JP2020502058A5 - - Google Patents
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- Publication number
- JP2020502058A5 JP2020502058A5 JP2019526217A JP2019526217A JP2020502058A5 JP 2020502058 A5 JP2020502058 A5 JP 2020502058A5 JP 2019526217 A JP2019526217 A JP 2019526217A JP 2019526217 A JP2019526217 A JP 2019526217A JP 2020502058 A5 JP2020502058 A5 JP 2020502058A5
- Authority
- JP
- Japan
- Prior art keywords
- indazole
- carboxamide
- fluorophenyl
- chlorophenyl
- alkyl
- 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.)
- Ceased
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- -1 tetrahydrothiophene-3-yl Chemical group 0.000 claims 123
- 125000000217 alkyl group Chemical group 0.000 claims 86
- 125000005842 heteroatom Chemical group 0.000 claims 45
- 229910052760 oxygen Inorganic materials 0.000 claims 45
- 229910052717 sulfur Inorganic materials 0.000 claims 45
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 40
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims 33
- 125000001072 heteroaryl group Chemical group 0.000 claims 32
- 125000003118 aryl group Chemical group 0.000 claims 28
- 125000005843 halogen group Chemical group 0.000 claims 27
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 201000001320 Atherosclerosis Diseases 0.000 claims 5
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- DQZNKQWAVMGUIN-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(2-hydroxycyclopentyl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC1C(CCC1)O)C1=CC=C(C=C1)F DQZNKQWAVMGUIN-UHFFFAOYSA-N 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 230000007850 degeneration Effects 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms 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
- 235000020824 obesity Nutrition 0.000 claims 2
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- CVJHDHLEPSCDGR-HSZRJFAPSA-N 3-(2-chloro-5-cyanophenyl)-1-(4-fluorophenyl)-N-[(2S)-1-hydroxy-3-methylbutan-2-yl]indazole-6-carboxamide Chemical compound ClC1=C(C=C(C=C1)C#N)C1=NN(C2=CC(=CC=C12)C(=O)N[C@@H](C(C)C)CO)C1=CC=C(C=C1)F CVJHDHLEPSCDGR-HSZRJFAPSA-N 0.000 claims 1
- OZMDDFOOQFKYES-UHFFFAOYSA-N 3-(2-chloro-5-cyanophenyl)-1-(4-fluorophenyl)-N-[1-(hydroxymethyl)cyclobutyl]indazole-6-carboxamide Chemical compound ClC1=C(C=C(C=C1)C#N)C1=NN(C2=CC(=CC=C12)C(=O)NC1(CCC1)CO)C1=CC=C(C=C1)F OZMDDFOOQFKYES-UHFFFAOYSA-N 0.000 claims 1
- AFZDSWYXAHLHGL-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(1,1,1-trifluoro-2-hydroxyheptan-3-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC(CCCC)C(C(F)(F)F)O)C1=CC=C(C=C1)F AFZDSWYXAHLHGL-UHFFFAOYSA-N 0.000 claims 1
- CMDKQFAAXJYWIE-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(1,2,5-thiadiazol-3-ylmethyl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NCC1=NSN=C1)C1=CC=C(C=C1)F CMDKQFAAXJYWIE-UHFFFAOYSA-N 0.000 claims 1
- AVRCLHVFFQEBPY-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(1,2-oxazol-4-ylmethyl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NCC=1C=NOC=1)C1=CC=C(C=C1)F AVRCLHVFFQEBPY-UHFFFAOYSA-N 0.000 claims 1
- HJHQKMCAMDYDNE-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(1-hydroxy-2-methylpropan-2-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC(CO)(C)C)C1=CC=C(C=C1)F HJHQKMCAMDYDNE-UHFFFAOYSA-N 0.000 claims 1
- XLIFNOAGNQUFBX-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(1-hydroxy-3-methoxy-1-phenylpropan-2-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC(C(C1=CC=CC=C1)O)COC)C1=CC=C(C=C1)F XLIFNOAGNQUFBX-UHFFFAOYSA-N 0.000 claims 1
- WEFMHENNKAJEMB-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(1-hydroxybutan-2-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC(CC)CO)C1=CC=C(C=C1)F WEFMHENNKAJEMB-UHFFFAOYSA-N 0.000 claims 1
- OYYOEXNYHFTCBP-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(1-hydroxypropan-2-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC(CO)C)C1=CC=C(C=C1)F OYYOEXNYHFTCBP-UHFFFAOYSA-N 0.000 claims 1
- MCDBVFGXXHEQJP-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(1-methyl-2-oxopyrrolidin-3-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC1C(N(CC1)C)=O)C1=CC=C(C=C1)F MCDBVFGXXHEQJP-UHFFFAOYSA-N 0.000 claims 1
- ZUDAILDJDCCLGW-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(1-methyl-5-oxopyrrolidin-3-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC1CN(C(C1)=O)C)C1=CC=C(C=C1)F ZUDAILDJDCCLGW-UHFFFAOYSA-N 0.000 claims 1
- DJSPZVKTYANFJJ-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(1-pyridin-2-ylpropan-2-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC(CC1=NC=CC=C1)C)C1=CC=C(C=C1)F DJSPZVKTYANFJJ-UHFFFAOYSA-N 0.000 claims 1
- ZJOLIZIWXRBNCC-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(2-hydroxy-1-phenylethyl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC(CO)C1=CC=CC=C1)C1=CC=C(C=C1)F ZJOLIZIWXRBNCC-UHFFFAOYSA-N 0.000 claims 1
- JWKSXTTXAYKCTH-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(2-hydroxy-5-methylcyclopentyl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC1C(CCC1C)O)C1=CC=C(C=C1)F JWKSXTTXAYKCTH-UHFFFAOYSA-N 0.000 claims 1
- XSZVJJFKPXZLRS-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(2-methoxyethyl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NCCOC)C1=CC=C(C=C1)F XSZVJJFKPXZLRS-UHFFFAOYSA-N 0.000 claims 1
- JSYKDXJJRYARSA-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(2-oxopyrrolidin-3-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC1C(NCC1)=O)C1=CC=C(C=C1)F JSYKDXJJRYARSA-UHFFFAOYSA-N 0.000 claims 1
- YCFMIVNQCDCPNF-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(2-sulfamoylethyl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NCCS(N)(=O)=O)C1=CC=C(C=C1)F YCFMIVNQCDCPNF-UHFFFAOYSA-N 0.000 claims 1
- XBSWANVTTHJAJT-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(3-hydroxy-3,4-dihydro-2H-chromen-4-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC1C(COC2=CC=CC=C12)O)C1=CC=C(C=C1)F XBSWANVTTHJAJT-UHFFFAOYSA-N 0.000 claims 1
- YIHNUNWNZXBXDQ-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(3-hydroxycyclopentyl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC1CC(CC1)O)C1=CC=C(C=C1)F YIHNUNWNZXBXDQ-UHFFFAOYSA-N 0.000 claims 1
- FTEWBMRAKORYPE-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(3-morpholin-4-yl-1-phenylpropyl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC(CCN1CCOCC1)C1=CC=CC=C1)C1=CC=C(C=C1)F FTEWBMRAKORYPE-UHFFFAOYSA-N 0.000 claims 1
- FMOWOPWZWWLPCP-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(3-oxocyclobutyl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC1CC(C1)=O)C1=CC=C(C=C1)F FMOWOPWZWWLPCP-UHFFFAOYSA-N 0.000 claims 1
- CSASAUOBCBTLHH-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(4,4,4-trifluoro-3-hydroxybutan-2-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC(C(C(F)(F)F)O)C)C1=CC=C(C=C1)F CSASAUOBCBTLHH-UHFFFAOYSA-N 0.000 claims 1
- NIVSDSCTVZNNAE-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(4-hydroxy-2-methylpentan-2-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC(CC(C)O)(C)C)C1=CC=C(C=C1)F NIVSDSCTVZNNAE-UHFFFAOYSA-N 0.000 claims 1
- DMIFRWVSDPBKEQ-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(oxan-4-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC1CCOCC1)C1=CC=C(C=C1)F DMIFRWVSDPBKEQ-UHFFFAOYSA-N 0.000 claims 1
- WRWWIBRHHZPZEE-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(oxetan-3-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC1COC1)C1=CC=C(C=C1)F WRWWIBRHHZPZEE-UHFFFAOYSA-N 0.000 claims 1
- ZDSFICODFSGWOR-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(oxolan-3-yl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NC1COCC1)C1=CC=C(C=C1)F ZDSFICODFSGWOR-UHFFFAOYSA-N 0.000 claims 1
