SI2978755T1 - New pyridine derivatives - Google Patents
New pyridine derivatives Download PDFInfo
- Publication number
- SI2978755T1 SI2978755T1 SI201430615T SI201430615T SI2978755T1 SI 2978755 T1 SI2978755 T1 SI 2978755T1 SI 201430615 T SI201430615 T SI 201430615T SI 201430615 T SI201430615 T SI 201430615T SI 2978755 T1 SI2978755 T1 SI 2978755T1
- Authority
- SI
- Slovenia
- Prior art keywords
- cyclopropyl
- pyridin
- oxadiazole
- butyl
- tert
- Prior art date
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- 150000003222 pyridines Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract 38
- -1 haloazetidinyl Chemical group 0.000 claims 26
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 17
- 238000010438 heat treatment Methods 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 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 2
- 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
- NYWVYTLJBSZCJZ-UHFFFAOYSA-N 5-tert-butyl-3-[5-cyclopropyl-4-(1-methylpyrrolidin-3-yl)oxypyridin-2-yl]-1,2,4-oxadiazole Chemical compound C1N(C)CCC1OC1=CC(C=2N=C(ON=2)C(C)(C)C)=NC=C1C1CC1 NYWVYTLJBSZCJZ-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
- BCIIWQHRWPXARK-UHFFFAOYSA-N 6-oxa-1-azaspiro[3.3]heptane Chemical compound N1CCC11COC1 BCIIWQHRWPXARK-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- YSHOWEKUVWPFNR-UHFFFAOYSA-N burgess reagent Chemical compound CC[N+](CC)(CC)S(=O)(=O)N=C([O-])OC YSHOWEKUVWPFNR-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims 2
- 229910052736 halogen Chemical group 0.000 claims 2
- 125000005059 halophenyl group Chemical group 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 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 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
- 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
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-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
- 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
- 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
- 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
- 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 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
- 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
- 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
- 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
- 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
- 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
- QQARDXULXGUIKC-UHFFFAOYSA-N 3-tert-butyl-5-[5-cyclopropyl-4-(cyclopropylmethoxy)pyridin-2-yl]-1,2,4-oxadiazole Chemical compound CC(C)(C)C1=NOC(C=2N=CC(=C(OCC3CC3)C=2)C2CC2)=N1 QQARDXULXGUIKC-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
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- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
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- 125000003566 oxetanyl group Chemical group 0.000 claims 1
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- 229910052763 palladium Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
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- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 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 1
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Classifications
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
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- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
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- Cardiology (AREA)
- Immunology (AREA)
- Ophthalmology & Optometry (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
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- Psychology (AREA)
- Hematology (AREA)
- Gastroenterology & Hepatology (AREA)
- Endocrinology (AREA)
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- Transplantation (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13161176 | 2013-03-26 | ||
| EP14712287.3A EP2978755B1 (en) | 2013-03-26 | 2014-03-24 | Novel pyridine derivatives |
| PCT/EP2014/055797 WO2014154612A1 (en) | 2013-03-26 | 2014-03-24 | Novel pyridine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI2978755T1 true SI2978755T1 (en) | 2018-03-30 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| SI201430615T SI2978755T1 (en) | 2013-03-26 | 2014-03-24 | New pyridine derivatives |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPWO2015190316A1 (ja) * | 2014-06-09 | 2017-04-20 | 住友化学株式会社 | ピリジン化合物の製造方法 |
| DK3386951T3 (en) * | 2015-12-09 | 2020-04-27 | Hoffmann La Roche | Phenylderivater som cannabinoidreceptor-2-agonister |
| KR102384529B1 (ko) * | 2016-07-07 | 2022-04-08 | 코르테바 애그리사이언스 엘엘씨 | 4-알콕시-3-(아실 또는 알킬)옥시피콜린아미드의 제조 방법 |
| TWI886480B (zh) * | 2017-04-06 | 2025-06-11 | 美商富曼西公司 | 殺真菌之噁二唑 |
| JP7300398B2 (ja) * | 2017-06-20 | 2023-06-29 | エフ． ホフマン－ラ ロシュ アーゲー | ピリジン誘導体 |
| WO2019003956A1 (ja) * | 2017-06-27 | 2019-01-03 | 住友化学株式会社 | オキサジアゾール化合物及びその用途 |
| CN108774220B (zh) * | 2018-05-27 | 2019-04-23 | 西安培华学院 | 用于治疗心肌缺血的化合物及其应用 |
| EP3995155A1 (en) | 2018-06-27 | 2022-05-11 | F. Hoffmann-La Roche AG | Radiolabeled cannabinoid receptor 2 ligand |
| CN112074513B (zh) * | 2018-06-27 | 2024-06-14 | 豪夫迈·罗氏有限公司 | 作为优先大麻素2激动剂的吡啶和吡嗪衍生物 |
| BR112020025013A2 (pt) | 2018-06-27 | 2021-03-23 | F. Hoffmann-La Roche Ag | novos compostos de piridina e pirazina como inibidores do receptor 2 de canabinoide |
| EP3814328A1 (en) | 2018-06-27 | 2021-05-05 | F. Hoffmann-La Roche AG | Novel azetidine-substituted pyridine and pyrazine compounds as inhibitors of cannabinoid receptor 2 |
| CN114195759B (zh) * | 2021-08-26 | 2023-10-20 | 上海零诺生物科技有限公司 | 一种2-甲基-5-（1-甲基吡咯烷-2-基）吡啶制备方法 |
| US20240425513A1 (en) * | 2021-10-22 | 2024-12-26 | Carmot Therapeutics, Inc. | Oxazole, oxadiazole, and indole derivatives for the inhibition of usp28 |
| CN115073366B (zh) * | 2022-06-08 | 2024-08-09 | 都创(重庆)医药科技有限公司 | 一种基于微通道技术快速制备3-氯吡啶-2-甲酸的方法 |
| WO2025104141A1 (en) * | 2023-11-16 | 2025-05-22 | F. Hoffmann-La Roche Ag | Novel reversible fluorescent probes for cb2 |
Family Cites Families (13)
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| US7271266B2 (en) * | 2002-03-28 | 2007-09-18 | Merck & Co., Inc. | Substituted 2,3-diphenyl pyridines |
| WO2008019357A2 (en) * | 2006-08-07 | 2008-02-14 | Ironwood Pharmaceuticals, Inc. | Indole compounds |
| WO2009051705A1 (en) * | 2007-10-18 | 2009-04-23 | Merck & Co., Inc. | Substituted 1,2,4-oxadiazoles and analogs thereof as cb2 receptor modulators, useful in the treatment of pain, respiratory and non-respiratory diseases |
| US9321727B2 (en) | 2011-06-10 | 2016-04-26 | Hoffmann-La Roche Inc. | Pyridine derivatives as agonists of the CB2 receptor |
| UA111640C2 (uk) | 2011-11-08 | 2016-05-25 | Ф. Хоффманн-Ля Рош Аг | ПОХІДНІ [1,2,3]ТРИАЗОЛО[4,5-d]ПІРИМІДИНУ ЯК АГОНІСТИ КАНАБІНОЇДНОГО РЕЦЕПТОРА 2 |
| KR20150027824A (ko) | 2012-07-04 | 2015-03-12 | 에프. 호프만-라 로슈 아게 | 칸나비노이드 수용체 2 작용제로서 신규한 아다만틸 유도체 |
| MX2015007156A (es) | 2012-12-07 | 2015-10-14 | Hoffmann La Roche | Piridina-2-amidas utiles como agonistas receptores de canabinoides 2 (cb2). |
| CA2885987A1 (en) | 2012-12-07 | 2014-06-12 | F. Hoffmann-La Roche Ag | Pyridine-2-amides useful as cb2 agonists |
| SG10201800170YA (en) | 2012-12-07 | 2018-02-27 | Hoffmann La Roche | Novel pyridine derivatives |
| RS55951B1 (sr) | 2012-12-07 | 2017-09-29 | Hoffmann La Roche | Derivati pirazina kao agonisti cb2 receptora |
| JP6514119B2 (ja) | 2013-03-07 | 2019-05-15 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 新規ピラゾール誘導体 |
| CA2943013A1 (en) | 2014-04-04 | 2015-10-08 | F. Hoffmann-La Roche Ag | Pyridine-2-amides useful as cb2 agonists |
| CR20160459A (es) | 2014-04-04 | 2016-12-02 | Eidgenoessische Technische Hochschule Zuerich | Nuevos derivados de piridina |
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- 2014-03-25 AR ARP140101336A patent/AR095721A1/es unknown
-
2015
- 2015-07-21 ZA ZA2015/05251A patent/ZA201505251B/en unknown
- 2015-08-10 IL IL240496A patent/IL240496B/en active IP Right Grant
- 2015-08-25 CR CR20150440A patent/CR20150440A/es unknown
- 2015-09-02 PH PH12015501933A patent/PH12015501933B1/en unknown
- 2015-09-23 CL CL2015002835A patent/CL2015002835A1/es unknown
- 2015-09-28 US US14/868,305 patent/US10308659B2/en not_active Expired - Fee Related
-
2019
- 2019-04-24 US US16/393,794 patent/US20190248803A1/en not_active Abandoned
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