CA2558908A1 - 10-deacetylbaccatine iii and 10-deacetyl 14.beta.-hydroxybaccatine iii derivatives and intermediates useful in the preparation thereof - Google Patents
10-deacetylbaccatine iii and 10-deacetyl 14.beta.-hydroxybaccatine iii derivatives and intermediates useful in the preparation thereof Download PDFInfo
- Publication number
- CA2558908A1 CA2558908A1 CA002558908A CA2558908A CA2558908A1 CA 2558908 A1 CA2558908 A1 CA 2558908A1 CA 002558908 A CA002558908 A CA 002558908A CA 2558908 A CA2558908 A CA 2558908A CA 2558908 A1 CA2558908 A1 CA 2558908A1
- Authority
- CA
- Canada
- Prior art keywords
- iii
- deacetyl
- beta
- preparation
- intermediates useful
- 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
- 239000000543 intermediate Substances 0.000 title claims abstract 3
- YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 title abstract 2
- YWLXLRUDGLRYDR-LUPIKGFISA-N 7-epi-10-deacetylbaccatin iii Chemical group O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-LUPIKGFISA-N 0.000 title 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical group NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- 229940123237 Taxane Drugs 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 231100000433 cytotoxic Toxicity 0.000 abstract 1
- 230000001472 cytotoxic effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
Landscapes
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention is directed to intermediates useful in the preparation of novel derivatives of 10-deacetylbaccatine III and of 10-deacetyl-14.beta.-hydroxybaccatine III. These novel derivatives have cytoxic and anti-tumoral activity. They are prepared starting from the so-called syntons or from other taxanes of natural origin, by selective oxidation of the hydroxyl in position 10 to keto function and subsequent esterfication in position 13, if necessary, with isoserine chains variously substituted. The products of the invention can be administered by injection or orally, when suitably formulated.
Claims
1. Intermediates of formula 9b:
wherein R2' is straight or branched alkyl or alkenyl group, containing one to five carbon atoms, or an aryl residue, or a tert-butoxy group.
wherein R2' is straight or branched alkyl or alkenyl group, containing one to five carbon atoms, or an aryl residue, or a tert-butoxy group.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI95A000533 | 1995-03-17 | ||
| IT95MI000533A IT1275936B1 (en) | 1995-03-17 | 1995-03-17 | DERIVATIVES OF 10-DEACETYLBACCATIN III AND OF 10-DEACETYL-14B- HYDROXYBACCATIN III THEIR METHOD OF PREPARATION AND FORMULATIONS |
| CA002215682A CA2215682C (en) | 1995-03-17 | 1996-03-04 | 10-deacetylbaccatine iii and 10-deacetyl 14.beta.-hydroxybaccatine iii derivatives, a process for the preparation thereof and pharmaceutical compositions containing them |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002215682A Division CA2215682C (en) | 1995-03-17 | 1996-03-04 | 10-deacetylbaccatine iii and 10-deacetyl 14.beta.-hydroxybaccatine iii derivatives, a process for the preparation thereof and pharmaceutical compositions containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2558908A1 true CA2558908A1 (en) | 1996-09-26 |
| CA2558908C CA2558908C (en) | 2009-12-22 |
Family
ID=37441499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002558908A Expired - Lifetime CA2558908C (en) | 1995-03-17 | 1996-03-04 | 10-deacetylbaccatine iii and 10-deacetyl 14.beta.-hydroxybaccatine iii derivatives and intermediates useful in the preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2558908C (en) |
-
1996
- 1996-03-04 CA CA002558908A patent/CA2558908C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2558908C (en) | 2009-12-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20160304 |