JP2006504793A5 - - Google Patents
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- Publication number
- JP2006504793A5 JP2006504793A5 JP2004571986A JP2004571986A JP2006504793A5 JP 2006504793 A5 JP2006504793 A5 JP 2006504793A5 JP 2004571986 A JP2004571986 A JP 2004571986A JP 2004571986 A JP2004571986 A JP 2004571986A JP 2006504793 A5 JP2006504793 A5 JP 2006504793A5
- Authority
- JP
- Japan
- Prior art keywords
- propyl
- hydroxy
- acetamide
- difluoro
- benzyl
- 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.)
- Pending
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- -1 aromatic iodides Chemical class 0.000 description 9
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 description 8
- 238000000034 method Methods 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- VKQBMFKBNMKUBE-UHFFFAOYSA-N 2-iodo-2H-chromene Chemical compound C1=CC=C2C=CC(I)OC2=C1 VKQBMFKBNMKUBE-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000006242 amine protecting group Chemical group 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- KLGNPEBEDZARRW-UHFFFAOYSA-N 2-iodo-3,4-dihydro-2h-chromene Chemical compound C1=CC=C2OC(I)CCC2=C1 KLGNPEBEDZARRW-UHFFFAOYSA-N 0.000 description 1
- AJVGILMUMCKDOA-IZZNHLLZSA-N 4-[[(2r,3s)-3-acetamido-4-(3,5-difluorophenyl)-2-hydroxybutyl]amino]-4-(3-tert-butylphenyl)-n-methylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)NC)CCC1(C=1C=C(C=CC=1)C(C)(C)C)NC[C@@H](O)[C@@H](NC(C)=O)CC1=CC(F)=CC(F)=C1 AJVGILMUMCKDOA-IZZNHLLZSA-N 0.000 description 1
- WKPYEYRMQAMPIL-LOSJGSFVSA-N 4-[[(2r,3s)-3-acetamido-4-(3,5-difluorophenyl)-2-hydroxybutyl]amino]-4-(3-tert-butylphenyl)piperidine-1-carboxamide Chemical class C([C@H](NC(=O)C)[C@H](O)CNC1(CCN(CC1)C(N)=O)C=1C=C(C=CC=1)C(C)(C)C)C1=CC(F)=CC(F)=C1 WKPYEYRMQAMPIL-LOSJGSFVSA-N 0.000 description 1
- OGRNVANZWCVHPG-UHFFFAOYSA-N CC(=O)NC(Cc1cc(F)cc(F)c1)C(O)CNCC1CNCCC1CC(C)(C)C Chemical compound CC(=O)NC(Cc1cc(F)cc(F)c1)C(O)CNCC1CNCCC1CC(C)(C)C OGRNVANZWCVHPG-UHFFFAOYSA-N 0.000 description 1
- HQCBJRGRUUOUDZ-UHFFFAOYSA-N CC(=O)NC(Cc1cc(F)cc(F)c1)C(O)CNCc1cc(CC(C)(C)C)ccc1C1CCN(CC1)S(C)(=O)=O Chemical compound CC(=O)NC(Cc1cc(F)cc(F)c1)C(O)CNCc1cc(CC(C)(C)C)ccc1C1CCN(CC1)S(C)(=O)=O HQCBJRGRUUOUDZ-UHFFFAOYSA-N 0.000 description 1
- MNJRMJVGHDFZIK-UHFFFAOYSA-N CC(=O)NC(Cc1cc(F)cc(F)c1)C(O)CNCc1cc(CC(C)(C)C)ccc1C1CCNC(=O)C1 Chemical compound CC(=O)NC(Cc1cc(F)cc(F)c1)C(O)CNCc1cc(CC(C)(C)C)ccc1C1CCNC(=O)C1 MNJRMJVGHDFZIK-UHFFFAOYSA-N 0.000 description 1
- YHBNQJFQOQDMAX-UHFFFAOYSA-N CC(=O)NC(Cc1cc(F)cc(F)c1)C(O)CNCc1cc(CC(C)(C)C)ccc1NS(C)(=O)=O Chemical compound CC(=O)NC(Cc1cc(F)cc(F)c1)C(O)CNCc1cc(CC(C)(C)C)ccc1NS(C)(=O)=O YHBNQJFQOQDMAX-UHFFFAOYSA-N 0.000 description 1
- HLUVFENNKGWFJS-UHFFFAOYSA-N CC(=O)NC(Cc1cc(F)cc(F)c1)C(O)CNCc1cc(CC(C)(C)C)ccc1S(=O)(=O)Nc1ccccc1 Chemical compound CC(=O)NC(Cc1cc(F)cc(F)c1)C(O)CNCc1cc(CC(C)(C)C)ccc1S(=O)(=O)Nc1ccccc1 HLUVFENNKGWFJS-UHFFFAOYSA-N 0.000 description 1
- BDGHWFBHHVKZDS-ZRRKCSAHSA-N CC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CN[C@@]1(CCCNCC1)c1cccc(c1)C(C)(C)C Chemical compound CC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CN[C@@]1(CCCNCC1)c1cccc(c1)C(C)(C)C BDGHWFBHHVKZDS-ZRRKCSAHSA-N 0.000 description 1
- BELZHPFFRRXWOG-LOSJGSFVSA-N CC(C)c1cccc(c1)C1(CCCCC1)NC[C@@H](O)[C@H](Cc1cc(F)c(O)c(F)c1)NC(C)=O Chemical compound CC(C)c1cccc(c1)C1(CCCCC1)NC[C@@H](O)[C@H](Cc1cc(F)c(O)c(F)c1)NC(C)=O BELZHPFFRRXWOG-LOSJGSFVSA-N 0.000 description 1
- QPHISGKKVAYVBI-RRPNLBNLSA-N CCN1CCC(CC1)(NC[C@@H](O)[C@H](Cc1cc(F)cc(F)c1)NC(C)=O)c1cccc(c1)C(C)C Chemical compound CCN1CCC(CC1)(NC[C@@H](O)[C@H](Cc1cc(F)cc(F)c1)NC(C)=O)c1cccc(c1)C(C)C QPHISGKKVAYVBI-RRPNLBNLSA-N 0.000 description 1
- ALZHZMWJXYTXFK-UHFFFAOYSA-N CNS(=O)(=O)c1ccc(CC(C)(C)C)cc1CNCC(O)C(Cc1cc(F)cc(F)c1)NC(C)=O Chemical compound CNS(=O)(=O)c1ccc(CC(C)(C)C)cc1CNCC(O)C(Cc1cc(F)cc(F)c1)NC(C)=O ALZHZMWJXYTXFK-UHFFFAOYSA-N 0.000 description 1
- GZLQGWNIIWORQV-BJKOFHAPSA-N N-[(2S,3R)-1-(3,5-difluorophenyl)-3-hydroxy-4-[[4-(3-propan-2-yloxyphenyl)oxan-4-yl]amino]butan-2-yl]-2-fluoroacetamide Chemical compound CC(C)Oc1cccc(c1)C1(CCOCC1)NC[C@@H](O)[C@H](Cc1cc(F)cc(F)c1)NC(=O)CF GZLQGWNIIWORQV-BJKOFHAPSA-N 0.000 description 1
- YZYIGLICEOAWTR-RBUKOAKNSA-N N-[(2S,3R)-1-(3,5-difluorophenyl)-4-[2-[2-(2,2-dimethylpropyl)-1,3-thiazol-5-yl]propan-2-ylamino]-3-hydroxybutan-2-yl]acetamide Chemical compound FC=1C=C(C[C@@H]([C@@H](CNC(C)(C)C2=CN=C(S2)CC(C)(C)C)O)NC(C)=O)C=C(C=1)F YZYIGLICEOAWTR-RBUKOAKNSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- USNPOTLKGIASRB-IZZNHLLZSA-N methyl 4-[[(2r,3s)-3-acetamido-4-(3,5-difluorophenyl)-2-hydroxybutyl]amino]-4-(3-tert-butylphenyl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1(C=1C=C(C=CC=1)C(C)(C)C)NC[C@@H](O)[C@@H](NC(C)=O)CC1=CC(F)=CC(F)=C1 USNPOTLKGIASRB-IZZNHLLZSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ZAMBIRFWYNEAHJ-RBUKOAKNSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-3-hydroxy-4-[2-[2-(2-methylpropyl)-1,3-thiazol-5-yl]propan-2-ylamino]butan-2-yl]acetamide Chemical compound S1C(CC(C)C)=NC=C1C(C)(C)NC[C@@H](O)[C@@H](NC(C)=O)CC1=CC(F)=CC(F)=C1 ZAMBIRFWYNEAHJ-RBUKOAKNSA-N 0.000 description 1
- BPYMYLLVJHEDAE-IZZNHLLZSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-methyl-4-(3-propan-2-ylphenyl)piperidin-4-yl]amino]butan-2-yl]acetamide Chemical compound CC(C)C1=CC=CC(C2(CCN(C)CC2)NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 BPYMYLLVJHEDAE-IZZNHLLZSA-N 0.000 description 1
