IL98495A - Indole derivatives process for their preparation and pharmaceutical compositions containing them - Google Patents

Indole derivatives process for their preparation and pharmaceutical compositions containing them

Info

Publication number: IL98495A
Authority: IL; Israel
Prior art keywords: indole; hydrogen; fluorophenyl; derivative; ethyl
Prior art date: 1990-07-02

Application number

IL9849591A

Other languages

English (en)

Other versions

IL98495A0 (en

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.)

1990-07-02

Filing date

1991-06-13

Publication date

1995-06-29

1991-06-13 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

1992-07-15 Publication of IL98495A0 publication Critical patent/IL98495A0/xx

1995-06-29 Publication of IL98495A publication Critical patent/IL98495A/en

Links

150000002475 indoles Chemical class 0.000 title claims abstract description 16
238000000034 method Methods 0.000 title claims description 60
238000002360 preparation method Methods 0.000 title claims description 9
229940054051 antipsychotic indole derivative Drugs 0.000 title description 3
239000008194 pharmaceutical composition Substances 0.000 title description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
239000001257 hydrogen Substances 0.000 claims abstract description 31
125000000217 alkyl group Chemical group 0.000 claims abstract description 22
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
150000002431 hydrogen Chemical group 0.000 claims abstract description 17
125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical class C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims abstract description 11
239000001301 oxygen Substances 0.000 claims abstract description 11
125000001424 substituent group Chemical group 0.000 claims abstract description 10
229910052717 sulfur Chemical group 0.000 claims abstract description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
239000011593 sulfur Chemical group 0.000 claims abstract description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052799 carbon Chemical group 0.000 claims abstract description 8
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
208000019695 Migraine disease Diseases 0.000 claims abstract description 7
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
150000002367 halogens Chemical group 0.000 claims abstract description 7
206010027599 migraine Diseases 0.000 claims abstract description 7
125000004981 cycloalkylmethyl group Chemical group 0.000 claims abstract description 6
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract description 6
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims abstract description 6
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
201000000980 schizophrenia Diseases 0.000 claims abstract description 5
208000024891 symptom Diseases 0.000 claims abstract description 5
208000019901 Anxiety disease Diseases 0.000 claims abstract description 4
208000018737 Parkinson disease Diseases 0.000 claims abstract description 4
230000036506 anxiety Effects 0.000 claims abstract description 4
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
208000019116 sleep disease Diseases 0.000 claims abstract description 4
208000022925 sleep disturbance Diseases 0.000 claims abstract description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
208000015114 central nervous system disease Diseases 0.000 claims abstract description 3
125000003282 alkyl amino group Chemical group 0.000 claims abstract 2
125000004663 dialkyl amino group Chemical group 0.000 claims abstract 2
230000001225 therapeutic effect Effects 0.000 claims abstract 2
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims abstract 2
239000003921 oil Substances 0.000 claims description 57
235000019198 oils Nutrition 0.000 claims description 57
150000001875 compounds Chemical class 0.000 claims description 37
150000003839 salts Chemical class 0.000 claims description 23
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
-1 alkyl mesylate Chemical compound 0.000 claims description 14
239000003814 drug Substances 0.000 claims description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 12
239000000651 prodrug Substances 0.000 claims description 11
229940002612 prodrug Drugs 0.000 claims description 11
239000003054 catalyst Substances 0.000 claims description 10
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 9
125000001246 bromo group Chemical group Br* 0.000 claims description 7
229910052727 yttrium Inorganic materials 0.000 claims description 7
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 5
125000004103 aminoalkyl group Chemical group 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
125000002346 iodo group Chemical group I* 0.000 claims description 5
238000007363 ring formation reaction Methods 0.000 claims description 5
230000002152 alkylating effect Effects 0.000 claims description 4
150000008064 anhydrides Chemical class 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 4
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
KGASELUWIGUZKN-UHFFFAOYSA-N 1-[2-[4-[1-(4-fluorophenyl)-6-methylindol-3-yl]piperidin-1-yl]ethyl]-3-propan-2-ylimidazolidin-2-one Chemical compound O=C1N(C(C)C)CCN1CCN1CCC(C=2C3=CC=C(C)C=C3N(C=3C=CC(F)=CC=3)C=2)CC1 KGASELUWIGUZKN-UHFFFAOYSA-N 0.000 claims description 3
235000019483 Peanut oil Nutrition 0.000 claims description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
239000004202 carbamide Substances 0.000 claims description 3
229940074993 carbon disulfide Drugs 0.000 claims description 3
235000005687 corn oil Nutrition 0.000 claims description 3
239000002285 corn oil Substances 0.000 claims description 3
239000002385 cottonseed oil Substances 0.000 claims description 3
235000012343 cottonseed oil Nutrition 0.000 claims description 3
235000014113 dietary fatty acids Nutrition 0.000 claims description 3
239000000194 fatty acid Substances 0.000 claims description 3
229930195729 fatty acid Natural products 0.000 claims description 3
150000004665 fatty acids Chemical class 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
239000012948 isocyanate Substances 0.000 claims description 3
150000002513 isocyanates Chemical class 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
239000004006 olive oil Substances 0.000 claims description 3
235000008390 olive oil Nutrition 0.000 claims description 3
239000000312 peanut oil Substances 0.000 claims description 3
150000004885 piperazines Chemical class 0.000 claims description 3
239000003549 soybean oil Substances 0.000 claims description 3
235000012424 soybean oil Nutrition 0.000 claims description 3
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 3
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
NIMNILHFXBBMBV-UHFFFAOYSA-N 1-[2-[4-[6-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-3-propan-2-ylimidazolidin-2-one Chemical group O=C1N(C(C)C)CCN1CCN1CCC(C=2C3=CC=C(Cl)C=C3N(C=3C=CC(F)=CC=3)C=2)CC1 NIMNILHFXBBMBV-UHFFFAOYSA-N 0.000 claims description 2
XKJJOWGAKBYIQV-UHFFFAOYSA-N 2-piperidin-3-yl-1h-indole Chemical compound C1CCNCC1C1=CC2=CC=CC=C2N1 XKJJOWGAKBYIQV-UHFFFAOYSA-N 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
150000001350 alkyl halides Chemical class 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
229910017053 inorganic salt Inorganic materials 0.000 claims description 2
150000002540 isothiocyanates Chemical class 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
HDCXQTPVTAIPNZ-UHFFFAOYSA-N n-({[4-(aminosulfonyl)phenyl]amino}carbonyl)-4-methylbenzenesulfonamide Chemical group C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 HDCXQTPVTAIPNZ-UHFFFAOYSA-N 0.000 claims description 2
150000005623 oxindoles Chemical class 0.000 claims description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 claims 1
150000002118 epoxides Chemical class 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 17
230000000694 effects Effects 0.000 abstract description 11
102000056834 5-HT2 Serotonin Receptors Human genes 0.000 abstract description 6
108091005479 5-HT2 receptors Proteins 0.000 abstract description 6
229940076279 serotonin Drugs 0.000 abstract description 5
230000009870 specific binding Effects 0.000 abstract description 5
230000005923 long-lasting effect Effects 0.000 abstract description 2
125000001072 heteroaryl group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 82
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
239000000243 solution Substances 0.000 description 54
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
239000000203 mixture Substances 0.000 description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000002904 solvent Substances 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
229910001868 water Inorganic materials 0.000 description 23
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 21
241000700159 Rattus Species 0.000 description 20
230000027455 binding Effects 0.000 description 19
238000001816 cooling Methods 0.000 description 17
239000000543 intermediate Substances 0.000 description 17
239000012074 organic phase Substances 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
238000012360 testing method Methods 0.000 description 15
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
210000001519 tissue Anatomy 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
239000000872 buffer Substances 0.000 description 12
229940079593 drug Drugs 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
229940086542 triethylamine Drugs 0.000 description 12
235000011054 acetic acid Nutrition 0.000 description 11
230000005764 inhibitory process Effects 0.000 description 11
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000004440 column chromatography Methods 0.000 description 9
238000000338 in vitro Methods 0.000 description 9
230000009467 reduction Effects 0.000 description 9
238000006722 reduction reaction Methods 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
238000010992 reflux Methods 0.000 description 8
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 7
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
239000012267 brine Substances 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000012458 free base Substances 0.000 description 7
238000002347 injection Methods 0.000 description 7
239000007924 injection Substances 0.000 description 7
239000008188 pellet Substances 0.000 description 7
229960001289 prazosin Drugs 0.000 description 7
XRXDAJYKGWNHTQ-UHFFFAOYSA-N quipazine Chemical compound C1CNCCN1C1=CC=C(C=CC=C2)C2=N1 XRXDAJYKGWNHTQ-UHFFFAOYSA-N 0.000 description 7
229950002315 quipazine Drugs 0.000 description 7
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 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
239000012043 crude product Substances 0.000 description 6
238000011534 incubation Methods 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
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
230000009871 nonspecific binding Effects 0.000 description 6
235000011181 potassium carbonates Nutrition 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
238000000746 purification Methods 0.000 description 6
