NO881530L - Acylderivater. - Google Patents

Acylderivater.

Info

Publication number: NO881530L
Authority: NO; Norway
Prior art keywords: methyl; compounds; oxo; carbamoyl; hydrogen
Prior art date: 1987-04-10

Application number

NO881530A

Other languages

English (en)

Norwegian (no)

Other versions

NO881530D0 (no

Inventor

Andre Furlenmeier

Erwing Goetschi

Paul Hebeisen

Werner Hofheinz

Helmut Link

Original Assignee

Hoffmann La Roche

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.)

1987-04-10

Filing date

1988-04-08

Publication date

1988-10-11

1988-04-08 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1988-04-08 Publication of NO881530D0 publication Critical patent/NO881530D0/no

1988-10-11 Publication of NO881530L publication Critical patent/NO881530L/no

Links

125000002252 acyl group Chemical group 0.000 title claims description 16
150000001875 compounds Chemical class 0.000 claims description 68
-1 carboxy, carbamoyl Chemical group 0.000 claims description 61
150000003839 salts Chemical class 0.000 claims description 54
150000002148 esters Chemical class 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 28
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 23
125000001841 imino group Chemical group [H]N=* 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 20
239000007858 starting material Substances 0.000 claims description 18
150000004677 hydrates Chemical class 0.000 claims description 17
238000000034 method Methods 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 14
125000006239 protecting group Chemical group 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical group 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
125000002619 bicyclic group Chemical group 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
125000002993 cycloalkylene group Chemical group 0.000 claims description 3
BUWGYXQLGQHANJ-QHIDJRCQSA-N (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-carbamoyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@@H]1C(N2C(=C(CSC=3N4N=C(N=C4N=C(C)C=3)C(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 BUWGYXQLGQHANJ-QHIDJRCQSA-N 0.000 claims description 2
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000000843 powder Substances 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000002585 base Substances 0.000 description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
125000001589 carboacyl group Chemical group 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000000463 material Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
MWLDRUITZXVYQA-AMIZOPFISA-N (6r,7r)-7-amino-3-[(2-carbamoyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C=1N2C(=O)[C@@H](N)[C@H]2SCC=1CSC1=CC(C)=NC2=NC(C(N)=O)=NN21 MWLDRUITZXVYQA-AMIZOPFISA-N 0.000 description 3
DEJHJMDMXFIMEP-UHFFFAOYSA-N 2-(aminooxymethyl)-5-hydroxy-1h-pyrimidin-6-one Chemical compound NOCC1=NC(=O)C(O)=CN1 DEJHJMDMXFIMEP-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
ULEJWTQLAJJXCL-BMLIUANNSA-N (6r,7r)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-oxoacetyl]amino]-3-[(2-carbamoyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)CSC1=CC(=NC2=NC(=NN21)C(N)=O)C)C(O)=O)C(=O)C(=O)C1=CSC(N)=N1 ULEJWTQLAJJXCL-BMLIUANNSA-N 0.000 description 2
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
HPCOTNDGWUUBKI-UHFFFAOYSA-M 2-fluoro-1-methylpyridin-1-ium;chloride Chemical compound [Cl-].C[N+]1=CC=CC=C1F HPCOTNDGWUUBKI-UHFFFAOYSA-M 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
WFZFAKXMOXWDEF-UHFFFAOYSA-N CC1=NC2=NC(C(N)=O)=NN2C(S)=C1.N Chemical compound CC1=NC2=NC(C(N)=O)=NN2C(S)=C1.N WFZFAKXMOXWDEF-UHFFFAOYSA-N 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
125000005041 acyloxyalkyl group Chemical group 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000011707 mineral Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
SGQMKVBJLRNAKX-UHFFFAOYSA-N n'-(2-aminooxy-2-methylpropanoyl)-5-hydroxy-4-oxo-1h-pyridine-2-carbohydrazide Chemical compound NOC(C)(C)C(=O)NNC(=O)C1=CC(=O)C(O)=CN1 SGQMKVBJLRNAKX-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000003791 organic solvent mixture Substances 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
239000003495 polar organic solvent Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
238000011282 treatment Methods 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
238000005406 washing Methods 0.000 description 2
NLARCUDOUOQRPB-WTKPLQERSA-N (2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetic acid Chemical compound CO\N=C(/C(O)=O)C1=CSC(N)=N1 NLARCUDOUOQRPB-WTKPLQERSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
NDVMCQUOSYOQMZ-UHFFFAOYSA-N 2,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)C(C(N)=O)[Si](C)(C)C NDVMCQUOSYOQMZ-UHFFFAOYSA-N 0.000 description 1
QZMNRXQEUDNVOS-UHFFFAOYSA-N 2-[(5-hydroxy-6-oxo-1h-pyrimidin-2-yl)methoxy]isoindole-1,3-dione Chemical compound O=C1C(O)=CNC(CON2C(C3=CC=CC=C3C2=O)=O)=N1 QZMNRXQEUDNVOS-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
ZNPNOVHKCAAQCG-UHFFFAOYSA-N 2-chloro-1-methylpyridin-1-ium Chemical compound C[N+]1=CC=CC=C1Cl ZNPNOVHKCAAQCG-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
SCNWTQPZTZMXBG-UHFFFAOYSA-N 2-methyloct-2-enoic acid Chemical compound CCCCCC=C(C)C(O)=O SCNWTQPZTZMXBG-UHFFFAOYSA-N 0.000 description 1
OVFJVGPVSMMTSA-UHFFFAOYSA-M 4-methylbenzenesulfonate;1-methylpyridin-1-ium Chemical compound C[N+]1=CC=CC=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 OVFJVGPVSMMTSA-UHFFFAOYSA-M 0.000 description 1
DMIHNTNTPOLSER-UHFFFAOYSA-N 5-hydroxy-2-(hydroxymethyl)-1h-pyrimidin-6-one Chemical compound OCC1=NC=C(O)C(O)=N1 DMIHNTNTPOLSER-UHFFFAOYSA-N 0.000 description 1
KIDVXDFSLNXGEA-UHFFFAOYSA-N 5-hydroxy-4-oxo-1h-pyridine-2-carbohydrazide Chemical compound NNC(=O)C1=CC(=O)C(O)=CN1 KIDVXDFSLNXGEA-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical class NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
241000588697 Enterobacter cloacae Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-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
241000588748 Klebsiella Species 0.000 description 1
150000000994 L-ascorbates Chemical class 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
FTAWEWYDQYTQBS-UHFFFAOYSA-N N1=C(C)C=C(S)N2N=C(C(=O)OC)N=C21 Chemical compound N1=C(C)C=C(S)N2N=C(C(=O)OC)N=C21 FTAWEWYDQYTQBS-UHFFFAOYSA-N 0.000 description 1
RDJCUOBLSZUWEJ-UHFFFAOYSA-N N1=C(C)C=C(S)N2N=C(C(N)=O)N=C21 Chemical compound N1=C(C)C=C(S)N2N=C(C(N)=O)N=C21 RDJCUOBLSZUWEJ-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
241000607715 Serratia marcescens Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
241000295644 Staphylococcaceae Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 description 1
125000004849 alkoxymethyl group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
238000007098 aminolysis reaction Methods 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
229940035674 anesthetics Drugs 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
150000001540 azides Chemical class 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
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000003115 biocidal effect 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
239000007853 buffer solution Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229940119563 enterobacter cloacae Drugs 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000003193 general anesthetic agent Substances 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
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229960004393 lidocaine hydrochloride Drugs 0.000 description 1
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
JOQJEWAXHQDQAG-UHFFFAOYSA-N methyl pyrimidine-2-carboxylate Chemical compound COC(=O)C1=NC=CC=N1 JOQJEWAXHQDQAG-UHFFFAOYSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
FUBXDUABJNXSJW-UHFFFAOYSA-N n'-[2-(1,3-dioxoisoindol-2-yl)oxy-2-methylpropanoyl]-5-hydroxy-4-oxo-1h-pyridine-2-carbohydrazide Chemical compound O=C1C2=CC=CC=C2C(=O)N1OC(C)(C)C(=O)NNC(=O)C1=CC(=O)C(O)=CN1 FUBXDUABJNXSJW-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
150000002940 palladium Chemical class 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
238000006177 thiolation reaction Methods 0.000 description 1
150000003573 thiols Chemical class 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
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Saccharide Compounds (AREA)
Cephalosporin Compounds (AREA)

NO881530A 1987-04-10 1988-04-08 Acylderivater. NO881530L (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH140787		1987-04-10
CH165787		1987-04-30
CH241487		1987-06-26

Publications (2)

Publication Number	Publication Date
NO881530D0 NO881530D0 (no)	1988-04-08
NO881530L true NO881530L (no)	1988-10-11

Family

ID=27172952

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO881530A NO881530L (no)	1987-04-10	1988-04-08	Acylderivater.

Country Status (15)

Country	Link
US (1)	US5055572A (fr)
EP (1)	EP0286144A3 (fr)
JP (1)	JPH01261392A (fr)
KR (1)	KR880012611A (fr)
AU (1)	AU611428B2 (fr)
DK (1)	DK170088A (fr)
FI (1)	FI881641A7 (fr)
HU (1)	HU201948B (fr)
IL (1)	IL85970A0 (fr)
MC (1)	MC1920A1 (fr)
NO (1)	NO881530L (fr)
NZ (1)	NZ224130A (fr)
PH (1)	PH24960A (fr)
PT (1)	PT87202B (fr)
YU (1)	YU70888A (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI872879A7 (fi) *	1986-07-21	1988-01-22	Sankei Yakuhin Kk	--laktamfoerening, foerfarande foer dess framstaellning, denna innehaollande laekemedelskomposition foer behandling av sjukdom med bakterieinfektion samt mellanprodukter foer dess syntes.
FI883320A7 (fi) *	1987-08-07	1989-02-08	Sankei Pharmaceutical Company Ltd	--Laktaami, sen valmistus ja välituotteetsen valmistamiseksi
EP0366189A3 (fr) *	1988-10-24	1992-01-02	Norwich Eaton Pharmaceuticals, Inc.	Lactames-quinolones antimicrobiennes
DE3939533A1 (de) *	1989-11-30	1991-06-06	Bayer Ag	Neue cephalosporine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
EP0544166A3 (en) *	1991-11-26	1993-11-03	Hoffmann La Roche	Cephalosporinderivatives
GB201111705D0 (en)	2011-07-07	2011-08-24	Takeda Pharmaceutical	Compounds and their use
JO3115B1 (ar)	2011-08-22	2017-09-20	Takeda Pharmaceuticals Co	مركبات بيريدازينون واستخدامها كمثبطات daao
AU2012337781B2 (en)	2011-11-15	2017-07-06	Takeda Pharmaceutical Company Limited	Dihydroxy aromatic heterocyclic compound
GB201222711D0 (en)	2012-12-17	2013-01-30	Takeda Pharmaceutical	Novel compounds
CN110655526A (zh) *	2018-06-28	2020-01-07	中国科学院上海药物研究所	头孢菌素-铁载体轭合物及其制备方法和用途

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS60142987A (ja) *	1983-12-29	1985-07-29	Mochida Pharmaceut Co Ltd	セフアロスポリン誘導体
EP0150507B1 (fr) *	1983-12-29	1992-08-05	Mochida Pharmaceutical Co., Ltd.	Dérivés de céphalosporine, procédés pour leur péparation et compositions pharmaceutiques
AU586215B2 (en) *	1985-01-21	1989-07-06	Nippon Pharmaceutical Development Institute Company Limited	Novel ```-lactam antibiotics
NZ215527A (en) *	1985-04-01	1989-06-28	Mochida Pharm Co Ltd	Cephalosporin derivatives and pharmaceutical compositions
FI872879A7 (fi) *	1986-07-21	1988-01-22	Sankei Yakuhin Kk	--laktamfoerening, foerfarande foer dess framstaellning, denna innehaollande laekemedelskomposition foer behandling av sjukdom med bakterieinfektion samt mellanprodukter foer dess syntes.
US4880798A (en) *	1986-11-25	1989-11-14	Mochida Pharmaceutical Co., Ltd.	Cephalosporin derivatives

1988
- 1988-03-28 DK DK170088A patent/DK170088A/da not_active IP Right Cessation
- 1988-04-04 IL IL85970A patent/IL85970A0/xx unknown
- 1988-04-06 HU HU881705A patent/HU201948B/hu not_active IP Right Cessation
- 1988-04-06 NZ NZ224130A patent/NZ224130A/xx unknown
- 1988-04-06 PH PH36757A patent/PH24960A/en unknown
- 1988-04-06 AU AU14310/88A patent/AU611428B2/en not_active Ceased
- 1988-04-07 MC MC881967A patent/MC1920A1/fr unknown
- 1988-04-08 YU YU00708/88A patent/YU70888A/xx unknown
- 1988-04-08 JP JP63085490A patent/JPH01261392A/ja active Pending
- 1988-04-08 US US07/179,199 patent/US5055572A/en not_active Expired - Fee Related
- 1988-04-08 PT PT87202A patent/PT87202B/pt not_active IP Right Cessation
- 1988-04-08 FI FI881641A patent/FI881641A7/fi not_active IP Right Cessation
- 1988-04-08 NO NO881530A patent/NO881530L/no unknown
- 1988-04-09 KR KR1019880004040A patent/KR880012611A/ko not_active Withdrawn
- 1988-04-11 EP EP19880105732 patent/EP0286144A3/fr not_active Withdrawn

Also Published As

Publication number	Publication date
EP0286144A3 (fr)	1990-10-03
AU1431088A (en)	1988-10-13
NO881530D0 (no)	1988-04-08
NZ224130A (en)	1991-02-26
AU611428B2 (en)	1991-06-13
FI881641A0 (fi)	1988-04-08
DK170088D0 (da)	1988-03-28
IL85970A0 (en)	1988-09-30
HUT46920A (en)	1988-12-28
PT87202B (pt)	1992-07-31
HU201948B (en)	1991-01-28
JPH01261392A (ja)	1989-10-18
FI881641A7 (fi)	1988-10-11
US5055572A (en)	1991-10-08
MC1920A1 (fr)	1989-04-06
EP0286144A2 (fr)	1988-10-12
PT87202A (pt)	1988-05-01
DK170088A (da)	1988-10-11
KR880012611A (ko)	1988-11-28
PH24960A (en)	1990-12-26
YU70888A (en)	1989-12-31

Publication	Publication Date	Title
AU604868B2 (en)	1991-01-03	3-(substituted-(pyrazolo/s-triazolo)(1,5-a) pyrimidinylthiomethyl)-7-acyl-cephalosporin derivatives
US4470983A (en)	1984-09-11	Cephalosporin derivatives
US4327210A (en)	1982-04-27	Thiazolylacelamide cephalosporins
SE437522B (sv)	1985-03-04	(6r,7r)-7-/2-(2-amino-4-tiazolyl)-2-(z-metoxiimino)-acetamido/-3-(substituerad tiometyl)-cefalosporinsyra samt legre alkanoylalkyl estar/etrar derav
CA1225390A (fr)	1987-08-11	Cephalosporines 3-bicyclopyridinium-methyliques
NO881530L (no)	1988-10-11	Acylderivater.
EP0153709A2 (fr)	1985-09-04	Dérivés de céphalosporine
US5202315A (en)	1993-04-13	Cephalosporin compounds
NZ225754A (en)	1991-04-26	Cephalosporin derivatives; medicaments and methods for preparation and treatment
NO801400L (no)	1980-11-12	Fremgangsmaate ved fremstilling av heterocyklylderivater av oksy-imino-substituerte cephalosporiner
CS204957B2 (en)	1981-04-30	Method of producing novel 7-2-/4-thiazolyl/-2-iminoacetamido-3-/4-alkyl-5-oxo-6-hydroxy-4,5-dihydro-1,2,4-triazin-3-ylthio/methyl-3-cephemderivatives
US4971962A (en)	1990-11-20	Cephalosporin compounds
US4489076A (en)	1984-12-18	Cephalosporins
US5138066A (en)	1992-08-11	Intermediates for cephalosporins with sulfur-containing oxyimino side chain
US5073550A (en)	1991-12-17	Cephalosphorins with sulfur-containing oxyimino side chain
NO813420L (no)	1982-04-13	Acylderivater.
US4349672A (en)	1982-09-14	Cephalosporin derivatives
CA1114808A (fr)	1981-12-22	Derives d'oxyiminoacetamidocephalosporines substituees en 7
US4358448A (en)	1982-11-09	N-substituted thiazolyl derivatives of oxy-imino-substituted cephalosporins useful as anti-bacterial agents
GB1582960A (en)	1981-01-21	Chemical synthesis of -lactam derivatives
US4482551A (en)	1984-11-13	Cephalosporin derivatives
SK279280B6 (sk)	1998-09-09	Spôsob výroby hemiheptahydrátu dvojsodnej soli 7-[
US4412070A (en)	1983-10-25	Cephalosporin derivatives
US4431804A (en)	1984-02-14	Thiazolylacetamido compounds
CA1177823A (fr)	1984-11-13	Derives de cephalosporine