DK169785B1 - 3-Substituerede-beta-carbolinderivater, analogifremgangsmåde til fremstilling af og lægemiddel indeholdende samme - Google Patents

3-Substituerede-beta-carbolinderivater, analogifremgangsmåde til fremstilling af og lægemiddel indeholdende samme Download PDF

Info

Publication number: DK169785B1
Authority: DK; Denmark
Prior art keywords: alkyl; residue; methoxymethyl; carboline; carboxylic acid
Prior art date: 1983-06-23

Application number

DK304484A

Other languages

Danish (da)

English (en)

Other versions

DK304484D0 (da

DK304484A (da

Inventor

Andreas Huth

Ralph Schmiechen

Dieter Seidelmann

Dieter Rahtz

Mogens Engelstoft

Claus Thyco Braestrup

Original Assignee

Schering Ag

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.)

1983-06-23

Filing date

1984-06-21

Publication date

1995-02-27

1984-06-21 Application filed by Schering Ag filed Critical Schering Ag

1984-06-21 Publication of DK304484D0 publication Critical patent/DK304484D0/da

1984-12-24 Publication of DK304484A publication Critical patent/DK304484A/da

1995-02-27 Application granted granted Critical

1995-02-27 Publication of DK169785B1 publication Critical patent/DK169785B1/da

Links

-1 3-Substituted-beta-carboline Chemical class 0.000 title claims abstract description 59
238000000034 method Methods 0.000 title claims abstract description 20
238000002360 preparation method Methods 0.000 title claims abstract description 6
239000003814 drug Substances 0.000 title claims description 4
229940079593 drug Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 34
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims abstract description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
125000001424 substituent group Chemical group 0.000 claims abstract description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 4
229910052794 bromium Inorganic materials 0.000 claims abstract 4
229910052801 chlorine Inorganic materials 0.000 claims abstract 4
239000000460 chlorine Substances 0.000 claims abstract 4
229910052731 fluorine Inorganic materials 0.000 claims abstract 4
239000011737 fluorine Substances 0.000 claims abstract 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 4
125000000217 alkyl group Chemical group 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 7
BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 6
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 3
125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 claims 3
125000001309 chloro group Chemical group Cl* 0.000 claims 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
125000002346 iodo group Chemical group I* 0.000 claims 1
AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical class N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 abstract description 7
210000003169 central nervous system Anatomy 0.000 abstract description 3
239000001257 hydrogen Substances 0.000 abstract description 3
229910052739 hydrogen Inorganic materials 0.000 abstract description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
150000005840 aryl radicals Chemical class 0.000 abstract 2
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000003277 amino group Chemical group 0.000 abstract 1
125000002648 azanetriyl group Chemical group *N(*)* 0.000 abstract 1
CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 abstract 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
229920006395 saturated elastomer Polymers 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
241000699670 Mus sp. Species 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 7
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
206010010904 Convulsion Diseases 0.000 description 5
239000007858 starting material Substances 0.000 description 5
ARLVFKCLBYUINL-UHFFFAOYSA-N 9h-pyrido[3,4-b]indole-3-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1C=NC(C(=O)O)=C2 ARLVFKCLBYUINL-UHFFFAOYSA-N 0.000 description 4
