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This ... |
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Novel soft N-chloroamino alcohol derivatives exhibiting antibacterial activity
| Details |
Inventors: Kaminski, James J.; Bodor, Nicolae S.;
Assignee: INTERx Research Corporation (Lawrence, KS)
Primary Examiner: Turner; V. D.
Assistant Examiner:
Attorney, Agent or Firm: Bacon & Thomas
There is provided, a novel class of compounds exhibiting antibacterial activity and having the formula: ##STR1## wherein X and Y each represent a member which may be the same or different selected from the group consisting of H and Cl with the proviso that X and Y cannot represent H simultaneously; R.sub.1 and R.sub.2 each represent a member which may be the same or different selected from the group consisting of an n- or branched alkyl group of from 1 to 20 carbon atoms, an aryl group (phenyl, naphthyl, etc.) and a ##STR2## WHEREIN M REPRESENTS AN INTEGER OF FROM 2 TO 5; N REPRESENTS AN INTEGER OF 1 TO 8; AND Z represents a member selected from the group consisting of an --OOCR.sub.3 group, an --OR.sub.3 group and an --OCH.sub.2 OR.sub.3 group, wherein R.sub.3 represents a member selected from the group consisting of an n- or branched alkyl group of 1 to 20 carbon atoms, a phenyl group, a naphthyl group, a benzyl group, ##STR3## WHEREIN X is a halogen atom (Cl, Br, I), ##STR4## WHEREIN R.sub.4 represents a member selected from the group consisting of H, an n- or branched alkyl group, a benzyl group, and a --(CH.sub.2).sub.p COOH group, wherein p represents an integer of 1 to 4, and wherein W.sup..theta. represents a non-toxic pharmaceutically acceptable inorganic or organic anion. |
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DETAILED DESCRIPTION OF THE INVENTION In the above formula, when each of R.
sub.
1, R.
sub.
2 and R.
sub.
3 represent an alkyl group, a carbon range of from 1 - 5 carbon atoms is preferred.
When R.
sub.
1 and R.
sub.
2 represent an aryl group or ##STR9## respectively, phenyl is the aryl group of choice and 4 is the integer of choice for m.
The phrase, "nontoxic pharmaceutically acceptable inorganic or organic anion" as used herein generally includes the nontoxic acid addition salts of the compounds of formula (I), formed with nontoxic inorganic or organic acids.
For example, the salts include those derived from inorganic acids such as hydrochloric, hydrobromic, sulfuric, phosphoric, nitric and the like; and the salts prepared from organic acids such as acetic, propionic, succinic, stearic, malonic, pamoic, phenylacetic, glutaric, benzoic, toluene-sulfonic, methanesulfonic and the like.
While all the compounds encompassed within the above-described generic formula will satisfy the objectives of the present invention, nevertheless, certain compounds are preferred as set out below: 1.
2-N-Chloroamino-2-methyl-1-propyl acetate.
2.
2-N-Chloroamino-2-methyl-1-propyl propionate.
3.
2-N-Chloroamino-2-methyl-1-propyl butyrate.
4.
2-N-Chloroamino-2-methyl-1-propyl isobutyrate.
5.
2-N-Chloroamino-2-methyl-1-propyl valerate.
6.
2-N-Chloroamino-2-methyl-1-propyl isovalerate.
7.
2-N-Chloroamino-2-methyl-1-propyl hexanoate.
8.
2-N-Chloroamino-2-methyl-1-propyl octanoate.
9.
2-N-Chloroamino-2-methyl-1-propyl decanoate.
10.
2-N-Chloroamino-2-methyl-1-propyl dodecanoate.
11.
2-N-Chloroamino-2-methyl-1-propyl tetradecanoate.
12.
2-N-Chloroamino-2-methyl-1-propyl hexadecanoate.
13.
2-N-Chloroamino-2-methyl-1-propyl octadecanoate.
14.
2-N-Chloroamino-2-methyl-1-propyl 2,2-dimethylpropionate.
15.
2-N-Chloroamino-2-methyl-1-propyl benzoate.
16.
2-N-Chloroamino-2-methyl-1-propyl nicotinoate.
17.
2-N-Chloroamino-2-methyl-1-propyl isonicotinoate.
18.
2-N-Chloroamino-2-methyl-1-propyl nicotinate N-oxide.
19.
2-N-Chloroamino-2-methyl-1-propyl isonicotinate N-oxide
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Vasodialators 
