MA27293A1 - Synthese d'analogues de la cyclosporine - Google Patents
Synthese d'analogues de la cyclosporineInfo
- Publication number
- MA27293A1 MA27293A1 MA27597A MA27597A MA27293A1 MA 27293 A1 MA27293 A1 MA 27293A1 MA 27597 A MA27597 A MA 27597A MA 27597 A MA27597 A MA 27597A MA 27293 A1 MA27293 A1 MA 27293A1
- Authority
- MA
- Morocco
- Prior art keywords
- ciclosporin
- isomers
- analogs
- weight
- isatx247
- Prior art date
Links
- 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 4
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 2
- 230000000707 stereoselective effect Effects 0.000 abstract 2
- 108010057559 voclosporin Proteins 0.000 abstract 2
- 229960005289 voclosporin Drugs 0.000 abstract 2
- 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 abstract 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- 229930105110 Cyclosporin A Natural products 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
- 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
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
- C07K7/645—Cyclosporins; Related peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
- A61K38/13—Cyclosporins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
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- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing 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
- Y10S530/806—Antigenic peptides or proteins
Abstract
L'invention concerne des mélanges isomères d'analogues de la ciclosporine qui sont structurellement semblables à la ciclosporine A. Les mélanges ont une efficacité améliorée et une toxicité réduite par rapport aux isomères individuels et par rapport aux ciclosporines et dérivés de la ciclosporine naturels et présentement connus. Les modes de réalisation de la présente invention concernent des isomères cis et trans d'analogues de la ciclosporine A cités ISATX247, et des dérivés de ceux-ci. Les isomères d'ISATX247 et les dérivés alkylés, arylés, et deutérés sont synthétisés par des processus stéréosélectifs oé les conditions particulières d'une réaction déterminent le degrée de stéréosélectivité. Les processus stéréosélectifs peuvent utiliser une réaction de Wittig, ou un réactif organométallique comprenant des éléments inorganiques tels que les bore, silicium, titanium et lithium. Le rapport des isomères dans un mélange peut varier de 10 à 90 pour cent environ en poids d'isomère (E) pour environ 90 à 10 pour cent en poids d'isomère (Z), basé sur le poids total du mélange.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US34620101P | 2001-10-19 | 2001-10-19 | |
US37059602P | 2002-04-05 | 2002-04-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
MA27293A1 true MA27293A1 (fr) | 2005-05-02 |
Family
ID=26994746
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
MA27597A MA27293A1 (fr) | 2001-10-19 | 2004-03-26 | Synthese d'analogues de la cyclosporine |
Country Status (28)
Country | Link |
---|---|
US (13) | US6998385B2 (fr) |
EP (2) | EP1714977B1 (fr) |
JP (3) | JP4261355B2 (fr) |
KR (2) | KR100982466B1 (fr) |
CN (1) | CN100334106C (fr) |
AT (2) | ATE332917T1 (fr) |
AU (2) | AU2002331509B2 (fr) |
BR (1) | BRPI0213658A8 (fr) |
CA (1) | CA2461740C (fr) |
CO (1) | CO5580836A2 (fr) |
CY (1) | CY1105111T1 (fr) |
DE (2) | DE60231570D1 (fr) |
DK (2) | DK1714977T3 (fr) |
ES (2) | ES2326040T3 (fr) |
HK (1) | HK1062568A1 (fr) |
HR (2) | HRP20040355B1 (fr) |
IL (3) | IL160763A0 (fr) |
MA (1) | MA27293A1 (fr) |
MX (1) | MXPA04003625A (fr) |
NO (1) | NO332459B1 (fr) |
NZ (1) | NZ531944A (fr) |
PL (2) | PL210841B1 (fr) |
PT (2) | PT1714977E (fr) |
RU (1) | RU2321593C9 (fr) |
SI (1) | SI1436321T1 (fr) |
TN (1) | TNSN04068A1 (fr) |
WO (1) | WO2003033526A2 (fr) |
ZA (1) | ZA200402269B (fr) |
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 |
PL210697B1 (pl) * | 2001-10-19 | 2012-02-29 | Isotechnika Inc | Kompozycja zawierająca mieszaninę izomerów analogu cyklosporyny i zastosowanie tej mieszaniny |
BRPI0213658A8 (pt) | 2001-10-19 | 2016-12-06 | F Hoffmann La Roche Ltd | 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 |
AU2004222306A1 (en) * | 2003-03-17 | 2004-09-30 | 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 (fr) * | 2004-07-29 | 2012-08-14 | Amr Technology, Inc. | Nouveaux procedes de synthese stereoselective d'un compose isa<sb>tx</sb>247 trans |
US7378391B2 (en) * | 2004-09-29 | 2008-05-27 | Amr Technology, Inc. | Cyclosporin alkyne analogues and their pharmaceutical uses |
US7511013B2 (en) * | 2004-09-29 | 2009-03-31 | Amr Technology, Inc. | Cyclosporin analogues and their pharmaceutical uses |
JP2008515886A (ja) * | 2004-10-06 | 2008-05-15 | エーエムアール テクノロジー インコーポレイテッド | シクロスポリンアルキンおよびそれらの医用薬剤としての有用性 |
CN101120012A (zh) * | 2004-12-17 | 2008-02-06 | 伊素制药公司 | 环孢菌素类似物的代谢物 |
WO2007028030A2 (fr) * | 2005-09-02 | 2007-03-08 | Picobella, Llc | Arn regulateurs oncogenes pour le diagnostic et la therapie |
US7459280B2 (en) * | 2006-02-27 | 2008-12-02 | Picobella, Llc | Methods for diagnosing and treating kidney cancer |
US20070232532A1 (en) * | 2006-03-28 | 2007-10-04 | Amr Technology, Inc. | Use of cyclosporin alkene analogues for preventing or treating viral-induced disorders |
US7696166B2 (en) * | 2006-03-28 | 2010-04-13 | Albany Molecular Research, Inc. | Use of cyclosporin alkyne/alkene analogues for preventing or treating viral-induced disorders |
US7696165B2 (en) * | 2006-03-28 | 2010-04-13 | Albany Molecular Research, Inc. | Use of cyclosporin alkyne analogues for preventing or treating viral-induced disorders |
US20080267977A1 (en) * | 2007-04-26 | 2008-10-30 | Friedrich-Alexander University Of Erlangen-Nuremberg | Combined immunological agent and sensitizing agent for the treatment of cancer |
CA3014633C (fr) * | 2007-10-08 | 2022-05-17 | Aurinia Pharmaceuticals Inc. | Compositions ophtalmiques comprenant des inhibiteurs de la calcineurine ou des inhibiteurs de mtor |
EP2151450A1 (fr) * | 2008-07-29 | 2010-02-10 | Sandoz AG | Procédé de préparation d'oligopeptides cycliques microbiologiques |
US20130190223A1 (en) * | 2008-07-30 | 2013-07-25 | Isotechnika Pharma Inc. | Nonimmunosuppressive cyclosporine analogue molecules |
DE102008060549A1 (de) | 2008-12-04 | 2010-06-10 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Wirkstoff-Peptid-Konstrukt zur extrazellulären Anreicherung |
CA2751210C (fr) | 2009-01-30 | 2015-04-21 | Enanta Pharmaceuticals, Inc. | Analogues de la cyclosporine pour prevenir ou traiter une infection par l'hepatite c |
US8481483B2 (en) | 2009-02-19 | 2013-07-09 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues |
CA2764635C (fr) | 2009-06-09 | 2018-05-22 | Lux Biosciences, Inc. | Systemes d'administration de medicament topique pour une utilisation ophtalmique |
US8685917B2 (en) | 2009-07-09 | 2014-04-01 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues |
US8367053B2 (en) | 2009-07-09 | 2013-02-05 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues |
US8349312B2 (en) | 2009-07-09 | 2013-01-08 | Enanta Pharmaceuticals, Inc. | Proline substituted cyclosporin analogues |
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