HRP970048A2 - New substituted oxazolidinone - Google Patents

New substituted oxazolidinone Download PDF

Info

Publication number: HRP970048A2
Authority: HR; Croatia
Prior art keywords: carbon atoms; chain; straight; branched alkyl; different
Prior art date: 1996-02-06

Application number

HR19604223.2A

Other languages

English (en)

Croatian (hr)

Inventor

Bernd Riedel

Dieter Haebich

Andreas Stolle

Martin Ruppelt

Stephan Bartel

Walter Guarnieri

Rainer Endermann

Hein-Peter Kroll

Original Assignee

Bayer Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-02-06

Filing date

1997-01-27

Publication date

1998-04-30

1997-01-27 Application filed by Bayer Ag filed Critical Bayer Ag

1998-04-30 Publication of HRP970048A2 publication Critical patent/HRP970048A2/hr

Links

IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 98
150000001875 compounds Chemical class 0.000 claims description 88
125000000217 alkyl group Chemical group 0.000 claims description 67
239000001257 hydrogen Substances 0.000 claims description 46
229910052739 hydrogen Inorganic materials 0.000 claims description 46
-1 cyano, mercapto, formyl Chemical group 0.000 claims description 40
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
150000002431 hydrogen Chemical class 0.000 claims description 31
238000000034 method Methods 0.000 claims description 25
229910052717 sulfur Inorganic materials 0.000 claims description 18
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 14
239000011737 fluorine Substances 0.000 claims description 14
229910052731 fluorine Inorganic materials 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 13
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 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
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 12
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
125000004434 sulfur atom Chemical group 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
125000001544 thienyl group Chemical group 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
239000012442 inert solvent Substances 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
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
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
125000003226 pyrazolyl group Chemical group 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
125000000842 isoxazolyl group Chemical group 0.000 claims description 5
125000005495 pyridazyl group Chemical group 0.000 claims description 5
125000005493 quinolyl group Chemical group 0.000 claims description 5
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000002971 oxazolyl group Chemical group 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 3
KCOPWUJJPSTRIZ-UHFFFAOYSA-N ethyl ethanedithioate Chemical compound CCSC(C)=S KCOPWUJJPSTRIZ-UHFFFAOYSA-N 0.000 claims description 3
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
125000000524 functional group Chemical group 0.000 claims description 2
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 2
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
RBIIKVXVYVANCQ-CUWPLCDZSA-N (2s,4s,5s)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-6-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-4-hydroxy-2-propan-2-ylhexanamide Chemical compound C1C(C)(C)N(C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)CC(=O)N1C1=CC=CC=C1Cl RBIIKVXVYVANCQ-CUWPLCDZSA-N 0.000 claims 2
201000010099 disease Diseases 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 52
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 27
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 23
239000002904 solvent Substances 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000002585 base Substances 0.000 description 15
229940093499 ethyl acetate Drugs 0.000 description 15
235000019439 ethyl acetate Nutrition 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000005160 1H NMR spectroscopy Methods 0.000 description 14
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
150000001721 carbon Chemical group 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000013543 active substance Substances 0.000 description 8
150000001298 alcohols Chemical class 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 8
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
239000011734 sodium Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
150000001408 amides Chemical class 0.000 description 7
238000001816 cooling Methods 0.000 description 7
229910052744 lithium Inorganic materials 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
238000003756 stirring Methods 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000003513 alkali Substances 0.000 description 6
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
239000008096 xylene Substances 0.000 description 6
BXQNSPXDWSNUKE-UHFFFAOYSA-N 1,3-benzothiazole 1-oxide Chemical compound C1=CC=C2S(=O)C=NC2=C1 BXQNSPXDWSNUKE-UHFFFAOYSA-N 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
230000008859 change Effects 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
229940052303 ethers for general anesthesia Drugs 0.000 description 5
238000001914 filtration Methods 0.000 description 5
235000019256 formaldehyde Nutrition 0.000 description 5
239000005457 ice water Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
239000000126 substance Substances 0.000 description 5
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 4
229920001817 Agar Polymers 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
YLNSNVGRSIOCEU-ZCFIWIBFSA-N [(2r)-oxiran-2-yl]methyl butanoate Chemical compound CCCC(=O)OC[C@H]1CO1 YLNSNVGRSIOCEU-ZCFIWIBFSA-N 0.000 description 4
239000008272 agar Substances 0.000 description 4
239000004599 antimicrobial Substances 0.000 description 4
150000001540 azides Chemical class 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
229940117389 dichlorobenzene Drugs 0.000 description 4
229960004132 diethyl ether Drugs 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
239000011259 mixed solution Substances 0.000 description 4
229910000069 nitrogen hydride Inorganic materials 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
229910001854 alkali hydroxide Inorganic materials 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
125000004744 butyloxycarbonyl group Chemical group 0.000 description 3
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
229910000024 caesium carbonate Inorganic materials 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
150000005826 halohydrocarbons Chemical class 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
150000007529 inorganic bases Chemical class 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
150000002924 oxiranes Chemical class 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 3
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 3
230000008569 process Effects 0.000 description 3
125000000719 pyrrolidinyl group Chemical group 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 3
125000000335 thiazolyl group Chemical group 0.000 description 3
PPQJCISYYXZCAE-UHFFFAOYSA-N 1,10-phenanthroline;hydrate Chemical compound O.C1=CN=C2C3=NC=CC=C3C=CC2=C1 PPQJCISYYXZCAE-UHFFFAOYSA-N 0.000 description 2
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
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NXPREMJKFLVDLA-UHFFFAOYSA-N n-(2-nitroprop-1-enyl)pyridin-2-amine Chemical compound [O-][N+](=O)C(C)=CNC1=CC=CC=N1 NXPREMJKFLVDLA-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
229960003531 phenolsulfonphthalein Drugs 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
238000012545 processing Methods 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000006479 redox reaction Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
230000008719 thickening Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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
239000012138 yeast extract 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
- C07D413/04—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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
- 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
- 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
- C07D413/14—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
- 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
- C07F9/65844—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a five-membered ring which may be condensed with another ring system

