LV13155B - Oxazolidinone derivatives and pharmaceutical compositions containing them - Google Patents
Oxazolidinone derivatives and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- LV13155B LV13155B LVP-04-20A LV040020A LV13155B LV 13155 B LV13155 B LV 13155B LV 040020 A LV040020 A LV 040020A LV 13155 B LV13155 B LV 13155B
- Authority
- LV
- Latvia
- Prior art keywords
- oxo
- oxazolidin
- phenyl
- fluoro
- acetamide
- Prior art date
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- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 title description 7
- 208000035473 Communicable disease Diseases 0.000 claims abstract description 6
- -1 [1,2,4] triazol-4-yl Chemical group 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- UWAHVVNOMMENRW-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(4-oxopiperidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(=O)CC1 UWAHVVNOMMENRW-AWEZNQCLSA-N 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- WMAKNXDMRUDJFA-AWEZNQCLSA-N n-[[(5s)-3-[4-(4-aminopiperidin-1-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(N)CC1 WMAKNXDMRUDJFA-AWEZNQCLSA-N 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 239000004599 antimicrobial Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- NDDMZTVOUVYFGY-VYRBHSGPSA-N n-[[(5s)-3-[3-fluoro-4-[3-(hydroxymethyl)-1,4-dioxa-8-azaspiro[4.5]decan-8-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC2(OC(CO)CO2)CC1 NDDMZTVOUVYFGY-VYRBHSGPSA-N 0.000 claims description 4
- FQHIZQRUIIBONF-INIZCTEOSA-N n-[[(5s)-3-[3-fluoro-4-[4-(1,3-thiazol-2-ylamino)piperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(NC=2SC=CN=2)CC1 FQHIZQRUIIBONF-INIZCTEOSA-N 0.000 claims description 4
- OSQOMFHQXBCOLL-INIZCTEOSA-N n-[[(5s)-3-[4-[4-(dimethylamino)piperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F OSQOMFHQXBCOLL-INIZCTEOSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- VKYTVTWRYPFJEN-KRWDZBQOSA-N [[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperidin-4-ylidene]amino] 2-acetyloxyacetate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(=NOC(=O)COC(C)=O)CC1 VKYTVTWRYPFJEN-KRWDZBQOSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- NNGDLHFWRWOGQF-KZUDCZAMSA-N methyl (3s)-1-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)[C@@H](C(=O)OC)CN1C1=CC=C(N2C(OC(CNC(C)=O)C2)=O)C=C1F NNGDLHFWRWOGQF-KZUDCZAMSA-N 0.000 claims description 3
- OZZBIBRKRAMJMI-KRWDZBQOSA-N n-[[(5s)-3-[3-fluoro-4-[4-(2-oxopropyl)piperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1CC(CC(=O)C)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F OZZBIBRKRAMJMI-KRWDZBQOSA-N 0.000 claims description 3
- DVHNGZMRRRNHJG-HNNXBMFYSA-N n-[[(5s)-3-[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC2(OCCO2)CC1 DVHNGZMRRRNHJG-HNNXBMFYSA-N 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- DVLGNTKUOQIJCC-AWEZNQCLSA-N n-[[(5s)-3-(3-fluoro-4-piperidin-1-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCCCC1 DVLGNTKUOQIJCC-AWEZNQCLSA-N 0.000 claims description 2
- MIOZZWQPNMNBRN-INIZCTEOSA-N n-[[(5s)-3-[3-fluoro-4-[4-(methoxymethoxy)piperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1CC(OCOC)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F MIOZZWQPNMNBRN-INIZCTEOSA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
- CGWXQLQTWMQYKC-QFIPXVFZSA-N [[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperidin-4-ylidene]amino] 2-phenylmethoxyacetate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N(CC1)CCC1=NOC(=O)COCC1=CC=CC=C1 CGWXQLQTWMQYKC-QFIPXVFZSA-N 0.000 claims 1
