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 (OSRAM) |
| EP (2) | EP1532157A4 (OSRAM) |
| JP (1) | JP4476811B2 (OSRAM) |
| AU (1) | AU2003299492B2 (OSRAM) |
| CA (1) | CA2485702C (OSRAM) |
| IL (2) | IL164809A0 (OSRAM) |
| NZ (1) | NZ536328A (OSRAM) |
| TW (1) | TWI347325B (OSRAM) |
| WO (1) | WO2004037161A2 (OSRAM) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6312662B1 (en) | 1998-03-06 | 2001-11-06 | Metabasis Therapeutics, Inc. | Prodrugs phosphorus-containing compounds |
| EP1504014B1 (en) * | 2002-05-13 | 2015-12-02 | Metabasis Therapeutics, Inc. | Process for preparation of cyclic prodrugs of pmea and pmpa |
| IL164809A0 (en) | 2002-05-13 | 2005-12-18 | Metabasis Therapeutics Inc | Novel phosphonic acid basdrugs of pmea and its analogues |
| CA2503730C (en) * | 2002-10-31 | 2011-10-18 | Metabasis Therapeutics, Inc. | Cytarabine monophosphate prodrugs |
| WO2005072748A1 (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 |
| AU2005254940A1 (en) | 2004-06-08 | 2005-12-29 | Metabasis Therapeutics, Inc. | Lewis acid mediated synthesis of cyclic esters |
| WO2006055525A2 (en) * | 2004-11-15 | 2006-05-26 | Ceptyr, Inc. | Protein tyrosine phosphatase inhibitors and methods of use thereof |
| WO2007013085A1 (en) * | 2005-07-26 | 2007-02-01 | Hetero Drugs Limited | Novel 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 |
| PL2020996T3 (pl) * | 2006-05-16 | 2012-04-30 | Gilead Sciences Inc | Sposób i kompozycje do leczenia chorób nowotworowych układu krwiotwórczego |
| 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 |
| FI2648701T3 (fi) | 2010-12-10 | 2023-06-12 | Sigmapharm Laboratories Llc | Hyvin stabiileja adefovirdipivoksiilin koostumuksia |
| US9550803B2 (en) | 2011-05-06 | 2017-01-24 | University Of Southern California | 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 |
| WO2015123352A1 (en) | 2014-02-13 | 2015-08-20 | Ligand Pharmaceuticals, Inc. | Prodrug compounds and their uses |
| KR102448455B1 (ko) | 2014-03-14 | 2022-09-28 | 올텍 법인회사 | 셀레노유기 화합물의 조성물 및 이의 사용 방법 |
| 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 |
| 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 |
| 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 |
| CN111788196A (zh) | 2018-01-09 | 2020-10-16 | 配体药物公司 | 缩醛化合物及其治疗用途 |
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR75178E (OSRAM) * | 1956-12-20 | 1961-09-08 | ||
| 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. |
| CS263951B1 (en) | 1985-04-25 | 1989-05-12 | Antonin Holy | 9-(phosponylmethoxyalkyl)adenines and method of their preparation |
| CS263952B1 (en) * | 1985-04-25 | 1989-05-12 | Holy Antonin | Remedy with antiviral effect |
| 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 |
| CS387190A3 (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 |
| ES2118069T3 (es) | 1990-09-14 | 1998-09-16 | Acad Of Science Czech Republic | Profarmacos de fosfonatos. |
| 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 |
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| EP0632048B1 (en) * | 1993-06-29 | 2001-03-21 | Mitsubishi Chemical Corporation | Phosphonate-nucleotide ester derivatives |
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| 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 |
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| DE4445829A1 (de) | 1994-12-22 | 1996-06-27 | Leybold Ag | Gegenstrom-Schnüffellecksucher |
| US5665386A (en) | 1995-06-07 | 1997-09-09 | Avmax, Inc. | Use of essential oils to increase bioavailability of oral pharmaceutical compounds |
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| US5962440A (en) * | 1996-05-09 | 1999-10-05 | Bristol-Myers Squibb Company | Cyclic phosphonate ester inhibitors of microsomal triglyceride transfer protein and method |
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| KR100700089B1 (ko) | 1997-07-25 | 2007-03-28 | 길리애드 사이언시즈, 인코포레이티드 | 뉴클레오티드 동족체의 제조에 사용되는 중간체의 제조방법 |
| 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 |
| HK1042496B (zh) * | 1998-09-09 | 2006-01-27 | 症变治疗公司 | 新的果糖1，6-二磷酸酶的杂芳族抑制剂 |
| CA2354053A1 (en) | 1998-12-24 | 2000-07-06 | Metabasis Therapeutics, Inc. | A combination of fbpase inhibitors and insulin sensitizers for the treatment of diabetes |
| JP5063837B2 (ja) | 1999-03-05 | 2012-10-31 | 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 | 新規リン含有プロドラッグ |
| US6752981B1 (en) * | 1999-09-08 | 2004-06-22 | Metabasis Therapeutics, Inc. | Prodrugs for liver specific drug delivery |
| DK1301519T4 (da) | 2000-07-21 | 2021-12-20 | Gilead Sciences Inc | Prodrugs af phosphonatnukleotidanaloger og fremgangsmåder til udvælgelse og fremstilling heraf |
| EP1504014B1 (en) * | 2002-05-13 | 2015-12-02 | Metabasis Therapeutics, Inc. | Process for preparation of cyclic prodrugs of pmea and pmpa |
| IL164809A0 (en) | 2002-05-13 | 2005-12-18 | Metabasis Therapeutics Inc | Novel phosphonic acid basdrugs of pmea and its analogues |
| CA2503730C (en) * | 2002-10-31 | 2011-10-18 | Metabasis Therapeutics, Inc. | Cytarabine monophosphate prodrugs |
| PL212403B1 (pl) * | 2003-12-30 | 2012-09-28 | Gilead Sciences | Pochodna fosfonianowa, kompozycja farmaceutyczna zawierajaca ten zwiazek oraz jego zastosowanie w leczeniu guzów |
| AU2005254940A1 (en) * | 2004-06-08 | 2005-12-29 | Metabasis Therapeutics, Inc. | Lewis acid mediated synthesis of cyclic esters |
-
2003
- 2003-05-12 IL IL16480903A patent/IL164809A0/xx unknown
- 2003-05-12 NZ NZ536328A patent/NZ536328A/en not_active IP Right Cessation
- 2003-05-12 WO PCT/US2003/014821 patent/WO2004037161A2/en not_active Ceased
- 2003-05-12 CA CA2485702A patent/CA2485702C/en not_active Expired - Lifetime
- 2003-05-12 EP EP03799779A patent/EP1532157A4/en not_active Withdrawn
- 2003-05-12 EP EP10005037.6A patent/EP2223927B1/en not_active Expired - Lifetime
- 2003-05-12 JP JP2004546667A patent/JP4476811B2/ja not_active Expired - Fee Related
- 2003-05-12 AU AU2003299492A patent/AU2003299492B2/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 |
|---|---|
| CA2485702A1 (en) | 2004-05-06 |
| WO2004037161A2 (en) | 2004-05-06 |
| IL164809A0 (en) | 2005-12-18 |
| US7214668B2 (en) | 2007-05-08 |
| IL164809A (en) | 2012-08-30 |
| TW200426152A (en) | 2004-12-01 |
| JP4476811B2 (ja) | 2010-06-09 |
| CA2485702C (en) | 2011-07-19 |
| WO2004037161A3 (en) | 2005-03-31 |
| AU2003299492A1 (en) | 2004-05-13 |
| EP2223927A3 (en) | 2010-09-15 |
| EP1532157A2 (en) | 2005-05-25 |
| NZ536328A (en) | 2007-11-30 |
| EP1532157A4 (en) | 2009-02-25 |
| EP2223927B1 (en) | 2014-10-15 |
| AU2003299492B2 (en) | 2010-06-10 |
| JP2006511490A (ja) | 2006-04-06 |
| EP2223927A2 (en) | 2010-09-01 |
| US20030229225A1 (en) | 2003-12-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |