BRPI0213658A8 - Método para preparar uma mistura isomérica predeterminada ou não dos análogos de ciclosporina a modificados no resíduo de 1-aminoácido, métodopara produzir uma mistura enriquecida com e-isômero ou com z-isômero de análogos de ciclosporina a modificados no resíduo de 1-aminoácido, mistura de (e) e (z)-isômeros, composição, método para a síntese estereoseletiva do z-isômero de isatx247, método para a preparação de aldeído do ciclosporina a - Google Patents
Método para preparar uma mistura isomérica predeterminada ou não dos análogos de ciclosporina a modificados no resíduo de 1-aminoácido, métodopara produzir uma mistura enriquecida com e-isômero ou com z-isômero de análogos de ciclosporina a modificados no resíduo de 1-aminoácido, mistura de (e) e (z)-isômeros, composição, método para a síntese estereoseletiva do z-isômero de isatx247, método para a preparação de aldeído do ciclosporina aInfo
- Publication number
- BRPI0213658A8 BRPI0213658A8 BRPI0213658A BR0213658A BRPI0213658A8 BR PI0213658 A8 BRPI0213658 A8 BR PI0213658A8 BR PI0213658 A BRPI0213658 A BR PI0213658A BR 0213658 A BR0213658 A BR 0213658A BR PI0213658 A8 BRPI0213658 A8 BR PI0213658A8
- Authority
- BR
- Brazil
- Prior art keywords
- isomer
- cyclosporin
- mixture
- amino acid
- isomers
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title abstract 12
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical class CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 title abstract 9
- 238000000034 method Methods 0.000 title abstract 6
- BICRTLVBTLFLRD-PTWUADNWSA-N voclosporin Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C=C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O BICRTLVBTLFLRD-PTWUADNWSA-N 0.000 title abstract 4
- 229930105110 Cyclosporin A Natural products 0.000 title abstract 3
- 108010036949 Cyclosporine Proteins 0.000 title abstract 3
- 108010057559 voclosporin Proteins 0.000 title abstract 3
- 229960005289 voclosporin Drugs 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 229960001265 ciclosporin Drugs 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- -1 CYCLOSPORIN A ALDEHYDE Chemical class 0.000 title 1
- 230000000707 stereoselective effect Effects 0.000 abstract 3
- 108010036941 Cyclosporins Proteins 0.000 abstract 2
- 229930182912 cyclosporin Natural products 0.000 abstract 2
- 230000037361 pathway Effects 0.000 abstract 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 1
- 238000007239 Wittig reaction Methods 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 229910052796 boron Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002524 organometallic group Chemical group 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 239000010703 silicon Substances 0.000 abstract 1
- 229910052719 titanium Inorganic materials 0.000 abstract 1
- 239000010936 titanium Substances 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
Classifications
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- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
- A61K38/13—Cyclosporins
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
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- C07K—PEPTIDES
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
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Abstract
MÉTODO PARA PREPARAR UMA MISTURA ISOMÉRICA PREDETERMINADA OU NÃO DOS ANÁLOGOS DE CICLOSPORINA A MODIFICADOS NO RESÍDUO DE 1-AMINOÁCIDO, MÉTODO PARA PRODUZIR UMA MISTURA ENRIQUECIDA COM E-ISÔMERO OU COM Z-ISÔMERO DE ANÁLOGOS DE CICLOSPORINA A MODIFICADOS NO RESÍDUO DE 1-AMINOÁCIDO, MISTURA DE (E) E (Z)-ISÔMEROS, COMPOSIÇÃO, MÉTODO PARA A SÍNTESE ESTEREOSELETIVA DO Z-ISÔMERO DE ISATX247, MÉTODO PARA A PREPARAÇÃO E ALDEÍDO DO CICLOSPORINA A. A invenção refere-se a misturas isoméricas dos análogos de ciclosporina que são estruturalmente similares à ciclosporina A. As misturas possuem uma maior eficácia e uma toxicidade reduzida em relação aos isômeros individuais e em relação a ciclosporinas de ocorrência natural e outras ciclosporinas atualmente conhecidas e derivados de ciclosporina. As realizações da presente invenção referem se a cis e trans-isômeros dos análogos de ciclosporina A indicados como ISATX247, e derivados destes. Os isômeros de ISATX247 e os derivados alquilados, arilados e deuterados são sintetizados por vias estereoseletivas onde as condições particulares de uma reação determinam o grau de estereoseletividade. As vias estereoseletivas podem utilizar uma reação de Wittig, ou um reagente organometálico que compreende elementos inorgânicos tais como o boro, o silício, o titânio, e o lítio. A razão dos isômeros em uma mistura pode variar de aproximadamente 10 a 90 por cento em peso do (E)-isômero para aproximadamente 90 a 10 por cento em peso do (Z)-isômero, com base no peso total da mistura.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34620101P | 2001-10-19 | 2001-10-19 | |
| US37059602P | 2002-04-05 | 2002-04-05 | |
| PCT/CA2002/001559 WO2003033526A2 (en) | 2001-10-19 | 2002-10-17 | Synthesis of cyclosporin analogs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR0213658A BR0213658A (pt) | 2004-10-26 |
| BRPI0213658A8 true BRPI0213658A8 (pt) | 2016-12-06 |
Family
ID=26994746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0213658A BRPI0213658A8 (pt) | 2001-10-19 | 2002-10-17 | Método para preparar uma mistura isomérica predeterminada ou não dos análogos de ciclosporina a modificados no resíduo de 1-aminoácido, métodopara produzir uma mistura enriquecida com e-isômero ou com z-isômero de análogos de ciclosporina a modificados no resíduo de 1-aminoácido, mistura de (e) e (z)-isômeros, composição, método para a síntese estereoseletiva do z-isômero de isatx247, método para a preparação de aldeído do ciclosporina a |
Country Status (28)
| Country | Link |
|---|---|
| US (13) | US6998385B2 (pt) |
| EP (2) | EP1714977B1 (pt) |
| JP (3) | JP4261355B2 (pt) |
| KR (2) | KR100982466B1 (pt) |
| CN (1) | CN100334106C (pt) |
| AT (2) | ATE332917T1 (pt) |
| AU (2) | AU2002331509B2 (pt) |
| BR (1) | BRPI0213658A8 (pt) |
| CA (1) | CA2461740C (pt) |
| CO (1) | CO5580836A2 (pt) |
| CY (1) | CY1105111T1 (pt) |
| DE (2) | DE60213115T2 (pt) |
| DK (2) | DK1436321T3 (pt) |
| ES (2) | ES2326040T3 (pt) |
| HK (1) | HK1062568A1 (pt) |
| HR (2) | HRP20040355B1 (pt) |
| IL (3) | IL160763A0 (pt) |
| MA (1) | MA27293A1 (pt) |
| MX (1) | MXPA04003625A (pt) |
| NO (1) | NO332459B1 (pt) |
| NZ (1) | NZ531944A (pt) |
| PL (2) | PL210795B1 (pt) |
| PT (2) | PT1436321E (pt) |
| RU (1) | RU2321593C9 (pt) |
| SI (1) | SI1436321T1 (pt) |
| TN (1) | TNSN04068A1 (pt) |
| WO (1) | WO2003033526A2 (pt) |
| ZA (1) | ZA200402269B (pt) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030220234A1 (en) * | 1998-11-02 | 2003-11-27 | Selvaraj Naicker | Deuterated cyclosporine analogs and their use as immunodulating agents |
| KR100992850B1 (ko) * | 2001-10-19 | 2010-11-09 | 이소테크니카 인코포레이티드 | 시클로스포린 유사체 혼합물 및 면역조절제로서 이들의 용도 |
| EP1714977B1 (en) * | 2001-10-19 | 2009-03-11 | Isotechnika Inc. | Synthesis of cyclosporin analogs |
| EP1603512A2 (en) * | 2003-03-17 | 2005-12-14 | Albany Molecular Research, Inc. | Novel cyclosporins |
| TW200505946A (en) * | 2003-04-08 | 2005-02-16 | Hoffmann La Roche | Process for preparation of cyclosporin a analog |
| US20040266669A1 (en) * | 2003-06-20 | 2004-12-30 | Wu Frank X. H. | Cyclosporin derivatives for the treatment of immune disorders |
| CA2575280C (en) * | 2004-07-29 | 2012-08-14 | Amr Technology, Inc. | Novel processes for stereoselective synthesis of trans isatx 247 |
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