TWI250983B - Cyclic aminoguanidines - Google Patents
Cyclic aminoguanidines Download PDFInfo
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- TWI250983B TWI250983B TW088107541A TW88107541A TWI250983B TW I250983 B TWI250983 B TW I250983B TW 088107541 A TW088107541 A TW 088107541A TW 88107541 A TW88107541 A TW 88107541A TW I250983 B TWI250983 B TW I250983B
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- TW
- Taiwan
- Prior art keywords
- group
- alkyl
- indoleamine
- substituted
- hydrogen
- Prior art date
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- -1 Cyclic aminoguanidines Chemical class 0.000 title claims description 45
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 29
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 19
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 88
- 150000003839 salts Chemical group 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 125000000623 heterocyclic group Chemical group 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 125000003277 amino group Chemical group 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 241000894006 Bacteria Species 0.000 claims description 6
- 241000588748 Klebsiella Species 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 230000000813 microbial effect Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 241000194033 Enterococcus Species 0.000 claims description 5
- 241000588722 Escherichia Species 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 208000035143 Bacterial infection Diseases 0.000 claims description 4
- 241000588914 Enterobacter Species 0.000 claims description 4
- 241000589516 Pseudomonas Species 0.000 claims description 4
- 241000194017 Streptococcus Species 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 241000588621 Moraxella Species 0.000 claims description 3
- 241000191940 Staphylococcus Species 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 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
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 13
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical group O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
- 229920006395 saturated elastomer Chemical class 0.000 claims 2
- OUZZSIOQTSNTTI-UHFFFAOYSA-N 2,6-dichloro-n-(1-propan-2-ylpiperidin-4-yl)benzamide Chemical group C1CN(C(C)C)CCC1NC(=O)C1=C(Cl)C=CC=C1Cl OUZZSIOQTSNTTI-UHFFFAOYSA-N 0.000 claims 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 1
- 241000588915 Klebsiella aerogenes Species 0.000 claims 1
- 241000282376 Panthera tigris Species 0.000 claims 1
- 229910052772 Samarium Inorganic materials 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 229940092559 enterobacter aerogenes Drugs 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical class C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims 1
- 239000004575 stone Substances 0.000 claims 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical group NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 155
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 113
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 112
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 68
- 239000000203 mixture Substances 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 46
- 239000002904 solvent Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000001704 evaporation Methods 0.000 description 17
- 230000008020 evaporation Effects 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 16
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
- 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 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 230000002079 cooperative effect Effects 0.000 description 8
- 150000003840 hydrochlorides Chemical group 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000003957 anion exchange resin Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 101150041968 CDC13 gene Proteins 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000004185 ester group Chemical group 0.000 description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- DYHSDKLCOJIUFX-UHFFFAOYSA-N Di-tert-butyl dicarbonate Substances CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GUTJTTSDGYOPNY-UHFFFAOYSA-N N1C(=CC2=CC=CC=C12)N.NN Chemical compound N1C(=CC2=CC=CC=C12)N.NN GUTJTTSDGYOPNY-UHFFFAOYSA-N 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
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- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 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 2
- YPXQSGWOGQPLQO-UHFFFAOYSA-N 5-nitro-1,3-dihydrobenzimidazole-2-thione Chemical compound [O-][N+](=O)C1=CC=C2N=C(S)NC2=C1 YPXQSGWOGQPLQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000588697 Enterobacter cloacae Species 0.000 description 2
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- 244000294411 Mirabilis expansa Species 0.000 description 2
- 235000015429 Mirabilis expansa Nutrition 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000002814 agar dilution Methods 0.000 description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229960000484 ceftazidime Drugs 0.000 description 2
- 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 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 229940113088 dimethylacetamide Drugs 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
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- 229910052751 metal Inorganic materials 0.000 description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
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- 239000012453 solvate Substances 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
- AFINAILKDBCXMX-PBHICJAKSA-N (2s,3r)-2-amino-3-hydroxy-n-(4-octylphenyl)butanamide Chemical compound CCCCCCCCC1=CC=C(NC(=O)[C@@H](N)[C@@H](C)O)C=C1 AFINAILKDBCXMX-PBHICJAKSA-N 0.000 description 1
- 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 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 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
- 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 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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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
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- 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 (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI250983B true TWI250983B (en) | 2006-03-11 |
Family
ID=3492649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088107541A TWI250983B (en) | 1998-03-23 | 1999-05-10 | Cyclic aminoguanidines |
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 |
| SK14152000A3 (sk) | 2001-05-10 |
| 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 |
| CA2324953A1 (en) | 1999-09-30 |
| EP1930335A1 (en) | 2008-06-11 |
| BR9908960A (pt) | 2000-12-05 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |