KR19990081970A - 중추신경계에 작용하는 약물로서 사용되는 1-피라졸-3-일-에틸-4-인돌-3-일-피페리딘 - Google Patents

중추신경계에 작용하는 약물로서 사용되는 1-피라졸-3-일-에틸-4-인돌-3-일-피페리딘 Download PDF

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Publication number: KR19990081970A
Authority: KR; South Korea
Prior art keywords: formula; ethyl; methyl; pyrazolyl; indole
Prior art date: 1996-01-25
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

KR1019980705688A

Other languages

English (en)

Korean (ko)

Inventor

헨닝 뵈트허

요아킴 매르츠

게르트 바르토스지크

하르트무트 그라이너

위르겐 하르팅

크리스토프 제이프리트

Original Assignee

플레믹 크리스티안

메르크 파텐트 게엠베하

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.)

1996-01-25

Filing date

1997-01-17

Publication date

1999-11-15

1997-01-17 Application filed by 플레믹 크리스티안, 메르크 파텐트 게엠베하 filed Critical 플레믹 크리스티안

1999-11-15 Publication of KR19990081970A publication Critical patent/KR19990081970A/ko

Status Withdrawn legal-status Critical Current

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 4
239000003814 drug Substances 0.000 title claims description 11
229940079593 drug Drugs 0.000 title claims description 8
210000003169 central nervous system Anatomy 0.000 title claims description 4
150000003839 salts Chemical class 0.000 claims abstract description 19
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
229910052740 iodine Inorganic materials 0.000 claims abstract description 5
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
230000009471 action Effects 0.000 claims abstract description 3
MFOBKQAGVZYMON-UHFFFAOYSA-N cyanoformohydrazide Chemical compound NNC(=O)C#N MFOBKQAGVZYMON-UHFFFAOYSA-N 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 76
238000006243 chemical reaction Methods 0.000 claims description 33
238000000034 method Methods 0.000 claims description 29
239000002253 acid Substances 0.000 claims description 13
239000002585 base Substances 0.000 claims description 9
201000010099 disease Diseases 0.000 claims description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 5
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 4
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 description 3
239000012458 free base Substances 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
SOWAOELEDSOPON-UHFFFAOYSA-N 3-[1-[2-(5-methyl-1h-pyrazol-3-yl)ethyl]-3,6-dihydro-2h-pyridin-4-yl]-1h-indole-5-carbonitrile Chemical compound N1C(C)=CC(CCN2CC=C(CC2)C=2C3=CC(=CC=C3NC=2)C#N)=N1 SOWAOELEDSOPON-UHFFFAOYSA-N 0.000 claims description 2
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
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 description 2
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 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
GSSXMSVJROTFRH-UHFFFAOYSA-N 6-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=C(F)C=C3NC=2)=N1 GSSXMSVJROTFRH-UHFFFAOYSA-N 0.000 claims description 2
DGWWKEFUAKAWDM-UHFFFAOYSA-N 6-methoxy-3-[1-[2-(5-methyl-1h-pyrazol-3-yl)ethyl]piperidin-4-yl]-1h-indole Chemical compound C=1NC2=CC(OC)=CC=C2C=1C(CC1)CCN1CCC=1C=C(C)NN=1 DGWWKEFUAKAWDM-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
MRFSAMYQFVMTOK-UHFFFAOYSA-N 7-methoxy-3-[1-[2-(5-methyl-1h-pyrazol-3-yl)ethyl]piperidin-4-yl]-1h-indole Chemical compound C=1NC=2C(OC)=CC=CC=2C=1C(CC1)CCN1CCC=1C=C(C)NN=1 MRFSAMYQFVMTOK-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
239000002552 dosage form Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
230000001270 agonistic effect Effects 0.000 claims 1
238000006722 reduction reaction Methods 0.000 claims 1
239000007787 solid Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
-1 ethylidene, trimethylene Chemical group 0.000 description 37
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
125000006239 protecting group Chemical group 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 16
239000007858 starting material Substances 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
229910052739 hydrogen Inorganic materials 0.000 description 12
239000001257 hydrogen Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
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 9
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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000012043 crude product Substances 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
239000003826 tablet Substances 0.000 description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
238000010992 reflux Methods 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
FVVOOKWAIOTJHY-UHFFFAOYSA-N 3-(2-chloroethyl)-5-methyl-1h-pyrazole Chemical compound CC1=CC(CCCl)=NN1 FVVOOKWAIOTJHY-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
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 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
150000007513 acids Chemical class 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
238000004587 chromatography analysis Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
238000003797 solvolysis reaction Methods 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
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 3
GYHBVAHWGBJKHA-UHFFFAOYSA-N 6-methylpyran-2,4-dione Chemical compound CC1=CC(=O)CC(=O)O1 GYHBVAHWGBJKHA-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZPRMAYOAKKWBCH-UHFFFAOYSA-N FC=1C=C2C(=CN(C2=CC1)C)C1CCN(CC1)C(=O)OC(C)(C)C Chemical compound FC=1C=C2C(=CN(C2=CC1)C)C1CCN(CC1)C(=O)OC(C)(C)C ZPRMAYOAKKWBCH-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
241000700159 Rattus Species 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
125000003118 aryl group Chemical group 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
238000005859 coupling reaction Methods 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
239000012153 distilled water Substances 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
238000007327 hydrogenolysis reaction Methods 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
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
235000011118 potassium hydroxide Nutrition 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
108090000765 processed proteins & peptides Proteins 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 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
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 description 2
LQVWVPZIVGZUNP-UHFFFAOYSA-N 5-fluoro-1-methyl-3-piperidin-4-ylindole Chemical compound C12=CC(F)=CC=C2N(C)C=C1C1CCNCC1 LQVWVPZIVGZUNP-UHFFFAOYSA-N 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
208000000103 Anorexia Nervosa Diseases 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
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
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CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
230000029142 excretion Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007789 gas Substances 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
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
235000013773 glyceryl triacetate Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
230000036541 health Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 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
230000000971 hippocampal effect Effects 0.000 description 1
150000004678 hydrides Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
229960004502 levodopa Drugs 0.000 description 1
239000003446 ligand Substances 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 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
229960002510 mandelic acid Drugs 0.000 description 1
238000002483 medication Methods 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 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
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
239000011664 nicotinic acid Substances 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003204 osmotic effect Effects 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
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
235000019271 petrolatum Nutrition 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 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
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 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
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000003755 preservative agent Substances 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
230000001012 protector Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
150000003217 pyrazoles Chemical class 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
230000005855 radiation Effects 0.000 description 1
230000011514 reflex Effects 0.000 description 1
201000000980 schizophrenia Diseases 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
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
238000000926 separation method Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
235000011182 sodium carbonates Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 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
230000002194 synthesizing effect Effects 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
QYTJFOBUAJLXAR-UHFFFAOYSA-N tert-butyl 4-(5-fluoro-1h-indol-3-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CNC2=CC=C(F)C=C12 QYTJFOBUAJLXAR-UHFFFAOYSA-N 0.000 description 1
125000005425 toluyl 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
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 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
229910052722 tritium Inorganic materials 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
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 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)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Neurosurgery (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

KR1019980705688A 1996-01-25 1997-01-17 중추신경계에 작용하는 약물로서 사용되는 1-피라졸-3-일-에틸-4-인돌-3-일-피페리딘 Withdrawn KR19990081970A (ko)

Applications Claiming Priority (2)

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

Publications (1)

Publication Number	Publication Date
KR19990081970A true KR19990081970A (ko)	1999-11-15

Family

ID=7783568

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
KR1019980705688A Withdrawn KR19990081970A (ko)	1996-01-25	1997-01-17	중추신경계에 작용하는 약물로서 사용되는 1-피라졸-3-일-에틸-4-인돌-3-일-피페리딘

Country Status (16)

Country	Link
EP (1)	EP0879234A1 (fr)
JP (1)	JP2000503972A (fr)
KR (1)	KR19990081970A (fr)
CN (1)	CN1209807A (fr)
AR (1)	AR005549A1 (fr)
AU (1)	AU715785B2 (fr)
BR (1)	BR9707467A (fr)
CA (1)	CA2244136A1 (fr)
CZ (1)	CZ231898A3 (fr)
DE (1)	DE19602505A1 (fr)
HU (1)	HUP9900980A2 (fr)
NO (1)	NO983439L (fr)
PL (1)	PL328228A1 (fr)
SK (1)	SK99298A3 (fr)
WO (1)	WO1997027186A1 (fr)
ZA (1)	ZA97572B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2001021614A1 (fr) *	1999-09-09	2001-03-29	H. Lundbeck A/S	Indoles substitues 5-aminoalkyle et 5-aminocarbonyle
IL149493A0 (en)	1999-11-10	2002-11-10	Takeda Chemical Industries Ltd	5-membered n-heterocyclic compounds with hypoglycemic and hypolipidemic activity
EP1309591B1 (fr)	2000-08-14	2007-01-24	Ortho-McNeil Pharmaceutical, Inc.	Pyrazoles substitues
US7332494B2 (en)	2000-08-14	2008-02-19	Janssen Pharmaceutica, N.V.	Method for treating allergies using substituted pyrazoles
CN1585768A (zh) *	2001-11-14	2005-02-23	默克专利股份有限公司	作为精神药物的吡唑衍生物
CN101287738B (zh)	2005-10-11	2011-08-10	弗·哈夫曼-拉罗切有限公司	咪唑并苯并二氮杂*衍生物
JP2009515833A (ja) *	2005-10-24	2009-04-16	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	３−ピペリジン−４−イル−インドールｏｒｌ−１受容体モジュレーター
TWI548630B (zh) *	2011-04-06	2016-09-11	Ｌｇ生命科學有限公司	１－（３－氰基－１－異丙基－吲哚－５－基）吡唑－４－羧酸結晶型及其製造方法
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 (fr) *	2023-07-24	2025-01-30	上海翊石医药科技有限公司	Agoniste du récepteur 5-ht2a, son procédé de préparation et son utilisation

Family Cites Families (5)

* Cited by examiner, † Cited by third party
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 CA CA002244136A patent/CA2244136A1/fr not_active Abandoned
- 1997-01-17 HU HU9900980A patent/HUP9900980A2/hu unknown
- 1997-01-17 CN CN97191852A patent/CN1209807A/zh active Pending
- 1997-01-17 AU AU14432/97A patent/AU715785B2/en not_active Ceased
- 1997-01-17 CZ CZ982318A patent/CZ231898A3/cs unknown
- 1997-01-17 EP EP97901049A patent/EP0879234A1/fr not_active Withdrawn
- 1997-01-17 JP JP9526493A patent/JP2000503972A/ja active Pending
- 1997-01-17 KR KR1019980705688A patent/KR19990081970A/ko not_active Withdrawn
- 1997-01-17 WO PCT/EP1997/000187 patent/WO1997027186A1/fr not_active Ceased
- 1997-01-17 PL PL97328228A patent/PL328228A1/xx unknown
- 1997-01-17 SK SK992-98A patent/SK99298A3/sk unknown
- 1997-01-17 BR BR9707467A patent/BR9707467A/pt 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

Also Published As

Publication number	Publication date
NO983439L (no)	1998-09-25
NO983439D0 (no)	1998-07-24
PL328228A1 (en)	1999-01-18
WO1997027186A1 (fr)	1997-07-31
EP0879234A1 (fr)	1998-11-25
HUP9900980A2 (hu)	1999-07-28
SK99298A3 (en)	1999-01-11
BR9707467A (pt)	1999-07-20
CA2244136A1 (fr)	1997-07-31
CN1209807A (zh)	1999-03-03
AU715785B2 (en)	2000-02-10
JP2000503972A (ja)	2000-04-04
AU1443297A (en)	1997-08-20
ZA97572B (en)	1997-08-04
AR005549A1 (es)	1999-06-23
CZ231898A3 (cs)	1998-10-14
DE19602505A1 (de)	1997-07-31

Publication	Publication Date	Title
RU2132848C1 (ru)	1999-07-10	Производные пиперидина и пиперазина, способ их получения, содержащие их фармацевтические композиции и способ их получения
RU2168508C2 (ru)	2001-06-10	Бензонитрилы и бензофториды, способ их получения, фармацевтическая композиция, способ ее получения
KR100347849B1 (ko)	2002-11-16	유착수용체길항물질(iii)
KR880002625B1 (ko)	1988-12-07	글루타르이미드 유도체 및 그의 제조방법
HU220061B (hu)	2001-10-28	Eljárás indolszármazékok és az e vegyületeket tartalmazó gyógyszerkészítmények előállítására
KR100384978B1 (ko)	2003-09-02	유착수용체길항물질
KR20000005505A (ko)	2000-01-25	피페리딘 및 피롤리딘
KR19990081970A (ko)	1999-11-15	중추신경계에 작용하는 약물로서 사용되는 1-피라졸-3-일-에틸-4-인돌-3-일-피페리딘
CA2128380C (fr)	2005-04-12	Derives de la 4-aryloxy- et de la 4-arylthiopiperidine
PT1641787E (pt)	2007-08-01	Dicetopiperazinas substituídas e sua utilização como antagonistas da oxitocina
RU2175970C2 (ru)	2001-11-20	Производные пиперидинилметилоксазолидин-2-она, способ их получения и фармацевтическая композиция на их основе
JPS6330908B2 (fr)	1988-06-21
HU218274B (en)	2000-07-28	N,n'-bis hydroxyalkyl and alkoxyalkyl-pyridine-2,4-dicarboxylic acid diamide derivatives and pharmaceutical compositions comprising such compounds and process for producing them
US5817815A (en)	1998-10-06	Pharmacologically active enantiomers
MXPA96003567A (es)	1997-06-01	Derivados de la piperidinilmetiloxazolidin-2-ona
HU196993B (en)	1989-02-28	Process for producing hydroxy-indole esters and pharmaceuticals comprising same
US5262432A (en)	1993-11-16	Derivatives of 4-(hetero)arylmethyloxy phenyl diazole, a method of preparing them and use thereof in therapy
JPS62226977A (ja)	1987-10-05	ピリジン誘導体
AU718075B2 (en)	2000-04-06	Intermediates for the preparation of pharmacologically active enantiomers of triazolone compounds
JPH03173868A (ja)	1991-07-29	ピペリジンアクリル酸誘導体

Legal Events

Date	Code	Title	Description
1998-07-24	PA0105	International application	Patent event date: 19980724 Patent event code: PA01051R01D Comment text: International Patent Application
1999-11-15	PG1501	Laying open of application
2003-03-19	PC1203	Withdrawal of no request for examination
2003-03-19	WITN	Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid