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    NITRATED HYDROCARBONS AND DERIVATIVES
    6.
    发明公开
    NITRATED HYDROCARBONS AND DERIVATIVES 审中-公开
    NIDRIERTE KOHLENWASSERSTOFFE UND DEREN DERIVATE

    公开(公告)号：EP3121162A1

    公开(公告)日：2017-01-25

    申请号：EP16184250.5

    申请日：2009-04-08

    Applicant: ANGUS CHEMICAL COMPANY

    Inventor： TRAUTH, Daniel M. ,  GREEN, George David ,  SWEDO, Raymond ,  JAMES, Richard L. ,  TOMLINSON, Ian A.

    IPC: C07C205/02 ,  C07C205/15 ,  C07C215/08 ,  C07C215/10 ,  C07C215/20 ,  C07C239/10 ,  C07D263/06 ,  C07D263/52 ,  C07C205/04 ,  C07C205/05 ,  C07C205/06 ,  C07C205/16 ,  C07C205/18 ,  C07C215/28 ,  C07C215/42 ,  C07D263/04 ,  C07D498/04 ,  C07D498/10

    CPC classification number: C07D498/10 ,  A01N43/76 ,  A01N43/90 ,  C07C201/08 ,  C07C201/12 ,  C07C205/02 ,  C07C205/04 ,  C07C205/05 ,  C07C205/06 ,  C07C205/15 ,  C07C205/16 ,  C07C205/18 ,  C07C215/08 ,  C07C215/20 ,  C07C215/28 ,  C07C215/42 ,  C07C239/10 ,  C07C2601/08 ,  C07C2601/14 ,  C07C2601/18 ,  C07C2602/10 ,  C07D263/04 ,  C07D263/52 ,  C07D498/04 ,  C08G18/3271 ,  Y02P20/582

    Abstract: A compound selected from the group consisting of formula I-1, II-1, III-1 and IV-1:

    or a compound selected from the group consisting of: 2-(hydroxylamino)hexane, 3-(hydroxylamino)hexane, 2-(hydroxylamino)octane, and 3-(hydroxylamino)octane, wherein: R 7 and R 9 are independently linear C 2 -C 17 alkyl; R 11 is an unsubstituted linear C 2 -C 17 alkyl; R 8 is H or linear C 1 -C 8 alkyl; R 10 and R 14 are independently H, linear C 1 -C 8 alkyl, or CH 2 OH, or R 9 , R 10 , and the carbon to which they are attached form an eight membered cycloalkyl ring; R 12 is H, an unsubstituted linear C 1 -C 8 alkyl, or CH 2 OH, or R 11 , R 12 , and the carbon to which they are attached form a C 9 -C 11 cycloalkyl ring; R 13 is C 2 -C 20 alkyl, C 3 -C 12 cycloalkyl, aryl, or aryl-alkyl-; R 14 is H or C 1 -C 12 alkyl, or R 13 and R 14 together with the carbon to which they are attached form a C 3 -C 12 cycloalkyl ring; R 15 is H, or R 14 , R 15 , and the atoms to which they are attached form an oxazolidine ring that is optionally substituted with C 1 -C 6 alkyl; and R 16 is H, C 1 -C 12 alkyl, C 3 -C 12 cycloalkyl, or aryl;
    provided that: when the compound is selected from formula I-1, the total number of carbons in R 7 and R 8 , together with the carbon to which they are attached, is 10 to 18; and the compound is not 1-nitrodecane, 2-nitrodecane, 1-nitroundecane, 2-nitroundecane, 3-nitroundecane, 4-nitroundecane, 5-nitroundecane, 6-nitroundecane, 1-nitrododecane, 2-nitrododecane, 3-nitrododecane, 4-nitrododecane, 5-nitrododecane, 6-nitrododecane, 1-nitrotridecane, 2-nitrotridecane, 3-nitrotridecane, 6-nitrotridecane, 1-nitrotetradecane, 1-nitropentadecane, 1-nitrohexadecane, 2-nitrohexadecane, 1-nitroheptadecane, 1-nitrooctadecane, or 2-nitrooctadecane; when the compound is selected from formula II-1, if R 10 is H or linear C 1 -C 8 alkyl, the total number of carbons in R 9 and R 10 , together with the carbon to which they are attached, is 5 to 18; or if R 10 is CH 2 OH, R 9 is linear C 12 -C 16 alkyl; and the compound is not 2-nitro-1-hexanol, 2-nitro-1-heptanol, 2-nitro-1-octanol, 2-methyl-2-nitro-1-heptanol, or 2-nitro-1-dodecanol; when the compound is selected from formula III-1, if R 12 is H or linear C 1 -C 8 alkyl, the total number of carbons in R 11 and R 12 , together with the carbon to which they are attached, is 6 to 18; or if R 12 is CH 2 OH, R 11 is linear C 7 -C 17 alkyl; and the compound is not 2-amino-1-heptanol, 2-amino-2-methyl-1-hexanol, 2-amino-1-octanol, 2-amino-2-ethyl-1-hexanol, 2-amino-1-nonanol, 2-amino-2-methyl-1-octanol, 2-amino-1-decanol, 2-amino-2-octyl-1,3-propanediol, 2-amino-2-butyl-1-hexanol, 2-amino-1-undecanol, 2-amino-1-dodecanol, 2-amino-2-decyl-1,3-propanediol, 2-amino-1-tridecanol, 2-amino-2-methyl-1-dodecanol, 2-amino-1-tetradecanol, 2-amino-2-dodecyl-1,3-propanediol, 2-amino-2-methyl-1-tridecanol, 2-amino-1-pentadecanol, 2-amino-2-tridecyl-1,3-propanediol, 2-amino-1-hexadecanol, 2-amino-2-tetradecyl-1,3-propanediol, 2-amino-2-methyl-1-pentadecanol, 2-amino-2-hexyl-1-decanol, 2-amino-1-heptadecanol, 2-amino-2-pentadecyl-1,3-propanediol, 2-amino-1-octadecanol, or 2-amino-2-hexadecyl-1,3-propanediol; and when the compound is selected from formula IV-1, if R 13 is an ethyl group, R 14 is not H; and the compound is not 5-propyl-1-aza-3,7-dioxabicyclo[3.3.0]octane, 4,4-diethyl-1-oxa-3-azacyclopentane, 3-oxa-1-azaspiro[4.4]nonane, 3-oxa-1-azaspiro[4.5]decane, or 3-oxa-1-azaspiro[4.7]dodecane.

    Abstract translation: 选自式I-1，II-1，III-1和IV-1的化合物或选自2-（羟基氨基）己烷，3-（羟基氨基）己烷，2 - （羟基氨基）辛烷和3-（羟基氨基）辛烷，其中：R 7和R 9独立地为直链C 2 -C 17烷基; R 11是未取代的直链C 2 -C 17烷基; R 8是H或直链C 1 -C 8烷基; R 10和R 14独立地为H，直链C 1 -C 8烷基或CH 2 OH或R 9，R 10，并且它们连接的碳形成八元环烷基环; R 12是H，未取代的直链C 1 -C 8烷基或CH 2 OH或R 11，R 12，并且它们连接的碳形成C 9 -C 11环烷基环; R 13是C 2 -C 20烷基，C 3 -C 12环烷基，芳基或芳基 - 烷基 - ; R 14是H或C 1 -C 12烷基，或R 13和R 14与它们所连接的碳一起形成C 3 -C 12环烷基环; R 15是H或R 14，R 15，并且它们所连接的原子形成任选被C 1 -C 6烷基取代的恶唑烷环; 和R 16是H，C 1 -C 12烷基，C 3 -C 12环烷基或芳基; 条件是：当化合物选自式I-1时，R 7和R 8中的碳总数与它们所连接的碳一起为10至18; 并且化合物不是1-硝基癸烷，2-硝基癸烷，1-硝基十四烷，2-硝基十四烷，3-硝基十四烷，4-硝基十四烷，5-硝基十四烷，6-硝基十二烷，1-硝基十二烷，2-硝基十二烷，3-硝基十二烷，4 - 硝基十二烷，6-硝基十二烷，1-硝基十三烷，2-硝基十三烷，3-硝基十三烷，6-硝基十三烷，1-硝基十四烷，1-硝基十五烷，1-硝基十六烷，2-硝基十六烷，1-硝基十五烷，1-硝基十八烷 ，或2-硝基十八烷; 当化合物选自式II-1时，如果R 10是H或直链C 1 -C 8烷基，则R 9和R 10中的碳总数与它们所连接的碳一起为5〜 18; 或者如果R 10是CH 2 OH，R 9是直链C 12 -C 16烷基; 该化合物不是2-硝基-1-己醇，2-硝基-1-庚醇，2-硝基-1-辛醇，2-甲基-2-硝基-1-庚醇或2-硝基-1-十二烷醇; 当化合物选自式III-1时，如果R 12是H或直链C 1 -C 8烷基，则R 11和R 12中的碳总数与它们所连接的碳一起为6〜 18; 或者如果R 12是CH 2 OH，则R 11是直链C 7 -C 17烷基; 该化合物不是2-氨基-1-庚醇，2-氨基-2-甲基-1-己醇，2-氨基-1-辛醇，2-氨基-2-乙基-1-己醇，2-氨基-1 - 壬醇，2-氨基-2-甲基-1-辛醇，2-氨基-1-癸醇，2-氨基-2-辛基-1,3-丙二醇，2-氨基-2-丁基-1-己醇，2 2-氨基-1-十一烷醇，2-氨基-1-十一烷醇，2-氨基-1-癸醇，2-氨基-1-十一烷醇，2-氨基-1-十一烷醇，2-氨基-1-十一烷醇， - 氨基-1-十四烷醇，2-氨基-2-十二烷基-1,3-丙二醇，2-氨基-2-甲基-1-十三烷醇，2-氨基-1-十五烷醇，2-氨基-2-十三烷基-1 3-丙二醇，2-氨基-1-十六烷醇，2-氨基-2-十四烷基-1,3-丙二醇，2-氨基-2-甲基-1-十五烷醇，2-氨基-2-己基-1-癸醇 2-氨基-1-十七烷醇，2-氨基-2-十五烷基-1,3-丙二醇，2-氨基-1-十八烷醇或2-氨基-2-十六烷基-1,3-丙二醇; 当化合物选自式IV-1时，如果R 13是乙基，则R 14不是H; 并且该化合物不是5-丙基-1-氮杂-3,7-二氧杂二环[3.3.0]辛烷，4,4-二乙基-1-氧杂-3-氮杂环戊烷，3-氧杂-1-氮杂螺[4.4]壬烷 ，3-氧杂-1-氮杂螺[4.5]癸烷或3-氧杂-1-氮杂螺[4.7]十二烷。

    PROCESS FOR THE PREPARATION OF IOPAMIDOL
    9.
    发明公开
    PROCESS FOR THE PREPARATION OF IOPAMIDOL 有权
    用于生产碘帕醇

    公开(公告)号：EP3066071A1

    公开(公告)日：2016-09-14

    申请号：EP14796024.9

    申请日：2014-11-04

    Applicant: Bracco Imaging S.p.A.

    Inventor： BATTISTINI, Elisa ,  BUONSANTI, Federica ,  IMPERIO, Daniela ,  LATTUADA, Luciano ,  NAPOLITANO, Roberta

    IPC: C07C231/02 ,  C07F5/02 ,  C07F5/04

    CPC classification number: C07C231/14 ,  C07C201/12 ,  C07C227/04 ,  C07C231/02 ,  C07C231/12 ,  C07F5/025 ,  C07F5/04 ,  C07F5/05 ,  Y02P20/55 ,  Y02P20/582 ,  C07C237/46

    Abstract: The present invention discloses a process for the preparation of Iopamidol of formula (II) and comprising the following steps: a) reacting the Compound (I) wherein X is OR2 or R3, and wherein R2 and R3 are a Ci-C6 linear or branched alkyl, C3-C6 cycloalkyl, C6 aryl, optionally substituted with a group selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, t-butyl and phenyl, with the acylating agent (S)-2-(acetyloxy)propanoyl chloride in a reaction medium to provide the acetyloxy derivative of Compound (I); b) hydrolyzing the intermediate from step a) with an aqueous solution at a pH comprised from 0 to 7, by adding water or a diluted alkaline solution such as sodium hydroxide or potassium hydroxide, freeing the hydroxyls from the boron-containing protective groups, obtaining the N—(S)-2-(acetyloxy)propanoyl derivative of Compound (II); c) alkaline hydrolysis to restore the (S)-2-(hydroxy)propanoyl group and to obtain Iopamidol (II) and optional recovery of the boron derivative from the solution obtained in step b). The boron-containing protective group is versatile, efficient and recyclable. A one-pot synthesis, without intermediate isolation is provided, leading to a decreasing of recovered and recycled solvents and a significant increasing in the yield, representing a significant advantage in terms of cost-effectiveness of the entire process and environmental awareness.

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