GB877318A - The manufacture of cytidines - Google Patents
The manufacture of cytidinesInfo
- Publication number
- GB877318A GB877318A GB17544/60A GB1754460A GB877318A GB 877318 A GB877318 A GB 877318A GB 17544/60 A GB17544/60 A GB 17544/60A GB 1754460 A GB1754460 A GB 1754460A GB 877318 A GB877318 A GB 877318A
- Authority
- GB
- United Kingdom
- Prior art keywords
- fluoro
- deoxy
- dioxo
- phenyl
- methyl
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 5
- -1 chlorobenzoyl Chemical group 0.000 abstract 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 229960004413 flucytosine Drugs 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 3
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 229960000583 acetic acid Drugs 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- WJZQUTIZBUJHRJ-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-methylpyridazine-3,6-dione Chemical compound ClC1=C(C=CC=C1)N1N(C(C=CC1=O)=O)C WJZQUTIZBUJHRJ-UHFFFAOYSA-N 0.000 abstract 1
- WHPFEQUEHBULBW-UHFFFAOYSA-N 2,4-dichloro-5-fluoropyrimidine Chemical compound FC1=CN=C(Cl)N=C1Cl WHPFEQUEHBULBW-UHFFFAOYSA-N 0.000 abstract 1
- FJAFBNURTGHKCR-UHFFFAOYSA-N 2-(2-chlorophenyl)-1h-pyridazine-3,6-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C=CC(=O)N1 FJAFBNURTGHKCR-UHFFFAOYSA-N 0.000 abstract 1
- SLQAJWTZUXJPNY-UHFFFAOYSA-N 2-chloro-5-fluoropyrimidin-4-amine Chemical compound NC1=NC(Cl)=NC=C1F SLQAJWTZUXJPNY-UHFFFAOYSA-N 0.000 abstract 1
- ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 abstract 1
- MROHOLVKUHALKK-UHFFFAOYSA-N 4,5-dibromo-1-(2-chlorophenyl)-2-methyldiazinane-3,6-dione Chemical compound ClC1=C(C=CC=C1)N1N(C(C(C(C1=O)Br)Br)=O)C MROHOLVKUHALKK-UHFFFAOYSA-N 0.000 abstract 1
- SPBXHODOBMVHQL-UHFFFAOYSA-N 4,6-dichloro-2-phenylpyridazin-3-one Chemical compound N1=C(Cl)C=C(Cl)C(=O)N1C1=CC=CC=C1 SPBXHODOBMVHQL-UHFFFAOYSA-N 0.000 abstract 1
- KDGOHVAREAHSOT-UHFFFAOYSA-N 4,6-dimethoxy-2-phenylpyridazin-3-one Chemical compound C1(=CC=CC=C1)N1N=C(C=C(C1=O)OC)OC KDGOHVAREAHSOT-UHFFFAOYSA-N 0.000 abstract 1
- YSQXHUNJVXCDIV-UHFFFAOYSA-N 4-bromo-2-(2-chlorophenyl)-1-methylpyridazine-3,6-dione Chemical compound ClC1=C(C=CC=C1)N1N(C(C=C(C1=O)Br)=O)C YSQXHUNJVXCDIV-UHFFFAOYSA-N 0.000 abstract 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 abstract 1
- KJEBAQNNTMWJJI-UHFFFAOYSA-N 6-hydroxy-2-phenylpyridazin-3-one Chemical class N1=C(O)C=CC(=O)N1C1=CC=CC=C1 KJEBAQNNTMWJJI-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- CKTSBUTUHBMZGZ-UHFFFAOYSA-N Deoxycytidine Natural products O=C1N=C(N)C=CN1C1OC(CO)C(O)C1 CKTSBUTUHBMZGZ-UHFFFAOYSA-N 0.000 abstract 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 abstract 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- 229910019213 POCl3 Inorganic materials 0.000 abstract 1
- NRCOAZOTWLCZKG-UHFFFAOYSA-N [Hg].FC=1C(=NC(NC1)=O)N Chemical compound [Hg].FC=1C(=NC(NC1)=O)N NRCOAZOTWLCZKG-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- GYIWFHXWLCXGQO-UHFFFAOYSA-N barium(2+);ethanolate Chemical compound [Ba+2].CC[O-].CC[O-] GYIWFHXWLCXGQO-UHFFFAOYSA-N 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 abstract 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 229960002949 fluorouracil Drugs 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000001035 methylating effect Effects 0.000 abstract 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
- C07F3/103—Mercury compounds without C-Mercury linkages
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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US817736A US3040026A (en) | 1959-06-03 | 1959-06-03 | Processes and intermediates for deoxyfluorocytidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB877318A true GB877318A (en) | 1961-09-13 |
Family
ID=25223771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17544/60A Expired GB877318A (en) | 1959-06-03 | 1960-05-18 | The manufacture of cytidines |
Country Status (7)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1219938B (de) * | 1962-05-01 | 1966-06-30 | Hoffmann La Roche | Verfahren zur Herstellung von 4-N-p-Toluoyl-5-fluor-2'-desoxycytidin |
| DE1264445B (de) * | 1963-10-09 | 1968-03-28 | Robugen Gmbh | Verfahren zur Herstellung von 2, 6-Dichlor-5-fluorpyrimidin |
| US4703121A (en) * | 1984-11-14 | 1987-10-27 | Bayer Aktiengesellschaft | Process for the preparation of 5-fluorocytosine |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3282919A (en) * | 1964-02-06 | 1966-11-01 | American Cyanamid Co | Process for preparing orotidine |
| US3328388A (en) * | 1964-09-02 | 1967-06-27 | Merck & Co Inc | Arabinofuranosyl pyrimidines and methods of preparing same |
| US3309359A (en) * | 1965-10-22 | 1967-03-14 | Hoffmann La Roche | N-mono-acyl-5-fluorocytosine derivatives and process |
| DE2359536C2 (de) * | 1972-12-08 | 1984-08-02 | Takeda Chemical Industries, Ltd., Osaka | 2,6-Diaminonebularinderivate |
| US4041037A (en) * | 1975-06-10 | 1977-08-09 | American Home Products Corporation | Antitumor derivatives of periodate-oxidized cytidine |
| US4177348A (en) * | 1977-12-13 | 1979-12-04 | United States Government | Carbocyclic analogs of cytosine nucleosides |
| US4232154A (en) * | 1977-12-13 | 1980-11-04 | United States Of America | Carbocyclic analogs of cytosine nucleosides exhibiting antiviral and antineoplasticactivity |
| US5155221A (en) * | 1992-03-06 | 1992-10-13 | Dowelanco | Process for the preparation of 2-alkylthio-4-hydrazino-5-fluoropyrimidines |
| CN106349169A (zh) * | 2016-08-25 | 2017-01-25 | 宿迁市万和泰化工有限公司 | 一种适用于工业生产的氟胞嘧啶的制备方法 |
| CN106632080A (zh) * | 2016-08-25 | 2017-05-10 | 宿迁市万和泰化工有限公司 | 一种氟胞嘧啶的生产工艺 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE870558C (de) * | 1942-09-06 | 1953-03-16 | Bayer Ag | Verfahren zur Herstellung von 2-Aminopyrimidin |
| US2688019A (en) * | 1951-08-25 | 1954-08-31 | Burroughs Wellcome Co | 6-aryl-2,4-diamino pyrimidines and process of preparing same |
| US2804459A (en) * | 1955-02-23 | 1957-08-27 | Pfizer & Co C | Preparation of 4-aminouracil |
| US2892840A (en) * | 1955-12-05 | 1959-06-30 | Kay Fries Chemicals Inc | Preparation of cytosine and intermediates |
| US2885396A (en) * | 1957-03-21 | 1959-05-05 | Heidelberger Charles | N-glycosides of 5-fluorouracil |
| US2937171A (en) * | 1958-06-13 | 1960-05-17 | Du Pont | Process for obtaining fluorinated organic compounds |
-
0
- NL NL299755D patent/NL299755A/xx unknown
-
1959
- 1959-06-03 US US817736A patent/US3040026A/en not_active Expired - Lifetime
-
1960
- 1960-05-18 GB GB17544/60A patent/GB877318A/en not_active Expired
- 1960-05-20 CH CH580060A patent/CH408024A/de unknown
- 1960-05-20 CH CH773265A patent/CH426841A/de unknown
- 1960-05-23 DE DEH39501A patent/DE1132926B/de active Pending
- 1960-05-23 DE DE19601745629 patent/DE1745629B1/de active Pending
- 1960-06-02 BE BE591486A patent/BE591486A/fr unknown
- 1960-06-03 SE SE5488/60A patent/SE309778B/xx unknown
-
1961
- 1961-09-14 US US137991A patent/US3185690A/en not_active Expired - Lifetime
-
1962
- 1962-06-06 SE SE6336/62A patent/SE320974B/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1219938B (de) * | 1962-05-01 | 1966-06-30 | Hoffmann La Roche | Verfahren zur Herstellung von 4-N-p-Toluoyl-5-fluor-2'-desoxycytidin |
| DE1264445B (de) * | 1963-10-09 | 1968-03-28 | Robugen Gmbh | Verfahren zur Herstellung von 2, 6-Dichlor-5-fluorpyrimidin |
| US4703121A (en) * | 1984-11-14 | 1987-10-27 | Bayer Aktiengesellschaft | Process for the preparation of 5-fluorocytosine |
Also Published As
| Publication number | Publication date |
|---|---|
| SE320974B (US07122547-20061017-C00273.png) | 1970-02-23 |
| CH408024A (de) | 1966-02-28 |
| US3040026A (en) | 1962-06-19 |
| NL299755A (US07122547-20061017-C00273.png) | |
| US3185690A (en) | 1965-05-25 |
| DE1132926B (de) | 1962-07-12 |
| SE309778B (US07122547-20061017-C00273.png) | 1969-04-08 |
| DE1745629B1 (de) | 1970-07-23 |
| CH426841A (de) | 1966-12-31 |
| BE591486A (fr) | 1960-12-02 |
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