NO309091B1 - Oksazolidinonderivater, deres fremstilling samt medikament og farmasøytisk preparat inneholdende disse - Google Patents
Oksazolidinonderivater, deres fremstilling samt medikament og farmasøytisk preparat inneholdende disse Download PDFInfo
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- NO309091B1 NO309091B1 NO975530A NO975530A NO309091B1 NO 309091 B1 NO309091 B1 NO 309091B1 NO 975530 A NO975530 A NO 975530A NO 975530 A NO975530 A NO 975530A NO 309091 B1 NO309091 B1 NO 309091B1
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- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000003814 drug Substances 0.000 title claims description 7
- 229940079593 drug Drugs 0.000 title claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 74
- -1 methylenedioxy group Chemical group 0.000 claims description 73
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 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 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- LSYOFPBORRARMF-UHFFFAOYSA-N 5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical class OCC1CNC(=O)O1 LSYOFPBORRARMF-UHFFFAOYSA-N 0.000 claims description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 6
- 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 claims description 6
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 claims description 3
- DNSGQMOSYDHNHO-UHFFFAOYSA-N 4-(methoxymethyl)-1,3-dioxolan-2-one Chemical class COCC1COC(=O)O1 DNSGQMOSYDHNHO-UHFFFAOYSA-N 0.000 claims description 2
- PLTALYMSSXETDZ-UHFFFAOYSA-N 4-(phenylmethoxymethyl)-1,3-dioxolan-2-one Chemical class O1C(=O)OCC1COCC1=CC=CC=C1 PLTALYMSSXETDZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- POXSDSRWVJZWCN-UHFFFAOYSA-N triphenylphosphanium;iodide Chemical compound I.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 POXSDSRWVJZWCN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000047 product Substances 0.000 description 41
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000000377 silicon dioxide Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000004587 chromatography analysis Methods 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- FNDBNJUWRRLOHU-UHFFFAOYSA-N 2-fluoro-4-phenylmethoxybenzonitrile Chemical compound C1=C(C#N)C(F)=CC(OCC=2C=CC=CC=2)=C1 FNDBNJUWRRLOHU-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 102000010909 Monoamine Oxidase Human genes 0.000 description 5
- 108010062431 Monoamine oxidase Proteins 0.000 description 5
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 238000001665 trituration Methods 0.000 description 5
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- DNSGQMOSYDHNHO-SCSAIBSYSA-N (4r)-4-(methoxymethyl)-1,3-dioxolan-2-one Chemical compound COC[C@@H]1COC(=O)O1 DNSGQMOSYDHNHO-SCSAIBSYSA-N 0.000 description 3
- FGATZKMMLFZPMC-MRVPVSSYSA-N (5R)-3-(6-hydroxy-1,2-benzoxazol-3-yl)-5-(methoxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](COC)CN1C1=NOC2=CC(O)=CC=C12 FGATZKMMLFZPMC-MRVPVSSYSA-N 0.000 description 3
- ALXDBDKUDRBYJW-HNNXBMFYSA-N (5s)-5-(methoxymethyl)-3-(6-phenylmethoxy-1,2-benzothiazol-3-yl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](COC)CN1C1=NSC2=CC(OCC=3C=CC=CC=3)=CC=C12 ALXDBDKUDRBYJW-HNNXBMFYSA-N 0.000 description 3