- UZJFGRLSOAJXKP-HNNXBMFYSA-N [[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperidin-4-ylidene]amino] methyl carbonate Chemical compound C1CC(=NOC(=O)OC)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F UZJFGRLSOAJXKP-HNNXBMFYSA-N 0.000 claims 1
- DJYPTCNBLWFHGW-INIZCTEOSA-N ethyl 1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F DJYPTCNBLWFHGW-INIZCTEOSA-N 0.000 claims 1
- NMWNMGCEBQAKLY-KRWDZBQOSA-N ethyl 3-[2-[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperidin-4-ylidene]hydrazinyl]-3-oxopropanoate Chemical compound C1CC(=NNC(=O)CC(=O)OCC)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F NMWNMGCEBQAKLY-KRWDZBQOSA-N 0.000 claims 1
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000007857 hydrazones Chemical class 0.000 claims 1
- GVBIWBBYCCEXNJ-HNNXBMFYSA-N methyl n-[[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperidin-4-ylidene]amino]carbamate Chemical compound C1CC(=NNC(=O)OC)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F GVBIWBBYCCEXNJ-HNNXBMFYSA-N 0.000 claims 1
- MAPDMEJNKGCWHC-INIZCTEOSA-N n-[[(5s)-3-[3-fluoro-4-[4-(1,2,4-triazol-4-ylimino)piperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N(CC1)CCC1=NN1C=NN=C1 MAPDMEJNKGCWHC-INIZCTEOSA-N 0.000 claims 1
- GKJREEGSBQEYJL-INIZCTEOSA-N n-[[(5s)-3-[3-fluoro-4-[4-(2-hydroxyethoxyimino)piperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(=NOCCO)CC1 GKJREEGSBQEYJL-INIZCTEOSA-N 0.000 claims 1
- PIARQUSOEZZUQA-FQEVSTJZSA-N n-[[(5s)-3-[3-fluoro-4-[4-[4-(2-hydroxyethyl)piperazin-1-yl]iminopiperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N(CC1)CCC1=NN1CCN(CCO)CC1 PIARQUSOEZZUQA-FQEVSTJZSA-N 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 169
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- 239000000243 solution Substances 0.000 description 65
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 239000000203 mixture Substances 0.000 description 61
- 239000002904 solvent Substances 0.000 description 51
- 238000005160 1H NMR spectroscopy Methods 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 238000000034 method Methods 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 23
- 238000010898 silica gel chromatography Methods 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 239000012267 brine Substances 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 230000000845 anti-microbial effect Effects 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 150000001540 azides Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 125000004663 dialkyl amino group Chemical group 0.000 description 5
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 201000008827 tuberculosis Diseases 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- 239000002253 acid Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 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
- QISAUDWTBBNJIR-UHFFFAOYSA-N 2-phenylmethoxyacetyl chloride Chemical compound ClC(=O)COCC1=CC=CC=C1 QISAUDWTBBNJIR-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 208000035143 Bacterial infection Diseases 0.000 description 3
- 241000606125 Bacteroides Species 0.000 description 3
- 241001112696 Clostridia Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000193996 Streptococcus pyogenes Species 0.000 description 3
