CN103002887B - 涉及类视黄醇受体选择性通路的方法和组合物 - Google Patents
涉及类视黄醇受体选择性通路的方法和组合物 Download PDFInfo
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- CN103002887B CN103002887B CN201180030974.9A CN201180030974A CN103002887B CN 103002887 B CN103002887 B CN 103002887B CN 201180030974 A CN201180030974 A CN 201180030974A CN 103002887 B CN103002887 B CN 103002887B
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- Prior art keywords
- rxrα
- sulindac
- cells
- tnfα
- akt
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- 0 CC(C(C*)c1cc(F)ccc11)C1=C(c1ccc(*)cc1)N Chemical compound CC(C(C*)c1cc(F)ccc11)C1=C(c1ccc(*)cc1)N 0.000 description 4
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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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- A61K31/01—Hydrocarbons
- A61K31/015—Hydrocarbons carbocyclic
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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
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- 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
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/402—1-aryl substituted, e.g. piretanide
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/19—Cytokines; Lymphokines; Interferons
- A61K38/191—Tumor necrosis factors [TNF], e.g. lymphotoxin [LT], i.e. TNF-beta
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/62—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
- G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
- G01N33/5011—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics for testing antineoplastic activity
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/435—Assays involving biological materials from specific organisms or of a specific nature from animals; from humans
- G01N2333/705—Assays involving receptors, cell surface antigens or cell surface determinants
- G01N2333/70567—Nuclear receptors, e.g. retinoic acid receptor [RAR], RXR, nuclear orphan receptors
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2510/00—Detection of programmed cell death, i.e. apoptosis
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Zoology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Toxicology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Biotechnology (AREA)
- Cell Biology (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Gastroenterology & Hepatology (AREA)
- Food Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611020419.9A CN107050007B (zh) | 2010-05-06 | 2011-05-06 | 涉及类视黄醇受体选择性通路的方法和组合物 |
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 |
|---|---|---|---|
| CN201611020419.9A Division CN107050007B (zh) | 2010-05-06 | 2011-05-06 | 涉及类视黄醇受体选择性通路的方法和组合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103002887A CN103002887A (zh) | 2013-03-27 |
| CN103002887B true CN103002887B (zh) | 2016-12-21 |
Family
ID=44904518
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180030974.9A Expired - Fee Related CN103002887B (zh) | 2010-05-06 | 2011-05-06 | 涉及类视黄醇受体选择性通路的方法和组合物 |
| CN201611020419.9A Expired - Fee Related CN107050007B (zh) | 2010-05-06 | 2011-05-06 | 涉及类视黄醇受体选择性通路的方法和组合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201611020419.9A Expired - Fee Related CN107050007B (zh) | 2010-05-06 | 2011-05-06 | 涉及类视黄醇受体选择性通路的方法和组合物 |
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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101365461A (zh) * | 2006-01-04 | 2009-02-11 | 南方研究所 | 舒林酸(sulindac)衍生物、其用途和其制备 |
Family Cites Families (11)
| 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 |
| 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
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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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101365461A (zh) * | 2006-01-04 | 2009-02-11 | 南方研究所 | 舒林酸(sulindac)衍生物、其用途和其制备 |
Non-Patent Citations (4)
| Title |
|---|
| Combination of Tumor Necrosis Factor-alpha with Sulindac Augments Its Apoptotic Potential and Suppresses Tumor Growth of Human Carcinoma Cells in Nude Mice;yasui et al.;《Cancer》;20031231;第97卷(第6期);第1412-1420页 * |
| COX-2抑制剂联合顺铂对胰腺癌细胞增生和凋亡的影响;刘江伟等;《世界华人消化杂志》;20040531;第12卷(第5期);第1139-1143页 * |
| Nonsteroidal Anti-inflammatory Drugs Induce Colorectal Cancer Cell Apoptosis by Suppressing 14-3-E;liou et al.;《Cancer Res》;20071231;第67卷(第7期);第3185-3191页 * |
| The R-enantiomer of the nonsteroidal antiinflammatory drug etodolac binds retinoid x receptor and induces tumor-selective apoptosis;kolluri et al.;《PNAS》;20051231;第102卷(第7期);第2525-2530页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2798692C (en) | 2019-04-30 |
| WO2011140525A2 (en) | 2011-11-10 |
| KR101889290B1 (ko) | 2018-08-20 |
| CA2798692A1 (en) | 2011-11-10 |
| CN107050007B (zh) | 2020-06-30 |
| US9611235B2 (en) | 2017-04-04 |
| KR20130113932A (ko) | 2013-10-16 |
| US20150266842A1 (en) | 2015-09-24 |
| EP2571497A2 (en) | 2013-03-27 |
| EP2571497A4 (en) | 2013-12-04 |
| JP2017008050A (ja) | 2017-01-12 |
| WO2011140525A3 (en) | 2012-03-22 |
| US10087156B2 (en) | 2018-10-02 |
| US20170313668A1 (en) | 2017-11-02 |
| AU2011249857B2 (en) | 2015-03-12 |
| AU2011249857A1 (en) | 2012-12-06 |
| JP6375340B2 (ja) | 2018-08-15 |
| CN107050007A (zh) | 2017-08-18 |
| CN103002887A (zh) | 2013-03-27 |
| EP2571497B1 (en) | 2018-09-19 |
| ES2702532T3 (es) | 2019-03-01 |
| JP2013533212A (ja) | 2013-08-22 |
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