DK167342B1 - Terapeutisk praeparat til behandling af virussygdomme samt anvendelse af et 9-(fosfonylmetoxyalkyl)adeninderivat til fremstilling af praeparatet - Google Patents

Terapeutisk praeparat til behandling af virussygdomme samt anvendelse af et 9-(fosfonylmetoxyalkyl)adeninderivat til fremstilling af praeparatet Download PDF

Info

Publication number: DK167342B1
Authority: DK; Denmark
Prior art keywords: preparation; compounds; formula; compound; treatment
Prior art date: 1985-04-25

Application number

DK184186A

Other languages

Danish (da)

English (en)

Other versions

DK184186A (da

DK184186D0 (da

Inventor

Erik De Clercq

Antonin Holy

Ivan Rosenberg

Original Assignee

Stichting Rega V Z W

Ceskoslovenska Akademie Ved

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.)

1985-04-25

Filing date

1986-04-22

Publication date

1993-10-18

1986-04-22 Application filed by Stichting Rega V Z W, Ceskoslovenska Akademie Ved filed Critical Stichting Rega V Z W

1986-04-22 Publication of DK184186D0 publication Critical patent/DK184186D0/da

1986-10-26 Publication of DK184186A publication Critical patent/DK184186A/da

1993-10-18 Application granted granted Critical

1993-10-18 Publication of DK167342B1 publication Critical patent/DK167342B1/da

Links

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CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
- 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
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Virology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Epidemiology (AREA)
Biotechnology (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)

DK184186A 1985-04-25 1986-04-22 Terapeutisk praeparat til behandling af virussygdomme samt anvendelse af et 9-(fosfonylmetoxyalkyl)adeninderivat til fremstilling af praeparatet DK167342B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CS853018A CS263952B1 (en)	1985-04-25	1985-04-25	Remedy with antiviral effect
CS301885		1985-04-25

Publications (3)

Publication Number	Publication Date
DK184186D0 DK184186D0 (da)	1986-04-22
DK184186A DK184186A (da)	1986-10-26
DK167342B1 true DK167342B1 (da)	1993-10-18

Family

ID=5369042

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK184186A DK167342B1 (da)	1985-04-25	1986-04-22	Terapeutisk praeparat til behandling af virussygdomme samt anvendelse af et 9-(fosfonylmetoxyalkyl)adeninderivat til fremstilling af praeparatet

Country Status (17)

Country	Link
US (1)	US4724233A (cs)
EP (1)	EP0205826B1 (cs)
JP (1)	JPH0692307B2 (cs)
AT (1)	ATE73663T1 (cs)
AU (1)	AU586860B2 (cs)
CA (1)	CA1272956A (cs)
CS (1)	CS263952B1 (cs)
DE (1)	DE3684363D1 (cs)
DK (1)	DK167342B1 (cs)
EG (1)	EG18436A (cs)
GR (1)	GR861089B (cs)
HK (1)	HK217296A (cs)
IL (1)	IL78553A (cs)
NZ (1)	NZ215939A (cs)
PH (1)	PH23112A (cs)
PT (1)	PT82457B (cs)
ZA (1)	ZA863133B (cs)

