Aqueous composition, in particular for treating mucosa and/or wounds

Patent metadata

Field	Value
Publication number	US-12097205-B2
Application number	US-201917293100-A
Country	US
Kind code	B2
Filing date	Oct 23, 2019
Priority date	Nov 29, 2018
Publication date	Sep 24, 2024
Grant date	Sep 24, 2024

Abstract

An aqueous composition includes a dihydrotriazine compound of the general formula below,

where
R 1 means (i) a phenyl group or phenylalkyl group, (ii) a naphthyl group or naphthylalkyl group, (iii) a heterocyclic group, heterocyclic alkyl group or heterocyclic aminoalkyl group, (iv) an alkyl group having 1 to 16 carbon atoms or (v) a cycloalkyl group or cycloalkylalkyl group, R 1 ′ means a hydrogen atom bonded to the nitrogen atom at position 1 or 3 of the dihydrotriazine ring, R 2 and R 3 each mean a hydrogen atom or a methyl group, R 4 means an alkyl group having 7 to 16 carbon atoms and the dashed line indicates that a double bond is positioned either between positions 1 and 2 or between positions 2 and 3 of the dihydrotriazine ring, or a tautomer thereof or a salt thereof and a defoamer.

First claim

The invention claimed is:

1. An aqueous composition comprising:
a dihydrotriazine compound of the general formula I below:

wherein
R 1 is (i) a phenyl group or a phenylalkyl group which is substituted with 1 to 3 substituents selected from the group consisting of C 1-6 -alkoxy group, hydroxy group, a halogen atom, C 1-6 -haloalkyl group, C 1-6 -alkyl group, a sulfonamido group and C 1-6 -haloalkoxy group, (ii) a naphthyl group or a naphthylalkyl group, (iii) a heterocyclic group, a heterocyclic alkyl group or a heterocyclic aminoalkyl group, (iv) an alkyl group having 1 to 16 carbon atoms or (v) a cycloalkyl group or a cycloalkylalkyl group,
R′ is a hydrogen atom which is bonded to the nitrogen atom at position 1 or 3 of the dihydrotriazine ring,
R 2 and R 3 independently of one another mean is a hydrogen atom or a methyl group,
R 4 is an alkyl group having 7 to 16 carbon atoms and
the dashed line indicates that the position of a double bond is either between positions 1 and 2 or between positions 2 and 3 of the dihydrotriazine ring,
or a tautomer thereof or a salt thereof and
a defoamer.

2. The aqueous composition as claimed in claim 1 , wherein R 1 is a phenyl group or a phenylalkyl group which is substituted by 1 to 3 substituents selected from the group consisting of fluorine atom, chlorine atom, hydroxy group, methyl group, tert-butyl group, trifluoromethyl group and methoxy group, R 1 ′ is a hydrogen atom which is bonded to the nitrogen atom at position 1 or 3 of the dihydrotriazine ring, R 2 and R 3 both mean a methyl group and R 4 is an n-octyl group, n-nonyl group or n-decyl group.

3. The aqueous composition as claimed in claim 2 , wherein the phenylalkyl group is benzyl group.

4. The aqueous composition as claimed in claim 1 , wherein R 1 is a phenyl group, 4-chlorophenyl group, 2,4-difluorophenyl group, 2,3,4-trifluorophenyl group, 4-tert-butylphenyl group, 4-methoxyphenyl group, 2-methoxy-4-tert-butylphenyl group, 4-trifluoromethoxyphenyl group, benzyl group, methylbenzyl group, 4-methylbenzyl group, 4-methoxybenzyl group, 3,4-dimethoxybenzyl group, 4-hydroxybenzyl group, 3,4-dichlorobenzyl group, 2,3,4-trichlorobenzyl group, 4-trifluoromethylbenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylpropyl group, 2-phenylpropyl group or 3-phenylpropyl group, R 1 ′ means is a hydrogen atom which is bonded to the nitrogen atom at position 1 or 3 of the dihydrotriazine ring, R 2 and R 3 both mean a methyl group and R 4 is an n-octyl group, n-nonyl group or n-decyl group.

5. The aqueous composition as claimed in claim 1 , wherein R 1 is a methylbenzyl group, and/or R 2 and R 3 both mean a methyl group and/or R 4 is an n-octyl group.