229960000652 sertindole Drugs 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
206010028347 Muscle twitching Diseases 0.000 description 5
239000002585 base Substances 0.000 description 5
230000036461 convulsion Effects 0.000 description 5
229960003638 dopamine Drugs 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229950001675 spiperone Drugs 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
FPCCSQOGAWCVBH-PSQIVULCSA-N 3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]-1,1,2,2-tetratritioethyl]-1h-quinazoline-2,4-dione Chemical compound O=C1NC2=CC=CC=C2C(=O)N1C([3H])([3H])C([3H])([3H])N(CC1)CCC1C(=O)C1=CC=C(F)C=C1 FPCCSQOGAWCVBH-PSQIVULCSA-N 0.000 description 4
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
238000009472 formulation Methods 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
230000003902 lesion Effects 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
YEHCICAEULNIGD-MZMPZRCHSA-N pergolide Chemical compound C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 YEHCICAEULNIGD-MZMPZRCHSA-N 0.000 description 4
229960004851 pergolide Drugs 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
JUQLTPCYUFPYKE-UHFFFAOYSA-N ritanserin Chemical compound CC=1N=C2SC=CN2C(=O)C=1CCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 JUQLTPCYUFPYKE-UHFFFAOYSA-N 0.000 description 4
229950009626 ritanserin Drugs 0.000 description 4
239000003215 serotonin 5-HT2 receptor antagonist Substances 0.000 description 4
239000000600 sorbitol Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
FGEQPHQXHJNFLV-UHFFFAOYSA-N 1-(2-chloroethyl)-3-propan-2-ylimidazolidin-2-one Chemical compound CC(C)N1CCN(CCCl)C1=O FGEQPHQXHJNFLV-UHFFFAOYSA-N 0.000 description 3
NCZRXRGIUPSHIH-UHFFFAOYSA-N 2-[4-[1-(4-fluorophenyl)-5-(trifluoromethyl)indol-3-yl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C(C1=CC(=CC=C11)C(F)(F)F)=CN1C1=CC=C(F)C=C1 NCZRXRGIUPSHIH-UHFFFAOYSA-N 0.000 description 3
CIRSPTXGPFAXRE-UHFFFAOYSA-N 3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-indole Chemical class C1NCCC(C=2C3=CC=CC=C3NC=2)=C1 CIRSPTXGPFAXRE-UHFFFAOYSA-N 0.000 description 3
KAIRZPVWWIMPFT-UHFFFAOYSA-N 3-piperidin-4-yl-1h-indole Chemical class C1CNCCC1C1=CNC2=CC=CC=C12 KAIRZPVWWIMPFT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 3
239000001828 Gelatine Substances 0.000 description 3
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239000007832 Na2SO4 Substances 0.000 description 1
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241000700157 Rattus norvegicus Species 0.000 description 1
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241001522306 Serinus serinus Species 0.000 description 1
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239000012280 lithium aluminium hydride Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
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NXQSBBOBZUOFIQ-UHFFFAOYSA-N n-[2-[4-[6-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-1,1-dimethoxyethanamine Chemical compound C1CN(CCNC(C)(OC)OC)CCC1C(C1=CC=C(Cl)C=C11)=CN1C1=CC=C(F)C=C1 NXQSBBOBZUOFIQ-UHFFFAOYSA-N 0.000 description 1
YHZPMPRIBOAHEO-UHFFFAOYSA-N n-[2-[4-[6-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-n'-propan-2-ylethane-1,2-diamine Chemical compound C1CN(CCNCCNC(C)C)CCC1C(C1=CC=C(Cl)C=C11)=CN1C1=CC=C(F)C=C1 YHZPMPRIBOAHEO-UHFFFAOYSA-N 0.000 description 1
YYDVBMSWBFMKLM-UHFFFAOYSA-N n-[2-[4-[6-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-2-yl]ethyl]acetamide Chemical compound C1CNC(CCNC(=O)C)CC1C(C1=CC=C(Cl)C=C11)=CN1C1=CC=C(F)C=C1 YYDVBMSWBFMKLM-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
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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239000003176 neuroleptic agent Substances 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
230000000926 neurological effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
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230000002474 noradrenergic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
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239000008363 phosphate buffer Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical class CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
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230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
229920006395 saturated elastomer Polymers 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
150000003335 secondary amines Chemical class 0.000 description 1
229950011041 sergolexole Drugs 0.000 description 1
239000003478 serotonin 5-HT2 receptor agonist Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000527 sonication Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
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239000000126 substance Substances 0.000 description 1
210000003523 substantia nigra Anatomy 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000003826 tablet Substances 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
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
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150000003672 ureas Chemical class 0.000 description 1
JQSHBVHOMNKWFT-DTORHVGOSA-N varenicline Chemical compound C12=CC3=NC=CN=C3C=C2[C@H]2C[C@@H]1CNC2 JQSHBVHOMNKWFT-DTORHVGOSA-N 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/24—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
- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)
Paints Or Removers (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicinal Preparation (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

