NO309038B1 - Fenylindolforbindelser - Google Patents

Fenylindolforbindelser Download PDF

Info

Publication number: NO309038B1
Authority: NO; Norway
Prior art keywords: chloro; fluorophenyl; indol; ethyl; piperidin
Prior art date: 1993-11-01

Application number

NO961746A

Other languages

English (en)

Norwegian (no)

Other versions

NO961746L (no

NO961746D0 (no

Inventor

Jens Kristian Perregaard

Ejner Knud Moltzen

Kim Andersen

Henrik Pedersen

Klaus Peter Boegesoe

Andre Pernet

Barbara Bopp

Darcy Mulford

Kiyoshi Sakamoto

Original Assignee

Lundbeck & Co As H

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.)

1993-11-01

Filing date

1996-04-30

Publication date

2000-12-04

1996-04-30 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

1996-04-30 Publication of NO961746D0 publication Critical patent/NO961746D0/no

1996-06-28 Publication of NO961746L publication Critical patent/NO961746L/no

2000-12-04 Publication of NO309038B1 publication Critical patent/NO309038B1/no

Links

150000001875 compounds Chemical class 0.000 claims description 61
150000003839 salts Chemical class 0.000 claims description 20
-1 Phenylindole compound Chemical class 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 7
125000004043 oxo group Chemical group O=* 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
201000000980 schizophrenia Diseases 0.000 claims description 4
208000024891 symptom Diseases 0.000 claims description 4
206010020772 Hypertension Diseases 0.000 claims description 3
208000028017 Psychotic disease Diseases 0.000 claims description 3
125000003003 spiro group Chemical group 0.000 claims description 3
GZKLJWGUPQBVJQ-KNXIQCGSSA-N 1-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-4,4-dideuterioimidazolidin-2-one Chemical compound O=C1NC([2H])([2H])CN1CCN1CCC(C=2C3=CC(Cl)=CC=C3N(C=3C=CC(F)=CC=3)C=2)CC1 GZKLJWGUPQBVJQ-KNXIQCGSSA-N 0.000 claims description 2
VHRGXGDHLXDLMC-UHFFFAOYSA-N 1-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-4,4-dimethylimidazolidin-2-one Chemical compound O=C1NC(C)(C)CN1CCN1CCC(C=2C3=CC(Cl)=CC=C3N(C=3C=CC(F)=CC=3)C=2)CC1 VHRGXGDHLXDLMC-UHFFFAOYSA-N 0.000 claims description 2
GZKLJWGUPQBVJQ-XUWBISKJSA-N 1-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-5,5-dideuterioimidazolidin-2-one Chemical compound [2H]C1([2H])CNC(=O)N1CCN1CCC(C=2C3=CC(Cl)=CC=C3N(C=3C=CC(F)=CC=3)C=2)CC1 GZKLJWGUPQBVJQ-XUWBISKJSA-N 0.000 claims description 2
CQWPRUAOHWCUHD-UHFFFAOYSA-N 1-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-5-methoxyimidazolidin-2-one Chemical compound COC1CNC(=O)N1CCN1CCC(C=2C3=CC(Cl)=CC=C3N(C=3C=CC(F)=CC=3)C=2)CC1 CQWPRUAOHWCUHD-UHFFFAOYSA-N 0.000 claims description 2
UEQQPRXNECSUTB-UHFFFAOYSA-N 3-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-1,3-diazaspiro[4.4]nonan-2-one Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NC4(CCCC4)C3)=O)CC2)=C1 UEQQPRXNECSUTB-UHFFFAOYSA-N 0.000 claims description 2
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
229910052805 deuterium Inorganic materials 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
LBWVARIQNSNHHF-UHFFFAOYSA-N 1-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-1,3-diazaspiro[4.4]nonan-2-one Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C4(CCCC4)CNC3=O)CC2)=C1 LBWVARIQNSNHHF-UHFFFAOYSA-N 0.000 claims 1
GZKLJWGUPQBVJQ-ZXSHKXLLSA-N 1-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-4,4,5,5-tetradeuterioimidazolidin-2-one Chemical compound [2H]C1([2H])C([2H])([2H])NC(=O)N1CCN1CCC(C=2C3=CC(Cl)=CC=C3N(C=3C=CC(F)=CC=3)C=2)CC1 GZKLJWGUPQBVJQ-ZXSHKXLLSA-N 0.000 claims 1
PZCFPIOIAWXVIO-UHFFFAOYSA-N 1-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-5,5-dimethylimidazolidin-2-one Chemical compound CC1(C)CNC(=O)N1CCN1CCC(C=2C3=CC(Cl)=CC=C3N(C=3C=CC(F)=CC=3)C=2)CC1 PZCFPIOIAWXVIO-UHFFFAOYSA-N 0.000 claims 1
QHYYMSNCBYDHDH-UHFFFAOYSA-N 1-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)C(C)(C)N1CCN1CCC(C=2C3=CC(Cl)=CC=C3N(C=3C=CC(F)=CC=3)C=2)CC1 QHYYMSNCBYDHDH-UHFFFAOYSA-N 0.000 claims 1
229940124604 anti-psychotic medication Drugs 0.000 claims 1
GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 abstract description 11
229960000652 sertindole Drugs 0.000 abstract description 10
KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical class N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 abstract description 3
239000003693 atypical antipsychotic agent Substances 0.000 abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
239000000203 mixture Substances 0.000 description 55
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
238000000034 method Methods 0.000 description 46
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 34
239000003921 oil Substances 0.000 description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
239000002904 solvent Substances 0.000 description 32
239000000243 solution Substances 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
230000015572 biosynthetic process Effects 0.000 description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
238000005481 NMR spectroscopy Methods 0.000 description 14
239000012074 organic phase Substances 0.000 description 14
238000003786 synthesis reaction Methods 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
238000010992 reflux Methods 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
239000007858 starting material Substances 0.000 description 11
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
238000010438 heat treatment Methods 0.000 description 10
238000003756 stirring Methods 0.000 description 10
241000700159 Rattus Species 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
