JP2018525353A5 - - Google Patents

Info

Publication number

JP2018525353A5

JP2018525353A5 JP2018500463A JP2018500463A JP2018525353A5 JP 2018525353 A5 JP2018525353 A5 JP 2018525353A5 JP 2018500463 A JP2018500463 A JP 2018500463A JP 2018500463 A JP2018500463 A JP 2018500463A JP 2018525353 A5 JP2018525353 A5 JP 2018525353A5

Authority

JP

Japan

Prior art keywords

alkyl

phenyl

alkoxy

independently selected

substituted

Prior art date

2016-07-08

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.)

Pending

Links

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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 80
• 150000003839 salts Chemical class 0.000 claims description 49
• 150000001875 compounds Chemical class 0.000 claims description 47
• -1 (5-methyl-2-oxo-1,3-dioxol-4-yl) methyl Chemical group 0.000 claims description 28
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 100
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 40
• 125000000217 alkyl group Chemical group 0.000 claims 39
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 21
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 17
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 16
• 125000005843 halogen group Chemical group 0.000 claims 15
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 12
• 229910052799 carbon Inorganic materials 0.000 claims 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims 10
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 9
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 6
• 229910052757 nitrogen Inorganic materials 0.000 claims 6
• 125000006413 ring segment Chemical group 0.000 claims 6
• 229910052736 halogen Inorganic materials 0.000 claims 5
• 150000002367 halogens Chemical class 0.000 claims 5
• 125000004043 oxo group Chemical group O=* 0.000 claims 5
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
• 125000005037 alkyl phenyl group Chemical group 0.000 claims 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
• 201000010099 disease Diseases 0.000 claims 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
• 125000000623 heterocyclic group Chemical group 0.000 claims 4
• 239000000203 mixture Substances 0.000 claims 4
• 229910052760 oxygen Inorganic materials 0.000 claims 4
• 239000001301 oxygen Substances 0.000 claims 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
• 125000003132 pyranosyl group Chemical group 0.000 claims 3
• 230000037390 scarring Effects 0.000 claims 3
• 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 2
• 125000004924 2-naphthylethyl group Chemical group C1=C(C=CC2=CC=CC=C12)CC* 0.000 claims 2
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
• 102000004152 Bone morphogenetic protein 1 Human genes 0.000 claims 2
• 108090000654 Bone morphogenetic protein 1 Proteins 0.000 claims 2
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
• 241000189705 Dunedin group Species 0.000 claims 2
• 206010019280 Heart failures Diseases 0.000 claims 2
• 101000637851 Homo sapiens Tolloid-like protein 1 Proteins 0.000 claims 2
• 101000637850 Homo sapiens Tolloid-like protein 2 Proteins 0.000 claims 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
• 102100031996 Tolloid-like protein 1 Human genes 0.000 claims 2
• 102100031997 Tolloid-like protein 2 Human genes 0.000 claims 2
• 208000020832 chronic kidney disease Diseases 0.000 claims 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
• 230000000694 effects Effects 0.000 claims 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
• 125000002950 monocyclic group Chemical group 0.000 claims 2
• 201000006938 muscular dystrophy Diseases 0.000 claims 2
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([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
• 239000008194 pharmaceutical composition Substances 0.000 claims 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
• 229910052717 sulfur Inorganic materials 0.000 claims 2
• 239000011593 sulfur Substances 0.000 claims 2
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
• 208000009304 Acute Kidney Injury Diseases 0.000 claims 1
• 206010006895 Cachexia Diseases 0.000 claims 1
• 208000029147 Collagen-vascular disease Diseases 0.000 claims 1
• 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
• 206010016654 Fibrosis Diseases 0.000 claims 1
• 208000010412 Glaucoma Diseases 0.000 claims 1
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
• 208000002260 Keloid Diseases 0.000 claims 1
• 206010023330 Keloid scar Diseases 0.000 claims 1
• 208000021642 Muscular disease Diseases 0.000 claims 1
• 208000033626 Renal failure acute Diseases 0.000 claims 1
• 206010039710 Scleroderma Diseases 0.000 claims 1
• 208000006011 Stroke Diseases 0.000 claims 1
• 201000011040 acute kidney failure Diseases 0.000 claims 1
• 125000003275 alpha amino acid group Chemical group 0.000 claims 1
• 150000001413 amino acids Chemical group 0.000 claims 1
• 206010003119 arrhythmia Diseases 0.000 claims 1
• 230000007882 cirrhosis Effects 0.000 claims 1
• 208000019425 cirrhosis of liver Diseases 0.000 claims 1
• 208000033679 diabetic kidney disease Diseases 0.000 claims 1
• 210000001508 eye Anatomy 0.000 claims 1
• 230000003176 fibrotic effect Effects 0.000 claims 1
• 210000002216 heart Anatomy 0.000 claims 1
• 125000005842 heteroatom Chemical group 0.000 claims 1
• 206010020871 hypertrophic cardiomyopathy Diseases 0.000 claims 1
• 230000001969 hypertrophic effect Effects 0.000 claims 1
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 1
• 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
• 210000001117 keloid Anatomy 0.000 claims 1
• 210000003734 kidney Anatomy 0.000 claims 1
• 230000003907 kidney function Effects 0.000 claims 1
• 210000004185 liver Anatomy 0.000 claims 1
• 210000004072 lung Anatomy 0.000 claims 1
• 208000020816 lung neoplasm Diseases 0.000 claims 1
• 238000005259 measurement Methods 0.000 claims 1
• 238000000034 method Methods 0.000 claims 1
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
• 201000006417 multiple sclerosis Diseases 0.000 claims 1
• 230000004220 muscle function Effects 0.000 claims 1
• 208000010125 myocardial infarction Diseases 0.000 claims 1
• 125000001624 naphthyl group Chemical group 0.000 claims 1
• 210000000653 nervous system Anatomy 0.000 claims 1
• 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 1
• 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 1
• 230000001575 pathological effect Effects 0.000 claims 1
• 125000003386 piperidinyl group Chemical group 0.000 claims 1
• 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
• 208000001076 sarcopenia Diseases 0.000 claims 1
• 210000002027 skeletal muscle Anatomy 0.000 claims 1
• 210000003491 skin Anatomy 0.000 claims 1
• 208000020431 spinal cord injury Diseases 0.000 claims 1
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
• 238000002054 transplantation Methods 0.000 claims 1
• 230000002792 vascular Effects 0.000 claims 1
• 230000029663 wound healing Effects 0.000 claims 1
• 0 C*1OCCC(C)(C)Oc(ccc(C)c2)c2OCC1 Chemical compound C*1OCCC(C)(C)Oc(ccc(C)c2)c2OCC1 0.000 description 1
• 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1