HRP20230243T1 - Alkoksi supstituirani derivati piridinila kao antagonisti receptora lpa1 i njihova uporaba u liječenju fibroze - Google Patents
Alkoksi supstituirani derivati piridinila kao antagonisti receptora lpa1 i njihova uporaba u liječenju fibroze Download PDFInfo
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- HRP20230243T1 HRP20230243T1 HRP20230243TT HRP20230243T HRP20230243T1 HR P20230243 T1 HRP20230243 T1 HR P20230243T1 HR P20230243T T HRP20230243T T HR P20230243TT HR P20230243 T HRP20230243 T HR P20230243T HR P20230243 T1 HRP20230243 T1 HR P20230243T1
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- Croatia
- Prior art keywords
- alkylene
- difluoromethoxy
- isopropylphenyl
- methylpyridin
- alkyl
- Prior art date
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- 206010016654 Fibrosis Diseases 0.000 title claims 3
- 230000004761 fibrosis Effects 0.000 title claims 3
- 125000004076 pyridyl group Chemical class 0.000 title claims 2
- 102000004137 Lysophosphatidic Acid Receptors Human genes 0.000 title 1
- 108090000642 Lysophosphatidic Acid Receptors Proteins 0.000 title 1
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 86
- 229910052739 hydrogen Inorganic materials 0.000 claims 64
- 239000001257 hydrogen Substances 0.000 claims 64
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 36
- 150000002431 hydrogen Chemical class 0.000 claims 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 22
- 229910052757 nitrogen Inorganic materials 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 8
- -1 cyclopent-1-en-1-yl Chemical group 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- VALZSZJVEFACEZ-UHFFFAOYSA-N azetidine-3-carboxamide Chemical compound NC(=O)C1CNC1 VALZSZJVEFACEZ-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 239000012634 fragment Substances 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- VHNLQFGFTLVHOM-UHFFFAOYSA-N 4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CC(C(=O)O)(C)C)=O)C1=C(C=CC=C1)C(C)C)C)F VHNLQFGFTLVHOM-UHFFFAOYSA-N 0.000 claims 2
- AHMHQDZHVSRILS-UHFFFAOYSA-N 4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2,2-dimethylbutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)CCC(C(=O)O)(C)C)C1=C(C=CC=C1)C(C)C)C)F AHMHQDZHVSRILS-UHFFFAOYSA-N 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- GGRMIHRJVAPNRY-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-(3-oxo-1,2-oxazole-5-carbonyl)-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(=O)C1=CC(=NO1)O)C1=C(C=CC=C1)C(C)C)C)F GGRMIHRJVAPNRY-UHFFFAOYSA-N 0.000 claims 2
- SHZFRMXCQTWAAL-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[2-(3-oxo-1,2-dihydropyrazol-4-yl)acetyl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CC=1C(=NNC=1)O)=O)C1=C(C=CC=C1)C(C)C)C)F SHZFRMXCQTWAAL-UHFFFAOYSA-N 0.000 claims 2
- YPWIYGPHEISLTB-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[2-(3-oxo-1,2-dihydropyrazol-4-yl)acetyl]-4-(2-propan-2-ylphenyl)piperidine-4-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CCN(CC1)C(CC=1C(=NNC=1)O)=O)C1=C(C=CC=C1)C(C)C)C)F YPWIYGPHEISLTB-UHFFFAOYSA-N 0.000 claims 2
- XZYKRCKNDIMYAI-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[2-(5-oxo-1,2-dihydropyrazol-3-yl)acetyl]-4-(2-propan-2-ylphenyl)piperidine-4-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CCN(CC1)C(CC1=CC(=NN1)O)=O)C1=C(C=CC=C1)C(C)C)C)F XZYKRCKNDIMYAI-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 230000036210 malignancy Effects 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- HYENSTZVOBGNRQ-DLBZAZTESA-N (1R,2S)-2-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidine-1-carbonyl]cyclopropane-1-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(=O)[C@@H]1[C@@H](C1)C(=O)O)C1=C(C=CC=C1)C(C)C)C)F HYENSTZVOBGNRQ-DLBZAZTESA-N 0.000 claims 1
- HYENSTZVOBGNRQ-SJORKVTESA-N (1S,2R)-2-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidine-1-carbonyl]cyclopropane-1-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(=O)[C@H]1[C@H](C1)C(=O)O)C1=C(C=CC=C1)C(C)C)C)F HYENSTZVOBGNRQ-SJORKVTESA-N 0.000 claims 1
- FOYDJHGKUNHNFP-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-[[3-(difluoromethoxy)-5-methylpyridin-2-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidine-1-carboxylate Chemical compound FC(OC=1C(=NC=C(C=1)C)NC(=O)C1(CN(C1)C(=O)OCC(=O)OC)C1=C(C=CC=C1)C(C)C)F FOYDJHGKUNHNFP-UHFFFAOYSA-N 0.000 claims 1
- GVROUKQKEMRGGR-OAHLLOKOSA-N (2R)-2-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidine-1-carbonyl]oxypropanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(=O)O[C@@H](C(=O)O)C)C1=C(C=CC=C1)C(C)C)C)F GVROUKQKEMRGGR-OAHLLOKOSA-N 0.000 claims 1
- XNUSWGRNROTIOB-DEOSSOPVSA-N (2S)-4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2-hydroxy-2-methyl-4-oxobutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(C[C@](C(=O)O)(C)O)=O)C1=C(C=CC=C1)C(C)C)C)F XNUSWGRNROTIOB-DEOSSOPVSA-N 0.000 claims 1
- UCEJFHRGABMOQB-HNNXBMFYSA-N (2S)-4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2-methyl-4-oxobutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(C[C@@H](C(=O)O)C)=O)C1=C(C=CC=C1)C(C)C)C)F UCEJFHRGABMOQB-HNNXBMFYSA-N 0.000 claims 1
- IWSZVEXEYBZCDH-OAHLLOKOSA-N (3R)-4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-3-methyl-4-oxobutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C([C@@H](CC(=O)O)C)=O)C1=C(C=CC=C1)C(C)C)C)F IWSZVEXEYBZCDH-OAHLLOKOSA-N 0.000 claims 1
- HAMJQEGFUJQQDP-ZHACJKMWSA-N (E)-3-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]sulfonylprop-2-enoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)S(=O)(=O)/C=C/C(=O)O)C1=C(C=CC=C1)C(C)C)C)F HAMJQEGFUJQQDP-ZHACJKMWSA-N 0.000 claims 1
- ZRBJBOWJTUPIJC-UHFFFAOYSA-N 1-(2-aminoethyl)-N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound NCCN1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C ZRBJBOWJTUPIJC-UHFFFAOYSA-N 0.000 claims 1
- ZESICJYPQDFCHA-UHFFFAOYSA-N 1-(2-aminopropyl)-N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound NC(CN1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C)C ZESICJYPQDFCHA-UHFFFAOYSA-N 0.000 claims 1
- KIEKGSMNXJTUEL-UHFFFAOYSA-N 1-(2-cyanoethyl)-N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound C(#N)CCN1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C KIEKGSMNXJTUEL-UHFFFAOYSA-N 0.000 claims 1
- UWEGTUUQSDLZEV-UHFFFAOYSA-N 1-(4-cyanobutanoyl)-N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound C(#N)CCCC(=O)N1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C UWEGTUUQSDLZEV-UHFFFAOYSA-N 0.000 claims 1
- JPUWTMCRTUXKEJ-UHFFFAOYSA-N 1-(5-cyanopyridin-2-yl)-N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound C(#N)C=1C=CC(=NC=1)N1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C JPUWTMCRTUXKEJ-UHFFFAOYSA-N 0.000 claims 1
- BLBSHZUCUGOSLX-UHFFFAOYSA-N 1-(5-cyanopyridin-2-yl)-N-[2-(difluoromethoxy)pyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound C(#N)C=1C=CC(=NC=1)N1CC(C1)(C(=O)NC=1C(=NC=CC=1)OC(F)F)C1=C(C=CC=C1)C(C)C BLBSHZUCUGOSLX-UHFFFAOYSA-N 0.000 claims 1
- QOBAWPGUHJGXMC-UHFFFAOYSA-N 1-(5-cyanopyrimidin-2-yl)-N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound C(#N)C=1C=NC(=NC=1)N1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C QOBAWPGUHJGXMC-UHFFFAOYSA-N 0.000 claims 1
- YPWMIKZDLKPJDS-UHFFFAOYSA-N 1-(5-cyanopyrimidin-2-yl)-N-[2-(difluoromethoxy)pyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound C(#N)C=1C=NC(=NC=1)N1CC(C1)(C(=O)NC=1C(=NC=CC=1)OC(F)F)C1=C(C=CC=C1)C(C)C YPWMIKZDLKPJDS-UHFFFAOYSA-N 0.000 claims 1
- DKDSSJXOQCAVMH-UHFFFAOYSA-N 1-(cyanomethyl)-N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound C(#N)CN1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C DKDSSJXOQCAVMH-UHFFFAOYSA-N 0.000 claims 1
- VHJSCKHFNYADGY-UHFFFAOYSA-N 1-(cyclopropylsulfamoyl)-N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound C1(CC1)NS(=O)(=O)N1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C VHJSCKHFNYADGY-UHFFFAOYSA-N 0.000 claims 1
- UADWBSUIQOBESC-UHFFFAOYSA-N 1-N-cyclopropyl-3-N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(3-propan-2-ylpyridin-2-yl)azetidine-1,3-dicarboxamide Chemical compound C1(CC1)NC(=O)N1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=NC=CC=C1C(C)C UADWBSUIQOBESC-UHFFFAOYSA-N 0.000 claims 1
- XVSJGVHFJBVVSW-HNNXBMFYSA-N 1-[(2S)-2-aminopropanoyl]-N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound N[C@@H](C)C(=O)N1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C XVSJGVHFJBVVSW-HNNXBMFYSA-N 0.000 claims 1
- ATLZMNIWJKIJGC-UHFFFAOYSA-N 1-[2-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2-oxoethyl]cyclobutane-1-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CC1(CCC1)C(=O)O)=O)C1=C(C=CC=C1)C(C)C)C)F ATLZMNIWJKIJGC-UHFFFAOYSA-N 0.000 claims 1
- DMOMTLWHUJPLJZ-UHFFFAOYSA-N 1-[2-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2-oxoethyl]cyclopropane-1-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CC1(CC1)C(=O)O)=O)C1=C(C=CC=C1)C(C)C)C)F DMOMTLWHUJPLJZ-UHFFFAOYSA-N 0.000 claims 1
- XXKXFZNYVSJCCD-UHFFFAOYSA-N 1-[2-[3-[[3-(difluoromethoxy)-5-methylpyridin-2-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2-oxoethyl]cyclobutane-1-carboxylic acid Chemical compound FC(OC=1C(=NC=C(C=1)C)NC(=O)C1(CN(C1)C(CC1(CCC1)C(=O)O)=O)C1=C(C=CC=C1)C(C)C)F XXKXFZNYVSJCCD-UHFFFAOYSA-N 0.000 claims 1
- QWQNYKOJBOPVPX-UHFFFAOYSA-N 1-[2-[acetyl(hydroxy)amino]acetyl]-N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound C(C)(=O)N(CC(=O)N1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C)O QWQNYKOJBOPVPX-UHFFFAOYSA-N 0.000 claims 1
- QYKBSFMIMDRZQF-UHFFFAOYSA-N 1-[3-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]propyl]cyclopropane-1-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)CCCC1(CC1)C(=O)O)C1=C(C=CC=C1)C(C)C)C)F QYKBSFMIMDRZQF-UHFFFAOYSA-N 0.000 claims 1
- LSJLJLQBCFGVEI-UHFFFAOYSA-N 1-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidine-1-carbonyl]oxycyclopropane-1-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(=O)OC1(CC1)C(=O)O)C1=C(C=CC=C1)C(C)C)C)F LSJLJLQBCFGVEI-UHFFFAOYSA-N 0.000 claims 1
- GDBSAKFCCFGTHU-UHFFFAOYSA-N 1-[3-[[3-(difluoromethoxy)-5-methylpyridin-2-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidine-1-carbonyl]oxycyclopropane-1-carboxylic acid Chemical compound FC(OC=1C(=NC=C(C=1)C)NC(=O)C1(CN(C1)C(=O)OC1(CC1)C(=O)O)C1=C(C=CC=C1)C(C)C)F GDBSAKFCCFGTHU-UHFFFAOYSA-N 0.000 claims 1
- BWRUBWBCMKUNOW-UHFFFAOYSA-N 1-[5-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]pyrimidin-2-yl]cyclopropane-1-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C=1C=NC(=NC=1)C1(CC1)C(=O)O)C1=C(C=CC=C1)C(C)C)C)F BWRUBWBCMKUNOW-UHFFFAOYSA-N 0.000 claims 1
- CWPZTAXAXQLIBR-UHFFFAOYSA-N 1-[[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidine-1-carbonyl]oxymethyl]cyclopropane-1-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(=O)OCC1(CC1)C(=O)O)C1=C(C=CC=C1)C(C)C)C)F CWPZTAXAXQLIBR-UHFFFAOYSA-N 0.000 claims 1
- BRACXXPRIVUCGI-UHFFFAOYSA-N 1-acetyl-N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound C(C)(=O)N1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C BRACXXPRIVUCGI-UHFFFAOYSA-N 0.000 claims 1
- GPFWKAYUJNDESI-UHFFFAOYSA-N 1-cyano-N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound C(#N)N1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C GPFWKAYUJNDESI-UHFFFAOYSA-N 0.000 claims 1
- USQDNWHZOYHLCT-UHFFFAOYSA-N 2-[1-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]sulfonylcyclopropyl]acetic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)S(=O)(=O)C1(CC1)CC(=O)O)C1=C(C=CC=C1)C(C)C)C)F USQDNWHZOYHLCT-UHFFFAOYSA-N 0.000 claims 1
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- SRTXZEZABAZZLW-UHFFFAOYSA-N 2-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidine-1-carbonyl]oxyacetic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(=O)OCC(=O)O)C1=C(C=CC=C1)C(C)C)C)F SRTXZEZABAZZLW-UHFFFAOYSA-N 0.000 claims 1
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- IBXSEJKRMCEICT-UHFFFAOYSA-N 3-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-3-oxopropanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CC(=O)O)=O)C1=C(C=CC=C1)C(C)C)C)F IBXSEJKRMCEICT-UHFFFAOYSA-N 0.000 claims 1
- OZBOSXMOBYAVAW-UHFFFAOYSA-N 3-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]propanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)CCC(=O)O)C1=C(C=CC=C1)C(C)C)C)F OZBOSXMOBYAVAW-UHFFFAOYSA-N 0.000 claims 1
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- RKFBUCFPERQPLG-UHFFFAOYSA-N 3-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]sulfonylpropanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)S(=O)(=O)CCC(=O)O)C1=C(C=CC=C1)C(C)C)C)F RKFBUCFPERQPLG-UHFFFAOYSA-N 0.000 claims 1
- WRNDWMFZGGVFFX-UHFFFAOYSA-N 3-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidine-1-carbonyl]oxy-2,2-dimethylpropanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(=O)OCC(C(=O)O)(C)C)C1=C(C=CC=C1)C(C)C)C)F WRNDWMFZGGVFFX-UHFFFAOYSA-N 0.000 claims 1
- WFJCLOPTFHBFOL-UHFFFAOYSA-N 3-[3-[[3-(difluoromethoxy)-5-methylpyridin-2-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]sulfonylpropanoic acid Chemical compound FC(OC=1C(=NC=C(C=1)C)NC(=O)C1(CN(C1)S(=O)(=O)CCC(=O)O)C1=C(C=CC=C1)C(C)C)F WFJCLOPTFHBFOL-UHFFFAOYSA-N 0.000 claims 1
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- IYOCECIXAKXRRN-UHFFFAOYSA-N 3-[4-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-4-(2-propan-2-ylphenyl)piperidin-1-yl]sulfonylpropanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CCN(CC1)S(=O)(=O)CCC(=O)O)C1=C(C=CC=C1)C(C)C)C)F IYOCECIXAKXRRN-UHFFFAOYSA-N 0.000 claims 1
- IRCSPSRANJIHMN-UHFFFAOYSA-N 3-[[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidine-1-carbonyl]amino]-2,2-dimethylpropanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(=O)NCC(C(=O)O)(C)C)C1=C(C=CC=C1)C(C)C)C)F IRCSPSRANJIHMN-UHFFFAOYSA-N 0.000 claims 1
- FSOJSIJQWXDNMA-UHFFFAOYSA-N 3-[[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidine-1-carbonyl]amino]-3-methylbutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(=O)NC(CC(=O)O)(C)C)C1=C(C=CC=C1)C(C)C)C)F FSOJSIJQWXDNMA-UHFFFAOYSA-N 0.000 claims 1
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- CRIPSKBJJSGWPY-UHFFFAOYSA-N 4-N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-4-(2-propan-2-ylphenyl)piperidine-1,4-dicarboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CCN(CC1)C(=O)N)C1=C(C=CC=C1)C(C)C)C)F CRIPSKBJJSGWPY-UHFFFAOYSA-N 0.000 claims 1
- GUXCLVKPVVSFPQ-UHFFFAOYSA-N 4-[2-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2-oxoethyl]oxane-4-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CC1(CCOCC1)C(=O)O)=O)C1=C(C=CC=C1)C(C)C)C)F GUXCLVKPVVSFPQ-UHFFFAOYSA-N 0.000 claims 1
- FGVYAZFIJVDHKK-UHFFFAOYSA-N 4-[3-(2-cyclobutylphenyl)-3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]azetidin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C1(CCC1)C1=C(C=CC=C1)C1(CN(C1)C(CC(C(=O)O)(C)C)=O)C(NC=1C(=NC(=CC=1)C)OC(F)F)=O FGVYAZFIJVDHKK-UHFFFAOYSA-N 0.000 claims 1
- TWKZCGJEIUBVGJ-UHFFFAOYSA-N 4-[3-(2-cyclohexylphenyl)-3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]azetidin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C1(CCCCC1)C1=C(C=CC=C1)C1(CN(C1)C(CC(C(=O)O)(C)C)=O)C(NC=1C(=NC(=CC=1)C)OC(F)F)=O TWKZCGJEIUBVGJ-UHFFFAOYSA-N 0.000 claims 1
- OFHDYZKNWGJFED-UHFFFAOYSA-N 4-[3-(2-cyclopentylphenyl)-3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]azetidin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C1(CCCC1)C1=C(C=CC=C1)C1(CN(C1)C(CC(C(=O)O)(C)C)=O)C(NC=1C(=NC(=CC=1)C)OC(F)F)=O OFHDYZKNWGJFED-UHFFFAOYSA-N 0.000 claims 1
- AMHDMEAHCATJEV-UHFFFAOYSA-N 4-[3-[(5-bromo-3-methoxypyridin-2-yl)carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound BrC=1C=C(C(=NC=1)NC(=O)C1(CN(C1)C(CC(C(=O)O)(C)C)=O)C1=C(C=CC=C1)C(C)C)OC AMHDMEAHCATJEV-UHFFFAOYSA-N 0.000 claims 1
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- CFCSRXFQTDWLTD-UHFFFAOYSA-N 4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-3,3-difluoro-4-oxobutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(C(CC(=O)O)(F)F)=O)C1=C(C=CC=C1)C(C)C)C)F CFCSRXFQTDWLTD-UHFFFAOYSA-N 0.000 claims 1
- XGBDNSNFWQOSFG-UHFFFAOYSA-N 4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-3,3-dimethyl-4-oxobutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(C(CC(=O)O)(C)C)=O)C1=C(C=CC=C1)C(C)C)C)F XGBDNSNFWQOSFG-UHFFFAOYSA-N 0.000 claims 1
- DCCQAGVZVURXKU-UHFFFAOYSA-N 4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-3,3-dimethylbutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)CC(CC(=O)O)(C)C)C1=C(C=CC=C1)C(C)C)C)F DCCQAGVZVURXKU-UHFFFAOYSA-N 0.000 claims 1
- UGMWBJYMPDMFFQ-UHFFFAOYSA-N 4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-4-oxobutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CCC(=O)O)=O)C1=C(C=CC=C1)C(C)C)C)F UGMWBJYMPDMFFQ-UHFFFAOYSA-N 0.000 claims 1
- MKQJLECRRRPXQB-UHFFFAOYSA-N 4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]butanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)CCCC(=O)O)C1=C(C=CC=C1)C(C)C)C)F MKQJLECRRRPXQB-UHFFFAOYSA-N 0.000 claims 1
- CXGNGQGHYWPHRY-UHFFFAOYSA-N 4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]sulfonylbutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)S(=O)(=O)CCCC(=O)O)C1=C(C=CC=C1)C(C)C)C)F CXGNGQGHYWPHRY-UHFFFAOYSA-N 0.000 claims 1
- BDXVIMZFBIPPMN-UHFFFAOYSA-N 4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propylphenyl)azetidin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CC(C(=O)O)(C)C)=O)C1=C(C=CC=C1)CCC)C)F BDXVIMZFBIPPMN-UHFFFAOYSA-N 0.000 claims 1
- ZGIACKXVMGCXOL-UHFFFAOYSA-N 4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(3-propan-2-ylpyridin-2-yl)azetidin-1-yl]-4-oxobutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CCC(=O)O)=O)C1=NC=CC=C1C(C)C)C)F ZGIACKXVMGCXOL-UHFFFAOYSA-N 0.000 claims 1
- GOEPNHHABWYQGP-UHFFFAOYSA-N 4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(5-fluoro-2-propan-2-ylphenyl)azetidin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CC(C(=O)O)(C)C)=O)C1=C(C=CC(=C1)F)C(C)C)C)F GOEPNHHABWYQGP-UHFFFAOYSA-N 0.000 claims 1
- PYDZWSDQMKTKPJ-UHFFFAOYSA-N 4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(5-methyl-2-propan-2-ylphenyl)azetidin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CC(C(=O)O)(C)C)=O)C1=C(C=CC(=C1)C)C(C)C)C)F PYDZWSDQMKTKPJ-UHFFFAOYSA-N 0.000 claims 1
- YZUAESDAMCLNLJ-UHFFFAOYSA-N 4-[3-[[3-(difluoromethoxy)-5-methylpyridin-2-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound FC(OC=1C(=NC=C(C=1)C)NC(=O)C1(CN(C1)C(CC(C(=O)O)(C)C)=O)C1=C(C=CC=C1)C(C)C)F YZUAESDAMCLNLJ-UHFFFAOYSA-N 0.000 claims 1
- SWYVDORIBDEZRV-UHFFFAOYSA-N 4-[3-[[5-bromo-3-(difluoromethoxy)pyridin-2-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2,2-dimethylbutanoic acid Chemical compound BrC=1C=C(C(=NC=1)NC(=O)C1(CN(C1)CCC(C(=O)O)(C)C)C1=C(C=CC=C1)C(C)C)OC(F)F SWYVDORIBDEZRV-UHFFFAOYSA-N 0.000 claims 1
- AHVXUSDAWIMMMW-UHFFFAOYSA-N 4-[3-[[5-chloro-3-(difluoromethoxy)pyridin-2-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound ClC=1C=C(C(=NC=1)NC(=O)C1(CN(C1)C(CC(C(=O)O)(C)C)=O)C1=C(C=CC=C1)C(C)C)OC(F)F AHVXUSDAWIMMMW-UHFFFAOYSA-N 0.000 claims 1
- RXYCIBABEYRZLW-UHFFFAOYSA-N 4-[3-[[5-chloro-3-(difluoromethoxy)pyridin-2-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2,2-dimethylbutanoic acid Chemical compound ClC=1C=C(C(=NC=1)NC(=O)C1(CN(C1)CCC(C(=O)O)(C)C)C1=C(C=CC=C1)C(C)C)OC(F)F RXYCIBABEYRZLW-UHFFFAOYSA-N 0.000 claims 1
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- VSYGOEMEQVUEQX-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-(2-methylpyrimidin-4-yl)-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C1=NC(=NC=C1)C)C1=C(C=CC=C1)C(C)C)C)F VSYGOEMEQVUEQX-UHFFFAOYSA-N 0.000 claims 1
- WGELXXQARBBGAV-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-(3-fluoro-6-methylpyridin-2-yl)-3-(3-propan-2-ylpyridin-2-yl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C1=NC(=CC=C1F)C)C1=NC=CC=C1C(C)C)C)F WGELXXQARBBGAV-UHFFFAOYSA-N 0.000 claims 1
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- VWEMBXFRVXTJFB-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-(3-hydroxy-3-methylbutyl)-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)CCC(C)(C)O)C1=C(C=CC=C1)C(C)C)C)F VWEMBXFRVXTJFB-UHFFFAOYSA-N 0.000 claims 1
- UEVAXSIFXPNUBY-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-(3-hydroxypropyl)-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)CCCO)C1=C(C=CC=C1)C(C)C)C)F UEVAXSIFXPNUBY-UHFFFAOYSA-N 0.000 claims 1
- LQYBZBRQYAYTSP-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-(4-fluoropyridin-2-yl)-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C1=NC=CC(=C1)F)C1=C(C=CC=C1)C(C)C)C)F LQYBZBRQYAYTSP-UHFFFAOYSA-N 0.000 claims 1
- RPYWSPGHHAMCJJ-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-(4-hydroxy-4-methylpentyl)-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)CCCC(C)(C)O)C1=C(C=CC=C1)C(C)C)C)F RPYWSPGHHAMCJJ-UHFFFAOYSA-N 0.000 claims 1
- RBPNNQWETUPGRP-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-(4-oxo-1,3-oxazol-2-yl)-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C=1OCC(N=1)=O)C1=C(C=CC=C1)C(C)C)C)F RBPNNQWETUPGRP-UHFFFAOYSA-N 0.000 claims 1
- ITIUDDVCONPFBD-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-(5-fluoro-2-methylpyrimidin-4-yl)-3-(3-propan-2-ylpyridin-2-yl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C1=NC(=NC=C1F)C)C1=NC=CC=C1C(C)C)C)F ITIUDDVCONPFBD-UHFFFAOYSA-N 0.000 claims 1
- GVWRNOJIXARVCR-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-(5-fluoropyrimidin-2-yl)-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C1=NC=C(C=N1)F)C1=C(C=CC=C1)C(C)C)C)F GVWRNOJIXARVCR-UHFFFAOYSA-N 0.000 claims 1
- PHFYUMAKEQMIAX-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-(5-fluoropyrimidin-4-yl)-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C1=NC=NC=C1F)C1=C(C=CC=C1)C(C)C)C)F PHFYUMAKEQMIAX-UHFFFAOYSA-N 0.000 claims 1
- HMTVDHKZZVKHCM-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-(5-oxo-4H-1,2,4-oxadiazol-3-yl)-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C1=NOC(=N1)O)C1=C(C=CC=C1)C(C)C)C)F HMTVDHKZZVKHCM-UHFFFAOYSA-N 0.000 claims 1
- UQDYKYRMZPSTEK-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-(methylsulfamoyl)-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)S(NC)(=O)=O)C1=C(C=CC=C1)C(C)C)C)F UQDYKYRMZPSTEK-UHFFFAOYSA-N 0.000 claims 1
