JP2016508132A5 - - Google Patents

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Publication number

JP2016508132A5

JP2016508132A5 JP2015549466A JP2015549466A JP2016508132A5 JP 2016508132 A5 JP2016508132 A5 JP 2016508132A5 JP 2015549466 A JP2015549466 A JP 2015549466A JP 2015549466 A JP2015549466 A JP 2015549466A JP 2016508132 A5 JP2016508132 A5 JP 2016508132A5

Authority

JP

Japan

Prior art keywords

alkyl

cycloalkyl

halogen

tert

benzyl

Prior art date

2013-12-10

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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• 125000000217 alkyl group Chemical group 0.000 claims 136
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 54
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 48
• 229910052736 halogen Inorganic materials 0.000 claims 42
• -1 1- (4- (tert-butyl) benzyl) -4-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl Chemical group 0.000 claims 26
• 125000005843 halogen group Chemical group 0.000 claims 25
• 125000001072 heteroaryl group Chemical group 0.000 claims 25
• 125000003118 aryl group Chemical group 0.000 claims 24
• 150000002367 halogens Chemical class 0.000 claims 24
• 125000003545 alkoxy group Chemical group 0.000 claims 18
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 17
• 150000001875 compounds Chemical class 0.000 claims 17
• 229910052739 hydrogen Inorganic materials 0.000 claims 17
• 239000001257 hydrogen Substances 0.000 claims 17
• 150000003839 salts Chemical class 0.000 claims 17
• 125000000000 cycloalkoxy group Chemical group 0.000 claims 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims 12
• 125000000623 heterocyclic group Chemical group 0.000 claims 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
• 125000001424 substituent group Chemical group 0.000 claims 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
• YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 5
• 125000002877 alkyl aryl group Chemical group 0.000 claims 4
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 4
• 235000010290 biphenyl Nutrition 0.000 claims 3
• 239000008194 pharmaceutical composition Substances 0.000 claims 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
• OFUNPTVMKDPITP-UHFFFAOYSA-N 2-[4-[3-[3-[1-[(4-tert-butylphenyl)methyl]-4-ethyl-5-oxo-1,2,4-triazol-3-yl]propyl]phenyl]-2-ethoxyphenyl]acetic acid Chemical compound C1=C(CC(O)=O)C(OCC)=CC(C=2C=C(CCCC=3N(C(=O)N(CC=4C=CC(=CC=4)C(C)(C)C)N=3)CC)C=CC=2)=C1 OFUNPTVMKDPITP-UHFFFAOYSA-N 0.000 claims 2
• SPGIRWGJYKEELM-UHFFFAOYSA-N 2-[4-[3-[3-[1-[(4-tert-butylphenyl)methyl]-4-ethyl-5-oxo-1,2,4-triazol-3-yl]propyl]phenyl]-2-propoxyphenyl]acetic acid Chemical compound C1=C(CC(O)=O)C(OCCC)=CC(C=2C=C(CCCC=3N(C(=O)N(CC=4C=CC(=CC=4)C(C)(C)C)N=3)CC)C=CC=2)=C1 SPGIRWGJYKEELM-UHFFFAOYSA-N 0.000 claims 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
• SWHSUFGIJQIABO-UHFFFAOYSA-N 4-[3-[3-[1-[(4-tert-butylphenyl)methyl]-4-ethyl-5-oxo-1,2,4-triazol-3-yl]propyl]phenyl]benzoic acid Chemical compound N=1N(CC=2C=CC(=CC=2)C(C)(C)C)C(=O)N(CC)C=1CCCC(C=1)=CC=CC=1C1=CC=C(C(O)=O)C=C1 SWHSUFGIJQIABO-UHFFFAOYSA-N 0.000 claims 2
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 2
• 206010028980 Neoplasm Diseases 0.000 claims 2
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
• 201000011510 cancer Diseases 0.000 claims 2
• 125000005842 heteroatom Chemical group 0.000 claims 2
• 229910052757 nitrogen Inorganic materials 0.000 claims 2
• 229910052760 oxygen Inorganic materials 0.000 claims 2
• 150000003216 pyrazines Chemical class 0.000 claims 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
• 150000003222 pyridines Chemical class 0.000 claims 2
• 150000003230 pyrimidines Chemical class 0.000 claims 2
• OIGOYHJSBSRMNU-UHFFFAOYSA-N 2-[(4-tert-butylphenyl)methyl]-4-ethyl-5-[3-[3-[3-(2h-tetrazol-5-yl)phenyl]phenyl]propyl]-1,2,4-triazol-3-one Chemical compound N=1N(CC=2C=CC(=CC=2)C(C)(C)C)C(=O)N(CC)C=1CCCC(C=1)=CC=CC=1C(C=1)=CC=CC=1C=1N=NNN=1 OIGOYHJSBSRMNU-UHFFFAOYSA-N 0.000 claims 1
