UA80326C2 - Antibacterial indolone oxazolidinones, intermediates for their preparation and pharmaceutical compositions containing them - Google Patents

Antibacterial indolone oxazolidinones, intermediates for their preparation and pharmaceutical compositions containing them Download PDF

Info

Publication number: UA80326C2
Authority: UA; Ukraine
Prior art keywords: alkyl; oxo; indol; difluoro; dihydro
Prior art date: 2003-02-24

Application number

UAA200509025A

Other languages

English (en)

Ukrainian (uk)

Inventor

Thony-Jo Poel

Priority date (The priority date 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 date listed.)

2003-02-24

Filing date

2004-12-02

Publication date

2007-09-10

2004-12-02 Application filed filed Critical

2007-09-10 Publication of UA80326C2 publication Critical patent/UA80326C2/uk

Links

238000002360 preparation method Methods 0.000 title claims abstract description 20
239000008194 pharmaceutical composition Substances 0.000 title claims description 9
239000000543 intermediate Substances 0.000 title abstract description 12
230000000844 anti-bacterial effect Effects 0.000 title description 4
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 67
125000000217 alkyl group Chemical group 0.000 claims description 34
125000003118 aryl group Chemical group 0.000 claims description 29
125000000753 cycloalkyl group Chemical group 0.000 claims description 29
229910052736 halogen Inorganic materials 0.000 claims description 24
150000002367 halogens Chemical class 0.000 claims description 24
125000000547 substituted alkyl group Chemical group 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 13
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
229910052757 nitrogen Chemical group 0.000 claims description 6
NZKREZAIZZAEIG-UHFFFAOYSA-N 5-amino-3,3-difluoro-1-methylindol-2-one Chemical compound NC1=CC=C2N(C)C(=O)C(F)(F)C2=C1 NZKREZAIZZAEIG-UHFFFAOYSA-N 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
229940079593 drug Drugs 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
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 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
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 4
229940126601 medicinal product Drugs 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000005017 substituted alkenyl group Chemical group 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
239000011593 sulfur Chemical group 0.000 claims description 4
AROWSJMUCOGVDJ-UHFFFAOYSA-N 3,3-difluoro-1-methyl-5-nitroindol-2-one Chemical compound [O-][N+](=O)C1=CC=C2N(C)C(=O)C(F)(F)C2=C1 AROWSJMUCOGVDJ-UHFFFAOYSA-N 0.000 claims description 3
241000124008 Mammalia Species 0.000 claims description 3
OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
ARRNIHYZUQTUGN-UHFFFAOYSA-N 1-ethyl-3,3-difluoro-5-nitroindol-2-one Chemical compound [O-][N+](=O)C1=CC=C2N(CC)C(=O)C(F)(F)C2=C1 ARRNIHYZUQTUGN-UHFFFAOYSA-N 0.000 claims description 2
NTSDOTAMHHORSQ-UHFFFAOYSA-N benzyl n-(1-ethyl-3,3-difluoro-2-oxoindol-5-yl)carbamate Chemical compound C=1C=C2N(CC)C(=O)C(F)(F)C2=CC=1NC(=O)OCC1=CC=CC=C1 NTSDOTAMHHORSQ-UHFFFAOYSA-N 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
238000012876 topography Methods 0.000 claims 1
239000003242 anti bacterial agent Substances 0.000 abstract description 3
239000000203 mixture Substances 0.000 description 37
-1 4-oxo-2-imidazolyl Chemical group 0.000 description 28
125000000392 cycloalkenyl group Chemical group 0.000 description 24
125000001424 substituent group Chemical group 0.000 description 21
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
238000000034 method Methods 0.000 description 15
239000002904 solvent Substances 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
241000282414 Homo sapiens Species 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
125000003277 amino group Chemical group 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000012298 atmosphere Substances 0.000 description 6
239000002585 base Chemical class 0.000 description 6
239000012267 brine Substances 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
229940002612 prodrug Drugs 0.000 description 5
239000000651 prodrug Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
229920001817 Agar Polymers 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000012907 medicinal substance 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
238000000746 purification Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
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 4
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 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000008272 agar Substances 0.000 description 3
150000001414 amino alcohols Chemical class 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000002401 inhibitory effect Effects 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
125000001624 naphthyl group Chemical group 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000005303 weighing Methods 0.000 description 3
BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 2
FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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
241000282412 Homo Species 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
230000004913 activation Effects 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
208000022362 bacterial infectious disease Diseases 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000006285 cell suspension Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
238000007429 general method Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
230000008569 process Effects 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
125000006413 ring segment Chemical group 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000003396 thiol group Chemical group [H]S* 0.000 description 2
229930192474 thiophene Natural products 0.000 description 2
CUYUBEFFEABTMX-UHFFFAOYSA-N (1-ethyl-3,3-difluoro-2-oxoindol-5-yl)carbamic acid Chemical compound OC(=O)NC1=CC=C2N(CC)C(=O)C(F)(F)C2=C1 CUYUBEFFEABTMX-UHFFFAOYSA-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
125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 description 1
125000001399 1,2,3-triazolyl group Chemical class N1N=NC(=C1)* 0.000 description 1
125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 1
125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 1
125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 description 1
125000004518 1,2,5-thiadiazol-3-yl group Chemical group S1N=C(C=N1)* 0.000 description 1
125000004522 1,3,4-thiadiazol-5-yl group Chemical group S1C=NN=C1* 0.000 description 1
KNWCDYSKJSREAQ-UHFFFAOYSA-N 1,3-oxazolidine-2-carboxylic acid Chemical compound OC(=O)C1NCCO1 KNWCDYSKJSREAQ-UHFFFAOYSA-N 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
QXMJAMBPNHRAPD-UHFFFAOYSA-N 1-oxido-3h-oxathiazol-1-ium Chemical compound [O-][O+]1SNC=C1 QXMJAMBPNHRAPD-UHFFFAOYSA-N 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
LYOPOVPPAPVXHE-UHFFFAOYSA-N 3,3-difluoro-5-nitro-1h-indol-2-one Chemical compound [O-][N+](=O)C1=CC=C2NC(=O)C(F)(F)C2=C1 LYOPOVPPAPVXHE-UHFFFAOYSA-N 0.000 description 1
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
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
KWIVRAVCZJXOQC-UHFFFAOYSA-N 3h-oxathiazole Chemical compound N1SOC=C1 KWIVRAVCZJXOQC-UHFFFAOYSA-N 0.000 description 1
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
HUHZAMBLEKHDBP-UHFFFAOYSA-N 5-(aminomethyl)-1,3-oxazolidin-2-one Chemical compound NCC1CNC(=O)O1 HUHZAMBLEKHDBP-UHFFFAOYSA-N 0.000 description 1
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241000256844 Apis mellifera Species 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
241000606125 Bacteroides Species 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
FAIFRACTBXWXGY-JTTXIWGLSA-N COc1ccc2C[C@H]3N(C)CC[C@@]45[C@@H](Oc1c24)[C@@]1(OC)C=C[C@@]35C[C@@H]1[C@](C)(O)CCc1ccccc1 Chemical compound COc1ccc2C[C@H]3N(C)CC[C@@]45[C@@H](Oc1c24)[C@@]1(OC)C=C[C@@]35C[C@@H]1[C@](C)(O)CCc1ccccc1 FAIFRACTBXWXGY-JTTXIWGLSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 1
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239000004375 Dextrin Substances 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
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108010010803 Gelatin Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
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238000010934 O-alkylation reaction Methods 0.000 description 1
PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
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241000295644 Staphylococcaceae Species 0.000 description 1
241000838698 Togo Species 0.000 description 1
HKNSIVFWRXBWCK-UHFFFAOYSA-N [N].NC1=CC=CC=C1 Chemical group [N].NC1=CC=CC=C1 HKNSIVFWRXBWCK-UHFFFAOYSA-N 0.000 description 1
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239000004480 active ingredient Substances 0.000 description 1
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238000002814 agar dilution Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
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229910052796 boron Inorganic materials 0.000 description 1
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AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
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125000006165 cyclic alkyl group Chemical group 0.000 description 1
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235000019425 dextrin Nutrition 0.000 description 1
238000010586 diagram Methods 0.000 description 1
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000013504 emergency use authorization Methods 0.000 description 1
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239000008393 encapsulating agent Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000000592 heterocycloalkyl group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000011534 incubation Methods 0.000 description 1
QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 1
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
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
239000000314 lubricant Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
150000004701 malic acid derivatives Chemical class 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
244000052769 pathogen Species 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000002304 perfume Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
238000011160 research Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
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
239000007909 solid dosage form Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
125000005415 substituted alkoxy group Chemical group 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
230000009466 transformation Effects 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
108010050327 trypticase-soy broth Proteins 0.000 description 1
UFVDXRZDNSEHDT-UHFFFAOYSA-N undec-2-ene Chemical compound [CH2]CCCCCCCC=CC UFVDXRZDNSEHDT-UHFFFAOYSA-N 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

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)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (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)

UAA200509025A 2003-02-24 2004-12-02 Antibacterial indolone oxazolidinones, intermediates for their preparation and pharmaceutical compositions containing them UA80326C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US44973403P	2003-02-24	2003-02-24
PCT/IB2004/000466 WO2004074282A1 (en)	2003-02-24	2004-02-12	Antibacterial indolone oxazolidinones, intermediates for their preparation and pharmaceutical compositions containing them

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UA80326C2 true UA80326C2 (en)	2007-09-10

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US (1)	US7012088B2 (pl)
EP (1)	EP1599470A1 (pl)
JP (1)	JP3887396B2 (pl)
KR (1)	KR100701226B1 (pl)
CN (1)	CN100349892C (pl)
AP (1)	AP2005003375A0 (pl)
AU (1)	AU2004213246A1 (pl)
BR (1)	BRPI0406824A (pl)
CA (1)	CA2515984A1 (pl)
CO (1)	CO5601039A2 (pl)
CR (1)	CR7956A (pl)
EA (1)	EA009725B1 (pl)
EC (1)	ECSP055980A (pl)
GE (1)	GEP20084306B (pl)
HR (1)	HRP20050658A2 (pl)
IS (1)	IS7883A (pl)
MA (1)	MA27661A1 (pl)
MX (1)	MXPA05008960A (pl)
NO (1)	NO20052794L (pl)
OA (1)	OA13032A (pl)
PL (1)	PL377428A1 (pl)
RS (1)	RS20050649A (pl)
TN (1)	TNSN05202A1 (pl)
UA (1)	UA80326C2 (pl)
WO (1)	WO2004074282A1 (pl)
ZA (1)	ZA200505225B (pl)

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US7141588B2 (en) *	2002-02-25	2006-11-28	Pfizer, Inc.	N-aryl-2-oxazolidinone-5-carboxamides and their derivatives
BRPI0513083A (pt) *	2004-08-06	2008-04-22	Pharmacia & Upjohn Co Llc	oxazolidinonas contendo oxindóis como agentes antibacterianos
CA2603943A1 (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
MX2007014114A (es)	2005-05-10	2008-03-14	Intermune Inc	Derivados de piridona para modular el sistema de proteina cinasa activada por estres.
WO2007088478A1 (en) *	2006-02-01	2007-08-09	Pfizer Products Inc.	Indazole oxazolidinones as antibacterial agents
WO2007091147A1 (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
EP2910547B1 (en) *	2012-10-17	2017-06-14	Okayama University	Compound; tautomer and geometric isomer thereof; salt of said compound, tautomer, or geometric isomer; method for manufacturing said compound, tautomer, isomer, or salt; antimicrobial agent; and anti-infective 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
US10233195B2 (en)	2014-04-02	2019-03-19	Intermune, Inc.	Anti-fibrotic pyridinones
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

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ATE112773T1 (de)	1988-09-15	1994-10-15	Upjohn Co	5-indolinyl-5-beta-amidomethyloxazolidin-2-one, 3-(substituierte kondensierte)phenyl-5-beta amidomethyloxazolidin-2-one und 3-(nitrogen- substituierte)phenyl-5-beta-amidomethyloxazolid n-2-one.
US5164510A (en) *	1988-09-15	1992-11-17	The Upjohn Company	5'Indolinyl-5β-amidomethyloxazolidin-2-ones
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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
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KR20010052615A (ko)	1998-06-05	2001-06-25	다비드 에 질레스	옥사졸리디논 유도체, 이것의 제조 방법 및 이것을함유하는 약학 조성물
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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
JP2005512975A (ja)	2001-10-25	2005-05-12	アストラゼネカアクチボラグ	抗菌薬として有用なイソキサゾリン誘導体

2004
- 2004-01-22 US US10/762,838 patent/US7012088B2/en not_active Expired - Fee Related
- 2004-02-12 EP EP04710451A patent/EP1599470A1/en not_active Withdrawn
- 2004-02-12 JP JP2005518544A patent/JP3887396B2/ja not_active Expired - Fee Related
- 2004-02-12 PL PL377428A patent/PL377428A1/pl not_active Application Discontinuation
- 2004-02-12 KR KR1020057015556A patent/KR100701226B1/ko not_active Expired - Fee Related
- 2004-02-12 GE GEAP20048948A patent/GEP20084306B/en unknown
- 2004-02-12 BR BR0406824-6A patent/BRPI0406824A/pt not_active IP Right Cessation
- 2004-02-12 OA OA1200500233A patent/OA13032A/en unknown
- 2004-02-12 CA CA002515984A patent/CA2515984A1/en not_active Abandoned
- 2004-02-12 AU AU2004213246A patent/AU2004213246A1/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 AP AP2005003375A patent/AP2005003375A0/xx unknown
- 2004-02-12 HR HR20050658A patent/HRP20050658A2/hr not_active Application Discontinuation
- 2004-02-12 CN CNB2004800027371A patent/CN100349892C/zh not_active Expired - Fee Related
- 2004-02-12 WO PCT/IB2004/000466 patent/WO2004074282A1/en not_active Ceased
- 2004-02-12 EA EA200501341A patent/EA009725B1/ru not_active IP Right Cessation
- 2004-12-02 UA UAA200509025A patent/UA80326C2/uk unknown
2005
- 2005-06-09 IS IS7883A patent/IS7883A/is unknown
- 2005-06-09 NO NO20052794A patent/NO20052794L/no not_active Application Discontinuation
- 2005-06-28 ZA ZA200505225A patent/ZA200505225B/en unknown
- 2005-08-19 CO CO05082195A patent/CO5601039A2/es not_active Application Discontinuation
- 2005-08-22 CR CR7956A patent/CR7956A/es unknown
- 2005-08-24 TN TNP2005000202A patent/TNSN05202A1/fr unknown
- 2005-08-24 MA MA28456A patent/MA27661A1/fr unknown
- 2005-08-24 EC EC2005005980A patent/ECSP055980A/es unknown

Also Published As

Publication number	Publication date
OA13032A (en)	2006-11-10
KR20050102135A (ko)	2005-10-25
EP1599470A1 (en)	2005-11-30
US20040176610A1 (en)	2004-09-09
HK1082253A1 (zh)	2006-06-02
NO20052794D0 (no)	2005-06-09
ZA200505225B (en)	2006-11-29
AP2005003375A0 (en)	2005-09-30
IS7883A (is)	2005-06-09
JP3887396B2 (ja)	2007-02-28
AU2004213246A1 (en)	2004-09-02
WO2004074282A1 (en)	2004-09-02
HRP20050658A2 (en)	2005-12-31
CR7956A (es)	2005-12-01
PL377428A1 (pl)	2006-02-06
NO20052794L (no)	2005-11-01
CO5601039A2 (es)	2006-01-31
CN1742008A (zh)	2006-03-01
CA2515984A1 (en)	2004-09-02
US7012088B2 (en)	2006-03-14
EA200501341A1 (ru)	2006-02-24
RS20050649A (sr)	2007-11-15
KR100701226B1 (ko)	2007-03-29
TNSN05202A1 (fr)	2007-06-11
BRPI0406824A (pt)	2005-12-27
GEP20084306B (en)	2008-02-11
CN100349892C (zh)	2007-11-21
ECSP055980A (es)	2006-01-16
MXPA05008960A (es)	2005-11-04
MA27661A1 (fr)	2005-12-01
EA009725B1 (ru)	2008-02-28
JP2006515012A (ja)	2006-05-18

Publication	Publication Date	Title
US5164510A (en)	1992-11-17	5'Indolinyl-5β-amidomethyloxazolidin-2-ones
EP1668005B1 (en)	2007-02-14	Acyloxymethylcarbamate prodrugs of oxazolidinones
KR100701226B1 (ko)	2007-03-29	항균성 인돌론 옥사졸리디논, 이의 제조를 위한 중간체 및이를 포함하는 약학 조성물
EA005567B1 (ru)	2005-04-28	Оксазолидиноны, обладающие сульфоксиминовой функциональностью
US20040127530A1 (en)	2004-07-01	Antimibicrobial [3.1.0.] bicyclic oxazolidinone derivatives
JP2006522791A (ja)	2006-10-05	抗微生物性［３．１．０］ビシクロヘキシルフェニルオキサゾリジノン誘導体および類似体
EP1539745B1 (en)	2006-03-29	N-aryl-2-oxazolidinones and their derivatives
US6825225B2 (en)	2004-11-30	Bicyclic isoxazolinones as antibacterial agents
US20040204463A1 (en)	2004-10-14	N-aryl-2-oxazolidinone-5-carboxamides and their derivatives
JP2007503426A (ja)	2007-02-22	新規な抗微生物性アリールオキサゾリジノン化合物
EP1565186B1 (en)	2006-11-02	N-(4-(piperazin-1-yl)-phenyl-2-oxazolidinone-5-carboxamide derivates and related compounds as antibacterial agents
KR100467309B1 (ko)	2005-07-18	옥사졸리디논유도체및그의제조방법및항균제조성물
HK1082253B (en)	2008-03-28	Antibacterial indolone oxazolidinones, intermediates for their preparation and pharmaceutical compositions containing them