JP2013542937A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013542937A5 JP2013542937A5 JP2013532965A JP2013532965A JP2013542937A5 JP 2013542937 A5 JP2013542937 A5 JP 2013542937A5 JP 2013532965 A JP2013532965 A JP 2013532965A JP 2013532965 A JP2013532965 A JP 2013532965A JP 2013542937 A5 JP2013542937 A5 JP 2013542937A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxyquinolin
- benzoic acid
- fluoro
- chloro
- acid
- 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
Links
- 206010067125 Liver injury Diseases 0.000 claims description 9
- 231100000753 hepatic injury Toxicity 0.000 claims description 9
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
- 208000004852 Lung Injury Diseases 0.000 claims description 6
- 206010069363 Traumatic lung injury Diseases 0.000 claims description 6
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 230000000302 ischemic effect Effects 0.000 claims description 5
- 231100000515 lung injury Toxicity 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 210000004072 lung Anatomy 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 3
- 206010021143 Hypoxia Diseases 0.000 claims description 3
- 208000032376 Lung infection Diseases 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 208000018875 hypoxemia Diseases 0.000 claims description 3
- 210000002460 smooth muscle Anatomy 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 11
- 208000019693 Lung disease Diseases 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- -1 chloro, fluoro, methyl Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- BXSZILNGNMDGSL-UHFFFAOYSA-N 3-chloro-4-(6-hydroxyquinolin-2-yl)benzoic acid Chemical compound ClC1=CC(C(=O)O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=N1 BXSZILNGNMDGSL-UHFFFAOYSA-N 0.000 claims 2
- QBSJAWWJFAPLFX-UHFFFAOYSA-N 3-fluoro-4-(6-hydroxyquinolin-2-yl)benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=N1 QBSJAWWJFAPLFX-UHFFFAOYSA-N 0.000 claims 2
- DSXMXYLVWMGWLL-UHFFFAOYSA-N 4-(6-hydroxyquinolin-2-yl)-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=N1 DSXMXYLVWMGWLL-UHFFFAOYSA-N 0.000 claims 2
- 208000008964 Chemical and Drug Induced Liver Injury Diseases 0.000 claims 2
- 206010072268 Drug-induced liver injury Diseases 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- KYNFTSBRGSYFPB-UHFFFAOYSA-N 1-(6-hydroxyquinolin-2-yl)piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=CC=C(C=C(O)C=C2)C2=N1 KYNFTSBRGSYFPB-UHFFFAOYSA-N 0.000 claims 1
- TXLKITDWTKXJCW-UHFFFAOYSA-N 1-[6-hydroxy-3-(trifluoromethyl)quinolin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=NC2=CC=C(O)C=C2C=C1C(F)(F)F TXLKITDWTKXJCW-UHFFFAOYSA-N 0.000 claims 1
- YLROCXBICGTVLO-UHFFFAOYSA-N 2-[2-chloro-4-(2H-tetrazol-5-yl)phenyl]quinolin-6-ol Chemical compound C1=CC2=CC(O)=CC=C2N=C1C(C(=C1)Cl)=CC=C1C=1N=NNN=1 YLROCXBICGTVLO-UHFFFAOYSA-N 0.000 claims 1
- WHBYFIFOBBQFIY-UHFFFAOYSA-N 2-[4-(2H-tetrazol-5-yl)phenyl]quinolin-6-ol Chemical compound C1=CC2=CC(O)=CC=C2N=C1C(C=C1)=CC=C1C1=NN=NN1 WHBYFIFOBBQFIY-UHFFFAOYSA-N 0.000 claims 1
- FSDMLPDPZZBXJD-UHFFFAOYSA-N 2-[5-(2H-tetrazol-5-yl)thiophen-2-yl]quinolin-6-ol Chemical compound C1=CC2=CC(O)=CC=C2N=C1C(S1)=CC=C1C=1N=NNN=1 FSDMLPDPZZBXJD-UHFFFAOYSA-N 0.000 claims 1
- UQFNJNUIXIBWMP-UHFFFAOYSA-N 2-chloro-4-(6-hydroxyquinolin-2-yl)benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=N1 UQFNJNUIXIBWMP-UHFFFAOYSA-N 0.000 claims 1
- PQANLCZDWHCJKJ-UHFFFAOYSA-N 2-fluoro-4-(6-hydroxyquinolin-2-yl)benzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=N1 PQANLCZDWHCJKJ-UHFFFAOYSA-N 0.000 claims 1
- NLDYTNQECLZWGE-UHFFFAOYSA-N 3-(dimethylamino)-4-(6-hydroxyquinolin-2-yl)benzoic acid Chemical compound CN(C)C1=CC(C(O)=O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=N1 NLDYTNQECLZWGE-UHFFFAOYSA-N 0.000 claims 1
- CRCLAUGZWXVRJF-UHFFFAOYSA-N 3-[2-fluoro-4-(6-hydroxyquinolin-2-yl)phenyl]-4H-1,2,4-oxadiazol-5-one Chemical compound C1=CC2=CC(O)=CC=C2N=C1C(C=C1F)=CC=C1C1=NOC(=O)N1 CRCLAUGZWXVRJF-UHFFFAOYSA-N 0.000 claims 1
- IVNVKLHFXHTCNU-UHFFFAOYSA-N 3-[3-fluoro-4-(6-hydroxyquinolin-2-yl)phenyl]-4H-1,2,4-oxadiazol-5-one Chemical compound C1=CC2=CC(O)=CC=C2N=C1C(C(=C1)F)=CC=C1C1=NOC(=O)N1 IVNVKLHFXHTCNU-UHFFFAOYSA-N 0.000 claims 1
- OOYHFBKYJFCMLH-UHFFFAOYSA-N 3-[4-(6-hydroxyquinolin-2-yl)phenyl]-4H-1,2,4-oxadiazol-5-one Chemical compound C1=CC2=CC(O)=CC=C2N=C1C(C=C1)=CC=C1C1=NC(=O)ON1 OOYHFBKYJFCMLH-UHFFFAOYSA-N 0.000 claims 1
- KUMJGMYZGRNHGX-UHFFFAOYSA-N 3-[4-(6-hydroxyquinolin-2-yl)phenyl]-4H-1,2,4-thiadiazol-5-one Chemical compound C1=CC2=CC(O)=CC=C2N=C1C(C=C1)=CC=C1C1=NC(=O)SN1 KUMJGMYZGRNHGX-UHFFFAOYSA-N 0.000 claims 1
- AXNXNPCHIBNRCD-UHFFFAOYSA-N 3-bromo-4-(6-hydroxyquinolin-2-yl)benzoic acid Chemical compound BrC1=CC(C(=O)O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=N1 AXNXNPCHIBNRCD-UHFFFAOYSA-N 0.000 claims 1
- AAIJLPWMZBMAPY-UHFFFAOYSA-N 3-chloro-4-(4-fluoro-6-hydroxyquinolin-2-yl)benzoic acid Chemical compound ClC1=CC(C(=O)O)=CC=C1C1=CC(F)=C(C=C(O)C=C2)C2=N1 AAIJLPWMZBMAPY-UHFFFAOYSA-N 0.000 claims 1
- QFJKNSTZTGHVHM-UHFFFAOYSA-N 3-chloro-4-(6-hydroxy-1-oxidoquinolin-1-ium-2-yl)benzoic acid Chemical compound ClC1=CC(C(=O)O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=[N+]1[O-] QFJKNSTZTGHVHM-UHFFFAOYSA-N 0.000 claims 1
- BYUKSIDDKOUZKF-UHFFFAOYSA-N 3-cyano-4-(6-hydroxyquinolin-2-yl)benzoic acid Chemical compound N#CC1=CC(C(=O)O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=N1 BYUKSIDDKOUZKF-UHFFFAOYSA-N 0.000 claims 1
- CHWJSWQWPMDIDJ-UHFFFAOYSA-N 3-fluoro-4-(4-fluoro-6-hydroxyquinolin-2-yl)benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C1=CC(F)=C(C=C(O)C=C2)C2=N1 CHWJSWQWPMDIDJ-UHFFFAOYSA-N 0.000 claims 1
- VCVOHFUPSSJRNW-UHFFFAOYSA-N 3-methyl-2-[4-(2H-tetrazol-5-yl)phenyl]quinolin-6-ol Chemical compound CC1=CC2=CC(O)=CC=C2N=C1C(C=C1)=CC=C1C1=NN=NN1 VCVOHFUPSSJRNW-UHFFFAOYSA-N 0.000 claims 1
- WBKISECURIAWNU-UHFFFAOYSA-N 4-(3-chloro-6-hydroxyquinolin-2-yl)-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C1=NC2=CC=C(O)C=C2C=C1Cl WBKISECURIAWNU-UHFFFAOYSA-N 0.000 claims 1
- YUAOFVPYZSAZBA-UHFFFAOYSA-N 4-(3-chloro-6-hydroxyquinolin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC2=CC=C(O)C=C2C=C1Cl YUAOFVPYZSAZBA-UHFFFAOYSA-N 0.000 claims 1
- NAKRTRONOIFMGC-UHFFFAOYSA-N 4-(3-cyano-6-hydroxyquinolin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC2=CC=C(O)C=C2C=C1C#N NAKRTRONOIFMGC-UHFFFAOYSA-N 0.000 claims 1
- KRMMONRQAIUDMV-UHFFFAOYSA-N 4-(3-fluoro-6-hydroxyquinolin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC2=CC=C(O)C=C2C=C1F KRMMONRQAIUDMV-UHFFFAOYSA-N 0.000 claims 1
- UXQWLOSKDHZWEO-UHFFFAOYSA-N 4-(4-chloro-3-fluoro-6-hydroxyquinolin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC2=CC=C(O)C=C2C(Cl)=C1F UXQWLOSKDHZWEO-UHFFFAOYSA-N 0.000 claims 1
- OCZNMARRFYIIJG-UHFFFAOYSA-N 4-(4-chloro-6-hydroxyquinolin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC(Cl)=C(C=C(O)C=C2)C2=N1 OCZNMARRFYIIJG-UHFFFAOYSA-N 0.000 claims 1
- ABLFLWUTFZYODT-UHFFFAOYSA-N 4-(4-fluoro-6-hydroxyquinolin-2-yl)-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1C1=CC(F)=C(C=C(O)C=C2)C2=N1 ABLFLWUTFZYODT-UHFFFAOYSA-N 0.000 claims 1
