ES2362871T3 - Indoles sustituidos y su uso como inhibidores de la reabsorción de 5ht y como ligandos 5-ht. - Google Patents
Indoles sustituidos y su uso como inhibidores de la reabsorción de 5ht y como ligandos 5-ht. Download PDFInfo
- Publication number
- ES2362871T3 ES2362871T3 ES03720455T ES03720455T ES2362871T3 ES 2362871 T3 ES2362871 T3 ES 2362871T3 ES 03720455 T ES03720455 T ES 03720455T ES 03720455 T ES03720455 T ES 03720455T ES 2362871 T3 ES2362871 T3 ES 2362871T3
- Authority
- ES
- Spain
- Prior art keywords
- propyl
- indole
- carbonitrile
- mhet
- mar
- 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.)
- Expired - Lifetime
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- 150000002475 indoles Chemical class 0.000 title abstract description 3
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 title description 18
- 239000003112 inhibitor Substances 0.000 title description 3
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- 208000023105 Huntington disease Diseases 0.000 claims abstract description 5
- 230000007574 infarction Effects 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 167
- 125000004432 carbon atom Chemical group C* 0.000 claims description 82
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 229910052760 oxygen Inorganic materials 0.000 claims description 36
- 229910052717 sulfur Inorganic materials 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 19
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 239000012453 solvate Substances 0.000 claims description 18
- 101100134925 Gallus gallus COR6 gene Proteins 0.000 claims description 15
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
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- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
- 229910021645 metal ion Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- GEFZYOPEZYLNCJ-UHFFFAOYSA-N 4-[1-[3-(3-cyano-1h-indol-6-yl)propyl]piperidin-4-yl]oxybenzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC1CCN(CCCC=2C=C3NC=C(C3=CC=2)C#N)CC1 GEFZYOPEZYLNCJ-UHFFFAOYSA-N 0.000 claims description 4
- MOWLYAKTKWMUQE-UHFFFAOYSA-N 4-[3-[4-(4-fluorophenoxy)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1OC1CCN(CCCC=2C=3C(C#N)=CNC=3C=CC=2)CC1 MOWLYAKTKWMUQE-UHFFFAOYSA-N 0.000 claims description 4
- ZIYLVELXOPYOGF-UHFFFAOYSA-N 4-[3-[4-[(2,4-difluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound FC1=CC(F)=CC=C1CC1CCN(CCCC=2C=3C(C#N)=CNC=3C=CC=2)CC1 ZIYLVELXOPYOGF-UHFFFAOYSA-N 0.000 claims description 4
- PXELOZKDYKBIJY-UHFFFAOYSA-N 4-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1CC1CCN(CCCC=2C=3C(C#N)=CNC=3C=CC=2)CC1 PXELOZKDYKBIJY-UHFFFAOYSA-N 0.000 claims description 4
- BFLZMCZQKOZXEG-UHFFFAOYSA-N 5-[3-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)propyl]-1h-indole-3-carbonitrile Chemical compound C1CN(CCCC=2C=C3C(C#N)=CNC3=CC=2)CCC11C(=O)NCN1C1=CC=CC=C1 BFLZMCZQKOZXEG-UHFFFAOYSA-N 0.000 claims description 4
- LGAAYAVRUVTFKS-UHFFFAOYSA-N 5-[3-[4-(1h-indol-3-yl)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC=C2C(C3CCN(CC3)CCCC3=CC=C4NC=C(C4=C3)C#N)=CNC2=C1 LGAAYAVRUVTFKS-UHFFFAOYSA-N 0.000 claims description 4
- QPLGCQCJAORPKN-UHFFFAOYSA-N 5-[3-[4-(4-fluoro-1h-indol-3-yl)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=C2NC=C(C#N)C2=CC(CCCN2CCC(CC2)C2=CNC=3C=CC=C(C2=3)F)=C1 QPLGCQCJAORPKN-UHFFFAOYSA-N 0.000 claims description 4
- VVVQINXECOLIRC-UHFFFAOYSA-N 5-[3-[4-(4-fluorophenoxy)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1OC1CCN(CCCC=2C=C3C(C#N)=CNC3=CC=2)CC1 VVVQINXECOLIRC-UHFFFAOYSA-N 0.000 claims description 4
- KDNJQJFKQOOBMJ-UHFFFAOYSA-N 5-[3-[4-(5-cyano-1h-indol-3-yl)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=C(C#N)C=C2C(C3CCN(CC3)CCCC3=CC=C4NC=C(C4=C3)C#N)=CNC2=C1 KDNJQJFKQOOBMJ-UHFFFAOYSA-N 0.000 claims description 4
- FICXHYVHQPSCLK-UHFFFAOYSA-N 5-[3-[4-(5-fluoro-1h-indol-3-yl)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=C2NC=C(C#N)C2=CC(CCCN2CCC(CC2)C2=CNC3=CC=C(C=C32)F)=C1 FICXHYVHQPSCLK-UHFFFAOYSA-N 0.000 claims description 4
