CA1150247A - (e)-5-(2-halogenovinyl)-arabinofuranosyluracil, process for preparation thereof, and uses thereof - Google Patents
(e)-5-(2-halogenovinyl)-arabinofuranosyluracil, process for preparation thereof, and uses thereofInfo
- Publication number
- CA1150247A CA1150247A CA000367108A CA367108A CA1150247A CA 1150247 A CA1150247 A CA 1150247A CA 000367108 A CA000367108 A CA 000367108A CA 367108 A CA367108 A CA 367108A CA 1150247 A CA1150247 A CA 1150247A
- Authority
- CA
- Canada
- Prior art keywords
- halogen
- arau
- compound
- halogenovinyl
- 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
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 25
- 150000002367 halogens Chemical class 0.000 claims abstract description 25
- ZUUCNUCXJJOBAT-RNQHSHRISA-N 5-[(3S,4S,5R)-3,4-dihydroxy-5-(1-hydroxyprop-2-enyl)oxolan-2-yl]-1H-pyrimidine-2,4-dione Chemical compound C(=C)C([C@@H]1[C@H]([C@@H](C(O1)C=1C(NC(NC=1)=O)=O)O)O)O ZUUCNUCXJJOBAT-RNQHSHRISA-N 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 241000700605 Viruses Species 0.000 abstract description 13
- 230000003172 anti-dna Effects 0.000 abstract description 9
- 230000003602 anti-herpes Effects 0.000 abstract description 2
- 208000007514 Herpes zoster Diseases 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 230000002155 anti-virotic effect Effects 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 8
- GCQYYIHYQMVWLT-HQNLTJAPSA-N Sorivudine Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(\C=C\Br)=C1 GCQYYIHYQMVWLT-HQNLTJAPSA-N 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- OIRDTQYFTABQOQ-UHTZMRCNSA-N Vidarabine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O OIRDTQYFTABQOQ-UHTZMRCNSA-N 0.000 description 6
- 230000004663 cell proliferation Effects 0.000 description 6
- 230000035755 proliferation Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- OIRDTQYFTABQOQ-UHFFFAOYSA-N ara-adenosine Natural products Nc1ncnc2n(cnc12)C1OC(CO)C(O)C1O OIRDTQYFTABQOQ-UHFFFAOYSA-N 0.000 description 5
- 101150035354 araA gene Proteins 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 241000450599 DNA viruses Species 0.000 description 4
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 230000001766 physiological effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000701085 Human alphaherpesvirus 3 Species 0.000 description 3
- 239000003443 antiviral agent Substances 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 239000012433 hydrogen halide Substances 0.000 description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 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
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 108010011356 Nucleoside phosphotransferase Proteins 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 241001529453 unidentified herpesvirus Species 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 1
- ODZBBRURCPAEIQ-DJLDLDEBSA-N Brivudine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(C=CBr)=C1 ODZBBRURCPAEIQ-DJLDLDEBSA-N 0.000 description 1
- 208000004449 DNA Virus Infections Diseases 0.000 description 1
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 description 1
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 1
- 239000006145 Eagle's minimal essential medium Substances 0.000 description 1
- 206010048461 Genital infection Diseases 0.000 description 1
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 1
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 210000000795 conjunctiva Anatomy 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000120 cytopathologic effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000035407 negative regulation of cell proliferation Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000036515 potency Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical class OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 208000010531 varicella zoster infection Diseases 0.000 description 1
- -1 vinyl IDU Chemical compound 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16402579A JPS5687599A (en) | 1979-12-19 | 1979-12-19 | E 55 22halogenovinyl arabinofuranosyluracil and its preparation |
| JP164025/1979 | 1979-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1150247A true CA1150247A (en) | 1983-07-19 |
Family
ID=15785357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000367108A Expired CA1150247A (en) | 1979-12-19 | 1980-12-18 | (e)-5-(2-halogenovinyl)-arabinofuranosyluracil, process for preparation thereof, and uses thereof |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4386076A (enExample) |
| EP (1) | EP0031128B1 (enExample) |
| JP (1) | JPS5687599A (enExample) |
| CA (1) | CA1150247A (enExample) |
| DE (1) | DE3064165D1 (enExample) |
| ES (1) | ES498020A0 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU183567B (en) * | 1981-09-07 | 1984-05-28 | Mta Koezponti Kemiai Kutato In | Process for preparing /e/-5-/2-bromo-vinyl/-uridine and derivatives thereof |
| JPS5843993A (ja) * | 1981-09-09 | 1983-03-14 | Yamasa Shoyu Co Ltd | １−β−Ｄ−アラビノフラノシル−（Ｅ）−５−（２−ハロゲノビニル）ウラシル−５′−りん酸およびその製造法 |
| US4782142A (en) * | 1982-01-05 | 1988-11-01 | The Research Foundation Of State University Of New York | Novel 5-substituted 2-pyrimidinone nucleosides and methods of use |
| JPS58225097A (ja) * | 1982-06-23 | 1983-12-27 | Yamasa Shoyu Co Ltd | ヌクレオシド５′−アルキルもしくはアルケニルりん酸 |
| HU192472B (en) * | 1984-10-12 | 1987-06-29 | Mta Koezponti Kemiai Kutato In | Process for preparing /e/-5-/2-bromo-vinyl/-uracyl derivatives |
| SE8605503D0 (sv) * | 1986-12-19 | 1986-12-19 | Astra Laekemedel Ab | Novel medicinal use |
| US5215971A (en) * | 1986-12-19 | 1993-06-01 | Medivir Ab | Antiviral pharmaceutical composition comprising 5-substituted pyrimidine nucleosides |
| WO1990001324A1 (en) * | 1988-08-10 | 1990-02-22 | Stephen Leslie Sacks | PRODUCTION OF RADIOIODINATED 1-β-D-ARABINOFURANOSYL)-5(E)-(2-IODOVINYL)URACIL, AND USES THEREOF, AND RELATED ANALOGUES INCORPORATING ALTERNATIVE HALOGEN RADIONUCLIDES, THE GENERAL RADIOHALOGENATION PRECURSORS, 1-(2,3,5-TRI-O-ACETYL-β-D-ARABINOFURANOSYL)-5(Z and E)-(2-TRIMETHYLSILYLVINYL)URACIL, PROCESSES FOR RADIOHA |
| GB8912972D0 (en) * | 1989-06-06 | 1989-07-26 | Wellcome Found | Therapeutic nucleosides |
| US5352584A (en) * | 1990-01-22 | 1994-10-04 | E. R. Squibb & Sons, Inc. | Monoclonal antibodies which bind (E)-5- (2-bromovinyl)-arabinofuranosyluracil and diagnostic methods based thereon |
| CA2085994A1 (en) * | 1991-04-24 | 1992-10-25 | Shinji Sakata | 1-beta-d-arabinofuranosyl-(e)-5- (2-halogenovinyl) uracil derivatives |
| US5446031A (en) * | 1991-04-24 | 1995-08-29 | Yamasa Shuyu Kabushiki Kaisha | 1-β-D-arabinofuranosyl-(E)-5-(2-halogenovinyl)uracil derivatives |
| US5248771A (en) * | 1991-06-26 | 1993-09-28 | Triumf | Process for preparing no-carrier-added radiohalogenated vinyl nucleosides |
| FI20012151A0 (fi) * | 2001-11-05 | 2001-11-05 | Danisco | Nestemäinen leivänparannusaine, sen käyttö ja valmistusmenetelmä |
| US7618950B2 (en) | 2004-07-07 | 2009-11-17 | Arigen Pharmaceuticals, Inc. | Method for treatment and prevention of herpes zoster by topical application |
| JP4964473B2 (ja) * | 2006-02-10 | 2012-06-27 | アリジェン製薬株式会社 | ピリミジンヌクレオシド誘導体及びその塩 |
| US8076302B2 (en) | 2007-02-15 | 2011-12-13 | Arigen Pharmaceuticals, Inc. | Pyrimidine nucleoside derivatives and salts thereof |
| US8658618B2 (en) | 2009-10-14 | 2014-02-25 | Adherex Technologies, Inc. | Methods for preventing or reducing neurotoxicity associated with administering DPD inhibitors in combination with 5-FU and 5-FU prodrugs |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1601020A (en) * | 1978-04-24 | 1981-10-21 | Stichting Grega Vzw | 2'-deoxy-5 (2-halogenovinyl)-uridines |
| US4247544A (en) * | 1979-07-02 | 1981-01-27 | The Regents Of The University Of California | C-5 Substituted uracil nucleosides |
-
1979
- 1979-12-19 JP JP16402579A patent/JPS5687599A/ja active Granted
-
1980
- 1980-12-12 US US06/215,928 patent/US4386076A/en not_active Expired - Lifetime
- 1980-12-16 DE DE8080107949T patent/DE3064165D1/de not_active Expired
- 1980-12-16 EP EP80107949A patent/EP0031128B1/en not_active Expired
- 1980-12-18 CA CA000367108A patent/CA1150247A/en not_active Expired
- 1980-12-19 ES ES498020A patent/ES498020A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4386076A (en) | 1983-05-31 |
| ES8205234A1 (es) | 1982-06-01 |
| JPS5687599A (en) | 1981-07-16 |
| DE3064165D1 (en) | 1983-08-18 |
| JPS5748160B2 (enExample) | 1982-10-14 |
| EP0031128B1 (en) | 1983-07-13 |
| EP0031128A1 (en) | 1981-07-01 |
| ES498020A0 (es) | 1982-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |