Urazole compounds

Patent metadata

Field	Value
Publication number	US-2016200707-A1
Application number	US-201414910058-A
Country	US
Kind code	A1
Filing date	Aug 8, 2014
Priority date	Aug 9, 2013
Publication date	Jul 14, 2016
Grant date	—

Abstract

The present invention relates to a compound of formula (I) or a stereoisomer, enantiomer, racemic, or tautomer thereof, (I) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , L 1 and Q 1 have the meaning defined in the claims and the description. The present invention also relates to a process for the preparation of the compound of formula (I). The present invention also relates to the use of a compound of formula (I) as an in situ precursor of a triazolinedione reagent for the functionalization of enes, dienes, aryl and heteroaryl systems via the ene reactions, Diels-Alder reactions, and electrophilic aromatic substitution reactions of said reagent. The present invention also relates to the use of a compound of formula (I) in polymers, membranes, adhesives, foams, sealants, molded articles, films, extruded articles, fibers, elastomers, polymer based additives, pharmaceutical and biomedical products, varnishes, paints, coatings, inks, composite material, organic LEDs, organic semiconductors, conducting organic polymers, or 3D printed articles. The present invention also relates to article comprising said compound of formula (I) and to a process for reshaping and/or repairing said article.

First claim

1 . A compound of formula (I) or a stereoisomer, enantiomer, racemic, or tautomer thereof,

wherein,
L 1 is selected from C 1-10 alkylene; C 2-10 alkenylene; or C 2-10 alkynylene; or L 1 and R 2 together with the carbon atoms to which they are attached form a saturated or unsaturated 4-, 5-, 6-, 7- or 8-membered ring;
wherein said C 1-10 alkylene; C 2-10 alkenylene; C 2-10 alkynylene, or saturated or unsaturated 4-, 5-, 6-, 7- or 8-membered ring, optionally comprises one or more heteroatoms in the alkylene, alkenylene, alkynylene, or saturated or unsaturated 4-, 5-, 6-, 7- or 8-membered ring moiety, said heteroatoms being each independently selected from O, S and N;
and wherein said C 1-10 alkylene; C 2-10 alkenylene; C 2-10 alkynylene, or saturated or unsaturated 4-, 5-, 6-, 7- or 8-membered ring, can be unsubstituted or substituted with one or more Z 1 ;

Q 1 is a single bond or is selected from the group consisting of —OC(O)—; —NH—C(O)—; —OS(O)—; —OS(O) 2 —; —NH—S(O)—; —NH—S(O) 2 —; —OC(O)—[CR 13 R 14 ] q —; and —OC(O)—[C(R 13 )(L 4 -O—R 15 )] q —[CR 16 R 17 ] p —O—; wherein each left side of said groups is attached to L 1 and the right side thereof is attached to R 5 ; and wherein,
q is an integer selected from 1; 2 or 3;
p is an integer selected from 0; 1 or 2;
L 4 is a single bond or is selected from the group consisting of C 1-10 alkylene; C 2-10 alkenylene; and C 2-10 alkynylene;
wherein said C 1-10 alkylene; C 2-10 alkenylene; and C 2-10 alkynylene, optionally comprises one or more heteroatoms in the alkylene, alkenylene, alkynylene moiety, said heteroatoms being each independently selected from O, S and N;
and wherein said C 1-10 alkylene; C 2-10 alkenylene; C 2-10 alkynylene, can be unsubstituted or substituted with one or more Z 2 ;

R 1 is selected from the group consisting of C 2-10 alkyl; C 6-12 aryl; C 6-12 arylC 1-6 alkyl; C 6-12 arylC 1-6 alkylC 6-12 aryl; heterocyclyl; heteroaryl; heterocyclylC 1-6 alkyl; heteroarylC 1-6 alkyl; and a polymeric group; and a pharmaceutically active moiety;
wherein said C 2-10 alkyl, C 6-12 arylC 1-6 alkyl, C 6-12 arylC 1-6 alkylC 6-12 aryl, heterocyclylC 1-6 alkyl; heteroarylC 1-6 alkyl, optionally comprises one or more heteroatoms in the alkyl moiety, said heteroatoms being each independently selected from O, S or N;
wherein at least one carbon atom or heteroatom of said C 2-10 alkyl; C 6-12 aryl; C 6-12 arylC 1-6 alkyl; C 6-12 arylC 1-6 alkylC 6-12 aryl; heterocyclyl; heteroaryl; heterocyclylC 1-6 alkyl; and heteroarylC 1-6 alkyl, can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;
wherein said C 2-10 alkyl, C 3-8 cycloalkyl, C 6-12 aryl, C 6-12 arylC 1-6 alkyl, C 6-12 arylC 1-6 alkylC 6-12 aryl, heterocyclyl; heteroaryl; heterocyclylC 1-6 alkyl; and heteroarylC 1-6 alkyl, can be unsubstituted or substituted with one or more Z 3 ;
and wherein said polymeric group is selected from the group comprising polyethylene oxide; polyacrylate; polymethacrylate; polystyrene; copolymer of acrylate; poly(methyl methacrylate); methacrylate and/or styrene; poly(isobornyl acrylate); polyacrylonitrile; polyether; polyester; polylactic acid; polyamide; polyester amide; polyurethane; polycarbonate; poly-alpha-olefin; ethylene propylene diene monomer (M-class) rubber (EPDM); ethylene propylene rubber (EPM); hydrogenated or unhydrogenated polybutadienes; acrylonitrile butadiene styrene (ABS); styrene-butadiene rubber (SBR); polysiloxanes; and/or block, comb and/or star copolymers of the polymeric group;