- JWJKRLHAJXYPOD-UHFFFAOYSA-N 5-[3-[4-(6-fluoro-1h-indol-3-yl)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=C2NC=C(C#N)C2=CC(CCCN2CCC(CC2)C=2C3=CC=C(C=C3NC=2)F)=C1 JWJKRLHAJXYPOD-UHFFFAOYSA-N 0.000 claims description 4
- WJQQNOKNWKZKEI-UHFFFAOYSA-N 5-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1CC1CCN(CCCC=2C=C3C(C#N)=CNC3=CC=2)CC1 WJQQNOKNWKZKEI-UHFFFAOYSA-N 0.000 claims description 4
- MGWLYPWRAOWAGO-UHFFFAOYSA-N 6-[3-[4-(4-fluorophenoxy)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1OC1CCN(CCCC=2C=C3NC=C(C3=CC=2)C#N)CC1 MGWLYPWRAOWAGO-UHFFFAOYSA-N 0.000 claims description 4
- GAOVZTNLDBPBEH-UHFFFAOYSA-N 6-[3-[4-[(2,4-difluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound FC1=CC(F)=CC=C1CC1CCN(CCCC=2C=C3NC=C(C3=CC=2)C#N)CC1 GAOVZTNLDBPBEH-UHFFFAOYSA-N 0.000 claims description 4
- DMWILBQJRHOAJR-UHFFFAOYSA-N 6-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1CC1CCN(CCCC=2C=C3NC=C(C3=CC=2)C#N)CC1 DMWILBQJRHOAJR-UHFFFAOYSA-N 0.000 claims description 4
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- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
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- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 4
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- 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 4
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Classifications
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- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10217006A DE10217006A1 (de) | 2002-04-16 | 2002-04-16 | Substituierte Indole |
| DE10217006 | 2002-04-16 |
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| ES2362871T3 true ES2362871T3 (es) | 2011-07-14 |
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| ES03720455T Expired - Lifetime ES2362871T3 (es) | 2002-04-16 | 2003-04-11 | Indoles sustituidos y su uso como inhibidores de la reabsorción de 5ht y como ligandos 5-ht. |
Country Status (10)
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| JP (1) | JP2005523310A (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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-
2002
- 2002-04-16 DE DE10217006A patent/DE10217006A1/de not_active Withdrawn
-
2003
- 2003-04-11 JP JP2003584042A patent/JP2005523310A/ja active Pending
- 2003-04-11 DK DK03720455.9T patent/DK1497279T3/da active
- 2003-04-11 DE DE50313528T patent/DE50313528D1/de not_active Expired - Lifetime
- 2003-04-11 AT AT03720455T patent/ATE501133T1/de active
- 2003-04-11 US US10/511,155 patent/US7572796B2/en not_active Expired - Fee Related
- 2003-04-11 WO PCT/EP2003/003806 patent/WO2003087086A2/de not_active Ceased
- 2003-04-11 EP EP03720455A patent/EP1497279B1/de not_active Expired - Lifetime
- 2003-04-11 CA CA2482655A patent/CA2482655C/en not_active Expired - Fee Related
- 2003-04-11 ES ES03720455T patent/ES2362871T3/es not_active Expired - Lifetime
- 2003-04-11 AU AU2003224064A patent/AU2003224064A1/en not_active Abandoned
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2008
- 2008-10-03 US US12/245,416 patent/US8058277B2/en not_active Expired - Fee Related
-
2009
- 2009-07-29 US US12/511,320 patent/US20090291963A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20050153980A1 (en) | 2005-07-14 |
| US20090054459A1 (en) | 2009-02-26 |
| EP1497279A2 (de) | 2005-01-19 |
| AU2003224064A8 (en) | 2003-10-27 |
| CA2482655A1 (en) | 2003-10-23 |
| JP2005523310A (ja) | 2005-08-04 |
| CA2482655C (en) | 2011-08-16 |
| US8058277B2 (en) | 2011-11-15 |
| ATE501133T1 (de) | 2011-03-15 |
| DK1497279T3 (da) | 2011-06-14 |
| US7572796B2 (en) | 2009-08-11 |
| US20090291963A1 (en) | 2009-11-26 |
| WO2003087086A2 (de) | 2003-10-23 |
| AU2003224064A1 (en) | 2003-10-27 |
| DE10217006A1 (de) | 2003-11-06 |
| DE50313528D1 (de) | 2011-04-21 |
| WO2003087086A3 (de) | 2004-07-22 |
| EP1497279B1 (de) | 2011-03-09 |
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