- 108010059993 Vancomycin Proteins 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 208000022362 bacterial infectious disease Diseases 0.000 description 3
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 229920002472 Starch Polymers 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
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- KEDYVZWXUHWODZ-UHFFFAOYSA-N ethyl 2-(4-aminopiperidin-1-yl)acetate Chemical compound CCOC(=O)CN1CCC(N)CC1 KEDYVZWXUHWODZ-UHFFFAOYSA-N 0.000 description 1
- RUJPPJYDHHAEEK-UHFFFAOYSA-N ethyl piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCNCC1 RUJPPJYDHHAEEK-UHFFFAOYSA-N 0.000 description 1
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- 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
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- QNFBOXWNAVZTSJ-INIZCTEOSA-N methyl 2-[[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperidin-4-ylidene]amino]oxyacetate Chemical compound C1CC(=NOCC(=O)OC)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F QNFBOXWNAVZTSJ-INIZCTEOSA-N 0.000 description 1
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- GWSCGOYPJMPOAT-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(4-hydroxypiperidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(O)CC1 GWSCGOYPJMPOAT-AWEZNQCLSA-N 0.000 description 1
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- HMNHEAVJYUVGEP-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-(4-methylpiperidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1CC(C)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F HMNHEAVJYUVGEP-HNNXBMFYSA-N 0.000 description 1
- CNTDHRBJSROZGM-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(4-methylsulfanylpiperidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1CC(SC)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F CNTDHRBJSROZGM-AWEZNQCLSA-N 0.000 description 1
- QTQHDOSQHSJHBF-HGMXIMQMSA-N n-[[(5s)-3-[3-fluoro-4-[3-(hydroxymethyl)-5-methyl-4-oxopiperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1C(CO)C(=O)C(C)CN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F QTQHDOSQHSJHBF-HGMXIMQMSA-N 0.000 description 1
- GUXLVOCQRJDXQH-KRWDZBQOSA-N n-[[(5s)-3-[3-fluoro-4-[4-[2-(hydroxymethyl)-1,3-dioxolan-2-yl]piperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(C2(CO)OCCO2)CC1 GUXLVOCQRJDXQH-KRWDZBQOSA-N 0.000 description 1
- CAGIVQMVZHPYSU-INIZCTEOSA-N n-[[(5s)-3-[4-(4-acetamidopiperidin-1-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(NC(C)=O)CC1 CAGIVQMVZHPYSU-INIZCTEOSA-N 0.000 description 1
- OAJRKBPUZFSOLD-HNNXBMFYSA-N n-[[(5s)-3-[4-(4-cyanoiminopiperidin-1-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(=NC#N)CC1 OAJRKBPUZFSOLD-HNNXBMFYSA-N 0.000 description 1
- QRULHFBEIKFQCR-DJNXLDHESA-N n-[[(5s)-3-[4-[4-(2,3-dihydroxypropoxyimino)piperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(=NOCC(O)CO)CC1 QRULHFBEIKFQCR-DJNXLDHESA-N 0.000 description 1
- CQUFLLBYLVGBNQ-AWEZNQCLSA-N n-[[(5s)-3-[4-[4-(diaminomethylidenehydrazinylidene)piperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(=NN=C(N)N)CC1 CQUFLLBYLVGBNQ-AWEZNQCLSA-N 0.000 description 1
- DNUFOPJPRRSIQW-KRWDZBQOSA-N n-[[(5s)-3-[4-[4-(dimethylaminomethylideneamino)piperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1CC(N=CN(C)C)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F DNUFOPJPRRSIQW-KRWDZBQOSA-N 0.000 description 1
- RRIWSQXXBIFKQM-UHFFFAOYSA-M n-benzylcarbamate Chemical compound [O-]C(=O)NCC1=CC=CC=C1 RRIWSQXXBIFKQM-UHFFFAOYSA-M 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 238000007911 parenteral administration Methods 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
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000003449 preventive 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
- 125000006308 propyl amino group Chemical group 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 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
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- 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
- C07D413/10—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 linked by a carbon chain containing aromatic rings
-
- 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
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- 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
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D263/36—One oxygen atom
- C07D263/38—One oxygen atom attached in position 2
-
- 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
- C07D417/14—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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oncology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pulmonology (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 Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4394994 | 1994-03-15 | ||
| JP14656594 | 1994-06-28 | ||
| JP6235167A JPH0873455A (ja) | 1994-03-15 | 1994-09-29 | 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LV13155B true LV13155B (en) | 2004-06-20 |
Family
ID=27291734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-04-20A LV13155B (en) | 1994-03-15 | 2004-02-19 | Oxazolidinone derivatives and pharmaceutical compositions containing them |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0750618B1 (fr) |
| JP (2) | JPH0873455A (fr) |
| KR (1) | KR100340365B1 (fr) |
| CN (1) | CN1143961A (fr) |
| AT (1) | ATE232862T1 (fr) |
| AU (1) | AU681953B2 (fr) |
| CA (1) | CA2183972C (fr) |
| DE (1) | DE69529670T2 (fr) |
| DK (1) | DK0750618T3 (fr) |
| ES (1) | ES2191048T3 (fr) |
| LV (1) | LV13155B (fr) |
| NZ (1) | NZ283011A (fr) |
| PT (1) | PT750618E (fr) |
| WO (1) | WO1995025106A1 (fr) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU702752B2 (en) * | 1995-05-11 | 1999-03-04 | Pharmacia & Upjohn Company | Spirocyclic and bicyclic diazinyl and carbazinyl oxazolidinones |
| PT1019385E (pt) * | 1995-09-15 | 2004-06-30 | Upjohn Co | N-oxidos de aminoaril-oxazolidinona |
| GB9601666D0 (en) * | 1996-01-27 | 1996-03-27 | Zeneca Ltd | Chemical compounds |
| GB9702213D0 (en) | 1996-02-24 | 1997-03-26 | Zeneca Ltd | Chemical compounds |
| PT892792E (pt) * | 1996-04-11 | 2002-05-31 | Upjohn Co | Processo para a preparacao de oxazolidinonas |
| GB9609919D0 (en) | 1996-05-11 | 1996-07-17 | Zeneca Ltd | Chemical compounds |
| DE19750968A1 (de) * | 1997-03-07 | 1998-09-10 | Clariant Gmbh | Verfahren zur Herstellung von N-Carboxyalkyl-3-fluor-4-dialkylaminoanilinen |
| DE19709443C1 (de) * | 1997-03-07 | 1998-10-08 | Clariant Gmbh | Verfahren zur Herstellung von N-Carboxyalkyl-3-fluor-4-dialkylaminoanilinen und N-Carboxymethyl-3-fluor-4-morpholinoanilin und N-Carboxyisobutyl-3-fluor-4-morpholinoanilin |
| US6037354A (en) * | 1997-06-18 | 2000-03-14 | Merck & Co., Inc. | Alpha 1a adrenergic receptor antagonists |
| GB9717807D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| GB9717804D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| KR100467309B1 (ko) * | 1997-09-04 | 2005-07-18 | 씨제이 주식회사 | 옥사졸리디논유도체및그의제조방법및항균제조성물 |
| KR100463111B1 (ko) * | 1997-10-30 | 2005-06-13 | 씨제이 주식회사 | 신규한옥사졸리디논유도체및제조방법및그를함유하는항균제조성물 |
| US5998406A (en) * | 1997-11-12 | 1999-12-07 | Pharmacia & Upjohn Company | Oxazolidinone derivatives and pharmaceutical compositions |
| GB9725244D0 (en) | 1997-11-29 | 1998-01-28 | Zeneca Ltd | Chemical compounds |
| DK1054874T3 (da) * | 1998-02-13 | 2002-12-30 | Upjohn Co | Substituerede aminophenylisoxazolinderivater, der er anvendelige som antimokrobielle midler |
| WO2002006278A1 (fr) * | 2000-07-17 | 2002-01-24 | Ranbaxy Laboratories Limited | Derives d'oxazolidinone utilises en tant qu'antimicrobiens |
| US6951863B2 (en) | 2001-02-07 | 2005-10-04 | Ortho-Mcneil Pharmaceutical, Inc. | Pyridoarylphenly oxazolidinone antibacterials, and related compositions and methods |
| US7232924B2 (en) | 2001-06-11 | 2007-06-19 | Xenoport, Inc. | Methods for synthesis of acyloxyalkyl derivatives of GABA analogs |
| US6818787B2 (en) | 2001-06-11 | 2004-11-16 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US7186855B2 (en) | 2001-06-11 | 2007-03-06 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US8048917B2 (en) | 2005-04-06 | 2011-11-01 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US6956040B2 (en) | 2001-07-16 | 2005-10-18 | Ranbaxy Laboratories Limited | Oxazolidinone piperazinyl derivatives as potential antimicrobials |
| EP1409464A4 (fr) * | 2001-07-16 | 2005-11-02 | Ranbaxy Lab Ltd | Derives d'oxazolidinone utilises comme antimicrobiens potentiels |
| KR100445437B1 (ko) * | 2002-02-08 | 2004-08-21 | 한국과학기술연구원 | 네오마이신-옥사졸리디논 헤테로 이합체, 그의 제조방법및 그의 용도 |
| 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 |
| WO2004007489A2 (fr) * | 2002-07-11 | 2004-01-22 | Wockhardt Limited | Antibacteriens a base de methylenepiperidinophenyl oxazolidinones a substitution cyano ciblant de multiples sites de ribonucleoproteines |
| CA2492743A1 (fr) * | 2002-07-11 | 2004-01-22 | Wockhardt Limited | Oxazolidinones anti-microbiennes a profil pharmacocinetique ameliore et avantages de surete |
| AU2003249983A1 (en) * | 2002-07-18 | 2004-02-09 | Actelion Pharmaceuticals Ltd | Piperidines useful for the treatment of central nervous system disorders |
| WO2004014897A1 (fr) | 2002-08-12 | 2004-02-19 | Pharmacia & Upjohn Company Llc | N-aryl-2-oxazolidinones et leurs derives |
| WO2004045616A1 (fr) | 2002-11-21 | 2004-06-03 | Pharmacia & Upjohn Company Llc | Derives de n-(4-(piperazine-1-yl)-phenyl-2-oxazolidinone-5-carboxamides et composes associes servant d'agents antibacteriens |
| BRPI0413838A (pt) * | 2003-08-25 | 2006-10-24 | Warner Lambert Co | compostos de ariloxazolidinona antimicrobianos |
| US7687627B2 (en) * | 2003-09-08 | 2010-03-30 | Wockhardt Limited | Substituted piperidino phenyloxazolidinones having antimicrobial activity with improved in vivo efficacy |
| CN100545150C (zh) * | 2003-09-12 | 2009-09-30 | 中国科学院上海药物研究所 | 含吡啶环的噁唑烷酮类化合物、制备方法及用途 |
| US7304050B2 (en) | 2003-09-16 | 2007-12-04 | Pfizer Inc. | Antibacterial agents |
| US20090018123A1 (en) * | 2005-06-20 | 2009-01-15 | Milind D Sindkhedkar | Oxazolidinones Bearing Antimicrobial Activity Composition and Methods of Preparation |
| JP5313126B2 (ja) * | 2006-05-09 | 2013-10-09 | ウォックハート リミテッド | 置換ピペリジノフェニルオキサゾリジノン |
| KR20130095850A (ko) * | 2006-09-25 | 2013-08-28 | 욱크하르트 리미티드 | 치환된 피페리디노페닐 옥사졸리디논 |
| BRPI1014213A2 (pt) * | 2009-03-27 | 2015-08-25 | Council Scient Ind Res | "1,4-dioxa-8-azaspiro [4,5] decanos substituídos úteis como fungicidas e processo para a preparação dos mesmos. |
| KR20130102614A (ko) | 2010-11-03 | 2013-09-17 | 욱크하르트 리미티드 | 인산 모노-(1-[4-[(s)-5-(아세틸아미노메틸)-2-옥소-옥사졸리딘-3-일]-2,6-디플루오로페닐]-4-메톡시메틸피페리딘-4-일) 에스테르의 제조 방법 |
| WO2013044845A1 (fr) | 2011-09-29 | 2013-04-04 | 山东轩竹医药科技有限公司 | Médicament antibactérien à base d'oxazolidinone substituée par un hétérocycle biarylique |
| WO2013182070A1 (fr) * | 2012-06-08 | 2013-12-12 | 四川贝力克生物技术有限责任公司 | Médicament pour la prévention ou le traitement de maladies mycobactériennes |
| WO2015173664A1 (fr) | 2014-05-14 | 2015-11-19 | Wockhardt Limited | Procédé pour la préparation de(5s)-n-{3- [3,5-difluoro-4- (4-hydroxy -4-méthoxyméthyl-pipéridine-1-yl)-phényl]-2-oxo-oxazolidine-5-ylméthyl}-acétamide |
| US12109203B2 (en) | 2018-07-25 | 2024-10-08 | Zydus Lifesciences Limited | Substituted oxazolidinones for the treatment of mammalian infections |
| JP7805319B2 (ja) | 2020-06-18 | 2026-01-23 | アカゲラ・メディスンズ，インコーポレイテッド | オキサゾリジノン化合物、オキサゾリジノン化合物を含むリポソーム組成物、およびそれらの使用方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4948801A (en) * | 1988-07-29 | 1990-08-14 | E. I. Du Pont De Nemours And Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| AU667198B2 (en) * | 1991-11-01 | 1996-03-14 | Pharmacia & Upjohn Company | Substituted aryl- and heteroarylphenyloxazolidinones useful as antibacterial agents |
| SK283420B6 (sk) * | 1992-05-08 | 2003-07-01 | Pharmacia & Upjohn Company | Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny |
-
1994
- 1994-09-29 JP JP6235167A patent/JPH0873455A/ja active Pending
-
1995
- 1995-03-14 DK DK95913624T patent/DK0750618T3/da active
- 1995-03-14 ES ES95913624T patent/ES2191048T3/es not_active Expired - Lifetime
- 1995-03-14 KR KR1019960705086A patent/KR100340365B1/ko not_active Expired - Fee Related
- 1995-03-14 DE DE69529670T patent/DE69529670T2/de not_active Expired - Lifetime
- 1995-03-14 WO PCT/US1995/002972 patent/WO1995025106A1/fr not_active Ceased
- 1995-03-14 EP EP95913624A patent/EP0750618B1/fr not_active Expired - Lifetime
- 1995-03-14 AU AU20999/95A patent/AU681953B2/en not_active Ceased
- 1995-03-14 JP JP52365595A patent/JP3628329B2/ja not_active Expired - Fee Related
- 1995-03-14 CA CA002183972A patent/CA2183972C/fr not_active Expired - Fee Related
- 1995-03-14 PT PT95913624T patent/PT750618E/pt unknown
- 1995-03-14 AT AT95913624T patent/ATE232862T1/de not_active IP Right Cessation
- 1995-03-14 NZ NZ283011A patent/NZ283011A/en unknown
- 1995-03-14 CN CN95192083A patent/CN1143961A/zh active Pending
-
2004
- 2004-02-19 LV LVP-04-20A patent/LV13155B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0750618A1 (fr) | 1997-01-02 |
| AU681953B2 (en) | 1997-09-11 |
| CA2183972A1 (fr) | 1995-09-21 |
| PT750618E (pt) | 2003-06-30 |
| WO1995025106A1 (fr) | 1995-09-21 |
| DK0750618T3 (da) | 2003-06-10 |
| EP0750618B1 (fr) | 2003-02-19 |
| KR100340365B1 (ko) | 2002-11-23 |
| ATE232862T1 (de) | 2003-03-15 |
| JPH0873455A (ja) | 1996-03-19 |
| DE69529670T2 (de) | 2003-09-18 |
| DE69529670D1 (de) | 2003-03-27 |
| NZ283011A (en) | 1997-09-22 |
| JP3628329B2 (ja) | 2005-03-09 |
| MX9604072A (es) | 1997-09-30 |
| CN1143961A (zh) | 1997-02-26 |
| CA2183972C (fr) | 2005-07-05 |
| ES2191048T3 (es) | 2003-09-01 |
| JPH09512785A (ja) | 1997-12-22 |
| AU2099995A (en) | 1995-10-03 |
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