IL9849591A 1990-07-02 1991-06-13 Indole derivatives process for their preparation and pharmaceutical compositions containing them IL98495A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DK158590A DK158590D0 (da)	1990-07-02	1990-07-02	Indolderivater
SG19895A SG19895G (en)	1990-07-02	1995-02-07	Novel indole derivatives

Publications (2)

Publication Number	Publication Date
IL98495A0 IL98495A0 (en)	1992-07-15
IL98495A true IL98495A (en)	1995-06-29

Family

ID=26065925

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9849591A IL98495A (en)	1990-07-02	1991-06-13	Indole derivatives process for their preparation and pharmaceutical compositions containing them

Country Status (20)

Country	Link
US (1)	US5216001A (de)
EP (1)	EP0465398B1 (de)
JP (1)	JP3057109B2 (de)
KR (1)	KR950010163B1 (de)
AT (1)	ATE115576T1 (de)
AU (1)	AU644186B2 (de)
CA (1)	CA2045955C (de)
DE (1)	DE69105839T2 (de)
DK (2)	DK158590D0 (de)
ES (1)	ES2064973T3 (de)
FI (1)	FI101223B (de)
GR (1)	GR3015286T3 (de)
HK (1)	HK52195A (de)
IE (1)	IE65339B1 (de)
IL (1)	IL98495A (de)
NO (1)	NO178191C (de)
NZ (1)	NZ238757A (de)
PT (1)	PT98168B (de)
SG (1)	SG19895G (de)
ZA (1)	ZA915110B (de)

