JP2010502664A5 - - Google Patents
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- Publication number
- JP2010502664A5 JP2010502664A5 JP2009527065A JP2009527065A JP2010502664A5 JP 2010502664 A5 JP2010502664 A5 JP 2010502664A5 JP 2009527065 A JP2009527065 A JP 2009527065A JP 2009527065 A JP2009527065 A JP 2009527065A JP 2010502664 A5 JP2010502664 A5 JP 2010502664A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- hydroxy
- cyclohexyl
- phenylethynyl
- 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.)
- Withdrawn
Links
- -1 N-[(1S , 3S) -3- (3-chloro-phenylethynyl) -3-hydroxy-cyclohexyl] -2-phenyl-acetamido N-[(1S, 3S) -3- (3-chloro-phenylethynyl) -3-hydroxy - cyclohexyl]-3-(1H-indol-4-yl) - propionamide Chemical compound 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 208000010877 cognitive disease Diseases 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- PFNVKPSTLQITDW-SIKLNZKXSA-N n-[(1s,3s)-3-[2-(3-chlorophenyl)ethynyl]-3-hydroxycyclohexyl]-2-[2-(trifluoromethoxy)phenyl]acetamide Chemical compound N([C@H]1CCC[C@@](C1)(O)C#CC=1C=C(Cl)C=CC=1)C(=O)CC1=CC=CC=C1OC(F)(F)F PFNVKPSTLQITDW-SIKLNZKXSA-N 0.000 description 2
- MWKYSPKUMNDLCU-RBBKRZOGSA-N n-[(1s,3s)-3-[2-(3-chlorophenyl)ethynyl]-3-hydroxycyclohexyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)N[C@@H]1C[C@](O)(C#CC=2C=C(Cl)C=CC=2)CCC1 MWKYSPKUMNDLCU-RBBKRZOGSA-N 0.000 description 2
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Chemical compound OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 2
- PUQAHZPHRXPSAW-UHFFFAOYSA-N 3-azabicyclo[2.2.1]heptan-3-yl-[5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(C)=CC=C1NC1=NC=C(C(=O)N2C3CCC(C3)C2)C=C1Cl PUQAHZPHRXPSAW-UHFFFAOYSA-N 0.000 description 1
- YJTXVDJWRQLIFW-NFJCIPKMSA-N CN1C(=CC=C1)C(=O)O.ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(=O)C=1NC2=CC=C(C=C2C1)O)O Chemical compound CN1C(=CC=C1)C(=O)O.ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(=O)C=1NC2=CC=C(C=C2C1)O)O YJTXVDJWRQLIFW-NFJCIPKMSA-N 0.000 description 1
- CQIZYWGJPPFZQA-BFBNMVJXSA-N COC(C(C=C1)=CC=C1C(N[C@@H](CCC1)C[C@@]1(C#CC1=CC(Cl)=CC=C1)O)=O)=O.N[C@@H](CCC1)C[C@@]1(C#CC1=CC(Cl)=CC=C1)O Chemical compound COC(C(C=C1)=CC=C1C(N[C@@H](CCC1)C[C@@]1(C#CC1=CC(Cl)=CC=C1)O)=O)=O.N[C@@H](CCC1)C[C@@]1(C#CC1=CC(Cl)=CC=C1)O CQIZYWGJPPFZQA-BFBNMVJXSA-N 0.000 description 1
- KMNCUFCQZBBWSD-WKRVVKTRSA-N ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)N1C(=C(C2=CC(=CC=C12)O)NC(CC1=C(C=CC=C1)F)=O)C(=O)O)O Chemical compound ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)N1C(=C(C2=CC(=CC=C12)O)NC(CC1=C(C=CC=C1)F)=O)C(=O)O)O KMNCUFCQZBBWSD-WKRVVKTRSA-N 0.000 description 1
- XEUVZDNPMDRRDC-RBKUWPRVSA-N ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(C1=CC(=CC=C1)F)=O)O.ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(C1=CC=C(C=C1)C)=O)O Chemical compound ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(C1=CC(=CC=C1)F)=O)O.ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(C1=CC=C(C=C1)C)=O)O XEUVZDNPMDRRDC-RBKUWPRVSA-N 0.000 description 1
- BPGOAVFIFREQPO-XSJRCKMOSA-N ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(C1=CC=C(C=C1)C)=O)O.ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(=O)C1=CNC=C1)O Chemical compound ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(C1=CC=C(C=C1)C)=O)O.ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(=O)C1=CNC=C1)O BPGOAVFIFREQPO-XSJRCKMOSA-N 0.000 description 1
- PQFXEJAQOFWZKF-IEVUOVSVSA-N ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(CC1=C(C=CC=C1)F)=O)O.ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(C(C)OC1=CC=CC=C1)=O)O Chemical compound ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(CC1=C(C=CC=C1)F)=O)O.ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(C(C)OC1=CC=CC=C1)=O)O PQFXEJAQOFWZKF-IEVUOVSVSA-N 0.000 description 1
