SK50096A3 - Benzocyclopentanoxyzolidinones which contains hetero-atom, process for producing them, their use and pharmaceutical composition containing these substances - Google Patents
Benzocyclopentanoxyzolidinones which contains hetero-atom, process for producing them, their use and pharmaceutical composition containing these substances Download PDFInfo
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- SK50096A3 SK50096A3 SK500-96A SK50096A SK50096A3 SK 50096 A3 SK50096 A3 SK 50096A3 SK 50096 A SK50096 A SK 50096A SK 50096 A3 SK50096 A3 SK 50096A3
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- 125000005842 heteroatom Chemical group 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 27
- 239000000126 substance Substances 0.000 title description 5
- 239000008194 pharmaceutical composition Substances 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 65
- -1 NHSO2R Chemical group 0.000 claims abstract description 50
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 28
- 125000002252 acyl group Chemical group 0.000 claims abstract description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
- 125000003944 tolyl group Chemical group 0.000 claims abstract description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 7
- 125000004001 thioalkyl group Chemical group 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 161
- 125000004432 carbon atom Chemical group C* 0.000 claims description 124
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 119
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 89
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000000460 chlorine Substances 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 26
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 239000012442 inert solvent Substances 0.000 claims description 22
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 21
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 125000004434 sulfur atom Chemical group 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001298 alcohols Chemical class 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 12
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 11
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 9
- 238000007127 saponification reaction Methods 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 229910052721 tungsten Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 238000007796 conventional method Methods 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- 230000029936 alkylation Effects 0.000 claims description 6
- 238000005804 alkylation reaction Methods 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 150000001540 azides Chemical class 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 4
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical group [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims description 4
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 150000001351 alkyl iodides Chemical class 0.000 claims description 3
- ABDBNWQRPYOPDF-UHFFFAOYSA-N carbonofluoridic acid Chemical compound OC(F)=O ABDBNWQRPYOPDF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000006479 redox reaction Methods 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 238000001149 thermolysis Methods 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229920001577 copolymer Chemical group 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 abstract 1
- 101100134925 Gallus gallus COR6 gene Proteins 0.000 abstract 1
- 101150020251 NR13 gene Proteins 0.000 abstract 1
- 229910006074 SO2NH2 Inorganic materials 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 abstract 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 110
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 57
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- 239000000243 solution Substances 0.000 description 40
