NO315798B1 - Oksazolidinon-antibakterielle midler med en tiokarbonylfunksjonalitet - Google Patents
Oksazolidinon-antibakterielle midler med en tiokarbonylfunksjonalitet Download PDFInfo
- Publication number
- NO315798B1 NO315798B1 NO19995846A NO995846A NO315798B1 NO 315798 B1 NO315798 B1 NO 315798B1 NO 19995846 A NO19995846 A NO 19995846A NO 995846 A NO995846 A NO 995846A NO 315798 B1 NO315798 B1 NO 315798B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- phenyl
- oxazolidinyl
- oxo
- fluoro
- Prior art date
Links
- 239000003242 anti bacterial agent Substances 0.000 title abstract 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 7
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- BWTWZIALANOYCK-ZDUSSCGKSA-N n-[[(5s)-3-(3-fluoro-4-thiomorpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C(C=C1F)=CC=C1N1CCSCC1 BWTWZIALANOYCK-ZDUSSCGKSA-N 0.000 claims description 11
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 claims description 7
- JTPOXGAVQGGEJA-ZDUSSCGKSA-N n-[[(5s)-2-oxo-3-[4-(1,2,4-triazol-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C1=CC=C(N2N=CN=C2)C=C1 JTPOXGAVQGGEJA-ZDUSSCGKSA-N 0.000 claims description 7
- QIEJDAIIANDOPK-ZDUSSCGKSA-N n-[[(5s)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]propanethioamide Chemical compound O=C1O[C@@H](CNC(=S)CC)CN1C(C=C1F)=CC=C1N1CCOCC1 QIEJDAIIANDOPK-ZDUSSCGKSA-N 0.000 claims description 7
- VYQGQLBCIZHAPY-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[4-(5-methyl-1,3,4-thiadiazol-2-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C(C=C1F)=CC=C1N1CCN(C=2SC(C)=NN=2)CC1 VYQGQLBCIZHAPY-HNNXBMFYSA-N 0.000 claims description 7
- LFXOOQHDEJOJIE-LBPRGKRZSA-N 1-[[(5s)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-3-methylthiourea Chemical compound O=C1O[C@@H](CNC(=S)NC)CN1C(C=C1F)=CC=C1N1CCOCC1 LFXOOQHDEJOJIE-LBPRGKRZSA-N 0.000 claims description 5
- SVSMPRQOCTYPAX-LBPRGKRZSA-N 2-chloro-n-[[(5s)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound FC1=CC(N2C(O[C@@H](CNC(=S)CCl)C2)=O)=CC=C1N1CCOCC1 SVSMPRQOCTYPAX-LBPRGKRZSA-N 0.000 claims description 5
- HHOYOSZHKNOVOI-ZDUSSCGKSA-N methyl 3-[[(5s)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methylamino]-3-sulfanylidenepropanoate Chemical compound O=C1O[C@@H](CNC(=S)CC(=O)OC)CN1C(C=C1F)=CC=C1N1CCOCC1 HHOYOSZHKNOVOI-ZDUSSCGKSA-N 0.000 claims description 5
- ARKKSPJWSZIEQK-ZDUSSCGKSA-N n-[[(5s)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C(C=C1F)=CC=C1N1CCOCC1 ARKKSPJWSZIEQK-ZDUSSCGKSA-N 0.000 claims description 5
- DBPLFXMXFJMCQM-LBPRGKRZSA-N n-[[(5s)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]methanethioamide Chemical compound FC1=CC(N2C(O[C@@H](CNC=S)C2)=O)=CC=C1N1CCOCC1 DBPLFXMXFJMCQM-LBPRGKRZSA-N 0.000 claims description 5
- VFCHLSMEQXDJQO-ZDUSSCGKSA-N n-[[(5s)-3-[1-(2-hydroxyacetyl)-2,3-dihydroindol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C1=CC=C(N(CC2)C(=O)CO)C2=C1 VFCHLSMEQXDJQO-ZDUSSCGKSA-N 0.000 claims description 5
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims description 4
- RNYUINWPIBQLJH-LBPRGKRZSA-N 2-fluoro-n-[[(5s)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)CF)CN1C(C=C1F)=CC=C1N1CCOCC1 RNYUINWPIBQLJH-LBPRGKRZSA-N 0.000 claims description 4
- INLSMIZFVBPRNN-NSHDSACASA-N [(5s)-2-oxo-3-[4-(1,2,4-triazol-1-yl)phenyl]-1,3-oxazolidin-5-yl]methylthiourea Chemical compound O=C1O[C@@H](CNC(=S)N)CN1C1=CC=C(N2N=CN=C2)C=C1 INLSMIZFVBPRNN-NSHDSACASA-N 0.000 claims description 4
- AIVMWDLYXWCKMI-NSHDSACASA-N [(5s)-3-[1-(2-hydroxyacetyl)-2,3-dihydroindol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methylthiourea Chemical compound O=C1O[C@@H](CNC(=S)N)CN1C1=CC=C(N(CC2)C(=O)CO)C2=C1 AIVMWDLYXWCKMI-NSHDSACASA-N 0.000 claims description 4
- HHAMYGJCRUADNI-LBPRGKRZSA-N [(5s)-3-[3-fluoro-4-[4-(2-hydroxyacetyl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methylthiourea Chemical compound O=C1O[C@@H](CNC(=S)N)CN1C(C=C1F)=CC=C1N1CCN(C(=O)CO)CC1 HHAMYGJCRUADNI-LBPRGKRZSA-N 0.000 claims description 4
- SYUFGFAMGWERAW-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-(2-hydroxyacetyl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C(C=C1F)=CC=C1N1CCN(C(=O)CO)CC1 SYUFGFAMGWERAW-AWEZNQCLSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- JQYWSYVDCGKSQE-ZDUSSCGKSA-N 2-cyano-n-[[(5s)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound FC1=CC(N2C(O[C@@H](CNC(=S)CC#N)C2)=O)=CC=C1N1CCOCC1 JQYWSYVDCGKSQE-ZDUSSCGKSA-N 0.000 claims description 2
- YRMHGBXDYQTEMM-NSHDSACASA-N [(5s)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methylthiourea Chemical compound O=C1O[C@@H](CNC(=S)N)CN1C(C=C1F)=CC=C1N1CCOCC1 YRMHGBXDYQTEMM-NSHDSACASA-N 0.000 claims description 2
- AYDMNAXXMUXEOZ-NSHDSACASA-N [(5s)-3-(3-fluoro-4-thiomorpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methylthiourea Chemical compound O=C1O[C@@H](CNC(=S)N)CN1C(C=C1F)=CC=C1N1CCSCC1 AYDMNAXXMUXEOZ-NSHDSACASA-N 0.000 claims description 2
- KFDTTXDYSBEMES-ZDUSSCGKSA-N n-[[(5s)-3-[3,5-difluoro-4-[4-(2-hydroxyacetyl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C(C=C1F)=CC(F)=C1N1CCN(C(=O)CO)CC1 KFDTTXDYSBEMES-ZDUSSCGKSA-N 0.000 claims description 2
- ZHGKXIUPTQZKAK-ZDUSSCGKSA-N n-[[(5s)-3-[4-(2,4-dioxo-1,3,8-triazaspiro[4.5]decan-8-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C(C=C1F)=CC=C1N1CCC2(C(NC(=O)N2)=O)CC1 ZHGKXIUPTQZKAK-ZDUSSCGKSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 104
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
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- 239000000243 solution Substances 0.000 description 73
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- 238000005481 NMR spectroscopy Methods 0.000 description 41
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- 239000012267 brine Substances 0.000 description 32
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- 229920006395 saturated elastomer Polymers 0.000 description 20
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 20
- 238000004587 chromatography analysis Methods 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- KCOPWUJJPSTRIZ-UHFFFAOYSA-N ethyl ethanedithioate Chemical compound CCSC(C)=S KCOPWUJJPSTRIZ-UHFFFAOYSA-N 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 17
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- 235000019439 ethyl acetate Nutrition 0.000 description 11
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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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—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
-
- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—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
- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US4834297P | 1997-05-30 | 1997-05-30 | |
PCT/US1998/009889 WO1998054161A1 (en) | 1997-05-30 | 1998-05-18 | Oxazolidinone antibacterial agents having a thiocarbonyl functionality |
Publications (3)
Publication Number | Publication Date |
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NO995846D0 NO995846D0 (no) | 1999-11-29 |
