CA2524511A1 - Isoxazole and isothiazole compounds for the treatment of neurodegenerative disorders - Google Patents

Info

Publication number

CA2524511A1

CA2524511A1 CA002524511A CA2524511A CA2524511A1 CA 2524511 A1 CA2524511 A1 CA 2524511A1 CA 002524511 A CA002524511 A CA 002524511A CA 2524511 A CA2524511 A CA 2524511A CA 2524511 A1 CA2524511 A1 CA 2524511A1

Authority

CA

Canada

Prior art keywords

isoxazol

amide

phenyl

pentanoic acid

hydroxy

Prior art date

2003-05-12

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 208000015122 neurodegenerative disease Diseases 0.000 title abstract description 6
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 title description 7
• 150000003854 isothiazoles Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 107
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 66
• 201000010099 disease Diseases 0.000 claims abstract description 52
• 238000000034 method Methods 0.000 claims abstract description 43
• 241000124008 Mammalia Species 0.000 claims abstract description 29
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• -1 hetreocycloalkyl Chemical group 0.000 claims description 129
• 125000000217 alkyl group Chemical group 0.000 claims description 99
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 79
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 65
• 125000001072 heteroaryl group Chemical group 0.000 claims description 52
• 125000003118 aryl group Chemical group 0.000 claims description 45
• 125000003342 alkenyl group Chemical group 0.000 claims description 43
• 125000001424 substituent group Chemical group 0.000 claims description 42
• 239000000203 mixture Substances 0.000 claims description 35
• 150000003839 salts Chemical class 0.000 claims description 29
• 125000000304 alkynyl group Chemical group 0.000 claims description 27
• 125000001246 bromo group Chemical group Br* 0.000 claims description 23
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 22
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
• 125000001153 fluoro group Chemical group F* 0.000 claims description 20
• 229910052760 oxygen Inorganic materials 0.000 claims description 19
• 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 239000003795 chemical substances by application Substances 0.000 claims description 14
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 13
• 201000010374 Down Syndrome Diseases 0.000 claims description 12
• 206010044688 Trisomy 21 Diseases 0.000 claims description 12
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 102000029797 Prion Human genes 0.000 claims description 9
• 108091000054 Prion Proteins 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 230000001404 mediated effect Effects 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 229940080818 propionamide Drugs 0.000 claims description 9
• 208000018282 ACys amyloidosis Diseases 0.000 claims description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 208000007487 Familial Cerebral Amyloid Angiopathy Diseases 0.000 claims description 8
• 208000032849 Hereditary cerebral hemorrhage with amyloidosis Diseases 0.000 claims description 8
• 208000006011 Stroke Diseases 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 201000008319 inclusion body myositis Diseases 0.000 claims description 8
• 201000006417 multiple sclerosis Diseases 0.000 claims description 8
• 239000000651 prodrug Substances 0.000 claims description 8
• 229940002612 prodrug Drugs 0.000 claims description 8
• 125000004104 aryloxy group Chemical group 0.000 claims description 7
• 150000002148 esters Chemical class 0.000 claims description 7
• 239000013543 active substance Substances 0.000 claims description 6
• 230000001430 anti-depressive effect Effects 0.000 claims description 6
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 6
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 6
• 239000000935 antidepressant agent Substances 0.000 claims description 6
• 229940005513 antidepressants Drugs 0.000 claims description 6
• 239000002220 antihypertensive agent Substances 0.000 claims description 6
• 229940030600 antihypertensive agent Drugs 0.000 claims description 6
• 239000003963 antioxidant agent Substances 0.000 claims description 6
• 239000000164 antipsychotic agent Substances 0.000 claims description 6
• 239000002249 anxiolytic agent Substances 0.000 claims description 6
• 230000000949 anxiolytic effect Effects 0.000 claims description 6
• 235000012000 cholesterol Nutrition 0.000 claims description 6
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
• 230000006993 memory improvement Effects 0.000 claims description 6
• 229940125707 sleep disorder agent Drugs 0.000 claims description 6
• DSLNWSQIHGHNRE-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-(1-hydroxyethyl)-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(C(C)O)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 DSLNWSQIHGHNRE-UHFFFAOYSA-N 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• HGOCUZUCEZABAF-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)-2-hydroxyacetyl]amino]-n-[5-(6-methoxy-2,6-dimethylheptyl)-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(CC(C)CCCC(C)(C)OC)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC(F)=CC(F)=C1 HGOCUZUCEZABAF-UHFFFAOYSA-N 0.000 claims description 4
• NAJLUYHMJIEKBT-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-(1-pyrrolidin-1-ylethyl)-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(C(C)N2CCCC2)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 NAJLUYHMJIEKBT-UHFFFAOYSA-N 0.000 claims description 4
• LGGQMUKJOLPKKU-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-[1-(4-methylpiperazin-1-yl)ethyl]-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(C(C)N2CCN(C)CC2)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 LGGQMUKJOLPKKU-UHFFFAOYSA-N 0.000 claims description 4
• NSXXOSJHRVISGK-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-[1-(dimethylamino)ethyl]-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(C(C)N(C)C)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 NSXXOSJHRVISGK-UHFFFAOYSA-N 0.000 claims description 4
• FAMSKBZGXIMEAK-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-[1-[2-(dimethylamino)ethylamino]ethyl]-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(C(C)NCCN(C)C)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 FAMSKBZGXIMEAK-UHFFFAOYSA-N 0.000 claims description 4
• REEWEQGWVGZMSK-UHFFFAOYSA-N n-(5-cyclohexyl-1,2-oxazol-3-yl)-2-[[2-(3,5-difluorophenyl)-2-hydroxyacetyl]amino]pentanamide Chemical compound C1=C(C2CCCCC2)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC(F)=CC(F)=C1 REEWEQGWVGZMSK-UHFFFAOYSA-N 0.000 claims description 4
• VMFZJMPQPHVPFZ-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)-2-[[2-(3,5-difluorophenyl)-2-hydroxyacetyl]amino]propanamide Chemical compound C1=C(C(C)(C)C)ON=C1NC(=O)C(C)NC(=O)C(O)C1=CC(F)=CC(F)=C1 VMFZJMPQPHVPFZ-UHFFFAOYSA-N 0.000 claims description 4
• KVHNWBYZYAFOKS-UHFFFAOYSA-N n-[1-[(5-tert-butyl-1,2-oxazol-3-yl)amino]-1-oxopropan-2-yl]-2-hydroxy-3-methylbutanamide Chemical compound CC(C)C(O)C(=O)NC(C)C(=O)NC=1C=C(C(C)(C)C)ON=1 KVHNWBYZYAFOKS-UHFFFAOYSA-N 0.000 claims description 4
• COOOHHOCZYPLEU-UHFFFAOYSA-N n-[3-(cyclopentylmethyl)-1,2-oxazol-5-yl]-2-[[2-(3,5-difluorophenyl)-2-hydroxyacetyl]amino]pentanamide Chemical compound C=1C(CC2CCCC2)=NOC=1NC(=O)C(CCC)NC(=O)C(O)C1=CC(F)=CC(F)=C1 COOOHHOCZYPLEU-UHFFFAOYSA-N 0.000 claims description 4
• JPVJWWHHDRCOTR-UHFFFAOYSA-N n-[5-(cyclopentylmethyl)-1,2-oxazol-3-yl]-2-[[2-(3,5-difluorophenyl)-2-hydroxyacetyl]amino]pentanamide Chemical compound C1=C(CC2CCCC2)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC(F)=CC(F)=C1 JPVJWWHHDRCOTR-UHFFFAOYSA-N 0.000 claims description 4
• HHYWDGNPLQVCGF-UHFFFAOYSA-N n-[5-[1-(4-tert-butylphenyl)propan-2-yl]-1,2-oxazol-3-yl]-2-[[2-(3,5-difluorophenyl)-2-hydroxyacetyl]amino]pentanamide Chemical compound C1=C(C(C)CC=2C=CC(=CC=2)C(C)(C)C)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC(F)=CC(F)=C1 HHYWDGNPLQVCGF-UHFFFAOYSA-N 0.000 claims description 4
• MPUYRMSULNLYKP-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-[(3-methoxypropylamino)methyl]-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(CNCCCOC)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 MPUYRMSULNLYKP-UHFFFAOYSA-N 0.000 claims description 3
• MWQCEISSYPLMBV-UHFFFAOYSA-N 2-[[2-(5-bromopyridin-3-yl)acetyl]amino]-n-(5-tert-butyl-1,2-oxazol-3-yl)propanamide Chemical compound C1=C(C(C)(C)C)ON=C1NC(=O)C(C)NC(=O)CC1=CN=CC(Br)=C1 MWQCEISSYPLMBV-UHFFFAOYSA-N 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• BTNSDUDBEAHGMX-UHFFFAOYSA-N n-(3-cyclohexyl-1,2-oxazol-5-yl)-2-[[2-(3,5-difluorophenyl)-2-hydroxyacetyl]amino]pentanamide Chemical compound C=1C(C2CCCCC2)=NOC=1NC(=O)C(CCC)NC(=O)C(O)C1=CC(F)=CC(F)=C1 BTNSDUDBEAHGMX-UHFFFAOYSA-N 0.000 claims description 3
• DHUAGBRLGOYTNY-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)-2-[[2-(3-phenoxyphenyl)acetyl]amino]propanamide Chemical compound C1=C(C(C)(C)C)ON=C1NC(=O)C(C)NC(=O)CC(C=1)=CC=CC=1OC1=CC=CC=C1 DHUAGBRLGOYTNY-UHFFFAOYSA-N 0.000 claims description 3
• YWYWRRBHGOAZGY-UHFFFAOYSA-N n-[1-[(5-tert-butyl-1,2-oxazol-3-yl)amino]-1-oxobutan-2-yl]-2-hydroxy-3,3-dimethylbutanamide Chemical compound CC(C)(C)C(O)C(=O)NC(CC)C(=O)NC=1C=C(C(C)(C)C)ON=1 YWYWRRBHGOAZGY-UHFFFAOYSA-N 0.000 claims description 3
• HABCRZZMCRYANK-UHFFFAOYSA-N n-[1-[(5-tert-butyl-1,2-oxazol-3-yl)amino]-1-oxopentan-2-yl]-2-hydroxy-3,3-dimethylbutanamide Chemical compound CC(C)(C)C(O)C(=O)NC(CCC)C(=O)NC=1C=C(C(C)(C)C)ON=1 HABCRZZMCRYANK-UHFFFAOYSA-N 0.000 claims description 3
• QCAAIRNXTUNVMR-UHFFFAOYSA-N n-[1-[(5-tert-butyl-1,2-oxazol-3-yl)amino]-1-oxopropan-2-yl]-2-hydroxy-3,3-dimethylbutanamide Chemical compound CC(C)(C)C(O)C(=O)NC(C)C(=O)NC=1C=C(C(C)(C)C)ON=1 QCAAIRNXTUNVMR-UHFFFAOYSA-N 0.000 claims description 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• DHKCQFRAXLGSGL-UHFFFAOYSA-N 1-[[3-[2-[[2-(3,5-difluorophenyl)acetyl]amino]pentanoylamino]-1,2-oxazol-5-yl]methyl]-n,n-diethylpiperidine-4-carboxamide Chemical compound C1=C(CN2CCC(CC2)C(=O)N(CC)CC)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 DHKCQFRAXLGSGL-UHFFFAOYSA-N 0.000 claims description 2
• RILQYCOUYNEUIA-UHFFFAOYSA-N 2-[(2-hydroxy-2-phenylacetyl)amino]-n-(5-phenyl-1,2-oxazol-3-yl)pentanamide Chemical compound C1=C(C=2C=CC=CC=2)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC=CC=C1 RILQYCOUYNEUIA-UHFFFAOYSA-N 0.000 claims description 2
• CLFNKFQWTWDQOZ-UHFFFAOYSA-N 2-[(2-hydroxy-2-phenylacetyl)amino]-n-[5-(6-methoxy-2,6-dimethylheptyl)-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(CC(C)CCCC(C)(C)OC)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC=CC=C1 CLFNKFQWTWDQOZ-UHFFFAOYSA-N 0.000 claims description 2
• WBQOCFQTBOYXRZ-UHFFFAOYSA-N 2-[(2-hydroxy-3-methylbutanoyl)amino]-n-(3-methyl-1,2-oxazol-5-yl)pentanamide Chemical compound CC(C)C(O)C(=O)NC(CCC)C(=O)NC1=CC(C)=NO1 WBQOCFQTBOYXRZ-UHFFFAOYSA-N 0.000 claims description 2
• JZJVQARVUVWZNW-UHFFFAOYSA-N 2-[(2-hydroxy-3-methylbutanoyl)amino]-n-(3-phenyl-1,2-oxazol-5-yl)pentanamide Chemical compound O1C(NC(=O)C(NC(=O)C(O)C(C)C)CCC)=CC(C=2C=CC=CC=2)=N1 JZJVQARVUVWZNW-UHFFFAOYSA-N 0.000 claims description 2
• CLDWQEHFHGRVGI-UHFFFAOYSA-N 2-[(2-hydroxy-3-methylbutanoyl)amino]-n-(5-methyl-1,2-oxazol-3-yl)pentanamide Chemical compound CC(C)C(O)C(=O)NC(CCC)C(=O)NC=1C=C(C)ON=1 CLDWQEHFHGRVGI-UHFFFAOYSA-N 0.000 claims description 2
• XPEGEZIBAFAHMC-UHFFFAOYSA-N 2-[(2-hydroxy-3-methylbutanoyl)amino]-n-(5-phenyl-1,2-oxazol-3-yl)pentanamide Chemical compound O1N=C(NC(=O)C(NC(=O)C(O)C(C)C)CCC)C=C1C1=CC=CC=C1 XPEGEZIBAFAHMC-UHFFFAOYSA-N 0.000 claims description 2
• PIAJCQUERJLFKD-UHFFFAOYSA-N 2-[(2-hydroxy-3-methylbutanoyl)amino]-n-[5-(2,4,4-trimethylpentyl)-1,2-oxazol-3-yl]pentanamide Chemical compound CC(C)C(O)C(=O)NC(CCC)C(=O)NC=1C=C(CC(C)CC(C)(C)C)ON=1 PIAJCQUERJLFKD-UHFFFAOYSA-N 0.000 claims description 2
• WVFWLYAXFPMZIM-UHFFFAOYSA-N 2-[(2-hydroxy-3-methylbutanoyl)amino]-n-[5-(3-hydroxypentan-3-yl)-1,2-oxazol-3-yl]pentanamide Chemical compound CC(C)C(O)C(=O)NC(CCC)C(=O)NC=1C=C(C(O)(CC)CC)ON=1 WVFWLYAXFPMZIM-UHFFFAOYSA-N 0.000 claims description 2
• FOKNOOCEIFUOSX-UHFFFAOYSA-N 2-[(2-hydroxy-3-methylbutanoyl)amino]-n-[5-(6-methoxy-2,6-dimethylheptyl)-1,2-oxazol-3-yl]pentanamide Chemical compound CC(C)C(O)C(=O)NC(CCC)C(=O)NC=1C=C(CC(C)CCCC(C)(C)OC)ON=1 FOKNOOCEIFUOSX-UHFFFAOYSA-N 0.000 claims description 2
• HVOVDOFORJVPHL-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)-2-hydroxyacetyl]amino]-n-(3-phenyl-1,2-oxazol-5-yl)pentanamide Chemical compound C=1C(C=2C=CC=CC=2)=NOC=1NC(=O)C(CCC)NC(=O)C(O)C1=CC(F)=CC(F)=C1 HVOVDOFORJVPHL-UHFFFAOYSA-N 0.000 claims description 2
• ZOHRPLMJYUQZGT-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)-2-hydroxyacetyl]amino]-n-(5-phenyl-1,2-oxazol-3-yl)pentanamide Chemical compound C1=C(C=2C=CC=CC=2)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC(F)=CC(F)=C1 ZOHRPLMJYUQZGT-UHFFFAOYSA-N 0.000 claims description 2
• XHMTUMISDDIOOC-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)-2-hydroxyacetyl]amino]-n-[5-(2,4,4-trimethylpentyl)-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(CC(C)CC(C)(C)C)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC(F)=CC(F)=C1 XHMTUMISDDIOOC-UHFFFAOYSA-N 0.000 claims description 2
• RVGVEBMTFWYZFZ-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-N-[5-[(3-propan-2-yloxypropylamino)methyl]-1,2-oxazol-3-yl]pentanamide Chemical compound C(C)(C)OCCCNCC1=CC(=NO1)NC(C(CCC)NC(CC1=CC(=CC(=C1)F)F)=O)=O RVGVEBMTFWYZFZ-UHFFFAOYSA-N 0.000 claims description 2
• NBSNXDKPMDPGMA-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-N-[5-[1-(3,3-dimethylbutoxy)ethyl]-1,2-oxazol-3-yl]pentanamide Chemical compound CCCC(NC(=O)Cc1cc(F)cc(F)c1)C(=O)Nc1cc(on1)C(C)OCCC(C)(C)C NBSNXDKPMDPGMA-UHFFFAOYSA-N 0.000 claims description 2
• NAALVNSRCRRVGA-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-N-[5-[1-(3-propan-2-yloxypropylamino)ethyl]-1,2-oxazol-3-yl]pentanamide Chemical compound C(C)(C)OCCCNC(C)C1=CC(=NO1)NC(C(CCC)NC(CC1=CC(=CC(=C1)F)F)=O)=O NAALVNSRCRRVGA-UHFFFAOYSA-N 0.000 claims description 2
• CISSWCSCYGRXIP-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-N-[5-[1-(4-phenylpiperazin-1-yl)ethyl]-1,2-oxazol-3-yl]pentanamide Chemical compound C1(=CC=CC=C1)N1CCN(CC1)C(C)C1=CC(=NO1)NC(C(CCC)NC(CC1=CC(=CC(=C1)F)F)=O)=O CISSWCSCYGRXIP-UHFFFAOYSA-N 0.000 claims description 2
• HXBQGMXWVBPDMS-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-N-[5-[1-[4-(2-phenylethyl)piperazin-1-yl]ethyl]-1,2-oxazol-3-yl]pentanamide Chemical compound C1(=CC=CC=C1)CCN1CCN(CC1)C(C)C1=CC(=NO1)NC(C(CCC)NC(CC1=CC(=CC(=C1)F)F)=O)=O HXBQGMXWVBPDMS-UHFFFAOYSA-N 0.000 claims description 2
• BFYZNUDBDUVWFJ-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-N-[5-[1-[methyl(2-pyridin-2-ylethyl)amino]ethyl]-1,2-oxazol-3-yl]pentanamide Chemical compound CN(C(C)C1=CC(=NO1)NC(C(CCC)NC(CC1=CC(=CC(=C1)F)F)=O)=O)CCC1=NC=CC=C1 BFYZNUDBDUVWFJ-UHFFFAOYSA-N 0.000 claims description 2
• VPBPJKMQQODESP-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-(3-phenyl-1,2-oxazol-5-yl)pentanamide Chemical compound C=1C(C=2C=CC=CC=2)=NOC=1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 VPBPJKMQQODESP-UHFFFAOYSA-N 0.000 claims description 2
• MNRQNJRNCRHNFB-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-(5-phenyl-1,2-oxazol-3-yl)pentanamide Chemical compound C1=C(C=2C=CC=CC=2)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 MNRQNJRNCRHNFB-UHFFFAOYSA-N 0.000 claims description 2
• CPQFFIHPRDYXEW-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-(3-hydroxypentan-3-yl)-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(C(O)(CC)CC)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 CPQFFIHPRDYXEW-UHFFFAOYSA-N 0.000 claims description 2
• SKAQQBMRPBNDMM-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-(6-methoxy-2,6-dimethylheptyl)-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(CC(C)CCCC(C)(C)OC)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 SKAQQBMRPBNDMM-UHFFFAOYSA-N 0.000 claims description 2
• CJXMXAMMMDBBLR-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-(hydroxymethyl)-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(CO)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 CJXMXAMMMDBBLR-UHFFFAOYSA-N 0.000 claims description 2
• UGHHGWVKEOEBLY-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-(pyrrolidin-1-ylmethyl)-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(CN2CCCC2)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 UGHHGWVKEOEBLY-UHFFFAOYSA-N 0.000 claims description 2
• PMQFZHKDSGUKFX-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-[(4-hydroxypiperidin-1-yl)methyl]-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(CN2CCC(O)CC2)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 PMQFZHKDSGUKFX-UHFFFAOYSA-N 0.000 claims description 2
• KPNYODGZQPIFBK-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(CN2CCC(CC2)N2CCCC2)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 KPNYODGZQPIFBK-UHFFFAOYSA-N 0.000 claims description 2
• HZIGDXFLTLXUHE-UHFFFAOYSA-N 2-[[2-hydroxy-2-(3-phenoxyphenyl)acetyl]amino]-n-[5-(2,4,4-trimethylpentyl)-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(CC(C)CC(C)(C)C)ON=C1NC(=O)C(CCC)NC(=O)C(O)C(C=1)=CC=CC=1OC1=CC=CC=C1 HZIGDXFLTLXUHE-UHFFFAOYSA-N 0.000 claims description 2
• HTMOKJOYQYILGG-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-n-[1-[(3-methyl-1,2-oxazol-5-yl)amino]-1-oxopentan-2-yl]butanamide Chemical compound CC(C)(C)C(O)C(=O)NC(CCC)C(=O)NC1=CC(C)=NO1 HTMOKJOYQYILGG-UHFFFAOYSA-N 0.000 claims description 2
• VEVXMFYLLIDCBP-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-n-[1-[(5-methyl-1,2-oxazol-3-yl)amino]-1-oxopentan-2-yl]butanamide Chemical compound CC(C)(C)C(O)C(=O)NC(CCC)C(=O)NC=1C=C(C)ON=1 VEVXMFYLLIDCBP-UHFFFAOYSA-N 0.000 claims description 2
• MLYKYBOJYVDUKJ-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-n-[1-[[5-(morpholin-4-ylmethyl)-1,2-oxazol-3-yl]amino]-1-oxopentan-2-yl]butanamide Chemical compound O1N=C(NC(=O)C(NC(=O)C(O)C(C)(C)C)CCC)C=C1CN1CCOCC1 MLYKYBOJYVDUKJ-UHFFFAOYSA-N 0.000 claims description 2
• MBDGBCQETOZJKI-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-n-[1-oxo-1-[(3-phenyl-1,2-oxazol-5-yl)amino]pentan-2-yl]butanamide Chemical compound O1C(NC(=O)C(NC(=O)C(O)C(C)(C)C)CCC)=CC(C=2C=CC=CC=2)=N1 MBDGBCQETOZJKI-UHFFFAOYSA-N 0.000 claims description 2
• DERNWPOJSQSQRG-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-n-[1-oxo-1-[(5-pent-2-en-3-yl-1,2-oxazol-3-yl)amino]pentan-2-yl]butanamide Chemical compound CC(C)(C)C(O)C(=O)NC(CCC)C(=O)NC=1C=C(C(CC)=CC)ON=1 DERNWPOJSQSQRG-UHFFFAOYSA-N 0.000 claims description 2
• YGUQUHSLOSBSPX-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-n-[1-oxo-1-[(5-phenyl-1,2-oxazol-3-yl)amino]pentan-2-yl]butanamide Chemical compound O1N=C(NC(=O)C(NC(=O)C(O)C(C)(C)C)CCC)C=C1C1=CC=CC=C1 YGUQUHSLOSBSPX-UHFFFAOYSA-N 0.000 claims description 2
• BPXVFDIFOLNQEG-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-n-[1-oxo-1-[[5-(pyrrolidin-1-ylmethyl)-1,2-oxazol-3-yl]amino]pentan-2-yl]butanamide Chemical compound O1N=C(NC(=O)C(NC(=O)C(O)C(C)(C)C)CCC)C=C1CN1CCCC1 BPXVFDIFOLNQEG-UHFFFAOYSA-N 0.000 claims description 2
• FDILXYFXDKBXAT-UHFFFAOYSA-N 2-hydroxy-n-[1-[[5-(3-hydroxypentan-3-yl)-1,2-oxazol-3-yl]amino]-1-oxopentan-2-yl]-3,3-dimethylbutanamide Chemical compound CC(C)(C)C(O)C(=O)NC(CCC)C(=O)NC=1C=C(C(O)(CC)CC)ON=1 FDILXYFXDKBXAT-UHFFFAOYSA-N 0.000 claims description 2
• RNFWXMLNAQFXRY-UHFFFAOYSA-N 2-hydroxy-n-[1-[[5-(6-methoxy-2,6-dimethylheptyl)-1,2-oxazol-3-yl]amino]-1-oxopentan-2-yl]-3,3-dimethylbutanamide Chemical compound CC(C)(C)C(O)C(=O)NC(CCC)C(=O)NC=1C=C(CC(C)CCCC(C)(C)OC)ON=1 RNFWXMLNAQFXRY-UHFFFAOYSA-N 0.000 claims description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• RDTGUNMIAPPUES-UHFFFAOYSA-N 4-[1-[3-[2-[[2-(3,5-difluorophenyl)acetyl]amino]pentanoylamino]-1,2-oxazol-5-yl]ethyl]-n,n-diethylpiperazine-1-carboxamide Chemical compound C1=C(C(C)N2CCN(CC2)C(=O)N(CC)CC)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 RDTGUNMIAPPUES-UHFFFAOYSA-N 0.000 claims description 2
• VRGSERBPEBYIDB-UHFFFAOYSA-N C1(=CC=CC=C1)C(C)NCCC1=CC(=NO1)NC(C(CCC)NC(CC1=CC(=CC(=C1)F)F)=O)=O Chemical compound C1(=CC=CC=C1)C(C)NCCC1=CC(=NO1)NC(C(CCC)NC(CC1=CC(=CC(=C1)F)F)=O)=O VRGSERBPEBYIDB-UHFFFAOYSA-N 0.000 claims description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• KYGFQRCNJNPJKV-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-[(2-hydroxy-3-methylbutanoyl)amino]pentanamide Chemical compound CC(C)C(O)C(=O)NC(CCC)C(=O)NC=1ON=C(C)C=1C KYGFQRCNJNPJKV-UHFFFAOYSA-N 0.000 claims description 2
• LHCODJYEPWSLQC-UHFFFAOYSA-N n-(3-cyclohexyl-1,2-oxazol-5-yl)-2-[(2-hydroxy-3-methylbutanoyl)amino]pentanamide Chemical compound O1C(NC(=O)C(NC(=O)C(O)C(C)C)CCC)=CC(C2CCCCC2)=N1 LHCODJYEPWSLQC-UHFFFAOYSA-N 0.000 claims description 2
• WRFBDCYKXXKLJA-UHFFFAOYSA-N n-(3-cyclohexyl-1,2-oxazol-5-yl)-2-[[2-(3,5-difluorophenyl)acetyl]amino]pentanamide Chemical compound C=1C(C2CCCCC2)=NOC=1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 WRFBDCYKXXKLJA-UHFFFAOYSA-N 0.000 claims description 2
• DKZJWKRBKOCLPD-UHFFFAOYSA-N n-(3-cyclohexyl-1,2-oxazol-5-yl)-2-[[2-(3-phenoxyphenyl)acetyl]amino]pentanamide Chemical compound C=1C(C2CCCCC2)=NOC=1NC(=O)C(CCC)NC(=O)CC(C=1)=CC=CC=1OC1=CC=CC=C1 DKZJWKRBKOCLPD-UHFFFAOYSA-N 0.000 claims description 2
• LAMYWZDUELEOFQ-UHFFFAOYSA-N n-(5-cyclohexyl-1,2-oxazol-3-yl)-2-[(2-hydroxy-2-phenylacetyl)amino]pentanamide Chemical compound C1=C(C2CCCCC2)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC=CC=C1 LAMYWZDUELEOFQ-UHFFFAOYSA-N 0.000 claims description 2
• GANGQEZPHSQDLG-UHFFFAOYSA-N n-(5-cyclohexyl-1,2-oxazol-3-yl)-2-[(2-hydroxy-3-methylbutanoyl)amino]pentanamide Chemical compound O1N=C(NC(=O)C(NC(=O)C(O)C(C)C)CCC)C=C1C1CCCCC1 GANGQEZPHSQDLG-UHFFFAOYSA-N 0.000 claims description 2
• JFQVSZXGVNEHID-UHFFFAOYSA-N n-(5-cyclohexyl-1,2-oxazol-3-yl)-2-[[2-(3,5-difluorophenyl)acetyl]amino]pentanamide Chemical compound C1=C(C2CCCCC2)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 JFQVSZXGVNEHID-UHFFFAOYSA-N 0.000 claims description 2
• SFZPBKNSNHZLJV-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)-2-[(2-hydroxy-2-phenylacetyl)amino]pentanamide Chemical compound C1=C(C(C)(C)C)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC=CC=C1 SFZPBKNSNHZLJV-UHFFFAOYSA-N 0.000 claims description 2
• WHJSSVRIIXWBBW-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)-2-[(2-hydroxy-3-methylbutanoyl)amino]pentanamide Chemical compound CC(C)C(O)C(=O)NC(CCC)C(=O)NC=1C=C(C(C)(C)C)ON=1 WHJSSVRIIXWBBW-UHFFFAOYSA-N 0.000 claims description 2
• JNOVCKSBTAVEFV-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)-2-[[2-(3-phenoxyphenyl)acetyl]amino]pentanamide Chemical compound C1=C(C(C)(C)C)ON=C1NC(=O)C(CCC)NC(=O)CC(C=1)=CC=CC=1OC1=CC=CC=C1 JNOVCKSBTAVEFV-UHFFFAOYSA-N 0.000 claims description 2
• GAZXGCVNGGRLMB-UHFFFAOYSA-N n-[1-[(3,4-dimethyl-1,2-oxazol-5-yl)amino]-1-oxopentan-2-yl]-2-hydroxy-3,3-dimethylbutanamide Chemical compound CC(C)(C)C(O)C(=O)NC(CCC)C(=O)NC=1ON=C(C)C=1C GAZXGCVNGGRLMB-UHFFFAOYSA-N 0.000 claims description 2
• ULWNJOUCAYRVPZ-UHFFFAOYSA-N n-[1-[(3-cyclohexyl-1,2-oxazol-5-yl)amino]-1-oxopentan-2-yl]-2-hydroxy-3,3-dimethylbutanamide Chemical compound O1C(NC(=O)C(NC(=O)C(O)C(C)(C)C)CCC)=CC(C2CCCCC2)=N1 ULWNJOUCAYRVPZ-UHFFFAOYSA-N 0.000 claims description 2
• GSRFPFYRPRBFSC-UHFFFAOYSA-N n-[1-[(4-ethyl-3-methyl-1,2-oxazol-5-yl)amino]-1-oxopentan-2-yl]-2-hydroxy-3,3-dimethylbutanamide Chemical compound CC(C)(C)C(O)C(=O)NC(CCC)C(=O)NC=1ON=C(C)C=1CC GSRFPFYRPRBFSC-UHFFFAOYSA-N 0.000 claims description 2
• FBINYPHXOOZBNT-UHFFFAOYSA-N n-[1-[(5-cyclohexyl-1,2-oxazol-3-yl)amino]-1-oxopentan-2-yl]-2-hydroxy-3,3-dimethylbutanamide Chemical compound O1N=C(NC(=O)C(NC(=O)C(O)C(C)(C)C)CCC)C=C1C1CCCCC1 FBINYPHXOOZBNT-UHFFFAOYSA-N 0.000 claims description 2
• OUSZXVXKPFTHBH-UHFFFAOYSA-N n-[1-[[3-(cyclopentylmethyl)-1,2-oxazol-5-yl]amino]-1-oxopentan-2-yl]-2-hydroxy-3,3-dimethylbutanamide Chemical compound O1C(NC(=O)C(NC(=O)C(O)C(C)(C)C)CCC)=CC(CC2CCCC2)=N1 OUSZXVXKPFTHBH-UHFFFAOYSA-N 0.000 claims description 2
• PGCVPZUZYOGXNY-UHFFFAOYSA-N n-[1-[[5-(1-adamantyl)-1,2-oxazol-3-yl]amino]-1-oxopentan-2-yl]-2-hydroxy-3,3-dimethylbutanamide Chemical compound O1N=C(NC(=O)C(NC(=O)C(O)C(C)(C)C)CCC)C=C1C1(C2)CC(C3)CC2CC3C1 PGCVPZUZYOGXNY-UHFFFAOYSA-N 0.000 claims description 2
• MSOYKLGIFPRAQN-UHFFFAOYSA-N n-[1-[[5-(4-tert-butylphenyl)-1,2-oxazol-3-yl]amino]-1-oxopentan-2-yl]-2-hydroxy-3,3-dimethylbutanamide Chemical compound O1N=C(NC(=O)C(NC(=O)C(O)C(C)(C)C)CCC)C=C1C1=CC=C(C(C)(C)C)C=C1 MSOYKLGIFPRAQN-UHFFFAOYSA-N 0.000 claims description 2
• PYFJWPCHUZVFHA-UHFFFAOYSA-N n-[1-[[5-[1-(3,3-dimethylbutoxy)ethyl]-1,2-oxazol-3-yl]amino]-1-oxopentan-2-yl]-2-hydroxy-3,3-dimethylbutanamide Chemical compound CC(C)(C)C(O)C(=O)NC(CCC)C(=O)NC=1C=C(C(C)OCCC(C)(C)C)ON=1 PYFJWPCHUZVFHA-UHFFFAOYSA-N 0.000 claims description 2
• YMQJKPOMUVUMBN-UHFFFAOYSA-N n-[1-[[5-[1-(3,3-dimethylbutylamino)ethyl]-1,2-oxazol-3-yl]amino]-1-oxopentan-2-yl]-2-hydroxy-3,3-dimethylbutanamide Chemical compound CC(C)(C)C(O)C(=O)NC(CCC)C(=O)NC=1C=C(C(C)NCCC(C)(C)C)ON=1 YMQJKPOMUVUMBN-UHFFFAOYSA-N 0.000 claims description 2
• QJMCNOBOAZNISY-UHFFFAOYSA-N n-[1-[[5-[1-(4-tert-butylphenyl)propan-2-yl]-1,2-oxazol-3-yl]amino]-1-oxopropan-2-yl]-2-hydroxy-3,3-dimethylbutanamide Chemical compound C=1C(NC(=O)C(C)NC(=O)C(O)C(C)(C)C)=NOC=1C(C)CC1=CC=C(C(C)(C)C)C=C1 QJMCNOBOAZNISY-UHFFFAOYSA-N 0.000 claims description 2
• KZAKPEZJDHVXFS-UHFFFAOYSA-N n-[3-(cyclopentylmethyl)-1,2-oxazol-5-yl]-2-[(2-hydroxy-2-phenylacetyl)amino]pentanamide Chemical compound C=1C(CC2CCCC2)=NOC=1NC(=O)C(CCC)NC(=O)C(O)C1=CC=CC=C1 KZAKPEZJDHVXFS-UHFFFAOYSA-N 0.000 claims description 2
• XVDGCJDABUFWNJ-UHFFFAOYSA-N n-[3-(cyclopentylmethyl)-1,2-oxazol-5-yl]-2-[(2-hydroxy-3-methylbutanoyl)amino]pentanamide Chemical compound O1C(NC(=O)C(NC(=O)C(O)C(C)C)CCC)=CC(CC2CCCC2)=N1 XVDGCJDABUFWNJ-UHFFFAOYSA-N 0.000 claims description 2
• JGPSWMBKSJMPGL-UHFFFAOYSA-N n-[3-(cyclopentylmethyl)-1,2-oxazol-5-yl]-2-[[2-(3,5-difluorophenyl)acetyl]amino]pentanamide Chemical compound C=1C(CC2CCCC2)=NOC=1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 JGPSWMBKSJMPGL-UHFFFAOYSA-N 0.000 claims description 2
• JOJDUMWJYCXEEH-UHFFFAOYSA-N n-[5-(1-adamantyl)-1,2-oxazol-3-yl]-2-[(2-hydroxy-2-phenylacetyl)amino]pentanamide Chemical compound C1=C(C23CC4CC(CC(C4)C2)C3)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC=CC=C1 JOJDUMWJYCXEEH-UHFFFAOYSA-N 0.000 claims description 2
• VBHDZUWHSOGGNX-UHFFFAOYSA-N n-[5-(1-adamantyl)-1,2-oxazol-3-yl]-2-[(2-hydroxy-3-methylbutanoyl)amino]pentanamide Chemical compound O1N=C(NC(=O)C(NC(=O)C(O)C(C)C)CCC)C=C1C1(C2)CC(C3)CC2CC3C1 VBHDZUWHSOGGNX-UHFFFAOYSA-N 0.000 claims description 2
• UWAYJRHDTSZNRV-UHFFFAOYSA-N n-[5-(1-adamantyl)-1,2-oxazol-3-yl]-2-[[2-(3,5-difluorophenyl)-2-hydroxyacetyl]amino]pentanamide Chemical compound C1=C(C23CC4CC(CC(C4)C2)C3)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC(F)=CC(F)=C1 UWAYJRHDTSZNRV-UHFFFAOYSA-N 0.000 claims description 2
• IQXVAHYLFJCELE-UHFFFAOYSA-N n-[5-(1-adamantyl)-1,2-oxazol-3-yl]-2-[[2-(3,5-difluorophenyl)acetyl]amino]pentanamide Chemical compound C1=C(C23CC4CC(CC(C4)C2)C3)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 IQXVAHYLFJCELE-UHFFFAOYSA-N 0.000 claims description 2
• AYBCVZOHQGVLLJ-UHFFFAOYSA-N n-[5-(1-hydroxyethyl)-1,2-oxazol-3-yl]-2-[(2-hydroxy-2-phenylacetyl)amino]pentanamide Chemical compound C1=C(C(C)O)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC=CC=C1 AYBCVZOHQGVLLJ-UHFFFAOYSA-N 0.000 claims description 2
• GERCOVGYVLWBBV-UHFFFAOYSA-N n-[5-(3-hydroxypentan-3-yl)-1,2-oxazol-3-yl]-2-[(2-hydroxy-2-phenylacetyl)amino]pentanamide Chemical compound C1=C(C(O)(CC)CC)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC=CC=C1 GERCOVGYVLWBBV-UHFFFAOYSA-N 0.000 claims description 2
• OCFNLILWOJIICJ-UHFFFAOYSA-N n-[5-(4-tert-butylphenyl)-1,2-oxazol-3-yl]-2-[(2-hydroxy-2-phenylacetyl)amino]pentanamide Chemical compound C1=C(C=2C=CC(=CC=2)C(C)(C)C)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC=CC=C1 OCFNLILWOJIICJ-UHFFFAOYSA-N 0.000 claims description 2
• UMNPYAVZXHUZNK-UHFFFAOYSA-N n-[5-(4-tert-butylphenyl)-1,2-oxazol-3-yl]-2-[(2-hydroxy-3-methylbutanoyl)amino]pentanamide Chemical compound O1N=C(NC(=O)C(NC(=O)C(O)C(C)C)CCC)C=C1C1=CC=C(C(C)(C)C)C=C1 UMNPYAVZXHUZNK-UHFFFAOYSA-N 0.000 claims description 2
• DGEXPENNTBDEHT-UHFFFAOYSA-N n-[5-(4-tert-butylphenyl)-1,2-oxazol-3-yl]-2-[[2-(3,5-difluorophenyl)acetyl]amino]pentanamide Chemical compound C1=C(C=2C=CC(=CC=2)C(C)(C)C)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 DGEXPENNTBDEHT-UHFFFAOYSA-N 0.000 claims description 2
• FNCRYIUGPOOHTI-UHFFFAOYSA-N n-[5-(6-methoxy-2,6-dimethylheptyl)-1,2-oxazol-3-yl]-2-[[2-(3-phenoxyphenyl)acetyl]amino]pentanamide Chemical compound C1=C(CC(C)CCCC(C)(C)OC)ON=C1NC(=O)C(CCC)NC(=O)CC(C=1)=CC=CC=1OC1=CC=CC=C1 FNCRYIUGPOOHTI-UHFFFAOYSA-N 0.000 claims description 2
• ZMUXYFNVTOSDEY-UHFFFAOYSA-N n-[5-(cyclopentylmethyl)-1,2-oxazol-3-yl]-2-[(2-hydroxy-2-phenylacetyl)amino]pentanamide Chemical compound C1=C(CC2CCCC2)ON=C1NC(=O)C(CCC)NC(=O)C(O)C1=CC=CC=C1 ZMUXYFNVTOSDEY-UHFFFAOYSA-N 0.000 claims description 2
• OLMIFWIAWAZNHR-UHFFFAOYSA-N n-[5-(cyclopentylmethyl)-1,2-oxazol-3-yl]-2-[(2-hydroxy-3-methylbutanoyl)amino]pentanamide Chemical compound O1N=C(NC(=O)C(NC(=O)C(O)C(C)C)CCC)C=C1CC1CCCC1 OLMIFWIAWAZNHR-UHFFFAOYSA-N 0.000 claims description 2
• GKOJGSFELRXZCW-UHFFFAOYSA-N n-[5-(cyclopentylmethyl)-1,2-oxazol-3-yl]-2-[[2-(3,5-difluorophenyl)acetyl]amino]pentanamide Chemical compound C1=C(CC2CCCC2)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 GKOJGSFELRXZCW-UHFFFAOYSA-N 0.000 claims description 2
• HJTCBDJTZKNFPY-UHFFFAOYSA-N n-[5-[1-(4-butylpiperazin-1-yl)ethyl]-1,2-oxazol-3-yl]-2-[[2-(3,5-difluorophenyl)acetyl]amino]pentanamide Chemical compound C1CN(CCCC)CCN1C(C)C1=CC(NC(=O)C(CCC)NC(=O)CC=2C=C(F)C=C(F)C=2)=NO1 HJTCBDJTZKNFPY-UHFFFAOYSA-N 0.000 claims description 2
• FOTMNDIKYUTKBS-UHFFFAOYSA-N n-[5-[1-(4-tert-butylphenyl)propan-2-yl]-1,2-oxazol-3-yl]-2-[[2-(3,5-difluorophenyl)acetyl]amino]pentanamide Chemical compound C1=C(C(C)CC=2C=CC(=CC=2)C(C)(C)C)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 FOTMNDIKYUTKBS-UHFFFAOYSA-N 0.000 claims description 2
• PSPPTOHOFCWKKZ-UHFFFAOYSA-N n-[5-[1-(tert-butylamino)ethyl]-1,2-oxazol-3-yl]-2-[[2-(3,5-difluorophenyl)acetyl]amino]pentanamide Chemical compound C1=C(C(C)NC(C)(C)C)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 PSPPTOHOFCWKKZ-UHFFFAOYSA-N 0.000 claims description 2
• WMNWEWXRXICEGC-UHFFFAOYSA-N n-[5-[1-[3-(diethylamino)propyl-methylamino]ethyl]-1,2-oxazol-3-yl]-2-[[2-(3,5-difluorophenyl)acetyl]amino]pentanamide Chemical compound C1=C(C(C)N(C)CCCN(CC)CC)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 WMNWEWXRXICEGC-UHFFFAOYSA-N 0.000 claims description 2
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
• 125000001309 chloro group Chemical group Cl* 0.000 claims 12
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
• 229910006074 SO2NH2 Inorganic materials 0.000 claims 3
• LJKZNMLKWMKJQU-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-[[3-(dimethylamino)pyrrolidin-1-yl]methyl]-1,2-oxazol-3-yl]pentanamide Chemical compound C1=C(CN2CC(CC2)N(C)C)ON=C1NC(=O)C(CCC)NC(=O)CC1=CC(F)=CC(F)=C1 LJKZNMLKWMKJQU-UHFFFAOYSA-N 0.000 claims 2
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
• 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims 1
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