238000001816 cooling Methods 0.000 description 8
239000003480 eluent Substances 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
239000012267 brine Substances 0.000 description 7
238000001035 drying Methods 0.000 description 7
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 7
238000000746 purification Methods 0.000 description 7
XJGVVOAKITWCAB-UHFFFAOYSA-N 2-phenylmethoxyethanamine Chemical compound NCCOCC1=CC=CC=C1 XJGVVOAKITWCAB-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
239000000725 suspension Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
239000004202 carbamide Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000000605 extraction Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000001727 in vivo Methods 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
239000012071 phase Substances 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
239000000164 antipsychotic agent Substances 0.000 description 4
239000002178 crystalline material Substances 0.000 description 4
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 4
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
AICIYIDUYNFPRY-UHFFFAOYSA-N 1,3-dihydro-2H-imidazol-2-one Chemical group O=C1NC=CN1 AICIYIDUYNFPRY-UHFFFAOYSA-N 0.000 description 3
102000056834 5-HT2 Serotonin Receptors Human genes 0.000 description 3
108091005479 5-HT2 receptors Proteins 0.000 description 3
208000009132 Catalepsy Diseases 0.000 description 3
102000004980 Dopamine D2 Receptors Human genes 0.000 description 3
108090001111 Dopamine D2 Receptors Proteins 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
206010047853 Waxy flexibility Diseases 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
230000000561 anti-psychotic effect Effects 0.000 description 3
239000002585 base Substances 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
239000012458 free base Substances 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
239000002207 metabolite Substances 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
XRXDAJYKGWNHTQ-UHFFFAOYSA-N quipazine Chemical compound C1CNCCN1C1=CC=C(C=CC=C2)C2=N1 XRXDAJYKGWNHTQ-UHFFFAOYSA-N 0.000 description 3
229950002315 quipazine Drugs 0.000 description 3
KVPBAVSLBHFLKY-UHFFFAOYSA-N 1-azido-n-(2-phenylmethoxyethyl)cyclopentane-1-carboxamide Chemical compound C=1C=CC=CC=1COCCNC(=O)C1(N=[N+]=[N-])CCCC1 KVPBAVSLBHFLKY-UHFFFAOYSA-N 0.000 description 2
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
229910010084 LiAlH4 Inorganic materials 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
241000009298 Trigla lyra Species 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
150000004657 carbamic acid derivatives Chemical class 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
230000001484 cataleptigenic effect Effects 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
210000001653 corpus striatum Anatomy 0.000 description 2
230000003111 delayed effect Effects 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000000295 fuel oil Substances 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
235000011087 fumaric acid Nutrition 0.000 description 2
150000002332 glycine derivatives Chemical class 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
150000001469 hydantoins Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229960005417 ketanserin Drugs 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
230000005923 long-lasting effect Effects 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
239000012528 membrane Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
SXTMQFFVVICKDI-UHFFFAOYSA-N n-methyl-2-phenylmethoxyethanamine Chemical compound CNCCOCC1=CC=CC=C1 SXTMQFFVVICKDI-UHFFFAOYSA-N 0.000 description 2
VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 2
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230000008018 melting Effects 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229940087646 methanolamine Drugs 0.000 description 1
ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
MRZNYTMWNPAOMW-UHFFFAOYSA-N n'-(2-phenylmethoxyethyl)oxamide Chemical compound NC(=O)C(=O)NCCOCC1=CC=CC=C1 MRZNYTMWNPAOMW-UHFFFAOYSA-N 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000002912 oxalic acid derivatives Chemical class 0.000 description 1
150000003901 oxalic acid esters Chemical class 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
229940095574 propionic acid Drugs 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
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000003478 serotonin 5-HT2 receptor agonist Substances 0.000 description 1
239000003215 serotonin 5-HT2 receptor antagonist Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
201000009032 substance abuse Diseases 0.000 description 1
231100000736 substance abuse Toxicity 0.000 description 1
208000011117 substance-related disease Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
235000002906 tartaric acid 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
238000010998 test method Methods 0.000 description 1
125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000003021 water soluble solvent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- 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
- A61P25/18—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
- A61P25/24—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Heart & Thoracic Surgery (AREA)
Pain & Pain Management (AREA)
Cardiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)
Sewing Machines And Sewing (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Polyurethanes Or Polyureas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

