JPWO2019234115A5 - - Google Patents
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- JPWO2019234115A5 JPWO2019234115A5 JP2020567808A JP2020567808A JPWO2019234115A5 JP WO2019234115 A5 JPWO2019234115 A5 JP WO2019234115A5 JP 2020567808 A JP2020567808 A JP 2020567808A JP 2020567808 A JP2020567808 A JP 2020567808A JP WO2019234115 A5 JPWO2019234115 A5 JP WO2019234115A5
- Authority
- JP
- Japan
- Prior art keywords
- alkylene
- difluoromethoxy
- azetidine
- isopropylphenyl
- methylpyridine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 cyclopenta-1-ene-1-yl Chemical group 0.000 claims 197
- 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 35
- 150000002431 hydrogen Chemical class 0.000 claims 27
- 229910052757 nitrogen Inorganic materials 0.000 claims 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 19
- 239000002253 acid Substances 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 17
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 11
- VALZSZJVEFACEZ-UHFFFAOYSA-N azetidine-3-carboxamide Chemical compound NC(=O)C1CNC1 VALZSZJVEFACEZ-UHFFFAOYSA-N 0.000 claims 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 150000002829 nitrogen Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000004761 fibrosis Effects 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-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
- 208000017520 skin disease Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur 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
- 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
- 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
- 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
- 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
- XDCHWGWGTMQYMI-UHFFFAOYSA-N 2-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-1,3-oxazole-4-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C=1OC=C(N=1)C(=O)O)C1=C(C=CC=C1)C(C)C)C)F XDCHWGWGTMQYMI-UHFFFAOYSA-N 0.000 claims 1
- UUMSDYZEJSRCCA-UHFFFAOYSA-N 2-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]pyrimidine-5-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C1=NC=C(C=N1)C(=O)O)C1=C(C=CC=C1)C(C)C)C)F UUMSDYZEJSRCCA-UHFFFAOYSA-N 0.000 claims 1
- MBMSKWLANGVRSY-UHFFFAOYSA-N 2-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]sulfonylacetic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)S(=O)(=O)CC(=O)O)C1=C(C=CC=C1)C(C)C)C)F MBMSKWLANGVRSY-UHFFFAOYSA-N 0.000 claims 1
- 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
- GKPZQBZDQWOLIP-UHFFFAOYSA-N 2-[3-[[3-(difluoromethoxy)-5-methylpyridin-2-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidine-1-carbonyl]oxyacetic acid Chemical compound FC(OC=1C(=NC=C(C=1)C)NC(=O)C1(CN(C1)C(=O)OCC(=O)O)C1=C(C=CC=C1)C(C)C)F GKPZQBZDQWOLIP-UHFFFAOYSA-N 0.000 claims 1
- CWCRIIMEHHESCR-UHFFFAOYSA-N 2-[4-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-4-(2-propan-2-ylphenyl)piperidin-1-yl]sulfonylacetic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CCN(CC1)S(=O)(=O)CC(=O)O)C1=C(C=CC=C1)C(C)C)C)F CWCRIIMEHHESCR-UHFFFAOYSA-N 0.000 claims 1
- QHDSCNKTJCQWGJ-UHFFFAOYSA-N 2-[4-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-4-(2-propan-2-ylphenyl)piperidine-1-carbonyl]oxyacetic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CCN(CC1)C(=O)OCC(=O)O)C1=C(C=CC=C1)C(C)C)C)F QHDSCNKTJCQWGJ-UHFFFAOYSA-N 0.000 claims 1
- HBDYYQXELWLAQC-UHFFFAOYSA-N 2-[[2-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2-oxoethyl]-ethylamino]acetic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CN(CC(=O)O)CC)=O)C1=C(C=CC=C1)C(C)C)C)F HBDYYQXELWLAQC-UHFFFAOYSA-N 0.000 claims 1
- FWQFQOZPZHBELP-UHFFFAOYSA-N 2-[[2-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2-oxoethyl]-propylamino]acetic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CN(CC(=O)O)CCC)=O)C1=C(C=CC=C1)C(C)C)C)F FWQFQOZPZHBELP-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 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
- 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
- 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
- HUGGNEAEXOAJKD-UHFFFAOYSA-N 3-[4-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-4-(2-propan-2-ylphenyl)piperidin-1-yl]-3-oxopropanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CCN(CC1)C(CC(=O)O)=O)C1=C(C=CC=C1)C(C)C)C)F HUGGNEAEXOAJKD-UHFFFAOYSA-N 0.000 claims 1
- 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
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-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
- 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
- PSSYKRDUBPAFNS-UHFFFAOYSA-N 4-[3-[(5-chloro-3-methoxypyridin-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 PSSYKRDUBPAFNS-UHFFFAOYSA-N 0.000 claims 1
- CGJDDMWEDAYXEM-UHFFFAOYSA-N 4-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-fluoro-6-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=C1C(C)C)F)C)F CGJDDMWEDAYXEM-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
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- 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
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- QJGRGFHZDARDCX-UHFFFAOYSA-N 4-[4-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-4-(2-propan-2-ylphenyl)piperidin-1-yl]-4-oxobutanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CCN(CC1)C(CCC(=O)O)=O)C1=C(C=CC=C1)C(C)C)C)F QJGRGFHZDARDCX-UHFFFAOYSA-N 0.000 claims 1
- AEVSKFPVHQEJGE-UHFFFAOYSA-N 5-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-2,2-dimethylpentanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)CCCC(C(=O)O)(C)C)C1=C(C=CC=C1)C(C)C)C)F AEVSKFPVHQEJGE-UHFFFAOYSA-N 0.000 claims 1
- LIIKWYQZJVQUOW-UHFFFAOYSA-N 5-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]-5-oxopentanoic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C(CCCC(=O)O)=O)C1=C(C=CC=C1)C(C)C)C)F LIIKWYQZJVQUOW-UHFFFAOYSA-N 0.000 claims 1
- AYQKJIDQUPZQFA-UHFFFAOYSA-N 5-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]pyrazine-2-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C=1N=CC(=NC=1)C(=O)O)C1=C(C=CC=C1)C(C)C)C)F AYQKJIDQUPZQFA-UHFFFAOYSA-N 0.000 claims 1
- LMTJEECWMFFBQR-UHFFFAOYSA-N 5-[[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]methyl]-1H-pyrrole-2-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)CC1=CC=C(N1)C(=O)O)C1=C(C=CC=C1)C(C)C)C)F LMTJEECWMFFBQR-UHFFFAOYSA-N 0.000 claims 1
- VBSWWVSMOVUBAD-UHFFFAOYSA-N 5-[[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]methyl]furan-2-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)CC1=CC=C(O1)C(=O)O)C1=C(C=CC=C1)C(C)C)C)F VBSWWVSMOVUBAD-UHFFFAOYSA-N 0.000 claims 1
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- STFUZHPJKUHDEB-UHFFFAOYSA-N 6-[3-[[2-(difluoromethoxy)-6-methylpyridin-3-yl]carbamoyl]-3-(2-propan-2-ylphenyl)azetidin-1-yl]pyridine-3-carboxylic acid Chemical compound FC(OC1=NC(=CC=C1NC(=O)C1(CN(C1)C1=NC=C(C(=O)O)C=C1)C1=C(C=CC=C1)C(C)C)C)F STFUZHPJKUHDEB-UHFFFAOYSA-N 0.000 claims 1
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- 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
- 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
- 206010028980 Neoplasm Diseases 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
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- 125000002541 furyl 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
- 230000036210 malignancy Effects 0.000 claims 1
