CN103596929B - 作为抗氧化发炎调节剂的吡唑及嘧啶三环烯酮 - Google Patents
作为抗氧化发炎调节剂的吡唑及嘧啶三环烯酮 Download PDFInfo
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- CN103596929B CN103596929B CN201180067948.3A CN201180067948A CN103596929B CN 103596929 B CN103596929 B CN 103596929B CN 201180067948 A CN201180067948 A CN 201180067948A CN 103596929 B CN103596929 B CN 103596929B
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- 0 CC1(CCC(C2(C)C)=*)C2=CCC1OCOC Chemical compound CC1(CCC(C2(C)C)=*)C2=CCC1OCOC 0.000 description 19
- KTLFWCKMRHNTLE-UHFFFAOYSA-N CC(C)(C1C(C)(CC2C#N)c3n[n](C)c(C(O)=O)c3CC1)C2=O Chemical compound CC(C)(C1C(C)(CC2C#N)c3n[n](C)c(C(O)=O)c3CC1)C2=O KTLFWCKMRHNTLE-UHFFFAOYSA-N 0.000 description 1
- HRVSMHUORGQWOD-FXWZCDFBSA-N CC(C)([C@H]1C(C)(C/C2=C/O)c3n[n](C)c(C(c4ccccc4)=O)c3CC1)C2=O Chemical compound CC(C)([C@H]1C(C)(C/C2=C/O)c3n[n](C)c(C(c4ccccc4)=O)c3CC1)C2=O HRVSMHUORGQWOD-FXWZCDFBSA-N 0.000 description 1
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- NNJGRVLXWWFDSL-UHFFFAOYSA-N CC1(CCC(C2(C)C)=O)c3n[n](C)cc3CC12N Chemical compound CC1(CCC(C2(C)C)=O)c3n[n](C)cc3CC12N NNJGRVLXWWFDSL-UHFFFAOYSA-N 0.000 description 1
- HMQAJUYTFRUSSF-MBIQTGHCSA-N CC12c3n[n](C)c(C#N)c3CC[C@H]1C(C)(C)OCCOCC2 Chemical compound CC12c3n[n](C)c(C#N)c3CC[C@H]1C(C)(C)OCCOCC2 HMQAJUYTFRUSSF-MBIQTGHCSA-N 0.000 description 1
- IGKLGUNWLMNMTQ-QGZVFWFLSA-N CCCCC(C(C)(C)[C@H]1Cc2n[n](C)c(C(c3ccccc3)=O)c2CC1)=O Chemical compound CCCCC(C(C)(C)[C@H]1Cc2n[n](C)c(C(c3ccccc3)=O)c2CC1)=O IGKLGUNWLMNMTQ-QGZVFWFLSA-N 0.000 description 1
- MJRJOBOEUCPRRX-UHFFFAOYSA-N CCCc1c[n](NC)nc1 Chemical compound CCCc1c[n](NC)nc1 MJRJOBOEUCPRRX-UHFFFAOYSA-N 0.000 description 1
- KWLVXIPZYGAABO-KURKYZTESA-N C[C@@](C1)([C@]11[C@](C)(CC2)c3n[n](C)c(-c4n[n](C)nn4)c3CC1)C21OCCO1 Chemical compound C[C@@](C1)([C@]11[C@](C)(CC2)c3n[n](C)c(-c4n[n](C)nn4)c3CC1)C21OCCO1 KWLVXIPZYGAABO-KURKYZTESA-N 0.000 description 1
- YYJKNOQRSRRGJA-RYUDHWBXSA-N C[C@@](CC1)([C@H](CC2)OCNC)C2=CC1=O Chemical compound C[C@@](CC1)([C@H](CC2)OCNC)C2=CC1=O YYJKNOQRSRRGJA-RYUDHWBXSA-N 0.000 description 1
- BMQFRTMNHUGXBR-CABCVRRESA-N C[C@@]1(C=C(C(C2(C)C)=O)C#N)c3n[n](C)cc3C[C@@]12N Chemical compound C[C@@]1(C=C(C(C2(C)C)=O)C#N)c3n[n](C)cc3C[C@@]12N BMQFRTMNHUGXBR-CABCVRRESA-N 0.000 description 1
- UWLYXTIFPAPOPA-PGZQCDFOSA-N C[C@@]1(CCC2(C3(C)C)[U]CCO2)c2n[n](C)cc2CC13N Chemical compound C[C@@]1(CCC2(C3(C)C)[U]CCO2)c2n[n](C)cc2CC13N UWLYXTIFPAPOPA-PGZQCDFOSA-N 0.000 description 1
- PCTYVBYWTOKBRB-MXPOGPBASA-N C[C@](CC1)([C@H](C/C2=C/O)C(C)(C)C11OCCO1)C2=[U] Chemical compound C[C@](CC1)([C@H](C/C2=C/O)C(C)(C)C11OCCO1)C2=[U] PCTYVBYWTOKBRB-MXPOGPBASA-N 0.000 description 1
- VPROZODPFLFWFM-AIEFZORHSA-N C[C@](CC1)([C@H](CC2)C(C)(C)C1=[U])C2OCOC Chemical compound C[C@](CC1)([C@H](CC2)C(C)(C)C1=[U])C2OCOC VPROZODPFLFWFM-AIEFZORHSA-N 0.000 description 1
- VFBKJZFQVABFEO-PZORYLMUSA-N C[C@](CCC1(C2(C)C)OCCO1)(C2(CC1)N)C1=O Chemical compound C[C@](CCC1(C2(C)C)OCCO1)(C2(CC1)N)C1=O VFBKJZFQVABFEO-PZORYLMUSA-N 0.000 description 1
