TWI281911B - Treatment of tumors with RARalpha selective retinoid compounds in combination with other anti-tumor agents - Google Patents
Treatment of tumors with RARalpha selective retinoid compounds in combination with other anti-tumor agents Download PDFInfo
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- TWI281911B TWI281911B TW090107695A TW90107695A TWI281911B TW I281911 B TWI281911 B TW I281911B TW 090107695 A TW090107695 A TW 090107695A TW 90107695 A TW90107695 A TW 90107695A TW I281911 B TWI281911 B TW I281911B
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- 238000010255 intramuscular injection Methods 0.000 description 1
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- 238000007912 intraperitoneal administration Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
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- 238000002372 labelling Methods 0.000 description 1
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- 208000012987 lip and oral cavity carcinoma Diseases 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
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- 208000026037 malignant tumor of neck Diseases 0.000 description 1
- UWPLTCWTTVMXCM-UHFFFAOYSA-N methyl 4-amino-2,6-difluorobenzoate Chemical compound COC(=O)C1=C(F)C=C(N)C=C1F UWPLTCWTTVMXCM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000035407 negative regulation of cell proliferation Effects 0.000 description 1
- 210000002445 nipple Anatomy 0.000 description 1
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- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 238000000159 protein binding assay Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 108010059301 retinoic acid receptor gamma Proteins 0.000 description 1
- 102000027478 retinoid receptor subtypes Human genes 0.000 description 1
- 108091008678 retinoid receptor subtypes Proteins 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
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- 231100000438 skin toxicity Toxicity 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
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- 238000011287 therapeutic dose Methods 0.000 description 1
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- 231100000027 toxicology Toxicity 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
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- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 206010046766 uterine cancer Diseases 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K31/16—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
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/66—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and singly-bound oxygen atoms, bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54214800A | 2000-04-04 | 2000-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI281911B true TWI281911B (en) | 2007-06-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090107695A TWI281911B (en) | 2000-04-04 | 2001-03-30 | Treatment of tumors with RARalpha selective retinoid compounds in combination with other anti-tumor agents |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6387950B2 (https=) |
| EP (2) | EP1650188A1 (https=) |
| JP (1) | JP2003534246A (https=) |
| AT (1) | ATE331703T1 (https=) |
| AU (1) | AU2001253045A1 (https=) |
| CA (1) | CA2405136C (https=) |
| DE (1) | DE60121145T2 (https=) |
| ES (1) | ES2267754T3 (https=) |
| TW (1) | TWI281911B (https=) |
| WO (1) | WO2001074759A1 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6903121B1 (en) * | 2000-08-17 | 2005-06-07 | Allergan, Inc. | Treatment of tumors with acetylenes disubstituted with a phenyl or heteroaromatic group and a substituted chromanyl, thiochromanyl or tetrahydroquinolinyl group in combination with other anti-tumor agents |
| DE60136477D1 (de) * | 2000-10-02 | 2008-12-18 | Hoffmann La Roche | Retinoide zur behandlung von emphysem |
| EP1935869A1 (en) * | 2000-10-02 | 2008-06-25 | F. Hoffmann-La Roche Ag | Retinoids for the treatment of emphysema |
| US6620963B1 (en) | 2002-09-19 | 2003-09-16 | Allergan, Inc. | TRICYCLO[6.2.202,7]DODECA-2(7),3,5-TRIEN-4-CARBONYLAMINO-PHENYL AND TRICYCLO[6.2.202,7]DODECA-2(7),3,5-TRIEN-4-CARBONYLAMINO-HETEROARYL AND RELATED COMPOUNDS HAVING RARα RECEPTOR SELECTIVE BIOLOGICAL ACTIVITY |
| WO2005093426A2 (en) * | 2004-03-26 | 2005-10-06 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with retinoic acid receptor alpha (rara) |
| BRPI0616454A2 (pt) | 2005-09-30 | 2011-06-21 | Vitae Pharmaceuticals, Inc. | métodos de tratamento de cáncer |
| US20120238623A1 (en) * | 2011-03-14 | 2012-09-20 | Chandraratna Roshantha A | Inflammation and Autoimmune Disorder Treatment using RARa Selective Agonists |
| 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 |
| MX352727B (es) | 2011-12-13 | 2017-12-06 | Dartmouth College | Tratamiento de trastorno autoinmune al usar agonistas de rxr. |
| MX391949B (es) | 2015-03-31 | 2025-03-21 | Syros Pharmaceuticals Inc | Metodos para estratificacion de pacientes para tratamiento con agonistas del receptor alfa de acido retinoico. |
| WO2017075607A1 (en) | 2015-10-31 | 2017-05-04 | Io Therapeutics, Inc. | Treatment of nervous system disorders using combinations of pxr agonists and thyroid hormones |
| DK3380086T3 (da) * | 2015-11-25 | 2021-11-22 | Io Therapeutics Inc | Cyp26-resistente rar-alpha-selektive agonister i behandling af cancer |
| CA3016876C (en) | 2016-03-10 | 2021-12-28 | Io Therapeutics, Inc. | Treatment of autoimmune diseases with combinations of rxr 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 |
| JP7034085B2 (ja) | 2016-04-08 | 2022-03-11 | サイロス ファーマシューティカルズ， インコーポレイテッド | Ａｍｌ及びｍｄｓの治療のためのｒａｒａアゴニスト |
| US9868994B2 (en) | 2016-04-08 | 2018-01-16 | Syros Pharmaceuticals, Inc. | Methods of stratifying patients for treatment with retinoic acid receptor-α agonists |
| KR20200029544A (ko) | 2017-07-13 | 2020-03-18 | 아이오 테라퓨틱스, 인크. | 암 면역요법을 위해 면역 조절제와 조합된 면역조절 레티노이드 및 렉시노이드 화합물 |
| KR20200044889A (ko) * | 2017-08-31 | 2020-04-29 | 아이오 테라퓨틱스, 인크. | 암 면역요법을 위해 면역 조절제와 조합된 rar 선택적 작용제 |
| US11517549B2 (en) | 2017-09-20 | 2022-12-06 | Io Therapeutics, Inc. | Treatment of disease with esters of selective RXR agonists |
| 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+. |
| CN114703227B (zh) * | 2022-01-27 | 2023-11-10 | 中国科学院生态环境研究中心 | 基于MCF-7细胞系构建的RARα效应物体外筛选方法 |
| US11976021B2 (en) | 2022-06-27 | 2024-05-07 | Io Therapeutics, Inc. | Synthesis of tetrahydronaphthalenols and uses thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69224660C5 (de) | 1991-12-18 | 2010-06-02 | The Salk Institute For Biological Studies, La Jolla | Mitteln zur modulierung von verfahren durch retinoid rezeptoren und dafür nützliche verbindungen |
| US5675024A (en) | 1995-11-22 | 1997-10-07 | Allergan | Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thiochroman and 1,2,3,4,-tetrahydroquinoline carboxylic acids, having an electron withdrawing substituent in the aromatic or heteroaromatic moiety, having retinoid-like biological activity |
| 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 |
-
2001
- 2001-03-30 TW TW090107695A patent/TWI281911B/zh not_active IP Right Cessation
- 2001-04-02 ES ES01926512T patent/ES2267754T3/es not_active Expired - Lifetime
- 2001-04-02 AU AU2001253045A patent/AU2001253045A1/en not_active Abandoned
- 2001-04-02 WO PCT/US2001/010410 patent/WO2001074759A1/en not_active Ceased
- 2001-04-02 AT AT01926512T patent/ATE331703T1/de not_active IP Right Cessation
- 2001-04-02 JP JP2001572454A patent/JP2003534246A/ja active Pending
- 2001-04-02 EP EP05025970A patent/EP1650188A1/en not_active Withdrawn
- 2001-04-02 CA CA002405136A patent/CA2405136C/en not_active Expired - Lifetime
- 2001-04-02 US US09/824,111 patent/US6387950B2/en not_active Expired - Fee Related
- 2001-04-02 EP EP01926512A patent/EP1268405B1/en not_active Expired - Lifetime
- 2001-04-02 DE DE60121145T patent/DE60121145T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2405136A1 (en) | 2001-10-11 |
| EP1268405B1 (en) | 2006-06-28 |
| JP2003534246A (ja) | 2003-11-18 |
| AU2001253045A1 (en) | 2001-10-15 |
| WO2001074759A1 (en) | 2001-10-11 |
| EP1268405A1 (en) | 2003-01-02 |
| EP1650188A1 (en) | 2006-04-26 |
| US6387950B2 (en) | 2002-05-14 |
| ATE331703T1 (de) | 2006-07-15 |
| CA2405136C (en) | 2009-06-16 |
| US20010039293A1 (en) | 2001-11-08 |
| DE60121145D1 (de) | 2006-08-10 |
| DE60121145T2 (de) | 2007-05-31 |
| ES2267754T3 (es) | 2007-03-16 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |