DD252829A5 - Verfahren zur herstellung von 5-aminoalkyl-beta-corbelinderivaten - Google Patents

Verfahren zur herstellung von 5-aminoalkyl-beta-corbelinderivaten Download PDF

Info

Publication number: DD252829A5
Authority: DD; German Democratic Republic
Prior art keywords: carboline; methoxymethyl; carboxylic acid; compound; ethyl ester
Prior art date: 1985-12-20

Application number

DD86297796A

Other languages

German (de)

English (en)

Inventor

Helmut Biere

Andreas Huth

Dieter Rahtz

Ralph Schmiechen

Dieter Seidelmann

Norman D Stephens

Original Assignee

��@��k��

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.)

1985-12-20

Filing date

1986-12-17

Publication date

1987-12-30

1986-12-17 Application filed by ��@��k�� filed Critical ��@��k��

1987-12-30 Publication of DD252829A5 publication Critical patent/DD252829A5/de

Links

238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 53
238000000034 method Methods 0.000 claims abstract description 19
230000008569 process Effects 0.000 claims abstract description 10
-1 Methoxymethyl- Chemical group 0.000 claims description 35
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
230000000144 pharmacologic effect Effects 0.000 abstract description 6
210000003169 central nervous system Anatomy 0.000 abstract description 5
238000002360 preparation method Methods 0.000 abstract description 5
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
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239000000243 solution Substances 0.000 description 33
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
238000002844 melting Methods 0.000 description 19
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238000006243 chemical reaction Methods 0.000 description 10
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238000006073 displacement reaction Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
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150000003254 radicals Chemical class 0.000 description 4
238000010992 reflux Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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239000007868 Raney catalyst Substances 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
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 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
210000004556 brain Anatomy 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
230000036461 convulsion Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
WUHLVXDDBHWHLQ-UHFFFAOYSA-N pentazole Chemical compound N=1N=NNN=1 WUHLVXDDBHWHLQ-UHFFFAOYSA-N 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000003586 protic polar solvent Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
238000005809 transesterification reaction Methods 0.000 description 3
239000008096 xylene Substances 0.000 description 3
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 2
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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241001465754 Metazoa Species 0.000 description 2
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125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
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XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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IPXLBHWDFKMYSU-UHFFFAOYSA-N ethyl 3-[4-(acetyloxymethyl)-1h-indol-3-yl]-2-amino-4-methoxybutanoate Chemical compound C1=CC(COC(C)=O)=C2C(C(COC)C(N)C(=O)OCC)=CNC2=C1 IPXLBHWDFKMYSU-UHFFFAOYSA-N 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
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229960003965 antiepileptics Drugs 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
150000001557 benzodiazepines Chemical class 0.000 description 1
230000027455 binding Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003518 caustics Substances 0.000 description 1
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 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000002566 clonic effect Effects 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
229960003529 diazepam Drugs 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000000975 dye 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
206010015037 epilepsy Diseases 0.000 description 1
RZFMEJAFFIWDCT-UHFFFAOYSA-N ethyl 3-[4-(acetyloxymethyl)-1h-indol-3-yl]-4-methoxy-2-nitrobutanoate Chemical compound C1=CC(COC(C)=O)=C2C(C(COC)C(C(=O)OCC)[N+]([O-])=O)=CNC2=C1 RZFMEJAFFIWDCT-UHFFFAOYSA-N 0.000 description 1
PWSUKFLQJCMJMP-UHFFFAOYSA-N ethyl 5-[(4-methylpiperazin-1-yl)methyl]-9h-pyrido[3,4-b]indole-3-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC(C=23)=C1NC3=CC=CC=2CN1CCN(C)CC1 PWSUKFLQJCMJMP-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
235000019253 formic acid Nutrition 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
239000011521 glass Substances 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
150000007928 imidazolide derivatives Chemical class 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000011630 iodine 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
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000036640 muscle relaxation Effects 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
150000002828 nitro derivatives Chemical class 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000004866 oxadiazoles Chemical class 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000011181 potassium carbonates Nutrition 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
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000003345 scintillation counting Methods 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 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
208000019116 sleep disease Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000011182 sodium carbonates Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
208000018198 spasticity Diseases 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 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
- 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
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- 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

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Anesthesiology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Fats And Perfumes (AREA)
Braking Arrangements (AREA)
Liquid Developers In Electrophotography (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD86297796A 1985-12-20 1986-12-17 Verfahren zur herstellung von 5-aminoalkyl-beta-corbelinderivaten DD252829A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853545776 DE3545776A1 (de)	1985-12-20	1985-12-20	5-aminoalkyl-ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel

Publications (1)

Publication Number	Publication Date
DD252829A5 true DD252829A5 (de)	1987-12-30

Family

ID=6289387

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86297796A DD252829A5 (de)	1985-12-20	1986-12-17	Verfahren zur herstellung von 5-aminoalkyl-beta-corbelinderivaten

Country Status (17)

Country	Link
US (2)	US4731365A (da)
EP (1)	EP0232675B1 (da)
JP (1)	JPH0780878B2 (da)
AT (1)	ATE58536T1 (da)
AU (1)	AU597923B2 (da)
CA (1)	CA1277319C (da)
DD (1)	DD252829A5 (da)
DE (2)	DE3545776A1 (da)
DK (1)	DK165878C (da)
ES (1)	ES2031457T3 (da)
FI (1)	FI82245C (da)
GR (1)	GR3001468T3 (da)
HU (1)	HU195656B (da)
IE (1)	IE59757B1 (da)
IL (1)	IL81003A (da)
NO (1)	NO165106C (da)
PT (1)	PT83975B (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP4144707A1 (de)	2021-09-07	2023-03-08	Biolac GmbH & Co. KG	Mischung zur herstellung eines formkörpers mit verbessertem bindemittel

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3609699A1 (de) *	1986-03-20	1987-09-24	Schering Ag	5- oder 6-substituierte-(beta)-carbolin-3-carbonsaeureester
DE4130933A1 (de) *	1991-09-13	1993-03-18	Schering Ag	Neue (beta)-carbolinderivate, deren herstellung und verwendung in arzneimitteln
DE4212529A1 (de) *	1992-04-10	1993-10-14	Schering Ag	Verwendung von µ-Carbolinen als nicht-kompetitive Glutamat-Antagonisten
DE4330175A1 (de) *	1993-08-31	1995-03-02	Schering Ag	Alkoxy-substituierte beta-Carboline

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ194747A (en) *	1979-08-29	1988-11-29	Schering Ag	9h-pyrido(3,4-b)indol-3-ylcarboxylic acid derivatives
JPS57123180A (en) *	1980-12-17	1982-07-31	Schering Ag	3-substituted beta-carboline, manufacture and psychotropic drug containing same
DE3322894A1 (de) *	1983-06-23	1985-01-03	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue (beta)-carboline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel (h)
DE3322895A1 (de) *	1983-06-23	1985-01-03	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue ss-carboline, verfahren zur ihrer herstellung und ihre verwendung als arzneimittel (s)
DE3335323A1 (de) *	1983-09-27	1985-04-04	Schering AG, 1000 Berlin und 4709 Bergkamen	Substituierte ss-carboline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DK240084D0 (da) *	1984-05-15	1984-05-15	Ferrosan As	New beta-carboline-3-oxadiazolyl derivatives
DE3504045A1 (de) *	1985-02-04	1986-08-07	Schering AG, 1000 Berlin und 4709 Bergkamen	Verfahren zur herstellung von ss-carbolinen durch dehydrierung

1985
- 1985-12-20 DE DE19853545776 patent/DE3545776A1/de not_active Withdrawn
1986
- 1986-12-16 IL IL81003A patent/IL81003A/xx not_active IP Right Cessation
- 1986-12-17 DD DD86297796A patent/DD252829A5/de not_active IP Right Cessation
- 1986-12-17 DK DK610586A patent/DK165878C/da active
- 1986-12-18 JP JP61300219A patent/JPH0780878B2/ja not_active Expired - Lifetime
- 1986-12-19 DE DE8686730212T patent/DE3675758D1/de not_active Expired - Lifetime
- 1986-12-19 PT PT83975A patent/PT83975B/pt not_active IP Right Cessation
- 1986-12-19 NO NO865180A patent/NO165106C/no unknown
- 1986-12-19 CA CA000525874A patent/CA1277319C/en not_active Expired - Lifetime
- 1986-12-19 AT AT86730212T patent/ATE58536T1/de not_active IP Right Cessation
- 1986-12-19 EP EP86730212A patent/EP0232675B1/de not_active Expired - Lifetime
- 1986-12-19 HU HU865361A patent/HU195656B/hu not_active IP Right Cessation
- 1986-12-19 FI FI865234A patent/FI82245C/fi not_active IP Right Cessation
- 1986-12-19 ES ES198686730212T patent/ES2031457T3/es not_active Expired - Lifetime
- 1986-12-19 AU AU66797/86A patent/AU597923B2/en not_active Ceased
- 1986-12-19 IE IE332986A patent/IE59757B1/en not_active IP Right Cessation
- 1986-12-22 US US06/944,165 patent/US4731365A/en not_active Expired - Fee Related
1987
- 1987-12-08 US US07/130,049 patent/US4757070A/en not_active Expired - Fee Related
1991
- 1991-02-12 GR GR90400958T patent/GR3001468T3/el not_active IP Right Cessation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP4144707A1 (de)	2021-09-07	2023-03-08	Biolac GmbH & Co. KG	Mischung zur herstellung eines formkörpers mit verbessertem bindemittel

