NO862134L - Amidderivater av kinolin samt deres fremstilling. - Google Patents
Amidderivater av kinolin samt deres fremstilling.Info
- Publication number
- NO862134L NO862134L NO862134A NO862134A NO862134L NO 862134 L NO862134 L NO 862134L NO 862134 A NO862134 A NO 862134A NO 862134 A NO862134 A NO 862134A NO 862134 L NO862134 L NO 862134L
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- formula
- phenyl
- alkyl
- groups
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 18
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 55
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 9
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 42
- -1 pyrrolidyl ring Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical group O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 150000002828 nitro derivatives Chemical class 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- MJYFVDNMTKLGTH-UHFFFAOYSA-N 4-bromo-6-(3,4-dichlorophenyl)sulfanyl-1-[[4-(dimethylcarbamoyl)phenyl]methyl]indole-2-carboxylic acid Chemical compound BrC1=C2C=C(N(C2=CC(=C1)SC1=CC(=C(C=C1)Cl)Cl)CC1=CC=C(C=C1)C(N(C)C)=O)C(=O)O MJYFVDNMTKLGTH-UHFFFAOYSA-N 0.000 claims 1
- 240000002791 Brassica napus Species 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract description 7
- 239000002249 anxiolytic agent Substances 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- GQJPKHSIFUZSGN-UHFFFAOYSA-N (2-phenylquinolin-4-yl) n,n-dimethylcarbamate Chemical compound N=1C2=CC=CC=C2C(OC(=O)N(C)C)=CC=1C1=CC=CC=C1 GQJPKHSIFUZSGN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 229940125681 anticonvulsant agent Drugs 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- 230000000949 anxiolytic effect Effects 0.000 abstract 1
- 229940005530 anxiolytics Drugs 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 88
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 79
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 78
- 230000008018 melting Effects 0.000 description 50
- 238000002844 melting Methods 0.000 description 50
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 26
- MICODESZTQZIAB-UHFFFAOYSA-N 2-(2-phenylquinolin-4-yl)oxyacetic acid Chemical compound N=1C2=CC=CC=C2C(OCC(=O)O)=CC=1C1=CC=CC=C1 MICODESZTQZIAB-UHFFFAOYSA-N 0.000 description 23
- 238000001953 recrystallisation Methods 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 19
- 229910000027 potassium carbonate Inorganic materials 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 15
- LLLQAMNGYJQUKK-UHFFFAOYSA-N 2-bromo-1-morpholin-4-ylethanone Chemical compound BrCC(=O)N1CCOCC1 LLLQAMNGYJQUKK-UHFFFAOYSA-N 0.000 description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000003480 eluent Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 229920000137 polyphosphoric acid Polymers 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- AYCCBGICWQDRLF-UHFFFAOYSA-N 1-morpholin-4-yl-2-(6-nitro-2-phenylquinolin-4-yl)oxyethanone Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=C(C=2C=CC=CC=2)C=C1OCC(=O)N1CCOCC1 AYCCBGICWQDRLF-UHFFFAOYSA-N 0.000 description 2
- YVQJBEAUYBBCGP-UHFFFAOYSA-N 2-(2-phenylquinolin-4-yl)oxy-1-pyrrolidin-1-ylethanone Chemical compound C1CCCN1C(=O)COC(C1=CC=CC=C1N=1)=CC=1C1=CC=CC=C1 YVQJBEAUYBBCGP-UHFFFAOYSA-N 0.000 description 2
- RWJAAQHDHXDHSA-UHFFFAOYSA-N 2-(2-phenylquinolin-4-yl)oxy-1-thiomorpholin-4-ylethanone Chemical compound C1CSCCN1C(=O)COC(C1=CC=CC=C1N=1)=CC=1C1=CC=CC=C1 RWJAAQHDHXDHSA-UHFFFAOYSA-N 0.000 description 2
- PVACEDOBJLBMTP-UHFFFAOYSA-N 2-[(4-chloro-2-phenyl-3h-quinolin-4-yl)oxy]acetic acid Chemical compound N=1C2=CC=CC=C2C(OCC(=O)O)(Cl)CC=1C1=CC=CC=C1 PVACEDOBJLBMTP-UHFFFAOYSA-N 0.000 description 2
- DRLFRJQGMSSSLJ-UHFFFAOYSA-N 2-bromo-n-tert-butyl-n-methylacetamide Chemical compound CC(C)(C)N(C)C(=O)CBr DRLFRJQGMSSSLJ-UHFFFAOYSA-N 0.000 description 2
- JGABMVVOXLQCKZ-UHFFFAOYSA-N 2-phenyl-1h-quinolin-4-one Chemical compound N=1C2=CC=CC=C2C(O)=CC=1C1=CC=CC=C1 JGABMVVOXLQCKZ-UHFFFAOYSA-N 0.000 description 2
- QKTGFMIEELHDSD-UHFFFAOYSA-N 6-chloro-2-phenyl-1h-quinolin-4-one Chemical compound C=1C(=O)C2=CC(Cl)=CC=C2NC=1C1=CC=CC=C1 QKTGFMIEELHDSD-UHFFFAOYSA-N 0.000 description 2
- CKFBIYVXNYYXAI-UHFFFAOYSA-N 6-methoxy-2-phenyl-1h-quinolin-4-one Chemical compound C1=C(O)C2=CC(OC)=CC=C2N=C1C1=CC=CC=C1 CKFBIYVXNYYXAI-UHFFFAOYSA-N 0.000 description 2
- SWRQHHJAXCNFGU-UHFFFAOYSA-N 6-methyl-2-phenyl-1h-quinolin-4-one Chemical compound C=1C(=O)C2=CC(C)=CC=C2NC=1C1=CC=CC=C1 SWRQHHJAXCNFGU-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 150000001557 benzodiazepines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- JSIGUUUNVYUWQT-UHFFFAOYSA-N n-methylcyclobutanamine Chemical compound CNC1CCC1 JSIGUUUNVYUWQT-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 2
- PYFSCIWXNSXGNS-RXMQYKEDSA-N (2r)-n-methylbutan-2-amine Chemical compound CC[C@@H](C)NC PYFSCIWXNSXGNS-RXMQYKEDSA-N 0.000 description 1
- QYSAAPFGRHELJE-UHFFFAOYSA-N (3-ethylpyridin-2-yl) acetate Chemical compound CCC1=CC=CN=C1OC(C)=O QYSAAPFGRHELJE-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- UDXRYTVHKDOQKZ-UHFFFAOYSA-N 1-(2,6-dimethylmorpholin-4-yl)-2-(2-phenylquinolin-4-yl)oxyethanone Chemical compound C1C(C)OC(C)CN1C(=O)COC1=CC(C=2C=CC=CC=2)=NC2=CC=CC=C12 UDXRYTVHKDOQKZ-UHFFFAOYSA-N 0.000 description 1
- GEYZHMDDYKLXDS-UHFFFAOYSA-N 1-(4-hydroxypiperidin-1-yl)-2-(2-phenylquinolin-4-yl)oxyethanone Chemical compound C1CC(O)CCN1C(=O)COC1=CC(C=2C=CC=CC=2)=NC2=CC=CC=C12 GEYZHMDDYKLXDS-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 1
- ORQVLOOOUXHZEJ-UHFFFAOYSA-N 1-cyclopropyl-n-methylmethanamine;hydrochloride Chemical compound Cl.CNCC1CC1 ORQVLOOOUXHZEJ-UHFFFAOYSA-N 0.000 description 1
- STOZYFSTBANQDF-UHFFFAOYSA-N 1-methyl-4-[2-(2-phenylquinolin-4-yl)oxyacetyl]piperazin-2-one Chemical compound C1C(=O)N(C)CCN1C(=O)COC1=CC(C=2C=CC=CC=2)=NC2=CC=CC=C12 STOZYFSTBANQDF-UHFFFAOYSA-N 0.000 description 1
- AYMSOJDBQCAGHF-UHFFFAOYSA-N 1-morpholin-4-yl-2-(2-phenylquinolin-4-yl)oxyethanone Chemical compound C1COCCN1C(=O)COC(C1=CC=CC=C1N=1)=CC=1C1=CC=CC=C1 AYMSOJDBQCAGHF-UHFFFAOYSA-N 0.000 description 1
- PSIYMNKNIGRGDI-UHFFFAOYSA-N 1-morpholin-4-yl-2-(2-thiophen-2-ylquinolin-4-yl)oxyethanone Chemical compound C1COCCN1C(=O)COC(C1=CC=CC=C1N=1)=CC=1C1=CC=CS1 PSIYMNKNIGRGDI-UHFFFAOYSA-N 0.000 description 1
- AKFKFFLTOLCHOM-UHFFFAOYSA-N 1-morpholin-4-yl-2-[2-(4-nitrophenyl)quinolin-4-yl]oxyethanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC(OCC(=O)N2CCOCC2)=C(C=CC=C2)C2=N1 AKFKFFLTOLCHOM-UHFFFAOYSA-N 0.000 description 1
- PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical compound CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 description 1
- VPESDZBNLLFLLN-UHFFFAOYSA-N 2-(2-phenylquinolin-4-yl)oxy-1-piperidin-1-ylethanone Chemical compound C1CCCCN1C(=O)COC(C1=CC=CC=C1N=1)=CC=1C1=CC=CC=C1 VPESDZBNLLFLLN-UHFFFAOYSA-N 0.000 description 1
- REZZPJUGBBYSJX-UHFFFAOYSA-N 2-(5-chloro-2-phenylquinolin-4-yl)oxy-1-morpholin-4-ylethanone Chemical compound C=12C(Cl)=CC=CC2=NC(C=2C=CC=CC=2)=CC=1OCC(=O)N1CCOCC1 REZZPJUGBBYSJX-UHFFFAOYSA-N 0.000 description 1
- TUWGRYSPPCQTEF-UHFFFAOYSA-N 2-(6-amino-2-phenylquinolin-4-yl)oxy-1-morpholin-4-ylethanone Chemical compound C12=CC(N)=CC=C2N=C(C=2C=CC=CC=2)C=C1OCC(=O)N1CCOCC1 TUWGRYSPPCQTEF-UHFFFAOYSA-N 0.000 description 1
- MYCNDYIKJLOQBI-UHFFFAOYSA-N 2-(6-chloro-2-phenylquinolin-4-yl)oxy-1-morpholin-4-ylethanone Chemical compound C12=CC(Cl)=CC=C2N=C(C=2C=CC=CC=2)C=C1OCC(=O)N1CCOCC1 MYCNDYIKJLOQBI-UHFFFAOYSA-N 0.000 description 1
- SARNYVGCRGOHFV-UHFFFAOYSA-N 2-(6-methyl-2-phenylquinolin-4-yl)oxy-1-morpholin-4-ylethanone Chemical compound C12=CC(C)=CC=C2N=C(C=2C=CC=CC=2)C=C1OCC(=O)N1CCOCC1 SARNYVGCRGOHFV-UHFFFAOYSA-N 0.000 description 1
- UFDKQYBGWQCJMS-UHFFFAOYSA-N 2-[2-(4-methylphenyl)quinolin-4-yl]oxy-1-morpholin-4-ylethanone Chemical compound C1=CC(C)=CC=C1C1=CC(OCC(=O)N2CCOCC2)=C(C=CC=C2)C2=N1 UFDKQYBGWQCJMS-UHFFFAOYSA-N 0.000 description 1
- SYZRZLUNWVNNNV-UHFFFAOYSA-N 2-bromoacetyl chloride Chemical compound ClC(=O)CBr SYZRZLUNWVNNNV-UHFFFAOYSA-N 0.000 description 1
- KOHBEDRJXKOYHL-UHFFFAOYSA-N 2-methoxy-n-methylethanamine Chemical compound CNCCOC KOHBEDRJXKOYHL-UHFFFAOYSA-N 0.000 description 1
- WZTOGZXZQJFJNS-UHFFFAOYSA-N 2-methoxy-n-methylethanamine;hydrochloride Chemical compound Cl.CNCCOC WZTOGZXZQJFJNS-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- AXDMLQKZWDUADP-UHFFFAOYSA-N 4-[2-(2-phenylquinolin-4-yl)oxyacetyl]piperazine-1-carbaldehyde Chemical compound C1CN(C=O)CCN1C(=O)COC1=CC(C=2C=CC=CC=2)=NC2=CC=CC=C12 AXDMLQKZWDUADP-UHFFFAOYSA-N 0.000 description 1
- UXWQDYWBGHNOFQ-UHFFFAOYSA-N 5-chloro-2-phenyl-1h-quinolin-4-one Chemical compound N=1C2=CC=CC(Cl)=C2C(O)=CC=1C1=CC=CC=C1 UXWQDYWBGHNOFQ-UHFFFAOYSA-N 0.000 description 1
- KFCTXLVNHOGMHX-UHFFFAOYSA-N 6-nitro-2-phenyl-1h-quinolin-4-one Chemical compound C=1C(=O)C2=CC([N+](=O)[O-])=CC=C2NC=1C1=CC=CC=C1 KFCTXLVNHOGMHX-UHFFFAOYSA-N 0.000 description 1
- XQOKFGZSHRSHMK-UHFFFAOYSA-N 7-chloro-2-phenyl-1h-quinolin-4-one Chemical compound C=1C(Cl)=CC=C(C(C=2)=O)C=1NC=2C1=CC=CC=C1 XQOKFGZSHRSHMK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101150039077 CRCP gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PYFSCIWXNSXGNS-UHFFFAOYSA-N N-methyl-sec-butylamine Natural products CCC(C)NC PYFSCIWXNSXGNS-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
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- 241000700159 Rattus Species 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
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- 230000029936 alkylation Effects 0.000 description 1
