NO770703L - Fremgangsm}te for fremstilling av cefalosporiner - Google Patents

Fremgangsm}te for fremstilling av cefalosporiner

Info

Publication number: NO770703L
Authority: NO; Norway
Prior art keywords: group; carboxylic acid; pharmaceutically acceptable; carboxamido; acceptable salts
Prior art date: 1976-03-03

Application number

NO770703A

Other languages

English (en)

Norwegian (no)

Inventor

Hirotada Yamada

Takenari Nakagome

Toshiaki Komatsu

Original Assignee

Sumitomo Chemical Co

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.)

1976-03-03

Filing date

1977-03-01

Publication date

1977-09-06

1976-03-03 Priority claimed from JP2348476A external-priority patent/JPS52106889A/ja

1976-03-03 Priority claimed from JP2348576A external-priority patent/JPS52106895A/ja

1976-03-03 Priority claimed from JP2348276A external-priority patent/JPS52106888A/ja

1976-03-03 Priority claimed from JP2348376A external-priority patent/JPS52106894A/ja

1977-03-01 Application filed by Sumitomo Chemical Co filed Critical Sumitomo Chemical Co

1977-09-06 Publication of NO770703L publication Critical patent/NO770703L/no

Links

238000000034 method Methods 0.000 title claims description 42
238000002360 preparation method Methods 0.000 title claims description 24
HOKIDJSKDBPKTQ-UHFFFAOYSA-N 3-(acetyloxymethyl)-7-[(5-amino-5-carboxypentanoyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C12 HOKIDJSKDBPKTQ-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 113
150000003839 salts Chemical class 0.000 claims description 54
231100000252 nontoxic Toxicity 0.000 claims description 32
230000003000 nontoxic effect Effects 0.000 claims description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
125000003277 amino group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
125000003282 alkyl amino group Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000001544 thienyl group Chemical group 0.000 claims description 7
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
CBHTTYDJRXOHHL-UHFFFAOYSA-N 2h-triazolo[4,5-c]pyridazine Chemical group N1=NC=CC2=C1N=NN2 CBHTTYDJRXOHHL-UHFFFAOYSA-N 0.000 claims description 5
125000004423 acyloxy group Chemical group 0.000 claims description 5
125000002950 monocyclic group Chemical group 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
125000003226 pyrazolyl group Chemical group 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
125000005236 alkanoylamino group Chemical group 0.000 claims description 3
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
229910052755 nonmetal Inorganic materials 0.000 claims 2
OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical group C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 claims 2
241000150551 Khabarovsk orthohantavirus Species 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
-1 cephalosporin compounds Chemical class 0.000 description 50
239000000203 mixture Substances 0.000 description 37
239000000243 solution Substances 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
239000013078 crystal Substances 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
125000004432 carbon atom Chemical group C* 0.000 description 18
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 17
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
159000000000 sodium salts Chemical class 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
238000000354 decomposition reaction Methods 0.000 description 9
229930186147 Cephalosporin Natural products 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
229940124587 cephalosporin Drugs 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 8
239000000725 suspension Substances 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
230000000845 anti-microbial effect Effects 0.000 description 7
150000001780 cephalosporins Chemical class 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
125000004414 alkyl thio group Chemical group 0.000 description 6
239000000047 product Substances 0.000 description 6
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 5
208000035473 Communicable disease Diseases 0.000 description 5
230000037396 body weight Effects 0.000 description 5
125000004663 dialkyl amino group Chemical group 0.000 description 5
125000001072 heteroaryl group Chemical group 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
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 4
241000894006 Bacteria Species 0.000 description 4
241000589517 Pseudomonas aeruginosa Species 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
125000003342 alkenyl group Chemical group 0.000 description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
125000004849 alkoxymethyl group Chemical group 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
239000002198 insoluble material Substances 0.000 description 4
239000008363 phosphate buffer Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 4
230000007017 scission Effects 0.000 description 4
AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
239000002246 antineoplastic agent Substances 0.000 description 3
125000005162 aryl oxy carbonyl amino group Chemical group 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
125000002993 cycloalkylene group Chemical group 0.000 description 3
229940127089 cytotoxic agent Drugs 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
CFGDUGSIBUXRMR-UHFFFAOYSA-N 1,2-dihydropyrrol-2-ide Chemical compound C=1C=[C-]NC=1 CFGDUGSIBUXRMR-UHFFFAOYSA-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
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
241000192125 Firmicutes Species 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-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
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000588769 Proteus <enterobacteria> Species 0.000 description 2
241000589516 Pseudomonas Species 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
125000004391 aryl sulfonyl group Chemical group 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
239000000872 buffer Substances 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
239000012043 crude product Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
