Interx Research Corporation

James J Kaminski

Nicolae S Bodor

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;

Antibacterially active N-chloroamino ester derivatives of alkyl

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), a 2, 3 or 4 ##STR4## A 2, 3, OR 4 ##STR5## WHEREIN R.sub.4 represents a member selected from the group consisting of H, an n- or branched alkyl group, a benzyl group, an O atom, and a --(CH.sub.2).sub.p COOH group, wherein p represents an integer of 1 to 4, and wherein W.sup..crclbar. represents a non-toxic pharmaceutically acceptable inorganic or organic anion.

Novel soft N-chloroamino alcohol derivatives exhibiting antibacterial

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 ##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..crclbar. represents a non-toxic pharmaceutically acceptable inorganic or organic anion.

Antibacterial novel soft n-chloroamino alcohol derivatives

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.

There is provided, novel 3-chloro-tetrahydro-1,3-oxazine or oxazolidine compounds, exhibiting antibacterial activity and being of low chlorine potential of the formula: ##STR1## wherein each of R.sub.1 and R.sub.2, which may be the same or different, represent an alkyl group of from 1 to 20 carbon atoms (C.sub.1 -C.sub.5 being preferred); wherein each of R.sub.5 and R.sub.6, which may be the same or different, represent a hydrogen atom or an alkyl group of from 1 to 20 carbon atoms (C.sub.1 -C.sub.5 being preferred); wherein l represents an integer of 1 or 2 and wherein each of R.sub.3 and R.sub.4, which may be the same or different, represent an alkyl group of from 1 to 20 carbon atoms (C.sub.1 -C.sub.5 being preferred) a --(CH.sub.2).sub.n X group, wherein n represents an integer of from 1 to 20 and wherein X represents a dimethylamino group, a diethylamino group, a trimethylammonium group, a triethylammonium group, a dimethylammonium group, a diethylammonium group, a --COOR.sub.7 group, a --OOCR.sub.8 group, and a --OR.sub.9 group, wherein each of R.sub.7 through R.sub.9, respectively, represent an alkyl group of from 1 to 5 carbon atoms or a benzyl group. In addition, R.sub.3 and R.sub.4 can also represent a ##STR2## group, wherein Y represents a --(CH.sub.2).sub.n --W--(CH.sub.2).sub.m -- group or a &gt;CH--Z group, wherein W represents a --O-- atom, a --CH.sub.2 -- group, a &gt;NCH.sub.3 -- group, a &gt;NHCH.sub.3.sup.+ group, a &gt;NC.sub.2 H.sub.5 group, a &gt;NHC.sub.2 H.sub.5.sup.+ group, a &gt;N(CH.sub.3).sub.2.sup.+ group, or a &gt;N(C.sub.2 H.sub.5).sub.2.sup.+ group, wherein n is the same or different from m and wherein each of n and m represent an integer of from 0 to 2; and wherein Z is defined in accordance with X above.

3-Chloro-1,3-oxazines or oxazolidines as antibacterial agents

There is provided, a novel class of compounds exhibiting antibacterial activity, said compounds 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.) ##STR2## WHEREIN N REPRESENTS AN INTEGER OF FROM 2 - 5; AND Z represents a member selected from the group consisting of an --OR.sub.3 group, ##STR3## WHEREIN R.sub.4 and R.sub.5 each represent a member which may be the same or different selected from the group consisting of H and an alkyl group of from 1 - 3 carbon atoms, wherein R.sub.6 and R.sub.7 each represent a member which may be the same or different selected from the group consisting of R.sub.1, R.sub.2, or H when X is not Cl or R.sub.1 and R.sub.2 when X is Cl, wherein R.sub.1 and R.sub.2 are as defined above, wherein X is as defined above, and wherein R.sub.3 in each case represents a member selected from the group consisting of an n- or branched alkyl group of from 2 - 20 carbon atoms, a --OCH.sub.2 CH.sub.2 --(OCH.sub.2 CH.sub.2).sub.n --OR.sub.1 group, wherein R.sub.1 is defined as above and n represents an integer of from 1 - 11, ##STR4## WHEREIN W represents a member selected from the group consisting of H, an- or branched alkyl group of from 1 - 20 carbon atoms, a halogen atom (Cl, Br, I), an --OR.sub.8 group, ##STR5## WHEREIN R.sub.4 and R.sub.5 are as defined above and R.sub.8 represents a member selected from the group consisting of H and R.sub.1, wherein R.sub.1 is as defined above, ##STR6## WHEREIN N REPRESENTS AN INTEGER OF FROM 1 - 20 AND R.sub.1 is as defined above,

N-chloro-amino acid derivatives exhibiting antibacterial activity

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## GROUP, 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.- represents a non-toxic pharmaceutically acceptable inorganic or organic anion.

