DE2560551C2 - - Google Patents
Info
- Publication number
- DE2560551C2 DE2560551C2 DE2560551A DE2560551A DE2560551C2 DE 2560551 C2 DE2560551 C2 DE 2560551C2 DE 2560551 A DE2560551 A DE 2560551A DE 2560551 A DE2560551 A DE 2560551A DE 2560551 C2 DE2560551 C2 DE 2560551C2
- Authority
- DE
- Germany
- Prior art keywords
- solution
- compounds
- acyl group
- triazole
- virus
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000005518 carboxamido group Chemical group 0.000 claims description 3
- 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 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 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 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 description 12
- 230000000694 effects Effects 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
- 230000002155 anti-virotic effect Effects 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 241000700605 Viruses Species 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000840 anti-viral effect Effects 0.000 description 3
- HMFHBZSHGGEWLO-TXICZTDVSA-N beta-D-ribose Chemical group OC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-TXICZTDVSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- -1 Alkali metal salts Chemical class 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
- 241000700618 Vaccinia virus Species 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000002777 nucleoside Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 241000709661 Enterovirus Species 0.000 description 1
- 241000712431 Influenza A virus Species 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
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000006143 cell culture medium Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 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
- 238000001727 in vivo Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-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)
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 |
|---|---|
| DE2560551C2 true DE2560551C2 (enrdf_load_stackoverflow) | 1989-02-23 |
Family
ID=23794869
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752511828 Granted DE2511828A1 (de) | 1974-03-18 | 1975-03-18 | 1-(beta-d-ribofuranosyl)-1,2,4-triazolsaeureester |
| DE2560551A Expired DE2560551C2 (enrdf_load_stackoverflow) | 1974-03-18 | 1975-03-18 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752511828 Granted DE2511828A1 (de) | 1974-03-18 | 1975-03-18 | 1-(beta-d-ribofuranosyl)-1,2,4-triazolsaeureester |
Country Status (13)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9307043D0 (en) * | 1993-04-05 | 1993-05-26 | Norsk Hydro As | Chemical compounds |
| 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 |
| CA2346447C (en) * | 1998-10-16 | 2006-01-31 | Schering Corporation | Ribavirin-interferon alfa combination therapy for eradicating detectable hcv-rna in patients having chronic hepatitis c infection |
| WO2001081359A1 (en) | 2000-04-20 | 2001-11-01 | Schering Corporation | Ribavirin-interferon alfa combination therapy for eradicating detectable hcv-rna in patients having chronic hepatitis c infection |
| JPWO2009028573A1 (ja) | 2007-08-27 | 2010-12-09 | 国立大学法人名古屋大学 | 血液凝固障害におけるリバビリンの利用 |
| EP2198870A4 (en) | 2007-08-27 | 2011-08-03 | Univ Nagoya Nat Univ Corp | ACTIVATOR FOR BLOOD CREATION FACTOR VII PROMOTER AND ITS USE |
| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2220246A1 (de) * | 1971-06-01 | 1972-12-14 | International Chemical & Nuclear Corp , Pasadena, Calif (V St A ) | 1,2,4 Tnazol Nukleoside |
-
1975
- 1975-03-14 GB GB10724/75A patent/GB1482736A/en not_active Expired
- 1975-03-17 BE BE154411A patent/BE826776R/xx active
- 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
- 1975-03-18 JP JP50032822A patent/JPS50154253A/ja active Pending
- 1975-03-18 CA CA222,365A patent/CA1060004A/en not_active Expired
- 1975-03-18 NL NL7503214A patent/NL7503214A/xx not_active Application Discontinuation
- 1975-03-18 DE DE19752511828 patent/DE2511828A1/de active Granted
- 1975-03-18 ZA ZA00751662A patent/ZA751662B/xx unknown
- 1975-03-18 FR FR7508454A patent/FR2264552B1/fr not_active Expired
- 1975-03-18 DE DE2560551A patent/DE2560551C2/de not_active Expired
- 1975-03-18 YU YU657/75A patent/YU42137B/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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2220246A1 (de) * | 1971-06-01 | 1972-12-14 | International Chemical & Nuclear Corp , Pasadena, Calif (V St A ) | 1,2,4 Tnazol Nukleoside |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50154253A (enrdf_load_stackoverflow) | 1975-12-12 |
| SE7502995L (enrdf_load_stackoverflow) | 1975-09-19 |
| GB1482736A (en) | 1977-08-10 |
| NL7503214A (nl) | 1975-09-22 |
| AR224992A1 (es) | 1982-02-15 |
| BE826776R (fr) | 1975-07-16 |
| FR2264552A2 (enrdf_load_stackoverflow) | 1975-10-17 |
| AU7914575A (en) | 1976-09-23 |
| CA1060004A (en) | 1979-08-07 |
| DE2511828C2 (enrdf_load_stackoverflow) | 1991-01-17 |
| ES435689A2 (es) | 1977-10-16 |
| ZA751662B (en) | 1976-02-25 |
| YU42137B (en) | 1988-06-30 |
| YU9287A (en) | 1988-04-30 |
| YU65775A (en) | 1983-01-21 |
| DE2511828A1 (de) | 1975-10-02 |
| YU43291B (en) | 1989-06-30 |
| DK106375A (enrdf_load_stackoverflow) | 1975-09-19 |
| FR2264552B1 (enrdf_load_stackoverflow) | 1980-12-19 |
| BE903674Q (fr) | 1986-05-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| Q172 | Divided out of (supplement): |
Ref country code: DE Ref document number: 2511828 |
|
| 8110 | Request for examination paragraph 44 | ||
| 8181 | Inventor (new situation) |
Free format text: WITKOWSKI, JOSEPH THEODORE, LAGUNA NIGUEL, CALIF., US ROBINS, ROLAND KENITH, SANTA ANA, CALIF., US |
|
| AC | Divided out of |
Ref country code: DE Ref document number: 2511828 Format of ref document f/p: P |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| AC | Divided out of |
Ref country code: DE Ref document number: 2511828 Format of ref document f/p: P |