AU614082B2 - Nucleosides and nucleoside analogues, pharmaceutical composition and processes for the preparation of the compounds - Google Patents

Nucleosides and nucleoside analogues, pharmaceutical composition and processes for the preparation of the compounds Download PDF

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Publication number: AU614082B2
Authority: AU; Australia
Prior art keywords: formula; international; document; compound; compounds
Prior art date: 1987-04-16
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

Application number

AU16899/88A

Other languages

English (en)

Other versions

AU1689988A (en

Inventor

Roelf Datema

Karl Nils Gunnar Johansson

Zsuzanna Maria Ilona Kovacs

Bjorn Gunnar Lindborg

Bo Fredrik Oberg

Goran Bertil Stening

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.)

Medivir AB

Original Assignee

Medivir AB

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.)

1987-04-16

Filing date

1988-04-06

Publication date

1991-08-22

1988-04-06 Application filed by Medivir AB filed Critical Medivir AB

1988-11-04 Publication of AU1689988A publication Critical patent/AU1689988A/en

1991-08-22 Application granted granted Critical

1991-08-22 Publication of AU614082B2 publication Critical patent/AU614082B2/en

2008-04-06 Anticipated expiration legal-status Critical

Status Ceased legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 82
239000002777 nucleoside Substances 0.000 title claims description 25
238000000034 method Methods 0.000 title claims description 23
238000002360 preparation method Methods 0.000 title claims description 20
125000003835 nucleoside group Chemical group 0.000 title claims description 10
230000008569 process Effects 0.000 title claims description 4
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
229940127073 nucleoside analogue Drugs 0.000 title description 5
241000725303 Human immunodeficiency virus Species 0.000 claims abstract description 23
150000003839 salts Chemical class 0.000 claims abstract description 18
238000011282 treatment Methods 0.000 claims abstract description 12
238000002560 therapeutic procedure Methods 0.000 claims abstract description 5
241000282414 Homo sapiens Species 0.000 claims description 11
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
150000003833 nucleoside derivatives Chemical class 0.000 claims description 10
241001430294 unidentified retrovirus Species 0.000 claims description 10
208000015181 infectious disease Diseases 0.000 claims description 8
241000700721 Hepatitis B virus Species 0.000 claims description 7
230000001225 therapeutic effect Effects 0.000 claims description 7
230000015572 biosynthetic process Effects 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 5
238000003786 synthesis reaction Methods 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 3
150000002338 glycosides Chemical class 0.000 claims description 3
238000011321 prophylaxis Methods 0.000 claims description 3
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
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150000001720 carbohydrates Chemical class 0.000 claims description 2
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UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 claims description 2
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JOZGNYDSEBIJDH-UHFFFAOYSA-N eniluracil Chemical compound O=C1NC=C(C#C)C(=O)N1 JOZGNYDSEBIJDH-UHFFFAOYSA-N 0.000 claims 1
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
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DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
229940045145 uridine Drugs 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229960000523 zalcitabine Drugs 0.000 description 1
229960002555 zidovudine Drugs 0.000 description 1
HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1

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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- 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
- 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

Landscapes

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

AU16899/88A 1987-04-16 1988-04-06 Nucleosides and nucleoside analogues, pharmaceutical composition and processes for the preparation of the compounds Ceased AU614082B2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
SE8701605A SE8701605D0 (sv)	1987-04-16	1987-04-16	Novel medicinal compounds
SE8701605		1987-04-16
CA000580141A CA1336088C (en)	1987-04-16	1988-10-14	1-(3'-substitued-2', 3'-dideoxy-d-ribofuranosyl) thymine and uracil

Publications (2)

Publication Number	Publication Date
AU1689988A AU1689988A (en)	1988-11-04
AU614082B2 true AU614082B2 (en)	1991-08-22

Family

ID=25672174

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU16899/88A Ceased AU614082B2 (en)	1987-04-16	1988-04-06	Nucleosides and nucleoside analogues, pharmaceutical composition and processes for the preparation of the compounds

Country Status (9)

Country	Link
JP (1)	JPH01503069A (de)
AT (1)	ATE115958T1 (de)
AU (1)	AU614082B2 (de)
CA (1)	CA1336088C (de)
DE (1)	DE3852531T2 (de)
DK (3)	DK168443B1 (de)
HU (1)	HU211547A9 (de)
SE (1)	SE8701605D0 (de)
WO (1)	WO1988008001A1 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU633065B2 (en) *	1989-04-06	1993-01-21	Bristol-Myers Squibb Company	3'-substituted methyl nucleosides as antiviral agents
AU635834B2 (en) *	1990-04-18	1993-04-01	Wellcome Foundation Limited, The	Antiviral compounds

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8629892D0 (en) *	1986-12-15	1987-01-28	Wellcome Found	Antiviral compounds
US5631370A (en) *	1988-01-20	1997-05-20	Regents Of The University Of Minnesota	Optically-active isomers of dideoxycarbocyclic nucleosides
US4950758A (en) *	1988-01-20	1990-08-21	Regents Of The University Of Minnesota	Optically-active isomers of dideoxycarbocyclic nucleosides
US5175292A (en) *	1988-01-20	1992-12-29	Regents Of The University Of Minnesota	Intermediates for the preparation of dideoxycarbocyclic nucleosides
DE68917479D1 (de) *	1988-02-24	1994-09-15	Inst Rech Chim Biolog	Derivate von deoxy-2'-uridin substituiert in der 5, 3' oder 5' stellung durch acylierte alpha-amino-gruppen, verfahren zur herstellung und arzneimittel daraus.
US7119202B1 (en)	1989-02-08	2006-10-10	Glaxo Wellcome Inc.	Substituted-1,3-oxathiolanes and substituted-1,3-dioxolanes with antiviral properties
US5157114A (en) *	1988-08-19	1992-10-20	Burroughs Wellcome Co.	2',3'-dideoxy-3'-fluoro-5-ethyngluridine
US5198539A (en) *	1988-08-19	1993-03-30	Burroughs Wellcome Co.	5'-esters of 2',3'-dideoxy-3'-fluoro-5-ethynyluridine
FR2648045B1 (fr) *	1989-06-13	1991-09-27	Centre Nat Rech Scient	Composes oligonucleotidiques anomeres alpha inhibant la replication des retrovirus
NZ234534A (en) *	1989-07-17	1994-12-22	Univ Birmingham	Pyrimidine 4'-thionucleoside derivatives and their preparation; intermediates therefor
ES2253732T3 (es) *	1989-09-15	2006-06-01	Southern Research Institute	2'-deoxi-4'-tioribonucleosidos como agentes antivirales y anticancerosos.
US5591722A (en) *	1989-09-15	1997-01-07	Southern Research Institute	2'-deoxy-4'-thioribonucleosides and their antiviral activity
US5827727A (en)	1990-02-01	1998-10-27	Emory University	Method of resolution of 1,3-oxathiolane nucleoside enantiomers
US5521163A (en) *	1990-07-13	1996-05-28	University Of Birmingham	Antiviral pyrimidine nucleosides and methods for using same
SE9003151D0 (sv) *	1990-10-02	1990-10-02	Medivir Ab	Nucleoside derivatives
US6369066B1 (en)	1990-11-13	2002-04-09	Biochem Pharma, Inc.	Substituted 1,3-oxathiolanes with antiviral properties
US5587480A (en) *	1990-11-13	1996-12-24	Biochem Pharma, Inc.	Substituted 1,3-oxathiolanes and substituted 1,3-dithiolanes with antiviral properties
EP0560794B1 (de) *	1990-11-13	1996-09-18	Biochem Pharma Inc	Substituierte 1,3-oxathiolane mit antiviralen eigenschaften
US6228860B1 (en)	1990-11-13	2001-05-08	Biochem Pharma Inc.	Substituted 1,3-oxathiolanes with antiviral properties
TW393513B (en) *	1991-11-26	2000-06-11	Isis Pharmaceuticals Inc	Enhanced triple-helix and double-helix formation with oligomers containing modified pyrimidines
AU3222793A (en) *	1991-11-26	1993-06-28	Gilead Sciences, Inc.	Enhanced triple-helix and double-helix formation with oligomers containing modified pyrimidines
US6235887B1 (en)	1991-11-26	2001-05-22	Isis Pharmaceuticals, Inc.	Enhanced triple-helix and double-helix formation directed by oligonucleotides containing modified pyrimidines
US20020120130A1 (en)	1993-09-10	2002-08-29	Gilles Gosselin	2' or 3' -deoxy and 2', 3' -dideoxy-beta-L-pentofuranonucleo-side compounds, method of preparation and application in therapy, especially as anti- viral agents
US5587362A (en) *	1994-01-28	1996-12-24	Univ. Of Ga Research Foundation	L-nucleosides
CA2190862A1 (en) *	1994-05-31	1995-12-07	Bo Oberg	Post exposure prevention of hiv
US5612319A (en) *	1994-05-31	1997-03-18	Medivir Ab	Postexposure prevention of HIV infection or seroconversion
US6391859B1 (en)	1995-01-27	2002-05-21	Emory University	[5-Carboxamido or 5-fluoro]-[2′,3′-unsaturated or 3′-modified]-pyrimidine nucleosides
US5703058A (en)	1995-01-27	1997-12-30	Emory University	Compositions containing 5-fluoro-2',3'-didehydro-2',3'-dideoxycytidine or a mono-, di-, or triphosphate thereof and a second antiviral agent
US5808040A (en) *	1995-01-30	1998-09-15	Yale University	L-nucleosides incorporated into polymeric structure for stabilization of oligonucleotides
EP0831852B1 (de)	1995-06-07	2006-11-29	Emory University	Nucleoside mit anti-hepatitis b virus wirksamkeit
US5869493A (en)	1996-02-16	1999-02-09	Medivir Ab	Acyclic nucleoside derivatives
US5753789A (en) *	1996-07-26	1998-05-19	Yale University	Oligonucleotides containing L-nucleosides
KR100719606B1 (ko)	1998-02-25	2007-05-17	에모리 유니버시티	2'-플루오로뉴클레오사이드
KR20090089922A (ko)	2000-10-18	2009-08-24	파마셋 인코포레이티드	바이러스 감염 및 비정상적인 세포 증식의 치료를 위한 변형된 뉴클레오시드
WO2008043704A1 (en)	2006-10-10	2008-04-17	Medivir Ab	Hcv nucleoside inhibitor
JP6270742B2 (ja) *	2013-01-10	2018-01-31	塩野義製薬株式会社	架橋型核酸誘導体の製造方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4247544A (en) *	1979-07-02	1981-01-27	The Regents Of The University Of California	C-5 Substituted uracil nucleosides
US4267171A (en) *	1979-07-02	1981-05-12	The Regents Of The University Of California	C-5 Substituted cytosine nucleosides
US4724232A (en) *	1985-03-16	1988-02-09	Burroughs Wellcome Co.	Treatment of human viral infections

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DD75084A (de) *
US3116282A (en) *	1960-04-27	1963-12-31	Upjohn Co	Pyrimidine nucleosides and process
FR2040177A1 (en) *	1969-01-31	1971-01-22	Robugen Gmbh	2-deoxyribosyl-uracil derivs
US3817982A (en) *	1971-12-29	1974-06-18	Syntex Inc	2{40 ,3{40 -unsaturated nucleosides and method of making
DE2918260A1 (de) *	1979-05-07	1980-11-27	Robugen Gmbh	Anwendung von 5-alkyl-2'-desoxyuridinen
DE2930904A1 (de) *	1979-07-30	1981-02-19	Kailash Kumar Dr Gauri	Verwendung von 5-alkyl-pyrimidinnucleosiden bei der bekaempfung von krebs
DE3002197A1 (de) *	1980-01-22	1981-07-23	Robugen Gmbh Pharmazeutische Fabrik Esslingen A.N., 7300 Esslingen	5-alkylsubstituierte pyrimidin-nukleoside, verfahren zu deren herstellung und daraus hergestellte virostatische und cytostatische mittel
DE3045375A1 (de) *	1980-12-02	1982-07-01	Robugen Gmbh Pharmazeutische Fabrik Esslingen A.N., 7300 Esslingen	Neue substituierte pyrimidin-nukleoside mit antiviraler wirkung, verfahren zu deren herstellung und daraus zubereitete arzneiformen
DE3229169A1 (de) *	1982-08-05	1984-02-09	Robugen GmbH Pharmazeutische Fabrik, 7300 Esslingen	Verwendung von 5-alkylpyrimidinnukleosiden und deren derivate als zytostatika
CA1285935C (en) *	1985-03-16	1991-07-09	Janet Lister Rideout	Therapeutic nucleosides
IL78158A (en) *	1985-03-16	1988-04-29	Wellcome Found	Pharmaceutical compositions containing 3'-azido-3'-deoxythymidine
ATE108794T1 (de) *	1985-05-15	1994-08-15	Wellcome Found	Therapeutische nucleoside und deren herstellung.
EP0217580A3 (de) *	1985-09-17	1990-11-07	The Wellcome Foundation Limited	Therapeutische Nukleoside

1987
- 1987-04-16 SE SE8701605A patent/SE8701605D0/xx unknown
1988
- 1988-04-06 JP JP63503532A patent/JPH01503069A/ja active Pending
- 1988-04-06 DE DE3852531T patent/DE3852531T2/de not_active Expired - Fee Related
- 1988-04-06 AT AT88903972T patent/ATE115958T1/de not_active IP Right Cessation
- 1988-04-06 AU AU16899/88A patent/AU614082B2/en not_active Ceased
- 1988-04-06 WO PCT/SE1988/000169 patent/WO1988008001A1/en not_active Ceased
- 1988-10-14 CA CA000580141A patent/CA1336088C/en not_active Expired - Fee Related
- 1988-12-15 DK DK696988A patent/DK168443B1/da not_active IP Right Cessation
1991
- 1991-06-07 DK DK108491A patent/DK108491A/da not_active Application Discontinuation
1994
- 1994-09-13 DK DK104994A patent/DK104994A/da not_active Application Discontinuation
1995
- 1995-05-12 HU HU95P/P00134P patent/HU211547A9/hu unknown

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4247544A (en) *	1979-07-02	1981-01-27	The Regents Of The University Of California	C-5 Substituted uracil nucleosides
US4267171A (en) *	1979-07-02	1981-05-12	The Regents Of The University Of California	C-5 Substituted cytosine nucleosides
US4724232A (en) *	1985-03-16	1988-02-09	Burroughs Wellcome Co.	Treatment of human viral infections

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU633065B2 (en) *	1989-04-06	1993-01-21	Bristol-Myers Squibb Company	3'-substituted methyl nucleosides as antiviral agents
AU635834B2 (en) *	1990-04-18	1993-04-01	Wellcome Foundation Limited, The	Antiviral compounds

Also Published As

Publication number	Publication date
DK104994A (da)	1994-09-13
DK168443B1 (da)	1994-03-28
CA1336088C (en)	1995-06-27
WO1988008001A1 (en)	1988-10-20
HU211547A9 (en)	1995-12-28
JPH01503069A (ja)	1989-10-19
ATE115958T1 (de)	1995-01-15
DK108491D0 (da)	1991-06-07
SE8701605D0 (sv)	1987-04-16
DE3852531T2 (de)	1995-08-10
DK696988D0 (da)	1988-12-15
DE3852531D1 (de)	1995-02-02
AU1689988A (en)	1988-11-04
DK108491A (da)	1991-06-07
DK696988A (da)	1989-01-31

Publication	Publication Date	Title
AU614082B2 (en)	1991-08-22	Nucleosides and nucleoside analogues, pharmaceutical composition and processes for the preparation of the compounds
US5952500A (en)	1999-09-14	Nucleoside derivatives
JP2851094B2 (ja)	1999-01-27	ピリミジン誘導体
AU615681B2 (en)	1991-10-10	Nucleoside derivatives useful in treating retroviral infections
US5830898A (en)	1998-11-03	Enantiomerically pure β-di-dioxolane-nucleosides with selective anti-hepatitis B virus activity
Secrist III et al.	1992	Synthesis and anti-HIV activity of 4'-thio-2', 3'-dideoxynucleosides
US5925643A (en)	1999-07-20	Enantiomerically pure β-D-dioxolane-nucleosides
WO1990001036A1 (en)	1990-02-08	Nucleoside derivatives
WO1990012023A1 (en)	1990-10-18	Antiviral compounds
WO1994004154A9 (en)	1994-05-26	ENANTIOMERICALLY PURE β-D-DIOXOLANE-NUCLEOSIDES
US5409906A (en)	1995-04-25	α nucleoside compounds and a method for treating HBV using said compounds
US5506215A (en)	1996-04-09	1-(3'-fluoro-2',3'-dideoxy-β-D-ribofuranosyl)-5-substituted pyrimidine nucleosides
EP0516186A2 (de)	1992-12-02	Nukleoside und Nukleosid-Analoge, pharmazeutische Zusammensetzung und Verfahren für die Herstellung der Bestandteile
EP0615975A1 (de)	1994-09-21	Nukleozide und Nukleozidanalogen, pharmazeutische Zusammensetzung und Verfahren zu ihrer Verwendung
Camara et al.	1999	Synthesis of L‐Analogues of 1‐(2′, 3′‐Dideoxy‐β‐D‐glycero‐pent‐2‐enofuranosyl) thymine
JPH02188A (ja)	1990-01-05	ヌクレオチド類縁体およびその製造法，ならびに抗ウイルス剤

AU614082B2 - Nucleosides and nucleoside analogues, pharmaceutical composition and processes for the preparation of the compounds - Google Patents

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Landscapes

Applications Claiming Priority (3)

Publications (2)

Family

ID=25672174

Family Applications (1)

Country Status (9)

Cited By (2)

Families Citing this family (36)

Citations (3)

Family Cites Families (13)

Patent Citations (3)

Cited By (2)

Also Published As

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