CA1336088C - 1-(3'-substitued-2', 3'-dideoxy-d-ribofuranosyl) thymine and uracil - Google Patents

1-(3'-substitued-2', 3'-dideoxy-d-ribofuranosyl) thymine and uracil

Info

Publication number: CA1336088C
Authority: CA; Canada
Prior art keywords: compound; formula; anomer; compound according; virus
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.): Expired - Fee Related

Application number

CA000580141A

Other languages

English (en)

French (fr)

Inventor

Roelf Dateman

Zsuzsanna M.I. Kovacs

Bjorn Gunnar Lindborg

Goran Bertil Stening

Karl Nils Gunnar Johansson

Bo Fredrik Oberg

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

1988-10-14

Publication date

1995-06-27

1987-04-16 Priority to SE8701605A priority Critical patent/SE8701605D0/xx

1988-04-06 Priority to EP19920112530 priority patent/EP0516186A3/en

1988-04-06 Priority to AU16899/88A priority patent/AU614082B2/en

1988-04-06 Priority to EP94108798A priority patent/EP0615975A1/de

1988-04-06 Priority to PCT/SE1988/000169 priority patent/WO1988008001A1/en

1988-04-06 Priority to JP63503532A priority patent/JPH01503069A/ja

1988-04-06 Priority to AT88903972T priority patent/ATE115958T1/de

1988-04-06 Priority to EP88903972A priority patent/EP0309560B1/de

1988-04-06 Priority to DE3852531T priority patent/DE3852531T2/de

1988-10-14 Priority to CA000580141A priority patent/CA1336088C/en

1988-10-14 Application filed by Medivir AB filed Critical Medivir AB

1988-12-15 Priority to DK696988A priority patent/DK168443B1/da

1991-06-07 Priority to DK911084A priority patent/DK108491D0/da

1991-11-20 Priority to US07/794,704 priority patent/US5215970A/en

1993-04-01 Priority to US08/041,165 priority patent/US5409906A/en

1994-09-13 Priority to DK104994A priority patent/DK104994A/da

1995-05-12 Priority to HU95P/P00134P priority patent/HU211547A9/hu

1995-06-27 Application granted granted Critical

1995-06-27 Publication of CA1336088C publication Critical patent/CA1336088C/en

2012-06-27 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 title claims description 6
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 title description 8
229940113082 thymine Drugs 0.000 title description 4
229940035893 uracil Drugs 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 68
241000725303 Human immunodeficiency virus Species 0.000 claims abstract description 25
150000003839 salts Chemical class 0.000 claims abstract description 14
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 11
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract description 9
150000003254 radicals Chemical class 0.000 claims abstract description 9
238000011282 treatment Methods 0.000 claims abstract description 9
-1 hydroxymetyl function Chemical group 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 4
125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 claims abstract description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract 2
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QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 7
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
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125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
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KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 2
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical group NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
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125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims description 2
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
238000012360 testing method Methods 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
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XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
RKVXJCQNTSYKJO-AEJSXWLSSA-N 1-[(2s,4s,5r)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-5-propylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(CCC)=CN1[C@H]1O[C@H](CO)[C@@H](F)C1 RKVXJCQNTSYKJO-AEJSXWLSSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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SSFQGWVTTOGGKN-YIZRAAEISA-N 5-ethyl-1-[(2s,4s,5r)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(CC)=CN1[C@H]1O[C@H](CO)[C@@H](F)C1 SSFQGWVTTOGGKN-YIZRAAEISA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
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UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
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JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
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TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 2
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 2
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WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 2
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WVXRAFOPTSTNLL-NKWVEPMBSA-N 2',3'-dideoxyadenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 WVXRAFOPTSTNLL-NKWVEPMBSA-N 0.000 description 1
WEEMDRWIKYCTQM-UHFFFAOYSA-N 2,6-dimethoxybenzenecarbothioamide Chemical compound COC1=CC=CC(OC)=C1C(N)=S WEEMDRWIKYCTQM-UHFFFAOYSA-N 0.000 description 1
OKQHSIGMOWQUIK-UHFFFAOYSA-N 2-[(2-aminopurin-9-yl)methoxy]ethanol Chemical compound NC1=NC=C2N=CN(COCCO)C2=N1 OKQHSIGMOWQUIK-UHFFFAOYSA-N 0.000 description 1
RHIULBJJKFDJPR-UHFFFAOYSA-N 5-ethyl-1h-pyrimidine-2,4-dione Chemical compound CCC1=CNC(=O)NC1=O RHIULBJJKFDJPR-UHFFFAOYSA-N 0.000 description 1
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125000003729 nucleotide group Chemical group 0.000 description 1
125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 1
125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
239000008188 pellet Substances 0.000 description 1
ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229960002385 streptomycin sulfate Drugs 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
235000011044 succinic acid Nutrition 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
LCJVIYPJPCBWKS-NXPQJCNCSA-N thymosin Chemical compound SC[C@@H](N)C(=O)N[C@H](CO)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CO)C(=O)N[C@H](CO)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@H](CCC(O)=O)C(O)=O LCJVIYPJPCBWKS-NXPQJCNCSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
241001529453 unidentified herpesvirus Species 0.000 description 1
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
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)
Biotechnology (AREA)
General Chemical & Material Sciences (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Genetics & Genomics (AREA)
Virology (AREA)
Epidemiology (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)

CA000580141A 1987-04-16 1988-10-14 1-(3'-substitued-2', 3'-dideoxy-d-ribofuranosyl) thymine and uracil Expired - Fee Related CA1336088C (en)

Priority Applications (16)

Application Number	Priority Date	Filing Date	Title
SE8701605A SE8701605D0 (sv)	1987-04-16	1987-04-16	Novel medicinal compounds
AU16899/88A AU614082B2 (en)	1987-04-16	1988-04-06	Nucleosides and nucleoside analogues, pharmaceutical composition and processes for the preparation of the compounds
EP94108798A EP0615975A1 (de)	1987-04-16	1988-04-06	Nukleozide und Nukleozidanalogen, pharmazeutische Zusammensetzung und Verfahren zu ihrer Verwendung
PCT/SE1988/000169 WO1988008001A1 (en)	1987-04-16	1988-04-06	Nucleosides and nucleoside analogues, pharmaceutical composition and processes for the preparation of the compounds
JP63503532A JPH01503069A (ja)	1987-04-16	1988-04-06	新規な医薬化合物
AT88903972T ATE115958T1 (de)	1987-04-16	1988-04-06	Nukleoside und nukleosid-analoge, pharmazeutische zusammensetzung und verfahren für die herstellung der bestandteile.
EP88903972A EP0309560B1 (de)	1987-04-16	1988-04-06	Nukleoside und nukleosid-analoge, pharmazeutische zusammensetzung und verfahren für die herstellung der bestandteile
DE3852531T DE3852531T2 (de)	1987-04-16	1988-04-06	Nukleoside und nukleosid-analoge, pharmazeutische zusammensetzung und verfahren für die herstellung der bestandteile.
EP19920112530 EP0516186A3 (en)	1987-04-16	1988-04-06	Nucleosides and nucleoside analogues, pharmaceutical composition and processes for the preparation of the compounds
CA000580141A CA1336088C (en)	1987-04-16	1988-10-14	1-(3'-substitued-2', 3'-dideoxy-d-ribofuranosyl) thymine and uracil
DK696988A DK168443B1 (da)	1987-04-16	1988-12-15	Pyrimid-2-on-1-yl-forbindelser, farmaceutiske præparater indeholdende disse forbindelser og fremgangsmåde til fremstilling af forbindelserne
DK911084A DK108491D0 (da)	1987-04-16	1991-06-07	Nucleosider og nucleosidanaloge samt farmaceutiske praeparater indeholdende disse forbindelser
US07/794,704 US5215970A (en)	1987-04-16	1991-11-20	Nucleosides and nucleotide analogues, pharmaceutical composition and processes for the preparation of the compounds
US08/041,165 US5409906A (en)	1987-04-16	1993-04-01	α nucleoside compounds and a method for treating HBV using said compounds
DK104994A DK104994A (da)	1987-04-16	1994-09-13	Anvendelse af beta-anomere forbindelser til fremstilling af farmaceutiske præparater til behandling eller forebyggelse af HIV eller hepatitis B Virus
HU95P/P00134P HU211547A9 (en)	1987-04-16	1995-05-12	Nucleosides and nucleoside analogues, pharmaceutical composition and processes for the preparation of the compounds

Applications Claiming Priority (2)

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

Publications (1)

Publication Number	Publication Date
CA1336088C true CA1336088C (en)	1995-06-27

Family

ID=25672174

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000580141A Expired - Fee Related CA1336088C (en)	1987-04-16	1988-10-14	1-(3'-substitued-2', 3'-dideoxy-d-ribofuranosyl) thymine and uracil

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)

Families Citing this family (38)

* 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
US5175292A (en) *	1988-01-20	1992-12-29	Regents Of The University Of Minnesota	Intermediates for the preparation of dideoxycarbocyclic nucleosides
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
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
FI95384C (fi) *	1989-04-06	1996-01-25	Squibb Bristol Myers Co	Menetelmä 3'-deoksi-3'-substituoitujen metyylinukleosidien valmistamiseksi ja menetelmässä käytettäviä välituotteita
FR2648045B1 (fr) *	1989-06-13	1991-09-27	Centre Nat Rech Scient	Composes oligonucleotidiques anomeres alpha inhibant la replication des retrovirus
IE902574A1 (en) *	1989-07-17	1991-02-27	Univ Birmingham	Antiviral pyrimidine nucleosides
US5591722A (en) *	1989-09-15	1997-01-07	Southern Research Institute	2'-deoxy-4'-thioribonucleosides and their antiviral activity
AU6401490A (en) *	1989-09-15	1991-04-18	Southern Research Institute	2'-deoxy-4'-thioribonucleosides as antiviral and anticancer agents
US5728575A (en)	1990-02-01	1998-03-17	Emory University	Method of resolution of 1,3-oxathiolane nucleoside enantiomers
GB9008696D0 (en) *	1990-04-18	1990-06-13	Wellcome Found	Anti-viral compounds
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
US6228860B1 (en)	1990-11-13	2001-05-08	Biochem Pharma Inc.	Substituted 1,3-oxathiolanes with antiviral properties
EP0560794B1 (de) *	1990-11-13	1996-09-18	Biochem Pharma Inc	Substituierte 1,3-oxathiolane mit antiviralen eigenschaften
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
TW393513B (en) *	1991-11-26	2000-06-11	Isis Pharmaceuticals Inc	Enhanced triple-helix and double-helix formation with oligomers 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
EP0763048A1 (de) *	1994-05-31	1997-03-19	Medivir Aktiebolag	Hiv-infektionsverhütung nach kontakt mit dem virus
US5612319A (en) *	1994-05-31	1997-03-18	Medivir Ab	Postexposure prevention of HIV infection or seroconversion
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
US6391859B1 (en)	1995-01-27	2002-05-21	Emory University	[5-Carboxamido or 5-fluoro]-[2′,3′-unsaturated or 3′-modified]-pyrimidine nucleosides
US5808040A (en) *	1995-01-30	1998-09-15	Yale University	L-nucleosides incorporated into polymeric structure for stabilization of oligonucleotides
CA2219132C (en)	1995-06-07	2007-03-06	Emory University	Nucleosides with anti-hepatitis b virus activity
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
EP2392580A1 (de)	1998-02-25	2011-12-07	Emory University	2'-Fluornucleoside
CN101862345B (zh)	2000-10-18	2014-06-04	吉利德制药有限责任公司	用于治疗病毒感染和异常细胞增殖的修饰核苷类化合物
CN101573370B (zh)	2006-10-10	2013-09-11	美迪维尔公司	Hcv核苷类抑制剂
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

Family Cites Families (16)

* 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
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
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
ATE135011T1 (de) *	1985-03-16	1996-03-15	Wellcome Found	Therapeutische nukleoside
DK164392C (da) *	1985-03-16	1992-11-09	Wellcome Found	Anvendelse af 3'-azido-3'-desoxythymidin til fremstilling af et laegemiddel til behandling af eller profylakse for en human retrovirusinfektion
US4724232A (en) *	1985-03-16	1988-02-09	Burroughs Wellcome Co.	Treatment of human viral infections
DE3689976T2 (de) *	1985-05-15	1995-03-16	Wellcome Found	Therapeutische Nucleoside und deren Herstellung.
ATE190064T1 (de) *	1985-09-17	2000-03-15	Wellcome Found	Kombination therapeutische nukleoside mit weiteren therapeutisch wirksamen komponenten.

1987
- 1987-04-16 SE SE8701605A patent/SE8701605D0/xx unknown
1988
- 1988-04-06 AU AU16899/88A patent/AU614082B2/en not_active Ceased
- 1988-04-06 AT AT88903972T patent/ATE115958T1/de not_active IP Right Cessation
- 1988-04-06 WO PCT/SE1988/000169 patent/WO1988008001A1/en not_active Ceased
- 1988-04-06 JP JP63503532A patent/JPH01503069A/ja active Pending
- 1988-04-06 DE DE3852531T patent/DE3852531T2/de not_active Expired - Fee Related
- 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 DK911084A patent/DK108491D0/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

Also Published As

Publication number	Publication date
DE3852531T2 (de)	1995-08-10
JPH01503069A (ja)	1989-10-19
WO1988008001A1 (en)	1988-10-20
AU1689988A (en)	1988-11-04
DK108491A (da)	1991-06-07
DK696988D0 (da)	1988-12-15
DK168443B1 (da)	1994-03-28
DK108491D0 (da)	1991-06-07
DK696988A (da)	1989-01-31
HU211547A9 (en)	1995-12-28
AU614082B2 (en)	1991-08-22
ATE115958T1 (de)	1995-01-15
DK104994A (da)	1994-09-13
SE8701605D0 (sv)	1987-04-16
DE3852531D1 (de)	1995-02-02

Legal Events

Date	Code	Title	Description
2001-06-27	MKLA	Lapsed

Publication	Publication Date	Title
CA1336088C (en)	1995-06-27	1-(3'-substitued-2', 3'-dideoxy-d-ribofuranosyl) thymine and uracil
EP0322384B1 (de)	1996-03-13	Nucleoside zur Verwendung für die Therapie
CA1336820C (en)	1995-08-29	Fluorinated nucleosides and process for treating retrovirus infections therewith
EP0352248A1 (de)	1990-01-24	Nucleosidderivate
US5952500A (en)	1999-09-14	Nucleoside derivatives
JP4980059B2 (ja)	2012-07-18	抗ウイルスヌクレオシド類似体およびウイルス感染特にｈｉｖ感染の処置方法
JP2851094B2 (ja)	1999-01-27	ピリミジン誘導体
JPS63290895A (ja)	1988-11-28	抗ウイルスヌクレオシド
US5215971A (en)	1993-06-01	Antiviral pharmaceutical composition comprising 5-substituted pyrimidine nucleosides
US5215970A (en)	1993-06-01	Nucleosides and nucleotide analogues, pharmaceutical composition and processes for the preparation of the compounds
US4710492A (en)	1987-12-01	3'-azido-2',3'-dideoxy-5-halouridine and its use in treating patients infected with retroviruses
EP0294443B1 (de)	1992-07-29	Verwendung von nukleosiden zur herstellung eines medikamentes zur behandlung von krankheiten, die durch einen retrovirus oder den hepatitis-b-virus verursacht werden
JPH07145058A (ja)	1995-06-06	レトロウイルスに感染した患者を治療するための２’，３’−ジデオキシシチジン−２’−エン（２’，３’−ジデオキシ−２’，３’−ジデヒドロシチジン）の製造方法
US5153180A (en)	1992-10-06	Fluorinated nucleosides and process for treating retrovirus infections therewith
JPH02108695A (ja)	1990-04-20	治療用ヌクレオシド
WO1991019727A1 (en)	1991-12-26	5'-hydrogenphosphonates and 5'-methylphosphonates of sugar modified nucleosides, compositions and uses thereof
EP0516186A2 (de)	1992-12-02	Nukleoside und Nukleosid-Analoge, pharmazeutische Zusammensetzung und Verfahren für die Herstellung der Bestandteile
EP0309560B1 (de)	1994-12-21	Nukleoside und nukleosid-analoge, pharmazeutische zusammensetzung und verfahren für die herstellung der bestandteile
JP2926257B2 (ja)	1999-07-28	抗ウイルス性で高い水溶性を持ち且つ安定な結晶性２′，３′‐ジデオキシイノシン・モノ水和物塩、２′，３′‐ジデオキシ‐２′，３′‐ジデヒドロチミジン・モノ水和物塩及び２′，３′‐ジデオキシ‐２′‐フルオロイノシン・ヘミ水和物塩
US5086044A (en)	1992-02-04	Treatment of human viral infections
IE67037B1 (en)	1996-02-21	Novel medicinal compounds
EP0365556A1 (de)	1990-05-02	Nucleosid-analoge.
EP0332626A1 (de)	1989-09-20	Zubereitungen zur behandlung viraler infektionen bei menschen
WO1993017035A1 (en)	1993-09-02	2'ISODIDEOXY-β-D-NUCLEOSIDES AS STABLE ANTIVIRAL AGENTS
JPH04173787A (ja)	1992-06-22	新規抗ウイルス剤及びその製造方法