- QPUYECUOLPXSFR-UHFFFAOYSA-N Cc1cccc2c1cccc2 Chemical compound Cc1cccc2c1cccc2 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Biochemistry (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Toxicology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201061424601P | 2010-12-17 | 2010-12-17 | |
| US61/424,601 | 2010-12-17 | ||
| PCT/US2011/065897 WO2012083306A2 (en) | 2010-12-17 | 2011-12-19 | Pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103596929A CN103596929A (zh) | 2014-02-19 |
| CN103596929B true CN103596929B (zh) | 2016-10-19 |
Family
ID=45470714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180067948.3A Active CN103596929B (zh) | 2010-12-17 | 2011-12-19 | 作为抗氧化发炎调节剂的吡唑及嘧啶三环烯酮 |
Country Status (32)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ME03529B (me) | 2008-01-11 | 2020-04-20 | Reata Pharmaceuticals Inc | Sintetički triterpenoidi i metode njihove upotrebe u tretmanu bolesti |
| TW201006474A (en) | 2008-04-18 | 2010-02-16 | Reata Pharmaceuticals Inc | Natural products including an anti-flammatory pharmacore and methods of use |
| 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 |
| PL2651918T3 (pl) | 2010-12-17 | 2017-12-29 | Novartis Ag | Krystaliczne formy 5-chloro-N2-(2-izopropoksy-5-metylo-4-piperydyn-4-ylofenylo)-N4-[2-(propano-2-sulfonylo)-fenylo]-pirymidyno-2,4-diaminy |
| ES2653717T3 (es) | 2010-12-17 | 2018-02-08 | Reata Pharmaceuticals, Inc. | Pirazolil- y pirimidinil-enonas tricíclicas como moduladores antioxidantes de la inflamación |
| EP2841445B1 (en) | 2012-04-27 | 2017-06-14 | 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 |
| TWI630212B (zh) | 2012-09-10 | 2018-07-21 | 瑞塔醫藥有限責任公司 | 丁香油素(oleanolic acid)之c17-烷二基與烯二基衍生物及其使用方法 |
| US9278912B2 (en) | 2012-09-10 | 2016-03-08 | Reata Pharmaceuticals, Inc. | C13-hydroxy derivatives of oleanolic acid 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 |
| 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 |
| WO2015112792A1 (en) * | 2014-01-24 | 2015-07-30 | Abbvie Inc. | Aryl and arylalkyl substituted pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators |
| AU2016219109B2 (en) * | 2015-02-12 | 2020-05-14 | Reata Pharmaceuticals, Inc. | Imidazolyl tricyclic enones as antioxidant iflammation modulators |
| BR112019009256A2 (pt) | 2016-11-08 | 2019-07-16 | Reata Pharmaceuticals, Inc. | métodos para tratar síndrome de alport usando bardoxolona metil ou análogos do mesmo |
| 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 |
| US11286226B2 (en) | 2017-09-21 | 2022-03-29 | Northwestern University | Polycyclic carbogenic molecules and uses thereof as anti-cancer agents |
| US11465963B2 (en) * | 2017-11-21 | 2022-10-11 | Biogen Ma Inc. | Tetrahydronaphthalene derivatives useful as Nrf2 activators |
| US11993574B2 (en) * | 2018-06-15 | 2024-05-28 | Reata Pharmaceuticals, Inc | Pyrazole and imidazole compounds for inhibition of IL-17 and RORgamma |
| US12060340B2 (en) | 2018-06-20 | 2024-08-13 | Reata Pharmaceuticals, Inc | Cysteine-dependent inverse agonists of nuclear receptors ROR-gamma/ROR-gamma-t and methods of treating diseases or disorders therewith |
| WO2021145655A1 (ko) | 2020-01-13 | 2021-07-22 | 압타바이오 주식회사 | 신규한 피라졸 유도체 |
| US20250025465A1 (en) * | 2021-11-17 | 2025-01-23 | Northwestern University | Wt-idh1 inhibition using a covalent and brain-penetrant small molecular inhibitor for ferroptosis induction in high-grade glioma |
| WO2024255851A1 (en) * | 2023-06-16 | 2024-12-19 | Nanjing Curegene Technology Co., Ltd. | Tumor-specific expression cassette and uses thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN85101752A (zh) * | 1983-10-03 | 1987-01-31 | 美国辉瑞有限公司 | 2-胺基-5-羟基-4-甲基嘧啶衍生物的制备方法 |
| CN1162918A (zh) * | 1994-09-09 | 1997-10-22 | 小山省三 | 分子表达功能抑制剂 |
| CN1491225A (zh) * | 2000-12-28 | 2004-04-21 | СҰҩƷ��ҵ��ʽ���� | 三杂环化合物和包括其作为活性组分的药物 |
| WO2009146218A2 (en) * | 2008-04-18 | 2009-12-03 | Reata Pharmaceuticals, Inc. | Compounds including an anti-inflammatory pharmacore and methods of use |
| WO2009146216A2 (en) * | 2008-04-18 | 2009-12-03 | Reata Pharmaceuticals. Inc. | Antioxidant inflammation modulators: novel derivatives of oleanolic acid |
Family Cites Families (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2875201A (en) | 1957-08-28 | 1959-02-24 | Searle & Co | Dehydrotigogenone intermediates |
| US3071577A (en) * | 1959-08-13 | 1963-01-01 | Syntex Corp | Pyrimidinyl androstanes |
| US3994935A (en) | 1975-11-24 | 1976-11-30 | E. R. Squibb & Sons, Inc. | Steroidal 16β-alkyl[16α,17-b]naphthalenes |
| NZ191586A (en) | 1978-10-10 | 1981-10-19 | Sterling Drug Inc | Cyanoketones derived from glycyrrhetinic acid and pharmaceutical compositions |
| US4395423A (en) | 1978-10-10 | 1983-07-26 | Sterling Drug Inc. | Polycyclic cyanoketones |
| US5064823A (en) | 1988-08-24 | 1991-11-12 | Research Triangle Institute | Pentacyclic triterpenoid compounds as topoisomerase inhibitors or cell differentiation inducers |
| DE4014171A1 (de) | 1990-05-03 | 1991-11-07 | Basf Ag | Cyanochinolinverbindungen |
| JPH08208479A (ja) * | 1994-04-29 | 1996-08-13 | Takeda Chem Ind Ltd | クラビンアルカロイド誘導体を含有する鎮痛剤 |
| AU2267995A (en) | 1994-04-29 | 1995-11-29 | Takeda Chemical Industries Ltd. | Ergoline derivatives as analgesics |
| US6326507B1 (en) | 1998-06-19 | 2001-12-04 | Trustees Of Dartmouth College | Therapeutic compounds and methods of use |
| US6369101B1 (en) | 1999-02-26 | 2002-04-09 | Regents Of The University Of Minnesota | Therapeutic method to treat herpes virus infection |
| PT1178952E (pt) | 1999-05-14 | 2007-12-04 | Univ California | Novos moduladores da interleucina-1 e do factor alfa de necrose tumoral, síntese dos referidos moduladores e métodos de utilização dos referidos moduladores |
| US6649654B1 (en) | 1999-11-23 | 2003-11-18 | The Regents Of The University Of California | Methods for identifying and using IKK inhibitors |
| US6890946B2 (en) | 1999-12-23 | 2005-05-10 | Indiana University Research And Technology Corporation | Use of parthenolide to inhibit cancer |
| JP4331913B2 (ja) | 2000-02-14 | 2009-09-16 | メルク エンド カムパニー インコーポレーテッド | エストロゲンレセプターモデュレーター |
| JP2001240573A (ja) | 2000-03-01 | 2001-09-04 | Meiji Seika Kaisha Ltd | トリテルペン誘導体及び肝疾患治療剤 |
| WO2002003996A1 (en) | 2000-07-12 | 2002-01-17 | RAJKUMAR, Sujatha | Use of dammarane-type tritepenoid saporins |
| US6689767B2 (en) | 2000-09-29 | 2004-02-10 | Regents Of The University Of Minnesota | Triterpenes having antibacterial activity |
| JP2004509972A (ja) | 2000-09-29 | 2004-04-02 | リージェンツ オブ ザ ユニバーシティ オブ ミネソタ | 酵母に対する殺真菌活性を有するトリテルペン |
| US6951847B2 (en) | 2000-09-29 | 2005-10-04 | Regents Of The University Of Minnesota | Methods of treating fungal infections using lupeol |
| US6878751B1 (en) | 2000-10-19 | 2005-04-12 | Imperial College Of Science Technology And Medicine | Administration of resveratrol to treat inflammatory respiratory disorders |
| US7435755B2 (en) | 2000-11-28 | 2008-10-14 | The Trustees Of Dartmouth College | CDDO-compounds and combination therapies thereof |
| WO2002047611A2 (en) | 2000-11-28 | 2002-06-20 | Board Of Regents, The University Of Texas System | Cddo-compounds and combination therapies thereof |
| CN1636058B (zh) | 2001-05-14 | 2011-06-08 | 龚大为 | 新型丙氨酸转氨酶及其应用方法 |
| JP2005502654A (ja) | 2001-08-13 | 2005-01-27 | メルク エンド カムパニー インコーポレーテッド | 選択的エストロゲン受容体調節剤 |
| EP1444207A2 (en) | 2001-09-19 | 2004-08-11 | Pharmacia Corporation | Substituted pyrazolyl-compounds for the treatment of inflammation |
| US6991814B2 (en) | 2001-12-13 | 2006-01-31 | Council Of Scientific And Industrial Research | Herbal medicaments for the treatment of neurocerebrovascular disorders |
| DK1465615T3 (da) | 2002-01-15 | 2012-11-12 | Dartmouth College | Tricykliske bisenonderivater og fremgangsmåder til anvendelse heraf |
| DE60325329D1 (de) | 2002-01-18 | 2009-01-29 | Univ Minnesota | Quaternäre terpensalze als biologisch aktive tenside |
| WO2003081210A2 (en) | 2002-03-21 | 2003-10-02 | Sunesis Pharmaceuticals, Inc. | Identification of kinase inhibitors |
| EP1507541A4 (en) | 2002-05-13 | 2009-06-03 | Dartmouth College | HEMMER AND APPLICATION METHOD THEREFOR |
| US20050014730A1 (en) | 2003-04-02 | 2005-01-20 | Carlson Robert M. | Anti-fungal formulation of triterpene and essential oil |
| NZ545565A (en) | 2003-09-02 | 2009-06-26 | Unigen Pharmaceuticals Inc | Formulation of a mixture of Free-B-Ring flavonoids and flavans for use in the prevention and treatment of cognitive decline and age-related memory impairments |
| AU2005282437B2 (en) | 2004-09-07 | 2013-01-10 | Pacific Arrow Limited | Anti-tumor compounds with angeloyl groups |
| US20050208151A1 (en) | 2003-10-30 | 2005-09-22 | Entelos, Inc. | Treatment of rheumatoid arthritis with FLIP antagonists |
| WO2005046732A2 (en) | 2003-11-04 | 2005-05-26 | THE UNITED SATES OF AMERICA as represented by THE SECRETARY OF HEALTH AND HUMAN SERVICES, NIH | Methods and compositions for the inhibition of hiv-1 replication |
| US20060258752A1 (en) | 2004-02-12 | 2006-11-16 | Vander Jagt David L | Method and compounds for cancer treatment utilizing NFkB as a direct or ultimate target for small molecule inhibitors |
| JP2005314381A (ja) | 2004-03-30 | 2005-11-10 | Anges Mg Inc | 増殖性腎疾患の予防・治療・改善剤 |
| WO2006089406A1 (en) * | 2005-02-22 | 2006-08-31 | Gemin X Biotechnologies Inc. | Diterpenoid compounds, compositions thereof and their use as anti-cancer or anti-fungal agents |
| CN101189229A (zh) | 2005-03-17 | 2008-05-28 | 哈佛大学校长及研究员协会 | 阿韦艾利酰胺、斯特伐希丁b和其类似物的合成 |
| AU2006265113A1 (en) | 2005-07-01 | 2007-01-11 | The Johns Hopkins University | Compositions and methods for the treatment or prevention of disorders relating to oxidative stress |
| DE102005041613A1 (de) | 2005-09-01 | 2007-03-08 | Ergonex Pharma Gmbh | Pharmazeutische Zusammensetzungen zur Behandlung von Karzinoid-Syndrom |
| US20070232577A1 (en) | 2006-03-23 | 2007-10-04 | Advanced Life Sciences, Inc. | Synthetic pentacyclic triterpenoids and derivatives of betulinic acid and betulin |
| WO2007127791A2 (en) | 2006-04-25 | 2007-11-08 | The Administrators Of The Tulane Educational Fund | New pharmacological method for treatment of neuropathic pain |
| WO2008000070A1 (en) | 2006-06-27 | 2008-01-03 | Wellington Laboratories Inc. | Glycyrrhetinic acid derivatives |
| WO2008016095A1 (en) | 2006-08-02 | 2008-02-07 | Santen Pharmaceutical Co., Ltd. | PREVENTIVE OR REMEDY FOR KERATOCONJUNCTIVAL DISORDERS CONTAINING Nrf2 ACTIVATOR AS THE ACTIVE INGREDIENT |
| JP2008110962A (ja) | 2006-08-02 | 2008-05-15 | Santen Pharmaceut Co Ltd | Nrf2活性化物質を有効成分として含む角結膜障害の予防または治療剤 |
| US8735411B2 (en) | 2006-10-02 | 2014-05-27 | Abbvie Inc. | Macrocyclic benzofused pyrimidine derivatives |
| WO2008063318A2 (en) | 2006-10-12 | 2008-05-29 | The Texas A & M University System And Safe Et Al | Betulinic acid, derivatives and analogs thereof and uses therefor |
| WO2008064132A2 (en) | 2006-11-17 | 2008-05-29 | Trustees Of Dartmouth College | Synthetic triterpenoids and tricyclic-bis-enones for use in stimulating bone and cartilage growth |
| EP2094651A1 (en) | 2006-11-17 | 2009-09-02 | Trustees Of Dartmouth College | Synthesis and biological activities of new tricyclic-bis-enones (tbes) |
| WO2012106190A1 (en) | 2011-01-31 | 2012-08-09 | Bristol-Myers Squibb Company | C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity |
| EP2653873B8 (en) | 2007-02-08 | 2022-08-24 | Biogen MA Inc. | Compositions and uses for treating Multiple Sclerosis |
| JP2008247898A (ja) | 2007-03-08 | 2008-10-16 | Santen Pharmaceut Co Ltd | トリテルペノイドを有効成分として含有する酸化ストレスが関連する眼疾患の予防又は治療剤 |
| WO2008136838A1 (en) | 2007-05-04 | 2008-11-13 | Trustees Of Dartmouth College | Novel amide derivatives of cddo and methods of use thereof |
| US8088824B2 (en) | 2007-08-15 | 2012-01-03 | Reata Pharmaceuticals Inc. | Forms of CDDO methyl ester |
| US20090048205A1 (en) | 2007-08-15 | 2009-02-19 | Colin Meyer | Combination therapy with synthetic triterpenoids and gemcitabine |
| US9012439B2 (en) | 2007-10-29 | 2015-04-21 | University Of Rochester | Use of electrophilic compounds for inducing platelet production or maintaining platelet function |
| ME03529B (me) | 2008-01-11 | 2020-04-20 | Reata Pharmaceuticals Inc | Sintetički triterpenoidi i metode njihove upotrebe u tretmanu bolesti |
| EP2279197B1 (en) | 2008-04-18 | 2014-11-05 | Reata Pharmaceuticals, Inc. | Antioxidant inflammation modulators: oleanolic acid derivatives with saturation in the c-ring |
| 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 |
| HUE033288T2 (en) | 2008-04-18 | 2017-11-28 | Reata Pharmaceuticals Inc | Antioxidant inflammation modulators: C-17 homologated oleic acid derivatives |
