SK14152000A3 - Cefalosporíny obsahujúce cyklické aminoguanidíny ako substituenty, spôsob ich prípravy a farmaceutický prostriedok, ktorý ich obsahuje - Google Patents
Cefalosporíny obsahujúce cyklické aminoguanidíny ako substituenty, spôsob ich prípravy a farmaceutický prostriedok, ktorý ich obsahuje Download PDFInfo
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- SK14152000A3 SK14152000A3 SK1415-2000A SK14152000A SK14152000A3 SK 14152000 A3 SK14152000 A3 SK 14152000A3 SK 14152000 A SK14152000 A SK 14152000A SK 14152000 A3 SK14152000 A3 SK 14152000A3
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- SK
- Slovakia
- Prior art keywords
- group
- lactam
- formula
- beta
- compound
- Prior art date
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- 239000003242 anti bacterial agent Substances 0.000 title description 4
- 229940088710 antibiotic agent Drugs 0.000 title description 3
- 125000001271 cephalosporin group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 109
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 39
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 95
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 43
- -1 aminoiminomethyl group Chemical group 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000004185 ester group Chemical group 0.000 claims description 9
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 230000000813 microbial effect Effects 0.000 claims description 8
- 241000894006 Bacteria Species 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 241000588748 Klebsiella Species 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
- 241000588914 Enterobacter Species 0.000 claims description 4
- 241000194033 Enterococcus Species 0.000 claims description 4
- 241000588722 Escherichia Species 0.000 claims description 4
- 241000588621 Moraxella Species 0.000 claims description 4
- 241000589516 Pseudomonas Species 0.000 claims description 4
- 241000191940 Staphylococcus Species 0.000 claims description 4
- 241000194017 Streptococcus Species 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 3
- 125000005277 alkyl imino group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 150000004677 hydrates Chemical group 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- HCUOEKSZWPGJIM-IYNMRSRQSA-N (e,2z)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N\O)\C(N)=O HCUOEKSZWPGJIM-IYNMRSRQSA-N 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical group NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 abstract description 3
- 125000004122 cyclic group Chemical group 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 174
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 52
- 239000002904 solvent Substances 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 8
- 239000003456 ion exchange resin Substances 0.000 description 8
- 229920003303 ion-exchange polymer Polymers 0.000 description 8
- 125000003282 alkyl amino group Chemical group 0.000 description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
- 125000000547 substituted alkyl group Chemical group 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229920001429 chelating resin Polymers 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 125000004663 dialkyl amino group Chemical group 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 6
- QUNHFZMXHPURNQ-UHFFFAOYSA-N 1-(benzylideneamino)-n-methyl-3-propylimidazolidin-2-imine Chemical compound CN=C1N(CCC)CCN1N=CC1=CC=CC=C1 QUNHFZMXHPURNQ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 150000003952 β-lactams Chemical class 0.000 description 5
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 239000003957 anion exchange resin Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- GKHNWZLUWJEZRC-UHFFFAOYSA-N 1-(benzylideneamino)-n-methyl-4,5-dihydroimidazol-2-amine Chemical compound CNC1=NCCN1N=CC1=CC=CC=C1 GKHNWZLUWJEZRC-UHFFFAOYSA-N 0.000 description 3
- GPLPAXVMGVVCOU-UHFFFAOYSA-N 4,5-dihydroimidazole-1,2-diamine Chemical compound NN1CCN=C1N GPLPAXVMGVVCOU-UHFFFAOYSA-N 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 229960000484 ceftazidime Drugs 0.000 description 3
- NMVPEQXCMGEDNH-TZVUEUGBSA-N ceftazidime pentahydrate Chemical compound O.O.O.O.O.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 NMVPEQXCMGEDNH-TZVUEUGBSA-N 0.000 description 3
- 239000013256 coordination polymer Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
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- 238000001256 steam distillation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BSCSTUOYFVJBNR-UHFFFAOYSA-N 1-(benzylideneamino)-n-(2-chloroethyl)-4,5-dihydroimidazol-2-amine Chemical compound ClCCN=C1NCCN1N=CC1=CC=CC=C1 BSCSTUOYFVJBNR-UHFFFAOYSA-N 0.000 description 2
- ATLGVDDWZNKGGN-UHFFFAOYSA-N 1-[2-[[1-(benzylideneamino)-4,5-dihydroimidazol-2-yl]amino]propyl]-3-methylthiourea Chemical compound CNC(=S)NCC(C)N=C1NCCN1N=CC1=CC=CC=C1 ATLGVDDWZNKGGN-UHFFFAOYSA-N 0.000 description 2
- GWSAKXBWBVWOOK-UHFFFAOYSA-N 1-[3-(benzylideneamino)-2-iminoimidazolidin-1-yl]-1,2-di(propan-2-yl)guanidine Chemical compound N=C1N(N(C(C)C)C(N)=NC(C)C)CCN1N=CC1=CC=CC=C1 GWSAKXBWBVWOOK-UHFFFAOYSA-N 0.000 description 2
- GJRGMYHXLXNROH-UHFFFAOYSA-N 1-amino-1-(2,2-diethoxyethyl)-3-methylthiourea Chemical compound CCOC(OCC)CN(N)C(=S)NC GJRGMYHXLXNROH-UHFFFAOYSA-N 0.000 description 2
- WSEUBGCUAJCBAE-UHFFFAOYSA-N 1-ethyl-3-nitrosoimidazolidine-2-thione Chemical compound CCN1CCN(N=O)C1=S WSEUBGCUAJCBAE-UHFFFAOYSA-N 0.000 description 2
- CGTZBCKWUFCPOA-UHFFFAOYSA-N 1-methyl-3-nitrosoimidazolidine-2-thione Chemical compound CN1CCN(N=O)C1=S CGTZBCKWUFCPOA-UHFFFAOYSA-N 0.000 description 2
- RYUMFMYVFWEKKW-UHFFFAOYSA-N 1-nitroso-3-propylimidazolidine-2-thione Chemical compound CCCN1CCN(N=O)C1=S RYUMFMYVFWEKKW-UHFFFAOYSA-N 0.000 description 2
- FNYYZYFPSXNOQM-UHFFFAOYSA-N 4-methyl-1-nitrosoimidazolidine-2-thione Chemical compound CC1CN(N=O)C(=S)N1 FNYYZYFPSXNOQM-UHFFFAOYSA-N 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000588697 Enterobacter cloacae Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241000124008 Mammalia Species 0.000 description 2
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000002814 agar dilution Methods 0.000 description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 2
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- 125000001769 aryl amino group Chemical group 0.000 description 2
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- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
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- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 2
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- DLDLXKKKTBIYNA-UHFFFAOYSA-N methyl n-[3-[[1-(benzylideneamino)-4,5-dihydroimidazol-2-yl]amino]propyl]-n'-methylcarbamimidothioate Chemical compound CSC(=NC)NCCCN=C1NCCN1N=CC1=CC=CC=C1 DLDLXKKKTBIYNA-UHFFFAOYSA-N 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
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- UCZLDXDIKXEGSR-HZRGNIKMSA-N (6R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(fluoromethoxyimino)acetyl]amino]-3-[(3-ethyl-2-methyliminoimidazolidin-1-yl)iminomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC1=NC(=NS1)/C(/C(=O)NC1[C@@H]2N(C(=C(CS2)C=NN2C(N(CC2)CC)=NC)C(=O)O)C1=O)=N/OCF UCZLDXDIKXEGSR-HZRGNIKMSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZOTVHONSLJSOLZ-UHFFFAOYSA-N 1-(2-aminoethyl)imidazolidine-2-thione Chemical compound NCCN1CCNC1=S ZOTVHONSLJSOLZ-UHFFFAOYSA-N 0.000 description 1
- AGZRADXSTWCBLN-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-nitrosoimidazolidine-2-thione Chemical compound OCCN1CCN(N=O)C1=S AGZRADXSTWCBLN-UHFFFAOYSA-N 0.000 description 1
- VEJBIZGCEAMIHE-UHFFFAOYSA-N 1-(benzylideneamino)-1-(2,2-diethoxyethyl)-2,3-dimethylguanidine Chemical compound CCOC(OCC)CN(C(NC)=NC)N=CC1=CC=CC=C1 VEJBIZGCEAMIHE-UHFFFAOYSA-N 0.000 description 1
- MQEVOKQZQDQGDB-UHFFFAOYSA-N 1-(benzylideneamino)-3-ethylimidazolidine-2-thione Chemical compound S=C1N(CC)CCN1N=CC1=CC=CC=C1 MQEVOKQZQDQGDB-UHFFFAOYSA-N 0.000 description 1
- FQQNGZKNLYOPNU-UHFFFAOYSA-N 1-(benzylideneamino)-3-methylimidazolidine-2-thione Chemical compound S=C1N(C)CCN1N=CC1=CC=CC=C1 FQQNGZKNLYOPNU-UHFFFAOYSA-N 0.000 description 1
- MULLVSURLGWENJ-UHFFFAOYSA-N 1-(benzylideneamino)-3-propylimidazolidine-2-thione Chemical compound S=C1N(CCC)CCN1N=CC1=CC=CC=C1 MULLVSURLGWENJ-UHFFFAOYSA-N 0.000 description 1
- FSXGHBVSWRFUKB-UHFFFAOYSA-N 1-(benzylideneamino)-4,4-dimethylimidazolidine-2-thione Chemical compound S=C1NC(C)(C)CN1N=CC1=CC=CC=C1 FSXGHBVSWRFUKB-UHFFFAOYSA-N 0.000 description 1
- FSIMESHVEWORPJ-UHFFFAOYSA-N 1-(benzylideneamino)-4,5-dihydroimidazol-2-amine Chemical compound NC1=NCCN1N=CC1=CC=CC=C1 FSIMESHVEWORPJ-UHFFFAOYSA-N 0.000 description 1
- SYSHVADGHDYFMD-UHFFFAOYSA-N 1-(benzylideneamino)-4-methylimidazolidine-2-thione Chemical compound S=C1NC(C)CN1N=CC1=CC=CC=C1 SYSHVADGHDYFMD-UHFFFAOYSA-N 0.000 description 1
- PIJUZODSURIXTO-UHFFFAOYSA-N 1-(benzylideneamino)imidazolidine-2-thione Chemical compound S=C1NCCN1N=CC1=CC=CC=C1 PIJUZODSURIXTO-UHFFFAOYSA-N 0.000 description 1
- OBZZVBITPIYLTA-UHFFFAOYSA-N 1-[3-[(1-aminoimidazolidin-2-yl)amino]propyl]-1,2-dimethylguanidine Chemical compound CN=C(N)N(C)CCCNC1NCCN1N OBZZVBITPIYLTA-UHFFFAOYSA-N 0.000 description 1
- YMXAXAWPIJDPEO-UHFFFAOYSA-N 1-[3-[[1-(benzylideneamino)imidazolidin-2-yl]amino]propyl]-1,2-dimethylguanidine Chemical class CN=C(N)N(C)CCCNC1NCCN1N=CC1=CC=CC=C1 YMXAXAWPIJDPEO-UHFFFAOYSA-N 0.000 description 1
- PVMURSYOQVEKJP-UHFFFAOYSA-N 1-ethylimidazolidine-2-thione Chemical compound CCN1CCNC1=S PVMURSYOQVEKJP-UHFFFAOYSA-N 0.000 description 1
- VPXVFRMBWSDPLV-UHFFFAOYSA-N 2,2-diethoxyethylhydrazine Chemical compound CCOC(CNN)OCC VPXVFRMBWSDPLV-UHFFFAOYSA-N 0.000 description 1
- SKWCZPYWFRTSDD-UHFFFAOYSA-N 2,3-bis(azaniumyl)propanoate;chloride Chemical compound Cl.NCC(N)C(O)=O SKWCZPYWFRTSDD-UHFFFAOYSA-N 0.000 description 1
- FDNUAMSGRORQFV-UHFFFAOYSA-N 2-[3-[(1-amino-4,5-dihydroimidazol-2-yl)amino]propyl]guanidine Chemical compound NN1CCN=C1NCCCN=C(N)N FDNUAMSGRORQFV-UHFFFAOYSA-N 0.000 description 1
