TWI628174B - 新穎吡啶衍生物 - Google Patents

Info

Publication number

TWI628174B

TWI628174B TW103111118A TW103111118A TWI628174B TW I628174 B TWI628174 B TW I628174B TW 103111118 A TW103111118 A TW 103111118A TW 103111118 A TW103111118 A TW 103111118A TW I628174 B TWI628174 B TW I628174B

Authority

TW

Taiwan

Prior art keywords

cyclopropyl

pyridin

oxadiazole

butyl

compound

Prior art date

2013-03-26

Links

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• 150000003222 pyridines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 367
• 239000003814 drug Substances 0.000 claims abstract description 7
• -1 6-oxa-1-aza-spiro [3.3] heptyl Chemical group 0.000 claims description 293
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 46
• 238000000034 method Methods 0.000 claims description 38
• 239000002585 base Substances 0.000 claims description 32
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
• 125000000217 alkyl group Chemical group 0.000 claims description 23
• 238000010438 heat treatment Methods 0.000 claims description 21
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 20
• 206010016654 Fibrosis Diseases 0.000 claims description 16
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 206010063837 Reperfusion injury Diseases 0.000 claims description 13
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
• 239000001257 hydrogen Substances 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 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
• 150000003839 salts Chemical class 0.000 claims description 12
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 11
• 125000001188 haloalkyl group Chemical group 0.000 claims description 11
• 125000003566 oxetanyl group Chemical group 0.000 claims description 11
• 230000004761 fibrosis Effects 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 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
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 9
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
• 239000003054 catalyst Substances 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 208000010125 myocardial infarction Diseases 0.000 claims description 9
• 239000007800 oxidant agent Substances 0.000 claims description 9
• 230000001590 oxidative effect Effects 0.000 claims description 9
• 229910052763 palladium Inorganic materials 0.000 claims description 9
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 9
• 201000001320 Atherosclerosis Diseases 0.000 claims description 8
• 206010003694 Atrophy Diseases 0.000 claims description 8
• 208000010412 Glaucoma Diseases 0.000 claims description 8
• 208000002193 Pain Diseases 0.000 claims description 8
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 8
• 208000006011 Stroke Diseases 0.000 claims description 8
• 206010042953 Systemic sclerosis Diseases 0.000 claims description 8
• 206010046851 Uveitis Diseases 0.000 claims description 8
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 8
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 8
• 230000037444 atrophy Effects 0.000 claims description 8
• 208000012947 ischemia reperfusion injury Diseases 0.000 claims description 8
• 208000017169 kidney disease Diseases 0.000 claims description 8
• 208000002780 macular degeneration Diseases 0.000 claims description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• 201000006417 multiple sclerosis Diseases 0.000 claims description 8
• 230000002265 prevention Effects 0.000 claims description 8
• 208000007788 Acute Liver Failure Diseases 0.000 claims description 7
• 206010000804 Acute hepatic failure Diseases 0.000 claims description 7
• 208000032544 Cicatrix Diseases 0.000 claims description 7
• 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 7
• 206010019280 Heart failures Diseases 0.000 claims description 7
• 206010061218 Inflammation Diseases 0.000 claims description 7
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
• 208000002260 Keloid Diseases 0.000 claims description 7
• 208000018737 Parkinson disease Diseases 0.000 claims description 7
• 206010037660 Pyrexia Diseases 0.000 claims description 7
• 201000009594 Systemic Scleroderma Diseases 0.000 claims description 7
• 206010052779 Transplant rejections Diseases 0.000 claims description 7
• 231100000836 acute liver failure Toxicity 0.000 claims description 7
• 239000000460 chlorine Substances 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• 206010012601 diabetes mellitus Diseases 0.000 claims description 7
• 208000033679 diabetic kidney disease Diseases 0.000 claims description 7
• 208000007565 gingivitis Diseases 0.000 claims description 7
• 230000001434 glomerular Effects 0.000 claims description 7
• 125000005059 halophenyl group Chemical group 0.000 claims description 7
• 150000002431 hydrogen Chemical class 0.000 claims description 7
• 230000004054 inflammatory process Effects 0.000 claims description 7
• 210000001117 keloid Anatomy 0.000 claims description 7
• 208000014018 liver neoplasm Diseases 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 7
• 210000001957 retinal vein Anatomy 0.000 claims description 7
• 231100000241 scar Toxicity 0.000 claims description 7
• 230000037387 scars Effects 0.000 claims description 7
• 230000009885 systemic effect Effects 0.000 claims description 7
• 208000024827 Alzheimer disease Diseases 0.000 claims description 6
• 208000031229 Cardiomyopathies Diseases 0.000 claims description 6
• 206010063209 Chronic allograft nephropathy Diseases 0.000 claims description 6
• 201000001200 Crouzon syndrome-acanthosis nigricans syndrome Diseases 0.000 claims description 6
• 206010019695 Hepatic neoplasm Diseases 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 206010069385 Ocular ischaemic syndrome Diseases 0.000 claims description 6
• 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 230000007882 cirrhosis Effects 0.000 claims description 6
• 230000001969 hypertrophic effect Effects 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
• 208000031225 myocardial ischemia Diseases 0.000 claims description 6
• 201000002793 renal fibrosis Diseases 0.000 claims description 6
• 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 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
• 206010061876 Obstruction Diseases 0.000 claims description 5
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
• 150000001721 carbon Chemical group 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 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
• VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 claims description 5
• 229940098779 methanesulfonic acid Drugs 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• BCIIWQHRWPXARK-UHFFFAOYSA-N 6-oxa-1-azaspiro[3.3]heptane Chemical compound N1CCC11COC1 BCIIWQHRWPXARK-UHFFFAOYSA-N 0.000 claims description 4
• JCHKXBWPGRTSEB-UHFFFAOYSA-N CCCCC1=NC(=NO1)C2=NC=C(C(=C2)OCC3=NC=C(C=C3)F)C4CC4 Chemical compound CCCCC1=NC(=NO1)C2=NC=C(C(=C2)OCC3=NC=C(C=C3)F)C4CC4 JCHKXBWPGRTSEB-UHFFFAOYSA-N 0.000 claims description 4
• BLIIMUVZCXRLKA-UHFFFAOYSA-N CCCCC1=NC(=NO1)C2=NC=C(C(=C2)OCC3COC3)C4CC4 Chemical compound CCCCC1=NC(=NO1)C2=NC=C(C(=C2)OCC3COC3)C4CC4 BLIIMUVZCXRLKA-UHFFFAOYSA-N 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 210000000988 bone and bone Anatomy 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
• 230000011164 ossification Effects 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• POLBNZVUVRPJSZ-UHFFFAOYSA-N 3-[3-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]oxetan-3-amine Chemical compound N=1C(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=NOC=1C1(N)COC1 POLBNZVUVRPJSZ-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 201000006474 Brain Ischemia Diseases 0.000 claims description 3
• WPVXQMNQRPGSHL-UHFFFAOYSA-N CCCCC1=NC(=NO1)C2=NC=C(C(=C2)OCCOCC)C3CC3 Chemical compound CCCCC1=NC(=NO1)C2=NC=C(C(=C2)OCCOCC)C3CC3 WPVXQMNQRPGSHL-UHFFFAOYSA-N 0.000 claims description 3
• 206010008120 Cerebral ischaemia Diseases 0.000 claims description 3
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
• 206010008118 cerebral infarction Diseases 0.000 claims description 3
• 239000012320 chlorinating reagent Substances 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
• 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 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 125000006542 morpholinylalkyl group Chemical group 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
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
• JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 201000010875 transient cerebral ischemia Diseases 0.000 claims description 3
• 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 description 2
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