NO995846L NO995846L (no) | 2000-01-28 |
NO315798B1 true NO315798B1 (no) | 2003-10-27 |
Family
ID=21954059
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19995846A NO315798B1 (no) | 1997-05-30 | 1999-11-29 | Oksazolidinon-antibakterielle midler med en tiokarbonylfunksjonalitet |
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US (1) | US6218413B1 (zh) |
EP (1) | EP0984947B8 (zh) |
JP (1) | JP2002501530A (zh) |
KR (1) | KR20010013192A (zh) |
CN (1) | CN1138765C (zh) |
AT (1) | ATE293609T1 (zh) |
AU (1) | AU737995B2 (zh) |
BR (1) | BR9815518A (zh) |
CA (1) | CA2288750A1 (zh) |
DE (1) | DE69829846T2 (zh) |
ES (1) | ES2242280T3 (zh) |
FI (1) | FI19992555A (zh) |
HK (1) | HK1027569A1 (zh) |
HU (1) | HUP0001393A3 (zh) |
NO (1) | NO315798B1 (zh) |
NZ (1) | NZ501412A (zh) |
PL (1) | PL337329A1 (zh) |
RU (1) | RU2208613C2 (zh) |
SK (1) | SK156499A3 (zh) |
WO (1) | WO1998054161A1 (zh) |
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JP2000204084A (ja) * | 1998-11-11 | 2000-07-25 | Hokuriku Seiyaku Co Ltd | チオカルバミド酸誘導体 |
AU1045300A (en) * | 1998-11-17 | 2000-06-05 | Bayer Aktiengesellschaft | Novel heterocyclyl-substituted oxazolidone derivatives |
AU1379900A (en) * | 1998-11-17 | 2000-06-05 | Bayer Aktiengesellschaft | Novel substituted phenyloxazolidone derivatives |
CN1322204A (zh) * | 1998-11-27 | 2001-11-14 | 法玛西雅厄普约翰美国公司 | 具有硫代羰基官能团的噁唑烷酮抗菌剂 |
JP2003513885A (ja) | 1999-07-28 | 2003-04-15 | ファルマシア・アンド・アップジョン・カンパニー | オキサゾリジノンおよび抗感染薬としてのその使用 |
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PE20010851A1 (es) * | 1999-12-14 | 2001-08-17 | Upjohn Co | Esteres del acido benzoico de oxazolidinonas que tienen un substituyente hidroxiacetilpiperazina |
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DE19962924A1 (de) | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
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US6642238B2 (en) * | 2000-02-10 | 2003-11-04 | Pharmacia And Upjohn Company | Oxazolidinone thioamides with piperazine amide substituents |
AU2001253113B2 (en) * | 2000-04-20 | 2005-02-03 | Pharmacia & Upjohn Company | Use of thioamide oxazolidinones for the treatment of bone resorption and osteoporosis |
GB0009803D0 (en) | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
US6562820B2 (en) | 2000-07-05 | 2003-05-13 | Pharmacia & Upjohn Company | Method for treatment and prevention of mastitis |
US6734307B2 (en) * | 2000-07-17 | 2004-05-11 | Ranbaxy Laboratories Limited | Oxazolidinone derivatives as antimicrobials |
PE20020689A1 (es) * | 2000-11-17 | 2002-08-03 | Upjohn Co | Oxazolidinonas con un heterociclo de 6 o 7 miembros unidos con enlace anular al benceno |
AU2002256995A1 (en) | 2001-02-07 | 2002-08-28 | Ortho-Mcneil Pharmaceutical, Inc. | Pyridoarylphenyl oxazolidinone antibacterials, and related compositions and methods |
US20050032861A1 (en) * | 2001-04-07 | 2005-02-10 | Betts Michael John | Oxazolidines containing a sulfonimid group as antibiotics |
DE10129725A1 (de) | 2001-06-20 | 2003-01-02 | Bayer Ag | Kombinationstherapie substituierter Oxazolidinone |
US7141588B2 (en) | 2002-02-25 | 2006-11-28 | Pfizer, Inc. | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
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BR0215921A (pt) * | 2002-07-29 | 2005-09-13 | Ranbaxy Lab Ltd | Derivados de oxazolidinona utilizáveis como antimicrobianos e processo de sua preparação |
ATE321760T1 (de) | 2002-08-12 | 2006-04-15 | Pharmacia & Upjohn Co Llc | N-aryl-2-oxazolidinone und deren derivate |