- JWXXEIXQDLSZSW-UHFFFAOYSA-N 2-[3-[[1-(benzylideneamino)-4,5-dihydroimidazol-2-yl]amino]propyl]guanidine Chemical compound NC(=N)NCCCN=C1NCCN1N=CC1=CC=CC=C1 JWXXEIXQDLSZSW-UHFFFAOYSA-N 0.000 description 1
- XLHVWIUTAFMFTA-UHFFFAOYSA-N 2-[[1-(benzylideneamino)-4,5-dihydroimidazol-2-yl]amino]ethanol Chemical compound OCCNC1=NCCN1N=CC1=CC=CC=C1 XLHVWIUTAFMFTA-UHFFFAOYSA-N 0.000 description 1
- YOFRXBUPVLMZNQ-UHFFFAOYSA-N 2-methylimino-3-propylimidazolidin-1-amine Chemical compound CCCN1CCN(N)C1=NC YOFRXBUPVLMZNQ-UHFFFAOYSA-N 0.000 description 1
- VZOPQRNXEOGYNT-UHFFFAOYSA-N 3,3-diaminopropan-1-ol Chemical compound NC(N)CCO VZOPQRNXEOGYNT-UHFFFAOYSA-N 0.000 description 1
- XBVZOSFPDGRHQN-UHFFFAOYSA-N 3-hydroxy-5-(hydroxymethyl)-2-(morpholin-4-ylmethyl)pyridine-4-carbaldehyde Chemical compound O1CCN(CC1)CC1=NC=C(C(=C1O)C=O)CO XBVZOSFPDGRHQN-UHFFFAOYSA-N 0.000 description 1
- TUEWZIYRHKESAC-UHFFFAOYSA-N 3-methyl-2-methyliminoimidazol-1-amine Chemical compound CN=C1N(C)C=CN1N TUEWZIYRHKESAC-UHFFFAOYSA-N 0.000 description 1
- TXRCQKVSGVJWAW-UHFFFAOYSA-N 4,4-dimethylimidazolidine-2-thione Chemical compound CC1(C)CNC(=S)N1 TXRCQKVSGVJWAW-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- CVGINOUVXZZMEY-UHFFFAOYSA-N 5,5-dimethyl-1-nitrosoimidazolidine-2-thione Chemical compound CC1(C)CNC(=S)N1N=O CVGINOUVXZZMEY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BAKZKIYQIMRGEQ-UHFFFAOYSA-N C(C1=CC=CC=C1)=N[N+]1=CNC=C1.[Cl-] Chemical compound C(C1=CC=CC=C1)=N[N+]1=CNC=C1.[Cl-] BAKZKIYQIMRGEQ-UHFFFAOYSA-N 0.000 description 1
- ZEADYULHQFHARY-UHFFFAOYSA-N CC1(NC(N(C1)N=O)=S)C Chemical compound CC1(NC(N(C1)N=O)=S)C ZEADYULHQFHARY-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 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
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 241000588655 Moraxella catarrhalis Species 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- SPOZXCNVUGTKAN-UHFFFAOYSA-N S=C1N(CCO)CCN1N=CC1=CC=CC=C1 Chemical compound S=C1N(CCO)CCN1N=CC1=CC=CC=C1 SPOZXCNVUGTKAN-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- 240000004922 Vigna radiata Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ZDOOLEFXPVFCDZ-UHFFFAOYSA-M [1-(benzylideneamino)-3-propylimidazolidin-2-ylidene]-dimethylazanium;iodide Chemical compound [I-].C[N+](C)=C1N(CCC)CCN1N=CC1=CC=CC=C1 ZDOOLEFXPVFCDZ-UHFFFAOYSA-M 0.000 description 1
- KRYWEAYKLGCRRH-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]azanium;chloride Chemical compound Cl.CSC(N)=N KRYWEAYKLGCRRH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000006307 alkoxy benzyl group Chemical group 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001411 amidrazones Chemical class 0.000 description 1
- 125000005122 aminoalkylamino group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 238000009635 antibiotic susceptibility testing Methods 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229940032049 enterococcus faecalis Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- QAEKVJNQDKJVGB-UHFFFAOYSA-N imidazol-1-amine;hydrochloride Chemical compound Cl.NN1C=CN=C1 QAEKVJNQDKJVGB-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- OCFIMHWCWRCAMN-UHFFFAOYSA-N n-(2-hydrazinyl-4,5-dihydroimidazol-1-yl)-1-phenylmethanimine Chemical compound NNC1=NCCN1N=CC1=CC=CC=C1 OCFIMHWCWRCAMN-UHFFFAOYSA-N 0.000 description 1
- WTMMMOIVJPLNDW-UHFFFAOYSA-N n-(2-methylsulfanyl-4,5-dihydroimidazol-1-yl)-1-phenylmethanimine Chemical compound CSC1=NCCN1N=CC1=CC=CC=C1 WTMMMOIVJPLNDW-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- JSIVBVHQFFIWAQ-UHFFFAOYSA-N n-imidazol-1-yl-1-phenylmethanimine Chemical compound C=1C=CC=CC=1C=NN1C=CN=C1 JSIVBVHQFFIWAQ-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 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
- 239000000047 product Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 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
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0051598A AT406772B (de) | 1998-03-23 | 1998-03-23 | Antibakterielle 7-acylamino-3-iminomethyl- cephalosporine und verfahren zu deren herstellung |
| PCT/EP1999/001853 WO1999048896A1 (en) | 1998-03-23 | 1999-03-19 | Cephalosporines having cyclic aminoguanidine substituents as antibiotics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK14152000A3 true SK14152000A3 (sk) | 2001-05-10 |
Family
ID=3492649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1415-2000A SK14152000A3 (sk) | 1998-03-23 | 1999-03-19 | Cefalosporíny obsahujúce cyklické aminoguanidíny ako substituenty, spôsob ich prípravy a farmaceutický prostriedok, ktorý ich obsahuje |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6440957B1 (enExample) |
| EP (2) | EP1930335A1 (enExample) |
| JP (1) | JP2002507616A (enExample) |
| KR (1) | KR100696422B1 (enExample) |
| CN (1) | CN1188418C (enExample) |
| AR (1) | AR015248A1 (enExample) |
| AT (1) | AT406772B (enExample) |
| AU (1) | AU749735B2 (enExample) |
| BR (1) | BR9908960A (enExample) |
| CA (1) | CA2324953C (enExample) |
| CO (1) | CO5080739A1 (enExample) |
| HU (1) | HUP0101603A3 (enExample) |
| ID (1) | ID26567A (enExample) |
| IL (2) | IL138477A0 (enExample) |
| MY (1) | MY119841A (enExample) |
| NO (1) | NO20004760L (enExample) |
| NZ (1) | NZ506908A (enExample) |
| PE (1) | PE20000360A1 (enExample) |
| PL (1) | PL343094A1 (enExample) |
| RU (1) | RU2245884C2 (enExample) |
| SK (1) | SK14152000A3 (enExample) |
| TR (1) | TR200002749T2 (enExample) |
| TW (1) | TWI250983B (enExample) |
| WO (1) | WO1999048896A1 (enExample) |
| ZA (1) | ZA200004850B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6693095B2 (en) * | 1997-04-01 | 2004-02-17 | Biochemie Gesellschaft M.B.H. | Antibacterial substituted 7-acylamino-3-(methylhydrazono) methyl-cephalosporins and intermediates |
| DE102007052891A1 (de) | 2007-11-02 | 2009-05-07 | Evonik Degussa Gmbh | Verfahren zur Stabilisierung von olefinisch ungesättigten Monomeren |
| DE102013204950A1 (de) | 2013-03-20 | 2014-09-25 | Evonik Industries Ag | Verfahren und Zusammensetzung zur Inhibierung der Polymerisation von Cyclopentadienverbindungen |
| ES2624415T3 (es) | 2014-09-08 | 2017-07-14 | Evonik Degussa Gmbh | (Tio)acetales fenólicos como agentes inhibidores de la polimerización de monómeros olefínicamente insaturados |
| TWI669317B (zh) | 2014-09-22 | 2019-08-21 | 德商贏創德固賽有限責任公司 | 反應性單體的改良製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE943408C (de) * | 1953-03-31 | 1956-05-17 | Bayer Ag | Verfahren zur Darstellung von Bisguanylhydrazonen |
| FI851934A7 (fi) * | 1984-05-30 | 1985-12-01 | Ici Plc | Kefalosporiinijohdannaisia. |
| GB8721568D0 (en) * | 1987-09-14 | 1987-10-21 | Fujisawa Pharmaceutical Co | Cephem compounds |
| NZ308518A (en) * | 1995-05-11 | 2000-01-28 | Biochemie Gmbh | Antibacterial cephalosporins |
| NZ337732A (en) * | 1997-04-01 | 2001-09-28 | Biochemie Gmbh | Antibacterial substituted 7-acylamino -3-(methylhydrazono) methyl-cephalosporins and intermediates |
-
1998
- 1998-03-23 AT AT0051598A patent/AT406772B/de not_active IP Right Cessation
-
1999
- 1999-03-19 AR ARP990101236A patent/AR015248A1/es not_active Application Discontinuation
- 1999-03-19 EP EP07021394A patent/EP1930335A1/en not_active Withdrawn
- 1999-03-19 RU RU2000126469/04A patent/RU2245884C2/ru not_active IP Right Cessation
- 1999-03-19 AU AU35188/99A patent/AU749735B2/en not_active Ceased
- 1999-03-19 IL IL13847799A patent/IL138477A0/xx not_active IP Right Cessation
- 1999-03-19 SK SK1415-2000A patent/SK14152000A3/sk unknown
- 1999-03-19 ID IDW20001853A patent/ID26567A/id unknown
- 1999-03-19 EP EP99916839A patent/EP1082326A1/en not_active Withdrawn
- 1999-03-19 CA CA002324953A patent/CA2324953C/en not_active Expired - Fee Related
- 1999-03-19 CO CO99017143A patent/CO5080739A1/es unknown
- 1999-03-19 BR BR9908960-2A patent/BR9908960A/pt not_active Application Discontinuation
- 1999-03-19 HU HU0101603A patent/HUP0101603A3/hu unknown
- 1999-03-19 TR TR2000/02749T patent/TR200002749T2/xx unknown
- 1999-03-19 CN CNB998043192A patent/CN1188418C/zh not_active Expired - Fee Related
- 1999-03-19 WO PCT/EP1999/001853 patent/WO1999048896A1/en not_active Ceased
- 1999-03-19 ZA ZA200004850A patent/ZA200004850B/en unknown
- 1999-03-19 JP JP2000537879A patent/JP2002507616A/ja not_active Withdrawn
- 1999-03-19 NZ NZ506908A patent/NZ506908A/xx unknown
- 1999-03-19 PL PL99343094A patent/PL343094A1/xx unknown
- 1999-03-19 KR KR1020007010434A patent/KR100696422B1/ko not_active Expired - Fee Related
- 1999-03-22 MY MYPI99001068A patent/MY119841A/en unknown
- 1999-03-22 PE PE1999000232A patent/PE20000360A1/es not_active Application Discontinuation
- 1999-05-10 TW TW088107541A patent/TWI250983B/zh not_active IP Right Cessation
-
2000
- 2000-09-14 IL IL138477A patent/IL138477A/en unknown
- 2000-09-21 US US09/667,075 patent/US6440957B1/en not_active Expired - Fee Related
- 2000-09-22 NO NO20004760A patent/NO20004760L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1082326A1 (en) | 2001-03-14 |
| ZA200004850B (en) | 2002-02-27 |
| JP2002507616A (ja) | 2002-03-12 |
| ID26567A (id) | 2001-01-18 |
| KR100696422B1 (ko) | 2007-03-20 |
| WO1999048896A1 (en) | 1999-09-30 |
| AR015248A1 (es) | 2001-04-18 |
| TR200002749T2 (tr) | 2000-12-21 |
| PE20000360A1 (es) | 2000-05-17 |
| CO5080739A1 (es) | 2001-09-25 |
| CA2324953C (en) | 2008-05-13 |
| AU749735B2 (en) | 2002-07-04 |
| AT406772B (de) | 2000-08-25 |
| CN1294593A (zh) | 2001-05-09 |
| NO20004760L (no) | 2000-11-21 |
| KR20010074666A (ko) | 2001-08-08 |
| IL138477A (en) | 2007-06-17 |
| NZ506908A (en) | 2003-04-29 |
| RU2245884C2 (ru) | 2005-02-10 |
| CN1188418C (zh) | 2005-02-09 |
| PL343094A1 (en) | 2001-07-30 |
| MY119841A (en) | 2005-07-29 |
| ATA51598A (de) | 2000-01-15 |
| US6440957B1 (en) | 2002-08-27 |
| AU3518899A (en) | 1999-10-18 |
| HUP0101603A2 (hu) | 2001-12-28 |
| IL138477A0 (en) | 2001-10-31 |
| HUP0101603A3 (en) | 2002-10-28 |
| NO20004760D0 (no) | 2000-09-22 |
| TWI250983B (en) | 2006-03-11 |
| CA2324953A1 (en) | 1999-09-30 |
| EP1930335A1 (en) | 2008-06-11 |
| BR9908960A (pt) | 2000-12-05 |
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