• XXPSWXBRZIDBGM-UHFFFAOYSA-N 2-[4-[3-[3-[1-[(4-tert-butylphenyl)methyl]-4-ethyl-5-oxo-1,2,4-triazol-3-yl]propyl]phenyl]-2-methoxyphenyl]acetic acid Chemical compound N=1N(CC=2C=CC(=CC=2)C(C)(C)C)C(=O)N(CC)C=1CCCC(C=1)=CC=CC=1C1=CC=C(CC(O)=O)C(OC)=C1 XXPSWXBRZIDBGM-UHFFFAOYSA-N 0.000 claims 1
• VLOJGNWSESNGHI-UHFFFAOYSA-N 2-[5-[3-[3-[1-[(4-tert-butylphenyl)methyl]-4-ethyl-5-oxo-1,2,4-triazol-3-yl]propyl]phenyl]-2-[2-(dimethylamino)ethoxy]phenyl]acetic acid Chemical compound N=1N(CC=2C=CC(=CC=2)C(C)(C)C)C(=O)N(CC)C=1CCCC(C=1)=CC=CC=1C1=CC=C(OCCN(C)C)C(CC(O)=O)=C1 VLOJGNWSESNGHI-UHFFFAOYSA-N 0.000 claims 1
• KUXHBSDSFDBFOV-UHFFFAOYSA-N 2-[5-[3-[3-[1-[(4-tert-butylphenyl)methyl]-4-ethyl-5-oxo-1,2,4-triazol-3-yl]propyl]phenyl]-2-phenylmethoxyphenyl]acetic acid Chemical compound N=1N(CC=2C=CC(=CC=2)C(C)(C)C)C(=O)N(CC)C=1CCCC(C=1)=CC=CC=1C(C=C1CC(O)=O)=CC=C1OCC1=CC=CC=C1 KUXHBSDSFDBFOV-UHFFFAOYSA-N 0.000 claims 1
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• YVVXGIIEXQIAOT-UHFFFAOYSA-N 3-[3-[3-[1-[(4-tert-butylphenyl)methyl]-4-ethyl-5-oxo-1,2,4-triazol-3-yl]propyl]phenyl]benzoic acid Chemical compound N=1N(CC=2C=CC(=CC=2)C(C)(C)C)C(=O)N(CC)C=1CCCC(C=1)=CC=CC=1C1=CC=CC(C(O)=O)=C1 YVVXGIIEXQIAOT-UHFFFAOYSA-N 0.000 claims 1
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
• UIHYSJICOZFFEV-UHFFFAOYSA-N 5-[3-[3-[1-[(4-tert-butylphenyl)methyl]-4-ethyl-5-oxo-1,2,4-triazol-3-yl]propyl]phenyl]-2-ethoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OCC)=CC=C1C1=CC=CC(CCCC=2N(C(=O)N(CC=3C=CC(=CC=3)C(C)(C)C)N=2)CC)=C1 UIHYSJICOZFFEV-UHFFFAOYSA-N 0.000 claims 1
• ZEYVDHXFZBHCJO-UHFFFAOYSA-N 5-[3-[3-[1-[(4-tert-butylphenyl)methyl]-4-ethyl-5-oxo-1,2,4-triazol-3-yl]propyl]phenyl]-2-methoxybenzoic acid Chemical compound N=1N(CC=2C=CC(=CC=2)C(C)(C)C)C(=O)N(CC)C=1CCCC(C=1)=CC=CC=1C1=CC=C(OC)C(C(O)=O)=C1 ZEYVDHXFZBHCJO-UHFFFAOYSA-N 0.000 claims 1
• IGRLKERSQGNVIP-UHFFFAOYSA-N 5-[3-[3-[1-[(4-tert-butylphenyl)methyl]-4-ethyl-5-oxo-1,2,4-triazol-3-yl]propyl]phenyl]-2-propoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OCCC)=CC=C1C1=CC=CC(CCCC=2N(C(=O)N(CC=3C=CC(=CC=3)C(C)(C)C)N=2)CC)=C1 IGRLKERSQGNVIP-UHFFFAOYSA-N 0.000 claims 1
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
• 206010006187 Breast cancer Diseases 0.000 claims 1
• 208000026310 Breast neoplasm Diseases 0.000 claims 1
• 206010009944 Colon cancer Diseases 0.000 claims 1
• 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 1
• 241000124008 Mammalia Species 0.000 claims 1
• 206010033128 Ovarian cancer Diseases 0.000 claims 1
• 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
• 206010060862 Prostate cancer Diseases 0.000 claims 1
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
• 206010038389 Renal cancer Diseases 0.000 claims 1
• 125000003342 alkenyl group Chemical group 0.000 claims 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 1
• 208000029742 colonic neoplasm Diseases 0.000 claims 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 230000004129 fatty acid metabolism Effects 0.000 claims 1
• 201000010982 kidney cancer Diseases 0.000 claims 1
• 201000007270 liver cancer Diseases 0.000 claims 1
• 208000014018 liver neoplasm Diseases 0.000 claims 1
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
• 201000001441 melanoma Diseases 0.000 claims 1
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
• AUNDLDUABXMSHF-UHFFFAOYSA-N n-[[3-[3-[3-[1-[(4-tert-butylphenyl)methyl]-4-ethyl-5-oxo-1,2,4-triazol-3-yl]propyl]phenyl]phenyl]methyl]benzenesulfonamide Chemical compound N=1N(CC=2C=CC(=CC=2)C(C)(C)C)C(=O)N(CC)C=1CCCC(C=1)=CC=CC=1C(C=1)=CC=CC=1CNS(=O)(=O)C1=CC=CC=C1 AUNDLDUABXMSHF-UHFFFAOYSA-N 0.000 claims 1
• 201000002528 pancreatic cancer Diseases 0.000 claims 1
• 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
• 235000019260 propionic acid Nutrition 0.000 claims 1
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
• 229910052717 sulfur Inorganic materials 0.000 claims 1