CA2338415C - Preparation of thioarabinofuranosyl compounds and use thereof - Google Patents
Preparation of thioarabinofuranosyl compounds and use thereof Download PDFInfo
- Publication number
- CA2338415C CA2338415C CA002338415A CA2338415A CA2338415C CA 2338415 C CA2338415 C CA 2338415C CA 002338415 A CA002338415 A CA 002338415A CA 2338415 A CA2338415 A CA 2338415A CA 2338415 C CA2338415 C CA 2338415C
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- Canada
- Prior art keywords
- cancer
- compound
- thio
- arabinofuranosyl
- beta
- 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 - Lifetime
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- JSRLJPSBLDHEIO-SHYZEUOFSA-N dUMP Chemical class O1[C@H](COP(O)(O)=O)[C@@H](O)C[C@@H]1N1C(=O)NC(=O)C=C1 JSRLJPSBLDHEIO-SHYZEUOFSA-N 0.000 description 1
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
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- 229940121354 immunomodulator Drugs 0.000 description 1
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- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 231100000338 sulforhodamine B assay Toxicity 0.000 description 1
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- 238000013268 sustained release Methods 0.000 description 1
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- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 239000005450 thionucleoside Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
-
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Transplantation (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2464681A CA2464681C (en) | 1998-07-23 | 1999-07-23 | Preparation of thioarabinofuranosyl compounds and use thereof |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9386998P | 1998-07-23 | 1998-07-23 | |
| US60/093,869 | 1998-07-23 | ||
| PCT/US1999/016630 WO2000004866A2 (en) | 1998-07-23 | 1999-07-23 | Preparation of thioarabinofuranosyl compounds and use thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2464681A Division CA2464681C (en) | 1998-07-23 | 1999-07-23 | Preparation of thioarabinofuranosyl compounds and use thereof |
Publications (2)
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| CA2338415A1 CA2338415A1 (en) | 2000-02-03 |
| CA2338415C true CA2338415C (en) | 2006-10-10 |
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| CA002338415A Expired - Lifetime CA2338415C (en) | 1998-07-23 | 1999-07-23 | Preparation of thioarabinofuranosyl compounds and use thereof |
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|---|---|
| US (5) | US6576621B1 (enExample) |
| EP (3) | EP2332551B1 (enExample) |
| JP (3) | JP4719356B2 (enExample) |
| AT (1) | ATE531376T1 (enExample) |
| AU (1) | AU747012B2 (enExample) |
| CA (1) | CA2338415C (enExample) |
| ES (3) | ES2402799T3 (enExample) |
| NZ (1) | NZ509405A (enExample) |
| WO (1) | WO2000004866A2 (enExample) |
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| NZ509405A (en) * | 1998-07-23 | 2004-10-29 | Southern Res Inst | Preparation of 1-(4-thio-thioarabinofuranosyl) cytosine derivatives and their use as anticancer agents and DNA replication inhibitors |
| US20060127990A1 (en) * | 2002-08-22 | 2006-06-15 | Geneticlab Co., Ltd | 4'-thionucleotide |
| US7524831B2 (en) * | 2005-03-02 | 2009-04-28 | Schering Corporation | Treatments for Flaviviridae virus infection |
| EP2124553B1 (en) * | 2007-03-23 | 2017-03-01 | Southern Research Institute | Method for treating and preventing arthritis |
| AR064165A1 (es) | 2007-12-06 | 2009-03-18 | Richmond Sa Com Ind Y Financie | Un procedimiento para la preparacion de capecitabina e intermediarios utilizables en dicho procedimiento |
| WO2009158412A2 (en) * | 2008-06-25 | 2009-12-30 | Endo Pharmaceuticals Solutions Inc. | Sustained delivery of exenatide and other polypeptides |
| US20110218170A1 (en) * | 2010-03-02 | 2011-09-08 | Southern Research Institute | Use of 2'-deoxy-4'-thiocytidine and its analogues as dna hypomethylating anticancer agents |
| SG10201603288XA (en) | 2012-03-28 | 2016-05-30 | Fujifilm Corp | Salt Of 1-(2-Deoxy-2-Fluoro-4-Thio-beta-D-Arabinofuranosyl)Cytosine |
| JP6175553B2 (ja) | 2014-02-18 | 2017-08-09 | 富士フイルム株式会社 | チオラン骨格型糖化合物の製造方法およびチオラン骨格型糖化合物 |
| JP6351107B2 (ja) * | 2014-02-18 | 2018-07-04 | 富士フイルム株式会社 | チオラン骨格型糖化合物の製造方法およびチオラン骨格型糖化合物 |
| JP6245527B2 (ja) * | 2014-03-24 | 2017-12-13 | 富士フイルム株式会社 | チオラン環もしくはチアン環骨格を有する化合物の製造方法 |
| TWI678373B (zh) | 2014-10-31 | 2019-12-01 | 日商富士軟片股份有限公司 | 硫代核苷衍生物或其鹽及醫藥組合物 |
| HK1252245A1 (zh) * | 2015-05-27 | 2019-05-24 | Idenix Pharmaceuticals Llc | 用於治疗癌症的核苷酸 |
| WO2017091836A1 (en) * | 2015-11-25 | 2017-06-01 | University Of South Carolina | Enhancement of cytarabine activity by inhibiting cdk8/19 |
| BR112019003946A2 (pt) | 2016-08-31 | 2019-05-21 | Fujifilm Corporation | agente antitumoral, reforçador do efeito antitumoral e kit antitumoral |
| MX2018002611A (es) | 2018-01-29 | 2019-07-30 | Fujifilm Corp | Agente antitumoral para cancer del tracto biliar y metodo para tratar cancer del tracto biliar. |
| AU2019256465B2 (en) * | 2018-04-19 | 2024-10-03 | Southern Research Institute | 4'-thio-nucleotide and -nucleoside prodrugs for the treatment of cancer |
| JP2022535849A (ja) * | 2019-06-05 | 2022-08-10 | サウザーン リサーチ インスチチュート | チアラビンベースおよびチアラビンのプロドラッグベースの治療 |
| CA3176543A1 (en) | 2020-04-23 | 2021-10-28 | Mark J. Suto | Composition for treating blood cancer using 4'-thio-5-aza-2'-deoxycytidine and uses thereof |
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| EP0491793B1 (en) * | 1989-09-15 | 2005-11-30 | Southern Research Institute | 2'-deoxy-4'-thioribonucleosides as antiviral and anticancer agents |
| IE74701B1 (en) * | 1989-10-04 | 1997-07-30 | Univ Birmingham | Further antiviral pyrimidine nucleosides |
| AU639973B2 (en) * | 1989-12-08 | 1993-08-12 | City Of Hope | Circumvention of human tumor drug resistance |
| JPH0925289A (ja) | 1995-07-14 | 1997-01-28 | Yamasa Shoyu Co Ltd | ４’−チオアラビノピリミジンヌクレオシドの製造方法 |
| JPH09249690A (ja) | 1995-07-14 | 1997-09-22 | Yamasa Shoyu Co Ltd | ４’−チオアラビノプリンヌクレオシド |
| JP2943690B2 (ja) | 1996-04-17 | 1999-08-30 | 日本電気株式会社 | セル衝突検出装置 |
| JP2001525667A (ja) | 1997-05-09 | 2001-12-11 | リボザイム・ファーマシューティカルズ・インコーポレーテッド | Ｃ−ｒａｆの発現レベルに関係した疾患または状態の酵素核酸処置 |
| US6548657B1 (en) * | 1997-06-09 | 2003-04-15 | Ribozyme Pharmaceuticals, Inc. | Method for screening nucleic acid catalysts |
| WO1999043690A1 (en) | 1998-02-25 | 1999-09-02 | Rational Drug Design Laboratories | L-4'-arabinofuranonucleoside compound and medicine composition comprising the same |
| NZ509405A (en) * | 1998-07-23 | 2004-10-29 | Southern Res Inst | Preparation of 1-(4-thio-thioarabinofuranosyl) cytosine derivatives and their use as anticancer agents and DNA replication inhibitors |
-
1999
- 1999-07-23 NZ NZ509405A patent/NZ509405A/en not_active IP Right Cessation
- 1999-07-23 ES ES10179999T patent/ES2402799T3/es not_active Expired - Lifetime
- 1999-07-23 JP JP2000560859A patent/JP4719356B2/ja not_active Expired - Fee Related
- 1999-07-23 ES ES10170453.4T patent/ES2438144T3/es not_active Expired - Lifetime
- 1999-07-23 ES ES99935854T patent/ES2376862T3/es not_active Expired - Lifetime
- 1999-07-23 AU AU51239/99A patent/AU747012B2/en not_active Expired
- 1999-07-23 WO PCT/US1999/016630 patent/WO2000004866A2/en not_active Ceased
- 1999-07-23 CA CA002338415A patent/CA2338415C/en not_active Expired - Lifetime
- 1999-07-23 EP EP10179999A patent/EP2332551B1/en not_active Expired - Lifetime
- 1999-07-23 AT AT99935854T patent/ATE531376T1/de active
- 1999-07-23 EP EP99935854A patent/EP1100512B1/en not_active Expired - Lifetime
- 1999-07-23 EP EP10170453.4A patent/EP2335706B1/en not_active Expired - Lifetime
-
2000
- 2000-01-28 US US09/493,247 patent/US6576621B1/en not_active Expired - Lifetime
-
2003
- 2003-04-07 US US10/407,135 patent/US6870052B2/en not_active Expired - Lifetime
-
2004
- 2004-09-13 US US10/938,542 patent/US7138385B2/en not_active Expired - Lifetime
-
2006
- 2006-08-24 US US11/509,030 patent/US7691820B2/en not_active Expired - Fee Related
-
2010
- 2010-02-23 US US12/710,537 patent/US8178510B2/en not_active Expired - Fee Related
- 2010-04-27 JP JP2010102499A patent/JP2010202655A/ja active Pending
- 2010-10-29 JP JP2010243705A patent/JP5357857B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000004866A3 (en) | 2000-04-20 |
| ES2376862T3 (es) | 2012-03-20 |
| WO2000004866A9 (en) | 2000-08-10 |
| US20050038025A1 (en) | 2005-02-17 |
| US6870052B2 (en) | 2005-03-22 |
| ES2402799T3 (es) | 2013-05-09 |
| US7138385B2 (en) | 2006-11-21 |
| JP2010202655A (ja) | 2010-09-16 |
| EP1100512A4 (en) | 2001-10-10 |
| EP2332551A1 (en) | 2011-06-15 |
| US6576621B1 (en) | 2003-06-10 |
| JP4719356B2 (ja) | 2011-07-06 |
| EP1100512B1 (en) | 2011-11-02 |
| EP2332551B1 (en) | 2013-01-09 |
| AU5123999A (en) | 2000-02-14 |
| EP2335706B1 (en) | 2013-10-23 |
| NZ509405A (en) | 2004-10-29 |
| US20100216797A1 (en) | 2010-08-26 |
| JP5357857B2 (ja) | 2013-12-04 |
| EP2335706A1 (en) | 2011-06-22 |
| US20060287320A1 (en) | 2006-12-21 |
| JP2011032281A (ja) | 2011-02-17 |
| ES2438144T3 (es) | 2014-01-16 |
| US8178510B2 (en) | 2012-05-15 |
| CA2338415A1 (en) | 2000-02-03 |
| AU747012B2 (en) | 2002-05-09 |
| US7691820B2 (en) | 2010-04-06 |
| JP2002521318A (ja) | 2002-07-16 |
| US20030203872A1 (en) | 2003-10-30 |
| EP1100512A2 (en) | 2001-05-23 |
| WO2000004866A2 (en) | 2000-02-03 |
| ATE531376T1 (de) | 2011-11-15 |
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