LV12538B - ESTERS OF EXCLUDED HYDROXYCETETHYL-PIPERAZIN-FENIL-OKSASOLIDINONE - Google Patents

ESTERS OF EXCLUDED HYDROXYCETETHYL-PIPERAZIN-FENIL-OKSASOLIDINONE Download PDF

Info

Publication number: LV12538B
Authority: LV; Latvia
Prior art keywords: oxo; piperazinyl; methyl; oxazolidinyl; acetylamino
Prior art date: 1993-11-22

Application number

LVP-00-91A

Other languages

English (en)

Latvian (lv)

Other versions

LV12538A (en

Inventor

Steven J. Brickner

Michael R. Barbachyn

Douglas K. Hutchinson

Original Assignee

Pharmacia & Upjohn Company

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.)

1993-11-22

Filing date

2000-07-14

Publication date

2000-12-20

2000-07-14 Application filed by Pharmacia & Upjohn Company filed Critical Pharmacia & Upjohn Company

2000-10-20 Publication of LV12538A publication Critical patent/LV12538A/xx

2000-12-20 Publication of LV12538B publication Critical patent/LV12538B/en

Links

-1 substituted-hydroxyacetyl piperazine phenyl oxazolidinones Chemical class 0.000 title claims abstract description 28
150000002148 esters Chemical class 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 claims abstract description 88
150000003839 salts Chemical class 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 15
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
208000015181 infectious disease Diseases 0.000 claims abstract description 10
230000000813 microbial effect Effects 0.000 claims abstract description 9
241001465754 Metazoa Species 0.000 claims abstract description 8
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract description 6
125000002883 imidazolyl group Chemical group 0.000 claims abstract description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 64
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 14
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 11
JOOXCMJARBKPKM-UHFFFAOYSA-N laevulinic acid Natural products CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 11
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
YUYHRSGXZZVNMS-UHFFFAOYSA-N 3-morpholin-4-ylpropanoic acid Chemical compound OC(=O)CCN1CCOCC1 YUYHRSGXZZVNMS-UHFFFAOYSA-N 0.000 claims description 5
229960004275 glycolic acid Drugs 0.000 claims description 5
239000001384 succinic acid Substances 0.000 claims description 4
OXOWTLDONRGYOT-UHFFFAOYSA-N 4-(dimethylamino)butanoic acid Chemical compound CN(C)CCCC(O)=O OXOWTLDONRGYOT-UHFFFAOYSA-N 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
159000000000 sodium salts Chemical class 0.000 claims description 3
JCXZKUZXVQKENT-UHFFFAOYSA-N 2-(4-methylpiperazin-1-ium-1-yl)acetate Chemical compound CN1CCN(CC(O)=O)CC1 JCXZKUZXVQKENT-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
OTBNTLUQTGOCFC-UHFFFAOYSA-N [2-[4-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2,6-difluorophenyl]piperazin-1-yl]-2-oxoethyl] 3-morpholin-4-ylpropanoate Chemical compound O=C1OC(CNC(=O)C)CN1C(C=C1F)=CC(F)=C1N1CCN(C(=O)COC(=O)CCN2CCOCC2)CC1 OTBNTLUQTGOCFC-UHFFFAOYSA-N 0.000 claims 1
SWFYBEBWZFROOW-UHFFFAOYSA-N [2-[4-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2,6-difluorophenyl]piperazin-1-yl]-2-oxoethyl] 4-(dimethylamino)benzoate Chemical compound C1=CC(N(C)C)=CC=C1C(=O)OCC(=O)N1CCN(C=2C(=CC(=CC=2F)N2C(OC(CNC(C)=O)C2)=O)F)CC1 SWFYBEBWZFROOW-UHFFFAOYSA-N 0.000 claims 1
SPYGYQACXFGZRL-UHFFFAOYSA-N [2-[4-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2,6-difluorophenyl]piperazin-1-yl]-2-oxoethyl] 4-oxopentanoate Chemical compound C1CN(C(=O)COC(=O)CCC(=O)C)CCN1C1=C(F)C=C(N2C(OC(CNC(C)=O)C2)=O)C=C1F SPYGYQACXFGZRL-UHFFFAOYSA-N 0.000 claims 1
FPNSAQWCWVFAGR-UHFFFAOYSA-N [2-[4-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2,6-difluorophenyl]piperazin-1-yl]-2-oxoethyl] acetate Chemical compound O=C1OC(CNC(=O)C)CN1C(C=C1F)=CC(F)=C1N1CCN(C(=O)COC(C)=O)CC1 FPNSAQWCWVFAGR-UHFFFAOYSA-N 0.000 claims 1
OTZCSHWGYZYBHV-UHFFFAOYSA-N [2-[4-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2,6-difluorophenyl]piperazin-1-yl]-2-oxoethyl] pyridine-3-carboxylate Chemical compound O=C1OC(CNC(=O)C)CN1C(C=C1F)=CC(F)=C1N1CCN(C(=O)COC(=O)C=2C=NC=CC=2)CC1 OTZCSHWGYZYBHV-UHFFFAOYSA-N 0.000 claims 1
MXSDWEYCJRYTCV-UHFFFAOYSA-N [2-[4-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperazin-1-yl]-2-oxoethyl] 2-methoxyacetate Chemical compound C1CN(C(=O)COC(=O)COC)CCN1C1=CC=C(N2C(OC(CNC(C)=O)C2)=O)C=C1F MXSDWEYCJRYTCV-UHFFFAOYSA-N 0.000 claims 1
MJUDZPHPIKREAM-UHFFFAOYSA-N [2-[4-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperazin-1-yl]-2-oxoethyl] 2-morpholin-4-ylacetate Chemical compound O=C1OC(CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C(=O)COC(=O)CN2CCOCC2)CC1 MJUDZPHPIKREAM-UHFFFAOYSA-N 0.000 claims 1
WGEXKXDCTHHADW-UHFFFAOYSA-N [2-[4-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperazin-1-yl]-2-oxoethyl] 3-(dimethylamino)propanoate Chemical compound C1CN(C(=O)COC(=O)CCN(C)C)CCN1C1=CC=C(N2C(OC(CNC(C)=O)C2)=O)C=C1F WGEXKXDCTHHADW-UHFFFAOYSA-N 0.000 claims 1
XKJMFAYTSIKMCW-UHFFFAOYSA-N [2-[4-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperazin-1-yl]-2-oxoethyl] 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate Chemical compound O=C1OC(CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C(=O)COC(=O)C(C)(CO)CO)CC1 XKJMFAYTSIKMCW-UHFFFAOYSA-N 0.000 claims 1
KPDUAXSTODNIKK-UHFFFAOYSA-N [2-[4-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperazin-1-yl]-2-oxoethyl] 4-aminobenzoate Chemical compound O=C1OC(CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C(=O)COC(=O)C=2C=CC(N)=CC=2)CC1 KPDUAXSTODNIKK-UHFFFAOYSA-N 0.000 claims 1
OTNZQYVTWHBLEI-UHFFFAOYSA-N [2-[4-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperazin-1-yl]-2-oxoethyl] acetate Chemical compound O=C1OC(CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C(=O)COC(C)=O)CC1 OTNZQYVTWHBLEI-UHFFFAOYSA-N 0.000 claims 1
ZUCNNVYWVZZXGZ-UHFFFAOYSA-N [2-[4-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperazin-1-yl]-2-oxoethyl] dihydrogen phosphate Chemical compound O=C1OC(CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C(=O)COP(O)(O)=O)CC1 ZUCNNVYWVZZXGZ-UHFFFAOYSA-N 0.000 claims 1
UHIRXVLQAULTGO-UHFFFAOYSA-N [2-[4-[4-[5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperazin-1-yl]-2-oxoethyl] pyridine-3-carboxylate Chemical compound O=C1OC(CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C(=O)COC(=O)C=2C=NC=CC=2)CC1 UHIRXVLQAULTGO-UHFFFAOYSA-N 0.000 claims 1
229940125898 compound 5 Drugs 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 8
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 abstract description 4
150000001733 carboxylic acid esters Chemical class 0.000 abstract description 4
150000003014 phosphoric acid esters Chemical class 0.000 abstract description 4
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 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
201000010099 disease Diseases 0.000 abstract 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 207
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 195
239000007787 solid Substances 0.000 description 86
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 83
235000019439 ethyl acetate Nutrition 0.000 description 74
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 46
229940093499 ethyl acetate Drugs 0.000 description 46
239000000203 mixture Substances 0.000 description 43
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
238000006243 chemical reaction Methods 0.000 description 39
239000000243 solution Substances 0.000 description 39
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 34
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
239000000047 product Substances 0.000 description 26
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
239000008363 phosphate buffer Substances 0.000 description 23
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
238000003756 stirring Methods 0.000 description 20
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
239000012267 brine Substances 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 19
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
239000000463 material Substances 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 13
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
239000000377 silicon dioxide Substances 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
239000003921 oil Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
239000010410 layer Substances 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
239000012043 crude product Substances 0.000 description 7
238000000034 method Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
235000011054 acetic acid Nutrition 0.000 description 6
150000001540 azides Chemical class 0.000 description 6
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
ADAMEOZKZQRNKP-UHFFFAOYSA-N n'-propylmethanediimine Chemical compound CCCN=C=N ADAMEOZKZQRNKP-UHFFFAOYSA-N 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
239000008194 pharmaceutical composition Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
239000013058 crude material Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
229960003512 nicotinic acid Drugs 0.000 description 5
235000001968 nicotinic acid Nutrition 0.000 description 5
239000011664 nicotinic acid Substances 0.000 description 5
238000011084 recovery Methods 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 4
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 4
239000004471 Glycine Substances 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
229960004050 aminobenzoic acid Drugs 0.000 description 4
239000000872 buffer Substances 0.000 description 4
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
239000006260 foam Substances 0.000 description 4
229960000443 hydrochloric acid Drugs 0.000 description 4
235000011167 hydrochloric acid Nutrition 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
229960001407 sodium bicarbonate Drugs 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
238000003828 vacuum filtration Methods 0.000 description 4
GRZHHTYDZVRPIC-UHFFFAOYSA-N (benzyloxy)acetic acid Chemical compound OC(=O)COCC1=CC=CC=C1 GRZHHTYDZVRPIC-UHFFFAOYSA-N 0.000 description 3
QISAUDWTBBNJIR-UHFFFAOYSA-N 2-phenylmethoxyacetyl chloride Chemical compound ClC(=O)COCC1=CC=CC=C1 QISAUDWTBBNJIR-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
108010059993 Vancomycin Proteins 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000000845 anti-microbial effect Effects 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000004587 chromatography analysis Methods 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
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
238000006073 displacement reaction Methods 0.000 description 3
VMWJCFLUSKZZDX-UHFFFAOYSA-N n,n-dimethylmethanamine Chemical compound [CH2]N(C)C VMWJCFLUSKZZDX-UHFFFAOYSA-N 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
239000010452 phosphate Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 3
MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 3
229960003165 vancomycin Drugs 0.000 description 3
MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 description 2
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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
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
241000894007 species Species 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
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000008719 thickening Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000002627 tracheal intubation Methods 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
238000001665 trituration Methods 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- 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
- C07D413/12—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 chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

