JP2003528096A5 - - Google Patents
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- Publication number
- JP2003528096A5 JP2003528096A5 JP2001568934A JP2001568934A JP2003528096A5 JP 2003528096 A5 JP2003528096 A5 JP 2003528096A5 JP 2001568934 A JP2001568934 A JP 2001568934A JP 2001568934 A JP2001568934 A JP 2001568934A JP 2003528096 A5 JP2003528096 A5 JP 2003528096A5
- Authority
- JP
- Japan
- Prior art keywords
- decahydro
- methanone
- piperazin
- propyl
- methyl
- 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.)
- Granted
Links
- -1 Hydrogen Chemical class 0.000 description 41
- 150000001875 compounds Chemical class 0.000 description 11
- 239000002253 acid Substances 0.000 description 9
- 239000012458 free base Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 6
- 125000005605 benzo group Chemical group 0.000 description 6
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 3
- 208000020925 Bipolar disease Diseases 0.000 description 3
- 230000036506 anxiety Effects 0.000 description 3
- 201000000980 schizophrenia Diseases 0.000 description 3
- 0 BN(CC1)CCN1C(C1C(CCCC2)C2CN(CC(*)C*)C1)=O Chemical compound BN(CC1)CCN1C(C1C(CCCC2)C2CN(CC(*)C*)C1)=O 0.000 description 2
- YIFHFKIAGWFMFR-CYUUXAIJSA-N CC1=NN2C=C(C=CC2=N1)C[C@H](C)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC(=C(C=C6)F)F Chemical compound CC1=NN2C=C(C=CC2=N1)C[C@H](C)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC(=C(C=C6)F)F YIFHFKIAGWFMFR-CYUUXAIJSA-N 0.000 description 2
- MZEIROPEHDVJSM-UICHKGEESA-N CCOC1=NC=C(C=C1)C[C@H](C)CN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC(=C(C=C5)F)F Chemical compound CCOC1=NC=C(C=C1)C[C@H](C)CN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC(=C(C=C5)F)F MZEIROPEHDVJSM-UICHKGEESA-N 0.000 description 2
- RDSAUPRYZCQORM-VBSYDLGNSA-N C[C@H](CC1=CN=C(C=C1)OC)CN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC(=C(C=C5)F)F Chemical compound C[C@H](CC1=CN=C(C=C1)OC)CN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC(=C(C=C5)F)F RDSAUPRYZCQORM-VBSYDLGNSA-N 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- LSHVDMSVIBRMJS-UHFFFAOYSA-N BN(CC1)CCN1C(C1C(CCCC2)C2CNC1)=O Chemical compound BN(CC1)CCN1C(C1C(CCCC2)C2CNC1)=O LSHVDMSVIBRMJS-UHFFFAOYSA-N 0.000 description 1
- PBIJFETZVGZXDS-UHFFFAOYSA-N C1CCC2C(C1)CN(CC2C(=O)N3CCN(CC3)C4=CC=C(C=C4)[N+](=O)[O-])CCCC5=CC6=C(C=C5)OCO6 Chemical compound C1CCC2C(C1)CN(CC2C(=O)N3CCN(CC3)C4=CC=C(C=C4)[N+](=O)[O-])CCCC5=CC6=C(C=C5)OCO6 PBIJFETZVGZXDS-UHFFFAOYSA-N 0.000 description 1
- FALYLKFOGKFFCZ-PZUNEJSGSA-N C1CC[C@H]2[C@H](C1)CN(C[C@H]2C(=O)N3CCN(CC3)C4=CC(=C(C=C4)F)F)CCCC5=CC6=C(C=C5)OCO6 Chemical compound C1CC[C@H]2[C@H](C1)CN(C[C@H]2C(=O)N3CCN(CC3)C4=CC(=C(C=C4)F)F)CCCC5=CC6=C(C=C5)OCO6 FALYLKFOGKFFCZ-PZUNEJSGSA-N 0.000 description 1
- KNKREEACRCCPBZ-TZFWCWEWSA-N CC(=O)C1=CC(=CC(=C1)CCCN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC6=NON=C6C=C5)C(=O)C Chemical compound CC(=O)C1=CC(=CC(=C1)CCCN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC6=NON=C6C=C5)C(=O)C KNKREEACRCCPBZ-TZFWCWEWSA-N 0.000 description 1
- UKACSKJZQHGMHF-QKBZBAIHSA-N CC(C)[C@H](CC1=CC2=C(C=C1)OCO2)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC7=NON=C7C=C6 Chemical compound CC(C)[C@H](CC1=CC2=C(C=C1)OCO2)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC7=NON=C7C=C6 UKACSKJZQHGMHF-QKBZBAIHSA-N 0.000 description 1
- ZZFYFCYIPZHOSH-DMTNHVFBSA-N CC1=NC2=C(O1)C=CC(=C2)CCCN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC(=C(C=C6)F)F Chemical compound CC1=NC2=C(O1)C=CC(=C2)CCCN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC(=C(C=C6)F)F ZZFYFCYIPZHOSH-DMTNHVFBSA-N 0.000 description 1
- ORWKFKYYOVHTJR-CYUUXAIJSA-N CC1=NC2=C(O1)C=CC(=C2)C[C@H](C)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC(=C(C=C6)F)F Chemical compound CC1=NC2=C(O1)C=CC(=C2)C[C@H](C)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC(=C(C=C6)F)F ORWKFKYYOVHTJR-CYUUXAIJSA-N 0.000 description 1
- DDNQJKWULPOEKJ-CYUUXAIJSA-N CC1=NC2=C(O1)C=CC(=C2)C[C@H](C)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC7=NON=C7C=C6 Chemical compound CC1=NC2=C(O1)C=CC(=C2)C[C@H](C)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC7=NON=C7C=C6 DDNQJKWULPOEKJ-CYUUXAIJSA-N 0.000 description 1
- SCMGZLCXEWZMAF-YQXNOVQFSA-N CC1=NC2=C(O1)C=CC(=C2)C[C@H](C)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC=C(C=C6)C#N Chemical compound CC1=NC2=C(O1)C=CC(=C2)C[C@H](C)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC=C(C=C6)C#N SCMGZLCXEWZMAF-YQXNOVQFSA-N 0.000 description 1
- VHVPOXNMDWTTLR-UICHKGEESA-N CCNC1=NC=C(C=C1)C[C@H](C)CN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC(=C(C=C5)F)F Chemical compound CCNC1=NC=C(C=C1)C[C@H](C)CN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC(=C(C=C5)F)F VHVPOXNMDWTTLR-UICHKGEESA-N 0.000 description 1
- AMCUTXLZCZZZGJ-MDMAHDEASA-N CCOC1=NC=C(C=C1)C[C@H](C)CN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC=C(C=C5)C#N Chemical compound CCOC1=NC=C(C=C1)C[C@H](C)CN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC=C(C=C5)C#N AMCUTXLZCZZZGJ-MDMAHDEASA-N 0.000 description 1
- KSSRLNAVLKWQQB-NRSKXHDUSA-N COC(=O)C1=CC(=CC(=C1)CCCN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC=C(C=C5)[N+](=O)[O-])C(=O)OC Chemical compound COC(=O)C1=CC(=CC(=C1)CCCN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC=C(C=C5)[N+](=O)[O-])C(=O)OC KSSRLNAVLKWQQB-NRSKXHDUSA-N 0.000 description 1
- NVRFWMASOFUUJK-IVTVSAFSSA-N C[C@@H](CC1=CC2=C(C=C1)OC=N2)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC(=C(C=C6)F)F Chemical compound C[C@@H](CC1=CC2=C(C=C1)OC=N2)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC(=C(C=C6)F)F NVRFWMASOFUUJK-IVTVSAFSSA-N 0.000 description 1
- PXKLEJCHPGUZTI-IVTVSAFSSA-N C[C@@H](CC1=CC2=C(C=C1)OCO2)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC7=NON=C7C=C6 Chemical compound C[C@@H](CC1=CC2=C(C=C1)OCO2)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC7=NON=C7C=C6 PXKLEJCHPGUZTI-IVTVSAFSSA-N 0.000 description 1
- CNPQNESZCIIZNH-MKLBEGSSSA-N C[C@@H](CC1=CC2=C(C=C1)ONO2)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC=C(C=C6)C#N Chemical compound C[C@@H](CC1=CC2=C(C=C1)ONO2)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC=C(C=C6)C#N CNPQNESZCIIZNH-MKLBEGSSSA-N 0.000 description 1
- WJLWPOMHOMKGEB-MDMAHDEASA-N C[C@@H](CC1=CC2=NC=CN=C2C=C1)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC=C(C=C6)C#N Chemical compound C[C@@H](CC1=CC2=NC=CN=C2C=C1)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC=C(C=C6)C#N WJLWPOMHOMKGEB-MDMAHDEASA-N 0.000 description 1
- FXULLNLFEFAYPW-UHRQBARKSA-N C[C@@H](CC1=CC2=NC=CN=C2C=C1)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=NC7=NON=C7C=C6 Chemical compound C[C@@H](CC1=CC2=NC=CN=C2C=C1)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=NC7=NON=C7C=C6 FXULLNLFEFAYPW-UHRQBARKSA-N 0.000 description 1
- RGQCQEXWUZOUCH-MKLBEGSSSA-N C[C@@H](CC1=CC2=NSN=C2C=C1)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC=C(C=C6)C#N Chemical compound C[C@@H](CC1=CC2=NSN=C2C=C1)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC=C(C=C6)C#N RGQCQEXWUZOUCH-MKLBEGSSSA-N 0.000 description 1
