CA2215930A1 - A process for the preparation of anthracycline antibiotics - Google Patents
A process for the preparation of anthracycline antibioticsInfo
- Publication number
- CA2215930A1 CA2215930A1 CA002215930A CA2215930A CA2215930A1 CA 2215930 A1 CA2215930 A1 CA 2215930A1 CA 002215930 A CA002215930 A CA 002215930A CA 2215930 A CA2215930 A CA 2215930A CA 2215930 A1 CA2215930 A1 CA 2215930A1
- Authority
- CA
- Canada
- Prior art keywords
- preparation
- epimerization
- anthracycline antibiotics
- group
- antibiotics
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title abstract 2
- 239000003817 anthracycline antibiotic agent Substances 0.000 title 1
- 238000006345 epimerization reaction Methods 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 229940045799 anthracyclines and related substance Drugs 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- WPJRFCZKZXBUNI-HCWXCVPCSA-N daunosamine Chemical group C[C@H](O)[C@@H](O)[C@@H](N)CC=O WPJRFCZKZXBUNI-HCWXCVPCSA-N 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
A process for the preparation of antibiotics of the anthracycline class of formula (A), wherein R1 is hydrogen, OH, or OCOR2, wherein R2 is a C1-C4-alkyl group; which comprises the epimerization of the 4' hydroxy group of the daunosamine residue by nucleophilic substitution of a triflate group with a carboxylate, which epimerization is carried out on the whole molecule with the hydroxy groups being protected, and subsequent transformation into the final product.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI95A000566 | 1995-03-22 | ||
| IT95MI000566A IT1275953B1 (en) | 1995-03-22 | 1995-03-22 | PROCEDURE FOR THE PREPARATION OF ANTIBIOTICS OF THE CLASS OF ANTHRACYCLINES |
| PCT/EP1996/001174 WO1996029335A1 (en) | 1995-03-22 | 1996-03-19 | A process for the preparation of anthracycline antibiotics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2215930A1 true CA2215930A1 (en) | 1996-09-26 |
| CA2215930C CA2215930C (en) | 2007-08-21 |
Family
ID=38434569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002215930A Expired - Fee Related CA2215930C (en) | 1995-03-22 | 1996-03-19 | A process for the preparation of anthracycline antibiotics |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2215930C (en) |
-
1996
- 1996-03-19 CA CA002215930A patent/CA2215930C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2215930C (en) | 2007-08-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |