JP2004532894A5 - - Google Patents
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- JP2004532894A5 JP2004532894A5 JP2003503588A JP2003503588A JP2004532894A5 JP 2004532894 A5 JP2004532894 A5 JP 2004532894A5 JP 2003503588 A JP2003503588 A JP 2003503588A JP 2003503588 A JP2003503588 A JP 2003503588A JP 2004532894 A5 JP2004532894 A5 JP 2004532894A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- alkyl
- methyl
- methylsulfonyl
- carboxamide
- 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 cyano, nitro, amino Chemical group 0.000 claims 100
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 85
- 125000000217 alkyl group Chemical group 0.000 claims 77
- 125000000753 cycloalkyl group Chemical group 0.000 claims 51
- 229910052736 halogen Inorganic materials 0.000 claims 50
- 150000002367 halogens Chemical class 0.000 claims 50
- 125000003118 aryl group Chemical group 0.000 claims 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims 28
- 125000000623 heterocyclic group Chemical group 0.000 claims 28
- 125000001072 heteroaryl group Chemical group 0.000 claims 26
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 24
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 20
- 125000000304 alkynyl group Chemical group 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000004663 dialkyl amino group Chemical group 0.000 claims 17
- 125000003342 alkenyl group Chemical group 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 206010012289 Dementia Diseases 0.000 claims 11
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 10
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 8
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 claims 8
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- HEBKCHPVOIAQTA-NGQZWQHPSA-N d-xylitol Chemical compound OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 5
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 230000003412 degenerative effect Effects 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 2
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 2
- 201000010374 Down Syndrome Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010033799 Paralysis Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010044688 Trisomy 21 Diseases 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 210000004227 basal ganglia Anatomy 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 230000001054 cortical effect Effects 0.000 claims 2
- 230000007850 degeneration Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 210000004558 lewy body Anatomy 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 230000000750 progressive effect Effects 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 230000002792 vascular Effects 0.000 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 1
- VOTQNKMWMRRTNF-UHFFFAOYSA-N 1-n-(3,4-dihydroxy-1-phenylnon-8-yn-2-yl)-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=CC=CC=2)C(O)C(O)CCCC#C)=C1 VOTQNKMWMRRTNF-UHFFFAOYSA-N 0.000 claims 1
- ALCHLYSYYJLTFT-UHFFFAOYSA-N 1-n-(3,4-dihydroxy-1-phenylnonan-2-yl)-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C=1C(C)=CC(C(=O)N(CCC)CCC)=CC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC=CC=C1 ALCHLYSYYJLTFT-UHFFFAOYSA-N 0.000 claims 1