- BDCQIKPPJIYFGF-XDWXJERXSA-N C[C@@H](CC1=CC2=NSN=C2C=C1)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=NC=C(C=C6)C#N Chemical compound C[C@@H](CC1=CC2=NSN=C2C=C1)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=NC=C(C=C6)C#N BDCQIKPPJIYFGF-XDWXJERXSA-N 0.000 description 1
- PSPZLMYZALLDRV-UICHKGEESA-N C[C@@H](CC1=CN2C=CN=C2C=C1)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC7=NON=C7C=C6 Chemical compound C[C@@H](CC1=CN2C=CN=C2C=C1)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC7=NON=C7C=C6 PSPZLMYZALLDRV-UICHKGEESA-N 0.000 description 1
- TWXRBKVFDJGPSS-IVTVSAFSSA-N C[C@@H](CC1=CN=C(C=C1)OC)CN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC6=NON=C6C=C5 Chemical compound C[C@@H](CC1=CN=C(C=C1)OC)CN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC6=NON=C6C=C5 TWXRBKVFDJGPSS-IVTVSAFSSA-N 0.000 description 1
- YBLVKGXHBMIOAB-IPGTZRFSSA-N C[C@@H](CC1=CN=C(C=C1)OC)CN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC=C(C=C5)C#N Chemical compound C[C@@H](CC1=CN=C(C=C1)OC)CN2C[C@H]3CCCC[C@@H]3[C@@H](C2)C(=O)N4CCN(CC4)C5=CC=C(C=C5)C#N YBLVKGXHBMIOAB-IPGTZRFSSA-N 0.000 description 1
- RGSBOQCPAPABQT-VBSYDLGNSA-N C[C@H](CC1=CC2=C(C=C1)OC=N2)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC7=NON=C7C=C6 Chemical compound C[C@H](CC1=CC2=C(C=C1)OC=N2)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC7=NON=C7C=C6 RGSBOQCPAPABQT-VBSYDLGNSA-N 0.000 description 1
- KUHJMKMRUIRJSL-VBSYDLGNSA-N C[C@H](CC1=CN2C(=NC=N2)C=C1)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC(=C(C=C6)F)F Chemical compound C[C@H](CC1=CN2C(=NC=N2)C=C1)CN3C[C@H]4CCCC[C@@H]4[C@@H](C3)C(=O)N5CCN(CC5)C6=CC(=C(C=C6)F)F KUHJMKMRUIRJSL-VBSYDLGNSA-N 0.000 description 1
- VXLCNTLWWUDBSO-UHFFFAOYSA-N Ethiazide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)NC(CC)NC2=C1 VXLCNTLWWUDBSO-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 241001275899 Salta Species 0.000 description 1
- ZUKSFLFVDPKYES-DAANFHMWSA-N [(4s,4as,8ar)-2-[(2s)-2-methyl-3-quinoxalin-6-ylpropyl]-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-4-yl]-[4-(3,4-difluorophenyl)piperazin-1-yl]methanone Chemical compound O=C([C@H]1[C@H]2CCCC[C@H]2CN(C1)C[C@@H](C)CC=1C=C2N=CC=NC2=CC=1)N(CC1)CCN1C1=CC=C(F)C(F)=C1 ZUKSFLFVDPKYES-DAANFHMWSA-N 0.000 description 1
- RDSAUPRYZCQORM-BJTUFNSYSA-N [(4s,4as,8ar)-2-[(2s)-3-(6-methoxypyridin-3-yl)-2-methylpropyl]-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-4-yl]-[4-(3,4-difluorophenyl)piperazin-1-yl]methanone Chemical compound C1=NC(OC)=CC=C1C[C@H](C)CN1C[C@@H](C(=O)N2CCN(CC2)C=2C=C(F)C(F)=CC=2)[C@H]2CCCC[C@H]2C1 RDSAUPRYZCQORM-BJTUFNSYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0007108.4A GB0007108D0 (en) | 2000-03-23 | 2000-03-23 | Organic compounds |
| GB0007108.4 | 2000-03-23 | ||
| PCT/EP2001/003211 WO2001070731A1 (en) | 2000-03-23 | 2001-03-21 | Decahydro-isoquinolines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003528096A JP2003528096A (ja) | 2003-09-24 |
| JP2003528096A5 true JP2003528096A5 (https=) | 2007-12-27 |
| JP4118565B2 JP4118565B2 (ja) | 2008-07-16 |
Family
ID=9888307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001568934A Expired - Fee Related JP4118565B2 (ja) | 2000-03-23 | 2001-03-21 | デカヒドロ−イソキノリン |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6635647B2 (https=) |
| EP (1) | EP1268466B1 (https=) |
| JP (1) | JP4118565B2 (https=) |
| AR (1) | AR029821A1 (https=) |
| AT (1) | ATE298332T1 (https=) |
| AU (1) | AU2001239310A1 (https=) |
| CA (1) | CA2402751C (https=) |
| CO (1) | CO5271675A1 (https=) |
| DE (1) | DE60111621T2 (https=) |
| DK (1) | DK1268466T3 (https=) |
| ES (1) | ES2243462T3 (https=) |
| GB (1) | GB0007108D0 (https=) |
| PE (1) | PE20011114A1 (https=) |
| PT (1) | PT1268466E (https=) |
| WO (1) | WO2001070731A1 (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0128996D0 (en) | 2001-12-04 | 2002-01-23 | Novartis Ag | Organic compounds |
| GB0420722D0 (en) | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| JP2009525304A (ja) * | 2006-01-30 | 2009-07-09 | シュペーデル・エクスペリメンタ・アーゲー | α，β−不飽和化合物からのアルコールの立体選択的製造方法 |
| AR059898A1 (es) | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| PL2200985T3 (pl) | 2007-09-14 | 2011-12-30 | Ortho Mcneil Janssen Pharmaceuticals Inc | 1,3-Dipodstawione-4-(arylo-X-fenylo)-1H-pirydyn-2-ony |
| SI2203439T1 (sl) | 2007-09-14 | 2011-05-31 | Ortho Mcneil Janssen Pharm | 1',3'-disubstituirani 4-fenil-3,4,5,6-tetrahidro-2H-1'H-(1,4')bipiridinil-2'-oni |
| EP2344470B1 (en) | 2008-09-02 | 2013-11-06 | Janssen Pharmaceuticals, Inc. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
| JP5690277B2 (ja) | 2008-11-28 | 2015-03-25 | ジャンセン ファーマシューティカルズ， インコーポレイテッド． | 代謝型グルタミン酸受容体の調節因子としてのインドールおよびベンゾオキサジン誘導体 |
| BRPI1010831A2 (pt) | 2009-05-12 | 2016-04-05 | Addex Pharmaceuticals Sa | derivados de 1,2,4-triazolo[4,3-a]piridina e seu como moduladores alostéricos positivos de receptores de mglur2 |
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| US9271967B2 (en) | 2010-11-08 | 2016-03-01 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
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| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
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| US11629135B2 (en) | 2017-11-06 | 2023-04-18 | Jubilant Prodell Llc | Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation |
| PT3704120T (pt) | 2017-11-24 | 2024-07-03 | Jubilant Episcribe Llc | Compostos heterocíclicos como inibidores de prmt5 |
| MX2020009517A (es) | 2018-03-13 | 2021-01-20 | Jubilant Prodel LLC | Compuestos biciclicos como inhibidores de la interaccion/activacio n de pdl/pd-l1. |
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|---|---|---|---|---|
| EP1070054A1 (en) * | 1998-04-08 | 2001-01-24 | Takeda Chemical Industries, Ltd. | Amine compounds, their production and their use as somatostatin receptor antagonists or agonists |
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2001
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- 2001-03-21 EP EP01913896A patent/EP1268466B1/en not_active Expired - Lifetime
- 2001-03-21 PE PE2001000262A patent/PE20011114A1/es not_active Application Discontinuation
- 2001-03-21 JP JP2001568934A patent/JP4118565B2/ja not_active Expired - Fee Related
- 2001-03-21 US US10/221,983 patent/US6635647B2/en not_active Expired - Fee Related
- 2001-03-21 DK DK01913896T patent/DK1268466T3/da active
- 2001-03-21 DE DE60111621T patent/DE60111621T2/de not_active Expired - Lifetime
- 2001-03-21 ES ES01913896T patent/ES2243462T3/es not_active Expired - Lifetime
- 2001-03-21 WO PCT/EP2001/003211 patent/WO2001070731A1/en not_active Ceased
- 2001-03-21 PT PT01913896T patent/PT1268466E/pt unknown
- 2001-03-21 AR ARP010101320A patent/AR029821A1/es unknown
- 2001-03-21 CO CO01022539A patent/CO5271675A1/es not_active Application Discontinuation
- 2001-03-21 AU AU2001239310A patent/AU2001239310A1/en not_active Abandoned
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