LVP-00-91A 1993-11-22 2000-07-14 ESTERS OF EXCLUDED HYDROXYCETETHYL-PIPERAZIN-FENIL-OKSASOLIDINONE LV12538B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US15598893A	1993-11-22	1993-11-22

Publications (2)

Publication Number	Publication Date
LV12538A LV12538A (en)	2000-10-20
LV12538B true LV12538B (en)	2000-12-20

Family

ID=22557606

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LVP-00-91A LV12538B (en)	1993-11-22	2000-07-14	ESTERS OF EXCLUDED HYDROXYCETETHYL-PIPERAZIN-FENIL-OKSASOLIDINONE

Country Status (20)

Country	Link
US (1)	US5652238A (fr)
EP (1)	EP0730591B1 (fr)
JP (1)	JP3698724B2 (fr)
KR (1)	KR100312903B1 (fr)
CN (1)	CN1046276C (fr)
AT (1)	ATE182142T1 (fr)
AU (1)	AU698699B2 (fr)
CA (1)	CA2174107C (fr)
CO (1)	CO4290433A1 (fr)
DE (1)	DE69419523T2 (fr)
DK (1)	DK0730591T3 (fr)
ES (1)	ES2133588T3 (fr)
GR (1)	GR3031420T3 (fr)
IL (1)	IL111215A0 (fr)
LV (1)	LV12538B (fr)
NZ (1)	NZ274966A (fr)
PE (1)	PE22896A1 (fr)
TW (1)	TW427987B (fr)
WO (1)	WO1995014684A1 (fr)
ZA (1)	ZA947885B (fr)

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ZA969622B (en) *	1995-12-13	1998-05-15	Upjohn Co	Oxazolidinone antibacterial agents having a six-membered heteroaromatic ring.
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GB9609919D0 (en)	1996-05-11	1996-07-17	Zeneca Ltd	Chemical compounds
GB9614238D0 (en) *	1996-07-06	1996-09-04	Zeneca Ltd	Chemical compounds
GB9614236D0 (en) *	1996-07-06	1996-09-04	Zeneca Ltd	Chemical compounds
GB9717807D0 (en) *	1997-08-22	1997-10-29	Zeneca Ltd	Chemical compounds
GB9717804D0 (en)	1997-08-22	1997-10-29	Zeneca Ltd	Chemical compounds
CA2303959A1 (fr) *	1997-11-12	1999-05-20	Pharmacia & Upjohn Company	Derives d'oxazolidinone et compositions pharmaceutiques
US6040306A (en) *	1997-11-18	2000-03-21	Pharmacia & Upjohn Company	Method of treating psoriasis, arthritis and reducing the toxicity of cancer chemotherapy
AU780197B2 (en) *	1997-11-18	2005-03-10	Pharmacia & Upjohn Company	Method of treating psoriasis, arthritis and reducing the toxicity of cancer chemotherapy
CN1546030A (zh) *	1997-11-18	2004-11-17	��Ŷ��Լ��˾	噁唑烷酮衍生物在治疗关节炎和减少癌症化学疗法毒性中的应用
EP1304107B1 (fr) *	1997-11-18	2005-07-06	Pharmacia & Upjohn Company LLC	Utilisation de dèrives d'oxazolidinone pour traiter le Psoriasis
GB9725244D0 (en)	1997-11-29	1998-01-28	Zeneca Ltd	Chemical compounds
US7002020B1 (en)	1998-01-23	2006-02-21	Pharmacia & Upjohn Company	Oxazolidinone combinatorial libraries, compositions and methods of preparation
US6562844B2 (en)	1998-01-23	2003-05-13	Pharmacia & Upjohn Company	Oxazolidinone combinatorial libraries, compositions and methods of preparation
US6239152B1 (en)	1998-01-23	2001-05-29	Pharmacia & Upjohn Company	Oxazolidinone combinatorial libraries, compositions and methods of preparation
CA2315735A1 (fr) *	1998-02-13	1999-08-19	Michael R. Barbachyn	Derives d'isoxazoline aminophenyle substitues utilises comme agents antimicrobiens
CA2333332A1 (fr)	1998-06-05	1999-12-16	Astrazeneca Ab	Composes chimiques
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US6337329B1 (en) *	1998-07-14	2002-01-08	Pharmacia & Upjohn Company	Oxazolidinones to treat eye infections
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WO2000045177A1 (fr)	1999-01-27	2000-08-03	Pharmacia & Upjohn Company	Dosages de modulateurs de l'activite du facteur d'elongation p
GB9928568D0 (en)	1999-12-03	2000-02-02	Zeneca Ltd	Chemical compounds
PE20010851A1 (es) *	1999-12-14	2001-08-17	Upjohn Co	Esteres del acido benzoico de oxazolidinonas que tienen un substituyente hidroxiacetilpiperazina
US6642238B2 (en)	2000-02-10	2003-11-04	Pharmacia And Upjohn Company	Oxazolidinone thioamides with piperazine amide substituents
GB0009803D0 (en) *	2000-04-25	2000-06-07	Astrazeneca Ab	Chemical compounds
HUP0301562A2 (hu)	2000-06-05	2003-12-29	Dong A Pharm. Co., Ltd.	Új oxazolidinonszármazékok és eljárás ezek előállítására, ezeket tartalmazó gyógyszerkészítmények
US6734307B2 (en)	2000-07-17	2004-05-11	Ranbaxy Laboratories Limited	Oxazolidinone derivatives as antimicrobials
PE20020300A1 (es) *	2000-08-22	2002-05-10	Pharmacia Corp	Composicion de solucion de un farmaco antibiotico a base de oxazolidinona con mejoramiento de la carga de farmaco
PE20020578A1 (es)	2000-10-10	2002-08-14	Upjohn Co	Una composicion de antibiotico topico para el tratamiento de infecciones oculares
US6861433B2 (en)	2000-12-15	2005-03-01	Pharmacia & Upjohn Company	Oxazolidinone photoaffinity probes
EP1409464A4 (fr) *	2001-07-16	2005-11-02	Ranbaxy Lab Ltd	Derives d'oxazolidinone utilises comme antimicrobiens potentiels
US6956040B2 (en)	2001-07-16	2005-10-18	Ranbaxy Laboratories Limited	Oxazolidinone piperazinyl derivatives as potential antimicrobials
TW200302095A (en) *	2002-01-25	2003-08-01	Upjohn Co	Oxazolidinone cotherapy
MXPA04008173A (es) *	2002-02-22	2004-11-26	Pharmacia Corp	Formulaciones de farmaco antibiotico oftalmico que contienen un compuesto de ciclodextrina y cloruro de cetil piridinio.
US7141588B2 (en) *	2002-02-25	2006-11-28	Pfizer, Inc.	N-aryl-2-oxazolidinone-5-carboxamides and their derivatives
AR038536A1 (es) *	2002-02-25	2005-01-19	Upjohn Co	N-aril-2-oxazolidinona-5- carboxamidas y sus derivados
US20030216330A1 (en) *	2002-03-29	2003-11-20	Pharmacia & Upjohn	Parenteral, intravenous, and oral administration of oxazolidinones for treating diabetic foot infections
ATE321760T1 (de) *	2002-08-12	2006-04-15	Pharmacia & Upjohn Co Llc	N-aryl-2-oxazolidinone und deren derivate
WO2004018439A1 (fr) *	2002-08-22	2004-03-04	Orchid Chemicals & Pharmaceuticals Ltd	Nouveaux agents antibacteriens
AU2002339721A1 (en) *	2002-09-20	2004-04-08	Lupin Limited	Oxazolidinone derivatives, process for their preperation and their use as antimycobacterial agents
ES2271660T3 (es) *	2002-11-21	2007-04-16	PHARMACIA & UPJOHN COMPANY LLC	Derivados de n-(4-piperazin-1-il)-fenil-2-oxazolidinona-5-carboxamida y compuestos relacionados como agentes antibacterianos.
AU2002357561A1 (en) *	2002-12-30	2004-07-22	Nanjing Chang'ao Pharmaceutical Science And Technology Limited Company	Oxazolidine derivative, methods of preparation and uses
US20040170686A1 (en) *	2003-01-31	2004-09-02	Fredrickson Jennifer K.	Suspension vehicle for coated drug particles
EP1594494A1 (fr) *	2003-02-07	2005-11-16	Warner-Lambert Company LLC	Derives d'oxazolidinone n-substitues par un noyau bicyclique, utilises comme agents antibacteriens
MXPA05007724A (es) *	2003-02-07	2005-09-30	Warner Lambert Co	Agentes antibacterianos.
US20040191326A1 (en) *	2003-03-31	2004-09-30	Reo Joseph P.	Taste-masking vehicle for coated oxazolidinone particles
US20040204463A1 (en) *	2003-04-01	2004-10-14	Harris Christina Renee	N-aryl-2-oxazolidinone-5-carboxamides and their derivatives
MXPA06002188A (es) *	2003-08-25	2006-04-27	Warner Lambert Co	Nuevos compuestos antimicrobianos de ariloxazolidinona.
US7304050B2 (en) *	2003-09-16	2007-12-04	Pfizer Inc.	Antibacterial agents
KR100854211B1 (ko)	2003-12-18	2008-08-26	동아제약주식회사	신규한 옥사졸리디논 유도체, 그의 제조방법 및 이를유효성분으로 하는 항생제용 약학 조성물
WO2008061954A1 (fr) *	2006-11-23	2008-05-29	Agfa Graphics Nv	Nouveaux co-initiateurs
EP1925609A1 (fr) *	2006-11-23	2008-05-28	Agfa Graphics N.V.	Nouveaux co-initiateurs
KR101023174B1 (ko) *	2008-09-24	2011-03-18	주식회사 레고켐 바이오사이언스	사이클릭 아미독심 또는 사이클릭 아미드라존 기를 가지는 신규한 옥사졸리디논 유도체 및 이를 함유하는 의약 조성물
KR101674146B1 (ko)	2008-10-10	2016-11-08	머크 샤프 앤드 돔 코포레이션	옥사졸리디논 및 이를 포함하는 조성물을 제조하는 방법
US8426389B2 (en)	2009-02-03	2013-04-23	Trius Therapeutics, Inc.	Crystalline form of R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-hydroxymethyl oxazolidin-2-one dihydrogen phosphate
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US5225565A (en) *	1988-09-15	1993-07-06	The Upjohn Company	Antibacterial 3-(fused-ring substituted)phenyl-5β-amidomethyloxazolidin-2-ones
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1994
- 1994-09-27 DK DK94931278T patent/DK0730591T3/da active
- 1994-09-27 KR KR1019960702714A patent/KR100312903B1/ko not_active IP Right Cessation
- 1994-09-27 US US08/640,899 patent/US5652238A/en not_active Expired - Fee Related
- 1994-09-27 DE DE69419523T patent/DE69419523T2/de not_active Expired - Fee Related
- 1994-09-27 ES ES94931278T patent/ES2133588T3/es not_active Expired - Lifetime
- 1994-09-27 WO PCT/US1994/010582 patent/WO1995014684A1/fr active IP Right Grant
- 1994-09-27 AU AU80103/94A patent/AU698699B2/en not_active Ceased
- 1994-09-27 NZ NZ274966A patent/NZ274966A/en unknown
- 1994-09-27 JP JP51504895A patent/JP3698724B2/ja not_active Expired - Fee Related
- 1994-09-27 AT AT94931278T patent/ATE182142T1/de not_active IP Right Cessation
- 1994-09-27 EP EP94931278A patent/EP0730591B1/fr not_active Expired - Lifetime
- 1994-09-27 CA CA002174107A patent/CA2174107C/fr not_active Expired - Fee Related
- 1994-09-27 CN CN94194241A patent/CN1046276C/zh not_active Expired - Fee Related
- 1994-10-07 ZA ZA947885A patent/ZA947885B/xx unknown
- 1994-10-10 IL IL11121594A patent/IL111215A0/xx unknown
- 1994-10-13 TW TW083109509A patent/TW427987B/zh not_active IP Right Cessation
- 1994-11-17 PE PE1994254930A patent/PE22896A1/es not_active Application Discontinuation
- 1994-11-17 CO CO94052446A patent/CO4290433A1/es unknown
1999
- 1999-10-07 GR GR990402509T patent/GR3031420T3/el unknown
2000
- 2000-07-14 LV LVP-00-91A patent/LV12538B/en unknown

Also Published As

Publication number	Publication date
TW427987B (en)	2001-04-01
CN1135752A (zh)	1996-11-13
AU698699B2 (en)	1998-11-05
DE69419523T2 (de)	1999-11-25
DE69419523D1 (en)	1999-08-19
PE22896A1 (es)	1996-06-07
IL111215A0 (en)	1994-12-29
CN1046276C (zh)	1999-11-10
LV12538A (en)	2000-10-20
CA2174107C (fr)	2005-04-12
AU8010394A (en)	1995-06-13
JP3698724B2 (ja)	2005-09-21
ATE182142T1 (de)	1999-07-15
DK0730591T3 (da)	2000-01-31
CA2174107A1 (fr)	1995-06-01
US5652238A (en)	1997-07-29
CO4290433A1 (es)	1996-04-17
NZ274966A (en)	1998-01-26
JPH09505582A (ja)	1997-06-03
WO1995014684A1 (fr)	1995-06-01
GR3031420T3 (en)	2000-01-31
KR960705818A (ko)	1996-11-08
KR100312903B1 (ko)	2002-02-28
ES2133588T3 (es)	1999-09-16
EP0730591A1 (fr)	1996-09-11
EP0730591B1 (fr)	1999-07-14
ZA947885B (en)	1996-04-09

Publication	Publication Date	Title
LV12538B (en)	2000-12-20	ESTERS OF EXCLUDED HYDROXYCETETHYL-PIPERAZIN-FENIL-OKSASOLIDINONE
RU2105003C1 (ru)	1998-02-20	Производное оксазолидинона или его фармацевтически приемлемая соль, способ лечения микробных инфекций у теплокровных животных
EP0717738B1 (fr)	1999-10-20	Agents antimicrobiens oxazolidinone a substitution oxazine et thiazine
US6689779B2 (en)	2004-02-10	Oxazolidinone derivatives and a process for the preparation thereof
EP0123444B1 (fr)	1989-01-25	Dérivés 4-substitués de 2-azétidinone, procédé pour la fabrication de dérivés et médicament contenant les dérivés
AU739055B2 (en)	2001-10-04	Oxazolidinone derivatives and pharmaceutical compositions
MXPA06003124A (es)	2006-06-20	Profarmacos de aciloximetilcarbamato-oxazolidinonas.
EP1242395B1 (fr)	2005-02-02	Esters d'acide benzoique d'oxazolidinones presentant un substituant d'hydroxyacetylpiperazine
US4900752A (en)	1990-02-13	Pyranobenzoxadiazole derivatives
WO2004002967A1 (fr)	2004-01-08	Difluorothioacetamides d'oxazolidinones utilises comme agents anti-microbiens
MXPA05000257A (es)	2005-07-15	Difluorotioacetamidas de oxazolidinonas con un sustituyente de glicoloilpiperazina.
US6348459B1 (en)	2002-02-19	Sultam and sultone derived oxazolidinones