CA2676066C - Nuclear receptor binding agents - Google Patents

Info

Publication number

CA2676066C

CA2676066C CA2676066A CA2676066A CA2676066C CA 2676066 C CA2676066 C CA 2676066C CA 2676066 A CA2676066 A CA 2676066A CA 2676066 A CA2676066 A CA 2676066A CA 2676066 C CA2676066 C CA 2676066C

Authority

CA

Canada

Prior art keywords

another embodiment

hydroxyphenyl

hydroxy

oxo

compound

Prior art date

2007-01-22

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.)

Expired - Fee Related

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• 108020005497 Nuclear hormone receptor Proteins 0.000 title abstract description 55
• 108020004017 nuclear receptors Proteins 0.000 title abstract description 30
• 239000011230 binding agent Substances 0.000 title abstract description 7
• 102000006255 nuclear receptors Human genes 0.000 title abstract 2
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
• 201000010099 disease Diseases 0.000 claims abstract description 19
• 206010060862 Prostate cancer Diseases 0.000 claims abstract description 9
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 9
• 210000002307 prostate Anatomy 0.000 claims abstract description 8
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 7
• 208000001132 Osteoporosis Diseases 0.000 claims abstract description 7
• 208000035475 disorder Diseases 0.000 claims abstract description 7
• 206010006187 Breast cancer Diseases 0.000 claims abstract description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 4
• 208000008589 Obesity Diseases 0.000 claims abstract description 4
• 235000020824 obesity Nutrition 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 168
• 239000001257 hydrogen Substances 0.000 claims description 132
• 229910052739 hydrogen Inorganic materials 0.000 claims description 132
• 239000000203 mixture Substances 0.000 claims description 128
• -1 -OCOR Chemical group 0.000 claims description 126
• 125000000217 alkyl group Chemical group 0.000 claims description 120
• 150000002431 hydrogen Chemical group 0.000 claims description 93
• 229910052736 halogen Inorganic materials 0.000 claims description 92
• 150000002367 halogens Chemical group 0.000 claims description 92
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 80
• 125000003118 aryl group Chemical group 0.000 claims description 76
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 68
• 150000003839 salts Chemical class 0.000 claims description 56
• 125000003342 alkenyl group Chemical group 0.000 claims description 55
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 55
• 125000001188 haloalkyl group Chemical group 0.000 claims description 55
• 230000000694 effects Effects 0.000 claims description 54
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 50
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 38
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 36
• 210000001519 tissue Anatomy 0.000 claims description 27
• 150000001204 N-oxides Chemical class 0.000 claims description 26
• 210000000988 bone and bone Anatomy 0.000 claims description 18
• 125000004982 dihaloalkyl group Chemical group 0.000 claims description 16
• 125000004385 trihaloalkyl group Chemical group 0.000 claims description 16
• 239000003085 diluting agent Substances 0.000 claims description 14
• 201000001320 Atherosclerosis Diseases 0.000 claims description 9
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 8
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 8
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• 108010010234 HDL Lipoproteins Proteins 0.000 claims description 6
• 102000015779 HDL Lipoproteins Human genes 0.000 claims description 6
• 108010007622 LDL Lipoproteins Proteins 0.000 claims description 6
• 102000007330 LDL Lipoproteins Human genes 0.000 claims description 6
• 230000006378 damage Effects 0.000 claims description 6
• 230000002401 inhibitory effect Effects 0.000 claims description 6
• 150000002632 lipids Chemical class 0.000 claims description 6
• OOOIOILEQULOBV-UHFFFAOYSA-N 4-bromo-6-methoxy-2-(4-methoxyphenyl)isoquinolin-1-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)C2=CC=C(OC)C=C2C(Br)=C1 OOOIOILEQULOBV-UHFFFAOYSA-N 0.000 claims description 5
• 208000006011 Stroke Diseases 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 230000004761 fibrosis Effects 0.000 claims description 5
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• 102000019197 Superoxide Dismutase Human genes 0.000 claims description 4
• 108010012715 Superoxide dismutase Proteins 0.000 claims description 4
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• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 239000002243 precursor Substances 0.000 claims description 4
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• BIUDJVBDYHJCCR-UHFFFAOYSA-N 4-bromo-6-hydroxy-2-(4-hydroxyphenyl)isoquinolin-1-one Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=CC=C(O)C=C2C(Br)=C1 BIUDJVBDYHJCCR-UHFFFAOYSA-N 0.000 claims description 3
• VACHIUUKYZPGPP-UHFFFAOYSA-N 4-bromo-6-hydroxy-2-(4-methoxyphenyl)isoquinolin-1-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)C2=CC=C(O)C=C2C(Br)=C1 VACHIUUKYZPGPP-UHFFFAOYSA-N 0.000 claims description 3
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• 206010060800 Hot flush Diseases 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 206010061218 Inflammation Diseases 0.000 claims description 3
• 208000018737 Parkinson disease Diseases 0.000 claims description 3
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• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 3
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
• HGWDDDLSFZNNPD-UHFFFAOYSA-N [4-(4-bromo-6-methoxy-1-oxoisoquinolin-2-yl)phenyl] acetate Chemical compound C=1C(OC)=CC=C(C2=O)C=1C(Br)=CN2C1=CC=C(OC(C)=O)C=C1 HGWDDDLSFZNNPD-UHFFFAOYSA-N 0.000 claims description 3
• 230000001413 cellular effect Effects 0.000 claims description 3
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• 230000001965 increasing effect Effects 0.000 claims description 3
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• 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
• 239000000543 intermediate Substances 0.000 claims description 3
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• 208000005264 motor neuron disease Diseases 0.000 claims description 3
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• 201000005112 urinary bladder cancer Diseases 0.000 claims description 3
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• NGNFBVGQCAVUCR-UHFFFAOYSA-N 4-bromo-6-hydroxy-2-(4-hydroxy-3-methylphenyl)isoquinolin-1-one Chemical compound C1=C(O)C(C)=CC(N2C(C3=CC=C(O)C=C3C(Br)=C2)=O)=C1 NGNFBVGQCAVUCR-UHFFFAOYSA-N 0.000 claims description 2
• OBMYVDPMHJENSJ-UHFFFAOYSA-N 4-chloro-6,8-dihydroxy-2-(4-hydroxyphenyl)isoquinolin-1-one Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=C(O)C=C(O)C=C2C(Cl)=C1 OBMYVDPMHJENSJ-UHFFFAOYSA-N 0.000 claims description 2
• IWXWZDBKLIOSJS-UHFFFAOYSA-N 5-bromo-6,8-dihydroxy-2-(4-hydroxyphenyl)isoquinolin-1-one Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=C(O)C=C(O)C(Br)=C2C=C1 IWXWZDBKLIOSJS-UHFFFAOYSA-N 0.000 claims description 2
• HKNUGPCAHQCTKA-UHFFFAOYSA-N 8-hydroxy-6-methoxy-2-(4-methoxyphenyl)isoquinolin-1-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)C2=C(O)C=C(OC)C=C2C=C1 HKNUGPCAHQCTKA-UHFFFAOYSA-N 0.000 claims description 2
• 201000004384 Alopecia Diseases 0.000 claims description 2
• 206010006313 Breast tenderness Diseases 0.000 claims description 2
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 2
• 206010007572 Cardiac hypertrophy Diseases 0.000 claims description 2
• 208000006029 Cardiomegaly Diseases 0.000 claims description 2
• 208000008964 Chemical and Drug Induced Liver Injury Diseases 0.000 claims description 2
• 206010012289 Dementia Diseases 0.000 claims description 2
• 206010019280 Heart failures Diseases 0.000 claims description 2
• 206010019799 Hepatitis viral Diseases 0.000 claims description 2
• 208000023105 Huntington disease Diseases 0.000 claims description 2
• 206010020772 Hypertension Diseases 0.000 claims description 2
• 206010025323 Lymphomas Diseases 0.000 claims description 2
• 206010063493 Premature ageing Diseases 0.000 claims description 2
• 208000032038 Premature aging Diseases 0.000 claims description 2
• 206010054880 Vascular insufficiency Diseases 0.000 claims description 2
• 206010003246 arthritis Diseases 0.000 claims description 2
• 208000026106 cerebrovascular disease Diseases 0.000 claims description 2
• 230000002526 effect on cardiovascular system Effects 0.000 claims description 2
• 208000024963 hair loss Diseases 0.000 claims description 2
• 230000003676 hair loss Effects 0.000 claims description 2
• 201000001421 hyperglycemia Diseases 0.000 claims description 2
• 208000017169 kidney disease Diseases 0.000 claims description 2
• 230000003902 lesion Effects 0.000 claims description 2
• 208000032839 leukemia Diseases 0.000 claims description 2
• 230000009245 menopause Effects 0.000 claims description 2
• 208000021046 prostate intraepithelial neoplasia Diseases 0.000 claims description 2
• 208000024891 symptom Diseases 0.000 claims description 2
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 2
• 208000023577 vascular insufficiency disease Diseases 0.000 claims description 2
• 201000001862 viral hepatitis Diseases 0.000 claims description 2
• 208000004930 Fatty Liver Diseases 0.000 claims 2
• 206010019708 Hepatic steatosis Diseases 0.000 claims 2
• 208000017442 Retinal disease Diseases 0.000 claims 2
• 206010038923 Retinopathy Diseases 0.000 claims 2
• 208000010706 fatty liver disease Diseases 0.000 claims 2
• 208000002780 macular degeneration Diseases 0.000 claims 2
• 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 2
• 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 2
• 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
• 231100000240 steatosis hepatitis Toxicity 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• TVOCNPSVVIIQRF-LZCJLJQNSA-N (e)-3-[6,8-dihydroxy-2-(4-hydroxyphenyl)-1-oxoisoquinolin-4-yl]prop-2-enoic acid Chemical compound O=C1C2=C(O)C=C(O)C=C2C(/C=C/C(=O)O)=CN1C1=CC=C(O)C=C1 TVOCNPSVVIIQRF-LZCJLJQNSA-N 0.000 claims 1
• RQUQUZXEFIIGJT-UNXLUWIOSA-N (e)-3-[6-hydroxy-2-(4-hydroxyphenyl)-1-oxoisoquinolin-4-yl]prop-2-enoic acid Chemical compound O=C1C2=CC=C(O)C=C2C(/C=C/C(=O)O)=CN1C1=CC=C(O)C=C1 RQUQUZXEFIIGJT-UNXLUWIOSA-N 0.000 claims 1
• KJAKOSACJWWFAE-UHFFFAOYSA-N 2-(3-fluoro-4-hydroxyphenyl)-6,8-dihydroxy-1-oxoisoquinoline-4-carbonitrile Chemical compound C=1C(O)=CC(O)=C(C2=O)C=1C(C#N)=CN2C1=CC=C(O)C(F)=C1 KJAKOSACJWWFAE-UHFFFAOYSA-N 0.000 claims 1
• HIMXYYUQWXTNIB-UHFFFAOYSA-N 2-(3-fluoro-4-hydroxyphenyl)-6,8-dihydroxyisoquinolin-1-one Chemical compound C=1C(O)=CC(O)=C(C2=O)C=1C=CN2C1=CC=C(O)C(F)=C1 HIMXYYUQWXTNIB-UHFFFAOYSA-N 0.000 claims 1
• CYOPMEZSMPDHMG-UHFFFAOYSA-N 2-(3-fluoro-4-hydroxyphenyl)-6-hydroxy-4-iodoisoquinolin-1-one Chemical compound C=1C(O)=CC=C(C2=O)C=1C(I)=CN2C1=CC=C(O)C(F)=C1 CYOPMEZSMPDHMG-UHFFFAOYSA-N 0.000 claims 1
• YZBDHJCQDCMPRH-UHFFFAOYSA-N 2-(3-fluoro-4-hydroxyphenyl)-8-hydroxy-6-methoxyisoquinolin-1-one Chemical compound C=1C(OC)=CC(O)=C(C2=O)C=1C=CN2C1=CC=C(O)C(F)=C1 YZBDHJCQDCMPRH-UHFFFAOYSA-N 0.000 claims 1
• VQWVUJRCBBKKQM-UHFFFAOYSA-N 4,5-dibromo-2-(3,5-dibromo-4-hydroxyphenyl)-6-hydroxyisoquinolin-1-one Chemical compound BrC=1C(O)=CC=C(C2=O)C=1C(Br)=CN2C1=CC(Br)=C(O)C(Br)=C1 VQWVUJRCBBKKQM-UHFFFAOYSA-N 0.000 claims 1
• MEDJRANHIIJXIE-UHFFFAOYSA-N 4,5-dibromo-6,8-dihydroxy-2-(4-hydroxyphenyl)isoquinolin-1-one Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=C(O)C=C(O)C(Br)=C2C(Br)=C1 MEDJRANHIIJXIE-UHFFFAOYSA-N 0.000 claims 1
• AOIOAHVABNCLAJ-UHFFFAOYSA-N 4-(1,2-dibromoethyl)-6-hydroxy-2-(4-hydroxyphenyl)isoquinolin-1-one Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=CC=C(O)C=C2C(C(Br)CBr)=C1 AOIOAHVABNCLAJ-UHFFFAOYSA-N 0.000 claims 1
• TYWJUKOBNZCZNP-UHFFFAOYSA-N 4-bromo-2-(3-fluoro-4-hydroxyphenyl)-6,8-dihydroxyisoquinolin-1-one Chemical compound C=1C(O)=CC(O)=C(C2=O)C=1C(Br)=CN2C1=CC=C(O)C(F)=C1 TYWJUKOBNZCZNP-UHFFFAOYSA-N 0.000 claims 1
• CJNRHMOCAFYPNU-UHFFFAOYSA-N 4-bromo-2-(3-fluoro-4-hydroxyphenyl)-6-hydroxyisoquinolin-1-one Chemical compound C=1C(O)=CC=C(C2=O)C=1C(Br)=CN2C1=CC=C(O)C(F)=C1 CJNRHMOCAFYPNU-UHFFFAOYSA-N 0.000 claims 1
• JHMDJCQHWGALEV-UHFFFAOYSA-N 4-bromo-2-(4-hydroxyphenyl)-6-methoxyisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C2=O)C=1C(Br)=CN2C1=CC=C(O)C=C1 JHMDJCQHWGALEV-UHFFFAOYSA-N 0.000 claims 1
• IYKXSJBWAQMFEC-UHFFFAOYSA-N 4-bromo-6-hydroxy-2-(4-hydroxyphenyl)-1-oxoisoquinoline-8-carbonitrile Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=C(C#N)C=C(O)C=C2C(Br)=C1 IYKXSJBWAQMFEC-UHFFFAOYSA-N 0.000 claims 1
• RMCDCECZLOHHME-UHFFFAOYSA-N 4-bromo-6-hydroxy-2-(4-hydroxyphenyl)-1-oxoisoquinoline-8-carboxamide Chemical compound O=C1C=2C(C(=N)O)=CC(O)=CC=2C(Br)=CN1C1=CC=C(O)C=C1 RMCDCECZLOHHME-UHFFFAOYSA-N 0.000 claims 1
• MEUSXTGMSNLMBW-UHFFFAOYSA-N 4-bromo-6-hydroxy-2-(4-hydroxyphenyl)-1-oxoisoquinoline-8-carboxylic acid Chemical compound O=C1C=2C(C(=O)O)=CC(O)=CC=2C(Br)=CN1C1=CC=C(O)C=C1 MEUSXTGMSNLMBW-UHFFFAOYSA-N 0.000 claims 1
• FSCSPCCXODGFCH-UHFFFAOYSA-N 4-bromo-6-methoxy-2-(4-methoxyphenyl)-1-oxoisoquinoline-8-carbonitrile Chemical compound C1=CC(OC)=CC=C1N1C(=O)C2=C(C#N)C=C(OC)C=C2C(Br)=C1 FSCSPCCXODGFCH-UHFFFAOYSA-N 0.000 claims 1
• KDIJFTYBJBYCJT-UHFFFAOYSA-N 4-bromo-8-ethenyl-6-hydroxy-2-(4-hydroxyphenyl)isoquinolin-1-one Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=C(C=C)C=C(O)C=C2C(Br)=C1 KDIJFTYBJBYCJT-UHFFFAOYSA-N 0.000 claims 1
• QJLDXJQEOCNNNN-UHFFFAOYSA-N 4-bromo-8-hydroxy-2-(4-hydroxyphenyl)-6-methoxyisoquinolin-1-one Chemical compound C=1C(OC)=CC(O)=C(C2=O)C=1C(Br)=CN2C1=CC=C(O)C=C1 QJLDXJQEOCNNNN-UHFFFAOYSA-N 0.000 claims 1
• AZVDUDPENBFRBD-UHFFFAOYSA-N 4-chloro-2-(3-fluoro-4-hydroxyphenyl)-6-hydroxyisoquinolin-1-one Chemical compound C=1C(O)=CC=C(C2=O)C=1C(Cl)=CN2C1=CC=C(O)C(F)=C1 AZVDUDPENBFRBD-UHFFFAOYSA-N 0.000 claims 1
• DOIDLZJLHMHFHM-UHFFFAOYSA-N 4-chloro-6-hydroxy-2-(4-hydroxyphenyl)-1-oxoisoquinoline-8-carbonitrile Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=C(C#N)C=C(O)C=C2C(Cl)=C1 DOIDLZJLHMHFHM-UHFFFAOYSA-N 0.000 claims 1
• OPZIIRQRKPWJSM-UHFFFAOYSA-N 4-chloro-6-hydroxy-2-(4-hydroxyphenyl)isoquinolin-1-one Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=CC=C(O)C=C2C(Cl)=C1 OPZIIRQRKPWJSM-UHFFFAOYSA-N 0.000 claims 1
• CZBBISPIFFGFNF-UHFFFAOYSA-N 4-chloro-6-methoxy-2-(4-methoxyphenyl)-1-oxoisoquinoline-8-carbonitrile Chemical compound C1=CC(OC)=CC=C1N1C(=O)C2=C(C#N)C=C(OC)C=C2C(Cl)=C1 CZBBISPIFFGFNF-UHFFFAOYSA-N 0.000 claims 1
• UZCGSEMPWJYIKG-UHFFFAOYSA-N 4-ethenyl-2-(3-fluoro-4-hydroxyphenyl)-6,8-dihydroxyisoquinolin-1-one Chemical compound C=1C(O)=CC(O)=C(C2=O)C=1C(C=C)=CN2C1=CC=C(O)C(F)=C1 UZCGSEMPWJYIKG-UHFFFAOYSA-N 0.000 claims 1
• PHJMFHYDJCTEFA-UHFFFAOYSA-N 4-ethenyl-6,8-dihydroxy-2-(4-hydroxyphenyl)isoquinolin-1-one Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=C(O)C=C(O)C=C2C(C=C)=C1 PHJMFHYDJCTEFA-UHFFFAOYSA-N 0.000 claims 1
• PPTSOUXIGWOEEF-UHFFFAOYSA-N 4-ethenyl-6-hydroxy-2-(4-hydroxyphenyl)-1-oxoisoquinoline-8-carbonitrile Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=C(C#N)C=C(O)C=C2C(C=C)=C1 PPTSOUXIGWOEEF-UHFFFAOYSA-N 0.000 claims 1
• DEDJPVYPSZIEAL-UHFFFAOYSA-N 4-ethenyl-6-hydroxy-2-(4-hydroxyphenyl)isoquinolin-1-one Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=CC=C(O)C=C2C(C=C)=C1 DEDJPVYPSZIEAL-UHFFFAOYSA-N 0.000 claims 1
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
• XRAULIOBQVWAHA-UHFFFAOYSA-N 5-bromo-8-hydroxy-2-(4-hydroxyphenyl)-6-methoxyisoquinolin-1-one Chemical compound BrC=1C(OC)=CC(O)=C(C2=O)C=1C=CN2C1=CC=C(O)C=C1 XRAULIOBQVWAHA-UHFFFAOYSA-N 0.000 claims 1
• VZSCCCSZIQBCNZ-UHFFFAOYSA-N 6,8-dihydroxy-2-(4-hydroxyphenyl)-1-oxoisoquinoline-4-carbonitrile Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=C(O)C=C(O)C=C2C(C#N)=C1 VZSCCCSZIQBCNZ-UHFFFAOYSA-N 0.000 claims 1
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• LRLIGCRQCHORKS-UHFFFAOYSA-N 6-hydroxy-2-(4-hydroxyphenyl)-1-oxoisoquinoline-4-carbonitrile Chemical compound C1=CC(O)=CC=C1N1C(=O)C2=CC=C(O)C=C2C(C#N)=C1 LRLIGCRQCHORKS-UHFFFAOYSA-N 0.000 claims 1
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