JP2004532894A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- -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
- XSZPAWSHCBKYKT-UHFFFAOYSA-N n-(3,4-dihydroxy-1-phenylnonan-2-yl)-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound C=1SC(NS(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC=CC=C1 XSZPAWSHCBKYKT-UHFFFAOYSA-N 0.000 claims 1
- YOPVCAFJGNBJHO-UHFFFAOYSA-N n-(3,4-dihydroxy-1-phenylnonan-2-yl)-2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxamide Chemical compound C=1OC(N(C)S(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC=CC=C1 YOPVCAFJGNBJHO-UHFFFAOYSA-N 0.000 claims 1
- YOGZLGLNOIHONC-UHFFFAOYSA-N n-(3,4-dihydroxy-1-phenylnonan-2-yl)-2-[methyl(methylsulfonyl)amino]-1,3-thiazole-4-carboxamide Chemical compound C=1SC(N(C)S(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC=CC=C1 YOGZLGLNOIHONC-UHFFFAOYSA-N 0.000 claims 1
- RRMIBABTGXERQS-UHFFFAOYSA-N n-(3,4-dihydroxy-1-phenyloctan-2-yl)-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound C=1SC(NS(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC=CC=C1 RRMIBABTGXERQS-UHFFFAOYSA-N 0.000 claims 1
- PFUFLTNHXQIMMF-UHFFFAOYSA-N n-(3,4-dihydroxy-1-phenyloctan-2-yl)-2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxamide Chemical compound C=1OC(N(C)S(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC=CC=C1 PFUFLTNHXQIMMF-UHFFFAOYSA-N 0.000 claims 1
- PBYNVXJYJYHLNA-UHFFFAOYSA-N n-(3,4-dihydroxy-1-phenyloctan-2-yl)-2-[methyl(methylsulfonyl)amino]-1,3-thiazole-4-carboxamide Chemical compound C=1SC(N(C)S(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC=CC=C1 PBYNVXJYJYHLNA-UHFFFAOYSA-N 0.000 claims 1
- OUXIFDDPZRQVIH-UHFFFAOYSA-N n-(3,4-dihydroxy-1-pyridin-4-ylnon-8-yn-2-yl)-2-(methanesulfonamido)-1,3-oxazole-4-carboxamide Chemical compound O1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=CN=CC=2)C(O)C(O)CCCC#C)=C1 OUXIFDDPZRQVIH-UHFFFAOYSA-N 0.000 claims 1
- ODBYAKDLFIHOPZ-UHFFFAOYSA-N n-(3,4-dihydroxy-1-pyridin-4-ylnon-8-yn-2-yl)-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound S1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=CN=CC=2)C(O)C(O)CCCC#C)=C1 ODBYAKDLFIHOPZ-UHFFFAOYSA-N 0.000 claims 1
- BRYIWUVIWJKGGB-UHFFFAOYSA-N n-(3,4-dihydroxy-1-pyridin-4-ylnon-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=CN=CC=2)C(O)C(O)CCCC#C)=C1 BRYIWUVIWJKGGB-UHFFFAOYSA-N 0.000 claims 1
- DZEFMMSNFRNBMB-UHFFFAOYSA-N n-(3,4-dihydroxy-1-pyridin-4-ylnon-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=CN=CC=2)C(O)C(O)CCCC#C)=C1 DZEFMMSNFRNBMB-UHFFFAOYSA-N 0.000 claims 1
- JYQGIWIBLFOEBW-UHFFFAOYSA-N n-(3,4-dihydroxy-1-pyridin-4-ylnonan-2-yl)-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound C=1SC(NS(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC=NC=C1 JYQGIWIBLFOEBW-UHFFFAOYSA-N 0.000 claims 1
- OERHBZQVAGVNAE-UHFFFAOYSA-N n-(3,4-dihydroxy-1-pyridin-4-ylnonan-2-yl)-2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxamide Chemical compound C=1OC(N(C)S(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC=NC=C1 OERHBZQVAGVNAE-UHFFFAOYSA-N 0.000 claims 1
- OLIWDSFQXZDABW-UHFFFAOYSA-N n-(3,4-dihydroxy-1-pyridin-4-ylnonan-2-yl)-2-[methyl(methylsulfonyl)amino]-1,3-thiazole-4-carboxamide Chemical compound C=1SC(N(C)S(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC=NC=C1 OLIWDSFQXZDABW-UHFFFAOYSA-N 0.000 claims 1
- CSRLBACOQGOZHZ-UHFFFAOYSA-N n-(3,4-dihydroxy-1-pyridin-4-yloctan-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)CCCC)CC1=CC=NC=C1 CSRLBACOQGOZHZ-UHFFFAOYSA-N 0.000 claims 1
- UKMVSXAZDSTTRU-UHFFFAOYSA-N n-(3,4-dihydroxy-1-pyridin-4-yloctan-2-yl)-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound C=1SC(NS(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC=NC=C1 UKMVSXAZDSTTRU-UHFFFAOYSA-N 0.000 claims 1
- OGSUNNQDNMVEES-UHFFFAOYSA-N n-(3,4-dihydroxy-1-pyridin-4-yloctan-2-yl)-2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxamide Chemical compound C=1OC(N(C)S(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC=NC=C1 OGSUNNQDNMVEES-UHFFFAOYSA-N 0.000 claims 1
- JWOVPOURQULVKH-UHFFFAOYSA-N n-(5-cyano-3,4-dihydroxy-1-phenylpentan-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)CC#N)=C1 JWOVPOURQULVKH-UHFFFAOYSA-N 0.000 claims 1
- GZFUHVDVTXJCHB-UHFFFAOYSA-N n-(5-cyano-3,4-dihydroxy-1-phenylpentan-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)CC#N)=C1 GZFUHVDVTXJCHB-UHFFFAOYSA-N 0.000 claims 1
- YCAXZAOSZRANEC-UHFFFAOYSA-N n-(5-cyano-3,4-dihydroxy-1-phenylpentan-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)CC#N)=C1 YCAXZAOSZRANEC-UHFFFAOYSA-N 0.000 claims 1
- UMAZHHLDJHDQIN-UHFFFAOYSA-N n-(5-cyano-3,4-dihydroxy-1-phenylpentan-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)CC#N)=C1 UMAZHHLDJHDQIN-UHFFFAOYSA-N 0.000 claims 1
- BPGNLUYIENRLDZ-UHFFFAOYSA-N n-(5-cyano-3,4-dihydroxy-1-pyridin-4-ylpentan-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=CN=CC=2)C(O)C(O)CC#N)=C1 BPGNLUYIENRLDZ-UHFFFAOYSA-N 0.000 claims 1
- HXDLUPCXCBZOAF-UHFFFAOYSA-N n-(5-cyano-3,4-dihydroxy-1-pyridin-4-ylpentan-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=CN=CC=2)C(O)C(O)CC#N)=C1 HXDLUPCXCBZOAF-UHFFFAOYSA-N 0.000 claims 1
- HKKIFOBUMFFRCB-UHFFFAOYSA-N n-(6-cyano-3,4-dihydroxy-1-phenylhexan-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)CCC#N)=C1 HKKIFOBUMFFRCB-UHFFFAOYSA-N 0.000 claims 1
- MZBTYENZJZQVOV-UHFFFAOYSA-N n-(6-cyano-3,4-dihydroxy-1-phenylhexan-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)CCC#N)=C1 MZBTYENZJZQVOV-UHFFFAOYSA-N 0.000 claims 1
- GVIFTQAQJODAGI-UHFFFAOYSA-N n-(6-cyano-3,4-dihydroxy-1-phenylhexan-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)CCC#N)=C1 GVIFTQAQJODAGI-UHFFFAOYSA-N 0.000 claims 1
- FKRNHURRWQGMNB-UHFFFAOYSA-N n-(6-cyano-3,4-dihydroxy-1-phenylhexan-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)CCC#N)=C1 FKRNHURRWQGMNB-UHFFFAOYSA-N 0.000 claims 1
- ANVXHMPIDHJOQF-UHFFFAOYSA-N n-(6-cyano-3,4-dihydroxy-1-pyridin-4-ylhexan-2-yl)-2-(methanesulfonamido)-1,3-oxazole-4-carboxamide Chemical compound O1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=CN=CC=2)C(O)C(O)CCC#N)=C1 ANVXHMPIDHJOQF-UHFFFAOYSA-N 0.000 claims 1
- BJHDSYBZJBCCNF-UHFFFAOYSA-N n-(6-cyano-3,4-dihydroxy-1-pyridin-4-ylhexan-2-yl)-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound S1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=CN=CC=2)C(O)C(O)CCC#N)=C1 BJHDSYBZJBCCNF-UHFFFAOYSA-N 0.000 claims 1
- SYTFALXDGMFWHL-UHFFFAOYSA-N n-(6-cyano-3,4-dihydroxy-1-pyridin-4-ylhexan-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=CN=CC=2)C(O)C(O)CCC#N)=C1 SYTFALXDGMFWHL-UHFFFAOYSA-N 0.000 claims 1
- INZYNNPHIUNARM-UHFFFAOYSA-N n-(6-cyano-3,4-dihydroxy-1-pyridin-4-ylhexan-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=CN=CC=2)C(O)C(O)CCC#N)=C1 INZYNNPHIUNARM-UHFFFAOYSA-N 0.000 claims 1
- TWIQPTBIJPNVOP-UHFFFAOYSA-N n-(7-cyano-3,4-dihydroxy-1-phenylheptan-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#N)=C1 TWIQPTBIJPNVOP-UHFFFAOYSA-N 0.000 claims 1
- XGDQYIUYQLDHSX-UHFFFAOYSA-N n-(7-cyano-3,4-dihydroxy-1-phenylheptan-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#N)=C1 XGDQYIUYQLDHSX-UHFFFAOYSA-N 0.000 claims 1
- ICURTBPAOYSVNI-UHFFFAOYSA-N n-(7-cyano-3,4-dihydroxy-1-phenylheptan-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#N)=C1 ICURTBPAOYSVNI-UHFFFAOYSA-N 0.000 claims 1
- QVUNSCXBESFMFN-UHFFFAOYSA-N n-(7-cyano-3,4-dihydroxy-1-phenylheptan-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#N)=C1 QVUNSCXBESFMFN-UHFFFAOYSA-N 0.000 claims 1
- NIUBBFWMXOGZGE-UHFFFAOYSA-N n-(7-cyano-3,4-dihydroxy-1-pyridin-4-ylheptan-2-yl)-2-(methanesulfonamido)-1,3-oxazole-4-carboxamide Chemical compound O1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=CN=CC=2)C(O)C(O)CCCC#N)=C1 NIUBBFWMXOGZGE-UHFFFAOYSA-N 0.000 claims 1
- XENVBZCKPVETBG-UHFFFAOYSA-N n-(7-cyano-3,4-dihydroxy-1-pyridin-4-ylheptan-2-yl)-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound S1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=CN=CC=2)C(O)C(O)CCCC#N)=C1 XENVBZCKPVETBG-UHFFFAOYSA-N 0.000 claims 1
- FWDVOPDUQIPVCK-UHFFFAOYSA-N n-(7-cyano-3,4-dihydroxy-1-pyridin-4-ylheptan-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=CN=CC=2)C(O)C(O)CCCC#N)=C1 FWDVOPDUQIPVCK-UHFFFAOYSA-N 0.000 claims 1
- AVNSVOBGZMKSRF-UHFFFAOYSA-N n-(7-cyano-3,4-dihydroxy-1-pyridin-4-ylheptan-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=CN=CC=2)C(O)C(O)CCCC#N)=C1 AVNSVOBGZMKSRF-UHFFFAOYSA-N 0.000 claims 1
- XRPHPHSELWRRSQ-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3,4-dihydroxynon-8-yn-2-yl]-2-(methanesulfonamido)-1,3-oxazole-4-carboxamide Chemical compound O1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)C(O)CCCC#C)=C1 XRPHPHSELWRRSQ-UHFFFAOYSA-N 0.000 claims 1
- QNQDJBDWDQDBLD-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3,4-dihydroxynon-8-yn-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#C)=C1 QNQDJBDWDQDBLD-UHFFFAOYSA-N 0.000 claims 1
- ZPIJWEQMCUXUQY-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3,4-dihydroxynon-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=C(F)C=C(F)C=2)C(O)C(O)CCCC#C)=C1 ZPIJWEQMCUXUQY-UHFFFAOYSA-N 0.000 claims 1
- CALYULJMNQZOMK-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3,4-dihydroxynon-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=C(F)C=C(F)C=2)C(O)C(O)CCCC#C)=C1 CALYULJMNQZOMK-UHFFFAOYSA-N 0.000 claims 1
- FXHVXXFIVVWDAT-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3,4-dihydroxynonan-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(F)=CC(F)=C1 FXHVXXFIVVWDAT-UHFFFAOYSA-N 0.000 claims 1
- PIRNVDSLNDTNIK-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3,4-dihydroxynonan-2-yl]-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound C=1SC(NS(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC(F)=CC(F)=C1 PIRNVDSLNDTNIK-UHFFFAOYSA-N 0.000 claims 1
- BAUVAAAADBKMGK-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3,4-dihydroxyoctan-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)CCCC)CC1=CC(F)=CC(F)=C1 BAUVAAAADBKMGK-UHFFFAOYSA-N 0.000 claims 1
- OQDUITWNUREFQL-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3,4-dihydroxyoctan-2-yl]-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound C=1SC(NS(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC(F)=CC(F)=C1 OQDUITWNUREFQL-UHFFFAOYSA-N 0.000 claims 1
- GVFBRPBVXVMVSW-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3,4-dihydroxyoctan-2-yl]-2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxamide Chemical compound C=1OC(N(C)S(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC(F)=CC(F)=C1 GVFBRPBVXVMVSW-UHFFFAOYSA-N 0.000 claims 1
- QKNRBDDPWVSDKC-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)-3,4-dihydroxyoctan-2-yl]-2-[methyl(methylsulfonyl)amino]-1,3-thiazole-4-carboxamide Chemical compound C=1SC(N(C)S(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC(F)=CC(F)=C1 QKNRBDDPWVSDKC-UHFFFAOYSA-N 0.000 claims 1
- PWJWNFFKDWDGBE-UHFFFAOYSA-N n-[3,4-dihydroxy-1-(4-hydroxyphenyl)non-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(O)=CC=2)C(O)C(O)CCCC#C)=C1 PWJWNFFKDWDGBE-UHFFFAOYSA-N 0.000 claims 1
- GGEKMIOXKSDROE-UHFFFAOYSA-N n-[3,4-dihydroxy-1-(4-hydroxyphenyl)non-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(O)=CC=2)C(O)C(O)CCCC#C)=C1 GGEKMIOXKSDROE-UHFFFAOYSA-N 0.000 claims 1
- MBNBYAPCXZJFPP-UHFFFAOYSA-N n-[3,4-dihydroxy-1-(4-hydroxyphenyl)non-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(O)=CC=2)C(O)C(O)CCCC#C)=C1 MBNBYAPCXZJFPP-UHFFFAOYSA-N 0.000 claims 1
- NQOBVBAZUZUUPX-UHFFFAOYSA-N n-[3,4-dihydroxy-1-(4-hydroxyphenyl)nonan-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=C(O)C=C1 NQOBVBAZUZUUPX-UHFFFAOYSA-N 0.000 claims 1
- CURQIYQIVCECSE-UHFFFAOYSA-N n-[3,4-dihydroxy-1-(4-hydroxyphenyl)nonan-2-yl]-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound C=1SC(NS(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC=C(O)C=C1 CURQIYQIVCECSE-UHFFFAOYSA-N 0.000 claims 1
- XQWPFTCGGFDJOW-UHFFFAOYSA-N n-[3,4-dihydroxy-1-(4-hydroxyphenyl)nonan-2-yl]-2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxamide Chemical compound C=1OC(N(C)S(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC=C(O)C=C1 XQWPFTCGGFDJOW-UHFFFAOYSA-N 0.000 claims 1
- NNJUXMWDUBHUGC-UHFFFAOYSA-N n-[3,4-dihydroxy-1-(4-hydroxyphenyl)nonan-2-yl]-2-[methyl(methylsulfonyl)amino]-1,3-thiazole-4-carboxamide Chemical compound C=1SC(N(C)S(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCCC)CC1=CC=C(O)C=C1 NNJUXMWDUBHUGC-UHFFFAOYSA-N 0.000 claims 1
- WFJGICCEFVXVPT-UHFFFAOYSA-N n-[3,4-dihydroxy-1-(4-hydroxyphenyl)octan-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)CCCC)CC1=CC=C(O)C=C1 WFJGICCEFVXVPT-UHFFFAOYSA-N 0.000 claims 1
- ZXKUCFQSYVVJSU-UHFFFAOYSA-N n-[3,4-dihydroxy-1-(4-hydroxyphenyl)octan-2-yl]-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound C=1SC(NS(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC=C(O)C=C1 ZXKUCFQSYVVJSU-UHFFFAOYSA-N 0.000 claims 1
- NAEYFZJGFWGELC-UHFFFAOYSA-N n-[3,4-dihydroxy-1-(4-hydroxyphenyl)octan-2-yl]-2-[methyl(methylsulfonyl)amino]-1,3-oxazole-4-carboxamide Chemical compound C=1OC(N(C)S(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC=C(O)C=C1 NAEYFZJGFWGELC-UHFFFAOYSA-N 0.000 claims 1
- XGFKSBZYSHTOLB-UHFFFAOYSA-N n-[3,4-dihydroxy-1-(4-hydroxyphenyl)octan-2-yl]-2-[methyl(methylsulfonyl)amino]-1,3-thiazole-4-carboxamide Chemical compound C=1SC(N(C)S(C)(=O)=O)=NC=1C(=O)NC(C(O)C(O)CCCC)CC1=CC=C(O)C=C1 XGFKSBZYSHTOLB-UHFFFAOYSA-N 0.000 claims 1
- SONIRVREQFAETJ-UHFFFAOYSA-N n-[5-cyano-1-(3,5-difluorophenyl)-3,4-dihydroxypentan-2-yl]-2-(methanesulfonamido)-1,3-oxazole-4-carboxamide Chemical compound O1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)C(O)CC#N)=C1 SONIRVREQFAETJ-UHFFFAOYSA-N 0.000 claims 1
- MUDHFAKDKREPDI-UHFFFAOYSA-N n-[5-cyano-1-(3,5-difluorophenyl)-3,4-dihydroxypentan-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)CC#N)=C1 MUDHFAKDKREPDI-UHFFFAOYSA-N 0.000 claims 1
- WVHQOHHLKUNXFI-UHFFFAOYSA-N n-[5-cyano-1-(3,5-difluorophenyl)-3,4-dihydroxypentan-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)CC#N)=C1 WVHQOHHLKUNXFI-UHFFFAOYSA-N 0.000 claims 1
- NUDMZQOKLWVRKJ-UHFFFAOYSA-N n-[5-cyano-1-(3,5-difluorophenyl)-3,4-dihydroxypentan-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=C(F)C=C(F)C=2)C(O)C(O)CC#N)=C1 NUDMZQOKLWVRKJ-UHFFFAOYSA-N 0.000 claims 1
- KTDKGIVLDJWQCG-UHFFFAOYSA-N n-[5-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)pentan-2-yl]-2-(methanesulfonamido)-1,3-oxazole-4-carboxamide Chemical compound O1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=CC(O)=CC=2)C(O)C(O)CC#N)=C1 KTDKGIVLDJWQCG-UHFFFAOYSA-N 0.000 claims 1
- LCTYKIWGDIWZOU-UHFFFAOYSA-N n-[5-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)pentan-2-yl]-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound S1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=CC(O)=CC=2)C(O)C(O)CC#N)=C1 LCTYKIWGDIWZOU-UHFFFAOYSA-N 0.000 claims 1
- MLKSAXOKSNIZMC-UHFFFAOYSA-N n-[5-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)pentan-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(O)=CC=2)C(O)C(O)CC#N)=C1 MLKSAXOKSNIZMC-UHFFFAOYSA-N 0.000 claims 1
- LYRHHCFIXANRLO-UHFFFAOYSA-N n-[5-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)pentan-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)CC#N)=C1 LYRHHCFIXANRLO-UHFFFAOYSA-N 0.000 claims 1
- XILOSQSWHCLGBH-UHFFFAOYSA-N n-[6-cyano-1-(3,5-difluorophenyl)-3,4-dihydroxyhexan-2-yl]-2-(methanesulfonamido)-1,3-oxazole-4-carboxamide Chemical compound O1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)C(O)CCC#N)=C1 XILOSQSWHCLGBH-UHFFFAOYSA-N 0.000 claims 1
- AOZJRFPYFNMRNG-UHFFFAOYSA-N n-[6-cyano-1-(3,5-difluorophenyl)-3,4-dihydroxyhexan-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)CCC#N)=C1 AOZJRFPYFNMRNG-UHFFFAOYSA-N 0.000 claims 1
- JQVFRUWJPTUFPW-UHFFFAOYSA-N n-[6-cyano-1-(3,5-difluorophenyl)-3,4-dihydroxyhexan-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)CCC#N)=C1 JQVFRUWJPTUFPW-UHFFFAOYSA-N 0.000 claims 1
- UERNBSWKTNJXPG-UHFFFAOYSA-N n-[6-cyano-1-(3,5-difluorophenyl)-3,4-dihydroxyhexan-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=C(F)C=C(F)C=2)C(O)C(O)CCC#N)=C1 UERNBSWKTNJXPG-UHFFFAOYSA-N 0.000 claims 1
- WKFPGGSNRHRNKU-UHFFFAOYSA-N n-[6-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)hexan-2-yl]-2-(methanesulfonamido)-1,3-oxazole-4-carboxamide Chemical compound O1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=CC(O)=CC=2)C(O)C(O)CCC#N)=C1 WKFPGGSNRHRNKU-UHFFFAOYSA-N 0.000 claims 1
- NLSKTFDAABSMDF-UHFFFAOYSA-N n-[6-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)hexan-2-yl]-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound S1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=CC(O)=CC=2)C(O)C(O)CCC#N)=C1 NLSKTFDAABSMDF-UHFFFAOYSA-N 0.000 claims 1
- OLKBLJHSTWMWDY-UHFFFAOYSA-N n-[6-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)hexan-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(O)=CC=2)C(O)C(O)CCC#N)=C1 OLKBLJHSTWMWDY-UHFFFAOYSA-N 0.000 claims 1
- IFDSHJSAEGGRQJ-UHFFFAOYSA-N n-[6-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)hexan-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)CCC#N)=C1 IFDSHJSAEGGRQJ-UHFFFAOYSA-N 0.000 claims 1
