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1. WO2006100568 - PREPARATION OF OPTICALLY PURE BETA-AMINO ACIDS HAVING AFFINITY FOR THE ALPHA-2-DELTA PROTEIN

Publication Number WO/2006/100568
Publication Date 28.09.2006
International Application No. PCT/IB2006/000637
International Filing Date 13.03.2006
Chapter 2 Demand Filed 06.06.2006
IPC
C07D 295/14 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
295Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
04with substituted hydrocarbon radicals attached to ring nitrogen atoms
14substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
C07C 229/30 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
229Compounds containing amino and carboxyl groups bound to the same carbon skeleton
02having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
30the carbon skeleton being acyclic and unsaturated
C07C 233/47 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
233Carboxylic acid amides
01having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
45having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
46with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
47having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
C07C 229/08 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
229Compounds containing amino and carboxyl groups bound to the same carbon skeleton
02having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
04the carbon skeleton being acyclic and saturated
06having only one amino and one carboxyl group bound to the carbon skeleton
08the nitrogen atom of the amino group being further bound to hydrogen atoms
C07C 227/32 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
227Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
30Preparation of optical isomers
32by stereospecific synthesis
C07C 227/20 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
227Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
14from compounds containing already amino and carboxyl groups or derivatives thereof
18by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
20by hydrolysis of N-acylated amino acids or derivatives thereof, e.g. hydrolysis of carbamates
CPC
C07C 227/20
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
227Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
14from compounds containing already amino and carboxyl groups or derivatives thereof
18by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
20by hydrolysis of N-acylated amino-acids or derivatives thereof, e.g. hydrolysis of carbamates
C07C 227/32
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
227Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
30Preparation of optical isomers
32by stereospecific synthesis
C07C 229/30
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
229Compounds containing amino and carboxyl groups bound to the same carbon skeleton
02having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
30the carbon skeleton being acyclic and unsaturated
C07C 233/47
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
233Carboxylic acid amides
01having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
45having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
46with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
47having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
C07D 295/145
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
295Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2.] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
04with substituted hydrocarbon radicals attached to ring nitrogen atoms
14substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
145with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
Y02P 20/582
YSECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
20Technologies relating to chemical industry
50Improvements relating to the production of products other than chlorine, adipic acid, caprolactam, or chlorodifluoromethane, e.g. bulk or fine chemicals or pharmaceuticals
58Recycling
582of unreacted starting or intermediate materials
Applicants
  • PHARMACIA & UPJOHN COMPANY LLC [US]/[US] (AllExceptUS)
  • FRANCZYK, Thaddeus, Stephan, Ii [US]/[US] (UsOnly)
  • HERRINTON, Paul, Matthew [US]/[US] (UsOnly)
  • PERRAULT, William, Roland [US]/[US] (UsOnly)
Inventors
  • FRANCZYK, Thaddeus, Stephan, Ii
  • HERRINTON, Paul, Matthew
  • PERRAULT, William, Roland
Agents
  • FULLER, Grover, F., Jr.
Priority Data
60/665,50224.03.2005US
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) PREPARATION OF OPTICALLY PURE BETA-AMINO ACIDS HAVING AFFINITY FOR THE ALPHA-2-DELTA PROTEIN
(FR) PREPARATION DE $G(B)-AMINO-ACIDES OPTIQUEMENT PURS PRESENTANT UNE AFFINITE AVEC LA PROTEINE ALPHA-2-DELTA
Abstract
(EN)
Disclosed are materials and methods for preparing optically active &bgr;-amino acids, which bind to the alpha-2-delta subunit of a calcium channel and are useful for treating pain, fibromyalgia, and a variety of psychiatric and sleep disorders. The method includes reacting a chiral allyl amine with a 2-alkynoate in the presence of a Lewis acid and a base to give a chiral tertiary enamine, which after reaction with ammonia, is hydrogenated to give optically active &bgr;-amino acids.
(FR)
Cette invention concerne des matériaux et des procédés permettant de préparer des ß-amino acides optiquement purs, lesquels se lient à la sous-unité alpha-2-delta d'un canal calcique et sont utilisés pour traiter la douleur, la fibromyalgie, ainsi qu'une large gamme de troubles psychiatriques et de troubles du sommeil. Le procédé décrit dans cette invention consiste à faire réagir une amine allyle chirale avec un 2-alkynoate en présence d'un acide de Lewis et d'une base pour obtenir une énamine tertiaire chirale, laquelle, après réaction avec l'ammoniac, est hydrogénée pour produire des ß-amino acides optiquement purs.
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