	7-acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof

1980
- 1980-11-11 ZA ZA00806977A patent/ZA806977B/xx unknown
- 1980-11-19 JP JP16399080A patent/JPS5686188A/ja active Pending
- 1980-11-19 JP JP16398980A patent/JPS5686187A/ja active Granted
1982
- 1982-10-29 JP JP19117582A patent/JPS5896092A/ja active Granted
1983
- 1983-11-29 JP JP22640283A patent/JPS59144788A/ja active Granted
1984
- 1984-12-29 JP JP27813884A patent/JPS60185787A/ja active Pending
1987
- 1987-02-26 JP JP62044400A patent/JPS62277391A/ja active Granted
- 1987-11-17 JP JP62290251A patent/JPS63152370A/ja active Granted
- 1987-11-17 JP JP29024887A patent/JPS63152387A/ja active Granted
- 1987-11-17 JP JP29025087A patent/JPS63152385A/ja active Granted
- 1987-11-17 JP JP62290252A patent/JPS63152371A/ja active Granted
- 1987-11-17 JP JP62290253A patent/JPS63146863A/ja active Granted
- 1987-11-17 JP JP29024987A patent/JPS63152388A/ja active Granted

Also Published As

Publication number	Publication date
JPH0225905B2 (fi)	1990-06-06
JPS5896092A (ja)	1983-06-07
JPH0369353B2 (fi)	1991-10-31
JPS5686187A (en)	1981-07-13
JPS5686188A (en)	1981-07-13
JPS63152388A (ja)	1988-06-24
JPS63146863A (ja)	1988-06-18
JPS63152385A (ja)	1988-06-24
JPH0215556B2 (fi)	1990-04-12
JPH0338277B2 (fi)	1991-06-10
JPS63152371A (ja)	1988-06-24
JPS60185787A (ja)	1985-09-21
JPS63152387A (ja)	1988-06-24
JPH0219828B2 (fi)	1990-05-07
JPH0333712B2 (fi)	1991-05-20
JPH0314832B2 (fi)	1991-02-27
JPS63152370A (ja)	1988-06-24
JPS62277391A (ja)	1987-12-02
JPS59144788A (ja)	1984-08-18
JPS6320435B2 (fi)	1988-04-27
JPH0338278B2 (fi)	1991-06-10
ZA806977B (en)	1981-10-28

Publication	Publication Date	Title
JPS6238357B2 (fi)	1987-08-17
EP0123024B1 (en)	1988-09-07	7-acylamino-3-vinylcephalosporanic acid derivatives, processes for their preparation, pharmaceutical compositions containing them; their starting compounds and their preparation
US4284631A (en)	1981-08-18	7-Substituted cephem compounds and pharmaceutical antibacterial compositions containing them
JPH0684338B2 (ja)	1994-10-26	置換酢酸誘導体
EP0048504B1 (en)	1988-08-17	Intermediate compounds for preparing cephem compounds; processes for their preparation and processes for preparing cephem compounds
EP0036510B1 (en)	1984-11-21	Synisomer cephalosporin compounds and processes for their preparation
EP0055466B1 (en)	1987-05-06	Cephem compounds, processes for their preparation, pharmaceutical compositions containing them and their starting compounds
HU192449B (en)	1987-06-29	New process for producing cepheme-carboxylic acid derivatives
EP0082498B1 (en)	1989-11-02	Beta-lactam compounds and process for the preparation thereof
JPH0560473B2 (fi)	1993-09-02
JPH0321544B2 (fi)	1991-03-22
JPH0521912B2 (fi)	1993-03-25
JPS6139952B2 (fi)	1986-09-06
JPH0316358B2 (fi)	1991-03-05
JPH051271B2 (fi)	1993-01-07
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