NO822807L - Fremgangsmaate ved fremstilling av 2-beta-d-ribofuranosylthiazol-4-carboxamid. - Google Patents
Fremgangsmaate ved fremstilling av 2-beta-d-ribofuranosylthiazol-4-carboxamid.Info
- Publication number
- NO822807L NO822807L NO822807A NO822807A NO822807L NO 822807 L NO822807 L NO 822807L NO 822807 A NO822807 A NO 822807A NO 822807 A NO822807 A NO 822807A NO 822807 L NO822807 L NO 822807L
- Authority
- NO
- Norway
- Prior art keywords
- product
- thioamide
- ethanol
- ribofuranosylthiazole
- carboxylic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- FVRDYQYEVDDKCR-DBRKOABJSA-N tiazofurine Chemical compound NC(=O)C1=CSC([C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)=N1 FVRDYQYEVDDKCR-DBRKOABJSA-N 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 239000000047 product Substances 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 3
- HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003729 cation exchange resin Substances 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000007112 amidation reaction Methods 0.000 claims description 2
- PRRZDZJYSJLDBS-UHFFFAOYSA-N 3-bromo-2-oxopropanoic acid Chemical compound OC(=O)C(=O)CBr PRRZDZJYSJLDBS-UHFFFAOYSA-N 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- VAZMWZPZBBMCQF-WCTZXXKLSA-N methyl 2-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C1=CSC([C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)=N1 VAZMWZPZBBMCQF-WCTZXXKLSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 6
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- JRRCGOOKGUSEFK-YRNFEDNZSA-N [(2r,3r,4r)-3,4-dibenzoyloxy-5-bromooxolan-2-yl]methyl benzoate Chemical compound C([C@H]1OC([C@@H]([C@@H]1OC(=O)C=1C=CC=CC=1)OC(=O)C=1C=CC=CC=1)Br)OC(=O)C1=CC=CC=C1 JRRCGOOKGUSEFK-YRNFEDNZSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 208000002606 Paramyxoviridae Infections Diseases 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- 239000002777 nucleoside Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- -1 thiazole nucleoside Chemical class 0.000 description 2
- 150000003557 thiazoles Chemical class 0.000 description 2
- 101100117236 Drosophila melanogaster speck gene Proteins 0.000 description 1
- 241000709661 Enterovirus Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000011210 chromatographic step Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- FQGYCXFLEQVDJQ-UHFFFAOYSA-N mercury dicyanide Chemical compound N#C[Hg]C#N FQGYCXFLEQVDJQ-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/294,368 US4451648A (en) | 1981-08-19 | 1981-08-19 | Process for the production of 2-β-D-ribofuranosylthiazole-4-carboxamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO822807L true NO822807L (no) | 1983-02-21 |
Family
ID=23133107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO822807A NO822807L (no) | 1981-08-19 | 1982-08-18 | Fremgangsmaate ved fremstilling av 2-beta-d-ribofuranosylthiazol-4-carboxamid. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4451648A (da) |
| EP (1) | EP0072977A1 (da) |
| JP (1) | JPS5841877A (da) |
| AU (1) | AU8742182A (da) |
| DK (1) | DK370582A (da) |
| NO (1) | NO822807L (da) |
| ZA (1) | ZA825858B (da) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU574866B2 (en) * | 1980-12-15 | 1988-07-14 | Viratek Inc. | 2-beta-d-ribofuranosylthiazole-4-carboxamide-5'-phosphate |
| AU5298096A (en) * | 1995-02-17 | 1996-09-11 | Icn Pharmaceuticals, Inc. | Procedures for obtaining ribo-c-nucleosides |
| YU67099A (sh) * | 1997-06-30 | 2002-06-19 | Icn Pharmaceuticals Inc. | Postupak za dobijanje tiazofurina i drugih c-nukleozida |
| AU2003261354A1 (en) * | 2002-08-02 | 2004-02-23 | The Regents Of The University Of California | New uses for inhibitors of inosine monophosphate dehydrogenase |
| EP2803357B1 (en) | 2004-06-25 | 2020-11-18 | The Johns-Hopkins University | Angiogenesis inhibitors |
| US20130344541A1 (en) | 2010-11-02 | 2013-12-26 | Codexis, Inc. | Compositions and methods for production of fermentable sugars |
| CA2815522C (en) | 2010-11-02 | 2020-03-24 | Codexis, Inc. | Improved myceliophthora thermophila strain having reduced cellobiose dehydrogenase i activity |
| CN102659856A (zh) * | 2012-04-10 | 2012-09-12 | 常州康丽制药有限公司 | 1-O-乙酰基-2，3，5-三-O-苯甲酰基-β-D-呋喃核糖的制备工艺 |
| EP3773579A4 (en) | 2018-03-26 | 2022-03-09 | Clear Creek Bio, Inc. | COMPOSITIONS AND METHODS FOR INHIBITING DIHYDROOROTATE DEHYDROGENASE |
| US12076315B2 (en) | 2020-03-20 | 2024-09-03 | Clear Creek Bio, Inc. | Stable polymorphic compositions of brequinar sodium and methods of use and manufacture thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US29835A (en) * | 1860-08-28 | Surveyor s instrument | ||
| US1684732A (en) * | 1926-10-30 | 1928-09-18 | Harrison William | Manufacture of carbohydrate derivatives |
| US3897415A (en) * | 1971-06-01 | 1975-07-29 | Icn Pharmaceuticals | 5-Substituted 1,2,4-triazole-3-carboxamido nucleosides and analogs thereof |
| US3927216A (en) * | 1971-06-01 | 1975-12-16 | Icn Pharmaceuticals | 1,2,4-Triazol E-3-carboxamides for inhibiting virus infections |
| US4211771A (en) * | 1971-06-01 | 1980-07-08 | Robins Ronald K | Treatment of human viral diseases with 1-B-D-ribofuranosyl-1,2,4-triazole-3-carboxamide |
| USRE29835E (en) | 1971-06-01 | 1978-11-14 | Icn Pharmaceuticals | 1,2,4-Triazole nucleosides |
| US3798209A (en) * | 1971-06-01 | 1974-03-19 | Icn Pharmaceuticals | 1,2,4-triazole nucleosides |
| US3976545A (en) * | 1973-03-12 | 1976-08-24 | Icn Pharmaceuticals, Inc. | 1,2,4-Triazol E-3-carboxamides as antiviral agents |
| US4138547A (en) * | 1977-12-22 | 1979-02-06 | Icn Pharmaceuticals, Inc. | Process for preparing 1,2,4-triazole nucleosides |
-
1981
- 1981-08-19 US US06/294,368 patent/US4451648A/en not_active Expired - Fee Related
-
1982
- 1982-08-12 EP EP82107309A patent/EP0072977A1/en not_active Withdrawn
- 1982-08-12 ZA ZA825858A patent/ZA825858B/xx unknown
- 1982-08-18 DK DK370582A patent/DK370582A/da not_active Application Discontinuation
- 1982-08-18 NO NO822807A patent/NO822807L/no unknown
- 1982-08-19 AU AU87421/82A patent/AU8742182A/en not_active Abandoned
- 1982-08-19 JP JP57144565A patent/JPS5841877A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK370582A (da) | 1983-02-20 |
| EP0072977A1 (en) | 1983-03-02 |
| ZA825858B (en) | 1983-06-29 |
| US4451648A (en) | 1984-05-29 |
| AU8742182A (en) | 1983-02-24 |
| JPS5841877A (ja) | 1983-03-11 |
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