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AR013669A1 (es) *	1997-10-07	2001-01-10	Smithkline Beecham Corp	Compuestos y metodos
GB9805716D0 (en) *	1998-03-17	1998-05-13	Merck Sharp & Dohme	Therapeutic agents
GB9815317D0 (en) *	1998-07-15	1998-09-16	Merck Sharp & Dohme	Therapeutic agents
GB9816263D0 (en)	1998-07-24	1998-09-23	Merck Sharp & Dohme	Therapeutic agents
US5994352A (en) *	1998-11-13	1999-11-30	Pfizer Inc.	5-arylindole derivatives
JP2002534426A (ja) *	1999-01-07	2002-10-15	ワイス	鬱病の処置のための新規な１，４−二基置換されたシクロヘキサン誘導体
US6200994B1 (en)	1999-01-07	2001-03-13	American Home Products Corp	1,4-Disubstituted cyclohexane derivatives for the treatment of depression
EP1173432B9 (de) *	1999-04-21	2008-10-15	NPS Allelix Corp.	Piperidin-indol derivate mit 5-ht6 affinität
US6281207B1 (en) *	1999-09-15	2001-08-28	Reed Richter	Treatment of movement disorders by administration of mirtazapine
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JP7732999B2 (ja)	2020-04-03	2025-09-02	バーテックスファーマシューティカルズインコーポレイテッド	アルファ１－アンチトリプシンのモジュレーター
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1990
- 1990-07-02 DK DK158590A patent/DK158590D0/da not_active IP Right Cessation
1991
- 1991-06-12 IE IE200091A patent/IE65339B1/en not_active IP Right Cessation
- 1991-06-13 IL IL9849591A patent/IL98495A/en not_active IP Right Cessation
- 1991-06-14 NO NO912301A patent/NO178191C/no not_active IP Right Cessation
- 1991-06-24 DK DK91610055.5T patent/DK0465398T3/da active
- 1991-06-24 EP EP91610055A patent/EP0465398B1/de not_active Expired - Lifetime
- 1991-06-24 AT AT91610055T patent/ATE115576T1/de not_active IP Right Cessation
- 1991-06-24 DE DE69105839T patent/DE69105839T2/de not_active Expired - Fee Related
- 1991-06-24 ES ES91610055T patent/ES2064973T3/es not_active Expired - Lifetime
- 1991-06-26 KR KR1019910010711A patent/KR950010163B1/ko not_active Expired - Fee Related
- 1991-06-27 US US07/722,081 patent/US5216001A/en not_active Expired - Fee Related
- 1991-06-27 NZ NZ238757A patent/NZ238757A/xx unknown
- 1991-06-28 CA CA002045955A patent/CA2045955C/en not_active Expired - Fee Related
- 1991-07-01 PT PT98168A patent/PT98168B/pt active IP Right Grant
- 1991-07-01 FI FI913194A patent/FI101223B/fi active
- 1991-07-01 JP JP3160289A patent/JP3057109B2/ja not_active Expired - Fee Related
- 1991-07-02 AU AU80144/91A patent/AU644186B2/en not_active Ceased
- 1991-07-02 ZA ZA915110A patent/ZA915110B/xx unknown
1995
- 1995-02-07 SG SG19895A patent/SG19895G/en unknown
- 1995-03-03 GR GR950400464T patent/GR3015286T3/el unknown
- 1995-04-06 HK HK52195A patent/HK52195A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU644186B2 (en)	1993-12-02
SG19895G (en)	1995-08-18
IL98495A0 (en)	1992-07-15
NZ238757A (en)	1993-08-26
EP0465398A2 (de)	1992-01-08
DK158590D0 (da)	1990-07-02
ZA915110B (en)	1992-05-27
KR950010163B1 (ko)	1995-09-11
DE69105839T2 (de)	1995-04-27
FI101223B1 (fi)	1998-05-15
JPH04253976A (ja)	1992-09-09
KR920002586A (ko)	1992-02-28
DK0465398T3 (da)	1995-05-22
CA2045955C (en)	2002-08-27
EP0465398B1 (de)	1994-12-14
ATE115576T1 (de)	1994-12-15
FI913194L (fi)	1992-01-03
IE65339B1 (en)	1995-10-18
HK52195A (en)	1995-04-13
IE912000A1 (en)	1992-01-15
PT98168A (pt)	1992-05-29
CA2045955A1 (en)	1992-01-03
NO178191C (no)	1996-02-07
AU8014491A (en)	1992-01-02
US5216001A (en)	1993-06-01
ES2064973T3 (es)	1995-02-01
NO912301D0 (no)	1991-06-14
PT98168B (pt)	1998-12-31
JP3057109B2 (ja)	2000-06-26
FI101223B (fi)	1998-05-15
DE69105839D1 (de)	1995-01-26
EP0465398A3 (en)	1992-03-04
NO178191B (no)	1995-10-30
GR3015286T3 (en)	1995-06-30
NO912301L (no)	1992-01-03
FI913194A0 (fi)	1991-07-01

Legal Events

Date	Code	Title
1997-11-20	KB	Patent renewed
2001-07-24	KB	Patent renewed
2006-03-12	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP0465398B1 (de)	1994-12-14	Neue Indolderivate
CA1338327B (en)	1996-05-14	1-(4'-Fluorophenyl)-3,5-Substituted Indoles Useful in the Treatment of Psychic Disorders
EP0376607B1 (de)	1994-03-02	Piperazine-Derivate
EP0470039B1 (de)	1994-12-07	3-Arylindol- und 3-Arylindazolderivate
CZ350796A3 (en)	1997-06-11	Piperazine derivatives as 5ht1a antagonists
IL109234A (en)	1998-04-05	Indole derivatives, their preparation and pharmaceutical compositions containing them
HUT70195A (en)	1995-09-28	Process for producing benzimidazolone derivatives and pharmaceutical preparations containing them
SK76195A3 (en)	1995-11-08	Condensed benzocompounds, pharmaceutical preparation containing them and their use
US5457115A (en)	1995-10-10	Indole derivatives
US5703087A (en)	1997-12-30	Phenyl indole compounds
EP0575429B1 (de)	1995-12-06	Behandlung von kognitiven störungen
JP2004501912A (ja)	2004-01-22	Ｃｎｓ障害の治療に有用なインドール誘導体
CN101010296B (zh)	2011-08-17	烷基羟吲哚的哌嗪衍生物