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Chemical & Material Sciences (AREA)
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Animal Behavior & Ethology (AREA)
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Communicable Diseases (AREA)
Oncology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

HR19604223.2A 1996-02-06 1997-01-27 New substituted oxazolidinone HRP970048A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19604223A DE19604223A1 (de)	1996-02-06	1996-02-06	Neue substituierte Oxazolidinone

Publications (1)

Publication Number	Publication Date
HRP970048A2 true HRP970048A2 (en)	1998-04-30

Family

ID=7784633

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR19604223.2A HRP970048A2 (en)	1996-02-06	1997-01-27	New substituted oxazolidinone

Country Status (36)

Country	Link
US (1)	US5792765A (es)
EP (1)	EP0789025B1 (es)
JP (1)	JPH09316073A (es)
KR (1)	KR970061888A (es)
CN (1)	CN1160051A (es)
AR (1)	AR005703A1 (es)
AT (1)	ATE200285T1 (es)
AU (1)	AU1251697A (es)
BG (1)	BG101193A (es)
BR (1)	BR9700885A (es)
CA (1)	CA2196862A1 (es)
CO (1)	CO4560411A1 (es)
CZ (1)	CZ34097A3 (es)
DE (2)	DE19604223A1 (es)
DK (1)	DK0789025T3 (es)
EE (1)	EE9700043A (es)
ES (1)	ES2157027T3 (es)
GR (1)	GR3036015T3 (es)
HR (1)	HRP970048A2 (es)
HU (1)	HUP9700358A3 (es)
ID (1)	ID15881A (es)
IL (1)	IL120125A0 (es)
MX (1)	MX9700886A (es)
NO (1)	NO970511L (es)
NZ (1)	NZ314179A (es)
PL (1)	PL318277A1 (es)
PT (1)	PT789025E (es)
SG (1)	SG50791A1 (es)
SI (1)	SI0789025T1 (es)
SK (1)	SK15897A3 (es)
SV (1)	SV1997000009A (es)
TN (1)	TNSN97032A1 (es)
TR (1)	TR199700092A2 (es)
TW (1)	TW350845B (es)
YU (1)	YU4397A (es)
ZA (1)	ZA97927B (es)

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US4948801A (en) *	1988-07-29	1990-08-14	E. I. Du Pont De Nemours And 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
US5164510A (en) *	1988-09-15	1992-11-17	The Upjohn Company	5'Indolinyl-5β-amidomethyloxazolidin-2-ones
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
DE4303303C1 (de)	1993-02-05	1994-02-17	Freudenberg Carl Fa	Antriebsstrang eines Kraftfahrzeugs
DE4332384A1 (de)	1993-09-23	1995-03-30	Merck Patent Gmbh	Adhäsionsrezeptor-Antagonisten III
TW286317B (es)	1993-12-13	1996-09-21	Hoffmann La Roche
DE4425613A1 (de)	1994-07-20	1996-01-25	Bayer Ag	5-gliedrige Heteroaryl-oxazolidinone
DE4425609A1 (de) *	1994-07-20	1996-01-25	Bayer Ag	Benzofuranyl- und Benzothienyloxazolidinone
DE4425612A1 (de)	1994-07-20	1996-04-04	Bayer Ag	6-gliedrige stickstoffhaltige Heteroaryl-oxazolidinone
DE19514313A1 (de) *	1994-08-03	1996-02-08	Bayer Ag	Benzoxazolyl- und Benzothiazolyloxazolidinone
HRP960159A2 (en)	1995-04-21	1997-08-31	Bayer Ag	Benzocyclopentane oxazolidinones containing heteroatoms

