DK175696B1 - 5'-Indolinyloxazolidin-2-oner med farmaceutisk acceptable salte deraf - Google Patents
5'-Indolinyloxazolidin-2-oner med farmaceutisk acceptable salte deraf Download PDFInfo
- Publication number
- DK175696B1 DK175696B1 DK199100455A DK45591A DK175696B1 DK 175696 B1 DK175696 B1 DK 175696B1 DK 199100455 A DK199100455 A DK 199100455A DK 45591 A DK45591 A DK 45591A DK 175696 B1 DK175696 B1 DK 175696B1
- Authority
- DK
- Denmark
- Prior art keywords
- alkyl
- acetamidomethyl
- oxazolidin
- optionally substituted
- defined above
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 10
- -1 phenyl furanyl Chemical group 0.000 claims abstract description 57
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 44
- MMTBDUQKEDQERD-UHFFFAOYSA-N 5-(2,3-dihydroindol-1-yl)-1,3-oxazolidin-2-one Chemical compound O1C(=O)NCC1N1C2=CC=CC=C2CC1 MMTBDUQKEDQERD-UHFFFAOYSA-N 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910006069 SO3H Inorganic materials 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 abstract description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 abstract 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 34
- 125000001424 substituent group Chemical group 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 230000002829 reductive effect Effects 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 238000007429 general method Methods 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 150000001721 carbon Chemical group 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- NVZIFMAZKAYQJR-UHFFFAOYSA-N 3-(aminomethyl)-1,3-oxazolidin-2-one Chemical compound NCN1CCOC1=O NVZIFMAZKAYQJR-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- WSDUFDGEYKOQRT-UHFFFAOYSA-N 1-(5-amino-2,3-dihydroindol-1-yl)ethanone Chemical compound NC1=CC=C2N(C(=O)C)CCC2=C1 WSDUFDGEYKOQRT-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 150000001540 azides Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- XPUGGFXNUVIKGP-UHFFFAOYSA-N 5-(iodomethyl)-1,3-oxazolidin-2-one Chemical class ICC1CNC(=O)O1 XPUGGFXNUVIKGP-UHFFFAOYSA-N 0.000 description 4
- WJQWYAJTPPYORB-UHFFFAOYSA-N 5-nitro-2,3-dihydro-1h-indole Chemical class [O-][N+](=O)C1=CC=C2NCCC2=C1 WJQWYAJTPPYORB-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 3
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- OJKKTNFCWMBYMT-UHFFFAOYSA-N 1-(5-nitro-2,3-dihydroindol-1-yl)ethanone Chemical compound [O-][N+](=O)C1=CC=C2N(C(=O)C)CCC2=C1 OJKKTNFCWMBYMT-UHFFFAOYSA-N 0.000 description 2
- MKDCJAPHKZPKOU-UHFFFAOYSA-N 1-nitro-2,3-dihydroindole Chemical class C1=CC=C2N([N+](=O)[O-])CCC2=C1 MKDCJAPHKZPKOU-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- DFRUQMGMUUOGBZ-UHFFFAOYSA-N C1=CC=C2N([N])CCC2=C1 Chemical compound C1=CC=C2N([N])CCC2=C1 DFRUQMGMUUOGBZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001923 cyclic compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UWTATZPHSA-N (R)-malic acid Chemical compound OC(=O)[C@H](O)CC(O)=O BJEPYKJPYRNKOW-UWTATZPHSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- CNSBIJRLKLHUIQ-UHFFFAOYSA-N 2,3-dihydro-1h-indol-5-amine Chemical class NC1=CC=C2NCCC2=C1 CNSBIJRLKLHUIQ-UHFFFAOYSA-N 0.000 description 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DAOZBJCTEPJGES-UHFFFAOYSA-N 4-chloro-2-methylpyridine Chemical compound CC1=CC(Cl)=CC=N1 DAOZBJCTEPJGES-UHFFFAOYSA-N 0.000 description 1
- HUHZAMBLEKHDBP-UHFFFAOYSA-N 5-(aminomethyl)-1,3-oxazolidin-2-one Chemical class NCC1CNC(=O)O1 HUHZAMBLEKHDBP-UHFFFAOYSA-N 0.000 description 1
- QQJDFBSOHQQLGC-UHFFFAOYSA-N 5-(aminomethyl)-3-phenyl-1,3-oxazolidin-2-one Chemical class O=C1OC(CN)CN1C1=CC=CC=C1 QQJDFBSOHQQLGC-UHFFFAOYSA-N 0.000 description 1
- WHXUEJAEOKJMAD-UHFFFAOYSA-N 5-(hydroxymethyl)-3-phenyl-1,3-oxazolidin-2-one Chemical class O=C1OC(CO)CN1C1=CC=CC=C1 WHXUEJAEOKJMAD-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SZEALPAXUKGEQL-UHFFFAOYSA-N C(Cl)(Cl)Cl.[I] Chemical compound C(Cl)(Cl)Cl.[I] SZEALPAXUKGEQL-UHFFFAOYSA-N 0.000 description 1
- 0 C*1(C)*(*)CC*C(C2)*(*)CC*2C1* Chemical compound C*1(C)*(*)CC*C(C2)*(*)CC*2C1* 0.000 description 1
- QIRLHDVLLITZAI-UHFFFAOYSA-N C1(=CC=CC=C1)C1N(C(OC1O)=O)C Chemical class C1(=CC=CC=C1)C1N(C(OC1O)=O)C QIRLHDVLLITZAI-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 101000845005 Macrovipera lebetina Disintegrin lebein-2-alpha Proteins 0.000 description 1
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
- 102000010909 Monoamine Oxidase Human genes 0.000 description 1
- 108010062431 Monoamine oxidase Proteins 0.000 description 1
- 241000186367 Mycobacterium avium Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- NNIDNYBZNJNHHA-UHFFFAOYSA-N N-[[3-[5-(cyclopentanecarbonyl)-2,3-dihydroindol-1-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1(CCCC1)C(=O)C=1C=C2CCN(C2=CC=1)N1C(OC(C1)CNC(C)=O)=O NNIDNYBZNJNHHA-UHFFFAOYSA-N 0.000 description 1
- 101001077374 Oryza sativa subsp. japonica UMP-CMP kinase 3 Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- VZCUDXSTYNADOY-UHFFFAOYSA-N [N].O=C1NCCO1 Chemical compound [N].O=C1NCCO1 VZCUDXSTYNADOY-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 238000000451 chemical ionisation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 210000004197 pelvis Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
-
- 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
-
- 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
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK200401246A DK175940B1 (da) | 1988-09-15 | 2004-08-18 | 3-(Nitrogensubstituerede)-phenyl-5beta-aminomethyloxazolidin-2-oner og farmaceutisk acceptable salte deraf samt anvendelse af disse forbindelser til fremstilling af et lægemiddel |
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24498888A | 1988-09-15 | 1988-09-15 | |
| US24498888 | 1988-09-15 | ||
| US25385088A | 1988-10-05 | 1988-10-05 | |
| US25385088 | 1988-10-05 | ||
| US32494289A | 1989-03-17 | 1989-03-17 | |
| US32494289 | 1989-03-17 | ||
| PCT/US1989/003548 WO1990002744A1 (en) | 1988-09-15 | 1989-08-22 | In position 3 substituted-5-beta-amidomethyl-oxazolidin-2-ones |
| US8903548 | 1989-08-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK45591D0 DK45591D0 (da) | 1991-03-13 |
| DK45591A DK45591A (da) | 1991-03-13 |
| DK175696B1 true DK175696B1 (da) | 2005-01-24 |
Family
ID=27399816
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK199100455A DK175696B1 (da) | 1988-09-15 | 1991-03-13 | 5'-Indolinyloxazolidin-2-oner med farmaceutisk acceptable salte deraf |
| DK200401246A DK175940B1 (da) | 1988-09-15 | 2004-08-18 | 3-(Nitrogensubstituerede)-phenyl-5beta-aminomethyloxazolidin-2-oner og farmaceutisk acceptable salte deraf samt anvendelse af disse forbindelser til fremstilling af et lægemiddel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK200401246A DK175940B1 (da) | 1988-09-15 | 2004-08-18 | 3-(Nitrogensubstituerede)-phenyl-5beta-aminomethyloxazolidin-2-oner og farmaceutisk acceptable salte deraf samt anvendelse af disse forbindelser til fremstilling af et lægemiddel |
Country Status (13)
| Country | Link |
|---|---|
| EP (3) | EP0609905B1 (enExample) |
| JP (2) | JP2865211B2 (enExample) |
| KR (1) | KR0138262B1 (enExample) |
| AT (2) | ATE201870T1 (enExample) |
| AU (1) | AU617871B2 (enExample) |
| CA (1) | CA1335103C (enExample) |
| DE (2) | DE68929303T2 (enExample) |
| DK (2) | DK175696B1 (enExample) |
| ES (1) | ES2157934T3 (enExample) |
| GR (1) | GR3036491T3 (enExample) |
| LV (1) | LV12888B (enExample) |
| TW (1) | TW219936B (enExample) |
| WO (1) | WO1990002744A1 (enExample) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5231188A (en) * | 1989-11-17 | 1993-07-27 | The Upjohn Company | Tricyclic [6.5.51]-fused oxazolidinone antibacterial agents |
| EP0636623B1 (en) * | 1990-06-07 | 2001-08-16 | AstraZeneca AB | Indole derivatives as 5-HT1- like agonists |
| BR9206353A (pt) * | 1991-08-14 | 1995-11-07 | Procter & Gamble Pharma | Uretanos cíclicos utilizáveis como agentes antiarrítmicos e antifibrilatórios |
| SK283420B6 (sk) * | 1992-05-08 | 2003-07-01 | Pharmacia & Upjohn Company | Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny |
| WO1994001110A1 (en) * | 1992-07-08 | 1994-01-20 | The Upjohn Company | 5'-INDOLINYL OXAZOLIDINONES USEFUL AGAINST $i(MYCOBACTERIUM TUBERCULOSIS) |
| US5688792A (en) * | 1994-08-16 | 1997-11-18 | Pharmacia & Upjohn Company | Substituted oxazine and thiazine oxazolidinone antimicrobials |
| DE4425609A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | Benzofuranyl- und Benzothienyloxazolidinone |
| DE4425613A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | 5-gliedrige Heteroaryl-oxazolidinone |
| DE4425612A1 (de) * | 1994-07-20 | 1996-04-04 | Bayer Ag | 6-gliedrige stickstoffhaltige Heteroaryl-oxazolidinone |
| DE19514313A1 (de) * | 1994-08-03 | 1996-02-08 | Bayer Ag | Benzoxazolyl- und Benzothiazolyloxazolidinone |
| CN1068325C (zh) * | 1994-10-26 | 2001-07-11 | 法玛西雅厄普约翰美国公司 | 苯基噁唑烷酮抗菌剂 |
| ATE233766T1 (de) * | 1994-11-15 | 2003-03-15 | Upjohn Co | Antibakterielle bizyklische oxazin und thiazin- oxazolidinone |
| ES2163004T3 (es) * | 1995-02-03 | 2002-01-16 | Upjohn Co | Feniloxazolidinona sustituida por un anillo heteroaromatico como agente antimicrobiano. |
| HRP960159A2 (en) * | 1995-04-21 | 1997-08-31 | Bayer Ag | Benzocyclopentane oxazolidinones containing heteroatoms |
