CA1060004A - Esters de derives acides de 1-(b-d-ribofuranosyl)-1,2,4-triazoles - Google Patents

Esters de derives acides de 1-(b-d-ribofuranosyl)-1,2,4-triazoles

Info

Publication number: CA1060004A
Authority: CA; Canada
Prior art keywords: triazole; ribofuranosyl; beta; acyl; carboxamide
Prior art date: 1974-03-18
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

Application number

CA222,365A

Other languages

English (en)

Inventor

Roland K. Robins

Joseph T. Witkowski

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.)

Bausch Health Americas Inc

Original Assignee

ICN Pharmaceuticals Inc

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.)

1974-03-18

Filing date

1975-03-18

Publication date

1979-08-07

1974-03-18 Priority claimed from US05/452,065 external-priority patent/US3984396A/en

1975-03-18 Application filed by ICN Pharmaceuticals Inc filed Critical ICN Pharmaceuticals Inc

1979-08-07 Application granted granted Critical

1979-08-07 Publication of CA1060004A publication Critical patent/CA1060004A/fr

Status Expired legal-status Critical Current

Links

239000002253 acid Substances 0.000 title claims abstract description 13
150000002148 esters Chemical class 0.000 title abstract 2
HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 title 2
HZCAHMRRMINHDJ-MVIOUDGNSA-N 1-(beta-D-ribofuranosyl)-1,2,4-triazole Natural products OC[C@H]1O[C@H]([C@@H](O)[C@@H]1O)n2cncn2 HZCAHMRRMINHDJ-MVIOUDGNSA-N 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 45
229910019142 PO4 Inorganic materials 0.000 claims abstract description 27
239000010452 phosphate Substances 0.000 claims abstract description 16
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 26
150000001875 compounds Chemical class 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
239000002777 nucleoside Substances 0.000 claims description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
125000004122 cyclic group Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 6
125000005518 carboxamido group Chemical group 0.000 claims description 6
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 6
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims description 5
229940005657 pyrophosphoric acid Drugs 0.000 claims description 5
-1 benzoyl halide Chemical class 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical class CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 3
238000003776 cleavage reaction Methods 0.000 claims description 3
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 3
230000007017 scission Effects 0.000 claims description 3
125000003147 glycosyl group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
150000004712 monophosphates Chemical group 0.000 claims description 2
239000000126 substance Substances 0.000 claims 11
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims 1
150000003857 carboxamides Chemical class 0.000 claims 1
230000000840 anti-viral effect Effects 0.000 abstract description 8
150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
239000000203 mixture Substances 0.000 description 16
235000021317 phosphate Nutrition 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
241000700605 Viruses Species 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
241000699670 Mus sp. Species 0.000 description 5
230000000875 corresponding effect Effects 0.000 description 5
238000005917 acylation reaction Methods 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
238000001914 filtration Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000001266 acyl halides Chemical class 0.000 description 2
230000010933 acylation Effects 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
150000003833 nucleoside derivatives Chemical class 0.000 description 2
125000003835 nucleoside group Chemical group 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000005723 virus inoculator Substances 0.000 description 2
ZEWJFUNFEABPGL-UHFFFAOYSA-N 1,2,4-triazole-3-carboxamide Chemical compound NC(=O)C=1N=CNN=1 ZEWJFUNFEABPGL-UHFFFAOYSA-N 0.000 description 1
SJCDBQHCQSIZHN-UHFFFAOYSA-N 1,2-dihydrotriazole-3-carboxamide Chemical compound NC(=O)N1NNC=C1 SJCDBQHCQSIZHN-UHFFFAOYSA-N 0.000 description 1
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
241000709661 Enterovirus Species 0.000 description 1
241000712431 Influenza A virus Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
208000002606 Paramyxoviridae Infections Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241000700584 Simplexvirus Species 0.000 description 1
241000700618 Vaccinia virus Species 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
239000006143 cell culture medium Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000020176 deacylation Effects 0.000 description 1
238000005947 deacylation reaction Methods 0.000 description 1
230000034994 death Effects 0.000 description 1
231100000517 death Toxicity 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000010828 elution Methods 0.000 description 1
229940093499 ethyl acetate Drugs 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
AFQIYTIJXGTIEY-UHFFFAOYSA-N hydrogen carbonate;triethylazanium Chemical compound OC(O)=O.CCN(CC)CC AFQIYTIJXGTIEY-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
206010022000 influenza Diseases 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- 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
- C07H19/056—Triazole or tetrazole radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA222,365A 1974-03-18 1975-03-18 Esters de derives acides de 1-(b-d-ribofuranosyl)-1,2,4-triazoles Expired CA1060004A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/452,065 US3984396A (en)	1971-06-01	1974-03-18	1-(β,-D-ribofuranosyl)-1,2,4-triazole acid esters

Publications (1)

Publication Number	Publication Date
CA1060004A true CA1060004A (fr)	1979-08-07

Family

ID=23794869

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA222,365A Expired CA1060004A (fr)	1974-03-18	1975-03-18	Esters de derives acides de 1-(b-d-ribofuranosyl)-1,2,4-triazoles

Country Status (13)

Country	Link
JP (1)	JPS50154253A (fr)
AR (1)	AR224992A1 (fr)
BE (2)	BE826776R (fr)
CA (1)	CA1060004A (fr)
DE (2)	DE2511828A1 (fr)
DK (1)	DK106375A (fr)
ES (1)	ES435689A2 (fr)
FR (1)	FR2264552B1 (fr)
GB (1)	GB1482736A (fr)
NL (1)	NL7503214A (fr)
SE (1)	SE7502995L (fr)
YU (2)	YU42137B (fr)
ZA (1)	ZA751662B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9307043D0 (en) *	1993-04-05	1993-05-26	Norsk Hydro As	Chemical compounds
TR200101085T2 (tr) *	1998-10-16	2001-08-21	Schering Corporation	Kronik hepatit C enfeksiyonlu hastalarda algılanabilir HCV-RNA'nın yok edilmesi için birleşik ribavirin-interferon alfa tedavisi
US6277830B1 (en)	1998-10-16	2001-08-21	Schering Corporation	5′-amino acid esters of ribavirin and the use of same to treat hepatitis C with interferon
AU2001255495A1 (en)	2000-04-20	2001-11-07	Schering Corporation	Ribavirin-interferon alfa combination therapy for eradicating detectable hcv-rnain patients having chronic hepatitis c infection
WO2009028573A1 (fr)	2007-08-27	2009-03-05	National University Corporation Nagoya University	Utilisation de la ribavirine dans un trouble de la coagulation du sang
EP2198870A4 (fr)	2007-08-27	2011-08-03	Univ Nagoya Nat Univ Corp	Activateur pour le promoteur du facteur vii de la coagulation du sang et son utilisation
CN111205344B (zh) *	2020-01-14	2023-03-14	华东理工大学	一种用于甲醇溶剂识别的纯有机磷光小分子材料及其制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3798209A (en) *	1971-06-01	1974-03-19	Icn Pharmaceuticals	1,2,4-triazole nucleosides

1975
- 1975-03-14 GB GB10724/75A patent/GB1482736A/en not_active Expired
- 1975-03-17 ES ES435689A patent/ES435689A2/es not_active Expired
- 1975-03-17 SE SE7502995A patent/SE7502995L/xx unknown
- 1975-03-17 DK DK106375A patent/DK106375A/da unknown
- 1975-03-17 BE BE154411A patent/BE826776R/fr active
- 1975-03-18 CA CA222,365A patent/CA1060004A/fr not_active Expired
- 1975-03-18 JP JP50032822A patent/JPS50154253A/ja active Pending
- 1975-03-18 DE DE19752511828 patent/DE2511828A1/de active Granted
- 1975-03-18 DE DE2560551A patent/DE2560551C2/de not_active Expired
- 1975-03-18 YU YU657/75A patent/YU42137B/xx unknown
- 1975-03-18 NL NL7503214A patent/NL7503214A/xx not_active Application Discontinuation
- 1975-03-18 FR FR7508454A patent/FR2264552B1/fr not_active Expired
- 1975-03-18 ZA ZA00751662A patent/ZA751662B/xx unknown
1979
- 1979-03-18 AR AR258018A patent/AR224992A1/es active
1985
- 1985-11-19 BE BE0/215890A patent/BE903674Q/fr not_active IP Right Cessation
1987
- 1987-01-23 YU YU92/87A patent/YU43291B/xx unknown

Also Published As

Publication number	Publication date
AR224992A1 (es)	1982-02-15
DK106375A (fr)	1975-09-19
FR2264552B1 (fr)	1980-12-19
AU7914575A (en)	1976-09-23
NL7503214A (nl)	1975-09-22
YU9287A (en)	1988-04-30
BE903674Q (fr)	1986-05-20
DE2511828C2 (fr)	1991-01-17
FR2264552A2 (fr)	1975-10-17
YU43291B (en)	1989-06-30
ES435689A2 (es)	1977-10-16
BE826776R (fr)	1975-07-16
ZA751662B (en)	1976-02-25
YU65775A (en)	1983-01-21
JPS50154253A (fr)	1975-12-12
YU42137B (en)	1988-06-30
GB1482736A (en)	1977-08-10
DE2511828A1 (de)	1975-10-02
SE7502995L (fr)	1975-09-19
DE2560551C2 (fr)	1989-02-23

Publication	Publication Date	Title
USRE29835E (en)	1978-11-14	1,2,4-Triazole nucleosides
US3798209A (en)	1974-03-19	1,2,4-triazole nucleosides
US3984396A (en)	1976-10-05	1-(β,-D-ribofuranosyl)-1,2,4-triazole acid esters
EP0587364B1 (fr)	1996-06-05	Procédé pour l'anomérisation des nucléosides
CA1336820C (fr)	1995-08-29	Nucleosides fluores et methode correspondante de traitement des infections par un retrovirus
JP4118958B2 (ja)	2008-07-16	テトラホスホネート二環式トリス無水物
CA2502109C (fr)	2010-02-23	Derive de 2-haloadenosine avec substitution sur le carbone en position 4'
Fox et al.	1961	Nucleosides. XII. Direct Synthesis of 2'-Deoxycytidine and its α-Anomer1, 2
Chambers et al.	1958	Nucleoside Polyphosphates. VII. 1 The Use of Phosphoramidic Acids in the Synthesis of Nucleoside-5'Pyrophosphates
Cushley et al.	1967	Nucleosides. XXXVIII. Proton magnetic resonance studies of acetylated nucleosides
CA1060004A (fr)	1979-08-07	Esters de derives acides de 1-(b-d-ribofuranosyl)-1,2,4-triazoles
US3300478A (en)	1967-01-24	Arabinofuranosyl 2', 5'-and 3'-5'-dinucleoside phosphates and process therefor
CA2442979C (fr)	2010-02-16	Procede de preparation de 2'-halo beta l-arabinofuranosyl nucleosides
US5530110A (en)	1996-06-25	4-ethoxy-5-fluoro-2'-deoxyuridine
US5153180A (en)	1992-10-06	Fluorinated nucleosides and process for treating retrovirus infections therewith
US3317512A (en)	1967-05-02	5', 5'-dinucleoside phosphates
KR880000094B1 (ko)	1988-02-23	뉴클레오시드 유도체의 제조방법
US3558595A (en)	1971-01-26	2'-cyclic esters and 5'-cyclic esters of 3'-deoxy - 3' - dihydroxyphosphinylmethyl - beta - d - ribofuranosylnucleoside derivatives and intermediates therefor
EP0360018B1 (fr)	1994-07-27	2'-Méthylidènepyrimidine nucléosides, leur utilisation et méthodes pour leur préparation
Brown et al.	1954	Nucleotides. Part XXVII. The structures of adenylic acids a and b
Alexandrova	2011	4′-C-nucleoside derivatives: Synthesis and antiviral properties
Watanabe et al.	1966	Nucleosides. XXXI. 3'-Amino-3'-deoxyhexopyranosyl Nucleosides. IV. Nucleoside Conversions in the 3'-Aminohexose Series1
EP0445258B1 (fr)	1994-03-30	5'-alkylphosphonylnucleosides comme agents antiviraux
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