150000003016 phosphoric acids Chemical class 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
230000002265 prevention Effects 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 2
239000012260 resinous material Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
125000003396 thiol group Chemical group [H]S* 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
ZCNSUUOYGUQILP-UHFFFAOYSA-N (1-chloro-2-methylpropyl) hydrogen carbonate Chemical compound CC(C)C(Cl)OC(O)=O ZCNSUUOYGUQILP-UHFFFAOYSA-N 0.000 description 1
125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
125000006526 (C1-C2) alkyl group Chemical group 0.000 description 1
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
GRWAIJBHBCCLGS-UHFFFAOYSA-N 2-(tetrazol-1-yl)acetic acid Chemical compound OC(=O)CN1C=NN=N1 GRWAIJBHBCCLGS-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 class CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
244000063299 Bacillus subtilis Species 0.000 description 1
235000014469 Bacillus subtilis Nutrition 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000193468 Clostridium perfringens Species 0.000 description 1
229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
229910021594 Copper(II) fluoride Inorganic materials 0.000 description 1
241000186227 Corynebacterium diphtheriae Species 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
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
241000588915 Klebsiella aerogenes Species 0.000 description 1
ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical group OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
125000002059 L-arginyl group Chemical class O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 description 1
125000001176 L-lysyl group Chemical class [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])C([H])([H])C(N([H])[H])([H])[H] 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
241000191938 Micrococcus luteus Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
241000588653 Neisseria Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000588770 Proteus mirabilis Species 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 1
241000607720 Serratia Species 0.000 description 1
241000607715 Serratia marcescens Species 0.000 description 1
241000607762 Shigella flexneri Species 0.000 description 1
241000607760 Shigella sonnei Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
241000191963 Staphylococcus epidermidis Species 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
CZWLTLZSKVJAHO-NQPNHJOESA-N [(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl carbamate Chemical compound C(N)(=O)OCC=1CS[C@H]2N(C=1)C(C2N)=O CZWLTLZSKVJAHO-NQPNHJOESA-N 0.000 description 1
GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical group CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000005910 alkyl carbonate group Chemical group 0.000 description 1
125000005422 alkyl sulfonamido group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
230000015572 biosynthetic process Effects 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
239000007853 buffer solution Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
125000005518 carboxamido group Chemical group 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
229960000603 cefalotin Drugs 0.000 description 1
MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 1
229960001139 cefazolin Drugs 0.000 description 1
VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
GWFAVIIMQDUCRA-UHFFFAOYSA-L copper(ii) fluoride Chemical compound [F-].[F-].[Cu+2] GWFAVIIMQDUCRA-UHFFFAOYSA-L 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
229960003280 cupric chloride Drugs 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
229940092559 enterobacter aerogenes Drugs 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
125000004185 ester group Chemical group 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
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
230000004927 fusion Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 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
239000012456 homogeneous solution Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-O hydron;1,2-oxazole Chemical compound C=1C=[NH+]OC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-O 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
238000011835 investigation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
229960005015 local anesthetics Drugs 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
239000000463 material Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
IWDCLRJOBJJRNH-UHFFFAOYSA-N para-hydroxytoluene Natural products CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 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
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
238000006552 photochemical reaction Methods 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl 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
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
244000144977 poultry Species 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229940115939 shigella sonnei Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO770703A 1976-03-03 1977-03-01 Fremgangsm}te for fremstilling av cefalosporiner NO770703L (no)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP2348476A JPS52106889A (en)	1976-03-03	1976-03-03	7-(n-acylamino-alpha-aryl or-thienylacetamido)-3-carbamoyl-3-cephem-4-carb oxylic acids
JP2348576A JPS52106895A (en)	1976-03-03	1976-03-03	77nnacylaminooaaaryl orrthienylacetamido33heterocyclic thiomethyl* 33cephemm44carboxylic acids
JP2348276A JPS52106888A (en)	1976-03-03	1976-03-03	7-(n-acylamino-alpha-arylacetamido0-3-azidomethyl acid
JP2348376A JPS52106894A (en)	1976-03-03	1976-03-03	7-(n-acylamino-alpha-aryl or-thienylacetamido)-3-(heterocyclic-thiomethyl) acids

Publications (1)

Publication Number	Publication Date
NO770703L true NO770703L (no)	1977-09-06

Family

ID=27457971

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO770703A NO770703L (no)	1976-03-03	1977-03-01	Fremgangsm}te for fremstilling av cefalosporiner

Country Status (17)