- ZOLMPEMHCWVHKY-LGOXGGHWSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-oxo-4-(3-propan-2-ylphenyl)thian-4-yl]amino]butan-2-yl]acetamide Chemical compound CC(C)C1=CC=CC(C2(CCS(=O)CC2)NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 ZOLMPEMHCWVHKY-LGOXGGHWSA-N 0.000 description 1
- RCOHUTULLLICIN-LHJLODMPSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-3-hydroxy-4-[[3-(3-propan-2-yloxyphenyl)oxan-3-yl]amino]butan-2-yl]acetamide Chemical compound CC(C)OC1=CC=CC(C2(COCCC2)NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 RCOHUTULLLICIN-LHJLODMPSA-N 0.000 description 1
- HBXRDCZVDPEBHE-LHJLODMPSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-3-hydroxy-4-[[3-(3-propan-2-ylphenyl)oxan-3-yl]amino]butan-2-yl]acetamide Chemical compound CC(C)C1=CC=CC(C2(COCCC2)NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 HBXRDCZVDPEBHE-LHJLODMPSA-N 0.000 description 1
- UOKUNDFNXUGJJC-LOSJGSFVSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-3-hydroxy-4-[[4-(3-propan-2-yloxyphenyl)oxan-4-yl]amino]butan-2-yl]acetamide Chemical compound CC(C)OC1=CC=CC(C2(CCOCC2)NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 UOKUNDFNXUGJJC-LOSJGSFVSA-N 0.000 description 1
- QEFGGKHLYDBREI-LOSJGSFVSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-3-hydroxy-4-[[4-(3-propan-2-ylphenyl)-1-(2,2,2-trifluoroacetyl)piperidin-4-yl]amino]butan-2-yl]acetamide Chemical compound CC(C)C1=CC=CC(C2(CCN(CC2)C(=O)C(F)(F)F)NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 QEFGGKHLYDBREI-LOSJGSFVSA-N 0.000 description 1
- AMRFQGHEIBTPHM-LOSJGSFVSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-3-hydroxy-4-[[4-(3-propan-2-ylphenyl)piperidin-4-yl]amino]butan-2-yl]acetamide Chemical compound CC(C)C1=CC=CC(C2(CCNCC2)NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 AMRFQGHEIBTPHM-LOSJGSFVSA-N 0.000 description 1
- CXZXEYUJQRWHPB-LOSJGSFVSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-3-hydroxy-4-[[4-(3-propan-2-ylphenyl)thian-4-yl]amino]butan-2-yl]acetamide Chemical compound CC(C)C1=CC=CC(C2(CCSCC2)NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 CXZXEYUJQRWHPB-LOSJGSFVSA-N 0.000 description 1
- RSZSSBCSMRWEFY-XZOQPEGZSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-4-[2-[3-(2,2-dimethylpropyl)phenyl]propan-2-ylamino]-3-hydroxybutan-2-yl]-2-fluoroacetamide Chemical compound CC(C)(C)CC1=CC=CC(C(C)(C)NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(=O)CF)=C1 RSZSSBCSMRWEFY-XZOQPEGZSA-N 0.000 description 1
- JMLHZBBCZLPDFD-LOSJGSFVSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-4-[[1,1-dioxo-4-(3-propan-2-ylphenyl)thian-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound CC(C)C1=CC=CC(C2(CCS(=O)(=O)CC2)NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 JMLHZBBCZLPDFD-LOSJGSFVSA-N 0.000 description 1
