BRPI0509854A - composto, métodos para a preparação regio-especìfica de um 42-éster de rapamicina ou 42-éster de prolina-rapamicina e para a preparação de um 42-éster de prolina-rapamicina, composição, e, produto - Google Patents
composto, métodos para a preparação regio-especìfica de um 42-éster de rapamicina ou 42-éster de prolina-rapamicina e para a preparação de um 42-éster de prolina-rapamicina, composição, e, produtoInfo
- Publication number
- BRPI0509854A BRPI0509854A BRPI0509854-8A BRPI0509854A BRPI0509854A BR PI0509854 A BRPI0509854 A BR PI0509854A BR PI0509854 A BRPI0509854 A BR PI0509854A BR PI0509854 A BRPI0509854 A BR PI0509854A
- Authority
- BR
- Brazil
- Prior art keywords
- ester
- rapamycin
- proline
- cci
- preparation
- Prior art date
Links
- 229960002930 sirolimus Drugs 0.000 title abstract 9
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 title abstract 7
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 title abstract 6
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 title abstract 4
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 title abstract 2
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 abstract 2
- CBPNZQVSJQDFBE-FUXHJELOSA-N Temsirolimus Chemical compound C1C[C@@H](OC(=O)C(C)(CO)CO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 CBPNZQVSJQDFBE-FUXHJELOSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229960000235 temsirolimus Drugs 0.000 abstract 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 108010079522 solysime Proteins 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
COMPOSTO, MéTODOS PARA A PREPARAçãO REGIO-ESPECìFICA DE UM 42-éSTER DE RAPAMICINA OU 42-éSTER DE PROLINARAPAMICINA E PARA A PREPARAçãO DE UM 42-éSTER DE PROLINA-RAPAMICINA, COMPOSIçãO, E, PRODUTO. é divulgado 42-éster de prolina-rapamicina com ácido 2,2- bis (hidroximetil) propiónico (prolina-CCI-779) bem como um método para a preparação regio-específica de um 42-éster de rapamicina ou 42-éster de prolina-rapamicina com ácido 2,2-bis (hidroximetil) propiónico (CCI-779 e prolina-CCI-779) que compreende as etapas de: (a) reagir rapamicina ou prolina-rapamicina com um derivado de éster ativado de ácido 2,2-bis (hidroximetil)propiónico tendo a estrutura (A) em que R~ 1~ e R~ 2~ são hidrogênio ou quando juntos formam um cetal com a estrutura (B) em que R~ 3~ e R~ 4~ são, cada um, independentemente, hidrogênio, alquila C~ 1-6~, linear ou ramificado ou quando juntos formam cicloalquila C~ 5-7~ ou quando juntos formam boronato cíclico com a estrutura (C) em que R~ 5~ é selecionado de metila, etila, n-propila, iso-propila, n-butila, iso-butila e fenila; em um solvente orgânico adequado na presença de uma quantidade eficaz de lipase microbiana e (b) desproteger o intermediário resultante da etapa (a) fornecer CCI-779 ou prolina-CCI-779.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56206904P | 2004-04-14 | 2004-04-14 | |
| US62359404P | 2004-10-29 | 2004-10-29 | |
| PCT/US2005/012030 WO2005100366A1 (en) | 2004-04-14 | 2005-04-12 | Proline cci-779 (proline-rapamycin 42-ester with 2,2-bis (hydroxymethyl) propionic acid) and two-step enzymatic synthesis of proline cci-779 and cci-779 using microbial lipase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0509854A true BRPI0509854A (pt) | 2007-10-23 |
Family
ID=34968422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0509854-8A BRPI0509854A (pt) | 2004-04-14 | 2005-04-12 | composto, métodos para a preparação regio-especìfica de um 42-éster de rapamicina ou 42-éster de prolina-rapamicina e para a preparação de um 42-éster de prolina-rapamicina, composição, e, produto |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7202256B2 (pt) |
| EP (1) | EP1751168A1 (pt) |
| JP (1) | JP2007532650A (pt) |
| AR (1) | AR048603A1 (pt) |
| AU (1) | AU2005233612A1 (pt) |
| BR (1) | BRPI0509854A (pt) |
| CA (1) | CA2564811A1 (pt) |
| MX (1) | MXPA06011883A (pt) |
| PA (1) | PA8630001A1 (pt) |
| PE (1) | PE20060335A1 (pt) |
| SV (1) | SV2005002082A (pt) |
| TW (1) | TW200533673A (pt) |
| WO (1) | WO2005100366A1 (pt) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0313024A (pt) | 2002-07-30 | 2005-07-12 | Wyeth Corp | Formulações parenterais contendo um hidroxiéster de rapamicina |
| JP2007532655A (ja) * | 2004-04-14 | 2007-11-15 | ワイス | ラパマイシンコンジュゲートおよび抗体のための前駆体である、ジカルボン酸とのラパマイシン４２−エステルおよびジカルボン酸とのｆｋ−５０６３２−エステルの調製プロセス |
| MXPA06012404A (es) * | 2004-04-27 | 2007-01-17 | Wyeth Corp | Marcado de rapamicina usando metilasas especificas de rapamicina. |
| GT200500216A (es) * | 2004-08-10 | 2006-03-02 | Derivados de cci-779 y metodos para su preparacion | |
| US7538119B2 (en) * | 2005-11-04 | 2009-05-26 | Wyeth | 41-Methoxy isotope labeled rapamycin 42-ester |
| BRPI0619578A2 (pt) | 2005-12-07 | 2011-10-04 | Wyeth Corp | processo para preparar um 42-éster de rapamicina, composto, método para isolar o boronato do 42-éster de rapamicina bruto a partir do licor mãe, método para purificação de um boronato do 42-éster de rapamicina, e, boronato de cci-779 |
| AU2006331874A1 (en) * | 2005-12-20 | 2007-07-05 | Wyeth | Control of CCI-779 dosage form stability through control of drug substance impurities |
| US8414525B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US8414910B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US8425459B2 (en) | 2006-11-20 | 2013-04-23 | Lutonix, Inc. | Medical device rapid drug releasing coatings comprising a therapeutic agent and a contrast agent |
| US20080276935A1 (en) | 2006-11-20 | 2008-11-13 | Lixiao Wang | Treatment of asthma and chronic obstructive pulmonary disease with anti-proliferate and anti-inflammatory drugs |
| US9737640B2 (en) | 2006-11-20 | 2017-08-22 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US9700704B2 (en) | 2006-11-20 | 2017-07-11 | Lutonix, Inc. | Drug releasing coatings for balloon catheters |
| US8414909B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US8414526B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Medical device rapid drug releasing coatings comprising oils, fatty acids, and/or lipids |
| US8998846B2 (en) | 2006-11-20 | 2015-04-07 | Lutonix, Inc. | Drug releasing coatings for balloon catheters |
| TW200845960A (en) * | 2007-04-05 | 2008-12-01 | Wyeth Corp | Wortmannin-rapalog conjugate and uses thereof |
| CL2009000844A1 (es) * | 2008-04-11 | 2009-06-12 | Galaxy Biotech Llc | Metodo para tratar cancer en un paciente que comprende la administracion de un primer agente que es inhibidor de factor de crecimiento de hepatocito (hgf) en combinacion con un segundo agente que es agonista de pten. |
| WO2010024898A2 (en) | 2008-08-29 | 2010-03-04 | Lutonix, Inc. | Methods and apparatuses for coating balloon catheters |
| US8754207B2 (en) | 2009-09-25 | 2014-06-17 | Cadila Healthcare Limited | Process for the preparation of rapamycin derivatives |
| AU2011260016B2 (en) | 2010-06-02 | 2013-08-22 | Fresenius Kabi Oncology Ltd. | Stable pharmaceutical compositions of Rapamycin esters |
| CN102020662B (zh) * | 2011-01-07 | 2013-02-13 | 天津市炜杰科技有限公司 | 一种驮瑞塞尔制备方法 |
| CN103517911B (zh) | 2011-04-01 | 2016-08-17 | 桑多斯股份公司 | 雷帕霉素在c-42位上的区域选择性酰化 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA737247B (en) | 1972-09-29 | 1975-04-30 | Ayerst Mckenna & Harrison | Rapamycin and process of preparation |
| CA2106034A1 (en) | 1992-09-24 | 1994-03-25 | Ralph J. Russo | 21-norrapamycin |
| US5362718A (en) | 1994-04-18 | 1994-11-08 | American Home Products Corporation | Rapamycin hydroxyesters |
| GB9710962D0 (en) | 1997-05-28 | 1997-07-23 | Univ Cambridge Tech | Polyketides and their synthesis |
| US6277983B1 (en) | 2000-09-27 | 2001-08-21 | American Home Products Corporation | Regioselective synthesis of rapamycin derivatives |
| TWI256395B (en) | 1999-09-29 | 2006-06-11 | Wyeth Corp | Regioselective synthesis of rapamycin derivatives |
| BR0313024A (pt) | 2002-07-30 | 2005-07-12 | Wyeth Corp | Formulações parenterais contendo um hidroxiéster de rapamicina |
| CA2496332A1 (en) | 2002-09-17 | 2004-04-01 | Wyeth | Oral formulations |
| AU2004265267A1 (en) | 2003-08-07 | 2005-02-24 | Wyeth | Regioselective synthesis of CCI-779 |
-
2005
- 2005-04-12 JP JP2007508408A patent/JP2007532650A/ja not_active Withdrawn
- 2005-04-12 CA CA002564811A patent/CA2564811A1/en not_active Abandoned
- 2005-04-12 MX MXPA06011883A patent/MXPA06011883A/es active IP Right Grant
- 2005-04-12 US US11/103,779 patent/US7202256B2/en not_active Expired - Fee Related
- 2005-04-12 BR BRPI0509854-8A patent/BRPI0509854A/pt not_active IP Right Cessation
- 2005-04-12 EP EP05744572A patent/EP1751168A1/en not_active Withdrawn
- 2005-04-12 AU AU2005233612A patent/AU2005233612A1/en not_active Withdrawn
- 2005-04-12 WO PCT/US2005/012030 patent/WO2005100366A1/en not_active Application Discontinuation
- 2005-04-13 PA PA20058630001A patent/PA8630001A1/es unknown
- 2005-04-13 SV SV2005002082A patent/SV2005002082A/es not_active Application Discontinuation
- 2005-04-13 TW TW094111636A patent/TW200533673A/zh unknown
- 2005-04-13 AR ARP050101448A patent/AR048603A1/es unknown
- 2005-04-13 PE PE2005000408A patent/PE20060335A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| SV2005002082A (es) | 2005-12-13 |
| AR048603A1 (es) | 2006-05-10 |
| AU2005233612A1 (en) | 2005-10-27 |
| CA2564811A1 (en) | 2005-10-27 |
| US20050234086A1 (en) | 2005-10-20 |
| US7202256B2 (en) | 2007-04-10 |
| TW200533673A (en) | 2005-10-16 |
| JP2007532650A (ja) | 2007-11-15 |
| EP1751168A1 (en) | 2007-02-14 |
| PA8630001A1 (es) | 2006-06-02 |
| PE20060335A1 (es) | 2006-05-25 |
| WO2005100366A1 (en) | 2005-10-27 |
| MXPA06011883A (es) | 2006-12-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B08F | Application dismissed because of non-payment of annual fees [chapter 8.6 patent gazette] |
Free format text: REFERENTE AS 6A E 7A ANUIDADES. |
|
| B08K | Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette] |
Free format text: REFERENTE AO DESPACHO 8.6 PUBLICADO NA RPI 2158 DE 15/05/2012. |