| US8278311B2 (en) | 2008-04-28 | 2012-10-02 | Abbott Laboratories | Substituted pyrimidine derivatives |
| ES2449396T3 (es) | 2008-07-22 | 2014-03-19 | Trustees Of Dartmouth College | Cianoenonas monocíclicas y métodos de uso de las mismas |
| WO2010053817A1 (en) | 2008-11-04 | 2010-05-14 | Trustees Of Dartmouth College | Betulinic acid derivatives and methods of use thereof |
| SG173601A1 (en) | 2009-02-13 | 2011-09-29 | Reata Pharmaceuticals Inc | Delayed release, oral dosage compositions that contain amorphous cddo-me |
| TWI481607B (zh) | 2009-12-17 | 2015-04-21 | Lundbeck & Co As H | 作為pde10a酵素抑制劑的2-芳基咪唑衍生物 |
| AU2011240690C1 (en) | 2010-04-12 | 2014-11-06 | Reata Pharmaceuticals Holdings, LLC | Method of treating obesity using antioxidant inflammation modulators |
| CN102079772A (zh) | 2010-12-09 | 2011-06-01 | 中国药科大学 | 一类五环三萜-13,28-内酯化合物、其制备方法和用途 |
| KR20140017520A (ko) | 2010-12-17 | 2014-02-11 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 살진균제 아조사이클릭 아미드 |
| ES2653717T3 (es) | 2010-12-17 | 2018-02-08 | Reata Pharmaceuticals, Inc. | Pirazolil- y pirimidinil-enonas tricíclicas como moduladores antioxidantes de la inflamación |
| EA026847B1 (ru) | 2011-03-11 | 2017-05-31 | Рита Фармасьютикалз, Инк. | C4-монометилтритерпеноидные производные и способы их применения |
| EP2841445B1 (en) | 2012-04-27 | 2017-06-14 | 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 |
| US9278912B2 (en) | 2012-09-10 | 2016-03-08 | Reata Pharmaceuticals, Inc. | C13-hydroxy derivatives of oleanolic acid 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 |
| TWI630212B (zh) | 2012-09-10 | 2018-07-21 | 瑞塔醫藥有限責任公司 | 丁香油素(oleanolic acid)之c17-烷二基與烯二基衍生物及其使用方法 |
| LT2892911T (lt) | 2012-09-10 | 2017-11-10 | Reata Pharmaceuticals, Inc. | Oleanolinės rūgšties c17 heteroarilo dariniai ir jų panaudojimo būdas |
| IL285832B2 (en) | 2013-08-23 | 2024-01-01 | Reata Pharmaceuticals Inc | Methods of treating and preventing endothelial dysfunction using bardoxolone methyl or analogs thereof |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN85101752A (zh) * | 1983-10-03 | 1987-01-31 | 美国辉瑞有限公司 | 2-胺基-5-羟基-4-甲基嘧啶衍生物的制备方法 |
| CN1162918A (zh) * | 1994-09-09 | 1997-10-22 | 小山省三 | 分子表达功能抑制剂 |
| CN1491225A (zh) * | 2000-12-28 | 2004-04-21 | СҰҩƷ��ҵ��ʽ���� | 三杂环化合物和包括其作为活性组分的药物 |
| WO2009146218A2 (en) * | 2008-04-18 | 2009-12-03 | Reata Pharmaceuticals, Inc. | Compounds including an anti-inflammatory pharmacore and methods of use |
| WO2009146216A2 (en) * | 2008-04-18 | 2009-12-03 | Reata Pharmaceuticals. Inc. | Antioxidant inflammation modulators: novel derivatives of oleanolic acid |
Non-Patent Citations (2)
| Title |
|---|
| NEW ENONE DERIVATIVES OF OLEANOLIC ACID AND URSOLIC ACID AS INHIBITORS OF NITRIC OXIDE PRODUCTION IN MOUSE MACROPHAGES;Tadashi Honda,等;《Bioorganic & Medicinal Chemistry Letters》;19970708;第7卷(第13期);第1623-1628页 * |
| Versatile Strategy to Access Tricycles Related to Quassinoids and Triterpenes;Pierre-Yves Caron,等;《Organic Letters》;20100107;第12卷(第3期);第510页方案7中化合物27 * |
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