CA2899168A1 - Novel pyridine derivatives - Google Patents

Info

Publication number

CA2899168A1

CA2899168A1 CA2899168A CA2899168A CA2899168A1 CA 2899168 A1 CA2899168 A1 CA 2899168A1 CA 2899168 A CA2899168 A CA 2899168A CA 2899168 A CA2899168 A CA 2899168A CA 2899168 A1 CA2899168 A1 CA 2899168A1

Authority

CA

Canada

Prior art keywords

pyridin

oxadiazole

tert

cyclopropyl

butyl

Prior art date

2013-03-26

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

• 150000003222 pyridines Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 370
• 239000003814 drug Substances 0.000 claims abstract description 7
• 238000006243 chemical reaction Methods 0.000 claims description 145
• -1 haloazetidinyl Chemical group 0.000 claims description 72
• 238000000034 method Methods 0.000 claims description 44
• 238000011282 treatment Methods 0.000 claims description 35
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 25
• 238000010438 heat treatment Methods 0.000 claims description 23
• 125000000217 alkyl group Chemical group 0.000 claims description 22
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 20
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 20
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 15
• 206010063837 Reperfusion injury Diseases 0.000 claims description 15
• 230000006378 damage Effects 0.000 claims description 15
• 229910052736 halogen Chemical group 0.000 claims description 15
• 238000011321 prophylaxis Methods 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 125000001188 haloalkyl group Chemical group 0.000 claims description 14
• 150000002367 halogens Chemical group 0.000 claims description 14
• 206010016654 Fibrosis Diseases 0.000 claims description 13
• 230000004761 fibrosis Effects 0.000 claims description 13
• 239000001257 hydrogen Substances 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
• 208000027418 Wounds and injury Diseases 0.000 claims description 12
• YSHOWEKUVWPFNR-UHFFFAOYSA-N burgess reagent Chemical compound CC[N+](CC)(CC)S(=O)(=O)N=C([O-])OC YSHOWEKUVWPFNR-UHFFFAOYSA-N 0.000 claims description 12
• 208000014674 injury Diseases 0.000 claims description 12
• 229910052763 palladium Inorganic materials 0.000 claims description 12
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 11
• 206010046851 Uveitis Diseases 0.000 claims description 11
• 208000010125 myocardial infarction Diseases 0.000 claims description 11
• 208000004644 retinal vein occlusion Diseases 0.000 claims description 11
• 201000001320 Atherosclerosis Diseases 0.000 claims description 10
• 208000008069 Geographic Atrophy Diseases 0.000 claims description 10
• 208000010412 Glaucoma Diseases 0.000 claims description 10
• 206010023421 Kidney fibrosis Diseases 0.000 claims description 10
• 206010069385 Ocular ischaemic syndrome Diseases 0.000 claims description 10
• 208000002193 Pain Diseases 0.000 claims description 10
• 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 10
• 208000006011 Stroke Diseases 0.000 claims description 10
• 206010042953 Systemic sclerosis Diseases 0.000 claims description 10
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 10
• 230000033228 biological regulation Effects 0.000 claims description 10
• 210000000988 bone and bone Anatomy 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 208000012947 ischemia reperfusion injury Diseases 0.000 claims description 10
• 208000002780 macular degeneration Diseases 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 201000006417 multiple sclerosis Diseases 0.000 claims description 10
• 230000009885 systemic effect Effects 0.000 claims description 10
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 10
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 10
• WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 10
• 208000007788 Acute Liver Failure Diseases 0.000 claims description 9
• 206010000804 Acute hepatic failure Diseases 0.000 claims description 9
• 208000024827 Alzheimer disease Diseases 0.000 claims description 9
• 208000031229 Cardiomyopathies Diseases 0.000 claims description 9
• 206010063209 Chronic allograft nephropathy Diseases 0.000 claims description 9
• 208000032544 Cicatrix Diseases 0.000 claims description 9
• 201000001200 Crouzon syndrome-acanthosis nigricans syndrome Diseases 0.000 claims description 9
• 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 9
• 206010051920 Glomerulonephropathy Diseases 0.000 claims description 9
• 206010019280 Heart failures Diseases 0.000 claims description 9
• 206010019695 Hepatic neoplasm Diseases 0.000 claims description 9
• 206010061218 Inflammation Diseases 0.000 claims description 9
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 9
• 208000002260 Keloid Diseases 0.000 claims description 9
• 208000018737 Parkinson disease Diseases 0.000 claims description 9
• 206010037660 Pyrexia Diseases 0.000 claims description 9
• 201000009594 Systemic Scleroderma Diseases 0.000 claims description 9
• 208000032109 Transient ischaemic attack Diseases 0.000 claims description 9
• 206010052779 Transplant rejections Diseases 0.000 claims description 9
• 231100000836 acute liver failure Toxicity 0.000 claims description 9
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
• 239000003054 catalyst Substances 0.000 claims description 9
• 206010012601 diabetes mellitus Diseases 0.000 claims description 9
• 208000033679 diabetic kidney disease Diseases 0.000 claims description 9
• 230000027950 fever generation Effects 0.000 claims description 9
• 208000007565 gingivitis Diseases 0.000 claims description 9
• 230000001969 hypertrophic effect Effects 0.000 claims description 9
• 230000004054 inflammatory process Effects 0.000 claims description 9
• 210000001117 keloid Anatomy 0.000 claims description 9
• 208000014018 liver neoplasm Diseases 0.000 claims description 9
• 208000031225 myocardial ischemia Diseases 0.000 claims description 9
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 9
• 231100000241 scar Toxicity 0.000 claims description 9
• 230000037387 scars Effects 0.000 claims description 9
• 201000010875 transient cerebral ischemia Diseases 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000005059 halophenyl group Chemical group 0.000 claims description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• 230000003647 oxidation Effects 0.000 claims description 8
• 238000007254 oxidation reaction Methods 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 125000006544 oxetanylalkyl group Chemical group 0.000 claims description 7
• 125000002393 azetidinyl group Chemical group 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 229940098779 methanesulfonic acid Drugs 0.000 claims description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 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 5
• 150000002148 esters Chemical class 0.000 claims description 5
• VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 claims description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 125000006001 difluoroethyl group Chemical group 0.000 claims description 4
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• BCIIWQHRWPXARK-UHFFFAOYSA-N 6-oxa-1-azaspiro[3.3]heptane Chemical compound N1CCC11COC1 BCIIWQHRWPXARK-UHFFFAOYSA-N 0.000 claims description 3
• 239000012320 chlorinating reagent Substances 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 125000006542 morpholinylalkyl group Chemical group 0.000 claims description 3
• 125000003566 oxetanyl group Chemical group 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
• 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
• 238000002360 preparation method Methods 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 239000013543 active substance Substances 0.000 claims description 2