or R 1 is a group of formula (i);

wherein,
L 2 is a single bond or is selected from the group consisting of C 1-10 alkylene; C 2-10 alkenylene; C 2-10 alkynylene; and C 6-12 arylene;
wherein said C 1-10 alkylene; C 2-10 alkenylene; C 2-10 alkynylene, or C 6-12 arylene, optionally comprises one or more heteroatoms in the alkylene, alkenylene, alkynylene, or arylene moiety, said heteroatoms being each independently selected from O, S and N;
and wherein said C 1-10 alkylene; C 2-10 alkenylene; C 2-10 alkynylene, or C 6-12 arylene, can be unsubstituted or substituted with one or more Z 4 ;

Q 2 is selected from the group consisting of C 1-10 alkylene; C 3-6 cycloalkylene; —OC(O)—; —NH—C(O)—; —NH—C(O)—[CR 13 R 14 ] q ; —OS(O)—; —OS(O) 2 —; —NH—S(O)—; and —NH—S(O) 2 ; wherein each left side of said groups is attached to L 2 and the right side thereof is attached to R 18 ;
wherein said C 1-10 alkylene, optionally comprises one or more heteroatoms, said heteroatoms being each independently selected from O, S and N;
and wherein said C 1-10 alkylene and said C 3-6 cycloalkylene; can be unsubstituted or substituted with one or more Z 5 ;

or Q 2 is a group of formula (ii);

wherein the left side of the group formula (ii) is attached to L 2 and the right side thereof is attached to R 18 ; and wherein,
or Q 2 -R 18 or is a group of formula (iii);

wherein the left side of the group formula (ii) is attached to L 2 and the right side thereof is attached to R 18 ; and wherein,
L 3 is a single bond or is selected from the group consisting of C 1-10 alkylene; C 2-10 alkenylene; C 2-10 alkynylene; and C 6-12 aryl;
wherein said C 1-10 alkylene; C 2-10 alkenylene; C 2-10 alkynylene, or C 6-12 aryl, optionally comprises one or more heteroatoms in the alkylene, alkenylene, alkynylene, or aryl moiety, said heteroatoms being each independently selected from O, S and N;
and wherein said C 1-10 alkylene; C 2-10 alkenylene; C 2-10 alkynylene, or C 6-12 aryl, can be unsubstituted or substituted with one or more Z 6 ;

R 2 is selected from the group consisting of halo; nitro; cyano; C 1-20 alkyl; C 2-20 alkenyl; C 2-20 alkynyl; C 6-12 aryl; C 3-8 cycloalkyl; C 6-12 arylC 1-6 alkyl; C 6-12 arylC 1-6 alkylC 6-12 aryl; heterocyclyl; heteroaryl; heterocyclylC 1-6 alkyl; heteroarylC 1-6 alkyl; and a polymeric group; and a pharmaceutically active moiety; R 3 is selected from the group consisting of halo; nitro; cyano; C 1-20 alkyl; C 2-20 alkenyl; C 2-20 alkynyl; C 6-12 aryl; C 3-8 cycloalkyl; C 6-12 arylC 1-6 alkyl; C 6-12 arylC 1-6 alkylC 6-12 aryl; heterocyclyl; heteroaryl; heterocyclylC 1-6 alkyl; heteroarylC 1-6 alkyl; and a polymeric group; and a pharmaceutically active moiety;
R 4 is selected from the group consisting of halo; nitro; cyano; C 1-20 alkyl; C 2-20 alkenyl; C 2-20 alkynyl; C 6-12 aryl; C 3-8 cycloalkyl; C 6-12 arylC 1-6 alkyl; C 6-12 arylC 1-6 alkylC 6-12 aryl; heterocyclyl; heteroaryl; heterocyclylC 1-6 alkyl; heteroarylC 1-6 alkyl; and a polymeric group; and a pharmaceutically active moiety;
or R 2 and R 3 and R 4 together with the carbon atom to which they are attached can form a saturated or unsaturated 4-, 5-, 6-, 7- or 8-membered ring;
or R 2 and L 1 together with the carbon atom to which they are attached can form a saturated or unsaturated 4-, 5-, 6-, 7- or 8-membered ring;
wherein for R 2 , R 3 and R 4 , each independently; said C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, C 6-12 arylC 1-6 alkyl, heterocyclylC 1-6 alkyl; heteroarylC 1-6 alkyl, or saturated or unsaturated 4-, 5-, 6-, 7- or 8-membered ring, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl, or unsaturated 4-, 5-, 6-, 7- or 8-membered ring moie

Assignees

• Univ Gent

Inventors

• Du Prez Filip
• Winne Johan
• Billiet Stijn
• De Bruycker Kevin

Classifications

• C07D403/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• C08G18/73

  acyclic · CPC title

• C08G2261/46

  Diels-Alder reactions · CPC title

• C08G18/3844

  containing one nitrogen atom in the ring · CPC title

• C08G18/6666

  Compounds of group C08G18/48 or C08G18/52 · CPC title