CS274486B2 - Method of 5-deoxy-5-fluorcytidine's new derivatives production - Google Patents
Method of 5-deoxy-5-fluorcytidine's new derivatives production Download PDFInfo
- Publication number
- CS274486B2 CS274486B2 CS747588A CS747588A CS274486B2 CS 274486 B2 CS274486 B2 CS 274486B2 CS 747588 A CS747588 A CS 747588A CS 747588 A CS747588 A CS 747588A CS 274486 B2 CS274486 B2 CS 274486B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- deoxy
- fluorocytidine
- fluoro
- group
- cytidine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 3
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- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 230000004962 physiological condition Effects 0.000 claims description 6
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- 238000001953 recrystallisation Methods 0.000 description 8
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- YSNABXSEHNLERR-ZIYNGMLESA-N 5'-Deoxy-5-fluorocytidine Chemical class O[C@@H]1[C@H](O)[C@@H](C)O[C@H]1N1C(=O)N=C(N)C(F)=C1 YSNABXSEHNLERR-ZIYNGMLESA-N 0.000 description 7
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- 238000003556 assay Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- JUOCBGGLQBUHJU-FRJWGUMJSA-N n-[1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]pyridine-3-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C)O[C@H]1N1C(=O)N=C(NC(=O)C=2C=NC=CC=2)C(F)=C1 JUOCBGGLQBUHJU-FRJWGUMJSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical group CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 description 1
- 229960001674 tegafur Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
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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
- C07H19/067—Pyrimidine radicals with ribosyl as the saccharide radical
-
- 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
- A61P35/00—Antineoplastic agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP87116926 | 1987-11-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
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| CS747588A CS274486B2 (en) | 1987-11-17 | 1988-11-15 | Method of 5-deoxy-5-fluorcytidine's new derivatives production |
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| EP (1) | EP0316704B1 (es) |
| JP (1) | JPH0678350B2 (es) |
| KR (1) | KR970000241B1 (es) |
| CN (1) | CN1022688C (es) |
| AR (1) | AR247217A1 (es) |
| AT (1) | ATE124951T1 (es) |
| AU (1) | AU619220B2 (es) |
| CA (1) | CA1327358C (es) |
| CS (1) | CS274486B2 (es) |
| DE (2) | DE10199027I2 (es) |
| DK (1) | DK170893B1 (es) |
| DZ (1) | DZ1270A1 (es) |
| ES (1) | ES2074429T3 (es) |
| FI (1) | FI89804C (es) |
| GR (1) | GR3017686T3 (es) |
| HK (1) | HK1003114A1 (es) |
| HU (1) | HU199866B (es) |
| IE (1) | IE883430L (es) |
| IL (1) | IL88363A0 (es) |
| IS (1) | IS1895B (es) |
| LT (1) | LT2185B (es) |
| LU (1) | LU90769I2 (es) |
| LV (1) | LV5624A3 (es) |
| MC (1) | MC1992A1 (es) |
| MX (1) | MX173347B (es) |
| NL (1) | NL300045I2 (es) |
| NO (2) | NO171167C (es) |
| NZ (1) | NZ226923A (es) |
| PH (1) | PH25641A (es) |
| PT (1) | PT89009B (es) |
| SU (1) | SU1736342A3 (es) |
| UA (1) | UA19333A (es) |
| YU (1) | YU47122B (es) |
| ZA (1) | ZA888428B (es) |
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| US3404144A (en) * | 1965-12-23 | 1968-10-01 | Research Corp | 1-beta-d-arabinofuranosyl-5-fluorocytosine compounds |
| GB1379410A (en) * | 1971-06-08 | 1975-01-02 | Upjohn Co | 1-beta-d-arabino-furanosyl-n4-alpha-aminoacylcytosines |
| JPS52153977A (en) * | 1976-06-11 | 1977-12-21 | Daikin Ind Ltd | Synthesis of 5-fluorouracil and its derivatives |
| US4071680A (en) * | 1976-12-20 | 1978-01-31 | Hoffmann-La Roche Inc. | 5'-Deoxy-5-fluoropyrimidine nucleosides |
| CH633810A5 (en) * | 1978-01-01 | 1982-12-31 | Hoffmann La Roche | Novel nucleosides and process for their preparation |
| FR2528311B1 (fr) * | 1982-06-14 | 1985-06-14 | Synthelabo | Compositions pharmaceutiques a base de xylosides et lyxosides de bases puriques et pyrimidiques |
| JPS61112093A (ja) * | 1984-11-05 | 1986-05-30 | Wakunaga Seiyaku Kk | ヌクレオチド誘導体 |
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- 1988-11-07 EP EP88118515A patent/EP0316704B1/de not_active Expired - Lifetime
- 1988-11-07 AT AT88118515T patent/ATE124951T1/de active
- 1988-11-07 ES ES88118515T patent/ES2074429T3/es not_active Expired - Lifetime
- 1988-11-07 DE DE2001199027 patent/DE10199027I2/de active Active
- 1988-11-07 DE DE3854148T patent/DE3854148D1/de not_active Expired - Lifetime
- 1988-11-08 US US07/268,437 patent/US4966891A/en not_active Expired - Lifetime
- 1988-11-10 ZA ZA888428A patent/ZA888428B/xx unknown
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- 1988-11-11 IL IL88363A patent/IL88363A0/xx not_active IP Right Cessation
- 1988-11-14 JP JP63285940A patent/JPH0678350B2/ja not_active Expired - Lifetime
- 1988-11-14 MC MC882015A patent/MC1992A1/fr unknown
- 1988-11-14 HU HU885799A patent/HU199866B/hu unknown
- 1988-11-15 CS CS747588A patent/CS274486B2/cs not_active IP Right Cessation
- 1988-11-15 KR KR1019880014983A patent/KR970000241B1/ko not_active Expired - Lifetime
- 1988-11-16 PT PT89009A patent/PT89009B/pt not_active IP Right Cessation
- 1988-11-16 NO NO885106A patent/NO171167C/no not_active IP Right Cessation
- 1988-11-16 IS IS3412A patent/IS1895B/is unknown
- 1988-11-16 SU SU884356869A patent/SU1736342A3/ru active
- 1988-11-16 PH PH37820A patent/PH25641A/en unknown
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- 1988-11-16 CN CN88107886A patent/CN1022688C/zh not_active Expired - Lifetime
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- 1988-11-16 DK DK640388A patent/DK170893B1/da not_active IP Right Cessation
- 1988-11-16 AU AU25168/88A patent/AU619220B2/en not_active Expired
- 1988-11-16 DZ DZ880179A patent/DZ1270A1/fr active
- 1988-11-16 UA UA4356869A patent/UA19333A/uk unknown
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1993
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1995
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| Date | Code | Title | Description |
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| IF00 | In force as of 2000-06-30 in czech republic | ||
| MK4A | Patent expired |
Effective date: 20081115 |