HRP20040355B1 - Sinteza ciklosporinskih analoga - Google Patents
Sinteza ciklosporinskih analogaInfo
- Publication number
- HRP20040355B1 HRP20040355B1 HRP20040355AA HRP20040355A HRP20040355B1 HR P20040355 B1 HRP20040355 B1 HR P20040355B1 HR P20040355A A HRP20040355A A HR P20040355AA HR P20040355 A HRP20040355 A HR P20040355A HR P20040355 B1 HRP20040355 B1 HR P20040355B1
- Authority
- HR
- Croatia
- Prior art keywords
- sub
- isomers
- cyclosporin
- isa
- 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
- 108010036941 Cyclosporins Proteins 0.000 abstract 2
- 229930182912 cyclosporin Natural products 0.000 abstract 2
- 230000037361 pathway Effects 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
- 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
- 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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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- 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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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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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
Izum je usmjeren prema izomernim smjesama ciklosporinskih analoga, strukturno sličnima ciklosporinu A. Smjese posjeduju povećanu djelotvornost i smanjenu toksičnost pred pojedinačnim izomerima i prirodnim i ostalim trenutno poznatim ciklosporinima i ciklosporinskim derivatima. Ostvarenja ovog izuma usmjerena su prema cis- i trans-izomerima analoga ciklosporina A, nazvanim ISA<SUB>TX</SUB>247, kao i njihovim derivatima. Smjese izomera ISA<SUB>TX</SUB>247 pokazuju kombinaciju povećane snage i smanjene toksičnosti pred prirodnim i trenutno poznatim ciklosporinima. Izomeri ISA<SUB>TX</SUB>247 i alkilirani, arilirani i deuterirani derivati sintetiziraju se stereoselektivnim putevima gdje određeni uvjeti reakcije određuju stupanj stereoselektivnosti. Stereoselektivni putevi mogu koristiti Wittigovu reakciju ili organometalni reagens, koji sadrži anorganske elemente, kao što su bor, silicij, titan i litij. Omjer izomera u smjesi može varirati od oko 10 do 90 posto mase (E)-izomera do oko 90 do 10 posto mase (Z)-izomera, na osnovi ukupne mase smjese.
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 |
---|---|
HRP20040355A2 HRP20040355A2 (en) | 2005-04-30 |
HRP20040355B1 true HRP20040355B1 (hr) | 2012-10-31 |
Family
ID=26994746
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20040355AA HRP20040355B1 (hr) | 2001-10-19 | 2004-04-19 | Sinteza ciklosporinskih analoga |
HRP20070058AA HRP20070058B1 (hr) | 2001-10-19 | 2007-02-14 | Sinteza ciklosporinskih analoga |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20070058AA HRP20070058B1 (hr) | 2001-10-19 | 2007-02-14 | Sinteza ciklosporinskih analoga |
Country Status (28)
Country | Link |
---|---|
US (13) | US6998385B2 (hr) |
EP (2) | EP1714977B1 (hr) |
JP (3) | JP4261355B2 (hr) |
KR (2) | KR101006206B1 (hr) |
CN (1) | CN100334106C (hr) |
AT (2) | ATE332917T1 (hr) |
AU (2) | AU2002331509B2 (hr) |
BR (1) | BRPI0213658A8 (hr) |
CA (1) | CA2461740C (hr) |
CO (1) | CO5580836A2 (hr) |
CY (1) | CY1105111T1 (hr) |
DE (2) | DE60213115T2 (hr) |
DK (2) | DK1436321T3 (hr) |
ES (2) | ES2326040T3 (hr) |
HK (1) | HK1062568A1 (hr) |
HR (2) | HRP20040355B1 (hr) |
IL (3) | IL160763A0 (hr) |
MA (1) | MA27293A1 (hr) |
MX (1) | MXPA04003625A (hr) |
NO (1) | NO332459B1 (hr) |
NZ (1) | NZ531944A (hr) |
PL (2) | PL210795B1 (hr) |
PT (2) | PT1714977E (hr) |
RU (1) | RU2321593C9 (hr) |
SI (1) | SI1436321T1 (hr) |
TN (1) | TNSN04068A1 (hr) |
WO (1) | WO2003033526A2 (hr) |
ZA (1) | ZA200402269B (hr) |
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 |
AR036853A1 (es) * | 2001-10-19 | 2004-10-06 | Isotechnika Inc | Mezclas de analogos de ciclosporina y su uso como agentes inmunomoduladores. |
PL210795B1 (pl) | 2001-10-19 | 2012-03-30 | Isotechnika Inc | Sposób wytwarzania mieszaniny ISATX247 wzbogaconej w izomer (E), sposób wytwarzania mieszaniny ISATX247 wzbogaconej w izomer (Z), sposób stereoselektywnej syntezy izomeru (E) ISATX247, sposób stereoselektywnej syntezy izomeru (Z) ISATX247 i sposób wytwarzania mieszaniny izomerów ISATX247 |
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 (en) | 2004-07-29 | 2012-08-14 | Amr Technology, Inc. | Novel processes for stereoselective synthesis of trans isatx 247 |
WO2006039164A2 (en) * | 2004-09-29 | 2006-04-13 | Amr Technology, Inc. | Novel cyclosporin analogues and their pharmaceutical uses |
JP2008514701A (ja) * | 2004-09-29 | 2008-05-08 | 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類似体およびそれらの薬学的使用 |
US7361636B2 (en) * | 2004-10-06 | 2008-04-22 | Amr Technology, Inc. | Cyclosporin alkynes and their utility as pharmaceutical agents |
JP2008524122A (ja) * | 2004-12-17 | 2008-07-10 | イソテクニカ インコーポレーテッド | シクロスポリン類似体の代謝体 |
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 |
US7696165B2 (en) | 2006-03-28 | 2010-04-13 | Albany Molecular Research, Inc. | Use of cyclosporin alkyne 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 |
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 |
CN101918019B (zh) | 2007-10-08 | 2014-11-26 | 奥里尼亚制药有限公司 | 包含钙调神经磷酸酶抑制剂或mTOR抑制剂的眼科组合物 |
EP2151450A1 (de) * | 2008-07-29 | 2010-02-10 | Sandoz AG | Verfahren zur Aufarbeitung von mikrobiologisch hergestellten zyklischen Oligopeptiden |
CA2732146A1 (en) * | 2008-07-30 | 2010-02-04 | 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 |
NZ594755A (en) | 2009-01-30 | 2013-12-20 | Enanta Pharm Inc | Cyclosporin analogues for preventing or treating hepatitis c infection |
US8481483B2 (en) | 2009-02-19 | 2013-07-09 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues |
AU2010259184B2 (en) | 2009-06-09 | 2015-08-13 | Aurinia Pharmaceuticals Inc. | Topical drug delivery systems for ophthalmic use |
US8685917B2 (en) | 2009-07-09 | 2014-04-01 | Enanta Pharmaceuticals, Inc. | Cyclosporin analogues |
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