Soft tertiary amine esters of bio-affecting carboxylic acids

Claim 2

A compound selected from the group consisting of: (a) compounds having the structural formula: ##STR523## wherein R--COO-- is the acyloxy residue of the cephalosporin antibiotic containing one carboxylic acid function; Y and Y', which can be the same or different, and each hydrogen or alkyl of 1 to 4 carbon atoms; n is zero or one; the depicted phenylene group is oriented such that R--COO-- and ##STR524## are positioned ortho or para to each other; R 1 and R 2 , which can be the same or different, are each alkyl or 1 to 10 carbon atoms; alkenyl of 2 to 10 carbon atoms; aryl of 6 to 10 carbon atoms; cycloalkyl or 3 to 8 carbon atoms; cycloalkenyl of 4 to 8 carbon atoms; alkynyl or 2 to 10 carbon atoms; aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl, or alkynylaryl, wherein the alkyl, alkenyl, alkynyl, and aryl portions are defined as above; or a substituted derivative of one of the above-defined alkyl, alkenyl, aryl, cycloalkyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl and alkynylaryl radicals, said derivative having one or more substituents each of which are selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkanoyl, C 1 -C 8 alkanoyloxy, halo, cyano, C 2 -C 9 carbalkoxy, C 1 -C 8 alkylthio, nitro, C 1 -C 8 haloalkyl having 1 or more halo substituents, dialkylamino wherein the alkyl portions each contain 1 to 8 carbon atoms, carboxy, dialkylcarbamyl wherein the alkyl portions each contain 1 to 8 carbon atoms, and C 1 -C 8 alkylsulfonyl; or R 1 and R 2 are combined so that --NR 1 R 2 represents the residue of a saturated or unsaturated heterocyclic compound containing one secondary nitrogen atom; and R 3 is hydrogen, R 1' , ##STR525## --CH 2 OCOR 1' , --CH 2 ONO 2 , CX 3 , 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, cyano, carbamyl or C 2 -C 9 alkylcarbamyl, wherein R 1 and R 2 are as defined above, X is Cl or Br and R 1' is any radical encompassed by the definition of R 1 above; and (b) the non-toxic pharmaceutically acceptable acid addition salts and N-oxides thereof.

Claim 3

A compound as defined by claim 1, wherein R--COO-- is the acyloxy residue of a compound selected from the group consisting of cefmetazole, cefazolin, cephalexin, cefoxitin, cephacetrile, cephalogylcin, cephaloridine, cephalothin, cephapirin and cephradine.

Claim 4

A compound as defined by claim 2, wherein R--COO-- is the acyloxy residue of cefmetazole.

Claim 5

A compound as defined by claim 2, wherein R--COO-- is the acyloxy residue of cefazolin.

Claim 6

A compound as defined by claim 2, wherein R--COO-- is the acyloxy residue of cephalexin.

Claim 7

A compound as defined by claim 1, wherein R--COO-- is the acyloxy residue of a penicillin antibiotic containing one carboxylic acid function.

Claim 8

A compound as defined by claim 6, wherein R--COO-- is the acyloxy residue of a compound selected from the group consisting of ampicillin, amoxicillin, hetacillin, carfecillin, carindacillin, amylpenicillin, azidocillin, benzylpenicillinic acid, clometacillin, cloxacillin, cyclacillin, methicillin, nafcillin, 2-pentenylpenicillin, penicillin BT, penicillin O, penicillin S, penicillin V, chlorobutin penicillin, dicloxacillin, diphenicillin, heptylpenicillin and metampicillin.

Claim 9

A compound as defined by claim 7, wherein R--COO-- is the acyloxy residue of ampicillin.

Claim 10

A compound as defined by claim 7, wherein R--COO-- is the acyloxy residue of penicillin V.

Claim 11

A compound as defined by claim 7, wherein R--COO-- is the acyloxy residue of amoxicillin.

Claim 12

A compound as defined by claim 7, wherein R--COO-- is the acyloxy residue of hetacillin.

Claim 13

A compound selected from the group consisting of: (a) compounds having the structural formula: ##STR526## wherein --OOC--R'--COO-- is the di(acyloxy) residue of a bio-affecting dicarboxylic acid selected from the group consisting of methotrexate, carbenicillin, penicillin N, and glutathione; Y and Y', which can be the same or different, and each hydrogen or alkyl of 1 to 4 carbon atoms; n is zero or one; the depicted phenylene group is oriented such that R--COO-- and ##STR527## are positioned ortho or para to each other; R 1 and R 2 , which can be the same or different, are each alkyl or 1 to 10 carbon atoms; alkenyl of 2 to 10 carbon atoms; aryl of 6 to 10 carbon atoms; cycloalkyl or 3 to 8 carbon atoms; cycloalkenyl of 4 to 8 carbon atoms; alkynyl or 2 to 10 carbon atoms; aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl, or alkynylaryl, wherein the alkyl, alkenyl, alkynyl, and aryl portions are defined as above; or a substituted derivative of one of the above-defined alkyl, alkenyl, aryl, cycloalkyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl and alkynylaryl radicals, said derivative having one or more substituents each of which are selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkanoyl, C 1 -C 8 alkanoyloxy, halo, cyano, C 2 -C 9 carbalkoxy, C 1 -C 8 alkylthio, nitro, C 1 -C 8 haloalkyl having 1 or more halo substituents, dialkylamino wherein the alkyl portions each contain 1 to 8 carbon atoms, carboxy, dialkylcarbamyl wherein the alkyl portions each contain 1 to 8 carbon atoms, and C 1 -C 8 alkylsulfonyl; or R 1 and R 2 are combined so that --NR 1 R 2 represents the residue of a saturated or unsaturated heterocyclic compound containing one secondary nitrogen atom; and R 3 is hydrogen, R 1' , ##STR528## --CH 2 OCOR 1' , --CH 2 ONO 2 , CX 3 , 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, cyano, carbamyl or C 2 -C 9 alkylcarbamyl, wherein R 1 and R 2 are as defined above, X is Cl or Br and R 1' is any radical encompassed by the definition of R 1 above; and (b) the non-toxic pharmaceutically acceptable acid addition salts and N-oxides thereof.

Claim 14

A compound selected from the group consisting of: (a) compounds having the structural formula: ##STR526## wherein --OOC--R'--COO-- is the di(acyloxy) residue of a bio-affecting dicarboxylic acid selected from the group consisting of methotrexate, carbenicillin, penicillin N, and glutathione; Y and Y', which can be the same or different, and each hydrogen or alkyl of 1 to 4 carbon atoms; n is zero or one; the depicted phenylene group is oriented such that R--COO-- and ##STR527## are positioned ortho or para to each other; R 1 and R 2 , which can be the same or different, are each alkyl or 1 to 10 carbon atoms; alkenyl of 2 to 10 carbon atoms; aryl of 6 to 10 carbon atoms; cycloalkyl or 3 to 8 carbon atoms; cycloalkenyl of 4 to 8 carbon atoms; alkynyl or 2 to 10 carbon atoms; aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl, or alkynylaryl, wherein the alkyl, alkenyl, alkynyl, and aryl portions are defined as above; or a substituted derivative of one of the above-defined alkyl, alkenyl, aryl, cycloalkyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl and alkynylaryl radicals, said derivative having one or more substituents each of which are selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkanoyl, C 1 -C 8 alkanoyloxy, halo, cyano, C 2 -C 9 carbalkoxy, C 1 -C 8 alkylthio, nitro, C 1 -C 8 haloalkyl having 1 or more halo substituents, dialkylamino wherein the alkyl portions each contain 1 to 8 carbon atoms, carboxy, dialkylcarbamyl wherein the alkyl portions each contain 1 to 8 carbon atoms, and C 1 -C 8 alkylsulfonyl; or R 1 and R 2 are combined so that --NR 1 R 2 represents the residue of a saturated or unsaturated heterocyclic compound containing one secondary nitrogen atom; and R 3 is hydrogen, R 1' , ##STR528## --CH 2 OCOR 1' , --CH 2 ONO 2 , CX 3 , 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, cyano, carbamyl or C 2 -C 9 alkylcarbamyl, wherein R 1 and R 2 are as defined above, X is Cl or Br and R 1' is any radical encompassed by the definition of R 1 above; and (b) the non-toxic pharmaceutically acceptable acid addition salts and N-oxides thereof.

Claim 15

A compound as defined by claim 12, wherein --OOC--R'--COO-- is the di(acyloxy) residue of methotrexate.

Claim 16

A compound as defined by claim 12, wherein --OOC--R'--COO-- is the di(acyloxy) residue or glutathione.

Claim 17

A pharmaceutical composition of matter comprising an antibiotic effective amount of a compound selected from the group consisting of: (a) compounds having the structural formula: ##STR529## wherein R--COO-- is the acyloxy residue of a cephalosporin antibiotic containing one carboxylic acid function; Y and Y', which can be the same or different, and each hydrogen or alkyl of 1 to 4 carbon atoms; n is zero or one; the depicted phenylene group is oriented such that R--COO-- and ##STR530## are positioned ortho or para to each other; R 1 and R 2 , which can be the same or different, are each alkyl or 1 to 10 carbon atoms; alkenyl of 2 to 10 carbon atoms; aryl of 6 to 10 carbon atoms; cycloalkyl or 3 to 8 carbon atoms; cycloalkenyl of 4 to 8 carbon atoms; alkynyl or 2 to 10 carbon atoms; aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl, or alkynylaryl, wherein the alkyl, alkenyl, alkynyl, and aryl portions are defined as above; or a substituted derivative of one of the above-defined alkyl, alkenyl, aryl, cycloalkyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl and alkynylaryl radicals, said derivative having one or more substituents each of which are selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkanoyl, C 1 -C 8 alkanoyloxy, halo, cyano, C 2 -C 9 carbalkoxy, C 1 -C 8 -alkylthio, nitro, C 1 -C 8 haloalkyl having 1 or more halo substitutents, dialkylamino wherein the alkyl portions each contain 1 to 8 carbon atoms, carboxy, dialkylcarbamyl wherein the alkyl portions each contain 1 to 8 carbon atoms, and C 1 -C 8 alkylsulfonyl; or R 1 and R 2 are combined so that --NR 1 R 2 represents the residue of a saturated or unsaturated heterocyclic compound containing one secondary nitrogen atom; and R 3 is hydrogen, R 1' , ##STR531## --CH 2 OCOR 1' , --CH 2 ONO 2 , CX 3 , 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, cyano, carbamyl or C 2 -C 9 alkylcarbamyl, wherein R 1 and R 2 are as defined above, X is Cl or Br and R 1 and R 2 , which can be the same or different, are each alkyl or 1 to 10 carbon atoms; alkenyl of 2 to 10 carbon atoms; aryl of 6 to 10 carbon atoms; cycloalkyl or 3 to 8 carbon atoms; cycloalkenyl of 4 to 8 carbon atoms; alkynyl or 2 to 10 carbon atoms; aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl, or alkynylaryl, wherein the alkyl, alkenyl, alkynyl, and aryl portions are defined as above; or a substituted derivative of one of the above-defined alkyl, alkenyl, aryl, cycloalkyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl and alkynylaryl radicals, said derivative having one or more substituents each of which are selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkanoyl, C 1 -C 8 alkanoyloxy, halo, cyano, C 2 -C 9 carbalkoxy, C 1 -C 8 alkylthio, nitro, C 1 -C 8 haloalkyl having 1 or more halo substituents, dialkylamino wherein the alkyl portions each contain 1 to 8 carbon atoms, carboxy, dialkylcarbamyl wherein the alkyl portions each contain 1 to 8 carbon atoms, and C 1 -C 8 alkylsulfonyl; or R 1 and R 2 are combined so that --NR 1 R 2 represents the residue of a saturated or unsaturated heterocyclic compound containing one secondary nitrogen atom; and R 3 is hydrogen, R 1' , ##STR532## --CH 2 OCOR 1' , --CH 2 ONO 2 , CX 3 , 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, cyano, carbamyl or C 2 -C 9 alkylcarbamyl, wherein R 1 and R 2 are as defined above, X is Cl or Br R 1' is any radical encompassed by the definition of R 1 above; and (b) the non-toxic pharmaceutically acceptable acid addition salts and N-oxides thereof, and a pharmaceutically acceptable carrier therefor.

Claim 18

A pharmaceutical composition of matter comprising an antibiotic effective amount of a compound selected from the group consisting of: (a) compounds having the structural formula: ##STR529## wherein R--COO-- is the acyloxy residue of a cephalosporin antibiotic containing one carboxylic acid function; Y and Y', which can be the same or different, and each hydrogen or alkyl of 1 to 4 carbon atoms; n is zero or one; the depicted phenylene group is oriented such that R--COO-- and ##STR530## are positioned ortho or para to each other; R 1 and R 2 , which can be the same or different, are each alkyl or 1 to 10 carbon atoms; alkenyl of 2 to 10 carbon atoms; aryl of 6 to 10 carbon atoms; cycloalkyl or 3 to 8 carbon atoms; cycloalkenyl of 4 to 8 carbon atoms; alkynyl or 2 to 10 carbon atoms; aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl, or alkynylaryl, wherein the alkyl, alkenyl, alkynyl, and aryl portions are defined as above; or a substituted derivative of one of the above-defined alkyl, alkenyl, aryl, cycloalkyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl and alkynylaryl radicals, said derivative having one or more substituents each of which are selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkanoyl, C 1 -C 8 alkanoyloxy, halo, cyano, C 2 -C 9 carbalkoxy, C 1 -C 8 -alkylthio, nitro, C 1 -C 8 haloalkyl having 1 or more halo substitutents, dialkylamino wherein the alkyl portions each contain 1 to 8 carbon atoms, carboxy, dialkylcarbamyl wherein the alkyl portions each contain 1 to 8 carbon atoms, and C 1 -C 8 alkylsulfonyl; or R 1 and R 2 are combined so that --NR 1 R 2 represents the residue of a saturated or unsaturated heterocyclic compound containing one secondary nitrogen atom; and R 3 is hydrogen, R 1' , ##STR531## --CH 2 OCOR 1' , --CH 2 ONO 2 , CX 3 , 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, cyano, carbamyl or C 2 -C 9 alkylcarbamyl, wherein R 1 and R 2 are as defined above, X is Cl or Br and R 1 and R 2 , which can be the same or different, are each alkyl or 1 to 10 carbon atoms; alkenyl of 2 to 10 carbon atoms; aryl of 6 to 10 carbon atoms; cycloalkyl or 3 to 8 carbon atoms; cycloalkenyl of 4 to 8 carbon atoms; alkynyl or 2 to 10 carbon atoms; aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl, or alkynylaryl, wherein the alkyl, alkenyl, alkynyl, and aryl portions are defined as above; or a substituted derivative of one of the above-defined alkyl, alkenyl, aryl, cycloalkyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl and alkynylaryl radicals, said derivative having one or more substituents each of which are selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkanoyl, C 1 -C 8 alkanoyloxy, halo, cyano, C 2 -C 9 carbalkoxy, C 1 -C 8 alkylthio, nitro, C 1 -C 8 haloalkyl having 1 or more halo substituents, dialkylamino wherein the alkyl portions each contain 1 to 8 carbon atoms, carboxy, dialkylcarbamyl wherein the alkyl portions each contain 1 to 8 carbon atoms, and C 1 -C 8 alkylsulfonyl; or R 1 and R 2 are combined so that --NR 1 R 2 represents the residue of a saturated or unsaturated heterocyclic compound containing one secondary nitrogen atom; and R 3 is hydrogen, R 1' , ##STR532## --CH 2 OCOR 1' , --CH 2 ONO 2 , CX 3 , 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, cyano, carbamyl or C 2 -C 9 alkylcarbamyl, wherein R 1 and R 2 are as defined above, X is Cl or Br R 1' is any radical encompassed by the definition of R 1 above; and (b) the non-toxic pharmaceutically acceptable acid addition salts and N-oxides thereof, and a pharmaceutically acceptable carrier therefor.

Claim 21

A pharmaceutical composition of matter comprising an antibiotic effective amount of a compound selected from the group consisting of: (a) compounds having the structural formula: ##STR535## wherein --OOC--R'--COO-- is the di(acyloxy) residue of a bio-affecting dicarboxylic acid selected from the group consisting of methotrexate, carbenicillin, penicillin n, and glutathione; Y and Y', which can be the same or different, and each hydrogen or alkyl of 1 to 4 carbon atoms; n is zero or one; the depicted phenylene group is oriented such that R--COO-- and ##STR536## are positioned ortho or para to each other; R 1 and R 2 , which can be the same or different, are each alkyl or 1 to 10 carbon atoms; alkenyl of 2 to 10 carbon atoms; aryl of 6 to 10 carbon atoms; cycloalkyl or 3 to 8 carbon atoms; cycloalkenyl of 4 to 8 carbon atoms; alkynyl or 2 to 10 carbon atoms; aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl, or alkynylaryl, wherein the alkyl, alkenyl, alkynyl, and aryl portions are defined as above; or a substituted derivative of one of the above-defined alkyl, alkenyl, aryl, cycloalkyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl and alkynylaryl radicals, said derivative having one or more substituents each of which are selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkanoyl, C 1 -C 8 alkanoyloxy, halo, cyano, C 2 -C 9 carbalkoxy, C 1 -C 8 alkylthio, nitro, C 1 -C 8 haloalkyl having 1 or more halo substituents, dialkylamino wherein the alkyl portions each contain 1 to 8 carbon atoms, carboxy, dialkylcarbamyl wherein the alkyl portions each contain 1 to 8 carbon atoms, and C 1 -C 8 alkylsulfonyl; or R 1 and R 2 are combined so that --NR 1 R 2 represents the residue of a saturated or unsaturated heterocyclic compound containing one secondary nitrogen atom; and R 3 is hydrogen, R 1' , ##STR537## --CH 2 OCOR 1' , --CH 2 ONO 2 , CX 3 , 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, cyano, carbamyl or C 2 -C 9 alkylcarbamyl, wherein R 1 and R 2 are as defined above, X is Cl or Br and R 1 , is any radical encompassed by the definition of R 1 above; and (b) the non-toxic pharmaceutically acceptable acid addition salts and N-oxides thereof, and a pharmaceutically acceptable carrier therefor.

Claim 22

A pharmaceutical composition of matter comprising an antibiotic effective amount of a compound selected from the group consisting of: (a) compounds having the structural formula: ##STR535## wherein --OOC--R'--COO-- is the di(acyloxy) residue of a bio-affecting dicarboxylic acid selected from the group consisting of methotrexate, carbenicillin, penicillin n, and glutathione; Y and Y', which can be the same or different, and each hydrogen or alkyl of 1 to 4 carbon atoms; n is zero or one; the depicted phenylene group is oriented such that R--COO-- and ##STR536## are positioned ortho or para to each other; R 1 and R 2 , which can be the same or different, are each alkyl or 1 to 10 carbon atoms; alkenyl of 2 to 10 carbon atoms; aryl of 6 to 10 carbon atoms; cycloalkyl or 3 to 8 carbon atoms; cycloalkenyl of 4 to 8 carbon atoms; alkynyl or 2 to 10 carbon atoms; aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl, or alkynylaryl, wherein the alkyl, alkenyl, alkynyl, and aryl portions are defined as above; or a substituted derivative of one of the above-defined alkyl, alkenyl, aryl, cycloalkyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aralkenyl, aralkynyl, alkenylaryl and alkynylaryl radicals, said derivative having one or more substituents each of which are selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkanoyl, C 1 -C 8 alkanoyloxy, halo, cyano, C 2 -C 9 carbalkoxy, C 1 -C 8 alkylthio, nitro, C 1 -C 8 haloalkyl having 1 or more halo substituents, dialkylamino wherein the alkyl portions each contain 1 to 8 carbon atoms, carboxy, dialkylcarbamyl wherein the alkyl portions each contain 1 to 8 carbon atoms, and C 1 -C 8 alkylsulfonyl; or R 1 and R 2 are combined so that --NR 1 R 2 represents the residue of a saturated or unsaturated heterocyclic compound containing one secondary nitrogen atom; and R 3 is hydrogen, R 1' , ##STR537## --CH 2 OCOR 1' , --CH 2 ONO 2 , CX 3 , 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, cyano, carbamyl or C 2 -C 9 alkylcarbamyl, wherein R 1 and R 2 are as defined above, X is Cl or Br and R 1 , is any radical encompassed by the definition of R 1 above; and (b) the non-toxic pharmaceutically acceptable acid addition salts and N-oxides thereof, and a pharmaceutically acceptable carrier therefor.

Claim 25

A compound as defined by claim 1 or 12, wherein R--COO-- is the acyloxy residue of a cephalosporin antibiotic containing one carboxylic acid function or of a penicillin antibiotic containing one carboxylic acid function.

Claim 26

A compound as defined by claim 19, wherein R--COO-- is the acyloxy residue of a compound selected from the group consisting of cefmetazole, cefazolin, cefalexin, cefoxitin, cephacetrile, cephaloglycin, cephaloridine, cephalothin, cephapirin, cephradine, ampicillin, amoxicillin, hetacillin, carfecillin, carindacillin, amylpenicillin, azidocillin, benzylpenicillinic acid, clometacillin, cloxacillin, cyclacillin, methicillin, nafcillin, 2-pentenylpenicillin, penicillin BT, penicillin O, penicillin S, penicillin V, chlorobutin penicillin, dicloxacillin, diphenicillin, heptylpenicillin and metampicillin.

Claim 27

A compound as defined by claim 20, wherein R--COO-- is the acyloxy residue of a compound selected from the group consisting of cephalexin, cefmetazole, cefazolin, cefoxitin, ampicillin, hetacillin, amoxicillin and amylpenicillin.

Claim 28

A compound as defined by claim 2, wherein R--COO-- is the acyloxy residue of cefoxitin.

Claim 29

A compound as defined by claim 7, wherein R--COO-- is the acyloxy residue of amylpenicillin.

Claim 30

The compound as defined by claim 21, wherein R--COO-- is the acyloxy residue of cephalexin, n is zero, R 3 is hydrogen and --NR 1 R 2 is 1-imidazolyl.

Claim 31

The compound as defined by claim 21, wherein R--COO-- is the acyloxy residue of cefmetazole, n is zero, R 3 is CCl 3 and --NR 1 R 2 is 1-imidazolyl.

Claim 32

The compound as defined by claim 21, wherein R--COO-- is the acyloxy residue of cefazolin, n is zero, R 3 is ##STR541## and --NR 1 R 2 is 1-imidazolyl.

Claim 33

The compound as defined by claim 21, wherein R--COO-- is the acyloxy residue of cefoxitin, n is zero, R 3 is hydrogen and --NR 1 R 2 is 1-imidazolyl.

Claim 34

The compound as defined by claim 21, wherein R--COO-- is the acyloxy residue of ampicillin, n is zero, R 3 is CCl 3 and --NR 1 R 2 is 1-imidazolyl.

Claim 35

The compound as defined by claim 21, wherein R--COO-- is the acyloxy residue of hetacillin, n is zero, R 3 is CCl 3 and --NR 1 R 2 is 1-imidazolyl.

Claim 36

The compound as defined by claim 21, wherein R--COO-- is the acyloxy residue of amoxicillin, n is zero, R 3 is ##STR542## and --NR 1 R 2 is 1-imidazolyl.

Claim 37

The compound as defined by claim 21, wherein R--COO-- is the acyloxy residue of amylpenicillin, n is zero, R 3 is hydrogen and --NR 1 R 2 is 1-imidazolyl.