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    Synthesis of labeled metabolites
    1.
    发明授权
    Synthesis of labeled metabolites 失效
    标记代谢物的合成

    公开(公告)号：US06709645B1

    公开(公告)日：2004-03-23

    申请号：US10419310

    申请日：2003-04-18

    申请人： Rodolfo A. Martinez ,  Louis A. Silks, III ,  Clifford J. Unkefer ,  Robert Atcher

    发明人： Rodolfo A. Martinez ,  Louis A. Silks, III ,  Clifford J. Unkefer ,  Robert Atcher

    IPC分类号： A61K5104

    CPC分类号： C07C317/04 ,  A61K51/0478 ,  C07B2200/05 ,  C07C317/18 ,  C07C323/65

    摘要： The present invention is directed to labeled compounds, for example, isotopically enriched mustard gas metabolites including: [1,1′,2,2′-13C4]ethane, 1,1′-sulfonylbis[2-(methylthio); [1,1′,2,2′-13C4]ethane, 1-[[2-(methylsulfinyl)ethyl]sulfonyl]-2-(methylthio); [1,1′,2,2′-13C4]ethane, 1,1′-sulfonylbis[2-(methylsulfinyl)]; and, 2,2′-sulfinylbis([1,2-13C2]ethanol of the general formula where Q1 is selected from the group consisting of sulfide (—S—), sulfone (—S(O)—), sulfoxide (—S(O2)—) and oxide (—O—), at least one C* is 13C, X is selected from the group consisting of hydrogen and deuterium, and Z is selected from the group consisting of hydroxide (—OH), and —Q2—R where Q2 is selected from the group consisting of sulfide (—S—), sulfone(—S(O)—), sulfoxide (—S(O2)—) and oxide (—O—), and R is selected from the group consisting of hydrogen, a C1 to C4 lower alkyl, and amino acid moieties, with the proviso that when Z is a hydroxide and Q1 is a sulfide, then at least one X is deuterium.

    摘要翻译： 本发明涉及标记的化合物，例如同位素富集的芥子气代谢物，包括：[1,1'，2,2'-C]]乙烷，1,1'-磺酰基双[2-（甲硫基）; [1,1'，2,2'-13 C]乙烷，1 - [[2-（甲基亚磺酰基）乙基]磺酰基] -2-（甲硫基）; [1,1'，2,2'-13 C]乙烷，1,1'-磺酰基双[2-（甲基亚磺酰基）]; 并且通式为Q 1的2,2'-亚磺酰基双（[1,2-，13C2]乙醇）选自硫化物（-S-），砜（-S（O） - ），亚砜（-S（O 2） - ）和氧化物（-O-），至少一个C *为13 C，X选自氢和氘，Z选自 的氢氧化物（-OH）和-Q 2 -R，其中Q 2选自硫化物（-S-），砜（-S（O） - ），亚砜（-S（O 2） ） - ）和氧化物（-O-），R选自氢，C1至C4低级烷基和氨基酸部分，条件是当Z为氢氧根且Q 1为 硫化物，那么至少一个X是氘。

    Synthesis of [2H1, 13C], [2H2, 13C] and [2H3, 13C]methyl aryl sulfones and sulfoxides
    2.
    发明授权
    Synthesis of [2H1, 13C], [2H2, 13C] and [2H3, 13C]methyl aryl sulfones and sulfoxides 失效
    [2H1,13C]，[2H2,13C]和[2H3,13C]甲基芳基砜和亚砜的合成

    公开(公告)号：US06764673B2

    公开(公告)日：2004-07-20

    申请号：US10342521

    申请日：2003-01-14

    申请人： Rodolfo A. Martinez ,  Marc A. Alvarez ,  Louis A. Silks, III ,  Clifford J. Unkefer ,  Jurgen G. Schmidt

    发明人： Rodolfo A. Martinez ,  Marc A. Alvarez ,  Louis A. Silks, III ,  Clifford J. Unkefer ,  Jurgen G. Schmidt

    IPC分类号： A61K5100

    CPC分类号： C07C321/28 ,  C07B2200/05 ,  C07C317/14

    摘要： The present invention is directed to labeled compounds, [2H1, 13C], [2H2, 13C] and [2H3, 13C]methyl aryl sulfones and [2H1, 13C], [2H2, 13C] and [2H3, 13C]methyl aryl sulfoxides, wherein the 13C methyl group attached to the sulfur of the sulfone or sulfoxide includes exactly one, two or three deuterium atoms and the aryl group is selected from the group consisting of 1-naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, and phenyl groups with the structure: wherein R1, R2, R3, R4 and R5 are each independently, hydrogen, a C1-C4 lower alkyl, a halogen, an amino group from the group consisting of NH2, NHR and NRR′ where R and R′ are each a C1-C4 lower alkyl, a phenyl, or an alkoxy group. The present invention is also directed to processes of preparing methyl aryl sulfones and methyl aryl sulfoxides.

    摘要翻译： 本发明涉及标记的化合物，[2 H 1，C 13 C]，[2 H 2，13 C]和[2 H 3，13 C]甲基芳基砜和[ 2> H1，13 C]，[2 H 2，13 C]和[2 H 3，13 C]甲基芳基亚砜，其中与硫连接的13 C甲基 砜或亚砜包括恰好一个，两个或三个氘原子，并且芳基选自1-萘基，取代的1-萘基，2-萘基，取代的2-萘基和具有以下结构的苯基：其中 R 1，R 2，R 3，R 4和R 5各自独立地为氢，C 1 -C 4低级烷基，卤素，由NH 2，NHR和NRR'组成的组中的氨基，其中R和R'各自为C 1 -C 4 低级烷基，苯基或烷氧基。 本发明还涉及制备甲基芳基砜和甲基芳基亚砜的方法。

    Synthesis of [2H1, 13C], [2H2, 13C] and [2H3, 13C]methyl aryl sulfides
    4.
    发明授权
    Synthesis of [2H1, 13C], [2H2, 13C] and [2H3, 13C]methyl aryl sulfides 失效
    [2H1,13C]，[2H2,13C]和[2H3,13C]甲基芳基硫化物的合成

    公开(公告)号：US06713044B2

    公开(公告)日：2004-03-30

    申请号：US10342577

    申请日：2003-01-14

    申请人： Rodolfo A. Martinez ,  Marc A. Alvarez ,  Louis A. Silks, III ,  Clifford J. Unkefer

    发明人： Rodolfo A. Martinez ,  Marc A. Alvarez ,  Louis A. Silks, III ,  Clifford J. Unkefer

    IPC分类号： A61K5100

    CPC分类号： C07C319/14 ,  C07B59/001 ,  C07B2200/05 ,  C07C17/093 ,  C07C19/07 ,  C07C321/28

    摘要： The present invention is directed to labeled compounds, [2H1, 13C], [2H2, 13C] and [2H3, 13C]methyl aryl sulfides wherein the 13C methyl group attached to the sulfur of the sulfide includes exactly one, two or three deuterium atoms and the aryl group is selected from the group consisting of 1-naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, and phenyl groups with the structure wherein R1, R2, R3, R4, and R5 are each independently, hydrogen, a C1-C4 lower alkyl, a halogen, an amino group from the group consisting of NH2, NHR and NRR′ where R and R′ are each a C1-C4 lower alkyl, a phenyl, or an alkoxy group. The present invention is also directed to processes of preparing [2H1, 13C], [2H2,13C] and [2H3, 13C]methyl aryl sulfides wherein the 13C methyl group attached to the sulfur of the sulfide includes exactly one, two or three deuterium atoms. The present invention is also directed to the labeled compounds of [2H1, 13C]methyl iodide and [2H2, 13C]methyl iodide.

    摘要翻译： 本发明涉及标记的化合物[2 H 1，C 13 C]，[2 H 2，13 C]和[2 H 3，13 C]甲基芳基硫化物， 连接硫化硫的13 C甲基包括正好一个，两个或三个氘原子，芳基选自1-萘基，取代的1-萘基，2-萘基，取代的2-萘基， 和具有其中R1，R2，R3，R4和R5的结构的苯基各自独立地为氢，C1-C4低级烷基，卤素，由NH2，NHR和NRR'组成的组的氨基，其中R和R '各自为C 1 -C 4低级烷基，苯基或烷氧基。 本发明还涉及制备[2 H 1，13 C]，[2 H 2，13 C]和[2 H 3，13 C]甲基芳基硫化物的方法，其中 连接硫化硫的13 C甲基包括恰好一个，两个或三个氘原子。 本发明还涉及[<2> H1，13 C]甲基碘和[2 H 2，13 C]甲基碘的标记化合物。

    Synthesis of [1-13C]pyruvic acid], [2-13C]pyruvic acid], [3-13C]pyruvic acid] and combinations thereof
    6.
    发明授权
    Synthesis of [1-13C]pyruvic acid], [2-13C]pyruvic acid], [3-13C]pyruvic acid] and combinations thereof 有权
    合成[1-13C]丙酮酸]，[2-13C]丙酮酸]，[3-13C]丙酮酸]及其组合

    公开(公告)号：US08198484B2

    公开(公告)日：2012-06-12

    申请号：US12220234

    申请日：2008-07-22

    申请人： Rodolfo A. Martinez ,  Clifford J. Unkefer ,  Marc A. Alvarez

    发明人： Rodolfo A. Martinez ,  Clifford J. Unkefer ,  Marc A. Alvarez

    IPC分类号： C07C233/05

    CPC分类号： C07C69/716 ,  C07B59/001 ,  C07B2200/05 ,  C07C59/347 ,  C07C235/80 ,  C07C317/24 ,  C07C317/46 ,  Y10T436/200833

    摘要： The present invention is directed to the labeled compounds, wherein C* is each either 13C and 12C where at least one C* is 13C, each hydrogen of the methylene group is hydrogen or deuterium, the methyl group includes either zero or three deuterium atoms, Q is sulfide, sulfinyl, or sulfone, Z is an aryl group such as 1-naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, or a phenyl group wherein R1, R2, R3, R4 and R5 are each independently either hydrogen, a C1-C4 lower alkyl, a halogen, and an amino group such as NH2, NHR and NRR′ where R and R′ are each independently either 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 the labeled compounds

    摘要翻译： 本发明涉及标记的化合物，其中C *各自为13 C和12 C，其中至少一个C *为13 C，亚甲基的每一个氢为氢或氘，甲基包括零或三个氘原子， Q是硫化物，亚磺酰基或砜，Z是1-萘基，取代的1-萘基，2-萘基，取代的2-萘基或其中R1，R2，R3，R4和R5各自的苯基的芳基 独立地是氢，C 1 -C 4低级烷基，卤素和氨基如NH 2，NHR和NRR'，其中R和R'各自独立地是C 1 -C 4低级烷基，苯基和烷氧基， 并且甲基可以包括零个或三个氘原子。 本发明还涉及标记的化合物

    Synthesis of [13C] and [2H] substituted methacrylic acid, [13C] and [2H] substituted methyl methacrylate and/or related compounds
    7.
    发明授权
    Synthesis of [13C] and [2H] substituted methacrylic acid, [13C] and [2H] substituted methyl methacrylate and/or related compounds 失效
    [13 C]和[2H]取代的甲基丙烯酸的合成[13 C]和[2H]取代的甲基丙烯酸甲酯和/或相关化合物

    公开(公告)号：US07662993B2

    公开(公告)日：2010-02-16

    申请号：US11591828

    申请日：2006-11-02

    申请人： Marc A. Alvarez ,  Rodolfo A. Martinez ,  Clifford J. Unkefer

    发明人： Marc A. Alvarez ,  Rodolfo A. Martinez ,  Clifford J. Unkefer

    IPC分类号： C07C317/12 ,  C07C321/22

    CPC分类号： C07C51/377 ,  C07B2200/05 ,  C07C67/317 ,  C07C317/44 ,  C07C323/52 ,  C07C57/04 ,  C07C69/54

    摘要： The present invention is directed to labeled compounds of the formulae wherein Q is selected from the group consisting of —S(═O)—, and —S(═O)2—, Z is selected from the group consisting of 1-naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, and phenyl groups with the structure wherein R1, R2, R3, R4 and R5 are each independently selected from the group consisting of hydrogen, a C1-C4 lower alkyl, a halogen, and an amino group selected from the group consisting of NH2, NHR and NRR′ where R and R′ are each independently selected from the group consisting of a C1-C4 lower alkyl, an aryl, and an alkoxy group, and X is selected from the group consisting of hydrogen, a C1-C4 lower alkyl group, and a fully-deuterated C1-C4 lower alkyl group.

    摘要翻译： 本发明涉及下式的标记化合物其中Q选自-S（ - ） - 和-S（ - O）2 - ，Z选自1-萘基， 取代的1-萘基，2-萘基，取代的2-萘基和具有以下结构的苯基：其中R 1，R 2，R 3，R 4和R 5各自独立地选自氢，C 1 -C 4低级烷基，卤素 和选自NH 2，NHR和NRR'的氨基，其中R和R'各自独立地选自C 1 -C 4低级烷基，芳基和烷氧基，并且X选自 由氢，C1-C4低级烷基和完全氘化的C1-C4低级烷基组成的组。

    Synthesis of [1-13C]pyruvic acid], [2-13C]pyruvic acid], [3-13C]pyruvic acid] and combinations thereof
    8.
    发明授权
    Synthesis of [1-13C]pyruvic acid], [2-13C]pyruvic acid], [3-13C]pyruvic acid] and combinations thereof 失效
    合成[1-13C]丙酮酸]，[2-13C]丙酮酸]，[3-13C]丙酮酸]及其组合

    公开(公告)号：US07582801B2

    公开(公告)日：2009-09-01

    申请号：US11052589

    申请日：2005-02-07

    申请人： Rodolfo A. Martinez ,  Clifford J. Unkefer ,  Marc A. Alvarez

    发明人： Rodolfo A. Martinez ,  Clifford J. Unkefer ,  Marc A. Alvarez

    IPC分类号： C07C49/04

    CPC分类号： C07C69/716 ,  C07B59/001 ,  C07B2200/05 ,  C07C59/347 ,  C07C235/80 ,  C07C317/24 ,  C07C317/46 ,  Y10T436/200833

    摘要： The present invention is directed to labeled compounds, of the formulae 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 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.

    摘要翻译： 本发明涉及下式的标记化合物，其中C *各自独立地选自13 C和12 C，条件是至少一个C *为13 C，亚甲基的每个氢可以独立地为氢 或氘，甲基包括零或三个氘原子，Q为硫醚，亚磺酰基和砜基，Z为1-萘基，取代的1-萘基，2-萘基，取代的芳基 2-萘基和具有其中R 1，R 2，R 3，R 4和R 5各自独立地为氢，C 1 -C 4低级烷基，卤素和氨基的基团的苯基，其中NH 2，NHR 和NRR'，其中R和R'各自独立地为C1-C4低级烷基，苯基和烷氧基的基团，甲基可以包括零或三个氘原子。

    Synthesis of isotopically labeled R- or S-[13C, 2H] glycerols
    9.
    发明授权
    Synthesis of isotopically labeled R- or S-[13C, 2H] glycerols 有权
    同位素标记的R-或S- [13C，2H]甘油的合成

    公开(公告)号：US07321070B2

    公开(公告)日：2008-01-22

    申请号：US10629982

    申请日：2003-07-30

    申请人： Rodolfo A. Martinez ,  Clifford J. Unkefer ,  Marc A. Alvarez

    发明人： Rodolfo A. Martinez ,  Clifford J. Unkefer ,  Marc A. Alvarez

    IPC分类号： C07C31/22

    CPC分类号： C07C31/225 ,  C07B2200/05 ,  C07B2200/07

    摘要： The present invention is directed to asymmetric chiral labeled glycerols including at least one chiral atom, from one to two 13C atoms and from zero to four deuterium atoms bonded directly to a carbon atom, e.g., (2S) [1,2-13C2]glycerol and (2R) [1,2-13C2]glycerol, and to the use of such chiral glycerols in the preparation of labeled amino acids.

    摘要翻译： 本发明涉及不对称手性标记的甘油，其包括至少一个手性原子，一个至两个13个C原子和从零到四个直接键合到碳原子上的氘原子，例如（2S） [1,2-D] 13 C]甘油和（2R）[1,2- 13 C 12] ]甘油，以及使用这些手性甘油来制备标记的氨基酸。

    Synthesis of labeled oxalic acid derivatives
    10.
    发明授权
    Synthesis of labeled oxalic acid derivatives 失效
    标记草酸衍生物的合成

    公开(公告)号：US06753446B1

    公开(公告)日：2004-06-22

    申请号：US10456081

    申请日：2003-06-05

    申请人： Rodolfo A. Martinez ,  Clifford J. Unkefer ,  Marc A. Alvarez

    发明人： Rodolfo A. Martinez ,  Clifford J. Unkefer ,  Marc A. Alvarez

    IPC分类号： C07C22900

    CPC分类号： C07C233/56 ,  C07B59/001 ,  C07B2200/05

    摘要： The present invention is directed to labeled compounds, specifically where each C* is selected from the group consisting of a carbon-12, i.e., 12C, or a carbon-13, i.e., 13C and at least one C* is 13C, R1 is selected from the group of C1-C4 lower alkyl and aryl, and X is selected from the group of —NR2R3 where R2 and R3 are each independently selected from the group of C1-C4 lower alkyl, alkoxy and aryl, —SR4 where R4 is selected from the group of C1-C4 lower alkyl, alkoxy and aryl, and —OR5 where R5 is selected from the group of C1-C4 lower alkyl, alkoxy and aryl with the proviso that when R1 is methyl then R5 is other than methyl, when R1 is ethyl then R5 is other than ethyl, and when R1 is benzyl then R5 is other than benzyl.

    摘要翻译： 本发明涉及标记化合物，特别是其中每个C *选自碳12，即12 C，或碳-13，即13 C和至少一个C * 是13 C，R 1选自C 1 -C 4低级烷基和芳基，X选自-NR 2 R 3基团，其中R 2和R 3 >各自独立地选自C 1 -C 4低级烷基，烷氧基和芳基-SR 4，其中R 4选自C 1 -C 4低级烷基，烷氧基和芳基，-OR 5 其中R 5选自C 1 -C 4低级烷基，烷氧基和芳基，条件是当R 1是甲基时，R 5不是甲基，当R 1是乙基时，则 R 5不是乙基，当R 1是苄基时，R 5不是苄基。