| FI974180A0 (fi) * | 1995-05-11 | 1997-11-10 | Upjohn Co | Spirosyklisiä ja bisyklisiä diatsinyyli- ja karbatsinyylioksatsolidinoneja |
| US5883093A (en) * | 1995-09-12 | 1999-03-16 | Pharmacia & Upjohn Company | Phenyloxazolidinone antimicrobials |
| ZA968661B (en) * | 1995-11-17 | 1998-04-14 | Upjohn Co | Oxazolidinone antibacterial agent with tricyclic substituents. |
| DE19601264A1 (de) | 1996-01-16 | 1997-07-17 | Bayer Ag | Pyrido-annellierte Thienyl- und Furanyl-Oxazolidinone |
| DE19601265A1 (de) * | 1996-01-16 | 1997-07-17 | Bayer Ag | 2-Oxo- und 2-Thio-1,2-dihydrochinolinyl-oxazolidinone |
| DE19601627A1 (de) * | 1996-01-18 | 1997-07-24 | Bayer Ag | Heteroatomhaltige Cyclopentanopyridyl-Oxazolidinone |
| GB9601666D0 (en) * | 1996-01-27 | 1996-03-27 | Zeneca Ltd | Chemical compounds |
| HRP970049A2 (en) | 1996-02-06 | 1998-04-30 | Bayer Ag | New heteroaryl oxazolidinones |
| DE19604223A1 (de) | 1996-02-06 | 1997-08-07 | Bayer Ag | Neue substituierte Oxazolidinone |
| GB9702213D0 (en) * | 1996-02-24 | 1997-03-26 | Zeneca Ltd | Chemical compounds |
| GB9609919D0 (en) * | 1996-05-11 | 1996-07-17 | Zeneca Ltd | Chemical compounds |
| NZ501412A (en) * | 1997-05-30 | 2001-11-30 | Upjohn Co | Oxazolidinone antibacterial agents having a thiocarbonyl functionality |
| US6255304B1 (en) | 1997-05-30 | 2001-07-03 | Pharmacia & Upjohn Company | Oxazolidinone antibacterial agents having a thiocarbonyl functionality |
| DE19730847A1 (de) * | 1997-07-18 | 1999-01-28 | Bayer Ag | Tricyclisch substituierte Oxazolidinone |
| GB9717807D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| GB9717804D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| AU739055B2 (en) * | 1997-11-12 | 2001-10-04 | Pharmacia & Upjohn Company | Oxazolidinone derivatives and pharmaceutical compositions |
| GB9725244D0 (en) | 1997-11-29 | 1998-01-28 | Zeneca Ltd | Chemical compounds |
| DE19802239A1 (de) * | 1998-01-22 | 1999-07-29 | Bayer Ag | Neue mit Bicyclen substituierte Oxazolidinone |
| EP1049682A1 (en) | 1998-01-23 | 2000-11-08 | Versicor, Inc. | Oxazolidinone combinatorial libraries, compositions and methods of preparation |
| US7002020B1 (en) | 1998-01-23 | 2006-02-21 | Pharmacia & Upjohn Company | Oxazolidinone combinatorial libraries, compositions and methods of preparation |
| US6562844B2 (en) | 1998-01-23 | 2003-05-13 | Pharmacia & Upjohn Company | Oxazolidinone combinatorial libraries, compositions and methods of preparation |
| BR0010982A (pt) | 1999-05-27 | 2002-03-05 | Upjohn Co | Novas oxazolidinonas bicìclicas como agentes antibacterianos |
| EP1200416A1 (en) | 1999-07-28 | 2002-05-02 | Pharmacia & Upjohn Company | Oxazolidinones and their use as antiinfectives |
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| GB0009803D0 (en) | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| CZ2003228A3 (cs) | 2000-07-17 | 2003-06-18 | Ranbaxy Laboratories Limited | Oxazolidinonové deriváty jako antimikrobiální látky |
| EP1659125B1 (en) | 2000-10-02 | 2010-06-02 | Emory University | Triptolide analogs for the treatment of autoimmune and inflammatory disorders |
| PE20020689A1 (es) | 2000-11-17 | 2002-08-03 | Upjohn Co | Oxazolidinonas con un heterociclo de 6 o 7 miembros unidos con enlace anular al benceno |
| US6956040B2 (en) | 2001-07-16 | 2005-10-18 | Ranbaxy Laboratories Limited | Oxazolidinone piperazinyl derivatives as potential antimicrobials |
| GB0118407D0 (en) * | 2001-07-27 | 2001-09-19 | Cipla Ltd | Oxazolidinone derivatives as antibacterial agents |
| TW200306819A (en) | 2002-01-25 | 2003-12-01 | Vertex Pharma | Indazole compounds useful as protein kinase inhibitors |
| US7012088B2 (en) * | 2003-02-24 | 2006-03-14 | Pharmacia & Upjohn Company | Indolone oxazolidinones and derivatives thereof |
| CA2575702A1 (en) * | 2004-08-06 | 2006-02-16 | Pharmacia & Upjohn Company Llc | Oxindole oxazolidinones as antibacterial agents |
| SE0402763D0 (sv) * | 2004-11-11 | 2004-11-11 | Astrazeneca Ab | Nitro indazole derivatives |
| AU2006231919A1 (en) | 2005-04-06 | 2006-10-12 | Pharmacia & Upjohn Company Llc | 7-fluoro-1,3-dihydro-indol-2-one oxazolidinones as antibacterial agents |
| CA2603943A1 (en) * | 2005-04-06 | 2006-10-12 | Pharmacia & Upjohn Company Llc | An oxindole oxazolidinone as antibacterial agent |
| JP5425806B2 (ja) * | 2007-12-24 | 2014-02-26 | シプラ・リミテッド | プロパルギル化アミノインダン誘導体の合成方法 |
| US8598156B2 (en) | 2010-03-25 | 2013-12-03 | Glaxosmithkline Llc | Chemical compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8506659A1 (es) * | 1983-06-07 | 1985-08-01 | Du Pont | Un procedimiento para la preparacion de nuevos derivados del amino-metil-oxooxazolidinil-benzeno. |
| CA1260948A (en) * | 1984-12-05 | 1989-09-26 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents |
| US4801600A (en) * | 1987-10-09 | 1989-01-31 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
-
1989
- 1989-08-22 EP EP94102762A patent/EP0609905B1/en not_active Expired - Lifetime
- 1989-08-22 JP JP1509255A patent/JP2865211B2/ja not_active Expired - Fee Related
- 1989-08-22 WO PCT/US1989/003548 patent/WO1990002744A1/en not_active Ceased
- 1989-08-22 DE DE68929303T patent/DE68929303T2/de not_active Expired - Fee Related
- 1989-08-22 AT AT94102762T patent/ATE201870T1/de not_active IP Right Cessation
- 1989-08-22 ES ES94102762T patent/ES2157934T3/es not_active Expired - Lifetime
- 1989-08-22 EP EP89308506A patent/EP0359418B1/en not_active Expired - Lifetime
- 1989-08-22 DE DE68918792T patent/DE68918792T2/de not_active Expired - Fee Related
- 1989-08-22 AT AT89308506T patent/ATE112773T1/de not_active IP Right Cessation
- 1989-08-22 EP EP89909990A patent/EP0434714A1/en active Pending
- 1989-08-22 AU AU41957/89A patent/AU617871B2/en not_active Ceased
- 1989-08-28 CA CA000609594A patent/CA1335103C/en not_active Expired - Fee Related
- 1989-08-29 TW TW078106662A patent/TW219936B/zh active
-
1990
- 1990-05-15 KR KR1019900701012A patent/KR0138262B1/ko not_active Expired - Fee Related
-
1991
- 1991-03-13 DK DK199100455A patent/DK175696B1/da not_active IP Right Cessation
-
1998
- 1998-07-07 JP JP19194998A patent/JP3188418B2/ja not_active Expired - Fee Related
-
2001
- 2001-08-31 GR GR20010401350T patent/GR3036491T3/el not_active IP Right Cessation
-
2002
- 2002-06-06 LV LVP-02-104A patent/LV12888B/en unknown
-
2004
- 2004-08-18 DK DK200401246A patent/DK175940B1/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE68918792D1 (de) | 1994-11-17 |
| EP0359418A1 (en) | 1990-03-21 |
| HK1002234A1 (en) | 1998-08-07 |
| ATE201870T1 (de) | 2001-06-15 |
| DE68918792T2 (de) | 1995-03-30 |
| KR0138262B1 (ko) | 1998-05-15 |
| KR900701780A (ko) | 1990-12-04 |
| CA1335103C (en) | 1995-04-04 |
| EP0609905B1 (en) | 2001-06-06 |
| ATE112773T1 (de) | 1994-10-15 |
| WO1990002744A1 (en) | 1990-03-22 |
| AU617871B2 (en) | 1991-12-05 |
| EP0609905A1 (en) | 1994-08-10 |
| DK45591D0 (da) | 1991-03-13 |
| LV12888B (en) | 2002-12-20 |
| EP0434714A1 (en) | 1991-07-03 |
| JP3188418B2 (ja) | 2001-07-16 |
| DK200401246A (da) | 2004-08-18 |
| JPH04500665A (ja) | 1992-02-06 |
| JP2865211B2 (ja) | 1999-03-08 |
| GR3036491T3 (en) | 2001-11-30 |
| DK175940B1 (da) | 2005-08-01 |
| DE68929303T2 (de) | 2002-05-02 |
| TW219936B (enExample) | 1994-02-01 |
| JPH1180139A (ja) | 1999-03-26 |
| AU4195789A (en) | 1990-04-02 |
| DK45591A (da) | 1991-03-13 |
| EP0359418B1 (en) | 1994-10-12 |
| ES2157934T3 (es) | 2001-09-01 |
| DE68929303D1 (de) | 2001-07-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK175696B1 (da) | 5'-Indolinyloxazolidin-2-oner med farmaceutisk acceptable salte deraf | |
| JP3628329B2 (ja) | オキサゾリジノン誘導体及びこれを有効成分とする医薬組成物 | |
| AU616185B2 (en) | Oxazolidinones | |
| US10533006B2 (en) | Nitrogen-containing heterocycle and carbocycle derivatives having TrkA inhibitory activity | |
| HRP20030522A2 (en) | Heterocyclic compounds having antibacterial activity, process for their preparatoin and pharmaceutical compositions containing them | |
| CZ2003228A3 (cs) | Oxazolidinonové deriváty jako antimikrobiální látky | |
| JP2000204084A (ja) | チオカルバミド酸誘導体 | |
| AU640783B2 (en) | Oxazolidinones | |
| JP2002501065A (ja) | 新規二環置換オキサゾリジノン | |
| NO325656B1 (no) | Anti-syrefaste bakterielle midler inneholdende pyridonkarboksylsyrer som den aktive bestanddel | |
| CZ299199A3 (cs) | Oxazolidinony jako 5-HT2A antagonisty | |
| TW200804358A (en) | Novel compound having heterocycle | |
| AU2003295171B2 (en) | Benzoxazocines and their use as monoamine-reuptake inhibitors | |
| JP7349567B2 (ja) | Ｍ４作動薬としての５－オキサ－２－アザスピロ［３．４］オクタン誘導体 | |
| JPH05501553A (ja) | 三環［６，５，５］／［６，６，５］―縮合オキサゾリジノン抗菌剤 | |
| ES2336047T3 (es) | Derivados de 3-azabiciclo-(4,1,0)heptano para el tratamiento de la depresion. | |
| JP2000229978A (ja) | オキサゾリジノン及び抗菌剤としてのそれらの使用 | |
| US12109203B2 (en) | Substituted oxazolidinones for the treatment of mammalian infections | |
| RU2798336C2 (ru) | Новые соединения для лечения инфекций млекопитающих | |
| HK40043248A (en) | Substituted oxazolidinones for the treatment of mammalian infections | |
| WO2006056877A2 (en) | Diazepine oxazolidinones as antibacterial agents | |
| WO2020234636A1 (en) | Novel compounds for the treatment of mammalian infections | |
| HK1002234B (en) | 5'-indolinyl-5beta-amidomethyloxazolidin-2-ones, 3-(fused-ring substituted)phenyl-5beta-amidomethy-loxazolidin-2-ones and 3-(nitrogen substituted)phenyl-5beta-amidomethyloxazolidin-2-ones |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |
Country of ref document: DK |