TWI347325B - Novel phosphonic acid based prodrugs of pmea and its analogues - Google Patents
Novel phosphonic acid based prodrugs of pmea and its analoguesInfo
- Publication number
- TWI347325B TWI347325B TW092132408A TW92132408A TWI347325B TW I347325 B TWI347325 B TW I347325B TW 092132408 A TW092132408 A TW 092132408A TW 92132408 A TW92132408 A TW 92132408A TW I347325 B TWI347325 B TW I347325B
- Authority
- TW
- Taiwan
- Prior art keywords
- pmea
- analogues
- phosphonic acid
- acid based
- based prodrugs
- Prior art date
Links
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title 1
- 229940002612 prodrug Drugs 0.000 title 1
- 239000000651 prodrug Substances 0.000 title 1
Classifications
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- 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
- A61P31/20—Antivirals for DNA viruses
-
- 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
- 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
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biochemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Gastroenterology & Hepatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38054502P | 2002-05-13 | 2002-05-13 | |
| PCT/US2003/014821 WO2004037161A2 (en) | 2002-05-13 | 2003-05-12 | Cyclic prodrugs of pmea one of its analogues |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200426152A TW200426152A (en) | 2004-12-01 |
| TWI347325B true TWI347325B (en) | 2011-08-21 |
Family
ID=32176361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092132408A TWI347325B (en) | 2002-05-13 | 2003-11-18 | Novel phosphonic acid based prodrugs of pmea and its analogues |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7214668B2 (enExample) |
| EP (2) | EP2223927B1 (enExample) |
| JP (1) | JP4476811B2 (enExample) |
| AU (1) | AU2003299492B2 (enExample) |
| CA (1) | CA2485702C (enExample) |
| IL (2) | IL164809A0 (enExample) |
| NZ (1) | NZ536328A (enExample) |
| TW (1) | TWI347325B (enExample) |
| WO (1) | WO2004037161A2 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6312662B1 (en) * | 1998-03-06 | 2001-11-06 | Metabasis Therapeutics, Inc. | Prodrugs phosphorus-containing compounds |
| AU2003235501A1 (en) * | 2002-05-13 | 2003-11-11 | Metabasis Therapeutics, Inc. | PMEA and PMPA cyclic producing synthesis |
| IL164809A0 (en) | 2002-05-13 | 2005-12-18 | Metabasis Therapeutics Inc | Novel phosphonic acid basdrugs of pmea and its analogues |
| PL376474A1 (en) * | 2002-10-31 | 2005-12-27 | Metabasis Therapeutics, Inc. | Novel cyclic phosphate diesters of 1,3-propane-1-aryl diols and their use in preparing prodrugs |
| CA2553455A1 (en) * | 2004-01-21 | 2005-08-11 | Gilead Sciences, Inc. | Use of adefovir or tenofovir for inhibiting mmtv-like viruses involved in breast cancer and primary biliary cirrhosis |
| US20050182252A1 (en) * | 2004-02-13 | 2005-08-18 | Reddy K. R. | Novel 2'-C-methyl nucleoside derivatives |
| MXPA06014013A (es) * | 2004-06-08 | 2007-03-15 | Metabasis Therapeutics Inc | Sintesis mediada por acidos de lewis de esteres ciclicos. |
| NZ554783A (en) * | 2004-11-15 | 2010-12-24 | Ceptyr Inc | Protein tyrosine phosphatase inhibitors and methods of use thereof |
| US7737273B2 (en) | 2005-07-26 | 2010-06-15 | Hetero Drugs Limited | Process for acyclic phosphonate nucleotide analogs |
