Antimicrobial compounds, methods of making the same and articles comprising them
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07D-251/20
A61K-031/53
C07D-251/16
C07D-251/32
A01N-043/66
A01N-059/16
출원번호
US-0516374
(2015-09-30)
등록번호
US-10189798
(2019-01-29)
국제출원번호
PCT/US2015/053354
(2015-09-30)
국제공개번호
WO2016/054284
(2016-04-07)
발명자
/ 주소
Karandikar, Bhalchandra M.
출원인 / 주소
MEDICAL TECHNOLOGY RESEARCH INC
대리인 / 주소
McCoy Russell LLP
인용정보
피인용 횟수 :
0인용 특허 :
2
초록▼
The present disclosure pertains to antimicrobial compounds that include silver (Ag) and an s-triazine ring with substitutions at nitrogen or carbon atoms of the s-triazine ring. In one example, the antimicrobial silver s-triazine may be readily incorporated in a variety of compositions and devices i
The present disclosure pertains to antimicrobial compounds that include silver (Ag) and an s-triazine ring with substitutions at nitrogen or carbon atoms of the s-triazine ring. In one example, the antimicrobial silver s-triazine may be readily incorporated in a variety of compositions and devices in both medical and non-medical settings. In another example, the said compounds may possess broad spectrum antimicrobial activity against bacteria, viruses, fungi and other microbes.
대표청구항▼
1. An antimicrobial silver s-triazine compound consisting of: silver with an s-triazine ring carrying at least one substituent R and/or R1 on a nitrogen atom;wherein R and/or R1 is not hydrogen;wherein the antimicrobial silver s-triazine compound has one of the following chemical structures: wherein
1. An antimicrobial silver s-triazine compound consisting of: silver with an s-triazine ring carrying at least one substituent R and/or R1 on a nitrogen atom;wherein R and/or R1 is not hydrogen;wherein the antimicrobial silver s-triazine compound has one of the following chemical structures: wherein, for structure (iv), R and R1 include one of the group consisting of a straight chain alkyl group of 1 to 20 carbon atoms, a branched alkyl group of 0.1 to 20 carbon atoms, an allyl group, a vinyl group, a napthyl group, and a heteroaryl group when R and R1 are different;wherein, for structure (iv), R and R1 include one of the group consisting of the straight chain alkyl group of 1 to 20 carbon atoms, the branched alkyl group of 1 to 20 carbon atoms, and the napthyl group when R and R1 are identical; andwherein, for structure (i), R includes one of the group consisting of the straight chain alkyl group of 1 to 20 carbon atoms, the branched alkyl group of 1 to 20 carbon atoms, the allyl group, the vinyl group, a phenyl group, a benzyl group, the napthyl group, and the heteroaryl group. 2. A method of making an antimicrobial silver s-triazine active agent, the method comprising steps of: (i) preparing a solution of a metal salt of an s-triazine;(ii) preparing a silver salt solution, where the silver salt solution comprises one of a silver nitrate solution, a silver lactate solution, a silver gluconate solution, and/or a silver acetate solution; and(iii) reacting the solution of the metal salt of the s-triazine with the silver salt solution to obtain the antimicrobial silver s-triazine active agentwherein the antimicrobial silver s-triazine active agent has one of the following chemical structures: wherein, for structure (iv), R and R1 include one of the group consisting of a straight chain alkyl group of 1 to 20 carbon atoms, a branched alkyl group of 1 to 20 carbon atoms, an allyl group, a vinyl group, a napthyl group, and a heteroaryl group when R and R1 are different;wherein, for structure (iv), R and R1 include one of the group consisting of the straight chain alkyl group of 1 to 20 carbon atoms, the branched alkyl group of 1 to 20 carbon atoms, and the napthyl group when R and R1 are identical; andwherein, for structure (i), R includes one of the group consisting of the straight chain alkyl group of 1 to 20 carbon atoms, the branched alkyl group of 1 to 20 carbon atoms, the allyl group, the vinyl group, a phenyl group, a benzyl group, the napthyl group, and the heteroaryl group. 3. The method of claim 2, wherein the metal salt of the s-triazine comprises one of the following chemical structures: wherein, for structure (xi), R and R1 include one of the group consisting of the straight chain alkyl group of 1 to 20 carbon atoms, the branched alkyl group of 1 to 20 carbon atoms, the allyl group, the vinyl group, the napthyl group, and the heteroaryl group when R and R1 are different;wherein, for structure (xi), R and R1 include one of the group consisting of the straight chain alkyl group of 1 to 20 carbon atoms, the branched alkyl group of 1 to 20 carbon atoms, and the napthyl group when R and R1 are identical;wherein, for structure (ix), R includes one of the group consisting of the straight chain alkyl group of 1 to 20 carbon atoms, the branched alkyl group of 1 to 20 carbon atoms, the allyl group, the vinyl group, the phenyl group, the benzyl group, the napthyl group, and the heteroaryl group; andwherein M is selected from the group consisting of sodium, potassium, lithium, quaternary ammonium, calcium, magnesium, copper, zinc, and aluminum. 4. The method of claim 2, wherein the metal salt of the s-triazine comprises a metal salt of mono-alkyl substituted s-triazine obtained by nitrating biuret to obtain 1-nitrobiuret; chemically substituting the 1-nitrobiuret to obtain an alkyl substituted biuret; andchemically reacting a 1-alkyl substituted biuret to form the metal salt of mono-alkyl substituted s-triazine. 5. The method of claim 2, wherein the metal salt of the s-triazine comprises a metal salt of di-substituted s-triazine obtained by heating 1-methyl urea to an elevated temperature to yield a di-substituted s-triazine, and treating the di-substituted s-triazine with an alkali solution to obtain the metal salt of di-substituted s-triazine. 6. The antimicrobial silver s-triazine compound of claim 1, wherein the at least one substituent R and/or R1 are selected as a function of a desired duration of sustenance of antimicrobial activity. 7. The antimicrobial silver s-triazine compound of claim 1, wherein the antimicrobial silver s-triazine compound is resistant to heat and light. 8. The antimicrobial silver s-triazine compound of claim 1, wherein the at least one substituent R and/or R1 are selected to tailor the antimicrobial silver s-triazine compound's solubility in nonpolar solvents and/or to improve the antimicrobial silver s-triazine compound's compatibility with hydrocarbon rich polymers. 9. The antimicrobial silver s-triazine compound of claim 1, wherein the at least one substituent R and/or R1 are selected to improve emulsification behavior of the antimicrobial silver s-triazine compound. 10. The antimicrobial silver s-triazine compound of claim 1, wherein the compound includes one of dimethyl cyanuric acid (DMCA), ethyl isocyanuric acid (EIC), methyl isocyanuric acid (MIC), and 6-phenyl 2,4 di-hydroxy 1,3,5 triazine (PDT); and wherein an aqueous solubility at 25° C. for each of DMCA, EIC, MIC, and PDT comprises 654 mg/L, 16.5 mg/L, 48 mg/L, and 18 mg/L, respectively. 11. The method of claim 2, wherein a silver to metal cation mole ratio is 1:1 for reacting the solution of the metal salt of the s-triazine with the silver salt solution to obtain the antimicrobial silver s-triazine active agent. 12. The method of claim 2, further comprising reacting the solution of the metal salt of the s-triazine with the silver salt solution at temperatures comprising 20° C.-25° C.
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이 특허에 인용된 특허 (2)
Martinez-Alvarez Francisco (Barcelona ES) Briones Antonio Gamero (Barcelona ES) Buron Enrique Dominguez (Badalona ES), Dichlorocyanurate silver complexes.
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