Also Published As

Publication number	Publication date
US4731365A (en)	1988-03-15
HUT43068A (en)	1987-09-28
JPS62195378A (ja)	1987-08-28
IL81003A0 (en)	1987-03-31
IE863329L (en)	1987-06-20
AU597923B2 (en)	1990-06-14
NO865180L (no)	1987-06-22
DE3675758D1 (de)	1991-01-03
DK610586D0 (da)	1986-12-17
NO865180D0 (no)	1986-12-19
DK165878C (da)	1993-06-21
DK165878B (da)	1993-02-01
ES2031457T3 (es)	1992-12-16
FI82245B (fi)	1990-10-31
CA1277319C (en)	1990-12-04
ATE58536T1 (de)	1990-12-15
AU6679786A (en)	1987-06-25
EP0232675B1 (de)	1990-11-22
DE3545776A1 (de)	1987-06-25
FI865234A7 (fi)	1987-06-21
IL81003A (en)	1990-04-29
JPH0780878B2 (ja)	1995-08-30
FI865234A0 (fi)	1986-12-19
NO165106B (no)	1990-09-17
NO165106C (no)	1990-12-27
US4757070A (en)	1988-07-12
HU195656B (en)	1988-06-28
IE59757B1 (en)	1994-03-23
EP0232675A1 (de)	1987-08-19
FI82245C (fi)	1991-02-11
PT83975B (pt)	1989-05-12
DK610586A (da)	1987-06-21
PT83975A (en)	1987-01-01
GR3001468T3 (en)	1992-10-08

Legal Events

Date	Code	Title	Description
1995-12-07	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE19834047A1 (de)	2000-02-03	Substituierte Pyrazolderivate
EP0338331A1 (de)	1989-10-25	1,3-Disubstituierte Pyrrolidine
EP0944631A1 (de)	1999-09-29	Neue substituierte pyrazolderivate zur behandlung von herzkreislauferkrankungen
DE3833008A1 (de)	1990-04-05	Pyrrolocarbozol-derivate, verfahren zu deren herstellung und deren verwendung als arzneimittel
EP0271040A2 (de)	1988-06-15	Neue Pyrrolobenzimidazole, Verfahren zu ihrer Herstellung, sowie Arzneimittel
EP0222693A2 (de)	1987-05-20	Neue 3-Oxadiazol- und 3-Carbonsäure-beta-Carbolinderivate, ihre Herstellung und ihre Verwendung als Arzneimittel
AT395009B (de)	1992-08-25	Verfahren zur herstellung neuer 1-(hydroxystyryl)-5h-2,3-benzodiazepin-derivate
EP0237467B1 (de)	1992-10-28	Hetaryl-oxy-beta-carbolinderivate, ihre Herstellung und Verwendung als Arzneimittel
EP0282502B1 (de)	1991-05-15	Imidazol-derivate
EP0130141B1 (de)	1990-09-12	Neue beta-Carboline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel (H)
EP0234173B1 (de)	1993-06-16	Phenoxy-substituierte beta-Carbolinderivate, ihre Herstellung und ihre Verwendung als Arzneimittel
EP0232675B1 (de)	1990-11-22	5-Aminoalkyl-Beta-Carbolinderivate, ihre Herstellung und Verwendung als Arzneimittel
EP0217737B1 (de)	1991-08-14	Tetrahydro-beta-carboline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0233483A2 (de)	1987-08-26	Pyrrolo[1,2-a][4,1]benzoxazepine, Verfahren zur ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen, sowie therapeutische Verwendung
EP0025501B1 (de)	1982-12-29	Neue N-Aminoalkylindol-Derivate und ihre Salze; Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0167045A1 (de)	1986-01-08	Benzo (c)(1,8)naphthyridine, Verfahren zu ihrer Herstellung und ihre Verwendung sowie diese Verbindungen enthaltende Zubereitungen
EP0301245B1 (de)	1993-09-08	3-Sulfonyl-3,7-diazabicyclo-(3,3,1)nonan-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
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DD252829A5 - Verfahren zur herstellung von 5-aminoalkyl-beta-corbelinderivaten - Google Patents

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