AR032433A1 - Proceso para la preparacion de un isomero de anillo de 5 miembros 3-sustituido y compuestos intermediarios utiles en el mismo - Google Patents

Proceso para la preparacion de un isomero de anillo de 5 miembros 3-sustituido y compuestos intermediarios utiles en el mismo

Info

Publication number
AR032433A1
AR032433A1 ARP000106492A ARP000106492A AR032433A1 AR 032433 A1 AR032433 A1 AR 032433A1 AR P000106492 A ARP000106492 A AR P000106492A AR P000106492 A ARP000106492 A AR P000106492A AR 032433 A1 AR032433 A1 AR 032433A1
Authority
AR
Argentina
Prior art keywords
formula
produce
add
product
solvent
Prior art date
Application number
ARP000106492A
Other languages
English (en)
Inventor
Justin Stephen Bryans
David Clive Blakemore
Sophie Caroline Williams
Original Assignee
Warner Lambert Co
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 Warner Lambert Co filed Critical Warner Lambert Co
Publication of AR032433A1 publication Critical patent/AR032433A1/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/30—Preparation of optical isomers
    • C07C227/32—Preparation of optical isomers by stereospecific synthesis
    • 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
    • C07C229/28—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 saturated and containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C07C265/02—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms
    • C07C265/06—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C07C265/08—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/608—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
    • C07C69/616—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Neurology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biomedical Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Un proceso para la preparacion de un isomero de anillo de 5 miembros 3-sustituidos estereoespecíficos de Formula (X) en donde R es alquilo de C1-10 o cicloalquilo de C3-10, y sales farmacéuticamente aceptables de él, dicho proceso comprende: a) agregar un cianoacetato de la formula (A) NC-CH2-CO2R1, en donde R1 es alquilo o bencilo, a una mezcla de una ciclopentanona quiral de la formula (1), un solvente, un ácido carboxílico, y un catalizador de la reaccion de Knoevenagel, y agitar la mezcla en la presencia de un medio para remover el agua para producir el alqueno de la formula (2); (b) agregar el producto del Paso a) precedente a una mezcla de cloruro de bencilmagnesio, bromuro de bencilmagnesio, o yoduro de bencilmagnesio, en un solvente para producir los productos de adicion de las formulas (3a) y (3b); c) agregar los productos del Paso b) precedente a la mezcla de una base seleccionada de hidroxido de potasio, hidroxido de sodio, hidroxido de litio, o hidroxido de cesio en un solvente y agitar, y luego acidificar para producir los ácidos carboxílicos de las formulas (4a) y (4b); o agregar los productos del paso b) precedente a una mezcla de ácidos y agitar para producir los ácidos carboxílicos de las formulas (4a) y (4b); d) poner a los productos del Paso c) precedente en contacto con una amina en un solvente y recristalizar la sal así formada para producir el diastereomero enriquecido de la formula (5) como la sal de amina; e) convertir al producto del Paso d) precedente en un ácido carboxílico de la formula (6); f) agregar el producto del Paso e) precedente a una mezcla de yodometano, un solvente y una base y agitar para producir el éster de la formula (7); o agregar el producto del Paso e) a metanol y un ácido para producir el éter de la formula (7); o agregar el producto del Paso e) precedente a trimetilsilildiazometano y metanol en un solvente para producir el éster de la formula (7); o agregar el producto del Paso e) a una solucion de diazometano o trimetilsilil-diazometano en un solvente para producir el éster de la formula (7); g) agregar el producto del Paso f) a una mezcla de tetracloruro de carbono o acetato de etilo, y acetonitrilo, agua, peryodato de sodio y cloruro de rutenio (III) y agitar para producir el ácido carboxílico de la formula (8); h) agregar el producto del Paso g) a una mezcla de una base de amina terciaria, un solvente una difenilfosforil azida (DPPA), y agitar para producir el isocianato de la formula (9); o agregar el producto del Paso g) precedente a cloroformato de etilo o cloroformato de isobutilo y una base en un solvente a una temperatura de û40 degree C a 78 degree C, y luego agregar una solucion de azida de sodio en agua y tetrahidrofuran o acetona, y luego agregar tolueno o benceno, y refluir para producir el isocianato de la formula (9); i) agregar el producto del Paso h) a una mezcla de un solvente y metanol, y agitar hasta producir el carbamato de la formula (10); j) agregar el producto del Paso i) a una mezcla de un solvente y ácido clorhídrico acuoso, y agitar para producir un compuesto de la formula (11); y k) convertir el producto del Paso j) en un compuesto de la formula (12); y además convertir, si se desea, en una sal farmacéuticamente aceptable por un medio conocido; un compuesto de la formula (4a) util como un intermediario de dicho proceso en donde es alquilo de C1-10 o cicloalquilo de C3-10, y sales farmacéuticamente aceptables de él; y un compuesto de la formula (13) util como un intermediario en dicho proceso en donde R es alquilo C1-10 o cicloalquilo de C3-10, y las sales farmacéuticamente aceptables de él.
ARP000106492A 1999-12-08 2000-12-07 Proceso para la preparacion de un isomero de anillo de 5 miembros 3-sustituido y compuestos intermediarios utiles en el mismo AR032433A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US16960299P 1999-12-08 1999-12-08

