HU189196B - Process for preparing 4-/2-oxo-oxazolidin -3-yl/-benzene-sulphonamides with antibacterial activity - Google Patents
Process for preparing 4-/2-oxo-oxazolidin -3-yl/-benzene-sulphonamides with antibacterial activity Download PDFInfo
- Publication number
- HU189196B HU189196B HU823896A HU389682A HU189196B HU 189196 B HU189196 B HU 189196B HU 823896 A HU823896 A HU 823896A HU 389682 A HU389682 A HU 389682A HU 189196 B HU189196 B HU 189196B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- alkyl
- hydroxymethyl
- hydrogen
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 title description 10
- 229960000649 oxyphenbutazone Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 91
- 238000000034 method Methods 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 15
- -1 alkali metal cations Chemical class 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
- YSXHFFYGMYBNIE-UHFFFAOYSA-N O=C1NC(OC1)C1=C(C=CC=C1)S(=O)(=O)N Chemical class O=C1NC(OC1)C1=C(C=CC=C1)S(=O)(=O)N YSXHFFYGMYBNIE-UHFFFAOYSA-N 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 abstract description 2
- QOSYRNNCNXXYTA-UHFFFAOYSA-N 2-(1,3-oxazolidin-2-yl)-4-oxocyclohexa-1,5-diene-1-sulfonamide Chemical class C1C(=O)C=CC(S(=O)(=O)N)=C1C1OCCN1 QOSYRNNCNXXYTA-UHFFFAOYSA-N 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 52
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- 239000011541 reaction mixture Substances 0.000 description 39
- 239000000047 product Substances 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- 239000007787 solid Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 239000003921 oil Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 10
- WHXUEJAEOKJMAD-VIFPVBQESA-N (5s)-5-(hydroxymethyl)-3-phenyl-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](CO)CN1C1=CC=CC=C1 WHXUEJAEOKJMAD-VIFPVBQESA-N 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- WHXUEJAEOKJMAD-UHFFFAOYSA-N 5-(hydroxymethyl)-3-phenyl-1,3-oxazolidin-2-one Chemical compound O=C1OC(CO)CN1C1=CC=CC=C1 WHXUEJAEOKJMAD-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 6
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000005708 Sodium hypochlorite Substances 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 6
- 150000003461 sulfonyl halides Chemical class 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- 229920001817 Agar Polymers 0.000 description 5
- 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 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- 150000002148 esters Chemical class 0.000 description 5
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- 239000000706 filtrate Substances 0.000 description 5
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- 229920006395 saturated elastomer Polymers 0.000 description 5
- INHHFZUVCCBNTO-SECBINFHSA-N (2r)-3-anilinopropane-1,2-diol Chemical group OC[C@H](O)CNC1=CC=CC=C1 INHHFZUVCCBNTO-SECBINFHSA-N 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 4
- QVDDLNAGDYFFOJ-UHFFFAOYSA-N 4-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(=O)OC(CO)C1 QVDDLNAGDYFFOJ-UHFFFAOYSA-N 0.000 description 4
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- 241000588724 Escherichia coli Species 0.000 description 4
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- 238000000338 in vitro Methods 0.000 description 4
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- VLVCWODDMDGANW-UHFFFAOYSA-N 4-methyl-n-phenylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=CC=C1 VLVCWODDMDGANW-UHFFFAOYSA-N 0.000 description 3
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- VQCSSMIZYGHLSP-UHFFFAOYSA-N n-diazo-4-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]benzenesulfonamide Chemical compound O=C1OC(CO)CN1C1=CC=C(S(=O)(=O)N=[N+]=[N-])C=C1 VQCSSMIZYGHLSP-UHFFFAOYSA-N 0.000 description 2
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- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000005720 sucrose Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Child & Adolescent Psychology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32758381A | 1981-12-04 | 1981-12-04 | |
| US41756982A | 1982-09-15 | 1982-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU189196B true HU189196B (en) | 1986-06-30 |
Family
ID=26985954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU823896A HU189196B (en) | 1981-12-04 | 1982-12-03 | Process for preparing 4-/2-oxo-oxazolidin -3-yl/-benzene-sulphonamides with antibacterial activity |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0081200B1 (OSRAM) |
| AU (1) | AU560666B2 (OSRAM) |
| CA (1) | CA1182824A (OSRAM) |
| DE (1) | DE3273626D1 (OSRAM) |
| DK (1) | DK538382A (OSRAM) |
| ES (1) | ES517852A0 (OSRAM) |
| FI (1) | FI78078C (OSRAM) |
| GR (1) | GR77795B (OSRAM) |
| HU (1) | HU189196B (OSRAM) |
| IL (1) | IL67397A (OSRAM) |
| NO (1) | NO156751C (OSRAM) |
| NZ (1) | NZ202695A (OSRAM) |
| PT (1) | PT75928B (OSRAM) |
| SU (1) | SU1194274A3 (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4461773A (en) * | 1982-09-15 | 1984-07-24 | E. I. Dupont De Nemours And Company | P-Oxooxazolidinylbenzene compounds as antibacterial agents |
| 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 |
| DE3525648A1 (de) * | 1985-07-18 | 1987-01-29 | Bokel Heinz Hermann Dr | 1-oxa-2-oxo-2-r-3-aza-5-z-cyclopentanderivate |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3456241A (en) * | 1965-08-10 | 1969-07-15 | Bell Telephone Labor Inc | Reed relay shift register and counter circuits |
| LU80081A1 (fr) * | 1977-08-26 | 1979-05-15 | Delalande Sa | Nouvelles hydroxymethyl-5 oxazolidinones-2,leur procede de preparation et leur application therapeutique |
| US4128654A (en) * | 1978-02-10 | 1978-12-05 | E. I. Du Pont De Nemours And Company | 5-Halomethyl-3-phenyl-2-oxazolidinones |
| FR2458547B2 (fr) * | 1978-06-09 | 1986-05-16 | Delalande Sa | Nouvelles n-aryle azolones, leur procede de preparation et leur application en therapeutique |
| US4340606A (en) * | 1980-10-23 | 1982-07-20 | E. I. Du Pont De Nemours And Company | 3-(p-Alkylsulfonylphenyl)oxazolidinone derivatives as antibacterial agents |
-
1982
- 1982-12-01 AU AU91032/82A patent/AU560666B2/en not_active Ceased
- 1982-12-01 ES ES517852A patent/ES517852A0/es active Granted
- 1982-12-02 EP EP82111135A patent/EP0081200B1/en not_active Expired
- 1982-12-02 DE DE8282111135T patent/DE3273626D1/de not_active Expired
- 1982-12-02 IL IL67397A patent/IL67397A/xx unknown
- 1982-12-02 CA CA000416882A patent/CA1182824A/en not_active Expired
- 1982-12-03 NO NO824072A patent/NO156751C/no unknown
- 1982-12-03 SU SU823519552A patent/SU1194274A3/ru active
- 1982-12-03 NZ NZ202695A patent/NZ202695A/en unknown
- 1982-12-03 FI FI824182A patent/FI78078C/fi not_active IP Right Cessation
- 1982-12-03 PT PT75928A patent/PT75928B/pt unknown
- 1982-12-03 HU HU823896A patent/HU189196B/hu not_active IP Right Cessation
- 1982-12-03 DK DK538382A patent/DK538382A/da not_active Application Discontinuation
- 1982-12-03 GR GR69986A patent/GR77795B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO824072L (no) | 1983-06-06 |
| NO156751B (no) | 1987-08-10 |
| FI824182L (fi) | 1983-06-05 |
| PT75928A (en) | 1983-01-01 |
| ES8401951A1 (es) | 1984-01-16 |
| FI78078C (fi) | 1989-06-12 |
| DK538382A (da) | 1983-06-05 |
| EP0081200A1 (en) | 1983-06-15 |
| IL67397A0 (en) | 1983-05-15 |
| DE3273626D1 (en) | 1986-11-13 |
| EP0081200B1 (en) | 1986-10-08 |
| IL67397A (en) | 1987-03-31 |
| FI824182A0 (fi) | 1982-12-03 |
| AU9103282A (en) | 1983-06-09 |
| NO156751C (no) | 1987-12-02 |
| GR77795B (OSRAM) | 1984-09-25 |
| FI78078B (fi) | 1989-02-28 |
| NZ202695A (en) | 1985-01-31 |
| AU560666B2 (en) | 1987-04-16 |
| CA1182824A (en) | 1985-02-19 |
| SU1194274A3 (ru) | 1985-11-23 |
| PT75928B (en) | 1985-12-20 |
| ES517852A0 (es) | 1984-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |