CZ283630B6 - Chromanový derivát, způsob jeho výroby a farmaceutický prostředek s jeho obsahem - Google Patents
Chromanový derivát, způsob jeho výroby a farmaceutický prostředek s jeho obsahem Download PDFInfo
- Publication number
- CZ283630B6 CZ283630B6 CS906578A CS657890A CZ283630B6 CZ 283630 B6 CZ283630 B6 CZ 283630B6 CS 906578 A CS906578 A CS 906578A CS 657890 A CS657890 A CS 657890A CZ 283630 B6 CZ283630 B6 CZ 283630B6
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- Czechia
- Prior art keywords
- formula
- group
- carbon atoms
- alkyl
- derivative
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 74
- 238000002360 preparation method Methods 0.000 title claims abstract description 57
- 230000008569 process Effects 0.000 title claims abstract description 53
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 title claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 178
- 238000011282 treatment Methods 0.000 claims abstract description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 208000035475 disorder Diseases 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 90
- 239000000203 mixture Substances 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 48
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 229910052760 oxygen Inorganic materials 0.000 claims description 31
- 239000001301 oxygen Chemical group 0.000 claims description 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 229910052717 sulfur Chemical group 0.000 claims description 30
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 27
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 27
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 27
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000011593 sulfur Chemical group 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
- 125000004122 cyclic group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 239000003153 chemical reaction reagent Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 210000003169 central nervous system Anatomy 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 208000024827 Alzheimer disease Diseases 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 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 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- 229910052723 transition metal Inorganic materials 0.000 claims description 9
- 150000003624 transition metals Chemical class 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 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 description 7
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- 208000020401 Depressive disease Diseases 0.000 claims description 6
- 230000036506 anxiety Effects 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 238000006464 oxidative addition reaction Methods 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- WPWNEKFMGCWNPR-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromene Chemical class C1=CC=C2CCCSC2=C1 WPWNEKFMGCWNPR-UHFFFAOYSA-N 0.000 claims description 5
- 208000019695 Migraine disease Diseases 0.000 claims description 5
- 206010039966 Senile dementia Diseases 0.000 claims description 5
- 208000022531 anorexia Diseases 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 206010061428 decreased appetite Diseases 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 206010027599 migraine Diseases 0.000 claims description 5
- 208000012201 sexual and gender identity disease Diseases 0.000 claims description 5
- 208000015891 sexual disease Diseases 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 230000028016 temperature homeostasis Effects 0.000 claims description 5
- USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical compound OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- GOHXEALVTBUNGX-UHFFFAOYSA-N 3,4-dihydro-2h-chromene-5-carboxylic acid Chemical class O1CCCC2=C1C=CC=C2C(=O)O GOHXEALVTBUNGX-UHFFFAOYSA-N 0.000 claims description 2
- LHCOEOUYRDDIJP-UHFFFAOYSA-N 5-bromo-3,4-dihydro-2h-chromene Chemical class O1CCCC2=C1C=CC=C2Br LHCOEOUYRDDIJP-UHFFFAOYSA-N 0.000 claims description 2
- 238000007239 Wittig reaction Methods 0.000 claims description 2
- 235000010338 boric acid Nutrition 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 229960002645 boric acid Drugs 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- 150000001843 chromanes Chemical class 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 208000027520 Somatoform disease Diseases 0.000 claims 2
- 208000027753 pain disease Diseases 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- WARGWAHJSGITSE-UHFFFAOYSA-N [3-(dipropylamino)-3,4-dihydro-2h-chromen-5-yl]-thiophen-2-ylmethanone Chemical compound C=12CC(N(CCC)CCC)COC2=CC=CC=1C(=O)C1=CC=CS1 WARGWAHJSGITSE-UHFFFAOYSA-N 0.000 claims 1
- 239000012445 acidic reagent Substances 0.000 claims 1
- 230000002862 amidating effect Effects 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 174
- 239000000243 solution Substances 0.000 description 156
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 150
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 108
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 103
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 71
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 58
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- 230000002829 reductive effect Effects 0.000 description 55
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- 239000003921 oil Substances 0.000 description 45
- 235000019198 oils Nutrition 0.000 description 45
- 239000000741 silica gel Substances 0.000 description 40
- 229910002027 silica gel Inorganic materials 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 35
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 34
- 238000002844 melting Methods 0.000 description 33
- 230000008018 melting Effects 0.000 description 33
- 239000002585 base Substances 0.000 description 32
- 229910052938 sodium sulfate Inorganic materials 0.000 description 31
- 235000011152 sodium sulphate Nutrition 0.000 description 31
- 239000007787 solid Substances 0.000 description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 29
- 238000003818 flash chromatography Methods 0.000 description 27
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 20
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 20
- 239000012299 nitrogen atmosphere Substances 0.000 description 19
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 18
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
- 238000004817 gas chromatography Methods 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 13
- 235000011114 ammonium hydroxide Nutrition 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- 229910052744 lithium Inorganic materials 0.000 description 12
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
- 229960001701 chloroform Drugs 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 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 description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- UUIXCSDQTGSSKG-UHFFFAOYSA-N 3-n,3-n-dipropyl-3,4-dihydro-2h-chromene-3,5-diamine Chemical compound C1=CC(N)=C2CC(N(CCC)CCC)COC2=C1 UUIXCSDQTGSSKG-UHFFFAOYSA-N 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 235000011167 hydrochloric acid Nutrition 0.000 description 8
- IVLKGOWYAWHDBT-UHFFFAOYSA-N methyl 3-(dipropylamino)-3,4-dihydro-2h-chromene-5-carboxylate Chemical compound C1=CC(C(=O)OC)=C2CC(N(CCC)CCC)COC2=C1 IVLKGOWYAWHDBT-UHFFFAOYSA-N 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- AJBQOMKVPQFQBV-UHFFFAOYSA-N n,n-dipropyl-5-(trifluoromethylsulfonyl)-3,4-dihydro-2h-chromen-3-amine Chemical compound C1=CC(S(=O)(=O)C(F)(F)F)=C2CC(N(CCC)CCC)COC2=C1 AJBQOMKVPQFQBV-UHFFFAOYSA-N 0.000 description 7
- 235000011181 potassium carbonates Nutrition 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 230000005062 synaptic transmission Effects 0.000 description 7
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
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- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
- 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
