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Water-soluble photochromic compound

Foreign code F160008904
File No. 92US
Posted date Nov 14, 2016
Country United States of America
Application number 201314427635
Gazette No. 20150307541
Gazette No. 9738675
Date of filing Sep 6, 2013
Gazette Date Oct 29, 2015
Gazette Date Aug 22, 2017
International application number JP2013074052
International publication number WO2014042087
Date of international filing Sep 6, 2013
Date of international publication Mar 20, 2014
Priority data
  • P2012-199292 (Sep 11, 2012) JP
  • 2013WO-JP74052 (Sep 6, 2013) WO
Title Water-soluble photochromic compound
Abstract (US9738675)
A diarylethene compound having high water-solubility is provided, and the compound is a diarylethene compound of formula (I) wherein, Sg is a monovalent sugar-type residue consisting of a sugar-type compound (in which some of hydroxyl groups may be protected) selected from a group consisting of a six-membered ring sugar, a five-membered ring sugar, cyclitol and oligosaccharides containing a six-membered ring sugar, a five-membered ring sugar, or cyclitol and excluding an hydroxyl group; U is ―(CH2)n-, ―CH2―U′―, or ―C(═O)― (wherein, n is an integer of 1 to 5, U′ is a C1-C10 alkyl group binding to Ar); and Ar is a group represented by formula (A1) or (A2); wherein, X is S, SO2, NR3 (R3 is a C1-C3 alkyl group) or O, R is C1-C4 alkyl group, R1 and R2 are independently a C1-C3 alkyl group, a is 0 or 1, b is an integer of 0-3, and * represents a bond with U); Y is a hydrogen atom or a halogen atom; m is an integer of 5-7.
Scope of claims [claim1]
1. A diarylethene compound represented by formula (I)

wherein, Sg is a monovalent sugar residue formed by removing one hydroxyl group from a sugar compound or a monovalent protected sugar residue formed by removing one hydroxyl groups from a sugar compound in which one or more other hydroxyl groups are protected, and wherein the sugar is selected from the group consisting of a six-membered ring sugar, a five-membered ring sugar, cyclitol and oligosaccharides containing a six-membered ring sugar, a five-membered ring sugar, or cyclitol; U is -- (CH2)n -- , -- CH2 -- U' -- , or -- C(.dbd.O) -- wherein
n is an integer of 1 to 5,
U' is a C2-C10 branched alkylene group binding to Ar, and
Ar is a group represented by formula (A1) or (A2);
wherein,
X is S, SO2, NR3 in which R3 is a C1-C3 alkyl group, or O,
R is a C1-C4 alkyl group,
R1 and R2 are independently a C1-C3 alkyl group,
a is 0 or 1,
b is an integer of 0-3, and
* represents a bond with U;
Y is a hydrogen atom or a halogen atom; and
m is an integer of 3 to 5.
[claim2]
2. The compound according to claim 1, wherein the Sg is a monovalent sugar residue formed by removing one hydroxyl group from pyranose.
[claim3]
3. The compound according to claim 1, wherein the Sg is a monovalent sugar residue formed by removing one hydroxyl group from pyranose at a position-1 carbon.
[claim4]
4. The compound according to claim 1, wherein the Sg is a monovalent sugar residue formed by removing one hydroxyl group from cyclitol.
[claim5]
5. The compound according to claim 1, wherein the X is S or SO2.
[claim6]
6. A method for producing a diarlyethene compound according to claim 1, comprising: (1) a step of preparing a halogenated sugar derivative derived from a sugar-type compound selected from the group consisting of a six-membered ring sugar, a five-membered ring sugar, cyclitol and oligosaccharides containing a six-membered ring sugar, a five-membered ring sugar, or cyclitol, and having 1 hydroxyl group substituted with a halogen atom, and all other hydroxyl groups protected by protection groups;
(2) an etherification step of reacting the halogenated sugar derivative with the compound represented by formula (a) to generate a compound represented by formula (b)

wherein, U, Ar, Y and m are as defined above;

wherein, U, Ar, Y and m are as defined above, and PSg shows a group in which all hydroxyl groups of the Sg are protected; and (3) a deprotection step of removing a protection group of the compound represented by formula (b).
[claim7]
7. The method according to claim 6, wherein step (1) is performed under a presence of Ag2O.
[claim8]
8. The method according to claim 6, wherein the halogen atom in the halogenated sugar derivative is bromine atom.
[claim9]
9. The method according to claim 6, wherein a protection group in the halogenated sugar derivative is an acyl group.
  • Inventor, and Inventor/Applicant
  • TOKIWA HIROAKI
  • IRIE MASAHIRO
  • IKEDA KIYOSHI
  • OTSUBO TADAMUNE
  • JOSHO GAKUEN EDUCATIONAL FOUNDATION
  • RIKKYO EDUCATIONAL CORPORATION
IPC(International Patent Classification)
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