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- 239000008346 aqueous phase Substances 0.000 description 1
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- 229910052794 bromium Inorganic materials 0.000 description 1
- QEHQYWGWJFAXBU-UHFFFAOYSA-N but-1-ene propan-2-one Chemical compound CCC=C.CC(C)=O QEHQYWGWJFAXBU-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010568 chiral column chromatography Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
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- 229960003529 diazepam Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- FGXQBTGOXRNNTR-UHFFFAOYSA-N ethyl 1-[2-(2-phenylquinolin-4-yl)oxyacetyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)COC1=CC(C=2C=CC=CC=2)=NC2=CC=CC=C12 FGXQBTGOXRNNTR-UHFFFAOYSA-N 0.000 description 1
- NTIFYILQVNLPPC-UHFFFAOYSA-N ethyl 2-(2-phenylquinolin-4-yl)oxyacetate Chemical compound N=1C2=CC=CC=C2C(OCC(=O)OCC)=CC=1C1=CC=CC=C1 NTIFYILQVNLPPC-UHFFFAOYSA-N 0.000 description 1
- YMUNUVJSNWUWDA-UHFFFAOYSA-N ethyl 3-(2-fluorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1F YMUNUVJSNWUWDA-UHFFFAOYSA-N 0.000 description 1
- GEQMJBPKCOZHMV-UHFFFAOYSA-N ethyl 3-(4-methylphenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(C)C=C1 GEQMJBPKCOZHMV-UHFFFAOYSA-N 0.000 description 1
- YCHPVUWFIZXXPI-UHFFFAOYSA-N ethyl 3-oxo-3-[3-(trifluoromethyl)phenyl]propanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC(C(F)(F)F)=C1 YCHPVUWFIZXXPI-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- ZQGJEUVBUVKZKS-UHFFFAOYSA-N n,2-dimethylpropan-2-amine Chemical compound CNC(C)(C)C ZQGJEUVBUVKZKS-UHFFFAOYSA-N 0.000 description 1
- ARPHFLOVGFJBKL-UHFFFAOYSA-N n-(2-methoxyethyl)-n-methyl-2-(2-phenylquinolin-4-yl)oxyacetamide Chemical compound N=1C2=CC=CC=C2C(OCC(=O)N(C)CCOC)=CC=1C1=CC=CC=C1 ARPHFLOVGFJBKL-UHFFFAOYSA-N 0.000 description 1
- CEHWQJUYPGVPQY-UHFFFAOYSA-N n-[4-(2-morpholin-4-yl-2-oxoethoxy)-2-phenylquinolin-6-yl]acetamide Chemical compound C12=CC(NC(=O)C)=CC=C2N=C(C=2C=CC=CC=2)C=C1OCC(=O)N1CCOCC1 CEHWQJUYPGVPQY-UHFFFAOYSA-N 0.000 description 1
- SEJOTGXNTFGNLN-UHFFFAOYSA-N n-benzyl-n-methyl-2-(2-phenylquinolin-4-yl)oxyacetamide Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1OCC(=O)N(C)CC1=CC=CC=C1 SEJOTGXNTFGNLN-UHFFFAOYSA-N 0.000 description 1
- LBLMFVBWBQAZGR-UHFFFAOYSA-N n-butan-2-yl-n-methyl-2-(2-phenylquinolin-4-yl)oxyacetamide;hydrochloride Chemical compound Cl.N=1C2=CC=CC=C2C(OCC(=O)N(C)C(C)CC)=CC=1C1=CC=CC=C1 LBLMFVBWBQAZGR-UHFFFAOYSA-N 0.000 description 1
- GGJNJQSPWHSREC-UHFFFAOYSA-N n-cyclobutyl-n-methyl-2-(2-phenylquinolin-4-yl)oxyacetamide Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1OCC(=O)N(C)C1CCC1 GGJNJQSPWHSREC-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- OYOUOBUGZWDEBU-UHFFFAOYSA-N n-methyl-2-(2-phenylquinolin-4-yl)oxy-n-propan-2-ylacetamide Chemical compound N=1C2=CC=CC=C2C(OCC(=O)N(C)C(C)C)=CC=1C1=CC=CC=C1 OYOUOBUGZWDEBU-UHFFFAOYSA-N 0.000 description 1
- WLRDHCQGBJSMLT-UHFFFAOYSA-N n-methyl-n-phenyl-2-(2-phenylquinolin-4-yl)oxyacetamide Chemical compound C=1C=CC=CC=1N(C)C(=O)COC(C1=CC=CC=C1N=1)=CC=1C1=CC=CC=C1 WLRDHCQGBJSMLT-UHFFFAOYSA-N 0.000 description 1
