JP2019526589A5 - - Google Patents
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- JP2019526589A5 JP2019526589A5 JP2019512639A JP2019512639A JP2019526589A5 JP 2019526589 A5 JP2019526589 A5 JP 2019526589A5 JP 2019512639 A JP2019512639 A JP 2019512639A JP 2019512639 A JP2019512639 A JP 2019512639A JP 2019526589 A5 JP2019526589 A5 JP 2019526589A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- small molecule
- disease
- loxl2 inhibitor
- inhibitor according
- 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.)
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- 101001043352 Homo sapiens Lysyl oxidase homolog 2 Proteins 0.000 claims 57
- 102100021948 Lysyl oxidase homolog 2 Human genes 0.000 claims 57
- 239000003112 inhibitor Substances 0.000 claims 53
- 150000003384 small molecules Chemical class 0.000 claims 53
- 239000002253 acid Substances 0.000 claims 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 16
- 201000010099 disease Diseases 0.000 claims 14
- 208000019423 liver disease Diseases 0.000 claims 14
- 206010016654 Fibrosis Diseases 0.000 claims 11
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 10
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 10
- 208000019693 Lung disease Diseases 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 208000029523 Interstitial Lung disease Diseases 0.000 claims 8
- 241000124008 Mammalia Species 0.000 claims 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 8
- 201000010063 epididymitis Diseases 0.000 claims 8
- 230000004761 fibrosis Effects 0.000 claims 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 8
- 208000019425 cirrhosis of liver Diseases 0.000 claims 7
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 6
- 208000017169 kidney disease Diseases 0.000 claims 6
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 6
- 206010028537 myelofibrosis Diseases 0.000 claims 6
- 206010061218 Inflammation Diseases 0.000 claims 5
- 230000004054 inflammatory process Effects 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 4
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 4
- 208000007082 Alcoholic Fatty Liver Diseases 0.000 claims 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims 4
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 4
- 208000026594 alcoholic fatty liver disease Diseases 0.000 claims 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 4
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 4
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 4
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 4
- 208000011580 syndromic disease Diseases 0.000 claims 4
- -1 3-((4- (aminomethyl) -6- (trifluoromethyl) pyridin-2-yl) oxy) phenyl Chemical group 0.000 claims 3
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 3
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 3
- 208000000102 Squamous Cell Carcinoma of Head and Neck Diseases 0.000 claims 3
- 208000003167 cholangitis Diseases 0.000 claims 3
- 230000007882 cirrhosis Effects 0.000 claims 3
- 210000001508 eye Anatomy 0.000 claims 3
- 208000010157 sclerosing cholangitis Diseases 0.000 claims 3
- 201000004595 synovitis Diseases 0.000 claims 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 2
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 claims 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 2
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 2
- AEMOLEFTQBMNLQ-UHFFFAOYSA-N 3,4,5,6-tetrahydroxyoxane-2-carboxylic acid Chemical compound OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 claims 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 2
- UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 claims 2
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- 208000009304 Acute Kidney Injury Diseases 0.000 claims 2
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 2
- 206010008609 Cholangitis sclerosing Diseases 0.000 claims 2
- 241000723347 Cinnamomum Species 0.000 claims 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- YVECGMZCTULTIS-HSUXUTPPSA-N D-galactal Chemical compound OC[C@H]1OC=C[C@@H](O)[C@H]1O YVECGMZCTULTIS-HSUXUTPPSA-N 0.000 claims 2
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- 208000004145 Endometritis Diseases 0.000 claims 2
- 208000004232 Enteritis Diseases 0.000 claims 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims 2
- 208000031071 Hamman-Rich Syndrome Diseases 0.000 claims 2
- 241000711549 Hepacivirus C Species 0.000 claims 2
- 206010019799 Hepatitis viral Diseases 0.000 claims 2
- 208000002972 Hepatolenticular Degeneration Diseases 0.000 claims 2
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 2
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims 2
- 239000005639 Lauric acid Substances 0.000 claims 2
- 208000009525 Myocarditis Diseases 0.000 claims 2
- 229910002651 NO3 Inorganic materials 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 2
- 239000005642 Oleic acid Substances 0.000 claims 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- 235000021314 Palmitic acid Nutrition 0.000 claims 2
- 206010035664 Pneumonia Diseases 0.000 claims 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 2
- 208000033626 Renal failure acute Diseases 0.000 claims 2
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims 2
- 206010039710 Scleroderma Diseases 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 206010042953 Systemic sclerosis Diseases 0.000 claims 2
- 208000018839 Wilson disease Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 201000004073 acute interstitial pneumonia Diseases 0.000 claims 2
- 201000011040 acute kidney failure Diseases 0.000 claims 2
- 239000001361 adipic acid Substances 0.000 claims 2
- 235000011037 adipic acid Nutrition 0.000 claims 2
- 206010064930 age-related macular degeneration Diseases 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 2
