CS258147B2 - Method of benzazecine's new derivatives production - Google Patents
Method of benzazecine's new derivatives production Download PDFInfo
- Publication number
- CS258147B2 CS258147B2 CS87418A CS41887A CS258147B2 CS 258147 B2 CS258147 B2 CS 258147B2 CS 87418 A CS87418 A CS 87418A CS 41887 A CS41887 A CS 41887A CS 258147 B2 CS258147 B2 CS 258147B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- chloro
- hexahydro
- dione
- starting materials
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- LOLJNNQHTPVJJR-UHFFFAOYSA-N 1-benzazecine Chemical compound N1=CC=CC=CC=CC2=CC=CC=C21 LOLJNNQHTPVJJR-UHFFFAOYSA-N 0.000 title description 11
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 71
- -1 chlorobenzoyl group Chemical group 0.000 claims description 45
- 239000007858 starting material Substances 0.000 claims description 21
- 239000000460 chlorine Substances 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- CMQYKJWGZSNGTD-UHFFFAOYSA-N 11-chloro-4-propanoyl-2,5,6,7-tetrahydro-1h-4-benzazecine-3,8-dione Chemical compound C1CC(=O)N(C(=O)CC)CCCC(=O)C2=CC=C(Cl)C=C21 CMQYKJWGZSNGTD-UHFFFAOYSA-N 0.000 claims description 3
- CTZBZMQWRGOCHE-UHFFFAOYSA-N 4-acetyl-12-methoxy-2,5,6,7-tetrahydro-1h-4-benzazecine-3,8-dione Chemical compound C1CC(=O)N(C(C)=O)CCCC(=O)C2=C1C(OC)=CC=C2 CTZBZMQWRGOCHE-UHFFFAOYSA-N 0.000 claims description 3
- IYJWRRYOWNRXSA-UHFFFAOYSA-N COC1=CC=C(C=C1)C(=O)N2CCCC(=O)C3=CC=CC=C3C(CC2=O)Cl Chemical compound COC1=CC=C(C=C1)C(=O)N2CCCC(=O)C3=CC=CC=C3C(CC2=O)Cl IYJWRRYOWNRXSA-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- QGPYUYVQXFQIGA-UHFFFAOYSA-N 11-chloro-4-(4-chlorobenzoyl)-2,5,6,7-tetrahydro-1h-4-benzazecine-3,8-dione Chemical compound C1=CC(Cl)=CC=C1C(=O)N1C(=O)CCC2=CC(Cl)=CC=C2C(=O)CCC1 QGPYUYVQXFQIGA-UHFFFAOYSA-N 0.000 claims description 2
- OUYJLGNFPRQFFW-UHFFFAOYSA-N 4-acetyl-11-chloro-2,5,6,7-tetrahydro-1h-4-benzazecine-3,8-dione Chemical compound C1CC(=O)N(C(=O)C)CCCC(=O)C2=CC=C(Cl)C=C21 OUYJLGNFPRQFFW-UHFFFAOYSA-N 0.000 claims description 2
- VZERFDLTCJAXQX-UHFFFAOYSA-N 11-chloro-4-(2-methoxybenzoyl)-2,5,6,7-tetrahydro-1h-4-benzazecine-3,8-dione Chemical compound COC1=CC=CC=C1C(=O)N1C(=O)CCC2=CC(Cl)=CC=C2C(=O)CCC1 VZERFDLTCJAXQX-UHFFFAOYSA-N 0.000 claims 1
- 150000008072 azecines Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 220
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 140
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
- 239000000243 solution Substances 0.000 description 104
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
- 239000011541 reaction mixture Substances 0.000 description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 30
- 239000000741 silica gel Substances 0.000 description 30
- 229910002027 silica gel Inorganic materials 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 28
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 26
- 239000000725 suspension Substances 0.000 description 26
- 238000003756 stirring Methods 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- 239000012071 phase Substances 0.000 description 20
- 238000010992 reflux Methods 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 239000012074 organic phase Substances 0.000 description 19
- 238000001953 recrystallisation Methods 0.000 description 19
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 18
- 239000002245 particle Substances 0.000 description 18
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000003480 eluent Substances 0.000 description 15
- 239000000155 melt Substances 0.000 description 15
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 14
- 239000008346 aqueous phase Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- 238000002425 crystallisation Methods 0.000 description 13
- 230000008025 crystallization Effects 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 11
- 238000000605 extraction Methods 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000012280 lithium aluminium hydride Substances 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000002026 chloroform extract Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 8
- 235000019345 sodium thiosulphate Nutrition 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 6
- IHNINSVQYKIZIC-UHFFFAOYSA-N 2h-quinolin-3-one Chemical compound C1=CC=CC2=CC(=O)CN=C21 IHNINSVQYKIZIC-UHFFFAOYSA-N 0.000 description 5
- LWBUFVBZEQZNDP-UHFFFAOYSA-N 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline Chemical compound N1CCCC2=C1CCC1=CC(Cl)=CC=C12 LWBUFVBZEQZNDP-UHFFFAOYSA-N 0.000 description 5
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 5
- 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 5
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 5
- 230000002490 cerebral effect Effects 0.000 description 5
- 239000008120 corn starch Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 5
- 229960002646 scopolamine Drugs 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000004133 Sodium thiosulphate Substances 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- QQSYTUUAEZUAKL-UHFFFAOYSA-N 6-chloro-3,4-dihydro-1h-naphthalen-2-one Chemical compound C1C(=O)CCC2=CC(Cl)=CC=C21 QQSYTUUAEZUAKL-UHFFFAOYSA-N 0.000 description 3
- ZBLPUKDWONQIMX-UHFFFAOYSA-N 8-chloro-3,4-dihydro-1h-naphthalen-2-one Chemical compound C1CC(=O)CC2=C1C=CC=C2Cl ZBLPUKDWONQIMX-UHFFFAOYSA-N 0.000 description 3
- WEYWMYUBBQDNDR-UHFFFAOYSA-N 8-methoxy-1,2-dihydronaphthalene Chemical compound C1=CCCC2=C1C=CC=C2OC WEYWMYUBBQDNDR-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 3
- 229910001623 magnesium bromide Inorganic materials 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 230000003285 pharmacodynamic effect Effects 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000006403 short-term memory Effects 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- MMZDDGUXEUYHOS-UHFFFAOYSA-N (4-chlorophenyl)-(8-chloro-2,3,5,6-tetrahydro-1h-benzo[f]quinolin-4-yl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1C(CCC=2C3=CC=C(Cl)C=2)=C3CCC1 MMZDDGUXEUYHOS-UHFFFAOYSA-N 0.000 description 2
- XKZANXGJSUCZRO-UHFFFAOYSA-N (8-chloro-2,3,5,6-tetrahydro-1h-benzo[f]quinolin-4-yl)-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)N1C(CCC=2C3=CC=C(Cl)C=2)=C3CCC1 XKZANXGJSUCZRO-UHFFFAOYSA-N 0.000 description 2
- ROYKODXAJLJALK-UHFFFAOYSA-N (8-chloro-2,3,5,6-tetrahydro-1h-benzo[f]quinolin-4-yl)-phenylmethanone Chemical compound C1CC2=CC(Cl)=CC=C2C(CCC2)=C1N2C(=O)C1=CC=CC=C1 ROYKODXAJLJALK-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VWBJGGGNEYKMBC-UHFFFAOYSA-N 1-(10-chloro-2,3,5,6-tetrahydro-1h-benzo[f]quinolin-4-yl)ethanone Chemical compound C1CC2=CC=CC(Cl)=C2C2=C1N(C(=O)C)CCC2 VWBJGGGNEYKMBC-UHFFFAOYSA-N 0.000 description 2
- RABFPLIPOMMNLE-UHFFFAOYSA-N 1-(5-methoxy-3,4-dihydronaphthalen-2-yl)pyrrolidine Chemical compound C1CC=2C(OC)=CC=CC=2C=C1N1CCCC1 RABFPLIPOMMNLE-UHFFFAOYSA-N 0.000 description 2
- UQKUXTVBDYZXFQ-UHFFFAOYSA-N 1-(6,8-dichloro-3,4-dihydronaphthalen-2-yl)pyrrolidine Chemical compound C1CC2=CC(Cl)=CC(Cl)=C2C=C1N1CCCC1 UQKUXTVBDYZXFQ-UHFFFAOYSA-N 0.000 description 2
- OHXASHBAWOZUNU-UHFFFAOYSA-N 1-(6-bromo-3,4-dihydronaphthalen-2-yl)pyrrolidine Chemical compound C1CC2=CC(Br)=CC=C2C=C1N1CCCC1 OHXASHBAWOZUNU-UHFFFAOYSA-N 0.000 description 2
- SXUOTTHOOVPEHW-UHFFFAOYSA-N 1-(7-chloro-3,4-dihydronaphthalen-2-yl)pyrrolidine Chemical compound C=1C2=CC(Cl)=CC=C2CCC=1N1CCCC1 SXUOTTHOOVPEHW-UHFFFAOYSA-N 0.000 description 2
- XYWWFYSQXKHWRA-UHFFFAOYSA-N 1-(8-chloro-2,3,5,6-tetrahydro-1h-benzo[f]quinolin-4-yl)-2-phenylethanone Chemical compound C1CC2=CC(Cl)=CC=C2C(CCC2)=C1N2C(=O)CC1=CC=CC=C1 XYWWFYSQXKHWRA-UHFFFAOYSA-N 0.000 description 2
- CBRPUYAZGPDZTP-UHFFFAOYSA-N 1-(8-chloro-2,3,5,6-tetrahydro-1h-benzo[f]quinolin-4-yl)ethanone Chemical compound C1CC2=CC(Cl)=CC=C2C2=C1N(C(=O)C)CCC2 CBRPUYAZGPDZTP-UHFFFAOYSA-N 0.000 description 2
- UXDINFGSAPBDAJ-UHFFFAOYSA-N 1-(8-chloro-2,3,5,6-tetrahydro-1h-benzo[f]quinolin-4-yl)propan-1-one Chemical compound C1CC2=CC(Cl)=CC=C2C2=C1N(C(=O)CC)CCC2 UXDINFGSAPBDAJ-UHFFFAOYSA-N 0.000 description 2
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- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000015654 memory Effects 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- ZDHURYWHEBEGHO-UHFFFAOYSA-N potassiopotassium Chemical compound [K].[K] ZDHURYWHEBEGHO-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose 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
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 208000027491 vestibular disease Diseases 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/02—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/04—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D225/06—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D227/00—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00
- C07D227/02—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D227/06—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with 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
- C07D227/08—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH26686 | 1986-01-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS41887A2 CS41887A2 (en) | 1987-11-12 |
| CS258147B2 true CS258147B2 (en) | 1988-07-15 |
Family
ID=4183090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS87418A CS258147B2 (en) | 1986-01-23 | 1987-01-20 | Method of benzazecine's new derivatives production |
Country Status (30)
| Country | Link |
|---|---|
| US (4) | US4732979A (xx) |
| EP (1) | EP0230967B1 (xx) |
| JP (1) | JPS62169770A (xx) |
| KR (1) | KR910000659B1 (xx) |
| CN (1) | CN1013111B (xx) |
| AT (1) | ATE68790T1 (xx) |
| AU (1) | AU590042B2 (xx) |
| CS (1) | CS258147B2 (xx) |
| DD (1) | DD264431A5 (xx) |
| DE (1) | DE3773950D1 (xx) |
| DK (1) | DK35887A (xx) |
| FI (1) | FI82931C (xx) |
| GB (1) | GB2185744B (xx) |
| HU (1) | HU197883B (xx) |
| IE (1) | IE870167L (xx) |
| IL (1) | IL81317A (xx) |
| IS (1) | IS3190A7 (xx) |
| MC (1) | MC1795A1 (xx) |
| MT (1) | MTP996B (xx) |
| MW (1) | MW187A1 (xx) |
| NO (1) | NO167385C (xx) |
| NZ (1) | NZ218987A (xx) |
| OA (1) | OA08469A (xx) |
| PH (1) | PH22879A (xx) |
| PL (1) | PL263796A1 (xx) |
| PT (1) | PT84181B (xx) |
| TN (1) | TNSN87006A1 (xx) |
| YU (1) | YU7087A (xx) |
| ZA (1) | ZA87407B (xx) |
| ZW (1) | ZW1087A1 (xx) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI82931C (fi) * | 1986-01-23 | 1991-05-10 | Hoffmann La Roche | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara bensazecinderivat. |
| IN167395B (xx) * | 1987-07-21 | 1990-10-20 | Hoffmann La Roche | |
| EP0591583B1 (en) * | 1991-08-21 | 2001-12-19 | Eli Lilly And Company | Benzo (f) quinolinones as 5-alpha-reductase inhibitors |
| ES2125884T3 (es) * | 1991-08-21 | 1999-03-16 | Lilly Co Eli | Hexahidrobenzo(f)quinolinonas como inhibidores de la 5-alfa-reductasa. |
| US5239075A (en) * | 1991-08-21 | 1993-08-24 | Eli Lilly And Company | Process for the preparation of benzo (f) quinolinones |
| US5250539A (en) * | 1991-08-21 | 1993-10-05 | Eli Lilly And Company | Hexahydrobenzo[f]quinolinones |
| WO1994022444A1 (en) * | 1993-03-29 | 1994-10-13 | Smithkline Beecham Corporation | Tricyclic compounds for inhibiting platelet aggregation |
| GB9317314D0 (en) * | 1993-08-20 | 1993-10-06 | Smithkline Beecham Corp | Compounds |
| KR970706271A (ko) | 1994-09-20 | 1997-11-03 | 스티븐슨 린다 에스. | 시냅스 전달 향상용 약제(drugs to improve synaptic transmission) |
| US20050067341A1 (en) * | 2003-09-25 | 2005-03-31 | Green Dennis H. | Continuous production membrane water treatment plant and method for operating same |
| US7094331B2 (en) * | 2003-11-05 | 2006-08-22 | Marathon Ashland Petroleum Llc | Viscosity modification of heavy hydrocarbons using dihydric alcohols |
| US20090263439A1 (en) * | 2008-04-18 | 2009-10-22 | The Procter & Gamble Company | Antimicrobial Preservative Free Wipe |
| CN106117028B (zh) * | 2016-06-14 | 2019-01-01 | 浙江永太药业有限公司 | 一种制备卤代-3,4-二氢-1h-2-萘酮的工艺方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE442586A (xx) * | 1940-07-31 | |||
| JPS5129710B2 (xx) * | 1972-09-09 | 1976-08-27 | ||
| US4341786A (en) * | 1981-03-02 | 1982-07-27 | Smithkline Corporation | Pharmaceutical compositions and method of producing central alpha1 agonist activity utilizing octahydrobenzo[f]quinoline compounds |
| US4521423A (en) * | 1983-10-31 | 1985-06-04 | Ayerst, Mckenna & Harrison, Ltd. | 7,8,9,10-Tetrahydrobenzo[h]quinolin-9-amine derivatives and compositions and methods for treating depression employing them |
| FI82931C (fi) * | 1986-01-23 | 1991-05-10 | Hoffmann La Roche | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara bensazecinderivat. |
-
1987
- 1987-01-20 FI FI870220A patent/FI82931C/fi not_active IP Right Cessation
- 1987-01-20 IL IL81317A patent/IL81317A/xx unknown
- 1987-01-20 CS CS87418A patent/CS258147B2/cs unknown
- 1987-01-20 NZ NZ218987A patent/NZ218987A/en unknown
- 1987-01-20 MW MW1/87A patent/MW187A1/xx unknown
- 1987-01-20 EP EP87100733A patent/EP0230967B1/de not_active Expired - Lifetime
- 1987-01-20 ZA ZA87407A patent/ZA87407B/xx unknown
- 1987-01-20 DE DE8787100733T patent/DE3773950D1/de not_active Expired - Lifetime
- 1987-01-20 YU YU00070/87A patent/YU7087A/xx unknown
- 1987-01-20 PH PH34744A patent/PH22879A/en unknown
- 1987-01-20 AT AT87100733T patent/ATE68790T1/de not_active IP Right Cessation
- 1987-01-21 US US07/005,712 patent/US4732979A/en not_active Expired - Fee Related
- 1987-01-21 ZW ZW10/87A patent/ZW1087A1/xx unknown
- 1987-01-21 HU HU87163A patent/HU197883B/hu not_active IP Right Cessation
- 1987-01-21 DD DD87299380A patent/DD264431A5/de unknown
- 1987-01-22 IE IE870167A patent/IE870167L/xx unknown
- 1987-01-22 AU AU67911/87A patent/AU590042B2/en not_active Ceased
- 1987-01-22 PT PT84181A patent/PT84181B/pt not_active IP Right Cessation
- 1987-01-22 GB GB8701416A patent/GB2185744B/en not_active Expired
- 1987-01-22 DK DK035887A patent/DK35887A/da not_active Application Discontinuation
- 1987-01-22 MT MT996A patent/MTP996B/xx unknown
- 1987-01-22 MC MC871868A patent/MC1795A1/fr unknown
- 1987-01-22 CN CN87100312A patent/CN1013111B/zh not_active Expired
- 1987-01-22 NO NO870280A patent/NO167385C/no unknown
- 1987-01-22 JP JP62011477A patent/JPS62169770A/ja active Pending
- 1987-01-22 TN TNTNSN87006A patent/TNSN87006A1/fr unknown
- 1987-01-22 IS IS3190A patent/IS3190A7/is unknown
- 1987-01-23 KR KR1019870000533A patent/KR910000659B1/ko not_active Expired
- 1987-01-23 PL PL1987263796A patent/PL263796A1/xx unknown
- 1987-01-23 OA OA59052A patent/OA08469A/xx unknown
- 1987-11-18 US US07/121,987 patent/US4749791A/en not_active Expired - Fee Related
-
1988
- 1988-02-11 US US07/154,760 patent/US4876340A/en not_active Expired - Fee Related
-
1989
- 1989-08-17 US US07/395,380 patent/US4957911A/en not_active Expired - Fee Related
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