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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. |
GB0229521D0 (en) * | 2002-12-19 | 2003-01-22 | Astrazeneca Ab | Chemical compounds |
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 |
EP1615916A1 (en) | 2003-04-09 | 2006-01-18 | Pharmacia & Upjohn Company LLC | Antimicrobial 3.1.0 bicyclohexylphenyl-oxazolidinone derivatives and analogues |
PT1656370E (pt) | 2003-06-03 | 2012-11-29 | Rib X Pharmaceuticals Inc | Compostos biaril-heterocíclicos e métodos de os produzir e de os utilizar |
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MXPA06002188A (es) * | 2003-08-25 | 2006-04-27 | Warner Lambert Co | Nuevos compuestos antimicrobianos de ariloxazolidinona. |
US7687627B2 (en) * | 2003-09-08 | 2010-03-30 | Wockhardt Limited | Substituted piperidino phenyloxazolidinones having antimicrobial activity with improved in vivo efficacy |
US7304050B2 (en) | 2003-09-16 | 2007-12-04 | Pfizer Inc. | Antibacterial agents |
DE10355461A1 (de) | 2003-11-27 | 2005-06-23 | Bayer Healthcare Ag | Verfahren zur Herstellung einer festen, oral applizierbaren pharmazeutischen Zusammensetzung |
JP2007514782A (ja) * | 2003-12-17 | 2007-06-07 | リブ−エックス ファーマシューティカルズ,インコーポレイテッド | ハロゲン化ビアリール複素環式化合物ならびにその作製方法および使用方法 |
WO2005082900A2 (en) * | 2004-01-28 | 2005-09-09 | Pharmacia & Upjohn Company Llc | Oxazolidinone amidoximes as antibacterial agents |
DE102004062475A1 (de) * | 2004-12-24 | 2006-07-06 | Bayer Healthcare Ag | Feste, oral applizierbare pharmazeutische Darreichungsformen mit modifizierter Freisetzung |
EP1685841A1 (en) * | 2005-01-31 | 2006-08-02 | Bayer Health Care Aktiengesellschaft | Prevention and treatment of thromboembolic disorders |
US7592335B2 (en) | 2005-04-15 | 2009-09-22 | Ranbaxy Laboratories Limited | Oxazolidinone derivatives as antimicrobials |
DE602006019870D1 (de) | 2005-06-08 | 2011-03-10 | Rib X Pharmaceuticals Inc | Verfahren zur synthese von triazolen |
DE102005045518A1 (de) * | 2005-09-23 | 2007-03-29 | Bayer Healthcare Ag | 2-Aminoethoxyessigsäure-Derivate und ihre Verwendung |
DE102005047561A1 (de) | 2005-10-04 | 2007-04-05 | Bayer Healthcare Ag | Feste, oral applizierbare pharmazeutische Darreichungsformen mit schneller Wirkstofffreisetzung |
DE102005047558A1 (de) * | 2005-10-04 | 2008-02-07 | Bayer Healthcare Ag | Kombinationstherapie substituierter Oxazolidinone zur Prophylaxe und Behandlung von cerebralen Durchblutungsstörungen |
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 |
WO2007114326A1 (ja) | 2006-03-31 | 2007-10-11 | Research Foundation Itsuu Laboratory | ヘテロ環を有する新規化合物 |
EP2170874A4 (en) * | 2007-06-22 | 2011-08-31 | Orchid Res Lab Ltd | NEW COMPOUNDS AND THEIR USE |
CN101883768A (zh) | 2007-10-02 | 2010-11-10 | 财团法人乙卯研究所 | 具有7元杂环的噁唑烷酮衍生物 |
US9173887B2 (en) | 2010-12-22 | 2015-11-03 | Abbvie Inc. | Hepatitis C inhibitors and uses thereof |
EP2766373B1 (en) * | 2011-10-11 | 2016-08-17 | Council of Scientific & Industrial Research | Sila analogs of oxazolidinone derivatives and synthesis thereof |
CN103360294B (zh) * | 2012-03-28 | 2015-11-25 | 复旦大学 | 具有抗结核活性的化合物及其制备方法和应用 |
CN103044341B (zh) * | 2012-12-20 | 2015-07-01 | 郑州大学 | 1,2,3-三唑-氨基二硫代甲酸酯-脲复合体、其制备方法及其应用 |
WO2015031036A1 (en) * | 2013-08-26 | 2015-03-05 | Purdue Pharma L.P. | Azaspiro[4.5] decane derivatives and use thereof |
CN108299329A (zh) * | 2018-03-28 | 2018-07-20 | 许传森 | 一种噁唑酮类衍生物及其在抗菌药物中的应用 |
CN115466253A (zh) * | 2021-06-16 | 2022-12-13 | 沈阳药科大学 | 含二硫代氨基甲酸酯结构的噁唑烷酮类化合物及其制备方法 |
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ES533097A0 (es) * | 1983-06-07 | 1985-08-01 | Du Pont | Un procedimiento para la preparacion de nuevos derivados del amino-metil-oxooxazolidinil-benzeno. |
CA1260948A (en) * | 1984-12-05 | 1989-09-26 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents |
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 | Upjohn Co | 3-(Stickstoff substituierte)phenyl-5-beta-amidomethyloxazoliden-2-one |
MY115155A (en) | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
DE4425612A1 (de) | 1994-07-20 | 1996-04-04 | Bayer Ag | 6-gliedrige stickstoffhaltige Heteroaryl-oxazolidinone |
GB9521508D0 (en) | 1995-10-20 | 1995-12-20 | Zeneca Ltd | Chemical compounds |
DE19601264A1 (de) * | 1996-01-16 | 1997-07-17 | Bayer Ag | Pyrido-annellierte Thienyl- und Furanyl-Oxazolidinone |
DE19604223A1 (de) | 1996-02-06 | 1997-08-07 | Bayer Ag | Neue substituierte Oxazolidinone |
DE69716925T2 (de) | 1996-08-21 | 2003-09-11 | Upjohn Co | Isoxazoline derivate und ihre verwendung als antimikroben |
-
1998
- 1998-05-18 NZ NZ501412A patent/NZ501412A/en unknown
- 1998-05-18 US US09/080,751 patent/US6218413B1/en not_active Expired - Fee Related
- 1998-05-18 KR KR19997011178A patent/KR20010013192A/ko active IP Right Grant
- 1998-05-18 AT AT98922303T patent/ATE293609T1/de not_active IP Right Cessation
- 1998-05-18 CA CA002288750A patent/CA2288750A1/en not_active Abandoned
- 1998-05-18 EP EP98922303A patent/EP0984947B8/en not_active Expired - Lifetime
- 1998-05-18 RU RU99128083/04A patent/RU2208613C2/ru not_active IP Right Cessation
- 1998-05-18 BR BR9815518-0A patent/BR9815518A/pt not_active Application Discontinuation
- 1998-05-18 SK SK1564-99A patent/SK156499A3/sk unknown
- 1998-05-18 PL PL98337329A patent/PL337329A1/xx unknown
- 1998-05-18 DE DE69829846T patent/DE69829846T2/de not_active Expired - Fee Related
- 1998-05-18 ES ES98922303T patent/ES2242280T3/es not_active Expired - Lifetime
- 1998-05-18 HU HU0001393A patent/HUP0001393A3/hu unknown
- 1998-05-18 CN CNB98805423XA patent/CN1138765C/zh not_active Expired - Fee Related
- 1998-05-18 WO PCT/US1998/009889 patent/WO1998054161A1/en not_active Application Discontinuation
- 1998-05-18 JP JP50072299A patent/JP2002501530A/ja not_active Withdrawn
- 1998-05-18 AU AU74883/98A patent/AU737995B2/en not_active Ceased
-
1999
- 1999-11-29 NO NO19995846A patent/NO315798B1/no unknown
- 1999-11-30 FI FI992555A patent/FI19992555A/fi not_active IP Right Cessation
-
2000
- 2000-10-23 HK HK00106696A patent/HK1027569A1/xx unknown
Also Published As
Publication number | Publication date |
---|---|
EP0984947B1 (en) | 2005-04-20 |
NO995846L (no) | 2000-01-28 |
CA2288750A1 (en) | 1998-12-03 |
EP0984947B8 (en) | 2005-06-15 |
US6218413B1 (en) | 2001-04-17 |
NZ501412A (en) | 2001-11-30 |
HUP0001393A2 (hu) | 2001-06-28 |
ATE293609T1 (de) | 2005-05-15 |
WO1998054161A1 (en) | 1998-12-03 |
KR20010013192A (ko) | 2001-02-26 |
WO1998054161A9 (en) | 1999-04-08 |
HUP0001393A3 (en) | 2001-07-30 |
ES2242280T3 (es) | 2005-11-01 |
PL337329A1 (en) | 2000-08-14 |
SK156499A3 (en) | 2000-06-12 |
EP0984947A1 (en) | 2000-03-15 |
AU737995B2 (en) | 2001-09-06 |
CN1138765C (zh) | 2004-02-18 |
DE69829846T2 (de) | 2006-02-23 |
AU7488398A (en) | 1998-12-30 |
HK1027569A1 (en) | 2001-01-19 |
DE69829846D1 (de) | 2005-05-25 |
RU2208613C2 (ru) | 2003-07-20 |
NO995846D0 (no) | 1999-11-29 |
JP2002501530A (ja) | 2002-01-15 |
BR9815518A (pt) | 2000-11-21 |
CN1257486A (zh) | 2000-06-21 |
FI19992555A (fi) | 1999-11-30 |
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