Dental restorative material based on an antimicrobially active compound

Patent metadata

Field	Value
Publication number	US-9339443-B2
Application number	US-201213368998-A
Country	US
Kind code	B2
Filing date	Feb 8, 2012
Priority date	Feb 15, 2011
Publication date	May 17, 2016
Grant date	May 17, 2016

Abstract

The invention relates to a dental restorative material which comprises (a) at least one antimicrobially active compound of Formula (I)

[AG] m -R 1 —Z—SP—Y—R 2 —[WG] p   (I),

or a filler that is surface-modified with at least one compound of Formula (I), (b) at least one radically polymerizable monomer and (c) at least one initiator for the radical polymerization. The invention also relates to a use of such dental restorative material for the preparation of an adhesive, primer, cement, coating material or filling material.

The invention also relates to a dental material which comprises at least one compound of Formula (I), as well as a use of a compound of Formula (I) for modifying the surface of a substrate selected from ceramic materials, noble and non-noble metals, hard tooth structure, tooth enamel, dentine, collagen, soft tissue, mucous membrane and leather.

First claim

The invention claimed is:

1. Dental restorative material which comprises
(a) at least one antimicrobially active compound of Formula (I)
[AG] m -R 1 —Z—SP—Y—R 2 —[WG] p   (I),

wherein the variables have the following meanings:
m=1, 2, 3 or 4;
p=1, 2 or 3;
R 1 =is absent or a linear or branched C 1 to C 20 alkylene radical which can be interrupted one or more times by O, S, NH, N + R 3 2 , SiR 3 2 , OSiR 3 2 , CONH, CONR 3 , COO and/or OCONH, a substituted or unsubstituted, aromatic C 6 to C 14 radical or a combination thereof;
R 2 =is absent or a linear or branched C 1 to C 20 alkylene radical which can be interrupted one or more times by O, S, NH, N + R 3 2 , SiR 3 2 , OSiR 3 2 , CONH, CONR 3 , COO and/or OCONH, a substituted or unsubstituted, aromatic C 6 to C 14 radical or a combination thereof;
R 3 =in each case independently a linear or branched C 1 to C 20 alkyl radical, a substituted or unsubstituted phenyl or benzyl radical;
AG=an anchor group selected from:

wherein R 11a and R 11b are independently selected from H, alkyl, aryl or —Si(alkyl) 3 ,

wherein R 16 is independently selected from alkoxy, aryloxy, Cl, alkyl or aryl,

wherein R 17a is selected from alkoxy, aryloxy, Cl or OH, and R 17b and R 17c are each independently selected from alkoxy, aryloxy, Cl, OH, alkyl or aryl,
WG=an antimicrobially active group;
Y=is absent, O, S, NH, N + R 3 2 , an ester, amide or urethane group,
Z=is absent, O, S, NH, N + R 3 2 , an ester, amide or urethane group;
or a filler that is surface-modified with at least one compound of Formula (I);
(b) at least one radically polymerizable monomer; and
(c) at least one initiator for the radical polymerization.

2. Dental restorative material according to claim 1 , wherein R 1 and/or R 2 is a linear or branched C 5 to C 20 alkylene radical.

3. Dental restorative material according to claim 1 , wherein AG is selected from phosphonate and phosphate groups.

4. Dental restorative material according to claim 1 , wherein the antimicrobially active group WG comprises
a pyridinium group of formula

which is attached in ortho, meta or para position to the rest of the compound of Formula (I), or
a pyridinium group of formula

which can be substituted with R 6 in ortho, meta or para position,
wherein R 6 in each case independently represents H or a linear or branched C 1 to C 20 alkyl radical;
N + R 7 R 8 R 9 A − , with
R 7 ═H, a linear or branched C 1 to C 20 alkyl radical;
R 8 ═H, a linear or branched C 1 to C 20 alkyl radical;
or R 7 and R 8 together with the nitrogen atom to which they are bonded form an aromatic or non-aromatic ring system or an aromatic or non-aromatic ring;
R 9 =is absent, H, a linear or branched C 1 to C 31 alkyl radical;
r=5 to 30;
A − =F − , Cl − , Br − , I − , triflate (Trf), mesylate (Mes), tosylate (Tos), palmitate, stearate, gluconate, hexafluorophosphate, phenolate, (meth) acrylphosphonate, phosphate, hydrogen phosphate or dihydrogen phosphate;
—P + R 7′ R 9′ R 9′ A − , with
R 7′ ═H, a linear or branched C 1 to C 20 alkyl radical;
R 8′ ═H, a linear or branched C 1 to C 20 alkyl radical;
R 9′ =is absent, H, a linear or branched C 1 to C 31 alkyl radical;
r=5 to 30;
A − =F − , Cl − , Br − , I − , triflate (Trf), mesylate (Mes), tosylate (Tos), palmitate, stearate, gluconate, hexafluorophosphate, phenolate, (meth)acrylphosphonate, phosphate, hydrogen phosphate or dihydrogen phosphate;

A − with
r=5 to 30; or
A − =F − , Cl − , Br − , I − , triflate (Trf), mesylate (Mes), tosylate (Tos), palmitate, stearate, gluconate, hexafluorophosphate, phenolate, (meth)acrylphosphonate, phosphate, hydrogen phosphate or dihydrogen phosphate;
a quaternary alkylphosphonium or alkylsulphonium group, octenidine or a derivative thereof, chlorhexidine or another bisguanidine, triclosan or another chlorophenol, an inorganic group with antimicrobial properties.

5. Dental restorative material according to claim 1 , wherein the antimicrobially active group WG is a quaternary alkylammonium group of formula

wherein R 9 is C 1 to C 31 alkyl.

6. Dental restorative material according to claim 1 , wherein the spacer SP is a polyoxazoline, polyester, polyamide, polyurea, polyurethane, polycyanoacrylate, polyacrylate, polyacrylic ester, polymethacrylate, polymethacrylic ester, N-alkylated polyethyleneimine, N-alkylated vinylpyridine or polyaminosaccharide.

7. Dental restorative material according to claim 1 , wherein the spacer SP is a polyoxazoline group of formula:

wherein n is 3 to 500 and R 5 is —CH 3 , —C 2 H 5 or —C 3 H 7 .

8. Dental restorative material according to claim 1 , wherein at least one of the variables has one of the following meanings:
m=1 or 2;
p=1 or 2;
R 1 =a linear or branched C 1 to C 20 alkylene radical which can be interrupted one or more times by O, S, NH, N+R 3 2 , SiR 3 2 , CONH, CONR 3 , COO and/or OCONH;
R 2 =a substituted or unsubstituted, aromatic C 6 to C 14 radical;
R 3 =a linear or branched C 1 to C 20 alkyl radical;
SP=a polyoxazoline, polyester, polyamide, polyurea, polyurethane, polycyanoacrylate, polyacrylate, polyacrylic ester, polymethacrylate or polymethacrylic ester group;
AG=a phosphonate or phosphate group;
WG=a pyridinium group of formula

which is attached in ortho, meta or para position to the rest of the compound of Formula (I) or
a pyridinium group of formula

which can be substituted with R 6 in ortho, meta or para position,
wherein R 6 in each case independently represents H or a linear or branched C 1 to C 20 alkyl radical;
—N + R 7 R 8 R 9 A − , with
R 7 ═H, a linear or branched C 1 to C 20 alkyl radical;
R 8 ═H, a linear or branched C 1 to C 20 alkyl radical;
or R 7 and R 8 together with the nitrogen atom to which they are bonded form a heteroaromatic ring system or an aromatic or non-aromatic ring,
R 9 =is absent, H, a linear or branched C 1 to C 31 alkyl radical;
r=5 to 30;
A − =F − , Cl − , Br − , I − , triflate (Trf), mesylate (Mes), tosylate (Tos), palmitate, stearate, gluconate, hexa-fluorophosphate, phenolate, (meth) acrylphosphonate, phosphate, hydrogen phosphate or dihydrogen phosphate;
—P + R 7′ R 9′ R 9′ A − , with
R 7′ ═H, a linear or branched C 1 to C 20 alkyl radical;

Assignees

• Salz Ulrich
• Bock Thorsten
• Fik Christoph Peter
• Tiller Jörg
• Rheinberger Volker
• Ivoclar Vivadent Ag

Inventors

• Salz Ulrich
• Bock Thorsten
• Fik Christoph Peter
• Tiller Jörg
• Rheinberger Volker

Classifications

• A61K6/887

  Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• A61K6/30 Primary

  Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives · CPC title

• A61K6/69 Primary

  Medicaments · CPC title

• A61K6/17

  Particle size · CPC title

• A61K6/20

  Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish · CPC title