- GMSXKMRRNMYAIY-UHFFFAOYSA-N n-[7-cyano-1-(3,5-difluorophenyl)-3,4-dihydroxyheptan-2-yl]-2-(methanesulfonamido)-1,3-oxazole-4-carboxamide Chemical compound O1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)C(O)CCCC#N)=C1 GMSXKMRRNMYAIY-UHFFFAOYSA-N 0.000 claims 1
- 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
- SCEVGOBWCWLWRK-UHFFFAOYSA-N n-[7-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)heptan-2-yl]-2-(methanesulfonamido)-1,3-oxazole-4-carboxamide Chemical compound O1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=CC(O)=CC=2)C(O)C(O)CCCC#N)=C1 SCEVGOBWCWLWRK-UHFFFAOYSA-N 0.000 claims 1
- PZYJRNITEREJRR-UHFFFAOYSA-N n-[7-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)heptan-2-yl]-2-(methanesulfonamido)-1,3-thiazole-4-carboxamide Chemical compound S1C(NS(=O)(=O)C)=NC(C(=O)NC(CC=2C=CC(O)=CC=2)C(O)C(O)CCCC#N)=C1 PZYJRNITEREJRR-UHFFFAOYSA-N 0.000 claims 1
- VKKPNUKKSFMUEK-UHFFFAOYSA-N n-[7-cyano-3,4-dihydroxy-1-(4-hydroxyphenyl)heptan-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(O)=CC=2)C(O)C(O)CCCC#N)=C1 VKKPNUKKSFMUEK-UHFFFAOYSA-N 0.000 claims 1
- 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
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29782701P | 2001-06-13 | 2001-06-13 | |
| US33308401P | 2001-11-19 | 2001-11-19 | |
| PCT/US2002/018845 WO2002100818A2 (en) | 2001-06-13 | 2002-06-13 | Aminediols as agents for the treatment of alzheimer's disease |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004532894A JP2004532894A (ja) | 2004-10-28 |
| JP2004532894A5 true JP2004532894A5 (https=) | 2006-01-05 |
Family
ID=26970331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003503588A Pending JP2004532894A (ja) | 2001-06-13 | 2002-06-13 | アルツハイマー病を治療するためのアミンジオール |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6906104B2 (https=) |
| EP (1) | EP1395251A2 (https=) |
| JP (1) | JP2004532894A (https=) |
| AU (1) | AU2002315131A1 (https=) |
| CA (1) | CA2450205A1 (https=) |
| MX (1) | MXPA03011521A (https=) |
| WO (1) | WO2002100818A2 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6989276B2 (en) * | 2001-05-10 | 2006-01-24 | Battelle Energy Alliance, Llc | Rapid classification of biological components |
| 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 |
| CA2467798A1 (en) * | 2001-11-19 | 2003-05-30 | Pharmacia & Upjohn Company | Amine 1,2- and 1,3-diol compounds and their use for treatment of alzheimer's disease |
| 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 |
| 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 |
| CA2445420A1 (en) | 2003-07-29 | 2005-01-29 | Invitrogen Corporation | Kinase and phosphatase assays |
| US7727752B2 (en) * | 2003-07-29 | 2010-06-01 | Life Technologies 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 |
| US20100286164A1 (en) * | 2007-10-12 | 2010-11-11 | The Brigham And Women's Hospital, Inc | Substituted aryl alkylamino-oxy-analogs and uses thereof |
| WO2009079566A2 (en) | 2007-12-18 | 2009-06-25 | Acumen Pharmaceuticals, Inc. | Novel addl receptor polypeptides, polynucleotides and host cells for recombinant production |
| 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 |
| 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 |
| 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 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4522811A (en) | 1982-07-08 | 1985-06-11 | Syntex (U.S.A.) Inc. | Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides |
| US5721131A (en) | 1987-03-06 | 1998-02-24 | United States Of America As Represented By The Secretary Of The Navy | Surface modification of polymers with self-assembled monolayers that promote adhesion, outgrowth and differentiation of biological cells |
| US5912410A (en) | 1990-06-15 | 1999-06-15 | Scios Inc. | Transgenic non-human mice displaying the amyloid-forming pathology of alzheimer's disease |
| US5387742A (en) | 1990-06-15 | 1995-02-07 | Scios Nova Inc. | Transgenic mice displaying the amyloid-forming pathology of alzheimer's disease |
| WO1992013069A1 (en) | 1991-01-21 | 1992-08-06 | Imperial College Of Science, Technology & Medicine | Test and model for alzheimer's disease |
| US5145684A (en) | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| EP0620849B1 (en) | 1992-01-07 | 2003-06-25 | Elan Pharmaceuticals, Inc. | Transgenic animal models for alzheimer's disease |
| US5604102A (en) | 1992-04-15 | 1997-02-18 | Athena Neurosciences, Inc. | Methods of screening for β-amyloid peptide production inhibitors |
| US5441870A (en) | 1992-04-15 | 1995-08-15 | Athena Neurosciences, Inc. | Methods for monitoring cellular processing of β-amyloid precursor protein |
| US5766846A (en) | 1992-07-10 | 1998-06-16 | Athena Neurosciences | Methods of screening for compounds which inhibit soluble β-amyloid peptide production |
| US5399763A (en) * | 1993-02-01 | 1995-03-21 | Nippon Kayaku Kabushiki Kaisha | Process for preparing optically active 2-aminopropanal |
| NZ264143A (en) * | 1993-08-09 | 1996-11-26 | Lilly Co Eli | Use of an aspartyl protease inhibitor to inhibit beta-amyloid peptide production |
| AU702293B2 (en) | 1993-10-27 | 1999-02-18 | Athena Neurosciences, Inc. | Transgenic animals harboring APP allele having Swedish mutation |
| US5877399A (en) | 1994-01-27 | 1999-03-02 | Johns Hopkins University | Transgenic mice expressing APP-Swedish mutation develop progressive neurologic disease |
| US5728718A (en) * | 1994-12-20 | 1998-03-17 | The United States Of America As Represented By The Department Of Health And Human Services | 2,5-diamino-3,4-disubstituted-1,6-diphenylhexane isosteres comprising benzamide, sulfonamide and anthranilamide subunits and methods of using same |
| US5744346A (en) | 1995-06-07 | 1998-04-28 | Athena Neurosciences, Inc. | β-secretase |
| US5942400A (en) | 1995-06-07 | 1999-08-24 | Elan Pharmaceuticals, Inc. | Assays for detecting β-secretase |
| US5763464A (en) * | 1995-11-22 | 1998-06-09 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Retroviral agents containing anthranilamide, substituted benzamide and other subunits, and methods of using same |
| WO1998022597A2 (en) | 1996-11-20 | 1998-05-28 | Oklahoma Medical Research Foundation | Cloning and characterization of napsin, an aspartic protease |
| US6191166B1 (en) | 1997-11-21 | 2001-02-20 | Elan Pharmaceuticals, Inc. | Methods and compounds for inhibiting β-amyloid peptide release and/or its synthesis |
| US6045829A (en) | 1997-02-13 | 2000-04-04 | Elan Pharma International Limited | Nanocrystalline formulations of human immunodeficiency virus (HIV) protease inhibitors using cellulosic surface stabilizers |
| US5962506A (en) * | 1997-07-07 | 1999-10-05 | Pharmacopeia, Inc. | Glycol and hydroxyphosphonate peptidomimetics as inhibitors of aspartyl proteases |
| GB9812189D0 (en) | 1998-06-05 | 1998-08-05 | Glaxo Group Ltd | Methods and compositions for increasing penetration of HIV protease inhibitors |
| AU5002399A (en) | 1998-07-17 | 2000-02-07 | National Broach And Machine Company | Full form roll finishing technique |
| CN1300320C (zh) | 1998-09-24 | 2007-02-14 | 法玛西雅厄普约翰美国公司 | 阿尔茨海默氏疾病分泌酶 |
| AU1727600A (en) * | 1998-11-16 | 2000-06-05 | C & D Technologies, Inc. | Selectable capacity fixed footprint lead-acid battery racking system with horizontal plates |
| CN1390232A (zh) | 1999-02-10 | 2003-01-08 | 艾兰制药公司 | 人β分泌酶、抑制剂、其组合物和用途 |
| AU7757400A (en) | 1999-08-09 | 2001-03-05 | Vanderbilt University | Antiviral therapy use of p-glycoprotein modulators |
| PT1224297E (pt) | 1999-09-23 | 2009-08-17 | Pharmacia & Upjohn Co Llc | Secretase da doença de alzheimer, seus substratos app e suas utilizações |
| JP2002370183A (ja) * | 2001-06-15 | 2002-12-24 | Yamaha Motor Co Ltd | 監視装置及び監視システム |
-
2002
- 2002-06-13 CA CA002450205A patent/CA2450205A1/en not_active Abandoned
- 2002-06-13 MX MXPA03011521A patent/MXPA03011521A/es not_active Application Discontinuation
- 2002-06-13 JP JP2003503588A patent/JP2004532894A/ja active Pending
- 2002-06-13 AU AU2002315131A patent/AU2002315131A1/en not_active Abandoned
- 2002-06-13 WO PCT/US2002/018845 patent/WO2002100818A2/en not_active Ceased
- 2002-06-13 US US10/171,343 patent/US6906104B2/en not_active Expired - Fee Related
- 2002-06-13 EP EP02742074A patent/EP1395251A2/en not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2004532894A5 (https=) | ||
| JP2005534614A5 (https=) | ||
| JP2006501295A5 (https=) | ||
| RU2003134544A (ru) | Амиды антраниловой кислоты, способы их получения, их применение в качестве антиаритмических средств, а также содержащие их фармацевтические композиции | |
| RU2005107314A (ru) | Пиримидопроизводные, характеризующиеся антипролиферативной активностью | |
| ES2399314T3 (es) | Gamma lactamas sustituidas como agentes terapeúticos | |
| JP2004516314A5 (https=) | ||
| RU2002101723A (ru) | Инданилзамещенные бензолкарбонамиды, способ их получения, их применение в качестве лекарственного средства, а также содержащие их фармацевтические композиции | |
| RU2006107653A (ru) | Связующее вспомогательное вещество и приготовленная на его основе таблетка в форме капли | |
| RU2003121236A (ru) | Арилированные амиды фуран- и тиофенкарбоновых кислот с блокирующим калиевый канал действием | |
| JP2006501181A5 (https=) | ||
| RU2001113733A (ru) | N-(2-арилпропионил) сульфонамиды и содержащие их фармацевтические препараты | |
| JP2014502979A5 (https=) | ||
| JP2005533811A5 (https=) | ||
| RU2006124856A (ru) | Гидронопольные производные в качестве агонистов по отношению к orl1 рецепторам человека | |
| JP2006516626A5 (https=) | ||
| JPS6042374A (ja) | 新規な１，５−ベンゾチアゼピン類、それらの製造方法およびそれらを含有している製薬学的組成物 | |
| HRP20130989T1 (hr) | (2r) -2-[(4-sulfonil)aminofenil] propanamidi i farmaceutski sastavi koji ih sadrže | |
| JP2010505869A5 (https=) | ||
| KR920000715A (ko) | 신규의 n- 벤질-n1- 페닐-및- 펜알킬- 티오우레아류 | |
| IE40869L (en) | Benzenesulphonyl ureas as hypoglycemic agents | |
| JPH10251225A5 (https=) | ||
| ES2034484T3 (es) | El uso de oxidos de tiadiazol para la preparacion de una composicion farmaceutica para el tratamiento de desordenes de motilidad gastrointestinal. | |
| JP2003523995A5 (https=) | ||
| RU2004111284A (ru) | Новое применение замещенных аминометилхроманов для лечения нарушений движений или нежелательных действий, вызываемых средствами, которые вводятся для лечения экстрапирамидных нарушений движений |