CA2442366C - Histone deacetylase inhibitors - Google Patents
Histone deacetylase inhibitors Download PDFInfo
- Publication number
- CA2442366C CA2442366C CA2442366A CA2442366A CA2442366C CA 2442366 C CA2442366 C CA 2442366C CA 2442366 A CA2442366 A CA 2442366A CA 2442366 A CA2442366 A CA 2442366A CA 2442366 C CA2442366 C CA 2442366C
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- CA
- Canada
- Prior art keywords
- compound
- alkyl
- bond
- alkoxy
- alkynyl
- 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.)
- Expired - Fee Related
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- 229940121372 histone deacetylase inhibitor Drugs 0.000 title description 3
- 239000003276 histone deacetylase inhibitor Substances 0.000 title description 3
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- 239000002253 acid Substances 0.000 claims abstract description 87
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZWSFAZTKSFSRU-UHFFFAOYSA-N tetracyclo[6.6.4.02,7.09,14]octadeca-2,4,6,9,11,13,16-heptaene Chemical compound C1=CC=CC=2C3C4=CC=CC=C4C(C1=2)CC=CC3 DZWSFAZTKSFSRU-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- 238000002723 toxicity assay Methods 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- LGSAOJLQTXCYHF-UHFFFAOYSA-N tri(propan-2-yl)-tri(propan-2-yl)silyloxysilane Chemical compound CC(C)[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)C(C)C LGSAOJLQTXCYHF-UHFFFAOYSA-N 0.000 description 1
- RTKIYFITIVXBLE-QEQCGCAPSA-N trichostatin A Chemical compound ONC(=O)/C=C/C(/C)=C/[C@@H](C)C(=O)C1=CC=C(N(C)C)C=C1 RTKIYFITIVXBLE-QEQCGCAPSA-N 0.000 description 1
- WILBTFWIBAOWLN-UHFFFAOYSA-N triethyl(triethylsilyloxy)silane Chemical compound CC[Si](CC)(CC)O[Si](CC)(CC)CC WILBTFWIBAOWLN-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the 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
- A61K31/16—Amides, e.g. hydroxamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2783647A CA2783647A1 (en) | 2001-03-27 | 2002-03-25 | Histone deacetylase inhibitors |
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81294001A | 2001-03-27 | 2001-03-27 | |
| US09/812,944 US6495719B2 (en) | 2001-03-27 | 2001-03-27 | Histone deacetylase inhibitors |
| US09/812,944 | 2001-03-27 | ||
| US09/812,945 US7312247B2 (en) | 2001-03-27 | 2001-03-27 | Histone deacetylase inhibitors |
| US09/812,940 | 2001-03-27 | ||
| US09/812,945 | 2001-03-27 | ||
| US10/025,947 US8026280B2 (en) | 2001-03-27 | 2001-12-26 | Histone deacetylase inhibitors |
| US10/025,947 | 2001-12-26 | ||
| PCT/US2002/008836 WO2002076941A2 (en) | 2001-03-27 | 2002-03-25 | Histone deacetylase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2783647A Division CA2783647A1 (en) | 2001-03-27 | 2002-03-25 | Histone deacetylase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2442366A1 CA2442366A1 (en) | 2002-10-03 |
| CA2442366C true CA2442366C (en) | 2012-09-25 |
Family
ID=27487458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2442366A Expired - Fee Related CA2442366C (en) | 2001-03-27 | 2002-03-25 | Histone deacetylase inhibitors |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1408946A4 (de) |
| AU (1) | AU2002250401A1 (de) |
| CA (1) | CA2442366C (de) |
| WO (1) | WO2002076941A2 (de) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1291015A1 (de) | 2001-09-10 | 2003-03-12 | Lunamed AG | Darreichungsformen mit verlängerter Wirkstofffreisetzung |
| WO2003088954A1 (en) * | 2002-04-15 | 2003-10-30 | Sloan-Kettering Institute For Cancer Research | Combination therapy for the treatment of cancer |
| US7154002B1 (en) | 2002-10-08 | 2006-12-26 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| US7250514B1 (en) | 2002-10-21 | 2007-07-31 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| GB0226855D0 (en) | 2002-11-18 | 2002-12-24 | Queen Mary & Westfield College | Histone deacetylase inhibitors |
| JP2006508986A (ja) | 2002-11-20 | 2006-03-16 | エルラント ゲネ セラペウチクス エルエルシー | ヒストンデアセチラーゼ阻害剤による肺細胞の治療方法 |
| WO2004076386A2 (en) | 2003-02-25 | 2004-09-10 | Topotarget Uk Limited | Carbamic acid compounds comprising a bicyclic heteroaryl group as hdac inhibitors |
| KR20050122210A (ko) | 2003-03-17 | 2005-12-28 | 다케다 샌디에고, 인코포레이티드 | 히스톤 탈아세틸화 효소 억제제 |
| US7842835B2 (en) | 2003-07-07 | 2010-11-30 | Georgetown University | Histone deacetylase inhibitors and methods of use thereof |
| AR050552A1 (es) * | 2004-09-02 | 2006-11-01 | Osi Pharm Inc | Mercaptoamidas como inhibidores de histona desacetilasa |
| WO2006029818A2 (en) * | 2004-09-16 | 2006-03-23 | Dsm Ip Assets B.V. | Cosmetic compositions containing an hydroxamic acid compound optionally in combination with a retinoid |
| JP2008524246A (ja) | 2004-12-16 | 2008-07-10 | タケダ サン ディエゴ インコーポレイテッド | ヒストンデアセチラーゼ阻害剤 |
| WO2006122319A2 (en) | 2005-05-11 | 2006-11-16 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| ZA200800901B (en) | 2005-07-14 | 2010-05-26 | Takeda San Diego Inc | Histone deacetylase inhibitors |
| GB0620823D0 (en) | 2006-10-19 | 2006-11-29 | Univ London | Histone deacetylase inhibitors |
| JP2019189648A (ja) * | 2019-07-08 | 2019-10-31 | 国立大学法人東京農工大学 | シス桂皮酸類縁体、重力屈性調節剤 |
| CN110523541B (zh) * | 2019-09-04 | 2021-09-28 | 中南大学 | 一种烷基硫醚基乙基羟肟酸药剂及其制备方法与应用 |
| CN114805235B (zh) * | 2022-05-09 | 2024-04-23 | 江苏中旗科技股份有限公司 | 一种多取代异恶唑烷酮及其中间体的合成制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3886278A (en) * | 1973-08-22 | 1975-05-27 | Mead Johnson & Co | Ammonium carboxylate sebum inhibition process |
| JPS6054339A (ja) * | 1983-09-05 | 1985-03-28 | Kuraray Co Ltd | 不飽和カルボン酸エステルの製造方法 |
| JP3065636B2 (ja) * | 1989-06-29 | 2000-07-17 | 塩野義製薬株式会社 | ［ジ―ｔｅｒｔ―ブチル（ヒドロキシ）フェニルチオ］置換ヒドロキサム酸誘導体 |
| GB9614366D0 (en) * | 1996-07-09 | 1996-09-04 | Smithkline Beecham Spa | Novel compounds |
| US6110955A (en) * | 1997-03-11 | 2000-08-29 | Beacon Laboratories, Inc. | Metabolically stabilized oxyalkylene esters and uses thereof |
| US6147224A (en) * | 1998-10-01 | 2000-11-14 | Allergan Sales, Inc. | 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors |
-
2002
- 2002-03-25 CA CA2442366A patent/CA2442366C/en not_active Expired - Fee Related
- 2002-03-25 EP EP02719311A patent/EP1408946A4/de not_active Withdrawn
- 2002-03-25 WO PCT/US2002/008836 patent/WO2002076941A2/en not_active Ceased
- 2002-03-25 AU AU2002250401A patent/AU2002250401A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1408946A2 (de) | 2004-04-21 |
| AU2002250401A1 (en) | 2002-10-08 |
| EP1408946A4 (de) | 2004-06-09 |
| WO2002076941A2 (en) | 2002-10-03 |
| CA2442366A1 (en) | 2002-10-03 |
| WO2002076941A3 (en) | 2004-02-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20180326 |