- IYXJKKSOTIEAPD-UHFFFAOYSA-N 1-n-(3,4-dihydroxy-1-phenyloctan-2-yl)-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C=1C(C)=CC(C(=O)N(CCC)CCC)=CC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC=CC=C1 IYXJKKSOTIEAPD-UHFFFAOYSA-N 0.000 claims 1
- WPAMKXTYYVGJER-UHFFFAOYSA-N 1-n-(3,4-dihydroxy-1-pyridin-4-ylnon-8-yn-2-yl)-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=CN=CC=2)C(O)C(O)CCCC#C)=C1 WPAMKXTYYVGJER-UHFFFAOYSA-N 0.000 claims 1
- BDPAFFSKXNRJTJ-UHFFFAOYSA-N 1-n-(3,4-dihydroxy-1-pyridin-4-ylnonan-2-yl)-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C=1C(C)=CC(C(=O)N(CCC)CCC)=CC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC=NC=C1 BDPAFFSKXNRJTJ-UHFFFAOYSA-N 0.000 claims 1
- ORAIVINDYDGYIZ-UHFFFAOYSA-N 1-n-(3,4-dihydroxy-1-pyridin-4-yloctan-2-yl)-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C=1C(C)=CC(C(=O)N(CCC)CCC)=CC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC=NC=C1 ORAIVINDYDGYIZ-UHFFFAOYSA-N 0.000 claims 1
- HCHXYKMGADRMPF-UHFFFAOYSA-N 1-n-(5-cyano-3,4-dihydroxy-1-phenylpentan-2-yl)-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=CC=CC=2)C(O)C(O)CC#N)=C1 HCHXYKMGADRMPF-UHFFFAOYSA-N 0.000 claims 1
- LZGBDIBWWSFJNJ-UHFFFAOYSA-N 1-n-(5-cyano-3,4-dihydroxy-1-pyridin-4-ylpentan-2-yl)-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=CN=CC=2)C(O)C(O)CC#N)=C1 LZGBDIBWWSFJNJ-UHFFFAOYSA-N 0.000 claims 1
- SSFQIVVDFOMWBB-UHFFFAOYSA-N 1-n-(6-cyano-3,4-dihydroxy-1-phenylhexan-2-yl)-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=CC=CC=2)C(O)C(O)CCC#N)=C1 SSFQIVVDFOMWBB-UHFFFAOYSA-N 0.000 claims 1
- PDVXUMMVAWACHL-UHFFFAOYSA-N 1-n-(6-cyano-3,4-dihydroxy-1-pyridin-4-ylhexan-2-yl)-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=CN=CC=2)C(O)C(O)CCC#N)=C1 PDVXUMMVAWACHL-UHFFFAOYSA-N 0.000 claims 1
- LLXIOCMEBLSORL-UHFFFAOYSA-N 1-n-(7-cyano-3,4-dihydroxy-1-phenylheptan-2-yl)-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=CC=CC=2)C(O)C(O)CCCC#N)=C1 LLXIOCMEBLSORL-UHFFFAOYSA-N 0.000 claims 1
- AOSMPTJYBUOPRJ-UHFFFAOYSA-N 1-n-(7-cyano-3,4-dihydroxy-1-pyridin-4-ylheptan-2-yl)-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=CN=CC=2)C(O)C(O)CCCC#N)=C1 AOSMPTJYBUOPRJ-UHFFFAOYSA-N 0.000 claims 1
- RWJSXDABPVWKTG-OYUWMTPXSA-N 1-n-[(2s,3r,4r)-1-(3,5-difluorophenyl)-3,4-dihydroxyoctan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C([C@@H]([C@@H](O)[C@H](O)CCCC)NC(=O)C=1C=C(C=C(C)C=1)C(=O)N(CCC)CCC)C1=CC(F)=CC(F)=C1 RWJSXDABPVWKTG-OYUWMTPXSA-N 0.000 claims 1
- QTTSZUAFBOPWSA-OJDZSJEKSA-N 1-n-[(2s,3r,4r)-3,4-dihydroxy-1,7-diphenylheptan-2-yl]-3-n,3-n-dipropylbenzene-1,3,5-tricarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C(N)=O)=CC(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@@H](O)[C@H](O)CCCC=2C=CC=CC=2)=C1 QTTSZUAFBOPWSA-OJDZSJEKSA-N 0.000 claims 1
- RWJSXDABPVWKTG-GMQQYTKMSA-N 1-n-[(2s,3r,4s)-1-(3,5-difluorophenyl)-3,4-dihydroxyoctan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C([C@@H]([C@@H](O)[C@@H](O)CCCC)NC(=O)C=1C=C(C=C(C)C=1)C(=O)N(CCC)CCC)C1=CC(F)=CC(F)=C1 RWJSXDABPVWKTG-GMQQYTKMSA-N 0.000 claims 1
- IYXJKKSOTIEAPD-GMQQYTKMSA-N 1-n-[(2s,3r,4s)-3,4-dihydroxy-1-phenyloctan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C([C@@H]([C@@H](O)[C@@H](O)CCCC)NC(=O)C=1C=C(C=C(C)C=1)C(=O)N(CCC)CCC)C1=CC=CC=C1 IYXJKKSOTIEAPD-GMQQYTKMSA-N 0.000 claims 1
- YHNUDRUAWHFWDB-UHFFFAOYSA-N 1-n-[1-(3,5-difluorophenyl)-3,4-dihydroxynon-8-yn-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)C(O)CCCC#C)=C1 YHNUDRUAWHFWDB-UHFFFAOYSA-N 0.000 claims 1
- WMDGYQCKMSZYOG-UHFFFAOYSA-N 1-n-[1-(3,5-difluorophenyl)-3,4-dihydroxynonan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C=1C(C)=CC(C(=O)N(CCC)CCC)=CC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC(F)=CC(F)=C1 WMDGYQCKMSZYOG-UHFFFAOYSA-N 0.000 claims 1
- RWJSXDABPVWKTG-UHFFFAOYSA-N 1-n-[1-(3,5-difluorophenyl)-3,4-dihydroxyoctan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C=1C(C)=CC(C(=O)N(CCC)CCC)=CC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC(F)=CC(F)=C1 RWJSXDABPVWKTG-UHFFFAOYSA-N 0.000 claims 1
- ZJWHWUVMSFIIDS-UHFFFAOYSA-N 1-n-[3,4-dihydroxy-1-(4-hydroxyphenyl)non-8-yn-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=CC(O)=CC=2)C(O)C(O)CCCC#C)=C1 ZJWHWUVMSFIIDS-UHFFFAOYSA-N 0.000 claims 1
- MNTOBJNGQLGOEM-UHFFFAOYSA-N 1-n-[3,4-dihydroxy-1-(4-hydroxyphenyl)nonan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C=1C(C)=CC(C(=O)N(CCC)CCC)=CC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC=C(O)C=C1 MNTOBJNGQLGOEM-UHFFFAOYSA-N 0.000 claims 1
- GCKMFOCAAVSDHT-UHFFFAOYSA-N 1-n-[3,4-dihydroxy-1-(4-hydroxyphenyl)octan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C=1C(C)=CC(C(=O)N(CCC)CCC)=CC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC=C(O)C=C1 GCKMFOCAAVSDHT-UHFFFAOYSA-N 0.000 claims 1
- YJMNLGJZBOJSET-UHFFFAOYSA-N 1-n-[5-cyano-1-(3,5-difluorophenyl)-3,4-dihydroxypentan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)C(O)CC#N)=C1 YJMNLGJZBOJSET-UHFFFAOYSA-N 0.000 claims 1
- SYOXZQFZLVFTSJ-UHFFFAOYSA-N 1-n-[5-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)pentan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=CC(O)=CC=2)C(O)C(O)CC#N)=C1 SYOXZQFZLVFTSJ-UHFFFAOYSA-N 0.000 claims 1
- AMXNYPPEONHPIA-UHFFFAOYSA-N 1-n-[6-cyano-1-(3,5-difluorophenyl)-3,4-dihydroxyhexan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)C(O)CCC#N)=C1 AMXNYPPEONHPIA-UHFFFAOYSA-N 0.000 claims 1
- HWVLPHLSQWMMCY-UHFFFAOYSA-N 1-n-[6-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)hexan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=CC(O)=CC=2)C(O)C(O)CCC#N)=C1 HWVLPHLSQWMMCY-UHFFFAOYSA-N 0.000 claims 1
- AHOBFZPTLKVJOP-UHFFFAOYSA-N 1-n-[7-cyano-1-(3,5-difluorophenyl)-3,4-dihydroxyheptan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)C(O)CCCC#N)=C1 AHOBFZPTLKVJOP-UHFFFAOYSA-N 0.000 claims 1
- QPVXVENZJINNGY-UHFFFAOYSA-N 1-n-[7-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)heptan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=CC(O)=CC=2)C(O)C(O)CCCC#N)=C1 QPVXVENZJINNGY-UHFFFAOYSA-N 0.000 claims 1
- 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
- MNJRFOQXRKWYNK-JIMJEQGWSA-N 5-bromo-1-n-[(2s,3r,4r)-1-(3,5-difluorophenyl)-3,4-dihydroxyoctan-2-yl]-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound C([C@@H]([C@@H](O)[C@H](O)CCCC)NC(=O)C=1C=C(C=C(Br)C=1)C(=O)N(CCC)CCC)C1=CC(F)=CC(F)=C1 MNJRFOQXRKWYNK-JIMJEQGWSA-N 0.000 claims 1
- RJEBHTRBRCSTAU-ISJGIBHGSA-N 5-bromo-1-n-[(2s,3r,4r)-3,4-dihydroxy-6-methylsulfanyl-1-phenylhexan-2-yl]-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(Br)=CC(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@@H](O)[C@H](O)CCSC)=C1 RJEBHTRBRCSTAU-ISJGIBHGSA-N 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- 241000239366 Euphausiacea Species 0.000 claims 1
- 240000002989 Euphorbia neriifolia Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000005025 alkynylaryl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- FQLOFJPZKGNMBN-UHFFFAOYSA-N n-(3,4-dihydroxy-1-phenylnon-8-yn-2-yl)-2-(methanesulfonamido)-1,3-oxazole-4-carboxamide Chemical compound O1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=CC=CC=2)C(O)C(O)CCCC#C)=C1 FQLOFJPZKGNMBN-UHFFFAOYSA-N 0.000 claims 1
- PIZGCXNUIKRZSS-UHFFFAOYSA-N n-(3,4-dihydroxy-1-phenylnon-8-yn-2-yl)-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound S1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=CC=CC=2)C(O)C(O)CCCC#C)=C1 PIZGCXNUIKRZSS-UHFFFAOYSA-N 0.000 claims 1
- SFEPQHQILIEWBE-UHFFFAOYSA-N n-(3,4-dihydroxy-1-phenylnon-8-yn-2-yl)-2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxamide Chemical compound O1C(N(C)S(C)(=O)=O)=NC(C(=O)NC(CC=2C=CC=CC=2)C(O)C(O)CCCC#C)=C1 SFEPQHQILIEWBE-UHFFFAOYSA-N 0.000 claims 1
- UMOCORDYZKMACY-UHFFFAOYSA-N n-(3,4-dihydroxy-1-phenylnon-8-yn-2-yl)-2-[methyl(methylsulfonyl)amino]-1,3-thiazole-4-carboxamide Chemical compound S1C(N(C)S(C)(=O)=O)=NC(C(=O)NC(CC=2C=CC=CC=2)C(O)C(O)CCCC#C)=C1 UMOCORDYZKMACY-UHFFFAOYSA-N 0.000 claims 1
- ZJNPPKUBLBYDRA-UHFFFAOYSA-N n-(3,4-dihydroxy-1-phenylnonan-2-yl)-2-(methanesulfonamido)-1,3-oxazole-4-carboxamide Chemical compound C=1OC(NS(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC=CC=C1 ZJNPPKUBLBYDRA-UHFFFAOYSA-N 0.000 claims 1
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- OJUGVPAZOPYCRW-UHFFFAOYSA-N n-[7-cyano-1-(3,5-difluorophenyl)-3,4-dihydroxyheptan-2-yl]-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound S1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)C(O)CCCC#N)=C1 OJUGVPAZOPYCRW-UHFFFAOYSA-N 0.000 claims 1
- TUCRQLAFGWOCQS-UHFFFAOYSA-N n-[7-cyano-1-(3,5-difluorophenyl)-3,4-dihydroxyheptan-2-yl]-2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxamide Chemical compound O1C(N(C)S(C)(=O)=O)=NC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)C(O)CCCC#N)=C1 TUCRQLAFGWOCQS-UHFFFAOYSA-N 0.000 claims 1
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- HERKZXKEXMMTOB-UHFFFAOYSA-N n-[7-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)heptan-2-yl]-2-[methyl(methylsulfonyl)amino]-1,3-thiazole-4-carboxamide Chemical compound S1C(N(C)S(C)(=O)=O)=NC(C(=O)NC(CC=2C=CC(O)=CC=2)C(O)C(O)CCCC#N)=C1 HERKZXKEXMMTOB-UHFFFAOYSA-N 0.000 claims 1
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| PCT/US2002/018845 WO2002100818A2 (en) | 2001-06-13 | 2002-06-13 | Aminediols as agents for the treatment of alzheimer's disease |
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| US7695919B2 (en) * | 2001-05-10 | 2010-04-13 | Battelle Energy Alliance, Llc | Antibody profiling sensitivity through increased reporter antibody layering |
| USRE44031E1 (en) | 2001-05-10 | 2013-02-26 | Battelle Energy Alliance, Llc | Antibody profiling sensitivity through increased reporter antibody layering |
| USRE46351E1 (en) | 2001-05-10 | 2017-03-28 | Battelle Energy Alliance, Llc | Antibody profiling sensitivity through increased reporter antibody layering |
| US6989276B2 (en) | 2001-05-10 | 2006-01-24 | Battelle Energy Alliance, Llc | Rapid classification of biological components |
| ATE359995T1 (de) * | 2001-11-19 | 2007-05-15 | Elan Pharm Inc | Amin-1,2- und -1,3-diolverbindungen und deren verwendung zur behandlung von alzheimer-krankheit |
| CA2497979A1 (en) * | 2002-09-06 | 2004-03-18 | Elan Pharmaceuticals, Inc. | 1, 3-diamino-2-hydroxypropane prodrug derivatives |
| US7521481B2 (en) | 2003-02-27 | 2009-04-21 | Mclaurin Joanne | Methods of preventing, treating and diagnosing disorders of protein aggregation |
| US7619059B2 (en) | 2003-07-29 | 2009-11-17 | Life Technologies Corporation | Bimolecular optical probes |
| US7727752B2 (en) * | 2003-07-29 | 2010-06-01 | Life Technologies Corporation | Kinase and phosphatase assays |
| CA2445420A1 (en) | 2003-07-29 | 2005-01-29 | Invitrogen Corporation | Kinase and phosphatase assays |
| US20070196860A1 (en) * | 2006-01-18 | 2007-08-23 | Invitrogen Corporation | Methods for Measuring Real Time Kinase Activity |
| US20080286881A1 (en) * | 2007-05-14 | 2008-11-20 | Apel William A | Compositions and methods for combining report antibodies |
| US8351674B2 (en) * | 2007-05-31 | 2013-01-08 | Battelle Energy Alliance, Llc | Image portion identification methods, image parsing methods, image parsing systems, and articles of manufacture |
| US8962677B2 (en) * | 2007-07-12 | 2015-02-24 | Acumen Pharmaceuticals, Inc. | Methods of restoring cognitive ability using non-peptidic compounds |
| US9006283B2 (en) | 2007-07-12 | 2015-04-14 | Acumen Pharmaceuticals, Inc. | Methods of modifying amyloid β oligomers using non-peptidic compounds |
| US20110098309A1 (en) * | 2007-07-12 | 2011-04-28 | Acumen Pharmaceuticals, Inc. | Methods of inhibiting the formation of amyloid-beta diffusable ligands using acylhydrazide compounds |
| WO2009051661A2 (en) * | 2007-10-12 | 2009-04-23 | The Brigham And Women's Hospital, Inc. | Substituted aryl alkylamino-oxy-analogs and uses thereof |
| US9217024B2 (en) | 2007-12-18 | 2015-12-22 | Acumen Pharmaceuticals, Inc. | ADDL receptor polypeptides, polynucleotides and host cells for recombinant production |
| US9410965B2 (en) * | 2009-09-17 | 2016-08-09 | Battelle Energy Alliance, Llc | Identification of discriminant proteins through antibody profiling, methods and apparatus for identifying an individual |
| US8969009B2 (en) * | 2009-09-17 | 2015-03-03 | Vicki S. Thompson | Identification of discriminant proteins through antibody profiling, methods and apparatus for identifying an individual |
| CN118047698A (zh) * | 2024-01-30 | 2024-05-17 | 山东科巢生物制药有限公司 | 一种n-[(1r)-2-[1,1'-联苯]-4-基-1-(羟基甲基)乙基]氨基甲酸叔丁酯的制备方法 |
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-
2002
- 2002-06-13 US US10/171,343 patent/US6906104B2/en not_active Expired - Fee Related
- 2002-06-13 WO PCT/US2002/018845 patent/WO2002100818A2/en not_active Ceased
- 2002-06-13 JP JP2003503588A patent/JP2004532894A/ja active Pending
- 2002-06-13 AU AU2002315131A patent/AU2002315131A1/en not_active Abandoned
- 2002-06-13 MX MXPA03011521A patent/MXPA03011521A/es not_active Application Discontinuation
- 2002-06-13 CA CA002450205A patent/CA2450205A1/en not_active Abandoned
- 2002-06-13 EP EP02742074A patent/EP1395251A2/en not_active Withdrawn
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