OA13032A - Antbacterial indolone oxazolidinones, intermediates for their preparation and pharmaceutical compositions containing them. - Google Patents
Antbacterial indolone oxazolidinones, intermediates for their preparation and pharmaceutical compositions containing them. Download PDFInfo
- Publication number
- OA13032A OA13032A OA1200500233A OA1200500233A OA13032A OA 13032 A OA13032 A OA 13032A OA 1200500233 A OA1200500233 A OA 1200500233A OA 1200500233 A OA1200500233 A OA 1200500233A OA 13032 A OA13032 A OA 13032A
- Authority
- OA
- OAPI
- Prior art keywords
- oxo
- indol
- dihydro
- difluoro
- methyl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 239000000543 intermediate Substances 0.000 title abstract description 12
- QSOIEACKWAXLAR-UHFFFAOYSA-N indol-2-one 1,3-oxazolidin-2-one Chemical class O=C1NCCO1.C1=CC=CC2=NC(=O)C=C21 QSOIEACKWAXLAR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 230000000813 microbial effect Effects 0.000 claims description 3
- UAQSLJSHPUOVTP-UHFFFAOYSA-N benzyl n-(3,3-difluoro-1-methyl-2-oxoindol-5-yl)carbamate Chemical compound C=1C=C2N(C)C(=O)C(F)(F)C2=CC=1NC(=O)OCC1=CC=CC=C1 UAQSLJSHPUOVTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- GUSGRNCCRWWBFS-UHFFFAOYSA-N 5-amino-1-ethyl-3,3-difluoroindol-2-one Chemical compound NC1=CC=C2N(CC)C(=O)C(F)(F)C2=C1 GUSGRNCCRWWBFS-UHFFFAOYSA-N 0.000 claims 1
- ZFGNSEPCIYIKCL-CYBMUJFWSA-N butyl (5r)-3-(3,3-difluoro-1-methyl-2-oxoindol-5-yl)-2-oxo-1,3-oxazolidine-5-carboxylate Chemical compound O=C1O[C@@H](C(=O)OCCCC)CN1C1=CC=C(N(C)C(=O)C2(F)F)C2=C1 ZFGNSEPCIYIKCL-CYBMUJFWSA-N 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 abstract description 3
- -1 2-oxindolyl Chemical group 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 125000000753 cycloalkyl group Chemical group 0.000 description 28
- 125000000392 cycloalkenyl group Chemical group 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 125000005843 halogen group Chemical group 0.000 description 16
- 239000000203 mixture Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- 229940002612 prodrug Drugs 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 3
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- MHNAXLAGKSOPBH-UHFFFAOYSA-N 1-amino-3h-indol-2-one Chemical compound C1=CC=C2N(N)C(=O)CC2=C1 MHNAXLAGKSOPBH-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 238000002814 agar dilution Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000005228 aryl sulfonate group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
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- 230000037396 body weight Effects 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
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- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
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- 238000007429 general method Methods 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000011176 pooling Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 125000006239 protecting group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 239000002002 slurry Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 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
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
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- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- NACONAPBNNDYHF-UHFFFAOYSA-N 1-nitro-3h-indol-2-one Chemical compound C1=CC=C2N([N+](=O)[O-])C(=O)CC2=C1 NACONAPBNNDYHF-UHFFFAOYSA-N 0.000 description 1
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- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
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- BGKABGGFJSTLIL-UHFFFAOYSA-N 3-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical class OCN1CCOC1=O BGKABGGFJSTLIL-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
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- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
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- FGFUBBNNYLNVLJ-UHFFFAOYSA-N indolone Natural products C1=CC=C2C(=O)C=NC2=C1 FGFUBBNNYLNVLJ-UHFFFAOYSA-N 0.000 description 1
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- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
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- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
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- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
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- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
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- 125000004306 triazinyl group Chemical group 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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
- C07D413/02—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44973403P | 2003-02-24 | 2003-02-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA13032A true OA13032A (en) | 2006-11-10 |
Family
ID=32908714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200500233A OA13032A (en) | 2003-02-24 | 2004-02-12 | Antbacterial indolone oxazolidinones, intermediates for their preparation and pharmaceutical compositions containing them. |
Country Status (27)
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|---|---|
| US (1) | US7012088B2 (is) |
| EP (1) | EP1599470A1 (is) |
| JP (1) | JP3887396B2 (is) |
| KR (1) | KR100701226B1 (is) |
| CN (1) | CN100349892C (is) |
| AP (1) | AP2005003375A0 (is) |
| AU (1) | AU2004213246A1 (is) |
| BR (1) | BRPI0406824A (is) |
| CA (1) | CA2515984A1 (is) |
| CO (1) | CO5601039A2 (is) |
| CR (1) | CR7956A (is) |
| EA (1) | EA009725B1 (is) |
| EC (1) | ECSP055980A (is) |
| GE (1) | GEP20084306B (is) |
| HK (1) | HK1082253A1 (is) |
| HR (1) | HRP20050658A2 (is) |
| IS (1) | IS7883A (is) |
| MA (1) | MA27661A1 (is) |
| MX (1) | MXPA05008960A (is) |
| NO (1) | NO20052794L (is) |
| OA (1) | OA13032A (is) |
| PL (1) | PL377428A1 (is) |
| RS (1) | RS20050649A (is) |
| TN (1) | TNSN05202A1 (is) |
| UA (1) | UA80326C2 (is) |
| WO (1) | WO2004074282A1 (is) |
| ZA (1) | ZA200505225B (is) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7141588B2 (en) * | 2002-02-25 | 2006-11-28 | Pfizer, Inc. | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
| BRPI0514020A (pt) * | 2004-08-06 | 2008-05-27 | Pharmacia & Upjohn Co Llc | oxindóis oxazolidinonas como agentes antibacterianos |
| WO2006106426A1 (en) * | 2005-04-06 | 2006-10-12 | Pharmacia & Upjohn Company Llc | An oxindole oxazolidinone as antibacterial agent |
| AU2006231919A1 (en) * | 2005-04-06 | 2006-10-12 | Pharmacia & Upjohn Company Llc | 7-fluoro-1,3-dihydro-indol-2-one oxazolidinones as antibacterial agents |
| SI1928454T1 (sl) | 2005-05-10 | 2015-01-30 | Intermune, Inc. | Piridonski derivati za moduliranje s stresom aktiviranega protein kinaznega sistema |
| WO2007088478A1 (en) * | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Indazole oxazolidinones as antibacterial agents |
| CA2637158A1 (en) * | 2006-02-08 | 2007-08-16 | Pfizer Products Inc. | Oxazolidinones containing oxindoles as antibacterial agents |
| JP5627574B2 (ja) | 2008-06-03 | 2014-11-19 | インターミューン， インコーポレイテッド | 炎症性および線維性疾患を治療するための化合物および方法 |
| FR2948940B1 (fr) * | 2009-08-04 | 2011-07-22 | Servier Lab | Nouveaux derives dihydroindolones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| JP5685384B2 (ja) * | 2010-03-29 | 2015-03-18 | 公益財団法人相模中央化学研究所 | ３，３−ジフルオロ−２，３−ジヒドロインドール−２−オン誘導体の製造方法 |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| HUE034106T2 (en) * | 2012-10-17 | 2018-01-29 | Univ Okayama | Compound, tautomer and geometric isomer thereof, compound, tautomer or salt of geometric isomer, process for preparing the compound, tautomer, isomer or salt, antimicrobial agent and anti-infectious drug |
| CN103193794B (zh) * | 2013-04-12 | 2016-04-06 | 中国药科大学 | 一种异吲哚酮并异噁唑类稠环化合物及其合成方法 |
| KR102373700B1 (ko) | 2014-04-02 | 2022-03-11 | 인터뮨, 인크. | 항섬유성 피리디논 |
| CN107151225B (zh) * | 2017-06-30 | 2020-05-08 | 贵州大学 | 2-羟基吲哚类衍生物、其制备方法和用途 |
| CN113773306B (zh) * | 2021-10-29 | 2023-11-10 | 四川农业大学 | 3,3-二取代吲哚酮类化合物及其制备方法和应用 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE201870T1 (de) | 1988-09-15 | 2001-06-15 | Upjohn Co | 3-(stickstoff substituierte)phenyl-5-beta- amidomethyloxazoliden-2-one |
| US5225565A (en) * | 1988-09-15 | 1993-07-06 | The Upjohn Company | Antibacterial 3-(fused-ring substituted)phenyl-5β-amidomethyloxazolidin-2-ones |
| US5164510A (en) * | 1988-09-15 | 1992-11-17 | The Upjohn Company | 5'Indolinyl-5β-amidomethyloxazolidin-2-ones |
| MY115155A (en) | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| DE19514313A1 (de) * | 1994-08-03 | 1996-02-08 | Bayer Ag | Benzoxazolyl- und Benzothiazolyloxazolidinone |
| HRP960159A2 (en) | 1995-04-21 | 1997-08-31 | Bayer Ag | Benzocyclopentane oxazolidinones containing heteroatoms |
