Synthetically produced substantially pure biologically active compounds having the general formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.20 alkyl, alkenyl, aryl, aralkyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkenyl, alkylcycloalkenyl, or cycloalkenylalkyl; PA1 R.sub.2 is hydrogen, C.sub.1 -C.sub.10 alkyl or an amide-substituted alkyl having up to 10 carbon atoms; PA1 R.sub.3 is a cyclic, straight or branched chain hydrocarbon group having 2-12 carbon atoms, particularly --(CH.sub.2).sub.n --, wherein n is 2-12; or PA1 R.sub.2 and R.sub.3 are linked together to form an alkylene chain; and PA1 R.sub.4 is selected from ##STR2## (substituted or unsubstituted carbamimidoyl), ##STR3## (dimethylpyrimidyl), or ##STR4## (carbamyl) wherein each of R.sub.5, R.sub.6, and R.sub.7 is hydrogen or the same or different C.sub.1 -C.sub.8 alkyl group. The compounds are useful as bactericides for a wide variety of bacteria, including S.pyogenes, B.subtilis, K.pneumoniae, M.avium, B.fragilis, C.perfringens and C.albicans.

This invention relates to novel chemical compounds and processes for 
producing the same. More particularly, the invention is concerned with 
novel acyl and carbamimidoyl alkanediamines and derivatives thereof, 
having bactericidal properties. 
BACKGROUND OF THE INVENTION 
We have previously reported (J.A.C.S. 100, 7409 and J.A.C.S. 100, 4302) the 
discovery that certain marine animals, i.e., a tunicate, Polyandrocarpa 
sp., and a sponge, Acarnus erithacus (de Laubenfels), and their extracts 
possessed bactericidal, cytotoxic and other biological activities. 
In accordance with the present invention, there are provided the 
synthetically produced substantially pure active materials described in 
the cited references and, in addition, other related compounds, all of 
which are biologically active. 
SUMMARY OF THE INVENTION 
The compounds of the invention have the general formula 
##STR5## 
wherein R.sub.1 is C.sub.1 -C.sub.20 alkyl, alkenyl, aryl, aralkyl, 
cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkenyl, 
alkylcycloalkenyl, or cycloalkenylalkyl; 
R.sub.2 is hydrogen, C.sub.1 -C.sub.10 alkyl or an amide-substituted alkyl 
having up to 10 carbon atoms; 
R.sub.3 is a cyclic, straight or branched chain hydrocarbon group having 
2-12 carbon atoms, particularly --(CH.sub.2).sub.n --, wherein n is 2-12; 
or 
R.sub.2 and R.sub.3 are linked together to form an alkylene chain; and 
R.sub.4 is selected from 
##STR6## 
(substituted or unsubstituted carbamimidoyl), 
##STR7## 
(dimethyl pyrimidyl), or 
##STR8## 
(carbamyl) wherein each of R.sub.5, R.sub.6, and R.sub.7 is hydrogen or 
the same or different C.sub.1 -C.sub.8 alkyl group. 
As used herein, the term "alkyl" means saturated, monovalent aliphatic 
radicals, including straight and branched chain radicals, having 1 to 20 
carbon atoms, and preferably 11 to 17 carbon atoms, as illustrated by, but 
not limited to, methyl; n-amyl; n-hexyl; 2-heptyl; n-heptyl; 3-methyl; 
2-octyl; n-octyl; 2-tetradecyl; n-hexadecyl; 2-eicosanyl, and the like. 
As used herein, the term "cycloalkyl" means cyclic, saturated aliphatic 
radicals having 3 to 20 carbon atoms and preferably 11-17 carbon atoms, as 
illustrated by, but not limited to, cyclopropyl, cyclobutyl, cyclohexyl, 
cyclooctyl and the like. 
As used herein, the terms "alkylcycloalkyl" and "cycloalkylalkyl" mean 
respectively a cycloalkyl group which is substituted with an alkyl group 
and an alkyl group which is substituted with a cycloalkyl group, as 
previously defined, the total of the carbon atoms in the alkylcycloalkyl 
group or the cycloalkylalkyl being 4 to 20 and preferably 11 to 17. 
Examples of said groups are octylcyclopropyl, 2-methylcyclobutyl, 
4-ethylcyclohexyl, cyclopropylethyl, 2-cyclobutyl-n-octyl and the like. 
The term "alkenyl" refers to straight or branched chain C.sub.2 -C.sub.20 
alkyl radicals from which a hydrogen atom has been removed from each of 
one or more pairs of adjacent carbon atoms to produce ethylenic 
unsaturation, such as vinyl, allyl, methallyl, 1-pentenyl, 4-undecenyl and 
3,7,10- tridecatrienyl. 
The terms "cycloalkenyl", "alkylcycloalkenyl", and "cycloalkenylalkyl" 
refer to cycloalkyl, alkylcycloalkyl and cyloalkylalkyl groups in which 
the cyclic structure is ethylenically unsaturated. 
The term "aralkyl" refers to an aryl group, which can be a single ring, 
such as phenyl, or a plurality of unsaturated rings which can be bonded or 
fused together, such as naphthyl, substituted with an alkyl group, as 
previously defined. 
Specific compounds which come within the scope of the invention include the 
following: 
1-(tetradecanamidomethyl)-4-(guanidinomethyl)cyclohexane 
1-(tetradecanoyl)-4-(4-guanidinomethyl)piperidine 
1-benzamido-5-guanidinopentane 
1-(5-phenylpentanamido)-5-guanidinopentane 
1-(N-methyltetradecanamido)-5-guanidinopentane 
1-[N-(7-methyloctyl)tetradecanamido]-5-guanidinopentane. 
In general, the compounds of the invention can be made by a process 
involving successive reactions of a suitable alkane or polymethylene 
diamine (NH.sub.2 --R.sub.3 --NH.sub.2) to introduce the appropriate 
R.sub.4 group and the appropriate R.sub.2 group in the molecule, followed 
by acylation to introduce the 
##STR9## 
group, in accordance with the following equations: 
##STR10## 
where X is a halide, such as bromine or chlorine. 
The compound in which R.sub.4 is dimethylpyrimidyl can be prepared by 
reacting the appropriate carbamimidoyl-substituted compound with 
2,4-pentanedione in accordance with the following equation: 
##STR11## 
The steps given above for the preparation of the compounds of the invention 
need not be carried out in the order given, but can be carried out in any 
appropriate order, as will be apparent to those skilled in the art. 
The reactants involved in the above reactions are all available or can be 
readily synthesized in a known manner. Similarly, appropriate conditions 
for carrying out the reactions will be obvious to those skilled in the 
art. 
The following examples are presented to further illustrate the invention.