EA014163B1 - Производные хинолина в качестве антибактериальных агентов - Google Patents

Info

Publication number

EA014163B1

EA014163B1 EA200800152A EA200800152A EA014163B1 EA 014163 B1 EA014163 B1 EA 014163B1 EA 200800152 A EA200800152 A EA 200800152A EA 200800152 A EA200800152 A EA 200800152A EA 014163 B1 EA014163 B1 EA 014163B1

Authority

EA

Eurasian Patent Office

Prior art keywords

compound

phenyl

alkyl

mol

alkyloxy

Prior art date

2005-06-28

Links

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• Global Dossier
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• 239000003242 anti bacterial agent Substances 0.000 title claims abstract description 33
• 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims description 5
• 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 181
• 150000003839 salts Chemical class 0.000 claims abstract description 32
• 239000002253 acid Substances 0.000 claims abstract description 31
• 208000035143 Bacterial infection Diseases 0.000 claims abstract description 27
• 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 26
• 238000011282 treatment Methods 0.000 claims abstract description 25
• 239000003814 drug Substances 0.000 claims abstract description 14
• 238000004519 manufacturing process Methods 0.000 claims abstract description 5
• 206010062207 Mycobacterial infection Diseases 0.000 claims abstract description 4
• 208000027531 mycobacterial infectious disease Diseases 0.000 claims abstract description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• -1 alkyloxyalkyloxy Chemical group 0.000 claims description 64
• 125000004432 carbon atom Chemical group C* 0.000 claims description 50
• 238000002360 preparation method Methods 0.000 claims description 50
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• 125000003545 alkoxy group Chemical group 0.000 claims description 46
• 239000001257 hydrogen Substances 0.000 claims description 46
• 229910052736 halogen Inorganic materials 0.000 claims description 39
• 150000002367 halogens Chemical class 0.000 claims description 39
• 229930195734 saturated hydrocarbon Natural products 0.000 claims description 36
• 125000001424 substituent group Chemical group 0.000 claims description 34
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 28
• 208000015181 infectious disease Diseases 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• 125000004122 cyclic group Chemical group 0.000 claims description 24
• 150000002431 hydrogen Chemical class 0.000 claims description 22
• 241000894006 Bacteria Species 0.000 claims description 15
• WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 claims description 14
• 125000001188 haloalkyl group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 125000001624 naphthyl group Chemical group 0.000 claims description 12
• 125000005843 halogen group Chemical group 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
• 239000005977 Ethylene Substances 0.000 claims description 8
• RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 229960003085 meticillin Drugs 0.000 claims description 8
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 239000003926 antimycobacterial agent Substances 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
• 239000004480 active ingredient Substances 0.000 claims description 5
• 239000011737 fluorine Substances 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 229930182555 Penicillin Natural products 0.000 claims description 4
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 4
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
• 229930195733 hydrocarbon Natural products 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• 239000004215 Carbon black (E152) Substances 0.000 claims description 2
• 229940049954 penicillin Drugs 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
• 241000295644 Staphylococcaceae Species 0.000 claims 2
• 125000001246 bromo group Chemical group Br* 0.000 claims 1
• 125000001309 chloro group Chemical group Cl* 0.000 claims 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
• 125000002346 iodo group Chemical group I* 0.000 claims 1
• 230000008520 organization Effects 0.000 claims 1
• 125000000815 N-oxide group Chemical group 0.000 abstract 1
• 239000000543 intermediate Substances 0.000 description 145
• 239000000203 mixture Substances 0.000 description 131
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 118
• 239000002904 solvent Substances 0.000 description 112
• 239000000243 solution Substances 0.000 description 69
• 239000012044 organic layer Substances 0.000 description 50
• 239000000460 chlorine Chemical group 0.000 description 47
• 239000003480 eluent Substances 0.000 description 38
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
• 238000000034 method Methods 0.000 description 36
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 34
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
• 150000003254 radicals Chemical class 0.000 description 32
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
• 238000004440 column chromatography Methods 0.000 description 30
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 27
• 239000000741 silica gel Substances 0.000 description 27
• 229910002027 silica gel Inorganic materials 0.000 description 27
• 239000002244 precipitate Substances 0.000 description 26
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• 238000006243 chemical reaction Methods 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
• 229910017976 MgO 4 Inorganic materials 0.000 description 23
• 239000002585 base Substances 0.000 description 22
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• 239000005457 ice water Substances 0.000 description 17
• 229910001868 water Inorganic materials 0.000 description 17
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
• 239000007787 solid Substances 0.000 description 15
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 13
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
• 238000012360 testing method Methods 0.000 description 13
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
• XEIGQMSIBJYILH-UHFFFAOYSA-N 1-(dimethylamino)-5-phenylpentan-3-one Chemical compound CN(C)CCC(=O)CCC1=CC=CC=C1 XEIGQMSIBJYILH-UHFFFAOYSA-N 0.000 description 11
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
• 229910052794 bromium Inorganic materials 0.000 description 10
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000000654 additive Substances 0.000 description 9
