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 | ||
| PCT/US2017/061223 WO2018093696A1 (en) | 2016-11-18 | 2017-11-13 | Indazole derivatives useful as inhibitors of diacylglyceride o-acyltransferase 2 |
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| MA41179A (fr) | 2014-12-19 | 2017-10-24 | Cancer Research Tech Ltd | Composés inhibiteurs de parg |
| WO2021236405A1 (en) * | 2020-05-18 | 2021-11-25 | Merck Sharp & Dohme Corp. | Novel diacylglyceride o-acyltransferase 2 inhibitors |
| TW202229243A (zh) | 2020-10-08 | 2022-08-01 | 美商默沙東藥廠 | 作為新穎二醯基甘油酯o-醯基轉移酶2抑制劑之苯并咪唑酮衍生物的製備 |
| AR123701A1 (es) * | 2020-10-08 | 2023-01-04 | Merck Sharp & Dohme | Preparación de derivados de oxindol como nuevos inhibidores de la diacilglicerol o-aciltransferasa 2 |
| US20240066027A1 (en) * | 2020-12-03 | 2024-02-29 | Domain Therapeutics | Novel par-2 inhibitors |
| EP4267135A4 (en) * | 2020-12-22 | 2024-05-15 | Merck Sharp & Dohme LLC | Preparation of tetrahydroindazole derivatives as novel diacylglyceride o-acyltransferase 2 inhibitors |
| MX2024011545A (es) | 2022-03-23 | 2024-09-26 | Ideaya Biosciences Inc | Compuestos de indazol sustituidos con piperazina como inhibidores de parg. |
| KR20250107282A (ko) | 2022-12-02 | 2025-07-11 | 머크 샤프 앤드 돔 엘엘씨 | 신규 디아실글리세리드 o-아실트랜스퍼라제 2 억제제로서의 융합된 아졸 유도체의 제조 |
| CN121045138A (zh) * | 2024-06-01 | 2025-12-02 | 中国药科大学 | 双环类化合物及其医药用途 |
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| EA002113B1 (ru) * | 1996-09-04 | 2001-12-24 | Пфайзер Инк. | Производные индазола и их использование в качестве ингибиторов фосфодиэстеразы (фдэ) типа iv и продуцирования фактора некроза опухоли (фно) |
| US6054587A (en) | 1997-03-07 | 2000-04-25 | Metabasis Therapeutics, Inc. | Indole and azaindole inhibitors of fructose-1,6-bisphosphatase |
| DE69819311T2 (de) | 1997-03-07 | 2004-07-29 | Metabasis Therapeutics Inc., San Diego | Neue benzimidazol inhibitoren der fructose-1,6-bisphosphatase |
| US6284748B1 (en) | 1997-03-07 | 2001-09-04 | Metabasis Therapeutics, Inc. | Purine inhibitors of fructose 1,6-bisphosphatase |
| KR100818845B1 (ko) | 1998-09-09 | 2008-04-01 | 메타베이시스 테라퓨틱스, 인크. | 신규한 프럭토스 1,6-비스포스파타제의 헤테로방향족 억제제 |
| AU7705601A (en) | 2000-07-25 | 2002-02-05 | Merck & Co Inc | N-substituted indoles useful in the treatment of diabetes |
| EP1357908A4 (en) | 2001-01-30 | 2009-07-15 | Merck & Co Inc | "ACYLSULFAMIDES FOR THE TREATMENT OF FATIBILITY, DIABETES AND LIPID DISORDERS" |
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| US6596718B1 (en) * | 2001-11-27 | 2003-07-22 | Hoffmann-La Roche Inc. | 7-Morpholin-4yl-benzothiazole amide derivatives |
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- 2017-11-13 BR BR112019010164A patent/BR112019010164A2/pt not_active IP Right Cessation
- 2017-11-13 RU RU2019117556A patent/RU2019117556A/ru unknown
- 2017-11-13 KR KR1020197016983A patent/KR20190078646A/ko not_active Withdrawn
- 2017-11-13 CA CA3043203A patent/CA3043203A1/en not_active Abandoned
- 2017-11-13 MX MX2019005786A patent/MX2019005786A/es unknown
- 2017-11-13 US US16/461,902 patent/US11104690B2/en active Active
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- 2017-11-13 WO PCT/US2017/061223 patent/WO2018093696A1/en not_active Ceased
- 2017-11-13 JP JP2019526217A patent/JP2020502058A/ja not_active Ceased
- 2017-11-13 MA MA046856A patent/MA46856A/fr unknown
- 2017-11-13 CN CN201780071343.9A patent/CN110121341A/zh active Pending
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