Country	Link
US (1)	US4165373A (de)
AT (3)	AT359186B (de)
AU (1)	AU498968B2 (de)
BE (1)	BE851983A (de)
CA (1)	CA1120466A (de)
CH (1)	CH621125A5 (de)
DE (1)	DE2709293A1 (de)
DK (1)	DK91277A (de)
ES (2)	ES456499A1 (de)
FR (1)	FR2342734A1 (de)
GB (1)	GB1537949A (de)
HU (1)	HU176615B (de)
MX (1)	MX5388E (de)
NL (1)	NL7702222A (de)
NO (1)	NO770703L (de)
NZ (1)	NZ183477A (de)
SE (1)	SE433081B (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2362146A1 (fr) *	1976-08-17	1978-03-17	Fujisawa Pharmaceutical Co	Procede de preparation de composes d'acide 7-(n-substitue-2-phenylglycinamido)-3-substitue-3-cephem-4-carboxylique et nouveaux produits ainsi obtenus, a activite antibacterienne
JPS5492991A (en)	1977-12-28	1979-07-23	Dainippon Pharmaceut Co Ltd	N-acyl cephalosporin derivative and its salt
FR2387235A1 (fr) *	1978-01-23	1978-11-10	Fujisawa Pharmaceutical Co	Procede de preparation de composes d'acide 3,7-disubstitue-3-cephem-4-carboxylique et nouveaux produits ainsi obtenus, ayant une forte activite antibacterienne
JPS6058239B2 (ja) *	1978-07-20	1985-12-19	山之内製薬株式会社	新規セフアロスポリン誘導体
JPS5572195A (en) *	1978-11-28	1980-05-30	Mitsui Toatsu Chem Inc	Novel cephalosporin and antibacterial comprising it as active constituent
JPS55139389A (en) *	1979-04-19	1980-10-31	Mitsui Toatsu Chem Inc	Novel cephalosporin
US4420477A (en) *	1979-11-30	1983-12-13	Fujisawa Pharmaceutical Co., Ltd.	Cephem compounds
US4288590A (en) *	1980-02-14	1981-09-08	Bristol-Myers Company	7-[Dα-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-α-arylacetamido]-3-(N,N-dimethyl-aminomethylpyridinium) methyl-3-cephem-4-carboxylates
CA1152489A (en) *	1980-03-05	1983-08-23	Takao Okuda	ANTIMICROBIAL 7- (.alpha.-ACYLAMINO-.alpha.-ARYLACETAMIDO)-3- (SUBSTITUTED METHYL) CEPHALOSPORIN COMPOUNDS, THEIR COMPOSITIONS AND PRODUCTION THEREOF
ES8201587A1 (es) *	1980-03-05	1982-01-01	Sumitomo Chemical Co	Procedimiento de producir compuestos cefalosporinicos anti- microbianos
JPS56158791A (en) *	1980-05-10	1981-12-07	Taisho Pharmaceut Co Ltd	Cephalosporin compound
WO2002086143A2 (en) *	2001-04-19	2002-10-31	Bioferma Murcia, S.A.	Enzymatic process for preparing cephalosporin derivatives

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5747672B2 (de) *	1973-10-13	1982-10-12
JPS5119765A (en) *	1974-08-09	1976-02-17	Takeda Chemical Industries Ltd	Aminochiazoorujudotaino seizoho
JPS51115491A (en) *	1975-04-03	1976-10-12	Sumitomo Chem Co Ltd	Method for preparing 77* 44hydroxyy15 naphthyridinee33carboxyamino ** phenylacetamido*cephalosporins
US4045438A (en) *	1975-10-24	1977-08-30	Yeda Research And Development Co. Ltd.	Cephalosporin antibiotics
US4025626A (en) *	1975-12-09	1977-05-24	Smithkline Corporation	7-Acyl-3-(ureidoalkyl substituted tetrazolylthiomethyl)-cephalosporins

1977
- 1977-03-01 AU AU22813/77A patent/AU498968B2/en not_active Expired
- 1977-03-01 NO NO770703A patent/NO770703L/no unknown
- 1977-03-01 GB GB8490/77A patent/GB1537949A/en not_active Expired
- 1977-03-02 DK DK91277A patent/DK91277A/da not_active Application Discontinuation
- 1977-03-02 CA CA000272985A patent/CA1120466A/en not_active Expired
- 1977-03-02 HU HU77SU941A patent/HU176615B/hu unknown
- 1977-03-02 NZ NZ183477A patent/NZ183477A/xx unknown
- 1977-03-02 NL NL7702222A patent/NL7702222A/xx unknown
- 1977-03-02 BE BE175387A patent/BE851983A/xx not_active IP Right Cessation
- 1977-03-02 SE SE7702332A patent/SE433081B/xx unknown
- 1977-03-02 US US05/773,729 patent/US4165373A/en not_active Expired - Lifetime
- 1977-03-03 MX MX775501U patent/MX5388E/es unknown
- 1977-03-03 DE DE19772709293 patent/DE2709293A1/de not_active Ceased
- 1977-03-03 AT AT140077A patent/AT359186B/de not_active IP Right Cessation
- 1977-03-03 FR FR7706305A patent/FR2342734A1/fr active Granted
- 1977-03-03 ES ES456499A patent/ES456499A1/es not_active Expired
1978
- 1978-03-16 ES ES468662A patent/ES468662A1/es not_active Expired
1979
- 1979-03-16 AT AT198679A patent/AT359193B/de not_active IP Right Cessation
- 1979-03-16 AT AT198779A patent/AT359194B/de not_active IP Right Cessation
1980
- 1980-04-15 CH CH264777A patent/CH621125A5/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
CA1120466A (en)	1982-03-23
DE2709293A1 (de)	1977-09-08
US4165373A (en)	1979-08-21
BE851983A (fr)	1977-07-01
ATA198779A (de)	1980-03-15
SE433081B (sv)	1984-05-07
ES456499A1 (es)	1978-11-16
SE7702332L (sv)	1977-09-04
NZ183477A (en)	1979-06-19
NL7702222A (nl)	1977-09-06
ATA198679A (de)	1980-03-15
DK91277A (da)	1977-09-04
FR2342734A1 (fr)	1977-09-30
HU176615B (en)	1981-03-28
ES468662A1 (es)	1979-11-01
FR2342734B1 (de)	1981-06-19
GB1537949A (en)	1979-01-10
AU2281377A (en)	1978-09-07
CH621125A5 (de)	1981-01-15
ATA140077A (de)	1980-03-15
AT359193B (de)	1980-10-27
MX5388E (es)	1983-07-07
AT359194B (de)	1980-10-27
AT359186B (de)	1980-10-27
AU498968B2 (en)	1979-03-29

Publication	Publication Date	Title
US3994885A (en)	1976-11-30	Process for etherifying β-lactam antibiotics
NO770703L (no)	1977-09-06	Fremgangsm}te for fremstilling av cefalosporiner
US4142046A (en)	1979-02-27	Intermediates for the preparation of 7-acyl-3-(substituted triazolylthiomethyl)cephalosporins
NO153573B (no)	1986-01-06	Analogifremgangsmaate for fremstilling av terapeutisk aktive n-acylamino-alfa-arylacet-amidocefalosporiner.
NO764054L (de)	1977-06-01
US4061748A (en)	1977-12-06	7-(α-(4-Hydroxy-1,5-naphthyridine-3-carbonamido)-α-phenylacetamido) cephalosporin derivatives
US4492692A (en)	1985-01-08	Cephalosporin derivatives
US4117126A (en)	1978-09-26	7-(α-(4-Hydroxy-1,5-naphthyridine-3-carbonamido)-α-phenylacetamido) cephalosporin derivatives
US4148997A (en)	1979-04-10	7-[Sulfomethyl)phenyl]acetamidocephalosporin derivatives
US4044000A (en)	1977-08-23	Substituted β-lactam antibiotics
CS205005B2 (cs)	1981-04-30	Způsob přípravy N-acylamins-a-arylacetamidocefalosporinu
DK159153B (da)	1990-09-10	Analogifremgangsmaade til fremstilling af penicillinforbindelser
US4368198A (en)	1983-01-11	Cephalosporins
US4302454A (en)	1981-11-24	Cephalosporins
US4390535A (en)	1983-06-28	Antimicrobial 7-(α-acylamino-α-arylacetamido)-3-(substituted methyl)cephalosporin compounds
JPH11279180A (ja)	1999-10-12	新規なセファロスポリン誘導体またはその塩並びにそれらを含有する抗菌剤
HU185685B (en)	1985-03-28	Process for preparing new cefem-carboxylic acid derivatives
AT359195B (de)	1980-10-27	Verfahren zur herstellung von neuen cephalos- porinverbindungen und deren pharmazeutisch anwendbaren salzen
KR840000408B1 (ko)	1984-03-31	세팔로스포린의 제조방법
KR830000551B1 (ko)	1983-03-12	세팔로스포린 유도체의 제조방법
SU993821A3 (ru)	1983-01-30	Способ получени 7-/ @ , @ -дизамещенный ацетамидо/-3-замещенных-3-цефем-4-карбоновых кислот или их низший алканоилокси/низший/алкиловых сложных эфиров или их фармацевтически приемлемых солей
EP0178527A2 (de)	1986-04-23	Cephalosporinverbindungen und Verfahren zu ihrer Herstellung
SU980626A3 (ru)	1982-12-07	Способ получени производных цефалоспорина или их щелочных солей
RU2017744C1 (ru)	1994-08-15	Способ получения соединений цефема или их кислотно-аддитивных солей
SU1482532A3 (ru)	1989-05-23	Способ получени цефемовых соединений или их приемлемых с физиологической или фармацевтической точки зрени солей