- 239000002904 solvent Substances 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000005160 1H NMR spectroscopy Methods 0.000 description 33
- 235000019441 ethanol Nutrition 0.000 description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
- 239000011541 reaction mixture Substances 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 229910052799 carbon Inorganic materials 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- 239000002244 precipitate Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- BXQNSPXDWSNUKE-UHFFFAOYSA-N 1,3-benzothiazole 1-oxide Chemical compound C1=CC=C2S(=O)C=NC2=C1 BXQNSPXDWSNUKE-UHFFFAOYSA-N 0.000 description 20
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 20
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 18
- 239000002585 base Substances 0.000 description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000010933 acylation Effects 0.000 description 6
- 238000005917 acylation reaction Methods 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 6
- 150000008282 halocarbons Chemical class 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- YTSRSHZBPTWWPQ-YBTMIULGSA-N N-[[(5S)-3-(3-methyl-2-methylsulfanyl-2H-1,3-benzothiazol-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide hydroiodide Chemical compound I.C=1C=C2N(C)C(SC)SC2=CC=1N1C[C@H](CNC(C)=O)OC1=O YTSRSHZBPTWWPQ-YBTMIULGSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 230000009435 amidation Effects 0.000 description 5
- 238000007112 amidation reaction Methods 0.000 description 5
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- BPXSNWOACLQLLY-QRPNPIFTSA-N (5s)-5-(aminomethyl)-3-(3-methyl-2-oxo-1,3-benzothiazol-6-yl)-1,3-oxazolidin-2-one;hydrochloride Chemical compound Cl.C1=C2SC(=O)N(C)C2=CC=C1N1C[C@H](CN)OC1=O BPXSNWOACLQLLY-QRPNPIFTSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
- C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D419/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
- C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19514769 | 1995-04-21 | ||
| DE19544106A DE19544106A1 (de) | 1995-04-21 | 1995-11-27 | Heteroatomhaltige Benzocyclopentanoxazolidinone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK50096A3 true SK50096A3 (en) | 1997-05-07 |
Family
ID=26014539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK500-96A SK50096A3 (en) | 1995-04-21 | 1996-04-19 | Benzocyclopentanoxyzolidinones which contains hetero-atom, process for producing them, their use and pharmaceutical composition containing these substances |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6069160A (ja) |
| EP (1) | EP0738726B1 (ja) |
| JP (1) | JP3967401B2 (ja) |
| CN (1) | CN1138582A (ja) |
| AT (1) | ATE206120T1 (ja) |
| AU (1) | AU705071B2 (ja) |
| BG (1) | BG100525A (ja) |
| CA (1) | CA2174473A1 (ja) |
| CZ (1) | CZ114296A3 (ja) |
| EE (1) | EE9600043A (ja) |
| ES (1) | ES2164182T3 (ja) |
| HR (1) | HRP960159A2 (ja) |
| HU (1) | HUP9601001A3 (ja) |
| IL (1) | IL117954A0 (ja) |
| MA (1) | MA23845A1 (ja) |
| MX (1) | MX9601399A (ja) |
| NO (1) | NO305909B1 (ja) |
| NZ (1) | NZ286400A (ja) |
| SG (1) | SG52774A1 (ja) |
| SK (1) | SK50096A3 (ja) |
| TR (1) | TR199600319A2 (ja) |
Families Citing this family (71)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9601666D0 (en) * | 1996-01-27 | 1996-03-27 | Zeneca Ltd | Chemical compounds |
| 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 |
| GB9717804D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| GB9717807D0 (en) * | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| US6617453B1 (en) | 1997-10-24 | 2003-09-09 | Clariant Finance (Bvi) Limited | Triphendioxazine compounds |
| DE19747175A1 (de) * | 1997-10-24 | 1999-04-29 | Clariant Int Ltd | Chlorhaltige Triphendioxazin-Verbindungen |
| RU2212407C2 (ru) | 1997-11-10 | 2003-09-20 | Бристол-Маерс Сквибб Компани | Бензотиазольные ингибиторы протеинтирозинкиназ |
| GB9725244D0 (en) | 1997-11-29 | 1998-01-28 | Zeneca Ltd | Chemical compounds |
| US6562844B2 (en) | 1998-01-23 | 2003-05-13 | Pharmacia & Upjohn Company | Oxazolidinone combinatorial libraries, compositions and methods of preparation |
| 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 |
| WO2000029409A1 (de) * | 1998-11-17 | 2000-05-25 | Bayer Aktiengesellschaft | Neue heterocyclyl-substituierte oxazolidon-derivate |
| DE19905278A1 (de) * | 1999-02-09 | 2000-08-10 | Bayer Ag | Oxazolidinone und ihre Verwendung als antibakterielle Mittel |
| DE19913401A1 (de) | 1999-03-25 | 2000-09-28 | Clariant Gmbh | Verfahren zur Herstellung von Dioxazin-Verbindungen |
| NZ516853A (en) | 1999-07-28 | 2003-11-28 | Upjohn Co | Oxazolidinones and their use as anti-infectives |
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| US6518285B2 (en) | 1999-12-21 | 2003-02-11 | Ortho Mcneil Pharmaceutical, Inc. | Piperidinyloxy and pyrrolidinyloxy oxazolidinone antibacterials |
| 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 |
| WO2002032857A1 (en) * | 2000-10-17 | 2002-04-25 | Pharmacia & Upjohn Company | Methods of producing oxazolidinone compounds |
| HUP0303494A3 (en) * | 2000-12-15 | 2009-08-28 | Vertex Pharma | Parmaceutical compositions containing bacterial gyrase inhibitors and uses thereof |
| ES2248633T3 (es) * | 2001-04-17 | 2006-03-16 | MERCK & CO., INC. | Antibioticos oxazolidinona que contienen biciclo (3,1,o)hexano y derivados de los mismos. |
| SI1598339T1 (sl) * | 2001-04-18 | 2009-12-31 | Euro Celtique Sa | Derivati 1-(4-amino.cikloheksil)-1,3-dihidro-2h-benzimidazol-2-ona in sorodne spojine kot nociceptinski analogi in ORL1 ligandi za zdravljenje bolečine |
| DE10129725A1 (de) * | 2001-06-20 | 2003-01-02 | Bayer Ag | Kombinationstherapie substituierter Oxazolidinone |
| WO2003048136A1 (en) * | 2001-11-29 | 2003-06-12 | Merck & Co., Inc. | Cyclopropyl hexane containing oxazolidinone antibiotics and derivatives thereof |
| AR038536A1 (es) * | 2002-02-25 | 2005-01-19 | Upjohn Co | N-aril-2-oxazolidinona-5- carboxamidas y sus derivados |
| US7141588B2 (en) * | 2002-02-25 | 2006-11-28 | Pfizer, Inc. | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
| CA2476545A1 (en) * | 2002-03-29 | 2003-10-16 | Pharmacia & Upjohn Company | Parenteral, intravenous, and oral administration of oxazolidinones for treating diabetic foot infections |
| EP1539745B1 (en) * | 2002-08-12 | 2006-03-29 | Pharmacia & Upjohn Company LLC | N-aryl-2-oxazolidinones and their derivatives |
| WO2004026848A1 (en) * | 2002-09-20 | 2004-04-01 | Lupin Limited | Oxazolidinone derivatives, process for their preperation and their use as antimycobacterial agents |
| BR0316483A (pt) * | 2002-11-21 | 2005-10-11 | Upjohn Co | Derivados de n-(4-(piperazin-1-il)-fenil-2-oxazolidinona-5-carboxami da e compostos relacionados como agentes antibacterianos |
| DE10300111A1 (de) * | 2003-01-07 | 2004-07-15 | Bayer Healthcare Ag | Verfahren zur Herstellung von 5-Chlor-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl}-methyl)-2-thiophencarboxamid |
| US7618974B2 (en) | 2003-01-31 | 2009-11-17 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US8404852B2 (en) | 2003-01-31 | 2013-03-26 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US7569591B2 (en) | 2003-01-31 | 2009-08-04 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US8193352B2 (en) | 2003-01-31 | 2012-06-05 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| AR042956A1 (es) | 2003-01-31 | 2005-07-13 | Vertex Pharma | Inhibidores de girasa y usos de los mismos |
| US7582641B2 (en) | 2003-01-31 | 2009-09-01 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| EP1594494A1 (en) * | 2003-02-07 | 2005-11-16 | Warner-Lambert Company LLC | Oxazolidinone derivatives n-substituted by a bicyclic ring, for use as antibacterial agents |
| EP1594865A2 (en) * | 2003-02-07 | 2005-11-16 | Warner-Lambert Company LLC | Antibacterial agents |
| US7012088B2 (en) | 2003-02-24 | 2006-03-14 | Pharmacia & Upjohn Company | Indolone oxazolidinones and derivatives thereof |
| US20040204463A1 (en) * | 2003-04-01 | 2004-10-14 | Harris Christina Renee | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
| KR20060113625A (ko) * | 2003-07-02 | 2006-11-02 | 머크 앤드 캄파니 인코포레이티드 | 시클로프로필기 치환된 옥사졸리디논 항생제 및 그의유도체 |
| WO2005005399A1 (en) * | 2003-07-02 | 2005-01-20 | Merck & Co., Inc. | Oxazolidinone antibiotics and derivatives thereof |
| CA2529294A1 (en) * | 2003-07-02 | 2005-01-20 | Merck & Co., Inc. | Oxazolidinone antibiotics and derivatives thereof |
| AU2004256085B2 (en) * | 2003-07-02 | 2007-12-06 | Kyorin, Pharmaceutical Co., Ltd. | Cyclopropyl Group Substituted Oxazolydinone Antibiotics and Derivatives Thereof |
| US7304050B2 (en) * | 2003-09-16 | 2007-12-04 | Pfizer Inc. | Antibacterial agents |
| DE10355461A1 (de) | 2003-11-27 | 2005-06-23 | Bayer Healthcare Ag | Verfahren zur Herstellung einer festen, oral applizierbaren pharmazeutischen Zusammensetzung |
| WO2005082897A1 (en) * | 2004-01-28 | 2005-09-09 | Pharmacia & Upjohn Company Llc | Oxazolidinone antibacterial agents |
| WO2005082900A2 (en) * | 2004-01-28 | 2005-09-09 | Pharmacia & Upjohn Company Llc | Oxazolidinone amidoximes as antibacterial agents |
| MX2007001568A (es) * | 2004-08-06 | 2007-04-16 | Pharmacia & Upjohn Co Llc | Oxindol oxazolidinonas como agentes antibacterianos. |
| DE102004062475A1 (de) * | 2004-12-24 | 2006-07-06 | Bayer Healthcare Ag | Feste, oral applizierbare pharmazeutische Darreichungsformen mit modifizierter Freisetzung |
| EP1685841A1 (en) | 2005-01-31 | 2006-08-02 | Bayer Health Care Aktiengesellschaft | Prevention and treatment of thromboembolic disorders |
| KR20070116989A (ko) * | 2005-04-06 | 2007-12-11 | 파마시아 앤드 업존 캄파니 엘엘씨 | 항균제로서의 옥신돌 옥사졸리디논 |
| DE102005045518A1 (de) | 2005-09-23 | 2007-03-29 | Bayer Healthcare Ag | 2-Aminoethoxyessigsäure-Derivate und ihre Verwendung |
| DE102005047561A1 (de) | 2005-10-04 | 2007-04-05 | Bayer Healthcare Ag | Feste, oral applizierbare pharmazeutische Darreichungsformen mit schneller Wirkstofffreisetzung |
| SG166126A1 (en) | 2005-10-04 | 2010-11-29 | Bayer Schering Pharma Ag | Novel polymorphous form and the amorphous form of 5-chloro-n-({(5s)-2-oxo- 3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidine-5-yl}-methyl)-2-thiophene carboxamide |
| DE102005048824A1 (de) * | 2005-10-10 | 2007-04-12 | Bayer Healthcare Ag | Behandlung und Prophylaxe von Mikroangiopathien |
| DE102006051625A1 (de) * | 2006-11-02 | 2008-05-08 | Bayer Materialscience Ag | Kombinationstherapie substituierter Oxazolidinone |
| BR112013017985B1 (pt) | 2011-01-14 | 2021-06-29 | Spero Therapeutics Inc. | Formas sólidas de inibidor de girase (r)-1-etil-3-[6-flúor-5-[2-(1-hidróxi-1-metil-etil)pirimidin- 5-il]-7-(tetra-hidrofuran-2-il)-1h-benzimidazol-2-il]ureia, seu sal de ácido clorídrico, método de preparação das mesmas e composição farmacêutica que os compreende |
| RU2609259C2 (ru) | 2011-01-14 | 2017-01-31 | Сперо Тринем, Инк. | Пиримидиновые ингибиторы гиразы и топоизомеразы iv |
| AU2012205420B2 (en) | 2011-01-14 | 2016-12-08 | Spero Therapeutics, Inc. | Process of making gyrase and topoisomerase IV inhibitors |
| RU2013137753A (ru) | 2011-01-14 | 2015-02-20 | Вертекс Фармасьютикалз Инкорпорейтед | Твердые формы ингибитора гиразы (r)-1-этил-3-[5-[2-(1-гидрокси-1-метилэтил)пиримидин-5-ил]-7-(тетрагидрофуран-2-ил)-1н-бензимидазол-2-ил]мочевины |
| EP2721026B1 (en) | 2011-06-20 | 2016-03-02 | Vertex Pharmaceuticals Incorporated | Phosphate esters of gyrase and topoisomerase inhibitors |
| US9572809B2 (en) | 2012-07-18 | 2017-02-21 | Spero Trinem, Inc. | Combination therapy to treat Mycobacterium diseases |
| TWI595002B (zh) | 2012-07-18 | 2017-08-11 | 思沛羅三南公司 | （Ｒ）－２－（５－（２－（３－乙基脲基）－６－氟－７－（四氫呋喃－２－基）－１Ｈ－苯并［ｄ］咪唑－５－基）嘧啶－２－基）丙烷－２－基磷酸二氫鹽之固體形式及其鹽 |
| MY182716A (en) * | 2013-01-30 | 2021-02-03 | Sumitomo Chemical Co | Method for controlling arthropod pest |
| CN114075439B (zh) * | 2021-12-07 | 2023-07-28 | 西安瑞联新材料股份有限公司 | 一种苯并戊烷类液晶化合物及其组合物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4705799A (en) * | 1983-06-07 | 1987-11-10 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents |
| DE3723797A1 (de) * | 1987-07-18 | 1989-01-26 | Merck Patent Gmbh | Oxazolidinone |
| US4965268A (en) * | 1987-10-09 | 1990-10-23 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4921869A (en) * | 1987-10-09 | 1990-05-01 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene 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 |
| CA1320730C (en) * | 1987-10-16 | 1993-07-27 | The Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl aroylbenzene derivatives useful as antibacterial agents |
| US5254577A (en) * | 1988-07-29 | 1993-10-19 | The Du Pont Merck Pharmaceutical Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| DE68929303T2 (de) * | 1988-09-15 | 2002-05-02 | Pharmacia & Upjohn Co., Kalamazoo | 3-(Stickstoff substituierte)phenyl-5-beta-amidomethyloxazoliden-2-one |
| JP2669579B2 (ja) * | 1991-10-23 | 1997-10-29 | エーザイ株式会社 | オキサゾリドン誘導体 |
| DE19514313A1 (de) * | 1994-08-03 | 1996-02-08 | Bayer Ag | Benzoxazolyl- und Benzothiazolyloxazolidinone |
-
1996
- 1996-04-04 HR HR19544106.0A patent/HRP960159A2/hr not_active Application Discontinuation
- 1996-04-09 EP EP96105539A patent/EP0738726B1/de not_active Expired - Lifetime
- 1996-04-09 ES ES96105539T patent/ES2164182T3/es not_active Expired - Lifetime
- 1996-04-09 AT AT96105539T patent/ATE206120T1/de not_active IP Right Cessation
- 1996-04-12 US US08/631,516 patent/US6069160A/en not_active Expired - Fee Related
- 1996-04-15 MX MX9601399A patent/MX9601399A/es unknown
- 1996-04-16 JP JP11711796A patent/JP3967401B2/ja not_active Expired - Fee Related
- 1996-04-17 AU AU50735/96A patent/AU705071B2/en not_active Ceased
- 1996-04-17 TR TR96/00319A patent/TR199600319A2/xx unknown
- 1996-04-17 HU HU9601001A patent/HUP9601001A3/hu unknown
- 1996-04-18 CA CA002174473A patent/CA2174473A1/en not_active Abandoned
- 1996-04-18 NZ NZ286400A patent/NZ286400A/en unknown
- 1996-04-18 IL IL11795496A patent/IL117954A0/xx unknown
- 1996-04-19 NO NO961559A patent/NO305909B1/no unknown
- 1996-04-19 CN CN96106152A patent/CN1138582A/zh active Pending
- 1996-04-19 SK SK500-96A patent/SK50096A3/sk unknown
- 1996-04-19 EE EE9600043A patent/EE9600043A/xx unknown
- 1996-04-19 CZ CZ961142A patent/CZ114296A3/cs unknown
- 1996-04-19 MA MA24205A patent/MA23845A1/fr unknown
- 1996-04-19 SG SG1996009312A patent/SG52774A1/en unknown
- 1996-04-19 BG BG100525A patent/BG100525A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO961559L (no) | 1996-10-22 |
| BG100525A (en) | 1997-03-31 |
| EP0738726B1 (de) | 2001-09-26 |
| HRP960159A2 (en) | 1997-08-31 |
| ATE206120T1 (de) | 2001-10-15 |
| HUP9601001A3 (en) | 1999-03-01 |
| US6069160A (en) | 2000-05-30 |
| SG52774A1 (en) | 1998-09-28 |
| NZ286400A (en) | 1998-04-27 |
| HUP9601001A2 (hu) | 1998-04-28 |
| IL117954A0 (en) | 1996-08-04 |
| CA2174473A1 (en) | 1996-10-22 |
| AU705071B2 (en) | 1999-05-13 |
| CZ114296A3 (en) | 1997-07-16 |
| NO961559D0 (no) | 1996-04-19 |
| EE9600043A (et) | 1996-12-16 |
| JP3967401B2 (ja) | 2007-08-29 |
| MX9601399A (es) | 1997-04-30 |
| CN1138582A (zh) | 1996-12-25 |
| AU5073596A (en) | 1996-10-31 |
| ES2164182T3 (es) | 2002-02-16 |
| TR199600319A2 (tr) | 1996-11-21 |
| JPH08301869A (ja) | 1996-11-19 |
| MA23845A1 (fr) | 1996-12-31 |
| HU9601001D0 (en) | 1996-06-28 |
| NO305909B1 (no) | 1999-08-16 |
| EP0738726A1 (de) | 1996-10-23 |
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