6. The aqueous composition as claimed in claim 5 , wherein the methylbenzyl group is 4-methylbenzyl group.

7. The aqueous composition as claimed in claim 1 , wherein R 1 means is a methylbenzyl group, R 1 ′ is a hydrogen atom which is bonded to the nitrogen atom at position 1 or 3 of the dihydrotriazine ring, R 2 and R 3 both mean a methyl group and R 4 is an n-octyl group.

8. The aqueous composition as claimed in claim 7 , wherein the methylbenzyl group is 4-methylbenzyl group.

9. The aqueous composition as claimed in claim 1 , wherein the dihydrotriazine compound is 4-octylamino-1,6-dihydro-6,6-dimethyl-2-(4′-methylbenzylamino)-1,3,5-triazine gluconate, 4-octylamino-3,6-dihydro-6,6-dimethyl-2-(4′-methylbenzylamino)-1,3,5-triazine gluconate, or a tautomer thereof.

10. The aqueous composition as claimed in claim 1 , wherein the dihydrotriazine compound has a proportion of 0.001% by weight to 1.00% by weight based on the total weight of the aqueous composition.

11. The aqueous composition as claimed in claim 1 , wherein the defoamer is selected from the group consisting of alkyl amide, silicone, poloxamer and combinations of at least two of the defoamers mentioned.

12. The aqueous composition as claimed in claim 1 , wherein the defoamer has a proportion of 0.0001% by weight to 2.0% by weight based on the total weight of the aqueous composition.

13. The aqueous composition as claimed in claim 1 , wherein the aqueous composition further comprises a surfactant, the defoamer and the surfactant being different from one another.

14. The aqueous composition as claimed in claim 13 , wherein the surfactant has an active proportion of 0.01% by weight to 10.0% by weight based on the total weight of the aqueous composition, and/or the emulsifier has a proportion of 0.001% by weight to 1.5% by weight based on the total weight of the aqueous composition.

15. The aqueous composition as claimed in claim 13 , wherein the surfactant is a nonionic surfactant.

16. The aqueous composition as claimed in claim 13 , wherein the surfactant is selected from the group consisting of poloxamer, fatty alcohol alkoxylate, polyvinylpyrrolidone, alkyl polyglucoside and combinations of at least two of the surfactants mentioned.

17. The aqueous composition as claimed in claim 1 , wherein the surfactant is a zwitterionic surfactant.

18. The aqueous composition as claimed in claim 17 , wherein the zwitterionic surfactant is an alkylamidoalkyl betaine.

19. The aqueous composition as claimed in claim 18 , wherein the alkylamidoalkyl betaine is an alkylamidoethyl betaine, alkylamidopropyl betaine or a combination thereof.

20. The aqueous composition as claimed in claim 1 , wherein the aqueous composition further comprises an emulsifier and a surfactant, the emulsifier and the surfactant being different from one another.

21. The aqueous composition as claimed in claim 20 , wherein the emulsifier is selected from the group consisting of alcohol ethoxylate, alkyl polyglucoside, polysorbate, ethoxylated castor oil and combinations of at least two of the emulsifiers mentioned.

22. The aqueous composition as claimed in claim 1 , wherein the aqueous composition further comprises an additive selected from the group consisting of thickener, complexing agent, humectant, acid, alkali, organic solvent and combinations of at least two of the additives mentioned.

23. The aqueous composition as claimed in claim 1 , wherein the aqueous composition is in the form of an aqueous solution or a hydrogel.

24. A method for preventing or treating mucosa and/or wounds and/or infections and/or infectious diseases comprising the step of administering an aqueous composition as claimed in claim 1 to a patient.

Assignees

• Braun Melsungen Ag

Inventors

• Arndt Andreas
• Dück Natalie
• Kurz Michael

Classifications

• A61K47/34

  Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence) · CPC title

• A61K47/32

  Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers {, poly(meth)acrylates, or polyvinyl pyrrolidone} · CPC title

• A61K47/26

  Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin · CPC title

• A61K47/186

  Quaternary ammonium compounds, e.g. benzalkonium chloride or cetrimide · CPC title

• A61K47/18

  Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids · CPC title