AR069268A1 - PREPARATION OF OPTICALLY ACTIVE CYCLINE AMINO ACIDS AND INTERMEDIATE COMPOUNDS USED IN THIS PROCESS - Google Patents

PREPARATION OF OPTICALLY ACTIVE CYCLINE AMINO ACIDS AND INTERMEDIATE COMPOUNDS USED IN THIS PROCESS

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Publication number
AR069268A1
AR069268A1 ARP080102671A ARP080102671A AR069268A1 AR 069268 A1 AR069268 A1 AR 069268A1 AR P080102671 A ARP080102671 A AR P080102671A AR P080102671 A ARP080102671 A AR P080102671A AR 069268 A1 AR069268 A1 AR 069268A1
Authority
AR
Argentina
Prior art keywords
alkyl
formula
compound
aryl
cycloalkyl
Prior art date
Application number
ARP080102671A
Other languages
Spanish (es)
Inventor
Bruce Allen Pearlman
Original Assignee
Pfizer
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 Pfizer filed Critical Pfizer
Publication of AR069268A1 publication Critical patent/AR069268A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/96—Spiro-condensed ring systems
    • 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

Abstract

Reivindicacion 1: Un método caracterizado porque es para preparar un compuesto de formula (1) o una de sus sales farmacéuticamente aceptable, o un enantiomero opuesto del compuesto de formula (1) o una de sus sales farmacéuticamente aceptable, en donde R1 y R2 son cada uno independientemente alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-6, cicloalquenilo C3-6, cicloalquil C3-6-alquiIo C1-3, cicloalquenil C3-6-alquilo C1-3, o aril-alquilo C1-3, en donde el arilo puede estar opcionalmente sustituido con uno a tres sustituyentes seleccionados entre alquilo C1-6, alcoxi C1-6, alcoxicarbonilo C1-6, carboxi, hidroxi, halogeno, fluoroalquilo C1-6 y nitro, comprendiendo dicho método: (a) reducir un resto ciano de un compuesto de formula (5), o su enantiomero opuesto, o una sal del compuesto de formula (5) o su enantiomero opuesto, a un resto amino, en donde R1 y R2 en la formula (5) son como se definio anteriormente para la formula (1), y R4 se selecciona a partir de un átomo de hidrogeno y alquilo C1-6; y (b) convertir opcionalmente el compuesto de formula (1) o su enantiomero opuesto a una sal farmacéuticamente aceptable del compuesto de formula (1) o su enantiomero opuesto. Reivindicacion 6: Un compuesto caracterizado porque es de formula (4) o su enantiomero contrario, en donde R1 y R2 son cada uno independientemente alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-6, cicloalquenilo C3-6, cicloalquil C3-6-alquilo C1-3, cicloalquenil C3-6-alquilo C1-3, o aril-alquilo C1-3, en donde el arilo puede estar opcionalmente sustituido con uno a tres sustituyentes seleccionados entre alquilo C1-6, alcoxi C1-6, alcoxicarbonilo C1-6, carboxi, hidroxi, halogeno, fluoroalquilo C1-6 y nitro, y R3 es un ácido carboxílico o grupo protector éster que tiene una estructura representada por formulas 7 y 8 en donde ôAö en la formula 7 y en la formula 8 representa un punto de union al resto del compuesto de formula (4); R6, R7 y R8 son cada uno independientemente alquilo C1-6 o, junto con los átomos a los que están unidos, forman un heterociclo bicíclico que tiene solamente miembros de anillo de carbono y oxígeno; Z1 y Z2 se seleccionan cada uno independientemente entre O y S; R9 es alquilo C1-6, R10 se selecciona entre alquilo C1-6, sililo y alquilsililo C1-6; o R9 y R10, junto con los átomos a los que están unidos, forman un heterociclo monocíclico que tiene solamente miembros de anillo de carbono y oxígeno, solamente miembros de anillo de carbono y azufre o solamente miembros de anillo de carbono, oxígeno y azufre. Reivindicacion 8: Un compuesto caracterizado porque es de formula (5) o uno de sus enantiomeros contrarios, o una de las sales del compuesto de formula (5) o su enantiomero contrario, en donde R1 y R2 son cada uno independientemente alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-6, cicloalquenilo C3-6, cicloalquil C3-6-alquilo C1-3, cicloalquenil C3-6-alquilo C1-3 o aril-alquilo C1-3; y R4 se selecciona entre H, alquilo C1-6, aril-alquilo C1-3, un ion metálico del Grupo 1, un ion metálico del Grupo 2, un ion de amonio primario o un ion de amonio secundario; en donde el arilo en cada uno de los grupos aril-alquilo C1-3 anteriores puede estar opcionalmente sustituido con uno a tres sustituyentes seleccionados entre alquilo C1-6, alcoxi C1-6, alcoxicarbonilo C1-6, carboxi, hidroxi, halogeno, fluoroalquilo C1-6 y nitro.Claim 1: A method characterized in that it is for preparing a compound of formula (1) or a pharmaceutically acceptable salt thereof, or an opposite enantiomer of the compound of formula (1) or a pharmaceutically acceptable salt thereof, wherein R1 and R2 are each independently C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C3-6 cycloalkenyl, C3-6 cycloalkyl C1-3 alkyl, C3-6 cycloalkenyl-C1-3 alkyl, or aryl - C1-3 alkyl, wherein the aryl may be optionally substituted with one to three substituents selected from C1-6 alkyl, C1-6 alkoxy, C1-6 alkoxycarbonyl, carboxy, hydroxy, halogen, C1-6 fluoroalkyl and nitro, comprising said method: (a) reducing a cyano moiety of a compound of formula (5), or its opposite enantiomer, or a salt of the compound of formula (5) or its opposite enantiomer, to an amino moiety, wherein R1 and R2 in the formula (5) are as defined above for the formula (1), and R4 is selected from an att as hydrogen and C1-6 alkyl; and (b) optionally converting the compound of formula (1) or its opposite enantiomer to a pharmaceutically acceptable salt of the compound of formula (1) or its opposite enantiomer. Claim 6: A compound characterized in that it is of formula (4) or its opposite enantiomer, wherein R1 and R2 are each independently C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C3- cycloalkenyl 6, C3-6 cycloalkyl-C1-3alkyl, C3-6cycloalkenyl-C1-3alkyl, or aryl-C1-3alkyl, wherein the aryl may be optionally substituted with one to three substituents selected from C1-6alkyl, C1-6 alkoxy, C1-6 alkoxycarbonyl, carboxy, hydroxy, halogen, C1-6 fluoroalkyl and nitro, and R3 is a carboxylic acid or ester protecting group having a structure represented by formulas 7 and 8 where "A" in formula 7 and in formula 8 represents a point of attachment to the rest of the compound of formula (4); R6, R7 and R8 are each independently C1-6 alkyl or, together with the atoms to which they are attached, form a bicyclic heterocycle having only carbon and oxygen ring members; Z1 and Z2 are each independently selected from O and S; R9 is C1-6 alkyl, R10 is selected from C1-6 alkyl, silyl and C1-6 alkylsilyl; or R9 and R10, together with the atoms to which they are attached, form a monocyclic heterocycle having only carbon and oxygen ring members, only carbon and sulfur ring members or only carbon, oxygen and sulfur ring members. Claim 8: A compound characterized in that it is of formula (5) or one of its opposite enantiomers, or one of the salts of the compound of formula (5) or its opposite enantiomer, wherein R1 and R2 are each independently C1-6 alkyl , C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C3-6 cycloalkenyl, C3-6 cycloalkyl-C1-3 alkyl, C3-6 cycloalkenyl-C1-3 alkyl or aryl-C1-3 alkyl; and R4 is selected from H, C1-6 alkyl, aryl-C1-3 alkyl, a Group 1 metal ion, a Group 2 metal ion, a primary ammonium ion or a secondary ammonium ion; wherein the aryl in each of the above aryl-C 1-3 alkyl groups may be optionally substituted with one to three substituents selected from C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxycarbonyl, carboxy, hydroxy, halogen, fluoroalkyl C1-6 and nitro.

