N-Substituted .omega.-(2-oxo-4-imidazolin-1-yl) alcanoic acids and salts and esters thereof

The present invention refers to N-substituted .omega.-(2-oxo-4-imidazolin-1-yl) alcanoic acids as well as salts and esters thereof having the general formula I ##STR1## The compounds are useful, for example, as antiallergics, antiasthmatics, etc.

As described in two own prior, non-published German patent applications 
Nos. (P 29 34 746.4 and P 29 50 478.7), 5- and 4.5-substituted 
.omega.-(2-oxo-4-imidazolin-1-yl) alcanoic acids as well as their salts 
and esters have valuable pharmacological properties such as 
antithrombotic, antiarteriosklerotic, antiinflammatory and analgetic 
properties. 
The present invention refers to new N-substituted 
.omega.-(2-oxo-4-imidazolin-1-yl) alcanoic acid derivatives having the 
general formula I 
##STR2## 
wherein 
n is an integer ranging from 1 to 10, preferably ranging from 6 to 8, 
R.sup.1 represents hydrogen, an alkali metal ion or a straight or branched 
hydrocarbon group having from 1 to 6 carbon atoms or the benzyl group, 
R.sup.2 is --(CH.sub.2).sub.m --R, m being 0, 1 or 2, 
R, R.sup.3 and R.sup.4, which may be identical or different from each 
other, represent hydrogen (with the exception of R if m is zero), the 
unsubstituted phenyl group or the phenyl group substituted by one or 
several identical or differing substituents selected from the group 
consisting of halogen (in particular chlorine or fluorine), CH.sub.3 --, 
CH.sub.3 O--, --CF.sub.3, at least one of R, R.sup.3 and R.sup.4 being a 
phenyl group or the phenyl group substituted by one or several identical 
or differing substituents selected from the group of halogen, --CH.sub.3, 
CH.sub.3 O--, --CF.sub.3. 
The present invention further refers to processes for producing the same. 
The new compounds show interesting pharmacological properties such as 
antiallergic, antiasthmatic, antithrombotic, antiarteriosklerotic and 
antiinflammatory properties. They furthermore show antagonistic activity 
in respect to some physiological processes regulated by PAF (platelet 
activation factor) as well as excellent compatibility by the stomach and 
may therefor in particular used for the treatment of thrombotic, allergic, 
asthmatic and arteriosclerotic as well as inflammatory deseases with at 
the same time favourable gastrointestinal properties. Furthermore, the 
compounds of formula I have a low toxicity. They furthermore may be 
produced in combination with anticoagulantia, in particular with heparin 
and heparinates. 
The new N-substituted .omega.-(2-oxo-4-imidazolin-1-yl)alcanoic acid 
derivatives in the form of the free acids or of the salts thereof with 
pharmacologically compatible bases or as esters thereof may be used as 
active ingredient in drugs together with usual carrier materials or 
diluents. 
The compounds of general formula I according to the present invention are 
used in dosages ranging from 0.1 to 100 mg/kg, in particular 1 to 50 
mg/kg. 
The compounds according to the present invention are produced according to 
the invention in that a 4-imidazolin-2-one of the general formula II 
##STR3## 
wherein R.sup.2, R.sup.3 and R.sup.4 have the same meaning as in formula 
I, which may be produced by known processes usual in the chemistry of 
heterocyclic compounds from isocyanates and .alpha.-aminoketones or, 
respectively, from benzoketones with substituted ureas, is subjected to 
reaction with an alkylating agent of the general formula III 
EQU X--(CH.sub.2).sub.n --COOR.sup.1 III 
wherein n and R.sup.1 have the same meaning as in formula I and X is a 
halogen atom, in an organic solvent such as acetone, methyl ethyl ketone, 
dimethylformamide with the addition of an auxiliary base such as sodium 
hydride, possibly in the presence of an alkali metal iodide as catalyst. 
The resulting esters of formula I may converted into the corresponding 
alkali metal salt of formula I (R.sup.1 =alkali metal) in usual manner for 
instance by reaction with an alkali metal hydroxide in an aqueous, 
alcoholic or alcohol-ethereal solvent and by subsequent addition of a 
mineral acid into the acid of formula I (R.sup.1 =H). 