1996
- 1996-02-06 DE DE19604223A patent/DE19604223A1/de not_active Withdrawn
1997
- 1997-01-27 HR HR19604223.2A patent/HRP970048A2/hr not_active Application Discontinuation
- 1997-01-31 PT PT97101509T patent/PT789025E/pt unknown
- 1997-01-31 DK DK97101509T patent/DK0789025T3/da active
- 1997-01-31 SI SI9730110T patent/SI0789025T1/xx unknown
- 1997-01-31 DE DE59703261T patent/DE59703261D1/de not_active Expired - Fee Related
- 1997-01-31 EP EP97101509A patent/EP0789025B1/de not_active Expired - Lifetime
- 1997-01-31 AT AT97101509T patent/ATE200285T1/de not_active IP Right Cessation
- 1997-01-31 ES ES97101509T patent/ES2157027T3/es not_active Expired - Lifetime
- 1997-02-03 IL IL12012597A patent/IL120125A0/xx unknown
- 1997-02-03 US US08/794,034 patent/US5792765A/en not_active Expired - Fee Related
- 1997-02-03 NZ NZ314179A patent/NZ314179A/xx unknown
- 1997-02-04 AR ARP970100439A patent/AR005703A1/es unknown
- 1997-02-04 BG BG101193A patent/BG101193A/xx unknown
- 1997-02-04 ID IDP970341A patent/ID15881A/id unknown
- 1997-02-04 TW TW086101259A patent/TW350845B/zh active
- 1997-02-04 AU AU12516/97A patent/AU1251697A/en not_active Abandoned
- 1997-02-04 MX MX9700886A patent/MX9700886A/es unknown
- 1997-02-04 TN TNTNSN97032A patent/TNSN97032A1/fr unknown
- 1997-02-04 PL PL97318277A patent/PL318277A1/xx unknown
- 1997-02-05 NO NO970511A patent/NO970511L/no unknown
- 1997-02-05 CZ CZ97340A patent/CZ34097A3/cs unknown
- 1997-02-05 TR TR97/00092A patent/TR199700092A2/xx unknown
- 1997-02-05 KR KR1019970003610A patent/KR970061888A/ko not_active Application Discontinuation
- 1997-02-05 YU YU4397A patent/YU4397A/sh unknown
- 1997-02-05 EE EE9700043A patent/EE9700043A/xx unknown
- 1997-02-05 ZA ZA9700927A patent/ZA97927B/xx unknown
- 1997-02-05 CA CA002196862A patent/CA2196862A1/en not_active Abandoned
- 1997-02-05 SK SK158-97A patent/SK15897A3/sk unknown
- 1997-02-05 SG SG1997000259A patent/SG50791A1/en unknown
- 1997-02-05 BR BR9700885A patent/BR9700885A/pt not_active Application Discontinuation
- 1997-02-05 HU HU9700358A patent/HUP9700358A3/hu unknown
- 1997-02-06 SV SV1997000009A patent/SV1997000009A/es unknown
- 1997-02-06 CN CN97101879A patent/CN1160051A/zh active Pending
- 1997-02-06 CO CO97006151A patent/CO4560411A1/es unknown
- 1997-02-06 JP JP9036908A patent/JPH09316073A/ja active Pending
2001
- 2001-06-08 GR GR20010400867T patent/GR3036015T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
CN1160051A (zh)	1997-09-24
SI0789025T1 (en)	2001-08-31
PT789025E (pt)	2001-07-31
NZ314179A (en)	1998-12-23
SG50791A1 (en)	1998-07-20
CZ34097A3 (en)	1997-08-13
MX9700886A (es)	1998-04-30
AU1251697A (en)	1997-08-14
SK15897A3 (en)	1997-10-08
HUP9700358A2 (hu)	1998-07-28
NO970511L (no)	1997-08-07
EP0789025B1 (de)	2001-04-04
KR970061888A (ko)	1997-09-12
CO4560411A1 (es)	1998-02-10
CA2196862A1 (en)	1997-08-07
US5792765A (en)	1998-08-11
TR199700092A2 (tr)	1997-08-21
ZA97927B (en)	1997-08-19
ES2157027T3 (es)	2001-08-01
EP0789025A1 (de)	1997-08-13
TW350845B (en)	1999-01-21
PL318277A1 (en)	1997-08-18
SV1997000009A (es)	1997-10-23
BR9700885A (pt)	1998-10-27
AR005703A1 (es)	1999-07-14
DK0789025T3 (da)	2001-06-18
HU9700358D0 (en)	1997-03-28
YU4397A (sh)	1999-09-27
EE9700043A (et)	1997-08-15
ATE200285T1 (de)	2001-04-15
NO970511D0 (no)	1997-02-05
JPH09316073A (ja)	1997-12-09
IL120125A0 (en)	1997-06-10
HUP9700358A3 (en)	1999-08-30
DE59703261D1 (de)	2001-05-10
BG101193A (en)	1999-02-26
ID15881A (id)	1997-08-14
DE19604223A1 (de)	1997-08-07
TNSN97032A1 (fr)	2005-03-15
GR3036015T3 (en)	2001-09-28

Publication	Publication Date	Title
HRP970048A2 (en)	1998-04-30	New substituted oxazolidinone
MXPA97000886A (es)	1998-04-01	Nuevas oxazolidinonas sustituidas
HRP970049A2 (en)	1998-04-30	New heteroaryl oxazolidinones
AU2004299413C1 (en)	2009-07-02	Novel oxazolidinone derivatives
US5869659A (en)	1999-02-09	Heteroatom-containing cyclopentanopyridyl-oxazolidinones
MXPA97000885A (es)	1998-04-01	Nuevas heteroariloxazolidinonas
HRP950391A2 (en)	1997-06-30	5-membered heteroaryl-oxazolidinones
HRP960615A2 (en)	1998-02-28	Pyridoannelated thienyl and furanyl-oxazolidinones
HRP960159A2 (en)	1997-08-31	Benzocyclopentane oxazolidinones containing heteroatoms
DE19649095A1 (de)	1997-08-07	Neue Heteroaryl-Oxazolidinone
MXPA97000388A (es)	1997-12-01	Ciclopentanopiridil-oxazolidinonas que contienenheteroatomos

Legal Events

Date	Code	Title
1998-04-30	A1OB	Publication of a patent application
1998-07-02	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
1999-11-03	OBST	Application withdrawn