- MHWAPMGKMFYZIG-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(pyridin-2-ylmethyl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NCC1=NC=CC=C1)C1=CC=C(C=C1)F MHWAPMGKMFYZIG-UHFFFAOYSA-N 0.000 claims 1
- WLENMOJGBQBHRO-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(pyridin-3-ylmethyl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NCC=1C=NC=CC=1)C1=CC=C(C=C1)F WLENMOJGBQBHRO-UHFFFAOYSA-N 0.000 claims 1
- LBTXEEXPGCBAIM-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(pyridin-4-ylmethyl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NCC1=CC=NC=C1)C1=CC=C(C=C1)F LBTXEEXPGCBAIM-UHFFFAOYSA-N 0.000 claims 1
- OLWRXIQBQMXVST-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-(pyrimidin-5-ylmethyl)indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NCC=1C=NC=NC=1)C1=CC=C(C=C1)F OLWRXIQBQMXVST-UHFFFAOYSA-N 0.000 claims 1
- CZJLQLVYHHQSMQ-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(1-hydroxycyclohexyl)methyl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NCC1(CCCCC1)O)C1=CC=C(C=C1)F CZJLQLVYHHQSMQ-UHFFFAOYSA-N 0.000 claims 1
- CGRBGLIYVQSQLP-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(1-hydroxycyclopropyl)methyl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)NCC1(CC1)O)C1=CC=C(C=C1)F CGRBGLIYVQSQLP-UHFFFAOYSA-N 0.000 claims 1
- MHAIAZMUAJUQLE-MRXNPFEDSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(1R)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)N[C@H](C)C=1C=NC(=CC=1)C(F)(F)F)C1=CC=C(C=C1)F MHAIAZMUAJUQLE-MRXNPFEDSA-N 0.000 claims 1
- NXLFGBLFRUYQHC-QHCPKHFHSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(1R)-2-hydroxy-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)N[C@@H](CO)C=1C=NC(=CC=1)C(F)(F)F)C1=CC=C(C=C1)F NXLFGBLFRUYQHC-QHCPKHFHSA-N 0.000 claims 1
- YWQMVOJRMLTSCY-WRHNGFHOSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)N[C@@H]([C@@H](C1=CC=CC=C1)O)C)C1=CC=C(C=C1)F YWQMVOJRMLTSCY-WRHNGFHOSA-N 0.000 claims 1
- DQZNKQWAVMGUIN-GGAORHGYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(1R,2S)-2-hydroxycyclopentyl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)N[C@H]1[C@H](CCC1)O)C1=CC=C(C=C1)F DQZNKQWAVMGUIN-GGAORHGYSA-N 0.000 claims 1
- UATLWZPBFHUFFO-INIZCTEOSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(1S)-1-(2-methylpyrimidin-5-yl)ethyl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)N[C@@H](C)C=1C=NC(=NC=1)C)C1=CC=C(C=C1)F UATLWZPBFHUFFO-INIZCTEOSA-N 0.000 claims 1
- ONNSYWJFONSNCL-HNNXBMFYSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(1S)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)N[C@@H](C)C=1C=NC(=NC=1)C(F)(F)F)C1=CC=C(C=C1)F ONNSYWJFONSNCL-HNNXBMFYSA-N 0.000 claims 1
- MHAIAZMUAJUQLE-INIZCTEOSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(1S)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)N[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F)C1=CC=C(C=C1)F MHAIAZMUAJUQLE-INIZCTEOSA-N 0.000 claims 1
- NXLFGBLFRUYQHC-HSZRJFAPSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(1S)-2-hydroxy-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)N[C@H](CO)C=1C=NC(=CC=1)C(F)(F)F)C1=CC=C(C=C1)F NXLFGBLFRUYQHC-HSZRJFAPSA-N 0.000 claims 1
- YWQMVOJRMLTSCY-KWMCUTETSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)N[C@@H]([C@H](C1=CC=CC=C1)O)C)C1=CC=C(C=C1)F YWQMVOJRMLTSCY-KWMCUTETSA-N 0.000 claims 1
- DQZNKQWAVMGUIN-GMAHTHKFSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(1S,2S)-2-hydroxycyclopentyl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)N[C@@H]1[C@H](CCC1)O)C1=CC=C(C=C1)F DQZNKQWAVMGUIN-GMAHTHKFSA-N 0.000 claims 1
- IHLUMLSKESFFBQ-CQSZACIVSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(2R)-1-sulfamoylpropan-2-yl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)N[C@@H](CS(N)(=O)=O)C)C1=CC=C(C=C1)F IHLUMLSKESFFBQ-CQSZACIVSA-N 0.000 claims 1
- OQIZMLKSBKOUMM-HSZRJFAPSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(2S)-1-hydroxy-3,3-dimethylbutan-2-yl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)N[C@@H](C(C)(C)C)CO)C1=CC=C(C=C1)F OQIZMLKSBKOUMM-HSZRJFAPSA-N 0.000 claims 1
- DUPVYISYNVJFAV-JOCHJYFZSA-N 3-(2-chlorophenyl)-1-(4-fluorophenyl)-N-[(2S)-1-hydroxy-3-methylbutan-2-yl]indazole-6-carboxamide Chemical compound ClC1=C(C=CC=C1)C1=NN(C2=CC(=CC=C12)C(=O)N[C@@H](C(C)C)CO)C1=CC=C(C=C1)F DUPVYISYNVJFAV-JOCHJYFZSA-N 0.000 claims 1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662424066P | 2016-11-18 | 2016-11-18 | |
| US62/424,066 | 2016-11-18 | ||
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| MA41179A (fr) | 2014-12-19 | 2017-10-24 | Cancer Research Tech Ltd | Composés inhibiteurs de parg |
| US20230174521A1 (en) | 2020-05-18 | 2023-06-08 | Merck Sharp & Dohme Llc | Novel diacylglyceride o-acyltransferase 2 inhibitors |
| AU2021356589A1 (en) * | 2020-10-08 | 2023-05-25 | Merck Sharp & Dohme Llc | Preparation of benzimidazolone derivatives as novel diacylglyceride o-acyltransferase 2 inhibitors |
| KR102993831B1 (ko) * | 2020-10-08 | 2026-07-23 | 머크 샤프 앤드 돔 엘엘씨 | 신규 디아실글리세리드 o-아실트랜스퍼라제 2 억제제로서의 옥스인돌 유도체의 제조 |
| US20240066027A1 (en) * | 2020-12-03 | 2024-02-29 | Domain Therapeutics | Novel par-2 inhibitors |
| AU2021409234A1 (en) * | 2020-12-22 | 2023-06-29 | Merck Sharp & Dohme Llc | Preparation of tetrahydroindazole derivatives as novel diacylglyceride o-acyltransferase 2 inhibitors |
| PL4496795T3 (pl) | 2022-03-23 | 2026-07-20 | Ideaya Biosciences, Inc. | Związki indazolowe podstawione piperazyną jako inhibitory parg |
| JP2025537517A (ja) * | 2022-11-01 | 2025-11-18 | メルク・シャープ・アンド・ドーム・エルエルシー | 新規ジアシルグリセリドｏ－アシルトランスフェラーゼ２阻害薬としてのピラゾロピリジン誘導体及びトリアゾロピリジン誘導体の調製 |
| AU2023400409A1 (en) | 2022-12-02 | 2025-06-26 | Merck Sharp & Dohme Llc | Preparation of fused azole derivatives as novel diacylglyceride o-acyltransferase 2 inhibitors |
| WO2025247370A1 (zh) * | 2024-06-01 | 2025-12-04 | 中国药科大学 | 双环类化合物及其医药用途 |
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| KR100338610B1 (ko) * | 1996-09-04 | 2002-05-27 | 디. 제이. 우드, 스피겔 알렌 제이 | 인다졸 유도체 및 포스포디에스터라제 (pde) 유형 iv 및 종양괴사인자 (tnf) 생산의 억제제로서 그의 용도 |
| DE69819311T2 (de) | 1997-03-07 | 2004-07-29 | Metabasis Therapeutics Inc., San Diego | Neue benzimidazol inhibitoren der fructose-1,6-bisphosphatase |
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| CZ297264B6 (cs) | 1998-09-09 | 2006-10-11 | Metabasis Therapeutics, Inc. | Nové heteroaromatické inhibitory fruktóza-1,6-bisfosfatázy |
| CA2415742A1 (en) | 2000-07-25 | 2002-01-31 | Merck & Co., Inc. | N-substituted indoles useful in the treatment of diabetes |
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| MXPA04004982A (es) * | 2001-11-27 | 2004-08-11 | Hoffmann La Roche | Derivados de benzotiazol. |
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-
2017
- 2017-11-13 RU RU2019117556A patent/RU2019117556A/ru unknown
- 2017-11-13 CA CA3043203A patent/CA3043203A1/en not_active Abandoned
- 2017-11-13 AU AU2017360939A patent/AU2017360939B2/en not_active Expired - Fee Related
- 2017-11-13 EP EP17871593.4A patent/EP3541374B1/en active Active
- 2017-11-13 US US16/461,902 patent/US11104690B2/en active Active
- 2017-11-13 JP JP2019526217A patent/JP2020502058A/ja not_active Ceased
- 2017-11-13 MX MX2019005786A patent/MX2019005786A/es unknown
- 2017-11-13 WO PCT/US2017/061223 patent/WO2018093696A1/en not_active Ceased
- 2017-11-13 BR BR112019010164-0A patent/BR112019010164A2/pt not_active IP Right Cessation
- 2017-11-13 MA MA046856A patent/MA46856A/fr unknown
- 2017-11-13 KR KR1020197016983A patent/KR20190078646A/ko not_active Withdrawn
- 2017-11-13 CN CN201780071343.9A patent/CN110121341A/zh active Pending
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