SK3612003A3 - Arylpiperazine derivatives and their use as psychotropic agents - Google Patents
Arylpiperazine derivatives and their use as psychotropic agents Download PDFInfo
- Publication number
- SK3612003A3 SK3612003A3 SK361-2003A SK3612003A SK3612003A3 SK 3612003 A3 SK3612003 A3 SK 3612003A3 SK 3612003 A SK3612003 A SK 3612003A SK 3612003 A3 SK3612003 A3 SK 3612003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- solvates
- acceptable salts
- treatment
- physiologically acceptable
- Prior art date
Links
- 239000004089 psychotropic agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 36
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 30
- 239000012453 solvate Substances 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 208000028017 Psychotic disease Diseases 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 210000003169 central nervous system Anatomy 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 208000020016 psychiatric disease Diseases 0.000 claims description 4
- 239000000556 agonist Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000002464 receptor antagonist Substances 0.000 claims description 2
- 229940044551 receptor antagonist Drugs 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 description 120
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 24
- 102000005962 receptors Human genes 0.000 description 16
- 108020003175 receptors Proteins 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 229960003638 dopamine Drugs 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- -1 3-cyanophenyl Chemical group 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 7
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 208000035475 disorder Diseases 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 239000001530 fumaric acid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 208000006011 Stroke Diseases 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 206010008118 cerebral infarction Diseases 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000011321 prophylaxis Methods 0.000 description 4
- 238000000159 protein binding assay Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- HAYMWIJSIJKEBS-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-[4-(2-methylquinolin-8-yl)piperazin-1-yl]butan-1-one Chemical compound C12=NC(C)=CC=C2C=CC=C1N(CC1)CCN1CCCC(=O)C1=CC=C(F)C=C1 HAYMWIJSIJKEBS-UHFFFAOYSA-N 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003693 atypical antipsychotic agent Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000002490 cerebral effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229940076279 serotonin Drugs 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZORSXSRUAULINY-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-(4-quinolin-8-ylpiperazin-1-yl)butan-1-one Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2C3=NC=CC=C3C=CC=2)CC1 ZORSXSRUAULINY-UHFFFAOYSA-N 0.000 description 2
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 2
- HXAOUYGZEOZTJO-UHFFFAOYSA-N 4-chloro-1-(4-fluorophenyl)butan-1-one Chemical compound FC1=CC=C(C(=O)CCCCl)C=C1 HXAOUYGZEOZTJO-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 208000031295 Animal disease Diseases 0.000 description 2
- 201000006474 Brain Ischemia Diseases 0.000 description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 description 2
- 206010008190 Cerebrovascular accident Diseases 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000000561 anti-psychotic effect Effects 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 208000015114 central nervous system disease Diseases 0.000 description 2
- 208000026106 cerebrovascular disease Diseases 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000012154 double-distilled water Substances 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 208000013403 hyperactivity Diseases 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- ZKZFPRUSWCYSGT-UHFFFAOYSA-N mazapertine Chemical compound CC(C)OC1=CC=CC=C1N1CCN(CC=2C=C(C=CC=2)C(=O)N2CCCCC2)CC1 ZKZFPRUSWCYSGT-UHFFFAOYSA-N 0.000 description 2
- 229950004476 mazapertine Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229960000607 ziprasidone Drugs 0.000 description 2
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 2
- WLFNETJSPCGPCW-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-(4-fluorophenyl)-4-(4-quinolin-8-ylpiperazin-1-yl)butan-1-ol Chemical compound OC(=O)\C=C\C(O)=O.C1CN(C=2C3=NC=CC=C3C=CC=2)CCN1CCCC(O)C1=CC=C(F)C=C1 WLFNETJSPCGPCW-WLHGVMLRSA-N 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- WBLSHIKDVMETTQ-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-(4-quinolin-8-ylpiperazin-1-yl)butan-1-one;dihydrate;trihydrochloride Chemical compound O.O.Cl.Cl.Cl.C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2C3=NC=CC=C3C=CC=2)CC1 WBLSHIKDVMETTQ-UHFFFAOYSA-N 0.000 description 1
- SJKRNBWFSFWVHZ-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-[4-(1h-indol-4-yl)piperazin-1-yl]butan-1-one Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 SJKRNBWFSFWVHZ-UHFFFAOYSA-N 0.000 description 1
- GPBONUQSVFNDGB-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-[4-(1h-indol-4-yl)piperazin-1-yl]butan-1-one;dihydrochloride Chemical compound Cl.Cl.C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 GPBONUQSVFNDGB-UHFFFAOYSA-N 0.000 description 1
- OOSZCNKVJAVHJI-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]piperazine Chemical compound C1=CC(F)=CC=C1CN1CCNCC1 OOSZCNKVJAVHJI-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- XPVCVGMLJYSAFN-UHFFFAOYSA-N 2-methyl-8-piperazin-1-ylquinoline Chemical compound C12=NC(C)=CC=C2C=CC=C1N1CCNCC1 XPVCVGMLJYSAFN-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 description 1
- YZKSXUIOKWQABW-UHFFFAOYSA-N 4-piperazin-1-yl-1h-indole Chemical compound C1CNCCN1C1=CC=CC2=C1C=CN2 YZKSXUIOKWQABW-UHFFFAOYSA-N 0.000 description 1
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 1
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 1
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DCUZDOXGNVJQQL-UHFFFAOYSA-N 8-piperazin-1-ylquinoline Chemical compound C1CNCCN1C1=CC=CC2=CC=CN=C12 DCUZDOXGNVJQQL-UHFFFAOYSA-N 0.000 description 1
- 206010000599 Acromegaly Diseases 0.000 description 1
- 201000010000 Agranulocytosis Diseases 0.000 description 1
- 206010001541 Akinesia Diseases 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 1
- 102000007527 Autoreceptors Human genes 0.000 description 1
- 108010071131 Autoreceptors Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- VQPMFTYCTANHFJ-UHFFFAOYSA-N C(C)(=O)O.C(C)(=O)O.C(C=CC(=O)O)(=O)O Chemical compound C(C)(=O)O.C(C)(=O)O.C(C=CC(=O)O)(=O)O VQPMFTYCTANHFJ-UHFFFAOYSA-N 0.000 description 1
- 208000009132 Catalepsy Diseases 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 208000012239 Developmental disease Diseases 0.000 description 1
- 208000014094 Dystonic disease Diseases 0.000 description 1
- 208000030814 Eating disease Diseases 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010058359 Hypogonadism Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 102000015636 Oligopeptides Human genes 0.000 description 1
- 108010038807 Oligopeptides Proteins 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010037180 Psychiatric symptoms Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 206010047853 Waxy flexibility Diseases 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 229940005529 antipsychotics Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 229940005530 anxiolytics Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 description 1
- 229960002495 buspirone Drugs 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 1
- 229960004170 clozapine Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 230000003931 cognitive performance Effects 0.000 description 1
- 231100000867 compulsive behavior Toxicity 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004212 difluorophenyl group Chemical group 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 235000014632 disordered eating Nutrition 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 239000000442 dopamine 2 receptor blocking agent Substances 0.000 description 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 208000010118 dystonia Diseases 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 229960003133 ergot alkaloid Drugs 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 230000002197 limbic effect Effects 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- BKTTWZADZNUOBW-UHFFFAOYSA-N roxindole Chemical compound C=12[CH]C(O)=CC=C2N=CC=1CCCCN(CC=1)CCC=1C1=CC=CC=C1 BKTTWZADZNUOBW-UHFFFAOYSA-N 0.000 description 1
- 229950000366 roxindole Drugs 0.000 description 1
- 230000000698 schizophrenic effect Effects 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([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
- 239000003723 serotonin 1A agonist Substances 0.000 description 1
- 239000003521 serotonin 5-HT1 receptor agonist Substances 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 230000011273 social behavior Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent 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
- C07D401/02—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
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10043659A DE10043659A1 (de) | 2000-09-05 | 2000-09-05 | Arylpiperazinderivate |
PCT/EP2001/009108 WO2002020491A1 (de) | 2000-09-05 | 2001-08-07 | Arylpiperazinderivate und deren verwendung als psychopharmaka |
Publications (1)
Publication Number | Publication Date |
---|---|
SK3612003A3 true SK3612003A3 (en) | 2003-07-01 |
Family
ID=7655009
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK361-2003A SK3612003A3 (en) | 2000-09-05 | 2001-08-07 | Arylpiperazine derivatives and their use as psychotropic agents |
Country Status (15)
Country | Link |
---|---|
US (1) | US20040014972A1 (zh) |
EP (1) | EP1326842A1 (zh) |
KR (1) | KR20030024913A (zh) |
CN (1) | CN1452614A (zh) |
AU (1) | AU2001291744A1 (zh) |
BR (1) | BR0113581A (zh) |
CA (1) | CA2421219A1 (zh) |
CZ (1) | CZ2003809A3 (zh) |
DE (1) | DE10043659A1 (zh) |
MX (1) | MXPA03001826A (zh) |
NO (1) | NO20030998D0 (zh) |
PL (1) | PL360289A1 (zh) |
SK (1) | SK3612003A3 (zh) |
WO (1) | WO2002020491A1 (zh) |
ZA (1) | ZA200302636B (zh) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1408976B3 (en) | 2001-07-20 | 2010-08-25 | Psychogenics Inc. | Treatment for attention-deficit hyperactivity disorder |
WO2004082570A2 (en) * | 2003-03-17 | 2004-09-30 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with dopamine receptor d2 (drd2) |
AU2004249621B2 (en) * | 2003-06-23 | 2009-08-06 | Dainippon Sumitomo Pharma Co., Ltd. | Therapeutic agent for senile dementia |
ES2250000B1 (es) * | 2004-09-29 | 2007-06-01 | Medichem, S.A. | Procedimiento para la preparacion de ziprasidona. |
ES2250001B1 (es) * | 2004-09-29 | 2007-06-01 | Medichem, S.A. | Proceso para la purificacion de ziprasidona. |
KR100660142B1 (ko) * | 2005-01-24 | 2006-12-20 | 이명섭 | 건식 모래 생산 방법 및 그 시스템 |
TWI320783B (en) | 2005-04-14 | 2010-02-21 | Otsuka Pharma Co Ltd | Heterocyclic compound |
TW200800959A (en) * | 2005-06-10 | 2008-01-01 | Wyeth Corp | Piperazine-piperidine antagonists and agonists of the 5-HT1a receptor |
TW200808730A (en) * | 2006-06-09 | 2008-02-16 | Wyeth Corp | Process for synthesizing piperazine-piperidine compounds |
CL2007003410A1 (es) * | 2006-11-28 | 2008-04-11 | Wyeth Corp | Compuestos derivados de 5-fluoro-8-{4-[4-(6-metoxiquinolin-8-il)piperazin-1-il]piperidin-1-il}quinolina; procedimiento de preparacion; compuestos intermediarios; procedimiento de preparacion; composicion farmaceutica; y uso en el tratamiento de trast |
UA100684C2 (uk) | 2007-03-15 | 2013-01-25 | Новартіс Аг | Похідні бензилу та піридинілу як модулятори сигнального шляху hedgehog |
US20100041663A1 (en) | 2008-07-18 | 2010-02-18 | Novartis Ag | Organic Compounds as Smo Inhibitors |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK148392D0 (da) * | 1992-12-09 | 1992-12-09 | Lundbeck & Co As H | Heterocykliske forbindelser |
JP3185222B2 (ja) * | 1997-01-21 | 2001-07-09 | ウェルファイド株式会社 | チオフェン化合物およびその医薬用途 |
ES2128266B1 (es) * | 1997-07-08 | 2000-01-16 | Vita Invest Sa | Compuestos derivados de tiofeno y benzotiofeno y utilizacion y composicion correspondientes. |
EP0900792B1 (en) * | 1997-09-02 | 2003-10-29 | Duphar International Research B.V | Piperazine and piperidine derivatives as 5-HT1A and dopamine D2-receptor (ant)agonists |
-
2000
- 2000-09-05 DE DE10043659A patent/DE10043659A1/de not_active Withdrawn
-
2001
- 2001-08-07 US US10/363,168 patent/US20040014972A1/en not_active Abandoned
- 2001-08-07 CN CN01815154A patent/CN1452614A/zh active Pending
- 2001-08-07 EP EP01971882A patent/EP1326842A1/de not_active Withdrawn
- 2001-08-07 KR KR10-2003-7002743A patent/KR20030024913A/ko not_active Application Discontinuation
- 2001-08-07 CZ CZ2003809A patent/CZ2003809A3/cs unknown
- 2001-08-07 BR BR0113581-3A patent/BR0113581A/pt not_active Application Discontinuation
- 2001-08-07 PL PL36028901A patent/PL360289A1/xx unknown
- 2001-08-07 CA CA002421219A patent/CA2421219A1/en not_active Abandoned
- 2001-08-07 SK SK361-2003A patent/SK3612003A3/sk unknown
- 2001-08-07 AU AU2001291744A patent/AU2001291744A1/en not_active Abandoned
- 2001-08-07 MX MXPA03001826A patent/MXPA03001826A/es unknown
- 2001-08-07 WO PCT/EP2001/009108 patent/WO2002020491A1/de not_active Application Discontinuation
-
2003
- 2003-03-04 NO NO20030998A patent/NO20030998D0/no unknown
- 2003-04-03 ZA ZA200302636A patent/ZA200302636B/en unknown
Also Published As
Publication number | Publication date |
---|---|
EP1326842A1 (de) | 2003-07-16 |
AU2001291744A1 (en) | 2002-03-22 |
MXPA03001826A (es) | 2003-06-04 |
DE10043659A1 (de) | 2002-03-14 |
KR20030024913A (ko) | 2003-03-26 |
BR0113581A (pt) | 2003-07-15 |
CZ2003809A3 (cs) | 2003-06-18 |
NO20030998L (no) | 2003-03-04 |
NO20030998D0 (no) | 2003-03-04 |
CA2421219A1 (en) | 2003-03-03 |
CN1452614A (zh) | 2003-10-29 |
ZA200302636B (en) | 2004-09-08 |
US20040014972A1 (en) | 2004-01-22 |
PL360289A1 (en) | 2004-09-06 |
WO2002020491A1 (de) | 2002-03-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP3880645B2 (ja) | アミノ(チオ)エーテル誘導体 | |
EP0648767B1 (de) | Piperidine und Piperazine, die Wirkungen auf das z.n.s. Zeigen | |
JP3834098B2 (ja) | ベンゾニトリル類およびベンゾフルオリド類 | |
SK282708B6 (sk) | Derivát piperazínu so selektivitou pre D-4 receptor, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje | |
RU2213743C2 (ru) | Производное тиенилазолилалкоксиэтанамина, способ его получения (варианты), фармацевтическая композиция, промежуточный продукт и способ его получения (варианты) | |
EP0683166B1 (de) | 3-Indolylpiperidine | |
SK352000A3 (en) | Piperazine derivatives, process for its preparation and pharmaceutical composition containing same | |
JPH05502682A (ja) | ピペラジン誘導体 | |
EP0529462A1 (de) | Benzodioxanderivate | |
SK3612003A3 (en) | Arylpiperazine derivatives and their use as psychotropic agents | |
EP0007399B1 (de) | Indolalkylamine, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung | |
SK77693A3 (en) | 1,4-benzodioxan derivatives, process for their preparation and their pharmaceutical compositions | |
CA2128380C (en) | 4-aryloxy- and 4-arylthiopiperidine derivatives | |
JP2006527707A (ja) | セロトニン再取り込み阻害剤としてのインドール誘導体 | |
EP1400510A1 (en) | Cyclic diamine compounds having fused-ring groups | |
SK17122002A3 (sk) | Derivát heterocyklického aminoalkylpyridínu ako psychofarmaceutické činidlo, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje | |
SK2942003A3 (en) | Chromenone derivatives and their use for treating diseases in conjunction with 5-HTA1 receptors and/or dopamine D2 receptors | |
US6333339B1 (en) | 3-Benzylpiperidine | |
JP2014139175A (ja) | 治療化合物 | |
DE2910367A1 (de) | Indolalkylamine, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung | |
CZ450999A3 (cs) | Derivát 3-benzylpiperidinu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje |