HUP0202448A2 - Eljárás paclitaxel C-4-metil-karbonát-analóg előállítására - Google Patents
Eljárás paclitaxel C-4-metil-karbonát-analóg előállításáraInfo
- Publication number
- HUP0202448A2 HUP0202448A2 HU0202448A HUP0202448A HUP0202448A2 HU P0202448 A2 HUP0202448 A2 HU P0202448A2 HU 0202448 A HU0202448 A HU 0202448A HU P0202448 A HUP0202448 A HU P0202448A HU P0202448 A2 HUP0202448 A2 HU P0202448A2
- Authority
- HU
- Hungary
- Prior art keywords
- paclitaxel
- methyl carbonate
- preparation
- groups
- dab
- Prior art date
Links
- 229930012538 Paclitaxel Natural products 0.000 title abstract 4
- 229960001592 paclitaxel Drugs 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 title abstract 2
- CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical class COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 title 1
- 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 abstract 6
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- -1 paclitaxel C-4 methyl carbonate analog Chemical class 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- HOJZAHQWDXAPDJ-UHFFFAOYSA-N 3-anilino-2-hydroxypropanoic acid Chemical group OC(=O)C(O)CNC1=CC=CC=C1 HOJZAHQWDXAPDJ-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000011944 chemoselective reduction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 1
- 125000005911 methyl carbonate group Chemical group 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Abstract
A találmány tárgya eljárás az képletű paclitaxel C-4 metil-karbonát-analóg előállítására 10-dezacetil-baccatin III-ból (10-DAB). Az újszintézis során 10-DAB C-7, C-10 és C-13 hidroxi-csoportjait előbbszilil-éterekként védik, majd Red-Al-lal végzett kemoszelektívredukcióval a C-4 acetátot eltávolítva egy kulcsintermediernektekintett vegyületet állítanak elő, amelyre felviszik a C-4 metil-karbonát-csoportot, majd a védőcsoportok eltávolítása és szelektívvédőcsoportcserék során szelektíve acetileznek C-10 helyzetben, ésutána kapcsolják a paclitaxel C-13 helyzetű fenil-izoszerinoldalláncát. Az eljárás nagy előnye, hogy elkerülik a C-10dezacetilezett melléktermékek képződését, amelyek nehezen távolíthatókel az (I) képletű paclitaxel C-4 metil-karbonát-analóg mellől. Ó
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14839299P | 1999-08-11 | 1999-08-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUP0202448A2 true HUP0202448A2 (hu) | 2002-11-28 |
| HUP0202448A3 HUP0202448A3 (en) | 2005-02-28 |
Family
ID=22525581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0202448A HUP0202448A3 (en) | 1999-08-11 | 2000-08-03 | Process for preparation of paclitaxel c-4 methyl carbonate analog |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US6248908B1 (hu) |
| EP (1) | EP1206461B8 (hu) |
| JP (1) | JP2003506446A (hu) |
| KR (1) | KR100634249B1 (hu) |
| AT (1) | ATE266015T1 (hu) |
| AU (1) | AU769858B2 (hu) |
| CA (1) | CA2381401A1 (hu) |
| DE (1) | DE60010476T2 (hu) |
| DK (1) | DK1206461T3 (hu) |
| ES (1) | ES2219372T3 (hu) |
| HU (1) | HUP0202448A3 (hu) |
| IL (2) | IL147851A0 (hu) |
| MX (1) | MXPA02001396A (hu) |
| PE (1) | PE20010493A1 (hu) |
| PT (1) | PT1206461E (hu) |
| TW (1) | TWI269792B (hu) |
| UY (1) | UY26284A1 (hu) |
| WO (1) | WO2001010856A1 (hu) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6916942B2 (en) * | 2000-02-03 | 2005-07-12 | Bristol-Myers Squibb Company | Process for the preparation of C-4 carbonate taxanes |
| US6750246B1 (en) | 2000-02-03 | 2004-06-15 | Bristol-Myers Squibb Company | C-4 carbonate taxanes |
| MXPA03002494A (es) * | 2000-09-22 | 2004-05-24 | Bristol Myers Squibb Co | Metodo para reducir toxicidad de quimio terapias combinadas. |
| RS52904A (en) * | 2001-12-20 | 2006-12-15 | Bristol-Myers Squib Company | Pharmaceutical compositions of orally active taxane derivatives having enhanced bioavailability |
| US20070105944A1 (en) * | 2002-10-25 | 2007-05-10 | Comezoglu S N | Taxane metabolites |
| US7312240B2 (en) * | 2004-01-14 | 2007-12-25 | Virginia Tech Intellectual Properties, Inc. | Conformationally constrained paclitaxel analogs and their use as anticancer and anti-Alzheimers agents |
| GB0521373D0 (en) | 2005-10-20 | 2005-11-30 | Kudos Pharm Ltd | Pthalazinone derivatives |
| PL217731B1 (pl) | 2006-06-01 | 2014-08-29 | Tomasz Byrski | Sposób wykrywania genetycznie uwarunkowanej obniżonej odpowiedzi na chemioterapię cytostatykiem taksanowym, zastosowanie mutacji założycielskiej oraz zestawu do wykrywania takiej odpowiedzi |
| UY30639A1 (es) | 2006-10-17 | 2008-05-31 | Kudos Pharm Ltd | Derivados sustituidos de 2h-ftalazin-1-ona, sus formas cristalinas, proceso de preparacion y aplicaciones |
| US20080280910A1 (en) * | 2007-03-22 | 2008-11-13 | Keith Allan Menear | Phthalazinone derivatives |
| HUE030800T2 (hu) | 2008-10-07 | 2017-05-29 | Astrazeneca Uk Ltd | 514 számú gyógyszerkészítmény |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE34277E (en) | 1988-04-06 | 1993-06-08 | Centre National De La Recherche Scientifique | Process for preparing taxol |
| US5990325A (en) * | 1993-03-05 | 1999-11-23 | Florida State University | Process for the preparation of 9-desoxotaxol, 9-desoxobaccatin III and analogs thereof |
| US5274124A (en) | 1991-09-23 | 1993-12-28 | Florida State University | Metal alkoxides |
| US5399726A (en) * | 1993-01-29 | 1995-03-21 | Florida State University | Process for the preparation of baccatin III analogs bearing new C2 and C4 functional groups |
| SE470504B (sv) * | 1992-10-27 | 1994-06-06 | Ellemtel Utvecklings Ab | Sätt att i ett GSM-nät ta emot data för tilläggstjänster i MSC/VLR. |
| CA2119261C (en) * | 1992-12-23 | 2006-01-31 | Michael A. Poss | Novel sidechain-bearing taxanes and intermediates thereof |
| CN1097044C (zh) * | 1996-07-15 | 2002-12-25 | 亚库尔特株式会社总社 | 紫杉烷衍生物以及含有该衍生物的药物 |
-
2000
- 2000-08-03 JP JP2001515665A patent/JP2003506446A/ja not_active Withdrawn
- 2000-08-03 CA CA002381401A patent/CA2381401A1/en not_active Abandoned
- 2000-08-03 AU AU65169/00A patent/AU769858B2/en not_active Ceased
- 2000-08-03 MX MXPA02001396A patent/MXPA02001396A/es active IP Right Grant
- 2000-08-03 EP EP00952478A patent/EP1206461B8/en not_active Expired - Lifetime
- 2000-08-03 IL IL14785100A patent/IL147851A0/xx not_active IP Right Cessation
- 2000-08-03 AT AT00952478T patent/ATE266015T1/de not_active IP Right Cessation
- 2000-08-03 ES ES00952478T patent/ES2219372T3/es not_active Expired - Lifetime
- 2000-08-03 DE DE60010476T patent/DE60010476T2/de not_active Expired - Fee Related
- 2000-08-03 DK DK00952478T patent/DK1206461T3/da active
- 2000-08-03 WO PCT/US2000/021260 patent/WO2001010856A1/en active IP Right Grant
- 2000-08-03 PT PT00952478T patent/PT1206461E/pt unknown
- 2000-08-03 HU HU0202448A patent/HUP0202448A3/hu unknown
- 2000-08-03 KR KR1020027001746A patent/KR100634249B1/ko not_active IP Right Cessation
- 2000-08-07 TW TW089115879A patent/TWI269792B/zh not_active IP Right Cessation
- 2000-08-08 PE PE2000000802A patent/PE20010493A1/es not_active Application Discontinuation
- 2000-08-08 UY UY26284A patent/UY26284A1/es not_active Application Discontinuation
- 2000-08-10 US US09/635,553 patent/US6248908B1/en not_active Expired - Fee Related
-
2001
- 2001-03-20 US US09/813,085 patent/US6353120B2/en not_active Expired - Fee Related
-
2005
- 2005-05-11 IL IL168553A patent/IL168553A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2219372T3 (es) | 2004-12-01 |
| PT1206461E (pt) | 2004-09-30 |
| DK1206461T3 (da) | 2004-08-16 |
| EP1206461A4 (en) | 2003-03-26 |
| JP2003506446A (ja) | 2003-02-18 |
| IL147851A0 (en) | 2002-08-14 |
| HUP0202448A3 (en) | 2005-02-28 |
| CA2381401A1 (en) | 2001-02-15 |
| UY26284A1 (es) | 2001-03-16 |
| US6353120B2 (en) | 2002-03-05 |
| KR100634249B1 (ko) | 2006-10-17 |
| US6248908B1 (en) | 2001-06-19 |
| AU769858B2 (en) | 2004-02-05 |
| DE60010476T2 (de) | 2005-04-14 |
| EP1206461B1 (en) | 2004-05-06 |
| AU6516900A (en) | 2001-03-05 |
| EP1206461A1 (en) | 2002-05-22 |
| PE20010493A1 (es) | 2001-07-06 |
| MXPA02001396A (es) | 2002-08-12 |
| EP1206461B8 (en) | 2004-07-21 |
| US20010044549A1 (en) | 2001-11-22 |
| IL168553A (en) | 2007-07-04 |
| TWI269792B (en) | 2007-01-01 |
| ATE266015T1 (de) | 2004-05-15 |
| DE60010476D1 (de) | 2004-06-09 |
| KR20020031405A (ko) | 2002-05-01 |
| WO2001010856A1 (en) | 2001-02-15 |
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