ARP080102671A 2007-06-21 2008-06-20 PREPARATION OF OPTICALLY ACTIVE CYCLINE AMINO ACIDS AND INTERMEDIATE COMPOUNDS USED IN THIS PROCESS AR069268A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US94558407P 2007-06-21 2007-06-21

Publications (1)

Publication Number Publication Date
AR069268A1 true AR069268A1 (en) 2010-01-13

Family

ID=40101023

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP080102671A AR069268A1 (en) 2007-06-21 2008-06-20 PREPARATION OF OPTICALLY ACTIVE CYCLINE AMINO ACIDS AND INTERMEDIATE COMPOUNDS USED IN THIS PROCESS

Country Status (4)

Country Link
JP (1) JP2009108024A (en)
AR (1) AR069268A1 (en)
TW (1) TW200906770A (en)
WO (1) WO2008155619A2 (en)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUP0004310A3 (en) * 1997-10-27 2001-11-28 Warner Lambert Co Cyclic amino acids, and derivatives thereof and pharmaceutical compositions comprising the said compounds as active agents
DE69826151T2 (en) * 1997-12-16 2005-01-27 Warner-Lambert Co. Llc 1-SUBSTITUTED-1-AMINOMETHYL-CYCLOALKAN DERIVATIVES (= GABAPENTIN ANALOGA), THEIR PREPARATION AND THEIR USE IN THE TREATMENT OF NEUROLOGICAL DISEASES
YU57401A (en) * 1999-12-08 2004-05-12 Warner-Lambert Company Branched chain amino acid-dependent aminotransferase inhibitors and their use in the treatment of diabetic retinopathy

Also Published As

Publication number Publication date
WO2008155619A3 (en) 2009-08-13
TW200906770A (en) 2009-02-16
JP2009108024A (en) 2009-05-21
WO2008155619A2 (en) 2008-12-24

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