NO20042031L - Syntese av syklosporin analoger - Google Patents
Syntese av syklosporin analogerInfo
- Publication number
- NO20042031L NO20042031L NO20042031A NO20042031A NO20042031L NO 20042031 L NO20042031 L NO 20042031L NO 20042031 A NO20042031 A NO 20042031A NO 20042031 A NO20042031 A NO 20042031A NO 20042031 L NO20042031 L NO 20042031L
- Authority
- NO
- Norway
- Prior art keywords
- cyclosporin
- isomers
- isa247
- mixture
- derivatives
- 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 5
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 5
- 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 3
- 108010036941 Cyclosporins Proteins 0.000 abstract 2
- 229930182912 cyclosporin Natural products 0.000 abstract 2
- 230000000707 stereoselective effect Effects 0.000 abstract 2
- 230000001988 toxicity Effects 0.000 abstract 2
- 231100000419 toxicity Toxicity 0.000 abstract 2
- 108010057559 voclosporin Proteins 0.000 abstract 2
- 229960005289 voclosporin Drugs 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
- 108010036949 Cyclosporine Proteins 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
- 229960001265 ciclosporin Drugs 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
- 230000037361 pathway Effects 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
-
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- 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
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- 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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- A61K9/10—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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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
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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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Nanotechnology (AREA)
- Gastroenterology & Hepatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Biotechnology (AREA)
- Dispersion Chemistry (AREA)
- Medical Informatics (AREA)
- General Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biomedical Technology (AREA)
- Virology (AREA)
Abstract
Oppfinnelsen angår isomeriske blandinger av syklosporin-analoger som strukturelt er lik syklosporin A. Blandingen innehar forbedret effektivitet og redusert toksisitet overfor de individuelle isomerene, og overfor de naturlig forekommende og andre nåværende kjente syklosporinene og syklosporin-derivatene. Utførelser av den foreliggende oppfinnelsen er rettet mot cis og trans-isomere av syklosporin A - analoger, omtalt som ISA247, og derivater av det. Blandinger av ISA247 isomere oppviser en kombinasjon av forbedret kraft og redusert toksisitet overfor de naturlig forekommende og ellers kjente syklosporinene. ISA247 isomere og alkylerte, arylerte og deuterierte derivater syntetiseres via stereoselektive baner hvor de særlige forholdene for en reaksjon bestemmer graden av stereoselektivitet. Stereoselektive baner kan utnytte en Wittig reaksjon, eller en organometallisk reagent omfattende uorganiske elementer så som bor, silisium, titan og litium. Forholdet mellom isomere i en blanding kan variere fra omtrent 10 til 90 vektprosent, basert på den totale vekten av blandingen.
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 |
---|---|
NO20042031L true NO20042031L (no) | 2004-05-19 |
NO332459B1 NO332459B1 (no) | 2012-09-24 |
Family
ID=26994746
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20042031A NO332459B1 (no) | 2001-10-19 | 2004-05-14 | Fremgangsmate for framstilling av en blanding av (E)- og (Z)-isomere av ISATX247. |
Country Status (28)
Country | Link |
---|---|
US (13) | US7141648B2 (no) |
EP (2) | EP1436321B9 (no) |
JP (3) | JP4261355B2 (no) |
KR (2) | KR101006206B1 (no) |
CN (1) | CN100334106C (no) |
AT (2) | ATE425178T1 (no) |
AU (2) | AU2002331509B2 (no) |
BR (1) | BRPI0213658A8 (no) |
CA (1) | CA2461740C (no) |
CO (1) | CO5580836A2 (no) |
CY (1) | CY1105111T1 (no) |
DE (2) | DE60231570D1 (no) |
DK (2) | DK1714977T3 (no) |
ES (2) | ES2326040T3 (no) |
HK (1) | HK1062568A1 (no) |
HR (2) | HRP20040355B1 (no) |
IL (3) | IL160763A0 (no) |
MA (1) | MA27293A1 (no) |
MX (1) | MXPA04003625A (no) |
NO (1) | NO332459B1 (no) |
NZ (1) | NZ531944A (no) |
PL (2) | PL210841B1 (no) |
PT (2) | PT1436321E (no) |
RU (1) | RU2321593C9 (no) |
SI (1) | SI1436321T1 (no) |
TN (1) | TNSN04068A1 (no) |
WO (1) | WO2003033526A2 (no) |
ZA (1) | ZA200402269B (no) |
Families Citing this family (53)
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 |
JP4261355B2 (ja) * | 2001-10-19 | 2009-04-30 | アイソテクニカ インコーポレイテッド | シクロスポリン類似体の合成法 |
EP1816138A1 (en) * | 2001-10-19 | 2007-08-08 | Isotechnika,Inc. | Cyclosporine analogue mixtures and their use as immunomodulating agents |
US7538084B2 (en) * | 2003-03-17 | 2009-05-26 | Amr Technology, Inc. | 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 |
WO2006014872A2 (en) * | 2004-07-29 | 2006-02-09 | Amr Technology, Inc. | Novel processes for stereoselective synthesis of trans isatx 247 |
US7378391B2 (en) * | 2004-09-29 | 2008-05-27 | Amr Technology, Inc. | Cyclosporin alkyne analogues and their pharmaceutical uses |
WO2006039164A2 (en) * | 2004-09-29 | 2006-04-13 | Amr Technology, Inc. | Novel cyclosporin analogues and their pharmaceutical uses |
US7361636B2 (en) * | 2004-10-06 | 2008-04-22 | Amr Technology, Inc. | Cyclosporin alkynes and their utility as pharmaceutical agents |
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 |
EP1928807A4 (en) * | 2005-09-02 | 2011-05-04 | Picobella Llc | ONCOGENIC REGULATORS RNA FOR DIAGNOSIS AND THERAPY |
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 |
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