JP2009511513A5 - - Google Patents
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- JP2009511513A5 JP2009511513A5 JP2008534890A JP2008534890A JP2009511513A5 JP 2009511513 A5 JP2009511513 A5 JP 2009511513A5 JP 2008534890 A JP2008534890 A JP 2008534890A JP 2008534890 A JP2008534890 A JP 2008534890A JP 2009511513 A5 JP2009511513 A5 JP 2009511513A5
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- radical
- formula
- alkyl
- solvate
- Prior art date
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000012453 solvate Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- -1 nitro, amino Chemical group 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 208000032759 Hemolytic-Uremic Syndrome Diseases 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 206010043561 Thrombocytopenic purpura Diseases 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 201000007023 Thrombotic Thrombocytopenic Purpura Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 206010014665 endocarditis Diseases 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 230000035935 pregnancy Effects 0.000 claims description 2
- 208000034841 Thrombotic Microangiopathies Diseases 0.000 claims 4
- 231100000252 nontoxic Toxicity 0.000 claims 2
- 230000003000 nontoxic effect Effects 0.000 claims 2
- 230000000414 obstructive effect Effects 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 206010012665 Diabetic gangrene Diseases 0.000 claims 1
- 206010054044 Diabetic microangiopathy Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 208000022461 Glomerular disease Diseases 0.000 claims 1
- 208000008899 Habitual abortion Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 241000242583 Scyphozoa Species 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 208000010353 central nervous system vasculitis Diseases 0.000 claims 1
- 201000009101 diabetic angiopathy Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 230000002440 hepatic effect Effects 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000036210 malignancy Effects 0.000 claims 1
- 208000019180 nutritional disease Diseases 0.000 claims 1
- 230000003169 placental effect Effects 0.000 claims 1
- 208000034213 recurrent susceptibility to 1 pregnancy loss Diseases 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 150000001204 N-oxides Chemical class 0.000 description 12
- 0 C*(*C(C*1c2ccc(*(CCOC3)C3=O)cc2)OC1=O)C(c1ccc(N)[n]1)=O Chemical compound C*(*C(C*1c2ccc(*(CCOC3)C3=O)cc2)OC1=O)C(c1ccc(N)[n]1)=O 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 11
- 150000002367 halogens Chemical class 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 208000007536 Thrombosis Diseases 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 3
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 102000004142 Trypsin Human genes 0.000 description 3
- 108090000631 Trypsin Proteins 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 229940012957 plasmin Drugs 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 239000012588 trypsin Substances 0.000 description 3
- PGOHTUIFYSHAQG-LJSDBVFPSA-N (2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-sulfanylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoyl]amino]hexanoic acid Chemical compound CSCC[C@H](N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(O)=O PGOHTUIFYSHAQG-LJSDBVFPSA-N 0.000 description 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 2
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 2
