DE1237123B - Verfahren zur Herstellung eines 5-Acyloxyuracils - Google Patents
Verfahren zur Herstellung eines 5-AcyloxyuracilsInfo
- Publication number
- DE1237123B DE1237123B DE1964W0036240 DEW0036240A DE1237123B DE 1237123 B DE1237123 B DE 1237123B DE 1964W0036240 DE1964W0036240 DE 1964W0036240 DE W0036240 A DEW0036240 A DE W0036240A DE 1237123 B DE1237123 B DE 1237123B
- Authority
- DE
- Germany
- Prior art keywords
- nicotinoyloxyuracil
- acyloxyuracil
- hydroxyuracil
- preparation
- mol
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- SUINBPLFTBNHLU-UHFFFAOYSA-N (2,4-dioxo-1H-pyrimidin-5-yl) pyridine-3-carboxylate Chemical compound C(C1=CN=CC=C1)(=O)OC=1C(NC(NC1)=O)=O SUINBPLFTBNHLU-UHFFFAOYSA-N 0.000 claims description 10
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 9
- OFJNVANOCZHTMW-UHFFFAOYSA-N 5-hydroxyuracil Chemical compound OC1=CNC(=O)NC1=O OFJNVANOCZHTMW-UHFFFAOYSA-N 0.000 claims description 8
- 229960003512 nicotinic acid Drugs 0.000 claims description 4
- 235000001968 nicotinic acid Nutrition 0.000 claims description 4
- 239000011664 nicotinic acid Substances 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- DSIXOYBJKMTFMC-UHFFFAOYSA-N (2,4-dioxo-1h-pyrimidin-5-yl) acetate Chemical compound CC(=O)OC1=CNC(=O)NC1=O DSIXOYBJKMTFMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- LAVLPYFKBNPFEE-UHFFFAOYSA-N imidazol-1-yl(pyridin-3-yl)methanone Chemical compound C1=CN=CN1C(=O)C1=CC=CN=C1 LAVLPYFKBNPFEE-UHFFFAOYSA-N 0.000 description 2
- 229960001428 mercaptopurine Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 101710154606 Hemagglutinin Proteins 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 101710093908 Outer capsid protein VP4 Proteins 0.000 description 1
- 101710135467 Outer capsid protein sigma-1 Proteins 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 101710176177 Protein A56 Proteins 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000001399 anti-metabolic effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000185 hemagglutinin Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7554/63A GB991988A (en) | 1963-02-25 | 1963-02-25 | Novel 5-acyloxyuracils |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1237123B true DE1237123B (de) | 1967-03-23 |
Family
ID=9835358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1964W0036240 Pending DE1237123B (de) | 1963-02-25 | 1964-02-25 | Verfahren zur Herstellung eines 5-Acyloxyuracils |
Country Status (10)
-
1963
- 1963-02-25 GB GB7554/63A patent/GB991988A/en not_active Expired
-
1964
- 1964-02-20 CH CH204564A patent/CH448101A/de unknown
- 1964-02-21 BE BE644200A patent/BE644200A/xx unknown
- 1964-02-24 AT AT154064A patent/AT252261B/de active
- 1964-02-24 ES ES0296793A patent/ES296793A1/es not_active Expired
- 1964-02-24 NL NL6401717A patent/NL6401717A/xx unknown
- 1964-02-24 DK DK89564A patent/DK107751C/da active
- 1964-02-25 SE SE227964A patent/SE305875B/xx unknown
- 1964-02-25 DE DE1964W0036240 patent/DE1237123B/de active Pending
- 1964-05-22 FR FR975576A patent/FR3487M/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| SE305875B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-11-11 |
| GB991988A (en) | 1965-05-12 |
| DK107751C (da) | 1967-07-03 |
| BE644200A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-08-21 |
| ES296793A1 (es) | 1964-09-01 |
| CH448101A (de) | 1967-12-15 |
| NL6401717A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-08-26 |
| FR3487M (fr) | 1965-08-16 |
| AT252261B (de) | 1967-02-10 |
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