JP2015536965A5 - - Google Patents
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- Publication number
- JP2015536965A5 JP2015536965A5 JP2015541169A JP2015541169A JP2015536965A5 JP 2015536965 A5 JP2015536965 A5 JP 2015536965A5 JP 2015541169 A JP2015541169 A JP 2015541169A JP 2015541169 A JP2015541169 A JP 2015541169A JP 2015536965 A5 JP2015536965 A5 JP 2015536965A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidine
- carbonyl
- carbonitrile
- compound
- benzyloxy
- 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
- 150000001875 compounds Chemical class 0.000 claims 22
- -1 benzyloxy, phenylcarbonyloxy, naphthylcarbonyloxy, quinolinylcarbonyloxy, isoquinolyl Chemical group 0.000 claims 7
- 208000010877 cognitive disease Diseases 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 239000000651 prodrug Substances 0.000 claims 5
- 229940002612 prodrug Drugs 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- RYGXYKCVBXEBDI-PMACEKPBSA-N (2s)-1-[(2s)-1-(3,5-dimethoxy-4-phenylmethoxybenzoyl)-4,4-difluoropyrrolidine-2-carbonyl]pyrrolidine-2-carbonitrile Chemical compound COC1=CC(C(=O)N2[C@@H](CC(F)(F)C2)C(=O)N2[C@@H](CCC2)C#N)=CC(OC)=C1OCC1=CC=CC=C1 RYGXYKCVBXEBDI-PMACEKPBSA-N 0.000 claims 1
- KPMLPBXDOBSUBP-ICSRJNTNSA-N (2s)-1-[(2s)-4,4-difluoro-1-(2-phenylmethoxybenzoyl)pyrrolidine-2-carbonyl]pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CC(C1)(F)F)C(=O)N1[C@@H](CCC1)C#N)C(=O)C1=CC=CC=C1OCC1=CC=CC=C1 KPMLPBXDOBSUBP-ICSRJNTNSA-N 0.000 claims 1
- KYOISHPHSGUAGP-ICSRJNTNSA-N (2s)-1-[(2s)-4,4-difluoro-1-[4-phenylmethoxy-3-(trifluoromethyl)benzoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonitrile Chemical compound FC(F)(F)C1=CC(C(=O)N2[C@@H](CC(F)(F)C2)C(=O)N2[C@@H](CCC2)C#N)=CC=C1OCC1=CC=CC=C1 KYOISHPHSGUAGP-ICSRJNTNSA-N 0.000 claims 1
- CDCQFMSWVXKTEI-BDTNDASRSA-N (2s)-1-[(2s,4r)-1-(3,5-dimethoxy-4-phenylmethoxybenzoyl)-4-methoxypyrrolidine-2-carbonyl]pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](C[C@H](C1)OC)C(=O)N1[C@@H](CCC1)C#N)C(=O)C(C=C1OC)=CC(OC)=C1OCC1=CC=CC=C1 CDCQFMSWVXKTEI-BDTNDASRSA-N 0.000 claims 1
- QHNGZPUFJVCMAC-BVSLBCMMSA-N (3r,5s)-5-[(2s)-2-cyanopyrrolidine-1-carbonyl]-1-(3,5-dimethoxy-4-phenylmethoxybenzoyl)pyrrolidine-3-carbonitrile Chemical compound COC1=CC(C(=O)N2[C@@H](C[C@H](C2)C#N)C(=O)N2[C@@H](CCC2)C#N)=CC(OC)=C1OCC1=CC=CC=C1 QHNGZPUFJVCMAC-BVSLBCMMSA-N 0.000 claims 1
- SLXVGFMNHXEBEB-GJZGRUSLSA-N [4-[(2s)-2-[(2s)-2-cyanopyrrolidine-1-carbonyl]-4,4-difluoropyrrolidine-1-carbonyl]-2,6-dimethoxyphenyl] acetate Chemical compound COC1=C(OC(C)=O)C(OC)=CC(C(=O)N2[C@@H](CC(F)(F)C2)C(=O)N2[C@@H](CCC2)C#N)=C1 SLXVGFMNHXEBEB-GJZGRUSLSA-N 0.000 claims 1
- AKPQWPSPFZAOLD-OALUTQOASA-N [4-[(2s)-2-[(2s)-2-cyanopyrrolidine-1-carbonyl]-4,4-difluoropyrrolidine-1-carbonyl]-2,6-dimethoxyphenyl] benzoate Chemical compound COC1=CC(C(=O)N2[C@@H](CC(F)(F)C2)C(=O)N2[C@@H](CCC2)C#N)=CC(OC)=C1OC(=O)C1=CC=CC=C1 AKPQWPSPFZAOLD-OALUTQOASA-N 0.000 claims 1
- UNRZBJNUJBINFC-HOTGVXAUSA-N [5-[(2s)-2-[(2s)-2-cyanopyrrolidine-1-carbonyl]-4,4-difluoropyrrolidine-1-carbonyl]-2,3-dimethoxyphenyl] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC1=C(OC)C(OC)=CC(C(=O)N2[C@@H](CC(F)(F)C2)C(=O)N2[C@@H](CCC2)C#N)=C1 UNRZBJNUJBINFC-HOTGVXAUSA-N 0.000 claims 1
- AOCAMLSIPXYBHW-GJZGRUSLSA-N [5-[(2s)-2-[(2s)-2-cyanopyrrolidine-1-carbonyl]-4,4-difluoropyrrolidine-1-carbonyl]-2,3-dimethoxyphenyl] acetate Chemical compound CC(=O)OC1=C(OC)C(OC)=CC(C(=O)N2[C@@H](CC(F)(F)C2)C(=O)N2[C@@H](CCC2)C#N)=C1 AOCAMLSIPXYBHW-GJZGRUSLSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- ALSCEGDXFJIYES-UHFFFAOYSA-N pyrrolidine-2-carbonitrile Chemical compound N#CC1CCCN1 ALSCEGDXFJIYES-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12382446.8A EP2730571A1 (en) | 2012-11-12 | 2012-11-12 | 1-[1-(benzoyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonitrile derivatives |
| EP12382446.8 | 2012-11-12 | ||
| PCT/EP2013/073460 WO2014072498A1 (en) | 2012-11-12 | 2013-11-11 | 1-[1-(benzoyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonitrile derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015536965A JP2015536965A (ja) | 2015-12-24 |
| JP2015536965A5 true JP2015536965A5 (OSRAM) | 2016-08-04 |
| JP6203278B2 JP6203278B2 (ja) | 2017-09-27 |
Family
ID=47278735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015541169A Active JP6203278B2 (ja) | 2012-11-12 | 2013-11-11 | １−［１−（ベンゾイル）−ピロリジン−２−カルボニル］−ピロリジン−２−カルボニトリル誘導体 |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US10125097B2 (OSRAM) |
| EP (2) | EP2730571A1 (OSRAM) |
| JP (1) | JP6203278B2 (OSRAM) |
| KR (1) | KR102151290B1 (OSRAM) |
| CN (1) | CN104903314B (OSRAM) |
| AU (1) | AU2013343430B2 (OSRAM) |
| BR (1) | BR112015010377A8 (OSRAM) |
| CA (1) | CA2890042C (OSRAM) |
| CY (1) | CY1118818T1 (OSRAM) |
| DK (1) | DK2917209T3 (OSRAM) |
| EA (1) | EA028422B1 (OSRAM) |
| ES (1) | ES2621672T3 (OSRAM) |
| HR (1) | HRP20170485T1 (OSRAM) |
| HU (1) | HUE032472T2 (OSRAM) |
| LT (1) | LT2917209T (OSRAM) |
| ME (1) | ME02706B (OSRAM) |
| MX (1) | MX367488B (OSRAM) |
| NZ (1) | NZ709096A (OSRAM) |
| PL (1) | PL2917209T3 (OSRAM) |
| PT (1) | PT2917209T (OSRAM) |
| RS (1) | RS55865B1 (OSRAM) |
| SI (1) | SI2917209T1 (OSRAM) |
| SM (1) | SMT201700202T1 (OSRAM) |
| WO (1) | WO2014072498A1 (OSRAM) |
| ZA (1) | ZA201504269B (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2730571A1 (en) | 2012-11-12 | 2014-05-14 | Universitat De Barcelona | 1-[1-(benzoyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonitrile derivatives |
| EP3031458A1 (en) * | 2014-12-09 | 2016-06-15 | Iproteos S.L. | Use of 1-[(2-phenylcycloprop-1-yl)carbonyl]-2-[(1,3-thiazolidin-3-yl)carbonyl]perhydroindole in the treatment of schizophrenia-associated cognitive deficits |
| MX2020006128A (es) | 2017-12-15 | 2020-09-21 | Praxis Biotech LLC | Inhibidores de la proteina de activacion de fibroblastos. |
| EP3898654A4 (en) | 2018-12-21 | 2022-10-26 | Praxis Biotech LLC | FIBROBLAST ACTIVATION PROTEIN INHIBITORS |
| CA3185064A1 (en) * | 2020-07-07 | 2022-01-13 | Teresa Tarrago Clua | 1-[1-(4-benzyloxy-3,5-difluoro-benzoyl)-4-fluoro-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonitrile |
| MY208099A (en) * | 2020-12-28 | 2025-04-15 | Sarawak Biodiversity Council | Compound for treating neurodegenerative diseases and its isolation method thereof |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991018891A1 (en) * | 1990-06-04 | 1991-12-12 | Pfizer Inc. | Aromatic pyrrolidine and thiazolidine amides |
| US6159938A (en) | 1994-11-21 | 2000-12-12 | Cortech, Inc. | Serine protease inhibitors comprising α-keto heterocycles |
| HUT76640A (en) * | 1995-08-17 | 1997-10-28 | Chinoin Gyogyszer Es Vegyeszet | Compounds of pharmaceutical activity cyclic amide derivatives, pharmaceutical compositions containing them, process for producing them and their use |
| DE19603510A1 (de) | 1996-02-01 | 1997-08-07 | Knoell Hans Forschung Ev | Die Verwendung von Terrecyclolsäure A und Terrecyclolsäure A-Derivate als neue Inhibitoren der humanen Prolyl-Oligopeptidase |
| CA2414311C (en) * | 2000-07-19 | 2008-01-08 | F. Hoffmann-La Roche Ag | Pyrrolidine derivatives as inhibitors of endothelin-converting enzyme |
| FI20011466A0 (fi) | 2001-07-04 | 2001-07-04 | Orion Corp | Prolyylioligopeptidaasia inhiboivaa aktiivisuutta omaavia yhdisteitä, niiden valmistusmenetelmiä ja käyttö |
| FI20030014A0 (fi) | 2003-01-03 | 2003-01-03 | Orion Corp | Prolyylioligopeptidaasia inhiboivaa aktiivisuutta omaavia yhdisteitä |
| FI20031018A0 (fi) | 2003-07-04 | 2003-07-04 | Orion Corp | Parannus aivovammasta toipumiseen |
| WO2005027934A1 (ja) | 2003-09-24 | 2005-03-31 | Nippon Kayaku Kabushiki Kaisha | プロリルオリゴペプチダーゼ阻害剤 |
| US7667044B2 (en) | 2003-11-03 | 2010-02-23 | Probiodrug Ag | Compounds for the treatment of neurological disorders |
| EP1760076A1 (en) * | 2005-09-02 | 2007-03-07 | Ferring B.V. | FAP Inhibitors |
| ES2302473B1 (es) | 2006-12-22 | 2009-06-12 | Universidad De Barcelona | Agente terapeutico para el tratamiento del desorden afectivo bipolar en mamiferos. |
| WO2010083570A1 (en) * | 2009-01-23 | 2010-07-29 | The University Of Sydney | Novel metabolic disease therapy |
| EP2730571A1 (en) | 2012-11-12 | 2014-05-14 | Universitat De Barcelona | 1-[1-(benzoyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonitrile derivatives |
-
2012
- 2012-11-12 EP EP12382446.8A patent/EP2730571A1/en not_active Withdrawn
-
2013
- 2013-11-11 SI SI201330601A patent/SI2917209T1/sl unknown
- 2013-11-11 KR KR1020157015736A patent/KR102151290B1/ko active Active
- 2013-11-11 LT LTEP13794837.8T patent/LT2917209T/lt unknown
- 2013-11-11 EA EA201590942A patent/EA028422B1/ru not_active IP Right Cessation
- 2013-11-11 ME MEP-2017-76A patent/ME02706B/me unknown
- 2013-11-11 HR HRP20170485TT patent/HRP20170485T1/hr unknown
- 2013-11-11 NZ NZ709096A patent/NZ709096A/en unknown
- 2013-11-11 HU HUE13794837A patent/HUE032472T2/en unknown
- 2013-11-11 ES ES13794837.8T patent/ES2621672T3/es active Active
- 2013-11-11 US US14/436,715 patent/US10125097B2/en active Active
- 2013-11-11 AU AU2013343430A patent/AU2013343430B2/en active Active
- 2013-11-11 SM SM20170202T patent/SMT201700202T1/it unknown
- 2013-11-11 PT PT137948378T patent/PT2917209T/pt unknown
- 2013-11-11 WO PCT/EP2013/073460 patent/WO2014072498A1/en not_active Ceased
- 2013-11-11 JP JP2015541169A patent/JP6203278B2/ja active Active
- 2013-11-11 BR BR112015010377A patent/BR112015010377A8/pt not_active Application Discontinuation
- 2013-11-11 MX MX2015005931A patent/MX367488B/es active IP Right Grant
- 2013-11-11 EP EP13794837.8A patent/EP2917209B1/en active Active
- 2013-11-11 DK DK13794837.8T patent/DK2917209T3/en active
- 2013-11-11 PL PL13794837T patent/PL2917209T3/pl unknown
- 2013-11-11 CN CN201380059126.XA patent/CN104903314B/zh active Active
- 2013-11-11 RS RS20170362A patent/RS55865B1/sr unknown
- 2013-11-11 CA CA2890042A patent/CA2890042C/en active Active
-
2015
- 2015-06-12 ZA ZA2015/04269A patent/ZA201504269B/en unknown
-
2017
- 2017-04-06 CY CY20171100410T patent/CY1118818T1/el unknown
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2018
- 2018-09-26 US US16/142,907 patent/US10611727B2/en active Active