ES366910A1 - A PROCEDURE TO PREPARE 1-GLYCOSYL-5-AZACITOSINS. - Google Patents
A PROCEDURE TO PREPARE 1-GLYCOSYL-5-AZACITOSINS.Info
- Publication number
- ES366910A1 ES366910A1 ES366910A ES366910A ES366910A1 ES 366910 A1 ES366910 A1 ES 366910A1 ES 366910 A ES366910 A ES 366910A ES 366910 A ES366910 A ES 366910A ES 366910 A1 ES366910 A1 ES 366910A1
- Authority
- ES
- Spain
- Prior art keywords
- glycosyl
- general formula
- alkyl group
- group
- peracylglycosyl
- 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003147 glycosyl group Chemical group 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
- C07H19/12—Triazine radicals
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)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1-Glycosyl-5-azacytosines of the general formula wherein R1 is a glycosyl residue, R2 is a hydrogen atom or a C 1-4 alkyl group and R3 and R4, which are the same or different, are each a hydrogen atom, a C 1-4 alkyl group or a C 7-10 aralkyl group, are prepared by reaction of a 1- peracylglycosyl - 1,2 - dihydro - 1,3,5 - triazin- 2-one of the general formula wherein R5 is a peracylglycosyl residue, the acyl group containing from 2 to 10 carbon atoms, and X is a C 1-4 alkoxy or alkylthio group, with an alkali metal C 1-6 alkoxide and treatment of the resulting 1 -glycosyl- 1 ,2-dihydro - 4 - alkoxy - 1,3,5 - triazin - 2 - one of the general formula wherein R6 is a C 1-6 alkyl group, with ammonia or an amine of the general formula R3R4NH. The two steps may be carried out simultaneously using the ammonia or amine in the form of an alkanol solution thereof, or the first step may be omitted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS339968 | 1968-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES366910A1 true ES366910A1 (en) | 1971-03-16 |
Family
ID=5373920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES366910A Expired ES366910A1 (en) | 1968-05-08 | 1969-05-07 | A PROCEDURE TO PREPARE 1-GLYCOSYL-5-AZACITOSINS. |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS4916435B1 (en) |
| AT (1) | AT306930B (en) |
| BE (1) | BE732268A (en) |
| BR (1) | BR6908600D0 (en) |
| CA (1) | CA921904A (en) |
| CH (1) | CH527207A (en) |
| DE (1) | DE1922702A1 (en) |
| ES (1) | ES366910A1 (en) |
| FR (1) | FR2008048A1 (en) |
| GB (1) | GB1227691A (en) |
| IT (1) | IT1037009B (en) |
| NL (1) | NL6906909A (en) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2012888C3 (en) * | 1970-03-14 | 1981-04-02 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Process for the preparation of 5-azapyrimidine nucleosides |
| US6905669B2 (en) | 2001-04-24 | 2005-06-14 | Supergen, Inc. | Compositions and methods for reestablishing gene transcription through inhibition of DNA methylation and histone deacetylase |
| US6982253B2 (en) | 2002-06-05 | 2006-01-03 | Supergen, Inc. | Liquid formulation of decitabine and use of the same |
| US6943249B2 (en) | 2003-03-17 | 2005-09-13 | Ash Stevens, Inc. | Methods for isolating crystalline Form I of 5-azacytidine |
| US7038038B2 (en) | 2003-03-17 | 2006-05-02 | Pharmion Corporation | Synthesis of 5-azacytidine |
| US6887855B2 (en) | 2003-03-17 | 2005-05-03 | Pharmion Corporation | Forms of 5-azacytidine |
| US20060014949A1 (en) * | 2004-07-13 | 2006-01-19 | Supergen Inc. | Compositions and formulations of decitabine polymorphs and methods of use thereof |
| US7250416B2 (en) | 2005-03-11 | 2007-07-31 | Supergen, Inc. | Azacytosine analogs and derivatives |
| US7700567B2 (en) | 2005-09-29 | 2010-04-20 | Supergen, Inc. | Oligonucleotide analogues incorporating 5-aza-cytosine therein |
| JP5528806B2 (en) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | Compound drug |
| JP5528807B2 (en) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | Compound drug |
| LT3692983T (en) | 2008-05-15 | 2021-11-10 | Celgene Corporation | ORAL COMPOSITIONS OF CITIDINE ANALOGS AND THEIR USE |
| AU2009279461B2 (en) | 2008-08-08 | 2014-01-23 | Scinopharm Taiwan, Ltd. | Process for making 5-azacytosine nucleosides and their derivatives |
| BR112013025167A2 (en) | 2011-03-31 | 2019-09-24 | Celgene Int Sarl | process for preparing 5-azacitidine, or a salt, solvate, hydrate, or polymorph thereof, 5-azacitidine, 5-azacitidine salt, or a salt, solvate, hydrate, or polymorph |
| PH12014500477A1 (en) | 2011-08-30 | 2024-04-03 | Astex Pharmaceuticals Inc | Decitabine derivative formulations |
| BR112018000054A2 (en) | 2015-07-02 | 2018-09-04 | Otsuka Pharmaceutical Co., Ltd. | lyophilized pharmaceutical compositions |
| WO2017090264A1 (en) | 2015-11-27 | 2017-06-01 | 大原薬品工業株式会社 | 5'-position dibenzyl phosphoric acid ester of 5-azacytidine or 2'-deoxy body thereof |
| US10227374B2 (en) | 2016-04-21 | 2019-03-12 | Ohara Pharmaceutical Co., Ltd. | Silyl etherified derivatives of 5-azacytidines in carbohydrate moiety |
| WO2017183215A1 (en) | 2016-04-21 | 2017-10-26 | 大原薬品工業株式会社 | Sugar moiety silyl ether derivative of 5-azacytidine |
| JP6162349B1 (en) | 2016-04-21 | 2017-07-12 | 大原薬品工業株式会社 | Sacyl moiety silyl ether derivatives of 5-azacytidines |
| SG11202000932XA (en) | 2017-08-03 | 2020-02-27 | Otsuka Pharma Co Ltd | Drug compound and purification methods thereof |
-
1969
- 1969-04-23 CH CH619669A patent/CH527207A/en not_active IP Right Cessation
- 1969-04-24 GB GB1227691D patent/GB1227691A/en not_active Expired
- 1969-04-29 IT IT1620369A patent/IT1037009B/en active
- 1969-04-29 BE BE732268D patent/BE732268A/xx unknown
- 1969-05-03 DE DE19691922702 patent/DE1922702A1/en active Pending
- 1969-05-06 NL NL6906909A patent/NL6906909A/xx unknown
- 1969-05-07 ES ES366910A patent/ES366910A1/en not_active Expired
- 1969-05-07 FR FR6914547A patent/FR2008048A1/fr active Pending
- 1969-05-07 BR BR20860069A patent/BR6908600D0/en unknown
- 1969-05-07 AT AT439269A patent/AT306930B/en not_active IP Right Cessation
- 1969-05-08 CA CA050902A patent/CA921904A/en not_active Expired
- 1969-05-08 JP JP3545969A patent/JPS4916435B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL6906909A (en) | 1969-11-11 |
| FR2008048A1 (en) | 1970-01-16 |
| BE732268A (en) | 1969-10-01 |
| IT1037009B (en) | 1979-11-10 |
| CA921904A (en) | 1973-02-27 |
| JPS4916435B1 (en) | 1974-04-22 |
| GB1227691A (en) | 1971-04-07 |
| AT306930B (en) | 1973-04-25 |
| CH527207A (en) | 1972-08-31 |
| DE1922702A1 (en) | 1969-11-20 |
| BR6908600D0 (en) | 1973-02-22 |
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