JP2000503972A - １―ピラゾール―３―イルエチル―４―インドール―３―イルピペリジン - Google Patents
１―ピラゾール―３―イルエチル―４―インドール―３―イルピペリジンInfo
- Publication number
- JP2000503972A JP2000503972A JP9526493A JP52649397A JP2000503972A JP 2000503972 A JP2000503972 A JP 2000503972A JP 9526493 A JP9526493 A JP 9526493A JP 52649397 A JP52649397 A JP 52649397A JP 2000503972 A JP2000503972 A JP 2000503972A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- ethyl
- indole
- pyrazolyl
- piperidyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- YLRRJIXSMHWUEC-UHFFFAOYSA-N 3-[1-[1-(1h-pyrazol-5-yl)ethyl]piperidin-4-yl]-1h-indole Chemical compound C1CC(C=2C3=CC=CC=C3NC=2)CCN1C(C)C1=CC=NN1 YLRRJIXSMHWUEC-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 239000011737 fluorine Substances 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 5
- -1 6-fluoro-3- (1- (2- (5-methyl-3-pyrazolyl) ethyl) -4-piperidyl) indole 6-methoxy-3- (1- (2- (5-methyl-3-pyrazolyl) ethyl) -4-piperidyl) indole Chemical compound 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 9
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 210000003169 central nervous system Anatomy 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- CEBGZJBXVJKVIV-UHFFFAOYSA-N 3-[1-[2-(5-methyl-1h-pyrazol-3-yl)ethyl]piperidin-4-yl]-1h-indole Chemical compound N1C(C)=CC(CCN2CCC(CC2)C=2C3=CC=CC=C3NC=2)=N1 CEBGZJBXVJKVIV-UHFFFAOYSA-N 0.000 claims description 2
- SFMUSFVDBRNZKM-UHFFFAOYSA-N 3-[1-[2-(5-methyl-1h-pyrazol-3-yl)ethyl]piperidin-4-yl]-1h-indole-5-carbonitrile Chemical compound N1C(C)=CC(CCN2CCC(CC2)C=2C3=CC(=CC=C3NC=2)C#N)=N1 SFMUSFVDBRNZKM-UHFFFAOYSA-N 0.000 claims description 2
- OATHMUXGLGOSFN-UHFFFAOYSA-N 5-fluoro-3-[1-[2-(5-methyl-1h-pyrazol-3-yl)ethyl]piperidin-4-yl]-1h-indole Chemical compound N1C(C)=CC(CCN2CCC(CC2)C=2C3=CC(F)=CC=C3NC=2)=N1 OATHMUXGLGOSFN-UHFFFAOYSA-N 0.000 claims description 2
- BGDSHWHGAUKHQA-UHFFFAOYSA-N 5-fluoro-3-[1-[2-[3-(4-fluorophenyl)-5-methyl-1h-pyrazol-4-yl]ethyl]piperidin-4-yl]-1h-indole Chemical compound C1CC(C=2C3=CC(F)=CC=C3NC=2)CCN1CCC1=C(C)NN=C1C1=CC=C(F)C=C1 BGDSHWHGAUKHQA-UHFFFAOYSA-N 0.000 claims description 2
- YXUNDZSEMSIBNE-UHFFFAOYSA-N 7-ethyl-3-[1-[2-(5-methyl-1h-pyrazol-3-yl)ethyl]piperidin-4-yl]-1h-indole Chemical compound C=1NC=2C(CC)=CC=CC=2C=1C(CC1)CCN1CCC=1C=C(C)NN=1 YXUNDZSEMSIBNE-UHFFFAOYSA-N 0.000 claims description 2
- SUGXJTXDXQSTOM-UHFFFAOYSA-N FC=1C=C2C(=CN(C2=CC1)C)C1CCN(CC1)CCC1=NNC(=C1)C Chemical compound FC=1C=C2C(=CN(C2=CC1)C)C1CCN(CC1)CCC1=NNC(=C1)C SUGXJTXDXQSTOM-UHFFFAOYSA-N 0.000 claims description 2
- 230000003042 antagnostic effect Effects 0.000 claims description 2
- 229960003638 dopamine Drugs 0.000 claims description 2
- 230000000862 serotonergic effect Effects 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 2
- GQMYQEAXTITUAE-UHFFFAOYSA-N 1H-indole-5-carboxamide Chemical compound NC(=O)C1=CC=C2NC=CC2=C1 GQMYQEAXTITUAE-UHFFFAOYSA-N 0.000 claims 1
- YHYLDEVWYOFIJK-UHFFFAOYSA-N 1h-indole-5-carbonitrile Chemical compound N#CC1=CC=C2NC=CC2=C1 YHYLDEVWYOFIJK-UHFFFAOYSA-N 0.000 claims 1
- GTNSQXVLBNZABY-UHFFFAOYSA-N 3-[1-[2-(5-methyl-1h-pyrazol-3-yl)ethyl]piperidin-4-yl]-1h-indole-5-carboxamide Chemical compound N1C(C)=CC(CCN2CCC(CC2)C=2C3=CC(=CC=C3NC=2)C(N)=O)=N1 GTNSQXVLBNZABY-UHFFFAOYSA-N 0.000 claims 1
- JMQGRRYBZZSUNR-UHFFFAOYSA-N 4-fluoro-3-[1-[2-(5-methyl-1h-pyrazol-3-yl)ethyl]piperidin-4-yl]-1h-indole Chemical compound N1C(C)=CC(CCN2CCC(CC2)C=2C3=C(F)C=CC=C3NC=2)=N1 JMQGRRYBZZSUNR-UHFFFAOYSA-N 0.000 claims 1
- SWRVUHGAIINOHL-UHFFFAOYSA-N 4-fluoro-3-[1-[2-[3-(4-fluorophenyl)-5-methyl-1h-pyrazol-4-yl]ethyl]piperidin-4-yl]-1h-indole Chemical compound C1CC(C=2C3=C(F)C=CC=C3NC=2)CCN1CCC1=C(C)NN=C1C1=CC=C(F)C=C1 SWRVUHGAIINOHL-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 230000004936 stimulating effect Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 5
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 abstract 4
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 125000006239 protecting group Chemical group 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- UNCXOQBRFONUFS-UHFFFAOYSA-N 7-ethyl-3-piperidin-4-yl-1h-indole Chemical compound C=1NC=2C(CC)=CC=CC=2C=1C1CCNCC1 UNCXOQBRFONUFS-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- FVVOOKWAIOTJHY-UHFFFAOYSA-N 3-(2-chloroethyl)-5-methyl-1h-pyrazole Chemical compound CC1=CC(CCCl)=NN1 FVVOOKWAIOTJHY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 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
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XSRSEEZCZRABDP-UHFFFAOYSA-N 2-(5-methyl-1h-pyrazol-3-yl)acetic acid Chemical compound CC1=CC(CC(O)=O)=NN1 XSRSEEZCZRABDP-UHFFFAOYSA-N 0.000 description 3
- WPHFQZQZJWGICL-UHFFFAOYSA-N 2-(5-methyl-1h-pyrazol-3-yl)acetohydrazide Chemical compound CC1=CC(CC(=O)NN)=NN1 WPHFQZQZJWGICL-UHFFFAOYSA-N 0.000 description 3
- OPEPDLKKQYIKIS-UHFFFAOYSA-N 2-(5-methyl-1h-pyrazol-3-yl)ethanol Chemical compound CC1=CC(CCO)=NN1 OPEPDLKKQYIKIS-UHFFFAOYSA-N 0.000 description 3
- GYHBVAHWGBJKHA-UHFFFAOYSA-N 6-methylpyran-2,4-dione Chemical compound CC1=CC(=O)CC(=O)O1 GYHBVAHWGBJKHA-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009739 binding Methods 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000003795 chemical substances by application 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
- 239000013078 crystal Substances 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000007429 general method Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 2
- KUUVBKVEIXUBHP-UHFFFAOYSA-N 3-(1-benzyl-3,6-dihydro-2h-pyridin-4-yl)-7-ethyl-1h-indole Chemical compound C=1NC=2C(CC)=CC=CC=2C=1C(CC1)=CCN1CC1=CC=CC=C1 KUUVBKVEIXUBHP-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- AKNIYUPCDLOSEC-UHFFFAOYSA-N CC1=CC(=NN1)CCN1CCC(CC1)N1C=CC2=CC=CC=C12 Chemical compound CC1=CC(=NN1)CCN1CCC(CC1)N1C=CC2=CC=CC=C12 AKNIYUPCDLOSEC-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- 229910052744 lithium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000012452 mother liquor Substances 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
- 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
- 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
- 210000001577 neostriatum Anatomy 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 208000019906 panic disease Diseases 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
- 238000005897 peptide coupling reaction Methods 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000006611 pharmacological activation Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 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
- 229910052705 radium Inorganic materials 0.000 description 1
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
- 210000001609 raphe nuclei Anatomy 0.000 description 1
- 201000000980 schizophrenia Diseases 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
- 229940076279 serotonin Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl 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
- 229960002622 triacetin Drugs 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 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
- C07D401/14—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
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19602505.2 | 1996-01-25 | ||
| DE19602505A DE19602505A1 (de) | 1996-01-25 | 1996-01-25 | 1-(Pyrazol-4-Indol-3-yl)-Piperidine |
| PCT/EP1997/000187 WO1997027186A1 (de) | 1996-01-25 | 1997-01-17 | 1-(pyrazol-3-yl-ethyl)-4-(indol-3-yl)-piperidine als das zentralnervensystem beeinflussende mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2000503972A true JP2000503972A (ja) | 2000-04-04 |
Family
ID=7783568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9526493A Pending JP2000503972A (ja) | 1996-01-25 | 1997-01-17 | １―ピラゾール―３―イルエチル―４―インドール―３―イルピペリジン |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0879234A1 (cs) |
| JP (1) | JP2000503972A (cs) |
| KR (1) | KR19990081970A (cs) |
| CN (1) | CN1209807A (cs) |
| AR (1) | AR005549A1 (cs) |
| AU (1) | AU715785B2 (cs) |
| BR (1) | BR9707467A (cs) |
| CA (1) | CA2244136A1 (cs) |
| CZ (1) | CZ231898A3 (cs) |
| DE (1) | DE19602505A1 (cs) |
| HU (1) | HUP9900980A2 (cs) |
| NO (1) | NO983439L (cs) |
| PL (1) | PL328228A1 (cs) |
| SK (1) | SK99298A3 (cs) |
| WO (1) | WO1997027186A1 (cs) |
| ZA (1) | ZA97572B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014510133A (ja) * | 2011-04-06 | 2014-04-24 | エルジー・ライフ・サイエンシーズ・リミテッド | １−（３−シアノ−１−イソプロピル−インドール−５−イル）ピラゾール−４−カルボン酸の結晶形とその製造方法 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2219385T3 (es) * | 1999-09-09 | 2004-12-01 | H. Lundbeck A/S | Indoles sustituidos con 5-aminoalquilo y 5-aminocarbonilo. |
| RU2252939C2 (ru) | 1999-11-10 | 2005-05-27 | Такеда Кемикал Индастриз, Лтд. | 5-членные n-гетероциклические соединения, обладающие гипогликемической и гиполипидемической активностью |
| NZ524193A (en) | 2000-08-14 | 2004-12-24 | Ortho Mcneil Pharm Inc | Substituted pyrazoles |
| US7332494B2 (en) | 2000-08-14 | 2008-02-19 | Janssen Pharmaceutica, N.V. | Method for treating allergies using substituted pyrazoles |
| HUP0402124A2 (hu) * | 2001-11-14 | 2005-02-28 | Merck Patent Gmbh | Pszichofarmakológiában alkalmazható pirazolszármazékok, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények |
| JP4885967B2 (ja) | 2005-10-11 | 2012-02-29 | エフ．ホフマン−ラ ロシュ アーゲー | イミダゾベンゾジアゼピン誘導体 |
| US20080015214A1 (en) * | 2005-10-24 | 2008-01-17 | Bignan Gilles C | 3-piperidin-4-yl-indole orl-1 receptor modulators |
| KR20220060488A (ko) * | 2020-11-04 | 2022-05-11 | 주식회사 엘지화학 | 1-(3-시아노-1-아이소프로필-인돌-5-일)피라졸-4-카르복실산의 결정성 입자의 제조방법 및 이를 포함하는 약학적 조성물 |
| WO2025021120A1 (zh) * | 2023-07-24 | 2025-01-30 | 上海翊石医药科技有限公司 | 一类5-ht2a受体激动剂及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2060816C3 (de) * | 1970-12-10 | 1980-09-04 | Merck Patent Gmbh, 6100 Darmstadt | 4-Phenylpiperidinderivate Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen enthaltend diese Verbindungen |
| DE2258033A1 (de) * | 1972-11-27 | 1974-05-30 | Merck Patent Gmbh | Verfahren zur herstellung von pyrazolderivaten |
| GB8719167D0 (en) * | 1987-08-13 | 1987-09-23 | Glaxo Group Ltd | Chemical compounds |
| US5045550A (en) * | 1990-09-20 | 1991-09-03 | Warner-Lambert Co. | Substituted tetrahydropyridines as central nervous system agents |
| US5521196A (en) * | 1994-10-05 | 1996-05-28 | Eli Lilly And Company | 5-HT1F agonists for the treatment of migraine |
-
1996
- 1996-01-25 DE DE19602505A patent/DE19602505A1/de not_active Withdrawn
-
1997
- 1997-01-17 SK SK992-98A patent/SK99298A3/sk unknown
- 1997-01-17 WO PCT/EP1997/000187 patent/WO1997027186A1/de not_active Ceased
- 1997-01-17 PL PL97328228A patent/PL328228A1/xx unknown
- 1997-01-17 AU AU14432/97A patent/AU715785B2/en not_active Ceased
- 1997-01-17 HU HU9900980A patent/HUP9900980A2/hu unknown
- 1997-01-17 CN CN97191852A patent/CN1209807A/zh active Pending
- 1997-01-17 JP JP9526493A patent/JP2000503972A/ja active Pending
- 1997-01-17 KR KR1019980705688A patent/KR19990081970A/ko not_active Withdrawn
- 1997-01-17 BR BR9707467A patent/BR9707467A/pt unknown
- 1997-01-17 EP EP97901049A patent/EP0879234A1/de not_active Withdrawn
- 1997-01-17 CA CA002244136A patent/CA2244136A1/en not_active Abandoned
- 1997-01-17 CZ CZ982318A patent/CZ231898A3/cs unknown
- 1997-01-23 ZA ZA9700572A patent/ZA97572B/xx unknown
- 1997-01-24 AR ARP970100297A patent/AR005549A1/es unknown
-
1998
- 1998-07-24 NO NO983439A patent/NO983439L/no unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014510133A (ja) * | 2011-04-06 | 2014-04-24 | エルジー・ライフ・サイエンシーズ・リミテッド | １−（３−シアノ−１−イソプロピル−インドール−５−イル）ピラゾール−４−カルボン酸の結晶形とその製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU715785B2 (en) | 2000-02-10 |
| SK99298A3 (en) | 1999-01-11 |
| HUP9900980A2 (hu) | 1999-07-28 |
| CZ231898A3 (cs) | 1998-10-14 |
| BR9707467A (pt) | 1999-07-20 |
| PL328228A1 (en) | 1999-01-18 |
| WO1997027186A1 (de) | 1997-07-31 |
| EP0879234A1 (de) | 1998-11-25 |
| CA2244136A1 (en) | 1997-07-31 |
| NO983439L (no) | 1998-09-25 |
| KR19990081970A (ko) | 1999-11-15 |
| AR005549A1 (es) | 1999-06-23 |
| ZA97572B (en) | 1997-08-04 |
| CN1209807A (zh) | 1999-03-03 |
| DE19602505A1 (de) | 1997-07-31 |
| AU1443297A (en) | 1997-08-20 |
| NO983439D0 (no) | 1998-07-24 |
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