BE844358A - Nouvelles benzodiazepines, leur preparation et compositions pharmaceutiques les contenant - Google Patents

Nouvelles benzodiazepines, leur preparation et compositions pharmaceutiques les contenant

Info

Publication number: BE844358A
Authority: BE; Belgium
Prior art keywords: emi; compounds; compounds according; benzodiazepin; fluoro
Prior art date: 1975-07-21

Application number

BE169103A

Other languages

English (en)

French (fr)

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-07-21

Filing date

1976-07-20

Publication date

1977-01-20

1976-07-20 Application filed filed Critical

1977-01-20 Publication of BE844358A publication Critical patent/BE844358A/fr

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 8
229940049706 benzodiazepine Drugs 0.000 title description 12
238000002360 preparation method Methods 0.000 title description 8
150000001557 benzodiazepines Chemical class 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims description 41
229910052801 chlorine Inorganic materials 0.000 claims description 19
230000000694 effects Effects 0.000 claims description 16
229910052794 bromium Inorganic materials 0.000 claims description 15
229910052731 fluorine Inorganic materials 0.000 claims description 13
238000000034 method Methods 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 8
230000002936 tranquilizing effect Effects 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
229940100198 alkylating agent Drugs 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
230000001624 sedative effect Effects 0.000 claims description 3
NINGMRSNYNFRCB-UHFFFAOYSA-N 7-chloro-3-fluoro-1-methyl-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1C(F)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 NINGMRSNYNFRCB-UHFFFAOYSA-N 0.000 claims 1
230000001939 inductive effect Effects 0.000 claims 1
210000002027 skeletal muscle Anatomy 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
239000011541 reaction mixture Substances 0.000 description 19
239000000460 chlorine Substances 0.000 description 18
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 18
238000012360 testing method Methods 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
239000000725 suspension Substances 0.000 description 15
239000003814 drug Substances 0.000 description 14
239000000203 mixture Substances 0.000 description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
-1 inorganic acid halide Chemical class 0.000 description 12
239000000047 product Substances 0.000 description 12
241000699666 Mus <mouse, genus> Species 0.000 description 11
239000011737 fluorine Substances 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
239000012044 organic layer Substances 0.000 description 11
239000007787 solid Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
241000699670 Mus sp. Species 0.000 description 9
229940079593 drug Drugs 0.000 description 9
239000005457 ice water Substances 0.000 description 9
229910052740 iodine Inorganic materials 0.000 description 9
239000011630 iodine Substances 0.000 description 9
230000011514 reflex Effects 0.000 description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
239000000843 powder Substances 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
239000003826 tablet Substances 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000002775 capsule Substances 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
150000002367 halogens Chemical group 0.000 description 6
239000003204 tranquilizing agent Substances 0.000 description 6
ZHYMGSPDEVXULU-UHFFFAOYSA-N 1,2-benzodiazepin-3-one Chemical class N1=NC(=O)C=CC2=CC=CC=C21 ZHYMGSPDEVXULU-UHFFFAOYSA-N 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000003981 vehicle Substances 0.000 description 5
RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000000463 material Substances 0.000 description 4
230000035939 shock Effects 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 3
IEAZSLKYQNZPRN-UHFFFAOYSA-N 7-chloro-3-fluoro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(F)N=C1C1=CC=CC=C1 IEAZSLKYQNZPRN-UHFFFAOYSA-N 0.000 description 3
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 3
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000002249 anxiolytic agent Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
235000013305 food Nutrition 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000008297 liquid dosage form Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000003158 myorelaxant agent Substances 0.000 description 3
230000001670 myorelaxant effect Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000932 sedative agent Substances 0.000 description 3
229940125723 sedative agent Drugs 0.000 description 3
239000002002 slurry Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 3
