JP2011518192A5 - - Google Patents
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- JP2011518192A5 JP2011518192A5 JP2011505260A JP2011505260A JP2011518192A5 JP 2011518192 A5 JP2011518192 A5 JP 2011518192A5 JP 2011505260 A JP2011505260 A JP 2011505260A JP 2011505260 A JP2011505260 A JP 2011505260A JP 2011518192 A5 JP2011518192 A5 JP 2011518192A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- groups
- acyl
- hydrogen
- aryl
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 181
- 125000002252 acyl group Chemical group 0.000 claims description 92
- -1 tautomer Substances 0.000 claims description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 239000001257 hydrogen Substances 0.000 claims description 84
- 230000003287 optical effect Effects 0.000 claims description 83
- 150000003839 salts Chemical class 0.000 claims description 83
- 239000012453 solvate Substances 0.000 claims description 74
- 125000003118 aryl group Chemical group 0.000 claims description 69
- 125000004423 acyloxy group Chemical group 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 63
- 229910019142 PO4 Inorganic materials 0.000 claims description 59
- 238000006467 substitution reaction Methods 0.000 claims description 59
- 239000010452 phosphate Substances 0.000 claims description 58
- 125000003545 alkoxy group Chemical group 0.000 claims description 57
- 125000004104 aryloxy group Chemical group 0.000 claims description 57
- 125000003282 alkyl amino group Chemical group 0.000 claims description 56
- 125000001769 aryl amino group Chemical group 0.000 claims description 56
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 55
- 125000000304 alkynyl group Chemical group 0.000 claims description 52
- 150000001408 amides Chemical class 0.000 claims description 52
- 125000003342 alkenyl group Chemical group 0.000 claims description 51
- 125000005843 halogen group Chemical group 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 51
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 51
- 150000002431 hydrogen Chemical class 0.000 claims description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 39
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 26
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 26
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 26
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 26
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 26
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 24
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 23
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 23
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 23
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 18
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 18
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 15
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 14
- 238000001727 in vivo Methods 0.000 claims description 14
- 229940002612 prodrug Drugs 0.000 claims description 14
- 239000000651 prodrug Substances 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000005035 acylthio group Chemical group 0.000 claims description 11
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 11
- 125000005108 alkenylthio group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000005139 alkynylsulfonyl group Chemical group 0.000 claims description 11
- 125000005109 alkynylthio group Chemical group 0.000 claims description 11
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 11
- 125000005110 aryl thio group Chemical group 0.000 claims description 11
- 125000003441 thioacyl group Chemical group 0.000 claims description 11
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 9
- 230000002757 inflammatory effect Effects 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000005136 alkenylsulfinyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 5
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
- 125000005134 alkynylsulfinyl group Chemical group 0.000 claims description 3
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical group [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims 23
- 125000003368 amide group Chemical group 0.000 claims 8
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 6
- 241000277306 Esocidae Species 0.000 claims 2
- 241001024304 Mino Species 0.000 claims 2
- 125000005549 heteroarylene group Chemical group 0.000 claims 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 150000001345 alkine derivatives Chemical class 0.000 description 7
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- SHGAZHPCJJPHSC-ZVCIMWCZSA-N 9-cis-retinoic acid Chemical compound OC(=O)/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-ZVCIMWCZSA-N 0.000 description 2
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|---|---|---|---|---|
| US6326507B1 (en) | 1998-06-19 | 2001-12-04 | Trustees Of Dartmouth College | Therapeutic compounds and methods of use |
| DE602006021142D1 (de) | 2005-02-03 | 2011-05-19 | Gen Hospital Corp | Verfahren zur behandlung von gefitinib-resistentem krebs |
| PE20070763A1 (es) | 2005-11-04 | 2007-08-08 | Wyeth Corp | COMBINACIONES ANTINEOPLASICAS DE UN INHIBIDOR DE mTOR, TRASTUZUMAB Y/O HKI-272 |
| US8022216B2 (en) | 2007-10-17 | 2011-09-20 | Wyeth Llc | Maleate salts of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof |
| EP3492077A1 (en) | 2008-01-11 | 2019-06-05 | Reata Pharmaceuticals, Inc. | Synthetic triterpenoids and methods of use in the treatment of disease |
| AU2009237578C1 (en) | 2008-04-18 | 2014-12-04 | Reata Pharmaceuticals, Inc. | Antioxidant inflammation modulators: oleanolic acid derivatives with saturation in the C-ring |
| KR101782020B1 (ko) | 2008-04-18 | 2017-09-26 | 리타 파마슈티컬스 잉크. | 산화방지성 염증 조절제 ｃ-17 일치된 올레아놀산 유도체 |
| TW201004627A (en) | 2008-04-18 | 2010-02-01 | Reata Pharmaceuticals Inc | Antioxidant inflammation modulators: novel derivatives of oleanolic acid |
| WO2009129546A1 (en) | 2008-04-18 | 2009-10-22 | Reata Pharmaceuticals, Inc. | Antioxidant inflammation modulators: oleanolic acid derivatives with amino and other modifications at c-17 |
| AU2009251437B2 (en) | 2008-04-18 | 2014-10-30 | Reata Pharmaceuticals, Inc. | Compounds including an anti-inflammatory pharmacore and methods of use |
| ES2692769T3 (es) | 2008-06-17 | 2018-12-05 | Wyeth Llc | Combinaciones antineoplásicas que contienen HKI-272 y vinorelbina |
| ES2449396T3 (es) | 2008-07-22 | 2014-03-19 | Trustees Of Dartmouth College | Cianoenonas monocíclicas y métodos de uso de las mismas |
| CN109464445A (zh) | 2008-08-04 | 2019-03-15 | 惠氏有限责任公司 | 4-苯胺基-3-氰基喹啉和卡培他滨的抗肿瘤组合 |
| LT3000467T (lt) | 2009-04-06 | 2023-04-11 | Wyeth Llc | Krūties vėžio gydymo schema naudojant neratinibą |
| ME03713B (me) | 2010-04-12 | 2021-01-20 | Reata Pharmaceuticals Inc | Bardoksolon meтil za lečenje gojaznosтi |
| CN103038245B (zh) * | 2010-06-04 | 2015-03-25 | 百时美施贵宝公司 | 作为hiv成熟抑制剂的c-3经修饰的桦木酸衍生物 |
| EP2576586B1 (en) * | 2010-06-04 | 2015-08-12 | Bristol-Myers Squibb Company | C-28 amides of modified c-3 betulinic acid derivatives as hiv maturation inhibitors |
| EA025568B1 (ru) | 2010-12-17 | 2017-01-30 | Рита Фармасьютикалз, Инк. | Пиразолильные и пиримидинильные трициклические еноны в качестве антиоксидантных модуляторов воспаления |
| BR112013023174B1 (pt) | 2011-03-11 | 2021-09-21 | Reata Pharmaceuticals, Inc | Compostos derivados de triterpenoide de c4-monometila e composição farmacêutica compreendendo os referidos compostos |
| MX357060B (es) | 2012-04-27 | 2018-06-25 | Reata Pharmaceuticals Inc | Derivados de 2,2-difluoropropionamida de bardoxolon metilo, formas polimorficas y metodo para su uso de los mismos. |
| US8921419B2 (en) | 2012-05-08 | 2014-12-30 | Trustees Of Dartmouth College | Triterpenoids and compositions containing the same |
| US8981144B2 (en) * | 2012-05-08 | 2015-03-17 | Trustees Of Dartmouth College | Method for synthesizing 2-cyano-3,12-dioxoolean-1, 9(11)-dien-28-oic acid methyl ester and derivatives thereof |
| 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 |
| WO2014040056A1 (en) * | 2012-09-10 | 2014-03-13 | Reata Pharmaceuticals, Inc. | C17-heteroaryl 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 |
| CA2884400A1 (en) * | 2012-09-10 | 2014-03-13 | Abbvie Inc. | Glycyrrhetinic acid derivatives and methods of use thereof |
| UY35023A (es) | 2012-09-10 | 2014-03-31 | Reata Pharmaceuticals Inc | Derivados c17-alcandiilo y alquendiilo del ácido oleanólico y sus métodos de uso |
| CN102861037B (zh) * | 2012-10-26 | 2014-04-16 | 吴俊华 | Gypensapogenin B在治疗动脉粥样硬化药物中的应用 |
| CN103800902A (zh) * | 2012-11-14 | 2014-05-21 | 中国药科大学 | 含有齐墩果酸的药物组合物及其医药用途 |
| WO2014091467A2 (en) * | 2012-12-16 | 2014-06-19 | Mahesh Kandula | Compositions and methods for the treatment of autoimmune diseases and inflammation |
| TW201514192A (zh) | 2013-03-19 | 2015-04-16 | Daiichi Sankyo Co Ltd | 萜類衍生物 |
| UY39092A (es) | 2013-04-24 | 2021-03-26 | Abbvie Inc | Derivados de 2,2-difluoropropanamida y metil bardoxolona, formas polimórficas y métodos de uso |
| IL285832B2 (en) | 2013-08-23 | 2024-01-01 | Reata Pharmaceuticals Inc | Methods for the treatment and prevention of impaired functioning of the endothelium using brodoxolone methyl or its analogs |
| US10189791B2 (en) | 2014-08-26 | 2019-01-29 | Trustees Of Dartmouth College | Pyridyl analogs of 1-(2-cyano-3,12-dioxooleana-1,9(11)dien-28-oyl) imidazole |
| WO2016033132A1 (en) | 2014-08-26 | 2016-03-03 | Trustees Of Dartmouth College | Pyridyl analogs of 1-(2-cyano-3,12-dioxooleana-1,9(11)dien-28-oyl) imidazole |
| US10208082B2 (en) | 2014-09-10 | 2019-02-19 | Daiichi Sankyo Company, Limited | Sustained-release pharmaceutical composition for treatment and prevention of eye disease |
| AU2016219109B2 (en) | 2015-02-12 | 2020-05-14 | Reata Pharmaceuticals, Inc. | Imidazolyl tricyclic enones as antioxidant iflammation modulators |
| CA2998681C (en) | 2015-09-23 | 2024-02-06 | Reata Pharmaceuticals, Inc. | C4-modified oleanolic acid derivatives for inhibition of il-17 and other uses |
| KR102475130B1 (ko) * | 2016-03-31 | 2022-12-07 | (주)아모레퍼시픽 | 펜타사이클릭 트리터펜 카페익 액씨드 에스터를 포함하는 피부 보습 또는 피부 미백용 조성물 |
| 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 |
