KR20150143720A - 항균성 이방향족 유도체 - Google Patents
항균성 이방향족 유도체 Download PDFInfo
- Publication number
- KR20150143720A KR20150143720A KR1020157032552A KR20157032552A KR20150143720A KR 20150143720 A KR20150143720 A KR 20150143720A KR 1020157032552 A KR1020157032552 A KR 1020157032552A KR 20157032552 A KR20157032552 A KR 20157032552A KR 20150143720 A KR20150143720 A KR 20150143720A
- Authority
- KR
- South Korea
- Prior art keywords
- oxo
- oxazolidin
- pyrido
- ethyl
- methoxy
- Prior art date
- 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.)
- Abandoned
Links
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- 150000001875 compounds Chemical class 0.000 claims abstract description 547
- -1 cyanomethoxy Chemical group 0.000 claims abstract description 203
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 141
- 150000003839 salts Chemical class 0.000 claims abstract description 63
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 61
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 36
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 29
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 27
- 150000002367 halogens Chemical class 0.000 claims abstract description 27
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
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- 206010057190 Respiratory tract infections Diseases 0.000 claims description 29
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- 238000011282 treatment Methods 0.000 claims description 26
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- 208000022362 bacterial infectious disease Diseases 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
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- 230000001404 mediated effect Effects 0.000 claims description 16
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
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- 150000003857 carboxamides Chemical class 0.000 claims description 5
- 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 4
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- 206010062255 Soft tissue infection Diseases 0.000 claims description 4
- 206010040872 skin infection Diseases 0.000 claims description 4
- 208000016604 Lyme disease Diseases 0.000 claims description 3
- 201000009906 Meningitis Diseases 0.000 claims description 3
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- 229910052739 hydrogen Inorganic materials 0.000 abstract description 15
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- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract description 4
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- 238000002360 preparation method Methods 0.000 description 195
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- HJBGZJMKTOMQRR-UHFFFAOYSA-N (3-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=O)=C1 HJBGZJMKTOMQRR-UHFFFAOYSA-N 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- 239000000725 suspension Substances 0.000 description 36
- 239000012044 organic layer Substances 0.000 description 35
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 35
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 34
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- 125000004432 carbon atom Chemical group C* 0.000 description 25
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- 241000894006 Bacteria Species 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
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- 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
- 238000004519 manufacturing process Methods 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
- 229920006395 saturated elastomer Polymers 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 14
- 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 14
- 239000002904 solvent Substances 0.000 description 14
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 13
- 239000012043 crude product Substances 0.000 description 13
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 12
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- 230000015572 biosynthetic process Effects 0.000 description 12
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
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- 238000003786 synthesis reaction Methods 0.000 description 10
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 238000001514 detection method Methods 0.000 description 8
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- 229910052753 mercury Inorganic materials 0.000 description 1
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- XEXWGJDREXTYFH-UHFFFAOYSA-N methyl 1,3-dioxole-4-carboxylate Chemical compound COC(=O)C1=COCO1 XEXWGJDREXTYFH-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
- BYSRVCQMGFTUBK-UHFFFAOYSA-N methyl 3-phenylbenzoate Chemical compound COC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 BYSRVCQMGFTUBK-UHFFFAOYSA-N 0.000 description 1
- ZZABXPYOKWIHHV-UHFFFAOYSA-N methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC(B2OC(C)(C)C(C)(C)O2)=C1 ZZABXPYOKWIHHV-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
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- 239000002808 molecular sieve Substances 0.000 description 1
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- PEECTLLHENGOKU-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=NC=C1 PEECTLLHENGOKU-UHFFFAOYSA-N 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-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
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- ZOUWOGOTHLRRLS-UHFFFAOYSA-N palladium;phosphane Chemical compound P.[Pd] ZOUWOGOTHLRRLS-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 238000005897 peptide coupling reaction Methods 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
- 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 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
- 239000000047 product Substances 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
- 239000013014 purified material Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000008261 resistance mechanism Effects 0.000 description 1
- 208000020029 respiratory tract infectious disease Diseases 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 229960001860 salicylate Drugs 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
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001544 silver hexafluoroantimonate(V) Inorganic materials 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
- 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
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- SLXHIJJXFFHHMS-UHFFFAOYSA-N tert-butyl n-(4-bromobut-3-ynyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCC#CBr SLXHIJJXFFHHMS-UHFFFAOYSA-N 0.000 description 1
- DAZJYWWNTKNWFP-UHFFFAOYSA-N tert-butyl n-(4-phenylmethoxybutanoylamino)carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)CCCOCC1=CC=CC=C1 DAZJYWWNTKNWFP-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
- 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-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
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 206010044008 tonsillitis Diseases 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 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
- 239000005051 trimethylchlorosilane Substances 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
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc 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
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
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- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring systems
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- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
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- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Neurology (AREA)
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- Pulmonology (AREA)
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- Biomedical Technology (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IBPCT/IB2013/053021 | 2013-04-16 | ||
| IB2013053021 | 2013-04-16 | ||
| PCT/IB2014/060724 WO2014170821A1 (en) | 2013-04-16 | 2014-04-15 | Antibacterial biaromatic derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150143720A true KR20150143720A (ko) | 2015-12-23 |
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| KR1020157032552A Abandoned KR20150143720A (ko) | 2013-04-16 | 2014-04-15 | 항균성 이방향족 유도체 |
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| JP (1) | JP6375365B2 (enExample) |
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| CN104151316B (zh) | 2008-10-07 | 2016-06-15 | 埃科特莱茵药品有限公司 | 三环噁唑烷酮抗生素化合物 |
| AR102256A1 (es) * | 2014-10-15 | 2017-02-15 | Actelion Pharmaceuticals Ltd | Derivados biaromáticos básicos antibacterianos con sustitución de aminoalcoxi |
| TW201722965A (zh) | 2015-08-16 | 2017-07-01 | 葛蘭素史密斯克藍智慧財產發展有限公司 | 用於抗菌應用之化合物 |
| TW201808906A (zh) | 2016-03-16 | 2018-03-16 | 拜耳作物科學股份有限公司 | 作為殺蟲劑之經取代吡啶化合物 |
| AR108108A1 (es) | 2016-04-14 | 2018-07-18 | Idorsia Pharmaceuticals Ltd | Derivados biaromáticos antibacterianos con sustitución de oxetan-3-iloxi |
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| TW201833120A (zh) * | 2017-02-17 | 2018-09-16 | 瑞士商愛杜西亞製藥有限公司 | 芳基噁唑啶酮抗生素化合物 |
| EP3284739A1 (de) | 2017-07-19 | 2018-02-21 | Bayer CropScience Aktiengesellschaft | Substituierte (het)arylverbindungen als schädlingsbekämpfungsmittel |
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| CN115785718B (zh) * | 2022-11-25 | 2023-08-22 | 四川大学 | 一种多基底表面的金属配位抗菌涂层及其制备方法 |
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| EP0297042A1 (de) | 1987-06-23 | 1988-12-28 | Ciba-Geigy Ag | Substituierte Penem-Verbindungen |
| DE19802239A1 (de) | 1998-01-22 | 1999-07-29 | Bayer Ag | Neue mit Bicyclen substituierte Oxazolidinone |
| AU1026901A (en) | 1999-10-29 | 2001-05-08 | Syngenta Participations Ag | Novel herbicides |
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| AR040335A1 (es) | 2002-06-26 | 2005-03-30 | Glaxo Group Ltd | Compuesto de ciclohexano o ciclohexeno, uso del mismo para preparar un medicamento, composicion farmaceutica que lo comprende, procedimiento y compuestos intermediarios de utilidad para preparar dicho compuesto |
| WO2006102674A2 (en) | 2005-03-24 | 2006-09-28 | Microbia, Inc. | Diphenylheterocycle cholesterol absorption inhibitors |
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| US7998992B2 (en) | 2007-03-30 | 2011-08-16 | Institute Of Medicinal Molecular Design, Inc. | Oxazolidinone derivative having inhibitory activity on 11β-hydroxysteroid dehydrogenase type 1 |
| CL2008001003A1 (es) * | 2007-04-11 | 2008-10-17 | Actelion Pharmaceuticals Ltd | Compuestos derivados de oxazolidinona; composicion farmaceutica que comprende a dichos compuestos; y su uso para preparar un medicamento para tratar una infeccion bacteriana. |
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| AU2009215327A1 (en) | 2008-02-20 | 2009-08-27 | Actelion Pharmaceuticals Ltd | Azatricyclic antibiotic compounds |
| AR070458A1 (es) | 2008-02-22 | 2010-04-07 | Actelion Pharmaceuticals Ltd | Derivados de oxazolidina, una composicion farmaceutica que los contiene y su uso en la preparacion de un medicamento para el tratamiento de una infeccion bacteriana. |
| EP2321307B1 (en) * | 2008-08-04 | 2012-12-19 | Actelion Pharmaceuticals Ltd. | Tricyclic alkylaminomethyloxazolidinone derivatives |
| CN104151316B (zh) | 2008-10-07 | 2016-06-15 | 埃科特莱茵药品有限公司 | 三环噁唑烷酮抗生素化合物 |
| JP2012505201A (ja) * | 2008-10-10 | 2012-03-01 | アクテリオン ファーマシューティカルズ リミテッド | ２−ベンゾチオフェニル−及び２−ナフチル−オキサゾリジノン、並びにそれらのアザアイソスター（ａｚａｉｓｏｓｔｅｒｅ）類似体 |
| AR088691A1 (es) | 2011-11-08 | 2014-06-25 | Actelion Pharmaceuticals Ltd | Derivados antibioticos de 2-oxo-oxazolidin-3,5-diilo |
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| BR112015026261A2 (pt) | 2017-07-25 |
| AU2014255326B2 (en) | 2018-09-13 |
| EA201501025A1 (ru) | 2016-08-31 |
| BR112015026261A8 (pt) | 2017-12-26 |
| WO2014170821A1 (en) | 2014-10-23 |
| HK1221459A1 (zh) | 2017-06-02 |
| CN105143216B (zh) | 2018-04-13 |
| MX2015014576A (es) | 2016-03-04 |
| MA38588A1 (fr) | 2017-05-31 |
| EP2986607A1 (en) | 2016-02-24 |
| CN105143216A (zh) | 2015-12-09 |
| PH12015502411A1 (en) | 2016-02-22 |
| EP2986607B1 (en) | 2017-06-14 |
| TW201516043A (zh) | 2015-05-01 |
| TWI631119B (zh) | 2018-08-01 |
| SG11201508479RA (en) | 2015-11-27 |
| JP6375365B2 (ja) | 2018-08-15 |
| AU2014255326A1 (en) | 2015-11-26 |
| US20160075722A1 (en) | 2016-03-17 |
| CA2907832A1 (en) | 2014-10-23 |
| CL2015003019A1 (es) | 2016-09-30 |
| ES2640482T3 (es) | 2017-11-03 |
| US9527867B2 (en) | 2016-12-27 |
| EA029361B1 (ru) | 2018-03-30 |
| JP2016516805A (ja) | 2016-06-09 |
| AR095884A1 (es) | 2015-11-18 |
| MX362338B (es) | 2019-01-11 |
| PL2986607T3 (pl) | 2017-11-30 |
| MA38588B1 (fr) | 2018-04-30 |
| SA515361261B1 (ar) | 2016-06-15 |
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