JP2009511589A5 - - Google Patents
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- Publication number
- JP2009511589A5 JP2009511589A5 JP2008535650A JP2008535650A JP2009511589A5 JP 2009511589 A5 JP2009511589 A5 JP 2009511589A5 JP 2008535650 A JP2008535650 A JP 2008535650A JP 2008535650 A JP2008535650 A JP 2008535650A JP 2009511589 A5 JP2009511589 A5 JP 2009511589A5
- Authority
- JP
- Japan
- Prior art keywords
- difluorophenyl
- acetamide
- cyclopropylamino
- hydroxybutan
- phenyl
- 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- Withdrawn
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- -1 3-benzyloxy-5-fluoro-benzyl Chemical group 0.000 claims 39
- 229910052736 halogen Inorganic materials 0.000 claims 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 18
- 239000008194 pharmaceutical composition Substances 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 8
- 125000002619 bicyclic group Chemical group 0.000 claims 8
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 claims 7
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- FJIMJPFTRLZRAJ-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-(3-pyrazol-1-ylphenyl)cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)N1N=CC=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 FJIMJPFTRLZRAJ-UHFFFAOYSA-N 0.000 claims 6
- 101800001718 Amyloid-beta protein Proteins 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 208000024891 symptom Diseases 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- SIEADBCQDXYWBD-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-(3-pyrazol-1-ylphenyl)cyclopropyl]amino]butan-2-yl]-5-oxohexanamide Chemical compound C1CC1(C=1C=C(C=CC=1)N1N=CC=C1)NCC(O)C(NC(=O)CCCC(=O)C)CC1=CC(F)=CC(F)=C1 SIEADBCQDXYWBD-UHFFFAOYSA-N 0.000 claims 4
- QGQLMQKKRGXLTO-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[1-(2,2-dimethylpropyl)pyrazol-3-yl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C1=NN(CC(C)(C)C)C=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 QGQLMQKKRGXLTO-UHFFFAOYSA-N 0.000 claims 4
- VGPRQBUXKLBDJH-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[1-(2,2-dimethylpropyl)pyrazol-4-yl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C1=CN(CC(C)(C)C)N=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 VGPRQBUXKLBDJH-UHFFFAOYSA-N 0.000 claims 4
- IVEXILNYIOKCOY-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[4-(2,2-dimethylpropyl)-1,3-thiazol-2-yl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1SC=C(CC(C)(C)C)N=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 IVEXILNYIOKCOY-UHFFFAOYSA-N 0.000 claims 4
- YEGCCSKZPHGALE-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[4-(2,2-dimethylpropyl)thiophen-2-yl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1SC=C(CC(C)(C)C)C=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 YEGCCSKZPHGALE-UHFFFAOYSA-N 0.000 claims 4
- WETWCOGJYRYKDB-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[5-(2,2-dimethylpropyl)pyridin-3-yl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(CC(C)(C)C)C=NC=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 WETWCOGJYRYKDB-UHFFFAOYSA-N 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 101710137189 Amyloid-beta A4 protein Proteins 0.000 claims 3
- 101710151993 Amyloid-beta precursor protein Proteins 0.000 claims 3
- 102100022704 Amyloid-beta precursor protein Human genes 0.000 claims 3
- 102000004580 Aspartic Acid Proteases Human genes 0.000 claims 3
- 108010017640 Aspartic Acid Proteases Proteins 0.000 claims 3
- 150000001413 amino acids Chemical class 0.000 claims 3
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 claims 3
- 238000003776 cleavage reaction Methods 0.000 claims 3
- 230000035772 mutation Effects 0.000 claims 3
- ZDWBVXDYSLNIIX-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[1-(2,2-dimethylpropyl)triazol-4-yl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1N=NN(CC(C)(C)C)C=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 ZDWBVXDYSLNIIX-UHFFFAOYSA-N 0.000 claims 3
- 230000007017 scission Effects 0.000 claims 3
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 206010002022 amyloidosis Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 239000002439 beta secretase inhibitor Substances 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- PNWYSNDMUPTSHD-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[(6-pyrazol-1-yl-6-bicyclo[3.1.0]hexanyl)amino]butan-2-yl]acetamide Chemical compound C12CCCC2C1(N1N=CC=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 PNWYSNDMUPTSHD-UHFFFAOYSA-N 0.000 claims 2
- KPMQZGRHZHWEMZ-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-(1-thiophen-3-yltriazol-4-yl)cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1N=NN(C=1)C1=CSC=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 KPMQZGRHZHWEMZ-UHFFFAOYSA-N 0.000 claims 2
- MVLKRGPDMFEWHT-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-(3-morpholin-4-ylphenyl)cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)N1CCOCC1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 MVLKRGPDMFEWHT-UHFFFAOYSA-N 0.000 claims 2
- OUEUEMKZZJYMIM-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-(3-pyrazol-1-ylphenyl)cyclopropyl]amino]butan-2-yl]-2-ethoxyacetamide Chemical compound C1CC1(C=1C=C(C=CC=1)N1N=CC=C1)NCC(O)C(NC(=O)COCC)CC1=CC(F)=CC(F)=C1 OUEUEMKZZJYMIM-UHFFFAOYSA-N 0.000 claims 2
- ZDPPYXJEHKYKGE-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-(3-pyrazol-1-ylphenyl)cyclopropyl]amino]butan-2-yl]-2-phenylacetamide Chemical compound C=1C(F)=CC(F)=CC=1CC(NC(=O)CC=1C=CC=CC=1)C(O)CNC1(C=2C=C(C=CC=2)N2N=CC=C2)CC1 ZDPPYXJEHKYKGE-UHFFFAOYSA-N 0.000 claims 2
- DMVPJCZBAVBQPC-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-(3-pyrazol-1-ylphenyl)cyclopropyl]amino]butan-2-yl]-4-oxopentanamide Chemical compound C1CC1(C=1C=C(C=CC=1)N1N=CC=C1)NCC(O)C(NC(=O)CCC(=O)C)CC1=CC(F)=CC(F)=C1 DMVPJCZBAVBQPC-UHFFFAOYSA-N 0.000 claims 2
- PIVCHUBLEMUOKM-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-(3-sulfanylphenyl)cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(S)C=CC=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 PIVCHUBLEMUOKM-UHFFFAOYSA-N 0.000 claims 2
- JTLFPCGNZLJTAK-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-(3-thiomorpholin-4-ylphenyl)cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)N1CCSCC1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 JTLFPCGNZLJTAK-UHFFFAOYSA-N 0.000 claims 2
- IKMNHRLIPMFGAL-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-(4-pyrazol-1-ylthiophen-2-yl)cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1SC=C(C=1)N1N=CC=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 IKMNHRLIPMFGAL-UHFFFAOYSA-N 0.000 claims 2
- JDXAAJLCRYSFNG-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-(5-pyrazol-1-ylpyridin-3-yl)cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=NC=1)N1N=CC=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 JDXAAJLCRYSFNG-UHFFFAOYSA-N 0.000 claims 2
- KAVOLWRXJFPGTL-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[3-(1,1,1-trifluoropropan-2-yl)phenyl]cyclopropyl]amino]butan-2-yl]acetamide Chemical compound FC(F)(F)C(C)C1=CC=CC(C2(CC2)NCC(O)C(CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 KAVOLWRXJFPGTL-UHFFFAOYSA-N 0.000 claims 2
- WAEYCNOIECTQOQ-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[3-(1,4-oxazepan-4-yl)phenyl]cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)N1CCOCCC1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 WAEYCNOIECTQOQ-UHFFFAOYSA-N 0.000 claims 2
- QJZPJRFZQVBYDT-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[3-(1-methoxy-2-methylpropan-2-yl)phenyl]cyclopropyl]amino]butan-2-yl]acetamide Chemical compound COCC(C)(C)C1=CC=CC(C2(CC2)NCC(O)C(CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 QJZPJRFZQVBYDT-UHFFFAOYSA-N 0.000 claims 2
- MPYBDRDFSBFESO-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[3-(2-methyloxolan-2-yl)phenyl]cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C1(C)OCCC1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 MPYBDRDFSBFESO-UHFFFAOYSA-N 0.000 claims 2
- VVZYJILCHBDRDY-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[3-(2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)phenyl]cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)N1C2CC(OC2)C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 VVZYJILCHBDRDY-UHFFFAOYSA-N 0.000 claims 2
- PMWZKFRZXLTHEJ-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[3-(3,3,3-trifluoroprop-1-en-2-yl)phenyl]cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C(=C)C(F)(F)F)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 PMWZKFRZXLTHEJ-UHFFFAOYSA-N 0.000 claims 2
- VSPUEQIYSUJPJH-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[3-(5-methylthiophen-2-yl)phenyl]cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C=1SC(C)=CC=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 VSPUEQIYSUJPJH-UHFFFAOYSA-N 0.000 claims 2
- OPNYLVKDDWJTDR-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[3-(oxan-2-yl)phenyl]cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C1OCCCC1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 OPNYLVKDDWJTDR-UHFFFAOYSA-N 0.000 claims 2
- DGXDCVZUXDMTLV-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[3-(oxolan-2-yl)phenyl]cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C1OCCC1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 DGXDCVZUXDMTLV-UHFFFAOYSA-N 0.000 claims 2
- IROUFPLAOXNCIN-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[3-(oxolan-3-yl)phenyl]cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C1COCC1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 IROUFPLAOXNCIN-UHFFFAOYSA-N 0.000 claims 2
- CNCUETDPNRPUSV-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[3-(pyrazol-1-ylmethyl)phenyl]cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(CN2N=CC=C2)C=CC=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 CNCUETDPNRPUSV-UHFFFAOYSA-N 0.000 claims 2
- AANUSVIEJFJQNH-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[2-hydroxy-1-(3-pyrazol-1-ylphenyl)cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1C(O)C1(C=1C=C(C=CC=1)N1N=CC=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 AANUSVIEJFJQNH-UHFFFAOYSA-N 0.000 claims 2
- YSQIOKPLVZROBE-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[2-methyl-1-(3-pyrazol-1-ylphenyl)cyclopropyl]amino]butan-2-yl]acetamide Chemical compound CC1CC1(C=1C=C(C=CC=1)N1N=CC=C1)NCC(O)C(NC(C)=O)CC1=CC(F)=CC(F)=C1 YSQIOKPLVZROBE-UHFFFAOYSA-N 0.000 claims 2
- RFBDMAJRPBJAJG-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[2-propan-2-yl-1-(3-pyrazol-1-ylphenyl)cyclopropyl]amino]butan-2-yl]acetamide Chemical compound CC(C)C1CC1(C=1C=C(C=CC=1)N1N=CC=C1)NCC(O)C(NC(C)=O)CC1=CC(F)=CC(F)=C1 RFBDMAJRPBJAJG-UHFFFAOYSA-N 0.000 claims 2
- IZGMSRGCRHWDAP-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[2-pyrazol-1-yl-1-(3-pyrazol-1-ylphenyl)cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1C(N2N=CC=C2)C1(C=1C=C(C=CC=1)N1N=CC=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 IZGMSRGCRHWDAP-UHFFFAOYSA-N 0.000 claims 2
- XUCPEEDRFNOSMV-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[6-(3-pyrazol-1-ylphenyl)-3-oxabicyclo[3.1.0]hexan-6-yl]amino]butan-2-yl]acetamide Chemical compound C12COCC2C1(C=1C=C(C=CC=1)N1N=CC=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 XUCPEEDRFNOSMV-UHFFFAOYSA-N 0.000 claims 2
- ZVMGGVCEJGGYGM-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[6-(3-pyrazol-1-ylphenyl)-6-bicyclo[3.1.0]hexanyl]amino]butan-2-yl]acetamide Chemical compound C12CCCC2C1(C=1C=C(C=CC=1)N1N=CC=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 ZVMGGVCEJGGYGM-UHFFFAOYSA-N 0.000 claims 2
- OVWZHAXEKGLFGE-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[2-(2,2-dimethylpropyl)-1,3-thiazol-4-yl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1N=C(CC(C)(C)C)SC=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 OVWZHAXEKGLFGE-UHFFFAOYSA-N 0.000 claims 2
- MQWSLMZURQCBTK-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[3-(1,3-dioxepan-5-yl)phenyl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C1COCOCC1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 MQWSLMZURQCBTK-UHFFFAOYSA-N 0.000 claims 2
- RDDKTENUGJLKIL-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[3-(1,3-dioxolan-4-yl)phenyl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C1OCOC1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 RDDKTENUGJLKIL-UHFFFAOYSA-N 0.000 claims 2
- NGSPCALCYZCXEJ-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[3-(1,4-dioxan-2-yl)phenyl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C1OCCOC1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 NGSPCALCYZCXEJ-UHFFFAOYSA-N 0.000 claims 2
- AIGWVGYYJFMMSE-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[3-(2,2-dimethylpropyl)-5-hydroxyphenyl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(CC(C)(C)C)C=C(O)C=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 AIGWVGYYJFMMSE-UHFFFAOYSA-N 0.000 claims 2
- ZQCQQZFYWOCMQQ-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[3-(2,2-dimethylpropyl)phenyl]cyclobutyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CCC1(C=1C=C(CC(C)(C)C)C=CC=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 ZQCQQZFYWOCMQQ-UHFFFAOYSA-N 0.000 claims 2
- IMQXGQTZVYVTCM-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[3-(3,5-difluorophenyl)phenyl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C=1C=C(F)C=C(F)C=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 IMQXGQTZVYVTCM-UHFFFAOYSA-N 0.000 claims 2
- JQMIMOHSWUTJON-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[3-(3,6-dihydro-2h-pyran-2-yl)phenyl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C1OCC=CC1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 JQMIMOHSWUTJON-UHFFFAOYSA-N 0.000 claims 2
- MIVSXFBYYKBPGG-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[4-(3,3-dimethylbut-1-ynyl)thiophen-2-yl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1SC=C(C=1)C#CC(C)(C)C)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 MIVSXFBYYKBPGG-UHFFFAOYSA-N 0.000 claims 2
- QDQCHWIZBDKMNR-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[4-(3,3-dimethylbutyl)thiophen-2-yl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1SC=C(CCC(C)(C)C)C=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 QDQCHWIZBDKMNR-UHFFFAOYSA-N 0.000 claims 2
- HKQXYIFUKGWWIW-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[5-(2,2-dimethylpropyl)-1-hydroxy-2h-pyridin-3-yl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1CN(O)C=C(CC(C)(C)C)C=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 HKQXYIFUKGWWIW-UHFFFAOYSA-N 0.000 claims 2
- CZKXEGXIEYHWJE-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[5-(2,2-dimethylpropyl)thiophen-2-yl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1SC(CC(C)(C)C)=CC=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 CZKXEGXIEYHWJE-UHFFFAOYSA-N 0.000 claims 2
- DDYVQZCCMNNVFX-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[2,2-dimethyl-1-(3-pyrazol-1-ylphenyl)cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1C(C)(C)C1(C=1C=C(C=CC=1)N1N=CC=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 DDYVQZCCMNNVFX-UHFFFAOYSA-N 0.000 claims 2
- CGJKTEPHXZHNFQ-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[2-ethyl-1-(3-pyrazol-1-ylphenyl)cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound CCC1CC1(C=1C=C(C=CC=1)N1N=CC=C1)NCC(O)C(NC(C)=O)CC1=CC(F)=CC(F)=C1 CGJKTEPHXZHNFQ-UHFFFAOYSA-N 0.000 claims 2
- QZJJBJQULIZPKJ-UHFFFAOYSA-N n-[4-[(2-benzyl-1-pyrazol-1-ylcyclopropyl)amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1C(CC=2C=CC=CC=2)C1(N1N=CC=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 QZJJBJQULIZPKJ-UHFFFAOYSA-N 0.000 claims 2
- VOSLCSAAEXCPJW-UHFFFAOYSA-N n-[4-[[1-(1-tert-butylpyrazol-3-yl)cyclopropyl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C1=NN(C=C1)C(C)(C)C)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 VOSLCSAAEXCPJW-UHFFFAOYSA-N 0.000 claims 2
- WEPJNZHCPOSLFU-UHFFFAOYSA-N n-[4-[[1-(1-tert-butylpyrazol-4-yl)cyclopropyl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C1=CN(N=C1)C(C)(C)C)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 WEPJNZHCPOSLFU-UHFFFAOYSA-N 0.000 claims 2
- NZGDAUFWGYKRKZ-UHFFFAOYSA-N n-[4-[[1-(3-cyclohexylphenyl)cyclopropyl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C1CCCCC1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 NZGDAUFWGYKRKZ-UHFFFAOYSA-N 0.000 claims 2
- WYHKWULUJIUILV-UHFFFAOYSA-N n-[4-[[1-(3-cyclopentylphenyl)cyclopropyl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C1CCCC1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 WYHKWULUJIUILV-UHFFFAOYSA-N 0.000 claims 2
- PJNDAZQEJOLDIW-UHFFFAOYSA-N n-[4-[[1-(3-tert-butylphenyl)cyclopropyl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C(C)(C)C)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 PJNDAZQEJOLDIW-UHFFFAOYSA-N 0.000 claims 2
- KDSLZYKVISFOTP-UHFFFAOYSA-N n-[4-[[1-(5-tert-butyl-1,3-oxazol-2-yl)cyclopropyl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1OC(=CN=1)C(C)(C)C)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 KDSLZYKVISFOTP-UHFFFAOYSA-N 0.000 claims 2
- BOZUJJDDLKJGKX-UHFFFAOYSA-N n-[4-[[1-(5-tert-butylthiophen-3-yl)cyclopropyl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(SC=1)C(C)(C)C)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 BOZUJJDDLKJGKX-UHFFFAOYSA-N 0.000 claims 2
- SXBWNENFIQGMLK-UHFFFAOYSA-N n-[4-[[1-[3-(1,1-difluoro-2-methylpropan-2-yl)phenyl]cyclopropyl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C(C)(C)C(F)F)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 SXBWNENFIQGMLK-UHFFFAOYSA-N 0.000 claims 2
- JMXPNIPCZVRIMT-UHFFFAOYSA-N n-[4-[[1-[3-(1,2-difluoro-2-methylpropyl)phenyl]cyclopropyl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C(F)C(C)(C)F)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 JMXPNIPCZVRIMT-UHFFFAOYSA-N 0.000 claims 2
- HBESBLSFMMMSSP-UHFFFAOYSA-N n-[4-[[1-[3-(3-azabicyclo[2.2.1]heptan-3-yl)phenyl]cyclopropyl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)N1C2CCC(C2)C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 HBESBLSFMMMSSP-UHFFFAOYSA-N 0.000 claims 2
- SQQKQGZDGDICAQ-UHFFFAOYSA-N n-[4-[[6-(3-bromophenyl)-6-bicyclo[3.1.0]hexanyl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C12CCCC2C1(C=1C=C(Br)C=CC=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 SQQKQGZDGDICAQ-UHFFFAOYSA-N 0.000 claims 2
- LNDBIGGNAVZCJB-UHFFFAOYSA-N n-[4-[[6-(4-tert-butylpyridin-2-yl)-6-bicyclo[3.1.0]hexanyl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C12CCCC2C1(C=1N=CC=C(C=1)C(C)(C)C)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 LNDBIGGNAVZCJB-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- YNAXKCRTFJQYDT-UHFFFAOYSA-N 2-hydroxy-5-methylbenzamide Chemical compound CC1=CC=C(O)C(C(N)=O)=C1 YNAXKCRTFJQYDT-UHFFFAOYSA-N 0.000 claims 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 1
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- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 1
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- CDRYJXDHQWBBGU-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-(3-pyrazol-1-ylphenyl)cyclopropyl]amino]butan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound C=1C(F)=CC(F)=CC=1CC(NC(=O)C1NC(=O)CC1)C(O)CNC1(C=2C=C(C=CC=2)N2N=CC=C2)CC1 CDRYJXDHQWBBGU-UHFFFAOYSA-N 0.000 claims 1
- ZOCZHKZWIYSWJT-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[3-(3-oxomorpholin-4-yl)phenyl]cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)N1C(COCC1)=O)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 ZOCZHKZWIYSWJT-UHFFFAOYSA-N 0.000 claims 1
- ZWUYVLYQVJVUAE-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[3-(5-methylthiophen-3-yl)phenyl]cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C=1C=C(C)SC=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 ZWUYVLYQVJVUAE-UHFFFAOYSA-N 0.000 claims 1
- IRYPDHDPDDSJAA-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[4-(pyrazol-1-ylmethyl)thiophen-2-yl]cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1CC1(C=1SC=C(CN2N=CC=C2)C=1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 IRYPDHDPDDSJAA-UHFFFAOYSA-N 0.000 claims 1
- FSGWAITTXZEQNG-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[2-(2-hydroxyethyl)-1-(3-pyrazol-1-ylphenyl)cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1C(CCO)C1(C=1C=C(C=CC=1)N1N=CC=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 FSGWAITTXZEQNG-UHFFFAOYSA-N 0.000 claims 1
- CCULZVPNHUEQJZ-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[2-(hydroxymethyl)-1-(3-pyrazol-1-ylphenyl)cyclopropyl]amino]butan-2-yl]acetamide Chemical compound C1C(CO)C1(C=1C=C(C=CC=1)N1N=CC=C1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 CCULZVPNHUEQJZ-UHFFFAOYSA-N 0.000 claims 1
- IXFUONUONXTQGK-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-(2,6-difluoro-3-pyrazol-1-ylphenyl)cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C(=C(C=CC=1F)N1N=CC=C1)F)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 IXFUONUONXTQGK-UHFFFAOYSA-N 0.000 claims 1
- POYTZWORRGLCCM-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-4-[[1-[3-(3,6-dihydro-2h-pyran-6-yl)phenyl]cyclopropyl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CC1(C=1C=C(C=CC=1)C1C=CCCO1)NCC(O)C(NC(=O)C)CC1=CC(F)=CC(F)=C1 POYTZWORRGLCCM-UHFFFAOYSA-N 0.000 claims 1
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| KR20090031331A (ko) * | 2007-09-21 | 2009-03-25 | 주식회사 엘지생명과학 | 옥소 디하이드로 피라졸을 포함하는 신규한 베타 세크리타제 저해용 화합물 |
| WO2011138285A1 (de) | 2010-05-05 | 2011-11-10 | Bayer Cropscience Ag | Thiazolderivate als schädlingsbekämpfungsmittel |
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| US20060014737A1 (en) * | 2004-03-09 | 2006-01-19 | Varghese John | Methods of treatment of amyloidosis using bi-aryl aspartyl protease inhibitors |
| WO2005095326A2 (en) * | 2004-03-25 | 2005-10-13 | Elan Pharmaceuticals, Inc. | 2-amino- and 2-thio-substituted 1,3-diaminopropanes |
| US7618978B2 (en) * | 2004-04-22 | 2009-11-17 | Eli Lilly And Company | Amides as BACE inhibitors |
| EP1773756A2 (en) * | 2004-07-09 | 2007-04-18 | Elan Pharmaceuticals, Inc. | Oxime derivative substituted hydroxyethylamine aspartyl protease inhibitors |
-
2006
- 2006-10-11 CA CA002624904A patent/CA2624904A1/en not_active Abandoned
- 2006-10-11 JP JP2008535650A patent/JP2009511589A/ja not_active Withdrawn
- 2006-10-11 EP EP06825760A patent/EP1937638A1/en not_active Withdrawn
- 2006-10-11 WO PCT/US2006/039725 patent/WO2007047306A1/en not_active Ceased
- 2006-10-12 US US11/546,347 patent/US20070149525A1/en not_active Abandoned
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