ES2560627T3 - Compuestos y procedimientos para la inhibición de HDAC - Google Patents

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Publication number

ES2560627T3

ES2560627T3 ES11733353.4T ES11733353T ES2560627T3 ES 2560627 T3 ES2560627 T3 ES 2560627T3 ES 11733353 T ES11733353 T ES 11733353T ES 2560627 T3 ES2560627 T3 ES 2560627T3

Authority

ES

Spain

Prior art keywords

trifluoromethyl

alkyl

oxadiazol

methyl

benzamide

Prior art date

2010-01-13

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.)

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 370
• 108090000353 Histone deacetylase Proteins 0.000 title description 34
• 102000003964 Histone deacetylase Human genes 0.000 title description 31
• 238000000034 method Methods 0.000 title description 22
• 230000005764 inhibitory process Effects 0.000 title description 10
• -1 halo (C1-C4) alkyl Chemical group 0.000 claims abstract description 475
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 221
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 85
• 150000003839 salts Chemical class 0.000 claims abstract description 84
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 83
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 69
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 63
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 63
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 62
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 52
• 150000002367 halogens Chemical class 0.000 claims abstract description 52
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 38
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 36
• 125000001424 substituent group Chemical group 0.000 claims abstract description 36
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 33
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 33
• 125000004429 atom Chemical group 0.000 claims abstract description 31
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 28
• 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 28
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract description 27
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 26
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 25
• 239000011737 fluorine Substances 0.000 claims abstract description 25
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 23
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 22
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
• 125000003118 aryl group Chemical group 0.000 claims abstract description 17
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 12
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims abstract description 12
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 12
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract description 11
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 11
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims abstract description 10
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 10
• 125000005843 halogen group Chemical group 0.000 claims abstract description 10
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims abstract description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
• 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims abstract description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
• SWCAWZMNVIXNKH-UHFFFAOYSA-N 3-[1-[3-(3-methyl-1,2-oxazol-5-yl)propyl]indol-5-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1N=C(C)C=C1CCCN1C2=CC=C(C=3N=C(ON=3)C(F)(F)F)C=C2C=C1 SWCAWZMNVIXNKH-UHFFFAOYSA-N 0.000 claims abstract description 5
• RVFHUKHEFRHUIX-UHFFFAOYSA-N 3-[7-methyl-1-[5-(3-methyl-1,2-oxazol-5-yl)pentyl]indol-5-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1N=C(C)C=C1CCCCCN1C2=C(C)C=C(C=3N=C(ON=3)C(F)(F)F)C=C2C=C1 RVFHUKHEFRHUIX-UHFFFAOYSA-N 0.000 claims abstract description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