102000004300 GABA-A Receptors Human genes 0.000 description 4
108090000839 GABA-A Receptors Proteins 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
230000001773 anti-convulsant effect Effects 0.000 description 4
238000006073 displacement reaction Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229960002200 flunitrazepam Drugs 0.000 description 4
GADIKQPUNWAMEB-UHFFFAOYSA-N methyl 4-ethyl-6,7-dimethoxy-9H-pyrido[5,4-b]indole-3-carboxylate Chemical compound N1C2=CC(OC)=C(OC)C=C2C2=C1C=NC(C(=O)OC)=C2CC GADIKQPUNWAMEB-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000000126 substance Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
208000007101 Muscle Cramp Diseases 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
210000004556 brain Anatomy 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002168 ethanoic acid esters Chemical class 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012528 membrane Substances 0.000 description 3
WUHLVXDDBHWHLQ-UHFFFAOYSA-N pentazole Chemical compound N=1N=NNN=1 WUHLVXDDBHWHLQ-UHFFFAOYSA-N 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
KWPQTFXULUUCGD-UHFFFAOYSA-N 3,4,5,7,8,9,10,10a-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1CCN=CC2CCCCN21 KWPQTFXULUUCGD-UHFFFAOYSA-N 0.000 description 2
LDQHOKOOVPRRIZ-UHFFFAOYSA-N C1=CC(O)=C2C3=C(C)C(C(=O)OCC)=NC=C3NC2=C1 Chemical compound C1=CC(O)=C2C3=C(C)C(C(=O)OCC)=NC=C3NC2=C1 LDQHOKOOVPRRIZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
208000005392 Spasm Diseases 0.000 description 2
239000001961 anticonvulsive agent Substances 0.000 description 2
229960003965 antiepileptics Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000027455 binding Effects 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000002566 clonic effect Effects 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
239000013078 crystal Substances 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
NHPTYLXWUNPVSI-UHFFFAOYSA-N ethyl 6-hydroxy-4-methyl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C(O)C=C2C3=C(C)C(C(=O)OCC)=NC=C3NC2=C1 NHPTYLXWUNPVSI-UHFFFAOYSA-N 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
239000008101 lactose Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
210000004129 prosencephalon Anatomy 0.000 description 2
230000003578 releasing effect Effects 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
230000009870 specific binding Effects 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
XBDXMDVEZLOGMC-UHFFFAOYSA-N 1-(chloromethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(CCl)=C1 XBDXMDVEZLOGMC-UHFFFAOYSA-N 0.000 description 1
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical class N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 description 1
FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical compound OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 description 1
WBBVBAOXUSMRAR-UHFFFAOYSA-N 3-ethoxycarbonyl-4-(methoxymethyl)-5-phenylmethoxy-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole-1-carboxylic acid Chemical compound C=12C=3C(COC)C(C(=O)OCC)NC(C(O)=O)C=3NC2=CC=CC=1OCC1=CC=CC=C1 WBBVBAOXUSMRAR-UHFFFAOYSA-N 0.000 description 1
QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
229920000856 Amylose Polymers 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
MXKCQDWYVYUPDP-UHFFFAOYSA-N C1=CC(O)=C2C3=C(COC)C(C(=O)OCC)=NC=C3NC2=C1 Chemical compound C1=CC(O)=C2C3=C(COC)C(C(=O)OCC)=NC=C3NC2=C1 MXKCQDWYVYUPDP-UHFFFAOYSA-N 0.000 description 1
BLGDYGLSCSKQMB-UHFFFAOYSA-N C1=CC(O)=C2C3=C(OC)C(C(=O)OCC)=NC(C)=C3NC2=C1 Chemical compound C1=CC(O)=C2C3=C(OC)C(C(=O)OCC)=NC(C)=C3NC2=C1 BLGDYGLSCSKQMB-UHFFFAOYSA-N 0.000 description 1
IMIYVFAGCLBPLF-UHFFFAOYSA-N COCC1=CN=CC=2NC3=CC=CC=C3C12 Chemical compound COCC1=CN=CC=2NC3=CC=CC=C3C12 IMIYVFAGCLBPLF-UHFFFAOYSA-N 0.000 description 1
206010053398 Clonic convulsion Diseases 0.000 description 1
229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
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108010010803 Gelatin Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
CWPNRKVRLRXTRF-UHFFFAOYSA-N N1C2=CC=CC(O)=C2C2=C1C=NC(C(=O)OCC)=C2 Chemical compound N1C2=CC=CC(O)=C2C2=C1C=NC(C(=O)OCC)=C2 CWPNRKVRLRXTRF-UHFFFAOYSA-N 0.000 description 1
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NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
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PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
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POIXGDDEJHANNV-UHFFFAOYSA-N butyl 4-ethyl-6-[(3-fluorophenyl)methoxy]-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C3=C(CC)C(C(=O)OCCCC)=NC=C3NC2=CC=C1OCC1=CC=CC(F)=C1 POIXGDDEJHANNV-UHFFFAOYSA-N 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
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239000002775 capsule Substances 0.000 description 1
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150000001720 carbohydrates Chemical class 0.000 description 1
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238000004587 chromatography analysis Methods 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
238000010411 cooking Methods 0.000 description 1
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239000008298 dragée Substances 0.000 description 1
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239000003995 emulsifying agent Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
ACNVQODEPUXASS-UHFFFAOYSA-N ethyl 2-amino-4-methoxy-3-(4-phenylmethoxy-1h-indol-3-yl)butanoate Chemical compound C=12C(C(COC)C(N)C(=O)OCC)=CNC2=CC=CC=1OCC1=CC=CC=C1 ACNVQODEPUXASS-UHFFFAOYSA-N 0.000 description 1
JHAHMOGOJUKPSU-UHFFFAOYSA-N ethyl 4-(methoxymethyl)-5-[(2-methyl-3-nitrophenyl)methoxy]-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC=CC([N+]([O-])=O)=C1C JHAHMOGOJUKPSU-UHFFFAOYSA-N 0.000 description 1
IONKBRQNEZHTSJ-UHFFFAOYSA-N ethyl 4-(methoxymethyl)-5-[(3,4,5-trimethoxyphenyl)methoxy]-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC(OC)=C(OC)C(OC)=C1 IONKBRQNEZHTSJ-UHFFFAOYSA-N 0.000 description 1
DPDMLKMZMXEVRV-UHFFFAOYSA-N ethyl 4-(methoxymethyl)-5-[(4-methylphenyl)methoxy]-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC=C(C)C=C1 DPDMLKMZMXEVRV-UHFFFAOYSA-N 0.000 description 1
QHLFHFNDYQVTTA-UHFFFAOYSA-N ethyl 4-(methoxymethyl)-5-[[3-(trifluoromethyl)phenyl]methoxy]-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC=CC(C(F)(F)F)=C1 QHLFHFNDYQVTTA-UHFFFAOYSA-N 0.000 description 1
NMYOPHUDJZMSBM-UHFFFAOYSA-N ethyl 4-(methoxymethyl)-6-(4-methoxyphenoxy)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=C1OC1=CC=C(OC)C=C1 NMYOPHUDJZMSBM-UHFFFAOYSA-N 0.000 description 1
RQSIHRHFWJHKIE-UHFFFAOYSA-N ethyl 4-(methoxymethyl)-6-[(4-nitrophenyl)methoxy]-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=C1OCC1=CC=C([N+]([O-])=O)C=C1 RQSIHRHFWJHKIE-UHFFFAOYSA-N 0.000 description 1
WDXAOMXVRFQZKK-UHFFFAOYSA-N ethyl 4-ethyl-6-hydroxy-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C(O)C=C2C3=C(CC)C(C(=O)OCC)=NC=C3NC2=C1 WDXAOMXVRFQZKK-UHFFFAOYSA-N 0.000 description 1
NYOGIANDFFICOE-UHFFFAOYSA-N ethyl 4-methyl-5-[[3-(trifluoromethyl)phenyl]methoxy]-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(C)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC=CC(C(F)(F)F)=C1 NYOGIANDFFICOE-UHFFFAOYSA-N 0.000 description 1
SAZWIAPGNYNKDF-UHFFFAOYSA-N ethyl 5-[(2,4-dimethoxyphenyl)methoxy]-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC=C(OC)C=C1OC SAZWIAPGNYNKDF-UHFFFAOYSA-N 0.000 description 1
UWSDKNKOVQGTKX-UHFFFAOYSA-N ethyl 5-[(2,4-dimethoxyphenyl)methoxy]-4-methyl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(C)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC=C(OC)C=C1OC UWSDKNKOVQGTKX-UHFFFAOYSA-N 0.000 description 1
PAJTYYLQINXMLE-UHFFFAOYSA-N ethyl 5-[(2,5-dichlorophenyl)methoxy]-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC(Cl)=CC=C1Cl PAJTYYLQINXMLE-UHFFFAOYSA-N 0.000 description 1
ZOXBCPZVONPSAK-UHFFFAOYSA-N ethyl 5-[(2-chlorophenyl)methoxy]-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC=CC=C1Cl ZOXBCPZVONPSAK-UHFFFAOYSA-N 0.000 description 1
SAOIZGSYMZKZJN-UHFFFAOYSA-N ethyl 5-[(2-chlorophenyl)methoxy]-4-methyl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(C)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC=CC=C1Cl SAOIZGSYMZKZJN-UHFFFAOYSA-N 0.000 description 1
KEUFMJISMKZDIB-UHFFFAOYSA-N ethyl 5-[(2-fluorophenyl)methoxy]-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC=CC=C1F KEUFMJISMKZDIB-UHFFFAOYSA-N 0.000 description 1
JAFKEMQMZHRCPL-UHFFFAOYSA-N ethyl 5-[(3,4,5-trimethoxyphenyl)methoxy]-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC(C=23)=C1NC3=CC=CC=2OCC1=CC(OC)=C(OC)C(OC)=C1 JAFKEMQMZHRCPL-UHFFFAOYSA-N 0.000 description 1
IUXKHHPNPJFBHI-UHFFFAOYSA-N ethyl 5-[(3,5-dichlorophenyl)methoxy]-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC(Cl)=CC(Cl)=C1 IUXKHHPNPJFBHI-UHFFFAOYSA-N 0.000 description 1
RJQIMHZCVJRTAZ-UHFFFAOYSA-N ethyl 5-[(3-chlorophenyl)methoxy]-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC=CC(Cl)=C1 RJQIMHZCVJRTAZ-UHFFFAOYSA-N 0.000 description 1
IPBLPJOIJTWJFO-UHFFFAOYSA-N ethyl 5-[(3-fluorophenyl)methoxy]-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC(C=23)=C1NC3=CC=CC=2OCC1=CC=CC(F)=C1 IPBLPJOIJTWJFO-UHFFFAOYSA-N 0.000 description 1
YBICKRLMVSCRIM-UHFFFAOYSA-N ethyl 5-[(3-methoxyphenyl)methoxy]-4-methyl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(C)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC=CC(OC)=C1 YBICKRLMVSCRIM-UHFFFAOYSA-N 0.000 description 1
WEOFPUXMDDYZOQ-UHFFFAOYSA-N ethyl 5-[(4-chlorophenyl)methoxy]-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC=C(Cl)C=C1 WEOFPUXMDDYZOQ-UHFFFAOYSA-N 0.000 description 1
ARJRZUOPYYOBEF-UHFFFAOYSA-N ethyl 5-[(4-fluorophenyl)methoxy]-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=CC=1OCC1=CC=C(F)C=C1 ARJRZUOPYYOBEF-UHFFFAOYSA-N 0.000 description 1
BDRVEEMPWMQMOI-UHFFFAOYSA-N ethyl 6-[(3-chlorophenyl)methoxy]-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C3=C(COC)C(C(=O)OCC)=NC=C3NC2=CC=C1OCC1=CC=CC(Cl)=C1 BDRVEEMPWMQMOI-UHFFFAOYSA-N 0.000 description 1
WCKROYDVSIHZLK-UHFFFAOYSA-N ethyl 6-hydroxy-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound N1C2=CC=C(O)C=C2C2=C1C=NC(C(=O)OCC)=C2 WCKROYDVSIHZLK-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000011152 fibreglass Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 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
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
IPHHFRIGRLIUCZ-UHFFFAOYSA-N methyl 6-[(4-chlorophenyl)methoxy]-4-ethyl-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=C2C=3C(CC)=C(C(=O)OC)N=CC=3NC2=CC=C1OCC1=CC=C(Cl)C=C1 IPHHFRIGRLIUCZ-UHFFFAOYSA-N 0.000 description 1
RLZPCFQNZGINRP-UHFFFAOYSA-N n'-hydroxypropanimidamide Chemical compound CCC(N)=NO RLZPCFQNZGINRP-UHFFFAOYSA-N 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
230000007935 neutral effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229960005152 pentetrazol Drugs 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
RRHZOLPNBLIBKH-UHFFFAOYSA-N propyl 5-[(4-chlorophenyl)methoxy]-4-(methoxymethyl)-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C=12C3=C(COC)C(C(=O)OCCC)=NC=C3NC2=CC=CC=1OCC1=CC=C(Cl)C=C1 RRHZOLPNBLIBKH-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000003345 scintillation counting Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000012222 talc Nutrition 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
238000005809 transesterification reaction Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Life Sciences & Earth Sciences (AREA)
Neurosurgery (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Diaphragms For Electromechanical Transducers (AREA)
Treating Waste Gases (AREA)
Photoreceptors In Electrophotography (AREA)