- BMYUOHROMQSSBD-UHFFFAOYSA-N n-methylmorpholin-4-amine Chemical compound CNN1CCOCC1 BMYUOHROMQSSBD-UHFFFAOYSA-N 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- CGRXUEJBXKMBKU-UHFFFAOYSA-N n-tert-butyl-n-methyl-2-(2-phenylquinolin-4-yl)oxyacetamide Chemical compound N=1C2=CC=CC=C2C(OCC(=O)N(C)C(C)(C)C)=CC=1C1=CC=CC=C1 CGRXUEJBXKMBKU-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
- C07D239/82—Oxygen atoms with an aryl radical attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
-
- 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
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (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)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Anesthesiology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Quinoline Compounds (AREA)
- Medicinal Preparation (AREA)
- Cephalosporin Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR858508111A FR2582514B1 (fr) | 1985-05-30 | 1985-05-30 | Medicaments a base d'amides, nouveaux amides et leur preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
NO862134L true NO862134L (no) | 1986-12-01 |
Family
ID=9319678
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO862134A NO862134L (no) | 1985-05-30 | 1986-05-29 | Amidderivater av kinolin samt deres fremstilling. |
NO862133A NO862133L (no) | 1985-05-30 | 1986-05-29 | Amider og deres fremstilling. |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO862133A NO862133L (no) | 1985-05-30 | 1986-05-29 | Amider og deres fremstilling. |
Country Status (20)
Country | Link |
---|---|
US (3) | US4728647A (pt) |
EP (2) | EP0210084B1 (pt) |
JP (2) | JPS625946A (pt) |
AT (2) | ATE47840T1 (pt) |
AU (2) | AU579472B2 (pt) |
CA (2) | CA1264160A (pt) |
DE (2) | DE3666813D1 (pt) |
DK (2) | DK252286A (pt) |
ES (7) | ES8704732A1 (pt) |
FR (1) | FR2582514B1 (pt) |
GR (2) | GR861368B (pt) |
HU (2) | HU195641B (pt) |
IL (2) | IL78969A (pt) |
MA (2) | MA20696A1 (pt) |
NO (2) | NO862134L (pt) |
NZ (2) | NZ216331A (pt) |
PT (2) | PT82673B (pt) |
SU (7) | SU1440342A3 (pt) |
TN (2) | TNSN86080A1 (pt) |
ZA (2) | ZA863992B (pt) |
Families Citing this family (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4876346A (en) * | 1985-05-02 | 1989-10-24 | American Home Products Corporation | Quinoline compounds |
FR2582514B1 (fr) * | 1985-05-30 | 1988-02-19 | Rhone Poulenc Sante | Medicaments a base d'amides, nouveaux amides et leur preparation |
HU199424B (en) * | 1987-04-24 | 1990-02-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing quinoline thioethers and pharmaceutical compositions comprising such compounds |
HU199423B (en) * | 1987-04-24 | 1990-02-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing 3-amino-4-/ethylthio/-quinoline and pharmaceutical compositions comprising such compounds |
GB8726735D0 (en) * | 1987-11-14 | 1987-12-16 | Wellcome Found | Pesticidal compounds |
DE68917024D1 (de) * | 1988-05-24 | 1994-09-01 | Kirin Brewery | 4(1H)-Chinolonderivate. |
FR2636327A1 (fr) * | 1988-09-13 | 1990-03-16 | Rhone Poulenc Sante | Derives de quinoleine, leurs procedes de preparation et les medicaments les contenant |
JP2669905B2 (ja) * | 1989-09-01 | 1997-10-29 | ファナック株式会社 | リレーの溶着検出方法 |
