JPS5791995A - Nucleoside-5'-o-morpholinoacyl ester and its preparation - Google Patents
Nucleoside-5'-o-morpholinoacyl ester and its preparationInfo
- Publication number
- JPS5791995A JPS5791995A JP56080228A JP8022881A JPS5791995A JP S5791995 A JPS5791995 A JP S5791995A JP 56080228 A JP56080228 A JP 56080228A JP 8022881 A JP8022881 A JP 8022881A JP S5791995 A JPS5791995 A JP S5791995A
- Authority
- JP
- Japan
- Prior art keywords
- nucleoside
- ester
- expressed
- morpholinoacyl
- formulai
- 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
- 150000002148 esters Chemical class 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 2
- 150000004671 saturated fatty acids Chemical class 0.000 abstract 2
- FHIDNBAQOFJWCA-UAKXSSHOSA-N 5-fluorouridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 FHIDNBAQOFJWCA-UAKXSSHOSA-N 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000009876 antimalignant effect Effects 0.000 abstract 1
- 239000003443 antiviral agent Substances 0.000 abstract 1
- 150000007514 bases Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000001900 immune effect Effects 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000002777 nucleoside Substances 0.000 abstract 1
- 150000003833 nucleoside derivatives Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000005270 trialkylamine group Chemical group 0.000 abstract 1
Classifications
-
- 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
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
NEW MATERIAL:A nucleoside-5'-O-morpholinoacyl ester expressed by formulaI (A is an acyl group of a saturated fatty acid having a morpholino group at the α- or ω-position; Z and Z' are H or OH, however not OH at the same time).
EXAMPLE: 5'-O-(5-Morpholinopentanoyl)-5-fluorouidine.
USE: An antimalignant tumor agent, antiviral agent and immunological inhibitor.
PROCESS: A saturated fatty acid having a morpholino group at the α- or the ω- position is esterified with a nucleoside expressed by formula II e.g. 5-fluorouridine, in an anhydrous solvent, e.g. benzene or chloroform, in the presence of a basic compound, e.g. a trialkylamine or pyridine, and a condensing agent, e.g. p-toluenesulfonyl chloride, at 40°C or below to form an ester bond and give the compound expressed by formulaI.
COPYRIGHT: (C)1982,JPO&Japio
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/210,796 US4340728A (en) | 1979-11-28 | 1980-11-26 | Nucleoside derivatives and process for preparing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5791995A true JPS5791995A (en) | 1982-06-08 |
Family
ID=22784293
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56079434A Pending JPS5791994A (en) | 1980-11-26 | 1981-05-27 | 5'-o-(n-alkylcarbamoylalanyl)-5-fluorouridine and its preparation |
| JP56080230A Granted JPS5791997A (en) | 1980-11-26 | 1981-05-28 | 5'-o-acylnucleoside and its preparation |
| JP56080231A Pending JPS5791998A (en) | 1980-11-26 | 1981-05-28 | Novel 5'-o-acylnucleoside derivative and its preparation |
| JP56080229A Granted JPS5791996A (en) | 1980-11-26 | 1981-05-28 | Novel nucleoside derivative and its preparation |
| JP56080228A Pending JPS5791995A (en) | 1980-11-26 | 1981-05-28 | Nucleoside-5'-o-morpholinoacyl ester and its preparation |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56079434A Pending JPS5791994A (en) | 1980-11-26 | 1981-05-27 | 5'-o-(n-alkylcarbamoylalanyl)-5-fluorouridine and its preparation |
| JP56080230A Granted JPS5791997A (en) | 1980-11-26 | 1981-05-28 | 5'-o-acylnucleoside and its preparation |
| JP56080231A Pending JPS5791998A (en) | 1980-11-26 | 1981-05-28 | Novel 5'-o-acylnucleoside derivative and its preparation |
| JP56080229A Granted JPS5791996A (en) | 1980-11-26 | 1981-05-28 | Novel nucleoside derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (5) | JPS5791994A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5925327A (en) * | 1982-07-31 | 1984-02-09 | Hidematsu Hirai | Preparation of antitumor complex |
| JPS63196519A (en) * | 1987-02-12 | 1988-08-15 | Mitsui Toatsu Chem Inc | Carcinostatic agent |
| US5470838A (en) * | 1987-10-28 | 1995-11-28 | Pro-Neuron, Inc. | Method of delivering exogenous uridine or cytidine using acylated uridine or cytidine |
| US5583117A (en) * | 1987-10-28 | 1996-12-10 | Pro-Neuron, Inc. | Acylated uridine and cytidine for elevating tissue uridine and cytidine |
| US5783689A (en) * | 1996-11-12 | 1998-07-21 | University Of Notre Dame | Antibacterial and antifungal nucleosides |
| US6020322A (en) * | 1993-11-09 | 2000-02-01 | Pro-Neuron, Inc. | Acyl deoxyribonucleoside derivatives and uses thereof |
| US6020320A (en) * | 1987-10-28 | 2000-02-01 | Pro-Neuron, Inc. | Acyl deoxyribonucleoside derivatives and uses thereof |
| US7169765B1 (en) | 1988-10-27 | 2007-01-30 | Wellstat Therapeutics Corporation | Acyl deoxyribonucleoside derivatives and uses thereof |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61134397A (en) * | 1984-12-01 | 1986-06-21 | Fuji Kagaku Kogyo Kk | 5'-o-oligopeptidyl-5-fluorouridine and production thereof |
| DE268678T1 (en) * | 1986-05-30 | 1988-11-24 | Fuji Kagaku Kogyo K.K., Toyama | NEW 5-FLUORURIDINE COMPOUNDS AND THEIR PRODUCTION. |
| AU610913B2 (en) * | 1987-07-31 | 1991-05-30 | Taiho Pharmaceutical Co., Ltd. | 2'-deoxy-5-fluorouridine derivatives |
| JP2631227B2 (en) * | 1988-07-11 | 1997-07-16 | 大鵬薬品工業株式会社 | 5'-benzyl-5-fluorouridine derivatives and intermediates thereof |
| WO1991012259A1 (en) * | 1990-02-08 | 1991-08-22 | Sankyo Company, Limited | 5-fu derivative |
| JP2526414B2 (en) * | 1994-05-20 | 1996-08-21 | 工業技術院長 | Anticancer drug ester compound and method for producing the same |
-
1981
- 1981-05-27 JP JP56079434A patent/JPS5791994A/en active Pending
- 1981-05-28 JP JP56080230A patent/JPS5791997A/en active Granted
- 1981-05-28 JP JP56080231A patent/JPS5791998A/en active Pending
- 1981-05-28 JP JP56080229A patent/JPS5791996A/en active Granted
- 1981-05-28 JP JP56080228A patent/JPS5791995A/en active Pending
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5925327A (en) * | 1982-07-31 | 1984-02-09 | Hidematsu Hirai | Preparation of antitumor complex |
| JPS63196519A (en) * | 1987-02-12 | 1988-08-15 | Mitsui Toatsu Chem Inc | Carcinostatic agent |
| US6020320A (en) * | 1987-10-28 | 2000-02-01 | Pro-Neuron, Inc. | Acyl deoxyribonucleoside derivatives and uses thereof |
| US5583117A (en) * | 1987-10-28 | 1996-12-10 | Pro-Neuron, Inc. | Acylated uridine and cytidine for elevating tissue uridine and cytidine |
| US5470838A (en) * | 1987-10-28 | 1995-11-28 | Pro-Neuron, Inc. | Method of delivering exogenous uridine or cytidine using acylated uridine or cytidine |
| US6103701A (en) * | 1987-10-28 | 2000-08-15 | Von Borstel; Reid Warren | Method for enhancing hematopoiesis with acyl deoxyribonucleosides |
| US6258795B1 (en) | 1987-10-28 | 2001-07-10 | Pro-Neuron, Inc. | Acylated uridine and cytidine and uses thereof |
| US6274563B1 (en) | 1987-10-28 | 2001-08-14 | Pro-Neuron, Inc. | Acylated uridine and cytidine and uses thereof |
| US6297222B1 (en) | 1987-10-28 | 2001-10-02 | Pro-Neuron, Inc. | Acyl deoxyribonucleoside derivatives and uses thereof |
| US6306834B1 (en) | 1987-10-28 | 2001-10-23 | Pro-Neuron, Inc. | Acyl deoxyribonucleoside derivatives and uses thereof |
| US6316426B1 (en) | 1987-10-28 | 2001-11-13 | Pro-Neuron, Inc. | Acylated uridine and cytidine and uses thereof |
| US7169765B1 (en) | 1988-10-27 | 2007-01-30 | Wellstat Therapeutics Corporation | Acyl deoxyribonucleoside derivatives and uses thereof |
| US6020322A (en) * | 1993-11-09 | 2000-02-01 | Pro-Neuron, Inc. | Acyl deoxyribonucleoside derivatives and uses thereof |
| US5783689A (en) * | 1996-11-12 | 1998-07-21 | University Of Notre Dame | Antibacterial and antifungal nucleosides |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5791996A (en) | 1982-06-08 |
| JPS5791994A (en) | 1982-06-08 |
| JPS5791997A (en) | 1982-06-08 |
| JPS6247198B2 (en) | 1987-10-06 |
| JPS6247196B2 (en) | 1987-10-06 |
| JPS5791998A (en) | 1982-06-08 |
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