ES2640482T3 - Derivados biaromáticos antibacterianos - Google Patents

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Publication number

ES2640482T3

ES2640482T3 ES14721539.6T ES14721539T ES2640482T3 ES 2640482 T3 ES2640482 T3 ES 2640482T3 ES 14721539 T ES14721539 T ES 14721539T ES 2640482 T3 ES2640482 T3 ES 2640482T3

Authority

ES

Spain

Prior art keywords

oxo

oxazolidin

ethyl

pyrido

methoxy

Prior art date

2013-04-16

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 230000000844 anti-bacterial effect Effects 0.000 title description 9
• 150000001875 compounds Chemical class 0.000 claims abstract description 524
• -1 cyanomethoxy Chemical group 0.000 claims abstract description 253
• 150000003839 salts Chemical class 0.000 claims abstract description 67
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 58
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract description 36
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 29
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 26
• 150000002367 halogens Chemical class 0.000 claims abstract description 26
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 25
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims abstract description 10
• 125000005518 carboxamido group Chemical group 0.000 claims abstract description 7
• 208000015181 infectious disease Diseases 0.000 claims description 38
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 31
• 238000011282 treatment Methods 0.000 claims description 25
• 208000035143 Bacterial infection Diseases 0.000 claims description 24
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 24
• 230000001404 mediated effect Effects 0.000 claims description 20
• 239000002253 acid Substances 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 18
• 230000002265 prevention Effects 0.000 claims description 18
• 241000588626 Acinetobacter baumannii Species 0.000 claims description 17
• 241000191967 Staphylococcus aureus Species 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical compound N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 claims description 4
• SYHJILPZUNKNHQ-UHFFFAOYSA-N 3-phenylbenzonitrile Chemical compound N#CC1=CC=CC(C=2C=CC=CC=2)=C1 SYHJILPZUNKNHQ-UHFFFAOYSA-N 0.000 claims description 4
• XISPDFMAOWZEQG-UHFFFAOYSA-N 4h-1,4-oxazin-3-one Chemical compound O=C1COC=CN1 XISPDFMAOWZEQG-UHFFFAOYSA-N 0.000 claims description 4
• 206010033078 Otitis media Diseases 0.000 claims description 4
• 206010035664 Pneumonia Diseases 0.000 claims description 4
• 206010057190 Respiratory tract infections Diseases 0.000 claims description 4
• 208000020029 respiratory tract infectious disease Diseases 0.000 claims description 4
• ANHQLUBMNSSPBV-UHFFFAOYSA-N 4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound C1=CN=C2NC(=O)COC2=C1 ANHQLUBMNSSPBV-UHFFFAOYSA-N 0.000 claims description 3
• 208000031729 Bacteremia Diseases 0.000 claims description 3
• 201000009906 Meningitis Diseases 0.000 claims description 3
• 206010031252 Osteomyelitis Diseases 0.000 claims description 3
• 206010014665 endocarditis Diseases 0.000 claims description 3
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• 210000001519 tissue Anatomy 0.000 claims description 3
• 208000019206 urinary tract infection Diseases 0.000 claims description 3
• AISJUFSMNZRJOE-LJQANCHMSA-N (5r)-5-[2-[[3-(4-methoxypyrimidin-2-yl)phenyl]methylamino]ethyl]-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound COC1=CC=NC(C=2C=C(CNCC[C@H]3OC(=O)N(C3)C=3C=C4NC(=O)CSC4=CC=3)C=CC=2)=N1 AISJUFSMNZRJOE-LJQANCHMSA-N 0.000 claims description 2
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 2
• 208000037384 Clostridium Infections Diseases 0.000 claims description 2
• 208000001860 Eye Infections Diseases 0.000 claims description 2
• 206010017964 Gastrointestinal infection Diseases 0.000 claims description 2
• 208000036209 Intraabdominal Infections Diseases 0.000 claims description 2
• 208000016604 Lyme disease Diseases 0.000 claims description 2
• 208000011323 eye infectious disease Diseases 0.000 claims description 2
• 150000004702 methyl esters Chemical class 0.000 claims description 2
• 230000000699 topical effect Effects 0.000 claims description 2
• 208000037972 tropical disease Diseases 0.000 claims description 2
• 201000008827 tuberculosis Diseases 0.000 claims description 2
• BPMBNLJJRKCCRT-UHFFFAOYSA-N 4-phenylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=CC=C1 BPMBNLJJRKCCRT-UHFFFAOYSA-N 0.000 claims 1
• GAGAICHLGQDUTL-UHFFFAOYSA-N 4h-thiazin-3-one Chemical compound O=C1CC=CSN1 GAGAICHLGQDUTL-UHFFFAOYSA-N 0.000 claims 1
• XEKAWZARUWARND-UHFFFAOYSA-N 6h-oxazin-3-one Chemical compound O=C1NOCC=C1 XEKAWZARUWARND-UHFFFAOYSA-N 0.000 claims 1
• 239000004480 active ingredient Substances 0.000 claims 1
• 210000004872 soft tissue Anatomy 0.000 claims 1
• 238000000034 method Methods 0.000 description 405
• 238000002360 preparation method Methods 0.000 description 261
• 238000000746 purification Methods 0.000 description 139
• 238000002953 preparative HPLC Methods 0.000 description 112
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 103
• 239000007787 solid Substances 0.000 description 98
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 90
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
• 239000000203 mixture Substances 0.000 description 77
• 239000000543 intermediate Substances 0.000 description 68
• 238000005160 1H NMR spectroscopy Methods 0.000 description 64
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 64
• 230000002829 reductive effect Effects 0.000 description 64
• 239000000843 powder Substances 0.000 description 62
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 46
• 238000006243 chemical reaction Methods 0.000 description 46
• 239000006260 foam Substances 0.000 description 45
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 45
• 235000019341 magnesium sulphate Nutrition 0.000 description 45
• HJBGZJMKTOMQRR-UHFFFAOYSA-N (3-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=O)=C1 HJBGZJMKTOMQRR-UHFFFAOYSA-N 0.000 description 43
• 239000000243 solution Substances 0.000 description 43
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 41
• 239000000725 suspension Substances 0.000 description 41
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
• 239000011541 reaction mixture Substances 0.000 description 40
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 38
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 30
• UFTCBKDCPYVACN-SECBINFHSA-N (5r)-5-(2-aminoethyl)-3-(3-oxo-4h-1,4-benzothiazin-6-yl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](CCN)CN1C1=CC=C(SCC(=O)N2)C2=C1 UFTCBKDCPYVACN-SECBINFHSA-N 0.000 description 28
• 238000001914 filtration Methods 0.000 description 28
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
• 125000004432 carbon atom Chemical group C* 0.000 description 24
• 239000000706 filtrate Substances 0.000 description 24
• 239000003921 oil Substances 0.000 description 24
• 235000019198 oils Nutrition 0.000 description 24
• YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
• 239000003480 eluent Substances 0.000 description 19
• 229910000027 potassium carbonate Inorganic materials 0.000 description 19
• 235000015320 potassium carbonate Nutrition 0.000 description 19
• 239000012267 brine Substances 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• 229910052799 carbon Inorganic materials 0.000 description 17
• 125000006239 protecting group Chemical group 0.000 description 17
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 17
• HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 15
• 239000002904 solvent Substances 0.000 description 15
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 14
• 239000003054 catalyst Substances 0.000 description 14
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
• 241000894006 Bacteria Species 0.000 description 13
• 235000017557 sodium bicarbonate Nutrition 0.000 description 13
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
• 238000000105 evaporative light scattering detection Methods 0.000 description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
• 238000004128 high performance liquid chromatography Methods 0.000 description 11
• 229910052739 hydrogen Inorganic materials 0.000 description 11
• 239000001257 hydrogen Substances 0.000 description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 10
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
• 230000015572 biosynthetic process Effects 0.000 description 10
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 10
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
• 239000012043 crude product Substances 0.000 description 9
• 238000001514 detection method Methods 0.000 description 9
• 229910052763 palladium Inorganic materials 0.000 description 9
• 238000001665 trituration Methods 0.000 description 9
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 8
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
• 241000588655 Moraxella catarrhalis Species 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
• 235000019270 ammonium chloride Nutrition 0.000 description 8
• 235000011114 ammonium hydroxide Nutrition 0.000 description 8
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 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 8
• 239000012071 phase Substances 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
• 241000194031 Enterococcus faecium Species 0.000 description 7
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
• 125000000217 alkyl group Chemical group 0.000 description 7
• 229910000024 caesium carbonate Inorganic materials 0.000 description 7
• 239000012230 colorless oil Substances 0.000 description 7
• 125000000753 cycloalkyl group Chemical group 0.000 description 7
• 239000003365 glass fiber Substances 0.000 description 7
• 229910052757 nitrogen Inorganic materials 0.000 description 7
• 150000003871 sulfonates Chemical class 0.000 description 7
• 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 6
• NLLGFYPSWCMUIV-UHFFFAOYSA-N (3-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1 NLLGFYPSWCMUIV-UHFFFAOYSA-N 0.000 description 6
• 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 6
• XLGRINRFBNCHQS-UHFFFAOYSA-N 3-chloro-5-methoxypyridazine Chemical compound COC1=CN=NC(Cl)=C1 XLGRINRFBNCHQS-UHFFFAOYSA-N 0.000 description 6
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
• 241000192125 Firmicutes Species 0.000 description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• 150000001298 alcohols Chemical class 0.000 description 6
• 150000001412 amines Chemical class 0.000 description 6
• 229910052786 argon Inorganic materials 0.000 description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• 229910052801 chlorine Inorganic materials 0.000 description 6
• MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• 239000000463 material Substances 0.000 description 6
• 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
• 239000003643 water by type Substances 0.000 description 6
• SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 5
• 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 5
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
• 241000193996 Streptococcus pyogenes Species 0.000 description 5
• 239000003242 anti bacterial agent Substances 0.000 description 5
• 230000001580 bacterial effect Effects 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
• 239000013078 crystal Substances 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 235000019253 formic acid Nutrition 0.000 description 5
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 5
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• 229910052720 vanadium Inorganic materials 0.000 description 5
• XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 4
• BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 4
• USIJZLBTVWMYBG-UHFFFAOYSA-N 3-(3-formylphenyl)benzonitrile Chemical compound O=CC1=CC=CC(C=2C=C(C=CC=2)C#N)=C1 USIJZLBTVWMYBG-UHFFFAOYSA-N 0.000 description 4
• GLGWNAPAIMXRGT-UHFFFAOYSA-N 3-(3-methoxyphenyl)benzaldehyde Chemical compound COC1=CC=CC(C=2C=C(C=O)C=CC=2)=C1 GLGWNAPAIMXRGT-UHFFFAOYSA-N 0.000 description 4
• 235000019502 Orange oil Nutrition 0.000 description 4
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
• 241000589517 Pseudomonas aeruginosa Species 0.000 description 4
• 150000001408 amides Chemical group 0.000 description 4
• 229940088710 antibiotic agent Drugs 0.000 description 4
• 150000001540 azides Chemical class 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 238000010790 dilution Methods 0.000 description 4
• 239000012895 dilution Substances 0.000 description 4
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
• 229910052731 fluorine Inorganic materials 0.000 description 4
• 239000011737 fluorine Substances 0.000 description 4
• 125000001153 fluoro group Chemical group F* 0.000 description 4
• 239000011521 glass Substances 0.000 description 4
• VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
• 238000007327 hydrogenolysis reaction Methods 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
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