230000001629 suppression Effects 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 3
229940029284 trichlorofluoromethane Drugs 0.000 description 3
XHPPBGZNBZMKNH-UHFFFAOYSA-N 1,2-dihydro-1,2-benzodiazepin-3-one Chemical compound C1=CC(O)=NNC2=CC=CC=C21 XHPPBGZNBZMKNH-UHFFFAOYSA-N 0.000 description 2
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
PZOZHMBWLDUJCP-UHFFFAOYSA-N 3-fluoro-1H-1,2-benzodiazepine Chemical class FC1=NNC2=C(C=C1)C=CC=C2 PZOZHMBWLDUJCP-UHFFFAOYSA-N 0.000 description 2
208000019901 Anxiety disease Diseases 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
206010039897 Sedation Diseases 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
230000000049 anti-anxiety effect Effects 0.000 description 2
238000003556 assay Methods 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
230000006399 behavior Effects 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
229960003529 diazepam Drugs 0.000 description 2
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 2
235000005911 diet Nutrition 0.000 description 2
230000037213 diet Effects 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012025 fluorinating agent Substances 0.000 description 2
150000002222 fluorine compounds Chemical class 0.000 description 2
CTIKAHQFRQTTAY-UHFFFAOYSA-N fluoro(trimethyl)silane Chemical group C[Si](C)(C)F CTIKAHQFRQTTAY-UHFFFAOYSA-N 0.000 description 2
230000008570 general process Effects 0.000 description 2
239000012729 immediate-release (IR) formulation Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000007972 injectable composition Substances 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000010410 layer Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
230000000978 myorelaxation Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
239000003182 parenteral nutrition solution Substances 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
230000036280 sedation Effects 0.000 description 2
239000011343 solid material Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000012730 sustained-release form Substances 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
238000002627 tracheal intubation Methods 0.000 description 2
FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
XDIYNQZUNSSENW-UUBOPVPUSA-N (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O XDIYNQZUNSSENW-UUBOPVPUSA-N 0.000 description 1
SPXBMMLIMAILLQ-UHFFFAOYSA-N (7-bromo-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl) 2,2,2-trifluoroacetate Chemical compound C12=CC(Br)=CC=C2NC(=O)C(OC(=O)C(F)(F)F)N=C1C1=CC=CC=C1 SPXBMMLIMAILLQ-UHFFFAOYSA-N 0.000 description 1
HLIGFUYIDLCBRN-UHFFFAOYSA-N 1,2-benzodiazepine-1-carboxamide Chemical compound NC(=O)N1N=CC=CC2=CC=CC=C12 HLIGFUYIDLCBRN-UHFFFAOYSA-N 0.000 description 1
QYXVOHOOLFKXPK-UHFFFAOYSA-N 1,2-dihydro-1,2-benzodiazepine-3-thione Chemical class C1=CC(=S)NNC2=CC=CC=C21 QYXVOHOOLFKXPK-UHFFFAOYSA-N 0.000 description 1
GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
NBAIWSSBSSJGTC-UHFFFAOYSA-N 1H-1,2-benzodiazepin-3-ylmethanol Chemical compound C1=CC(CO)=NNC2=CC=CC=C21 NBAIWSSBSSJGTC-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
NOXIPAREWUQUGI-UHFFFAOYSA-N 3,7-dichloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(Cl)N=C1C1=CC=CC=C1 NOXIPAREWUQUGI-UHFFFAOYSA-N 0.000 description 1
LVUFMEUZYQQOQT-UHFFFAOYSA-N 3-chloro-1H-1,2-benzodiazepine Chemical class ClC1=NNc2ccccc2C=C1 LVUFMEUZYQQOQT-UHFFFAOYSA-N 0.000 description 1
KXDGFSQJNOOZLJ-UHFFFAOYSA-N 3-fluoro-1-methyl-7-nitro-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1C(F)C(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 KXDGFSQJNOOZLJ-UHFFFAOYSA-N 0.000 description 1
JJACTJCMCKSYQL-UHFFFAOYSA-N 7-bromo-3-fluoro-1-methyl-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1C(F)C(=O)N(C)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1 JJACTJCMCKSYQL-UHFFFAOYSA-N 0.000 description 1
LJEAWFCRPWEPNO-UHFFFAOYSA-N 7-bromo-3-fluoro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(Br)=CC=C2NC(=O)C(F)N=C1C1=CC=CC=C1 LJEAWFCRPWEPNO-UHFFFAOYSA-N 0.000 description 1
FQKPLPMFWKFKKP-UHFFFAOYSA-N 7-bromo-4-hydroxy-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound ON1CC(=O)N=C2C=CC(Br)=CC2=C1C1=CC=CC=C1 FQKPLPMFWKFKKP-UHFFFAOYSA-N 0.000 description 1
SRJBKJYPBGPEHL-UHFFFAOYSA-N 7-chloro-5-phenyl-1,4-benzodiazepin-2-one Chemical compound C=12C=C(Cl)C=CC2=NC(=O)C=NC=1C1=CC=CC=C1 SRJBKJYPBGPEHL-UHFFFAOYSA-N 0.000 description 1
KUNAEPADWAFUHL-UHFFFAOYSA-N 7-chloro-5-phenyl-2,3-dihydro-1h-1,4-benzodiazepin-3-ol Chemical compound N=1C(O)CNC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 KUNAEPADWAFUHL-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
