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1. WO2007092007 - SYNTHESIS OF [1-13 C]PYRUVIC ACID, [2-13C]PYRUVIC ACID, [3-13C]PYRUVIC ACID AND COMBINATIONS THEREOF

Publication Number WO/2007/092007
Publication Date 16.08.2007
International Application No. PCT/US2006/004435
International Filing Date 07.02.2006
Chapter 2 Demand Filed 06.09.2006
IPC
C07C 49/11 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
49Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
04Saturated compounds containing keto groups bound to acyclic carbon atoms
105containing rings
11monocyclic
C07C 49/115 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
49Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
04Saturated compounds containing keto groups bound to acyclic carbon atoms
105containing rings
115containing condensed ring systems
CPC
C07B 2200/05
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
2200Indexing scheme relating to specific properties of organic compounds
05Isotopically modified compounds, e.g. labelled
C07B 59/001
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
59Introduction of isotopes of elements into organic compounds ; ; Labelled organic compounds per se
001Acyclic or carbocyclic compounds
C07C 235/80
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
235Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
70having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
72with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
80having carbon atoms of carboxamide groups and keto groups bound to the same carbon atom, e.g. acetoacetamides
C07C 317/24
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
317Sulfones; Sulfoxides
24having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
C07C 317/46
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
317Sulfones; Sulfoxides
44having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
46the carbon skeleton being further substituted by singly-bound oxygen atoms
C07C 59/347
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
59Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
235Saturated compounds containing more than one carboxyl group
347containing keto groups
Applicants
  • THE REGENTS OF THE UNIVERSITY OF CALIFORNIA [US]/[US]
Inventors
  • MARTINEZ, Rodolfo, A.
  • UNKEFER, Clifford, J.
  • ALVAREZ, Marc, A.
Agents
  • COTTRELL, Bruce, H.
Priority Data
11/052,58907.02.2005US
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) SYNTHESIS OF [1-13 C]PYRUVIC ACID, [2-13C]PYRUVIC ACID, [3-13C]PYRUVIC ACID AND COMBINATIONS THEREOF
(FR) SYNTHESE DE L'ACIDE [1-13 C]PYRUVIQUE, DE L'ACIDE [2-13C]PYRUVIQUE, DE L'ACIDE [3-13C]PYRUVIQUE ET DE COMBINAISONS DE CES ACIDES
Abstract
(EN)
The present invention is directed to labeled compounds, of the formulae: (A, B, C) wherein C* is each independently selected from the group consisting of 13C and 12C with the proviso that at least one C* is 13C, each hydrogen of the methylene group can independently be either hydrogen or deuterium, the methyl group includes either zero or three deuterium atoms, Q is from the group of sulfide, sulfinyl, and sulfone, Z is an aryl group from the group of 1 -naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, and phenyl groups with the structure: (D) wherein R1, R2, R3, R4 and R5 are each independently from the group of hydrogen, a C1-C4 lower alkyl, a halogen, and an amino group from the group of NH2, NHR and NRR' where R and R' are each independently from the group of a C1-C4 lower alkyl, a phenyl, and an alkoxy group, and the methyl group can include either zero or three deuterium atoms. The present invention is also directed to labeled compounds of the formula: (E) or (F) where X is from the group of NR6R7 and -OR8 where R6 and R7 are each independently selected from the group of C1-C4 lower alkyl, alkoxy and aryl and R8 is from the group of C1-C4 lower alkyl, alkoxy and aryl, T is from the group of -CH3, - CD3, -CH2-S-R9, -CH2-S(O)-R9, and -CH2-(O)S(O)-R9, J is from the group of -CH(OH)-CH2-S-R9, -CH(OH)-CH2-S(O)-R9, and -CH(OH)-CH2-(O)S(O)-R9 where R9 is an aryl group from the group of 1-naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, and phenyl groups with the structure: (G) wherein R1, R2, R3, R4 and R5 are each independently from the group of hydrogen, a C1-C4 lower alkyl, a halogen, and an amino group from the group of NH2, NHR and NRR' where R and R' are each independently from the group of a Cl-C4 lower alkyl, a phenyl, and an alkoxy group, and C* are each independently selected from the group consisting of 13C and 12C with the proviso that at least one C* is 13C.
(FR)
La présente invention concerne des composés marqués répondant aux formules (A), (B), (C) dans lesquelles : chaque C* est choisi indépendamment dans le groupe comprenant 13C et 12C, à condition qu'au moins l'un des C* soit 13C ; chaque atome d'hydrogène du groupe méthylène peut être indépendamment de l'hydrogène ou du deutérium ; le groupe méthyle ne comprend aucun ou comprend trois atomes de deutérium ; Q est choisi parmi les groupes sulfure, sulfinyle et sulfone ; Z est un groupe aryle choisi parmi les groupes 1-naphtyle, 1-naphtyle substitué, 2-naphtyle, 2-naphtyle substitué et les groupes phényle de structure (D), dans laquelle R1, R2, R3, R4 et R5 sont chacun indépendamment un atome d'hydrogène, un alkyle inférieur en C1 à C4, un halogène ou un groupe amino choisi dans le groupe comprenant NH2, NHR et NRR', R et R' étant chacun indépendamment un alkyle inférieur en C1 à C4, un phényle ou un alcoxy ; enfin le groupe méthyle peut en outre ne comprendre aucun ou comprendre trois atomes de deutérium. La présente invention concerne également des composés marqués répondant aux formules (E) ou (F), dans lesquelles X est choisi parmi NR6R7 et -OR8, R6 et R7 étant chacun indépendamment un alkyle inférieur en C1 à C4, un alcoxy ou un aryle et R8 étant un alkyle inférieur en C1 à C4, un alcoxy ou un aryle ; T est un groupe -CH3, - CD3, -CH2-S-R9, -CH2-S(O)-R9 ou -CH2-(O)S(O)-R9 ; J est un groupe -CH(OH)-CH2-S-R9, -CH(OH)-CH2-S(O)-R9 ou -CH(OH)-CH2-(O)S(O)-R9, R9 étant un groupe aryle choisi parmi les groupes 1-naphtyle, 1-naphtyle substitué, 2-naphtyle, 2-naphtyle substitué et les groupes phényle de structure (G), dans laquelle R1, R2, R3, R4 et R5 sont chacun indépendamment un atome d'hydrogène, un alkyle inférieur en C1 à C4, un halogène ou un groupe amino choisi dans le groupe comprenant NH2, NHR et NRR', R et R' étant chacun indépendamment un alkyle inférieur en C1 à C4, un phényle ou un alcoxy ; enfin chaque C* est choisi indépendamment dans le groupe comprenant 13C et 12C, à condition qu'au moins l'un des C* soit 13C.
Also published as
EP6734591
Latest bibliographic data on file with the International Bureau