In another way the acids of formula I (R.sup.1 =H) and the alkali metal 
salts thereof of formula I (R.sup.1 =alkali metal) may be converted into 
the esters of formula (R.sup.1 =C.sub.1-6 -alkyl or benzyl) in manners 
usual in organic chemistry, for instance by the treatment of the compounds 
of formula I with a solution of hydrochloric acid in the corresponding 
alcohol or by subjecting the acid or the salt of formula I to reaction 
with thionyl chloride and subsequent reaction with the corresponding 
alcohol. 
The compounds of formula I may also be produced by subjecting an 
.omega.-(2-oxo-4-imidazolin-1-yl)-alcanoic acid or a derivative thereof 
having the general formula IV 
##STR4## 
wherein R.sup.1, R.sup.3 and R.sup.4 have the same meaning as in formula 
I, which may be produced by the synthesis described in the German patent 
application No. P 29 50 478.7, to reaction with an alkylating agent of 
formula V 
EQU R.sup.2 -Y V 
wherein Y has the same meaning of X in formula III or Y is another usual 
favourable group to be split off, for instance the N.sub.2 -group or the 
radical of a sulphuric acid ester, in particular of a sulphuric acid lower 
alkyl ester. 
Substituted phenyl groups R.sup.2 (or, respectively, R), R.sup.3 and 
R.sup.4 are for instance: 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 
2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methoxyphenyl, 
3-methoxyphenyl, 4-methoxyphenyl, 2.5-dimethoxyphenyl, 
3.4-dimethoxyphenyl, 3.4.5-trimethoxyphenyl, 2-methylphenyl, 
3-methylphenyl, 4-methylphenyl, 2-trifluoromethylphenyl, 
3-trifluoromethylphenyl, 4-trifluoromethylphenyl. 
Alkylating agents of formula III are for instance the esters of the 
following .omega.-halogeno alcanoic acids: 
chloroacetic acid, bromoacetic acid, iodoacetic acid, 3-chloropropionic 
acid, 3-bromopropionic acid, 3-iodopropionic acid, 4-chlorobutyric acid, 
4-bromobutyric acid, 4-iodobutyric acid, 5-chlorovaleric acid, 
5-bromovaleric acid, 5-iodovaleric acid, 6-chlorocapronic acid, 
6-bromocapronic acid, 6-iodocapronic acid, 7-chloroenanthic acid, 
7-bromoenanthic acid, 7-iodoenanthic acid, 8-chlorocaprylic acid, 
8-bromocaprylic acid, 8-iodocaprylic acid, 9-chloropelargonic acid, 
9-bromopelargonic acid, 9-iodopelargonic acid, 10-chlorocaprinic acid, 
10-bromocaprinic acid, 10-iodocaprinic acid, 11-chloroundecanoic acid, 
11-bromoundecanoic acid, 11-iodoundecanoic acid. 
Examples for the alkylating agents of formula V are: 
Diazomethane, dimethylsulfate, chloromethane, bromomethane, iodomethane, 
chloroethane, bromoethane, iodoethane, benzylchloride, benzylbromide, 
benzyliodide, phenylethylchloride, phenylethylbromide, phenylethyliodide 
as well as those substituted benzyl- and phenylethyl halogenides 
corresponding to R. 
The alcohols R.sup.1 OH preferably are such alcohols with straight or 
secondary branched saturated hydrocarbon groups with 1 to 6 carbon atoms 
such as methanol, ethanol, propanol, isopropanol, butanol, pentanol, 
hexanol as well as benzylalcohols. 
The new compounds of formula I may be administered orally or by injection 
or rectally as suitable pharmaceutical products which may be solid or 
liquid, in the form of suspensions or solutions. Examples for such 
pharmaceutical products are tablets, powders, capsules, granules, 
ampoules, sirups and suppositories. 
The production of the compounds according to the present invention are 
further illustrated in the following examples. 
The given melting points have been determined on a BUCHI 510 melting point 
determination apparatus and are not corrected. The IR-spektra have been 
determined on a PERKIN ELMER 257 and the mass spektra on a VARIAN MAT-311 
A (70 eV).

EXAMPLE 1 
[3-(4-Chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] acetic acid ethyl 
ester 
1.5 g of sodium hydride (80% suspension in mineral oil) are washed with 
n-pentane and added to a mixture of 13.5 g 
1-(4-chlorophenyl)-5-phenyl-4-imidazolin-2-one and 100 cc. of anhydrous 
dimethylformamide (DMF). The mixture is stirred at room temperature and 
heated to 60.degree. C. with continuation of stirring towards the end of 
hydrogen formation. Thereafter, 6.2 g of chloroacetic acid ethyl ester and 
1.5 g of sodiumiodide (NaJ) are added and the mixture is heated to 
80.degree. C. for 8 hours. After cooling, the reaction product is diluted 
with water, extracted with ether, the ether phase is washed consequetively 
with water, with 5% NaHCO.sub.3 solution and again with water. The 
ethereal solution is dried over Na.sub.2 SO.sub.4, the solvent is 
distilled off in a vacuum and the residue is purified chromatographically 
on silicic acid gel using chloroform as eluant. 
Yield: 14.5 g. Fp. 96.degree. to 97.degree. C. IR (in KBr): 1755 and 1700 
cm.sup.-1. 
EXAMPLE 2 
7-[3-(4-Chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] enanthic acid ethyl 
ester 
The product is obtained as described in example 1 from 1.35 g NaJ (80% 
suspension in mineral oil), 12.2 g of 
1-(4-chlorophenyl)-5-phenyl-4-imidazolin-2-one, 100 cc. of DMF, 8.7 g of 
7-chloroenanthic acid ethyl ester and 1.35 g of NaJ. Eluant in 
chromatographic purification: hexane/ethyl acetate. 
Yield: 15.7 g (oil) IR (film): 1735 and 1700 cm.sup.-1. 
EXAMPLE 3 
7-(3-ethyl-4.5-diphenyl-2-oxo-4-imidazolin-1-yl) enanthic acid ethyl ester 
The product is obtained as described in example 1 from 2.1 g of NaH (80% 
suspension in mineral oil), 18.5 g of 
1-ethyl-4.5-diphenyl-4-imidazolin-2-one, 140 cc. of DMF, 13.5 g of 
7-chloroenanthic acid ethyl ester and 2.1 g of NaJ. 
Yield: 14.5 g (oil) IR (film): 1735 and 1690 cm.sup.-1. 
EXAMPLE 4 
8-(3.4-Diphenyl-2-oxo-4-imidazolin-1-yl)-caprylic acid methyl ester 
The product is produced as described in example 1 from 2.34 g of NaH (80% 
suspension in mineral oil), 18.5 g of 1.5-diphenyl-4-imidazolin-2-one, 160 
cc. of DMF, 18.5 g of 8-bromocaprylic acid methyl ester and 2.34 g of NaJ. 
Eluant in chromatographic purification: hexane/ethyl acetate. 
Yield: 14 g, Fp. 45.degree. to 47.degree. C. IR (film): 1740 and 1695 
cm.sup.-1. 
EXAMPLE 5 
8-[3-(4-Chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] caprylic acid 
methyl ester 
The product is produced as described in example 1 from 2.4 g of NaH (80% 
suspension in mineral oil), 21.6 g of 
1-(4-chlorophenyl)-5-phenyl-4-imidazolin-2-one, 160 cc. of DMF, 19.0 g of 
8-bromocaprylic acid methyl ester and 2.4 g of NaJ. 
Yield: 33 g (oil) IR (FILM): 1740 and 1700 cm.sup.-1. 
EXAMPLE 6 
8-[2-Oxo-4-phenyl-3-(3-trifluoromethylphenyl)-4-imidazolin-1-yl] caprylic 
acid methyl ester 
The product is produced as described in example 1 from 1.41 g of NaH (80% 
suspension in mineral oil), 14.3 g of 
5-phenyl-1-(3-trifluoromethylphenyl)-4-imidazolin-2-one, 100 cc. of DMF, 
11.1 g of 8-bromocaprylic acid methyl ester and 1.41 g of NaJ. 
Eluant in chromatographic purification: hexane/ethyl acetate. 
Yield: 7.0 g (oil) IR (film): 1740 and 1700 cm.sup.-1. 
EXAMPLE 7 
8-[3-(4-Methoxyphenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] caprylic acid 
methyl ester 
The product is produced as described in example 1 from 2.4 g of NaH (80% 
suspension in mineral oil), 21.3 g of 
1-(4-methoxyphenyl)-5-phenyl-4-imidazolin-2-one, 160 cc. of DMF 19 g of 
8-bromocaprylic acid methyl ester and 2.4 g of NaJ. Eluant in 
chromatographic purification: hexane/ethyl acetate. 
Yield: 18.9 g (oil) IR (film) 1740 and 1695 cm.sup.-1. 
EXAMPLE 8 
8-[3-(4-Methylphenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] caprylic acid 
methyl ester 
The product is produced as described in example 1 from 2.25 g of NaH (80% 
suspension in mineral oil), 18.7 g of 
1-(4-methylphenyl)-5-phenyl-4-imidazolin-2-one, 150 cc. of DMF, 17.8 g of 
8-bromocaprylic acid methyl ester and 2.25 g of NaJ. 
Yield: 18.4 g (oil) IR (film): 1740 and 1695 cm.sup.-1. 
EXAMPLE 9 
8-[3-(4-Fluorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] caprylic acid 
methyl ester 
The product is product as described in example 1 from 2.16 g of NaH (80% 
suspension in mineral oil), 18.3 g of 
1-(4-Fluorophenyl)-5-phenyl-4-imidazolin-2-one, 150 cc. of DMF, 17.1 g of 
8-bromocaprylic acid methyl ester and 2.16 g of NaJ. 
Yield: 16.7 g (oil) IR (film): 1740 and 1700 cm.sup.-1. 
EXAMPLE 10 
8-[4-(4-Chlorophenyl)-2-oxo-3-phenyl-4-imidazolin-1-yl] caprylic acid 
methyl ester 
The product is produced as described in example 1 from 1.05 g of NaH (80% 
suspension in mineral oil), 9.5 g of 
5-(4-chlorophenyl)-1-phenyl-4-imidazolin-2-one, 70 cc. of DMF, 8.3 g of 
8-bromocaprylic acid methyl ester and 1.05 g of NaJ. 
Eluant in chromatographic purification: hexane/ethyl acetate. 
Yield: 8.3 g, Fp. 83.degree. to 84.degree. C. IR (in KBr): 1740 and 1690 
cm.sup.-1. 
EXAMPLE 11 
8-(3-Benzyl-2-oxo-4-phenyl-4-imidazolin-1-yl) caprylic acid methyl ester 
The product is produced as described in example 1 from 1.8 g of NaH (80% 
suspension in mineral oil), 15 g of 1-benzyl-5-phenyl-4-imidazolin-2-one, 
120 cc. of DMF, 14.2 g of 8-bromocaprylic acid methyl ester and 1.8 g of 
NaJ. 
Yield: 18.8 g (oil) IR (film): 1735 and 1685 cm.sup.-1. 
EXAMPLE 12 
8-(2-Oxo-3.4.5-triphenyl-4-imidazolin-1-yl) caprylic acid methyl ester 
The product is produced as described in example 1 from 1.2 g of NaH (80% 
suspension in mineral oil), 12 g of 1.4.5-triphenyl-4-imidazolin-2-one, 80 
cc. of DMF, 9.5 g of 8-bromocaprylic acid methyl ester and 1.2 g of NaJ. 
Yield: 12.9 g (oil) IR (film): 1740 and 1700 cm.sup.-1. 
EXAMPLE 13 
8-[4.5-Bis-(2-fluorophenyl)-3-methyl-2-oxo-4-imidazolin-1-yl] caprylic acid 
methyl ester 
The product is produced as described in example 1 from 0.63 of NaH (80% 
suspension in mineral oil), 5.9 g of 
4.5-bis-(2-fluorophenyl)-1-methyl-4-imidazolin-2-one, 40 cc. of DMF, 5.0 g 
of 8-bromo caprylic methyl ester and 0.63 g of NaJ. 
Eluant in chromatographic purification: hexane/ethyl acetate. 
Yield: 5.3 g (oil) IR (film): 1740 and 1695 cm.sup.-1. 
EXAMPLE 14 
8-(4.5-Diphenyl-3-methyl-2-oxo-4-imidazolin-1-yl) caprylic acid methyl 
ester 
The product is produced as described in example 1 from 2.4 g of NaH (80% 
suspension in mineral oil), 20 g of 
4.5-diphenyl-1-methyl-4-imidazolin-2-one, 160 cc. of DMF, 19 g of 
8-bromocaprylic acid methyl ester and 2.4 g of NaJ. 
Eluant in chromatographic purification: hexane/ethyl acetate. 
Yield: 17.5 g (oil) IR (film): 1740 and 1690 cm.sup.-1. 
EXAMPLE 15 
9-[3-(4-Chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] pelargonic acid 
methyl ester 
The product is produced as described in example 1 from 1.35 g of NaH (80% 
suspension in mineral oil), 12.2 g of 
1-(4-chlorophenyl)-5-phenyl-4-imidazolin-2-one, 90 cc. of DMF, 11.3 g of 
9-bromo-nonanic acid methyl ester and 1.35 g of NaJ. 
Eluant in chromatographic purification: hexane/ethyl acetate. 
Yield: 5.4 g, Fp. 54.degree. to 56.degree. C. IR (in KBr): 1740 and 1690 
cm.sup.-1. 
EXAMPLE 16 
11-(3-ethyl-4.5-diphenyl-2-oxo-4-imidazolin-1-yl) undecanoic acid methyl 
ester 
The product is produced as described in example 1 from 0.45 g of NaH (80% 
suspension in mineral oil), 4 g of 
1-ethyl-4.5-diphenyl-4-imidazolin-2-one, 30 cc. of DMF, 4.2 g of 
11-bromoundecanoic acid methyl ester and 0.45 g of NaJ. 
Eluant in chromatographic purification: hexane/ethyl acetate. 
Yield: 1.5 g (oil) IR (film): 1740 and 1690 cm.sup.-1. 
EXAMPLE 17 
8-(3-Methyl-2-oxo-5-phenyl-4-imidazolin-1-yl) caprylic acid 
3.2 g of 8-(2-oxo-5-phenyl-4-imidazolin-1-yl) caprylic acid sodium salt 
(preparation see German patent application No. P 29 34 746.4) are 
suspended in 20 cc. of acetone together with 2.8 g of pulverized potassium 
hydroxide. The mixture is refluxed and converted into a homogenous 
solution by the addition of some drops of water. Thereafter, 2.8 g of 
methyliodide are added at boiling temperature, the mixture is refluxed for 
30 minutes and cooled to room temperature. After cooling, so much of water 
is added that precipitated solids are dissolved. The solution is stirred 
at room temperature for 4 hours, is acidified and diluted with water until 
the crude acid is separated as oil. The oil is dissolved in a small amount 
of chloroform, the chloroform phase is washed with water several times and 
is finally extracted with 5% soda lye. The soda lye extract is washed with 
chloroform, the aqueous solution is acidified with dilute hydrochloric 
acid and is separated from the acid precipitated as an oil. Purification 
occurs by chromatography on silicic acid gel using a mixture of chloroform 
and methanol as eluant. 
Yield: 2.6 g (oil) 
MS (m/e): 316 (100%), 187 (29%), 174 (65%), 159 (4.8%), 105 (7.7%). 
EXAMPLE 18 
[3-(4-Chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] acetic acid 
13.6 g of [3-(4-chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] acetic acid 
ethyl ester and 1.52 g of NaOH are dissolved in 80 cc. of ethanol and the 
mixture is stirred at room temperature for 24 hours. The alcohol is 
distilled off in a vacuum and the residue is dissolved in water. The 
aqueous solution is shaken with ether, the aqueous phase is acidified with 
dilute hydrochloric acid and the precipitated acid is separated and dried. 
Yield: 6.0 g, Fp. 214.degree. to 215.degree. C. 
MS (m/e): 328 (100%), 284 (30%), 269 (2.5%), 214 (14%). 
EXAMPLE 19 
7-[3-(4-Chlorophenyl-2-oxo-4-phenyl-4-imidazolin-1-yl] enanthic acid 
The product is produced as described in example 18 from 13.5 g of 
7-[3-(4-chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] enanthic acid 
ethel ester, 1.28 g of NaOH in 60 cc. of ethanol. 
Yield: 10.0 g, Fp. 141.degree. C. 
MS (m/e): 398 (100%), 284 (17%), 270 (27%), 214 (22%). 
EXAMPLE 20 
7-(3-Ethyl-4.5-diphenyl-2-oxo-4-imidazolin-1-yl) enanthic acid 
The product is produced as described in example 18 from 12.3 g of 
7-(3-ethyl-4.5-diphenyl-2-oxo-4-imidazolin-1-yl) enanthic acid ethyl ester 
and 1.16 g of NaOH in 60 cc. of ethanol. Further purification by 
chromatography on silicic acid gel using chloroform as eluant. 
Yield: 4.2 g, Fp. 111.degree. to 112.degree. C. 
MS (m/e): 392 (100%), 277 (8%), 264 (18%), 104 (6%). 
EXAMPLE 21 
8-(3.4-Diphenyl-2-oxo-4-imidazolin-1-yl) caprylic acid 
The product is produced as described in example 18 from 8.2 g of 
8-(3.4-diphenyl-2-oxo-4-imidazolin-1-yl) caprylic acid methyl ester and 
0.84 g of NaOH in 20 cc. of ethanol. Further purification by 
chromatography on silicic acid gel using chloroform as eluant. 
Yield: 1.4 g, Fp. 108.degree. C. 
MS (m/e): 378 (100%), 249 (20%), 236 (26%), 180 (24%). 
EXAMPLE 22 
8-[3-(4-Chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] caprylic acid 
The product is produced as described in example 18 from 20 g of 
8-[3-(4-chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] caprylic acid 
methyl ester and 1.88 g of NaOH in 100 cc. of methanol. Further 
purification by chromatography on silicic acid gel using a mixture of 
hexane annd ethyl acetate as eluant. 
Yield: 8.5 g, Fp. 100.degree. to 101.degree. C. 
MS (m/e): 412 (100%), 284 (11%), 270 (18%), 214 (16%). 
EXAMPLE 23 
8-[2-Oxo-4-phenyl-3-(3-trifluoromethyl-phenyl)-4-imidazolin-1-yl] caprylic 
acid 
The product is produced as described in example 18 from 6.9 g of 
8-[2-oxo-4-phenyl-3-(3-trifluoromethyl-phenyl)-4-imidazolin-1-yl] caprylic 
acid methyl ester and 0.66 g of NaOH in 30 cc. of methanol. Further 
purification by chromatography on silicic acid gel using chloroform as 
eluant. 
Yield: 4.55 g, Fp. 113.degree. to 114.degree. C. 
MS (m/e): 466 (100%), 318 (10%), 304 (21%), 248 (14%). 
EXAMPLE 24 
8-[3-(4-Methoxyphenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] caprylic acid 
The product is produced as described in example 18 from 18.8 g of 
8-[3-(4-methoxyphenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] caprylic acid 
methyl ester and 2.12 g of NaOH in 100 cc. of methanol. Further 
purification by chromatography on silicic acid gel using chloroform as 
eluant. 
Yield: 6.6 g, Fp. 110.degree. C. 
MS (m/e): 408 (100%), 279 (14%), 266 (18%), 210 (26%). 
EXAMPLE 25 
8-[3-(4-Methylphenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] caprylic acid 
The product is produced as described in example 18 from 18.1 g of 
8-[3-(4-methylphenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] caprylic acid 
methyl ester and 1.8 g of NaOH in 90 cc. of methanol. Further purification 
by chromatography on silicic acid gel using chloroform as eluant. 
Yield: 6.6 g, Fp. 110.degree. to 101.degree. C. 
MS (m/e): 392 (100%), 264 (11%), 250 (14%), 194 (12%). 
EXAMPLE 26 
8-[3-(4-Fluorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] caprylic acid 
The product is produced as described in example 18 from 16.4 g of 
8-[3-(4-fluorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] caprylic acid 
methyl ester and 1.6 g of NaOH in 80 cc. of methanol. Further purification 
by chromatography on silicic acid gel using chloroform as eluant. 
Yield: 3.6 g, Fp. 110.degree. C. 
M/S (m/e): 396 (100%), 268 (11%), 254 (18%), 198 (16%). 
EXAMPLE 27 
8-[4-(4-Chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] caprylic acid 
The product is produced as described in example 18 from 6.1 g of 
8-[4-(4-chlorophenyl)-2-oxo-3-phenyl-4-imidazolin-1-yl] caprylic acid 
ethyl ester and 0.56 g of NaOH in 30 cc. of methanol. The product is 
finally boiled in a small amount of ether, filtered off with suction and 
dried. 
Yield: 3.6 g, Fp. 156.degree. to 157.degree. C. 
MS (m/e): 412 (100%), 284(14%), 270 (23%), 214 (16%). 
EXAMPLE 28 
8-(3-Benzyl-2-oxo-4-phenyl-4-imidazolin-1-yl) caprylic acid 
The product is produced as described in example 18 from 20.3 g of 
8-(3-benzyl-2-oxo-4-phenyl-4-imidazolin-1-yl) caprylic acid methyl ester. 
Further purification by chromatography on silicic acid gel using 
chloroform as eluant. 
Yield: 9.5 g, Fp. 95.degree. C. 
MS (m/e): 392 (82%), 173 (13%), 159 (10%), 91 (100%). 
EXAMPLE 29 
8-(2-Oxo-3.4.5-triphenyl-4-imidazolin-1-yl)-caprylic acid 
The product is prepared as described in example 18 from 7.5 g of 
8-(2-oxo-3.4.5-triphenyl-4-imidazolin-1-yl)-caprylic acid methyl ester and 
0.64 g of NaOH in 30 cc. of methanol. Further purification by 
chromatography on silicic acid gel using chloroform as eluant. 
Yield: 3.5 g, Fp. 142.degree. to 143.degree. C. 
MS (m/e): 454 (100%), 325 (14%), 312 (23%), 180 (11%). 
EXAMPLE 30 
8-[4.5-Bis-(2-fluorophenyl)-3-methyl-2-oxo-4-imidazolin-1-yl] caprylic acid 
The product is produced as described in example 18 from 5.2 g of 
8-[4.5-bis-(2-fluorophenyl)-3-methyl-2-oxo-4-imidazolin-1-yl] caprylic 
acid methyl ester and 0.53 g of NaOH in 25 cc. of methanol. 
Recrystallization from ether/hexane. 
Yield: 3.9 g, Fp. 130.degree. to 131.degree. C. 
MS (m/e): 428 (100%), 299 (24%), 286 (53%). 
EXAMPLE 31 
8-(4.5-Diphenyl-3-methyl-2-oxo-4-imidazolin-1-yl) caprylic acid 
The product is produced as described in example 18 from 17.5 g of 
8-(4.5-diphenyl-3-methyl-2-oxo-4-imidazolin-1-yl) caprylic acid methyl 
ester and 2.1 g of NaOH in 100 cc. of methanol. Further purification by 
chromatography on silicic acid gel using chloroform as eluant. 
Yield: 10.2 g, Fp. 112.degree. to 114.degree. C. 
MS (m/e): 392 (100%), 263 (10%), 250 (33%). 
EXAMPLE 32 
9-[3-(4-Chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] pelargonic acid 
The product is produced as described in example 18 from 4.4 g of 
9-[3-(4-chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] pelargonic acid 
methyl ester and 0.4 g of NaOH in 20 cc. of methanol. Further purification 
by chromatography on silicic acid gel using chloroform as eluant. 
Yield: 2.8 g, Fp. 143.degree. to 144.degree. C. 
MS (m/e): 426 (100%), 284 (11%), 270 (20%), 214 (17%). 
EXAMPLE 33 
[3-(4-Chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] acetic acid sodium 
salt 
5 g of [3-(4-chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] acetic acid 
are dissolved in ethanol, the solution is neutralized with the equivalent 
amount of alcoholic soda lye and the resulting solution is evaporated to 
dryness in a vacuum. The solid residue is pulverized. 
Yield: 100% IR (in KBr): 1675 and 1600 cm.sup.-1. 
As described in example 33, examples 34 to 47 (see table 1) have been 
executed. 
TABLE 1 
__________________________________________________________________________ 
##STR5## 
Example IR maxima 
No. R.sup.1 
R.sup.2 R.sup.3 
R.sup.4 
n in KBr in cm.sup.-1 
corresponding acid 
__________________________________________________________________________ 
34 Na 
##STR6## 
##STR7## 
H 6 1690, 1570 
7-[3-(4-Chlorophenyl)-2-oxo-4-phenyl 
-4-imida- zolin-1-yl] enanthic 
acid 
35 Na 
C.sub.2 H.sub.5 
##STR8## 
##STR9## 
6 1690, 1575 
7-(3-Ethyl-4.5-diphenyl-2-oxo-4-imid 
azolin-1- yl) enanthic acid 
36 Na 
##STR10## 
##STR11## 
H 7 1690, 1570 
8-(3.4-Diphenyl-2-oxo-4-imidazolin-1 
-yl) caprylic acid 
37 Na 
##STR12## 
##STR13## 
H 7 1690, 1570 
8-[3-(4-Chlorophenyl)-2-oxo-4-phenyl 
-4-imida- zolin-1-yl] caprylic 
acid 
38 Na 
##STR14## 
##STR15## 
H 7 1695, 1570 
8-[2-Oxo-4-phenyl-3-(3-trifluorometh 
ylphenyl)- 4-imidazolin-1-yl] 
caprylic acid 
39 Na 
##STR16## 
##STR17## 
H 7 1690, 1570 
8-[3-(4-Methoxyphenyl)-2-oxo-4-pheny 
l-4-imida- zolin-1-yl] caprylic 
acid 
40 Na 
##STR18## 
##STR19## 
H 7 1690, 1570 
8-[3-(4-Methylphenyl)-2-oxo-4-phenyl 
-4-imidazo- lin-1-yl] caprylic 
acid 
41 Na 
##STR20## 
##STR21## 
H 7 1690, 1570 
8-[3-(4-Fluorophenyl)-2-oxo-4-phenyl 
-4-imidazo- lin-1-yl] caprylic 
acid 
42 Na 
##STR22## 
##STR23## 
H 7 1685, 1565 
8-[4-(4-Chlorophenyl)-2-oxo-3-phenyl 
-4-imidazo- lin-1-yl] caprylic 
acid 
43 Na 
##STR24## 
##STR25## 
H 7 1690, 1570 
8-(3-Benzyl-2-oxo-4-phenyl-4-imidazo 
lin-1-yl) caprylic acid 
44 Na 
##STR26## 
##STR27## 
##STR28## 
7 1700, 1565 
8-(2-Oxo-3.4.5-triphenyl-4-imidazoli 
n-1-yl)- caprylic acid 
45 Na 
CH.sub.3 
##STR29## 
##STR30## 
7 1690, 1570 
8-[4.5-Bis-(2-fluorophenyl)-3-methyl 
-2-oxo- 4-imidazolin-1-yl] caprylic 
acid 
46 Na 
CH.sub.3 
##STR31## 
##STR32## 
7 1690, 1570 
8-(4.5-Diphenyl-3-methyl-2-oxo-4-imi 
dazolin- 1-yl) caprylic acid 
47 Na 
##STR33## 
##STR34## 
H 8 1695, 1570 
9-[3-(4-Chlorophenyl)-2-oxo-4-phenyl 
-4-imida- zolin-1-yl] pelargonic 
acid 
__________________________________________________________________________ 
EXAMPLE 48 
[3-(4-Chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] acetic acid hexyl 
ester 
1 g of [3-(4-chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] acetic acid 
are dissolved in a small amount of anhydrous chloroform. 0.7 g of 
thionylchloride are added thereto and the mixture is stirred at about 
50.degree. C. for 2 hours. The mixture is evaporated in a vacuum, the 
residue is mixed with a small amount of chloroform and 0.31 g of hexanol 
are added to the mixture. After stirring for one hour at room temperature, 
the CHCl.sub.3 -solution is first extracted with an NaHCO.sub.3 -solution 
and then with water. It finally is dried over Na.sub.2 SO.sub.4. The 
CHCl.sub.3 -solution is evaporated, remaining hexanol is distilled off a 
high vacuum and the residue is further purified chromatographically on 
silicic acid gel using CHCl.sub.3 as eluant. 
Yield: 0.5 g (oil) 
IR (film): 1750 and 1710 cm.sup.-1. 
EXAMPLE 49 
8-(4.5-Diphenyl-3-methyl-2-oxo-4-imidazolin-1-yl) caprylic acid benzyl 
ester 
The product is prepared as described in Example 48 from 1.5 g of 
8-(4.5-diphenyl-3-methyl-2-oxo-4-midazolin-1-yl) caprylic acid, 0.55 g of 
thionyl chloride and 0.37 g of benzyl alcohol. 
Yield: 1.4 g (oil) 
IR (film: 1740 and 1700 cm.sup.-1.