Publications (1)

Publication Number Publication Date
AR032433A1 true AR032433A1 (es) 2003-11-12

Family

ID=22616383

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP000106492A AR032433A1 (es) 1999-12-08 2000-12-07 Proceso para la preparacion de un isomero de anillo de 5 miembros 3-sustituido y compuestos intermediarios utiles en el mismo

Country Status (24)

Country Link
EP (1) EP1237847B1 (es)
JP (1) JP2003516378A (es)
KR (1) KR20020060988A (es)
CN (2) CN1607201A (es)
AR (1) AR032433A1 (es)
AT (1) ATE326443T1 (es)
AU (1) AU1808401A (es)
BR (1) BR0016201A (es)
CA (1) CA2392761A1 (es)
CO (1) CO5280085A1 (es)
DE (1) DE60028076T2 (es)
DK (1) DK1237847T3 (es)
EA (1) EA004984B1 (es)
ES (1) ES2264424T3 (es)
HU (1) HUP0203812A3 (es)
IL (1) IL149575A0 (es)
MX (1) MXPA02004829A (es)
PE (1) PE20010927A1 (es)
PL (1) PL355787A1 (es)
PT (1) PT1237847E (es)
UY (1) UY26475A1 (es)
WO (1) WO2001042190A1 (es)
YU (1) YU41602A (es)
ZA (1) ZA200203628B (es)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK1296671T3 (da) 2000-06-26 2008-06-16 Warner Lambert Co Gabapentinanaloger til sövnforstyrrelser
AR031473A1 (es) * 2000-11-20 2003-09-24 Lundbeck & Co As H Intensificadores de gaba en el tratamiento de enfermedades relacionadas con una reducida actividad neuroesteroide
US6818787B2 (en) 2001-06-11 2004-11-16 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
US8048917B2 (en) 2005-04-06 2011-11-01 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
US7186855B2 (en) 2001-06-11 2007-03-06 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
CA2451267A1 (en) * 2002-12-13 2004-06-13 Warner-Lambert Company Llc Pharmaceutical uses for alpha2delta ligands
EP1572184A1 (en) * 2002-12-13 2005-09-14 Warner-Lambert Company Gabapentin analogues for fibromyalgia and other related disorders
CN101515737B (zh) * 2008-02-20 2010-10-06 中国科学院工程热物理研究所 应用三甲基叠氮硅烷为发电机定子蒸发冷却介质的方法
CN102557922A (zh) * 2010-12-20 2012-07-11 上海药明康德新药开发有限公司 顺式-3-羟基-3-甲基环丁基甲酸的合成方法
DE102010055499A1 (de) * 2010-12-22 2011-06-16 W.C. Heraeus Gmbh Prozess zur Herstellung von Bendamustinalkylester, Bendarmustin sowie Derivaten davon
CN102249833B (zh) * 2011-05-27 2013-12-11 中国科学院化学研究所 一种制备手性γ-氨基酸及其衍生物的方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT1032555E (pt) * 1997-10-27 2006-07-31 Warner Lambert Co Aminoacidos ciclicos e derivados uteis como agentes farmaceuticos

Also Published As

Publication number Publication date
BR0016201A (pt) 2002-08-13
YU41602A (sh) 2005-07-19
EP1237847B1 (en) 2006-05-17
CN1607201A (zh) 2005-04-20
CN1407967A (zh) 2003-04-02
EP1237847A1 (en) 2002-09-11
EA004984B1 (ru) 2004-10-28
PE20010927A1 (es) 2001-09-08
MXPA02004829A (es) 2003-10-14
PL355787A1 (en) 2004-05-17
JP2003516378A (ja) 2003-05-13
DK1237847T3 (da) 2006-09-04
AU1808401A (en) 2001-06-18
ATE326443T1 (de) 2006-06-15
UY26475A1 (es) 2001-01-31
KR20020060988A (ko) 2002-07-19
CA2392761A1 (en) 2001-06-14
IL149575A0 (en) 2002-11-10
PT1237847E (pt) 2006-08-31
HUP0203812A2 (hu) 2003-03-28
HUP0203812A3 (en) 2004-12-28
ES2264424T3 (es) 2007-01-01
ZA200203628B (en) 2003-08-07
CO5280085A1 (es) 2003-05-30
DE60028076D1 (de) 2006-06-22
EA200200463A1 (ru) 2002-12-26
WO2001042190A1 (en) 2001-06-14
DE60028076T2 (de) 2006-11-02

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