CA2261619A1 - Nucleotide analogs - Google Patents

Nucleotide analogs

Info

Publication number
CA2261619A1
CA2261619A1 CA002261619A CA2261619A CA2261619A1 CA 2261619 A1 CA2261619 A1 CA 2261619A1 CA 002261619 A CA002261619 A CA 002261619A CA 2261619 A CA2261619 A CA 2261619A CA 2261619 A1 CA2261619 A1 CA 2261619A1
Authority
CA
Canada
Prior art keywords
alkyl
independently
antiviral
useful
compounds
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.)
Granted
Application number
CA002261619A
Other languages
French (fr)
Other versions
CA2261619C (en
Inventor
Murty N. Arimilli
Kenneth C. Cundy
Joseph P. Dougherty
Choung U. Kim
Reza Oliyai
Valentino J. Stella
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gilead Sciences Inc
Original Assignee
Gilead Sciences, Inc.
Murty N. Arimilli
Kenneth C. Cundy
Joseph P. Dougherty
Choung U. Kim
Reza Oliyai
Valentino J. Stella
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26696272&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2261619(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Gilead Sciences, Inc., Murty N. Arimilli, Kenneth C. Cundy, Joseph P. Dougherty, Choung U. Kim, Reza Oliyai, Valentino J. Stella filed Critical Gilead Sciences, Inc.
Publication of CA2261619A1 publication Critical patent/CA2261619A1/en
Application granted granted Critical
Publication of CA2261619C publication Critical patent/CA2261619C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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 System
    • 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
    • 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
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
    • 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 System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6509—Six-membered rings
    • C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3

Abstract

Novel compounds are provided that comprise esters of antiviral phosphonomethoxy nucleotide analogs with carbonates and/or carbamates having the structure -OC(R2)2OC(O)X(R)a, wherein R2 independently is H, C1-C12 alkyl, aryl, alkenyl, alkynyl, alkyenylaryl, alkynylaryl, alkaryl, arylalkynyl, arylalkenyl or arylalkyl which is unsubstituted or is substituted with halo, azido, nitro or OR3 in which R3 is C1-C12 alkyl; X is N or O; R is independently H, C1-C12 alkyl, aryl, alkenyl, alkynyl, alkyenylaryl, alkynylaryl, alkaryl, arylalkynyl, arylalkenyl or arylalkyl which is unsubstituted or is substituted with halo, azido, nitro, -O-, -N-, -NR4-, -N(R4)2- or OR3, R4 independently is -H or C1-C8 alkyl, provided that at least one R is not H; and a is 1 or 2, with the proviso that when a is 2 and X is N, (a) two R groups can be taken together to form a carbocycle or oxygen-containing heterocycle, or (b) one R additionally can be OR3. The compounds are useful as intermediates for the preparation of antiviral compounds or oligonucleotides, or are useful for administration directly to patients for antiviral therapy or prophylaxis. Embodiments are particularly useful when administered orally.
CA002261619A 1996-07-26 1997-07-25 Nucleotide analogs Expired - Lifetime CA2261619C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US68683896A 1996-07-26 1996-07-26
US2270896P 1996-07-26 1996-07-26
US08/686,838 1996-07-26
PCT/US1997/013244 WO1998004569A1 (en) 1996-07-26 1997-07-25 Nucleotide analogs

Publications (2)

Publication Number Publication Date
CA2261619A1 true CA2261619A1 (en) 1998-02-05
CA2261619C CA2261619C (en) 2006-05-23

Family

ID=26696272

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002261619A Expired - Lifetime CA2261619C (en) 1996-07-26 1997-07-25 Nucleotide analogs

Country Status (4)

Country Link
JP (6) JP4033494B2 (en)
CA (1) CA2261619C (en)
TW (2) TW470748B (en)
WO (1) WO1998004569A1 (en)

Families Citing this family (44)

* Cited by examiner, † Cited by third party
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JP4033494B2 (en) * 1996-07-26 2008-01-16 ギリヤド サイエンシーズ， インコーポレイテッド Nucleotide analogs
PT1256584E (en) * 1997-07-25 2004-12-31 Gilead Sciences Inc PROCESS FOR THE PREPARATION OF ADEFOVIR-DIPIVOXYL
EP1243593B1 (en) * 1997-07-25 2005-09-21 Gilead Sciences, Inc. Nucleotide analog composition and synthesis method
WO1999005150A1 (en) * 1997-07-25 1999-02-04 Gilead Sciences, Inc. Nucleotide analog composition and synthesis method
AU4716299A (en) * 1998-06-24 2000-01-10 Emory University Use of 3'-azido-2',3'-dideoxyuridine in combination with further anti-hiv drugs for the manufacture of a medicament for the treatment of hiv
CZ304734B6 (en) * 2000-07-21 2014-09-10 Gilead Sciences, Inc. Process for preparing 9-[2-(phosphonomethoxy)propyl]adenine and 9-[2-(phosphonomethoxy)ethyl]adenine
CA2481449A1 (en) 2002-04-26 2003-11-06 Gilead Sciences, Inc. Method and compositions for identifying anti-hiv therapeutic compounds
EP1923063A3 (en) 2003-01-14 2009-04-08 Gilead Sciences, Inc. Compositions and methods for combination antiviral therapy
US7432261B2 (en) 2003-04-25 2008-10-07 Gilead Sciences, Inc. Anti-inflammatory phosphonate compounds
US7452901B2 (en) 2003-04-25 2008-11-18 Gilead Sciences, Inc. Anti-cancer phosphonate analogs
US7273716B2 (en) 2003-04-25 2007-09-25 Gilead Sciences, Inc. Methods and compositions for identifying therapeutic compounds with GS-7340 ester hydrolase
US7427636B2 (en) 2003-04-25 2008-09-23 Gilead Sciences, Inc. Inosine monophosphate dehydrogenase inhibitory phosphonate compounds
WO2004096285A2 (en) 2003-04-25 2004-11-11 Gilead Sciences, Inc. Anti-infective phosphonate conjugates
CN101410120A (en) * 2003-04-25 2009-04-15 吉里德科学公司 Anti-inflammatory phosphonate compounds
US7470724B2 (en) 2003-04-25 2008-12-30 Gilead Sciences, Inc. Phosphonate compounds having immuno-modulatory activity
US7407965B2 (en) 2003-04-25 2008-08-05 Gilead Sciences, Inc. Phosphonate analogs for treating metabolic diseases
EP1620109A2 (en) 2003-04-25 2006-02-01 Gilead Sciences, Inc. Kinase inhibitor phosphonate conjugates
NZ542342A (en) 2003-04-25 2009-05-31 Gilead Sciences Inc Antiviral phosphonate analogs
WO2005002626A2 (en) 2003-04-25 2005-01-13 Gilead Sciences, Inc. Therapeutic phosphonate compounds
ATE496056T1 (en) 2003-06-16 2011-02-15 Acad Of Science Czech Republic PYRIMIDINE COMPOUNDS WITH PHOSPHONATE GROUPS AS ANTIVIRAL NUCLEOTIDE ANALOGS
WO2005044279A1 (en) 2003-10-24 2005-05-19 Gilead Sciences, Inc. Purine nucleoside phosphonate conjugates
WO2005044308A1 (en) 2003-10-24 2005-05-19 Gilead Sciences, Inc. Phosphonate analogs of antimetabolites
EP1715871A1 (en) * 2003-12-22 2006-11-02 Gilead Sciences, Inc. Kinase inhibitor phosphonate conjugates
WO2005063751A1 (en) 2003-12-22 2005-07-14 Gilead Sciences, Inc. 4’-substituted carbovir-and abacavir-derivatives as well as related compounds with hiv and hcv antiviral activity
AU2005330489B2 (en) 2004-07-27 2011-08-25 Gilead Sciences, Inc. Nucleoside phosphonate conjugates as anti HIV agents
CN102228463B (en) * 2005-06-13 2012-12-19 博瑞生物医药技术(苏州)有限公司 Tenofovir crystals
TWI375560B (en) 2005-06-13 2012-11-01 Gilead Sciences Inc Composition comprising dry granulated emtricitabine and tenofovir df and method for making the same
TWI471145B (en) 2005-06-13 2015-02-01 Bristol Myers Squibb & Gilead Sciences Llc Unitary pharmaceutical dosage form
CA2681267C (en) 2007-04-13 2013-11-19 Southern Research Institute Anti-angiogenic agents and methods of use
CN101778855A (en) * 2007-05-22 2010-07-14 阿尔迪默菲克斯技术有限责任公司 Tenofovir disoproxil hemi-fumaric acid co-crystal
WO2009064174A1 (en) * 2007-11-14 2009-05-22 Ultimorphix Technologies B.V. Polymorphic form of tenofovir disoproxil fumarate, method for its preparation and use
EP2937356A1 (en) * 2008-04-25 2015-10-28 Cipla Limited Crystalline form of tenofovir disoproxil and a process for its preparation
WO2010005986A1 (en) 2008-07-08 2010-01-14 Gilead Sciences, Inc. Salts of hiv inhibitor compounds
CN102093422B (en) 2009-12-10 2015-02-25 中国人民解放军军事医学科学院毒物药物研究所 Acyclic nucleoside phosphonate derivative and medicinal application thereof
WO2012152317A1 (en) * 2011-05-10 2012-11-15 Okapi Sciences Nv Compounds for use in the treatment of feline retroviral infections
CA2845553C (en) 2011-08-16 2019-05-28 Gilead Sciences, Inc. Tenofovir alafenamide hemifumarate
CN103626802A (en) * 2012-08-23 2014-03-12 重庆药友制药有限责任公司 Novel method used for preparing tenofovir
CN103665043B (en) 2012-08-30 2017-11-10 江苏豪森药业集团有限公司 A kind of tenofovir prodrug and its application in medicine
WO2014068265A1 (en) 2012-10-29 2014-05-08 Cipla Limited Antiviral phosphonate analogues and process for preparation thereof
EP2860184B1 (en) 2013-10-09 2018-08-29 Zentiva, k.s. Dihydrogenphosphate salt of Tenofovir disoproxil
EP2860185A1 (en) 2013-10-09 2015-04-15 Zentiva, k.s. An improved process for the preparation of Tenofovir disoproxil and pharmaceutically acceptable salts thereof
TWI660965B (en) * 2014-01-15 2019-06-01 美商基利科學股份有限公司 Solid forms of tenofovir
SI3661937T1 (en) 2017-08-01 2021-11-30 Gilead Sciences, Inc. Crystalline forms of ethyl ((s)-((((2r,5r)-5-(6-amino-9h-purin-9-yl)-4-fluoro-2,5-dihydrofuran-2-yl)oxy)methyl)(phenoxy)phosphoryl)-l-alaninate (gs-9131) for treating viral infections
CN107805202A (en) * 2017-12-01 2018-03-16 内蒙古圣氏化学股份有限公司 A kind of chloromethyl butylperoxyisopropyl carbonate continuous reacting device and method

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ222553A (en) * 1986-11-18 1991-07-26 Bristol Myers Co Phosphonomethoxyalkylene purine and pyrimidine derivatives and pharmaceutical compositions
EP0481214B1 (en) * 1990-09-14 1998-06-24 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Prodrugs of phosphonates
GB9026164D0 (en) * 1990-12-01 1991-01-16 Beecham Group Plc Pharmaceuticals
AU691527B2 (en) * 1993-09-17 1998-05-21 Gilead Sciences, Inc. Nucleotide analogs
JP4033494B2 (en) * 1996-07-26 2008-01-16 ギリヤド サイエンシーズ， インコーポレイテッド Nucleotide analogs

Also Published As

Publication number Publication date
TW470748B (en) 2002-01-01
JP2017031212A (en) 2017-02-09
CA2261619C (en) 2006-05-23
JP2015164934A (en) 2015-09-17
TW444020B (en) 2001-07-01
JP2011016847A (en) 2011-01-27
JP2007297406A (en) 2007-11-15
JP2000515866A (en) 2000-11-28
JP4033494B2 (en) 2008-01-16
JP2014159450A (en) 2014-09-04
WO1998004569A1 (en) 1998-02-05

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Effective date: 20170725