AR092506A1 - Derivados c17-alcandiilo y alquendiilo del acido oleanolico y sus metodos de uso - Google Patents
Derivados c17-alcandiilo y alquendiilo del acido oleanolico y sus metodos de usoInfo
- Publication number
- AR092506A1 AR092506A1 ARP130103221A ARP130103221A AR092506A1 AR 092506 A1 AR092506 A1 AR 092506A1 AR P130103221 A ARP130103221 A AR P130103221A AR P130103221 A ARP130103221 A AR P130103221A AR 092506 A1 AR092506 A1 AR 092506A1
- Authority
- AR
- Argentina
- Prior art keywords
- hetero
- ral
- que
- alkyl
- hydrogen
- Prior art date
Links
- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 title 1
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000003368 amide group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- 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
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- 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]
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/47—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of rings being part of condensed ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/08—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring atoms
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)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
- Epidemiology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Abstract
Reivindicación 1: Un compuesto, caracterizado porque es de la fórmula (1), en donde: Y es un enlace covalente, -CH₂-, -C(O)-, -O- o -NH-; R¹ y R² son, cada uno de manera independiente, -H, -OH, metilo o como se definen más adelante; y R³ es: hidrógeno, hidroxi, halo, amino, -NHOH o mercapto; alquilo C£₈, alquenilo C£₈, alquinilo C£₈, arilo C£₈, aralquilo C£₈, heteroarilo C£₈, heterocicloalquilo C£₈, acilo C£₈, alcoxi C£₈, alqueniloxi C£₈, ariloxi C£₈, aralcoxi C£₈, heteroariloxi C£₈, aciloxi C£₈, heterocicloalcoxi C£₈, alquilamino C£₈, dialquilamino C£₈, alquenilamino C£₈, alcoxiamino C£₈, arilamino C£₈, aralquilamino C£₈, heteroarilamino C£₈, heterocicloalquilamino C£₈, alquilsulfonilamino C£₈, amido C£₈, -NH-amido C£₈ o una versión sustituida de cualquiera de estos grupos; R³ y R¹, tomados juntos, son -O-, -NRᵃ- o un enlace covalente entre Y y el átomo de carbono 13, en donde Rᵃ es hidrógeno o alquilo C£₄; o R³ y R², tomados juntos, son -O-, NRᵃ- o un enlace covalente entre Y y el átomo de carbono 14, en donde Rᵃ es hidrógeno o alquilo C£₄; o una sal farmacéuticamente aceptable de los mismos.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261699122P | 2012-09-10 | 2012-09-10 | |
| US201361780540P | 2013-03-13 | 2013-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR092506A1 true AR092506A1 (es) | 2015-04-22 |
Family
ID=49253402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP130103221A AR092506A1 (es) | 2012-09-10 | 2013-09-10 | Derivados c17-alcandiilo y alquendiilo del acido oleanolico y sus metodos de uso |
Country Status (38)
| Country | Link |
|---|---|
| US (2) | US9593074B2 (es) |
| EP (1) | EP2892912B1 (es) |
| JP (1) | JP6243428B2 (es) |
| KR (1) | KR102237359B1 (es) |
| CN (1) | CN104955833B (es) |
| AR (1) | AR092506A1 (es) |
| AU (1) | AU2013312106B2 (es) |
| BR (1) | BR112015005168A2 (es) |
| CA (1) | CA2882418C (es) |
| CL (1) | CL2015000543A1 (es) |
| CR (1) | CR20150117A (es) |
| CY (1) | CY1121776T1 (es) |
| DK (1) | DK2892912T3 (es) |
| DO (1) | DOP2015000054A (es) |
| EA (1) | EA029174B1 (es) |
| ES (1) | ES2731758T3 (es) |
| HR (1) | HRP20191165T1 (es) |
| HU (1) | HUE044126T2 (es) |
| IL (1) | IL237639B (es) |
| IN (1) | IN2015DN01442A (es) |
| LT (1) | LT2892912T (es) |
| ME (1) | ME03522B (es) |
| MX (1) | MX366913B (es) |
| MY (1) | MY180903A (es) |
| NZ (1) | NZ630967A (es) |
| PE (1) | PE20150627A1 (es) |
| PH (1) | PH12015500491A1 (es) |
| PL (1) | PL2892912T3 (es) |
| PT (1) | PT2892912T (es) |
| RS (1) | RS59194B1 (es) |
| SG (1) | SG11201501792RA (es) |
| SI (1) | SI2892912T1 (es) |
| SM (1) | SMT201900436T1 (es) |
| TW (1) | TWI630212B (es) |
| UA (1) | UA115672C2 (es) |
| UY (1) | UY35023A (es) |
| WO (1) | WO2014040060A1 (es) |
| ZA (1) | ZA201501206B (es) |
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| KR101780382B1 (ko) | 2008-01-11 | 2017-10-10 | 리타 파마슈티컬스 잉크. | 합성 트리테르페노이드 및 질병 치료시의 사용 방법 |
| CN103588678A (zh) | 2008-04-18 | 2014-02-19 | 里亚塔医药公司 | 包含抗炎症药效团的化合物以及使用方法 |
| RS58392B1 (sr) | 2008-04-18 | 2019-04-30 | Reata Pharmaceuticals Inc | Antioksidantni modulatori inflamacije: derivati oleanoličke kiseline sa amino i drugim modifikacijama na c-17 |
| CA2822071C (en) | 2010-12-17 | 2019-07-16 | Reata Pharmaceuticals, Inc. | Pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators |
| MX349739B (es) * | 2012-03-20 | 2017-08-10 | Firmenich & Cie | Compuestos para una liberacion controlada de moleculas perfumantes activas. |
| WO2013163344A1 (en) | 2012-04-27 | 2013-10-31 | Reata Pharmaceuticals, Inc. | 2.2-difluoropropionamide derivatives of bardoxolone methyl, polymorphic forms and methods of use thereof |
| US9556222B2 (en) | 2012-06-15 | 2017-01-31 | Reata Pharmaceuticals, Inc. | A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof |
| US9512094B2 (en) | 2012-09-10 | 2016-12-06 | Reata Pharmaceuticals, Inc. | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
| AU2013312106B2 (en) * | 2012-09-10 | 2018-03-08 | Reata Pharmaceuticals, Inc. | C17-alkanediyl and alkenediyl derivatives of oleanolic acid and methods of use thereof |
| 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 |
| JP6748652B2 (ja) | 2015-02-12 | 2020-09-02 | 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 | 抗酸化性炎症調節剤としてのイミダゾリル三環式エノン |
| NZ741082A (en) | 2015-09-23 | 2023-06-30 | Reata Pharmaceuticals Inc | C4-modified oleanolic acid derivatives for inhibition of il-17 and other uses |
| MX2019005401A (es) | 2016-11-08 | 2019-08-05 | Reata Pharmaceuticals Inc | Metodos para tratar el sindrome de alport con bardoxolona metilo o analogos de la misma. |
| 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 |
| CA3075023A1 (en) | 2017-09-14 | 2019-03-21 | Phoenix Biotechnology, Inc. | Method and improved neuroprotective composition for treating neurological conditions |
| AU2018334386B2 (en) | 2017-09-14 | 2021-11-04 | Phoenix Biotechnology, Inc. | Method and composition for treating viral infection |
| US9896476B1 (en) | 2017-09-21 | 2018-02-20 | King Saud University | Glycyrrhetic acid derivatives |
| CA3103726A1 (en) | 2018-06-15 | 2019-12-19 | Reata Pharmaceuticals, Inc. | Pyrazole and imidazole compounds for inhibition of il-17 and rorgamma |
| EP3810141A1 (en) | 2018-06-20 | 2021-04-28 | Reata Pharmaceuticals, Inc. | Cysteine-dependent inverse agonists of nuclear receptors ror-gamma/ror-gamma-t and methods of treating diseases or disorders therewith |
| CN108640965B (zh) * | 2018-06-23 | 2021-11-05 | 沈阳药科大学 | 2-取代-18β-甘草次酸衍生物及其应用 |
| CA3144603C (en) | 2019-07-19 | 2025-10-21 | Reata Pharmaceuticals, Inc. | C17 Polar Substitution Heteroaromatic Synthetic Triterpenoids and Their Methods of Use |
| EP4295854A3 (en) | 2020-03-31 | 2024-04-03 | Phoenix Biotechnology, Inc. | Method and compositions for treating coronavirus infection |
| MX394337B (es) | 2020-03-31 | 2025-03-24 | Phoenix Biotechnology Inc | Metodo y composiciones para el tratamiento de infeccion por coronavirus |
| EP4259155A1 (en) | 2020-12-11 | 2023-10-18 | Reata Pharmaceuticals Holdings, LLC | Synthetic triterpenoids for use in therapy |
| CA3204434A1 (en) * | 2021-01-18 | 2022-07-21 | Xin Jiang | Synthetic ursolic acid derivatives and methods of use thereof |
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