| AU2018334467B2 (en) | 2017-09-14 | 2022-10-20 | Phoenix Biotechnology, Inc. | Method and improved neuroprotective composition for treating neurological conditions |
| MX2020002883A (es) | 2017-09-14 | 2020-10-05 | Phoenix Biotechnology Inc | Método y composiciones para tratar la infección viral. |
| US10137138B1 (en) | 2018-05-29 | 2018-11-27 | King Saud University | Sulfonylurea derivatives of oleanolic acid |
| IL322405A (en) | 2018-06-15 | 2025-09-01 | Reata Pharmaceuticals Inc | Decahydro-2h-naphth[1,2-d]imidazole compounds for inhibition of IL-17 and ROR-gamma |
| 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 |
| SG11202108541RA (en) * | 2019-02-07 | 2021-09-29 | Ardelyx Inc | Glycyrrhetinic acid derivatives for use in treating hyperkalemia |
| CN114641483B (zh) | 2019-07-19 | 2024-12-06 | 里亚塔医药公司 | C17极性的-取代的杂芳族合成三萜类化合物及其使用方法 |
| CR20220345A (es) * | 2019-12-19 | 2023-01-12 | Reata Pharmaceuticals Inc | Triterpenoides sintéticos con sustituyentes a base de nitrógeno en c-17 y métodos de uso de los mismos |
| CN111205346B (zh) * | 2020-02-10 | 2022-01-28 | 中国药科大学 | 齐墩果酸的衍生物及其医药用途 |
| EP4295854A3 (en) | 2020-03-31 | 2024-04-03 | Phoenix Biotechnology, Inc. | Method and compositions for treating coronavirus infection |
| RU2020130238A (ru) | 2020-03-31 | 2022-03-14 | Феникс Байотекнолоджи, Инк. | Способ и композиции для лечения коронавирусной инфекции |
| CN115697319A (zh) * | 2020-04-01 | 2023-02-03 | 四川海思科制药有限公司 | 三萜系化合物nrf2抑制剂的用途 |
| IL298008A (en) | 2020-05-09 | 2023-01-01 | Reata Pharmaceuticals Holdings Llc | Methods for treating covid-19 with the help of bardoxolone methyl or its analogs |
| WO2022126129A1 (en) | 2020-12-11 | 2022-06-16 | Reata Pharmaceuticals, Inc. | Synthetic triterpenoids for use in therapy |
| AU2022208727A1 (en) | 2021-01-18 | 2023-08-03 | Reata Pharmaceuticals, Inc. | Synthetic ursolic acid derivatives and methods of use thereof |
| CN115626947B (zh) * | 2022-09-27 | 2024-07-02 | 中山大学 | 五环三萜类天然产物的合成及其应用 |
| CN115501237B (zh) * | 2022-10-27 | 2023-09-05 | 五邑大学 | 齐墩果酸衍生物在制备抑菌药物中的应用 |
| WO2025029691A1 (en) | 2023-07-28 | 2025-02-06 | Reata Pharmaceuticals Holdings, LLC | Methods for producing triterpenoid derivatives |
Family Cites Families (95)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1435622A (en) | 1973-11-07 | 1976-05-12 | Biorex Laboratories Ltd | Erythrodiol derivatives |
| JPS5555153U (cg-RX-API-DMAC7.html) | 1978-10-06 | 1980-04-14 | ||
| US4395423A (en) | 1978-10-10 | 1983-07-26 | Sterling Drug Inc. | Polycyclic cyanoketones |
| US4634208A (en) | 1983-01-31 | 1987-01-06 | Amp Incorporated | Electrical plug connector and method of terminating a cable therewith |
| US4526988A (en) | 1983-03-10 | 1985-07-02 | Eli Lilly And Company | Difluoro antivirals and intermediate therefor |
| DE3321117A1 (de) | 1983-06-10 | 1984-12-13 | Siemens AG, 1000 Berlin und 8000 München | Magnetische multipolanordnung n-ter ordnung |
| ATE92499T1 (de) | 1984-12-04 | 1993-08-15 | Lilly Co Eli | Tumorbehandlung bei saeugetieren. |
| US4635208A (en) | 1985-01-18 | 1987-01-06 | Hewlett-Packard Company | Computer-aided design of systems |
| US4636308A (en) | 1985-06-13 | 1987-01-13 | Summers Don D | Method and apparatus for reclaiming drilling fluids from undesirable solids in a drilling operation |
| US4636608A (en) | 1985-11-15 | 1987-01-13 | Benteler Corporation | Laser contour cut door beams |
| US5013649A (en) | 1986-07-01 | 1991-05-07 | Genetics Institute, Inc. | DNA sequences encoding osteoinductive products |
| IL84842A0 (en) | 1986-12-24 | 1988-06-30 | Lilly Co Eli | Immunoglobulin conjugates |
| ES2075040T3 (es) | 1988-02-16 | 1995-10-01 | Lilly Co Eli | 2',3'-dideoxi-2',2'-difluoronucleosidos. |
| US5443826A (en) | 1988-08-02 | 1995-08-22 | Borody; Thomas J. | Treatment of gastro-intestinal disorders with a fecal composition or a composition of bacteroides and E. Coli |
| US5064823A (en) | 1988-08-24 | 1991-11-12 | Research Triangle Institute | Pentacyclic triterpenoid compounds as topoisomerase inhibitors or cell differentiation inducers |
| CA2004695C (en) | 1988-12-12 | 1999-08-10 | Rosanne Bonjouklian | Phospholipid nucleosides |
| JPH05505815A (ja) | 1990-04-04 | 1993-08-26 | ニユコメド・イメージング・アクシエセルカペト | ヌクレオシド誘導体 |
| SE502569C2 (sv) | 1991-05-31 | 1995-11-13 | British Tech Group | Användning av en immunologiskt inert matris av en sterol och saponiner som kan bilda sfäriska nanopartiklar med snäv storleksfördelning som läkemedelsbärare, partiklar, komposition samt kit |
| YU43193A (sh) | 1992-06-22 | 1997-01-08 | Eli Lilly And Company | 2'-deoksi-2',2'-difluoro(4-supstituisani)pirimidinski nukleozidi antivirusnog i antikancerogenog dejstva i međuproizvodi |
| US5401838A (en) | 1992-06-22 | 1995-03-28 | Eli Lilly And Company | Stereoselective fusion glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides |
| US5606048A (en) | 1992-06-22 | 1997-02-25 | Eli Lilly And Company | Stereoselective glycosylation process for preparing 2'-Deoxy-2', 2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides |
| UA41261C2 (uk) | 1992-06-22 | 2001-09-17 | Елі Ліллі Енд Компані | Спосіб одержання збагачених бета-аномером нуклеозидів |
| US5426183A (en) | 1992-06-22 | 1995-06-20 | Eli Lilly And Company | Catalytic stereoselective glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides |
| DE4308042C2 (de) | 1993-03-13 | 2000-10-12 | Alstom Energy Syst Gmbh | Wälzmühle |
| US6025395A (en) | 1994-04-15 | 2000-02-15 | Duke University | Method of preventing or delaying the onset and progression of Alzheimer's disease and related disorders |
| US5972703A (en) | 1994-08-12 | 1999-10-26 | The Regents Of The University Of Michigan | Bone precursor cells: compositions and methods |
| US5599795A (en) | 1994-08-19 | 1997-02-04 | Mccann; Michael | Method for treatment of idiopathic inflammatory bowel disease (IIBD) |
| US5521294A (en) | 1995-01-18 | 1996-05-28 | Eli Lilly And Company | 2,2-difluoro-3-carbamoyl ribose sulfonate compounds and process for the preparation of beta nucleosides |
| DE69724964T2 (de) | 1996-07-03 | 2004-07-22 | Pharmacia & Upjohn Co., Kalamazoo | Zielgerichte arzneimittel abgabe für zulphonamide-derivate |
| NZ336676A (en) | 1997-01-24 | 2000-01-28 | Norsk Hydro As | Gemcitabine esters or amides useful as anti-cancer and anti-viral agents |
| US20050276836A1 (en) | 1997-06-11 | 2005-12-15 | Michelle Wilson | Coated vaginal devices for vaginal delivery of therapeutically effective and/or health-promoting agents |
| US5965119A (en) | 1997-12-30 | 1999-10-12 | Enzon, Inc. | Trialkyl-lock-facilitated polymeric prodrugs of amino-containing bioactive agents |
| 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 |
| US6485756B1 (en) | 1999-04-06 | 2002-11-26 | Collaborative Technologies, Inc. | Stable, homogeneous natural product extracts containing polar and apolar fractions |
| ATE370928T1 (de) | 1999-05-14 | 2007-09-15 | Nereus Pharmaceuticals Inc | Interleukin-1 und tumornekrosefaktor-alpha modulatoren,synthese dieser modulatoren und methoden zur anwendung dieser modulatoren |
| JP3737968B2 (ja) | 1999-06-25 | 2006-01-25 | ロシュ ダイアグノスティックス コーポレーション | 酵素阻害イムノアッセイ |
| US6649654B1 (en) | 1999-11-23 | 2003-11-18 | The Regents Of The University Of California | Methods for identifying and using IKK inhibitors |
| 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 |
| US6951847B2 (en) | 2000-09-29 | 2005-10-04 | Regents Of The University Of Minnesota | Methods of treating fungal infections using lupeol |
| EP1322661A1 (en) | 2000-09-29 | 2003-07-02 | Regents Of The University Of Minnesota | Triterpenes having fungicidal activity against yeast |
| WO2002026762A1 (en) | 2000-09-29 | 2002-04-04 | Regents Of The University Of Minnesota | Triterpenes having antibacterial activity |
| US6878751B1 (en) | 2000-10-19 | 2005-04-12 | Imperial College Of Science Technology And Medicine | Administration of resveratrol to treat inflammatory respiratory disorders |
| WO2002047611A2 (en) | 2000-11-28 | 2002-06-20 | Board Of Regents, The University Of Texas System | Cddo-compounds and combination therapies thereof |
| US7435755B2 (en) | 2000-11-28 | 2008-10-14 | The Trustees Of Dartmouth College | CDDO-compounds and combination therapies thereof |
| AU2002308701A1 (en) | 2001-05-14 | 2002-11-25 | University Of Maryland, Baltimore | Novel alanine transaminase enzyme and methods of use |
| US6794801B2 (en) | 2001-10-31 | 2004-09-21 | Toshiba Lighting & Technology Corporation | Compact selfballasted fluorescent lamp and luminaire |
| EP1492523A2 (en) | 2001-11-23 | 2005-01-05 | Chugai Seiyaku Kabushiki Kaisha | Method for identification of tumor targeting enzymes |
| EP1465615B1 (en) | 2002-01-15 | 2012-08-01 | Trustees of Dartmouth College | Tricyclic-bis-enone derivatives and methods of use thereof |
| MXPA04006953A (es) | 2002-01-18 | 2005-06-20 | Univ Minnesota | Sales cuaternarias de triperpeno como surfactantes biologicamente activos. |
| CA2485565A1 (en) * | 2002-05-13 | 2004-08-05 | Trustees Of Dartmouth College | Inhibitors and methods of use thereof |
| EP1567169A4 (en) | 2002-11-04 | 2009-10-21 | Xenoport Inc | GEMCITABINE PROMOTERS, THEIR PHARMACEUTICAL COMPOSITIONS AND USES THEREOF |
| WO2004089357A2 (en) | 2003-04-02 | 2004-10-21 | Regents Of The University Of Minnesota | Anti-fungal formulation of triterpene and essential oil |
| US20050208151A1 (en) | 2003-10-30 | 2005-09-22 | Entelos, Inc. | Treatment of rheumatoid arthritis with FLIP antagonists |
| US8288439B2 (en) | 2003-11-04 | 2012-10-16 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Methods and compositions for the inhibition of HIV-1 replication |
| PL1803468T3 (pl) | 2003-12-22 | 2012-05-31 | Novartis Ag | Środki do leczenia retinopatii jaskrowej i neuropatii wzrokowej |
| 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 |
| JP5087400B2 (ja) | 2004-09-07 | 2012-12-05 | パシフィック アロー リミテッド | アンゲロイル基を有する抗腫瘍化合物 |
| US7714726B2 (en) | 2005-05-06 | 2010-05-11 | Dominic M. Kotab | Semi-transparent RFID tags |
| JP2006347952A (ja) * | 2005-06-16 | 2006-12-28 | Yoshihiro Futamura | リパーゼ活性化作用を呈するアントラキノン誘導体、それからなる抗肥満薬、食品製剤及び化粧品 |
| WO2007005879A2 (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 |
| NZ569078A (en) | 2005-12-12 | 2012-01-12 | Mosamedix Bv | Annexin derivatives suitable for pretargeting in therapy and diagnosis |
| JP2009530405A (ja) | 2006-03-23 | 2009-08-27 | アドバンスト ライフ サイエンシズ インコーポレイテッド | 合成五環性トリテルペノイド、ならびにベツリン酸およびベツリンの誘導体 |
| 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 |
| CN101117348B (zh) * | 2006-08-01 | 2010-12-29 | 浙江海正药业股份有限公司 | A环和c环多氧化取代的五环三萜及其制备方法和用途 |
| 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 |
| US20090203661A1 (en) | 2006-10-12 | 2009-08-13 | Safe Stephen H | Betulinic acid, derivatives and analogs thereof and uses therefor |
| JP2010510243A (ja) | 2006-11-17 | 2010-04-02 | トラスティーズ オブ ダートマス カレッジ | 三環系−ビス−エノン（ｔｂｅ）の合成および生物学的活性 |
| 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 |
| DK2629097T1 (da) | 2007-02-08 | 2022-05-30 | Biogen Ma Inc | NRF2-screeningsassays og relaterede fremgangsmåder og sammensætninger |
| 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 |
| WO2009023845A2 (en) | 2007-08-15 | 2009-02-19 | The Board Of Regents Of The University Of Texas System | Combination therapy with synthetic triterpenoids and gemcitabine |
| US8088824B2 (en) | 2007-08-15 | 2012-01-03 | Reata Pharmaceuticals Inc. | Forms of CDDO methyl ester |
| US9012439B2 (en) | 2007-10-29 | 2015-04-21 | University Of Rochester | Use of electrophilic compounds for inducing platelet production or maintaining platelet function |
| EP3492077A1 (en) | 2008-01-11 | 2019-06-05 | Reata Pharmaceuticals, Inc. | Synthetic triterpenoids and methods of use in the treatment of disease |
| AU2009251437B2 (en) | 2008-04-18 | 2014-10-30 | Reata Pharmaceuticals, Inc. | Compounds including an anti-inflammatory pharmacore and methods of use |
| KR101782020B1 (ko) | 2008-04-18 | 2017-09-26 | 리타 파마슈티컬스 잉크. | 산화방지성 염증 조절제 ｃ-17 일치된 올레아놀산 유도체 |
| TW201004627A (en) | 2008-04-18 | 2010-02-01 | Reata Pharmaceuticals Inc | Antioxidant inflammation modulators: novel derivatives of oleanolic acid |
| AU2009237578C1 (en) | 2008-04-18 | 2014-12-04 | Reata Pharmaceuticals, Inc. | Antioxidant inflammation modulators: oleanolic acid derivatives with saturation in the C-ring |
| WO2009129546A1 (en) | 2008-04-18 | 2009-10-22 | Reata Pharmaceuticals, Inc. | Antioxidant inflammation modulators: oleanolic acid derivatives with amino and other modifications at c-17 |
| 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 |
| HUE035013T2 (en) | 2009-02-13 | 2018-05-02 | Reata Pharmaceuticals Inc | Delayed release, oral dosage compositions that contain amorphous cddo-me |
| RU2401273C1 (ru) | 2009-03-30 | 2010-10-10 | Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) (статус государственного учреждения) | Противоопухолевое средство тритерпеновой природы, полученное путем модификации глицирретовой кислоты |
| ME03713B (me) | 2010-04-12 | 2021-01-20 | Reata Pharmaceuticals Inc | Bardoksolon meтil za lečenje gojaznosтi |
| EP2670765B1 (en) | 2011-01-31 | 2017-10-18 | Viiv Healthcare Uk (No. 4) Limited | C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity |
| BR112013023174B1 (pt) | 2011-03-11 | 2021-09-21 | Reata Pharmaceuticals, Inc | Compostos derivados de triterpenoide de c4-monometila e composição farmacêutica compreendendo os referidos compostos |
| CN208692323U (zh) | 2018-08-13 | 2019-04-05 | 深圳市优维尔科技有限公司 | 一种抽吸装置 |
| US11133308B2 (en) | 2019-05-03 | 2021-09-28 | International Business Machines Corporation | Uniform work function metal recess for vertical transistor complementary metal oxide semiconductor technology |
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