New thiazolotriazines having the formula ##STR1## (where R.sup.1 is aryl and R.sup.2 is ar(lower)alkyl, lower alkyl or lower alkenyl) and their pharmaceutically acceptable acid addition salts are described. The corresponding thiazolotriazinium compounds comprising a cation having the formula ##STR2## (where R.sup.1 and R.sup.2 are as explained above and R.sup.3 is ar(lower)alkyl, lower alkyl or lower alkenyl) and a pharmaceutically acceptable anion are also described. The compounds are indicated for use as anti-ulcer agents.

The present invention concerns novel heterocyclic compounds. In particular 
the invention provides new thiazolotriazine derivatives and 
thiazolotriazinium compounds, a process for their preparation and 
pharmaceutical compositions containing them. 
The invention provides novel compounds having the formula I 
##STR3## 
their pharmaceutically acceptable acid addition salts and their 
derivatives comprising a cation having the formula II 
##STR4## 
and a pharmaceutically acceptable anion. In formulae I and II R.sup.1 
represents aryl and R.sup.2 represents ar(lower)alkyl, lower alkyl or 
lower alkenyl. In formula II R.sup.3 represents ar(lower)alkyl, lower 
alkyl or lower alkenyl. 
More specifically, R.sup.1 may be selected from phenyl and phenyl 
substituted by one to two substituents selected from halogen, 
trifluoromethyl, lower alkoxy, lower alkyl, nitro, amino, mono(lower 
alkyl)amino and di(lower alkyl)amino, R.sup.2 may be selected from 
phen(lower)alkyl, lower alkyl and lower alkenyl and R.sup.3 may be 
selected from phen(lower)alkyl, lower alkyl and lower alkenyl. 
The aryl group denoted by R.sup.1 may be, for example, unsubstituted phenyl 
or phenyl substituted by one or more substituents. As substituents there 
may be mentioned, halogen, for instance, chlorine or bromine; 
trifluoromethyl; lower alkoxy, for instance, methoxy, ethoxy, propoxy or 
butoxy; lower alkyl, for instance, methyl, ethyl, propyl or butyl; nitro; 
and amino or substituted amino, for instance, mono (lower) alkylamino, for 
example, methylamino or ethylamino or di(lower alkyl)amino, for example, 
dimethylamino, ethylmethylamino or diethylamino. R.sup.2 represents an 
ar(lower)alkyl group, that is an aralkyl group whose alkyl moiety is lower 
alkyl, preferably phen(lower)alkyl, for instance, benzyl or phenethyl, a 
lower alkyl group, for instance, methyl, ethyl, propyl or butyl, or lower 
alkenyl, for instance, allyl, but-2-enyl, 2-methylbut-2-enyl, 
3-methylbut-2-enyl or pent-2-enyl. R.sup.3, where present, represents 
ar(lower)alkyl, preferably, phen(lower)alkyl, for example, benzyl or 
phenethyl, lower alkyl, for instance, methyl, ethyl, propyl or butyl, or 
lower alkenyl, for instance, allyl, but-2-enyl, 2-methylbut-2-enyl, 
3-methylbut-2-enyl or pent-2-enyl. R.sup.3 preferably represents lower 
alkyl, advantageously methyl or ethyl. 
The term "lower" as used herein in connection with alkyl and alkoxy groups 
means that the group contains up to 6 carbon atoms, preferably up to 4 
carbon atoms. The term "lower alkenyl" as used herein means a univalent 
radical derived by removal of a hydrogen atom from a saturated carbon atom 
of an ethylenically unsaturated aliphatic hydrocarbon of 3 to 6 carbon 
atoms, preferably 3 to 4 carbon atoms. 
It will be appreciated that the carbon atom at the 6-position in formulae I 
and II, that is the carbon atom bearing the aryl group R.sup.1, is 
asymmetric and thus the compounds of the invention possess the property of 
optical isomerism. The invention includes the optical isomers as well as 
their racemic mixtures. Mixtures of optical isomers may be resolved in 
known manner. 
Although the positive charge of the ion of formula II is illustrated on the 
nitrogen atom at the 1-position, it will be appreciated by those skilled 
in the art that the charge is believed to be delocalised between the 
1-position and the 5-position. Thus the ion may equally well be 
illustrated by means of the formula IIa 
##STR5## 
The compounds having formula I, their pharmaceutically acceptable acid 
addition salts and their derivatives containing the cation of formula II 
may be prepared by a process wherein a compound having the formula R.sup.1 
COCH.sub.2 Y (wherein R.sup.1 is as defined above and Y is a replaceable 
atom or group, for example, a bromine atom or an organosulphonyloxy group, 
for instance, p-toluenesulphonyloxy) is reacted with a triazine derivative 
having the formula 
##STR6## 
(where R.sup.2 is as defined above and R.sup.4 is hydrogen or the same as 
R.sup.3). When R.sup.4 is hydrogen the reaction product is generally the 
compound having the formula I in the form of its acid addition salt with 
the acid HY. If desired, the acid addition salt may be neutralised to 
yield the compound having formula I in the form of the free base. Other 
acid addition salts may be formed by treatment of the free base with an 
acid. When R.sup.4 is the same as R.sup.3, the product obtained is a 
thiazolotriazinium compound containing the ion of formula II. 
Amongst the new compounds provided by the invention are those of formula I 
where R.sup.1 is aryl and R.sup.2 is phen(lower)alkyl or lower alkyl and 
their pharmaceutically acceptable acid addition salts. They may be 
obtained by the aforesaid process by using a compound having the formula 
##STR7## 
where R.sup.2 is phen(lower)alkyl or lower alkyl. 
The starting materials of formula R.sup.1 COCH.sub.2 Y are known compounds 
or may be prepared in known manner. The triazine derivatives of formula 
III are known in some cases and, in the other cases, may be prepared in 
known manner. A literature reference relating to the preparation of the 
triazine derivatives is Journal of American Chemical Society, 69, 2136 
(1947). 
We prefer to carry out the process of the invention by using starting 
materials of formula R.sup.1 COCH.sub.2 Y where Y is a bromine atom. The 
aracylbromide may be reacted with the triazine derivative of formula III 
in solution in a suitable organic solvent, for instance, acetone. Normally 
this reaction proceeds at ambient laboratory temperature and therefore no 
heating is generally necessary. We have found it convenient to carry out 
the process by mixing a solution of the aracylbromide in acetone and a 
solution of the triazine derivative in acetone and allowing the 
thiazolotriazine derivative product to separate out from the solution. 
The compounds of formula I in the form of the free base may be prepared by 
neutralisation of an acid addition salt in known manner. The free base may 
be converted to an acid addition salt by addition of an acid. For example, 
the hydrochloride may be prepared by treatment with ethereal hydrogen 
chloride. 
The acid addition salts of the compound having formula I include these 
formed from inorganic acids such as the sulphate, hydrochloride, 
hydrobromide, hydroiodide, nitrate, phosphate, and organic acids, for 
example, sulphonates (such as the methane-sulphonate and 
p-toluenesulphonate), acetate, maleate, fumarate, tartrate and formate. 
The thiazolothiazinium compounds of the invention comprise the cation of 
formula II and a pharmaceutically acceptable anion. The anion may be 
derived from inorganic acids, for instance, chloride, bromide, sulphate, 
iodide nitrate, phosphate, and organic acids, for instance, sulphonates 
(such as the methanesulphonate and p-toluenesulphonate), acetate, maleate, 
fumarate, tartrate and formate.

The compounds of the invention are usefully pharmaceutically. In particular 
they are indicated for use as anti-ulcer agents. The following procedures 
may be used to test activity. 
PROCEDURE A 
GASTRIC SECRETION: PYLORUS - LIGATED RAT 
Reference: Shay, H; Sun, D. & Gruentstein, M. Gastroenterology 26: 906-913 
(1954) 
Test Animal: Rat 
Procedure: 
Male Charles River rats, weighing 180-220 g, are deprived of food 
overnight, but allowed water. They are housed in separate cages with 
widemesh grids to avoid coprophagy. Next morning each rat is anaesthetised 
with halothane, a small mid-line incision is made and the pylorus is 
ligated. The test compound or vehicle is administered by an appropriate 
route, usually by injecting a volume of 5 ml/kg into the stomach, or 1 
ml/kg into the duodenum. The wound is sutured, and the animal allowed to 
recover. The operation takes 3-5 minutes. Four hours after pylorus 
ligation each rat is killed, its stomach is removed and the volume of the 
gastric contents is measured; the sample is discarded if it contains food 
or faeces. 
Gastric juice is titrated against N NaOH, using a Metrohm automatic 
titrator. The following variables are evaluated. 
1. Concentration of acid. 
2. Amount of "free acid", but titrating to pH3. 
3. "total acid", by further titration to pH10. 
These variables are expressed in milliequivalents per milliliter. The mean 
volume of gastric contents, and the three variables above, are expressed 
as percentage of the corresponding control values. 
PROCEDURE B 
GASTRIC ULCERS CAUSED BY COLD-RESTRAINT STRESS 
Reference: Modification of procedure of Brodie, D. A. and Hanson, H, 
J.Appl. Physiol. 15:291-294 (1960) 
Test Animal: Rat 
Object: To detect compounds which will prevent ulcer formation in the 
glandular portion of the rat stomach. 
Procedure: 
Male Charles River rats weighing between 120-160 gm. are deprived of food 
for 18 hr. with water ad lib. The rats are divided into groups of 10 and 
dosed by the oral route with test compound, 50 mg/kg. or a vehicle 
control, 0.5% carboxymethylcellulose, in a volume of 5 ml/kg. Immediately 
after dosing the animals are inserted into aluminium restraining tubes 
measuring 15/8 inches in diameter by 8 inches and placed in the cold 
(4.degree. .+-. 1.degree. C.). The time in the cold is adjusted so that 
90% of the control animals exhibit ulcers. At the end of the test period 
the animals are killed, the duodenum and esophagus ligated, and the 
stomach removed. The stomachs are inflated with water, opened along the 
lesser curvature, spread over the index finger, and the mucosa wiped off 
to expose the submucosa. The number of hemorrhage sites in the submucosa 
is counted by visual observation and recorder; however, since these 
numbers are so variable, only the incidence of ulcer (i.e., the number of 
rats with ulcers) are used for evaluation. 
Compounds are reported by determining a percent inhibition which is 
calculated as follows: 
##EQU1## 
The compounds having formula I and their pharmaceutically acceptable acid 
addition salts show activity in Procedure A. For instance the products of 
Examples 1 to 6 and 9 and 10 herein show activity in Procedure A at a dose 
of 30 milligrams per kilogram i.d. The thiazolothiazinium compounds of the 
invention show activity in Procedure B. For instance the products of 
Examples 7 and 8 herein show activity in Procedure B at a dose of 100 
milligrams per kilogram p.o. 
The invention also includes pharmaceutical compositions containing as 
active ingredients a compound of formula I, a pharmaceutically acceptable 
acid addition salt thereof or a thiazolothiazinium compound comprising the 
cation of formula II and a pharmaceutically acceptable anion. The active 
ingredient may be micronised, if desired. In addition to the active 
ingredient, said compositions may also contain a non-toxic carrier. Any 
suitable carrier known in the art can be used to prepare the 
pharmaceutical compositions. In such a composition the carrier may be a 
solid, liquid or mixture of a solid and a liquid. Solid form compositions 
include powders, tablets and capsules. A solid carrier can be one or more 
substances which may also act as flavouring agents, lubricants, 
solubilisers, suspending agents, binders, or tablet-disintegrating agents; 
it can also be an encapsulating material. In powders the carrier is a 
finely divided solid which is in admixture with the finely divided active 
ingredient. 
In tablets the active ingredient is mixed with a carrier having the 
necessary binding properties in suitable proportions and compacted in the 
shape and size desired. The powders and tablets preferably contain from 5 
to 99, preferably 10-80% of the active ingredient. Suitable solid carriers 
are magnesium carbonate, magnesium stearate, talc, sugar, lactose, pectin, 
dextrin, starch, gelatin, tragacanth, methyl cellulose, sodium 
carboxymethyl cellulose, a low melting wax, and cocoa butter. The term 
"composition" is intended to include the formation of an active ingredient 
with encapsulating material as carrier to give a capsule in which the 
active ingredient (with or without other carriers) is surrounded by 
carrier, which is thus in association with it. Similarly cachets are 
included. 
Sterile liquid form compositions include sterile solutions, suspensions, 
emulsions, syrups and exilirs. The active ingredient can be dissolved or 
suspended in a pharmaceutically acceptable sterile liquid carrier, such as 
sterile water, sterile organic solvent or a mixture of both. Preferably a 
liquid carrier is one suitable for parenteral injection. Where the active 
ingredient is sufficiently soluble it can be dissolved in normal saline as 
a carrier; if it is too insoluble for this it can often be dissolved in a 
suitable organic solvent, for instance aqueous propylene glycol or 
polyethylene glycol solutions. Aqueous propylene glycol containing from 10 
to 75% of the glycol by weight is generally suitable. 
In other instances compositions can be made by dispersing the 
finely-divided active ingrdient in aqueous starch or sodium carboxymethyl 
cellulose solution, or in a suitable oil, for instance arachis oil. Liquid 
pharmaceutical compositions which are sterile or suspensions can be 
utilised by intramuscular, intraperitoneal or subcutaneous injection. In 
many instances a compound is orally active and can be administered orally 
either in liquid or solid composition form. 
Preferably the pharmaceutical composition is in unit dosage form. In such 
form, the composition is sub-divided in unit doses containing appropriate 
quantities of the active ingredient; the unit dosage form can be a 
packaged composition, the package containing specific quantities of 
compositions, for example packeted powders or vials or ampoules. The unit 
dosage form can be a capsule, cachet or tablet itself, or it can be the 
appropriate number of any of these in package form. The quantity of active 
ingredient in a unit dose of composition may be varied or adjusted from 5 
mg. or less to 500 or more, according to the particular need and the 
activity of the active ingredient. The invention also includes the 
compounds in the absence of carrier where the compounds are in unit dosage 
form. 
The invention is illustrated by the following Examples: 
EXAMPLE 1 
6-Hydroxy-3-methyl-6-phenyl-3,4,6,7-tetrahydro-2H-thiazolo[3,2-a]-s-triazin 
e 
A solution of 5.0 grams (0.025 moles) of phenacylbromide in 40 milliliters 
of acetone was mixed with a solution of 3.27 grams (0.025 moles) of 
3,4,5,6-tetrahydro-5-methyl-s-triazin 2(1H)thione in 450 milliliters of 
acetone. 
6-Hydroxy-3-methyl-6-phenyl-3,4,6,7-tetrahydro-2H-thiazolo[3,2-a]-s-triazi 
ne hydrobromide crystallized out as a colourless solid, m.p. 
149.degree.-150.degree. C. (decomposition). The yield was 7.35 grams 
(89%). 
Analysis. Found = C, 43.2; H, 4.86%; N, 12.6%. C.sub.12 H.sub.16 BrN.sub.3 
OS requires C, 43.6%; H, 4.89%; N, 12.7%. 
EXAMPLE 2 
6-p-Bromophenyl-6-hydroxy-3-methyl-3,4,6,7-tetrahydro-2H-thiazolo[3,2-a]-s- 
triazine 
A solution of 6.95 grams (0.025 moles) of p-bromophenacylbromide in 60 
milliliters of acetone was mixed with a solution of 3.27 grams (0.025 
moles) of 3,4,5,6-tetrahydro-5-methyl-s-triazin 2(1H) thione in 450 
milliliters of acetone. 
6-p-Bromophenyl-6-hydroxy-3,4,6,7-tetrahydro-2H-thiazolo[3,2-a-]-s-triazin 
e hydrobromide crystallized out as a colourless solid, m.p. 
138.degree.-140.degree. C. (decomposition). The yield was 7.5 grams (75%). 
Analysis. Found = 35.5%; H, 3.68%; N, 10.1%. C.sub.12 H.sub.15 Br.sub.2 
N.sub.3 OS requires C, 35.2%; H, 3.69%; N, 103%. 
EXAMPLE 3 
6-p-Bromophenyl-3-ethyl-6-hydroxy-3,4,6,7-tetrahydro-2H-thiazolo[3,2-a]-s-t 
riazine 
A solution of 6.95 grams (0.025 moles) of p-bromophenacylbromide in 60 
milliliters of acetone was mixed with a solution of 3.62 grams (0.025 
moles) of 5-ethyl 3,4,5,6-tetrahydro-s-triazin 2(1H) thione in 500 
milliliters of acetone. After 10 minutes 
6-p-bromophenyl-3-ethyl-6-hydroxy-3,4,6,7-tetrahydro-2H-thiazolo(3,2-a)-s- 
triazine hydrobromide crystallized out as a colourless solid, m.p. 
132.degree.-134.degree. C. The yield was 9.27 grams (88%). 
Analysis. Found = C, 37.2%; H, 4.16%; N, 9.93%. C.sub.13 H.sub.17 Br.sub.2 
N.sub.3 OS requires C, 36.9%; H, 4.05%; N, 9.93%. 
EXAMPLE 4 
3-Benzyl-6-hydroxy-6-phenyl-3,4,6,7-tetrahydro-2H-thiazolo-[3,2-a]-s-triazi 
ne 
A solution of 5.0 grams (0.025 moles) of phenacyl bromide in 40 milliliters 
of acetone was mixed with a solution of 5.2 grams (0.025 moles) of 
5-benzyl-3,4,5,6-tetrahydro-s-triazine-2(1H)-thione in 1200 milliliters of 
the same solvent and left for 2 hours at room temperature. The solution 
was then concentrated to 300 milliliters and left overnight. 
3-Benzyl-6-hydroxy-6-phenyl-3,4,6,7-tetrahydro-2H-thiazolo[3,2-a]-s-triazi 
ne hydrobromide acetonate crystallized as a pale brown solid, m.p. 
97.degree.-99.degree. C. The yield was 9.5 grams (82%). 
Analysis. Found = C, 54.7%; H, 5.80%; N, 9.24%. C.sub.21 H.sub.26 BrN.sub.3 
O.sub.2 S requires C, 54.3%; H, 5.64%; N, 9.04%. 
EXAMPLE 5 
6-(3,4-Dichlorophenyl)-6-hydroxy-3-methyl-3,4,6,7-tetrahydro-2H-thiazolo-[3 
,2-a]-s-triazine 
A solution of 6.7 grams (0.025 mole) of 3,4-dichlorophenacyl bromide in 65 
milliliters of acetone was mixed with a solution of 3.27 grams (0.025 
mole) of 3,4,5,6-tetrahydro-5-methyl-s-triazin-2(1H-thione in 500 
milliliters of acetone. After five minutes, 
6-(3,4-dichlorophenyl)-6-hydroxy-3-methyl-3,4,6,7-tetrahydro-2H-thiazolo-[ 
3,2-a]-s-triazine hydrobromide crystallised as the hemiacetonate, melting 
point 155.degree.-156.degree. C. (with decomposition). The yield was 8.0 
grams (75%). 
Analysis. Found: C, 37.8%; H, 4.06; N, 9.80%. C.sub.12 H.sub.14 BrCl.sub.2 
OS.1/2C.sub.3 H.sub.6 O requires C, 37.9%; H, 4.00%; N, 9.81%. 
Example 6 
6-(2,4-Dichlorophenyl)-6-hydroxy-3-methyl-3,4,6,7-tetrahydro-2H-thiazolo-[3 
,2-a]-s-triazine 
A solution of 6.7 grams (0.025 mole) of 2,4-dichlorophenacyl bromide in 80 
milliliters of acetone was mixed with a solution of 3.27 grams (0.025 
mole) of 3,4,5,6-tetrahydro-5-methyl-5-triazine-2(1H)-thione in 450 
milliliters of acetone. The mixture was left for 30 minutes at room 
temperature. 7.4 Grams (74% yield) of the title compound as the 
hydrobromide crystallised as a colourless solid, melting point 
153.degree.-155.degree. C. (with decomposition). 
Analysis. Found: C, 36.56%; H, 3.60%; N, 10.29%. C.sub.12 H.sub.14 
BrCl.sub.2 N.sub.3 OS requires C, 36.11%; H, 3.54%; N, 10.53%. 
EXAMPLE 7 
6-(p-Bromophenyl)-3-ethyl-6-hydroxy-1-methyl-3,4,6,7-tetrahydro-2H-thiazolo 
-[3,2-a]-triazinium bromide 
A solution of 3.7 grams (0.015 mole) of p-bromophenacyl bromide in 30 
milliliters of acetone was added to a solution of 2.12 grams (0.015 mole) 
of 5-ethyl-1-methyl-3,4,5,6-tetrahydro-s-triazine-2(1H)-thione in 100 
milliliters of acetone. The mixture was stirred for 4 hours, then allowed 
to stand. The resulting white precipitate was collected to give 4.52 grams 
(70% yield) of the title compound, melting point 151.degree.-153.degree. 
C. 
Analysis. Found: C, 38.4%; H, 4.51%; N, 9.50%. C.sub.14 H.sub.19 Br.sub.2 
N.sub.3 OS requires C, 38.5%, H, 4.38%; N, 9.62%. 
EXAMPLE 8 
3-Ethyl-6-hydroxy-1-methyl-6-phenyl-3,4,6,7-tetrahydro-2H-thiazolo-[3,2-a]- 
triazinium bromide 
A solution of 3.98 grams (0.02 mole) of phenacyl bromide in 30 milliliters 
of acetone was added to a solution of 3.18 grams (0.02 mole) of 
5-ethyl-1-methyl-3,4,5,6-tetrahydro-s-triazine-2(1H)-thione in 150 
milliliters of acetone. The mixture was stirred for 30 minutes and then 
allowed to stand. The resulting white precipitate was collected to give 
5.7 grams (80% yield) of the title compound, melting point 
135.degree.-137.degree. C. 
Analysis. Found: C, 47.1%; H, 5.65%; N, 11.4%. C.sub.14 H.sub.20 N.sub.3 
OSBr requires C, 46.9%; H, 5.63%; N, 11.7%. 
EXAMPLE 9 
3-Allyl-6-(p-bromophenyl)-6-hydroxy-3,4,6,7-tetrahydro-2H-thiazole 
[3,2-a]-s-triazine 
A solution of 6.95 grams (0.025 mole) of p-bromophenacyl bromide in 60 
milliliters of acetone was mixed with a solution of 3.93 grams (0.025 
mole) 5-allyl-3,4,5,6-tetrahydro-s-triazin-2(1H)-thione in 1100 
milliliters of acetone and the mixture was left for 1 hour at room 
temperature. The solution was then concentrated to 200 milliliters. 10.1 
Grams (89% yield) of 
3-allyl-6-(p-bromophenyl)-6-hydroxy-3,4,6,7-tetrahydro-2H-thiazolo[3,2-a]- 
s-triazine hydrobromide 1/3 acetonate crystallised as a colourless solid of 
melting point 146.degree.-148.degree. C. (with decomposition). 
Analysis. Found: C, 39.5%; H, 4.02%; N, 9.34%. C.sub.14 H.sub.17 Br.sub.2 
N.sub.3 OS.1/3C.sub.3 H.sub.6 O requires C, 39.6%; H, 4.21%; N, 9.24%. 
EXAMPLE 10 
3-Allyl-6-hydroxy-6-phenyl-3,4,6,7-tetrahydro-2H-thiazolo 
[3,2-a]-s-triazine 
A solution of 5.0 grams (0.025 mole) of phenacyl bromide in 40 milliliters 
of acetone was mixed with a solution of 3.93 grams (0.025 mole) of 
5-allyl-3,4,5,6-tetrahydro-s-triazin-2(1H)-thione in 1100 milliliters of 
acetone and the mixture was left for 1 hour at room temperature. The 
solution was concentrated to 100 milliliters and left overnight. 8.1 Grams 
(86% yield) of 
3-allyl-6-hydroxy-6-phenyl-3,4,6,7-tetrahydro-2H-thiazolo[3,2-a]-s-triazin 
e hydrobromide 1/3 acetonate crystallised out as a colourless solid, 
melting point 118.degree.-120.degree. C. 
Analysis. Found: C, 48.3%; H, 5.36%; N, 11.5%. C.sub.14 H.sub.18 BrN.sub.3 
OS.1/3C.sub.3 H.sub.6 O requires C, 48.0%; H, 5.37%; N, 11.2%. 
EXAMPLE 11 
In a similar manner to the preceeding Examples, the following reactants are 
reacted with 3,4,5,6-tetrahydro-5-methyl-s-triazin-2(1H)-thione to give 
the following products as hydrobromides: 
______________________________________ 
REACTANT PRODUCT 
______________________________________ 
1. m-Methoxyphenacyl bromide 
6-Hydroxy-6-(m-methoxy- 
phenyl)-3-methyl-3,4,6,7- 
tetrahydro-2H-thiazolo- 
[3,2-a]-s-triazine 
2. p-Nitrophenacyl bromide 
6-Hydroxy-3-methyl-6- 
(p-nitrophenyl)-3,4,6,7- 
tetrahydro-2H-thiazolo- 
[3,2-a]-s-triazine 
3. p-Dimethylaminophenacyl 
6-(p-Dimethylaminophenyl)- 
bromide 6-hydroxy-3-methyl-3,4,6,7- 
tetrahydro-2H-thiazolo-[3,2- 
a]-s-triazine 
4. m-Trifluoromethylphenacyl 
6-Hydroxy-3-methyl-6-(m- 
bromide trifluoromethylphenyl)- 
3,4,6,7-tetrahydro-2H- 
thiazolo-[3,2-a]-s-triazine 
5. p-Methylphenacyl bromide 
6-Hydroxy-3-methyl-6-(p- 
methylphenyl)-3,4,6,7- 
tetrahydro-2H-thiazolo- 
[3,2-a]-s-triazine 
6. m-Aminophenacyl bromide 
6-(m-Aminophenyl)-6-hydroxy- 
3-methyl-3,4,6,7-tetrahydro- 
2H-thiazolo-[3,2-a]-s- 
triazine. 
7. p-Methylaminophenyl bromide 
6-Hydroxy-3-methyl-6-(p- 
methylaminophenyl)-3,4,6,7- 
tetrahydro-2H-thiazolo- 
[3,2-a]-s-triazine 
______________________________________ 
EXAMPLE 12 
In a similar manner to the preceeding Examples, phenacyl bromide is reacted 
with 1-benzyl-5-ethyl-3,4,5,6-tetrahydro-s-triazin-2(1H)-thione and 
1-allyl-5-ethyl-3,4,5,6-tetrahydro-s-triazin-2(1H)-thione to give, 
respectively, 
1-benzyl-3-ethyl-6-hydroxy-6-phenyl-3,4,6,7-tetrahydro-2H-thiazolo-[3,2-a] 
-triazinium bromide and 
1-allyl-3-ethyl-6hydroxy-6-phenyl-3,4,6,7-tetrahydro-2H-thiazolo-[3,2-a]-t 
riazinium bromide.