JP2013533212A5 - - Google Patents
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- JP2013533212A5 JP2013533212A5 JP2013509316A JP2013509316A JP2013533212A5 JP 2013533212 A5 JP2013533212 A5 JP 2013533212A5 JP 2013509316 A JP2013509316 A JP 2013509316A JP 2013509316 A JP2013509316 A JP 2013509316A JP 2013533212 A5 JP2013533212 A5 JP 2013533212A5
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- JP
- Japan
- Prior art keywords
- analog
- group
- compound
- alkyl
- fluoro
- 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.)
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- 102100035178 Retinoic acid receptor RXR-alpha Human genes 0.000 claims description 9
- 101001093899 Homo sapiens Retinoic acid receptor RXR-alpha Proteins 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims 28
- 206010028980 Neoplasm Diseases 0.000 claims 16
- 201000011510 cancer Diseases 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- -1 cycloalkylO Chemical group 0.000 claims 4
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims 3
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims 3
- 108091008611 Protein Kinase B Proteins 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 claims 3
- 229960000894 sulindac Drugs 0.000 claims 3
- PZJFUNZDCRKXPZ-UHFFFAOYSA-N 2,5-dihydro-1h-tetrazole Chemical compound C1NNN=N1 PZJFUNZDCRKXPZ-UHFFFAOYSA-N 0.000 claims 2
- 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 230000006907 apoptotic process Effects 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 238000012216 screening Methods 0.000 claims 2
- AQQMERSMRLTKCK-VOTSOKGWSA-N (e)-3-(4-fluorophenyl)-2-methylprop-2-enoic acid Chemical compound OC(=O)C(/C)=C/C1=CC=C(F)C=C1 AQQMERSMRLTKCK-VOTSOKGWSA-N 0.000 claims 1
- NEQPIGQSLNSVDO-MDWZMJQESA-N 2-[(3e)-6-fluoro-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetic acid Chemical compound C1=CC(SC)=CC=C1\C=C/1C2=CC=C(F)C=C2C(CC(O)=O)=C\1 NEQPIGQSLNSVDO-MDWZMJQESA-N 0.000 claims 1
- LZXBOEDEEXSPDW-ZDLGFXPLSA-N 2-[(3z)-3-[(4-ethylphenyl)methylidene]-6-fluoro-2-methylinden-1-yl]acetic acid Chemical compound C1=CC(CC)=CC=C1\C=C\1C2=CC=C(F)C=C2C(CC(O)=O)=C/1C LZXBOEDEEXSPDW-ZDLGFXPLSA-N 0.000 claims 1
- BZRWYHUKBKGVAO-MFOYZWKCSA-N 2-[(3z)-6-fluoro-2-methyl-3-[(4-methylphenyl)methylidene]inden-1-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(C)C=C1 BZRWYHUKBKGVAO-MFOYZWKCSA-N 0.000 claims 1
- KPWBMCKJLTZFFT-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-methylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=C(F)C=C1 KPWBMCKJLTZFFT-UHFFFAOYSA-N 0.000 claims 1
- BABIQLUCYVRCIX-UHFFFAOYSA-N 6-fluoro-2-methyl-2,3-dihydroinden-1-one Chemical compound C1=C(F)C=C2C(=O)C(C)CC2=C1 BABIQLUCYVRCIX-UHFFFAOYSA-N 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 102000005765 Proto-Oncogene Proteins c-akt Human genes 0.000 claims 1
- 108010066463 Retinoid X Receptor alpha Proteins 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- RYKMJTNMCOIXGT-UHFFFAOYSA-N ethyl 2-(6-fluoro-2-methyl-3h-inden-1-yl)acetate Chemical compound C1=C(F)C=C2C(CC(=O)OCC)=C(C)CC2=C1 RYKMJTNMCOIXGT-UHFFFAOYSA-N 0.000 claims 1
- NDLXGCYDMUGQLL-UHFFFAOYSA-N ethyl 2-(6-fluoro-3h-inden-1-yl)acetate Chemical compound C1=C(F)C=C2C(CC(=O)OCC)=CCC2=C1 NDLXGCYDMUGQLL-UHFFFAOYSA-N 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- KPVCQZRUGWGAKD-UHFFFAOYSA-N methyl 3-(6-fluoro-3h-inden-1-yl)propanoate Chemical compound C1=C(F)C=C2C(CCC(=O)OC)=CCC2=C1 KPVCQZRUGWGAKD-UHFFFAOYSA-N 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- LFWHFZJPXXOYNR-MFOYZWKCSA-N sulindac sulfide Chemical compound C1=CC(SC)=CC=C1\C=C\1C2=CC=C(F)C=C2C(CC(O)=O)=C/1C LFWHFZJPXXOYNR-MFOYZWKCSA-N 0.000 claims 1
- 238000003752 polymerase chain reaction Methods 0.000 description 4
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33212410P | 2010-05-06 | 2010-05-06 | |
| US61/332,124 | 2010-05-06 | ||
| PCT/US2011/035651 WO2011140525A2 (en) | 2010-05-06 | 2011-05-06 | Methods and compositions related to a retinoid receptor-selective pathway |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016132716A Division JP6375340B2 (ja) | 2010-05-06 | 2016-07-04 | レチノイド受容体に選択的な経路に関する方法および組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013533212A JP2013533212A (ja) | 2013-08-22 |
| JP2013533212A5 true JP2013533212A5 (enExample) | 2014-07-10 |
Family
ID=44904518
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013509316A Pending JP2013533212A (ja) | 2010-05-06 | 2011-05-06 | レチノイド受容体に選択的な経路に関する方法および組成物 |
| JP2016132716A Expired - Fee Related JP6375340B2 (ja) | 2010-05-06 | 2016-07-04 | レチノイド受容体に選択的な経路に関する方法および組成物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016132716A Expired - Fee Related JP6375340B2 (ja) | 2010-05-06 | 2016-07-04 | レチノイド受容体に選択的な経路に関する方法および組成物 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US9611235B2 (enExample) |
| EP (1) | EP2571497B1 (enExample) |
| JP (2) | JP2013533212A (enExample) |
| KR (1) | KR101889290B1 (enExample) |
| CN (2) | CN103002887B (enExample) |
| AU (1) | AU2011249857B2 (enExample) |
| CA (1) | CA2798692C (enExample) |
| ES (1) | ES2702532T3 (enExample) |
| WO (1) | WO2011140525A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9611235B2 (en) | 2010-05-06 | 2017-04-04 | Sanford-Burnham Medical Research Institute | Methods and compositions related to a retinoid receptor-selective pathway |
| CN103491772A (zh) * | 2011-04-01 | 2014-01-01 | 南方研究所 | 舒林酸衍生物、其用途及其制备 |
| WO2015100267A1 (en) * | 2013-12-23 | 2015-07-02 | Sanford-Burnham Medical Research Institute | Methods and compositions for treating cancer |
| WO2017193086A1 (en) * | 2016-05-06 | 2017-11-09 | Tarrex Biopharma Inc. | Therapeutic compounds and methods |
| KR20230024976A (ko) * | 2020-06-12 | 2023-02-21 | 누크미토 파마슈티컬스 컴퍼니, 리미티드 | 인덴 화합물, 이의 약제학적 조성물, 및 이의 치료학적 적용 |
| CN117916215A (zh) * | 2021-05-15 | 2024-04-19 | 藤济(厦门)生物医药科技有限公司 | 茚化合物、其药物组合物及其治疗应用 |
| EP4619369A1 (en) * | 2022-11-16 | 2025-09-24 | Nucmito Pharmaceuticals Co., Ltd. | Indene compounds, pharmaceutical compositions thereof, and their therapeutic applications |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001012858A1 (en) | 1999-08-16 | 2001-02-22 | The Johns Hopkins University | PPARδ LINKS APC TO CHEMOPREVENTIVE DRUGS |
| DE10163426A1 (de) * | 2001-12-21 | 2003-07-03 | Max Planck Gesellschaft | Pharmakologisch wirksame Inden-Derivate |
| AU2003298020A1 (en) * | 2002-11-26 | 2004-06-18 | Florida Atlantic University | Catalytic antioxidants and methods of use |
| EP1668362A4 (en) | 2003-08-13 | 2007-07-04 | Burnham Inst | CYTOPLASMATIC ACTIVITY OF THE RETINOID-X RECEPTOR AND ITS REGULATION BY LIGANDING AND DIMERIZATION |
| JP2005247807A (ja) | 2004-03-08 | 2005-09-15 | Japan Science & Technology Agency | Ｎｓａｉｄを利用した癌治療用組成物 |
| WO2006102439A2 (en) * | 2005-03-23 | 2006-09-28 | Florida Atlantic University | Treatment or prevention of cancer and precancerous disorders |
| JP5337491B2 (ja) * | 2006-01-04 | 2013-11-06 | サザン リサーチ インスティテュート | スリンダクの誘導体類、その使用及びその調製 |
| WO2010070379A1 (en) | 2008-12-17 | 2010-06-24 | Centre National De La Recherche Scientifique | Rxr-ppargamma agonist/growth factor inhibitor combination therapy for inducing apoptosis and the treatment of cancer |
| US9611235B2 (en) | 2010-05-06 | 2017-04-04 | Sanford-Burnham Medical Research Institute | Methods and compositions related to a retinoid receptor-selective pathway |
| CN102030642A (zh) | 2010-12-03 | 2011-04-27 | 厦门大学 | 舒林酸类似物的中间体的合成方法与应用 |
| WO2015100267A1 (en) | 2013-12-23 | 2015-07-02 | Sanford-Burnham Medical Research Institute | Methods and compositions for treating cancer |
| WO2017193086A1 (en) | 2016-05-06 | 2017-11-09 | Tarrex Biopharma Inc. | Therapeutic compounds and methods |
-
2011
- 2011-05-06 US US13/102,475 patent/US9611235B2/en not_active Expired - Fee Related
- 2011-05-06 ES ES11778467T patent/ES2702532T3/es active Active
- 2011-05-06 CN CN201180030974.9A patent/CN103002887B/zh not_active Expired - Fee Related
- 2011-05-06 CN CN201611020419.9A patent/CN107050007B/zh not_active Expired - Fee Related
- 2011-05-06 JP JP2013509316A patent/JP2013533212A/ja active Pending
- 2011-05-06 KR KR1020127031894A patent/KR101889290B1/ko not_active Expired - Fee Related
- 2011-05-06 CA CA2798692A patent/CA2798692C/en not_active Expired - Fee Related
- 2011-05-06 AU AU2011249857A patent/AU2011249857B2/en not_active Ceased
- 2011-05-06 WO PCT/US2011/035651 patent/WO2011140525A2/en not_active Ceased
- 2011-05-06 EP EP11778467.8A patent/EP2571497B1/en not_active Not-in-force
-
2016
- 2016-07-04 JP JP2016132716A patent/JP6375340B2/ja not_active Expired - Fee Related
-
2017
- 2017-02-16 US US15/435,125 patent/US10087156B2/en not_active Expired - Fee Related
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