FR2665159B1 (fr) * | 1990-07-24 | 1992-11-13 | Rhone Poulenc Sante | Nouveaux derives de la pyridine et de la quinoleine, leur preparation et les compositions pharmaceutiques qui les contiennent. |
EP0575097B1 (en) * | 1992-06-19 | 2000-11-02 | Eli Lilly And Company | 2,3-Bis-carboxamidomethyl substituted oxiranes as inhibitors of HIV protease and their use for the treatment of AIDS |
JP3408300B2 (ja) * | 1993-11-10 | 2003-05-19 | シチズン時計株式会社 | プリンタ |
DE4420337A1 (de) * | 1994-06-10 | 1995-12-14 | Bayer Ag | N-Heterocyclyl-heteroaryloxyacetamide |
US5658902A (en) * | 1994-12-22 | 1997-08-19 | Warner-Lambert Company | Quinazolines as inhibitors of endothelin converting enzyme |
IL117659A (en) * | 1995-04-13 | 2000-12-06 | Dainippon Pharmaceutical Co | Substituted 2-phenyl pyrimidino amino acetamide derivative process for preparing the same and a pharmaceutical composition containing same |
US5648448A (en) * | 1995-06-06 | 1997-07-15 | Hitachi Chemical Company, Ltd. | Method of preparation of polyquinolines |
US5776946A (en) * | 1995-08-28 | 1998-07-07 | Mcgeer; Patrick L. | Peripheral benzodiazepine receptor ligands as antiinflammatory agents |
FR2750427B1 (fr) * | 1996-06-28 | 1998-08-07 | Synthelabo | Derives de 1-oxo-1, 2-dihydroisoquinoleine-4-propanamide, leur preparation et leur application en therapeutique |
US5998624A (en) * | 1997-05-07 | 1999-12-07 | Emory University | Haloisoquinoline carboxamide |
ZA9810490B (en) | 1997-12-03 | 1999-05-20 | Dainippon Pharmaceutical Co | 2-Aryl-8-oxodihydropurine derivative process for the preparation thereof pharmaceutical composition containing the same and intermediate therefor |
FR2778564B1 (fr) * | 1998-05-13 | 2001-07-13 | Sanofi Sa | Utilisation de composes reduisant l'apoptose |
WO1999058117A1 (fr) * | 1998-05-13 | 1999-11-18 | Sanofi-Synthelabo | Utilisation de composes reduisant l'apoptose |
FR2779963A1 (fr) | 1998-06-22 | 1999-12-24 | Centre Nat Rech Scient | Utilisation d'un compose possedant une affinite pour le recepteur mitochondrial des benzodiazepines en therapie du cancer |
EP1140107B1 (en) | 1998-12-18 | 2006-07-19 | Scios Inc. | Agonists and antagonists of peripheral-type benzodiazepine receptors |
US6297256B1 (en) * | 1999-06-15 | 2001-10-02 | Neurogen Corporation | Aryl and heteroaryl substituted pyridino derivatives GABA brain receptor ligands |
AR026748A1 (es) * | 1999-12-08 | 2003-02-26 | Vertex Pharma | Un compuesto inhibidor de caspasas, una composicion farmaceutica que lo comprende, un metodo para la sintesis del mismo y un compuesto intermediario paradicha sintesis |
EP1110552A1 (en) * | 1999-12-22 | 2001-06-27 | Aventis Pharma S.A. | Use of a compound with affinity for the mitochondrial benzodiazepine receptor in cancer therapy |
WO2002000623A2 (en) * | 2000-06-26 | 2002-01-03 | Neurogen Corporation | Aryl fused substituted 4-oxy-pyridines |
CN100503572C (zh) | 2002-06-28 | 2009-06-24 | 沃泰克斯药物股份有限公司 | 天冬氨酸特异性半胱氨酸蛋白酶抑制剂及其用途 |
US7612091B2 (en) * | 2002-12-20 | 2009-11-03 | Vertex Pharmaceuticals Incorporated | Caspase inhibitors and uses thereof |
CA2505195C (en) * | 2002-12-23 | 2012-07-10 | Icagen, Inc. | Quinazolinones as potassium channel modulators |
PE20050159A1 (es) * | 2003-05-27 | 2005-04-19 | Vertex Pharma | Derivados de acido 3-[2-(3-amino-2-oxo-2h-piridin-1-il)-acetilamino]-4-oxo-pentanoico como inhibidores de caspasa |
US7423176B2 (en) * | 2004-04-13 | 2008-09-09 | Cephalon, Inc. | Bicyclic aromatic sulfinyl derivatives |
EP1889837A1 (en) * | 2006-07-10 | 2008-02-20 | Pharmeste S.r.l. | VR1 vanilloid receptor antagonists with a iononic substructure |
EP2139879B1 (en) * | 2007-03-22 | 2012-07-11 | AstraZeneca AB | Quinoline derivatives for the treatment of inflammatory diseases |
US8382751B2 (en) * | 2009-09-10 | 2013-02-26 | Covidien Lp | System and method for power supply noise reduction |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR964545A (pt) * | 1947-04-11 | 1950-08-18 | ||
US2568037A (en) * | 1947-10-24 | 1951-09-18 | Sterling Drug Inc | Tertiary-aminoalkyl esters and amides of 4-quinolylmercaptoalkanoic acids and their preparation |
US2785165A (en) * | 1953-12-22 | 1957-03-12 | Abbott Lab | Preparation of 4-aminoquinoline |
GB1013224A (en) * | 1962-06-21 | 1965-12-15 | Ici Ltd | Heterocyclic aminoethanols |
GB1064252A (en) * | 1963-09-19 | 1967-04-05 | Ici Ltd | Amides and pharmaceutical compositions containing them |
IL26022A (en) * | 1966-06-23 | 1971-06-23 | Haber R | Nitrofuryl quinoline derivatives |
GB1177548A (en) * | 1967-11-28 | 1970-01-14 | Ici Ltd | Phenoxy-and Anilino-Alkanoic Acid Amides |
US3595861A (en) * | 1967-12-08 | 1971-07-27 | American Home Prod | Novel synthesis of 2-quinazolinepropionic acids and derivatives |
FR8411M (pt) * | 1968-12-31 | 1971-03-31 | ||
DE2361438C3 (de) * | 1973-12-10 | 1979-12-13 | Hoechst Ag, 6000 Frankfurt | 4-Hydroxychinoün- und 4-Hydroxytetrahydrochinolin-N^N-dimethylcarbamate, Verfahren zu ihrer Herstellung und diese enthaltende insektizide Mittel |
DE2411662A1 (de) | 1974-03-12 | 1975-09-25 | Lechler Elring Dichtungswerke | Vorrichtung zum einseitigen anheben und lenkbarmachen einer palette insbesondere einer rollpalette |
GB1574019A (en) * | 1977-01-14 | 1980-09-03 | Joullie International Sa | Therapeutically useful 3,4,5-trimethoxybenzene derivatives |
FR2471981A1 (fr) * | 1979-12-21 | 1981-06-26 | Pharmindustrie | Nouveaux derives de la (piperidyl-4)-2 (quinolyl-4)-1 ethanone, produits intermediaires et procedes pour leur preparation, et leur utilisation comme medicaments |
FR2485014A1 (fr) * | 1980-06-20 | 1981-12-24 | Pharmindustrie | Nouveaux derives de (quinolyl-2, -3 ou -4)-1 (piperidyl ou pyrrolidinyl-2 ou -3)-2 ou -3 ethanone ou propanone, procedes pour leur preparation, et leur utilisation comme medicaments |
FR2525595A1 (fr) * | 1982-04-27 | 1983-10-28 | Pharmuka Lab | Nouveaux derives d'arene et d'heteroarenecarboxamides et leur utilisation comme medicaments |
FR2538388B1 (fr) * | 1982-12-24 | 1985-06-21 | Pharmuka Lab | Nouveaux derives de naphtalene- ou azanaphtalenecarboxamide, leurs procedes de preparation et leur utilisation comme medicaments |
NZ209710A (en) * | 1983-09-29 | 1988-02-12 | Akzo Nv | Quinazoline and isoquinoline derivatives and pharmaceutical and veterinary compositions containing such |
FR2582514B1 (fr) * | 1985-05-30 | 1988-02-19 | Rhone Poulenc Sante | Medicaments a base d'amides, nouveaux amides et leur preparation |
-
1985
- 1985-05-30 FR FR858508111A patent/FR2582514B1/fr not_active Expired
-
1986
- 1986-05-28 GR GR861368A patent/GR861368B/el unknown
- 1986-05-28 ZA ZA863992A patent/ZA863992B/xx unknown
- 1986-05-28 PT PT82673A patent/PT82673B/pt not_active IP Right Cessation
- 1986-05-28 NZ NZ216331A patent/NZ216331A/xx unknown
- 1986-05-28 PT PT82674A patent/PT82674B/pt not_active IP Right Cessation
- 1986-05-28 GR GR861369A patent/GR861369B/el unknown
- 1986-05-28 US US06/867,474 patent/US4728647A/en not_active Expired - Fee Related
- 1986-05-28 US US06/867,555 patent/US4788204A/en not_active Expired - Fee Related
- 1986-05-28 AU AU58030/86A patent/AU579472B2/en not_active Ceased
- 1986-05-28 NZ NZ216330A patent/NZ216330A/xx unknown
- 1986-05-28 ZA ZA863993A patent/ZA863993B/xx unknown
- 1986-05-28 AU AU58031/86A patent/AU579473B2/en not_active Ceased
- 1986-05-29 SU SU864027526A patent/SU1440342A3/ru active
- 1986-05-29 NO NO862134A patent/NO862134L/no unknown
- 1986-05-29 MA MA20922A patent/MA20696A1/fr unknown
- 1986-05-29 HU HU862265A patent/HU195641B/hu unknown
- 1986-05-29 AT AT86401141T patent/ATE47840T1/de not_active IP Right Cessation
- 1986-05-29 IL IL78969A patent/IL78969A/xx unknown
- 1986-05-29 SU SU864027667A patent/SU1508957A3/ru active
- 1986-05-29 EP EP86401140A patent/EP0210084B1/fr not_active Expired
- 1986-05-29 EP EP86401141A patent/EP0205375B1/fr not_active Expired
- 1986-05-29 CA CA000510308A patent/CA1264160A/fr not_active Expired - Lifetime
- 1986-05-29 AT AT86401140T patent/ATE40689T1/de active
- 1986-05-29 DE DE8686401141T patent/DE3666813D1/de not_active Expired
- 1986-05-29 HU HU862266A patent/HU195642B/hu unknown
- 1986-05-29 MA MA20923A patent/MA20697A1/fr unknown
- 1986-05-29 NO NO862133A patent/NO862133L/no unknown
- 1986-05-29 DK DK252286A patent/DK252286A/da not_active Application Discontinuation
- 1986-05-29 DE DE8686401140T patent/DE3662045D1/de not_active Expired
- 1986-05-29 IL IL78968A patent/IL78968A/xx unknown
- 1986-05-29 CA CA000510311A patent/CA1251206A/fr not_active Expired
- 1986-05-29 DK DK252386A patent/DK252386A/da not_active Application Discontinuation
- 1986-05-30 TN TNTNSN86080A patent/TNSN86080A1/fr unknown
- 1986-05-30 JP JP61123872A patent/JPS625946A/ja active Pending
- 1986-05-30 TN TNTNSN86081A patent/TNSN86081A1/fr unknown
- 1986-05-30 JP JP61123873A patent/JPS6264A/ja active Pending
- 1986-05-30 ES ES555558A patent/ES8704732A1/es not_active Expired
- 1986-05-30 ES ES555557A patent/ES8704731A1/es not_active Expired
- 1986-10-31 ES ES557167A patent/ES8800660A1/es not_active Expired
- 1986-10-31 ES ES557169A patent/ES8705227A1/es not_active Expired
- 1986-10-31 ES ES557166A patent/ES8705225A1/es not_active Expired
- 1986-10-31 ES ES557168A patent/ES8705226A1/es not_active Expired
- 1986-10-31 ES ES557170A patent/ES8705228A1/es not_active Expired
-
1987
- 1987-03-09 SU SU874202112A patent/SU1470183A3/ru active
- 1987-04-06 SU SU874202297A patent/SU1470182A3/ru active
- 1987-04-06 SU SU874202362A patent/SU1544186A3/ru active
- 1987-04-06 SU SU874202398A patent/SU1537135A3/ru active
- 1987-04-06 SU SU874202412A patent/SU1614759A3/ru active
-
1988
- 1988-03-11 US US07/167,126 patent/US4788199A/en not_active Expired - Fee Related
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