KR20080108977A - 항균 활성을 지닌 디카르보닐 화합물 - Google Patents

Info

Publication number

KR20080108977A

KR20080108977A KR1020087020277A KR20087020277A KR20080108977A KR 20080108977 A KR20080108977 A KR 20080108977A KR 1020087020277 A KR1020087020277 A KR 1020087020277A KR 20087020277 A KR20087020277 A KR 20087020277A KR 20080108977 A KR20080108977 A KR 20080108977A

Authority

KR

South Korea

Prior art keywords

isoxazol

nre

fluoro

phenyl

piperazin

Prior art date

2006-01-19

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.)

Withdrawn

Links

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• 230000000845 anti-microbial effect Effects 0.000 title description 12
• 125000004989 dicarbonyl group Chemical group 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 144
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 150000002367 halogens Chemical class 0.000 claims abstract description 15
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
• 239000012453 solvate Substances 0.000 claims abstract description 6
• 241001465754 Metazoa Species 0.000 claims abstract description 5
• 208000035143 Bacterial infection Diseases 0.000 claims abstract description 4
• 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 57
• 239000000203 mixture Substances 0.000 claims description 37
• 125000005843 halogen group Chemical group 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 125000002950 monocyclic group Chemical group 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 238000011282 treatment Methods 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 150000001204 N-oxides Chemical class 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 229910052739 hydrogen Inorganic materials 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 238000011321 prophylaxis Methods 0.000 claims description 2
• 229910052703 rhodium Inorganic materials 0.000 claims description 2
• 125000001183 hydrocarbyl group Chemical group 0.000 abstract 5
• 125000003545 alkoxy group Chemical group 0.000 abstract 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
• -1 1,3-butadienyl Chemical group 0.000 description 63
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
• 238000000034 method Methods 0.000 description 47
• 239000007858 starting material Substances 0.000 description 42
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 28
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• 239000000243 solution Substances 0.000 description 18
• 239000002904 solvent Substances 0.000 description 17
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• 238000006243 chemical reaction Methods 0.000 description 15
• 235000019439 ethyl acetate Nutrition 0.000 description 15
• 230000002829 reductive effect Effects 0.000 description 15
• 238000002360 preparation method Methods 0.000 description 13
• 239000000047 product Substances 0.000 description 13
• RZOKQIPOABEQAM-UHFFFAOYSA-N 6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C=N1 RZOKQIPOABEQAM-UHFFFAOYSA-N 0.000 description 12
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• 150000001412 amines Chemical class 0.000 description 12
• 239000000543 intermediate Substances 0.000 description 12
• 238000003786 synthesis reaction Methods 0.000 description 11
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
• 239000002244 precipitate Substances 0.000 description 10
• COYPLDIXZODDDL-UHFFFAOYSA-N 3h-benzimidazole-5-carboxylic acid Chemical class OC(=O)C1=CC=C2N=CNC2=C1 COYPLDIXZODDDL-UHFFFAOYSA-N 0.000 description 9
• ZCIFWRHIEBXBOY-UHFFFAOYSA-N 6-aminonicotinic acid Chemical compound NC1=CC=C(C(O)=O)C=N1 ZCIFWRHIEBXBOY-UHFFFAOYSA-N 0.000 description 9
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
• 239000012267 brine Substances 0.000 description 9
• 238000004440 column chromatography Methods 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• 239000012074 organic phase Substances 0.000 description 9
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 9
• 239000000741 silica gel Substances 0.000 description 9
• 229910002027 silica gel Inorganic materials 0.000 description 9
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• 230000015572 biosynthetic process Effects 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• 239000002253 acid Substances 0.000 description 7
• 125000001309 chloro group Chemical group Cl* 0.000 description 7
• XRTKWPWDSUNLHS-UHFFFAOYSA-N methyl 4-chloro-3-nitrobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 XRTKWPWDSUNLHS-UHFFFAOYSA-N 0.000 description 7
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
• UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical compound C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 238000004587 chromatography analysis Methods 0.000 description 6
• 244000000059 gram-positive pathogen Species 0.000 description 6
• 125000006239 protecting group Chemical group 0.000 description 6
• 150000003254 radicals Chemical class 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• FYEQKMAVRYRMBL-UHFFFAOYSA-N 3-aminopyridine-4-carboxylic acid Chemical compound NC1=CN=CC=C1C(O)=O FYEQKMAVRYRMBL-UHFFFAOYSA-N 0.000 description 5
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 5
• 239000010409 thin film Substances 0.000 description 5
• 238000004809 thin layer chromatography Methods 0.000 description 5
• OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 4
• KAJLCBKTWRUQOI-UHFFFAOYSA-N 1-methylbenzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2N(C)C=NC2=C1 KAJLCBKTWRUQOI-UHFFFAOYSA-N 0.000 description 4
• VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 4
• BOOMHTFCWOJWFO-UHFFFAOYSA-N 3-aminopyridine-2-carboxylic acid Chemical compound NC1=CC=CN=C1C(O)=O BOOMHTFCWOJWFO-UHFFFAOYSA-N 0.000 description 4
• IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 4
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
• IMBBXSASDSZJSX-UHFFFAOYSA-N 4-Carboxypyrazole Chemical compound OC(=O)C=1C=NNC=1 IMBBXSASDSZJSX-UHFFFAOYSA-N 0.000 description 4
• HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 4
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
• 241000191940 Staphylococcus Species 0.000 description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
• 125000000217 alkyl group Chemical group 0.000 description 4
• 238000009835 boiling Methods 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• 238000000576 coating method Methods 0.000 description 4
• 230000000694 effects Effects 0.000 description 4
• 238000001704 evaporation Methods 0.000 description 4
• 230000008020 evaporation Effects 0.000 description 4
• 235000019253 formic acid Nutrition 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 229960003907 linezolid Drugs 0.000 description 4
• TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• 235000005152 nicotinamide Nutrition 0.000 description 4
• 235000017557 sodium bicarbonate Nutrition 0.000 description 4
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 3
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 3
• BIUCOFQROHIAEO-UHFFFAOYSA-N 7-nitroindole-2-carboxylic acid Chemical compound C1=CC([N+]([O-])=O)=C2NC(C(=O)O)=CC2=C1 BIUCOFQROHIAEO-UHFFFAOYSA-N 0.000 description 3
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 3
• 241000194033 Enterococcus Species 0.000 description 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• 108010059993 Vancomycin Proteins 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 150000001263 acyl chlorides Chemical class 0.000 description 3
• 239000012298 atmosphere Substances 0.000 description 3
• 230000003115 biocidal effect Effects 0.000 description 3
• 238000010511 deprotection reaction Methods 0.000 description 3
• 239000006185 dispersion Substances 0.000 description 3
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• 238000010438 heat treatment Methods 0.000 description 3
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
• 150000002430 hydrocarbons Chemical group 0.000 description 3
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
• ONOJJCTXSDBVSP-UHFFFAOYSA-N imidazo[1,2-a]pyridine-6-carboxylic acid Chemical compound C1=C(C(=O)O)C=CC2=NC=CN21 ONOJJCTXSDBVSP-UHFFFAOYSA-N 0.000 description 3
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• 239000003755 preservative agent Substances 0.000 description 3
• DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Natural products OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 3
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
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• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
• 239000000080 wetting agent Substances 0.000 description 3
• QVHJQCGUWFKTSE-YFKPBYRVSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)OC(C)(C)C QVHJQCGUWFKTSE-YFKPBYRVSA-N 0.000 description 2
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 2
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
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