- 206010053567 Coagulopathies Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000002429 anti-coagulating effect Effects 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 229940039716 prothrombin Drugs 0.000 description 2
- 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 2
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- 125000005859 (C1-C6)alkanoyloxymethyl group Chemical group 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- VWZJPRSLXFXBIU-AWEZNQCLSA-N 5-chloro-n-[[(5s)-2-oxo-3-(6-pyridin-4-ylpyridin-3-yl)-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=NC(=CC=2)C=2C=CN=CC=2)C1 VWZJPRSLXFXBIU-AWEZNQCLSA-N 0.000 description 1
- QHHSMTMRHRZXPG-HNNXBMFYSA-N 5-chloro-n-[[(5s)-2-oxo-3-[4-(2-oxopiperidin-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(CCCC2)=O)C1 QHHSMTMRHRZXPG-HNNXBMFYSA-N 0.000 description 1
- IQOWGQZZKKHHOD-UHFFFAOYSA-N 5-chloro-n-[[2-oxo-3-(4-pyrrolidin-1-ylphenyl)-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(=CC=2)N2CCCC2)C1 IQOWGQZZKKHHOD-UHFFFAOYSA-N 0.000 description 1
- 125000000290 5-chloropentanoyl group Chemical group ClCCCCC(=O)* 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
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- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
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- VCMGMSHEPQENPE-UHFFFAOYSA-N ketamine hydrochloride Chemical compound [Cl-].C=1C=CC=C(Cl)C=1C1([NH2+]C)CCCCC1=O VCMGMSHEPQENPE-UHFFFAOYSA-N 0.000 description 1
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- UKTGQGAYMHWGBC-UHFFFAOYSA-N n-[3-(benzylamino)-2-hydroxypropyl]-5-chlorothiophene-2-carboxamide Chemical compound C=1C=C(Cl)SC=1C(=O)NCC(O)CNCC1=CC=CC=C1 UKTGQGAYMHWGBC-UHFFFAOYSA-N 0.000 description 1
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| DE19962924A1 (de) | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
| DE10129725A1 (de) | 2001-06-20 | 2003-01-02 | Bayer Ag | Kombinationstherapie substituierter Oxazolidinone |
| 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 |
| DE10355461A1 (de) | 2003-11-27 | 2005-06-23 | Bayer Healthcare Ag | Verfahren zur Herstellung einer festen, oral applizierbaren pharmazeutischen Zusammensetzung |
| EP1685841A1 (en) | 2005-01-31 | 2006-08-02 | Bayer Health Care Aktiengesellschaft | Prevention and treatment of thromboembolic disorders |
| DE102005045518A1 (de) | 2005-09-23 | 2007-03-29 | Bayer Healthcare Ag | 2-Aminoethoxyessigsäure-Derivate und ihre Verwendung |
| PT1934208E (pt) | 2005-10-04 | 2011-06-01 | Bayer Schering Pharma Ag | Nova forma polimorfa de 5-cloro-n-({(5s)-2-oxo-3-[4-(3- oxo-4-morfolinil)-fenil]-1,3-oxazolidin-5-il}-metil)-2- tiofenocarboxamida |
| DE102005047561A1 (de) | 2005-10-04 | 2007-04-05 | Bayer Healthcare Ag | Feste, oral applizierbare pharmazeutische Darreichungsformen mit schneller Wirkstofffreisetzung |
| US7700590B2 (en) | 2006-02-09 | 2010-04-20 | University Of New Orleans Research And Technology Foundation, Inc. | Antibacterial agents |
| CN101679266B (zh) * | 2007-03-01 | 2015-05-06 | 诺华股份有限公司 | Pim激酶抑制剂及其应用方法 |
| DE102007018662A1 (de) * | 2007-04-20 | 2008-10-23 | Bayer Healthcare Ag | Oxazolidinone zur Behandlung und Prophylaxe von pulmonaler Hypertonie |
| WO2009018807A1 (de) * | 2007-08-06 | 2009-02-12 | Schebo Biotech Ag | Oxazolidinone als faktor xa- inhibitoren, verfahren zu ihrer herstellung und ihre verwendung in der therapie |
| JP5422569B2 (ja) * | 2008-02-21 | 2014-02-19 | サノフイ | 凝固第Ｘａ因子及びトロンビンの阻害剤としてのクロロチオフェン−イソオキサゾール類 |
| US7816355B1 (en) | 2009-04-28 | 2010-10-19 | Apotex Pharmachem Inc | Processes for the preparation of rivaroxaban and intermediates thereof |
| CN104693139B (zh) * | 2011-01-07 | 2017-04-19 | 浙江九洲药业股份有限公司 | 一种合成利伐沙班中间体的新工艺 |
| CN102746287B (zh) * | 2012-06-21 | 2014-05-28 | 成都苑东药业有限公司 | 一种恶唑烷酮化合物及其制备方法 |
| CN103724336B (zh) * | 2013-12-24 | 2015-10-21 | 悦康药业集团有限公司 | 一种新型抗凝血药物的合成方法 |
| CN104402876A (zh) * | 2014-11-25 | 2015-03-11 | 沈阳药科大学 | 噁唑烷酮类化合物及其应用 |
| CN104478869B (zh) * | 2014-12-05 | 2017-04-12 | 广东东阳光药业有限公司 | 噁唑烷酮类化合物及其在药物中的应用 |
| CN104447728B (zh) * | 2014-12-05 | 2017-01-04 | 广东东阳光药业有限公司 | 噁唑烷酮类化合物及其在药物中的应用 |
| CN104478866B (zh) * | 2014-12-05 | 2017-07-07 | 广东东阳光药业有限公司 | 噁唑烷酮类化合物及其在药物中的应用 |
| CN104447730B (zh) * | 2014-12-05 | 2017-11-07 | 广东东阳光药业有限公司 | 噁唑烷酮类化合物及其在药物中的应用 |
| CN104497008B (zh) * | 2014-12-09 | 2016-11-16 | 广东东阳光药业有限公司 | 取代噁唑烷酮类化合物及其使用方法和用途 |
| EP3078378B1 (en) | 2015-04-08 | 2020-06-24 | Vaiomer | Use of factor xa inhibitors for regulating glycemia |
| US11608320B2 (en) | 2020-02-02 | 2023-03-21 | Kuwait University | Oxazolidinone hydroxamic acid derivatives |
| WO2021184339A1 (en) | 2020-03-20 | 2021-09-23 | Merck Sharp & Dohme Corp. | Oxazolidinone compound and methods of use thereof as an antibacterial agent |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2811555A (en) * | 1955-05-02 | 1957-10-29 | Eastman Kodak Co | Reduction of 2-nitroso-5-diethylaminotoluene |
| LU80081A1 (fr) * | 1977-08-26 | 1979-05-15 | Delalande Sa | Nouvelles hydroxymethyl-5 oxazolidinones-2,leur procede de preparation et leur application therapeutique |
| US4128654A (en) * | 1978-02-10 | 1978-12-05 | E. I. Du Pont De Nemours And Company | 5-Halomethyl-3-phenyl-2-oxazolidinones |
| DE3822650A1 (de) * | 1988-07-05 | 1990-02-01 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| CA2119556C (en) * | 1991-11-01 | 2004-07-06 | Michael Robert Barbachyn | Substituted aryl- and heteroaryl-phenyloxazolidinones |
| US5349045A (en) * | 1993-01-26 | 1994-09-20 | United States Surgical Corporation | Polymer derived from cyclic amide and medical devices manufactured therefrom |
| ES2134870T3 (es) * | 1993-05-01 | 1999-10-16 | Merck Patent Gmbh | Antagonistas del receptor de adhesion. |
| HRP960159A2 (en) * | 1995-04-21 | 1997-08-31 | Bayer Ag | Benzocyclopentane oxazolidinones containing heteroatoms |
| DE19524765A1 (de) * | 1995-07-07 | 1997-01-09 | Boehringer Mannheim Gmbh | Neue Oxazolidinonderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE19962924A1 (de) * | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
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- 2006-09-27 WO PCT/EP2006/009373 patent/WO2007042146A1/de not_active Ceased
- 2006-09-27 KR KR1020087011170A patent/KR20080067647A/ko not_active Withdrawn
- 2006-09-27 JP JP2008534890A patent/JP2009511513A/ja active Pending
- 2006-09-27 EP EP06792284A patent/EP1937271A1/de not_active Withdrawn
- 2006-09-27 AU AU2006301650A patent/AU2006301650A1/en not_active Abandoned
- 2006-09-27 BR BRPI0617202-4A patent/BRPI0617202A2/pt not_active IP Right Cessation
- 2006-09-27 CA CA002624963A patent/CA2624963A1/en not_active Abandoned
- 2006-09-27 RU RU2008118100/15A patent/RU2008118100A/ru not_active Application Discontinuation
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2008
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- 2008-04-09 EC EC2008008358A patent/ECSP088358A/es unknown
- 2008-04-09 SV SV2008002865A patent/SV2009002865A/es not_active Application Discontinuation
- 2008-04-09 CR CR9878A patent/CR9878A/es not_active Application Discontinuation
- 2008-05-06 NO NO20082120A patent/NO20082120L/no not_active Application Discontinuation
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