AR065792A1 - PROCESS TO PREPARE (ROS) -5- (1 -AZIDO-3- (6-METOXI-5- (3-METOXI-PROPOXI) -PIRIDIN-3-ILMETIL) -4-METHYL-PENTIL) -3-ALQUIL-DIHIDRO -FURAN-2-ONA - Google Patents

PROCESS TO PREPARE (ROS) -5- (1 -AZIDO-3- (6-METOXI-5- (3-METOXI-PROPOXI) -PIRIDIN-3-ILMETIL) -4-METHYL-PENTIL) -3-ALQUIL-DIHIDRO -FURAN-2-ONA

Info

Publication number
AR065792A1
AR065792A1 ARP080101139A AR065792A1 AR 065792 A1 AR065792 A1 AR 065792A1 AR P080101139 A ARP080101139 A AR P080101139A AR 065792 A1 AR065792 A1 AR 065792A1
Authority
AR
Argentina
Prior art keywords
formula
compound
configuration
isopropyl
attached
Prior art date
Application number
Other languages
Spanish (es)
Original Assignee
Speedel Experimenta Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Speedel Experimenta Ag filed Critical Speedel Experimenta Ag
Publication of AR065792A1 publication Critical patent/AR065792A1/en

Links

Classifications

    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Reivindicacion 1: Proceso caracterizado porque, de acuerdo con la variante de proceso 1: 1A) un compuesto de la formula 2 donde X es bromuro, yoduro u -Otriflato se convierte en un compuesto de la formula 3, 1B) el compuesto de la formula 3 se hacereaccionar con un compuesto de la formula 4 donde R'3 es isopropilo, y R'7 es alquilo C1-12, cicloalquilo C3-8, fenilo o bencilo, para dar una mezcla diastereomérica de la formula 5 o un compuesto de la formula 5a donde R'3 y R'7 son cada uno comose definen con anterioridad; luego, de acuerdo con la subvariante de proceso 1, 1C) el grupo OH de la mezcla diastereomérica de la formula 5 o el grupo OH del compuesto de la formula 5a se convierte en un grupo saliente, y el compuesto que ahoracontiene un grupo saliente se elimina en presencia de una base fuerte para dar un éster acrílico de la formula 6, 1D el éster acrílico de la formula 6 se convierte po hidrolisis en un compuesto de la formula 7; 1E) el ácido de la formula 7 sehidrogena en presencia de hidrogeno y cantidades catalíticas de un complejo metálico como un catalizador de hidrogenacion asimétrica, en cuyo centro metálico se unen ligandos bidentados quirales, para dar un compuesto de la formula 8; y 1F) el ácidode la formula 8 se reduce en un compuesto de la formula 1, donde R'3 es isopropilo, y donde el átomo de carbono al que está unido el radical R'3 tiene la configuracion (R) o (S), dando preferencia a la configuracion (R); o, de acuerdo con lasubvariante de proceso 2: 2C) el grupo OH de la mezcla diastereomérica de la formula 5 o el grupo OH del compuesto de la formula 5a se convierte en un grupo saliente y el compuesto que ahora contiene un grupo saliente se elimina en presencia de unabase fuerte para dar un éster acrílico de la formula 6, 2D) el éster acrílico de la formula 6 se reduce a un compuesto de la formula 9, y 2E) el alcohol de la formula 9 se hidrogena en presencia de hidrogeno y cantidades catalíticas de un complejometálico en forma de un catalizador de hidrogenacion asimétrica, a cuyo centro metálico se unen ligandos bidentados quirales, para dar un compuesto de la formula 1, donde R'3 es isopropilo, y donde el átomo de carbono al que está unido el radicalR'3 tiene la configuracion (R) o (S), dando preferencia a la configuracion (R); o, de acuerdo con la subvariante de proceso 3, 3C) el grupo OH de la mezcla diastereomérica de la formula 5 o el grupo OH del compuesto de la formula 5a se convierte enun grupo saliente, el compuesto que ahora contiene un grupo saliente se convierte en presencia de una base fuerte en un éster acrílico, y luego, en un proceso en un recipiente, se hidroliza a un compuesto de la formula 7, 3D) el ácido de la formula7 se hidrogena en presencia de hidrogeno y cantidades catalíticas de un complejo metálico en forma de un catalizador de hidrogenacion asimétrica, a cuyo centro metálico se unen ligandos bidentados quirales, para dar un compuesto de la formula 8, y3E) el ácido de la formula 8 se reduce a un compuesto de la formula 1 donde R'3 es isopropilo, y donde el átomo de carbono al que está unido el radical R'3 tiene la configuracion (R) o (S), dando preferencia a la configuracion (R); o, de acuerdo conla variante de proceso 2; 2A) un compuesto de la formula 2 donde X es bromuro, yoduro u -Otriflato se convierte en un compuesto de la formula 10, 2B) el compuesto de la formula X se convierte en un compuesto de la formula 9, y 2C) el alcohol de laformula 9 se hidrogena en presencia de hidrogeno y cantidades catalíticas de un complejo metálico en forma de un catalizador de hidrogenacion asimétrica, a cuyo centro metálico se unen ligandos bidentados quirales, para dar un compuesto de laformula 1 donde R'3 es isopropilo, y donde el átomo de carbono al que está unido el radical R'3 tiene la configuracion (R) o (S), dando preferencia a la configuracion (R). Reivindicacion 6: Compuesto de la formula 6 donde R'3 es isopropilo y R'7 esalquilo C1-12, cicloalquilo C3-8, fenilo o bencilo. Reivindicacion 7: Compuesto de la formula 7 donde R'3 es isopropilo. Reivindicacion 8: Compuesto de la formula 8 donde R'3 es isopropil, y donde el átomo de carbono al que está unido el radicalR'3 tiene la configuracion (R) o (S), dando preferencia a la configuracion (R). Reivindicacion 9: Compuesto de la formula 9 donde R'3 es isopropilo. Reivindicacion 10: Compuesto de la formula 5 donde R'3 es isopropilo, y R'7 es alquilo C1-12,cicloalquilo C3-8, fenilo o bencilo. Reivindicacion 11: Compuesto de la formula 5a , donde R'3 es isopropilo, y R'7 es alquilo C1-12, cicloalquilo C3-8, fenilo o bencilo. Reivindicacion 12: Compuesto de la formula 1 donde R'3 es isopropilo, ydonde el átomo de carbono al que está unido el radical R'3 tiene la configuracion (R) o (S), dando preferencia a la configuracion (R). Reivindicacion 13: Compuesto de la formula B donde R'3 es isopropilo, y donde el átomo de carbono al que estáunido el radical R'3 tiene la configuracion (R) o (S), dando preferencia a la configuracion (R). Reivindicacion 14: Compuesto de la formula A donde R'3 es isopropilo, R'4 es alquilo C1-8, R'5 es alquilo C1-8 o alcoxi C1-8, R'6 es alquilo C1-8, oR'5 y R'6 son juntos tetrametileno, pentametileno, 3-oxa-1,5-pentileno o -CH2CH2O-C(O)- opcionalmente sustituidos con alquilo C1-4, fenilo o bencilo, y donde el átomo de carbono al que está unido el radical R'3 tiene la configuracion (R) o (S),dando preferencia a la configuracion (R). Reivindicacion 15: Compuesto de la formula D donde R'3 es isopropilo, R'4 es alquilo C1-8 y X' es CI, Br o I, y donde el átomo de carbono al que está unido el radical R'3 tiene la configuracion (R) o (S),dando preferencia a la configuracion (R).Claim 1: Process characterized in that, according to process variant 1: 1A) a compound of the formula 2 where X is bromide, iodide or -Otriflate is converted into a compound of the formula 3, 1B) the compound of the formula 3 is reacted with a compound of formula 4 where R'3 is isopropyl, and R'7 is C1-12 alkyl, C3-8 cycloalkyl, phenyl or benzyl, to give a diastereomeric mixture of formula 5 or a compound of the formula 5a where R'3 and R'7 are each as defined above; then, according to process subvariant 1, 1C) the OH group of the diastereomeric mixture of formula 5 or the OH group of the compound of formula 5a is converted into a leaving group, and the compound that now contains a leaving group is removed in the presence of a strong base to give an acrylic ester of the formula 6, 1D the acrylic ester of the formula 6 is converted by hydrolysis into a compound of the formula 7; 1E) the acid of the formula 7 is hydrogenated in the presence of hydrogen and catalytic amounts of a metal complex as an asymmetric hydrogenation catalyst, in whose metal center chiral bidentate ligands are attached, to give a compound of the formula 8; and 1F) the acid of formula 8 is reduced in a compound of formula 1, where R'3 is isopropyl, and where the carbon atom to which the radical R'3 is attached has the configuration (R) or (S) , giving preference to the configuration (R); or, according to the process