AR082621A1 - Procedimiento para preparar formas enantiomericas de derivados de acido 2,3-diaminopropionico - Google Patents
Procedimiento para preparar formas enantiomericas de derivados de acido 2,3-diaminopropionicoInfo
- Publication number
- AR082621A1 AR082621A1 ARP110102908A ARP110102908A AR082621A1 AR 082621 A1 AR082621 A1 AR 082621A1 AR P110102908 A ARP110102908 A AR P110102908A AR P110102908 A ARP110102908 A AR P110102908A AR 082621 A1 AR082621 A1 AR 082621A1
- Authority
- AR
- Argentina
- Prior art keywords
- biphenyl
- naphthyl
- series consisting
- alkyl
- formula
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
La presente se refiere a un procedimiento para preparar las formas enantioméricas de derivados de ácido 2,3-diaminopropiónico de fórmula (1), en donde R1, R2 y R3 están definidos como en las reivindicaciones, por resolución de racemato. La separación del racemato en sus enantiómeros tiene lugar a través de la formación de sales diastereómeras al añadir un auxiliar enantioméricamente puro, y la separación subsiguiente mediante cristalización fraccionada.Reivindicación 1: Un procedimiento para obtener un compuesto de fórmula (1), en donde R1 es un átomo de hidrógeno, F, Cl, I, Br, alquilo C1-4 o -CN; R2 es un resto heteroarilo seleccionado de la serie consistente en pirrol, furano, tiofeno, imidazol, pirazol, oxazol, isoxazol, tiazol, isotiazol, tetrazol, 1,2,3,5-oxatiadiazol-2-óxidos, triazolonas, oxadiazolona, isoxazolona, oxadiazolidindiona, triazol, 3-hidroxipirrol-2,4-dionas, 5-oxo-1,2,4-tiadiazoles, piridina, pirazina, pirimidina, indol, isoindol, indazol, ftalazina, quinolina, isoquinolina, quinoxalina, quinazolina, cinolina y b-carbolina, en donde el resto heteroarilo está sin sustituir o bien está sustituido una vez, dos veces o tres veces, de manera independiente entre sí, con sustituyentes seleccionados de la serie consistente en alquilo C1-5, alcoxi C1-5, halógeno, nitro, amino, trifluorometilo, hidroxi, hidroxi-alquilo C1-4, metilendioxi, etilendioxi, formilo, acetilo, ciano, hidroxicarbonilo, aminocarbonilo y alcoxi C1-4-carbonilo, o un resto arilo seleccionado de la serie consistente en fenilo, naftilo, 1-naftilo, 2-naftilo, bifenililo, 2-bifenililo, 3-bifenililo, 4-bifenililo, antrilo y fluorenilo, en donde el resto arilo está sin sustituir o bien está sustituido una vez, dos veces o tres veces, de manera independiente entre sí, con sustituyentes seleccionados de la serie consistente en alquilo C1-5, alcoxi C1-5, halógeno, nitro, amino, trifluorometilo, hidroxi, hidroxi-alquilo C1-4, metilendioxi, etilendioxi, formilo, acetilo, ciano, hidroxicarbonilo, aminocarbonilo y alcoxi C1-4-carbonilo; R3 es un átomo de hidrógeno, o alquilo C1-4, o un resto arilo seleccionado de la serie consistente en fenilo, naftilo, 1-naftilo, 2-naftilo, bifenililo, 2-bifenililo, 3-bifenililo, 4-bifenililo, antrilo y fluorenilo, en donde el resto arilo está sin sustituir o bien está sustituido, de manera independiente entre sí, una vez, dos veces o tres veces con sustituyentes seleccionados de la serie consistente en -NO2, -O-alquilo C1-4, F, Cl y Br, u -O-C(CH3)3, u -O-CH(R7)-arilo, en donde el resto arilo está seleccionado de la serie consistente en fenilo, naftilo, 1-naftilo, 2-naftilo, bifenililo, 2-bifenililo, 3-bifenililo, 4-bifenililo, antrilo y fluorenilo y está sin sustituir o bien está sustituido, de manera independiente entre sí, una vez, dos veces o tres veces con sustituyentes seleccionados de la serie consistente en -NO2, -O-CH3, F, Cl y Br, y en donde R7 es un átomo de hidrógeno o alquilo C1-4; que comprende a) mezclar un compuesto de fórmula (2), en donde R1, R2 y R3 están definidos como en el compuesto de fórmula (1), en un disolvente orgánico o una mezcla de disolventes orgánicos con un auxiliar enantioméricamente puro; b) separar la sal compuesta de auxiliar enantioméricamente puro y compuesto de fórmula (1), mediante cristalización fraccionada; y c) aislar el compuesto de fórmula (1) a partir de la sal compuesta de auxiliar enantioméricamente puro y compuesto de fórmula (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10305884 | 2010-08-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR082621A1 true AR082621A1 (es) | 2012-12-19 |
Family
ID=43598042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP110102908A AR082621A1 (es) | 2010-08-12 | 2011-08-10 | Procedimiento para preparar formas enantiomericas de derivados de acido 2,3-diaminopropionico |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US8877926B2 (es) |
| EP (1) | EP2603491B1 (es) |
| JP (1) | JP6000248B2 (es) |
| KR (1) | KR20130099044A (es) |
| CN (1) | CN103209961A (es) |
| AR (1) | AR082621A1 (es) |
| AU (1) | AU2011288533A1 (es) |
| BR (1) | BR112013002985A2 (es) |
| CA (1) | CA2807979A1 (es) |
| CL (1) | CL2013000420A1 (es) |
| CO (1) | CO6690757A2 (es) |
| CR (1) | CR20130059A (es) |
| DO (1) | DOP2013000035A (es) |
| EC (1) | ECSP13012434A (es) |
| GT (1) | GT201300038A (es) |
| MA (1) | MA34464B1 (es) |
| MX (1) | MX2013001647A (es) |
| PE (1) | PE20131326A1 (es) |
| RU (1) | RU2013110525A (es) |
| SG (1) | SG187791A1 (es) |
| TW (1) | TW201221504A (es) |
| UY (1) | UY33552A (es) |
| WO (1) | WO2012019967A1 (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI2787998T1 (sl) | 2011-12-06 | 2017-02-28 | Sanofi | Kristalinične oblike 2-(2-metilamino-pirimidin-4-il)-1H-indol-5-karboksilne kisline ((S)-1- karbamoil-2-(fenil-pirimidin-2-il-amino)etil)-amida |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19850301A1 (de) * | 1998-10-30 | 2000-05-04 | Basf Ag | Verfahren zur Racematspaltung von 2-Hydroxypropionsäuren |
| DE19951360A1 (de) | 1999-10-26 | 2001-05-03 | Aventis Pharma Gmbh | Substituierte Indole |
| DE10237722A1 (de) | 2002-08-17 | 2004-08-19 | Aventis Pharma Deutschland Gmbh | Indol- oder Benzimidazolderivate zur Modulation der IKappaB-Kinase |
| US7462638B2 (en) | 2002-08-17 | 2008-12-09 | Sanofi-Aventis Deutschland Gmbh | Use of IκB-kinase inhibitors in pain therapy |
| DE102004033406A1 (de) * | 2004-07-10 | 2006-02-16 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Herstellung der enantiomeren Formen von 2,3-Diaminopropionsäurederivaten |
| US20070142417A1 (en) | 2005-05-11 | 2007-06-21 | Aventis Pharmaceuticals Inc | Substantially Pure 2-{[2-(2-Methylamino-Pyrimidin-4-YL)-1H-Indole-5-Carbonyl]-Amino}-3-Phenylpyridin-2-YL-Amino)-Propionic Acid as an IkB Kinase Inhibitor |
| DE102005025225A1 (de) | 2005-06-01 | 2006-12-07 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Herstellung von 2-(2-Amino-pyrimidin-4-yl)-1H-indol-5-carbonsäure-derivaten |
-
2011
- 2011-08-05 KR KR1020137006179A patent/KR20130099044A/ko not_active Application Discontinuation
- 2011-08-05 CN CN2011800493516A patent/CN103209961A/zh active Pending
- 2011-08-05 JP JP2013523574A patent/JP6000248B2/ja active Active
- 2011-08-05 BR BR112013002985A patent/BR112013002985A2/pt not_active IP Right Cessation
- 2011-08-05 MX MX2013001647A patent/MX2013001647A/es unknown
- 2011-08-05 EP EP11743050.4A patent/EP2603491B1/en active Active
- 2011-08-05 AU AU2011288533A patent/AU2011288533A1/en not_active Abandoned
- 2011-08-05 MA MA35657A patent/MA34464B1/fr unknown
- 2011-08-05 CA CA2807979A patent/CA2807979A1/en not_active Abandoned
- 2011-08-05 RU RU2013110525/04A patent/RU2013110525A/ru not_active Application Discontinuation
- 2011-08-05 WO PCT/EP2011/063504 patent/WO2012019967A1/en active Application Filing
- 2011-08-05 PE PE2013000263A patent/PE20131326A1/es not_active Application Discontinuation
- 2011-08-05 SG SG2013009899A patent/SG187791A1/en unknown
- 2011-08-10 AR ARP110102908A patent/AR082621A1/es unknown
- 2011-08-10 TW TW100128464A patent/TW201221504A/zh unknown
- 2011-08-10 UY UY0001033552A patent/UY33552A/es not_active Application Discontinuation
-
2013
- 2013-02-08 EC ECSP13012434 patent/ECSP13012434A/es unknown
- 2013-02-11 CL CL2013000420A patent/CL2013000420A1/es unknown
- 2013-02-11 DO DO2013000035A patent/DOP2013000035A/es unknown
- 2013-02-11 US US13/763,975 patent/US8877926B2/en active Active
- 2013-02-11 CR CR20130059A patent/CR20130059A/es unknown
- 2013-02-11 GT GT201300038A patent/GT201300038A/es unknown
- 2013-03-08 CO CO13046970A patent/CO6690757A2/es unknown
