JP2005511516A5 - - Google Patents
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- Publication number
- JP2005511516A5 JP2005511516A5 JP2003530678A JP2003530678A JP2005511516A5 JP 2005511516 A5 JP2005511516 A5 JP 2005511516A5 JP 2003530678 A JP2003530678 A JP 2003530678A JP 2003530678 A JP2003530678 A JP 2003530678A JP 2005511516 A5 JP2005511516 A5 JP 2005511516A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- tetrahydro
- naphthalenyl
- compound according
- tetramethyl
- 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.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 claims 71
- 150000001875 compounds Chemical class 0.000 claims 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 239000000047 product Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical group O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 150000004492 retinoid derivatives Chemical class 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 2
- 150000001336 alkenes Chemical class 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 230000022244 formylation Effects 0.000 claims 2
- 238000006170 formylation reaction Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 2
- 125000002524 organometallic group Chemical group 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- IOYHUMXQADXBLL-MDZDMXLPSA-N (e)-3-[4-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)-4,5,6,7-tetrahydro-1-benzofuran-2-yl]prop-2-enoic acid Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C1CCCC2=C1C=C(\C=C\C(O)=O)O2 IOYHUMXQADXBLL-MDZDMXLPSA-N 0.000 claims 1
- RJQKKTLAFODUMP-MDZDMXLPSA-N (e)-3-[4-(3-methoxy-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-4,5,6,7-tetrahydro-1-benzofuran-2-yl]prop-2-enoic acid Chemical compound COC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C1CCCC2=C1C=C(\C=C\C(O)=O)O2 RJQKKTLAFODUMP-MDZDMXLPSA-N 0.000 claims 1
- DMDWYOQQQYJTER-JLHYYAGUSA-N (e)-3-[4-(4-propan-2-yloxynaphthalen-1-yl)-2,3,3a,4-tetrahydro-1-benzofuran-2-yl]prop-2-enoic acid Chemical compound C12=CC=CC=C2C(OC(C)C)=CC=C1C1C2CC(\C=C\C(O)=O)OC2=CC=C1 DMDWYOQQQYJTER-JLHYYAGUSA-N 0.000 claims 1
- CWCPUIFVSMQHCH-ZHACJKMWSA-N (e)-3-[4-(5,5,8,8-tetramethyl-3-propoxy-6,7-dihydronaphthalen-2-yl)-4,5,6,7-tetrahydro-1-benzofuran-2-yl]prop-2-enoic acid Chemical compound CCCOC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C1CCCC2=C1C=C(\C=C\C(O)=O)O2 CWCPUIFVSMQHCH-ZHACJKMWSA-N 0.000 claims 1
- XLKGWBOSNUIFTI-PKNBQFBNSA-N (e)-3-[4-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1-benzofuran-2-yl]prop-2-enoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C1=CC=CC2=C1C=C(\C=C\C(O)=O)O2 XLKGWBOSNUIFTI-PKNBQFBNSA-N 0.000 claims 1
- KNZXLBCIIUUTAC-PKNBQFBNSA-N (e)-3-[4-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-2,3,3a,4-tetrahydro-1-benzofuran-2-yl]prop-2-enoic acid Chemical compound C1=CC=C2OC(\C=C\C(O)=O)CC2C1C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 KNZXLBCIIUUTAC-PKNBQFBNSA-N 0.000 claims 1
- FGQBLCYSBHFGFH-ZHACJKMWSA-N (e)-3-[4-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-4,5,6,7-tetrahydro-1,3-benzoxazol-2-yl]prop-2-enoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C1CCCC2=C1N=C(\C=C\C(O)=O)O2 FGQBLCYSBHFGFH-ZHACJKMWSA-N 0.000 claims 1
- IQLISKYOLFJFEL-PKNBQFBNSA-N (e)-3-[4-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]prop-2-enoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C1CCCC2=C1C=C(\C=C\C(O)=O)S2 IQLISKYOLFJFEL-PKNBQFBNSA-N 0.000 claims 1
- MLKGIWBMODUWFL-MDZDMXLPSA-N (e)-3-[4-[(2,6,6-trimethylcyclohexen-1-yl)methylamino]-1-benzofuran-2-yl]prop-2-enoic acid Chemical compound CC1(C)CCCC(C)=C1CNC1=CC=CC2=C1C=C(\C=C\C(O)=O)O2 MLKGIWBMODUWFL-MDZDMXLPSA-N 0.000 claims 1
- CTAQOCMZDLDVSH-VOTSOKGWSA-N (e)-3-[4-[(3-methoxy-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)methyl]furan-2-yl]prop-2-enoic acid Chemical compound COC1=CC(C(CCC2(C)C)(C)C)=C2C=C1CC1=COC(\C=C\C(O)=O)=C1 CTAQOCMZDLDVSH-VOTSOKGWSA-N 0.000 claims 1
- GPLSMLHEZAREAH-SOFGYWHQSA-N (e)-3-[4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)methyl]furan-2-yl]prop-2-enoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CC1=COC(\C=C\C(O)=O)=C1 GPLSMLHEZAREAH-SOFGYWHQSA-N 0.000 claims 1
- RCEOUDLEKDHFOM-SOFGYWHQSA-N (e)-3-[4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)methyl]thiophen-2-yl]prop-2-enoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CC1=CSC(\C=C\C(O)=O)=C1 RCEOUDLEKDHFOM-SOFGYWHQSA-N 0.000 claims 1
- UIXXSJQPMXCKRV-WGDLNXRISA-N (e)-3-[4-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]-1-benzofuran-2-yl]prop-2-enoic acid Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC2=C1C=C(\C=C\C(O)=O)O2 UIXXSJQPMXCKRV-WGDLNXRISA-N 0.000 claims 1
- PCLGZAGPVGBVBQ-VQHVLOKHSA-N (e)-3-[5-methyl-4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)methyl]furan-2-yl]prop-2-enoic acid Chemical compound O1C(\C=C\C(O)=O)=CC(CC=2C=C3C(C(CCC3(C)C)(C)C)=CC=2)=C1C PCLGZAGPVGBVBQ-VQHVLOKHSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- ORVWRLJXZZBPEJ-UHFFFAOYSA-N 4-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-4,5,6,7-tetrahydro-1-benzofuran-2-carboxylic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C1CCCC2=C1C=C(C(O)=O)O2 ORVWRLJXZZBPEJ-UHFFFAOYSA-N 0.000 claims 1
- -1 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl Chemical group 0.000 claims 1
- 238000003747 Grignard reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000001979 organolithium group Chemical group 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 102000027483 retinoid hormone receptors Human genes 0.000 claims 1
- 108091008679 retinoid hormone receptors Proteins 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32509201P | 2001-09-25 | 2001-09-25 | |
| PCT/US2002/029298 WO2003027090A2 (en) | 2001-09-25 | 2002-09-16 | Bicyclic heterocycles as rxr ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005511516A JP2005511516A (ja) | 2005-04-28 |
| JP2005511516A5 true JP2005511516A5 (https=) | 2005-12-22 |
Family
ID=23266396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003530678A Pending JP2005511516A (ja) | 2001-09-25 | 2002-09-16 | 選択的ｒｘｒリガンド |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US7173134B2 (https=) |
| EP (1) | EP1430042A2 (https=) |
| JP (1) | JP2005511516A (https=) |
| AU (1) | AU2002333655A1 (https=) |
| WO (1) | WO2003027090A2 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7264813B2 (en) | 2003-09-24 | 2007-09-04 | Nikken Sohonsha Corporation | Therapeutic uses of Dunaliella powder |
| US7435837B2 (en) | 2003-10-24 | 2008-10-14 | Wyeth | Dihydrobenzofuranyl alkanamine derivatives and methods for using same |
| BRPI0616454A2 (pt) | 2005-09-30 | 2011-06-21 | Vitae Pharmaceuticals, Inc. | métodos de tratamento de cáncer |
| WO2007076260A2 (en) | 2005-12-19 | 2007-07-05 | Smithkline Beecham Corporation | Farnesoid x receptor agonists |
| JP5211322B2 (ja) * | 2008-03-07 | 2013-06-12 | 国立医薬品食品衛生研究所長 | ピリミジン−５−カルボン酸誘導体の抗肥満剤としての新規用途 |
| DE102008022221A1 (de) | 2008-05-06 | 2009-11-12 | Universität des Saarlandes | Inhibitoren der humanen Aldosteronsynthase CYP11B2 |
| WO2010041449A1 (ja) * | 2008-10-09 | 2010-04-15 | 国立大学法人 岡山大学 | Rxr作動性物質を有効成分とする抗アレルギー剤 |
| IN2012DN00352A (https=) * | 2009-06-16 | 2015-08-21 | Bikam Pharmaceuticals Inc | |
| US8541404B2 (en) | 2009-11-09 | 2013-09-24 | Elexopharm Gmbh | Inhibitors of the human aldosterone synthase CYP11B2 |
| JP6322142B2 (ja) * | 2011-12-01 | 2018-05-09 | ビカム ファーマスーティカルス，インコーポレイテッド | オプシン結合性リガンド、組成物、及び使用方法 |
| MX352727B (es) | 2011-12-13 | 2017-12-06 | Dartmouth College | Tratamiento de trastorno autoinmune al usar agonistas de rxr. |
| US10653650B2 (en) | 2011-12-13 | 2020-05-19 | Io Therapeutics, Inc. | Treatment of diseases by concurrently eliciting remyelination effects and immunomodulatory effects using selective RXR agonists |
| WO2017075607A1 (en) | 2015-10-31 | 2017-05-04 | Io Therapeutics, Inc. | Treatment of nervous system disorders using combinations of pxr agonists and thyroid hormones |
| KR20180121983A (ko) | 2016-03-10 | 2018-11-09 | 아이오 테라퓨틱스, 인크. | Rxr 작용제 및 갑상선 호르몬의 조합을 사용한 근육 질환의 치료 |
| CA3016876C (en) | 2016-03-10 | 2021-12-28 | Io Therapeutics, Inc. | Treatment of autoimmune diseases with combinations of rxr agonists and thyroid hormones |
| CN105884823B (zh) * | 2016-05-31 | 2018-10-26 | 肇庆巨元生化有限公司 | 一种制备2,6,6-三甲基-1-环己烯基甲基膦酸酯的方法 |
| US11517549B2 (en) | 2017-09-20 | 2022-12-06 | Io Therapeutics, Inc. | Treatment of disease with esters of selective RXR agonists |
| CA3092682A1 (en) * | 2018-03-01 | 2019-09-06 | DJ Therapeutics LLC | Bexarotene derivatives and their use in treating cancer |
| US10966950B2 (en) | 2019-06-11 | 2021-04-06 | Io Therapeutics, Inc. | Use of an RXR agonist in treating HER2+ cancers |
| CA3242047A1 (en) | 2021-12-07 | 2023-06-15 | Io Therapeutics, Inc. | Use of an rxr agonist in treating drug resistant her2+ cancers |
| MX2024006978A (es) | 2021-12-07 | 2024-07-19 | Io Therapeutics Inc | Uso de un agonista de rxr y taxanos en el tratamiento de cáncer her2+. |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL71661A0 (en) * | 1983-04-27 | 1984-07-31 | Boehringer Ingelheim Kg | 4-phenyl-tetrahydro-furano-pyridines,their preparation and pharmaceutical compositions containing them |
| ATE187434T1 (de) * | 1993-01-11 | 1999-12-15 | Ligand Pharm Inc | Selektivitaet fuer retinoid x rezeptoren enthaltende verbindungen |
| US5399586A (en) * | 1993-03-11 | 1995-03-21 | Allergan, Inc. | Treatment of mammals afflicted with tumors with compounds having RXR retinoid receptor agonist activity |
| US6162815A (en) * | 1994-04-26 | 2000-12-19 | Centre International De Recherches Dermatologiques Galderma | RXR-agonist polycyclic aromatic compounds, pharmaceutical/cosmetic compositions comprising said compound and uses thereof |
| US5965606A (en) | 1995-12-29 | 1999-10-12 | Allergan Sales, Inc. | Methods of treatment with compounds having RAR.sub.α receptor specific or selective activity |
| FR2753091B1 (fr) | 1996-09-09 | 2001-03-16 | Oreal | Utilisation d'un agoniste des recepteurs des retinoides de type rxr pour stimuler ou induire la pousse des cheveux et/ou stopper leur chute |
| FR2756561B1 (fr) * | 1996-12-04 | 1999-01-08 | Cird Galderma | Composes heteroaryles, compositions pharmaceutiques et cosmetiques les contenant et utilisations |
| US6005007A (en) * | 1997-07-18 | 1999-12-21 | Farmer; Luc J. | Retinoids, methods for their production and use |
| AU2160899A (en) | 1997-12-11 | 1999-06-28 | Janssen Pharmaceutica N.V. | Retinoic acid mimetic anilides |
| EP1373240B1 (en) | 2001-03-14 | 2005-06-15 | Eli Lilly And Company | Retinoid x receptor modulators |
-
2002
- 2002-09-16 AU AU2002333655A patent/AU2002333655A1/en not_active Abandoned
- 2002-09-16 JP JP2003530678A patent/JP2005511516A/ja active Pending
- 2002-09-16 WO PCT/US2002/029298 patent/WO2003027090A2/en not_active Ceased
- 2002-09-16 US US10/490,805 patent/US7173134B2/en not_active Expired - Fee Related
- 2002-09-16 EP EP02799584A patent/EP1430042A2/en not_active Withdrawn
-
2006
- 2006-12-21 US US11/614,091 patent/US20070099991A1/en not_active Abandoned