CH634321A5 - trans-5-Aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles, process for their preparation and pharmaceutical composition containing them - Google Patents

trans-5-Aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles, process for their preparation and pharmaceutical composition containing them Download PDF

Info

Publication number: CH634321A5
Authority: CH; Switzerland
Prior art keywords: fluoro; hexahydro; pyrido; indole; fluorophenyl
Prior art date: 1977-05-23

Application number

CH552678A

Other languages

English (en)

French (fr)

Inventor

Willard Mckowan Jun Welch

Original Assignee

Pfizer

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.)

1977-05-23

Filing date

1978-05-22

Publication date

1983-01-31

1978-05-22 Application filed by Pfizer filed Critical Pfizer

1983-01-31 Publication of CH634321A5 publication Critical patent/CH634321A5/fr

Links

238000000034 method Methods 0.000 title claims description 25
230000008569 process Effects 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 10
150000002475 indoles Chemical class 0.000 title claims description 5
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 67
-1 trans-5-phenyl-2- (4-hydroxy-phenylbutyl) -2,3,4,4a, 5,9b-hexa-hydro-1H-pyrido [4,3-b] indole Chemical compound 0.000 claims description 38
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 31
150000003839 salts Chemical class 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 23
239000002904 solvent Substances 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 11
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 10
125000001153 fluoro group Chemical group F* 0.000 claims description 10
239000003960 organic solvent Substances 0.000 claims description 10
239000011541 reaction mixture Substances 0.000 claims description 10
229910000085 borane Inorganic materials 0.000 claims description 9
239000012280 lithium aluminium hydride Substances 0.000 claims description 8
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
230000000698 schizophrenic effect Effects 0.000 claims description 3
239000007800 oxidant agent Substances 0.000 claims description 2
AWISSRZCWPZUAC-JYFHCDHNSA-N (4ar,9br)-8-fluoro-5-(2-fluorophenyl)-2-[4-(4-fluorophenyl)but-3-enyl]-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indole Chemical compound C1=CC(F)=CC=C1C=CCCN1C[C@@H](C=2C(=CC=C(F)C=2)N2C=3C(=CC=CC=3)F)[C@H]2CC1 AWISSRZCWPZUAC-JYFHCDHNSA-N 0.000 claims 1
UCFNSWNHHHLIAY-FUHWJXTLSA-N (4ar,9br)-8-fluoro-5-(4-fluorophenyl)-2-methyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indole Chemical compound C1([C@H]2[C@H]3CCN(C2)C)=CC(F)=CC=C1N3C1=CC=C(F)C=C1 UCFNSWNHHHLIAY-FUHWJXTLSA-N 0.000 claims 1
YYTDSKXSYPHJOS-YABLSAKWSA-N 4-[(4ar,9br)-5-phenyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indol-2-yl]-1-(4-fluorophenyl)butan-1-ol Chemical compound C1([C@H]2[C@H]3CCN(C2)CCCC(O)C=2C=CC(F)=CC=2)=CC=CC=C1N3C1=CC=CC=C1 YYTDSKXSYPHJOS-YABLSAKWSA-N 0.000 claims 1
PUKLPXOUAIYTPA-AZGAKELHSA-N 4-[(4ar,9br)-5-phenyl-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indol-2-yl]-1-(4-fluorophenyl)butan-1-one Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1C[C@@H](C=2C(=CC=CC=2)N2C=3C=CC=CC=3)[C@H]2CC1 PUKLPXOUAIYTPA-AZGAKELHSA-N 0.000 claims 1
HVWWOIDJLSKQLV-YABLSAKWSA-N 4-[(4ar,9br)-8-fluoro-5-(4-fluorophenyl)-3,4,4a,9b-tetrahydro-1h-pyrido[4,3-b]indol-2-yl]-1-(4-fluorophenyl)butan-1-ol Chemical compound C1([C@H]2[C@H]3CCN(C2)CCCC(O)C=2C=CC(F)=CC=2)=CC(F)=CC=C1N3C1=CC=C(F)C=C1 HVWWOIDJLSKQLV-YABLSAKWSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
239000000203 mixture Substances 0.000 description 46
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
239000000047 product Substances 0.000 description 37
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
239000000725 suspension Substances 0.000 description 19
230000002936 tranquilizing effect Effects 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
238000010992 reflux Methods 0.000 description 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
239000003204 tranquilizing agent Substances 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 12
238000001914 filtration Methods 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
239000012458 free base Substances 0.000 description 11
239000007787 solid Substances 0.000 description 10
239000007858 starting material Substances 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical group CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 9
238000001704 evaporation Methods 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
230000009467 reduction Effects 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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 8
230000015572 biosynthetic process Effects 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
229940025084 amphetamine Drugs 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
230000000694 effects Effects 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
KMQLIDDEQAJAGJ-UHFFFAOYSA-N 4-oxo-4-phenylbutyric acid Chemical class OC(=O)CCC(=O)C1=CC=CC=C1 KMQLIDDEQAJAGJ-UHFFFAOYSA-N 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
229940117975 chromium trioxide Drugs 0.000 description 4
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 4
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000007789 gas Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
RDMFHRSPDKWERA-UHFFFAOYSA-N 5H-Pyrido[4,3-b]indole Chemical class C1=NC=C2C3=CC=CC=C3NC2=C1 RDMFHRSPDKWERA-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
230000006399 behavior Effects 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000006264 debenzylation reaction Methods 0.000 description 3
238000010586 diagram Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000000638 solvent extraction Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
BPPMRCNUQCVVFJ-UHFFFAOYSA-N 2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound N1C2=CC=CC=C2C2C1CCNC2 BPPMRCNUQCVVFJ-UHFFFAOYSA-N 0.000 description 2
BAPCUXNMDQTRAW-UHFFFAOYSA-N 2-benzyl-5-phenyl-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C=1C=CC=CC=1CN(C1)CCC2=C1C1=CC=CC=C1N2C1=CC=CC=C1 BAPCUXNMDQTRAW-UHFFFAOYSA-N 0.000 description 2
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
SHKWSBAVRQZYLE-UHFFFAOYSA-N 5-oxo-5-phenylpentanoic acid Chemical class OC(=O)CCCC(=O)C1=CC=CC=C1 SHKWSBAVRQZYLE-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
244000166102 Eucalyptus leucoxylon Species 0.000 description 2
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
241001465754 Metazoa Species 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
150000007514 bases Chemical class 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 2
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000006260 foam Substances 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
239000008101 lactose Substances 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
150000004031 phenylhydrazines Chemical class 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000002243 precursor Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
230000009466 transformation Effects 0.000 description 2
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
BPPMRCNUQCVVFJ-GXSJLCMTSA-N (4ar,9br)-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical class N1C2=CC=CC=C2[C@H]2[C@H]1CCNC2 BPPMRCNUQCVVFJ-GXSJLCMTSA-N 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 description 1
VLGVSQZQQGRTDA-UHFFFAOYSA-N 2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole hydrochloride Chemical compound Cl.N1C2=CC=CC=C2C2C1CCNC2 VLGVSQZQQGRTDA-UHFFFAOYSA-N 0.000 description 1
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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239000002184 metal Substances 0.000 description 1
QRNDDJXJUHBGSG-UHFFFAOYSA-N methoxyethyne Chemical group COC#C QRNDDJXJUHBGSG-UHFFFAOYSA-N 0.000 description 1
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239000012452 mother liquor Substances 0.000 description 1
IXRNQIKIVWWFBH-UHFFFAOYSA-N n-(1-phenylethenyl)acetamide Chemical compound CC(=O)NC(=C)C1=CC=CC=C1 IXRNQIKIVWWFBH-UHFFFAOYSA-N 0.000 description 1
239000003176 neuroleptic agent Substances 0.000 description 1
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OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
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BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
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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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Neurosurgery (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Psychiatry (AREA)
Anesthesiology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH552678A 1977-05-23 1978-05-22 trans-5-Aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles, process for their preparation and pharmaceutical composition containing them CH634321A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US79939277A	1977-05-23	1977-05-23

Publications (1)

Publication Number	Publication Date
CH634321A5 true CH634321A5 (en)	1983-01-31

Family

ID=25175793

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH552678A CH634321A5 (en)	1977-05-23	1978-05-22	trans-5-Aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles, process for their preparation and pharmaceutical composition containing them

Country Status (31)

Country	Link
JP (1)	JPS53144600A (de)
AR (2)	AR217688A1 (de)
AT (1)	AT368995B (de)
AU (1)	AU499618B1 (de)
BE (1)	BE867249A (de)
CA (1)	CA1094071A (de)
CH (1)	CH634321A5 (de)
CS (1)	CS207612B2 (de)
DD (4)	DD145536A5 (de)
DE (1)	DE2822465C2 (de)
DK (1)	DK226678A (de)
EG (1)	EG13590A (de)
FI (1)	FI63402C (de)
FR (1)	FR2392023A1 (de)
GB (1)	GB1586655A (de)
GR (1)	GR69985B (de)
HU (3)	HU185009B (de)
IE (1)	IE46975B1 (de)
IL (1)	IL54755A (de)
IT (1)	IT1096307B (de)
LU (1)	LU79684A1 (de)
NL (1)	NL7804210A (de)
NO (2)	NO150204C (de)
NZ (1)	NZ187333A (de)
PH (1)	PH13756A (de)
PL (5)	PL116944B1 (de)
PT (1)	PT68058B (de)
SE (2)	SE441448B (de)
SU (4)	SU873883A3 (de)
YU (4)	YU91478A (de)
ZA (1)	ZA782918B (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE20204239U1 (de)	2002-03-16	2002-05-29	Funke Kunststoffe GmbH, 48324 Sendenhorst	Universal-Rohrdichtung

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4224329A (en) *	1979-01-23	1980-09-23	Pfizer Inc.	2-Substituted-trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles
US4451655A (en) *	1982-05-17	1984-05-29	Pfizer Inc.	Process for preparing carboline derivatives and compounds used in their preparation
RU2106864C1 (ru) *	1995-10-23	1998-03-20	Николай Серафимович Зефиров	Средство для лечения болезни альцгеймера
SE9604786D0 (sv)	1996-12-20	1996-12-20	Astra Pharma Inc	New compounds
US6974825B1 (en)	1996-12-20	2005-12-13	Astrazeneca Canada Inc.	Compounds with analgesic effect
SE9904675D0 (sv)	1999-12-20	1999-12-20	Astra Pharma Inc	Novel compounds
SE0101769D0 (sv)	2001-05-18	2001-05-18	Astrazeneca Ab	Novel compounds
SE0101771D0 (sv)	2001-05-18	2001-05-18	Astrazeneca Ab	Novel compounds
SE0101773D0 (sv)	2001-05-18	2001-05-18	Astrazeneca Ab	Novel compounds
SE0101770D0 (sv)	2001-05-18	2001-05-18	Astrazeneca Ab	Novel compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR205452A1 (es) *	1973-12-06	1976-05-07	Endo Lab	Metodo para preparar nuevos trans-2, 3, 4, 4a, 5, 9b-hexahidro-5-fenil-1h-pirido(4,3-b) indoles
JPS50126699A (de) *	1974-03-20	1975-10-04
US4001263A (en) *	1974-04-01	1977-01-04	Pfizer Inc.	5-Aryl-1,2,3,4-tetrahydro-γ-carbolines

1978
- 1978-03-30 SE SE7803625A patent/SE441448B/sv unknown
- 1978-04-17 PH PH21013A patent/PH13756A/en unknown
- 1978-04-18 YU YU00914/78A patent/YU91478A/xx unknown
- 1978-04-20 NL NL7804210A patent/NL7804210A/xx not_active Application Discontinuation
- 1978-04-24 AU AU35377/78A patent/AU499618B1/en not_active Expired
- 1978-04-25 EG EG276/78A patent/EG13590A/xx active
- 1978-04-28 AR AR271956A patent/AR217688A1/es active
- 1978-05-18 GB GB20350/78A patent/GB1586655A/en not_active Expired
- 1978-05-18 CS CS783239A patent/CS207612B2/cs unknown
- 1978-05-18 HU HU78PI626A patent/HU185009B/hu unknown
- 1978-05-18 HU HU822638A patent/HU188802B/hu unknown
- 1978-05-18 PL PL1978215923A patent/PL116944B1/pl unknown
- 1978-05-18 HU HU822639A patent/HU187782B/hu unknown
- 1978-05-18 PL PL1978215922A patent/PL114541B1/pl unknown
- 1978-05-18 SU SU782615898A patent/SU873883A3/ru active
- 1978-05-18 PL PL1978206903A patent/PL114547B1/pl unknown
- 1978-05-18 PL PL1978215921A patent/PL117107B1/pl unknown
- 1978-05-19 CA CA303,710A patent/CA1094071A/en not_active Expired
- 1978-05-19 DD DD78215015A patent/DD145536A5/de unknown
- 1978-05-19 PT PT68058A patent/PT68058B/pt unknown
- 1978-05-19 BE BE187842A patent/BE867249A/xx not_active IP Right Cessation
- 1978-05-19 DD DD78215017A patent/DD145537A5/de unknown
- 1978-05-19 DD DD78205479A patent/DD138321A5/de unknown
- 1978-05-19 DD DD215016A patent/DD146186A5/de unknown
- 1978-05-20 GR GR56281A patent/GR69985B/el unknown
- 1978-05-22 JP JP6087278A patent/JPS53144600A/ja active Granted
- 1978-05-22 CH CH552678A patent/CH634321A5/fr not_active IP Right Cessation
- 1978-05-22 NO NO781770A patent/NO150204C/no unknown
- 1978-05-22 ZA ZA00782918A patent/ZA782918B/xx unknown
- 1978-05-22 AT AT0369678A patent/AT368995B/de not_active IP Right Cessation
- 1978-05-22 IT IT23673/78A patent/IT1096307B/it active
- 1978-05-22 DK DK226678A patent/DK226678A/da not_active Application Discontinuation
- 1978-05-22 IL IL54755A patent/IL54755A/xx unknown
- 1978-05-22 FR FR7815029A patent/FR2392023A1/fr active Granted
- 1978-05-22 IE IE1013/78A patent/IE46975B1/en unknown
- 1978-05-22 NZ NZ187333A patent/NZ187333A/en unknown
- 1978-05-22 FI FI781612A patent/FI63402C/fi not_active IP Right Cessation
- 1978-05-22 LU LU79684A patent/LU79684A1/xx unknown
- 1978-05-23 DE DE2822465A patent/DE2822465C2/de not_active Expired
1979
- 1979-04-16 AR AR276191A patent/AR221721A1/es active
- 1979-04-24 SU SU792753359A patent/SU843749A3/ru active
- 1979-04-26 SU SU792759902A patent/SU818484A3/ru active
- 1979-05-18 SU SU792763595A patent/SU841589A3/ru active
- 1979-05-18 PL PL20690379A patent/PL206903A1/xx unknown
1982
- 1982-10-01 YU YU2217/82A patent/YU40796B/xx unknown
- 1982-10-01 YU YU02218/82A patent/YU221882A/xx unknown
- 1982-10-01 YU YU02216/82A patent/YU221682A/xx unknown
1983
- 1983-05-20 NO NO831790A patent/NO151862C/no unknown
- 1983-10-27 SE SE8305917A patent/SE448459B/sv not_active IP Right Cessation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE20204239U1 (de)	2002-03-16	2002-05-29	Funke Kunststoffe GmbH, 48324 Sendenhorst	Universal-Rohrdichtung

Also Published As

Publication number	Publication date
NL7804210A (nl)	1978-11-27
FR2392023B1 (de)	1980-11-07
FI63402C (fi)	1983-06-10
AR217688A1 (es)	1980-04-15
YU40796B (en)	1986-06-30
YU221782A (en)	1983-01-21
IT1096307B (it)	1985-08-26
NO150204B (no)	1984-05-28
HU188802B (en)	1986-05-28
JPS53144600A (en)	1978-12-15
PL206903A1 (pl)	1979-10-22
SE7803625L (sv)	1978-11-24
AR221721A1 (es)	1981-03-13
AU499618B1 (en)	1979-04-26
PT68058A (en)	1978-06-01
IE46975B1 (en)	1983-11-16
BE867249A (fr)	1978-11-20
NO781770L (no)	1978-11-24
DD145537A5 (de)	1980-12-17
HU187782B (en)	1986-02-28
IL54755A0 (en)	1978-07-31
SU818484A3 (ru)	1981-03-30
SU841589A3 (ru)	1981-06-23
YU221682A (en)	1983-01-21
DD145536A5 (de)	1980-12-17
SU873883A3 (ru)	1981-10-15
SE8305917L (sv)	1983-10-27
CA1094071A (en)	1981-01-20
NO150204C (no)	1984-09-05
FR2392023A1 (fr)	1978-12-22
HU185009B (en)	1984-11-28
ATA369678A (de)	1982-04-15
GB1586655A (en)	1981-03-25
DE2822465C2 (de)	1986-08-28
NO151862B (no)	1985-03-11
PH13756A (en)	1980-09-17
PL116944B1 (en)	1981-07-31
NZ187333A (en)	1984-05-31
PT68058B (en)	1979-10-24
JPS5711912B2 (de)	1982-03-08
DD138321A5 (de)	1979-10-24
PL114541B1 (en)	1981-02-28
SU843749A3 (ru)	1981-06-30
AT368995B (de)	1982-11-25
SE448459B (sv)	1987-02-23
DD146186A5 (de)	1981-01-28
DK226678A (da)	1978-11-24
IE781013L (en)	1978-11-23
FI63402B (fi)	1983-02-28
ZA782918B (en)	1979-06-27
CS207612B2 (en)	1981-08-31
GR69985B (de)	1982-07-22
PL114547B1 (en)	1981-02-28
PL117107B1 (en)	1981-07-31
NO831790L (no)	1978-11-24
NO151862C (no)	1985-06-19
FI781612A (fi)	1978-11-24
YU91478A (en)	1983-01-21
LU79684A1 (fr)	1979-12-06
IL54755A (en)	1981-02-27
IT7823673A0 (it)	1978-05-22
DE2822465A1 (de)	1978-11-30
SE8305917D0 (sv)	1983-10-27
YU221882A (en)	1983-01-21
SE441448B (sv)	1985-10-07
EG13590A (en)	1982-03-31