variant 2: 2C) the OH group of the diastereomeric mixture of formula 5 or the OH group of the compound of formula 5a is converted into a leaving group and the compound that now contains a leaving group is removed in the presence of a strong base to give an acrylic ester of the formula 6, 2D) the acrylic ester of the formula 6 is reduced to a compound of the formula 9, and 2E) the alcohol of the formula 9 is hydrogenated in the presence of hydrogen and Catalytic amounts of a metal complex in the form of an asymmetric hydrogenation catalyst, to whose metal center chiral bidentate ligands are attached, to give a compound of formula 1, where R'3 is isopropyl, and where the carbon atom to which it is attached the radical R'3 has the configuration (R) or (S), giving preference to the configuration (R); or, according to process subvariant 3, 3C) the OH group of the diastereomeric mixture of formula 5 or the OH group of the compound of formula 5a becomes a leaving group, the compound that now contains a leaving group becomes in the presence of a strong base in an acrylic ester, and then, in a process in a container, a compound of the formula 7, 3D is hydrolyzed) the acid of the formula7 is hydrogenated in the presence of hydrogen and catalytic amounts of a complex metal in the form of an asymmetric hydrogenation catalyst, whose metal center binds chiral bidentate ligands, to give a compound of formula 8, and 3E) the acid of formula 8 is reduced to a compound of formula 1 where R'3 it is isopropyl, and where the carbon atom to which the radical R'3 is attached has the configuration (R) or (S), giving preference to the configuration (R); or, according to process variant 2; 2A) a compound of formula 2 where X is bromide, iodide or -Otriflate becomes a compound of formula 10, 2B) the compound of formula X becomes a compound of formula 9, and 2C) alcohol of laformula 9 is hydrogenated in the presence of hydrogen and catalytic amounts of a metal complex in the form of an asymmetric hydrogenation catalyst, to whose metal center chiral bidentate ligands are attached, to give a compound of laformula 1 where R'3 is isopropyl, and where the carbon atom to which the radical R'3 is attached has the configuration (R) or (S), giving preference to the configuration (R). Claim 6: Compound of formula 6 wherein R'3 is isopropyl and R'7 is C1-12 alkyl, C3-8 cycloalkyl, phenyl or benzyl. Claim 7: Compound of formula 7 wherein R'3 is isopropyl. Claim 8: Compound of formula 8 wherein R'3 is isopropyl, and where the carbon atom to which the radical R'3 is attached has the configuration (R) or (S), giving preference to the configuration (R). Claim 9: Compound of formula 9 wherein R'3 is isopropyl. Claim 10: Compound of formula 5 wherein R'3 is isopropyl, and R'7 is C1-12 alkyl, C3-8 cycloalkyl, phenyl or benzyl. Claim 11: Compound of formula 5a, wherein R'3 is isopropyl, and R'7 is C1-12 alkyl, C3-8 cycloalkyl, phenyl or benzyl. Claim 12: Compound of formula 1 wherein R'3 is isopropyl, and where the carbon atom to which the radical R'3 is attached has the configuration (R) or (S), giving preference to the configuration (R). Claim 13: Compound of the formula B wherein R'3 is isopropyl, and wherein the carbon atom to which the radical R'3 is attached has the configuration (R) or (S), giving preference to the configuration (R). Claim 14: Compound of the formula A wherein R'3 is isopropyl, R'4 is C1-8 alkyl, R'5 is C1-8 alkyl or C1-8 alkoxy, R'6 is C1-8 alkyl, or R'5 and R'6 are together tetramethylene, pentamethylene, 3-oxa-1,5-pentylene or -CH2CH2O-C (O) - optionally substituted with C1-4 alkyl, phenyl or benzyl, and where the carbon atom to which it is attached the radical R'3 has the configuration (R) or (S), giving preference to the configuration (R). Claim 15: Compound of the formula D wherein R'3 is isopropyl, R'4 is C1-8 alkyl and X 'is CI, Br or I, and wherein the carbon atom to which the radical R'3 is attached has the configuration (R) or (S), giving preference to the configuration (R).

ARP080101139 2007-03-21 2008-03-19 PROCESS TO PREPARE (ROS) -5- (1 -AZIDO-3- (6-METOXI-5- (3-METOXI-PROPOXI) -PIRIDIN-3-ILMETIL) -4-METHYL-PENTIL) -3-ALQUIL-DIHIDRO -FURAN-2-ONA AR065792A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07104611 2007-03-21
EP07113309 2007-07-27

Publications (1)

Publication Number Publication Date
AR065792A1 true AR065792A1 (en) 2009-07-01

Family

ID=39332025

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP080101139 AR065792A1 (en) 2007-03-21 2008-03-19 PROCESS TO PREPARE (ROS) -5- (1 -AZIDO-3- (6-METOXI-5- (3-METOXI-PROPOXI) -PIRIDIN-3-ILMETIL) -4-METHYL-PENTIL) -3-ALQUIL-DIHIDRO -FURAN-2-ONA

Country Status (3)

Country Link
AR (1) AR065792A1 (en)
TW (1) TW200906797A (en)
WO (1) WO2008113835A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG182223A1 (en) 2007-06-25 2012-07-30 Novartis Ag N5-(2-ethoxyethyl)-n3-(2-pyridinyl)-3,5-piperidinedicarboxamide derivatives for use as renin inhibitors
CN103804431A (en) * 2014-02-25 2014-05-21 中国人民解放军第四军医大学 Chiral ferrocene diphosphine ligand and preparation method thereof

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5432786B2 (en) * 1972-06-24 1979-10-16
MY119161A (en) * 1994-04-18 2005-04-30 Novartis Ag Delta-amino-gamma-hydroxy-omega-aryl-alkanoic acid amides with enzyme especially renin inhibiting activities
AUPO735997A0 (en) * 1997-06-17 1997-07-10 Fujisawa Pharmaceutical Co., Ltd. Piperazine derivatives
CA2414844C (en) * 2000-07-03 2010-05-11 Speedel Pharma Ag Process for the preparation of (r)-2-alkyl-3-phenyl-1-propanols
DE122007000077I2 (en) * 2000-07-25 2008-08-21 Speedel Pharma Ag Hirchgaessle METHOD FOR THE PRODUCTION OF SUBSTITUTED OCTANOYL AMIDES
WO2003103653A1 (en) * 2002-06-11 2003-12-18 Elan Pharmaceuticals, Inc. Methods of treating alzheimer's disease using aryl alkanoic acid amides
JP2007509934A (en) * 2003-10-31 2007-04-19 アストラゼネカ アクチボラグ Alkynes III
EP1717226B1 (en) * 2004-03-19 2009-01-21 Speedel Experimenta AG 2,7-substituted 5-amino-4-hydroxy-8-(1h-indol-5-yl)-octan amide derivatives as renin inhibitors for the treatment of hypertension
US20050245529A1 (en) * 2004-04-14 2005-11-03 Boehringer Ingelheim International Gmbh Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds
GB0410238D0 (en) * 2004-05-07 2004-06-09 Merck Sharp & Dohme Therapeutic agents
CA2599250A1 (en) * 2005-03-09 2006-09-14 F. Hoffmann-La Roche Ag Benzothiazole, thiazolopyridine, benzooxazole and oxazolopyridine derivatives as antidiabetic compounds

Also Published As

Publication number Publication date
TW200906797A (en) 2009-02-16
WO2008113835A9 (en) 2009-02-19
WO2008113835A1 (en) 2008-09-25

Similar Documents

Publication Publication Date Title
ES2579175T3 (en) Process for the production of estetrol intermediaries
AR058050A1 (en) PROCESS FOR THE PREPARATION OF AMIDAS
AR061924A1 (en) PROCESS TO ELABORATE 2- AMINO -5 - HALOBENZAMIDS 3- REPLACED
DOP2013000088A (en) REINFORCEMENT BAR AND METHOD FOR MANUFACTURING THE SAME
CO6640320A2 (en) Composition of phyto-disease control and method of phyto-disease control
AR066210A1 (en) PROCESS TO PRODUCE AMIDA COMPOUND
CO6251313A2 (en) PROCESS FOR THE PREPARATION OF PIRAZOLES
DOP2013000046A (en) PEST CONTROL AGENT
MX344936B (en) Stabilizing additives for thermochromic pigments.
CL2004000687A1 (en) PROCEDURE FOR THE PREPARATION OF TELMISARTAN.
JP2012149068A5 (en)
PE20090758A1 (en) A PROCESS FOR THE PREPARATION OF AMINODIOL COMPOUNDS PROTECTED WITH OXAZOLINE, USEFUL AS INTERMEDIARIES FOR FLORPHENICOL
AR085022A1 (en) PROCESS FOR THE PREPARATION OF 4-AMINO-3-CHLORO-5-FLUORO-6-PICOLINATES (REPLACED)
AR052067A1 (en) PROCESS FOR SYNTHESIS OF AZETIDINONES
AR074982A1 (en) METHODS FOR THE PREPARATION OF FUNGICIDES
AR079662A1 (en) INDOLIL-PIPERIDINIL BENCILAMINAS AS INHIBITORS OF BETA-TRIPTASA
CO7121339A2 (en) Malonic acid disals and method for preparing malonyl diahalides
PH12015502684B1 (en) New compounds having triple activities of thrombolysis, antithrombotic and radical scavenging, and synthesis, nano-structure and use thereof
AR079579A1 (en) METHOD FOR THE PRODUCTION OF METACRYLIC AND ACRYLIC ACID
BR112014016825A2 (en) process for asymmetric oxidation of organic compounds with peroxides in the presence of a chiral acid catalyst
AR065792A1 (en) PROCESS TO PREPARE (ROS) -5- (1 -AZIDO-3- (6-METOXI-5- (3-METOXI-PROPOXI) -PIRIDIN-3-ILMETIL) -4-METHYL-PENTIL) -3-ALQUIL-DIHIDRO -FURAN-2-ONA
AR064658A1 (en) PROCESS TO PREPARE DULOXETINE AND ITS RELATED COMPOUNDS, AS WELL AS ALSO USEFUL INTERMEDIARIES IN THE SAME
PE20090699A1 (en) METHODS FOR PREPARING IMIDAZOLE-BASED COMPOUNDS
AR092355A1 (en) FLUOROPICOLINOYL FLUORURES AND PROCESSES FOR THEIR PREPARATION
AR077332A1 (en) PROCESSES FOR THE RENTAL OF PIRAZOLES

Legal Events

Date Code Title Description
FB Suspension of granting procedure