- TWZDUIPNCURWOU-UHFFFAOYSA-N 4-phenylmethoxy-2-(propan-2-ylideneamino)oxybenzonitrile Chemical compound C1=C(C#N)C(ON=C(C)C)=CC(OCC=2C=CC=CC=2)=C1 TWZDUIPNCURWOU-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- RNVYQYLELCKWAN-RXMQYKEDSA-N [(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Chemical compound CC1(C)OC[C@@H](CO)O1 RNVYQYLELCKWAN-RXMQYKEDSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- PSJBSUHYCGQTHZ-BYPYZUCNSA-N (2s)-3-methoxypropane-1,2-diol Chemical compound COC[C@@H](O)CO PSJBSUHYCGQTHZ-BYPYZUCNSA-N 0.000 description 2
- FKXMKWWWEXEOFI-QMMMGPOBSA-N (5S)-3-(6-hydroxy-1,2-benzothiazol-3-yl)-5-(methoxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](COC)CN1C1=NSC2=CC(O)=CC=C12 FKXMKWWWEXEOFI-QMMMGPOBSA-N 0.000 description 2
- KIUVYTNSVRFRJO-ZETCQYMHSA-N (5S)-3-(6-hydroxy-1,2-benzoxazol-3-yl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](CO)CN1C1=NOC2=CC(O)=CC=C12 KIUVYTNSVRFRJO-ZETCQYMHSA-N 0.000 description 2
- REPMOCPOBKGVKX-VIFPVBQESA-N (5S)-3-(6-hydroxy-1-methylindazol-3-yl)-5-(methoxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](COC)CN1C1=NN(C)C2=CC(O)=CC=C12 REPMOCPOBKGVKX-VIFPVBQESA-N 0.000 description 2
- QRLLCMNCDIZEPW-NRFANRHFSA-N (5s)-3-(6-phenylmethoxy-1,2-benzoxazol-3-yl)-5-(phenylmethoxymethyl)-1,3-oxazolidin-2-one Chemical compound C([C@H]1OC(N(C1)C=1C2=CC=C(OCC=3C=CC=CC=3)C=C2ON=1)=O)OCC1=CC=CC=C1 QRLLCMNCDIZEPW-NRFANRHFSA-N 0.000 description 2
- RDNRKPBLIWVWMB-INIZCTEOSA-N (5s)-5-(methoxymethyl)-3-(1-methyl-6-phenylmethoxyindazol-3-yl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](COC)CN1C1=NN(C)C2=CC(OCC=3C=CC=CC=3)=CC=C12 RDNRKPBLIWVWMB-INIZCTEOSA-N 0.000 description 2
- DRULDXHUZDNVAN-HNNXBMFYSA-N (5s)-5-(methoxymethyl)-3-(6-phenylmethoxy-1,2-benzoxazol-3-yl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](COC)CN1C1=NOC2=CC(OCC=3C=CC=CC=3)=CC=C12 DRULDXHUZDNVAN-HNNXBMFYSA-N 0.000 description 2
- ZWTMSEROLHBUQZ-NSHDSACASA-N (5s)-5-(methoxymethyl)-3-[6-(4,4,4-trifluorobutoxy)-1,2-benzothiazol-3-yl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](COC)CN1C1=NSC2=CC(OCCCC(F)(F)F)=CC=C12 ZWTMSEROLHBUQZ-NSHDSACASA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WAXVPYHFYALUQB-UHFFFAOYSA-N 1-methyl-6-phenylmethoxyindazol-3-amine Chemical compound C1=C2N(C)N=C(N)C2=CC=C1OCC1=CC=CC=C1 WAXVPYHFYALUQB-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- REIVHYDACHXPNH-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C(F)=C1 REIVHYDACHXPNH-UHFFFAOYSA-N 0.000 description 2
- BDUFQZUCYCXBAU-SECBINFHSA-N 3-[(5r)-5-(methoxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-1,2-benzoxazole-6-carbaldehyde Chemical compound O=C1O[C@@H](COC)CN1C1=NOC2=CC(C=O)=CC=C12 BDUFQZUCYCXBAU-SECBINFHSA-N 0.000 description 2
- RGLYKOYBLQUSSF-UHFFFAOYSA-N 6-phenylmethoxy-1,2-benzothiazol-3-amine Chemical compound C=1C=C2C(N)=NSC2=CC=1OCC1=CC=CC=C1 RGLYKOYBLQUSSF-UHFFFAOYSA-N 0.000 description 2
- VUJMLRJWXXZRGU-UHFFFAOYSA-N 6-phenylmethoxy-1,2-benzoxazol-3-amine Chemical compound C=1C=C2C(N)=NOC2=CC=1OCC1=CC=CC=C1 VUJMLRJWXXZRGU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
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- 238000010520 demethylation reaction Methods 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 125000000904 isoindolyl group Chemical class C=1(NC=C2C=CC=CC12)* 0.000 description 2
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
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- ATRLVVVJFBQMEX-ZCFIWIBFSA-N (4r)-4-(methoxymethyl)-2,2-dimethyl-1,3-dioxolane Chemical compound COC[C@@H]1COC(C)(C)O1 ATRLVVVJFBQMEX-ZCFIWIBFSA-N 0.000 description 1
- PLTALYMSSXETDZ-SNVBAGLBSA-N (4r)-4-(phenylmethoxymethyl)-1,3-dioxolan-2-one Chemical compound O1C(=O)OC[C@H]1COCC1=CC=CC=C1 PLTALYMSSXETDZ-SNVBAGLBSA-N 0.000 description 1
- DNSGQMOSYDHNHO-BYPYZUCNSA-N (4s)-4-(methoxymethyl)-1,3-dioxolan-2-one Chemical compound COC[C@H]1COC(=O)O1 DNSGQMOSYDHNHO-BYPYZUCNSA-N 0.000 description 1
- FGATZKMMLFZPMC-QMMMGPOBSA-N (5S)-3-(6-hydroxy-1,2-benzoxazol-3-yl)-5-(methoxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](COC)CN1C1=NOC2=CC(O)=CC=C12 FGATZKMMLFZPMC-QMMMGPOBSA-N 0.000 description 1
- DFLGUEDWRDCQCH-SNVBAGLBSA-N (5r)-3-(6-ethenyl-1,2-benzoxazol-3-yl)-5-(methoxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](COC)CN1C1=NOC2=CC(C=C)=CC=C12 DFLGUEDWRDCQCH-SNVBAGLBSA-N 0.000 description 1
- DRULDXHUZDNVAN-OAHLLOKOSA-N (5r)-5-(methoxymethyl)-3-(6-phenylmethoxy-1,2-benzoxazol-3-yl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](COC)CN1C1=NOC2=CC(OCC=3C=CC=CC=3)=CC=C12 DRULDXHUZDNVAN-OAHLLOKOSA-N 0.000 description 1
- IOGPJCPJAQQLFL-OIUHTZQUSA-N (5r)-5-(methoxymethyl)-3-[6-[(e,4r)-5,5,5-trifluoro-4-hydroxypent-1-enyl]-1,2-benzoxazol-3-yl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](COC)CN1C1=NOC2=CC(\C=C\C[C@@H](O)C(F)(F)F)=CC=C12 IOGPJCPJAQQLFL-OIUHTZQUSA-N 0.000 description 1
- JAJDBNALJZYMAL-JTQLQIEISA-N (5s)-5-(hydroxymethyl)-3-[6-(4,4,4-trifluorobutoxy)-1,2-benzoxazol-3-yl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](CO)CN1C1=NOC2=CC(OCCCC(F)(F)F)=CC=C12 JAJDBNALJZYMAL-JTQLQIEISA-N 0.000 description 1
- QXMCTTHQHAWMSC-LBPRGKRZSA-N (5s)-5-(methoxymethyl)-3-[1-methyl-6-(4,4,4-trifluorobutoxy)indazol-3-yl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](COC)CN1C1=NN(C)C2=CC(OCCCC(F)(F)F)=CC=C12 QXMCTTHQHAWMSC-LBPRGKRZSA-N 0.000 description 1
- SQMNCLANJWZZOG-NSHDSACASA-N (5s)-5-(methoxymethyl)-3-[6-(4,4,4-trifluorobutoxy)-1,2-benzoxazol-3-yl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](COC)CN1C1=NOC2=CC(OCCCC(F)(F)F)=CC=C12 SQMNCLANJWZZOG-NSHDSACASA-N 0.000 description 1
- 206010050013 Abulia Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
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- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 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 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 206010033664 Panic attack Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- 206010041250 Social phobia Diseases 0.000 description 1
- DHNCFAWJNPJGHS-UHFFFAOYSA-J [C+4].[O-]C([O-])=O.[O-]C([O-])=O Chemical compound [C+4].[O-]C([O-])=O.[O-]C([O-])=O DHNCFAWJNPJGHS-UHFFFAOYSA-J 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 230000004596 appetite loss Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 235000021266 loss of appetite Nutrition 0.000 description 1
- 208000019017 loss of appetite Diseases 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 238000007833 oxidative deamination reaction Methods 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- GCWKZDAYUIQXLD-ZMBIFBSDSA-M triphenyl-[(3r)-4,4,4-trifluoro-3-hydroxybutyl]phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC[C@@H](O)C(F)(F)F)C1=CC=CC=C1 GCWKZDAYUIQXLD-ZMBIFBSDSA-M 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
-
- 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
- A61K31/425—Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9506564A FR2734821B1 (fr) | 1995-06-02 | 1995-06-02 | Derives de 5-methoxymethyl-3-(1,2-benzisoxazol-3-yl) oxazolidin-2-one, leur preparation et leur application en therapeutique |
| FR9506563A FR2734820B1 (fr) | 1995-06-02 | 1995-06-02 | Derives de 3-(1,2-benzisoxazol-3-yl)oxazolidin-2-one, leur preparation et leur application en therapeutique |
| PCT/FR1996/000792 WO1996038444A1 (fr) | 1995-06-02 | 1996-05-28 | Derives d'oxazolidinone, leur preparation et leur application en therapeutique |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO975530D0 NO975530D0 (no) | 1997-12-01 |
| NO975530L NO975530L (no) | 1998-02-02 |
| NO309091B1 true NO309091B1 (no) | 2000-12-11 |
Family
ID=26232004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO975530A NO309091B1 (no) | 1995-06-02 | 1997-12-01 | Oksazolidinonderivater, deres fremstilling samt medikament og farmasøytisk preparat inneholdende disse |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5843975A (de) |
| EP (1) | EP0835254B1 (de) |
| JP (1) | JP3856829B2 (de) |
| KR (1) | KR100457502B1 (de) |
| CN (1) | CN1075072C (de) |
| AR (1) | AR006301A1 (de) |
| AT (1) | ATE184005T1 (de) |
| AU (1) | AU699367B2 (de) |
| BR (1) | BR9608896A (de) |
| CA (1) | CA2223011C (de) |
| CO (1) | CO4700462A1 (de) |
| CZ (1) | CZ378497A3 (de) |
| DE (1) | DE69604071T2 (de) |
| DK (1) | DK0835254T3 (de) |
| ES (1) | ES2138346T3 (de) |
| GR (1) | GR3031710T3 (de) |
| HK (1) | HK1014938A1 (de) |
| HU (1) | HU224879B1 (de) |
| MX (1) | MX9709410A (de) |
| NO (1) | NO309091B1 (de) |
| NZ (1) | NZ310487A (de) |
| PL (1) | PL183919B1 (de) |
| RU (1) | RU2164226C2 (de) |
| SK (1) | SK281934B6 (de) |
| TW (1) | TW360654B (de) |
| WO (1) | WO1996038444A1 (de) |
| ZA (1) | ZA964563B (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1078632A1 (de) * | 1999-08-16 | 2001-02-28 | Sanofi-Synthelabo | Verwendung von Monoamin Oxydase Inhibitoren zu Herstellung eines Medikaments zur Behandlung der Fettleibigkeit |
| CA2438582C (en) * | 2001-01-31 | 2012-06-26 | Synaptic Pharmaceutical Corporation | Use of gal3 receptor antagonists for the treatment of depression and/or anxiety and compounds useful in such methods |
| KR20040047869A (ko) * | 2001-09-26 | 2004-06-05 | 파마시아 이탈리아 에스.피.에이. | 키나제 억제제로서 활성인 아미노인다졸 유도체, 이의제조방법 및 이를 함유하는 약제학적 조성물 |
| CA2637811A1 (en) * | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Benzisoxazole oxazolidinones as antibacterial agents |
| US7998992B2 (en) * | 2007-03-30 | 2011-08-16 | Institute Of Medicinal Molecular Design, Inc. | Oxazolidinone derivative having inhibitory activity on 11β-hydroxysteroid dehydrogenase type 1 |
| EP2123159A1 (de) * | 2008-05-21 | 2009-11-25 | Bayer CropScience AG | (1,2-Benzisothiazol-3-yl)(thio)carbamate und (1,2-Benzisothiazol-3-yl)(thio)oxamate und deren Oxidationsformen als Pestizide |
| CA2784753A1 (en) * | 2009-12-18 | 2011-06-23 | Janssen Pharmaceutica Nv | Substituted aminothiazolone indazoles as estrogen related receptor-.alpha. modulators |
| AU2011218268A1 (en) * | 2010-02-17 | 2012-09-06 | Janssen Pharmaceutica Nv | Aminothiazolones as estrogen related receptor-alpha modulators |
| WO2016097355A1 (en) * | 2014-12-19 | 2016-06-23 | Ge Healthcare Limited | Labelled oxazolidinone derivatives |
| DE102015012050A1 (de) * | 2015-09-15 | 2017-03-16 | Merck Patent Gmbh | Verbindungen als ASIC-Inhibitoren und deren Verwendungen |
| RU2637643C1 (ru) * | 2016-09-05 | 2017-12-05 | Федеральное государственное бюджетное научное учреждение "Научно-исследовательский институт фундаментальной и клинической иммунологии" (НИИФКИ) | Иммунодепрессант |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2653017B1 (fr) * | 1989-10-17 | 1995-05-05 | Delalande Sa | Derives d'aryl-3 oxazolidinone-2, leur procede de preparation et leur application en therapeutique. |
| US5196543A (en) * | 1989-10-17 | 1993-03-23 | Delalande S.A. | 3-aryloxazolidinone derivatives, process for their preparation and their use in therapy |
| US5235063A (en) * | 1989-10-17 | 1993-08-10 | Delalande S.A. | Process of preparing by condensation certain |
| US5182296A (en) * | 1989-10-26 | 1993-01-26 | Tanabe Seiyaky Co., Ltd. | Naphthyloxazolidone derivatives |
| FR2671350A1 (fr) * | 1991-01-08 | 1992-07-10 | Adir | Nouveaux derives de benzisoxazole et de benzisothiazole, leur procede de preparation, et les compositions pharmaceutiques les renfermant. |
| WO1992014418A1 (fr) * | 1991-02-20 | 1992-09-03 | Yusaku Koda | Articulateur |
-
1996
- 1996-05-28 CZ CZ973784A patent/CZ378497A3/cs unknown
- 1996-05-28 SK SK1614-97A patent/SK281934B6/sk not_active IP Right Cessation
- 1996-05-28 US US08/973,246 patent/US5843975A/en not_active Expired - Lifetime
- 1996-05-28 BR BR9608896A patent/BR9608896A/pt active IP Right Grant
- 1996-05-28 AU AU61288/96A patent/AU699367B2/en not_active Expired
- 1996-05-28 ES ES96918719T patent/ES2138346T3/es not_active Expired - Lifetime
- 1996-05-28 EP EP96918719A patent/EP0835254B1/de not_active Expired - Lifetime
- 1996-05-28 JP JP53624596A patent/JP3856829B2/ja not_active Expired - Lifetime
- 1996-05-28 DE DE69604071T patent/DE69604071T2/de not_active Expired - Lifetime
- 1996-05-28 CA CA002223011A patent/CA2223011C/en not_active Expired - Lifetime
- 1996-05-28 RU RU98100257/04A patent/RU2164226C2/ru active
- 1996-05-28 HU HU9901349A patent/HU224879B1/hu unknown
- 1996-05-28 KR KR1019970708666A patent/KR100457502B1/ko not_active IP Right Cessation
- 1996-05-28 AT AT96918719T patent/ATE184005T1/de active
- 1996-05-28 WO PCT/FR1996/000792 patent/WO1996038444A1/fr active IP Right Grant
- 1996-05-28 NZ NZ310487A patent/NZ310487A/xx not_active IP Right Cessation
- 1996-05-28 PL PL96323673A patent/PL183919B1/pl unknown
- 1996-05-28 CN CN96195713A patent/CN1075072C/zh not_active Expired - Lifetime
- 1996-05-28 DK DK96918719T patent/DK0835254T3/da active
- 1996-05-31 CO CO96028173A patent/CO4700462A1/es unknown
- 1996-06-01 TW TW085106564A patent/TW360654B/zh not_active IP Right Cessation
- 1996-06-03 ZA ZA964563A patent/ZA964563B/xx unknown
- 1996-06-03 AR ARP960102870A patent/AR006301A1/es active IP Right Grant
-
1997
- 1997-12-01 NO NO975530A patent/NO309091B1/no not_active IP Right Cessation
- 1997-12-02 MX MX9709410A patent/MX9709410A/es unknown
-
1998
- 1998-12-30 HK HK98119245A patent/HK1014938A1/xx not_active IP Right Cessation
-
1999
- 1999-11-03 GR GR990402802T patent/GR3031710T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |