NZ509405A - Preparation of 1-(4-thio-thioarabinofuranosyl) cytosine derivatives and their use as anticancer agents and DNA replication inhibitors - Google Patents
Preparation of 1-(4-thio-thioarabinofuranosyl) cytosine derivatives and their use as anticancer agents and DNA replication inhibitorsInfo
- Publication number
- NZ509405A NZ509405A NZ509405A NZ50940599A NZ509405A NZ 509405 A NZ509405 A NZ 509405A NZ 509405 A NZ509405 A NZ 509405A NZ 50940599 A NZ50940599 A NZ 50940599A NZ 509405 A NZ509405 A NZ 509405A
- Authority
- NZ
- New Zealand
- Prior art keywords
- cancer
- compound
- group
- thio
- cytosine
- Prior art date
Links
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical class NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 title claims description 68
- 238000002360 preparation method Methods 0.000 title description 5
- 239000002246 antineoplastic agent Substances 0.000 title description 2
- 230000007524 negative regulation of DNA replication Effects 0.000 title 1
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- 201000011510 cancer Diseases 0.000 claims abstract description 24
- -1 monoalkylamino Chemical group 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 125000002252 acyl group Chemical group 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 8
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 230000004543 DNA replication Effects 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
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- 239000011737 fluorine Chemical group 0.000 claims abstract 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 6
- 229940104302 cytosine Drugs 0.000 claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 19
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- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 16
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- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 9
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- PYMYPHUHKUWMLA-WISUUJSJSA-N aldehydo-L-xylose Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WISUUJSJSA-N 0.000 claims description 3
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- MXHRCPNRJAMMIM-SHYZEUOFSA-N 2'-deoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 MXHRCPNRJAMMIM-SHYZEUOFSA-N 0.000 description 3
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- 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
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Landscapes
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| US9386998P | 1998-07-23 | 1998-07-23 | |
| PCT/US1999/016630 WO2000004866A2 (en) | 1998-07-23 | 1999-07-23 | Preparation of thioarabinofuranosyl compounds and use thereof |
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| EP2303226B1 (en) * | 2008-06-25 | 2016-03-23 | 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 |
| 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 |
| EP3109245B1 (en) | 2014-02-18 | 2018-01-03 | FUJIFILM Corporation | Method for producting thiolane skeleton-type glycoconjugate, and thiolane skeleton-type glycoconjugate |
| 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 |
| US10815264B2 (en) * | 2015-05-27 | 2020-10-27 | Southern Research Institute | Nucleotides for the treatment of cancer |
| WO2017091836A1 (en) * | 2015-11-25 | 2017-06-01 | University Of South Carolina | Enhancement of cytarabine activity by inhibiting cdk8/19 |
| IL265044B2 (en) | 2016-08-31 | 2025-02-01 | Fujifilm Corp | An antitumor preparation containing the substances nab-paclitaxel and 1-(2-deoxy-2-fluoro-4-thio-D-beta-arabinofurnosyl)cytosine, a kit containing these substances and their uses |
| WO2019146130A1 (ja) | 2018-01-29 | 2019-08-01 | 富士フイルム株式会社 | 胆道がん用抗腫瘍剤および胆道がんの処置方法 |
| WO2019204637A1 (en) * | 2018-04-19 | 2019-10-24 | Southern Research Institute | 4'-thio-nucleotide and -nucleoside prodrugs for the treatment of cancer |
| EP3993806A4 (en) * | 2019-06-05 | 2023-09-13 | Southern Research Institute | Thiarabine- and thiarabine prodrug-based treatments |
| EP4138843A4 (en) | 2020-04-23 | 2024-07-10 | Southern Research Institute | COMPOSITION FOR THE TREATMENT OF BLOOD CANCER USING 4'-THIO-5-AZA-2'-DEOXYCYTIDINE AND USES THEREOF |
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| AU6401490A (en) * | 1989-09-15 | 1991-04-18 | 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 |
| JPH04505929A (ja) * | 1989-12-08 | 1992-10-15 | シティ・オブ・ホープ | ヒトの抗癌剤の耐性の回避 |
| 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 |
| 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 |
| JP2943690B2 (ja) | 1996-04-17 | 1999-08-30 | 日本電気株式会社 | セル衝突検出装置 |
| AU749561B2 (en) | 1997-05-09 | 2002-06-27 | Ribozyme Pharmaceuticals, Inc. | Nucleic acid molecules having endonuclease and/or catalytic activity |
| 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 |
| CA2338415C (en) * | 1998-07-23 | 2006-10-10 | Southern Research Institute | Preparation of thioarabinofuranosyl compounds and use thereof |
-
1999
- 1999-07-23 CA CA002338415A patent/CA2338415C/en not_active Expired - Lifetime
- 1999-07-23 JP JP2000560859A patent/JP4719356B2/ja not_active Expired - Fee Related
- 1999-07-23 ES ES99935854T patent/ES2376862T3/es not_active Expired - Lifetime
- 1999-07-23 WO PCT/US1999/016630 patent/WO2000004866A2/en not_active Ceased
- 1999-07-23 AU AU51239/99A patent/AU747012B2/en not_active Expired
- 1999-07-23 EP EP99935854A patent/EP1100512B1/en not_active Expired - Lifetime
- 1999-07-23 ES ES10170453.4T patent/ES2438144T3/es not_active Expired - Lifetime
- 1999-07-23 ES ES10179999T patent/ES2402799T3/es not_active Expired - Lifetime
- 1999-07-23 EP EP10179999A patent/EP2332551B1/en not_active Expired - Lifetime
- 1999-07-23 EP EP10170453.4A patent/EP2335706B1/en not_active Expired - Lifetime
- 1999-07-23 NZ NZ509405A patent/NZ509405A/en not_active IP Right Cessation
- 1999-07-23 AT AT99935854T patent/ATE531376T1/de active
-
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 |
|---|---|
| US20060287320A1 (en) | 2006-12-21 |
| EP2335706A1 (en) | 2011-06-22 |
| WO2000004866A2 (en) | 2000-02-03 |
| JP2002521318A (ja) | 2002-07-16 |
| AU747012B2 (en) | 2002-05-09 |
| US20030203872A1 (en) | 2003-10-30 |
| US8178510B2 (en) | 2012-05-15 |
| CA2338415C (en) | 2006-10-10 |
| ATE531376T1 (de) | 2011-11-15 |
| EP1100512A2 (en) | 2001-05-23 |
| US6576621B1 (en) | 2003-06-10 |
| EP2332551B1 (en) | 2013-01-09 |
| EP1100512A4 (en) | 2001-10-10 |
| US7691820B2 (en) | 2010-04-06 |
| US20050038025A1 (en) | 2005-02-17 |
| US6870052B2 (en) | 2005-03-22 |
| JP2010202655A (ja) | 2010-09-16 |
| EP1100512B1 (en) | 2011-11-02 |
| US20100216797A1 (en) | 2010-08-26 |
| WO2000004866A9 (en) | 2000-08-10 |
| AU5123999A (en) | 2000-02-14 |
| EP2332551A1 (en) | 2011-06-15 |
| WO2000004866A3 (en) | 2000-04-20 |
| ES2402799T3 (es) | 2013-05-09 |
| CA2338415A1 (en) | 2000-02-03 |
| EP2335706B1 (en) | 2013-10-23 |
| JP2011032281A (ja) | 2011-02-17 |
| JP4719356B2 (ja) | 2011-07-06 |
| ES2438144T3 (es) | 2014-01-16 |
| ES2376862T3 (es) | 2012-03-20 |
| JP5357857B2 (ja) | 2013-12-04 |
| US7138385B2 (en) | 2006-11-21 |
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