Synthesis of [1-13C]pyruvic acid], [2-13C]pyruvic acid], [3-13C]pyruvic acid] and combinations thereof
    2.
    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

    IPC分类号: C07C233/05

    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 [2H1, 13C], [2H2, 13C] and [2H3, 13C]methyl aryl sulfides
    3.
    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

    IPC分类号: A61K5100

    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
    4.
    发明申请
    SYNTHESIS OF [1-13C]PYRUVIC ACID], [2-13C]PYRUVIC ACID], [3-13C]PYRUVIC ACID] AND COMBINATIONS THEREOF 审中-公开
    合成[1-13C]吡咯烷酸],[2-13C]吡咯烷酮],[3-13C]吡咯烷酮]及其组合

    公开(公告)号:US20100069675A1

    公开(公告)日:2010-03-18

    申请号:US12552135

    申请日:2009-09-01

    IPC分类号: C07C317/14

    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 [1-13C]pyruvic acid], [2-13C]pyruvic acid], [3-13C]pyruvic acid] and combinations thereof
    5.
    发明申请
    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:US20090030232A1

    公开(公告)日:2009-01-29

    申请号:US12220234

    申请日:2008-07-22

    IPC分类号: C07C321/02 C07C237/40

    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

    公开(公告)号:US07321049B2

    公开(公告)日:2008-01-22

    申请号:US11268227

    申请日:2005-11-04

    摘要: The present invention is directed to labeled compounds of the formulae wherein Q is selected from the group consisting of —S—, —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. The present invention is also directed to a process of preparing labeled compounds, e.g., process of preparing [13C]methacrylic acid by reacting a (CH3CH2O—13C(O)—13CH2)— aryl sulfone precursor with 13CHI to form a (CH3CH2O—13C(O)—13C(13CH3)2)— aryl sulfone intermediate, and, reacting the (CH3CH2O—13C(O)—13C(13CH3)2)— aryl sulfone intermediate with sodium hydroxide, followed by acid to form [13C]methacrylic acid. The present invention is further directed to a process of preparing [2H8]methyl methacrylate by reacting a (HOOC—C(C2H3)2— aryl sulfinyl intermediate with CD3I to form a (2H3COOC—C(C2H3)2)— aryl sulfinyl intermediate, and heating the(2H3COOC—C(C2H3)2)— aryl sulfinyl intermediate at temperatures and for time sufficient to form [2H8]methyl methacrylate.

    Synthesis of isotopically labeled R- or S-[13C, 2H] glycerols
    7.
    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

    IPC分类号: C07C31/22

    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
    8.
    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

    IPC分类号: C07C22900

    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。

    Synthesis of [13C] and [2H] substituted methacrylic acid, [13C] and [2H] substituted methyl methacrylate and/or related compounds
    10.
    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

    IPC分类号: C07C317/12 C07C321/22

    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。