BIPWOEUPDFDHQV-UHFFFAOYSA-N C12=CC(Br)=CC=C2NC(=O)C[N+]([O-])=C1C1=CC=CC=C1F Chemical compound C12=CC(Br)=CC=C2NC(=O)C[N+]([O-])=C1C1=CC=CC=C1F BIPWOEUPDFDHQV-UHFFFAOYSA-N 0.000 description 1
101100074836 Caenorhabditis elegans lin-22 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
241000557626 Corvus corax Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
206010021118 Hypotonia Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
208000010428 Muscle Weakness Diseases 0.000 description 1
206010062575 Muscle contracture Diseases 0.000 description 1
206010028372 Muscular weakness Diseases 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910021607 Silver chloride Inorganic materials 0.000 description 1
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
238000000692 Student's t-test Methods 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
SEQDDYPDSLOBDC-UHFFFAOYSA-N Temazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 SEQDDYPDSLOBDC-UHFFFAOYSA-N 0.000 description 1
244000290333 Vanilla fragrans Species 0.000 description 1
235000009499 Vanilla fragrans Nutrition 0.000 description 1
235000012036 Vanilla tahitensis Nutrition 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000013543 active substance Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000036592 analgesia Effects 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
VTUOVBVMHPBQLX-UHFFFAOYSA-N benzene heptane Chemical compound CCCCCCC.C1=CC=CC=C1.C1=CC=CC=C1 VTUOVBVMHPBQLX-UHFFFAOYSA-N 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
230000037396 body weight Effects 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
229960004782 chlordiazepoxide Drugs 0.000 description 1
ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
230000008602 contraction Effects 0.000 description 1
208000006111 contracture Diseases 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000001934 delay Effects 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000011152 fibreglass Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000007850 fluorescent dye Substances 0.000 description 1
150000002221 fluorine Chemical class 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
210000004209 hair Anatomy 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction 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
239000002198 insoluble material Substances 0.000 description 1
206010022437 insomnia Diseases 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000015250 liver sausages Nutrition 0.000 description 1
230000003137 locomotive effect Effects 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910001509 metal bromide Inorganic materials 0.000 description 1
229910001510 metal chloride Inorganic materials 0.000 description 1
229910001512 metal fluoride Inorganic materials 0.000 description 1
229910001511 metal iodide Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
229960004715 morphine sulfate Drugs 0.000 description 1
GRVOTVYEFDAHCL-RTSZDRIGSA-N morphine sulfate pentahydrate Chemical compound O.O.O.O.O.OS(O)(=O)=O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O GRVOTVYEFDAHCL-RTSZDRIGSA-N 0.000 description 1
230000036640 muscle relaxation Effects 0.000 description 1
XXZNFWHGOMHWCO-UHFFFAOYSA-N n,n-diethylthiohydroxylamine Chemical compound CCN(S)CC XXZNFWHGOMHWCO-UHFFFAOYSA-N 0.000 description 1
SAVQQRYWWAGSQW-UHFFFAOYSA-N n-methyl-n-(trifluoro-$l^{4}-sulfanyl)methanamine Chemical compound CN(C)S(F)(F)F SAVQQRYWWAGSQW-UHFFFAOYSA-N 0.000 description 1
239000003176 neuroleptic agent Substances 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 1
229960004535 oxazepam Drugs 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229960005152 pentetrazol Drugs 0.000 description 1
208000022821 personality disease Diseases 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
230000001107 psychogenic effect Effects 0.000 description 1
229940085605 saccharin sodium Drugs 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
229940096017 silver fluoride Drugs 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
210000003699 striated muscle Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 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
229910052623 talc Inorganic materials 0.000 description 1
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
LSJNBGSOIVSBBR-UHFFFAOYSA-N thionyl fluoride Chemical compound FS(F)=O LSJNBGSOIVSBBR-UHFFFAOYSA-N 0.000 description 1
229940098465 tincture Drugs 0.000 description 1
CCKAYTBOIIPZGA-UHFFFAOYSA-N trifluoro(pyrrolidin-1-yl)-$l^{4}-sulfane Chemical compound FS(F)(F)N1CCCC1 CCKAYTBOIIPZGA-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BE169103A 1975-07-21 1976-07-20 Nouvelles benzodiazepines, leur preparation et compositions pharmaceutiques les contenant BE844358A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US59750275A	1975-07-31	1975-07-31

Publications (1)

Publication Number	Publication Date
BE844358A true BE844358A (fr)	1977-01-20

Family

ID=24391788

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE169103A BE844358A (fr)	1975-07-21	1976-07-20	Nouvelles benzodiazepines, leur preparation et compositions pharmaceutiques les contenant

Country Status (3)

Country	Link
AT (1)	AT355027B (de)
BE (1)	BE844358A (de)
ZA (1)	ZA764304B (de)

1976
- 1976-07-20 BE BE169103A patent/BE844358A/fr unknown
- 1976-07-20 ZA ZA00764304A patent/ZA764304B/xx unknown
- 1976-07-21 AT AT536676A patent/AT355027B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATA536676A (de)	1979-07-15
AT355027B (de)	1980-02-11
ZA764304B (en)	1978-03-29

Publication	Publication Date	Title
EP0471609B1 (de)	1996-11-27	Benzofuranderivate, Benzothiophene, Indole oder Indolizine, Verfahren zu ihrer Herstellung und diese enthaltende Zusammensetzungen
LU86032A1 (fr)	1986-02-18	Derive d'indole
MC1475A1 (fr)	1983-06-17	Procede de preparation de derives de la purine a action anti-virale
FR2534580A1 (fr)	1984-04-20	Derives de phenyl-1 piperidino-2 propanol, leur preparation, et medicaments qui les contiennent
FR2498601A1 (fr)	1982-07-30	Nouveaux chromannes substitues utiles notamment comme anti-inflammatoires
BE898278A (fr)	1984-05-22	Benzoxazines antipsychotiques.
LU80219A1 (fr)	1980-04-21	Procede de preparation de nouveaux 3-(2-hydroxy-4(substituant)-phenyl)-azacycloalcanes et d'un medicament les contenant
FR2669029A1 (fr)	1992-05-15	Nouveaux derives de la n-benzoyl proline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
MC1498A1 (fr)	1983-11-17	Procede de preparation de composes pyridyliques ayant une activite antihistaminique
US3922305A (en)	1975-11-25	Chemical compounds
CH661046A5 (fr)	1987-06-30	Derives de benzodioxinopyrrole et procedes de preparation.
JPH06135958A (ja)	1994-05-17	ベンゾシクロヘプテン誘導体及びその製法
CH647233A5 (fr)	1985-01-15	Composes de methylene-3-azetidine utiles comme medicaments et compositions therapeutiques les contenant.
BE1008622A3 (fr)	1996-06-04	Derives de l'epi-epibatidine.
LU81676A1 (fr)	1981-04-17	Nouveaux derives d'aurones,leur procede de preparation et leur utilisation comme produits pharmaceutiques
MC1156A1 (fr)	1978-04-17	Composes cycliques
BE844358A (fr)	1977-01-20	Nouvelles benzodiazepines, leur preparation et compositions pharmaceutiques les contenant
FR2463136A1 (fr)	1981-02-20	Nouveaux acides alcoxybenzofuranne-2-carboxyliques, leurs sels et esters, utiles notamment comme agents hypolipemiants, et leur procede de preparation
BE854655A (fr)	1977-11-16	9-hydroxyhexahydrobenzo (c) quinoleines et intermediaires de synthese
LU80720A1 (fr)	1980-01-22	Polyfluorohydroxyisopropyl carbostyriles bicycliques et tricycliques antihypertensifs,leur preparation et compositions pharmaceutiques les contenant
CA2036920A1 (fr)	1991-08-28	Sels de metaux alcalinoterreux d'oxa-polyacides leur procede de preparation et les compositions pharmaceutiques qui les contiennent
MC1562A1 (fr)	1984-11-12	Phenothiazines,leur procede de preparation et produits en contenant
BE839365R (fr)	1976-09-09	Derives de diazepine
MC1616A1 (fr)	1985-07-18	Derives d'imidazobenzodiazepine
US3978121A (en)	1976-08-31	5H Dibenzo[a,d]cycloheptene derivatives