JP2013542937A5 - - Google Patents
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- 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
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- 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
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- 235000020824 obesity Nutrition 0.000 description 1
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- 230000003979 response to food Effects 0.000 description 1
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- 230000000472 traumatic effect Effects 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
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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) | EP2624695B1 (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 |
|---|---|---|---|---|
| PT2624695E (pt) | 2010-10-08 | 2015-12-01 | Nivalis Therapeutics Inc | Novos compostos de quinolina substituídos como inibidores de s-nitrosoglutationa redutase |
| CN103328430A (zh) | 2010-12-16 | 2013-09-25 | N30医药品公司 | 作为s-亚硝基谷胱甘肽还原酶抑制剂的新型取代的双环芳族化合物 |
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