AR092951A1 - Procesos basados en acetales de aldehidos para la fabricacion de depsipeptidos macrociclicos e intermedios - Google Patents
Procesos basados en acetales de aldehidos para la fabricacion de depsipeptidos macrociclicos e intermediosInfo
- Publication number
- AR092951A1 AR092951A1 ARP130103657A ARP130103657A AR092951A1 AR 092951 A1 AR092951 A1 AR 092951A1 AR P130103657 A ARP130103657 A AR P130103657A AR P130103657 A ARP130103657 A AR P130103657A AR 092951 A1 AR092951 A1 AR 092951A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- amino acid
- alkanoyl
- salt
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 6
- 108010002156 Depsipeptides Proteins 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000001241 acetals Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 10
- 150000003839 salts Chemical class 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 2
- 125000003275 alpha amino acid group Chemical group 0.000 abstract 2
- 150000001413 amino acids Chemical class 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- -1 aldehyde acetal Chemical class 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000007086 side reaction Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K11/00—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K11/02—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof cyclic, e.g. valinomycins ; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/164—Unsaturated ethers containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K11/00—Depsipeptides having up 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
- C07K7/02—Linear peptides containing at least one abnormal peptide link
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Peptides Or Proteins (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Método o proceso para la fabricación química de depsipéptidos de la fórmula (1) empleando un intermedio de acetal de aldehído. Reivindicación 1: Un método o proceso para la preparación de un compuesto de depsipéptido cíclico de la fórmula (1), en donde A¹ es una fracción bivalente de un aminoácido con un grupo carboxilo o carbamoilo terminal, y se une en su lado derecho en la fórmula (1) a través de un carbonilo al resto de la molécula, o es alcanoilo C₁₋₈ o hidroxi-alcanoilo C₁₋₈ fosforilado; X está unido a través de un N de A¹ y es acilo o está ausente si A¹ es alcanoilo C₁₋₈ o hidroxi-alcanoilo C₁₋₈ fosforilado; R² es alquilo C₁₋₈; R³ es la cadena lateral del aminoácido; R⁵ es la cadena lateral del aminoácido; R⁶ es la cadena lateral del hidroxi aminoácido; R⁷ es la cadena lateral de un aminoácido; e Y es hidrógeno o alquilo C₁₋₈; o una sal del mismo; dicho método que comprende desproteger un compuesto de la fórmula (2) en donde los grupos protectores de aldehído Rᵏ y Rˡ son independientemente el uno del otro alquilo sin sustituir o sustituido o junto con los dos átomos de O de unión y el átomo de carbono al que los dos átomos de O están unidos forman un anillo que es no sustituido o sustituido, Y es como se define para un compuesto de la fórmula (1) y X*, A¹*, R²*, R³*, R⁵*, R⁶*, y R⁷* corresponden a X, A¹, R², R³, R⁵, R⁶, y R⁷ en la fórmula (1), respectivamente, pero con la condición de que los grupos funcionales reactivos en estas fracciones están presentes en forma protegida, al menos, si podían participar en reacciones secundarias no deseadas, para dar lugar a un compuesto de la fórmula (1); y, si se desea, convertir un compuesto libre de la fórmula (1) en una sal, una sal de un compuesto de la fórmula (1) en una sal diferente de un compuesto de la fórmula (1) o en el compuesto libre de la fórmula (1) y/o convertir un análogo deshidratado y/o análogo de cinco miembros de un compuesto de la fórmula (1) en el correspondiente compuesto de la fórmula (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261711282P | 2012-10-09 | 2012-10-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR092951A1 true AR092951A1 (es) | 2015-05-06 |
Family
ID=49880855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP130103657A AR092951A1 (es) | 2012-10-09 | 2013-10-09 | Procesos basados en acetales de aldehidos para la fabricacion de depsipeptidos macrociclicos e intermedios |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US8987413B2 (es) |
| EP (1) | EP2906586A2 (es) |
| JP (1) | JP2016500668A (es) |
| KR (1) | KR20150065710A (es) |
| CN (1) | CN104797592A (es) |
| AR (1) | AR092951A1 (es) |
| AU (1) | AU2013328285B2 (es) |
| BR (1) | BR112015006293A2 (es) |
| CA (1) | CA2884401A1 (es) |
| EA (1) | EA201590718A1 (es) |
| IN (1) | IN2015DN01812A (es) |
| MX (1) | MX2015004628A (es) |
| TW (1) | TW201420596A (es) |
| WO (1) | WO2014057419A2 (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2183273T (pt) | 2007-08-17 | 2017-05-22 | Novartis Ag | Depsipéptidos cíclicos |
| US8614289B2 (en) | 2011-04-20 | 2013-12-24 | Novartis Ag | Processes for the manufacture of macrocyclic depsipeptides and new intermediates |
| US8680054B2 (en) | 2011-04-20 | 2014-03-25 | Novartis Ag | Suspension type topical formulations comprising cyclic depsipeptide |
| US9067978B2 (en) | 2012-10-09 | 2015-06-30 | Novartis Ag | Solution phase processes for the manufacture of macrocyclic depsipeptides and new intermediates |
| CN106029684A (zh) * | 2014-04-08 | 2016-10-12 | 诺华股份有限公司 | 用于生产大环缩酚酸肽和新中间体的新型缩醛类方法 |
| US20190062260A1 (en) * | 2017-08-31 | 2019-02-28 | Rohm And Haas Company | Antimicrobial compositions, methods of making, and methods of use |
| US11643438B2 (en) | 2018-07-20 | 2023-05-09 | The Board Of Regents Of The University Of Oklahoma | Antimicrobial peptides and methods of use |
| CN111072622B (zh) * | 2019-12-27 | 2023-01-17 | 江苏广域化学有限公司 | 一种3-卤代丙醛的缩醛类化合物的合成方法 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3043252C2 (de) | 1980-11-15 | 1982-12-02 | Degussa Ag, 6000 Frankfurt | Cyclische Acetale von N-Acylglutaminsäure -γ- semialdehyden, Verfahren zu deren Herstellung und ihre Verwendung |
| US5595756A (en) | 1993-12-22 | 1997-01-21 | Inex Pharmaceuticals Corporation | Liposomal compositions for enhanced retention of bioactive agents |
| DE4421113A1 (de) | 1994-06-16 | 1995-12-21 | Biotechnolog Forschung Gmbh | Chondramide, Gewinnungsverfahren, Mittel mit Chondramiden und Mischkultur zur Chondramid-Gewinnung |
| DE19828043A1 (de) | 1998-06-24 | 1999-12-30 | Bayer Ag | Ektoparasitizide Mittel |
| JP2000154198A (ja) | 1998-11-20 | 2000-06-06 | Nisshin Flour Milling Co Ltd | 環状デプシペプチドの固相合成方法及びその中間体 |
| GB0108234D0 (en) | 2001-04-02 | 2001-05-23 | Pharma Mar Sa | Process for producing trunkamide A compounds |
| US7662960B2 (en) * | 2001-04-26 | 2010-02-16 | Choongwae Pharma Corporation | Beta-strand mimetics and method relating thereto |
| US20040110228A1 (en) | 2002-04-01 | 2004-06-10 | Mcalpine Shelli R. | Combinatorial organic synthesis of unique biologically active compounds |
| DE602004025803D1 (de) | 2003-06-06 | 2010-04-15 | Arexis Ab | Verwendung von kondensierten heterozyklischen verbindungen als scce-hemmern zur behandlung von hautzuständen |
| GB0322140D0 (en) | 2003-09-22 | 2003-10-22 | Pfizer Ltd | Combinations |
| WO2005075667A1 (en) | 2004-02-03 | 2005-08-18 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with kallikrein 7 (klk7) |
| CA2651796A1 (en) | 2006-02-27 | 2007-09-07 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Identification and use of novopeptides for the treatment of cancer |
| PT2183273T (pt) * | 2007-08-17 | 2017-05-22 | Novartis Ag | Depsipéptidos cíclicos |
| JP5401459B2 (ja) | 2007-08-17 | 2014-01-29 | ノバルティス アーゲー | カリクレイン７を阻害するための環状デプシペプチドの使用 |
| DE102007052391A1 (de) | 2007-10-31 | 2009-05-07 | Henkel Ag & Co. Kgaa | Mattwachs |
| US20110112121A1 (en) | 2009-07-06 | 2011-05-12 | Joerg Berghausen | Pharmaceutical Compositions and Solid Forms |
| US20120064013A1 (en) | 2010-02-03 | 2012-03-15 | David Marcos | Foamable topical composition |
| KR101004362B1 (ko) | 2010-03-19 | 2010-12-28 | 가톨릭대학교 산학협력단 | 자가 면역 질환 예방 및 치료용 ＴＮＦ－α와 ＴＷＥＡＫ 이중 길항제 |
| US20120064136A1 (en) | 2010-09-10 | 2012-03-15 | Nanobio Corporation | Anti-aging and wrinkle treatment methods using nanoemulsion compositions |
| BR112013018918A2 (pt) | 2011-01-24 | 2016-10-04 | Anterios Inc | composições de nanopartículas |
| SG10201804552WA (en) | 2011-01-24 | 2018-07-30 | Anterios Inc | Nanoparticle compositions, formulations thereof, and uses therefor |
| US8680054B2 (en) | 2011-04-20 | 2014-03-25 | Novartis Ag | Suspension type topical formulations comprising cyclic depsipeptide |
| US8614289B2 (en) | 2011-04-20 | 2013-12-24 | Novartis Ag | Processes for the manufacture of macrocyclic depsipeptides and new intermediates |
| US9067978B2 (en) * | 2012-10-09 | 2015-06-30 | Novartis Ag | Solution phase processes for the manufacture of macrocyclic depsipeptides and new intermediates |
-
2013
- 2013-10-01 US US14/042,950 patent/US8987413B2/en active Active
- 2013-10-08 BR BR112015006293A patent/BR112015006293A2/pt not_active IP Right Cessation
- 2013-10-08 IN IN1812DEN2015 patent/IN2015DN01812A/en unknown
- 2013-10-08 WO PCT/IB2013/059197 patent/WO2014057419A2/en active Application Filing
- 2013-10-08 KR KR1020157008835A patent/KR20150065710A/ko not_active Application Discontinuation
- 2013-10-08 MX MX2015004628A patent/MX2015004628A/es unknown
- 2013-10-08 CN CN201380052592.5A patent/CN104797592A/zh active Pending
- 2013-10-08 CA CA2884401A patent/CA2884401A1/en not_active Abandoned
- 2013-10-08 TW TW102136396A patent/TW201420596A/zh unknown
- 2013-10-08 AU AU2013328285A patent/AU2013328285B2/en not_active Ceased
- 2013-10-08 JP JP2015535163A patent/JP2016500668A/ja active Pending
- 2013-10-08 EP EP13812093.6A patent/EP2906586A2/en not_active Withdrawn
- 2013-10-08 EA EA201590718A patent/EA201590718A1/ru unknown
- 2013-10-09 AR ARP130103657A patent/AR092951A1/es unknown
-
2015
- 2015-01-14 US US14/596,561 patent/US20150141615A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP2906586A2 (en) | 2015-08-19 |
| IN2015DN01812A (es) | 2015-05-29 |
| AU2013328285B2 (en) | 2016-07-14 |
| WO2014057419A2 (en) | 2014-04-17 |
| CN104797592A (zh) | 2015-07-22 |
| JP2016500668A (ja) | 2016-01-14 |
| MX2015004628A (es) | 2015-07-14 |
| BR112015006293A2 (pt) | 2017-07-04 |
| KR20150065710A (ko) | 2015-06-15 |
| AU2013328285A1 (en) | 2015-03-12 |
| US8987413B2 (en) | 2015-03-24 |
| CA2884401A1 (en) | 2014-04-17 |
| US20150141615A1 (en) | 2015-05-21 |
| TW201420596A (zh) | 2014-06-01 |
| US20140100353A1 (en) | 2014-04-10 |
| EA201590718A1 (ru) | 2015-07-30 |
| WO2014057419A3 (en) | 2014-07-03 |
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| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |