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Publication numberUS3758471 A
Publication typeGrant
Publication dateSep 11, 1973
Filing dateJun 15, 1971
Priority dateApr 10, 1968
Also published asDE1907589A1, DE1907589B2, DE1907589C3, DE1913154A1, DE1913154B2, DE1913154C3, US3759911
Publication numberUS 3758471 A, US 3758471A, US-A-3758471, US3758471 A, US3758471A
InventorsA Maeda, F Morinaga, K Okamura, K Higo, T Irikura, Y Abe
Original AssigneeKyorin Seiyaku Kk
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Triazine derivatives
US 3758471 A
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Description  (OCR text may contain errors)

United States Patent 3,758,471 TRIAZINE DERIVATIVES Tsutomu Irikura, Yasuo Abe, Kyuya Okamura, Kyoichi Higo, Akitoshi Maeda, and F umihiko Morinaga, Tokyo, Japan, assignors to Kyorin Seiyaku Kabushiki Kaisha No Drawing. Continuation of abandoned application Ser. No. 808,683, Mar. 19, 1971. This application June 15, 1971, Ser. No. 153,396

Claims priority, application Japan, Apr. 10, 1968, 43/23,906, 43/23,907; June 6, 1968, 43/318,831; June 28, 1968, 43/44,996

Int. Cl. C07d 55/20, 55/22 U.S. Cl. 260249.6 3 Claims ABSTRACT OF THE DISCLOSURE Novel s-triazine derivatives having anti-inflammatory and anti-atherosclerotic activity and of the formula R stands for phenethylamino, aral-kylamino, pyrrolidino, piperidino, 2-ketopiperazine-4-yl, cyclohexylamino or straight or branched hexylamino;

R stands for amino, aralkylamino, pyrrolidino, piperidino, 2-ketopiperazine-4-y1, cyclohexylamino or straight or branched hexylamino; and

R stands for straight or branched alkyl of from 1-6 carbon atoms, pyrrolidino, piperidino, Z-ketopiperazine- 4-yl or NR R in which R, is hydrogen or straight or branched alkyl of from 1-6 carbon atoms and R is straight or branched alkyl with from 1-6 carbon atoms, with the proviso that (a) when R is phenethylamino, R is amino and R is straight or branched alkyl of from 26 carbon atoms;

(b) when R is aralkylamino, pyrrolidino, piperidino or 2-ketopiperazine-4-yl, R is the same or one of said groups and R is straight or branched alkyl of from 1-6 carbon atoms;

(0) when R, is cyclohexylamino or straight or branched hexylamino, R is the same or one of said groups and R is straight or branched alkyl of from 1-6 carbon atoms; and

(d) when R is cyclohexylamino, R is amino and R is pyrrolidino, piperidino, 2-ketopiperazine-4-yl or NR R wherein R and R have the above meaning.

wherein CROSS-REFERENCE TO PRIOR APPLICATION This is a continuation application of Ser. No. 808,683, filed Mar. 19, 1969, now abandoned.

SUMMARY OF THE INVENTION The invention relates to s-triazine derivatives of the formula N F i k a wherem R stands for phenethylamino, aralkylamino, pyrrolidino, piperidino, 2-ketopiperazine-4-y1, cyclohexylamino or straight or branched hexylamino;

R stands for amino, aralkylamino, pyrrolidino, piperidino, 2-ketopiperazine-4-yl, cyclohexylamino or straight or branched hexylamino; and

R stands for straight or branched alkyl of from 1-6 carbon atoms, pyrrolidino, piperidino, Z-ketopiperazine- 4-yl or NR R in which R is hydrogen or straight or branched alkyl of from 1-6 carbon atoms and R is straight or branched alkyl with from 1-6 carbon atoms, with the proviso that (a) when R is phenethylarnino, R is amino and R is straight or branched alkyl of from 2-6 carbon atoms;

(b) when R is aralkylamino, pyrrolidino, piperidino or 2-ketopiperazine-4-yl, R is the same or one of said groups and R is straight or branched alkyl of from 1-6 carbon atoms;

(c) when R is cyclohexylamino or straight or branched hexylamino, R is the same or one of said groups and R is straight or branched alkyl of from 1-6 carbon atoms; and

(d) when R is cyclohexylamino, R is amino and R is pyrrolidino, piperidino, 2-ketopiperazine-4-y1 or NR R wherein R and R have the above meaning.

The invention also embraces the acid addition salts of the compounds with organic or inorganic acids such as hydrochloric acid, maleic acid, tartaric acid, citric acid and lactic acid.

Activation of the reticuloendothelial system (RES) in mice is remarkably suppressed by preadministration of a compound having anti-inflammatory and auti-atherosclerotic activity. Therefore it is found that there is a strong correlation between RES and the compound and this correlation is used as a screening means to determine the utility of the present inventive compounds. The results of the physiological activities of the present inventive compounds by the above method are shown in Table I.

TABLE I Compound of Mean compound Example No.: activity 1 2 129.9 3 211.5

The correlation between the results of the above screening and the anti-inflammatory and anti-atherosclerotic activity is explained in a copending application.

The s-triazine derivatives of the present invention exhibit anti-inflammatory and/ or anti-atherosclerotic activity. Further, various cortison-like or oortison-inhibitory activities have also been observed in the novel s-tri azine derivatives. The inventive compounds are therefore not only pharmacologically useful as anti-atherosiclerotic agents, but they are also anti-inflammatory agents which may replace steroidal anti-inflammatory agents.

The compounds of the present invention can be prepared by two processes which are represented by the following schemes:

Process A:

wherein X is amino or alkyl and Y and Z are the same or different amino radicals.

Process B:

RCOOR b/ N W$|1NHC-NH, L I

wherein Wis phenethylamino, R is straight or branched alkyl of from 26 carbon atoms and R is lower alkyl.

Example 1.2-methyl-4,6-diphenethylamino-s-triazine A solution of phenethylamine (4.8 g.) in chloroform (20 ml.) is added in dropwise manner and under cooling to a solution of 2-methyl-4,6-dichloro-s-triazine (3.2 g.) in chloroform (80 ml.). A solution of potassium icarbonate (8.2 g.) in water (10 m1.) is also added to the reaction mixture. After completing the addition, stirring is continued for some time. The chloroform solution is washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield a crystalline precipitate. The precipitate is recrystallized from ethanol to yield 2-methyl-4,6-diphenethylamino-s-triazine as colorless crystals, M.P. 213-214 C. The yield is 1.0 g.

Analysis.--Calcd. for C H N (percent): C, 72.04; H, 6.95; N, 21.01. Found (percent): C, 72.18; H, 7.08; N, 21.12.

Example 2.-2-n-butyl-4,G-diphenethylamino-s-triazine Phenethylamine (9.7 g.) is added, with stirring, to a mixture of 2-n-butyl-4,6-dichloro-s-triazine (4.2 g.) in water (100 ml.). The mixture is slowly heated to reflux, and the refluxing temperature is maintained for 2 hours. After cooling, the product is collected by filtration and recrystallized from acetonitrile to give 2-n-butyl-4,6-diphenethylamino-s-triazine as colorless needles, M.P. 66- 67" C. The yield is 4.0 g.

Analysis.-Calcd. for C H N (percent): C, 73.56; H, 7.78; N, 18.65. Found (percent): C, 73.00; H, 7.80; N, 18.69.

Example 3.-2-methyl-4,6-dicyclohexylamino-s-triazine Cyclohexylamine (8.0 g.) is added, with stirring, to a mixture of 2-methyl-4,6-dichloro-s-triazine (3.2 g.) in Water (100 ml.). The mixture is slowly heated to reflux, and the refluxing temperature is maintained for 2 hours. After cooling, the product is collected by filtration and recrystallized from ethyl acetate to give 2-methyl-4,6-dicyclohexylamino-s-triazine as colorless needles, M.P. 187- 189 C. The yield is 3.7 g.

4 Analysis.Calcd. for C H N (percent): C, 66.39; H, 9.40; N, 24.21. Found (percent): C, 66.23; H, 9.29; N, 23.05.

Example 4.2-n-butyl-4,6-dicyclohexylamino-s-triazine The compound is obtained by following the same process as in Example 3, except that 2-n-butyl-4,6-dichloro-striazine (4.2 g.) is employed instead of 2-methyl-4,6-dichloro-s-triazine. Recrystallization from n-hexane yields 3.0 g. of the compound, M.P. l36137 C.

Analysis.Calcd. for C H N (percent): C, 68.84; H, 10.03; N, 21.13. Found (percent): C, 69.35; H, 10.17; N, 21.14.

Example 5.2-methyl-4,6-dipyrrolidino-s-triazine The compound is obtained by following the same process as in Example 1. Recrystallization from petroleum ether yields 1.0 g. of the compound, M.P. 83-85 C.

Analysis.-Calcd. for C H N (percent): C, 61.77; H, 8.21; N, 30.02. Found (percent): C, 61.53; H, 8.11; N, 30.35.

Example 6.2-methyl-4,6-di(2-ketopiperazine- 4-yl)-s-triazine The compound is obtained by following the same process as in Example 2. Recrystallization from ethanol yields 1.0 g. of the compound, M.P. 303 C. (dec.).

Analysis.Calcd. for C H N 0 (percent): C, 49.47; H, 5.88; N, 33.66. Found (percent): C, 49.18; H, 5.87; N, 34.34.

Example 7.2-methyl-4,6-dipiperidino-s-triazine The compound is obtained by following the same process as in Example 1. Recrystallization from petroleum ether yields 1.2 g. of the compound, M.P. 81-83" C.

Analysis.-Calcd. for C H N (percent): 0, 64.33; H, 8.87; N, 26.80. Found (percent): C, 64.09; H, 8.70; N, 27.19.

Example 8.2-methyl-4-pyrrolidino-6-phenethylamino s-triazine Example 9.-2-methyl-4-phenethylamino-6-(2-ketopiperazine-4-yl)-s-triazine The compound is obtained by following the same process as in Example 8. Recrystallization from ethanol yields 10.0 g. of the compound, M.P. 231-233 C.

Analysis.-Calcd. for C H N O (percent): C, 61.52; H, 6.45; N, 26.91. Found (percent): C, 61.14; H, 6.38; N, 26.32.

Example 10.-2-methyl-4,6-di-n-hexylamino-s-triazine The compound is obtained by following the same process as in Example 2. Recrystallization from ethyl acetate yields 3.0 g. of the compound, M.P. 154-155 C.

Analysis.-Calcd. for C H N (percent): C, 65.48; H, 10.65; N, 23.87. Found (percent): C, 65.61; H, 10.60; N, 23.84.

Example 11.-2-n-butyl-4,6-di-n-hexylamino-s-triazine The compound is obtained by following the same process as in Example 2. Recrystallization from ethyl acetate yields 1.0 g. of the compound, M.P. 97-98 C.

Analysis.-Calcd. for C H N (percent): C, 68.01; H, 11.12; N, 20.87. Found (percent): C, 67.90; H, 11.03; N, 20.76.

Example 12.-2-amino-4-cyclohexylamino-6- piperidino-s-triazine Piperidine (5.1 g.) is added, with stirring, to a mixture of 2-amino-4-cyclohexylamino-6-chloro-s-triazine (6.8 g.) in water (150 ml.). The mixture is slowly heated to reflux and the refluxing temperature is maintained for 2.5 hours. After cooling, the reaction mixture is extracted with chloroform, and the chloroform solution is washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a syrup which is treated with ethanol-water to yield a crystalline precipitate. The precipitate is collected by filtration and recrystallized from 60% ethanol to give the compound as colorless needles, M.P. 123-127 C. Yield is 3.0 g.

Analysis.-Calcd. for C H N (percent): C, 60.84; H, 8.75; N, 30.41. Found (percent): C, 60.31; H, 8.64; N, 30.48.

I Example 13.2-amino-4-cyclohexy1amino-6-(Z-ketd piperazine-4-yl)-s-triazine A solution of 2-ketopiperazine (5.4 g.) in water (50 ml.) is added, with stirring, to a mixture of 2-amino-4- cyclohexylamino-6-chloro-s-triazine (6.1 g.) in water (150 ml.). The mixture is slowly heated to reflux and the refluxing temperature is maintained for 3 hours. After cooling, the product is collected by filtration and recrystallized from ethanol to give 2-amino-4-cyclohexylamino-6-(2- ketopiperazine-4-yl)-s-triazine as colorless crystals, M.P. 266-269 C. Yield is 2.3 g.

Analysis.Calcd. for C13H21N70 (percent): C, 53.59; H, 7.27; N, 33.66. Found (percent): C, 53.80; H, 7.37; N, 34.02.

Example 14.2-ethyl-4,6-diphenethylamino-s-triazine The compound is obtained by following the same process as in Example 2, except that 2-ethyl-4,6-dichloro-striazine (3.6 g.) is employed instead of 2-n-butyl-4,6- dichloro-s-triazine. Recrystallization from acetonitrile yields 4.4 g. of the compound, M.P. 147-148 C.

Analysis.Calcd. for C H N (percent): C, 72.59; H, 7.25; N, 20.16. Found (percent): C, 72.45; H, 7.11; N, 20.26.

Example 15.2-n-propyl-4,6-diphenethylaminos-triazine The compound is obtained by following the same process as in Example 2, except that 2-n-propyl-4,6-dichloros-triazine (3.8 g.) is employed instead of 2-n-butyl-4,6- dichloro-s-triazine. Recrystallization from acetonitrile yields 5.9 g. of the compound, M.P. 96-97 C.

Analysis.Calcd. for C H N (percent): C, 73.09; H, 7.53; N, 19.38. Found (percent): C, 73.08; H, 7.35; N, 19.23.

Example 16.2-isopropyl-4,6-diphenethylamino-striazine I The compound is obtained by following the same process as in Example 2, except that 2-isopropyl-4,6-dichloros-triazine (3.8 g.) is employed instead of 2-n-butyl-4,6- dichloro-s-triazine. Recrystallization from acetonitrile yields 5.0 g. of the compound, M.P. 90-91 C.

Analysis.-Calcd. for C22H2'1N5 (percent): C, 73.09; H, 7.53; N, 19.38. Found (percent): C, 72.98; H, 7.59; N, 19.04.

Example 17.-2-ethyl-4,6-dicyclohexylamino-s-triazine The compound is obtained by following the same process as in Example 3, except that 2-ethyl-4,6-dichloro-striazine (3.6 g.) is employed instead of 2-methyl-4,6-dichloro-s-triazine. Recrystallization from acetonitrile yields 4.5 g. of the compound, M.P. 179 C.

6 Analysis.-Calcd. for C H N (percent): C, 67.29; H, 9.63; N, 23.08. Found (percent): C, 67.27; H, 9.60; N, 23.17.

Example 18.2-n-propyl-4,6-dicyclohexylaminos-triazine The compound is obtained by following the same process as in Example 3, except that 2-n-propyl-4,6-dichloros-triazine (3.8 g.) is employed instead of 2-methyl-4,6- dichloro-s-triazine. Recrystallization from acetonitrile yields 4.3 g. of the compound, M.P. 145146 C.

Analysis.-Calcd. for C H N (percent): C, 68.10; H, 9.84; N, 22.06. Found (percent): C, 67.85; H, 9.73; N, 22.06.

Example 19.-2-isopropyl-4,6-dicyclohexylaminos-triazine The compound is obtained by following the same process as in Example 3, except that 2-isopropyl-4,6-dichloros-triazine (3.8 g.) is employed instead of 2-methyl-4,6- dichloro-s-triazine. Recrystallization from acetonitrile yields 5.5 g. of compound, M.P. 149-150 C.

Analysis.--Calcd. for C H N (percent): C, 68.10; 113, 9.84; N, 22.06. Found (percent): C, 68.07; H, 9.85;

Example 20.2-n-hexyl-4,6-dicyclohexylamino-s-triazine The compound is obtained by following the same process as in Example 3, except that 2-n-hexyl-4,6-dichloro-striazine (4.7 g.) is employed instead of 2-methyl-4,6-dichloro-s-triazine. Recrystallization from acetonitrile yields 6.3 g. of the compound, M.P. 114 C.

Analysis.Calcd. for C H N (percent): C, 70.15; H, 10.37; N, 19.48. Found (percent): C, 70.18; H, 10.32; N, 19.60.

Example 21.-2-amino-4-phenethylamino-6-ethyl-striazine Phenethylbiguanide hydrochloride (24.1 g.) is added to a solution of sodium (2.3 g.) methanol and sodium chloride formed is removed by filtration. To the filtrate is added, with stirring, ethyl propionate (10.2 g.) under cooling (40 C.). The mixture is stirred at room temperature for 4 hours and treated with water (800 ml.). On standing several days, the product is collected by filtration and recrystallized from isopropylalcohol to give 2-amino-4-phenethyl-6-ethyl-s-triazine as colorless prismatic crystals, M.P. 140.5-142 C. Yield is 11.4 g.

Analysis.Calcd. for C H N (percent): C, 64.17; H, 7.04; N, 28.79. Found (percent): C, 64.07; H, 7.12; N, 28.59.

Example 22.2-amino-4-phenethylamino-6-n-propyl-striazine The compound is obtained by following the same process as in Example 21, except that ethyl butylate (15.0 g.) is employed instead of ethyl propionate. Recrystallization from isopropanol yields 12.2 g. of the compound, M.P. 8991 C.

Analysis.Calcd. for C H N (percent): C, 65.34; H, 7.44; N, 27.22. Found (percent): C, 64.94; H, 7.77; N, 2709.

Example 23 .2-amino-4-phenethylamino-6-isopropyl-striazine The compound is obtained by following the same process as in Example 21, except that ethyl isobutylate (15.0 g.) is employed instead of ethyl propionate. Recrystallization from acetonitrile yields 12.2 g. of the compound, M.P. -81 C.

Analysis.Calcd. for C H N (percent): C, 65.34; H, 7.44; N, 27.22. Found (percent): C, 65.12; H, 7.36; N, 27.57.

Example 24.2-amino-4-phenethylamino-6-n-butyl-striazine The compound is obtained by following the same process as in Example 21, except that ethyl valerate (17.0 g.) is employed instead of ethyl propionate. Recrystallization from isopropanol yields 13.4 g. of the compound, M.P. 93-95 C.

Analysis.Calcd. for C H N (percent): C, 66.39; H, 7.80; N, 25.18. Found (percent): C, 65.70; H, 7.68; N, 25.90.

Example 25.-2-amino-4-phenethylamino 6-isobutyl-striazine The compound is obtained by following the same process as in Example 21. Recrystallization from isopropanol yields 11.3 g. of the compound, M.P. 109-1105 C.

Analysis.Calcd. for C H N (percent): C, 66.39; H, 7.80; N, 25.81. Found (percent): C, 66.19; H, 7.86; N, 26.06.

Example 26.2-'amino-4cyclohexylamino-G-methylamino-s-triazine 40% methylamine (4.7 g.) is added, with stirring, to a mixture of 2-amino-4-cyclohexylamino-6-chloro-s-triazine (6.8 g.) in water (150 ml.). The mixture is slowly heated to reflux and the refluxing temperature is maintained for 2 hours. After cooling, the product is collected by filtration and recrystallized from acetonitrile to give the com pound as white crystals, M.P. 189-190 C. Yield is 4.9 g.

Analysis.Calcd. for C H N (percent): C, 54.03; H, 8.16; N, 37.81. Found (percent): C, 54.12; H, 8.25; N, 37.94.

Example 27.-2-amino-4-1cyclohexylamino-6-ethy1- amino-s-triazine maleate 70% ethylamine (3.9 g.) is added, with stirring, to a mixture of 2 amino 4 cyclohexylamino 6 chloro-striazine (6.8 g.) in water (150 ml.). The mixture is slowly heated to reflux and the refluxing temperature is maintained for 2 hours. After cooling, the reaction mixture is extracted with ethyl acetate and the ethyl acetate solution is washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a syrup. The syrup is dissolved in methanol (20 ml.), added to a solution of maleic acid (2.3 g.) in methanol (10 ml.) and the mixture is refluxed for 1 hour to yield a crystalline precipitate. The precipitate is collected by filtration and recrystallized from ethanol to give the compound as white crystal-powder, M.P. 160161 C. Yield is 3.6 g.

Analysis.Calcd. for C H N O (percent): C, 51.12; H, 6.87; N, 23.85. Found (percent): C, 51.20; H, 6.86; N, 23.63.

Example 28.2-amino-4-cyclohexylamino-6-n-propylamino-s-triazine maleate The compound is obtained by following the same process as in Example 27. Recrystallization from acetonitrile yields 4.5 g. of the compound, M.P. 169-170 C.

Analysis.Calcd. for C H N O (percent): C, 52.44; H, 7.15; N, 22.94. Found (percent): C, 52.57; H, 7.29; N, 22.96.

Example 29.-2-amino-4-cyclohexylamino-6-n-butylamino-s-triazine maleate The -compound is obtained by following the same process as in Example 27. Recrystallization from methanol yields 3.7 g. of the compound, M.P. 156158 C.

Analysis.Calcd. for C H N O (percent): C, 53.66; H, 7.42; N, 22.09. 'Found (percent): C, 53.62; H, 7.55; N, 22.16.

Example 30.2-amino-4-cyclohexylamino-6-dimethy1- amino-s-triazine maleate The compound is obtained by following the same process as in Example 13. Recrystallization from lacetonitrile yields 5.2 g. of the compound, M.P. 134-136" C.

Analysis.Calcd. for C H N (percent): C, 55.90; H, 8.53; N, 35.57. Found (percent): C, 55.97; H, 8.69; N, 35.27.

Example 31.-2-amino-4-cyclohexylamino-6-diethylamino-s-triazine maleate The compound is obtained by following the same process as in Example 27. Recrystallization from acetonitrile yields g. of the compound, M.P. 167169 C.

Analysis.Calcd. for C17H28N6O4 (percent): C, 53.66; H, 7.42; N, 22.09. Found (percent): C, 53.66; H, 7.26; N, 22.06.

Example 32.-2-amino-4-cyclohexylamino-6-di-npropylamino-s-triazine maleate The compound is obtained by following the same process as in Example 27. Recrystallization from acetonitrile yields 5.0 g. of the compound, M.P. 132 C.

AnaIysis.--Calcd. for C H N O (percent): C, 55.86; H, 7.90; N, 20.58. Found (percent): C, 55.50; H, 7.96; N, 20.69.

Example 33.-2-amino-4-cyclohexylamino-6-di-nbutylamino-s-triazine maleate References Cited UNITED STATES PATENTS 2,909,420 10/1959 Gysin et al. 260-249.9 X 2,909,421 10/1959 Gysin et al. 260-249.6 X

JOHN M. FORD, Primary Examiner US. Cl. X.R.

Referenced by
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US6239071Aug 22, 1996May 29, 2001Hoecht Schering Agrevo Gmbh2,4-diamino-1,3,5-triazines, processes for their preparation and their use as herbicides and plant growth regulators
US7112587Mar 26, 2003Sep 26, 2006Reddy Us Therapeutics, Inc.Methods and compositions of novel triazine compounds
US7132423Mar 26, 2003Nov 7, 2006Reddy Us Therapeutics, Inc.Methods and compositions of novel triazine compounds
US7163943Mar 26, 2003Jan 16, 2007Reddy Us Therapeutics, Inc.Methods and compositions of novel triazine compounds
US7169784Sep 27, 2004Jan 30, 2007Reddy Us Therapeutics, Inc.Medical devices employing triazine compounds and compositions thereof
US7169785 *Mar 26, 2003Jan 30, 2007Reddy Us Therapeutics, Inc.Methods and compositions of novel triazine compounds
US7173032Mar 17, 2003Feb 6, 2007Reddy Us Therapeutics, Inc.Methods and compositions of novel triazine compounds
US7238692Sep 27, 2004Jul 3, 2007Reddy Us Therapeutics, Inc.Medical devices employing triazine compounds and compositions thereof
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US7268134Sep 27, 2004Sep 11, 2007Reddy Us Therapeutics, Inc.Medical devices employing triazine compounds and compositions thereof
US7332488Aug 28, 2006Feb 19, 2008Reddy Us Therapeutics, Inc.Methods and compositions of novel triazine compounds
US7332489Mar 26, 2003Feb 19, 2008Reddy Us Therapeutics, Inc.Methods and compositions of novel triazine compounds
US7332490May 25, 2006Feb 19, 2008Reddy Us Therapeutics, Inc.Methods and compositions of novel triazine compounds
US7335656Aug 30, 2006Feb 26, 2008Reddy Us Therapeutics, Inc.Medical devices employing triazine compounds and compositions thereof
US7335770Mar 24, 2004Feb 26, 2008Reddy U5 Therapeutics, Inc.Triazine compounds and their analogs, compositions, and methods
WO1997008156A1 *Aug 5, 1996Mar 6, 1997Hoechst Schering Agrevo Gmbh2,4- diamino-1,3,5-triazines, process for the production thereof, and the use thereof as herbicides and plant growth regulators
Classifications
U.S. Classification544/198, 544/207, 514/824
International ClassificationG01L11/00, A61K31/53, C07D401/04, C07D403/04, C07D251/70, C07D401/14, C07D251/18, F16K31/12
Cooperative ClassificationC07D401/14, C07D251/18, F16K31/12, C07D403/04, C07D401/04, G01L11/00, C07D251/70, Y10S514/824, A61K31/53
European ClassificationG01L11/00, F16K31/12, C07D401/04, C07D251/18, A61K31/53, C07D401/14, C07D403/04, C07D251/70