JP2016528300A5 - - Google Patents
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- JP2016528300A5 JP2016528300A5 JP2016536495A JP2016536495A JP2016528300A5 JP 2016528300 A5 JP2016528300 A5 JP 2016528300A5 JP 2016536495 A JP2016536495 A JP 2016536495A JP 2016536495 A JP2016536495 A JP 2016536495A JP 2016528300 A5 JP2016528300 A5 JP 2016528300A5
- Authority
- JP
- Japan
- Prior art keywords
- patient
- alkyl
- medicament according
- alkoxy
- hydrogen
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims description 62
- 239000001257 hydrogen Substances 0.000 claims description 62
- 208000020832 chronic kidney disease Diseases 0.000 claims description 58
- 239000003814 drug Substances 0.000 claims description 56
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 125000003282 alkyl amino group Chemical group 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 claims description 44
- 125000004423 acyloxy group Chemical group 0.000 claims description 40
- 125000001769 aryl amino group Chemical group 0.000 claims description 40
- 125000004104 aryloxy group Chemical group 0.000 claims description 40
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 40
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 30
- 125000000304 alkynyl group Chemical group 0.000 claims description 30
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000001475 halogen functional group Chemical group 0.000 claims description 30
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 30
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 229940109239 creatinine Drugs 0.000 claims description 22
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 20
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 20
- 150000001408 amides Chemical class 0.000 claims description 20
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 20
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 18
- -1 hydroxy, methyl Chemical group 0.000 claims description 18
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 17
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 15
- 208000031229 Cardiomyopathies Diseases 0.000 claims description 14
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 14
- 201000001320 Atherosclerosis Diseases 0.000 claims description 12
- 210000001147 pulmonary artery Anatomy 0.000 claims description 12
- 208000037803 restenosis Diseases 0.000 claims description 12
- 208000024891 symptom Diseases 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 101800000407 Brain natriuretic peptide 32 Proteins 0.000 claims description 10
- 125000005035 acylthio group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 230000036772 blood pressure Effects 0.000 claims description 10
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 9
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 208000007536 Thrombosis Diseases 0.000 claims description 7
- 102000009027 Albumins Human genes 0.000 claims description 6
- 108010088751 Albumins Proteins 0.000 claims description 6
- 238000002441 X-ray diffraction Methods 0.000 claims description 6
- 206010037437 Pulmonary thrombosis Diseases 0.000 claims description 5
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 4
- 229940118365 Endothelin receptor antagonist Drugs 0.000 claims description 4
- LMHIPJMTZHDKEW-XQYLJSSYSA-M Epoprostenol sodium Chemical class [Na+].O1\C(=C/CCCC([O-])=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 LMHIPJMTZHDKEW-XQYLJSSYSA-M 0.000 claims description 4
- 229940118547 Guanylate cyclase stimulant Drugs 0.000 claims description 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 4
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 4
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 4
- 102000007637 Soluble Guanylyl Cyclase Human genes 0.000 claims description 4
- 108010007205 Soluble Guanylyl Cyclase Proteins 0.000 claims description 4
- 239000003420 antiserotonin agent Substances 0.000 claims description 4
- 239000000480 calcium channel blocker Substances 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000002308 endothelin receptor antagonist Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 239000003590 rho kinase inhibitor Substances 0.000 claims description 4
- 229940121356 serotonin receptor antagonist Drugs 0.000 claims description 4
- BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 claims description 4
- 239000005483 tyrosine kinase inhibitor Substances 0.000 claims description 4
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 claims description 4
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 3
- HMJIYCCIJYRONP-UHFFFAOYSA-N (+-)-Isradipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12 HMJIYCCIJYRONP-UHFFFAOYSA-N 0.000 claims description 2
- PVHUJELLJLJGLN-INIZCTEOSA-N (S)-nitrendipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 PVHUJELLJLJGLN-INIZCTEOSA-N 0.000 claims description 2
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 claims description 2
- UIAGMCDKSXEBJQ-IBGZPJMESA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-IBGZPJMESA-N 0.000 claims description 2
- 206010048554 Endothelial dysfunction Diseases 0.000 claims description 2
- 239000005517 L01XE01 - Imatinib Substances 0.000 claims description 2
- ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 claims description 2
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 claims description 2
- SECKRCOLJRRGGV-UHFFFAOYSA-N Vardenafil Chemical compound CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 SECKRCOLJRRGGV-UHFFFAOYSA-N 0.000 claims description 2
- 229960002414 ambrisentan Drugs 0.000 claims description 2
- OUJTZYPIHDYQMC-LJQANCHMSA-N ambrisentan Chemical compound O([C@@H](C(OC)(C=1C=CC=CC=1)C=1C=CC=CC=1)C(O)=O)C1=NC(C)=CC(C)=N1 OUJTZYPIHDYQMC-LJQANCHMSA-N 0.000 claims description 2
- 229960000528 amlodipine Drugs 0.000 claims description 2
- HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 claims description 2
- 229960002105 amrinone Drugs 0.000 claims description 2
- RNLQIBCLLYYYFJ-UHFFFAOYSA-N amrinone Chemical group N1C(=O)C(N)=CC(C=2C=CN=CC=2)=C1 RNLQIBCLLYYYFJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960002890 beraprost Drugs 0.000 claims description 2
- CTPOHARTNNSRSR-APJZLKAGSA-N beraprost Chemical compound O([C@H]1C[C@@H](O)[C@@H]([C@@H]21)/C=C/[C@@H](O)C(C)CC#CC)C1=C2C=CC=C1CCCC(O)=O CTPOHARTNNSRSR-APJZLKAGSA-N 0.000 claims description 2
- 229960003065 bosentan Drugs 0.000 claims description 2
- GJPICJJJRGTNOD-UHFFFAOYSA-N bosentan Chemical group COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 GJPICJJJRGTNOD-UHFFFAOYSA-N 0.000 claims description 2
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims description 2
- 229960004166 diltiazem Drugs 0.000 claims description 2
- 230000008694 endothelial dysfunction Effects 0.000 claims description 2
- 229960000972 enoximone Drugs 0.000 claims description 2
- ZJKNESGOIKRXQY-UHFFFAOYSA-N enoximone Chemical compound C1=CC(SC)=CC=C1C(=O)C1=C(C)NC(=O)N1 ZJKNESGOIKRXQY-UHFFFAOYSA-N 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 claims description 2
- 229940080856 gleevec Drugs 0.000 claims description 2
- 239000007902 hard capsule Substances 0.000 claims description 2
- 229960002240 iloprost Drugs 0.000 claims description 2
- HIFJCPQKFCZDDL-ACWOEMLNSA-N iloprost Chemical compound C1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(C)CC#CC)[C@H](O)C[C@@H]21 HIFJCPQKFCZDDL-ACWOEMLNSA-N 0.000 claims description 2
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical group C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 229960004427 isradipine Drugs 0.000 claims description 2
- 229960001039 macitentan Drugs 0.000 claims description 2
- JGCMEBMXRHSZKX-UHFFFAOYSA-N macitentan Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCCC)=NC=NC=1OCCOC1=NC=C(Br)C=N1 JGCMEBMXRHSZKX-UHFFFAOYSA-N 0.000 claims description 2
- VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 claims description 2
- 229960003574 milrinone Drugs 0.000 claims description 2
- PZRHRDRVRGEVNW-UHFFFAOYSA-N milrinone Chemical compound N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1C PZRHRDRVRGEVNW-UHFFFAOYSA-N 0.000 claims description 2
- IAYNHDZSSDUYHY-UHFFFAOYSA-N n-(2-acetyl-4,6-dimethylphenyl)-3-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]thiophene-2-carboxamide Chemical compound CC(=O)C1=CC(C)=CC(C)=C1NC(=O)C1=C(S(=O)(=O)NC2=C(C(C)=NO2)C)C=CS1 IAYNHDZSSDUYHY-UHFFFAOYSA-N 0.000 claims description 2
- 229960001783 nicardipine Drugs 0.000 claims description 2
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 claims description 2
- 229960001597 nifedipine Drugs 0.000 claims description 2
- 229960000715 nimodipine Drugs 0.000 claims description 2
- 229960000227 nisoldipine Drugs 0.000 claims description 2
- 229960005425 nitrendipine Drugs 0.000 claims description 2
- 229960000529 riociguat Drugs 0.000 claims description 2
- WXXSNCNJFUAIDG-UHFFFAOYSA-N riociguat Chemical group N1=C(N)C(N(C)C(=O)OC)=C(N)N=C1C(C1=CC=CN=C11)=NN1CC1=CC=CC=C1F WXXSNCNJFUAIDG-UHFFFAOYSA-N 0.000 claims description 2
- FFYNAVGJSYHHFO-UHFFFAOYSA-N sarpogrelate Chemical group COC1=CC=CC(CCC=2C(=CC=CC=2)OCC(CN(C)C)OC(=O)CCC(O)=O)=C1 FFYNAVGJSYHHFO-UHFFFAOYSA-N 0.000 claims description 2
- 229950005789 sarpogrelate Drugs 0.000 claims description 2
- 229960003310 sildenafil Drugs 0.000 claims description 2
- 229960002578 sitaxentan Drugs 0.000 claims description 2
- PHWXUGHIIBDVKD-UHFFFAOYSA-N sitaxentan Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC=2C(=CC=3OCOC=3C=2)C)=C1Cl PHWXUGHIIBDVKD-UHFFFAOYSA-N 0.000 claims description 2
- 239000007901 soft capsule Substances 0.000 claims description 2
- 239000007962 solid dispersion Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 229960000835 tadalafil Drugs 0.000 claims description 2
- IEHKWSGCTWLXFU-IIBYNOLFSA-N tadalafil Chemical compound C1=C2OCOC2=CC([C@@H]2C3=C([C]4C=CC=CC4=N3)C[C@H]3N2C(=O)CN(C3=O)C)=C1 IEHKWSGCTWLXFU-IIBYNOLFSA-N 0.000 claims description 2
- 229960005032 treprostinil Drugs 0.000 claims description 2
- PAJMKGZZBBTTOY-ZFORQUDYSA-N treprostinil Chemical group C1=CC=C(OCC(O)=O)C2=C1C[C@@H]1[C@@H](CC[C@@H](O)CCCCC)[C@H](O)C[C@@H]1C2 PAJMKGZZBBTTOY-ZFORQUDYSA-N 0.000 claims description 2
- 229960000438 udenafil Drugs 0.000 claims description 2
- IYFNEFQTYQPVOC-UHFFFAOYSA-N udenafil Chemical compound C1=C(C=2NC=3C(CCC)=NN(C)C=3C(=O)N=2)C(OCCC)=CC=C1S(=O)(=O)NCCC1CCCN1C IYFNEFQTYQPVOC-UHFFFAOYSA-N 0.000 claims description 2
- 229960002381 vardenafil Drugs 0.000 claims description 2
- 229960001722 verapamil Drugs 0.000 claims description 2
- 208000021066 Pulmonary arterial hypertension associated with connective tissue disease Diseases 0.000 claims 4
- 208000026151 Chronic thromboembolic pulmonary hypertension Diseases 0.000 claims 1
- 229910016523 CuKa Inorganic materials 0.000 claims 1
- 208000004248 Familial Primary Pulmonary Hypertension Diseases 0.000 claims 1
- 208000020875 Idiopathic pulmonary arterial hypertension Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 238000001361 intraarterial administration Methods 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000000034 method Methods 0.000 description 276
- 239000000090 biomarker Substances 0.000 description 24
- 208000017169 kidney disease Diseases 0.000 description 20
- 210000002966 serum Anatomy 0.000 description 16
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 8
- 239000003550 marker Substances 0.000 description 8
- 206010024119 Left ventricular failure Diseases 0.000 description 7
- 230000024924 glomerular filtration Effects 0.000 description 6
- 230000037396 body weight Effects 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 102000012192 Cystatin C Human genes 0.000 description 4
- 108010061642 Cystatin C Proteins 0.000 description 4
- 206010019280 Heart failures Diseases 0.000 description 4
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical group N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 4
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 229940116269 uric acid Drugs 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 206010039163 Right ventricular failure Diseases 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361869527P | 2013-08-23 | 2013-08-23 | |
| US61/869,527 | 2013-08-23 | ||
| PCT/US2014/052382 WO2015027206A1 (en) | 2013-08-23 | 2014-08-22 | Methods of treating and preventing endothelial dysfunction using bardoxololone methyl or analogs thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018220800A Division JP6526306B2 (ja) | 2013-08-23 | 2018-11-27 | バルドキソロンメチルまたはその類似体を使用して内皮機能障害を処置および予防する方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016528300A JP2016528300A (ja) | 2016-09-15 |
| JP2016528300A5 true JP2016528300A5 (https=) | 2017-09-28 |
| JP6564372B2 JP6564372B2 (ja) | 2019-08-21 |
Family
ID=51794949
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016536495A Active JP6564372B2 (ja) | 2013-08-23 | 2014-08-22 | バルドキソロンメチルまたはその類似体を使用して内皮機能障害を処置および予防する方法 |
| JP2018220800A Active JP6526306B2 (ja) | 2013-08-23 | 2018-11-27 | バルドキソロンメチルまたはその類似体を使用して内皮機能障害を処置および予防する方法 |
| JP2019074559A Active JP6701407B2 (ja) | 2013-08-23 | 2019-04-10 | バルドキソロンメチルまたはその類似体を使用して内皮機能障害を処置および予防する方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018220800A Active JP6526306B2 (ja) | 2013-08-23 | 2018-11-27 | バルドキソロンメチルまたはその類似体を使用して内皮機能障害を処置および予防する方法 |
| JP2019074559A Active JP6701407B2 (ja) | 2013-08-23 | 2019-04-10 | バルドキソロンメチルまたはその類似体を使用して内皮機能障害を処置および予防する方法 |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US20150080465A1 (https=) |
| EP (2) | EP4736949A2 (https=) |
| JP (3) | JP6564372B2 (https=) |
| KR (1) | KR102322057B1 (https=) |
| CN (2) | CN105517554B (https=) |
| AU (2) | AU2014308600B2 (https=) |
| BR (1) | BR112016003454B1 (https=) |
| CA (1) | CA2921386A1 (https=) |
| CL (1) | CL2016000405A1 (https=) |
| EA (1) | EA201690456A1 (https=) |
| IL (3) | IL285832B2 (https=) |
| MX (2) | MX380589B (https=) |
| MY (2) | MY198522A (https=) |
| NZ (4) | NZ744036A (https=) |
| PH (1) | PH12016500358B1 (https=) |
| SG (2) | SG11201601202WA (https=) |
| TW (2) | TWI716341B (https=) |
| WO (1) | WO2015027206A1 (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0907423A2 (pt) | 2008-01-11 | 2020-10-27 | Reata Pharmaceuticals, Inc. | composto triterpenoide sintético para uso em um método de melhoria da função renal em um indivíduo, e uso do referido composto |
| JP5529851B2 (ja) | 2008-04-18 | 2014-06-25 | リアタ ファーマシューティカルズ インコーポレイテッド | 抗酸化炎症モジュレーター：ｃ−１７においてアミノ改変およびその他の改変を加えたオレアノール酸誘導体 |
| WO2009146218A2 (en) | 2008-04-18 | 2009-12-03 | Reata Pharmaceuticals, Inc. | Compounds including an anti-inflammatory pharmacore and methods of use |
| CN103596929B (zh) | 2010-12-17 | 2016-10-19 | 里亚塔医药公司 | 作为抗氧化发炎调节剂的吡唑及嘧啶三环烯酮 |
| TWI623548B (zh) | 2012-04-27 | 2018-05-11 | 瑞塔醫藥有限責任公司 | 齊墩果酸（ｂａｒｄｏｘｏｌｏｎｅ ｍｅｔｈｙｌ）之２，２-二氟基丙醯胺衍生物、多晶型及其使用方法 |
| WO2013188818A1 (en) | 2012-06-15 | 2013-12-19 | Reata Pharmaceuticals, Inc. | A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof |
| WO2014040073A1 (en) | 2012-09-10 | 2014-03-13 | Reata Pharmaceuticals, Inc. | C13-hydroxy derivatives of oleanolic acid and methods of use thereof |
| JP6243428B2 (ja) | 2012-09-10 | 2017-12-06 | リアタ ファーマシューティカルズ インコーポレイテッド | オレアノール酸のｃ１７−アルカンジイルおよびアルケンジイル誘導体ならびにその使用方法 |
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| AR096046A1 (es) | 2013-04-24 | 2015-12-02 | Abbvie Inc | Derivados de 2,2-difluoropropanamida de metil bardoxolona, formas polimórficas y métodos de uso |
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