NZ574313A - Antibacterial compositions - Google Patents

Info

Publication number

NZ574313A

NZ574313A NZ574313A NZ57431307A NZ574313A NZ 574313 A NZ574313 A NZ 574313A NZ 574313 A NZ574313 A NZ 574313A NZ 57431307 A NZ57431307 A NZ 57431307A NZ 574313 A NZ574313 A NZ 574313A

Authority

NZ

New Zealand

Prior art keywords

compound

optionally substituted

pyridin

substituent

ethyl

Prior art date

2006-06-22

Links

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• 239000000203 mixture Substances 0.000 title claims abstract description 49
• 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 140
• 238000000034 method Methods 0.000 claims abstract description 41
• 150000003839 salts Chemical class 0.000 claims abstract description 15
• 238000002360 preparation method Methods 0.000 claims abstract description 9
• 239000012453 solvate Substances 0.000 claims abstract description 8
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 7
• -1 pyridine-3-yl ring Chemical group 0.000 claims description 108
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 63
• 125000001424 substituent group Chemical group 0.000 claims description 63
• 229910052739 hydrogen Inorganic materials 0.000 claims description 41
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• 239000001257 hydrogen Substances 0.000 claims description 38
• 125000006413 ring segment Chemical group 0.000 claims description 33
• 125000005843 halogen group Chemical group 0.000 claims description 29
• 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 26
• 125000000217 alkyl group Chemical group 0.000 claims description 25
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
• 230000001580 bacterial effect Effects 0.000 claims description 18
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 125000004450 alkenylene group Chemical group 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 238000011109 contamination Methods 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 125000002837 carbocyclic group Chemical group 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
• 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 241000191967 Staphylococcus aureus Species 0.000 claims description 7
• 150000003568 thioethers Chemical class 0.000 claims description 7
• 208000035143 Bacterial infection Diseases 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 claims description 5
• 239000000758 substrate Substances 0.000 claims description 5
• 239000003981 vehicle Substances 0.000 claims description 5
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical class C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical class 0.000 claims description 4
• 150000003222 pyridines Chemical class 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 150000003216 pyrazines Chemical group 0.000 claims description 3
• 150000003230 pyrimidines Chemical group 0.000 claims description 3
• 241001465754 Metazoa Species 0.000 claims description 2
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical class C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
• 230000004083 survival effect Effects 0.000 claims 3
• 125000003277 amino group Chemical group 0.000 claims 2
• 125000004122 cyclic group Chemical group 0.000 claims 2
• 238000007912 intraperitoneal administration Methods 0.000 claims 2
• 239000008194 pharmaceutical composition Substances 0.000 claims 2
• 241001529936 Murinae Species 0.000 claims 1
• 241000699670 Mus sp. Species 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 238000011081 inoculation Methods 0.000 claims 1
• 231100000636 lethal dose Toxicity 0.000 claims 1
• 230000002265 prevention Effects 0.000 claims 1
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract description 10
• 150000004677 hydrates Chemical class 0.000 abstract description 2
• BBAWTPDTGRXPDG-UHFFFAOYSA-N [1,3]thiazolo[4,5-b]pyridine Chemical class C1=CC=C2SC=NC2=N1 BBAWTPDTGRXPDG-UHFFFAOYSA-N 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 187
• 239000011541 reaction mixture Substances 0.000 description 111
• 239000000243 solution Substances 0.000 description 96
• 238000005160 1H NMR spectroscopy Methods 0.000 description 91
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 86
• 239000007787 solid Substances 0.000 description 82
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 72
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 65
• 235000019439 ethyl acetate Nutrition 0.000 description 64
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 59
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 59
• 239000004202 carbamide Substances 0.000 description 58
• 229940093499 ethyl acetate Drugs 0.000 description 57
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 52
• 239000002904 solvent Substances 0.000 description 43
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 40
• 238000006243 chemical reaction Methods 0.000 description 35
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
• 239000012299 nitrogen atmosphere Substances 0.000 description 30
• 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 description 27
• 238000001816 cooling Methods 0.000 description 26
• 238000012544 monitoring process Methods 0.000 description 26
• 238000004128 high performance liquid chromatography Methods 0.000 description 23
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 22
• 239000012044 organic layer Substances 0.000 description 22
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 21
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 20
• 238000000746 purification Methods 0.000 description 20
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
• 239000000725 suspension Substances 0.000 description 19
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 19
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
• 239000000047 product Substances 0.000 description 18
• 239000000377 silicon dioxide Substances 0.000 description 18
• 230000000694 effects Effects 0.000 description 17
• 239000012258 stirred mixture Substances 0.000 description 16
• 238000003756 stirring Methods 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 14
• 238000002953 preparative HPLC Methods 0.000 description 14
• 239000011369 resultant mixture Substances 0.000 description 14
• 239000000741 silica gel Substances 0.000 description 14
• 229910002027 silica gel Inorganic materials 0.000 description 14
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
• 101710183280 Topoisomerase Proteins 0.000 description 13
• 239000012267 brine Substances 0.000 description 13
• 235000019441 ethanol Nutrition 0.000 description 13
• 150000003254 radicals Chemical class 0.000 description 13
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
• 238000005481 NMR spectroscopy Methods 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
• 238000004587 chromatography analysis Methods 0.000 description 11
• 229910052763 palladium Inorganic materials 0.000 description 11
• 239000000706 filtrate Substances 0.000 description 10
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
• HFLVEWBPLLPPMX-UHFFFAOYSA-N 1-(7-bromo-5-pyridin-3-yl-1,3-benzothiazol-2-yl)-3-ethylurea Chemical compound C=1C(Br)=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 HFLVEWBPLLPPMX-UHFFFAOYSA-N 0.000 description 9
• 235000017557 sodium bicarbonate Nutrition 0.000 description 9
• OXJWGXOCTDLNRC-UHFFFAOYSA-N 1-(5-bromo-7-pyridin-3-yl-1,3-benzothiazol-2-yl)-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(Br)=CC=1C1=CC=CN=C1 OXJWGXOCTDLNRC-UHFFFAOYSA-N 0.000 description 8
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• 238000001914 filtration Methods 0.000 description 8
• 239000003208 petroleum Substances 0.000 description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
• ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 8
• 235000011121 sodium hydroxide Nutrition 0.000 description 8
• 229910000404 tripotassium phosphate Inorganic materials 0.000 description 8
• 241000894006 Bacteria Species 0.000 description 7
• 241000193998 Streptococcus pneumoniae Species 0.000 description 7
• 239000003242 anti bacterial agent Substances 0.000 description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
• 229940031000 streptococcus pneumoniae Drugs 0.000 description 7
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
• 229910014455 Ca-Cb Inorganic materials 0.000 description 6
• 108020004414 DNA Proteins 0.000 description 6
• 108090000790 Enzymes Proteins 0.000 description 6
• 102000004190 Enzymes Human genes 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• 235000011114 ammonium hydroxide Nutrition 0.000 description 6
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 6
• 229910000024 caesium carbonate Inorganic materials 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 6
• WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 6
• 125000001072 heteroaryl group Chemical group 0.000 description 6
• 125000000842 isoxazolyl group Chemical group 0.000 description 6
• 235000011056 potassium acetate Nutrition 0.000 description 6
• 229920006395 saturated elastomer Polymers 0.000 description 6
• 235000019798 tripotassium phosphate Nutrition 0.000 description 6
• FUCJAPOSIFKDLA-UHFFFAOYSA-N 1-(5-bromo-7-pyridin-2-yl-1,3-benzothiazol-2-yl)-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(Br)=CC=1C1=CC=CC=N1 FUCJAPOSIFKDLA-UHFFFAOYSA-N 0.000 description 5
• WXMMYNLMFRCZJR-UHFFFAOYSA-N 1-ethyl-3-(7-iodo-5-pyridin-3-yl-1,3-benzothiazol-2-yl)urea Chemical compound C=1C(I)=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 WXMMYNLMFRCZJR-UHFFFAOYSA-N 0.000 description 5
• 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
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
• ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 5
• 229960000583 acetic acid Drugs 0.000 description 5
• 125000003118 aryl group Chemical group 0.000 description 5
• 238000003556 assay Methods 0.000 description 5
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 5
• 239000003814 drug Substances 0.000 description 5
• 229940079593 drug Drugs 0.000 description 5
• 238000003818 flash chromatography Methods 0.000 description 5
• 235000019253 formic acid Nutrition 0.000 description 5
• FSAFVTMBEIXIOA-UHFFFAOYSA-N methyl 2-(ethylcarbamoylamino)-5-pyridin-3-yl-1,3-benzothiazole-7-carboxylate Chemical compound C=1C(C(=O)OC)=C2SC(NC(=O)NCC)=NC2=CC=1C1=CC=CN=C1 FSAFVTMBEIXIOA-UHFFFAOYSA-N 0.000 description 5
• 125000002950 monocyclic group Chemical group 0.000 description 5
• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 5
• QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 5
• 125000003226 pyrazolyl group Chemical group 0.000 description 5
• 125000004076 pyridyl group Chemical group 0.000 description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 description 5
• 235000010288 sodium nitrite Nutrition 0.000 description 5
• 125000000335 thiazolyl group Chemical group 0.000 description 5
• CUNOWHOWWKHSKC-UHFFFAOYSA-N 1-[7-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-pyridin-3-yl-1,3-benzothiazol-2-yl]-3-ethylurea Chemical compound C=12SC(NC(=O)NCC)=NC2=CC(C=2C=NC=CC=2)=CC=1B1OCC(C)(C)CO1 CUNOWHOWWKHSKC-UHFFFAOYSA-N 0.000 description 4
• 108091006112 ATPases Proteins 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
• 102000057290 Adenosine Triphosphatases Human genes 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• 108010054814 DNA Gyrase Proteins 0.000 description 4
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
• 241000194032 Enterococcus faecalis Species 0.000 description 4
• 241000194031 Enterococcus faecium Species 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• 241000202934 Mycoplasma pneumoniae Species 0.000 description 4
• 239000002253 acid Substances 0.000 description 4
• 230000002378 acidificating effect Effects 0.000 description 4
• 229940088710 antibiotic agent Drugs 0.000 description 4
• CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 4
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
• 229940032049 enterococcus faecalis Drugs 0.000 description 4
• 125000002541 furyl group Chemical group 0.000 description 4
• 239000012362 glacial acetic acid Substances 0.000 description 4
• 150000002430 hydrocarbons Chemical group 0.000 description 4
• 125000002883 imidazolyl group Chemical group 0.000 description 4
• 125000001041 indolyl group Chemical group 0.000 description 4
• 208000015181 infectious disease Diseases 0.000 description 4
• 239000003112 inhibitor Substances 0.000 description 4
• 125000001786 isothiazolyl group Chemical group 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• YRSVGJVTXQDYFG-UHFFFAOYSA-N methyl 2-amino-5-pyridin-3-yl-1,3-benzothiazole-7-carboxylate Chemical compound C=1C=2N=C(N)SC=2C(C(=O)OC)=CC=1C1=CC=CN=C1 YRSVGJVTXQDYFG-UHFFFAOYSA-N 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
• 125000002971 oxazolyl group Chemical group 0.000 description 4
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• VHXPMXQCMIGWIS-UHFFFAOYSA-M zinc;5-methyl-2h-pyridin-2-ide;bromide Chemical compound Br[Zn+].CC1=CC=[C-]N=C1 VHXPMXQCMIGWIS-UHFFFAOYSA-M 0.000 description 1