DE2944084A1 - 3'-polyphosphate von pyrimidinnucleosiden oder von guanosin und deren salze sowie die verwendung dieser verbindungen zur behandlung von leukaemie - Google Patents
3'-polyphosphate von pyrimidinnucleosiden oder von guanosin und deren salze sowie die verwendung dieser verbindungen zur behandlung von leukaemieInfo
- Publication number
- DE2944084A1 DE2944084A1 DE19792944084 DE2944084A DE2944084A1 DE 2944084 A1 DE2944084 A1 DE 2944084A1 DE 19792944084 DE19792944084 DE 19792944084 DE 2944084 A DE2944084 A DE 2944084A DE 2944084 A1 DE2944084 A1 DE 2944084A1
- Authority
- DE
- Germany
- Prior art keywords
- guanosine
- salts
- diphosphate
- polyphosphates
- triphosphate
- 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.)
- Withdrawn
Links
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 title claims description 18
- 239000001205 polyphosphate Substances 0.000 title claims description 15
- 150000001875 compounds Chemical class 0.000 title claims description 10
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 title claims description 9
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 title claims description 9
- 229940029575 guanosine Drugs 0.000 title claims description 9
- 208000032839 leukemia Diseases 0.000 title claims description 7
- 239000002718 pyrimidine nucleoside Substances 0.000 title claims description 7
- 150000003839 salts Chemical class 0.000 claims description 17
- 229920000388 Polyphosphate Polymers 0.000 claims description 14
- 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 claims description 14
- 239000001177 diphosphate Substances 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 claims description 7
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 claims description 7
- 229940045145 uridine Drugs 0.000 claims description 7
- PCDQPRRSZKQHHS-XVFCMESISA-N CTP Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 PCDQPRRSZKQHHS-XVFCMESISA-N 0.000 claims description 6
- PTZOXEJVEINCFT-UUOKFMHZSA-N [(2r,3s,4r,5r)-5-(2-amino-6-oxo-3h-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [hydroxy(phosphonooxy)phosphoryl] hydrogen phosphate Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](OP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@H]1O PTZOXEJVEINCFT-UUOKFMHZSA-N 0.000 claims description 6
- GNKPWIYRLONLSO-UUOKFMHZSA-N [(2r,3s,4r,5r)-5-(2-amino-6-oxo-3h-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] phosphono hydrogen phosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](CO)[C@@H](OP(O)(=O)OP(O)(O)=O)[C@H]1O GNKPWIYRLONLSO-UUOKFMHZSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- HSQZVTPEUFOJIX-XVFCMESISA-N [(2r,3s,4r,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] phosphono hydrogen phosphate Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@H](OP(O)(=O)OP(O)(O)=O)[C@@H](CO)O1 HSQZVTPEUFOJIX-XVFCMESISA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000000034 method Methods 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 12
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 12
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 12
- 229910052816 inorganic phosphate Inorganic materials 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
- 239000002777 nucleoside Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 8
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 8
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 8
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 8
- 150000003833 nucleoside derivatives Chemical class 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 8
- 239000001226 triphosphate Substances 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 239000011609 ammonium molybdate Substances 0.000 description 6
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 6
- 235000018660 ammonium molybdate Nutrition 0.000 description 6
- 229940010552 ammonium molybdate Drugs 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- ZDPUTNZENXVHJC-UHFFFAOYSA-N cumingianoside D Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(OP(O)(O)=O)C1O ZDPUTNZENXVHJC-UHFFFAOYSA-N 0.000 description 6
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 6
- 235000011180 diphosphates Nutrition 0.000 description 6
- ZDPUTNZENXVHJC-UUOKFMHZSA-N guanosine 3'-monophosphate Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](OP(O)(O)=O)[C@H]1O ZDPUTNZENXVHJC-UUOKFMHZSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- OQUKIQWCVTZJAF-UHFFFAOYSA-N phenol;sulfuric acid Chemical compound OS(O)(=O)=O.OC1=CC=CC=C1 OQUKIQWCVTZJAF-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 6
- 229960005294 triamcinolone Drugs 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 5
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- 238000004519 manufacturing process Methods 0.000 description 5
- 235000011178 triphosphate Nutrition 0.000 description 5
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- SPZSFCHFSIPCSG-UUOKFMHZSA-N [(2r,3s,4r,5r)-5-(2-amino-6-oxo-3h-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyphosphonamidic acid Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](CO)[C@@H](OP(N)(O)=O)[C@H]1O SPZSFCHFSIPCSG-UUOKFMHZSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 description 2
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- FOGRQMPFHUHIGU-XVFCMESISA-L 3'-UMP(2-) Chemical compound O[C@@H]1[C@H](OP([O-])([O-])=O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 FOGRQMPFHUHIGU-XVFCMESISA-L 0.000 description 2
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- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- QGWNDRXFNXRZMB-UHFFFAOYSA-N guanidine diphosphate Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O QGWNDRXFNXRZMB-UHFFFAOYSA-N 0.000 description 1
- RQFCJASXJCIDSX-UUOKFMHZSA-N guanosine 5'-monophosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O RQFCJASXJCIDSX-UUOKFMHZSA-N 0.000 description 1
- 238000010438 heat treatment 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
- 238000011835 investigation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OZNYZQOTXQSUJM-UHFFFAOYSA-N n,n'-dicyclohexylmorpholine-4-carboximidamide Chemical class C1CCCCC1NC(N1CCOCC1)=NC1CCCCC1 OZNYZQOTXQSUJM-UHFFFAOYSA-N 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- XKMLYUALXHKNFT-UHFFFAOYSA-N rGTP Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O XKMLYUALXHKNFT-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- VZWGHDYJGOMEKT-UHFFFAOYSA-J sodium pyrophosphate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O VZWGHDYJGOMEKT-UHFFFAOYSA-J 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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
- C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- 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
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13470878A JPS55102600A (en) | 1978-10-31 | 1978-10-31 | Guanosine derivative, and antileukemic agent containing the same |
| JP256479A JPS5594400A (en) | 1979-01-11 | 1979-01-11 | Guanosine derivative and anti-leukemic agent containing the same |
| JP256579A JPS5594399A (en) | 1979-01-11 | 1979-01-11 | Pyrimidine-nucleoside derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2944084A1 true DE2944084A1 (de) | 1980-06-04 |
Family
ID=27275413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792944084 Withdrawn DE2944084A1 (de) | 1978-10-31 | 1979-10-31 | 3'-polyphosphate von pyrimidinnucleosiden oder von guanosin und deren salze sowie die verwendung dieser verbindungen zur behandlung von leukaemie |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4297347A (enExample) |
| DE (1) | DE2944084A1 (enExample) |
| FR (1) | FR2440375A1 (enExample) |
| GB (1) | GB2037289B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19618727A1 (de) * | 1996-05-09 | 1997-11-13 | Deutsches Krebsforsch | Herstellung alkylierter Nucleosid-3'-Phosphate |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5735516A (en) | 1980-08-11 | 1982-02-26 | Yamasa Shoyu Co Ltd | Agent for increasing radiosensitivity or agent for increasing effect of substance having activity similar to radiation |
| JPS61112093A (ja) * | 1984-11-05 | 1986-05-30 | Wakunaga Seiyaku Kk | ヌクレオチド誘導体 |
| US5187266A (en) * | 1986-06-30 | 1993-02-16 | Board Of Regents The University Of Texas System | Antitumor aldophosphamide glycoside and dideoxyuridine derivatives |
| US5654286A (en) * | 1993-05-12 | 1997-08-05 | Hostetler; Karl Y. | Nucleotides for topical treatment of psoriasis, and methods for using same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2510327A1 (de) * | 1974-03-29 | 1975-10-09 | Sanraku Ocean Co | Purinnukleosid-5'-phosphat-(mono-, di- oder tri-)-3'-(2')-diphosphate |
| DE2530862A1 (de) * | 1974-07-11 | 1976-01-29 | Chugai Pharmaceutical Co Ltd | Arzneimittel zur verhuetung und behandlung von alkoholismus |
| DE2546073A1 (de) * | 1974-10-15 | 1976-04-22 | Asahi Chemical Ind | Nucleotid-derivate und verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1433279A (fr) * | 1964-05-19 | 1966-03-25 | Kyowa Hakko Kogyo Kk | Procédé de préparation de l'acide 5'-guanylique |
| US3299042A (en) * | 1964-06-22 | 1967-01-17 | Lipkin David | Iodination of the heterocyclic bases in nucleosides, nucleotides, nucleoside-5'-polyphosphates, and nucleic acids |
| US3475409A (en) * | 1966-07-14 | 1969-10-28 | Asahi Chemical Ind | Process for preparing ribonucleoside-5'-monophosphate |
| US3462416A (en) * | 1967-01-30 | 1969-08-19 | Upjohn Co | Hydrogenated pyrimidine nucleosides and nucleotides |
| US3830798A (en) * | 1968-03-22 | 1974-08-20 | Ralston Purina Co | Hydrolysis of ribonucleic acid containing material |
| US4141972A (en) * | 1974-03-29 | 1979-02-27 | Sanraku-Ocean Co., Ltd. | Purine nucleoside 5'-phosphate (mono, di or tri) 3'(2')-diphosphates and processes for their preparation |
-
1979
- 1979-10-29 GB GB7937442A patent/GB2037289B/en not_active Expired
- 1979-10-31 US US06/089,887 patent/US4297347A/en not_active Expired - Lifetime
- 1979-10-31 FR FR7927023A patent/FR2440375A1/fr active Granted
- 1979-10-31 DE DE19792944084 patent/DE2944084A1/de not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2510327A1 (de) * | 1974-03-29 | 1975-10-09 | Sanraku Ocean Co | Purinnukleosid-5'-phosphat-(mono-, di- oder tri-)-3'-(2')-diphosphate |
| DE2530862A1 (de) * | 1974-07-11 | 1976-01-29 | Chugai Pharmaceutical Co Ltd | Arzneimittel zur verhuetung und behandlung von alkoholismus |
| DE2546073A1 (de) * | 1974-10-15 | 1976-04-22 | Asahi Chemical Ind | Nucleotid-derivate und verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
Non-Patent Citations (1)
| Title |
|---|
| KOZARICH, John W. et al: Ribonucleoside 3'-Di-and-Triphosphates. In: Biochemistry 1975, Nr. 5, S.981-5 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19618727A1 (de) * | 1996-05-09 | 1997-11-13 | Deutsches Krebsforsch | Herstellung alkylierter Nucleosid-3'-Phosphate |
| DE19618727C2 (de) * | 1996-05-09 | 2000-02-17 | Deutsches Krebsforsch | Herstellung alkylierter Nucleosid-3'-Phosphate |
Also Published As
| Publication number | Publication date |
|---|---|
| US4297347A (en) | 1981-10-27 |
| FR2440375A1 (fr) | 1980-05-30 |
| GB2037289B (en) | 1983-05-05 |
| FR2440375B1 (enExample) | 1983-03-04 |
| GB2037289A (en) | 1980-07-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAR | Request for search filed | ||
| OC | Search report available | ||
| 8128 | New person/name/address of the agent |
Representative=s name: VOSSIUS, V., DIPL.-CHEM. DR.RER.NAT. VOSSIUS, D., |
|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: A61K 31/70 |
|
| 8128 | New person/name/address of the agent |
Representative=s name: VOSSIUS, V., DIPL.-CHEM. DR.RER.NAT. TAUCHNER, P., |
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| 8139 | Disposal/non-payment of the annual fee |