JP2020512289A5 - - Google Patents
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- JP2020512289A5 JP2020512289A5 JP2019531921A JP2019531921A JP2020512289A5 JP 2020512289 A5 JP2020512289 A5 JP 2020512289A5 JP 2019531921 A JP2019531921 A JP 2019531921A JP 2019531921 A JP2019531921 A JP 2019531921A JP 2020512289 A5 JP2020512289 A5 JP 2020512289A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- cycloalkyl
- heteroaryl
- aryl
- 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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- 150000001875 compounds Chemical class 0.000 claims description 192
- 125000001072 heteroaryl group Chemical group 0.000 claims description 137
- 125000000217 alkyl group Chemical group 0.000 claims description 129
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 100
- 125000003118 aryl group Chemical group 0.000 claims description 98
- -1 hydroxy, amino Chemical group 0.000 claims description 91
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 86
- 125000002252 acyl group Chemical group 0.000 claims description 74
- 238000006467 substitution reaction Methods 0.000 claims description 74
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 66
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 52
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 50
- 125000003545 alkoxy group Chemical group 0.000 claims description 47
- 125000003282 alkyl amino group Chemical group 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 150000001408 amides Chemical class 0.000 claims description 43
- 125000004423 acyloxy group Chemical group 0.000 claims description 37
- 125000005842 heteroatom Chemical group 0.000 claims description 34
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 29
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 29
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 27
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 125000003107 substituted aryl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 150000002390 heteroarenes Chemical class 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 15
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 10
- 201000001119 neuropathy Diseases 0.000 claims description 5
- 230000007823 neuropathy Effects 0.000 claims description 5
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 208000017442 Retinal disease Diseases 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000001361 intraarterial administration Methods 0.000 claims description 4
- 238000007912 intraperitoneal administration Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 208000022371 chronic pain syndrome Diseases 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 230000004968 inflammatory condition Effects 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 238000007918 intramuscular administration Methods 0.000 claims description 3
- 238000001990 intravenous administration Methods 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims description 2
- 206010013774 Dry eye Diseases 0.000 claims description 2
- 206010028372 Muscular weakness Diseases 0.000 claims description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 2
- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 2
- 201000009594 Systemic Scleroderma Diseases 0.000 claims description 2
- 206010042953 Systemic sclerosis Diseases 0.000 claims description 2
- 206010046851 Uveitis Diseases 0.000 claims description 2
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims description 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 206010025135 lupus erythematosus Diseases 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 230000036473 myasthenia Effects 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000001185 psoriatic effect Effects 0.000 claims description 2
- 208000020016 psychiatric disease Diseases 0.000 claims description 2
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 11
- 125000000732 arylene group Chemical group 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 4
- 125000003368 amide group Chemical group 0.000 claims 3
- 125000000033 alkoxyamino group Chemical group 0.000 claims 1
- 208000002741 leukoplakia Diseases 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 238000000034 method Methods 0.000 description 25
- 150000001345 alkine derivatives Chemical class 0.000 description 14
- 125000004414 alkyl thio group Chemical group 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 125000005605 benzo group Chemical group 0.000 description 6
- 208000020832 chronic kidney disease Diseases 0.000 description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- 208000008589 Obesity Diseases 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 235000020824 obesity Nutrition 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241000222722 Leishmania <genus> Species 0.000 description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000008482 dysregulation Effects 0.000 description 2
- 230000028709 inflammatory response Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- XPVSVVMQAZGYHQ-SSEXGKCCSA-N (10aR)-4-(2-fluorophenyl)-2-(8-fluoroquinolin-4-yl)-7,10a-dimethyl-8-oxo-5,6-dihydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=C2CCc3c(nc(nc3[C@]2(C)C=C(C#N)C1=O)-c1ccnc2c(F)cccc12)-c1ccccc1F XPVSVVMQAZGYHQ-SSEXGKCCSA-N 0.000 description 1
- NQHYDDWYIPZOPX-SSEXGKCCSA-N (10aR)-4-(2-fluorophenyl)-7,10a-dimethyl-8-oxo-2-quinolin-4-yl-5,6-dihydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC1=C2CCc3c(nc(nc3[C@]2(C)C=C(C#N)C1=O)-c1ccnc2ccccc12)-c1ccccc1F NQHYDDWYIPZOPX-SSEXGKCCSA-N 0.000 description 1
- KFZMMZGJJTWWCC-WCADHIDISA-N (5aR,6R,9aS)-2-(2-cyclopropylpyridin-4-yl)-4-(2-fluorophenyl)-6,9a-dimethyl-7-oxo-5a,6-dihydro-5H-indeno[1,2-d]pyrimidine-8-carbonitrile Chemical compound C[C@@H]1[C@H]2Cc3c(nc(nc3-c3ccccc3F)-c3ccnc(c3)C3CC3)[C@]2(C)C=C(C#N)C1=O KFZMMZGJJTWWCC-WCADHIDISA-N 0.000 description 1
- JXBGWOZBAOPHKT-CDSKMIAASA-N (5aR,6R,9aS)-2-(8-fluoro-2-methylquinolin-4-yl)-4-(2-fluorophenyl)-6,9a-dimethyl-7-oxo-5a,6-dihydro-5H-indeno[1,2-d]pyrimidine-8-carbonitrile Chemical compound C[C@@H]1[C@H]2Cc3c(nc(nc3-c3ccccc3F)-c3cc(C)nc4c(F)cccc34)[C@]2(C)C=C(C#N)C1=O JXBGWOZBAOPHKT-CDSKMIAASA-N 0.000 description 1
- IWMOTEAUMWYIDT-SONIDQRYSA-N (5aR,6R,9aS)-2-[2-(fluoromethyl)pyridin-4-yl]-4-(2-fluorophenyl)-6,9a-dimethyl-7-oxo-5a,6-dihydro-5H-indeno[1,2-d]pyrimidine-8-carbonitrile Chemical compound C[C@@H]1[C@H]2Cc3c(nc(nc3-c3ccccc3F)-c3ccnc(CF)c3)[C@]2(C)C=C(C#N)C1=O IWMOTEAUMWYIDT-SONIDQRYSA-N 0.000 description 1
- TXORJKASDUMNTF-VSUWZMIJSA-N (5aR,6R,9aS)-4-(2-fluorophenyl)-6,9a-dimethyl-7-oxo-2-quinolin-4-yl-5a,6-dihydro-5H-indeno[1,2-d]pyrimidine-8-carbonitrile Chemical compound C[C@@H]1[C@H]2Cc3c(nc(nc3-c3ccccc3F)-c3ccnc4ccccc34)[C@]2(C)C=C(C#N)C1=O TXORJKASDUMNTF-VSUWZMIJSA-N 0.000 description 1
- FVRLOTRSLKXKKG-VSUWZMIJSA-N (5aR,6R,9aS)-4-(2-fluorophenyl)-6,9a-dimethyl-7-oxo-2-quinolin-5-yl-5a,6-dihydro-5H-indeno[1,2-d]pyrimidine-8-carbonitrile Chemical compound C[C@@H]1[C@H]2Cc3c(nc(nc3-c3ccccc3F)-c3cccc4ncccc34)[C@]2(C)C=C(C#N)C1=O FVRLOTRSLKXKKG-VSUWZMIJSA-N 0.000 description 1
- VHHCYGIBPHPTJF-IIMAJNMQSA-N (6aR,10aS)-2-(2-cyclopropylpyridin-4-yl)-4-(2-fluorophenyl)-8-oxo-10a-propyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CCC[C@@]12C=C(C#N)C(=O)C[C@H]1CCc1c(nc(nc21)-c1ccnc(c1)C1CC1)-c1ccccc1F VHHCYGIBPHPTJF-IIMAJNMQSA-N 0.000 description 1
- RXXFLHZMWMJERT-IIMAJNMQSA-N (6aR,10aS)-2-[2-(fluoromethyl)pyridin-4-yl]-4-(2-fluorophenyl)-10a-(3-methylbutyl)-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound CC(C)CC[C@@]12C=C(C#N)C(=O)C[C@H]1CCc1c(nc(nc21)-c1ccnc(CF)c1)-c1ccccc1F RXXFLHZMWMJERT-IIMAJNMQSA-N 0.000 description 1
- UHUOYCMYXVULPM-WHLCRQNOSA-N (6aR,10aS)-2-[2-(fluoromethyl)pyridin-4-yl]-4-(2-fluorophenyl)-8-oxo-10a-propyl-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound FCC1=NC=CC(=C1)C1=NC=2[C@]3([C@H](CCC=2C(=N1)C1=C(C=CC=C1)F)CC(C(=C3)C#N)=O)CCC UHUOYCMYXVULPM-WHLCRQNOSA-N 0.000 description 1
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- IOYBGKKAHHCRLS-YIPKYWMUSA-N (6aR,7R,10aR)-4-(2-fluorophenyl)-8-hydroxy-7,10a-dimethyl-2-(3-methylpyridin-4-yl)-6,6a,7,10-tetrahydro-5H-benzo[h]quinazoline-9-carbonitrile Chemical compound C[C@@H]1[C@H]2CCc3c(nc(nc3[C@]2(C)CC(C#N)=C1O)-c1ccncc1C)-c1ccccc1F IOYBGKKAHHCRLS-YIPKYWMUSA-N 0.000 description 1
- LNCCPNVKXMXVRD-BRLBNAAPSA-N (6aR,7R,10aR)-4-(4-fluorophenyl)-7,10a-dimethyl-2-(2-methylpyridin-4-yl)-8-oxo-5,6,6a,7,9,10-hexahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C[C@@H]1[C@H]2CCc3c(nc(nc3[C@]2(C)CC(C#N)C1=O)-c1ccnc(C)c1)-c1ccc(F)cc1 LNCCPNVKXMXVRD-BRLBNAAPSA-N 0.000 description 1
- VIKHZNFBSDFCPM-KTJLQDPHSA-N (6aR,7R,10aR)-4-(4-fluorophenyl)-7,10a-dimethyl-2-(2-methylpyridin-4-yl)-8-oxo-5,6,6a,7,9,10-hexahydrobenzo[h]quinazoline-9-carboxamide Chemical compound O=C1C(C(=O)N)C[C@]2(C3=NC(=NC(C4=CC=C(F)C=C4)=C3CC[C@@H]2[C@H]1C)C1=CC=NC(=C1)C)C VIKHZNFBSDFCPM-KTJLQDPHSA-N 0.000 description 1
- SELICGZYAMKPIA-ASNKJTAVSA-N (6aR,7R,10aR)-4-methoxy-7,10a-dimethyl-2-pyridin-4-yl-5,6,6a,7-tetrahydrobenzo[h]quinazolin-8-one Chemical compound COc1nc(nc2c1CC[C@@H]1[C@@H](C)C(=O)C=C[C@@]21C)-c1ccncc1 SELICGZYAMKPIA-ASNKJTAVSA-N 0.000 description 1
- PQTRAVHVNAORMS-LNHOJHAFSA-N (6aR,7R,10aR)-8-hydroxy-7,10a-dimethyl-4-phenyl-2-pyridin-4-yl-6,6a,7,10-tetrahydro-5H-benzo[h]quinazoline-9-carbonitrile Chemical compound C[C@@H]1[C@H]2CCc3c(nc(nc3[C@]2(C)CC(C#N)=C1O)-c1ccncc1)-c1ccccc1 PQTRAVHVNAORMS-LNHOJHAFSA-N 0.000 description 1
- YLKKCMWFHXWXJE-TXKHULRWSA-N (6aR,7R,10aS)-2,4-bis(2-fluorophenyl)-7,10a-dimethyl-8-oxo-5,6,6a,7-tetrahydrobenzo[h]quinazoline-9-carbonitrile Chemical compound C[C@@H]1[C@H]2CCc3c(nc(nc3[C@]2(C)C=C(C#N)C1=O)-c1ccccc1F)-c1ccccc1F YLKKCMWFHXWXJE-TXKHULRWSA-N 0.000 description 1
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| TWI623548B (zh) | 2012-04-27 | 2018-05-11 | 瑞塔醫藥有限責任公司 | 齊墩果酸（ｂａｒｄｏｘｏｌｏｎｅ ｍｅｔｈｙｌ）之２，２-二氟基丙醯胺衍生物、多晶型及其使用方法 |
| EP3256451B1 (en) * | 2015-02-12 | 2021-10-20 | Reata Pharmaceuticals, Inc. | Imidazolyl tricyclic enones as antioxidant inflammation modulators |
| EP3640251B1 (en) | 2016-10-24 | 2021-12-08 | Astrazeneca AB | 6,7,8,9-tetrahydro-3h-pyrazolo[4,3-f]isoquinoline derivatives useful in the treatment of cancer |
| TWI831738B (zh) * | 2016-12-16 | 2024-02-11 | 美商瑞塔醫藥有限責任公司 | 用於抑制ＲＯＲγ及其他用途的嘧啶三環烯酮衍生物 |
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| US12060340B2 (en) | 2018-06-20 | 2024-08-13 | Reata Pharmaceuticals, Inc | Cysteine-dependent inverse agonists of nuclear receptors ROR-gamma/ROR-gamma-t and methods of treating diseases or disorders therewith |
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