- WAHIMGHKKYULHH-RRPNLBNLSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-4-[[1-ethylsulfonyl-4-(3-propan-2-ylphenyl)piperidin-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound C1CN(S(=O)(=O)CC)CCC1(C=1C=C(C=CC=1)C(C)C)NC[C@@H](O)[C@@H](NC(C)=O)CC1=CC(F)=CC(F)=C1 WAHIMGHKKYULHH-RRPNLBNLSA-N 0.000 description 1
- NRNBKONHSZAGCO-IZZNHLLZSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-4-[[1-formyl-4-(3-propan-2-ylphenyl)piperidin-4-yl]amino]-3-hydroxybutan-2-yl]acetamide Chemical compound CC(C)C1=CC=CC(C2(CCN(CC2)C=O)NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 NRNBKONHSZAGCO-IZZNHLLZSA-N 0.000 description 1
- WTTXUEPBGFULOK-ATTQYFOMSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-4-[[6-(2,2-dimethylpropyl)-3,4-dihydro-2h-chromen-4-yl]amino]-3-hydroxybutan-2-yl]-2-fluoroacetamide Chemical compound C([C@@H]([C@H](O)CNC1CCOC2=CC=C(C=C21)CC(C)(C)C)NC(=O)CF)C1=CC(F)=CC(F)=C1 WTTXUEPBGFULOK-ATTQYFOMSA-N 0.000 description 1
- UEJHCNVNHBILHU-YIKNKFAXSA-N n-[(2s,3r)-4-[[(4r)-4-(3-tert-butylphenyl)-1-methylsulfonylazepan-4-yl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@]1(CCN(CCC1)S(C)(=O)=O)C=1C=C(C=CC=1)C(C)(C)C)C1=CC(F)=CC(F)=C1 UEJHCNVNHBILHU-YIKNKFAXSA-N 0.000 description 1
- UEJHCNVNHBILHU-GKRYNVPLSA-N n-[(2s,3r)-4-[[(4s)-4-(3-tert-butylphenyl)-1-methylsulfonylazepan-4-yl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@]1(CCN(CCC1)S(C)(=O)=O)C=1C=C(C=CC=1)C(C)(C)C)C1=CC(F)=CC(F)=C1 UEJHCNVNHBILHU-GKRYNVPLSA-N 0.000 description 1
- BDGHWFBHHVKZDS-REUBFRLUSA-N n-[(2s,3r)-4-[[(4s)-4-(3-tert-butylphenyl)azepan-4-yl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CN[C@@]1(CCNCCC1)C=1C=C(C=CC=1)C(C)(C)C)C1=CC(F)=CC(F)=C1 BDGHWFBHHVKZDS-REUBFRLUSA-N 0.000 description 1
- MZYUFFBIBGWZPG-RRPNLBNLSA-N n-[(2s,3r)-4-[[1-acetyl-4-(3-propan-2-ylphenyl)piperidin-4-yl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound CC(C)C1=CC=CC(C2(CCN(CC2)C(C)=O)NC[C@@H](O)[C@H](CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 MZYUFFBIBGWZPG-RRPNLBNLSA-N 0.000 description 1
- YFVOANNZUKFDLA-RRPNLBNLSA-N n-[(2s,3r)-4-[[4-(3-tert-butylphenyl)-1-ethylsulfonylpiperidin-4-yl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1CN(S(=O)(=O)CC)CCC1(C=1C=C(C=CC=1)C(C)(C)C)NC[C@@H](O)[C@@H](NC(C)=O)CC1=CC(F)=CC(F)=C1 YFVOANNZUKFDLA-RRPNLBNLSA-N 0.000 description 1
- VTOCROULHXLCTO-IZZNHLLZSA-N n-[(2s,3r)-4-[[4-(3-tert-butylphenyl)-1-methylsulfonylpiperidin-4-yl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C([C@H](NC(=O)C)[C@H](O)CNC1(CCN(CC1)S(C)(=O)=O)C=1C=C(C=CC=1)C(C)(C)C)C1=CC(F)=CC(F)=C1 VTOCROULHXLCTO-IZZNHLLZSA-N 0.000 description 1
- ZZNPZEDXBOXPKP-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[(2-hydroxy-2-methyl-6-propan-2-yl-1,3-dihydroinden-1-yl)amino]butan-2-yl]acetamide Chemical compound C12=CC(C(C)C)=CC=C2CC(C)(O)C1NCC(O)C(NC(C)=O)CC1=CC(F)=CC(F)=C1 ZZNPZEDXBOXPKP-UHFFFAOYSA-N 0.000 description 1
- UBVSMOCCQXRAEM-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[(2-oxo-5-propan-2-yl-1,3-dihydroindol-3-yl)amino]butan-2-yl]acetamide Chemical compound C12=CC(C(C)C)=CC=C2NC(=O)C1NCC(O)C(NC(C)=O)CC1=CC(F)=CC(F)=C1 UBVSMOCCQXRAEM-UHFFFAOYSA-N 0.000 description 1
- UMUKWUJRBWTHPM-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[(2-oxo-6-propan-2-yl-1,3-dihydroinden-1-yl)amino]butan-2-yl]acetamide Chemical compound C12=CC(C(C)C)=CC=C2CC(=O)C1NCC(O)C(NC(C)=O)CC1=CC(F)=CC(F)=C1 UMUKWUJRBWTHPM-UHFFFAOYSA-N 0.000 description 1
- SIRXEBJNBLTORW-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[(2-oxo-6-propan-2-yl-3,4-dihydro-1h-quinolin-4-yl)amino]butan-2-yl]acetamide Chemical compound C12=CC(C(C)C)=CC=C2NC(=O)CC1NCC(O)C(NC(C)=O)CC1=CC(F)=CC(F)=C1 SIRXEBJNBLTORW-UHFFFAOYSA-N 0.000 description 1
- FVCGLJGTGULRQK-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[(3-hydroxy-3-methyl-7-propan-2-yl-2,4-dihydro-1h-naphthalen-1-yl)amino]butan-2-yl]acetamide Chemical compound C12=CC(C(C)C)=CC=C2CC(C)(O)CC1NCC(O)C(NC(C)=O)CC1=CC(F)=CC(F)=C1 FVCGLJGTGULRQK-UHFFFAOYSA-N 0.000 description 1
- INDOQRFKUMFKIU-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[(3-oxo-7-propan-2-yl-2,4-dihydro-1h-naphthalen-1-yl)amino]butan-2-yl]acetamide Chemical compound C12=CC(C(C)C)=CC=C2CC(=O)CC1NCC(O)C(NC(C)=O)CC1=CC(F)=CC(F)=C1 INDOQRFKUMFKIU-UHFFFAOYSA-N 0.000 description 1
- BQZAWEGAYUNKOO-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-(3-propan-2-ylphenyl)cyclobutyl]amino]butan-2-yl]acetamide Chemical compound CC(C)C1=CC=CC(C2(CCC2)NCC(O)C(CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 BQZAWEGAYUNKOO-UHFFFAOYSA-N 0.000 description 1
- JXXJIXOVFJAARM-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-(3-propan-2-ylphenyl)cyclopentyl]amino]butan-2-yl]acetamide Chemical compound CC(C)C1=CC=CC(C2(CCCC2)NCC(O)C(CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 JXXJIXOVFJAARM-UHFFFAOYSA-N 0.000 description 1
- SFUTUZARGZOSMO-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[2,2,4,4-tetramethyl-3-oxo-1-(3-propan-2-ylphenyl)cyclobutyl]amino]butan-2-yl]acetamide Chemical compound CC(C)C1=CC=CC(C2(NCC(O)C(CC=3C=C(F)C=C(F)C=3)NC(C)=O)C(C(=O)C2(C)C)(C)C)=C1 SFUTUZARGZOSMO-UHFFFAOYSA-N 0.000 description 1
- STIZOSVVIKQECX-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3-hydroxy-4-[[2-(4-methylpiperazin-1-yl)-5-(2-methylpropyl)phenyl]methylamino]butan-2-yl]acetamide Chemical compound C=1C(F)=CC(F)=CC=1CC(NC(C)=O)C(O)CNCC1=CC(CC(C)C)=CC=C1N1CCN(C)CC1 STIZOSVVIKQECX-UHFFFAOYSA-N 0.000 description 1
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- UXTXWUSOMKQZFS-UHFFFAOYSA-N n-[4-[[4-(3-tert-butylphenyl)oxan-4-yl]amino]-1-(3,5-difluorophenyl)-3-hydroxypentan-2-yl]acetamide Chemical compound C=1C(F)=CC(F)=CC=1CC(NC(C)=O)C(O)C(C)NC1(C=2C=C(C=CC=2)C(C)(C)C)CCOCC1 UXTXWUSOMKQZFS-UHFFFAOYSA-N 0.000 description 1
- LVRREEDPVDGRTD-UHFFFAOYSA-N n-[4-[[6-(2,2-dimethylpropyl)-3,4-dihydro-2h-chromen-4-yl]amino]-1-(3-fluoro-4-hydroxyphenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1COC2=CC=C(CC(C)(C)C)C=C2C1NCC(O)C(NC(=O)C)CC1=CC=C(O)C(F)=C1 LVRREEDPVDGRTD-UHFFFAOYSA-N 0.000 description 1
- IJYFXCLFIWWIDE-UHFFFAOYSA-N n-[4-[[6-(2,2-dimethylpropyl)-3,4-dihydro-2h-chromen-4-yl]amino]-3-hydroxy-1-(5-hydroxypyridin-2-yl)butan-2-yl]acetamide Chemical compound C1COC2=CC=C(CC(C)(C)C)C=C2C1NCC(O)C(NC(=O)C)CC1=CC=C(O)C=N1 IJYFXCLFIWWIDE-UHFFFAOYSA-N 0.000 description 1
- ASEBRBPOHPQWKD-UHFFFAOYSA-N n-[4-[[6-acetyl-3-(3-propan-2-ylphenyl)-6-azabicyclo[3.1.0]hexan-3-yl]amino]-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound CC(C)C1=CC=CC(C2(CC3C(N3C(C)=O)C2)NCC(O)C(CC=2C=C(F)C=C(F)C=2)NC(C)=O)=C1 ASEBRBPOHPQWKD-UHFFFAOYSA-N 0.000 description 1
- KSUBPNQRUAPZAN-UHFFFAOYSA-N n-[4-[[7-(2,2-dimethylpropyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino]-1-(3-fluoro-4-hydroxyphenyl)-3-hydroxybutan-2-yl]acetamide Chemical compound C1CCC2=CC=C(CC(C)(C)C)C=C2C1NCC(O)C(NC(=O)C)CC1=CC=C(O)C(F)=C1 KSUBPNQRUAPZAN-UHFFFAOYSA-N 0.000 description 1
- JLZHHXVXYUTXQY-UHFFFAOYSA-N n-[4-[[7-(2,2-dimethylpropyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino]-3-hydroxy-1-(5-hydroxypyridin-2-yl)butan-2-yl]acetamide Chemical compound C1CCC2=CC=C(CC(C)(C)C)C=C2C1NCC(O)C(NC(=O)C)CC1=CC=C(O)C=N1 JLZHHXVXYUTXQY-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
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| US45223103P | 2003-03-05 | 2003-03-05 | |
| US49175703P | 2003-08-01 | 2003-08-01 | |
| PCT/US2003/028503 WO2004024081A2 (en) | 2002-09-10 | 2003-09-10 | Acetyl 2-hydroxy-1,3 diaminoalkanes |
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| JP (2) | JP2006504793A (https=) |
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| US9296698B2 (en) | 2009-11-23 | 2016-03-29 | Amgen Inc. | Amino heteroaryl compounds as beta-secretase modulators and methods of use |
| AU2011207679B2 (en) | 2010-01-19 | 2013-10-10 | Amgen Inc. | Amino heteroaryl compounds as beta-secretase modulators and methods of use |
| EP2547685A1 (en) | 2010-03-15 | 2013-01-23 | Amgen Inc. | Spiro-tetracyclic ring compounds as beta - secretase modulators |
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| EP2673279A1 (en) | 2011-02-07 | 2013-12-18 | Amgen Inc. | 5-amino-oxazepine and 5-amino-thiazepane compounds as beta-secretase antagonists and methods of use |
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| CN113189089B (zh) * | 2021-03-19 | 2022-05-17 | 四川轻化工大学 | 一种臭氧检测试剂及其制备装置和制备方法 |
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| BR0214736A (pt) * | 2001-12-06 | 2004-11-23 | Elan Pharm Inc | Composto e seus sais farmaceuticamente aceitáveis, composição farmacêutica e método de tratar seres humanos ou animais que sofrem de doenças ou condições |
| CN1732161A (zh) * | 2002-09-06 | 2006-02-08 | 艾伦药物公司 | 1,3－二氨基－2－羟基丙烷前体药物衍生物 |
-
2003
- 2003-09-09 UY UY27967A patent/UY27967A1/es not_active Application Discontinuation
- 2003-09-10 BR BR0314188-8A patent/BR0314188A/pt not_active IP Right Cessation
- 2003-09-10 AU AU2003267132A patent/AU2003267132A1/en not_active Abandoned
- 2003-09-10 GE GEAP20038737A patent/GEP20074166B/en unknown
- 2003-09-10 PL PL376511A patent/PL376511A1/pl not_active Application Discontinuation
- 2003-09-10 NZ NZ539095A patent/NZ539095A/en not_active IP Right Cessation
- 2003-09-10 TW TW092125081A patent/TWI336320B/zh not_active IP Right Cessation
- 2003-09-10 UA UAA200502191A patent/UA84407C2/ru unknown
- 2003-09-10 US US10/658,959 patent/US7244725B2/en not_active Expired - Fee Related
- 2003-09-10 OA OA1200500066A patent/OA12919A/en unknown
- 2003-09-10 AR ARP030103276A patent/AR043679A1/es unknown
- 2003-09-10 PE PE2003000914A patent/PE20041079A1/es not_active Application Discontinuation
- 2003-09-10 JP JP2004571986A patent/JP2006504793A/ja active Pending
- 2003-09-10 MX MXPA05002695A patent/MXPA05002695A/es active IP Right Grant
- 2003-09-10 KR KR1020057004161A patent/KR20060057520A/ko not_active Ceased
- 2003-09-10 CA CA002498248A patent/CA2498248A1/en not_active Abandoned
- 2003-09-10 EA EA200500472A patent/EA009196B1/ru not_active IP Right Cessation
- 2003-09-10 WO PCT/US2003/028503 patent/WO2004024081A2/en not_active Ceased
- 2003-09-10 EP EP03749607A patent/EP1565443A4/en not_active Withdrawn
-
2005
- 2005-03-09 IS IS7732A patent/IS7732A/is unknown
- 2005-03-10 NO NO20051239A patent/NO20051239L/no not_active Application Discontinuation
- 2005-03-21 EC EC2005005696A patent/ECSP055696A/es unknown
- 2005-04-06 MA MA28202A patent/MA27472A1/fr unknown
-
2006
- 2006-06-06 US US11/447,789 patent/US7645780B2/en not_active Expired - Fee Related
-
2009
- 2009-11-23 US US12/624,100 patent/US20100145056A1/en not_active Abandoned
-
2010
- 2010-12-08 JP JP2010273586A patent/JP2011084568A/ja active Pending
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