NO961746A 1993-11-01 1996-04-30 Fenylindolforbindelser NO309038B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DK931234A DK123493D0 (da)	1993-11-01	1993-11-01	Compounds
PCT/DK1994/000407 WO1995012591A1 (fr)	1993-11-01	1994-10-28	Composes de phenylindole

Publications (3)

Publication Number	Publication Date
NO961746D0 NO961746D0 (no)	1996-04-30
NO961746L NO961746L (no)	1996-06-28
NO309038B1 true NO309038B1 (no)	2000-12-04

Family

ID=8102507

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO961746A NO309038B1 (no)	1993-11-01	1996-04-30	Fenylindolforbindelser

Country Status (26)

Country	Link
US (1)	US5703087A (fr)
EP (1)	EP0726898B1 (fr)
JP (1)	JP3898219B2 (fr)
KR (1)	KR100350550B1 (fr)
CN (1)	CN1134149A (fr)
AT (1)	ATE198199T1 (fr)
AU (1)	AU683700B2 (fr)
CA (1)	CA2175498C (fr)
CZ (1)	CZ291403B6 (fr)
DE (1)	DE69426462T2 (fr)
DK (2)	DK123493D0 (fr)
ES (1)	ES2154303T3 (fr)
FI (1)	FI116623B (fr)
GR (1)	GR3035462T3 (fr)
HU (1)	HUT76063A (fr)
IL (2)	IL111394A (fr)
LV (1)	LV12805B (fr)
NO (1)	NO309038B1 (fr)
NZ (1)	NZ275086A (fr)
PL (1)	PL176391B1 (fr)
PT (1)	PT726898E (fr)
RU (1)	RU2156249C2 (fr)
SI (1)	SI0726898T1 (fr)
SK (1)	SK281761B6 (fr)
WO (1)	WO1995012591A1 (fr)
ZA (1)	ZA948589B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6489341B1 (en)	1999-06-02	2002-12-03	Sepracor Inc.	Methods for the treatment of neuroleptic and related disorders using sertindole derivatives
JP2003509509A (ja)	1999-09-09	2003-03-11	ハー・ルンドベック・アクチエゼルスカベット	５−アミノアルキル及び５−アミノカルボニル置換されたインドール類
US20070212412A1 (en) *	2005-09-08	2007-09-13	H. Lundbeck A/S	Stable solid formulation of sertindole
TW200821296A (en) *	2006-06-01	2008-05-16	Lundbeck & Co As H	Use of sertindole for the preventive treatment of suicidal behaviour
EP2509961B1 (fr) *	2009-12-11	2016-03-09	Autifony Therapeutics Limited	Dérivés d'imidazolidinedione
EP2582698B1 (fr)	2010-06-16	2016-09-14	Vitae Pharmaceuticals, Inc.	Hétérocycles à 5, 6 et 7 chaînons substitués, médicaments contenant ces composés et leur utilisation
KR101862375B1 (ko)	2010-12-06	2018-05-29	오티포니 세라피틱스 리미티드	Kv3 억제제로서 유용한 하이단토인 유도체
US9193704B2 (en)	2011-06-07	2015-11-24	Autifony Therapeutics Limited	Hydantoin derivatives as KV3 inhibitors
PL2788339T3 (pl) *	2011-12-06	2016-09-30		Pochodne hydantoiny przydatne jako inhibitory KV3
CN104334547B (zh)	2012-05-22	2017-06-06	奥蒂福尼疗法有限公司	作为kv3抑制剂的三唑类
JP2015517563A (ja)	2012-05-22	2015-06-22	アウトイフオンイトヘラペウトイクスリミテッド	Ｋｖ３阻害剤としてのヒダントイン誘導体

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE58370B1 (en) *	1985-04-10	1993-09-08	Lundbeck & Co As H	Indole derivatives
GB8908085D0 (en) *	1989-04-11	1989-05-24	Lundbeck & Co As H	New therapeutic use
DK152090D0 (da) *	1990-06-22	1990-06-22	Lundbaek A S H	Piperidylsubstituerede indolderivater

1993
- 1993-11-01 DK DK931234A patent/DK123493D0/da not_active Application Discontinuation
1994
- 1994-10-25 IL IL11139494A patent/IL111394A/en not_active IP Right Cessation
- 1994-10-25 IL IL11139594A patent/IL111395A/xx not_active IP Right Cessation
- 1994-10-28 CN CN94193987A patent/CN1134149A/zh active Pending
- 1994-10-28 DE DE69426462T patent/DE69426462T2/de not_active Expired - Fee Related
- 1994-10-28 WO PCT/DK1994/000407 patent/WO1995012591A1/fr not_active Ceased
- 1994-10-28 CA CA002175498A patent/CA2175498C/fr not_active Expired - Fee Related
- 1994-10-28 US US08/635,905 patent/US5703087A/en not_active Expired - Fee Related
- 1994-10-28 PL PL94314181A patent/PL176391B1/pl not_active IP Right Cessation
- 1994-10-28 AU AU80577/94A patent/AU683700B2/en not_active Ceased
- 1994-10-28 KR KR1019960702237A patent/KR100350550B1/ko not_active Expired - Fee Related
- 1994-10-28 DK DK94931520T patent/DK0726898T3/da active
- 1994-10-28 SI SI9430356T patent/SI0726898T1/xx unknown
- 1994-10-28 SK SK534-96A patent/SK281761B6/sk not_active IP Right Cessation
- 1994-10-28 CZ CZ19961248A patent/CZ291403B6/cs not_active IP Right Cessation
- 1994-10-28 AT AT94931520T patent/ATE198199T1/de not_active IP Right Cessation
- 1994-10-28 NZ NZ275086A patent/NZ275086A/en not_active IP Right Cessation
- 1994-10-28 EP EP94931520A patent/EP0726898B1/fr not_active Expired - Lifetime
- 1994-10-28 JP JP51296895A patent/JP3898219B2/ja not_active Expired - Fee Related
- 1994-10-28 RU RU96110902/04A patent/RU2156249C2/ru not_active IP Right Cessation
- 1994-10-28 HU HU9601144A patent/HUT76063A/hu not_active Application Discontinuation
- 1994-10-28 ES ES94931520T patent/ES2154303T3/es not_active Expired - Lifetime
- 1994-10-28 PT PT94931520T patent/PT726898E/pt unknown
- 1994-11-01 ZA ZA948589A patent/ZA948589B/xx unknown
1996
- 1996-04-30 NO NO961746A patent/NO309038B1/no not_active IP Right Cessation
- 1996-04-30 FI FI961844A patent/FI116623B/fi active IP Right Grant
2001
- 2001-02-22 GR GR20010400296T patent/GR3035462T3/el not_active IP Right Cessation
- 2001-12-20 LV LV010178A patent/LV12805B/xx unknown