- C07D413/06—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 only aliphatic carbon atoms
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
- Liquid Crystal Substances (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Threshing Machine Elements (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
- Harvester Elements (AREA)
- Apparatuses For Bulk Treatment Of Fruits And Vegetables And Apparatuses For Preparing Feeds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE8904361A SE8904361D0 (sv) | 1989-12-22 | 1989-12-22 | New chroman and thiochroman derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
CZ657890A3 CZ657890A3 (cs) | 1998-02-18 |
CZ283630B6 true CZ283630B6 (cs) | 1998-05-13 |
Family
ID=20377869
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS906578A CZ283630B6 (cs) | 1989-12-22 | 1990-12-21 | Chromanový derivát, způsob jeho výroby a farmaceutický prostředek s jeho obsahem |
Country Status (42)
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5420151A (en) * | 1989-12-22 | 1995-05-30 | Aktiebolaget Astra | Chroman derivatives |
CA2048846A1 (en) * | 1990-08-15 | 1992-02-16 | Craig Steven Hoechstetter | Ring-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes, 3-aminochromanes, and aminothiochromanes |
DK0498590T3 (da) * | 1991-02-08 | 1997-05-05 | Lilly Co Eli | Ringsubstituerede 2-amino-1,2,3,4-tetrahydronaphthalener |
HRP920935A2 (en) * | 1991-10-08 | 1995-08-31 | Astra Ab | New therapeutically active compound |
SE9103745D0 (sv) * | 1991-12-18 | 1991-12-18 | Wikstroem Haakan | Aryl-triflates and related compounds |
FR2691149B1 (fr) * | 1992-05-18 | 1994-07-08 | Adir | Nouveaux composes thiochromaniques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
US5434174A (en) * | 1992-07-17 | 1995-07-18 | Eli Lilly And Company | Isoxazole derivatives for the treatment of irritable bowel syndrome |
SE9301732D0 (sv) * | 1993-05-18 | 1993-05-18 | Haakan Wilhelm Wikstroem | New centrally acting 5-,6-,7-, and 8-substituted sulphone esters of n-monosubstituted 2-aminotetralins |
SE9703377D0 (sv) * | 1997-09-18 | 1997-09-18 | Astra Ab | New compounds |
SE9703378D0 (sv) * | 1997-09-18 | 1997-09-18 | Astra Ab | New compounds |
TW555757B (en) * | 1998-07-31 | 2003-10-01 | Akzo Nobel Nv | Aminomethylcarboxylic acid derivatives |
US6184226B1 (en) | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
WO2002055013A2 (en) | 2001-01-16 | 2002-07-18 | Astrazeneca Ab | Therapeutic chromone compounds |
WO2002055014A2 (en) * | 2001-01-16 | 2002-07-18 | Astrazeneca Ab | Therapeutic chroman compounds |
BR0206512A (pt) | 2001-01-16 | 2004-01-06 | Astrazeneca Ab | Composto, método de tratamento de um ser humano ou animal que sofre de depressão, ansiedade generalizada, distúrbios da alimentação, demência, distúrbio do p nico, distúrbios do sono, distúrbios gastrointestinais, distúrbios motores, distúrbios endócrinos, vasoespasmo e disfunção sexual, uso de um composto, e, processo para preparar um composto. |
RU2193559C1 (ru) * | 2001-05-16 | 2002-11-27 | Пермская государственная фармацевтическая академия | 2,4-ксилидид и м-фенетидид 2-ацетилиминокумарин-3-карбоновой кислоты, обладающие антикоагулянтной активностью |
WO2003007956A1 (en) | 2001-07-20 | 2003-01-30 | Psychogenics, Inc. | Treatment for attention-deficit hyperactivity disorder |
US7125904B2 (en) | 2002-10-11 | 2006-10-24 | Portela & C.A., S.A. | Peripherally-selective inhibitors of dopamine-β-hydroxylase and method of their preparation |
SE0301796D0 (sv) * | 2003-06-19 | 2003-06-19 | Astrazeneca Ab | New use II |
SE0301795D0 (sv) * | 2003-06-19 | 2003-06-19 | Astrazeneca Ab | New use I |
WO2008080120A2 (en) * | 2006-12-22 | 2008-07-03 | Wyeth | 3-amino chromane derivatives |
SA08290245B1 (ar) * | 2007-04-23 | 2012-02-12 | استرازينيكا ايه بي | مشتقات كربو كساميد جديدة من -n (8-اريل رباعي هيدرو نفثالين غير متجانس- 2- يل) أو -n (5-اريل كرومان غير متجانس -3-يل) لعلاج الألم |
CN101712672B (zh) * | 2008-10-06 | 2013-02-06 | 中国中医科学院中药研究所 | 一种治疗心脑血管系统疾病新化合物及其制备方法、用途 |
DE102010041948A1 (de) | 2010-10-04 | 2012-04-05 | Mahle International Gmbh | Filtereinrichtung |
GB201316410D0 (en) | 2013-09-13 | 2013-10-30 | Bial Portela & Ca Sa | Processes for preparing peripherally-selective inhibitors of dopamine-?-hydroxylase and intermediates for use therein |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE63744T1 (de) * | 1985-09-03 | 1991-06-15 | Ciba Geigy Ag | 3-amino-dihydro-(1>-benzopyrane und benzothiopyrane. |
US4801605A (en) * | 1986-08-29 | 1989-01-31 | Ciba-Geigy Corporation | 3-amino-dihydro-[1]-benzopyrans and benzothiopyrans |
SE8605504D0 (sv) * | 1986-12-19 | 1986-12-19 | Astra Laekemedel Ab | Novel chroman derivatives |
US5258287A (en) * | 1988-03-22 | 1993-11-02 | Genentech, Inc. | DNA encoding and methods of production of insulin-like growth factor binding protein BP53 |
-
1989
- 1989-12-22 SE SE8904361A patent/SE8904361D0/xx unknown
-
1990
- 1990-12-03 ZA ZA909708A patent/ZA909708B/xx unknown
- 1990-12-10 NZ NZ236407A patent/NZ236407A/xx unknown
- 1990-12-11 PH PH41705A patent/PH30797A/en unknown
- 1990-12-12 DZ DZ900224A patent/DZ1469A1/fr active
- 1990-12-17 IE IE453590A patent/IE80753B1/en not_active IP Right Cessation
- 1990-12-18 IL IL9671290A patent/IL96712A/en not_active IP Right Cessation
- 1990-12-19 UA UA5001901A patent/UA34416C2/uk unknown
- 1990-12-19 WO PCT/SE1990/000863 patent/WO1991009853A1/en active IP Right Grant
- 1990-12-19 AT AT91901496T patent/ATE138918T1/de not_active IP Right Cessation
- 1990-12-19 RU SU905001901A patent/RU2092483C1/ru not_active IP Right Cessation
- 1990-12-19 IS IS3662A patent/IS1665B/is unknown
- 1990-12-19 EP EP91901496A patent/EP0460169B1/en not_active Expired - Lifetime
- 1990-12-19 SG SG1996006565A patent/SG48043A1/en unknown
- 1990-12-19 DK DK91901496.9T patent/DK0460169T3/da active
- 1990-12-19 DE DE69027311T patent/DE69027311T2/de not_active Expired - Fee Related
- 1990-12-19 KR KR1019910700957A patent/KR0178991B1/ko not_active Expired - Fee Related
- 1990-12-19 ES ES91901496T patent/ES2087993T3/es not_active Expired - Lifetime
- 1990-12-19 AU AU69770/91A patent/AU641204B2/en not_active Ceased
- 1990-12-19 JP JP3501912A patent/JP2879972B2/ja not_active Expired - Fee Related
- 1990-12-19 CA CA002047237A patent/CA2047237C/en not_active Expired - Fee Related
- 1990-12-20 EG EG75290A patent/EG19749A/xx active
- 1990-12-20 PT PT96304A patent/PT96304B/pt not_active IP Right Cessation
- 1990-12-21 TW TW079110767A patent/TW221056B/zh active
- 1990-12-21 MX MX2388990A patent/MX23889A/es unknown
- 1990-12-21 YU YU242990A patent/YU47936B/sh unknown
- 1990-12-21 CN CN90106068A patent/CN1037438C/zh not_active Expired - Fee Related
- 1990-12-21 SI SI9012429A patent/SI9012429B/sl not_active IP Right Cessation
- 1990-12-21 PL PL90293065A patent/PL164608B1/pl not_active IP Right Cessation
- 1990-12-21 PL PL90293066A patent/PL164609B1/pl not_active IP Right Cessation
- 1990-12-21 CZ CS906578A patent/CZ283630B6/cs not_active IP Right Cessation
- 1990-12-21 PL PL90288405A patent/PL164592B1/pl not_active IP Right Cessation
- 1990-12-21 SK SK6578-90A patent/SK657890A3/sk unknown
- 1990-12-22 SA SA90110186A patent/SA90110186B1/ar unknown
-
1991
- 1991-04-22 YU YU72191A patent/YU47923B/sh unknown
- 1991-08-21 FI FI913943A patent/FI102177B/fi not_active IP Right Cessation
- 1991-08-21 NO NO913273A patent/NO180336C/no unknown
-
1992
- 1992-01-30 ID IDP185892A patent/ID945B/id unknown
- 1992-10-02 HR HRP-2429/90A patent/HRP920851B1/xx not_active IP Right Cessation
-
1993
- 1993-06-30 LV LVP-93-819A patent/LV10449B/en unknown
- 1993-12-30 LT LTIP1730A patent/LT3967B/lt not_active IP Right Cessation
-
1995
- 1995-06-30 HU HU95P/P00717P patent/HU211860A9/hu unknown
-
1996
- 1996-07-10 GR GR960401865T patent/GR3020497T3/el unknown
-
1997
- 1997-05-01 HK HK55897A patent/HK55897A/en not_active IP Right Cessation
- 1997-06-05 LV LVP-97-111A patent/LV11894B/xx unknown
- 1997-09-05 CY CY199197A patent/CY1991A/xx unknown
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
IF00 | In force as of 2000-06-30 in czech republic | ||
MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20061221 |