- 230000003211 malignant effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
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- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
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- 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
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| 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 |
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| JP2021527046A JP2021527046A (ja) | 2021-10-11 |
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| AR119162A1 (es) * | 2019-06-18 | 2021-12-01 | Idorsia Pharmaceuticals Ltd | Derivados de piridin-3-ilo |
| KR20220109439A (ko) | 2019-12-04 | 2022-08-04 | 이도르시아 파마슈티컬스 리미티드 | 섬유증 질환의 치료에서 사용하기 위한 아제티딘 lpa1 수용체 길항제와 피르페니돈 및/또는 닌테다닙의 조합 |
| 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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| GB9919776D0 (en) | 1998-08-31 | 1999-10-27 | Zeneca Ltd | Compoujnds |
| WO2001032173A1 (en) | 1999-10-29 | 2001-05-10 | 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 |
| JP4847868B2 (ja) | 2003-05-14 | 2011-12-28 | ニューロジェネティック ファーマシューティカルズ、 インコーポレイテッド | 化合物、及び、アミロイドベータの調節におけるその使用 |
| US7749999B2 (en) | 2003-09-11 | 2010-07-06 | Itherx Pharmaceuticals, Inc. | Alpha-ketoamides and derivatives thereof |
| EP1679069A4 (en) | 2003-10-21 | 2009-05-13 | Dainippon Sumitomo Pharma Co | NEW PIPERIDINE DERIVATIVE |
| 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 |
| HRP20130719T1 (en) | 2005-08-24 | 2013-09-30 | Eisai R&D Management Co., Ltd. | Novel pyridine derivative and pyrimidine derivative (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 |
| ATE552257T1 (de) | 2007-10-18 | 2012-04-15 | Merck Sharp & Dohme | Positive allosterische chinolizidinon-m1- rezeptormodulatoren |
| US8193202B2 (en) | 2008-04-21 | 2012-06-05 | Lexicon Pharmaceuticals, Inc. | LIMK2 inhibitors, compositions comprising them, and methods of their use |
| RU2529484C2 (ru) | 2008-05-05 | 2014-09-27 | Санофи-Авентис | Ациламино-замещенные производные конденсированных циклопентанкарбоновых кислот и их применение в качестве фармацевтических средств |
| MX2011001938A (es) | 2008-08-26 | 2011-03-29 | Boehringer Ingelheim Int | Tienopirimidinas para composiciones farmaceuticas. |
| BR112012006686B8 (pt) * | 2009-09-25 | 2021-05-25 | Astellas Pharma Inc | compostos de amida substituída, composições farmacêuticas contendo os ditos compostos, e uso dos mesmos para prevenir e/ou tratar doenças causadas pelo lpa |
| CN103270036B (zh) | 2010-08-05 | 2015-11-25 | 佐蒂斯有限责任公司 | 作为抗寄生物剂的异噁唑啉衍生物 |
| TW201305178A (zh) | 2010-10-29 | 2013-02-01 | Glenmark Pharmaceuticals Sa | 作為ｍＰＧＥＳ－１抑制物的三環化合物 |
| EP3360552A1 (en) | 2010-12-07 | 2018-08-15 | Amira Pharmaceuticals, Inc. | Polycyclic lpa1 antagonist and uses thereof |
| US9073895B2 (en) | 2010-12-16 | 2015-07-07 | Boehringer Ingelheim International Gmbh | Biarylamide inhibitors of leukotriene production |
| ME02412B (me) | 2011-03-10 | 2016-09-20 | Zoetis Services Llc | Spirociklični derivati izoksazolina kao antiparazitska sredstva |
| JP2015506349A (ja) | 2011-12-21 | 2015-03-02 | アルデリックス， インコーポレイテッド | 非全身性ｔｇｒ５アゴニスト |
| US20140148484A1 (en) | 2012-11-23 | 2014-05-29 | Boehringer Ingelheim International Gmbh | Pyrazole compounds for treating hairloss |
| TW201444820A (zh) * | 2013-03-13 | 2014-12-01 | Abbvie Inc | 吡啶ｃｄｋ９激酶抑制劑 |
| 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 |
| KR20220109439A (ko) | 2019-12-04 | 2022-08-04 | 이도르시아 파마슈티컬스 리미티드 | 섬유증 질환의 치료에서 사용하기 위한 아제티딘 lpa1 수용체 길항제와 피르페니돈 및/또는 닌테다닙의 조합 |
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2019
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