Publication	Publication Date	Title
EP1680421B1 (de)	2008-02-13	Verwendung tricyclischer verbindungen als inhibitoren des glycintransports
EP0302788B1 (de)	1992-02-05	2-[Methyl(4-piperidinyl)]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indolderivate, ihre Herstellung und therapeutische Verwendung
LU79761A1 (fr)	1980-01-22	Procede de preparation de nouveaux composes de phtalazine et de composition pharmaceutique les contenant
EP1682503A2 (de)	2006-07-26	Derivate von n-[phenyl(alkylpiperidin-2-yl)methyl]benzamid, verfahren zu deren herstellung und deren anwendung in therapeutika
EP0042781B1 (de)	1985-03-06	1-(4- Chinolyl), 2- oder 3- (2- oder 3-piperidyl oder pyrrolidinyl)-Äthanon oder -Propanon, Verfahren zu seiner Herstellung und seine Anwendung als Arzneimittel
BE898278A (fr)	1984-05-22	Benzoxazines antipsychotiques.
NO155490B (no)	1986-12-29	Analogifremgangsmaate for fremstilling av terapeutisk aktivt 4-)1"-hydroksy-2"-(n-imidazolyl)etyl)bibenzyl.
CH651040A5 (fr)	1985-08-30	Procedes de preparation de trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido(4,3-b)-indoles substitues en position 2 dextrogyres et medicament les contenant.
CH634321A5 (en)	1983-01-31	trans-5-Aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles, process for their preparation and pharmaceutical composition containing them
EP0031753B1 (de)	1984-09-19	2-(4-Piperidyl)-1-(4-chinolyl)-ethanon-Derivate, Zwischenprodukte und Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0008249B1 (de)	1981-08-26	Fluoren- und Fluoranthenderivate, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung
GB2091251A (en)	1982-07-28	Derivatives of anti-phlogistically active carboxylic acids
EP0178201B1 (de)	1989-02-01	Furo[3,2-c]pyridinderivate, ihre Herstellung und ihre therapeutische Verwendung
FR2495470A1 (fr)	1982-06-11	Nouveaux medicaments a base de derives de (quinolyl-4)-1 (piperidyl-4)-2 ethanol ou (quinolyl-4)-1 (piperidyl-4)-3 propanol
FR2510575A1 (fr)	1983-02-04	Nouveaux composes bicycliques, leur procede de preparation et composition pharmaceutique les renfermant
CH644379A5 (fr)	1984-07-31	Hexahydro-trans-pyrido-indoles et composition pharmaceutique les contenant.
FR2690917A1 (fr)	1993-11-12	Aminoesters, leur procédé de préparation et leur application en thérapeutique.
FR2609715A1 (fr)	1988-07-22	Nouveaux diazepinoindoles, leur preparation et leur utilisation comme medicaments
BE874322R (fr)	1979-08-21	Nouveaux composes heterocycliques, leur preparation et leur application comme medicaments
EP0848707A1 (de)	1998-06-24	4-(cycloalkyl)piperidine und 4-(cycloalkylalkyl)-piperidine, ihre herstellung und therapeutische verwendung
JPS6352028B2 (de)	1988-10-17
LU84664A1 (fr)	1984-11-08	Alkyl-4-indolonaphtyridines et leur application therapeutique
JPS6038392B2 (ja)	1985-08-31	ナフチリジン誘導体およびその製造方法
BE848963A (fr)	1977-04-01	Phenylindolines et procede pour les produire
FR2553772A1 (fr)	1985-04-26	Derives de 2h-azeto(2,1-a)-isoquinoleine, procede pour les preparer et compositions pharmaceutiques les contenant

Legal Events

Date	Code	Title	Description
1988-01-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

CH634321A5 - trans-5-Aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles, process for their preparation and pharmaceutical composition containing them - Google Patents

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