IN2014DN08483A - - Google Patents
Info
- Publication number
- IN2014DN08483A IN2014DN08483A IN8483DEN2014A IN2014DN08483A IN 2014DN08483 A IN2014DN08483 A IN 2014DN08483A IN 8483DEN2014 A IN8483DEN2014 A IN 8483DEN2014A IN 2014DN08483 A IN2014DN08483 A IN 2014DN08483A
- Authority
- IN
- India
- Prior art keywords
- leu
- subjected
- val
- linear
- methyl
- Prior art date
Links
- 239000000543 intermediate Substances 0.000 abstract 3
- 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 abstract 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 abstract 2
- OLROWHGDTNFZBH-XEMWPYQTSA-N Alisporivir Chemical compound 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](C(C)C)N(CC)C(=O)[C@@H](C)N(C)C1=O OLROWHGDTNFZBH-XEMWPYQTSA-N 0.000 abstract 1
- 229930105110 Cyclosporin A Natural products 0.000 abstract 1
- 108010036949 Cyclosporine Proteins 0.000 abstract 1
- 125000000729 N-terminal amino-acid group Chemical group 0.000 abstract 1
- 108010077895 Sarcosine Proteins 0.000 abstract 1
- 108010058359 alisporivir Proteins 0.000 abstract 1
- 229950004789 alisporivir Drugs 0.000 abstract 1
- 230000015556 catabolic process Effects 0.000 abstract 1
- 229960001265 ciclosporin Drugs 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 229930182912 cyclosporin Natural products 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- 230000001506 immunosuppresive effect Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- XJODGRWDFZVTKW-ZCFIWIBFSA-N n-methylleucine Chemical group CN[C@@H](C(O)=O)CC(C)C XJODGRWDFZVTKW-ZCFIWIBFSA-N 0.000 abstract 1
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 1
- 238000007142 ring opening reaction Methods 0.000 abstract 1
- 229940043230 sarcosine Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/12—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by hydrolysis, i.e. solvolysis in general
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention relates to processes and intermediates useful for the manufacture of cyclic undecapeptides such as Alisporivir a non immunosuppressive cyclosporine A derivative. The cyclosporin is acylated on the butenyl methyl threonine side chain and then subjected to a ring opening reaction (the ring opens between the sarcosine and the N methyl leucine residues). This linear peptide intermediate is subjected to Edman degradation (removal of the N terminal residue) as to give the second linear decapeptide intermediate e.g. of sequence Val N(Me)Leu Ala Ala N(Me)Leu N(Me) Leu N(Me)Val N(Me)Bmt Abu Sar when starting from CsA.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261644616P | 2012-05-09 | 2012-05-09 | |
| PCT/EP2013/059672 WO2013167703A1 (en) | 2012-05-09 | 2013-05-08 | Process for the manufacture of cyclic undecapeptides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IN2014DN08483A true IN2014DN08483A (en) | 2015-05-08 |
Family
ID=48444372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IN8483DEN2014 IN2014DN08483A (en) | 2012-05-09 | 2013-05-08 |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US20150087808A1 (en) |
| EP (1) | EP2847211A1 (en) |
| JP (3) | JP2015517481A (en) |
| KR (1) | KR20150006435A (en) |
| CN (2) | CN104284902A (en) |
| AR (1) | AR090964A1 (en) |
| AU (2) | AU2013257989A1 (en) |
| BR (1) | BR112014027648A2 (en) |
| CA (1) | CA2868940A1 (en) |
| CL (1) | CL2014003014A1 (en) |
| CO (1) | CO7141428A2 (en) |
| EA (1) | EA024903B1 (en) |
| EC (1) | ECSP14030537A (en) |
| HK (1) | HK1202555A1 (en) |
| IL (1) | IL235428A0 (en) |
| IN (1) | IN2014DN08483A (en) |
| MA (1) | MA20150231A1 (en) |
| MX (1) | MX2014013613A (en) |
| PE (1) | PE20142433A1 (en) |
| PH (1) | PH12014502499A1 (en) |
| SG (1) | SG11201406303XA (en) |
| TN (1) | TN2014000411A1 (en) |
| TW (1) | TW201350508A (en) |
| WO (1) | WO2013167703A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105693820A (en) * | 2014-11-27 | 2016-06-22 | 武汉药明康德新药开发有限公司 | Degradation method of cyclosporine A |
| EP3623378B1 (en) | 2017-05-12 | 2025-07-02 | Chugai Seiyaku Kabushiki Kaisha | Method for producing cyclic organic compound |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT401177B (en) * | 1993-10-22 | 1996-07-25 | Biochemie Gmbh | PROCESS FOR THE PREPARATION OF 7-AMINO-3-CEPHEM-4-CARBONIC ACID DERIVATIVES |
| ES2255275T3 (en) * | 1998-07-01 | 2006-06-16 | Debiopharm S.A. | NEW CYCLOSPORINE WITH IMPROVED ACTIVITY PROFILE. |
| DE60028936T2 (en) * | 1999-02-05 | 2007-01-11 | Debiopharm S.A. | CYCLOSPORIN DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF |
| ES2256450T3 (en) * | 2001-04-20 | 2006-07-16 | Debiopharm S.A. | MODIFIED CYCLOSPORIN USED AS A PROFARMACO AND ITS USE. |
| CN100334106C (en) * | 2001-10-19 | 2007-08-29 | 伊索泰克尼卡股份有限公司 | Synthesis of cyclosporin analogs |
| TW200505946A (en) | 2003-04-08 | 2005-02-16 | Hoffmann La Roche | Process for preparation of cyclosporin a analog |
| EP1793844B1 (en) * | 2004-10-01 | 2010-12-08 | Debiopharm S.A. | Use of [d-meala]3-[etval]4-cyclosporin for the treatment of hepatitis c infection |
| TW200635954A (en) * | 2004-12-17 | 2006-10-16 | Isotechnika Inc | Metabolites of cyclosporin analogs |
| AU2008204344B2 (en) | 2007-01-04 | 2013-01-31 | Debiopharm Sa | Non-immunosuppressive cyclosporin for treatment of Ullrich congenital muscular dystrophy |
| NZ584356A (en) | 2007-09-26 | 2011-10-28 | Univ Oregon Health & Science | Cyclic undecapeptides and derivatives as multiple sclerosis therapies |
| US7910378B2 (en) * | 2007-12-14 | 2011-03-22 | Siemens Healthcare Diagnostics Inc. | Methods for detection of hydrophobic drugs |
| WO2009098533A1 (en) | 2008-02-08 | 2009-08-13 | Debiopharm Sa | Non -immunosuppressive cyclosporin for the treatment of muscular dystrophy |
| MX2011004881A (en) | 2008-11-06 | 2011-08-12 | Debio Rech Pharma Sa | Cycloundecadepsipeptide compounds and use of said compounds as a medicament. |
| JP5780969B2 (en) * | 2008-12-31 | 2015-09-16 | サイネクシス，インコーポレーテッド | Cyclosporine A derivative |
| EP2391376A4 (en) * | 2009-01-30 | 2012-08-01 | Enanta Pharm Inc | Cyclosporin analogues for preventing or treating hepatitis c infection |
| US9573978B2 (en) * | 2010-08-12 | 2017-02-21 | S&T Global, Inc. | Cyclosporin derivatives for the treatment and prevention of a viral infection |
-
2013
- 2013-05-07 AR ARP130101557A patent/AR090964A1/en unknown
- 2013-05-08 AU AU2013257989A patent/AU2013257989A1/en not_active Abandoned
- 2013-05-08 CN CN201380023760.8A patent/CN104284902A/en active Pending
- 2013-05-08 TW TW102116414A patent/TW201350508A/en unknown
- 2013-05-08 IN IN8483DEN2014 patent/IN2014DN08483A/en unknown
- 2013-05-08 BR BR112014027648A patent/BR112014027648A2/en not_active IP Right Cessation
- 2013-05-08 SG SG11201406303XA patent/SG11201406303XA/en unknown
- 2013-05-08 MA MA37498A patent/MA20150231A1/en unknown
- 2013-05-08 CA CA2868940A patent/CA2868940A1/en not_active Abandoned
- 2013-05-08 US US14/399,261 patent/US20150087808A1/en not_active Abandoned
- 2013-05-08 KR KR1020147031112A patent/KR20150006435A/en not_active Withdrawn
- 2013-05-08 HK HK15102858.0A patent/HK1202555A1/en unknown
- 2013-05-08 MX MX2014013613A patent/MX2014013613A/en unknown
- 2013-05-08 JP JP2015510823A patent/JP2015517481A/en not_active Withdrawn
- 2013-05-08 WO PCT/EP2013/059672 patent/WO2013167703A1/en not_active Ceased
- 2013-05-08 PE PE2014001983A patent/PE20142433A1/en not_active Application Discontinuation
- 2013-05-08 EA EA201492036A patent/EA024903B1/en not_active IP Right Cessation
- 2013-05-08 CN CN201810575515.2A patent/CN108715606A/en active Pending
- 2013-05-08 EP EP13722740.1A patent/EP2847211A1/en not_active Withdrawn
-
2014
- 2014-09-30 TN TNP2014000411A patent/TN2014000411A1/en unknown
- 2014-10-30 IL IL235428A patent/IL235428A0/en unknown
- 2014-11-07 CL CL2014003014A patent/CL2014003014A1/en unknown
- 2014-11-10 PH PH12014502499A patent/PH12014502499A1/en unknown
- 2014-11-10 CO CO14248207A patent/CO7141428A2/en unknown
- 2014-12-08 EC ECIEPI201430537A patent/ECSP14030537A/en unknown
-
2016
- 2016-06-30 US US15/198,152 patent/US9840534B2/en not_active Expired - Fee Related
- 2016-08-31 AU AU2016222370A patent/AU2016222370B2/en not_active Ceased
-
2017
- 2017-08-29 JP JP2017164867A patent/JP2018035154A/en not_active Withdrawn
-
2019
- 2019-09-30 JP JP2019179311A patent/JP2020033349A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU2016222370B2 (en) | 2017-10-05 |
| WO2013167703A9 (en) | 2014-11-20 |
| TN2014000411A1 (en) | 2015-12-21 |
| JP2018035154A (en) | 2018-03-08 |
| SG11201406303XA (en) | 2014-11-27 |
| AU2013257989A1 (en) | 2014-10-23 |
| EA201492036A1 (en) | 2015-02-27 |
| JP2020033349A (en) | 2020-03-05 |
| MA20150231A1 (en) | 2015-07-31 |
| US9840534B2 (en) | 2017-12-12 |
| US20160304554A1 (en) | 2016-10-20 |
| ECSP14030537A (en) | 2015-09-30 |
| CN108715606A (en) | 2018-10-30 |
| AR090964A1 (en) | 2014-12-17 |
| CL2014003014A1 (en) | 2015-03-06 |
| EA024903B1 (en) | 2016-10-31 |
| CO7141428A2 (en) | 2014-12-12 |
| CN104284902A (en) | 2015-01-14 |
| JP2015517481A (en) | 2015-06-22 |
| CA2868940A1 (en) | 2013-11-14 |
| PH12014502499A1 (en) | 2014-12-22 |
| IL235428A0 (en) | 2014-12-31 |
| KR20150006435A (en) | 2015-01-16 |
| TW201350508A (en) | 2013-12-16 |
| HK1202555A1 (en) | 2015-10-02 |
| BR112014027648A2 (en) | 2017-06-27 |
| MX2014013613A (en) | 2015-02-12 |
| PE20142433A1 (en) | 2015-02-02 |
| EP2847211A1 (en) | 2015-03-18 |
| US20150087808A1 (en) | 2015-03-26 |
| WO2013167703A1 (en) | 2013-11-14 |
| AU2016222370A1 (en) | 2016-09-15 |
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