-
2014
- 2014-09-30 US US14/502,141 patent/US9434696B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US9434696B2 (en) | 2016-09-06 |
| CA2807979A1 (en) | 2012-02-16 |
| CR20130059A (es) | 2013-03-25 |
| SG187791A1 (en) | 2013-03-28 |
| GT201300038A (es) | 2015-06-24 |
| CL2013000420A1 (es) | 2013-04-05 |
| PE20131326A1 (es) | 2013-11-12 |
| WO2012019967A1 (en) | 2012-02-16 |
| ECSP13012434A (es) | 2013-03-28 |
| AU2011288533A1 (en) | 2013-02-28 |
| MX2013001647A (es) | 2013-03-21 |
| CN103209961A (zh) | 2013-07-17 |
| EP2603491B1 (en) | 2014-09-24 |
| DOP2013000035A (es) | 2013-03-15 |
| MA34464B1 (fr) | 2013-08-01 |
| UY33552A (es) | 2012-03-30 |
| JP2013533296A (ja) | 2013-08-22 |
| US8877926B2 (en) | 2014-11-04 |
| CO6690757A2 (es) | 2013-06-17 |
| BR112013002985A2 (pt) | 2017-11-07 |
| US20150018554A1 (en) | 2015-01-15 |
| KR20130099044A (ko) | 2013-09-05 |
| TW201221504A (en) | 2012-06-01 |
| US20130211085A1 (en) | 2013-08-15 |
| EP2603491A1 (en) | 2013-06-19 |
| RU2013110525A (ru) | 2014-09-20 |
| JP6000248B2 (ja) | 2016-09-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zhao et al. | Alkyltriflate-triggered annulation of arylisothiocyanates and alkynes leading to multiply substituted quinolines through domino electrophilic activation | |
| ES2616458T3 (es) | Pirimidil pirroles sustituidos activos como inhibidores de quinasas | |
| Fan et al. | Iodine-mediated domino oxidative cyclization: one-pot synthesis of 1, 3, 4-oxadiazoles via oxidative cleavage of C (sp2)–H or C (sp)–H bond | |
| PE20221579A1 (es) | Derivados de indol mono o disustituidos como inhibidores de la replicacion viral del dengue | |
| AR083542A1 (es) | Piperidin-4-il-azetidin diamidas como inhibidores de monoacilglicerol lipasa | |
| Galenko et al. | Fe (II)/Au (I) relay catalyzed propargylisoxazole to pyridine isomerization: Access to 6-halonicotinates | |
| PE20190329A1 (es) | Compuestos moduladores de fxr (nr1h4) | |
| Xu et al. | Efficient and C2-selective arylation of indoles, benzofurans, and benzothiophenes with iodobenzenes in water at room temperature | |
| Rassokhina et al. | Synthesis of imidazo [2, 1-b] thiazoles via copper-catalyzed A3-coupling in batch and continuous flow | |
| PE20160521A1 (es) | Inhibidores de autotaxina que comprenden un nucleo ciclico de anillo heteroaromatico-bencil-amida | |
| Vijay Kumar et al. | Synthesis of 2-phenyl-4, 5-substituted oxazoles by copper-catalyzed intramolecular cyclization of functionalized enamides | |
| AR078193A1 (es) | Proceso para preparar derivados de bencil-benceno sustituidos con glucopiranosilo | |
| NI200900139A (es) | Derivados de espirocromanona sustituidos como inhibidores de acc. | |
| EA201291409A1 (ru) | Производные индолизина, способ их получения и их терапевтическое применение | |
| AR094346A1 (es) | Derivados de azaindol como inhibidores de las proteína quinasas | |
| Boggu et al. | Exploration of 2-benzylbenzimidazole scaffold as novel inhibitor of NF-κB | |
| AR104528A1 (es) | Compuestos y derivados de sulfonimidoilpurinona para el tratamiento y profilaxis de infecciones víricas | |
| RU2016150518A (ru) | Алкильные производные 1-окса-4,9-диазаспироундекановых соединений, обладающих мультимодальной активностью, направленной против боли | |
| Ding et al. | A mild and regioselective Ullmann reaction of indazoles with aryliodides in water | |
| JP2016145229A5 (es) | ||
| PE20191787A1 (es) | Derivados de indol n-sustituidos | |
| CL2020002588A1 (es) | Compuestos derivados de indol, composiciones que los contienen, útiles en el tratamiento de infestación por helmintos, preferentemente trematodos, en mamíferos. (divisional de solicitud n° 03258-2016) | |
| Zhang et al. | Direct asymmetric aldol addition–isomerization of α, β-unsaturated γ-butyrolactam with aryl α-ketoesters: synthesis of MBH-type products | |
| Liu et al. | Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes | |
| HRP20201638T1 (hr) | Postupci pripreme spojeva alkiliranog arilpiperazina i alkaliziranog arilpiperidina uključujući nove međuspojeve |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |