DD224588A5 - Verfahren zur herstellung von n-pyridylindolen - Google Patents
Verfahren zur herstellung von n-pyridylindolen Download PDFInfo
- Publication number
- DD224588A5 DD224588A5 DD84263081A DD26308184A DD224588A5 DD 224588 A5 DD224588 A5 DD 224588A5 DD 84263081 A DD84263081 A DD 84263081A DD 26308184 A DD26308184 A DD 26308184A DD 224588 A5 DD224588 A5 DD 224588A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- formula
- pyridyl
- indole
- compound
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 64
- 238000002360 preparation method Methods 0.000 title claims description 18
- -1 carboxy, carbamoyl Chemical group 0.000 claims abstract description 135
- 150000003839 salts Chemical class 0.000 claims abstract description 72
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 57
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
- 239000001257 hydrogen Substances 0.000 claims abstract description 45
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 31
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 19
- 150000002367 halogens Chemical class 0.000 claims abstract description 18
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 16
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 11
- 125000003349 3-pyridyl group Chemical class N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 10
- 125000004419 alkynylene group Chemical group 0.000 claims abstract description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 5
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract description 4
- 125000000339 4-pyridyl group Chemical class N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 193
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 34
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001041 indolyl group Chemical group 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 230000002829 reductive effect Effects 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- MCAPFZFMMUIMEH-UHFFFAOYSA-N 5-(2-methyl-1-pyridin-3-ylindol-3-yl)pentanoic acid Chemical compound CC1=C(CCCCC(O)=O)C2=CC=CC=C2N1C1=CC=CN=C1 MCAPFZFMMUIMEH-UHFFFAOYSA-N 0.000 claims description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 230000002452 interceptive effect Effects 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- VMYNZSGRXMWFQI-UHFFFAOYSA-N 3-(1-pyridin-3-ylindol-3-yl)propanoic acid Chemical compound C12=CC=CC=C2C(CCC(=O)O)=CN1C1=CC=CN=C1 VMYNZSGRXMWFQI-UHFFFAOYSA-N 0.000 claims description 2
- NOSDTQKCYJKFBL-UHFFFAOYSA-N 5-(5-bromo-1-pyridin-3-ylindol-3-yl)pentanoic acid Chemical compound C12=CC=C(Br)C=C2C(CCCCC(=O)O)=CN1C1=CC=CN=C1 NOSDTQKCYJKFBL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- GUXQOVBGUZZBPJ-MKMNVTDBSA-N (e)-2-methyl-5-(1-pyridin-3-ylindol-3-yl)pent-2-enoic acid Chemical compound C12=CC=CC=C2C(CC\C=C(/C)C(O)=O)=CN1C1=CC=CN=C1 GUXQOVBGUZZBPJ-MKMNVTDBSA-N 0.000 claims 1
- GUXQOVBGUZZBPJ-NSIKDUERSA-N (z)-2-methyl-5-(1-pyridin-3-ylindol-3-yl)pent-2-enoic acid Chemical compound C12=CC=CC=C2C(CC/C=C(/C)C(O)=O)=CN1C1=CC=CN=C1 GUXQOVBGUZZBPJ-NSIKDUERSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 7
- 108010069102 Thromboxane-A synthase Proteins 0.000 abstract description 6
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- VSKZGHVPGOMFAV-UHFFFAOYSA-N 1-pyridin-2-ylindole Chemical class C1=CC2=CC=CC=C2N1C1=CC=CC=N1 VSKZGHVPGOMFAV-UHFFFAOYSA-N 0.000 abstract 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 96
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 78
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
- 239000011541 reaction mixture Substances 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 239000002585 base Substances 0.000 description 28
- 239000007858 starting material Substances 0.000 description 28
- 239000002253 acid Substances 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 150000003254 radicals Chemical class 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- 239000000543 intermediate Substances 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
- 235000011152 sodium sulphate Nutrition 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 125000005907 alkyl ester group Chemical group 0.000 description 14
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 14
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 13
- 125000004970 halomethyl group Chemical group 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 8
- UETRKVDAHIACJW-UHFFFAOYSA-N 5-(1-pyridin-3-ylindol-3-yl)pentanoic acid Chemical compound C12=CC=CC=C2C(CCCCC(=O)O)=CN1C1=CC=CN=C1 UETRKVDAHIACJW-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- JHMUBQSCLBFHSR-UHFFFAOYSA-N 1-pyridin-3-ylindole-3-carbaldehyde Chemical compound C12=CC=CC=C2C(C=O)=CN1C1=CC=CN=C1 JHMUBQSCLBFHSR-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 229940043279 diisopropylamine Drugs 0.000 description 5
- 229960001123 epoprostenol Drugs 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 230000002285 radioactive effect Effects 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
- NFLKJMSYUXZFDF-UHFFFAOYSA-N 1-pyridin-3-ylindole Chemical compound C1=CC2=CC=CC=C2N1C1=CC=CN=C1 NFLKJMSYUXZFDF-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 4
- 239000005751 Copper oxide Substances 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 4
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229940114079 arachidonic acid Drugs 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910000431 copper oxide Inorganic materials 0.000 description 4
- 230000002526 effect on cardiovascular system Effects 0.000 description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- 125000003431 oxalo group Chemical group 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 150000003180 prostaglandins Chemical class 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 238000003797 solvolysis reaction Methods 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- AUNBMXVIRXVMHE-UHFFFAOYSA-N 1-phenyl-1-pyridin-3-ylhydrazine Chemical compound C=1C=CN=CC=1N(N)C1=CC=CC=C1 AUNBMXVIRXVMHE-UHFFFAOYSA-N 0.000 description 3
- DLQUYEDFKTVVRM-UHFFFAOYSA-N 3-(1-pyridin-3-ylindol-3-yl)propanal Chemical compound C12=CC=CC=C2C(CCC=O)=CN1C1=CC=CN=C1 DLQUYEDFKTVVRM-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical class NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
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- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229940080237 sodium caseinate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical class O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003595 thromboxanes Chemical class 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/495,370 US4536505A (en) | 1983-05-17 | 1983-05-17 | Certain N-(pyridyl) indoles |
Publications (1)
Publication Number | Publication Date |
---|---|
DD224588A5 true DD224588A5 (de) | 1985-07-10 |
Family
ID=23968377
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DD84263081A DD224588A5 (de) | 1983-05-17 | 1984-05-16 | Verfahren zur herstellung von n-pyridylindolen |
Country Status (15)
Country | Link |
---|---|
US (1) | US4536505A (es) |
EP (1) | EP0126401A1 (es) |
JP (1) | JPS59212489A (es) |
KR (1) | KR840009302A (es) |
AU (1) | AU2809484A (es) |
DD (1) | DD224588A5 (es) |
DK (1) | DK242484A (es) |
ES (5) | ES8602652A1 (es) |
FI (1) | FI841925A (es) |
GR (1) | GR79934B (es) |
HU (1) | HUT34182A (es) |
IL (1) | IL71832A0 (es) |
NO (1) | NO841958L (es) |
PT (1) | PT78582A (es) |
ZA (1) | ZA843677B (es) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4675332A (en) * | 1984-12-10 | 1987-06-23 | Warner-Lambert Company | Acidic tetrazolyl substituted indole compounds and their use as antiallergy agents |
US4609733A (en) * | 1984-12-27 | 1986-09-02 | Ciba-Geigy Corporation | 3-keto-substituted-N-pyridylindoles |
US4758586A (en) * | 1985-02-01 | 1988-07-19 | Usv Pharmaceutical Corp. | Indolyl compounds and hyposensitivity use thereof |
US4880822A (en) * | 1987-04-24 | 1989-11-14 | Hoechst-Roussel Pharmaceuticals, Inc. | N-(pyridinyl)-1H-indol-1-amines |
US4970218A (en) * | 1987-04-24 | 1990-11-13 | Hoechst-Roussel Pharmaceuticals Inc. | N-(pyridinyl)-1H-indol-1-amines |
US5039811A (en) * | 1987-04-24 | 1991-08-13 | Hoechst-Roussel Pharmaceuticals Inc. | Preparation of N-(pyridinyl)-1H-indol-1-amines |
US5550118A (en) * | 1994-01-31 | 1996-08-27 | Eli Lilly And Company | Polyhydronorharman synthase inhibitors |
US5977125A (en) * | 1994-10-31 | 1999-11-02 | Eisai Co., Ltd. | Mono-or polyenic carboxylic acid derivatives |
GB2295151B (en) * | 1994-11-18 | 1998-12-09 | Nmc | Polymerization of substituted heterocyclic monomers |
BR9908165A (pt) * | 1998-02-23 | 2000-10-31 | Univ South Alabama | Processos de prevenção de um citotóxico de proteìna beta amilóide em células, de tratamento de uma fibrilogênica em um sujeito humano, de diminuição da oxidação em uma amostra biológica e de tratamento de doenças ou outros quadros em que radicais livres e/ou tensão oxidativa desempenham um papel, e, uso de ácido indol-3-propiÈnico ou um seu sal ou éster. |
WO2003027107A1 (en) * | 2001-09-26 | 2003-04-03 | Bayer Pharmaceuticals Corporation | Substituted 3-pyridyl oxazoles as c17,20 lyase inhibitors |
BRPI0617271A2 (pt) * | 2005-10-11 | 2011-07-19 | Intermune Inc | inibidores de replicação viral |
KR100807718B1 (ko) * | 2006-10-17 | 2008-02-28 | 한국생명공학연구원 | 인돌 유도체를 유효성분으로 함유하는 대사성 질환 예방 및치료용 약학적 조성물 |
US20090047246A1 (en) * | 2007-02-12 | 2009-02-19 | Intermune, Inc. | Novel inhibitors of hepatitis c virus replication |
US8293781B2 (en) * | 2007-03-29 | 2012-10-23 | Daiichi Sankyo Company, Limited | Indole derivatives having cPLA2 inhibiting activity and applications and production methods of the same |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3449348A (en) * | 1968-01-08 | 1969-06-10 | Merck & Co Inc | Alpha-halomethyl-1-pyridine or quinoline carbonyl-3-indolylacetic acids |
AT299938B (de) * | 1971-02-03 | 1972-07-10 | Italiana Sint Spa | Verfahren zur Herstellung des neuen Natriumsalzes der (1-Nicotinoyl-2-methyl-5-methoxy-3-indolyl)-essigsäure, gegebenenfalls im Gemisch mit der freien Säure |
FR2171936B1 (es) * | 1972-02-16 | 1975-04-25 | Clin Midy | |
FR2171937A1 (en) * | 1972-02-16 | 1973-09-28 | Clin Midy | Aminoketo indoles - analgesics and antidepressants |
AT323154B (de) * | 1973-02-02 | 1975-06-25 | Hurka Wilhelm | Verfahren zur herstellung von neuen 5-methoxy-2-methylindol-3-essigsäurederivaten sowie von deren salzen |
DE2862340D1 (en) * | 1978-02-01 | 1983-11-24 | Wellcome Found | Imidazole derivatives and salts thereof, their synthesis, and pharmaceutical formulations thereof |
US4322533A (en) * | 1980-03-17 | 1982-03-30 | Lesher George Y | 1H-Indole-2,3-dione derivatives |
US4363912A (en) * | 1980-12-15 | 1982-12-14 | Pfizer Inc. | Indole thromboxane synthetase inhibitors |
CS229934B2 (en) * | 1981-07-07 | 1984-07-16 | Pfizer | Production method subst.indolylacryte acid derivative |
GB2102795A (en) * | 1981-07-31 | 1983-02-09 | Pfizer Ltd | Indole derivatives |
US4478842A (en) * | 1981-11-19 | 1984-10-23 | Ciba-Geigy Corporation | N-Substituted-2-pyridylindoles |
US4460777A (en) * | 1981-11-19 | 1984-07-17 | Ciba-Geigy Corporation | N-Substituted-2-pyridylindoles |
US4511573A (en) * | 1983-05-17 | 1985-04-16 | Ciba-Geigy Corporation | 3-Substituted-2-(heteroaryl) indoles |
-
1983
- 1983-05-17 US US06/495,370 patent/US4536505A/en not_active Expired - Fee Related
-
1984
- 1984-05-14 FI FI841925A patent/FI841925A/fi not_active Application Discontinuation
- 1984-05-14 EP EP84105449A patent/EP0126401A1/de not_active Ceased
- 1984-05-15 IL IL71832A patent/IL71832A0/xx unknown
- 1984-05-15 GR GR74706A patent/GR79934B/el unknown
- 1984-05-15 PT PT78582A patent/PT78582A/pt unknown
- 1984-05-15 JP JP59095771A patent/JPS59212489A/ja active Pending
- 1984-05-16 AU AU28094/84A patent/AU2809484A/en not_active Abandoned
- 1984-05-16 KR KR1019840002658A patent/KR840009302A/ko not_active Application Discontinuation
- 1984-05-16 DK DK242484A patent/DK242484A/da not_active Application Discontinuation
- 1984-05-16 NO NO841958A patent/NO841958L/no unknown
- 1984-05-16 ZA ZA843677A patent/ZA843677B/xx unknown
- 1984-05-16 DD DD84263081A patent/DD224588A5/de unknown
- 1984-05-16 HU HU841893A patent/HUT34182A/hu unknown
- 1984-05-17 ES ES532572A patent/ES8602652A1/es not_active Expired
-
1985
- 1985-07-12 ES ES545151A patent/ES8604195A1/es not_active Expired
- 1985-07-12 ES ES545153A patent/ES8604197A1/es not_active Expired
- 1985-07-12 ES ES545154A patent/ES8604922A1/es not_active Expired
- 1985-07-12 ES ES545152A patent/ES8604196A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
IL71832A0 (en) | 1984-09-30 |
US4536505A (en) | 1985-08-20 |
ES532572A0 (es) | 1985-12-01 |
JPS59212489A (ja) | 1984-12-01 |
FI841925A0 (fi) | 1984-05-14 |
ES8604196A1 (es) | 1986-01-16 |
PT78582A (en) | 1984-06-01 |
NO841958L (no) | 1984-11-19 |
DK242484D0 (da) | 1984-05-16 |
ES8604922A1 (es) | 1986-02-16 |
KR840009302A (ko) | 1984-12-26 |
ES545153A0 (es) | 1986-01-16 |
ZA843677B (en) | 1985-02-27 |
DK242484A (da) | 1984-11-18 |
ES545154A0 (es) | 1986-02-16 |
AU2809484A (en) | 1984-11-22 |
ES8604195A1 (es) | 1986-01-16 |
ES8602652A1 (es) | 1985-12-01 |
EP0126401A1 (de) | 1984-11-28 |
ES545151A0 (es) | 1986-01-16 |
ES8604197A1 (es) | 1986-01-16 |
ES545152A0 (es) | 1986-01-16 |
HUT34182A (en) | 1985-02-28 |
FI841925A (fi) | 1984-11-18 |
GR79934B (es) | 1984-10-31 |
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