Isothiuronium salts

Details Isothiuronium salts Isothiuronium salts

1985-11-25

1987-12-01

Lone, Warren B.

Organic compounds -- part of the class 532-570 series

Organic compounds

Thioimidate esters

558 5, 514508, C07C15714

Patent

active

047105780

DESCRIPTION:

BRIEF SUMMARY
CROSS REFERENCE TO RELATED APPLICATIONS

This application is a national phase application based, in turn, upon a Hungarian application 1324/84 of 3 Apr. 1984 and a modification thereof of 19 Mar. 1985.


FIELD OF THE INVENTION

This invention relates to isothiuronium salts, a process for the preparation thereof and pharmaceutical compositions comprising the same. The majority of the said isothiuronium salts are new compounds. The said compounds possess useful antitumor and antistimulant, antiparasitic effect and can be used in human and veterinary therapy.


BACKGROUND OF THE INVENTION

Compounds of the Formula I ##STR3## wherein R.sup.1 is methyl, ethyl or benzyl and R.sup.2 stands for hydrogen are known (French Pat. No. 788,429 and DOS No. 2,426,683). In these publications however the said compounds were only mentioned as intermediates and the publications were completely silent in disclosing any biological activity thereof or any use of these compounds in therapy.


DESCRIPTION OF THE INVENTION

According to an aspect of the present invention there are provided new compounds and salts of the Formula I ##STR4## wherein R.sup.1 is C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-6 cycloalkyl, aralkyl or aryl, which groups can be substituted by one or more hydroxy, mercapto and/or halogen; alkynyl or C.sub.3-6 cycloalkyl; methyl, ethyl or benzyl.
The term "C.sub.1-6 alkyl" relates to straight or branched chain saturated aliphatic hydrocarbon groups (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl and isobutyl (etc.). The term "C.sub.2-6 alkenyl" covers straight or branched chain olephinic unsaturated groups (e.g. vinyl, allyl and methallyl) (etc.). The term "C.sub.2-6 alkynyl" relates to straight or branched chain aliphatic groups comprising at least one triple bond (e.g. propargyl) (etc.). The term "C.sub.3-6 cycloalkyl" relates to cyclic saturated aliphatic hycrocarbon groups (e.g. cyclobutyl, cyclopentyl and cyclohexyl) (etc.). The term "aryl" group encompasses mono- and polycyclic aromatic hydrocarbon groups (e.g. phenyl and naphthyl) (etc.). The term "aralkyl" relates to alkyl groups substituted by at least one aryl group (e.g. benzyl, .beta.-phenyl-ethyl) (etc.). The term "halogen" encompasses the fluorine, chlorine, bromine and iodine atoms.
The said alkyl, alkenyl, alkynyl, cycloalkyl, aryl and aralkyl groups may optionally bear one or more substituents selected from the group consisting of hydroxy, mercapto and halogen. Thus as examples of the said substituted groups the following groups may be mentioned: 2-chloro-ethyl, 3-bromo-propyl, 2-hydroxy-ethyl, 3-chloro-2-hydroxy-propyl etc.
A preferred group of the compounds of the Formula I are those derivatives in which R.sup.1 is allyl.
A further preferred group of the compounds of the Formula I are those derivatives in which R.sup.1 is 2-halogeno-ethyl.
R.sup.2 stands preferably for hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, allyl or cyclohexyl.
X stands preferably for a halide anion, particularly for chloride, bromide or iodide.
Particularly preferred representatives of the compounds of the Formula I are pharmaceutically acceptable salts of the following derivatives:
Further preferred compounds of the Formula I are the N-aminoiminomethyl-N'-alkyl-S-allyl-isothiuronium salts, particularly the corresponding N'-methyl, N'-ethyl, N'-n-propyl and N'-isopropyl compounds. According to a further aspect of the present invention there is provided a process for the preparation of compounds of the general Formula I and salts thereof which comprises ##STR5## (wherein R.sup.2 is as stated above) or a suitable salt thereof with an alkylating agent capable of introducing a R.sup.1 group, preferably with an alkylating agent of the Formula R.sup.1 --Y (wherein R.sup.1 is as stated above and Y stands for a leaving group, preferably halogen); or ##STR6## with a compound of the Formula R.sup.1 --SH (wherein R.sup.1 is as stated above) with an acid of the Formula HX (wherein X is an anion of an organic or inorganic acid).
In the said reactions

REFERENCES:
patent: 4017539 (1977-04-01), Bosies et al.

Affiliated with

Also associated with

Rating

Isothiuronium salts does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Isothiuronium salts, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Isothiuronium salts will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1932349