- 229960004909 aminosalicylic acid Drugs 0.000 claims 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 2
- 235000010323 ascorbic acid Nutrition 0.000 claims 2
- 229960005070 ascorbic acid Drugs 0.000 claims 2
- 239000011668 ascorbic acid Substances 0.000 claims 2
- 235000003704 aspartic acid Nutrition 0.000 claims 2
- YINMBLWEHNCLFF-UHFFFAOYSA-N benzenesulfonic acid;benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OS(=O)(=O)C1=CC=CC=C1 YINMBLWEHNCLFF-UHFFFAOYSA-N 0.000 claims 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 2
- RLDQYSHDFVSAPL-UHFFFAOYSA-L calcium;dithiocyanate Chemical compound [Ca+2].[S-]C#N.[S-]C#N RLDQYSHDFVSAPL-UHFFFAOYSA-L 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 239000001569 carbon dioxide Substances 0.000 claims 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 2
- 235000017803 cinnamon Nutrition 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 201000009805 cryptogenic organizing pneumonia Diseases 0.000 claims 2
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 claims 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims 2
- HABLENUWIZGESP-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O.CCCCCCCCCC(O)=O HABLENUWIZGESP-UHFFFAOYSA-N 0.000 claims 2
- NXMUXTAGFPJGTQ-UHFFFAOYSA-N decanoic acid;octanoic acid Chemical compound CCCCCCCC(O)=O.CCCCCCCCCC(O)=O NXMUXTAGFPJGTQ-UHFFFAOYSA-N 0.000 claims 2
- 201000001981 dermatomyositis Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 claims 2
- 229940043264 dodecyl sulfate Drugs 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- RATDTFKSUHXONC-UHFFFAOYSA-N ethanesulfonic acid;formic acid Chemical compound OC=O.CCS(O)(=O)=O RATDTFKSUHXONC-UHFFFAOYSA-N 0.000 claims 2
- 239000001530 fumaric acid Substances 0.000 claims 2
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 claims 2
- 239000000174 gluconic acid Substances 0.000 claims 2
- 235000012208 gluconic acid Nutrition 0.000 claims 2
- 229930195712 glutamate Natural products 0.000 claims 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 2
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims 2
- 229940099563 lactobionic acid Drugs 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 201000003265 lymphadenitis Diseases 0.000 claims 2
- 208000002780 macular degeneration Diseases 0.000 claims 2
- 239000011976 maleic acid Substances 0.000 claims 2
- 239000001630 malic acid Substances 0.000 claims 2
- 235000011090 malic acid Nutrition 0.000 claims 2
- 229960002510 mandelic acid Drugs 0.000 claims 2
- 125000005341 metaphosphate group Chemical group 0.000 claims 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims 2
- NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 claims 2
- 229940005650 monomethyl fumarate Drugs 0.000 claims 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 2
- 201000008383 nephritis Diseases 0.000 claims 2
- 235000001968 nicotinic acid Nutrition 0.000 claims 2
- 229960003512 nicotinic acid Drugs 0.000 claims 2
- 239000011664 nicotinic acid Substances 0.000 claims 2
- 201000004071 non-specific interstitial pneumonia Diseases 0.000 claims 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 claims 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 2
- 206010034674 peritonitis Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 claims 2
- 208000003476 primary myelofibrosis Diseases 0.000 claims 2
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- 235000019260 propionic acid Nutrition 0.000 claims 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 229960004889 salicylic acid Drugs 0.000 claims 2
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 2
- 229940095064 tartrate Drugs 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 201000001862 viral hepatitis Diseases 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- WWGCKRAFNGJJGY-UHFFFAOYSA-N 3-fluoro-4-hydroxypyrrolidine-1-carbaldehyde Chemical compound FC1CN(CC1O)C=O WWGCKRAFNGJJGY-UHFFFAOYSA-N 0.000 claims 1
- 208000007122 AIDS-Associated Nephropathy Diseases 0.000 claims 1
- 208000026872 Addison Disease Diseases 0.000 claims 1
- 201000004384 Alopecia Diseases 0.000 claims 1
- 208000024985 Alport syndrome Diseases 0.000 claims 1
- 206010001881 Alveolar proteinosis Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims 1
- 206010003694 Atrophy Diseases 0.000 claims 1
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims 1
- 208000023328 Basedow disease Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 208000002177 Cataract Diseases 0.000 claims 1
- 206010009346 Clonus Diseases 0.000 claims 1
- 208000015943 Coeliac disease Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 206010010996 Corneal degeneration Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 201000003066 Diffuse Scleroderma Diseases 0.000 claims 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 1
- 206010013774 Dry eye Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 208000032027 Essential Thrombocythemia Diseases 0.000 claims 1
- 208000004930 Fatty Liver Diseases 0.000 claims 1
- 208000007882 Gastritis Diseases 0.000 claims 1
- 208000005577 Gastroenteritis Diseases 0.000 claims 1
- 206010061979 Genital pain Diseases 0.000 claims 1
- 208000007465 Giant cell arteritis Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 208000024869 Goodpasture syndrome Diseases 0.000 claims 1
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| US20210002641A1 (en) * | 2018-03-16 | 2021-01-07 | The Regents Of The University Of Michigan | Compositions and methods for treating graves disease |
| CN112441916A (zh) * | 2019-08-29 | 2021-03-05 | 广东药科大学 | 新型苯乙酸衍生物、其制备方法及其作为药物的用途 |
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| CN112662763A (zh) * | 2020-03-10 | 2021-04-16 | 博尔诚（北京）科技有限公司 | 一种检测常见两性癌症的探针组合物 |
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