• NLUHMENALNPHJA-UHFFFAOYSA-N 3-[7-methyl-1-[3-(3-methyl-1,2-oxazol-5-yl)propyl]-2,3-dihydroindol-5-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1N=C(C)C=C1CCCN1C2=C(C)C=C(C=3N=C(ON=3)C(F)(F)F)C=C2CC1 NLUHMENALNPHJA-UHFFFAOYSA-N 0.000 claims abstract description 4
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
• BRMIYYWPBPHSQY-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-[5-(2,2,2-trifluoroacetyl)thiophen-2-yl]benzamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=CC(C=2SC(=CC=2)C(=O)C(F)(F)F)=C1 BRMIYYWPBPHSQY-UHFFFAOYSA-N 0.000 claims abstract 2
• JQYWWORDYVNBGY-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-[5-(2,2,2-trifluoroacetyl)thiophen-2-yl]benzamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=C(C=2SC(=CC=2)C(=O)C(F)(F)F)C=C1 JQYWWORDYVNBGY-UHFFFAOYSA-N 0.000 claims abstract 2
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 156
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 141
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 64
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 40
• 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 36
• 125000004076 pyridyl group Chemical group 0.000 claims description 24
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 22
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
• 125000001544 thienyl group Chemical group 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• 238000011282 treatment Methods 0.000 claims description 20
• 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 description 17
• 239000000460 chlorine Substances 0.000 claims description 16
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 15
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
• 229910052794 bromium Inorganic materials 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
• 206010052779 Transplant rejections Diseases 0.000 claims description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
• 125000002883 imidazolyl group Chemical group 0.000 claims description 10
• 208000023275 Autoimmune disease Diseases 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims description 7
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• 230000001225 therapeutic effect Effects 0.000 claims description 6
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 208000027866 inflammatory disease Diseases 0.000 claims description 5
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
• LIUHKQNWTKDRIU-UHFFFAOYSA-N 3-[7-methyl-1-[4-(3-methyl-1,2-oxazol-5-yl)butyl]indol-5-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1N=C(C)C=C1CCCCN1C2=C(C)C=C(C=3N=C(ON=3)C(F)(F)F)C=C2C=C1 LIUHKQNWTKDRIU-UHFFFAOYSA-N 0.000 claims description 4
• NVCUFLNOWZTXPQ-UHFFFAOYSA-N 3-[7-methyl-2-[4-(3-methyl-1,2-oxazol-5-yl)butyl]-1-benzofuran-5-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1N=C(C)C=C1CCCCC1=CC2=CC(C=3N=C(ON=3)C(F)(F)F)=CC(C)=C2O1 NVCUFLNOWZTXPQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• 241000282979 Alces alces Species 0.000 claims description 4
• 208000009329 Graft vs Host Disease Diseases 0.000 claims description 4
• 206010025327 Lymphopenia Diseases 0.000 claims description 4
• 208000024908 graft versus host disease Diseases 0.000 claims description 4
• 208000026278 immune system disease Diseases 0.000 claims description 4
• 231100001023 lymphopenia Toxicity 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 230000002265 prevention Effects 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• UKTWGDPKMISRFV-UHFFFAOYSA-N 3-[3-[4-(4-phenyl-1,3-thiazol-2-yl)butyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1C(C(F)(F)F)=NC(C=2C=C(CCCCC=3SC=C(N=3)C=3C=CC=CC=3)C=CC=2)=N1 UKTWGDPKMISRFV-UHFFFAOYSA-N 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• UGHITQRMICHJDI-UHFFFAOYSA-N 4-[4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzenesulfonyl chloride Chemical group C1=CC(C(F)(F)F)=CC=C1C1=CSC(C=2C=CC(=CC=2)S(Cl)(=O)=O)=N1 UGHITQRMICHJDI-UHFFFAOYSA-N 0.000 claims description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 3
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
• 230000006872 improvement Effects 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• KBAQTAYYVDXFCZ-UHFFFAOYSA-N n-[2-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]-2-methylpropyl]-3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C=1OC(C=2C=CC(F)=CC=2)=NC=1C(C)(C)CNC(=O)C(C=1)=CC=CC=1C1=NOC(C(F)(F)F)=N1 KBAQTAYYVDXFCZ-UHFFFAOYSA-N 0.000 claims description 3
• 239000011570 nicotinamide Substances 0.000 claims description 3
• 229960003966 nicotinamide Drugs 0.000 claims description 3
• 235000005152 nicotinamide Nutrition 0.000 claims description 3
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
• SHSGFJTVGHYXID-UHFFFAOYSA-N n-[2-(dimethylamino)-2-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]ethyl]-3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C=1OC(C=2C=CC(F)=CC=2)=NC=1C(N(C)C)CNC(=O)C(C=1)=CC=CC=1C1=NOC(C(F)(F)F)=N1 SHSGFJTVGHYXID-UHFFFAOYSA-N 0.000 claims description 2
• QTCSXAUJBQZZSN-UHFFFAOYSA-N n-[2-methyl-2-(2-phenyl-1,3-oxazol-4-yl)propyl]-3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical group C=1OC(C=2C=CC=CC=2)=NC=1C(C)(C)CNC(=O)C(C=1)=CC=CC=1C1=NOC(C(F)(F)F)=N1 QTCSXAUJBQZZSN-UHFFFAOYSA-N 0.000 claims description 2
• DYVPKPAXSFKEEQ-UHFFFAOYSA-N n-[4-(dimethylamino)-2-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]butyl]-3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C=1OC(C=2C=CC(F)=CC=2)=NC=1C(CCN(C)C)CNC(=O)C(C=1)=CC=CC=1C1=NOC(C(F)(F)F)=N1 DYVPKPAXSFKEEQ-UHFFFAOYSA-N 0.000 claims description 2
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 2
• 239000000126 substance Substances 0.000 claims description 2
• WOWNBLBQRLBPQB-UHFFFAOYSA-N n-[[4-(4-phenyl-1,3-thiazol-2-yl)oxan-4-yl]methyl]-1-[3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine Chemical compound O1C(C(F)(F)F)=NC(C=2C=C(CNCC3(CCOCC3)C=3SC=C(N=3)C=3C=CC=CC=3)C=CC=2)=N1 WOWNBLBQRLBPQB-UHFFFAOYSA-N 0.000 claims 2
• FGISCEWFJDKCGC-UHFFFAOYSA-N 2-fluoro-n-[2-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]-2-methylpropyl]-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C=1OC(C=2C=CC(F)=CC=2)=NC=1C(C)(C)CNC(=O)C(C(=CC=1)F)=CC=1C1=NOC(C(F)(F)F)=N1 FGISCEWFJDKCGC-UHFFFAOYSA-N 0.000 claims 1
• WMFPLALDPXLMKY-UHFFFAOYSA-N Cl.FC(C1=NC=NO1)(F)F Chemical compound Cl.FC(C1=NC=NO1)(F)F WMFPLALDPXLMKY-UHFFFAOYSA-N 0.000 claims 1
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
• KZXXDHYHDXENJB-UHFFFAOYSA-N n-[2-(3-methyl-2-phenylimidazol-4-yl)propyl]-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pyridine-3-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)N(C)C=1C(C)CNC(=O)C(C=1)=CN=CC=1C1=NOC(C(F)(F)F)=N1 KZXXDHYHDXENJB-UHFFFAOYSA-N 0.000 claims 1
• UUEVQXMIQOYWAA-UHFFFAOYSA-N n-[2-[2-(2-fluorophenyl)-1,3-oxazol-4-yl]ethyl]-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pyridine-3-carboxamide Chemical compound FC1=CC=CC=C1C1=NC(CCNC(=O)C=2C=C(C=NC=2)C=2N=C(ON=2)C(F)(F)F)=CO1 UUEVQXMIQOYWAA-UHFFFAOYSA-N 0.000 claims 1
• GAUWIXTYPAGXLI-UHFFFAOYSA-N n-[2-[2-(4-chlorophenyl)-1,3-oxazol-4-yl]-2-methylpropyl]-3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C=1OC(C=2C=CC(Cl)=CC=2)=NC=1C(C)(C)CNC(=O)C(C=1)=CC=CC=1C1=NOC(C(F)(F)F)=N1 GAUWIXTYPAGXLI-UHFFFAOYSA-N 0.000 claims 1
• FRWFZTNMTFPQPP-UHFFFAOYSA-N n-[2-[2-(4-chlorophenyl)-1,3-oxazol-4-yl]ethyl]-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pyridine-3-carboxamide Chemical compound O1C(C(F)(F)F)=NC(C=2C=C(C=NC=2)C(=O)NCCC=2N=C(OC=2)C=2C=CC(Cl)=CC=2)=N1 FRWFZTNMTFPQPP-UHFFFAOYSA-N 0.000 claims 1
• TYEXMPXKPYQMSQ-UHFFFAOYSA-N n-[2-[2-(4-cyanophenyl)-1,3-oxazol-4-yl]ethyl]-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pyridine-3-carboxamide Chemical compound O1C(C(F)(F)F)=NC(C=2C=C(C=NC=2)C(=O)NCCC=2N=C(OC=2)C=2C=CC(=CC=2)C#N)=N1 TYEXMPXKPYQMSQ-UHFFFAOYSA-N 0.000 claims 1
• LNZACOCISFIZIM-UHFFFAOYSA-N n-[2-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]-2-hydroxyethyl]-3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C=1OC(C=2C=CC(F)=CC=2)=NC=1C(O)CNC(=O)C(C=1)=CC=CC=1C1=NOC(C(F)(F)F)=N1 LNZACOCISFIZIM-UHFFFAOYSA-N 0.000 claims 1
• CKCAORORKZXIHK-UHFFFAOYSA-N n-[2-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]-2-hydroxyethyl]-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pyridine-3-carboxamide Chemical compound C=1OC(C=2C=CC(F)=CC=2)=NC=1C(O)CNC(=O)C(C=1)=CN=CC=1C1=NOC(C(F)(F)F)=N1 CKCAORORKZXIHK-UHFFFAOYSA-N 0.000 claims 1
• XPSWQMUPUJZDQT-UHFFFAOYSA-N n-[2-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]-2-methoxyethyl]-3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C=1OC(C=2C=CC(F)=CC=2)=NC=1C(OC)CNC(=O)C(C=1)=CC=CC=1C1=NOC(C(F)(F)F)=N1 XPSWQMUPUJZDQT-UHFFFAOYSA-N 0.000 claims 1
• YOJXFKIZZSVOLH-UHFFFAOYSA-N n-[2-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]-2-methylpropyl]-2-methoxy-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound COC1=CC=C(C=2N=C(ON=2)C(F)(F)F)C=C1C(=O)NCC(C)(C)C(N=1)=COC=1C1=CC=C(F)C=C1 YOJXFKIZZSVOLH-UHFFFAOYSA-N 0.000 claims 1
• MABKODZHLWEHEZ-UHFFFAOYSA-N n-[2-[2-(4-fluorophenyl)-1,3-oxazol-5-yl]-2-methylpropyl]-3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C=1N=C(C=2C=CC(F)=CC=2)OC=1C(C)(C)CNC(=O)C(C=1)=CC=CC=1C1=NOC(C(F)(F)F)=N1 MABKODZHLWEHEZ-UHFFFAOYSA-N 0.000 claims 1
• MDODQPSUACGYML-UHFFFAOYSA-N n-[2-[2-(4-fluorophenyl)-1,3-oxazol-5-yl]ethyl]-3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C1=CC(F)=CC=C1C(O1)=NC=C1CCNC(=O)C1=CC=CC(C=2N=C(ON=2)C(F)(F)F)=C1 MDODQPSUACGYML-UHFFFAOYSA-N 0.000 claims 1
• HWOXOKBPYRHSBG-UHFFFAOYSA-N n-[2-[2-(4-methoxyphenyl)-1,3-oxazol-4-yl]ethyl]-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC(CCNC(=O)C=2C=C(C=NC=2)C=2N=C(ON=2)C(F)(F)F)=CO1 HWOXOKBPYRHSBG-UHFFFAOYSA-N 0.000 claims 1
• UMZASEKBAUOOAJ-UHFFFAOYSA-N n-[2-methyl-2-(2-phenyl-1,3-oxazol-4-yl)propyl]-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pyridine-3-carboxamide Chemical compound C=1OC(C=2C=CC=CC=2)=NC=1C(C)(C)CNC(=O)C(C=1)=CN=CC=1C1=NOC(C(F)(F)F)=N1 UMZASEKBAUOOAJ-UHFFFAOYSA-N 0.000 claims 1
• VBKPUFNDAJUPFL-UHFFFAOYSA-N n-[2-methyl-2-(3-phenyl-1h-pyrazol-5-yl)propyl]-3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C=1C(C=2C=CC=CC=2)=NNC=1C(C)(C)CNC(=O)C(C=1)=CC=CC=1C1=NOC(C(F)(F)F)=N1 VBKPUFNDAJUPFL-UHFFFAOYSA-N 0.000 claims 1
• SAECVQIOJNCTLG-UHFFFAOYSA-N n-[4-(dimethylamino)-2-[2-(4-fluorophenyl)-1,3-oxazol-4-yl]butyl]-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pyridine-3-carboxamide Chemical compound C=1OC(C=2C=CC(F)=CC=2)=NC=1C(CCN(C)C)CNC(=O)C(C=1)=CN=CC=1C1=NOC(C(F)(F)F)=N1 SAECVQIOJNCTLG-UHFFFAOYSA-N 0.000 claims 1
• PCRNYVUJVYOTLV-UHFFFAOYSA-N n-[[4-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-2,2-dimethyloxan-4-yl]methyl]-3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C1COC(C)(C)CC1(C=1SC=C(N=1)C=1C=CC(F)=CC=1)CNC(=O)C1=CC=CC(C=2N=C(ON=2)C(F)(F)F)=C1 PCRNYVUJVYOTLV-UHFFFAOYSA-N 0.000 claims 1
• 229940124597 therapeutic agent Drugs 0.000 claims 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 4
• MFGOBRZBIXOVQL-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenyl]-n-[3-(trifluoromethyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]propanamide Chemical compound O1C(C(F)(F)F)=NC(C=2C(=CC(NC(=O)CCC=3C=CC(=CC=3)C(F)(F)F)=CC=2)C(F)(F)F)=N1 MFGOBRZBIXOVQL-UHFFFAOYSA-N 0.000 abstract description 2
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