AU2003286816B2 - Novel cytarabine monophosphate prodrugs - Google Patents
Novel cytarabine monophosphate prodrugs Download PDFInfo
- Publication number
- AU2003286816B2 AU2003286816B2 AU2003286816A AU2003286816A AU2003286816B2 AU 2003286816 B2 AU2003286816 B2 AU 2003286816B2 AU 2003286816 A AU2003286816 A AU 2003286816A AU 2003286816 A AU2003286816 A AU 2003286816A AU 2003286816 B2 AU2003286816 B2 AU 2003286816B2
- Authority
- AU
- Australia
- Prior art keywords
- compound
- liver
- formula
- pharmaceutically acceptable
- cytarabine
- 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.)
- Ceased
Links
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- -1 cytarabine monophosphate Chemical class 0.000 title claims description 72
- 239000000651 prodrug Substances 0.000 title abstract description 125
- 229940002612 prodrug Drugs 0.000 title abstract description 125
- 150000001875 compounds Chemical class 0.000 claims abstract description 151
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- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 239000000203 mixture Substances 0.000 claims description 112
- 210000004185 liver Anatomy 0.000 claims description 107
- 238000000034 method Methods 0.000 claims description 72
- 239000003814 drug Substances 0.000 claims description 55
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- 238000011282 treatment Methods 0.000 claims description 26
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- 230000001965 increasing effect Effects 0.000 claims description 20
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- LQCLVBQBTUVCEQ-QTFUVMRISA-N troleandomycin Chemical compound O1[C@@H](C)[C@H](OC(C)=O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](OC(C)=O)[C@@H](C)C(=O)[C@@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)OC(C)=O)[C@H]1C LQCLVBQBTUVCEQ-QTFUVMRISA-N 0.000 description 1
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Classifications
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- 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
- C07H19/06—Pyrimidine radicals
- C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Genetics & Genomics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42325902P | 2002-10-31 | 2002-10-31 | |
| US42321102P | 2002-10-31 | 2002-10-31 | |
| US60/423,259 | 2002-10-31 | ||
| US60/423,211 | 2002-10-31 | ||
| PCT/US2003/034690 WO2004041837A1 (en) | 2002-10-31 | 2003-10-31 | Novel cytarabine monophosphate prodrugs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2003286816A1 AU2003286816A1 (en) | 2004-06-07 |
| AU2003286816B2 true AU2003286816B2 (en) | 2010-08-19 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003286816A Ceased AU2003286816B2 (en) | 2002-10-31 | 2003-10-31 | Novel cytarabine monophosphate prodrugs |
| AU2003287389A Expired AU2003287389B2 (en) | 2002-10-31 | 2003-10-31 | Novel cyclic phosphate diesters of 1,3-propane-1-aryl diols and their use in preparing prodrugs |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| AU2003287389A Expired AU2003287389B2 (en) | 2002-10-31 | 2003-10-31 | Novel cyclic phosphate diesters of 1,3-propane-1-aryl diols and their use in preparing prodrugs |
Country Status (13)
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| US (4) | US7148349B2 (https=) |
| EP (2) | EP1556398B1 (https=) |
| JP (2) | JP5046219B2 (https=) |
| KR (2) | KR101115210B1 (https=) |
| AT (1) | ATE442375T1 (https=) |
| AU (2) | AU2003286816B2 (https=) |
| BR (2) | BR0315795A (https=) |
| CA (2) | CA2503729C (https=) |
| DE (1) | DE60329211D1 (https=) |
| IL (2) | IL167990A (https=) |
| MX (2) | MXPA05004504A (https=) |
| PL (2) | PL212929B1 (https=) |
| WO (2) | WO2004041837A1 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6312662B1 (en) | 1998-03-06 | 2001-11-06 | Metabasis Therapeutics, Inc. | Prodrugs phosphorus-containing compounds |
| NZ536328A (en) * | 2002-05-13 | 2007-11-30 | Metabasis Therapeutics Inc | Novel phosphonic acid based prodrugs of PMEA and its analogues |
| AU2003235501A1 (en) * | 2002-05-13 | 2003-11-11 | Metabasis Therapeutics, Inc. | PMEA and PMPA cyclic producing synthesis |
| JP5046219B2 (ja) * | 2002-10-31 | 2012-10-10 | リガンド・ファーマシューティカルズ・インコーポレイテッド | １，３−プロパン−１−アリールジオールの新規環状リン酸ジエステルおよびそのプロドラッグへの使用 |
| US20050182252A1 (en) * | 2004-02-13 | 2005-08-18 | Reddy K. R. | Novel 2'-C-methyl nucleoside derivatives |
| WO2005123729A1 (en) * | 2004-06-08 | 2005-12-29 | Metabasis Therapeutics, Inc. | Lewis acid mediated synthesis of cyclic esters |
| US20090118223A1 (en) * | 2005-08-12 | 2009-05-07 | Erion Mark D | Novel 2'-c-methyl and 4'c-methyl nucleoside derivatives |
| US20070241502A1 (en) * | 2006-04-14 | 2007-10-18 | Campbell Darrell C | Poker game and apparatus for play thereof |
| US7584968B2 (en) * | 2006-04-14 | 2009-09-08 | Seven Generations, Inc. | Poker game and apparatus for play thereof |
| US20100305060A1 (en) * | 2007-11-29 | 2010-12-02 | Ligand Pharmaceuticals Incorporated | Nucleoside Prodrugs and Uses Thereof |
| TW200936146A (en) * | 2007-11-29 | 2009-09-01 | Metabasis Therapeutics Inc | Antiviral nucleoside compounds |
| CA2722858C (en) | 2008-04-30 | 2017-08-29 | Siemens Medical Solutions Usa, Inc. | Substrate based pet imaging agents |
| CN101787064B (zh) * | 2009-01-23 | 2013-03-13 | 高峰 | 阿糖胞苷衍生物及其在抗癌抗肿瘤中的用途 |
| CN102712668A (zh) * | 2010-01-15 | 2012-10-03 | 巴斯夫欧洲公司 | 经磷取代的烷氧胺化合物 |
| WO2011113174A1 (zh) * | 2010-03-15 | 2011-09-22 | Gao Feng | 阿糖胞苷衍生物及其在抗癌抗肿瘤中的用途 |
| EP3013351B1 (en) * | 2013-06-24 | 2019-10-30 | CanBas Co., Ltd. | Peptides and peptidomimetics in combination uses and treatments for cancer patient subpopulations |
| GB201317166D0 (en) * | 2013-09-27 | 2013-11-06 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| JP2017512183A (ja) | 2014-02-13 | 2017-05-18 | リガンド・ファーマシューティカルズ・インコーポレイテッド | プロドラッグ化合物およびそれらの使用 |
| CN106687118A (zh) | 2014-07-02 | 2017-05-17 | 配体药物公司 | 前药化合物及其用途 |
| EA201890454A1 (ru) | 2015-08-06 | 2018-07-31 | Чимерикс, Инк. | Пирролопиримидиновые нуклеозиды и их аналоги, которые можно использовать в качестве противовирусных средств |
| US11104698B2 (en) * | 2015-12-03 | 2021-08-31 | Biosight Ltd. | Salts of conjugates for cancer therapy |
| US12071450B2 (en) | 2015-12-03 | 2024-08-27 | Biosight Ltd. | Salts of conjugates for cancer therapy |
| US12064445B2 (en) | 2015-12-03 | 2024-08-20 | Biosight Ltd. | Cytarabine conjugates for cancer therapy |
| BR112018011177A2 (pt) | 2015-12-03 | 2018-11-21 | Biosight Ltd | conjugados de citarabina para terapia de câncer |
| WO2018055681A1 (ja) * | 2016-09-20 | 2018-03-29 | 株式会社 島津製作所 | 両親媒性ブロックポリマーを用いた薬剤内包分子集合体 |
| WO2019060692A1 (en) | 2017-09-21 | 2019-03-28 | Chimerix, Inc. | MORPHIC FORMS OF 4-AMINO-7- (3,4-DIHYDROXY-5- (HYDROXYMETHYL) -ETRAHYDROFURAN-2-YL) -2-METHYL-7H-PYRROLO [2,3-D] PYRIMIDINE-5-CARBOXAMIDE AND THEIR USES |
| CN109956985A (zh) * | 2017-12-22 | 2019-07-02 | 浙江柏拉阿图医药科技有限公司 | 肝递送阿糖胞苷前体药物核苷环磷酸酯化合物及应用 |
| RU2020126177A (ru) | 2018-01-09 | 2022-02-10 | Лиганд Фармасьютикалз, Инк. | Ацетальные соединения и их терапевтическое применение |
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| US6312662B1 (en) * | 1998-03-06 | 2001-11-06 | Metabasis Therapeutics, Inc. | Prodrugs phosphorus-containing compounds |
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2003
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- 2003-10-31 DE DE60329211T patent/DE60329211D1/de not_active Expired - Lifetime
- 2003-10-31 AT AT03778030T patent/ATE442375T1/de not_active IP Right Cessation
- 2003-10-31 WO PCT/US2003/034690 patent/WO2004041837A1/en not_active Ceased
- 2003-10-31 JP JP2004550339A patent/JP4689274B2/ja not_active Expired - Fee Related
- 2003-10-31 EP EP03778030A patent/EP1556398B1/en not_active Expired - Lifetime
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- 2003-10-31 CA CA2503730A patent/CA2503730C/en not_active Expired - Lifetime
- 2003-10-31 EP EP03781623.8A patent/EP1556393B1/en not_active Expired - Lifetime
- 2003-10-31 BR BR0315795-4A patent/BR0315795A/pt not_active IP Right Cessation
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- 2003-10-31 AU AU2003287389A patent/AU2003287389B2/en not_active Expired
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2005
- 2005-04-12 IL IL167990A patent/IL167990A/en unknown
- 2005-04-12 IL IL167984A patent/IL167984A/en active IP Right Grant
-
2006
- 2006-09-28 US US11/528,283 patent/US7498320B2/en not_active Expired - Lifetime
- 2006-10-18 US US11/582,383 patent/US7553826B2/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6312662B1 (en) * | 1998-03-06 | 2001-11-06 | Metabasis Therapeutics, Inc. | Prodrugs phosphorus-containing compounds |
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