- FVWKUGOEPLBPRZ-IOCIPSDNSA-N ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(CCC(=O)C1=C(C=CC(=C1)OC)OC)=O)O.ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(C(CC)CC)=O)O Chemical compound ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(CCC(=O)C1=C(C=CC(=C1)OC)OC)=O)O.ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(C(CC)CC)=O)O FVWKUGOEPLBPRZ-IOCIPSDNSA-N 0.000 description 1
- YIQSLQQXFSRPQU-XTOOVZATSA-N ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(CCC1=C2C=CNC2=CC=C1)=O)O.ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(CC1=CC=CC=C1)=O)O Chemical compound ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(CCC1=C2C=CNC2=CC=C1)=O)O.ClC=1C=C(C=CC1)C#C[C@]1(C[C@H](CCC1)NC(CC1=CC=CC=C1)=O)O YIQSLQQXFSRPQU-XTOOVZATSA-N 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- ZVUJPFSWEVYLFO-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-piperidin-1-ylmethanone Chemical compound C1=NC(C)=CC=C1NC1=NC=C(C(=O)N2CCCCC2)C=C1Cl ZVUJPFSWEVYLFO-UHFFFAOYSA-N 0.000 description 1
- XNGQCBQDFMQYDG-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-thiomorpholin-4-ylmethanone Chemical compound C1=NC(C)=CC=C1NC1=NC=C(C(=O)N2CCSCC2)C=C1Cl XNGQCBQDFMQYDG-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 230000037007 arousal Effects 0.000 description 1
- BJUSXUSIBPEZSP-UHFFFAOYSA-N azepan-1-yl-[5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(C)=CC=C1NC1=NC=C(C(=O)N2CCCCCC2)C=C1Cl BJUSXUSIBPEZSP-UHFFFAOYSA-N 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001073 episodic memory Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 230000015654 memory Effects 0.000 description 1
- APFVXKCPFIDUDS-UKILVPOCSA-N n-[(1s,3s)-3-[2-(3-chlorophenyl)ethynyl]-3-hydroxycyclohexyl]-2-(2-phenylmethoxyethoxy)acetamide Chemical compound N([C@H]1CCC[C@@](C1)(O)C#CC=1C=C(Cl)C=CC=1)C(=O)COCCOCC1=CC=CC=C1 APFVXKCPFIDUDS-UKILVPOCSA-N 0.000 description 1
- FYXKJFAHICHKRR-NZQKXSOJSA-N n-[(1s,3s)-3-[2-(3-chlorophenyl)ethynyl]-3-hydroxycyclohexyl]-4-(dimethylamino)benzamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N[C@@H]1C[C@](O)(C#CC=2C=C(Cl)C=CC=2)CCC1 FYXKJFAHICHKRR-NZQKXSOJSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000003936 working memory Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06120424 | 2006-09-11 | ||
| US86881406P | 2006-12-06 | 2006-12-06 | |
| US86880506P | 2006-12-06 | 2006-12-06 | |
| US88525507P | 2007-01-17 | 2007-01-17 | |
| PCT/EP2007/007873 WO2008031550A2 (en) | 2006-09-11 | 2007-09-10 | Nicotinic acid derivatives as modulators of metabotropic glutanate receptors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013260495A Division JP5860865B2 (ja) | 2006-09-11 | 2013-12-17 | 代謝型グルタミン酸受容体の調節剤としてのニコチン酸誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010502664A JP2010502664A (ja) | 2010-01-28 |
| JP2010502664A5 true JP2010502664A5 (https=) | 2010-10-21 |
Family
ID=39184158
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009527065A Withdrawn JP2010502664A (ja) | 2006-09-11 | 2007-09-10 | 代謝型グルタミン酸受容体の調節剤としてのニコチン酸誘導体 |
| JP2013260495A Expired - Fee Related JP5860865B2 (ja) | 2006-09-11 | 2013-12-17 | 代謝型グルタミン酸受容体の調節剤としてのニコチン酸誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013260495A Expired - Fee Related JP5860865B2 (ja) | 2006-09-11 | 2013-12-17 | 代謝型グルタミン酸受容体の調節剤としてのニコチン酸誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US20100041641A1 (https=) |
| EP (2) | EP2272509A1 (https=) |
| JP (2) | JP2010502664A (https=) |
| KR (1) | KR20090061041A (https=) |
| AU (1) | AU2007296964B2 (https=) |
| CA (1) | CA2663113A1 (https=) |
| MX (1) | MX2009002684A (https=) |
| RU (1) | RU2014104384A (https=) |
| WO (1) | WO2008031550A2 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2012254934B2 (en) * | 2007-10-12 | 2013-10-17 | Novartis Ag | Metabotropic glutamate receptor modulators for the treatment of Parkinson's disease |
| KR101572280B1 (ko) * | 2007-10-12 | 2015-11-26 | 노파르티스 아게 | 파킨슨병의 치료를 위한 대사성 글루타메이트 수용체 조절제 |
| EP2320892A2 (en) * | 2008-06-30 | 2011-05-18 | Novartis AG | Combination products |
| RU2513856C2 (ru) * | 2008-08-12 | 2014-04-20 | Новартис Аг | Способы получения метилового эфира 4-оксооктагидроиндол-1-карбоновой кислоты и ее производные |
| MX2012003394A (es) * | 2009-09-21 | 2012-08-15 | Univ Vanderbilt | Analogos de la nicotinamida de o-bencilo como moduladores alostéricos positivos del mglur5. |
| WO2012084873A1 (en) * | 2010-12-20 | 2012-06-28 | Novartis Ag | 4- (hetero) aryl - ethynyl - octahydro - indole - 1 - carboxylic acid esters |
| TW201444821A (zh) | 2013-03-13 | 2014-12-01 | Janssen Pharmaceutica Nv | 經取代之哌啶化合物及其作為食慾素受體調節劑之用途 |
| TWI621618B (zh) | 2013-03-13 | 2018-04-21 | 比利時商健生藥品公司 | 經取代２－氮雜雙環類及其作為食慾素受體調控劑之用途 |
| TW201444849A (zh) | 2013-03-13 | 2014-12-01 | Janssen Pharmaceutica Nv | 經取代的7-氮雜雙環類及其作為食慾激素受體調節劑之用途 |
| AU2015314851B2 (en) * | 2014-09-11 | 2020-01-02 | Janssen Pharmaceutica Nv | Substituted 2-azabicycles and their use as orexin receptor modulators |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5521297A (en) | 1993-06-04 | 1996-05-28 | Salk Institute Biotechnology/Industrial Associates | Nucleic acids encoding human metabotropic glutamate receptors |
| WO2000051614A1 (en) | 1999-03-03 | 2000-09-08 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferases |
| CN1361768A (zh) * | 1999-06-02 | 2002-07-31 | Nps药物有限公司 | 代谢移变的谷氨酸盐受体拮抗剂和它们治疗中枢神经系统疾病的用途 |
| GB0128996D0 (en) * | 2001-12-04 | 2002-01-23 | Novartis Ag | Organic compounds |
| SE0201943D0 (sv) | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | New use |
| IL166510A0 (en) | 2002-08-09 | 2006-01-15 | Nps Pharma Inc | 1,2,4"oxadiazole as modulators of metabotropic glutamate receptor-5 |
| ES2316968T3 (es) * | 2003-03-04 | 2009-04-16 | Addex Pharma Sa | Nuevos derivados de aminopiridina utilizados como antagonistas de mglur5. |
| WO2005030128A2 (en) * | 2003-09-23 | 2005-04-07 | Merck & Co., Inc. | Pyrazole modulators of metabotropic glutamate receptors |
| CA2549965A1 (en) | 2003-10-31 | 2005-05-19 | Astrazeneca Ab | Alkynes iii |
| CA2549967A1 (en) | 2003-10-31 | 2005-05-19 | Astrazeneca Ab | Alkynes i |
| EP1677790A1 (en) | 2003-10-31 | 2006-07-12 | AstraZeneca AB | Alkynes ii |
| EP1715867A4 (en) | 2004-02-12 | 2009-04-15 | Merck & Co Inc | BIPYRIDYLAMIDE AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5 |
| DE102004020908A1 (de) * | 2004-04-28 | 2005-11-17 | Grünenthal GmbH | Substituierte 5,6,7,8,-Tetrahydro-pyrido[4,3-d]pyrimidin-2-yl- und 5,6,7,8,-Tetrahydro-chinazolin-2-yl-Verbindungen |
| GB0508319D0 (en) | 2005-04-25 | 2005-06-01 | Novartis Ag | Organic compounds |
| TW200801005A (en) | 2005-08-15 | 2008-01-01 | Astrazeneca Ab | Acetylenic piperazines as metabotropic glutamate receptor antagonists |
| AU2006329007A1 (en) * | 2005-12-20 | 2007-06-28 | Novartis Ag | Nicotinic acid derivatives as modulators of metabotropic glutamate receptors |
-
2007
- 2007-09-10 EP EP20100172443 patent/EP2272509A1/en not_active Withdrawn
- 2007-09-10 CA CA002663113A patent/CA2663113A1/en not_active Abandoned
- 2007-09-10 US US12/440,284 patent/US20100041641A1/en not_active Abandoned
- 2007-09-10 AU AU2007296964A patent/AU2007296964B2/en not_active Ceased
- 2007-09-10 WO PCT/EP2007/007873 patent/WO2008031550A2/en not_active Ceased
- 2007-09-10 EP EP07818088A patent/EP2069305A2/en not_active Withdrawn
- 2007-09-10 KR KR1020097007379A patent/KR20090061041A/ko not_active Ceased
- 2007-09-10 JP JP2009527065A patent/JP2010502664A/ja not_active Withdrawn
- 2007-09-10 MX MX2009002684A patent/MX2009002684A/es not_active Application Discontinuation
-
2012
- 2012-08-08 US US13/569,734 patent/US20120309742A1/en not_active Abandoned
-
2013
- 2013-12-17 JP JP2013260495A patent/JP5860865B2/ja not_active Expired - Fee Related
-
2014
- 2014-02-07 RU RU2014104384/04A patent/RU2014104384A/ru not_active Application Discontinuation
- 2014-03-07 US US14/200,085 patent/US20140187600A1/en not_active Abandoned
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