Families Citing this family (58)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5047533A (en) *	1983-05-24	1991-09-10	Sri International	Acyclic purine phosphonate nucleotide analogs
CS264222B1 (en) *	1986-07-18	1989-06-13	Holy Antonin	N-phosphonylmethoxyalkylderivatives of bases of pytimidine and purine and method of use them
US5650510A (en) *	1986-11-18	1997-07-22	Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic	Antiviral phosphonomethoxyalkylene purine and pyrimidine derivatives
IL84477A (en) *	1986-11-18	1995-12-08	Bristol Myers Squibb Co	History of Phosphonomethoxyalkylene Purinopyrimidine and Pharmaceutical Preparations Containing Them
US5284837A (en) *	1988-05-06	1994-02-08	Medivir Ab	Derivatives of purine, process for their preparation and a pharmaceutical preparation
EP0353955A3 (en) *	1988-08-02	1991-08-14	Beecham Group Plc	Novel compounds
US5688778A (en) *	1989-05-15	1997-11-18	Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic	Nucleoside analogs
US5302585A (en) *	1990-04-20	1994-04-12	Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic	Use of chiral 2-(phosphonomethoxy)propyl guanines as antiviral agents
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
CZ287745B6 (cs) *	1991-10-11	2001-01-17	Ústav organické chemie a biochemie AV ČR	Acyklické fosfonomethoxyalkylsubstituované alkenylové a alkinylové deriváty purinu a pyrimidinu
US6057305A (en) *	1992-08-05	2000-05-02	Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic	Antiretroviral enantiomeric nucleotide analogs
US5514798A (en) *	1993-06-02	1996-05-07	Gilead Sciences, Inc.	Method and cyclic carbonates for nucleotide analogues
US5798340A (en) *	1993-09-17	1998-08-25	Gilead Sciences, Inc.	Nucleotide analogs
EP0719274A1 (en) *	1993-09-17	1996-07-03	Gilead Sciences, Inc.	Method for dosing therapeutic compounds
WO1995026734A1 (en) *	1994-04-04	1995-10-12	Freeman William R	Use of phosphonylmethoxyalkyl nucleosides for the treatment of raised intraocular pressure
US5468752A (en) *	1994-04-04	1995-11-21	Freeman; William R.	Treatment of conditions of abnormally increased intraocular pressure by administration of HPMPC and related phosphonylmethoxyalkylcytosines
US5977061A (en) *	1995-04-21	1999-11-02	Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic	N6 - substituted nucleotide analagues and their use
US6093816A (en)	1996-06-27	2000-07-25	Isis Pharmaceuticals, Inc.	Cationic lipids
US6635278B1 (en)	1998-12-15	2003-10-21	Gilead Sciences, Inc.	Pharmaceutical formulations
TWI230618B (en) *	1998-12-15	2005-04-11	Gilead Sciences Inc	Pharmaceutical compositions of 9-[2-[[bis[(pivaloyloxy)methyl]phosphono]methoxy]ethyl]adenine and tablets or capsules containing the same
US7205404B1 (en) *	1999-03-05	2007-04-17	Metabasis Therapeutics, Inc.	Phosphorus-containing prodrugs
ATE322494T1 (de) *	2000-01-07	2006-04-15	Universitaire Instelling Antwe	Purin derivate, ihre herstellung und verwendung
CZ304734B6 (cs)	2000-07-21	2014-09-10	Gilead Sciences, Inc.	Způsob přípravy 9-[2-(fosfonomethoxy)propyl]adeninu a 9-[2-(fosfonomethoxy)ethyl]adeninu
WO2003002580A1 (en) *	2001-06-29	2003-01-09	Institute Of Organic Chemistry And Biochemistry Ofthe Academy Of Sciences Of The Czech Republic	6-`2-(phosphonomethoxy)alkoxy pyrimidine derivatives having antiviral activity
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
RU2225223C1 (ru) *	2002-06-14	2004-03-10	Закрытое акционерное общество Фирма "ВИТАФАРМА"	Лиофилизированная антигерпетическая вакцина
KR20050086519A (ko) *	2002-11-12	2005-08-30	티안진 킨슬리 파마슈티컬 컴퍼니 리미티드	새로운 결정 형태를 가진 아데포비어 디피복실 및 그조성물
MXPA05007016A (es)	2003-01-14	2005-09-12	Gilead Sciences Inc	Composiciones y metodos para terapia antiviral de combinacion.
DE602004031115D1 (de)	2003-06-16	2011-03-03	Acad Of Science Czech Republic	Pyrimidinverbindungen mit phosphonatgruppen als antivirale nucleotidanaloga
WO2005123729A1 (en) *	2004-06-08	2005-12-29	Metabasis Therapeutics, Inc.	Lewis acid mediated synthesis of cyclic esters
CN100338080C (zh) *	2004-06-16	2007-09-19	山东中科泰斗化学有限公司	9－[2－(膦羧基甲氧基)乙基]腺嘌呤双环醇酯及其制备方法
ME03423B (me)	2004-07-27	2020-01-20	Gilead Sciences Inc	Fosfonatni analozi jedinjenja hiv inhibitora
WO2006066074A2 (en) *	2004-12-16	2006-06-22	The Regents Of The University Of California	Lung-targeted drugs
US20090156545A1 (en) *	2005-04-01	2009-06-18	Hostetler Karl Y	Substituted Phosphate Esters of Nucleoside Phosphonates
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 (zh)	2005-06-13	2015-02-01	Bristol Myers Squibb & Gilead Sciences Llc	單一式藥學劑量型
FR2908133B1 (fr) *	2006-11-08	2012-12-14	Centre Nat Rech Scient	Nouveaux analogues de nucleotides comme molecules precurseurs d'antiviraux
RU2443703C2 (ru)	2007-06-18	2012-02-27	Саншайн Лейк Фарма Ко., Лтд	Бром-фенил замещенные тиазолилдигидропиримидины
TWI444384B (zh)	2008-02-20	2014-07-11	Gilead Sciences Inc	核苷酸類似物及其在治療惡性腫瘤上的用途
US7935817B2 (en) *	2008-03-31	2011-05-03	Apotex Pharmachem Inc.	Salt form and cocrystals of adefovir dipivoxil and processes for preparation thereof
ES2467108T3 (es)	2008-12-09	2014-06-11	Gilead Sciences, Inc.	Moduladores de receptores tipo toll
WO2010110622A2 (en)	2009-03-26	2010-09-30	Daewoong Pharmaceutical Co., Ltd.	Novel crystal forms of adefovir dipivoxil and processes for preparing the same
US20110223131A1 (en)	2010-02-24	2011-09-15	Gilead Sciences, Inc.	Antiviral compounds
RU2606845C2 (ru)	2010-12-10	2017-01-10	СИГМАФАРМ ЛЭБОРЭТОРИЗ, ЭлЭлСи	Высокостабильные композиции перорально активных аналогов нуклеотидов или перорально активных пролекарств аналогов нуклеотидов
EA201892769A3 (ru)	2013-03-15	2019-08-30	Дзе Риджентс Оф Дзе Юниверсити Оф Калифорния	Сложные диэфиры ациклических нуклеозидфосфонатов
WO2015038421A1 (en)	2013-09-10	2015-03-19	Dow Corning Corporation	Wear-resistant silicon eutectic alloy components and methods of making the same
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
WO2015195538A1 (en)	2014-06-17	2015-12-23	Dow Corning Corporation	Decorative shape-cast articles made from silicon eutectic alloys, and methods for producing the same
WO2016001907A1 (en)	2014-07-02	2016-01-07	Prendergast Patrick T	Mogroside iv and mogroside v as agonist/stimulator/un-blocking agent for toll-like receptor 4 and adjuvant for use in human/animal vaccine and to stimulate immunity against disease agents.
CN106687118A (zh)	2014-07-02	2017-05-17	配体药物公司	前药化合物及其用途
PT3166607T (pt)	2014-07-11	2022-12-07	Gilead Sciences Inc	Moduladores de receptores de tipo toll para o tratamento do vih
BR112017005111B1 (pt)	2014-09-15	2023-02-14	The Regents Of The University Of California	Compostos análogos de nucleotídeo acíclico, composição farmacêutica contendo tais compostos, e usos da composição no tratamento de uma infecção por papilomavírus
WO2017048956A1 (en)	2015-09-15	2017-03-23	The Regents Of The University Of California	Nucleotide analogs
HK1257270A1 (zh)	2015-09-15	2019-10-18	Gilead Sciences, Inc.	用於治疗hiv的toll样受体(tlr)调节剂
EP3372227A1 (en)	2017-03-06	2018-09-12	MH10 Spolka z ograniczona odpowiedzialnoscia	Tablet formulation of adefovir dipivoxil
RU2020126177A (ru)	2018-01-09	2022-02-10	Лиганд Фармасьютикалз, Инк.	Ацетальные соединения и их терапевтическое применение
IL318465A (en)	2022-07-21	2025-03-01	Antiva Biosciences Inc	Compositions and dosage forms for the treatment of HPV infection and HPV-induced neoplasia

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1523865A (en) *	1974-09-02	1978-09-06	Wellcome Found	Purine compunds and salts thereof
JPS52105195A (en) *	1976-03-01	1977-09-03	Wellcome Found	Substituted purine
US4230708A (en) *	1977-10-20	1980-10-28	Stichting Rega V.Z.W.	Therapeutic application of (S) -or (RS)-9-(2, 3-dihydroxypropyl) adenine for use as antiviral agents
CS233665B1 (en) *	1983-01-06	1985-03-14	Antonin Holy	Processing of isomere o-phosphonylmethylderivative of anantiomere racemic vicinal diene
CS238038B1 (en) *	1983-10-07	1985-11-13	Antonin Holy	Medical drug with antivirus effect

1985
- 1985-04-25 CS CS853018A patent/CS263952B1/cs not_active IP Right Cessation
1986
- 1986-04-21 IL IL78553A patent/IL78553A/xx not_active IP Right Cessation
- 1986-04-21 US US06/854,087 patent/US4724233A/en not_active Expired - Lifetime
- 1986-04-22 AU AU56468/86A patent/AU586860B2/en not_active Ceased
- 1986-04-22 DK DK184186A patent/DK167342B1/da not_active IP Right Cessation
- 1986-04-24 NZ NZ215939A patent/NZ215939A/xx unknown
- 1986-04-24 PH PH33699A patent/PH23112A/en unknown
- 1986-04-24 GR GR861089A patent/GR861089B/el unknown
- 1986-04-24 CA CA000507510A patent/CA1272956A/en not_active Expired - Lifetime
- 1986-04-24 EG EG241/86A patent/EG18436A/xx active
- 1986-04-24 PT PT82457A patent/PT82457B/pt unknown
- 1986-04-25 DE DE8686105776T patent/DE3684363D1/de not_active Expired - Lifetime
- 1986-04-25 EP EP86105776A patent/EP0205826B1/en not_active Expired - Lifetime
- 1986-04-25 AT AT86105776T patent/ATE73663T1/de not_active IP Right Cessation
- 1986-04-25 ZA ZA863133A patent/ZA863133B/xx unknown
- 1986-04-25 JP JP61097811A patent/JPH0692307B2/ja not_active Expired - Lifetime
1996
- 1996-12-19 HK HK217296A patent/HK217296A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
GR861089B (en)	1986-08-26
CA1272956A (en)	1990-08-21
DK184186A (da)	1986-10-26
EP0205826A2 (en)	1986-12-30
ATE73663T1 (de)	1992-04-15
DE3684363D1 (de)	1992-04-23
CS263952B1 (en)	1989-05-12
ZA863133B (en)	1987-02-25
US4724233A (en)	1988-02-09
PH23112A (en)	1989-04-19
NZ215939A (en)	1988-09-29
PT82457B (pt)	1988-03-03
JPH0692307B2 (ja)	1994-11-16
AU5646886A (en)	1986-10-30
DK184186D0 (da)	1986-04-22
IL78553A (en)	1989-09-28
EP0205826B1 (en)	1992-03-18
JPS61275218A (ja)	1986-12-05
EG18436A (en)	1993-02-28
HK217296A (en)	1996-12-27
EP0205826A3 (en)	1989-05-10
IL78553A0 (en)	1986-08-31
PT82457A (en)	1986-05-01
AU586860B2 (en)	1989-07-27

Legal Events

Date	Code	Title	Description
1993-10-18	B1	Patent granted (law 1993)
2006-05-08	PUP	Patent expired

Publication	Publication Date	Title
DK167342B1 (da)	1993-10-18	Terapeutisk praeparat til behandling af virussygdomme samt anvendelse af et 9-(fosfonylmetoxyalkyl)adeninderivat til fremstilling af praeparatet
US6057305A (en)	2000-05-02	Antiretroviral enantiomeric nucleotide analogs
CA2479846C (en)	2007-07-24	Phosphonomethoxymethylpurine/pyrimidine derivatives
DK170646B1 (da)	1995-11-20	N-fosfonylmetoxyalkylderivater af pyrimidinbaser og purinbaser, fremgangsmåder til fremstilling heraf, samt lægemiddelpræparat med antiviral virkning indeholdende et sådant derivat
KR101840479B1 (ko)	2018-03-20	바이러스 감염 치료를 위한 ２＇―플루오로―６＇―메틸렌 카보사이클릭 뉴클레오사이드 및 방법
JP2866688B2 (ja)	1999-03-08	プリン誘導体を含有する抗ウィルス剤
DK148279B (da)	1985-05-28	Analogifremgangsmaade til fremstilling af 9-substituerede guaninderivater eller fysiologisk acceptable salte eller optiske isomerer deraf
HUT59152A (en)	1992-04-28	Process for producing cyclic analogs of nucleosides and pharmaceutical compositions comprising same as active ingredient
JPH0680061B2 (ja)	1994-10-12	新規なプリン誘導体
EP0138656B1 (en)	1989-09-27	Cyclic pyrophosphates of purine and pyrimidine acyclonucleosides, their preparation and their application in anti-viral compositions
Qiu et al.	1999	Synthesis and antiviral activity of phosphoralaninate derivatives of methylenecyclopropane analogues of nucleosides
PL207187B1 (pl)	2010-11-30	Pochodne 6-[2-(fosfonometoksy) alkoksy] pirymidyny, sposób ich wytwarzania, kompozycja farmaceutyczna zawierająca te pochodne oraz ich zastosowanie
GB2122198A (en)	1984-01-11	Antiviral guanine derivatives
US20110287111A1 (en)	2011-11-24	Substituted 6-(2-aminobenzylamino)purine derivatives, their use as medicaments and preparations containing these compounds
Valiaeva et al.	2011	Synthesis and antiviral evaluation of 9-(S)-[3-alkoxy-2-(phosphonomethoxy) propyl] nucleoside alkoxyalkyl esters: inhibitors of hepatitis C virus and HIV-1 replication
US6825348B2 (en)	2004-11-30	Antiviral compounds
HUT57764A (en)	1991-12-30	Process for producing substituted purines and antiviral agents comprising such compounds
Hocková et al.	2011	Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy) ethyl chain: Efficient synthesis and antiviral activity
HU190787B (en)	1986-11-28	Process for producing new guanine derivatives
EP3145939A1 (en)	2017-03-29	Phosphonate nucleosides useful in the treatment of viral diseases
CA2015671C (en)	2000-04-25	Phosphonomethoxytetrahydrofuranyl-purine/pyrimidine derivatives
CA1112571A (en)	1981-11-17	Therapeutic application of (s)- and (rs)-9-(2,3- dihydroxypropyl) adenine
AU646594B2 (en)	1994-02-24	Nucleoside analogs
CS248005B2 (cs)	1987-01-15	Způsob výroby derivátů 9-hydroxyethoxymethylguaninu