Certain chloroamino esters of pyridine carboxylates and derivatives

There is provided, novel N-chloramine compounds of the 1,4-dichloro-2,2,5,5-tetrasubstituted-3,6-piperazinedione type, having the formula: ##STR1## WHERE R.sub.1, R.sub.2, R.sub.3, R.sub.4, which may be the same or different, each represent a member selected from the group consisting of an alkyl group of from 1 to 20 carbon atoms and an aryl group. The compounds encompassed by the above generic formula exhibit antibacterial activity, but most importantly, the compounds encompassed within the above generic formula exhibit enhanced stability over the closest related prior art compounds, when such compounds are employed in aqueous solution for antibacterial application.

Method of arresting bacterial growth with certain selected

There is provided a brominating and oxidizing agent of the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different, represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.22 straight or branched alkyl group, a phenyl group, and a substituted phenyl group whose substituents are selected from the group consisting of a methoxy group, a nitro group, a cyano group, a halogen atom (Br, Cl, I), a C.sub.1 -C.sub.2 dialkylamino group, a C.sub.1 -C.sub.2 dialkylaminomethyl group, a C.sub.1 -C.sub.2 dialkylaminoethyl group, a C.sub.1 -C.sub.2 dialkylammoniummethyl group, a C.sub.1 -C.sub.2 dialkylammoniumethyl group, a C.sub.1 -C.sub.2 trialkylammoniummethyl group, a C.sub.1 -C.sub.2 trialkylammoniumethyl group, a COOR.sub.5 group, and a CON(R.sub.5).sub.2 group, wherein R.sub.5 represents a C.sub.1 -C.sub.8 straight or branched alkyl group. The compounds falling within formula (I) find wide application as brominating and oxidizing agents in a number of organic reactions in which the prior art compound, N-bromosuccinimide has been employed to date. In comparison to N-bromosuccinimide, the compounds of the instant invention are characterized as being extremely stable to degradation and less polar with respect to their N-Br bond than N-bromosuccinimide such that promotion of 'radical' bromine release is achieved with minimal positive bromine release.

Brominating and oxidizing agent and method of using same

Antibacterially effective 3-chloro-2-oxazolidinones are prepared by chlorination of an appropriate 2-oxazolidinone either with elemental chlorine in an aqueous medium or with a mono-, di- or trichloroisocyanuric acid (cyanuric chloride) in an inert organic solvent. The 2-oxazolidinones are, in turn, prepared by reaction of an appropriate ethanolamine either with a di-lower-alkyl carbonate in the presence of a strong base or with urea at an elevated temperature.

Method of inhibiting bacterial growth with certain selected

There is provided, a novel class of compounds exhibiting antibacterial activity, said compounds having the formula: ##EQU1## 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 priviso 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 ##EQU2## (CH.sub.2).sub.n group, wherein n represents an integer of from 2 - 5; and Z represents a member selected from the group consisting of an --OR.sub.3 group, a a ##EQU3## wherein R.sub.4 and R.sub.5 each represent a member which may be the same or different selected from the group consisting of H and an alkyl group of from 1 - 3 carbon atoms, wherein R.sub.6 and R.sub.7 each represent a member which may be the same or different selected from the group consisting of R.sub.1, R.sub.2, or H when X is not Cl or R.sub.1 and R.sub.2 when X is Cl, wherein R.sub.1 and R.sub.2 are defined above, wherein X is as defined above, and wherein R.sub.3 in each case represents a member selected from the group consisting of an n- or branched alkyl group of from 2 - 20 carbon atoms, a --OCH.sub.2 CH.sub.2 (OCH.sub.2 CH.sub.2).sub.n --OR.sub.1 group, wherein R.sub.1 is defined as above and n represents an integer of from 1 - 11, a Group, wherein W represents a member selected from the group consisting of H, an n- or branched alkyl group of from 1 - 20 carbon atoms, a halogen atom, (Cl, Br, I), an --OR.sub.8 group, and a ##EQU4## group, wherein R.sub.4 and R.sub.5 are as defined above and R.sub.8 represents a member selcted from the group consisting of H and R.sub.1, wherein R.sub.1 is as defined above, and --CH.sub.2 CH.sub.2 --(OCH.sub.2 CH.sub.2).sub.n -- ##SPC1## Group, wherein n represens an integer of from 1 - 20 and R.sub.1 is as defined above,

N-chloro-amino acid derivatives activity

There is provided, novel 3-chloro-tetrahydro-1,3-oxazine or oxazolidine compounds, exhibiting antibacterial activity and being of low chlorine potential of the formula: ##SPC1## Wherein each of R.sub.1 and R.sub.2, which may be the same or different, represent an alkyl group of from 1 to 20 carbon atoms (C.sub.1 -C.sub.5 being preferred); wherein each of R.sub.5 and R.sub.6, which may be the same or different, represent a hydrogen atom or an alkyl group of from 1 to 20 carbon atoms (C.sub.1 -C.sub.5 being preferred); wherein l represents an integer of 1 or 2 and wherein each of R.sub.3 and R.sub.4, which may be the same or different, represent an alkyl group of from 1 to 20 carbon atoms (C.sub.1 -C.sub.5 being preferred), a --(CH.sub.2).sub.n X group, wherein n represents an integer of from 1 to 20 and wherein X represents a dimethylamino group, a diethylamino group, a trimethylammonium group, a triethylammonium group, a dimethylammonium group, a diethylammonium group, a --COOR.sub.7 group, a --OOCR.sub.8 group and, a --OR.sub.9 group, wherein each of R.sub.7 through R.sub.9, respectively, represent an alkyl group of from 1 to 5 carbon atoms or a benzyl group. In addition, R.sub.3 and R.sub.4 can also represent a ##EQU1## group, wherein Y represents a --(CH.sub.2).sub.n --W--(CH.sub.2).sub.m -- group or a &gt;CH--Z group, wherein W represents a --O-- atom, a --CH.sub.2 -- group, a &gt;NCH.sub.3 -- group, a &gt;NHCH.sub.3 .sup.+ group, a &gt;NC.sub.2 H.sub.5 group, a &gt;NHC.sub.2 H.sub.5 .sup.+ group, a &gt;N(CH.sub.3).sub.2 .sup.+ group, or a &gt;N(C.sub.2 H.sub.5).sub.2 .sup.+ group, wherein n is the same or different from m and wherein each of n and m represent an integer of from 0 to 2; and wherein Z is defined in accordance with X above.

Method for inhibiting bacterial growth with certain selected

There is provided, novel 3-chloro-tetrahydro 1,3-oxazine or oxazolidine compounds, exhibiting antibacterial activity and being of low chlorine potential of the formula: ##EQU1## WHEREIN EACH OF R.sub.1 and R.sub.2, which may be the same or different, represent an alkyl group of from 1 to 20 carbon atoms (C.sub.1 -C.sub.5 being preferred); wherein each of R.sub.5 and R.sub.6, which may be the same or different, represent a hydrogen atom or an alkyl group of from 1 to 20 carbon atoms (C.sub.1 -C.sub.5 being preferred); wherein l represents an integer of 1 or 2 and wherein each of R.sub.3 and R.sub.4, which may be the same or different, represent an alkyl group of from 1 to 20 carbon atoms (C.sub.1 -C.sub.5 being preferred), a --(CH.sub.2).sub.n X group, wherein n represents an integer of from 1 to 20 and wherein X represents a dimethylamino group, a diethylamino group, a trimethylammonium group, a triethylammonium group, a dimethylammonium group, a diethylammonium group, a --COOR.sub.7 group, a --OOCR.sub.8 group, and a --OR.sub.9 group, wherein each of R.sub.7 through R.sub.9, respectively, represent an alkyl group of from 1 to 5 carbon atoms or a benzyl group. In addition, R.sub.3 and R.sub.4 can also represent a ##EQU2## group, wherein Y represents a --(CH.sub.2).sub.n --W--(CH.sub.2).sub.m -- group or a &gt; CH--Z group, wherein W represents a --O-- atom, a --CH.sub.2 -- group, a &gt; NCH.sub.3 -- group, a &gt; NHCH.sub.3 .sup.+ group, a &gt; NC.sub.2 H.sub.5 group, a &gt; NHC.sub.2 H.sub.5 .sup.+ group, a &gt; N(CH.sub.3).sub.2 .sup.+ group, or a &gt; N(C.sub.2 H.sub.5).sub.2 .sup.+ group, wherein n is the same or different from m and wherein each of n and m represent an integer of from 0 to 2; and wherein Z is defined in accordance with X above.

Growing community of inventors

Lawrence, KS, United States of America

James J Kaminski