• 230000000996 additive effect Effects 0.000 description 9
• 229940043279 diisopropylamine Drugs 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
• 230000001580 bacterial effect Effects 0.000 description 8
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
• 238000002347 injection Methods 0.000 description 8
• 239000007924 injection Substances 0.000 description 8
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
• 229940088710 antibiotic agent Drugs 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• 101100520660 Drosophila melanogaster Poc1 gene Proteins 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• 101100520662 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PBA1 gene Proteins 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 6
• 229910052786 argon Inorganic materials 0.000 description 6
• 125000002618 bicyclic heterocycle group Chemical group 0.000 description 6
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
• 230000008859 change Effects 0.000 description 6
• JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical class CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 6
• 229910052734 helium Inorganic materials 0.000 description 6
• 239000003921 oil Substances 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
• 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 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
• 230000000844 anti-bacterial effect Effects 0.000 description 5
• 239000012267 brine Substances 0.000 description 5
• 229910052801 chlorine Inorganic materials 0.000 description 5
• 235000019253 formic acid Nutrition 0.000 description 5
• 230000010287 polarization Effects 0.000 description 5
• 239000000651 prodrug Substances 0.000 description 5
• 229940002612 prodrug Drugs 0.000 description 5
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 4
• MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 description 4
• UNBMPKNTYKDYCG-UHFFFAOYSA-N 4-methylpentan-2-amine Chemical compound CC(C)CC(C)N UNBMPKNTYKDYCG-UHFFFAOYSA-N 0.000 description 4
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
• 229920001817 Agar Polymers 0.000 description 4
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
• 239000005695 Ammonium acetate Substances 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
• 241000206672 Gelidium Species 0.000 description 4
• OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 4
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• 235000010419 agar Nutrition 0.000 description 4
• 235000019257 ammonium acetate Nutrition 0.000 description 4
• 229940043376 ammonium acetate Drugs 0.000 description 4
• 230000000845 anti-microbial effect Effects 0.000 description 4
• 239000012298 atmosphere Substances 0.000 description 4
• 244000052616 bacterial pathogen Species 0.000 description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
• 229940126086 compound 21 Drugs 0.000 description 4
• 230000006378 damage Effects 0.000 description 4
• 238000010790 dilution Methods 0.000 description 4
• 239000012895 dilution Substances 0.000 description 4
• 239000002552 dosage form Substances 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 230000002401 inhibitory effect Effects 0.000 description 4
• 238000001819 mass spectrum Methods 0.000 description 4
• 239000002777 nucleoside Substances 0.000 description 4
• 229910052700 potassium Inorganic materials 0.000 description 4
• 239000011591 potassium Substances 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• QJBZDBLBQWFTPZ-UHFFFAOYSA-N pyrrolnitrin Chemical compound [O-][N+](=O)C1=C(Cl)C=CC=C1C1=CNC=C1Cl QJBZDBLBQWFTPZ-UHFFFAOYSA-N 0.000 description 4
• 125000000168 pyrrolyl group Chemical group 0.000 description 4
• 150000003248 quinolines Chemical class 0.000 description 4
• 238000004007 reversed phase HPLC Methods 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
• AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
• WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 3
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
• 229940126639 Compound 33 Drugs 0.000 description 3
• 241000192125 Firmicutes Species 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• 241000124008 Mammalia Species 0.000 description 3
• 229930040373 Paraformaldehyde Natural products 0.000 description 3
• PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 3
• 239000003513 alkali Substances 0.000 description 3
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
• 239000004599 antimicrobial Substances 0.000 description 3
• 239000003963 antioxidant agent Substances 0.000 description 3
• 230000003078 antioxidant effect Effects 0.000 description 3
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
• 230000003115 biocidal effect Effects 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 239000003054 catalyst Substances 0.000 description 3
• 230000001413 cellular effect Effects 0.000 description 3
• 238000004587 chromatography analysis Methods 0.000 description 3
• 229940126208 compound 22 Drugs 0.000 description 3
• 230000034994 death Effects 0.000 description 3
• 238000003821 enantio-separation Methods 0.000 description 3
• 244000000059 gram-positive pathogen Species 0.000 description 3
• 125000002883 imidazolyl group Chemical group 0.000 description 3
• 239000002054 inoculum Substances 0.000 description 3
• UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 238000004811 liquid chromatography Methods 0.000 description 3
• 239000003120 macrolide antibiotic agent Substances 0.000 description 3
• 229940041033 macrolides Drugs 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• 244000005700 microbiome Species 0.000 description 3
• 125000002950 monocyclic group Chemical group 0.000 description 3
• 125000002911 monocyclic heterocycle group Chemical group 0.000 description 3
• 125000002757 morpholinyl group Chemical group 0.000 description 3
• 229920002866 paraformaldehyde Polymers 0.000 description 3
• 235000019371 penicillin G benzathine Nutrition 0.000 description 3
• 229910000027 potassium carbonate Inorganic materials 0.000 description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 description 3
• 230000002829 reductive effect Effects 0.000 description 3
• 230000035945 sensitivity Effects 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• 230000009885 systemic effect Effects 0.000 description 3
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