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US 4,358,448 AGranted
N-substituted thiazolyl derivatives of oxy-imino-substituted cephalosporins useful as anti-bacterial agents
AssigneeFarmitalia Carlo Erba S.p.A.
InventorsEttore Perrone, Giuliano Nannini, Marco Alpegiani, Franco Giudici, Giuseppe Meinardi
Life of this patent
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Abstract
Derivatives of N-substituted thiazolyl oxy-imino-substituted cephalosporins, such as, for instance, the compound 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamino]-3- [(tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carboxylic acid, are disclosed. The disclosed compounds have high anti-bacterial activity against Gram-positive and Gram-negative bacteria normally susceptible to cephalosporins.
Claims11
Compound of the formula (I) ##STR93## wherein R is (1) --OR.sub.2 in which R.sub.2 is a hydrogen atom or a saturated or unsaturated C.sub.1 -C.sub.6 branched or straight chain aliphatic hydrocarbon group which is unsubstituted or substituted by a substituent selected from the group consisting (a) cyano;
- (b) -COOR.sub.4 in which R.sub.4 is hydrogen, or C.sub.1 -C.sub.6 alkyl and (c) ##STR94## in which each of the groups R.sub.5 and R.sub.6, which may be the same or different, represents a hydrogen atom, a C.sub.1 -C.sub.6 alkyl or a C.sub.2 -C.sub.6 alkanoyl group or (2) ##STR95## wherein R.sub.5 and R.sub.6 are as defined above;
- R.sub.1 represents a hydrogen atom;
- R.sub.3 represents a hydrogen atom, or a branched or straight chain saturated or unsaturated C.sub.1 -C.sub.6 aliphatic hydrocarbon group, which may be unsubstituted or substituted by one or more substituents selected from (a') hydroxy;
- (b') cyano;
- (c') C.sub.1 -C.sub.6 alkyl, (d') ##STR96## in which R.sub.5 and R.sub.6 are as defined above;
- (e') -COOR.sub.7 in which R.sub.7 may be hydrogen, C.sub.1 -C.sub.6 alkyl, aryl, indanyl, or acetoxymethyl, or (f') halo-C.sub.1 -C.sub.6 alkyl;
- n is zero, 1 or 2;
- Y is hydrogen;
- halogen;
- hydroxy;
- C.sub.1 -C.sub.6 alkoxy;
- C.sub.1 -C.sub.6 alkyl or a group --CH.sub.2 --Z is which Z is (1) ##STR97## or (2) ##STR98## where R' is hydrogen, C.sub.1 -C.sub.6 alkyl, carboxy, cyano or carbamoyl;
- or (3) --S--Het, wherein Het is:
- (1) a tetrazolyl radical, unsubstituted or substituted by C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.4 alkenyl, (CH.sub.2)m.sub.1 --COOR.sub.4 wherein m.sub.1 is 1, 2 or 3 and R.sub.4 is as defined above, --CH.dbd.CH--COOR.sub.4 wherein R.sub.4 is as defined above, --(CH.sub.2)m.sub.1 --CN;
- --(CH.sub.2)m.sub.1 --CONH.sub.2 or --(CH.sub.2)m.sub.1 --SO.sub.3 H wherein m.sub.1 is as defined above, ##STR99## wherein m.sub.1 is as defined above and R.sub.5 and R.sub.6 are as defined above;
- (2) a thiadiazolyl radical, unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, --SH;
- --SCH.sub.3, --SCH.sub.2 COOH, --(CH.sub.2).sub.m --COOH, ##STR100## wherein each of R'.sub.5 and R'.sub.6 is hydrogen or C.sub.1 -C.sub.3 alkyl and m is 0, 1, 2 or 3;
- (3) a heterobicyclic ring selected from tetrazolopyridazinyl, tetrazolopyrazinyl, thiadiazolopyridazinyl, and triazolopyridazinyl, each optionally substituted by hydroxy, --SH, ##STR101## wherein R'.sub.5 and R'.sub.6 are as defined above, --COOR.sub.4 wherein R.sub.4 is as defined above, C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.4 alkenyl, --S--CH.sub.2 COOR.sub.4, --CH.sub.2 COOR.sub.4, or --CH.dbd.CH--COOR.sub.4, wherein R.sub.4 is as defined above;
- or ##STR102## wherein R'.sub.5 and R'.sub.6 are as defined above;
- and X is a free carboxy group or a pharmaceutically acceptable ester thereof;
- and the pharmaceutically and veterinarily acceptable salts thereof.
18 more elements
Syn-isomer of the compound of claim 1, wherein
- R.sub.1 is hydrogen;
- R is hydroxy, --O--C.sub.1 -C.sub.6 alkyl, amino;
- R.sub.3 is hydrogen;
- C.sub.1 -C.sub.6 alkyl;
- C.sub.2 -C.sub.4 alkenyl;
- --(CH.sub.2)m.sub.1 --COOH wherein m.sub.1 is as defined in claim 1, ##STR106## or --CH.dbd.CH--COOH;
- Y is hydrogen, halogen, hydroxy, methoxy, methyl, ##STR107## or CH.sub.2 --S--Het, wherein Het is (1) tetrazolyl unsubstituted or substituted by C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.4 alkenyl, --(CH.sub.2)m.sub.1 --COOH, --(CH.sub.2)m.sub.1 --CN or ##STR108## wherein m.sub.1 is as defined above and R.sub.5 and R.sub.6 are independently hydrogen, C.sub.1 -C.sub.6 alkyl or C.sub.2 -C.sub.6 alkanoyl (2) a thiadiazolyl radical, unsubstituted or substituted by methyl, C.sub.2 -C.sub.4 alkenyl;
- --SH;
- --SCH.sub.3 ;
- --SCH.sub.2 COOH;
- --(CH.sub.2).sub.m --COOH;
- ##STR109## wherein R'.sub.5 and R'.sub.6 are independently hydrogen or C.sub.1 -C.sub.3 alkyl and m is as defined in claim 1;
- (3) tetrazolopyridazinyl, optionally substituted by hydroxy, --SH, ##STR110## wherein R'.sub.5 and R'.sub.6 are as defined above;
- --COOR.sub.4 wherein R.sub.4 is as defined in claim 15;
- C.sub.1 -C.sub.3 alkyl;
- C.sub.2 -C.sub.4 alkenyl;
- --CH.sub.2 COOR.sub.4 or --CH.dbd.CH--COOR.sub.4, wherein R.sub.4 is as defined above or ##STR111## wherein R'.sub.5 and R'.sub.6 are as defined above;
- n is zero;
- X is a free carboxy group, and the pharmaceutically and veterinarily acceptable salts thereof.
16 more elements
Syn-isomer of the compound of claim 1, wherein
- R.sub.1 is hydrogen;
- R is hydroxy;
- R.sub.3 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.4 alkenyl, --(CH.sub.2)m.sub.1 --COOH wherein m.sub.1 is 1, 2 or 3, ##STR112## or --CH.dbd.CH--COOH;
- Y is hydrogen, halogen, hydroxy, methoxy, ##STR113## or --CH.sub.2 --S--Het, wherein Het is (1) tetrazolyl unsubstituted or substituted by C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.4 alkenyl, --(CH.sub.2)m.sub.1 --COOH, --(CH.sub.2)m.sub.1 --CN or ##STR114## wherein m.sub.1 is as defined above and R.sub.5 and R.sub.6 are independently hydrogen, C.sub.1 -C.sub.6 alkyl or C.sub.2 -C.sub.4 alkanoyl;
- (2) a thiadiazolyl radical, unsubstituted or substituted by methyl, C.sub.2 -C.sub.4 alkenyl;
- --SH;
- --SCH.sub.3 ;
- --SCH.sub.2 COOH;
- --(CH.sub.2).sub.m --COOH;
- ##STR115## wherein m, R'.sub.5 and R'.sub.6 are as defined in claim 1;
- (3) tetrazolopyridazinyl, optionally substituted by hydroxy, --SH, ##STR116## wherein R'.sub.5 and R'.sub.6 are as defined above;
- --COOR.sub.4 wherein R.sub.4 is as defined in claim 15;
- C.sub.1 -C.sub.3 alkyl;
- C.sub.2 -C.sub.4 alkenyl, --CH.sub.2 COOR.sub.4 or --CH.dbd.CH--COOR.sub.4, wherein R.sub.4 is as defined above or ##STR117## wherein R'.sub.5 and R'.sub.6 are as defined above n is zero;
- X is a free carboxy group, and the pharmaceutically and veterinarily acceptable salts thereof.
12 more elements
7.beta.-[2-(2-imino-3-h ydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[(tetrazolo[1,5-b]pyrida zin-6-yl)-thiomethyl]-3-cephem-4-carboxylic acid and its pharmaceutically and veterinarily acceptable salts and esters.
7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl )-2-methoxy-imino-acetamido]-3-[(tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl ]-3-cephem-4-carboxylic acid (syn-isomer) and its pharmaceutically and veterinarily acceptable salts and esters.
A compound selected from
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-hydroxy-imino-acetamido]-3-c ephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-c ephem-4-carboxylic acid (syn-isomer);
- .beta. -[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(R )-sulphoxide-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(S )-sulphoxide-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-c hloro-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-h ydroxy-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-m ethoxy-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-a cetoxy-methyl-3-cephem-4-carboxylic acid;
- (syn-isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(R )-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(S )-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ -(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ 1-(2-propenyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-( 1-[2-cyanoethyl]-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ (5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ (5-methyl-mercapto-1,3,4-thiadiazol-2-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ (5-amino-1,3,4-thiadiazol-2-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- .beta. -[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ (8-amino-tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ (8-carboxy-tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carboxyli c acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ (8-carboxy-methyl-tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-ca rboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ (2,3dihydro-2-methyl-3-oxo-1,2,4-triazolo-[4,3,b]-pyridazin-6-yl)-thiomethy l]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetami do]-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetami do]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetami do]-3-[(8-amino-tetrazolo[1,5-b]pyridazin-6-yl) -thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-(.beta.-carboxyvinyleneoxy-i mino)-acetamido]-3-[(8-amino-tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3- cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1-s ulphone-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1-s ulphone-3-acetoxy methyl-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-(.alpha.-methyl-.alpha.-carb oxy-ethoxyimino)-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxyimino-acetamido]-3-[8 -aminocarbonyl-tetrazolo[1,5-b]pyridazin-6-yl-]thiomethyl]-3-cephem-4-carbo xylic acid (syn-isomer);
- and the pharmaceutically and veterinarily acceptable salts and esters thereof.
27 more elements
A compound selected from
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-c ephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-a cetoxy-methyl-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(R )-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(S )-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ (1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-( 1-[2-propenyl]-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ 1-(2-cyanoethyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ (5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ (tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ (8-amino-tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ (8-carboxy-tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carboxyli c acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ (8-carboxymethyl-tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-car boxylic acid (syn-isomer);
- .beta. -[2-(2-imino-3-methoxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetami do]-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetami do]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetami do]-3-[(8-amino-tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carb oxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1-s ulphone-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-(.alpha.-methyl-.alpha.-carb oxy-ethoxy-imino)-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[ 8-aminocarbonyl-tetrazolo[1,5-b]pyridazin-6-ylthiomethyl]-3-cephem-4-carbox ylic acid (syn-isomer);
- and the pharmaceutically and veterinarily acceptable salts and esters thereof.
16 more elements
A compound selected from
- 7.beta.-[2-(2-imino-3-amino-4-thiazolinyl)2-methoxy-imino-acetamido]-3-ceph em-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-ace toxy-methyl-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(R)- sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(S)- sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[(1 -methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[(5 -methyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- .beta. -[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[(t etrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[(8 -amino-tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-amino-4-thiazolinyl)-2-carboxymethoxy-imino-acetamido ]-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-amino-4-thiazolinyl)-2-(.beta.-carboxyvinyleneoxy-imi no)-acetamido]-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-c arboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-1-sul phone-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn isomer);
- 7.beta.-[2-(2-imino-3-amino-4-thiazolinyl)-2-(.beta.-methyl-.alpha.-carboxy ethoxyimino)-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn-isomer);
- 7.beta.-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxyimino-acetamido]-3-[8-a minocarbonyl-tetrazolo[1,5-b]pyridazin-6-ylthiomethyl]-3-cephem-4-carboxyli c acid (syn-isomer),
- and the pharmaceutically and veterinarily acceptable salts and esters thereof.
11 more elements
Dependencies are inferred from the claim text.