DK304484A 1983-06-23 1984-06-21 3-Substituerede-beta-carbolinderivater, analogifremgangsmåde til fremstilling af og lægemiddel indeholdende samme DK169785B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3322895		1983-06-23
DE19833322895 DE3322895A1 (de)	1983-06-23	1983-06-23	Neue ss-carboline, verfahren zur ihrer herstellung und ihre verwendung als arzneimittel (s)

Publications (3)

Publication Number	Publication Date
DK304484D0 DK304484D0 (da)	1984-06-21
DK304484A DK304484A (da)	1984-12-24
DK169785B1 true DK169785B1 (da)	1995-02-27

Family

ID=6202362

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK304484A DK169785B1 (da)	1983-06-23	1984-06-21	3-Substituerede-beta-carbolinderivater, analogifremgangsmåde til fremstilling af og lægemiddel indeholdende samme

Country Status (17)

Country	Link
US (1)	US4894377A (fr)
EP (1)	EP0130140B1 (fr)
JP (1)	JPS6013790A (fr)
AT (1)	ATE60332T1 (fr)
AU (1)	AU575566B2 (fr)
CA (1)	CA1254895A (fr)
DE (2)	DE3322895A1 (fr)
DK (1)	DK169785B1 (fr)
ES (1)	ES8502998A1 (fr)
FI (1)	FI79109C (fr)
GR (1)	GR82124B (fr)
HU (1)	HU190573B (fr)
IE (1)	IE57623B1 (fr)
IL (1)	IL72165A (fr)
NO (1)	NO160612C (fr)
SU (2)	SU1376946A3 (fr)
ZA (1)	ZA844767B (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3240514A1 (de) *	1982-10-29	1984-05-03	Schering AG, 1000 Berlin und 4709 Bergkamen	Ss-carboline, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate
DE3504045A1 (de) *	1985-02-04	1986-08-07	Schering AG, 1000 Berlin und 4709 Bergkamen	Verfahren zur herstellung von ss-carbolinen durch dehydrierung
DE3540654A1 (de) *	1985-11-13	1987-05-14	Schering Ag	Phenoxy-substituierte ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel
DE3540653A1 (de) *	1985-11-13	1987-05-14	Schering Ag	Neue 3-oxadiazol- und 3-carbonsaeure-ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel
DE3545776A1 (de) *	1985-12-20	1987-06-25	Schering Ag	5-aminoalkyl-ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel
US4952584A (en) *	1986-01-11	1990-08-28	Beecham Group P.L.C.	9H-pyrido[2,B-8]indole-3-carboxylic acid ester compounds having useful pharmaceutical activity
DE3609699A1 (de) *	1986-03-20	1987-09-24	Schering Ag	5- oder 6-substituierte-(beta)-carbolin-3-carbonsaeureester
DE3608089A1 (de) *	1986-03-08	1987-09-10	Schering Ag	Heteroaryl-oxy-ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel
AU619203B2 (en) *	1987-08-28	1992-01-23	Schering Aktiengesellschaft	Isoxazole-beta-carboline derivatives
DE4029389A1 (de) *	1990-09-13	1992-03-26	Schering Ag	Verfahren zur herstellung von (beta)-carbolin-derivaten
DE4109342A1 (de) *	1991-03-19	1992-09-24	Schering Ag	Selektive phenylierung von 5-hydroxy-ss-carbolinderivaten
US5350750A (en) *	1991-04-27	1994-09-27	Schering Aktiengesellschaft	β-carboline-3-hydroxyalkylcarboxylic acid ester derivatives, process for their production and their use in pharmaceutical agents
US5543519A (en) *	1991-06-15	1996-08-06	Schering Aktiengesellschaft	3-aryl or 3-hetaryl-β-carbolines, their production and use in pharmaceutical agents
DE4120109A1 (de) *	1991-06-15	1992-12-17	Schering Ag	3-aryl- oder 3-hetaryl-(beta)-carboline, deren herstellung und verwendung in arzneimitteln
DE19514524A1 (de) *	1995-04-12	1996-10-17	Schering Ag	Anellierte beta-Carboline
FR2754262B1 (fr) *	1996-10-08	1998-10-30	Synthelabo	Derives de 1h-pyrido[3,4-b]indole-4-carboxamide, leur preparation et leur application en therapeutique

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3023567A1 (de) *	1980-06-20	1982-01-21	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Substituierte (beta) -carbolin-3-carbonsaeurederivate
NZ194747A (en) *	1979-08-29	1988-11-29	Schering Ag	9h-pyrido(3,4-b)indol-3-ylcarboxylic acid derivatives
DE3136857A1 (de) *	1981-09-14	1983-03-31	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Substituierte (beta)-carbolin-3-carbonsaeurealkylester, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE3048318A1 (de) *	1980-12-17	1982-07-22	Schering Ag, 1000 Berlin Und 4619 Bergkamen	4-alkoxyalkyl substituierte (beta)-carbolin-3-carbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
JPS57123180A (en) *	1980-12-17	1982-07-31	Schering Ag	3-substituted beta-carboline, manufacture and psychotropic drug containing same
DE3240511A1 (de) *	1982-10-29	1984-05-03	Schering AG, 1000 Berlin und 4709 Bergkamen	Verfahren zur herstellung von ss-carbolinderivaten
DE3240514A1 (de) *	1982-10-29	1984-05-03	Schering AG, 1000 Berlin und 4709 Bergkamen	Ss-carboline, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate
DK149270C (da) *	1983-05-27	1986-08-25	Schering Ag	Analogifremgangsmaade til fremstilling af beta-carbolin-3-carboxylsyrederivater

1983
- 1983-06-23 DE DE19833322895 patent/DE3322895A1/de not_active Withdrawn
1984
- 1984-06-07 SU SU843747801A patent/SU1376946A3/ru active
- 1984-06-13 ES ES533377A patent/ES8502998A1/es not_active Expired
- 1984-06-20 AU AU29552/84A patent/AU575566B2/en not_active Ceased
- 1984-06-20 IL IL72165A patent/IL72165A/xx not_active IP Right Cessation
- 1984-06-20 FI FI842499A patent/FI79109C/fi not_active IP Right Cessation
- 1984-06-20 NO NO842483A patent/NO160612C/no unknown
- 1984-06-21 DE DE8484730069T patent/DE3483980D1/de not_active Expired - Lifetime
- 1984-06-21 EP EP84730069A patent/EP0130140B1/fr not_active Expired - Lifetime
- 1984-06-21 DK DK304484A patent/DK169785B1/da active
- 1984-06-21 AT AT84730069T patent/ATE60332T1/de not_active IP Right Cessation
- 1984-06-21 GR GR75074A patent/GR82124B/el unknown
- 1984-06-22 JP JP59127677A patent/JPS6013790A/ja active Granted
- 1984-06-22 CA CA000457217A patent/CA1254895A/fr not_active Expired
- 1984-06-22 HU HU842433A patent/HU190573B/hu not_active IP Right Cessation
- 1984-06-22 IE IE1573/84A patent/IE57623B1/en not_active IP Right Cessation
- 1984-06-22 ZA ZA844767A patent/ZA844767B/xx unknown
1985
- 1985-10-25 SU SU853967804A patent/SU1428202A3/ru active
1987
- 1987-01-14 US US07/003,179 patent/US4894377A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ZA844767B (en)	1985-02-27
FI842499A7 (fi)	1984-12-24
AU2955284A (en)	1985-01-03
NO160612C (no)	1989-05-10
FI79109B (fi)	1989-07-31
JPH0585552B2 (fr)	1993-12-07
ATE60332T1 (de)	1991-02-15
EP0130140A2 (fr)	1985-01-02
SU1376946A3 (ru)	1988-02-23
IE57623B1 (en)	1993-02-10
EP0130140A3 (en)	1985-09-25
GR82124B (fr)	1984-12-13
HUT34484A (en)	1985-03-28
CA1254895A (fr)	1989-05-30
ES533377A0 (es)	1985-02-16
DK304484D0 (da)	1984-06-21
DE3483980D1 (de)	1991-02-28
EP0130140B1 (fr)	1991-01-23
DK304484A (da)	1984-12-24
IL72165A0 (en)	1984-10-31
AU575566B2 (en)	1988-08-04
IL72165A (en)	1987-11-30
FI79109C (fi)	1989-11-10
JPS6013790A (ja)	1985-01-24
SU1428202A3 (ru)	1988-09-30
NO160612B (no)	1989-01-30
ES8502998A1 (es)	1985-02-16
NO842483L (no)	1984-12-27
US4894377A (en)	1990-01-16
DE3322895A1 (de)	1985-01-03
FI842499A0 (fi)	1984-06-20
IE841573L (en)	1984-12-23
HU190573B (en)	1986-09-29

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CA1264748A (fr)	1990-01-23	Derives de .beta.-carboline-3-oxadiazolyl; preparation et utilisation
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JPS58167573A (ja)	1983-10-03	新規な６−アリ−ル−４，５−ジヒドロ−３（２ｈ）−ピリダジノン、その製法及び用途