| DE19601627A1 (de) * | 1996-01-18 | 1997-07-24 | Bayer Ag | Heteroatomhaltige Cyclopentanopyridyl-Oxazolidinone |
| DE19604223A1 (de) * | 1996-02-06 | 1997-08-07 | Bayer Ag | Neue substituierte Oxazolidinone |
| DE19805117A1 (de) | 1998-02-09 | 1999-08-12 | Bayer Ag | Neue Oxazolidinone mit azolhaltigen Tricyclen |
| CN1311787A (zh) | 1998-06-05 | 2001-09-05 | 阿斯特拉曾尼卡有限公司 | 噁唑烷酮衍生物、其制备方法以及含有它们的药物组合物 |
| GB9812019D0 (en) | 1998-06-05 | 1998-07-29 | Zeneca Ltd | Chemical compounds |
| GB9821938D0 (en) | 1998-10-09 | 1998-12-02 | Zeneca Ltd | Chemical compounds |
| AU1045300A (en) | 1998-11-17 | 2000-06-05 | Bayer Aktiengesellschaft | Novel heterocyclyl-substituted oxazolidone derivatives |
| DE19962924A1 (de) | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
| PE20011124A1 (es) | 2000-03-31 | 2001-10-28 | Upjohn Co | Nuevos agentes antibacterianos de benzosultam oxazolidinona |
| GB0009803D0 (en) | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| US8048386B2 (en) | 2002-02-25 | 2011-11-01 | Cepheid | Fluid processing and control |
| PE20030044A1 (es) | 2000-11-17 | 2003-02-09 | Upjohn Co | Isoxazolinonas biciclicas de formula i |
| EP1443930A1 (en) | 2001-10-25 | 2004-08-11 | AstraZeneca AB | Isoxazoline derivatives useful as antimicrobials |
-
2004
- 2004-01-22 US US10/762,838 patent/US7012088B2/en not_active Expired - Fee Related
- 2004-02-12 WO PCT/IB2004/000466 patent/WO2004074282A1/en active Application Filing
- 2004-02-12 JP JP2005518544A patent/JP3887396B2/ja not_active Expired - Fee Related
- 2004-02-12 OA OA1200500233A patent/OA13032A/en unknown
- 2004-02-12 EP EP04710451A patent/EP1599470A1/en not_active Withdrawn
- 2004-02-12 EA EA200501341A patent/EA009725B1/ru not_active IP Right Cessation
- 2004-02-12 KR KR1020057015556A patent/KR100701226B1/ko not_active IP Right Cessation
- 2004-02-12 CA CA002515984A patent/CA2515984A1/en not_active Abandoned
- 2004-02-12 RS YUP-2005/0649A patent/RS20050649A/sr unknown
- 2004-02-12 MX MXPA05008960A patent/MXPA05008960A/es active IP Right Grant
- 2004-02-12 PL PL377428A patent/PL377428A1/pl not_active Application Discontinuation
- 2004-02-12 AU AU2004213246A patent/AU2004213246A1/en not_active Abandoned
- 2004-02-12 BR BR0406824-6A patent/BRPI0406824A/pt not_active IP Right Cessation
- 2004-02-12 GE GEAP20048948A patent/GEP20084306B/en unknown
- 2004-02-12 AP AP2005003375A patent/AP2005003375A0/xx unknown
- 2004-02-12 CN CNB2004800027371A patent/CN100349892C/zh not_active Expired - Fee Related
- 2004-12-02 UA UAA200509025A patent/UA80326C2/uk unknown
-
2005
- 2005-06-09 NO NO20052794A patent/NO20052794L/no not_active Application Discontinuation
- 2005-06-09 IS IS7883A patent/IS7883A/is unknown
- 2005-06-28 ZA ZA200505225A patent/ZA200505225B/en unknown
- 2005-07-19 HR HR20050658A patent/HRP20050658A2/hr not_active Application Discontinuation
- 2005-08-19 CO CO05082195A patent/CO5601039A2/es not_active Application Discontinuation
- 2005-08-22 CR CR7956A patent/CR7956A/es unknown
- 2005-08-24 MA MA28456A patent/MA27661A1/fr unknown
- 2005-08-24 EC EC2005005980A patent/ECSP055980A/es unknown
- 2005-08-24 TN TNP2005000202A patent/TNSN05202A1/fr unknown
-
2006
- 2006-04-11 HK HK06104354A patent/HK1082253A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050102135A (ko) | 2005-10-25 |
| HRP20050658A2 (en) | 2005-12-31 |
| CN100349892C (zh) | 2007-11-21 |
| EP1599470A1 (en) | 2005-11-30 |
| KR100701226B1 (ko) | 2007-03-29 |
| CA2515984A1 (en) | 2004-09-02 |
| PL377428A1 (pl) | 2006-02-06 |
| TNSN05202A1 (fr) | 2007-06-11 |
| AP2005003375A0 (en) | 2005-09-30 |
| NO20052794D0 (no) | 2005-06-09 |
| CO5601039A2 (es) | 2006-01-31 |
| UA80326C2 (en) | 2007-09-10 |
| EA200501341A1 (ru) | 2006-02-24 |
| MA27661A1 (fr) | 2005-12-01 |
| ZA200505225B (en) | 2006-11-29 |
| JP3887396B2 (ja) | 2007-02-28 |
| CN1742008A (zh) | 2006-03-01 |
| RS20050649A (en) | 2007-11-15 |
| HK1082253A1 (en) | 2006-06-02 |
| NO20052794L (no) | 2005-11-01 |
| US20040176610A1 (en) | 2004-09-09 |
| GEP20084306B (en) | 2008-02-11 |
| WO2004074282A1 (en) | 2004-09-02 |
| AU2004213246A1 (en) | 2004-09-02 |
| IS7883A (is) | 2005-06-09 |
| MXPA05008960A (es) | 2005-11-04 |
| EA009725B1 (ru) | 2008-02-28 |
| ECSP055980A (es) | 2006-01-16 |
| CR7956A (es) | 2005-12-01 |
| US7012088B2 (en) | 2006-03-14 |
| BRPI0406824A (pt) | 2005-12-27 |
| JP2006515012A (ja) | 2006-05-18 |
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