EA029361B1 - Антибактериальные биароматические производные - Google Patents

Info

Publication number

EA029361B1

EA029361B1 EA201501025A EA201501025A EA029361B1 EA 029361 B1 EA029361 B1 EA 029361B1 EA 201501025 A EA201501025 A EA 201501025A EA 201501025 A EA201501025 A EA 201501025A EA 029361 B1 EA029361 B1 EA 029361B1

Authority

EA

Eurasian Patent Office

Prior art keywords

oxo

ethyl

oxazin

oxooxazolidin

pyrido

Prior art date

2013-04-16

Links

• Espacenet
• Global Dossier
• Discuss

• 230000000844 anti-bacterial effect Effects 0.000 title abstract description 9
• 150000001875 compounds Chemical class 0.000 claims abstract description 545
• -1 Uand U Inorganic materials 0.000 claims abstract description 303
• 208000035143 Bacterial infection Diseases 0.000 claims abstract description 30
• 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 30
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• XISPDFMAOWZEQG-UHFFFAOYSA-N 4h-1,4-oxazin-3-one Chemical compound O=C1COC=CN1 XISPDFMAOWZEQG-UHFFFAOYSA-N 0.000 claims description 85
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 84
• 150000003839 salts Chemical class 0.000 claims description 64
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 60
• 208000015181 infectious disease Diseases 0.000 claims description 49
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
• 125000003545 alkoxy group Chemical group 0.000 claims description 32
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 30
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
• 241000894006 Bacteria Species 0.000 claims description 27
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 150000002367 halogens Chemical class 0.000 claims description 24
• 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 21
• 230000001404 mediated effect Effects 0.000 claims description 20
• SYHJILPZUNKNHQ-UHFFFAOYSA-N 3-phenylbenzonitrile Chemical compound N#CC1=CC=CC(C=2C=CC=CC=2)=C1 SYHJILPZUNKNHQ-UHFFFAOYSA-N 0.000 claims description 17
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• UIRSLBDCOYTZPH-UHFFFAOYSA-N 4h-1,4-thiazin-3-one Chemical compound O=C1CSC=CN1 UIRSLBDCOYTZPH-UHFFFAOYSA-N 0.000 claims description 15
• 230000002265 prevention Effects 0.000 claims description 14
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 11
• WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical compound N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 claims description 11
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• GAGAICHLGQDUTL-UHFFFAOYSA-N 4h-thiazin-3-one Chemical compound O=C1CC=CSN1 GAGAICHLGQDUTL-UHFFFAOYSA-N 0.000 claims description 9
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
• 229940079593 drug Drugs 0.000 claims description 8
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 7
• 206010035664 Pneumonia Diseases 0.000 claims description 6
• 125000005518 carboxamido group Chemical group 0.000 claims description 6
• 238000004891 communication Methods 0.000 claims description 6
• 125000004494 ethyl ester group Chemical group 0.000 claims description 6
• GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 claims description 6
• BPMBNLJJRKCCRT-UHFFFAOYSA-N 4-phenylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=CC=C1 BPMBNLJJRKCCRT-UHFFFAOYSA-N 0.000 claims description 5
• 150000001408 amides Chemical class 0.000 claims description 5
• 206010033078 Otitis media Diseases 0.000 claims description 4
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 210000004872 soft tissue Anatomy 0.000 claims description 4
• GVUSWMIMPJDWNW-UHFFFAOYSA-N 4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound C1=CN=C2NC(=O)CSC2=C1 GVUSWMIMPJDWNW-UHFFFAOYSA-N 0.000 claims description 3
• XEKAWZARUWARND-UHFFFAOYSA-N 6h-oxazin-3-one Chemical compound O=C1NOCC=C1 XEKAWZARUWARND-UHFFFAOYSA-N 0.000 claims description 3
• 208000031729 Bacteremia Diseases 0.000 claims description 3
• 208000016604 Lyme disease Diseases 0.000 claims description 3
• 201000009906 Meningitis Diseases 0.000 claims description 3
• 206010031252 Osteomyelitis Diseases 0.000 claims description 3
• GFBLFDSCAKHHGX-UHFFFAOYSA-N cyclobutanecarbonitrile Chemical compound N#CC1CCC1 GFBLFDSCAKHHGX-UHFFFAOYSA-N 0.000 claims description 3
• 206010014665 endocarditis Diseases 0.000 claims description 3
• KAHFELSLQNZONT-UHFFFAOYSA-N 3-[3-[[2-[2-oxo-3-(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)-1,3-oxazol-5-yl]ethylamino]methyl]phenyl]benzonitrile Chemical compound N1=C2NC(=O)COC2=CC=C1N(C(O1)=O)C=C1CCNCC(C=1)=CC=CC=1C1=CC=CC(C#N)=C1 KAHFELSLQNZONT-UHFFFAOYSA-N 0.000 claims description 2
• SEVKZXVRKIZTQF-UHFFFAOYSA-N 3-[3-[[2-[5-oxo-4-(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)-1,3,4-oxadiazol-2-yl]ethylamino]methyl]phenyl]benzonitrile Chemical compound N1=C2NC(=O)COC2=CC=C1N(C(O1)=O)N=C1CCNCC(C=1)=CC=CC=1C1=CC=CC(C#N)=C1 SEVKZXVRKIZTQF-UHFFFAOYSA-N 0.000 claims description 2
• HWRVVYPJVZHVSY-UHFFFAOYSA-N 3-[4-[[2-[2-oxo-3-(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)-1,3-oxazol-5-yl]ethylamino]methyl]pyridin-2-yl]benzonitrile Chemical compound N1=C2NC(=O)COC2=CC=C1N(C(O1)=O)C=C1CCNCC(C=1)=CC=NC=1C1=CC=CC(C#N)=C1 HWRVVYPJVZHVSY-UHFFFAOYSA-N 0.000 claims description 2
• XNLWJFYYOIRPIO-UHFFFAOYSA-N 3-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 XNLWJFYYOIRPIO-UHFFFAOYSA-N 0.000 claims description 2
• NGLUCDAVCQONCD-UHFFFAOYSA-N 4-methoxy-2-[3-[[2-[2-oxo-3-(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)-1,3-oxazol-5-yl]ethylamino]methyl]phenyl]benzonitrile Chemical compound COC1=CC=C(C#N)C(C=2C=C(CNCCC=3OC(=O)N(C=4N=C5NC(=O)COC5=CC=4)C=3)C=CC=2)=C1 NGLUCDAVCQONCD-UHFFFAOYSA-N 0.000 claims description 2
• WMXIPLUNDNMUIL-UHFFFAOYSA-N 4-methoxy-2-[3-[[2-[5-oxo-4-(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)-1,3,4-oxadiazol-2-yl]ethylamino]methyl]phenyl]benzonitrile Chemical compound COC1=CC=C(C#N)C(C=2C=C(CNCCC=3OC(=O)N(C=4N=C5NC(=O)COC5=CC=4)N=3)C=CC=2)=C1 WMXIPLUNDNMUIL-UHFFFAOYSA-N 0.000 claims description 2
• NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims description 2
• CDDXGMSKEASLEP-UHFFFAOYSA-N 6-[2-hydroxy-3-[[2-[2-oxo-3-(3-oxo-4H-pyrido[3,2-b][1,4]oxazin-6-yl)-1,3-oxazol-5-yl]ethylamino]methyl]phenyl]pyridine-2-carbonitrile Chemical compound OC1=C(C=CC=C1CNCCC1=CN(C(O1)=O)C=1C=CC=2OCC(NC=2N=1)=O)C1=CC=CC(=N1)C#N CDDXGMSKEASLEP-UHFFFAOYSA-N 0.000 claims description 2
• KYFKFYWCJMQFFL-UHFFFAOYSA-N 6-[2-hydroxy-3-[[2-[5-oxo-4-(3-oxo-4H-pyrido[3,2-b][1,4]oxazin-6-yl)-1,3,4-oxadiazol-2-yl]ethylamino]methyl]phenyl]pyridine-2-carbonitrile Chemical compound OC1=C(C=CC=C1CNCCC=1OC(N(N=1)C=1C=CC=2OCC(NC=2N=1)=O)=O)C1=CC=CC(=N1)C#N KYFKFYWCJMQFFL-UHFFFAOYSA-N 0.000 claims description 2
• 206010070245 Foreign body Diseases 0.000 claims description 2
• 206010057190 Respiratory tract infections Diseases 0.000 claims description 2
• 210000000683 abdominal cavity Anatomy 0.000 claims description 2
• PJESVVYWPFAJCS-UHFFFAOYSA-N pyridazine-3-carbonitrile Chemical compound N#CC1=CC=CN=N1 PJESVVYWPFAJCS-UHFFFAOYSA-N 0.000 claims description 2
• QXOXHGUPISQLPW-UHFFFAOYSA-N pyridazine-4-carbonitrile Chemical compound N#CC1=CC=NN=C1 QXOXHGUPISQLPW-UHFFFAOYSA-N 0.000 claims description 2
• 208000037972 tropical disease Diseases 0.000 claims description 2
• 201000008827 tuberculosis Diseases 0.000 claims description 2
• 208000019206 urinary tract infection Diseases 0.000 claims description 2
• QDUHQAQMOAHLRW-UHFFFAOYSA-N 4h-1,4-benzoxazine Chemical compound C1=CC=C2NC=COC2=C1 QDUHQAQMOAHLRW-UHFFFAOYSA-N 0.000 claims 1
• 206010017964 Gastrointestinal infection Diseases 0.000 claims 1
• 239000004480 active ingredient Substances 0.000 claims 1
• 125000005605 benzo group Chemical group 0.000 claims 1
• 210000000959 ear middle Anatomy 0.000 claims 1
• 229910052720 vanadium Inorganic materials 0.000 abstract description 145
• 230000015572 biosynthetic process Effects 0.000 description 271
• 238000003786 synthesis reaction Methods 0.000 description 267
• 238000000034 method Methods 0.000 description 224
• 238000000746 purification Methods 0.000 description 131
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
• 239000007787 solid Substances 0.000 description 98
• 238000004128 high performance liquid chromatography Methods 0.000 description 94
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 92
• 239000000203 mixture Substances 0.000 description 91
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 84
• 239000000543 intermediate Substances 0.000 description 70
• 230000002829 reductive effect Effects 0.000 description 64
• 239000000843 powder Substances 0.000 description 62
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
• 238000005481 NMR spectroscopy Methods 0.000 description 59
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 55
• 238000006243 chemical reaction Methods 0.000 description 50
• 229910052740 iodine Inorganic materials 0.000 description 49
• 239000010410 layer Substances 0.000 description 48
• 239000006260 foam Substances 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 44
• 239000000243 solution Substances 0.000 description 44
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 43
• 239000011541 reaction mixture Substances 0.000 description 42
• 239000000725 suspension Substances 0.000 description 41
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 34
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 31
• 125000004432 carbon atom Chemical group C* 0.000 description 25
• 239000000706 filtrate Substances 0.000 description 24
• 239000003921 oil Substances 0.000 description 23
• 235000019198 oils Nutrition 0.000 description 23
• 229910017976 MgO 4 Inorganic materials 0.000 description 22
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
• 238000001914 filtration Methods 0.000 description 20
• 239000003480 eluent Substances 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
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
• 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 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• 229910052799 carbon Inorganic materials 0.000 description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
• 239000002904 solvent Substances 0.000 description 15
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 14
• 239000003054 catalyst Substances 0.000 description 14
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 13
• 229910052739 hydrogen Inorganic materials 0.000 description 13
• 239000012044 organic layer Substances 0.000 description 13
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 13
• 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 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
• 239000000126 substance Substances 0.000 description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
• 239000001257 hydrogen Substances 0.000 description 11
• 229910052757 nitrogen Inorganic materials 0.000 description 11
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
• 239000012043 crude product Substances 0.000 description 10
• 238000007429 general method Methods 0.000 description 10
• 238000001514 detection method Methods 0.000 description 9
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
• 239000000460 chlorine Substances 0.000 description 8
• 238000004140 cleaning Methods 0.000 description 8
• 125000006239 protecting group Chemical group 0.000 description 8
• 238000001665 trituration Methods 0.000 description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
• 125000000217 alkyl group Chemical group 0.000 description 7
• PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
• 229910052794 bromium Inorganic materials 0.000 description 7
• 239000012230 colorless oil Substances 0.000 description 7
• 125000000753 cycloalkyl group Chemical group 0.000 description 7
• 239000011737 fluorine Substances 0.000 description 7
• 229910052731 fluorine Inorganic materials 0.000 description 7
• 239000003365 glass fiber Substances 0.000 description 7
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• 150000003871 sulfonates Chemical class 0.000 description 7
• NLLGFYPSWCMUIV-UHFFFAOYSA-N (3-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1 NLLGFYPSWCMUIV-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
• GTFMIJNXNMDHAB-UHFFFAOYSA-N 4h-1,4-benzothiazin-3-one Chemical compound C1=CC=C2NC(=O)CSC2=C1 GTFMIJNXNMDHAB-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
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• 241000192125 Firmicutes Species 0.000 description 6
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
• 150000001412 amines Chemical class 0.000 description 6
• 239000003242 anti bacterial agent Substances 0.000 description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 6
• 229910052801 chlorine Inorganic materials 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• 229910052763 palladium Inorganic materials 0.000 description 6
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
• SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 5
• 229940126062 Compound A Drugs 0.000 description 5
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
• 101000587820 Homo sapiens Selenide, water dikinase 1 Proteins 0.000 description 5
• 101000701815 Homo sapiens Spermidine synthase Proteins 0.000 description 5
• 102100030413 Spermidine synthase Human genes 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
• 150000001299 aldehydes Chemical class 0.000 description 5
• 229910052786 argon Inorganic materials 0.000 description 5
• 239000012298 atmosphere Substances 0.000 description 5
• 235000019253 formic acid Nutrition 0.000 description 5
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
• 229940126601 medicinal product Drugs 0.000 description 5
• 229910000510 noble metal Inorganic materials 0.000 description 5
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
• 229910052700 potassium Inorganic materials 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 150000007660 quinolones Chemical class 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 238000010561 standard procedure Methods 0.000 description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• 238000004809 thin layer chromatography Methods 0.000 description 5
• KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 5
• 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 4
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 4
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 235000019502 Orange oil Nutrition 0.000 description 4
• 150000001298 alcohols Chemical class 0.000 description 4
• 229940088710 antibiotic agent Drugs 0.000 description 4
• 150000001540 azides Chemical class 0.000 description 4
• 125000005620 boronic acid group Chemical class 0.000 description 4
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
• 150000001721 carbon Chemical group 0.000 description 4
• 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 4
• 238000001816 cooling Methods 0.000 description 4
• 239000013078 crystal Substances 0.000 description 4
• 230000001419 dependent effect Effects 0.000 description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
• DGODWNOPHMXOTR-UHFFFAOYSA-N dipotassium;dioxido(dioxo)osmium;dihydrate Chemical compound O.O.[K+].[K+].[O-][Os]([O-])(=O)=O DGODWNOPHMXOTR-UHFFFAOYSA-N 0.000 description 4
• 239000011521 glass Substances 0.000 description 4
• 239000010931 gold Substances 0.000 description 4
• 238000007327 hydrogenolysis reaction Methods 0.000 description 4
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
• 238000004519 manufacturing process Methods 0.000 description 4
• 239000010502 orange oil Substances 0.000 description 4
• 229910052760 oxygen Inorganic materials 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
• 239000000377 silicon dioxide Substances 0.000 description 4
• HNCABRWZPCRMMA-UHFFFAOYSA-N (5-formyl-2-phenylmethoxyphenyl)boronic acid Chemical compound OB(O)C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 HNCABRWZPCRMMA-UHFFFAOYSA-N 0.000 description 3
• WTAPZWXVSZMMDG-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 WTAPZWXVSZMMDG-UHFFFAOYSA-N 0.000 description 3
• KMODISUYWZPVGV-UHFFFAOYSA-N 2-bromo-6-methoxypyridine Chemical compound COC1=CC=CC(Br)=N1 KMODISUYWZPVGV-UHFFFAOYSA-N 0.000 description 3
• YLKLNODUMSCTIV-UHFFFAOYSA-N 2-chloro-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C(Cl)=C1 YLKLNODUMSCTIV-UHFFFAOYSA-N 0.000 description 3
• 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 3
• JZSAUQMXKHBZEO-UHFFFAOYSA-N 3,5-dichloropyridazine Chemical compound ClC1=CN=NC(Cl)=C1 JZSAUQMXKHBZEO-UHFFFAOYSA-N 0.000 description 3
• IFTQDOZCEQMAOS-UHFFFAOYSA-N 3-(6-methoxypyridin-2-yl)benzaldehyde Chemical compound COc1cccc(n1)-c1cccc(C=O)c1 IFTQDOZCEQMAOS-UHFFFAOYSA-N 0.000 description 3
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 3
• 102100029721 DnaJ homolog subfamily B member 1 Human genes 0.000 description 3
• 101000866018 Homo sapiens DnaJ homolog subfamily B member 1 Proteins 0.000 description 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
• 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 description 3
• NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 3
• 101100293693 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) STO1 gene Proteins 0.000 description 3
• DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 108010059993 Vancomycin Proteins 0.000 description 3
• 125000005083 alkoxyalkoxy group Chemical group 0.000 description 3
• 125000003118 aryl group Chemical group 0.000 description 3
• 230000001580 bacterial effect Effects 0.000 description 3
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
• 150000001642 boronic acid derivatives Chemical class 0.000 description 3
• 229910000024 caesium carbonate Inorganic materials 0.000 description 3
• 101150050497 cbc1 gene Proteins 0.000 description 3
• 239000003153 chemical reaction reagent Substances 0.000 description 3
• 229910052805 deuterium Inorganic materials 0.000 description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
• 150000002148 esters Chemical class 0.000 description 3
• 239000002360 explosive Substances 0.000 description 3
• 125000001072 heteroaryl group Chemical group 0.000 description 3
• 125000005842 heteroatom Chemical group 0.000 description 3
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
• 150000004694 iodide salts Chemical class 0.000 description 3
• 229910052742 iron Inorganic materials 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
• 229960003085 meticillin Drugs 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 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 3
• 244000052769 pathogen Species 0.000 description 3
• 229910052701 rubidium Inorganic materials 0.000 description 3
• 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
• 239000007858 starting material Substances 0.000 description 3
• 125000003944 tolyl group Chemical group 0.000 description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
• MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 3
• 229960003165 vancomycin Drugs 0.000 description 3
• MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 3
• 150000003952 β-lactams Chemical class 0.000 description 3
• IITREVBIIYAMMS-UHFFFAOYSA-N (3-formyl-2-phenylmethoxyphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=O)=C1OCC1=CC=CC=C1 IITREVBIIYAMMS-UHFFFAOYSA-N 0.000 description 2
• QXWBHAJKEPWEBD-UHFFFAOYSA-N (5-cyano-2-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC(C#N)=CC=C1O QXWBHAJKEPWEBD-UHFFFAOYSA-N 0.000 description 2
• GQWZKBTZAFEQJZ-UHFFFAOYSA-N (6-methoxypyridin-2-yl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=N1 GQWZKBTZAFEQJZ-UHFFFAOYSA-N 0.000 description 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
• 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 2
• LPHWEYJVBHTFQX-UHFFFAOYSA-N 1-(6-chloropyridin-2-yl)pyrrolidin-3-ol Chemical compound C1C(O)CCN1C1=CC=CC(Cl)=N1 LPHWEYJVBHTFQX-UHFFFAOYSA-N 0.000 description 2
• MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 2
• PLDWAJLZAAHOGG-UHFFFAOYSA-N 1-bromo-3-methoxybenzene Chemical compound COC1=CC=CC(Br)=C1 PLDWAJLZAAHOGG-UHFFFAOYSA-N 0.000 description 2
• LQHDXWVXUCTFMD-UHFFFAOYSA-N 2-(3-methoxyphenyl)pyrimidine-4-carbaldehyde Chemical compound COC1=CC=CC(C=2N=C(C=O)C=CN=2)=C1 LQHDXWVXUCTFMD-UHFFFAOYSA-N 0.000 description 2
• SEQZOHCWUCCKOM-UHFFFAOYSA-N 2-(6-bromo-2-nitropyridin-3-yl)oxyacetic acid Chemical compound OC(=O)COC1=CC=C(Br)N=C1[N+]([O-])=O SEQZOHCWUCCKOM-UHFFFAOYSA-N 0.000 description 2
• BRGJGSKDCPXSHB-UHFFFAOYSA-N 2-bromo-6-methoxybenzonitrile Chemical compound COC1=CC=CC(Br)=C1C#N BRGJGSKDCPXSHB-UHFFFAOYSA-N 0.000 description 2
• PMTPFBWHUOWTNN-UHFFFAOYSA-N 2-chloro-4-methoxypyridine Chemical compound COC1=CC=NC(Cl)=C1 PMTPFBWHUOWTNN-UHFFFAOYSA-N 0.000 description 2
• YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 description 2
• STXAVEHFKAXGOX-UHFFFAOYSA-N 3-bromobenzonitrile Chemical compound BrC1=CC=CC(C#N)=C1 STXAVEHFKAXGOX-UHFFFAOYSA-N 0.000 description 2
• 125000001137 3-hydroxypropoxy group Chemical group [H]OC([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
• CXEFZVVLTJQWBF-UHFFFAOYSA-N 4-phenylmethoxybutanoic acid Chemical compound OC(=O)CCCOCC1=CC=CC=C1 CXEFZVVLTJQWBF-UHFFFAOYSA-N 0.000 description 2
• WZKSIYMHHOYABL-UHFFFAOYSA-N 5-(3-formylphenyl)pyridazine-3-carbonitrile Chemical compound C(=O)C=1C=C(C=CC1)C=1C=C(N=NC1)C#N WZKSIYMHHOYABL-UHFFFAOYSA-N 0.000 description 2
• IDTOVLHWDFERBL-UHFFFAOYSA-N 5-(3-methoxyphenyl)pyridazine-3-carbaldehyde Chemical compound COC=1C=C(C=CC1)C=1C=C(N=NC1)C=O IDTOVLHWDFERBL-UHFFFAOYSA-N 0.000 description 2
• OPODPXCDRCYNIG-UHFFFAOYSA-N 5-(5-methoxypyridazin-3-yl)pyridine-3-carbaldehyde Chemical compound COC=1C=C(N=NC1)C=1C=NC=C(C=O)C1 OPODPXCDRCYNIG-UHFFFAOYSA-N 0.000 description 2
• GHQXQWSNSIAPRJ-UHFFFAOYSA-N 6-(3-formylphenyl)pyridazine-4-carbonitrile Chemical compound O=Cc1cccc(c1)-c1cc(cnn1)C#N GHQXQWSNSIAPRJ-UHFFFAOYSA-N 0.000 description 2
• IERSBVRIEGXCLM-UHFFFAOYSA-N 6-(3-methoxyphenyl)pyrazine-2-carbaldehyde Chemical compound COC=1C=C(C=CC1)C1=CN=CC(=N1)C=O IERSBVRIEGXCLM-UHFFFAOYSA-N 0.000 description 2
• MEOFAFOFIFNIRL-UHFFFAOYSA-N 6-(3-methoxyphenyl)pyridazine-4-carbaldehyde Chemical compound COc1cccc(c1)-c1cc(C=O)cnn1 MEOFAFOFIFNIRL-UHFFFAOYSA-N 0.000 description 2
• RJCJXKUDNKVVMG-UHFFFAOYSA-N 6-bromo-4-[(4-methoxyphenyl)methyl]pyrido[3,2-b][1,4]oxazin-3-one Chemical compound C1=CC(OC)=CC=C1CN1C2=NC(Br)=CC=C2OCC1=O RJCJXKUDNKVVMG-UHFFFAOYSA-N 0.000 description 2
• 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 2
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
• UAEPNZWRGJTJPN-UHFFFAOYSA-N Methylcyclohexane Natural products CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
• YNCVZMMBPFIWTH-UHFFFAOYSA-N OC=O.NCCc1cn(-c2ccc3OCC(=O)Nc3n2)c(=O)o1 Chemical compound OC=O.NCCc1cn(-c2ccc3OCC(=O)Nc3n2)c(=O)o1 YNCVZMMBPFIWTH-UHFFFAOYSA-N 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 125000006241 alcohol protecting group Chemical group 0.000 description 2
• 235000019270 ammonium chloride Nutrition 0.000 description 2
• 125000004429 atom Chemical group 0.000 description 2
• 235000019445 benzyl alcohol Nutrition 0.000 description 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
• 239000004305 biphenyl Substances 0.000 description 2
• 150000001649 bromium compounds Chemical class 0.000 description 2
• 230000005587 bubbling Effects 0.000 description 2
• QUWAWKOUPYMZJS-UHFFFAOYSA-N butanedioic acid ethylsulfanylethane Chemical group C(C)SCC.C(CCC(=O)O)(=O)O QUWAWKOUPYMZJS-UHFFFAOYSA-N 0.000 description 2
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
• 238000004296 chiral HPLC Methods 0.000 description 2
• DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
• 229960003405 ciprofloxacin Drugs 0.000 description 2
• 229940125782 compound 2 Drugs 0.000 description 2
• 238000010586 diagram Methods 0.000 description 2
• IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
• 201000010099 disease Diseases 0.000 description 2
• 238000010828 elution Methods 0.000 description 2
• 238000005516 engineering process Methods 0.000 description 2
• 239000012634 fragment Substances 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 125000005113 hydroxyalkoxy group Chemical group 0.000 description 2
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
• 239000003120 macrolide antibiotic agent Substances 0.000 description 2
• 229940041033 macrolides Drugs 0.000 description 2
• GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 2
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
• 150000004702 methyl esters Chemical class 0.000 description 2
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
• 244000005700 microbiome Species 0.000 description 2
• 150000004682 monohydrates Chemical class 0.000 description 2
• XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 2
• 239000011368 organic material Substances 0.000 description 2
• 239000000123 paper Substances 0.000 description 2
• 229910052698 phosphorus Inorganic materials 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• 235000015320 potassium carbonate Nutrition 0.000 description 2
• 235000019260 propionic acid Nutrition 0.000 description 2
• 150000003254 radicals Chemical class 0.000 description 2
• 210000002345 respiratory system Anatomy 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 230000009885 systemic effect Effects 0.000 description 2
• DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 2
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
• PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
• JRHPOFJADXHYBR-HTQZYQBOSA-N (1r,2r)-1-n,2-n-dimethylcyclohexane-1,2-diamine Chemical compound CN[C@@H]1CCCC[C@H]1NC JRHPOFJADXHYBR-HTQZYQBOSA-N 0.000 description 1
• GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
• YJXJCPZHXDDRNH-UHFFFAOYSA-N (2-fluoro-3-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=O)=C1F YJXJCPZHXDDRNH-UHFFFAOYSA-N 0.000 description 1
• SQSWYWCEKCVQEA-UHFFFAOYSA-N (2-fluoro-5-formylphenyl)boronic acid Chemical compound OB(O)C1=CC(C=O)=CC=C1F SQSWYWCEKCVQEA-UHFFFAOYSA-N 0.000 description 1
• RCIVUMDLBQZEHP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxycarbamic acid Chemical group CC(C)(C)ONC(O)=O RCIVUMDLBQZEHP-UHFFFAOYSA-N 0.000 description 1
• 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 1
• XDBHWPLGGBLUHH-UHFFFAOYSA-N (3-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C#N)=C1 XDBHWPLGGBLUHH-UHFFFAOYSA-N 0.000 description 1
• KFCWJXULHYUQKL-UHFFFAOYSA-N (4-bromophenyl)sulfonyl 4-bromobenzenesulfonate Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=C(Br)C=C1 KFCWJXULHYUQKL-UHFFFAOYSA-N 0.000 description 1
• SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical class O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 1
• XBFJPIZCCLHLHV-UHFFFAOYSA-N (6-methoxypyridin-2-yl)boronic acid;hydrochloride Chemical compound Cl.COC1=CC=CC(B(O)O)=N1 XBFJPIZCCLHLHV-UHFFFAOYSA-N 0.000 description 1
• DHADXDMPEUWEAS-UHFFFAOYSA-N (6-methoxypyridin-3-yl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=N1 DHADXDMPEUWEAS-UHFFFAOYSA-N 0.000 description 1
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
• PPQJCISYYXZCAE-UHFFFAOYSA-N 1,10-phenanthroline;hydrate Chemical compound O.C1=CN=C2C3=NC=CC=C3C=CC2=C1 PPQJCISYYXZCAE-UHFFFAOYSA-N 0.000 description 1
• BNMNQUBPZZSXQU-UHFFFAOYSA-N 1,3-dioxole-4-carboxylic acid Chemical compound OC(=O)C1=COCO1 BNMNQUBPZZSXQU-UHFFFAOYSA-N 0.000 description 1
• FCQZYZMMXDHMRA-UHFFFAOYSA-N 1-[(3-bromophenoxy)methyl]cyclobutane-1-carbonitrile Chemical compound Brc1cccc(OCC2(CCC2)C#N)c1 FCQZYZMMXDHMRA-UHFFFAOYSA-N 0.000 description 1
• BRKHXJWFOXVFRT-UHFFFAOYSA-N 1-[[3-(3-formylphenyl)phenoxy]methyl]cyclobutane-1-carbonitrile Chemical compound O=Cc1cccc(c1)-c1cccc(OCC2(CCC2)C#N)c1 BRKHXJWFOXVFRT-UHFFFAOYSA-N 0.000 description 1
• CFUFZUWSBHTKRQ-UHFFFAOYSA-N 1-bromo-3-(2-methoxyethoxy)benzene Chemical compound COCCOC1=CC=CC(Br)=C1 CFUFZUWSBHTKRQ-UHFFFAOYSA-N 0.000 description 1
• NRBGCJODKBODKA-UHFFFAOYSA-N 1-bromo-3-(cyclobutylmethoxy)benzene Chemical compound BrC1=CC=CC(OCC2CCC2)=C1 NRBGCJODKBODKA-UHFFFAOYSA-N 0.000 description 1
• QYVPRMAOEXVFHH-UHFFFAOYSA-N 1-bromo-3-(cyclopropylmethoxy)benzene Chemical compound BrC1=CC=CC(OCC2CC2)=C1 QYVPRMAOEXVFHH-UHFFFAOYSA-N 0.000 description 1
• PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical compound C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
• RLMRVKKDBUFIHN-UHFFFAOYSA-N 2-(3-bromophenoxy)acetonitrile Chemical compound BrC1=CC=CC(OCC#N)=C1 RLMRVKKDBUFIHN-UHFFFAOYSA-N 0.000 description 1
• PDDPLXANEWCRKY-UHFFFAOYSA-N 2-(3-formylphenyl)-4-methoxybenzonitrile Chemical compound C(=O)C=1C=C(C=CC=1)C=1C(=CC=C(C=1)OC)C#N PDDPLXANEWCRKY-UHFFFAOYSA-N 0.000 description 1
• KDXLYWQZDOLKSO-UHFFFAOYSA-N 2-(3-formylphenyl)-6-methoxybenzonitrile Chemical compound C(=O)C=1C=C(C=CC=1)C=1C(=C(C=CC=1)OC)C#N KDXLYWQZDOLKSO-UHFFFAOYSA-N 0.000 description 1
• SUFYQBNNXATHMB-UHFFFAOYSA-N 2-(3-formylphenyl)pyridine-3-carbonitrile Chemical compound O=CC1=CC=CC(C=2C(=CC=CN=2)C#N)=C1 SUFYQBNNXATHMB-UHFFFAOYSA-N 0.000 description 1
• WWNBGWIFYXGXHX-UHFFFAOYSA-N 2-(dimethoxymethyl)-6-(3-methoxyphenyl)pyrazine Chemical compound COC(C1=NC(=CN=C1)C1=CC(=CC=C1)OC)OC WWNBGWIFYXGXHX-UHFFFAOYSA-N 0.000 description 1
• VUBROXJRYJKFSN-UHFFFAOYSA-N 2-[3-(3-formylphenyl)phenoxy]acetonitrile Chemical compound C(=O)C=1C=C(C=CC=1)C1=CC(=CC=C1)OCC#N VUBROXJRYJKFSN-UHFFFAOYSA-N 0.000 description 1
• ZSZAVRFDRSBDJR-UHFFFAOYSA-N 2-[4-(dimethoxymethyl)pyridin-2-yl]-6-methoxypyridine Chemical group COC(C1=CC(=NC=C1)C1=NC(=CC=C1)OC)OC ZSZAVRFDRSBDJR-UHFFFAOYSA-N 0.000 description 1
• HCSSXZQBFPBQIO-UHFFFAOYSA-N 2-bromo-4-(dimethoxymethyl)pyridine Chemical compound COC(OC)C1=CC=NC(Br)=C1 HCSSXZQBFPBQIO-UHFFFAOYSA-N 0.000 description 1
• AWBDARKONATUHX-UHFFFAOYSA-N 2-bromo-4-methoxypyridine Chemical compound COC1=CC=NC(Br)=C1 AWBDARKONATUHX-UHFFFAOYSA-N 0.000 description 1
• JWTZSVLLPKTZJP-UHFFFAOYSA-N 2-bromo-6-chloropyridine Chemical compound ClC1=CC=CC(Br)=N1 JWTZSVLLPKTZJP-UHFFFAOYSA-N 0.000 description 1
• RTWLIQFKXMWEJY-UHFFFAOYSA-N 2-bromopyridine-4-carbaldehyde Chemical compound BrC1=CC(C=O)=CC=N1 RTWLIQFKXMWEJY-UHFFFAOYSA-N 0.000 description 1
• GPIQOFWTZXXOOV-UHFFFAOYSA-N 2-chloro-4,6-dimethoxy-1,3,5-triazine Chemical compound COC1=NC(Cl)=NC(OC)=N1 GPIQOFWTZXXOOV-UHFFFAOYSA-N 0.000 description 1
• PBEKEFWBLFBSGQ-UHFFFAOYSA-N 2-chloro-4,6-dimethoxypyrimidine Chemical compound COC1=CC(OC)=NC(Cl)=N1 PBEKEFWBLFBSGQ-UHFFFAOYSA-N 0.000 description 1
• FKTWAFBZSPUCSC-UHFFFAOYSA-N 2-chloro-4-(dimethoxymethyl)pyrimidine Chemical compound COC(OC)c1ccnc(Cl)n1 FKTWAFBZSPUCSC-UHFFFAOYSA-N 0.000 description 1
• BDXYNMVQMBCTDB-UHFFFAOYSA-N 2-chloro-4-methoxypyrimidine Chemical compound COC1=CC=NC(Cl)=N1 BDXYNMVQMBCTDB-UHFFFAOYSA-N 0.000 description 1
• UHUBNUHDEHDDJJ-UHFFFAOYSA-N 2-chloro-6-(dimethoxymethyl)pyrazine Chemical compound ClC1=NC(=CN=C1)C(OC)OC UHUBNUHDEHDDJJ-UHFFFAOYSA-N 0.000 description 1
• VAVGOGHLNAJECD-UHFFFAOYSA-N 2-chloro-6-methoxypyridine Chemical compound COC1=CC=CC(Cl)=N1 VAVGOGHLNAJECD-UHFFFAOYSA-N 0.000 description 1
• XHQQYIWTUFWASX-UHFFFAOYSA-N 2-chloro-6-methoxypyridine-4-carbonitrile Chemical compound COC1=CC(C#N)=CC(Cl)=N1 XHQQYIWTUFWASX-UHFFFAOYSA-N 0.000 description 1
• JAUPUQRPBNDMDT-UHFFFAOYSA-N 2-chloropyridine-3-carbonitrile Chemical compound ClC1=NC=CC=C1C#N JAUPUQRPBNDMDT-UHFFFAOYSA-N 0.000 description 1
• PCWBLFVVQBNIBD-UHFFFAOYSA-N 2-fluoro-3-(3-methoxyphenyl)benzaldehyde Chemical compound FC1=C(C=CC=C1C=O)C1=CC(=CC=C1)OC PCWBLFVVQBNIBD-UHFFFAOYSA-N 0.000 description 1
• ZCAAWAFWYQIAFF-UHFFFAOYSA-N 2-hydroxy-3-(6-methoxypyridin-2-yl)benzaldehyde Chemical compound COc1cccc(n1)-c1cccc(C=O)c1O ZCAAWAFWYQIAFF-UHFFFAOYSA-N 0.000 description 1
• VYWCRVNLPOVYJH-UHFFFAOYSA-N 2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=CC=CC(B2OC(C)(C)C(C)(C)O2)=N1 VYWCRVNLPOVYJH-UHFFFAOYSA-N 0.000 description 1
• ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical compound C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 description 1
• OVSKGTONMLKNPZ-UHFFFAOYSA-N 3-(1-methylindol-3-yl)-4-(1-methyl-6-nitroindol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(C)C=C1C1=C(C=2C3=CC=C(C=C3N(C)C=2)[N+]([O-])=O)C(=O)NC1=O OVSKGTONMLKNPZ-UHFFFAOYSA-N 0.000 description 1
• CPFJCSLRFAKWGH-UHFFFAOYSA-N 3-(2,5-dimethoxyphenyl)benzaldehyde Chemical compound COC1=CC=C(OC)C(C=2C=C(C=O)C=CC=2)=C1 CPFJCSLRFAKWGH-UHFFFAOYSA-N 0.000 description 1
• MKPUDBNIYWPDHQ-UHFFFAOYSA-N 3-(2,6-dimethoxypyrimidin-4-yl)benzaldehyde Chemical compound COC1=NC(OC)=CC(C=2C=C(C=O)C=CC=2)=N1 MKPUDBNIYWPDHQ-UHFFFAOYSA-N 0.000 description 1
• PEIHWSWXATULIX-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)benzaldehyde Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=CC(C=O)=C1 PEIHWSWXATULIX-UHFFFAOYSA-N 0.000 description 1
• LJACQNZRKNJEHV-UHFFFAOYSA-N 3-(3-bromophenoxy)propan-1-ol Chemical compound OCCCOC1=CC=CC(Br)=C1 LJACQNZRKNJEHV-UHFFFAOYSA-N 0.000 description 1
• TYGIOFJINGKRSF-UHFFFAOYSA-N 3-(3-ethoxyphenyl)benzaldehyde Chemical compound CCOC1=CC=CC(C=2C=C(C=O)C=CC=2)=C1 TYGIOFJINGKRSF-UHFFFAOYSA-N 0.000 description 1
• PHHZGMQJVJZIJN-UHFFFAOYSA-N 3-(3-formylphenyl)-4-hydroxybenzonitrile Chemical compound C(=O)C=1C=C(C=CC=1)C1=CC(=CC=C1O)C#N PHHZGMQJVJZIJN-UHFFFAOYSA-N 0.000 description 1
• QGMWHEBQRKSKEO-UHFFFAOYSA-N 3-(3-formylphenyl)-4-methoxybenzonitrile Chemical compound C(=O)C=1C=C(C=CC=1)C1=CC(=CC=C1OC)C#N QGMWHEBQRKSKEO-UHFFFAOYSA-N 0.000 description 1
• YDGGCRIRQDRYJT-UHFFFAOYSA-N 3-(3-formylphenyl)-5-methoxybenzonitrile Chemical compound C(=O)C=1C=C(C=CC=1)C1=CC(=CC(=C1)OC)C#N YDGGCRIRQDRYJT-UHFFFAOYSA-N 0.000 description 1
• PSOZFNWWGYSPSC-UHFFFAOYSA-N 3-(3-formylphenyl)pyridine-2-carbonitrile Chemical compound O=Cc1cccc(c1)-c1cccnc1C#N PSOZFNWWGYSPSC-UHFFFAOYSA-N 0.000 description 1
• AFKOLILXXLQCFN-UHFFFAOYSA-N 3-(3-hydroxy-5-methoxyphenyl)benzaldehyde Chemical compound COC1=CC(O)=CC(C=2C=C(C=O)C=CC=2)=C1 AFKOLILXXLQCFN-UHFFFAOYSA-N 0.000 description 1
• KUOSZXIUAZCMLP-UHFFFAOYSA-N 3-(4,6-dimethoxy-1,3,5-triazin-2-yl)benzaldehyde Chemical compound COC1=NC(=NC(=N1)OC)C=1C=C(C=O)C=CC=1 KUOSZXIUAZCMLP-UHFFFAOYSA-N 0.000 description 1
• OFESSXPDZHFFQR-UHFFFAOYSA-N 3-(4,6-dimethoxypyrimidin-2-yl)benzaldehyde Chemical compound COC1=NC(=NC(=C1)OC)C=1C=C(C=O)C=CC1 OFESSXPDZHFFQR-UHFFFAOYSA-N 0.000 description 1
• CUOMPHNZIQKWMP-UHFFFAOYSA-N 3-(4-formylpyridin-2-yl)-4-hydroxybenzonitrile Chemical compound C(=O)C1=CC(=NC=C1)C=1C=C(C#N)C=CC1O CUOMPHNZIQKWMP-UHFFFAOYSA-N 0.000 description 1
• ZUHXHOMOCDIYIL-UHFFFAOYSA-N 3-(4-formylpyridin-2-yl)benzonitrile Chemical compound C(=O)C1=CC(=NC=C1)C=1C=C(C#N)C=CC1 ZUHXHOMOCDIYIL-UHFFFAOYSA-N 0.000 description 1
• SSAKINHQROUJAE-UHFFFAOYSA-N 3-(4-hydroxy-3-methoxyphenyl)benzaldehyde Chemical compound C1=C(O)C(OC)=CC(C=2C=C(C=O)C=CC=2)=C1 SSAKINHQROUJAE-UHFFFAOYSA-N 0.000 description 1
• MMXLQHMKFDEKHM-UHFFFAOYSA-N 3-(4-methoxyphenyl)benzaldehyde Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(C=O)=C1 MMXLQHMKFDEKHM-UHFFFAOYSA-N 0.000 description 1
• RNCOWQRNQXXADJ-UHFFFAOYSA-N 3-(4-methoxypyridin-2-yl)-2-phenylmethoxybenzaldehyde Chemical compound COc1ccnc(c1)-c1cccc(C=O)c1OCc1ccccc1 RNCOWQRNQXXADJ-UHFFFAOYSA-N 0.000 description 1
• NWMSDSQVXOKVTD-UHFFFAOYSA-N 3-(4-methoxypyridin-2-yl)-4-phenylmethoxybenzaldehyde Chemical compound COc1ccnc(c1)-c1cc(C=O)ccc1OCc1ccccc1 NWMSDSQVXOKVTD-UHFFFAOYSA-N 0.000 description 1
• MWNSPJMYLOFPKA-UHFFFAOYSA-N 3-(4-methoxypyridin-2-yl)benzaldehyde Chemical compound COC1=CC(=NC=C1)C=1C=C(C=O)C=CC1 MWNSPJMYLOFPKA-UHFFFAOYSA-N 0.000 description 1
• MQXNZKUXQNJFPZ-UHFFFAOYSA-N 3-(4-methoxypyrimidin-2-yl)benzaldehyde Chemical compound COc1ccnc(n1)-c1cccc(C=O)c1 MQXNZKUXQNJFPZ-UHFFFAOYSA-N 0.000 description 1
• RTYUBKQTFNAFQC-UHFFFAOYSA-N 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile Chemical compound O1CC(C)(C)COB1C1=CC=CC(C#N)=C1 RTYUBKQTFNAFQC-UHFFFAOYSA-N 0.000 description 1
• KQQUCKKQBCHOEO-UHFFFAOYSA-N 3-(5-chloropyridazin-3-yl)benzaldehyde Chemical compound ClC=1C=C(N=NC1)C=1C=C(C=O)C=CC1 KQQUCKKQBCHOEO-UHFFFAOYSA-N 0.000 description 1
• QQUISKCSXMRTMK-UHFFFAOYSA-N 3-(5-methoxypyridazin-3-yl)-4-phenylmethoxybenzaldehyde Chemical compound COc1cnnc(c1)-c1cc(C=O)ccc1OCc1ccccc1 QQUISKCSXMRTMK-UHFFFAOYSA-N 0.000 description 1
• HVROWPFUUNGYGJ-UHFFFAOYSA-N 3-(5-methoxypyridazin-3-yl)benzaldehyde Chemical compound COC=1C=C(N=NC1)C=1C=C(C=O)C=CC1 HVROWPFUUNGYGJ-UHFFFAOYSA-N 0.000 description 1
• XGTLHIXQWLDEST-UHFFFAOYSA-N 3-(5-methoxypyridin-3-yl)benzaldehyde Chemical compound COC1=CN=CC(C=2C=C(C=O)C=CC=2)=C1 XGTLHIXQWLDEST-UHFFFAOYSA-N 0.000 description 1
• JPJQDGGTTAJGLU-UHFFFAOYSA-N 3-(6-methoxypyrazin-2-yl)benzaldehyde Chemical compound COC1=CN=CC(=N1)C=1C=C(C=O)C=CC1 JPJQDGGTTAJGLU-UHFFFAOYSA-N 0.000 description 1
• KGIJSCHQXFZBSY-UHFFFAOYSA-N 3-(6-methoxypyridazin-3-yl)benzaldehyde Chemical compound COc1ccc(nn1)-c1cccc(C=O)c1 KGIJSCHQXFZBSY-UHFFFAOYSA-N 0.000 description 1
• ILNNPGDBYVOIBH-UHFFFAOYSA-N 3-(6-methoxypyridazin-4-yl)benzaldehyde Chemical compound COC1=CC(=CN=N1)C=1C=C(C=O)C=CC1 ILNNPGDBYVOIBH-UHFFFAOYSA-N 0.000 description 1
• AGTWJNKIGNLERK-UHFFFAOYSA-N 3-(6-methoxypyridin-2-yl)-4-phenylmethoxybenzaldehyde Chemical compound C(C1=CC=CC=C1)OC1=C(C=C(C=O)C=C1)C1=NC(=CC=C1)OC AGTWJNKIGNLERK-UHFFFAOYSA-N 0.000 description 1
• ZVONWYZOKJCKEJ-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)benzaldehyde Chemical compound C1=NC(OC)=CC=C1C1=CC=CC(C=O)=C1 ZVONWYZOKJCKEJ-UHFFFAOYSA-N 0.000 description 1
• ZTOCGFKGRYBFSV-UHFFFAOYSA-N 3-(6-methoxypyrimidin-4-yl)benzaldehyde Chemical compound COC1=CC(=NC=N1)C=1C=C(C=O)C=CC1 ZTOCGFKGRYBFSV-UHFFFAOYSA-N 0.000 description 1
• VUTLYXXDJRUUIX-UHFFFAOYSA-N 3-[3-(4-hydroxybutoxy)phenyl]benzaldehyde Chemical compound OCCCCOC=1C=C(C=CC1)C1=CC(=CC=C1)C=O VUTLYXXDJRUUIX-UHFFFAOYSA-N 0.000 description 1
• GFEXNVREBBHEGA-UHFFFAOYSA-N 3-[3-(oxiran-2-ylmethoxy)phenyl]benzaldehyde Chemical compound O=Cc1cccc(c1)-c1cccc(OCC2CO2)c1 GFEXNVREBBHEGA-UHFFFAOYSA-N 0.000 description 1
• GDPZLNBLFAQBHZ-UHFFFAOYSA-N 3-[5-(2-methoxyethoxy)pyridin-3-yl]benzaldehyde Chemical compound COCCOc1cncc(c1)-c1cccc(C=O)c1 GDPZLNBLFAQBHZ-UHFFFAOYSA-N 0.000 description 1
• ZSJWXTGYGMZEQK-UHFFFAOYSA-N 3-[6-(3-hydroxypyrrolidin-1-yl)pyridin-2-yl]benzaldehyde Chemical compound OC1CCN(C1)c1cccc(n1)-c1cccc(C=O)c1 ZSJWXTGYGMZEQK-UHFFFAOYSA-N 0.000 description 1
• STBGLXMINLWCNL-UHFFFAOYSA-N 3-bromo-2-hydroxybenzaldehyde Chemical compound OC1=C(Br)C=CC=C1C=O STBGLXMINLWCNL-UHFFFAOYSA-N 0.000 description 1
• QHWZMDRKTYTPEE-UHFFFAOYSA-N 3-bromo-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1Br QHWZMDRKTYTPEE-UHFFFAOYSA-N 0.000 description 1
• FYUMRYNAZSTXJV-UHFFFAOYSA-N 3-bromo-5-ethoxypyridine Chemical compound CCOC1=CN=CC(Br)=C1 FYUMRYNAZSTXJV-UHFFFAOYSA-N 0.000 description 1
• NNWRYZGZCCTKQW-UHFFFAOYSA-N 3-bromo-5-methoxybenzonitrile Chemical compound COC1=CC(Br)=CC(C#N)=C1 NNWRYZGZCCTKQW-UHFFFAOYSA-N 0.000 description 1
• MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 1
• HCOPIUVJCIZALB-UHFFFAOYSA-N 3-bromopyridine-2-carbonitrile Chemical compound BrC1=CC=CN=C1C#N HCOPIUVJCIZALB-UHFFFAOYSA-N 0.000 description 1
• JNETYVLEGPSOFY-UHFFFAOYSA-N 3-bromopyrrolidine-2,5-dione Chemical compound BrC1CC(=O)NC1=O JNETYVLEGPSOFY-UHFFFAOYSA-N 0.000 description 1
• UFOCFIUPDRXWTJ-UHFFFAOYSA-N 3-chloro-5-(3-methoxyphenyl)pyridazine Chemical compound ClC=1N=NC=C(C1)C1=CC(=CC=C1)OC UFOCFIUPDRXWTJ-UHFFFAOYSA-N 0.000 description 1
• XBJLKXOOHLLTPG-UHFFFAOYSA-N 3-chloro-6-methoxypyridazine Chemical compound COC1=CC=C(Cl)N=N1 XBJLKXOOHLLTPG-UHFFFAOYSA-N 0.000 description 1
• FJCSSEXBMUHOGV-UHFFFAOYSA-N 3-ethenyl-5-(3-methoxyphenyl)pyridazine Chemical compound COC=1C=C(C=CC1)C=1C=C(N=NC1)C=C FJCSSEXBMUHOGV-UHFFFAOYSA-N 0.000 description 1
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
• HENXUFOAGXNWKH-UHFFFAOYSA-N 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=CN=CC(B2OC(C)(C)C(C)(C)O2)=C1 HENXUFOAGXNWKH-UHFFFAOYSA-N 0.000 description 1
• OLSCCVCNHXJADN-UHFFFAOYSA-N 4-(3-bromophenoxy)butan-1-ol Chemical compound OCCCCOC1=CC=CC(Br)=C1 OLSCCVCNHXJADN-UHFFFAOYSA-N 0.000 description 1
• PDSHFWQMLONAMR-UHFFFAOYSA-N 4-(3-formylphenyl)-2-methoxybenzonitrile Chemical compound C(=O)C=1C=C(C=CC=1)C1=CC(=C(C=C1)C#N)OC PDSHFWQMLONAMR-UHFFFAOYSA-N 0.000 description 1
• MJIMSRCIWUJRHC-UHFFFAOYSA-N 4-(3-formylphenyl)benzonitrile Chemical compound O=CC1=CC=CC(C=2C=CC(=CC=2)C#N)=C1 MJIMSRCIWUJRHC-UHFFFAOYSA-N 0.000 description 1
• KACKJFVOFZLOIK-UHFFFAOYSA-N 4-(dimethoxymethyl)-2-(3-methoxyphenyl)pyrimidine Chemical compound COC(C1=NC(=NC=C1)C1=CC(=CC=C1)OC)OC KACKJFVOFZLOIK-UHFFFAOYSA-N 0.000 description 1
• FPXGWOZNYGASQM-UHFFFAOYSA-N 4-(hydroxymethyl)-2-(5-methoxypyridazin-3-yl)phenol Chemical compound COc1cnnc(c1)-c1cc(CO)ccc1O FPXGWOZNYGASQM-UHFFFAOYSA-N 0.000 description 1
• IVYKCTGCJDBWMQ-UHFFFAOYSA-N 4-bromo-2-methoxybenzamide Chemical compound COC1=CC(Br)=CC=C1C(N)=O IVYKCTGCJDBWMQ-UHFFFAOYSA-N 0.000 description 1
• QRUOZMVYROKPOO-UHFFFAOYSA-N 4-bromo-2-methoxybenzonitrile Chemical compound COC1=CC(Br)=CC=C1C#N QRUOZMVYROKPOO-UHFFFAOYSA-N 0.000 description 1
• YFTGMMXMLPTTAY-UHFFFAOYSA-N 4-bromo-2-methoxypyridine Chemical compound COC1=CC(Br)=CC=N1 YFTGMMXMLPTTAY-UHFFFAOYSA-N 0.000 description 1
• CKVQWOKUEZYWRQ-UHFFFAOYSA-N 4-bromopyridine-2-carbaldehyde Chemical compound BrC1=CC=NC(C=O)=C1 CKVQWOKUEZYWRQ-UHFFFAOYSA-N 0.000 description 1
• NHMLZGFOEYLZEN-UHFFFAOYSA-N 4-chloro-1h-pyridazin-6-one Chemical compound ClC=1C=NNC(=O)C=1 NHMLZGFOEYLZEN-UHFFFAOYSA-N 0.000 description 1
• JHNRTJRDRWKAIW-UHFFFAOYSA-N 4-chloro-2,6-dimethoxypyrimidine Chemical compound COC1=CC(Cl)=NC(OC)=N1 JHNRTJRDRWKAIW-UHFFFAOYSA-N 0.000 description 1
• KLJGSQVYUGQOAW-UHFFFAOYSA-N 4-chloro-6-methoxypyrimidine Chemical compound COC1=CC(Cl)=NC=N1 KLJGSQVYUGQOAW-UHFFFAOYSA-N 0.000 description 1
• PKEOWBOSYQGFFC-UHFFFAOYSA-N 4-fluoro-3-(3-methoxyphenyl)benzaldehyde Chemical compound COC1=CC=CC(C=2C(=CC=C(C=O)C=2)F)=C1 PKEOWBOSYQGFFC-UHFFFAOYSA-N 0.000 description 1
• WKSRZNZUMDPUQK-UHFFFAOYSA-N 4-hydroxy-3-(4-methoxypyridin-2-yl)benzaldehyde Chemical compound OC1=C(C=C(C=O)C=C1)C1=NC=CC(=C1)OC WKSRZNZUMDPUQK-UHFFFAOYSA-N 0.000 description 1
• PRTXMBXCCJELRC-UHFFFAOYSA-N 4-hydroxy-3-(5-methoxypyridazin-3-yl)benzaldehyde Chemical compound OC1=C(C=C(C=O)C=C1)C=1N=NC=C(C1)OC PRTXMBXCCJELRC-UHFFFAOYSA-N 0.000 description 1
• MXEWGAFSEKUQRP-UHFFFAOYSA-N 4-methyl-1-oxidomorpholin-1-ium Chemical compound CN1CC[O+]([O-])CC1 MXEWGAFSEKUQRP-UHFFFAOYSA-N 0.000 description 1
• SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 description 1
• OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
• ZLILRRGWBOKBIG-UHFFFAOYSA-N 4h-1,4-benzothiazine Chemical compound C1=CC=C2NC=CSC2=C1 ZLILRRGWBOKBIG-UHFFFAOYSA-N 0.000 description 1
• QRCGFTXRXYMJOS-UHFFFAOYSA-N 4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)COC2=C1 QRCGFTXRXYMJOS-UHFFFAOYSA-N 0.000 description 1
• AHVZNKYZNODJFK-UHFFFAOYSA-N 5-(3-formylphenyl)-6-oxo-1H-pyridine-3-carbonitrile Chemical compound C(=O)C=1C=C(C=CC1)C=1C(=NC=C(C#N)C1)O AHVZNKYZNODJFK-UHFFFAOYSA-N 0.000 description 1
• XZWZJZPWQBKKPH-UHFFFAOYSA-N 5-(3-formylphenyl)pyridine-3-carbonitrile Chemical compound O=CC1=CC=CC(C=2C=C(C=NC=2)C#N)=C1 XZWZJZPWQBKKPH-UHFFFAOYSA-N 0.000 description 1
• SHHGRBQBFYDHFN-UHFFFAOYSA-N 5-(3-methoxyphenyl)pyridine-3-carbaldehyde Chemical compound COC1=CC=CC(C=2C=C(C=O)C=NC=2)=C1 SHHGRBQBFYDHFN-UHFFFAOYSA-N 0.000 description 1
• NCIBXYJEJGGUFF-UHFFFAOYSA-N 5-bromo-6-oxo-1h-pyridine-3-carbonitrile Chemical compound OC1=NC=C(C#N)C=C1Br NCIBXYJEJGGUFF-UHFFFAOYSA-N 0.000 description 1
• FTFFHWWIPOQCBC-UHFFFAOYSA-N 5-bromopyridine-3-carbonitrile Chemical compound BrC1=CN=CC(C#N)=C1 FTFFHWWIPOQCBC-UHFFFAOYSA-N 0.000 description 1
• MRPWHLMYGOENNC-UHFFFAOYSA-N 5-ethenyl-3-(3-methoxyphenyl)pyridazine Chemical compound COC=1C=C(C=CC1)C=1N=NC=C(C1)C=C MRPWHLMYGOENNC-UHFFFAOYSA-N 0.000 description 1
• QFDDPFQWYPBORA-UHFFFAOYSA-N 6-(3-formyl-2-hydroxyphenyl)pyridine-2-carbonitrile Chemical compound C(=O)C=1C(=C(C=CC1)C1=CC=CC(=N1)C#N)O QFDDPFQWYPBORA-UHFFFAOYSA-N 0.000 description 1
• QVVOSICYVBXTMS-UHFFFAOYSA-N 6-(3-formyl-2-phenylmethoxyphenyl)pyridine-2-carbonitrile Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC=C1C=O)C1=CC=CC(=N1)C#N QVVOSICYVBXTMS-UHFFFAOYSA-N 0.000 description 1
• CCXXUBKOESZHIL-UHFFFAOYSA-N 6-(3-formylphenyl)pyridine-2-carbonitrile Chemical compound C(=O)C=1C=C(C=CC1)C1=CC=CC(=N1)C#N CCXXUBKOESZHIL-UHFFFAOYSA-N 0.000 description 1
• VOEKNDLNFFBAOY-UHFFFAOYSA-N 6-(3-methoxyphenyl)pyridine-2-carbaldehyde Chemical compound COC1=CC=CC(C=2N=C(C=O)C=CC=2)=C1 VOEKNDLNFFBAOY-UHFFFAOYSA-N 0.000 description 1
• SOWHTXOZYGWTJV-UHFFFAOYSA-N 6-(6-methoxypyridin-2-yl)pyridine-2-carbaldehyde Chemical compound COc1cccc(n1)-c1cccc(C=O)n1 SOWHTXOZYGWTJV-UHFFFAOYSA-N 0.000 description 1
• APVMYCSPPJXYAR-UHFFFAOYSA-N 6-[5-(2-hydroxyethyl)-2-oxo-1,3-oxazol-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound OCCC1=CN(C(O1)=O)C=1C=CC=2OCC(NC=2N=1)=O APVMYCSPPJXYAR-UHFFFAOYSA-N 0.000 description 1
• QWFHFNGMCPMOCD-UHFFFAOYSA-N 6-bromopyridine-2-carbaldehyde Chemical compound BrC1=CC=CC(C=O)=N1 QWFHFNGMCPMOCD-UHFFFAOYSA-N 0.000 description 1
• HNEBPTAKURBYRM-UHFFFAOYSA-N 6-bromopyridine-2-carbonitrile Chemical compound BrC1=CC=CC(C#N)=N1 HNEBPTAKURBYRM-UHFFFAOYSA-N 0.000 description 1
• NWLIHAPBHUZMAD-UHFFFAOYSA-N 6-chloropyrazine-2-carbaldehyde Chemical compound ClC1=CN=CC(C=O)=N1 NWLIHAPBHUZMAD-UHFFFAOYSA-N 0.000 description 1
• PGZHSVWXFKKCNR-UHFFFAOYSA-N 6-chloropyridine-2-carbonitrile Chemical compound ClC1=CC=CC(C#N)=N1 PGZHSVWXFKKCNR-UHFFFAOYSA-N 0.000 description 1
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
• 102100030674 ADP-ribosylation factor-like protein 6-interacting protein 1 Human genes 0.000 description 1
• 101710199050 ADP-ribosylation factor-like protein 6-interacting protein 1 Proteins 0.000 description 1
• ZHGNHOOVYPHPNJ-UHFFFAOYSA-N Amigdalin Chemical compound FC(F)(F)C(=O)OCC1OC(OCC2OC(OC(C#N)C3=CC=CC=C3)C(OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C2OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C1OC(=O)C(F)(F)F ZHGNHOOVYPHPNJ-UHFFFAOYSA-N 0.000 description 1
• 101100132433 Arabidopsis thaliana VIII-1 gene Proteins 0.000 description 1
• 201000001320 Atherosclerosis Diseases 0.000 description 1
• 241000304886 Bacilli Species 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• 101150077194 CAP1 gene Proteins 0.000 description 1
• ONSSERMKWUZEBZ-UHFFFAOYSA-N COC=1C=C(N=NC1)C1=CC(=NC=C1)CO Chemical compound COC=1C=C(N=NC1)C1=CC(=NC=C1)CO ONSSERMKWUZEBZ-UHFFFAOYSA-N 0.000 description 1
• BAYSBPKILGQNOD-UHFFFAOYSA-N COC=1C=C(N=NC1)C=1C=C(C=NC1)CO Chemical compound COC=1C=C(N=NC1)C=1C=C(C=NC1)CO BAYSBPKILGQNOD-UHFFFAOYSA-N 0.000 description 1
• 241000282472 Canis lupus familiaris Species 0.000 description 1
• 241000283707 Capra Species 0.000 description 1
• 208000024172 Cardiovascular disease Diseases 0.000 description 1
• 229930186147 Cephalosporin Natural products 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• 208000017667 Chronic Disease Diseases 0.000 description 1
• KFEYGDVVUWBCSQ-UHFFFAOYSA-N ClC=1C=C(N=NC1)C1=CC(=CC=C1)OC Chemical compound ClC=1C=C(N=NC1)C1=CC(=CC=C1)OC KFEYGDVVUWBCSQ-UHFFFAOYSA-N 0.000 description 1
• 206010010741 Conjunctivitis Diseases 0.000 description 1
• 206010011224 Cough Diseases 0.000 description 1
• 244000110556 Cyclopia subternata Species 0.000 description 1
• 206010011844 Dacryocystitis Diseases 0.000 description 1
• 108010032363 ERRalpha estrogen-related receptor Proteins 0.000 description 1
• 241000588921 Enterobacteriaceae Species 0.000 description 1
• 241000283086 Equidae Species 0.000 description 1
• 241000588724 Escherichia coli Species 0.000 description 1
• PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• 206010016952 Food poisoning Diseases 0.000 description 1
• 208000019331 Foodborne disease Diseases 0.000 description 1
• 201000000628 Gas Gangrene Diseases 0.000 description 1
• 208000005577 Gastroenteritis Diseases 0.000 description 1
• 206010018364 Glomerulonephritis Diseases 0.000 description 1
• 208000008745 Healthcare-Associated Pneumonia Diseases 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101000798707 Homo sapiens Transmembrane protease serine 13 Proteins 0.000 description 1
• 101150044367 MKC1 gene Proteins 0.000 description 1
• 208000010315 Mastoiditis Diseases 0.000 description 1
• 101100245221 Mus musculus Prss8 gene Proteins 0.000 description 1
• BMIAHCCEJUDIGR-UHFFFAOYSA-N N(=[N+]=[N-])CCC1=CN(C(O1)=O)C=1C=CC=2OCC(NC=2N=1)=O Chemical compound N(=[N+]=[N-])CCC1=CN(C(O1)=O)C=1C=CC=2OCC(NC=2N=1)=O BMIAHCCEJUDIGR-UHFFFAOYSA-N 0.000 description 1
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
• 229930182555 Penicillin Natural products 0.000 description 1
• 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 description 1
• 208000008469 Peptic Ulcer Diseases 0.000 description 1
• 208000037581 Persistent Infection Diseases 0.000 description 1
• 201000007100 Pharyngitis Diseases 0.000 description 1
• QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
• 206010036422 Postpartum sepsis Diseases 0.000 description 1
• 206010037075 Protozoal infections Diseases 0.000 description 1
• 208000020264 Puerperal Infection Diseases 0.000 description 1
• 241000282849 Ruminantia Species 0.000 description 1
• 101100103009 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) WSS1 gene Proteins 0.000 description 1
• 206010040070 Septic Shock Diseases 0.000 description 1
• 208000019802 Sexually transmitted disease Diseases 0.000 description 1
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
• 241000295644 Staphylococcaceae Species 0.000 description 1
• 102100036832 Steroid hormone receptor ERR1 Human genes 0.000 description 1
• 241000194017 Streptococcus Species 0.000 description 1
• 241000282887 Suidae Species 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• 239000004098 Tetracycline Substances 0.000 description 1
• 206010044248 Toxic shock syndrome Diseases 0.000 description 1
• 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
• 102100032467 Transmembrane protease serine 13 Human genes 0.000 description 1
• 208000025865 Ulcer Diseases 0.000 description 1
• 208000006374 Uterine Cervicitis Diseases 0.000 description 1
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
• 206010000269 abscess Diseases 0.000 description 1
• 239000006096 absorbing agent Substances 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
• 230000004913 activation Effects 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 241001148470 aerobic bacillus Species 0.000 description 1
• 230000002152 alkylating effect Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• 229940126575 aminoglycoside Drugs 0.000 description 1
• 244000037640 animal pathogen Species 0.000 description 1
• 239000004599 antimicrobial Substances 0.000 description 1
• 239000000010 aprotic solvent Substances 0.000 description 1
• 239000012300 argon atmosphere Substances 0.000 description 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
• 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 235000010290 biphenyl Nutrition 0.000 description 1
• UBXYXCRCOKCZIT-UHFFFAOYSA-N biphenyl-3-ol Chemical compound OC1=CC=CC(C=2C=CC=CC=2)=C1 UBXYXCRCOKCZIT-UHFFFAOYSA-N 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 210000000481 breast Anatomy 0.000 description 1
• 206010006451 bronchitis Diseases 0.000 description 1
• 229940045348 brown mixture Drugs 0.000 description 1
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 239000012876 carrier material Substances 0.000 description 1
• 238000006555 catalytic reaction Methods 0.000 description 1
• 125000002091 cationic group Chemical group 0.000 description 1
• 229940124587 cephalosporin Drugs 0.000 description 1
• 150000001780 cephalosporins Chemical class 0.000 description 1
• 206010008323 cervicitis Diseases 0.000 description 1
• 238000012512 characterization method Methods 0.000 description 1
• 239000003638 chemical reducing agent Substances 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 230000000973 chemotherapeutic effect Effects 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
• 229960005091 chloramphenicol Drugs 0.000 description 1
• 150000001805 chlorine compounds Chemical class 0.000 description 1
• 239000003245 coal Substances 0.000 description 1
• 229940125758 compound 15 Drugs 0.000 description 1
• 229940126208 compound 22 Drugs 0.000 description 1
• 229940126545 compound 53 Drugs 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 238000007366 cycloisomerization reaction Methods 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 239000002274 desiccant Substances 0.000 description 1
• 125000004431 deuterium atom Chemical group 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
• WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
• YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
• MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
• KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
• 208000035475 disorder Diseases 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 238000000132 electrospray ionisation Methods 0.000 description 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• SOKSJIDLQWRXTN-UHFFFAOYSA-N ethyl 2-(3-bromophenoxy)acetate Chemical compound CCOC(=O)COC1=CC=CC(Br)=C1 SOKSJIDLQWRXTN-UHFFFAOYSA-N 0.000 description 1
• NNMBFGGFJNGEHG-UHFFFAOYSA-N ethyl 2-[3-(3-formylphenyl)phenoxy]acetate Chemical compound CCOC(=O)COc1cccc(c1)-c1cccc(C=O)c1 NNMBFGGFJNGEHG-UHFFFAOYSA-N 0.000 description 1
• ZKGQTSJZFBTEOB-UHFFFAOYSA-N ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC(B2OC(C)(C)C(C)(C)O2)=C1 ZKGQTSJZFBTEOB-UHFFFAOYSA-N 0.000 description 1
• PZQZUDHBJOCDOO-UHFFFAOYSA-N ethyl 5-(5-methoxypyridazin-3-yl)pyridine-3-carboxylate Chemical compound CCOC(=O)c1cncc(c1)-c1cc(OC)cnn1 PZQZUDHBJOCDOO-UHFFFAOYSA-N 0.000 description 1
• 238000000105 evaporative light scattering detection Methods 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
• 239000000835 fiber Substances 0.000 description 1
• 239000012065 filter cake Substances 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
• 229910052737 gold Inorganic materials 0.000 description 1
• 238000000227 grinding Methods 0.000 description 1
• 208000019622 heart disease Diseases 0.000 description 1
• 244000052637 human pathogen Species 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• 238000005984 hydrogenation reaction Methods 0.000 description 1
• 150000002466 imines Chemical class 0.000 description 1
• 230000036039 immunity Effects 0.000 description 1
• 239000007943 implant Substances 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 239000011147 inorganic material Substances 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 230000000968 intestinal effect Effects 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 230000000155 isotopic effect Effects 0.000 description 1
• 206010023332 keratitis Diseases 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 239000010985 leather Substances 0.000 description 1
• 239000003446 ligand Substances 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 230000014759 maintenance of location Effects 0.000 description 1
• 201000004792 malaria Diseases 0.000 description 1
• 238000004949 mass spectrometry Methods 0.000 description 1
• 235000013372 meat Nutrition 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
• UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
• CPAIYDIGLIGAEN-UHFFFAOYSA-N methyl 3-(3-formylphenyl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=C(C=O)C=CC=2)=C1 CPAIYDIGLIGAEN-UHFFFAOYSA-N 0.000 description 1
• KMFJVYMFCAIRAN-UHFFFAOYSA-N methyl 3-bromobenzoate Chemical compound COC(=O)C1=CC=CC(Br)=C1 KMFJVYMFCAIRAN-UHFFFAOYSA-N 0.000 description 1
• VKQJRCIFKHNEMI-UHFFFAOYSA-N methyl 4-(5-methoxypyridazin-3-yl)pyridine-2-carboxylate Chemical compound COC(=O)c1cc(ccn1)-c1cc(OC)cnn1 VKQJRCIFKHNEMI-UHFFFAOYSA-N 0.000 description 1
• CEOILRYKIJRPBZ-UHFFFAOYSA-N methyl cyclopent-3-ene-1-carboxylate Chemical compound COC(=O)C1CC=CC1 CEOILRYKIJRPBZ-UHFFFAOYSA-N 0.000 description 1
• 244000000010 microbial pathogen Species 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• FEKRFYZGYUTGRY-UHFFFAOYSA-N n'-ethylmethanediimine Chemical compound CCN=C=N FEKRFYZGYUTGRY-UHFFFAOYSA-N 0.000 description 1
• KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
• YCJZWBZJSYLMPB-UHFFFAOYSA-N n-(2-chloropyrimidin-4-yl)-2,5-dimethyl-1-phenylimidazole-4-carboxamide Chemical compound CC=1N(C=2C=CC=CC=2)C(C)=NC=1C(=O)NC1=CC=NC(Cl)=N1 YCJZWBZJSYLMPB-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
• 125000005151 nonafluorobutanesulfonyl group Chemical group FC(C(C(S(=O)(=O)*)(F)F)(F)F)(C(F)(F)F)F 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 238000005457 optimization Methods 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 125000004043 oxo group Chemical group O=* 0.000 description 1
• LVSJDHGRKAEGLX-UHFFFAOYSA-N oxolane;2,2,2-trifluoroacetic acid Chemical compound C1CCOC1.OC(=O)C(F)(F)F LVSJDHGRKAEGLX-UHFFFAOYSA-N 0.000 description 1
• 244000045947 parasite Species 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 230000001717 pathogenic effect Effects 0.000 description 1
• 229940049954 penicillin Drugs 0.000 description 1
• 239000012026 peptide coupling reagents‎ Substances 0.000 description 1
• 229940124531 pharmaceutical excipient Drugs 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
• 150000003003 phosphines Chemical class 0.000 description 1
• SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
• QHXLIQMGIGEHJP-UHFFFAOYSA-N picoline - borane complex Substances [B].CC1=CC=CC=N1 QHXLIQMGIGEHJP-UHFFFAOYSA-N 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 244000144977 poultry Species 0.000 description 1
• 239000012041 precatalyst Substances 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 238000004321 preservation Methods 0.000 description 1
• 238000012545 processing Methods 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000003586 protic polar solvent Substances 0.000 description 1
• 208000028172 protozoa infectious disease Diseases 0.000 description 1
• BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
• 229940070891 pyridium Drugs 0.000 description 1
• 238000010791 quenching Methods 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 230000009467 reduction Effects 0.000 description 1
• 238000006722 reduction reaction Methods 0.000 description 1
• 238000006268 reductive amination reaction Methods 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 230000008261 resistance mechanism Effects 0.000 description 1
• 230000000241 respiratory effect Effects 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 239000000741 silica gel Substances 0.000 description 1
• 229910002027 silica gel Inorganic materials 0.000 description 1
• 238000010898 silica gel chromatography Methods 0.000 description 1
• 229910052709 silver Inorganic materials 0.000 description 1
• 239000004332 silver Substances 0.000 description 1
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
• 201000009890 sinusitis Diseases 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• 239000002594 sorbent Substances 0.000 description 1
• 241000894007 species Species 0.000 description 1
• VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• 229910052717 sulfur Inorganic materials 0.000 description 1
• 239000011593 sulfur Substances 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 238000001308 synthesis method Methods 0.000 description 1
• 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
• LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
• BWNQTGRBVMERHU-UHFFFAOYSA-N tert-butyl n-but-3-ynylcarbamate Chemical compound CC(C)(C)OC(=O)NCCC#C BWNQTGRBVMERHU-UHFFFAOYSA-N 0.000 description 1
• QCIWZIYBBNEPKB-UHFFFAOYSA-N tert-butyl(dimethyl)silane Chemical compound C[SiH](C)C(C)(C)C QCIWZIYBBNEPKB-UHFFFAOYSA-N 0.000 description 1
• JENWKUPKYMNMMA-UHFFFAOYSA-N tert-butyl-dimethyl-[2-(oxiran-2-yl)ethoxy]silane Chemical compound CC(C)(C)[Si](C)(C)OCCC1CO1 JENWKUPKYMNMMA-UHFFFAOYSA-N 0.000 description 1
• 235000019364 tetracycline Nutrition 0.000 description 1
• 150000003522 tetracyclines Chemical class 0.000 description 1
• 229940040944 tetracyclines Drugs 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
• WJZPIORVERXPPR-UHFFFAOYSA-L tetramethylazanium;carbonate Chemical compound [O-]C([O-])=O.C[N+](C)(C)C.C[N+](C)(C)C WJZPIORVERXPPR-UHFFFAOYSA-L 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• 206010044008 tonsillitis Diseases 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 239000003053 toxin Substances 0.000 description 1
• 231100000765 toxin Toxicity 0.000 description 1
• 108700012359 toxins Proteins 0.000 description 1
• DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
• WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
• 239000005051 trimethylchlorosilane Substances 0.000 description 1
• 229910052721 tungsten Inorganic materials 0.000 description 1
• 231100000397 ulcer Toxicity 0.000 description 1
• 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
• 208000000143 urethritis Diseases 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 239000002023 wood Substances 0.000 description 1
• GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
• 239000002132 β-lactam antibiotic Substances 0.000 description 1
• 229940124586 β-lactam antibiotics Drugs 0.000 description 1