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
• 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 2
• 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 description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims description 2
• 239000007800 oxidant agent Substances 0.000 claims description 2
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 3
• AOWAIUQTZMRKFW-UHFFFAOYSA-N 3-tert-butyl-5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound CC(C)(C)C1=NOC(C=2N=CC(=C(OCC(F)(F)F)C=2)C2CC2)=N1 AOWAIUQTZMRKFW-UHFFFAOYSA-N 0.000 claims 2
• UAWJZDSNZLBNHZ-UHFFFAOYSA-N 3-tert-butyl-5-[5-cyclopropyl-4-(2,2-difluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound CC(C)(C)C1=NOC(C=2N=CC(=C(OCC(F)F)C=2)C2CC2)=N1 UAWJZDSNZLBNHZ-UHFFFAOYSA-N 0.000 claims 2
• FNTFQKRXWGZWIY-UHFFFAOYSA-N 3-tert-butyl-5-[5-cyclopropyl-4-(oxan-4-yloxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound CC(C)(C)c1noc(n1)-c1cc(OC2CCOCC2)c(cn1)C1CC1 FNTFQKRXWGZWIY-UHFFFAOYSA-N 0.000 claims 2
• IGIGFJUOSNGGEA-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(OCC(F)(F)F)C=2)C2CC2)=N1 IGIGFJUOSNGGEA-UHFFFAOYSA-N 0.000 claims 2
• UJKBYEMHLKTICY-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(2-ethoxyethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound CCOCCOC1=CC(C=2N=C(ON=2)C(C)(C)C)=NC=C1C1CC1 UJKBYEMHLKTICY-UHFFFAOYSA-N 0.000 claims 2
• ZUGIJKPPOJHXRW-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(3-methoxybutoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound COC(C)CCOC1=CC(C=2N=C(ON=2)C(C)(C)C)=NC=C1C1CC1 ZUGIJKPPOJHXRW-UHFFFAOYSA-N 0.000 claims 2
• JIVTXHUQNIITHJ-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(4-fluorophenoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(OC=3C=CC(F)=CC=3)C=2)C2CC2)=N1 JIVTXHUQNIITHJ-UHFFFAOYSA-N 0.000 claims 2
• OAYJCQBZUOXJSK-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(oxan-4-yloxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(OC3CCOCC3)C=2)C2CC2)=N1 OAYJCQBZUOXJSK-UHFFFAOYSA-N 0.000 claims 2
• VMSHTNPDBYFZHE-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(oxetan-3-ylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(OCC3COC3)C=2)C2CC2)=N1 VMSHTNPDBYFZHE-UHFFFAOYSA-N 0.000 claims 2
• XETZVHSZEJBYHI-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(oxolan-2-ylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(OCC3OCCC3)C=2)C2CC2)=N1 XETZVHSZEJBYHI-UHFFFAOYSA-N 0.000 claims 2
• YUKWEOINOQTYRZ-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(oxolan-3-yloxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(OC3COCC3)C=2)C2CC2)=N1 YUKWEOINOQTYRZ-UHFFFAOYSA-N 0.000 claims 2
• XUBLJNIOGAIIMR-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-[(3-methyloxetan-3-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(OCC3(C)COC3)C=2)C2CC2)=N1 XUBLJNIOGAIIMR-UHFFFAOYSA-N 0.000 claims 2
• XFXOXFLOMYPHBI-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-[(5-fluoropyridin-2-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole Chemical compound CC(C)(C)c1nc(no1)-c1cc(OCc2ccc(F)cn2)c(cn1)C1CC1 XFXOXFLOMYPHBI-UHFFFAOYSA-N 0.000 claims 2
• 150000001721 carbon Chemical group 0.000 claims 2
• ZKRFJBHBTQUQKQ-QGZVFWFLSA-N (4s)-4-tert-butyl-2-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-4,5-dihydro-1,3-oxazole Chemical compound CC(C)(C)[C@H]1COC(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=N1 ZKRFJBHBTQUQKQ-QGZVFWFLSA-N 0.000 claims 1
• NORGKQSFMOVZTH-UHFFFAOYSA-N 1-[2-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-5-cyclopropylpyridin-4-yl]pyrrolidin-3-ol Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(N3CC(O)CC3)C=2)C2CC2)=N1 NORGKQSFMOVZTH-UHFFFAOYSA-N 0.000 claims 1
• OKKGAGJJWHYLNZ-UHFFFAOYSA-N 1-[3-[5-(3,3-difluoroazetidin-1-yl)-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]cyclopropan-1-ol Chemical compound N=1C(C=2N=CC(=C(OCC(F)(F)F)C=2)N2CC(F)(F)C2)=NOC=1C1(O)CC1 OKKGAGJJWHYLNZ-UHFFFAOYSA-N 0.000 claims 1
• AKSFJNNWWVUINI-UHFFFAOYSA-N 1-[3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]cyclopropan-1-ol Chemical compound N=1C(C=2N=CC(=C(OCC(F)(F)F)C=2)C2CC2)=NOC=1C1(O)CC1 AKSFJNNWWVUINI-UHFFFAOYSA-N 0.000 claims 1
• YBLVURTZMKBLSJ-UHFFFAOYSA-N 1-[3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]cyclopropan-1-ol Chemical compound N=1C(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=NOC=1C1(O)CC1 YBLVURTZMKBLSJ-UHFFFAOYSA-N 0.000 claims 1
• ZSUFXHBCKIVLBE-UHFFFAOYSA-N 1-[3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]cyclopropane-1-carboxamide Chemical compound N=1C(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=NOC=1C1(C(=O)N)CC1 ZSUFXHBCKIVLBE-UHFFFAOYSA-N 0.000 claims 1
• TWZOZGASCPQPBA-UHFFFAOYSA-N 1-[6-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-4-(cyclopropylmethoxy)pyridin-3-yl]-6-oxa-1-azaspiro[3.3]heptane Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(OCC3CC3)C=2)N2C3(COC3)CC2)=N1 TWZOZGASCPQPBA-UHFFFAOYSA-N 0.000 claims 1
• KVFRXZASAOBHCO-UHFFFAOYSA-N 2-(5-tert-butyl-1h-imidazol-2-yl)-5-(3,3-difluoroazetidin-1-yl)-4-(2,2,2-trifluoroethoxy)pyridine Chemical compound N1C(C(C)(C)C)=CN=C1C1=CC(OCC(F)(F)F)=C(N2CC(F)(F)C2)C=N1 KVFRXZASAOBHCO-UHFFFAOYSA-N 0.000 claims 1
• FQYPAAAXASPZTR-UHFFFAOYSA-N 2-[2-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-5-cyclopropylpyridin-4-yl]oxy-N,N-diethylpropan-1-amine Chemical compound CCN(CC)CC(C)Oc1cc(ncc1C1CC1)-c1noc(n1)C(C)(C)C FQYPAAAXASPZTR-UHFFFAOYSA-N 0.000 claims 1
• VPMWTKZJXOPHMS-UHFFFAOYSA-N 2-[3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]propan-2-ol Chemical compound O1C(C(C)(O)C)=NC(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=N1 VPMWTKZJXOPHMS-UHFFFAOYSA-N 0.000 claims 1
• SMXTZXKFGFEANC-UHFFFAOYSA-N 2-[5-(3,3-difluoroazetidin-1-yl)-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-4,4-diethyl-5h-1,3-oxazole Chemical compound CCC1(CC)COC(C=2N=CC(=C(OCC(F)(F)F)C=2)N2CC(F)(F)C2)=N1 SMXTZXKFGFEANC-UHFFFAOYSA-N 0.000 claims 1
• QRUKRVCFWSNDTN-UHFFFAOYSA-N 2-[5-bromo-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-4-methyl-4-propan-2-yl-1h-imidazol-5-one Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=CC(OCC(F)(F)F)=C(Br)C=N1 QRUKRVCFWSNDTN-UHFFFAOYSA-N 0.000 claims 1
• POEMRGVWNWEWHJ-UHFFFAOYSA-N 2-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-3-oxa-1-azaspiro[4.5]dec-1-ene Chemical compound FC(F)(F)COC1=CC(C=2OCC3(N=2)CCCCC3)=NC=C1C1CC1 POEMRGVWNWEWHJ-UHFFFAOYSA-N 0.000 claims 1
• YTRYLIDQOLNHSK-UHFFFAOYSA-N 2-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-4,4-diethyl-5h-1,3-oxazole Chemical compound CCC1(CC)COC(C=2N=CC(=C(OCC(F)(F)F)C=2)C2CC2)=N1 YTRYLIDQOLNHSK-UHFFFAOYSA-N 0.000 claims 1
• VUIOGDKXTPVFSW-UHFFFAOYSA-N 2-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-4-ethyl-4-methyl-1h-imidazol-5-one Chemical compound N1C(=O)C(CC)(C)N=C1C1=CC(OCC(F)(F)F)=C(C2CC2)C=N1 VUIOGDKXTPVFSW-UHFFFAOYSA-N 0.000 claims 1
• WYWLXKCEFJPFTK-UHFFFAOYSA-N 2-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-4-methyl-4-(2-methylpropyl)-1h-imidazol-5-one Chemical compound N1C(=O)C(CC(C)C)(C)N=C1C1=CC(OCC(F)(F)F)=C(C2CC2)C=N1 WYWLXKCEFJPFTK-UHFFFAOYSA-N 0.000 claims 1
• QCKGGBWGYDTGSW-UHFFFAOYSA-N 2-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-4-methyl-4-propan-2-yl-1h-imidazol-5-one Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=CC(OCC(F)(F)F)=C(C2CC2)C=N1 QCKGGBWGYDTGSW-UHFFFAOYSA-N 0.000 claims 1
• OIJDLVWTTOVNHT-UHFFFAOYSA-N 2-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-5,5-dimethyl-4h-1,3-oxazole Chemical compound O1C(C)(C)CN=C1C1=CC(OCC(F)(F)F)=C(C2CC2)C=N1 OIJDLVWTTOVNHT-UHFFFAOYSA-N 0.000 claims 1
• OTHNBCCZCWKBPD-UHFFFAOYSA-N 2-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-3-oxa-1-azaspiro[4.5]dec-1-ene Chemical compound C1CC1COC1=CC(C=2OCC3(N=2)CCCCC3)=NC=C1C1CC1 OTHNBCCZCWKBPD-UHFFFAOYSA-N 0.000 claims 1
• NMHFZCVAQZPHOP-UHFFFAOYSA-N 2-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-4,4-diethyl-5h-1,3-oxazole Chemical compound CCC1(CC)COC(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=N1 NMHFZCVAQZPHOP-UHFFFAOYSA-N 0.000 claims 1
• KENVCMHAFPIUMM-UHFFFAOYSA-N 2-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-4-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1COC(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=N1 KENVCMHAFPIUMM-UHFFFAOYSA-N 0.000 claims 1
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• RJAVWJXYLHZJBO-UHFFFAOYSA-N 2-tert-butyl-5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,3,4-oxadiazole Chemical compound CC(C)(C)c1nnc(o1)-c1cc(OCC(F)(F)F)c(cn1)C1CC1 RJAVWJXYLHZJBO-UHFFFAOYSA-N 0.000 claims 1
• XJXRVGULPJQRKD-UHFFFAOYSA-N 2-tert-butyl-5-[5-cyclopropyl-4-(oxan-4-yloxy)pyridin-2-yl]-1,3,4-oxadiazole Chemical compound CC(C)(C)c1nnc(o1)-c1cc(OC2CCOCC2)c(cn1)C1CC1 XJXRVGULPJQRKD-UHFFFAOYSA-N 0.000 claims 1
• XPVDYKBEEAXZIS-VIFPVBQESA-N 2-tert-butyl-5-[5-cyclopropyl-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,3,4-oxadiazole Chemical compound C(C)(C)(C)C=1OC(=NN1)C1=NC=C(C(=C1)O[C@H](C(F)(F)F)C)C1CC1 XPVDYKBEEAXZIS-VIFPVBQESA-N 0.000 claims 1
• UASAFNNTYJHQOD-UHFFFAOYSA-N 3-[2-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-4-methyl-5H-1,3-oxazol-4-yl]-5-methyl-1,2,4-oxadiazole Chemical compound Cc1nc(no1)C1(C)COC(=N1)c1cc(OCC(F)(F)F)c(cn1)C1CC1 UASAFNNTYJHQOD-UHFFFAOYSA-N 0.000 claims 1
• UCTPRPVWILHNJG-UHFFFAOYSA-N 3-[5-(3,3-difluoroazetidin-1-yl)-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-5-(1-methylcyclopropyl)-1,2,4-oxadiazole Chemical compound N=1C(C=2N=CC(=C(OCC(F)(F)F)C=2)N2CC(F)(F)C2)=NOC=1C1(C)CC1 UCTPRPVWILHNJG-UHFFFAOYSA-N 0.000 claims 1
• NBFYLLZYWUQAFK-UHFFFAOYSA-N 3-[5-(3,3-difluoroazetidin-1-yl)-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-5-(3-methyloxetan-3-yl)-1,2,4-oxadiazole Chemical compound N=1C(C=2N=CC(=C(OCC(F)(F)F)C=2)N2CC(F)(F)C2)=NOC=1C1(C)COC1 NBFYLLZYWUQAFK-UHFFFAOYSA-N 0.000 claims 1
• LPTSSHYYSYEFJQ-UHFFFAOYSA-N 3-[5-(3,3-difluoroazetidin-1-yl)-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-5-propan-2-yl-1,2,4-oxadiazole Chemical compound O1C(C(C)C)=NC(C=2N=CC(=C(OCC(F)(F)F)C=2)N2CC(F)(F)C2)=N1 LPTSSHYYSYEFJQ-UHFFFAOYSA-N 0.000 claims 1
• HMUPXUIISJZXTJ-UHFFFAOYSA-N 3-[5-chloro-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-5-cyclopropyl-1,2,4-oxadiazole Chemical compound C1=C(Cl)C(OCC(F)(F)F)=CC(C=2N=C(ON=2)C2CC2)=N1 HMUPXUIISJZXTJ-UHFFFAOYSA-N 0.000 claims 1
• DWXXOPWEWPSUAD-UHFFFAOYSA-N 3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound FC(F)(F)COC1=CC(C2=NOC=N2)=NC=C1C1CC1 DWXXOPWEWPSUAD-UHFFFAOYSA-N 0.000 claims 1
• MMXBYBGUZBDTCY-UHFFFAOYSA-N 3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-5-(1-methylcyclopropyl)-1,2,4-oxadiazole Chemical compound N=1C(C=2N=CC(=C(OCC(F)(F)F)C=2)C2CC2)=NOC=1C1(C)CC1 MMXBYBGUZBDTCY-UHFFFAOYSA-N 0.000 claims 1
• FIXZMDZCTAEHPP-UHFFFAOYSA-N 3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-5-(3-methyloxetan-3-yl)-1,2,4-oxadiazole Chemical compound N=1C(C=2N=CC(=C(OCC(F)(F)F)C=2)C2CC2)=NOC=1C1(C)COC1 FIXZMDZCTAEHPP-UHFFFAOYSA-N 0.000 claims 1
• BRRAYCPXSNTFOH-UHFFFAOYSA-N 3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-5-propan-2-yl-1,2,4-oxadiazole Chemical compound O1C(C(C)C)=NC(C=2N=CC(=C(OCC(F)(F)F)C=2)C2CC2)=N1 BRRAYCPXSNTFOH-UHFFFAOYSA-N 0.000 claims 1
• XFUQNVJIKLIIFB-UHFFFAOYSA-N 3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-(1-methylcyclopropyl)-1,2,4-oxadiazole Chemical compound N=1C(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=NOC=1C1(C)CC1 XFUQNVJIKLIIFB-UHFFFAOYSA-N 0.000 claims 1
• JJJIBHNTULMIAN-UHFFFAOYSA-N 3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-(3-methyloxetan-3-yl)-1,2,4-oxadiazole Chemical compound N=1C(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=NOC=1C1(C)COC1 JJJIBHNTULMIAN-UHFFFAOYSA-N 0.000 claims 1
• QVIXNVNASKMGFT-UHFFFAOYSA-N 3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-(methoxymethyl)-1,2,4-oxadiazole Chemical compound O1C(COC)=NC(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=N1 QVIXNVNASKMGFT-UHFFFAOYSA-N 0.000 claims 1
• BQBHDPAUBFFWDQ-UHFFFAOYSA-N 3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1C(C(F)(F)F)=NC(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=N1 BQBHDPAUBFFWDQ-UHFFFAOYSA-N 0.000 claims 1
• GKEGYWKEZZYQMZ-UHFFFAOYSA-N 3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-ethyl-1,2,4-oxadiazole Chemical compound O1C(CC)=NC(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=N1 GKEGYWKEZZYQMZ-UHFFFAOYSA-N 0.000 claims 1
• SPSXDNHXWIHNHC-UHFFFAOYSA-N 3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-5-propan-2-yl-1,2,4-oxadiazole Chemical compound O1C(C(C)C)=NC(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=N1 SPSXDNHXWIHNHC-UHFFFAOYSA-N 0.000 claims 1
• WXTVDVXPGHFUDM-UHFFFAOYSA-N 3-[[2-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-5-cyclopropylpyridin-4-yl]oxymethyl]morpholine Chemical compound C(C)(C)(C)C1=NC(=NO1)C1=NC=C(C(=C1)OCC1NCCOC1)C1CC1 WXTVDVXPGHFUDM-UHFFFAOYSA-N 0.000 claims 1
• IGDPJCVOFYOBAV-UHFFFAOYSA-N 3-benzyl-5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound C1CC1COC1=CC(C=2ON=C(CC=3C=CC=CC=3)N=2)=NC=C1C1CC1 IGDPJCVOFYOBAV-UHFFFAOYSA-N 0.000 claims 1
• MLOMEZJFPCGBNY-UHFFFAOYSA-N 3-cyclopentyl-5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound C1CC1COC1=CC(C=2ON=C(N=2)C2CCCC2)=NC=C1C1CC1 MLOMEZJFPCGBNY-UHFFFAOYSA-N 0.000 claims 1
• YOULCKZIZCRFKI-UHFFFAOYSA-N 3-cyclopropyl-5-[5-(3,3-difluoroazetidin-1-yl)-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound FC(F)(F)COC1=CC(C=2ON=C(N=2)C2CC2)=NC=C1N1CC(F)(F)C1 YOULCKZIZCRFKI-UHFFFAOYSA-N 0.000 claims 1
• ZSASVUGBERTODS-UHFFFAOYSA-N 3-cyclopropyl-5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound FC(F)(F)COC1=CC(C=2ON=C(N=2)C2CC2)=NC=C1C1CC1 ZSASVUGBERTODS-UHFFFAOYSA-N 0.000 claims 1
• HKMMKQPWICDJTA-UHFFFAOYSA-N 3-cyclopropyl-5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound C1CC1COC1=CC(C=2ON=C(N=2)C2CC2)=NC=C1C1CC1 HKMMKQPWICDJTA-UHFFFAOYSA-N 0.000 claims 1
• FKOFXQIDZILMJU-UHFFFAOYSA-N 3-tert-butyl-5-[5-(3,3-difluoroazetidin-1-yl)-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound CC(C)(C)C1=NOC(C=2N=CC(=C(OCC(F)(F)F)C=2)N2CC(F)(F)C2)=N1 FKOFXQIDZILMJU-UHFFFAOYSA-N 0.000 claims 1
• JGUYCZXAMPOLSJ-SECBINFHSA-N 3-tert-butyl-5-[5-cyclopropyl-4-[(2r)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,2,4-oxadiazole Chemical compound FC(F)(F)[C@@H](C)OC1=CC(C=2ON=C(N=2)C(C)(C)C)=NC=C1C1CC1 JGUYCZXAMPOLSJ-SECBINFHSA-N 0.000 claims 1
• JGUYCZXAMPOLSJ-VIFPVBQESA-N 3-tert-butyl-5-[5-cyclopropyl-4-[(2s)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,2,4-oxadiazole Chemical compound FC(F)(F)[C@H](C)OC1=CC(C=2ON=C(N=2)C(C)(C)C)=NC=C1C1CC1 JGUYCZXAMPOLSJ-VIFPVBQESA-N 0.000 claims 1
• PASLNGKADCBMLZ-AWEZNQCLSA-N 3-tert-butyl-5-[5-cyclopropyl-4-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]pyridin-2-yl]-1,2,4-oxadiazole Chemical compound CN1CCC[C@H]1COc1cc(ncc1C1CC1)-c1nc(no1)C(C)(C)C PASLNGKADCBMLZ-AWEZNQCLSA-N 0.000 claims 1
• XMFPWDZWYFCLCV-UHFFFAOYSA-N 4-[2-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-5-cyclopropylpyridin-4-yl]morpholine Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(N3CCOCC3)C=2)C2CC2)=N1 XMFPWDZWYFCLCV-UHFFFAOYSA-N 0.000 claims 1
• NFJZDGARXUMYRP-UHFFFAOYSA-N 4-[2-[2-(5-tert-butyl-1,2,4-oxadiazol-3-yl)-5-cyclopropylpyridin-4-yl]oxyethyl]morpholine Chemical compound CC(C)(C)c1nc(no1)-c1cc(OCCN2CCOCC2)c(cn1)C1CC1 NFJZDGARXUMYRP-UHFFFAOYSA-N 0.000 claims 1
• YCCGAOVHKNJCAU-UHFFFAOYSA-N 5-(azetidin-3-yl)-3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound C1CC1COC1=CC(C=2N=C(ON=2)C2CNC2)=NC=C1C1CC1 YCCGAOVHKNJCAU-UHFFFAOYSA-N 0.000 claims 1
• QISCIRQTNVSUMN-UHFFFAOYSA-N 5-[5-(3,3-difluoroazetidin-1-yl)-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(C=2N=CC(=C(OCC(F)(F)F)C=2)N2CC(F)(F)C2)=N1 QISCIRQTNVSUMN-UHFFFAOYSA-N 0.000 claims 1
• SOZHFYIMWLIKPE-UHFFFAOYSA-N 5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-3-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound FC(F)(F)COC1=CC(C=2ON=C(N=2)C(F)(F)F)=NC=C1C1CC1 SOZHFYIMWLIKPE-UHFFFAOYSA-N 0.000 claims 1
• VCWSYCZYDTXTBY-UHFFFAOYSA-N 5-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-3-propan-2-yl-1,2,4-oxadiazole Chemical compound CC(C)C1=NOC(C=2N=CC(=C(OCC(F)(F)F)C=2)C2CC2)=N1 VCWSYCZYDTXTBY-UHFFFAOYSA-N 0.000 claims 1
• QVMMRHICIJCFLC-UHFFFAOYSA-N 5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=N1 QVMMRHICIJCFLC-UHFFFAOYSA-N 0.000 claims 1
• XIHDSSMRXFSTSS-UHFFFAOYSA-N 5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-3-phenyl-1,2,4-oxadiazole Chemical compound C1CC1COC1=CC(C=2ON=C(N=2)C=2C=CC=CC=2)=NC=C1C1CC1 XIHDSSMRXFSTSS-UHFFFAOYSA-N 0.000 claims 1
• XQWCWFZAPKNWNU-UHFFFAOYSA-N 5-cyclopropyl-3-[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound FC(F)(F)COC1=CC(C=2N=C(ON=2)C2CC2)=NC=C1C1CC1 XQWCWFZAPKNWNU-UHFFFAOYSA-N 0.000 claims 1
• HPUCMPUYNUTGLJ-UHFFFAOYSA-N 5-cyclopropyl-3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound C1CC1COC1=CC(C=2N=C(ON=2)C2CC2)=NC=C1C1CC1 HPUCMPUYNUTGLJ-UHFFFAOYSA-N 0.000 claims 1
• WQKDDZZDVUBBER-QMMMGPOBSA-N 5-cyclopropyl-3-[5-cyclopropyl-4-[(2s)-1,1,1-trifluoropropan-2-yl]oxypyridin-2-yl]-1,2,4-oxadiazole Chemical compound FC(F)(F)[C@H](C)OC1=CC(C=2N=C(ON=2)C2CC2)=NC=C1C1CC1 WQKDDZZDVUBBER-QMMMGPOBSA-N 0.000 claims 1
• RLIQVMMSZNAHLH-UHFFFAOYSA-N 5-tert-butyl-2-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,3-oxazole Chemical compound O1C(C(C)(C)C)=CN=C1C1=CC(OCC2CC2)=C(C2CC2)C=N1 RLIQVMMSZNAHLH-UHFFFAOYSA-N 0.000 claims 1
• MEVFOUJZZVFDRI-UHFFFAOYSA-N 5-tert-butyl-3-(5-cyclopropyl-4-cyclopropylsulfonylpyridin-2-yl)-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(C=2)S(=O)(=O)C2CC2)C2CC2)=N1 MEVFOUJZZVFDRI-UHFFFAOYSA-N 0.000 claims 1
• QYLKJUFYMHWCKH-UHFFFAOYSA-N 5-tert-butyl-3-(5-cyclopropyl-4-piperidin-3-yloxypyridin-2-yl)-1,2,4-oxadiazole Chemical compound CC(C)(C)c1nc(no1)-c1cc(OC2CCCNC2)c(cn1)C1CC1 QYLKJUFYMHWCKH-UHFFFAOYSA-N 0.000 claims 1
• LAXQRHUWJZBDFA-UHFFFAOYSA-N 5-tert-butyl-3-(5-cyclopropyl-4-pyrrolidin-1-ylpyridin-2-yl)-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(N3CCCC3)C=2)C2CC2)=N1 LAXQRHUWJZBDFA-UHFFFAOYSA-N 0.000 claims 1
• RESZPWREOKJYOD-UHFFFAOYSA-N 5-tert-butyl-3-[4-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(OCC3CC3)C=2)N2CC(F)(F)C2)=N1 RESZPWREOKJYOD-UHFFFAOYSA-N 0.000 claims 1
• OABRLYVFUBJJPZ-UHFFFAOYSA-N 5-tert-butyl-3-[4-(cyclopropylmethoxy)-5-methylsulfonylpyridin-2-yl]-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(OCC3CC3)C=2)S(C)(=O)=O)=N1 OABRLYVFUBJJPZ-UHFFFAOYSA-N 0.000 claims 1
• MPGAWRWCELQBBI-UHFFFAOYSA-N 5-tert-butyl-3-[5-(3,3-difluoroazetidin-1-yl)-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(OCC(F)(F)F)C=2)N2CC(F)(F)C2)=N1 MPGAWRWCELQBBI-UHFFFAOYSA-N 0.000 claims 1
• ITHFRKFWHGUPIW-UHFFFAOYSA-N 5-tert-butyl-3-[5-(3-fluorooxetan-3-yl)-4-(4-fluorophenoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound CC(C)(C)c1nc(no1)-c1cc(Oc2ccc(F)cc2)c(cn1)C1(F)COC1 ITHFRKFWHGUPIW-UHFFFAOYSA-N 0.000 claims 1
• BZKCRABBWHSWAK-UHFFFAOYSA-N 5-tert-butyl-3-[5-(3-fluorooxetan-3-yl)-4-(oxan-4-yloxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound CC(C)(C)c1nc(no1)-c1cc(OC2CCOCC2)c(cn1)C1(F)COC1 BZKCRABBWHSWAK-UHFFFAOYSA-N 0.000 claims 1
• HTUYGJMIBCCOFV-UHFFFAOYSA-N 5-tert-butyl-3-[5-chloro-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(Cl)=C(OCC(F)(F)F)C=2)=N1 HTUYGJMIBCCOFV-UHFFFAOYSA-N 0.000 claims 1
• AQEKKKCPWNRPKX-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(1-ethylpiperidin-3-yl)oxypyridin-2-yl]-1,2,4-oxadiazole Chemical compound CCN1CCCC(C1)Oc1cc(ncc1C1CC1)-c1noc(n1)C(C)(C)C AQEKKKCPWNRPKX-UHFFFAOYSA-N 0.000 claims 1
• CXONGJWNQWOHDR-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(1-ethylpyrrolidin-3-yl)oxypyridin-2-yl]-1,2,4-oxadiazole Chemical compound C1N(CC)CCC1OC1=CC(C=2N=C(ON=2)C(C)(C)C)=NC=C1C1CC1 CXONGJWNQWOHDR-UHFFFAOYSA-N 0.000 claims 1
• BCQYNJOHJDJRHR-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(1-methoxybutan-2-yloxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound COCC(CC)OC1=CC(C=2N=C(ON=2)C(C)(C)C)=NC=C1C1CC1 BCQYNJOHJDJRHR-UHFFFAOYSA-N 0.000 claims 1
• PEYIQKRZOWIHGU-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(1-methoxypropan-2-yloxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound COCC(C)OC1=CC(C=2N=C(ON=2)C(C)(C)C)=NC=C1C1CC1 PEYIQKRZOWIHGU-UHFFFAOYSA-N 0.000 claims 1
• XDKWAFOSQNNEDA-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(1-methylpiperidin-3-yl)oxypyridin-2-yl]-1,2,4-oxadiazole Chemical compound CN1CCCC(C1)Oc1cc(ncc1C1CC1)-c1noc(n1)C(C)(C)C XDKWAFOSQNNEDA-UHFFFAOYSA-N 0.000 claims 1
• MUJCJCLTFMHDQA-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(1-piperidin-1-ylpropan-2-yloxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound C=1C(C=2N=C(ON=2)C(C)(C)C)=NC=C(C2CC2)C=1OC(C)CN1CCCCC1 MUJCJCLTFMHDQA-UHFFFAOYSA-N 0.000 claims 1
• SAZDJVMEWWQNCL-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(1-propan-2-ylpyrrolidin-3-yl)oxypyridin-2-yl]-1,2,4-oxadiazole Chemical compound C1N(C(C)C)CCC1OC1=CC(C=2N=C(ON=2)C(C)(C)C)=NC=C1C1CC1 SAZDJVMEWWQNCL-UHFFFAOYSA-N 0.000 claims 1
• XAIZFSWQRNKAFS-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(2,2-difluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound CC(C)(C)c1nc(no1)-c1cc(OCC(F)F)c(cn1)C1CC1 XAIZFSWQRNKAFS-UHFFFAOYSA-N 0.000 claims 1
• GEYUYVULXXGHJA-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(2-fluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound CC(C)(C)c1nc(no1)-c1cc(OCCF)c(cn1)C1CC1 GEYUYVULXXGHJA-UHFFFAOYSA-N 0.000 claims 1
• YXFOURCEWXDBOF-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(2-piperidin-1-ylethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(OCCN3CCCCC3)C=2)C2CC2)=N1 YXFOURCEWXDBOF-UHFFFAOYSA-N 0.000 claims 1
• JIMPSFQQWYIOIF-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(2-pyrrolidin-1-ylethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(OCCN3CCCC3)C=2)C2CC2)=N1 JIMPSFQQWYIOIF-UHFFFAOYSA-N 0.000 claims 1
• TUSBRWJJUOSOSX-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(3,3,4,4-tetrafluoropyrrolidin-1-yl)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NC(C=2N=CC(=C(N3CC(F)(F)C(F)(F)C3)C=2)C2CC2)=N1 TUSBRWJJUOSOSX-UHFFFAOYSA-N 0.000 claims 1
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• 230000004044 response Effects 0.000 description 1
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• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
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• UIJXHKXIOCDSEB-UHFFFAOYSA-N tert-butyl 3-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(O)C1 UIJXHKXIOCDSEB-UHFFFAOYSA-N 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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• 125000001302 tertiary amino group Chemical group 0.000 description 1
• PCZOZSATUTWXIC-UHFFFAOYSA-N tetraethylazanium;cyanide Chemical compound N#[C-].CC[N+](CC)(CC)CC PCZOZSATUTWXIC-UHFFFAOYSA-N 0.000 description 1
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• YSHOWEKUVWPFNR-UHFFFAOYSA-O triethyl(methoxycarbonylsulfamoyl)azanium Chemical compound CC[N+](CC)(CC)S(=O)(=O)NC(=O)OC YSHOWEKUVWPFNR-UHFFFAOYSA-O 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
• PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 description 1
• 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
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