- MAOHQVURAXYWNQ-UHFFFAOYSA-N 4-(4-fluoro-6-hydroxyquinolin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC(F)=C(C=C(O)C=C2)C2=N1 MAOHQVURAXYWNQ-UHFFFAOYSA-N 0.000 claims 1
- NEARSXGUJANBAQ-UHFFFAOYSA-N 4-(5-bromo-6-hydroxyquinolin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(Br)=C(O)C=C2)C2=N1 NEARSXGUJANBAQ-UHFFFAOYSA-N 0.000 claims 1
- YVCYIJMGNZWISV-UHFFFAOYSA-N 4-(5-chloro-6-hydroxyquinolin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(Cl)=C(O)C=C2)C2=N1 YVCYIJMGNZWISV-UHFFFAOYSA-N 0.000 claims 1
- HHGLVSDQIATOMW-UHFFFAOYSA-N 4-(5-fluoro-6-hydroxyquinolin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(F)=C(O)C=C2)C2=N1 HHGLVSDQIATOMW-UHFFFAOYSA-N 0.000 claims 1
- MXOCZSLXESCHIM-UHFFFAOYSA-N 4-(6-hydroxy-1-oxidoquinolin-1-ium-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=[N+]1[O-] MXOCZSLXESCHIM-UHFFFAOYSA-N 0.000 claims 1
- XBWKWSRTMBNUFA-UHFFFAOYSA-N 4-(6-hydroxy-3-methylquinolin-2-yl)benzoic acid Chemical compound CC1=CC2=CC(O)=CC=C2N=C1C1=CC=C(C(O)=O)C=C1 XBWKWSRTMBNUFA-UHFFFAOYSA-N 0.000 claims 1
- RCIPVMPVYIKZFU-UHFFFAOYSA-N 4-(6-hydroxyquinolin-2-yl)-3-(trifluoromethyl)benzoic acid Chemical compound FC(F)(F)C1=CC(C(=O)O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=N1 RCIPVMPVYIKZFU-UHFFFAOYSA-N 0.000 claims 1
- GNLNPVVOJYUSPV-UHFFFAOYSA-N 4-(6-hydroxyquinolin-2-yl)-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=N1 GNLNPVVOJYUSPV-UHFFFAOYSA-N 0.000 claims 1
- ZVOPSHFZQOCHBV-UHFFFAOYSA-N 4-(6-hydroxyquinolin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=N1 ZVOPSHFZQOCHBV-UHFFFAOYSA-N 0.000 claims 1
- UVECQQDHXYMXHQ-UHFFFAOYSA-N 4-(6-hydroxyquinolin-2-yl)cyclohex-3-ene-1-carboxylic acid Chemical compound C1C(C(=O)O)CCC(C=2N=C3C=CC(O)=CC3=CC=2)=C1 UVECQQDHXYMXHQ-UHFFFAOYSA-N 0.000 claims 1
- KYFKVSXTGWAHRT-UHFFFAOYSA-N 4-(8-fluoro-6-hydroxyquinolin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C=C(O)C=C2F)C2=N1 KYFKVSXTGWAHRT-UHFFFAOYSA-N 0.000 claims 1
- XSTGYDUGZGCIGK-UHFFFAOYSA-N 4-[4-(dimethylamino)-6-hydroxyquinolin-2-yl]benzoic acid Chemical compound N=1C2=CC=C(O)C=C2C(N(C)C)=CC=1C1=CC=C(C(O)=O)C=C1 XSTGYDUGZGCIGK-UHFFFAOYSA-N 0.000 claims 1
- RBIDSEHBJRKAGX-UHFFFAOYSA-N 4-[6-hydroxy-3-(trifluoromethyl)quinolin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC2=CC=C(O)C=C2C=C1C(F)(F)F RBIDSEHBJRKAGX-UHFFFAOYSA-N 0.000 claims 1
- HSBQRVLTVCDLAY-UHFFFAOYSA-N 4-chloro-2-[4-(2H-tetrazol-5-yl)phenyl]quinolin-6-ol Chemical compound C1=C(Cl)C2=CC(O)=CC=C2N=C1C(C=C1)=CC=C1C=1N=NNN=1 HSBQRVLTVCDLAY-UHFFFAOYSA-N 0.000 claims 1
- AKWGLUKFDBOKEF-UHFFFAOYSA-N 5-(6-hydroxyquinolin-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=N1 AKWGLUKFDBOKEF-UHFFFAOYSA-N 0.000 claims 1
- VKGYZPPBWRJGHJ-UHFFFAOYSA-N 5-[4-(6-hydroxyquinolin-2-yl)phenyl]-1,2,4-oxadiazol-3-one Chemical compound C1=CC2=CC(O)=CC=C2N=C1C(C=C1)=CC=C1C1=NC(=O)NO1 VKGYZPPBWRJGHJ-UHFFFAOYSA-N 0.000 claims 1
- ZTRLIBRAJQWATA-UHFFFAOYSA-N 5-[4-(6-hydroxyquinolin-2-yl)phenyl]-1,2,4-thiadiazol-3-one Chemical compound C1=CC2=CC(O)=CC=C2N=C1C(C=C1)=CC=C1C1=NC(=O)NS1 ZTRLIBRAJQWATA-UHFFFAOYSA-N 0.000 claims 1
- XMJYYKHBKJAZAI-UHFFFAOYSA-N 5-[4-(6-hydroxyquinolin-2-yl)phenyl]-3H-1,3,4-oxadiazol-2-one Chemical compound C1=CC2=CC(O)=CC=C2N=C1C(C=C1)=CC=C1C1=NNC(=O)O1 XMJYYKHBKJAZAI-UHFFFAOYSA-N 0.000 claims 1
- ZNNJDTUCMLMVFN-UHFFFAOYSA-N 5-[4-(6-hydroxyquinolin-2-yl)phenyl]-3H-1,3,4-thiadiazol-2-one Chemical compound C1=CC2=CC(O)=CC=C2N=C1C(C=C1)=CC=C1C1=NNC(=O)S1 ZNNJDTUCMLMVFN-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 208000035475 disorder Diseases 0.000 description 5
- 201000010099 disease Diseases 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 208000011231 Crohn disease Diseases 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 206010065040 AIDS dementia complex Diseases 0.000 description 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000193163 Clostridioides difficile Species 0.000 description 1
- 208000014997 Crohn colitis Diseases 0.000 description 1
- 208000025962 Crush injury Diseases 0.000 description 1
- 206010056465 Food craving Diseases 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000029523 Interstitial Lung disease Diseases 0.000 description 1
- 208000029549 Muscle injury Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 230000003979 response to food Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 201000002859 sleep apnea Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39122510P | 2010-10-08 | 2010-10-08 | |
| US61/391,225 | 2010-10-08 | ||
| US42380510P | 2010-12-16 | 2010-12-16 | |
| US61/423,805 | 2010-12-16 | ||
| PCT/US2011/055200 WO2012048181A1 (en) | 2010-10-08 | 2011-10-07 | Novel substituted quinoline compounds as s-nitrosoglutathione reductase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015205282A Division JP2016074667A (ja) | 2010-10-08 | 2015-10-19 | Ｓ−ニトロソグルタチオン還元酵素阻害薬としての新規置換キノリン化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013542937A JP2013542937A (ja) | 2013-11-28 |
| JP2013542937A5 true JP2013542937A5 (enExample) | 2015-12-10 |
| JP5855113B2 JP5855113B2 (ja) | 2016-02-09 |
Family
ID=45928135
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013532965A Expired - Fee Related JP5855113B2 (ja) | 2010-10-08 | 2011-10-07 | Ｓ−ニトロソグルタチオン還元酵素阻害薬としての新規置換キノリン化合物 |
| JP2015205282A Pending JP2016074667A (ja) | 2010-10-08 | 2015-10-19 | Ｓ−ニトロソグルタチオン還元酵素阻害薬としての新規置換キノリン化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015205282A Pending JP2016074667A (ja) | 2010-10-08 | 2015-10-19 | Ｓ−ニトロソグルタチオン還元酵素阻害薬としての新規置換キノリン化合物 |
Country Status (23)
| Country | Link |
|---|---|
| US (5) | US8921562B2 (enExample) |
| EP (2) | EP2977050A1 (enExample) |
| JP (2) | JP5855113B2 (enExample) |
| KR (1) | KR101886459B1 (enExample) |
| CN (1) | CN103200820B (enExample) |
| AU (1) | AU2011311920B2 (enExample) |
| BR (1) | BR112013007907A2 (enExample) |
| CA (1) | CA2811791C (enExample) |
| DK (1) | DK2624695T3 (enExample) |
| ES (1) | ES2553771T3 (enExample) |
| HK (1) | HK1215862A1 (enExample) |
| HR (1) | HRP20151405T1 (enExample) |
| HU (1) | HUE025653T2 (enExample) |
| IL (1) | IL223829A (enExample) |
| IN (1) | IN2013MN00501A (enExample) |
| PL (1) | PL2624695T3 (enExample) |
| PT (1) | PT2624695E (enExample) |
| RS (1) | RS54369B1 (enExample) |
| RU (1) | RU2599144C2 (enExample) |
| SI (1) | SI2624695T1 (enExample) |
| SM (1) | SMT201600021B (enExample) |
| WO (1) | WO2012048181A1 (enExample) |
| ZA (1) | ZA201303257B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI2624695T1 (sl) | 2010-10-08 | 2016-01-29 | Nivalis Therapeutics, Inc. | Nove substituirane kinolinske spojine kot inhibitorji S-nitrozoglutation reduktaze |
| WO2012083165A1 (en) | 2010-12-16 | 2012-06-21 | N30 Pharmaceuticals, Llc | Novel substituted bicyclic aromatic compounds as s-nitrosoglutathione reductase inhibitors |
| WO2012170371A1 (en) * | 2011-06-10 | 2012-12-13 | N30 Pharmaceuticals, Llc | Compounds as s-nitrosoglutathione reductase inhibitors |
| EP3204010A1 (en) * | 2014-10-08 | 2017-08-16 | Nivalis Therapeutics, Inc. | Methods for the treatment of cystic fibrosis |
| CN104496998B (zh) * | 2014-12-15 | 2017-07-11 | 陕西嘉禾生物科技股份有限公司 | 一种1′‑苄基‑2′‑酮‑5′，7′，8′‑三氢‑螺‑[1，3‑二氧五环‑2]‑喹啉的制备方法 |
| WO2016128905A1 (en) * | 2015-02-10 | 2016-08-18 | Glenmark Pharmaceuticals S.A. | Thienopyrrole compounds as s-nitrosoglutathione reductase inhibitors |
| US9840513B2 (en) | 2015-07-16 | 2017-12-12 | Abbvie S.Á.R.L. | Substituted tricyclics and method of use |
| WO2017044766A1 (en) | 2015-09-10 | 2017-03-16 | Nivalis Therapeutics, Inc. | Solid forms of an s-nitrosoglutathione reductase inhibitor |
| WO2017044788A1 (en) * | 2015-09-10 | 2017-03-16 | Nivalis Therapeutics, Inc. | Formulations of an s-nitrosoglutathione reductase inhibitor |
| WO2017062611A1 (en) * | 2015-10-07 | 2017-04-13 | Nivalis Therapeutics, Inc. | Methods for the treatment of cystic fibrosis |
| JP6779992B2 (ja) | 2015-10-09 | 2020-11-04 | アッヴィ・エス・ア・エール・エル | Ｎ−スルホニル化ピラゾロ［３，４−ｂ］ピリジン−６−カルボキサミドおよび使用法 |
| BR112018007145A2 (pt) | 2015-10-09 | 2018-11-06 | AbbVie S.à.r.l. | ácidos pirazolo[3,4-b]piridin-6-carboxílicos substituídos e o seu uso |
| CA3000802A1 (en) | 2015-10-09 | 2017-04-13 | Abbvie S.A.R.L. | Compounds for treatment of cystic fibrosis |
| WO2017151725A1 (en) * | 2016-03-03 | 2017-09-08 | Nivalis Therapeutics, Inc. | Formulations of an s-nitrosoglutathione reductase inhibitor |
| BR112018072047A2 (pt) | 2016-04-26 | 2019-02-12 | AbbVie S.à.r.l. | moduladores da proteína reguladora de condutância transmembranar de fibrose cística |
| US10138227B2 (en) | 2016-06-03 | 2018-11-27 | Abbvie S.Á.R.L. | Heteroaryl substituted pyridines and methods of use |
| US9981910B2 (en) | 2016-10-07 | 2018-05-29 | Abbvie S.Á.R.L. | Substituted pyrrolidines and methods of use |
| US10399940B2 (en) | 2016-10-07 | 2019-09-03 | Abbvie S.Á.R.L. | Substituted pyrrolidines and methods of use |
| WO2018116185A1 (en) | 2016-12-20 | 2018-06-28 | AbbVie S.à.r.l. | Deuterated cftr modulators and methods of use |
| TW201831471A (zh) | 2017-02-24 | 2018-09-01 | 盧森堡商艾伯維公司 | 囊腫纖化症跨膜傳導調節蛋白的調節劑及其使用方法 |
| US10988454B2 (en) | 2017-09-14 | 2021-04-27 | Abbvie Overseas S.À.R.L. | Modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| WO2019193062A1 (en) | 2018-04-03 | 2019-10-10 | Abbvie S.Á.R.L | Substituted pyrrolidines and their use |
| CN108794395B (zh) * | 2018-07-06 | 2021-04-20 | 大连理工大学 | 一种2-喹啉酮类化合物的制备方法 |
| EP3747882A1 (en) | 2019-06-03 | 2020-12-09 | AbbVie Overseas S.à r.l. | Prodrug modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| US11236067B2 (en) | 2019-07-12 | 2022-02-01 | Orphomed, Inc. | Compound for treating cystic fibrosis |
| WO2021217028A1 (en) * | 2020-04-23 | 2021-10-28 | University Hospitals - Cleveland Medical Center | Compositions and methods for in vivo lung and blood sno repletion |
| US20220211692A1 (en) | 2021-01-06 | 2022-07-07 | AbbVie Global Enterprises Ltd. | Modulators of the Cystic Fibrosis Transmembrane Conductance Regulator Protein and Methods of Use |
| US20220213041A1 (en) | 2021-01-06 | 2022-07-07 | AbbVie Global Enterprises Ltd. | Modulators of the Cystic Fibrosis Transmembrane Conductance Regulator Protein and Methods of Use |
| WO2025132358A1 (en) | 2023-12-21 | 2025-06-26 | Galapagos Nv | Novel compounds and pharmaceutical compositions thereof for the treatment of infectious diseases |
Family Cites Families (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4431440A (en) | 1981-02-20 | 1984-02-14 | American Cyanamid Company | Method to alter or control the development and/or the life cycle of various plant species |
| US4522811A (en) | 1982-07-08 | 1985-06-11 | Syntex (U.S.A.) Inc. | Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides |
| US5480883A (en) | 1991-05-10 | 1996-01-02 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| DE19517060A1 (de) | 1995-05-10 | 1996-11-14 | Hoechst Ag | 1-Fluorisochinolinderivate und ihre Verwendung in flüssigkristallinen Mischungen |
| DE19517038A1 (de) | 1995-05-10 | 1996-11-14 | Hoechst Ag | 1,8-Difluorisochinolinderivate und ihre Verwendung in flüssigkristallinen Mischungen |
| BR9711805A (pt) | 1996-06-20 | 2002-01-15 | Regents The Univesity Of Texas | Compostos e métodos para providenciar preparações farmacologicamente ativas e uso dos mesmos |
| US6057367A (en) | 1996-08-30 | 2000-05-02 | Duke University | Manipulating nitrosative stress to kill pathologic microbes, pathologic helminths and pathologically proliferating cells or to upregulate nitrosative stress defenses |
| EP0991628B1 (en) | 1997-05-28 | 2005-01-12 | Aventis Pharmaceuticals Inc | QUINOLINE AND QUINOXALINE COMPOUNDS WHICH INHIBIT PLATELET-DERIVED GROWTH FACTOR AND/OR P56lck TYROSINE KINASES |
| US6180632B1 (en) | 1997-05-28 | 2001-01-30 | Aventis Pharmaceuticals Products Inc. | Quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or p56lck tyrosine kinases |
| US6200995B1 (en) | 1998-01-29 | 2001-03-13 | Tularik Inc. | PPAR-γ modulators |
| AU3176800A (en) | 1999-03-30 | 2000-10-16 | British Telecommunications Public Limited Company | Network printing method in apparatus |
| US6608053B2 (en) | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| WO2001083456A1 (en) | 2000-04-27 | 2001-11-08 | Yamanouchi Pharmaceutical Co., Ltd. | Condensed heteroaryl derivatives |
| JP2004510767A (ja) | 2000-10-02 | 2004-04-08 | モレキュラー・プロウブズ・インコーポレーテッド | アルデヒド部分またはケトン部分を有する生物分子を標識するための試薬 |
| US6359182B1 (en) | 2000-10-26 | 2002-03-19 | Duke University | C-nitroso compounds and use thereof |
| US7049308B2 (en) | 2000-10-26 | 2006-05-23 | Duke University | C-nitroso compounds and use thereof |
| US7179791B2 (en) | 2001-01-11 | 2007-02-20 | Duke University | Inhibiting GS-FDH to modulate NO bioactivity |
| JP2002226464A (ja) | 2001-01-30 | 2002-08-14 | Sumitomo Pharmaceut Co Ltd | トリアリール類縁体およびその利用 |
| NZ530198A (en) * | 2001-07-02 | 2005-11-25 | Akzo Nobel Nv | Tetrahydroquinoline derivatives |
| CA2454080A1 (en) | 2001-08-13 | 2003-02-27 | Robert Edward Detlefsen | Ultraviolet light absorbers |
| AT500490A1 (de) | 2001-10-16 | 2006-01-15 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von substituierten thiazolinen und deren zwischenprodukte |
| WO2004035522A1 (ja) | 2002-08-30 | 2004-04-29 | Bf Research Institute, Inc. | プリオン蛋白蓄積性疾患の診断プローブおよび治療薬ならびにプリオン蛋白の染色剤 |
| CA2465554A1 (en) | 2002-12-16 | 2004-06-16 | Bf Research Institute, Inc. | Quinoline derivatives as probes for the diagnosis of diseases in which tau protein accumulates |
| WO2004080170A2 (en) | 2003-03-10 | 2004-09-23 | Basf Aktiengesellschaft | Amino substituted benzo(hetero)cyclic derivatives |
| CL2004000985A1 (es) | 2003-05-16 | 2005-01-14 | Wyeth Corp | Compuestos derivados de fenilquinolinas; composicion farmaceutica, proceso de preparacion; y uso para tratar osteoporosis, enfermedad de paget, dano vascular, osteoartritis, cancer oseo, cancer ovarico, cancer prostatico, hipercolesterolemia, aterosc |
| WO2005000229A2 (en) | 2003-06-04 | 2005-01-06 | Duke University | Compositions and methods for modulating s-nitrosoglutathione reductase |
| AU2003304416A1 (en) | 2003-08-13 | 2005-03-07 | Bf Research Institute, Inc. | Probe for disease with amyloid deposit, amyloid-staining agent, remedy and preventive for disease with amyloid deposit and diagnostic probe and staining agent for neurofibril change |
| US7638519B2 (en) | 2003-12-23 | 2009-12-29 | Myogen, Inc. | Compounds, pharmaceutical compositions, and methods for the treatment of cardiovascular disease |
| ITTO20040125A1 (it) | 2004-03-01 | 2004-06-01 | Rotta Research Lab | Nuove amidine eterocicliche inibitrici la produzione di ossido d'azoto (no) ad attivita' antinfiammatoria ed analgesica |
| WO2005118580A2 (en) | 2004-05-12 | 2005-12-15 | The Government Of The United States Of America As Represented By The Secretary, Department Of Health | Tricyclic compounds as inhibitors of the hypoxic signaling pathway |
| US20060014705A1 (en) | 2004-06-30 | 2006-01-19 | Howitz Konrad T | Compositions and methods for selectively activating human sirtuins |
| WO2006034512A2 (en) * | 2004-09-23 | 2006-03-30 | Bayer Pharmaceuticals Corporation | Phenyl-substituted quinoline and quinazoline compounds for the treatment of diabetes |
| SE0402925D0 (sv) * | 2004-11-30 | 2004-11-30 | Astrazeneca Ab | Novel Compounds |
| JP2008521905A (ja) * | 2004-12-03 | 2008-06-26 | メルク エンド カムパニー インコーポレーテッド | キノリンタキキニン受容体拮抗薬 |
| EP1683523A1 (en) | 2005-01-25 | 2006-07-26 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | 2-Phenylquinoxalines as inhibitors for MPP1 |
| EP1891039A1 (en) | 2005-05-20 | 2008-02-27 | Vertex Pharmaceuticals Incorporated | Quinoline derivatives useful as modulators of ion channels |
| EP2277872B1 (en) | 2005-05-31 | 2016-03-23 | Promega Corporation | Luminogenic and fluorogenic compounds and methods to detect molecules or conditions |
| EP1896461A2 (en) | 2005-06-30 | 2008-03-12 | Amgen Inc. | Bis-aryl kinase inhibitors and their use in the treatment of inflammation, angiogenesis and cancer |
| NZ566180A (en) | 2005-07-29 | 2011-04-29 | Resverlogix Corp | Pharmaceutical compositions for the prevention and treatment of complex diseases and their delivery by insertable medical devices |
| GB0618168D0 (en) | 2006-09-15 | 2006-10-25 | Babraham Inst | Compounds |
| KR101299233B1 (ko) | 2006-10-31 | 2013-08-22 | 삼성디스플레이 주식회사 | 유기 금속 착물 및 이를 이용한 유기 전계 발광 소자 |
| CA2707449A1 (en) | 2006-12-01 | 2009-06-12 | President And Fellows Of Harvard College | Compounds and methods for enzyme-mediated tumor imaging and therapy |
| WO2009008906A2 (en) | 2007-02-06 | 2009-01-15 | The Trustees Of The University Of Pennsylvania | Therapeutic compounds for blocking dna synthesis of pox viruses |
| DE102007015169A1 (de) * | 2007-03-27 | 2008-10-02 | Universität des Saarlandes Campus Saarbrücken | 17Beta-Hydroxysteroid-Dehydrogenase-Typ1-Inhibitoren zur Behandlung hormonabhängiger Erkrankungen |
| BRPI0701664A2 (pt) | 2007-05-28 | 2009-01-13 | Fundacao Universidade Fed De Sco Carlos | 4-quinolinonas e quinolinas, processo de preparaÇço, formulaÇÕes farmacÊuticas e uso das mesmas |
| WO2008157500A1 (en) | 2007-06-17 | 2008-12-24 | Kalypsys, Inc. | Aminoquinazoline cannabinoid receptor modulators for treatment of disease |
| EP2014651A1 (en) | 2007-07-12 | 2009-01-14 | Exonhit Therapeutics SA | Compounds and methods for modulating Rho GTPases |
| WO2009076665A1 (en) | 2007-12-13 | 2009-06-18 | Indiana University Research And Technology Corporation | Materials and methods for inhibiting mammalian s-nitrosoglutathione reductase |
| US20100144733A1 (en) | 2008-04-28 | 2010-06-10 | Institute For Oneworld Health | Compounds, compositions and methods comprising heteroaromatic derivatives |
| WO2010004761A1 (ja) * | 2008-07-10 | 2010-01-14 | 一般社団法人ファルマＩｐ | キノリンカルボキサミド誘導体を有効成分とするｓｔａｔ３阻害剤 |
| WO2010018458A2 (en) | 2008-08-12 | 2010-02-18 | Crystalgenomics, Inc. | Phenol derivatives and methods of use thereof |
| DK2318007T3 (da) | 2008-08-15 | 2013-03-25 | N30 Pharmaceuticals Inc | Nye pyrrol-inhibitorer af s-nitrosoglutathion-reduktase som terapeutiske midler |
| JP2012500219A (ja) * | 2008-08-15 | 2012-01-05 | エヌサーティー・ファーマシューティカルズ，エルエルシー | 治療薬剤としての、ｓ−ニトロソグルタチオンレダクターゼの新規ピロール阻害剤 |
| DK2315590T3 (da) * | 2008-08-15 | 2012-11-19 | N30 Pharmaceuticals Inc | Pyrrolinhibitorer af S-nitrosoglutathionreduktase |
| MX2011004088A (es) * | 2008-10-15 | 2011-09-06 | Kissei Pharmaceutical | Derivado de anillo fusionado y su aplicacion medica. |
| CA2741718A1 (en) | 2008-10-23 | 2010-04-29 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| WO2010107476A1 (en) | 2009-03-19 | 2010-09-23 | Duke University | Inhibiting gsnor |
| WO2011069951A1 (en) | 2009-12-11 | 2011-06-16 | Glaxo Group Limited | Imidazolidinedione derivatives |
| SI2533638T1 (sl) | 2010-02-12 | 2016-05-31 | Nivalis Therapeutics, Inc. | Novi inhibitorji S-nitrozoglutation reduktaze |
| SI2624695T1 (sl) | 2010-10-08 | 2016-01-29 | Nivalis Therapeutics, Inc. | Nove substituirane kinolinske spojine kot inhibitorji S-nitrozoglutation reduktaze |
| WO2012083165A1 (en) | 2010-12-16 | 2012-06-21 | N30 Pharmaceuticals, Llc | Novel substituted bicyclic aromatic compounds as s-nitrosoglutathione reductase inhibitors |
| WO2012170371A1 (en) | 2011-06-10 | 2012-12-13 | N30 Pharmaceuticals, Llc | Compounds as s-nitrosoglutathione reductase inhibitors |
-
2011
- 2011-10-07 SI SI201130672T patent/SI2624695T1/sl unknown
- 2011-10-07 DK DK11831651.2T patent/DK2624695T3/en active
- 2011-10-07 HR HRP20151405TT patent/HRP20151405T1/hr unknown
- 2011-10-07 PT PT118316512T patent/PT2624695E/pt unknown
- 2011-10-07 JP JP2013532965A patent/JP5855113B2/ja not_active Expired - Fee Related
- 2011-10-07 RU RU2013112122/04A patent/RU2599144C2/ru active IP Right Revival
- 2011-10-07 AU AU2011311920A patent/AU2011311920B2/en not_active Ceased
- 2011-10-07 BR BR112013007907A patent/BR112013007907A2/pt not_active Application Discontinuation
- 2011-10-07 ES ES11831651.2T patent/ES2553771T3/es active Active
- 2011-10-07 CN CN201180052350.7A patent/CN103200820B/zh active Active
- 2011-10-07 HU HUE11831651A patent/HUE025653T2/hu unknown
- 2011-10-07 PL PL11831651T patent/PL2624695T3/pl unknown
- 2011-10-07 IN IN501MUN2013 patent/IN2013MN00501A/en unknown
- 2011-10-07 KR KR1020137010664A patent/KR101886459B1/ko not_active Expired - Fee Related
- 2011-10-07 US US13/824,430 patent/US8921562B2/en active Active
- 2011-10-07 WO PCT/US2011/055200 patent/WO2012048181A1/en not_active Ceased
- 2011-10-07 CA CA2811791A patent/CA2811791C/en not_active Expired - Fee Related
- 2011-10-07 EP EP15180449.9A patent/EP2977050A1/en not_active Withdrawn
- 2011-10-07 RS RS20150786A patent/RS54369B1/sr unknown
- 2011-10-07 EP EP11831651.2A patent/EP2624695B1/en active Active
-
2012
- 2012-12-24 IL IL223829A patent/IL223829A/en not_active IP Right Cessation
-
2013
- 2013-05-06 ZA ZA2013/03257A patent/ZA201303257B/en unknown
-
2014
- 2014-11-13 US US14/540,216 patent/US9139528B2/en not_active Expired - Fee Related
-
2015
- 2015-08-04 US US14/817,329 patent/US9315462B2/en not_active Expired - Fee Related
- 2015-10-19 JP JP2015205282A patent/JP2016074667A/ja active Pending
-
2016
- 2016-01-21 SM SM201600021T patent/SMT201600021B/it unknown
- 2016-04-06 HK HK16103862.1A patent/HK1215862A1/en unknown
- 2016-04-13 US US15/097,378 patent/US9433618B2/en not_active Expired - Fee Related
- 2016-08-04 US US15/228,088 patent/US9856219B2/en active Active