- SBXWENLNJFRLOO-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-(oxetan-3-yl)-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C1COC1)C1=C(C=CC=C1)C(C)C)C)F SBXWENLNJFRLOO-UHFFFAOYSA-N 0.000 claims 1
- BYPQSCXMSKGEAU-MRXNPFEDSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[(2R)-2,3-dihydroxypropyl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C[C@H](CO)O)C1=C(C=CC=C1)C(C)C)C)F BYPQSCXMSKGEAU-MRXNPFEDSA-N 0.000 claims 1
- OOPCQDRNPFCRRB-GOSISDBHSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[(2R)-2,3-dihydroxypropyl]-4-(2-propan-2-ylphenyl)piperidine-4-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CCN(CC1)C[C@H](CO)O)C1=C(C=CC=C1)C(C)C)C)F OOPCQDRNPFCRRB-GOSISDBHSA-N 0.000 claims 1
- KBSCSHFNUUPBJV-KRWDZBQOSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[(2S)-2-hydroxy-3-[(2-hydroxyacetyl)amino]propyl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C[C@H](CNC(CO)=O)O)C1=C(C=CC=C1)C(C)C)C)F KBSCSHFNUUPBJV-KRWDZBQOSA-N 0.000 claims 1
- OELXGYAIRHWTHQ-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[2-(1-hydroxycyclopropyl)ethyl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)CCC1(CC1)O)C1=C(C=CC=C1)C(C)C)C)F OELXGYAIRHWTHQ-UHFFFAOYSA-N 0.000 claims 1
- PMNFCSAPCWOOEH-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[2-(2-hydroxyethylamino)acetyl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CNCCO)=O)C1=C(C=CC=C1)C(C)C)C)F PMNFCSAPCWOOEH-UHFFFAOYSA-N 0.000 claims 1
- WPVJAQJHZKPJTE-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[2-(2-hydroxyethylamino)acetyl]-4-(2-propan-2-ylphenyl)piperidine-4-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CCN(CC1)C(CNCCO)=O)C1=C(C=CC=C1)C(C)C)C)F WPVJAQJHZKPJTE-UHFFFAOYSA-N 0.000 claims 1
- OKBMSRJFSJNMCD-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[2-(2-methoxyethylamino)acetyl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CNCCOC)=O)C1=C(C=CC=C1)C(C)C)C)F OKBMSRJFSJNMCD-UHFFFAOYSA-N 0.000 claims 1
- KEXGXVRZAXMSTI-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[2-(2-methoxyethylamino)acetyl]-4-(2-propan-2-ylphenyl)piperidine-4-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CCN(CC1)C(CNCCOC)=O)C1=C(C=CC=C1)C(C)C)C)F KEXGXVRZAXMSTI-UHFFFAOYSA-N 0.000 claims 1
- LLIMYKSVEODPTG-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[2-(3-hydroxyoxetan-3-yl)acetyl]-4-(2-propan-2-ylphenyl)piperidine-4-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CCN(CC1)C(CC1(COC1)O)=O)C1=C(C=CC=C1)C(C)C)C)F LLIMYKSVEODPTG-UHFFFAOYSA-N 0.000 claims 1
- JWPGBTSVEOJNEX-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[2-(methanesulfonamido)acetyl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CNS(=O)(=O)C)=O)C1=C(C=CC=C1)C(C)C)C)F JWPGBTSVEOJNEX-UHFFFAOYSA-N 0.000 claims 1
- VQPKJQOIRMEYME-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[2-(methanesulfonamido)ethyl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)CCNS(=O)(=O)C)C1=C(C=CC=C1)C(C)C)C)F VQPKJQOIRMEYME-UHFFFAOYSA-N 0.000 claims 1
- FBELHHJSHUINBZ-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[2-(methylsulfamoyl)acetyl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CS(NC)(=O)=O)=O)C1=C(C=CC=C1)C(C)C)C)F FBELHHJSHUINBZ-UHFFFAOYSA-N 0.000 claims 1
- OIEXTCVFCYGTJI-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[2-[methyl(sulfamoyl)amino]acetyl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CN(S(N)(=O)=O)C)=O)C1=C(C=CC=C1)C(C)C)C)F OIEXTCVFCYGTJI-UHFFFAOYSA-N 0.000 claims 1
- DSSJEHKLVYSAQX-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-1-[3-(hydroxyamino)-3-oxopropyl]sulfonyl-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)S(=O)(=O)CCC(=O)NO)C1=C(C=CC=C1)C(C)C)C)F DSSJEHKLVYSAQX-UHFFFAOYSA-N 0.000 claims 1
- LSRHVVDBWVAXRD-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-fluoro-6-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CNC1)C1=C(C=CC=C1C(C)C)F)C)F LSRHVVDBWVAXRD-UHFFFAOYSA-N 0.000 claims 1
- DHIZRRYUSGBFHY-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)-1-(3-sulfamoylpropanoyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CCS(N)(=O)=O)=O)C1=C(C=CC=C1)C(C)C)C)F DHIZRRYUSGBFHY-UHFFFAOYSA-N 0.000 claims 1
- YNTGJSDPHMBXLM-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)-1-(5,5,5-trifluoro-4-hydroxypentanoyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CCC(C(F)(F)F)O)=O)C1=C(C=CC=C1)C(C)C)C)F YNTGJSDPHMBXLM-UHFFFAOYSA-N 0.000 claims 1
- HBJPDVLNBCLSEE-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)-1-(5,5,5-trifluoro-4-oxopentanoyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CCC(C(F)(F)F)=O)=O)C1=C(C=CC=C1)C(C)C)C)F HBJPDVLNBCLSEE-UHFFFAOYSA-N 0.000 claims 1
- LMPPWSKVZUXDOM-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)-1-[2-(2H-tetrazol-5-yl)ethyl]azetidine-3-carboxamide Chemical compound N1N=NN=C1CCN1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C LMPPWSKVZUXDOM-UHFFFAOYSA-N 0.000 claims 1
- USBGVXDWRLFONC-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)-1-[2-(sulfamoylamino)acetyl]azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CNS(N)(=O)=O)=O)C1=C(C=CC=C1)C(C)C)C)F USBGVXDWRLFONC-UHFFFAOYSA-N 0.000 claims 1
- VSWWTLMTEHCBQI-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)-1-[2-(sulfamoylamino)ethyl]azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)CCNS(N)(=O)=O)C1=C(C=CC=C1)C(C)C)C)F VSWWTLMTEHCBQI-UHFFFAOYSA-N 0.000 claims 1
- GWHBDJYPVDEUOD-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)-1-[2-(triazol-2-yl)acetyl]azetidine-3-carboxamide Chemical compound N=1N(N=CC=1)CC(=O)N1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C GWHBDJYPVDEUOD-UHFFFAOYSA-N 0.000 claims 1
- MGDKPMAQFAFWJY-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)-1-[3-(2H-tetrazol-5-yl)propyl]azetidine-3-carboxamide Chemical compound N1N=NN=C1CCCN1CC(C1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C MGDKPMAQFAFWJY-UHFFFAOYSA-N 0.000 claims 1
- YXRNQUBUJDLVPK-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)-1-sulfamoylazetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)S(N)(=O)=O)C1=C(C=CC=C1)C(C)C)C)F YXRNQUBUJDLVPK-UHFFFAOYSA-N 0.000 claims 1
- FPSBJDJNQIVNIK-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CNC1)C1=C(C=CC=C1)C(C)C)C)F FPSBJDJNQIVNIK-UHFFFAOYSA-N 0.000 claims 1
- MYEALICAAXZMMJ-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(2-propan-2-ylphenyl)pyrrolidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CNCC1)C1=C(C=CC=C1)C(C)C)C)F MYEALICAAXZMMJ-UHFFFAOYSA-N 0.000 claims 1
- RTCRWFQZKIDYBP-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(3-propan-2-ylpyrazin-2-yl)-1-sulfamoylazetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)S(N)(=O)=O)C1=NC=CN=C1C(C)C)C)F RTCRWFQZKIDYBP-UHFFFAOYSA-N 0.000 claims 1
- FFLSEKHALLAYTP-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(3-propan-2-ylpyrazin-2-yl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CNC1)C1=NC=CN=C1C(C)C)C)F FFLSEKHALLAYTP-UHFFFAOYSA-N 0.000 claims 1
- ZBAKAINKYSEOQF-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(3-propan-2-ylpyridin-2-yl)-1-sulfamoylazetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)S(N)(=O)=O)C1=NC=CC=C1C(C)C)C)F ZBAKAINKYSEOQF-UHFFFAOYSA-N 0.000 claims 1
- DYKVTQOWNNBYQE-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(3-propan-2-ylpyridin-2-yl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CNC1)C1=NC=CC=C1C(C)C)C)F DYKVTQOWNNBYQE-UHFFFAOYSA-N 0.000 claims 1
- KMBUHIQQJQJEKA-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(3-propan-2-ylpyridin-4-yl)-1-sulfamoylazetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)S(N)(=O)=O)C1=C(C=NC=C1)C(C)C)C)F KMBUHIQQJQJEKA-UHFFFAOYSA-N 0.000 claims 1
- OBXBXRWDKQKPIL-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-3-(3-propan-2-ylpyridin-4-yl)azetidine-3-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CNC1)C1=C(C=NC=C1)C(C)C)C)F OBXBXRWDKQKPIL-UHFFFAOYSA-N 0.000 claims 1
- FQUKQIQHOAGFLH-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-4-(2-propan-2-ylphenyl)-1-(5,5,5-trifluoro-4-oxopentanoyl)piperidine-4-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CCN(CC1)C(CCC(C(F)(F)F)=O)=O)C1=C(C=CC=C1)C(C)C)C)F FQUKQIQHOAGFLH-UHFFFAOYSA-N 0.000 claims 1
- CFWDZASGKCUTTG-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-4-(2-propan-2-ylphenyl)-1-[2-(tetrazol-1-yl)acetyl]piperidine-4-carboxamide Chemical compound N1(N=NN=C1)CC(=O)N1CCC(CC1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C CFWDZASGKCUTTG-UHFFFAOYSA-N 0.000 claims 1
- ASLJZZRXRASSLU-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-4-(2-propan-2-ylphenyl)-1-[2-(triazol-2-yl)acetyl]piperidine-4-carboxamide Chemical compound N=1N(N=CC=1)CC(=O)N1CCC(CC1)(C(=O)NC=1C(=NC(=CC=1)C)OC(F)F)C1=C(C=CC=C1)C(C)C ASLJZZRXRASSLU-UHFFFAOYSA-N 0.000 claims 1
- YJKVGWIKVLBGBL-UHFFFAOYSA-N N-[2-(difluoromethoxy)-6-methylpyridin-3-yl]-4-(2-propan-2-ylphenyl)piperidine-4-carboxamide Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CCNCC1)C1=C(C=CC=C1)C(C)C)C)F YJKVGWIKVLBGBL-UHFFFAOYSA-N 0.000 claims 1
- GSOZOIFXBBVAFB-UHFFFAOYSA-N N-[2-(difluoromethoxy)pyridin-3-yl]-1-(5-fluoropyrimidin-4-yl)-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC1=NC=CC=C1NC(=O)C1(CN(C1)C1=NC=NC=C1F)C1=C(C=CC=C1)C(C)C)F GSOZOIFXBBVAFB-UHFFFAOYSA-N 0.000 claims 1
- UPGRYXFUZOLSLV-UHFFFAOYSA-N N-[2-(difluoromethoxy)pyridin-3-yl]-3-(2-propan-2-ylphenyl)-1-sulfamoylazetidine-3-carboxamide Chemical compound FC(OC1=NC=CC=C1NC(=O)C1(CN(C1)S(N)(=O)=O)C1=C(C=CC=C1)C(C)C)F UPGRYXFUZOLSLV-UHFFFAOYSA-N 0.000 claims 1
- ZAHILQBAPANEDO-UHFFFAOYSA-N N-[3-(difluoromethoxy)-5-methylpyridin-2-yl]-1-(4-oxo-1,3-oxazol-2-yl)-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC=1C(=NC=C(C=1)C)NC(=O)C1(CN(C1)C=1OCC(N=1)=O)C1=C(C=CC=C1)C(C)C)F ZAHILQBAPANEDO-UHFFFAOYSA-N 0.000 claims 1
- ZELZMZDZQZKANU-UHFFFAOYSA-N N-[3-(difluoromethoxy)-5-methylpyridin-2-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound FC(OC=1C(=NC=C(C=1)C)NC(=O)C1(CNC1)C1=C(C=CC=C1)C(C)C)F ZELZMZDZQZKANU-UHFFFAOYSA-N 0.000 claims 1
- BXDZOYLPNAIDOC-UHFFFAOYSA-N N-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-[2-[2-[2-[2-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethoxy]ethoxy]ethoxy]ethylamino]-2-oxoethyl]piperidine-4-carboxamide Chemical compound CC(C)(C)c1cnc(CSc2cnc(NC(=O)C3CCN(CC(=O)NCCOCCOCCOCCNc4cccc5C(=O)N(C6CCC(=O)NC6=O)C(=O)c45)CC3)s2)o1 BXDZOYLPNAIDOC-UHFFFAOYSA-N 0.000 claims 1
- SWODPLDGWOVKAK-UHFFFAOYSA-N N-[5-bromo-3-(difluoromethoxy)pyridin-2-yl]-3-(2-propan-2-ylphenyl)-1-sulfamoylazetidine-3-carboxamide Chemical compound BrC=1C=C(C(=NC=1)NC(=O)C1(CN(C1)S(N)(=O)=O)C1=C(C=CC=C1)C(C)C)OC(F)F SWODPLDGWOVKAK-UHFFFAOYSA-N 0.000 claims 1
- DLCSINRSOWLSSU-UHFFFAOYSA-N N-[5-bromo-3-(difluoromethoxy)pyridin-2-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound BrC=1C=C(C(=NC=1)NC(=O)C1(CNC1)C1=C(C=CC=C1)C(C)C)OC(F)F DLCSINRSOWLSSU-UHFFFAOYSA-N 0.000 claims 1
- NZBXNHLEPHDEBT-UHFFFAOYSA-N N-[5-chloro-3-(difluoromethoxy)pyridin-2-yl]-3-(2-cyclopentylphenyl)-1-sulfamoylazetidine-3-carboxamide Chemical compound ClC=1C=C(C(=NC=1)NC(=O)C1(CN(C1)S(N)(=O)=O)C1=C(C=CC=C1)C1CCCC1)OC(F)F NZBXNHLEPHDEBT-UHFFFAOYSA-N 0.000 claims 1
- MUQCHPCYEONRSA-UHFFFAOYSA-N N-[5-chloro-3-(difluoromethoxy)pyridin-2-yl]-3-(2-cyclopentylphenyl)azetidine-3-carboxamide Chemical compound ClC=1C=C(C(=NC=1)NC(=O)C1(CNC1)C1=C(C=CC=C1)C1CCCC1)OC(F)F MUQCHPCYEONRSA-UHFFFAOYSA-N 0.000 claims 1
- SUDIFGBBAUYSBV-UHFFFAOYSA-N N-[5-chloro-3-(difluoromethoxy)pyridin-2-yl]-3-(2-propan-2-ylphenyl)-1-sulfamoylazetidine-3-carboxamide Chemical compound ClC=1C=C(C(=NC=1)NC(=O)C1(CN(C1)S(N)(=O)=O)C1=C(C=CC=C1)C(C)C)OC(F)F SUDIFGBBAUYSBV-UHFFFAOYSA-N 0.000 claims 1
- RGWOJUROYGSDJG-UHFFFAOYSA-N N-[5-chloro-3-(difluoromethoxy)pyridin-2-yl]-3-(2-propan-2-ylphenyl)azetidine-3-carboxamide Chemical compound ClC=1C=C(C(=NC=1)NC(=O)C1(CNC1)C1=C(C=CC=C1)C(C)C)OC(F)F RGWOJUROYGSDJG-UHFFFAOYSA-N 0.000 claims 1
- URTMKOUANQQMHE-UHFFFAOYSA-N N-[5-chloro-3-(difluoromethoxy)pyridin-2-yl]-3-(3-propan-2-ylpyridin-2-yl)-1-sulfamoylazetidine-3-carboxamide Chemical compound ClC=1C=C(C(=NC=1)NC(=O)C1(CN(C1)S(N)(=O)=O)C1=NC=CC=C1C(C)C)OC(F)F URTMKOUANQQMHE-UHFFFAOYSA-N 0.000 claims 1
- PEHNQLALDCRTNU-UHFFFAOYSA-N N-[5-chloro-3-(difluoromethoxy)pyridin-2-yl]-3-(3-propan-2-ylpyridin-2-yl)azetidine-3-carboxamide Chemical compound ClC=1C=C(C(=NC=1)NC(=O)C1(CNC1)C1=NC=CC=C1C(C)C)OC(F)F PEHNQLALDCRTNU-UHFFFAOYSA-N 0.000 claims 1
- 206010029216 Nervousness Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- IFGZYIPCYZHOSG-UHFFFAOYSA-N benzyl 3-[3-[[3-(difluoromethoxy)-5-methylpyridin-2-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]sulfonylpropanoate Chemical compound FC(OC=1C(=NC=C(C=1)C)NC(=O)C1(CN(C1)S(=O)(=O)CCC(=O)OCC1=CC=CC=C1)C1=C(C=CC=C1)C(C)C)F IFGZYIPCYZHOSG-UHFFFAOYSA-N 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- QCLJRNSXRYDTRQ-UHFFFAOYSA-N methyl 2-[[2-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2-oxoethyl]amino]acetate Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CNCC(=O)OC)=O)C1=C(C=CC=C1)C(C)C)C)F QCLJRNSXRYDTRQ-UHFFFAOYSA-N 0.000 claims 1
- BEJGTJRHYQCRTN-UHFFFAOYSA-N methyl 4-[3-[[5-bromo-3-(difluoromethoxy)pyridin-2-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2,2-dimethyl-4-oxobutanoate Chemical compound BrC=1C=C(C(=NC=1)NC(=O)C1(CN(C1)C(CC(C(=O)OC)(C)C)=O)C1=C(C=CC=C1)C(C)C)OC(F)F BEJGTJRHYQCRTN-UHFFFAOYSA-N 0.000 claims 1
- VTVFQEHGXSMPGF-UHFFFAOYSA-N methyl 4-[3-[[5-chloro-3-(difluoromethoxy)pyridin-2-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2,2-dimethylbutanoate Chemical compound ClC=1C=C(C(=NC=1)NC(=O)C1(CN(C1)CCC(C(=O)OC)(C)C)C1=C(C=CC=C1)C(C)C)OC(F)F VTVFQEHGXSMPGF-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 210000000653 nervous system Anatomy 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Classifications
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP2018065016 | 2018-06-07 | ||
| PCT/EP2019/064690 WO2019234115A1 (en) | 2018-06-07 | 2019-06-05 | Alkoxy-substituted pyridinyl derivatives as lpa1 receptor antagonists and their use in the treatment of fibrosis |
| EP19731163.2A EP3802517B1 (en) | 2018-06-07 | 2019-06-05 | Alkoxy-substituted pyridinyl derivatives as lpa1 receptor antagonists and their use in the treatment of fibrosis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20230243T1 true HRP20230243T1 (hr) | 2023-04-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20230243TT HRP20230243T1 (hr) | 2018-06-07 | 2019-06-05 | Alkoksi supstituirani derivati piridinila kao antagonisti receptora lpa1 i njihova uporaba u liječenju fibroze |
Country Status (22)
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|---|---|
| US (1) | US12344597B2 (https=) |
| EP (1) | EP3802517B1 (https=) |
| JP (1) | JP7386183B2 (https=) |
| KR (1) | KR102826034B1 (https=) |
| CN (1) | CN112236424B (https=) |
| AU (1) | AU2019282274A1 (https=) |
| BR (1) | BR112020024879A2 (https=) |
| CA (1) | CA3102683A1 (https=) |
| DK (1) | DK3802517T3 (https=) |
| EA (1) | EA202092955A1 (https=) |
| ES (1) | ES2940695T3 (https=) |
| FI (1) | FI3802517T3 (https=) |
| HR (1) | HRP20230243T1 (https=) |
| HU (1) | HUE061559T2 (https=) |
| LT (1) | LT3802517T (https=) |
| MX (1) | MX2020013291A (https=) |
| PL (1) | PL3802517T3 (https=) |
| PT (1) | PT3802517T (https=) |
| RS (1) | RS63990B1 (https=) |
| SI (1) | SI3802517T1 (https=) |
| TW (1) | TW202016090A (https=) |
| WO (1) | WO2019234115A1 (https=) |
Families Citing this family (4)
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| AR119162A1 (es) * | 2019-06-18 | 2021-12-01 | Idorsia Pharmaceuticals Ltd | Derivados de piridin-3-ilo |
| JP7665619B2 (ja) | 2019-12-04 | 2025-04-21 | イドルシア・ファーマシューティカルズ・リミテッド | 線維性疾患の治療に使用するためのアゼチジンｌｐａ１受容体アンタゴニストのピルフェニドン及び／又はニンテダニブとの合剤 |
| FI20225388A1 (en) | 2022-05-05 | 2023-11-06 | Equinorm Ltd | New heterocyclic compounds, preparation methods and their uses |
| WO2025169931A1 (ja) * | 2024-02-05 | 2025-08-14 | Ｕｂｅ株式会社 | カルボキサミド化合物 |
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| NL130088C (https=) | 1960-03-14 | |||
| GB9420763D0 (en) | 1994-10-14 | 1994-11-30 | Glaxo Inc | Acetamide derivatives |
| GB9919776D0 (en) | 1998-08-31 | 1999-10-27 | Zeneca Ltd | Compoujnds |
| AU7961300A (en) | 1999-10-29 | 2001-05-14 | Yamanouchi Pharmaceutical Co., Ltd. | Kainic acid neurocytotoxicity inhibitors |
| AU2001262185A1 (en) | 2000-04-10 | 2001-10-23 | Novartis Ag | Substituted (hetero)aryl carboxamide derivatives as microsomal triglyceride transfer protein (mtp) and apolipoprotein b (apo b) secretion |
| WO2002062389A1 (en) | 2001-02-08 | 2002-08-15 | Ono Pharmaceutical Co., Ltd. | Remedies for urinary diseases comprising lpa receptor controlling agents |
| TW200403058A (en) * | 2002-04-19 | 2004-03-01 | Bristol Myers Squibb Co | Heterocyclo inhibitors of potassium channel function |
| US7435824B2 (en) | 2002-04-19 | 2008-10-14 | Bristol-Myers Squibb Company | Prodrugs of potassium channel inhibitors |
| TW200505902A (en) | 2003-03-20 | 2005-02-16 | Schering Corp | Cannabinoid receptor ligands |
| WO2004110350A2 (en) | 2003-05-14 | 2004-12-23 | Torreypines Therapeutics, Inc. | Compouds and uses thereof in modulating amyloid beta |
| WO2005023761A2 (en) | 2003-09-11 | 2005-03-17 | Kemia, Inc. | Cytokine inhibitors |
| JPWO2005037269A1 (ja) | 2003-10-21 | 2006-12-28 | 住友製薬株式会社 | 新規ピペリジン誘導体 |
| EP1687296A1 (en) | 2003-11-18 | 2006-08-09 | Warner-Lambert Company LLC | Antibacterial aminoquinazolidinedione derivatives |
| WO2006091862A2 (en) | 2005-02-24 | 2006-08-31 | Kemia, Inc. | Cytokine inhibitors and their use in therapy |
| CN101198590B (zh) | 2005-08-24 | 2012-05-09 | 卫材R&D管理有限公司 | 吡啶衍生物及嘧啶衍生物（3） |
| WO2007058990A2 (en) | 2005-11-14 | 2007-05-24 | Kemia, Inc. | Therapy using cytokine inhibitors |
| CA2691214A1 (en) | 2006-06-09 | 2007-12-21 | Kemia, Inc. | Therapy using cytokine inhibitors |
| JP5164510B2 (ja) | 2006-10-06 | 2013-03-21 | 日本曹達株式会社 | 含窒素複素環化合物および有害生物防除剤 |
| WO2008115281A2 (en) | 2006-10-16 | 2008-09-25 | Myriad Genetics, Inc. | Compounds for treating viral infections |
| EP2212322B1 (en) | 2007-10-18 | 2012-04-04 | Merck Sharp & Dohme Corp. | Quinolizidinone m1 receptor positive allosteric modulators |
| AU2009239500B2 (en) | 2008-04-21 | 2014-01-30 | Lexicon Pharmaceuticals, Inc. | LIMK2 inhibitors, compositions comprising them, and methods of their use |
| PT2303270T (pt) | 2008-05-05 | 2017-08-25 | Sanofi Sa | Derivados fundidos do ácido ciclopentanocarboxílico substituídos por acilamino e sua utilização como produtos farmacêuticos |
| UY32072A (es) | 2008-08-26 | 2010-03-26 | Boehringer Ingelheim Int | Tienopirimidinas para composiciones farmacéuticas |
| KR101678255B1 (ko) * | 2009-09-25 | 2016-11-21 | 아스텔라스세이야쿠 가부시키가이샤 | 치환 아미드 화합물 |
| ES2682303T3 (es) | 2010-08-05 | 2018-09-19 | Zoetis Services Llc | Derivados de isoxazolina como agentes antiparasitarios |
| TW201305178A (zh) | 2010-10-29 | 2013-02-01 | Glenmark Pharmaceuticals Sa | 作為ｍＰＧＥＳ－１抑制物的三環化合物 |
| DK2648726T3 (da) | 2010-12-07 | 2018-07-16 | Amira Pharmaceuticals Inc | Polycyklisk lpa1-antagonist og anvendelser deraf |
| JP6097998B2 (ja) | 2010-12-16 | 2017-03-22 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ロイコトリエン生成のビアリールアミドインヒビター |
| PH12013501831B1 (en) | 2011-03-10 | 2019-06-14 | Zoetis Services Llc | Spirocyclic isoxazoline derivatives as antiparasitic agents |
| CA2859965A1 (en) | 2011-12-21 | 2013-06-27 | Ardelyx, Inc. | Non-systemic tgr5 agonists |
| WO2014079805A1 (en) | 2012-11-23 | 2014-05-30 | Boehringer Ingelheim International Gmbh | Pyrazole compounds for treating hairloss |
| EP2970200A1 (en) * | 2013-03-13 | 2016-01-20 | Abbvie Inc. | Pyridine cdk9 kinase inhibitors |
| AR108185A1 (es) | 2016-04-06 | 2018-07-25 | Abbvie Inc | Amidas terciarias y método para su uso |
| AR119162A1 (es) | 2019-06-18 | 2021-12-01 | Idorsia Pharmaceuticals Ltd | Derivados de piridin-3-ilo |
| JP7665619B2 (ja) | 2019-12-04 | 2025-04-21 | イドルシア・ファーマシューティカルズ・リミテッド | 線維性疾患の治療に使用するためのアゼチジンｌｐａ１受容体アンタゴニストのピルフェニドン及び／又はニンテダニブとの合剤 |
-
2019
- 2019-06-05 PT PT197311632T patent/PT3802517T/pt unknown
- 2019-06-05 FI FIEP19731163.2T patent/FI3802517T3/fi active
- 2019-06-05 CN CN201980036967.6A patent/CN112236424B/zh active Active
- 2019-06-05 DK DK19731163.2T patent/DK3802517T3/da active
- 2019-06-05 CA CA3102683A patent/CA3102683A1/en active Pending
- 2019-06-05 BR BR112020024879-7A patent/BR112020024879A2/pt not_active IP Right Cessation
- 2019-06-05 PL PL19731163.2T patent/PL3802517T3/pl unknown
- 2019-06-05 ES ES19731163T patent/ES2940695T3/es active Active
- 2019-06-05 EP EP19731163.2A patent/EP3802517B1/en active Active
- 2019-06-05 SI SI201930472T patent/SI3802517T1/sl unknown
- 2019-06-05 LT LTEPPCT/EP2019/064690T patent/LT3802517T/lt unknown
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- 2019-06-05 US US16/972,878 patent/US12344597B2/en active Active
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- 2019-06-05 HU HUE19731163A patent/HUE061559T2/hu unknown
- 2019-06-05 WO PCT/EP2019/064690 patent/WO2019234115A1/en not_active Ceased
- 2019-06-05 HR HRP20230243TT patent/HRP20230243T1/hr unknown
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- 2019-06-05 AU AU2019282274A patent/AU2019282274A1/en not_active Abandoned
- 2019-06-05 RS RS20230148A patent/RS63990B1/sr unknown
- 2019-06-05 TW TW108119605A patent/TW202016090A/zh unknown
- 2019-06-05 MX MX2020013291A patent/MX2020013291A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR102826034B1 (ko) | 2025-06-27 |
| MX2020013291A (es) | 2021-04-29 |
| JP2021527046A (ja) | 2021-10-11 |
| EA202092955A1 (ru) | 2021-04-08 |
| LT3802517T (lt) | 2023-03-10 |
| PL3802517T3 (pl) | 2023-05-22 |
| RS63990B1 (sr) | 2023-03-31 |
| EP3802517A1 (en) | 2021-04-14 |
| ES2940695T3 (es) | 2023-05-10 |
| KR20210018900A (ko) | 2021-02-18 |
| PT3802517T (pt) | 2023-03-20 |
| TW202016090A (zh) | 2020-05-01 |
| SI3802517T1 (sl) | 2023-04-28 |
| BR112020024879A2 (pt) | 2021-03-09 |
| FI3802517T3 (fi) | 2023-03-23 |
| US12344597B2 (en) | 2025-07-01 |
| US20210246116A1 (en) | 2021-08-12 |
| CA3102683A1 (en) | 2019-12-12 |
| CN112236424A (zh) | 2021-01-15 |
| CN112236424B (zh) | 2024-03-15 |
| HUE061559T2 (hu) | 2023-07-28 |
| AU2019282274A1 (en) | 2021-01-28 |
| DK3802517T3 (da) | 2023-03-13 |
| EP3802517B1 (en) | 2022-12-21 |
| JP7386183B2 (ja) | 2023-11-24 |
| WO2019234115A1 (en) | 2019-12-12 |
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