Also Published As

Publication number	Publication date
AU8057794A (en)	1995-05-23
EP0726898A1 (fr)	1996-08-21
CA2175498A1 (fr)	1995-05-11
NO961746L (no)	1996-06-28
SK281761B6 (sk)	2001-07-10
CA2175498C (fr)	2005-07-26
CZ124896A3 (en)	1996-09-11
WO1995012591A1 (fr)	1995-05-11
KR960705814A (ko)	1996-11-08
PL314181A1 (en)	1996-08-19
JP3898219B2 (ja)	2007-03-28
KR100350550B1 (ko)	2002-12-12
PT726898E (pt)	2001-05-31
FI961844A0 (fi)	1996-04-30
FI116623B (fi)	2006-01-13
HK1013817A1 (en)	1999-09-10
LV12805B (lv)	2002-05-20
IL111394A (en)	1998-08-16
EP0726898B1 (fr)	2000-12-20
SK53496A3 (en)	1996-11-06
LV12805A (en)	2002-03-20
IL111395A (en)	1999-06-20
JPH09506083A (ja)	1997-06-17
HU9601144D0 (en)	1996-07-29
DE69426462T2 (de)	2001-04-26
US5703087A (en)	1997-12-30
ATE198199T1 (de)	2001-01-15
SI0726898T1 (en)	2001-04-30
IL111395A0 (en)	1994-12-29
GR3035462T3 (en)	2001-05-31
ES2154303T3 (es)	2001-04-01
CZ291403B6 (cs)	2003-03-12
FI961844L (fi)	1996-04-30
IL111394A0 (en)	1994-12-29
NO961746D0 (no)	1996-04-30
DK0726898T3 (da)	2001-04-30
RU2156249C2 (ru)	2000-09-20
HUT76063A (en)	1997-06-30
CN1134149A (zh)	1996-10-23
NZ275086A (en)	1997-10-24
AU683700B2 (en)	1997-11-20
PL176391B1 (pl)	1999-05-31
DK123493D0 (da)	1993-11-01
DE69426462D1 (de)	2001-01-25
ZA948589B (en)	1995-06-26

Legal Events

Date	Code	Title	Description
2010-05-31	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
US5585378A (en)	1996-12-17	Composition containing an oxoindole compound
US6294555B1 (en)	2001-09-25	1-[(1-Substituted-4-piperidinyl)methyl]-4-piperidine derivative, process for producing the same, medicinal compositions containing the same and intermediates of these compounds
US5159083A (en)	1992-10-27	Certain aminomethyl phenylimidazole derivatives; a class of dopamine receptor subtype specific ligands
JP3057109B2 (ja)	2000-06-26	新規インドール誘導体
EP1581492B1 (fr)	2008-07-16	Indoles n-arylsulfonyl-3-substitues presentant une affinite pour le recepteur de la serotonine, methode de preparation et composition pharmaceutique contenant ces indoles
DE69028934T2 (de)	1997-03-20	Tetrahydrobenzimidazol-Derivate
SK280899B6 (sk)	2000-09-12	Použitie piperidínových derivátov, piperidínový derivát a farmaceutický prostriedok
CZ283398B6 (cs)	1998-04-15	Indolové deriváty jako 5-HT1A a/nebo 5-HT2 ligandy
SK280881B6 (sk)	2000-08-14	Derivát 3-indolylpiperidínu, spôsob jeho prípravy, jeho použitie na prípravu farmaceutického prostriedku a farmaceutický prostriedok, ktorý ho obsahuje
JP3898219B2 (ja)	2007-03-28	フエニルインドール化合物
AU639581B2 (en)	1993-07-29	1-(substituted pyridinylamino)-1h-indole-5-yl substituted carbamates, a process and intermediates for their preparation and their use as medicaments
US5317025A (en)	1994-05-31	Piperidinylthioindole derivatives, their methods of preparation and pharmaceutical compositions in which they are present, useful especially as analgesics
US5559246A (en)	1996-09-24	Indole derivatives
US5344927A (en)	1994-09-06	Tetrahydrobenzimidazole derivatives and pharmaceutical compositions containing same
HK1013817B (en)	2001-07-13	Phenylindole compounds
US5496942A (en)	1996-03-05	5-substituted tetrahydrobenzimidazole compounds
DD291761A5 (de)	1991-07-11	Verfahren zur herstellung von tetrahydrobenzimidazol-derivaten
HK1031869B (en)	2005-04-22	1-[(1-substituted-4-piperidinyl)methyl]-4-piperidine derivatives, process for producing the same, medicinal compositions containing the same and intermediates of these compounds
HK1083217B (en)	2011-10-21	N-arylsulfonyl-3-substituted indoles having serotonin receptor affinity, process for their preparation and pharmaceutical composition containing them