| US20070042501A1 (en) * | 2005-08-20 | 2007-02-22 | Institute Of Nuclear Energy Research | A novel technology for the purity assay of TRODAT-1 raw material |
| ATE534377T1 (de) * | 2006-05-16 | 2011-12-15 | Gilead Sciences Inc | Verfahren und zusammensetzungen zur behandlung von hämatologischen erkrankungen |
| CN101371841A (zh) * | 2007-08-23 | 2009-02-25 | 浙江医药股份有限公司新昌制药厂 | 结晶型恩替卡韦制剂及其制备方法和应用 |
| JP2009196959A (ja) * | 2008-02-25 | 2009-09-03 | Yamaguchi Univ | がん治療用医薬組成物 |
| CN101475594B (zh) * | 2009-02-06 | 2012-05-30 | 廖国超 | 肝靶向抗病毒前体药物环状磷酸酯及其应用 |
| CN101659676B (zh) * | 2009-09-07 | 2012-06-20 | 徐奎 | 一种硫代阿德福韦、替诺福韦肝靶向酯前体药物 |
| US8940313B2 (en) | 2010-04-23 | 2015-01-27 | University Of Southern California | Tyrosine-based prodrugs of antiviral agents |
| US8884027B2 (en) | 2010-10-22 | 2014-11-11 | University Of Rochester | Melampomagnolide B derivatives as antileukemic and cytotoxic agents |
| WO2012062835A1 (en) * | 2010-11-12 | 2012-05-18 | Glaxo Wellcome Manufacturing Pte Ltd | Novel pharmaceutical compositions |
| WO2012079035A1 (en) | 2010-12-10 | 2012-06-14 | Sigmapharm Laboratories, Llc | Highly stable compositions of orally active nucleotide analogues or orally active nucleotide analogue prodrugs |
| WO2012154698A2 (en) | 2011-05-06 | 2012-11-15 | Mckenna Charles E | Method to improve antiviral activity of nucleotide analogue drugs |
| CA2857490C (en) | 2011-12-22 | 2020-03-31 | Geron Corporation | Guanine analogs as telomerase substrates and telomere length affectors |
| CN107312039B (zh) | 2012-08-30 | 2019-06-25 | 江苏豪森药业集团有限公司 | 一种替诺福韦前药的制备方法 |
| CN103333209B (zh) * | 2013-07-05 | 2015-09-30 | 西安新通药物研究有限公司 | 替诺福韦前药(hts)新晶体 |
| CN104710477A (zh) * | 2013-12-16 | 2015-06-17 | 安徽贝克联合制药有限公司 | 替诺福韦环膦酸酯化合物及其药学上可接受的盐和其制备方法及应用 |
| EP3623364A1 (en) | 2014-02-13 | 2020-03-18 | Ligand Pharmaceuticals, Inc. | Prodrug compounds and their uses |
| MX2016011897A (es) | 2014-03-14 | 2017-04-27 | Alltech Inc | Composiciones de compuestos selenoorganicos y metodos de uso de los mismos. |
| CN106687118A (zh) | 2014-07-02 | 2017-05-17 | 配体药物公司 | 前药化合物及其用途 |
| WO2017048252A1 (en) | 2015-09-15 | 2017-03-23 | Alltech, Inc. | Compositions of selenoorganic compounds and methods of use thereof |
| CN107540710B (zh) * | 2016-06-24 | 2020-10-16 | 浙江柏拉阿图医药科技有限公司 | 肝递送抗病毒前体药物核苷环磷酸酯化合物及应用 |
| WO2017220028A1 (zh) | 2016-06-24 | 2017-12-28 | 浙江柏拉阿图医药科技有限公司 | 肝递送抗病毒前体药物核苷环磷酸酯化合物及应用 |
| WO2019139919A1 (en) | 2018-01-09 | 2019-07-18 | Ligand Pharmaceuticals, Inc. | Acetal compounds and therapeutic uses thereof |
| CN108863797B (zh) * | 2018-07-02 | 2021-01-15 | 吉首大学 | 一类3-(取代/非取代苯基)-3-羟基丙酰氧肟酸的制备方法 |
| CN116178440B (zh) * | 2022-12-23 | 2025-12-30 | 杏林中医药科技(广州)有限公司 | 一种肝脏靶向烷化剂及其应用 |
Family Cites Families (42)
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|---|---|---|---|---|
| BE554888A (enExample) * | 1956-12-20 | |||
| CS233665B1 (en) * | 1983-01-06 | 1985-03-14 | Antonin Holy | Processing of isomere o-phosphonylmethylderivative of anantiomere racemic vicinal diene |
| US4579849A (en) | 1984-04-06 | 1986-04-01 | Merck & Co., Inc. | N-alkylguanine acyclonucleosides as antiviral agents |
| FR2562543B1 (fr) * | 1984-04-10 | 1987-09-25 | Elf Aquitaine | Nouveaux phosphonites cycliques, leur preparation et applications |
| NL8403224A (nl) | 1984-10-24 | 1986-05-16 | Oce Andeno Bv | Dioxafosforinanen, de bereiding ervan en de toepassing voor het splitsen van optisch actieve verbindingen. |
| CS263952B1 (en) * | 1985-04-25 | 1989-05-12 | Holy Antonin | Remedy with antiviral effect |
| CS263951B1 (en) | 1985-04-25 | 1989-05-12 | Antonin Holy | 9-(phosponylmethoxyalkyl)adenines and method of their preparation |
| CS264222B1 (en) | 1986-07-18 | 1989-06-13 | Holy Antonin | N-phosphonylmethoxyalkylderivatives of bases of pytimidine and purine and method of use them |
| EP0338372A3 (en) | 1988-04-22 | 1991-10-09 | American Cyanamid Company | Solubilized pro-drugs |
| DE68924456T2 (de) | 1988-08-02 | 1996-05-30 | Nissan Chemical Ind Ltd | Mittel zur Verbesserung von Arzneimitteleffekten für Antitumormittel. |
| US5658889A (en) * | 1989-01-24 | 1997-08-19 | Gensia Pharmaceuticals, Inc. | Method and compounds for aica riboside delivery and for lowering blood glucose |
| CS276072B6 (en) * | 1990-08-06 | 1992-03-18 | Ustav Organicke Chemie A Bioch | (2R)-2-/DI(2-PROPYL)PHOSPHONYLMETHOXY/-3-p-TOLUENESULFONYLOXY -1- TRIMETHYLACETOXYPROPANE AND PROCESS FOR PREPARING THEREOF |
| DK0481214T3 (da) | 1990-09-14 | 1999-02-22 | Acad Of Science Czech Republic | Prolægemidler af phosphonater |
| US5157027A (en) * | 1991-05-13 | 1992-10-20 | E. R. Squibb & Sons, Inc. | Bisphosphonate squalene synthetase inhibitors and method |
| GB9205917D0 (en) | 1992-03-18 | 1992-04-29 | Smithkline Beecham Plc | Pharmaceuticals |
| US5514798A (en) * | 1993-06-02 | 1996-05-07 | Gilead Sciences, Inc. | Method and cyclic carbonates for nucleotide analogues |
| DE69426904T2 (de) | 1993-06-29 | 2001-10-11 | Mitsubishi Chemical Corp., Tokio/Tokyo | Phosphonat-Nukleotid Ester-Derivate |
| ATE486882T1 (de) | 1993-09-17 | 2010-11-15 | Gilead Sciences Inc | Nukleotidanaloge |
| US5567592A (en) * | 1994-02-02 | 1996-10-22 | Regents Of The University Of California | Screening method for the identification of bioenhancers through the inhibition of P-glycoprotein transport in the gut of a mammal |
| AU2808495A (en) | 1994-07-04 | 1996-01-25 | Takeda Chemical Industries Ltd. | Phosphonic acid compounds, their production and use |
| DE4445829A1 (de) | 1994-12-22 | 1996-06-27 | Leybold Ag | Gegenstrom-Schnüffellecksucher |
| US5716928A (en) | 1995-06-07 | 1998-02-10 | Avmax, Inc. | Use of essential oils to increase bioavailability of oral pharmaceutical compounds |
| US5665386A (en) | 1995-06-07 | 1997-09-09 | Avmax, Inc. | Use of essential oils to increase bioavailability of oral pharmaceutical compounds |
| DK0871454T3 (da) | 1995-07-17 | 2004-03-22 | Cephalon Inc | Phosphorholdige inhibitorer af cystein- og serinprotease |
| US5962440A (en) * | 1996-05-09 | 1999-10-05 | Bristol-Myers Squibb Company | Cyclic phosphonate ester inhibitors of microsomal triglyceride transfer protein and method |
| WO1998039344A1 (en) | 1997-03-07 | 1998-09-11 | Metabasis Therapeutics, Inc. | Novel purine inhibitors of fructose-1,6-bisphosphatase |
| DE69819311T2 (de) | 1997-03-07 | 2004-07-29 | Metabasis Therapeutics Inc., San Diego | Neue benzimidazol inhibitoren der fructose-1,6-bisphosphatase |
| AU6691798A (en) * | 1997-03-07 | 1998-09-22 | Metabasis Therapeutics, Inc. | Novel indole and azaindole inhibitors of fructose-1,6-bisphosphatase |
| ES2187991T3 (es) | 1997-07-25 | 2003-06-16 | Gilead Sciences Inc | Composiciones de analogo de nucleotido. |
| US6180666B1 (en) | 1997-09-05 | 2001-01-30 | Anmax, Inc. | Use of gallic acid esters to increase bioavailability of orally administered pharmaceutical compounds |
| US5962522A (en) * | 1997-09-05 | 1999-10-05 | Avmax, Inc. | Propyl gallate to increase bioavailability of orally administered pharmaceutical compounds |
| US6312662B1 (en) * | 1998-03-06 | 2001-11-06 | Metabasis Therapeutics, Inc. | Prodrugs phosphorus-containing compounds |
| CZ297264B6 (cs) * | 1998-09-09 | 2006-10-11 | Metabasis Therapeutics, Inc. | Nové heteroaromatické inhibitory fruktóza-1,6-bisfosfatázy |
| WO2000038666A2 (en) | 1998-12-24 | 2000-07-06 | Metabasis Therapeutics, Inc. | A COMBINATION OF FBPase INHIBITORS AND INSULIN SENSITIZERS FOR THE TREATMENT OF DIABETES |
| SK12442001A3 (sk) | 1999-03-05 | 2002-06-04 | Metabasis Therapeutics, Inc. | Cyklické fosforamidáty, spôsob ich prípravy a farmaceutické kompozície, ktoré ich obsahujú |
| JP4979866B2 (ja) * | 1999-09-08 | 2012-07-18 | 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 | 肝臓に特異的なドラッグデリバリーのためのプロドラッグ |
| HRP20030047B1 (hr) | 2000-07-21 | 2016-02-26 | Gilead Sciences, Inc. | Prolijekovi koji su fosfonatni analozi nukleotida i metode njihovog odabira te njihova priprava |
| AU2003235501A1 (en) * | 2002-05-13 | 2003-11-11 | Metabasis Therapeutics, Inc. | PMEA and PMPA cyclic producing synthesis |
| IL164809A0 (en) | 2002-05-13 | 2005-12-18 | Metabasis Therapeutics Inc | Novel phosphonic acid basdrugs of pmea and its analogues |
| PL376474A1 (en) * | 2002-10-31 | 2005-12-27 | Metabasis Therapeutics, Inc. | Novel cyclic phosphate diesters of 1,3-propane-1-aryl diols and their use in preparing prodrugs |
| US7553825B2 (en) * | 2003-12-30 | 2009-06-30 | Gilead Sciences, Inc. | Anti-proliferative compounds, compositions, and methods of use thereof |
| MXPA06014013A (es) * | 2004-06-08 | 2007-03-15 | Metabasis Therapeutics Inc | Sintesis mediada por acidos de lewis de esteres ciclicos. |
-
2003
- 2003-05-12 IL IL16480903A patent/IL164809A0/xx unknown
- 2003-05-12 AU AU2003299492A patent/AU2003299492B2/en not_active Ceased
- 2003-05-12 EP EP10005037.6A patent/EP2223927B1/en not_active Expired - Lifetime
- 2003-05-12 NZ NZ536328A patent/NZ536328A/en not_active IP Right Cessation
- 2003-05-12 CA CA2485702A patent/CA2485702C/en not_active Expired - Lifetime
- 2003-05-12 JP JP2004546667A patent/JP4476811B2/ja not_active Expired - Fee Related
- 2003-05-12 EP EP03799779A patent/EP1532157A4/en not_active Withdrawn
- 2003-05-12 WO PCT/US2003/014821 patent/WO2004037161A2/en not_active Ceased
- 2003-05-12 US US10/436,922 patent/US7214668B2/en not_active Expired - Lifetime
- 2003-11-18 TW TW092132408A patent/TWI347325B/zh not_active IP Right Cessation
-
2004
- 2004-10-25 IL IL164809A patent/IL164809A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| IL164809A (en) | 2012-08-30 |
| AU2003299492A1 (en) | 2004-05-13 |
| US20030229225A1 (en) | 2003-12-11 |
| NZ536328A (en) | 2007-11-30 |
| JP4476811B2 (ja) | 2010-06-09 |
| EP1532157A4 (en) | 2009-02-25 |
| CA2485702A1 (en) | 2004-05-06 |
| TW200426152A (en) | 2004-12-01 |
| EP2223927A3 (en) | 2010-09-15 |
| EP1532157A2 (en) | 2005-05-25 |
| EP2223927A2 (en) | 2010-09-01 |
| US7214668B2 (en) | 2007-05-08 |
| CA2485702C (en) | 2011-07-19 |
| JP2006511490A (ja) | 2006-04-06 |
| IL164809A0 (en) | 2005-12-18 |
| WO2004037161A2 (en) | 2004-05-06 |
| WO2004037161A3 (en) | 2005-03-31 |
| AU2003299492B2 (en) | 2010-06-10 |
| EP2223927B1 (en) | 2014-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |