HRP20171565T1 - C17-heteroaril derivati oleanolne kiseline i postupci njihove uporabe - Google Patents
C17-heteroaril derivati oleanolne kiseline i postupci njihove uporabe Download PDFInfo
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- HRP20171565T1 HRP20171565T1 HRP20171565TT HRP20171565T HRP20171565T1 HR P20171565 T1 HRP20171565 T1 HR P20171565T1 HR P20171565T T HRP20171565T T HR P20171565TT HR P20171565 T HRP20171565 T HR P20171565T HR P20171565 T1 HRP20171565 T1 HR P20171565T1
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- Prior art keywords
- aromatic
- ring
- compound according
- atoms
- alkyl
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- JKLISIRFYWXLQG-UHFFFAOYSA-N Epioleonolsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4CCC3C21C JKLISIRFYWXLQG-UHFFFAOYSA-N 0.000 title 1
- YBRJHZPWOMJYKQ-UHFFFAOYSA-N Oleanolic acid Natural products CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C1)C(=O)O YBRJHZPWOMJYKQ-UHFFFAOYSA-N 0.000 title 1
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 title 1
- 229940100243 oleanolic acid Drugs 0.000 title 1
- HZLWUYJLOIAQFC-UHFFFAOYSA-N prosapogenin PS-A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OCC(O)C(O)C1O HZLWUYJLOIAQFC-UHFFFAOYSA-N 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- 239000005864 Sulphur Substances 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000005035 acylthio group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 2
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 230000008798 inflammatory stress Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 1
- 230000036542 oxidative stress Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Biochemistry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epidemiology (AREA)
- Lubricants (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Claims (15)
1. Spoj s formulom:
[image]
naznačen time da:
n je 0-3;
Ar je heteroarendiil(C≤8) ili njegova supstituirana verzija; i
Y je:
vodik, hidroksi, halo, amino, ili cijano ili -NCO; ili
alkil(C≤8), cikloalkil(C≤8), alkenil(C≤8), alkinil(C≤8), aril(C≤12), aralkil(C≤12), heteroaril(C≤8), heterocikloalkil(C≤12), acil(C≤12), alkoksi(C≤8), ariloksi(C≤12), aciloksi(C≤8), alkilamino(C≤8), dialkilamino(C≤8), arilamino(C≤8), aralkilamino(C≤8), alkiltio(C≤8), aciltio(C≤8), alkilsulfonilamino(C≤8), ili supstituirane verzije bilo koje od navedenih skupina;
ili njihova farmaceutski prihvatljiva sol;
i pri čemu
u supstituiranim verzijama alkil(C≤8), cikloalkil(C≤8), alkenil(C≤8), alkinil(C≤8), aril(C≤8), aralkil(C≤12), heteroaril(C≤8), acil(C≤12), alkoksi(C≤8), ariloksi(C≤12), aciloksi(C≤8), alkilamino(C≤8), dialkilamino(C≤8), arilamino(C≤8), aralkilamino(C≤8), alkiltio(C≤8), aciltio(C≤8), alkilsulfonilamino(C≤8) jedan ili više vodikovih atoma je neovisno zamijenjen sa -OH, -F, -Cl, -Br, -I, -NH2, -NO2, -CO2H, -CO2CH3, -CN, -SH, -OCH3, -OCH2CH3, -C(O)CH3, -NHCH3, -NHCH2CH3, -N(CH3)2, -C(O)NH2, -OC(O)CH3, ili -S(O)2NH2
u supstituiranoj verziji heterocikloalkila(C≤8), jedan ili više vodikovih atoma je neovisno zamijenjen sa -OH, -F, -Cl, -Br, -I, -NH2, -NO2, -CO2H, -CO2CH3, -CN, -SH, -OCH3, -OCH2CH3, -C(O)CH3, -NHCH3, -NHCH2CH3, -N(CH3)2, -C(O)NH2, -OC(O)CH3, -S(O)2NH2 ili -C(O)OC(CH3)3;
izraz "aril" odnosi se na jednovalentnu aromatsku skupinu s aromatskim ugljikovim atomom as kao točkom spajanja koja tvori dio jedne ili više šestero-članih aromatskih prstenskih struktura, pri čemu atomi u prstenu su svi ugljik, te pri čemu, ako je prisutan više od jednog prstena, prstenovi mogu biti kondenzirani ili nekondenzirani, i pri čemu jedna ili više skupina alkil ili aralkil može biti spojena na prvi aromatski prsten ili bilo koji prisutan dodatni aromatski prsten, ako to dozvoljava ograničenje broja ugljika;
izraz "heteroaril" odnosi se na jednovalentnu aromatsku skupinu s aromatskim ugljikovim atomom ili dušikovim atomom kao točkom spajanja, navedeni ugljikov atom ili dušikov atom tvori dio jedne ili više aromatskih prstenskih struktura pri čemu barem jedan od prstenskih atoma je dušik, kisik ili sumpor, pri čemu heteroarilna skupina ne sadrži druge atome osim ugljika, vodika, aromatskog dušika, aromatskog kisika i aromatskog sumpora, pri čemu ako je prisutan više od jednog prstena, prstenovi mogu biti kondenzirani ili nekondenzirani, i pri čemu jedna ili više skupina alkil, aril, i/ili aralkil može biti spojena na aromatski prsten ili aromatski prstenski sustav, ako to dozvoljava ograničenje broja ugljika;
izraz "heteroarendiil" odnosi se na dvovalentnu aromatsku skupinu, sa dva aromatska ugljikova atoma, dva aromatska dušikova atoma, ili jedan aromatski ugljikov atom i jedan aromatski dušikov atom kao dvije točke spajanja, navedeni atomi tvore dio jedne ili više aromatskih prstenskih struktura pri čemu je barem jedan od atoma u prstenu dušik, kisik ili sumpor, pri čemu dvovalentna skupina ne sadrži druge atome osim ugljika, vodika, aromatskog dušika, aromatskog kisika i aromatskog sumpora, pri čemu, ako je prisutan više od jedan prsten, prstenovi mogu biti kondenzirani ili nekondenzirani, pri čemu nekondenzirani prstenovi mogu biti povezani preko jednog ili više od slijedećeg: kovalentne veze, alkendiila, ili alkendiilnih skupina, ako to dozvoljava ograničenje broja ugljika, i pri čemu jedna ili više skupina alkil, aril, i/ili aralkil može biti spojena na aromatski prsten ili aromatski prstenski sustav, ako to dozvoljava ograničenje broja ugljika;
izraz "heterocikloalkil" odnosi se na jednovalentnu ne-aromatsku skupinu s ugljikovim atomom ili dušikovim atomom kao točkom spajanja, navedeni ugljikov atom ili dušikov atom tvore dio jedne ili više ne-aromatskih prstenastih struktura pri čemu barem jedan od atoma prstena je dušik, kisik ili sumpor, pri čemu heterocikloalkilna skupina ne sadrži atome osim ugljika, vodika, dušika, kisika i sumpora, pri čemu, ako je prisutan više od jednog prstena, prstenovi mogu biti kondenzirani ili nekondenzirani, pri čemu, jedna ili više alkilnih skupina može biti spojena na prsten ili prstenski sustav, ako to dozvoljava ograničenje broja ugljika, te pri čemu jedna ili više dvostrukih veza može biti prisutna u prstenu ili prstenskom sustavu, pod uvjetom da nastala skupina ostaje ne-aromatska;
izraz "acil" odnosi se na skupinu -C(O)R, u kojoj R je vodik, alkil, aril, aralkil ili heteroaril; i
izraz "dialkilamino" odnosi se na skupinu -NRR', u kojoj R i R' mogu biti iste ili različite alkilne skupine, ili R i R' mogu se uzeti zajedno da predstavljaju alkandiil.
2. Spoj prema zahtjevu 1, naznačen time da Y je -H.
3. Spoj prema zahtjevu 1, naznačen time da Y je alkil(C≤4) ili cikloalkil(C≤4).
4. Spoj prema zahtjevu 3, naznačen time da Y je metil, n-propil, izopropil ili ciklopropil.
5. Spoj prema zahtjevu 1, naznačen time da Y je supstituirani alkil(C≤4) ili supstituirani cikloalkil(C≤4).
6. Spoj prema zahtjevu 5, naznačen time da Y je metoksimetil.
7. Spoj prema bilo kojem od zahtjeva 1-6, naznačen time da Ar je
[image]
ili
[image]
8. Spoj prema bilo kojem od zahtjeva 1-7, naznačen time da n = 0.
9. Spoj prema bilo kojem od zahtjeva 1-7, naznačen time da n = 1.
10. Spoj prema zahtjevu 1, naznačen time da je nadalje definiran kao:
[image]
[image]
[image]
ili
[image]
ili njihova farmaceutski prihvatljiva sol.
11. Spoj prema zahtjevu 1, naznačen time da je nadalje definiran kao:
[image]
ili njihova farmaceutski prihvatljiva sol.
12. Spoj prema zahtjevu 1, naznačen time da je nadalje definiran kao:
[image]
ili njegova farmaceutski prihvatljiva sol.
13. Farmaceutski pripravak naznačen time da sadrži:
a) spoj prema bilo kojem od zahtjeva 1-12; i
b) ekscipijent.
14. Spoj prema bilo kojem od zahtjeva 1-12 naznačen time da je za uporabu kao lijek.
15. Spoj za uporabu prema zahtjevu 14, naznačen time da lijek je za tretman pacijenta kod upale i/ili oksidacijskog stresa.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261699199P | 2012-09-10 | 2012-09-10 | |
PCT/US2013/059015 WO2014040056A1 (en) | 2012-09-10 | 2013-09-10 | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
EP13767175.6A EP2892911B1 (en) | 2012-09-10 | 2013-09-10 | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
Publications (1)
Publication Number | Publication Date |
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HRP20171565T1 true HRP20171565T1 (hr) | 2017-12-15 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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HRP20171565TT HRP20171565T1 (hr) | 2012-09-10 | 2017-10-16 | C17-heteroaril derivati oleanolne kiseline i postupci njihove uporabe |
Country Status (28)
Country | Link |
---|---|
US (1) | US20140088163A1 (hr) |
EP (1) | EP2892911B1 (hr) |
JP (1) | JP6272870B2 (hr) |
KR (1) | KR102237364B1 (hr) |
CN (1) | CN104768965B (hr) |
AU (1) | AU2013312102B2 (hr) |
BR (1) | BR112015005200B1 (hr) |
CA (1) | CA2882417C (hr) |
CY (1) | CY1119762T1 (hr) |
DK (1) | DK2892911T3 (hr) |
EA (1) | EA029069B1 (hr) |
ES (1) | ES2644615T3 (hr) |
HK (1) | HK1211295A1 (hr) |
HR (1) | HRP20171565T1 (hr) |
HU (1) | HUE036797T2 (hr) |
IL (1) | IL237638B (hr) |
IN (1) | IN2015DN01547A (hr) |
LT (1) | LT2892911T (hr) |
ME (1) | ME02911B (hr) |
MX (1) | MX366954B (hr) |
NZ (1) | NZ705213A (hr) |
PL (1) | PL2892911T3 (hr) |
PT (1) | PT2892911T (hr) |
RS (1) | RS56563B1 (hr) |
SG (1) | SG11201501800UA (hr) |
SI (1) | SI2892911T1 (hr) |
WO (1) | WO2014040056A1 (hr) |
ZA (1) | ZA201501203B (hr) |
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US9512094B2 (en) | 2012-09-10 | 2016-12-06 | Reata Pharmaceuticals, Inc. | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
PL2892912T3 (pl) | 2012-09-10 | 2019-10-31 | Reata Pharmaceuticals Inc | C17-alkanodiylowe i alkenodiylowe pochodne kwasu oleanolowego i sposoby ich zastosowania |
TWI649330B (zh) | 2013-04-24 | 2019-02-01 | 艾伯維有限公司 | 甲基巴多索龍之2,2-二氟丙醯胺衍生物、其多晶形及其使用方法 |
KR102686868B1 (ko) | 2015-02-12 | 2024-07-19 | 리아타 파마슈티컬즈, 아이엔씨. | 항산화 염증 조절제로서의 이미다졸릴 트리사이클릭 에논 |
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CN106632574B (zh) * | 2016-12-07 | 2018-05-29 | 广东天键生物科技有限公司 | 一种化合物、其制备方法及用途 |
TWI831738B (zh) | 2016-12-16 | 2024-02-11 | 美商瑞塔醫藥有限責任公司 | 用於抑制RORγ及其他用途的嘧啶三環烯酮衍生物 |
IL285232B (en) | 2017-09-14 | 2022-07-01 | Phoenix Biotechnology Inc | Preparations containing oleandrin for the treatment of viral infection |
MX2020002884A (es) | 2017-09-14 | 2020-10-05 | Phoenix Biotechnology Inc | Método y composición neuroprotectora mejorada para tratar afecciones neurológicas. |
KR20210032936A (ko) | 2018-06-15 | 2021-03-25 | 리아타 파마슈티컬즈, 아이엔씨. | Il-17 및 ror감마의 저해를 위한 피라졸 및 이미다졸 화합물 |
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CN113366010A (zh) * | 2018-09-28 | 2021-09-07 | 四川海思科制药有限公司 | 萜类化合物衍生物及其用途 |
JP2022541545A (ja) * | 2019-07-19 | 2022-09-26 | 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 | C17極性置換ヘテロ芳香族合成トリテルペノイドおよびその使用方法 |
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CA2485565A1 (en) * | 2002-05-13 | 2004-08-05 | Trustees Of Dartmouth College | Inhibitors and methods of use thereof |
CN108434151A (zh) | 2008-01-11 | 2018-08-24 | 里亚塔医药公司 | 合成三萜类化合物及用以治病之方法 |
MX2010011439A (es) | 2008-04-18 | 2011-01-25 | Reata Pharmaceuticals Inc | Moduladores de inflamacion antioxidantes: derivados del acido oleanolico homologacion c-17. |
EA022588B1 (ru) * | 2008-04-18 | 2016-01-29 | Ритэ Фамэсутикл, Инк. | Антиоксидантные модуляторы воспаления: производные олеанолевой кислоты с насыщением в с-кольце |
TW201004627A (en) | 2008-04-18 | 2010-02-01 | Reata Pharmaceuticals Inc | Antioxidant inflammation modulators: novel derivatives of oleanolic acid |
US8124799B2 (en) | 2008-04-18 | 2012-02-28 | Reata Pharmaceuticals, Inc. | Antioxidant inflammation modulators: oleanolic acid derivatives with amino and other modifications at C-17 |
LT2683731T (lt) * | 2011-03-11 | 2019-07-10 | Reata Pharmaceuticals, Inc. | C4-monometiltriterpenoido dariniai ir jų panaudojimo būdai |
US9556222B2 (en) * | 2012-06-15 | 2017-01-31 | Reata Pharmaceuticals, Inc. | A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof |
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