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1. WO1996040674 - SYNTHESES OF OPTICALLY PURE COMPOUNDS USEFUL AS GARFT INHIBITORS AND THEIR INTERMEDIATES

Publication Number WO/1996/040674
Publication Date 19.12.1996
International Application No. PCT/US1996/008953
International Filing Date 07.06.1996
Chapter 2 Demand Filed 06.01.1997
IPC
C07D 333/70 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
333Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
50condensed with carbocyclic rings or ring systems
52Benzo thiophenes; Hydrogenated benzo thiophenes
62with 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 carbon atoms of the hetero ring
68Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
70attached in position 2
C07D 409/06 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
409Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
02containing two hetero rings
06linked by a carbon chain containing only aliphatic carbon atoms
C07D 417/06 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
417Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/196
02containing two hetero rings
06linked by a carbon chain containing only aliphatic carbon atoms
C07D 513/04 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
513Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/, C07D477/232
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
CPC
C07D 333/70
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
333Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
50condensed with carbocyclic rings or ring systems
52Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
62with 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 carbon atoms of the hetero ring
68Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
70attached in position 2
C07D 409/06
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
409Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
02containing two hetero rings
06linked by a carbon chain containing only aliphatic carbon atoms
C07D 417/06
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
417Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
02containing two hetero rings
06linked by a carbon chain containing only aliphatic carbon atoms
C07D 513/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
513Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
Applicants
  • AGOURON PHARMACEUTICALS, INC. [US]/[US]
Inventors
  • VARNEY, Michael, D.
  • ROMINES, William, H.
  • PALMER, Cynthia, L.
Agents
  • GARRETT, Arthur, S.
Priority Data
08/472,23307.06.1995US
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) SYNTHESES OF OPTICALLY PURE COMPOUNDS USEFUL AS GARFT INHIBITORS AND THEIR INTERMEDIATES
(FR) SYNTHESES DE COMPOSES OPTIQUEMENT PURS UTILES EN TANT QU'INHIBITEURS DE GARFT ET LEURS INTERMEDIAIRES
Abstract
(EN)
The invention relates to methods of making compounds of formula (VII) and their enantiomers, where Ar is a substituted or unsubstituted five- or six-membered aromatic group and B is either an amino acid linked through the amino portion to form an amide or a C1-C6 alcohol linked through the alcohol portion to form an ester. These compounds are advantageously employed as intermediates to prepare optically pure compounds that are active GARFT inhibitors. In one method, a compound of formula (III) or (XVII) is reacted with a compound of formula (IV), where X is a halogen.
(FR)
L'invention concerne des procédés de production de composés de la formule (VII) ainsi que leurs énantiomères, formule dans laquelle Ar représente un groupe aromatique à 5 ou 6 éléments à substitution ou sans substitution, B représente soit un acide aminé lié par la partie amino pour former un amide, soit un alcool C1-C6 lié par la partie alcool pour former un ester. On peut utiliser avantageusement ces composés comme intermédiaires pour préparer des composés optiquement purs constituant des inhibiteurs actifs de GARFT (glycinamyde rhibonucléotide formyl transférase). Dans un procédé, on fait réagir un composé de la formule (III) ou (XVII) avec un composé de la formule (IV) dans laquelle X représente un halogène.
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