JP2010502664A5 - - Google Patents

Info

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

2007-09-10

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Withdrawn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

• Espacenet
• Global Dossier
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• -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