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US4358448A
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N-substituted thiazolyl derivatives of oxy-imino-substituted cephalosporins useful as anti-bacterial agents
Assignee: Pfizer Italia SRL
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Filing: 1980-11-12
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Granted: 1982-11-09
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Expires: 2000-11-12
Abstract
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-[(t etrazolo[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.
Inventors
- 👤 Ettore Perrone
- 👤 Giuliano Nannini
- 👤 Marco Alpegiani
- 👤 Franco Giudici
- 👤 Giuseppe Meinardi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 01:13
CPC Classifications
C; C07; C07D; C07D277/00; C07D277/02; C07D277/20; C07D277/587; A; A61; A61P; A61P31/00; A61P31/04; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
512 words
Compound of the formula (I) ##STR93## wherein R is (1) --OR 2 in which R 2 is a hydrogen atom or a saturated or unsaturated C 1 -C 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 4 in which R 4 is hydrogen, or C 1 -C 6 alkyl and (c) ##STR94## in which each of the groups R 5 and R 6 , which may be the same or different, represents a hydrogen atom, a C 1 -C 6 alkyl or a C 2 -C 6 alkanoyl group or (2) ##STR95## wherein R 5 and R 6 are as defined above; R 1 represents a hydrogen atom; R 3 represents a hydrogen atom, or a branched or straight chain saturated or unsaturated C 1 -C 6 aliphatic hydrocarbon group, which may be unsubstituted or substituted by one or more substituents selected from (a') hydroxy; (b') cyano; (c') C 1 -C 6 alkyl, (d') ##STR96## in which R 5 and R 6 are as defined above; (e') -COOR 7 in which R 7 may be hydrogen, C 1 -C 6 alkyl, aryl, indanyl, or acetoxymethyl, or (f') halo-C 1 -C 6 alkyl; n is zero, 1 or 2; Y is hydrogen; halogen; hydroxy; C 1 -C 6 alkoxy; C 1 -C 6 alkyl or a group --CH 2 --Z is which Z is (1) ##STR97## or (2) ##STR98## where R' is hydrogen, C 1 -C 6 alkyl, carboxy, cyano or carbamoyl; or (3) --S--Het, wherein Het is: (1) a tetrazolyl radical, unsubstituted or substituted by C 1 -C 3 alkyl, C 2 -C 4 alkenyl, (CH 2 )m 1 --COOR 4 wherein m 1 is 1, 2 or 3 and R 4 is as defined above, --CH═CH--COOR 4 wherein R 4 is as defined above, --(CH 2 )m 1 --CN; --(CH 2 )m 1 --CONH 2 or --(CH 2 )m 1 --SO 3 H wherein m 1 is as defined above, ##STR99## wherein m 1 is as defined above and R 5 and R 6 are as defined above; (2) a thiadiazolyl radical, unsubstituted or substituted by C 1 -C 4 alkyl, C 2 -C 4 alkenyl, --SH; --SCH 3 , --SCH 2 COOH, --(CH 2 ) m --COOH, ##STR100## wherein each of R' 5 and R' 6 is hydrogen or C 1 -C 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' 5 and R' 6 are as defined above, --COOR 4 wherein R 4 is as defined above, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, --S--CH 2 COOR 4 , --CH 2 COOR 4 , or --CH═CH--COOR 4 , wherein R 4 is as defined above; or ##STR102## wherein R' 5 and R' 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.
Claim 2
Dependent Claim
512 words
Compound of the formula (I) ##STR93## wherein R is (1) --OR 2 in which R 2 is a hydrogen atom or a saturated or unsaturated C 1 -C 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 4 in which R 4 is hydrogen, or C 1 -C 6 alkyl and (c) ##STR94## in which each of the groups R 5 and R 6 , which may be the same or different, represents a hydrogen atom, a C 1 -C 6 alkyl or a C 2 -C 6 alkanoyl group or (2) ##STR95## wherein R 5 and R 6 are as defined above; R 1 represents a hydrogen atom; R 3 represents a hydrogen atom, or a branched or straight chain saturated or unsaturated C 1 -C 6 aliphatic hydrocarbon group, which may be unsubstituted or substituted by one or more substituents selected from (a') hydroxy; (b') cyano; (c') C 1 -C 6 alkyl, (d') ##STR96## in which R 5 and R 6 are as defined above; (e') -COOR 7 in which R 7 may be hydrogen, C 1 -C 6 alkyl, aryl, indanyl, or acetoxymethyl, or (f') halo-C 1 -C 6 alkyl; n is zero, 1 or 2; Y is hydrogen; halogen; hydroxy; C 1 -C 6 alkoxy; C 1 -C 6 alkyl or a group --CH 2 --Z is which Z is (1) ##STR97## or (2) ##STR98## where R' is hydrogen, C 1 -C 6 alkyl, carboxy, cyano or carbamoyl; or (3) --S--Het, wherein Het is: (1) a tetrazolyl radical, unsubstituted or substituted by C 1 -C 3 alkyl, C 2 -C 4 alkenyl, (CH 2 )m 1 --COOR 4 wherein m 1 is 1, 2 or 3 and R 4 is as defined above, --CH═CH--COOR 4 wherein R 4 is as defined above, --(CH 2 )m 1 --CN; --(CH 2 )m 1 --CONH 2 or --(CH 2 )m 1 --SO 3 H wherein m 1 is as defined above, ##STR99## wherein m 1 is as defined above and R 5 and R 6 are as defined above; (2) a thiadiazolyl radical, unsubstituted or substituted by C 1 -C 4 alkyl, C 2 -C 4 alkenyl, --SH; --SCH 3 , --SCH 2 COOH, --(CH 2 ) m --COOH, ##STR100## wherein each of R' 5 and R' 6 is hydrogen or C 1 -C 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' 5 and R' 6 are as defined above, --COOR 4 wherein R 4 is as defined above, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, --S--CH 2 COOR 4 , --CH 2 COOR 4 , or --CH═CH--COOR 4 , wherein R 4 is as defined above; or ##STR102## wherein R' 5 and R' 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.
Claim 3
Dependent Claim
132 words
Compounds of claim 1, wherein R 1 is hydrogen; R is --hydroxy; --O--C 1 -C 6 alkyl; --O--C 2 -C 4 alkenyl; --O--(CH 2 )m 1 ---COOR 4 , wherein m 1 and R 4 are as defined in claim 1; amino; --NHCH 3 ; --N(CH 3 ) 2 or ##STR103## R 3 is hydrogen, C 1 -C 6 alkyl, C 2 -C 4 alkenyl, --(CH 2 )m 1 --COOH ##STR104## --(CH 2 )m 1 --CN, --(CH 2 )m 1 --CONH 2 wherein m 1 is as defined above; or --CH═CH--COOH; Y is hydrogen, halogen, hydroxy, C 1 -C 6 alkoxy, methyl, ##STR105## or CH 2 --S--HET, wherein HET is as defined in claim 1; n is zero; X is a free carboxy group, and the pharmaceutically and veterinarily acceptable salts thereof.
Claim 4
Dependent Claim
255 words
Syn-isomer of the compound of claim 1, wherein R 1 is hydrogen; R is hydroxy, --O--C 1 -C 6 alkyl, amino; R 3 is hydrogen; C 1 -C 6 alkyl; C 2 -C 4 alkenyl; --(CH 2 )m 1 --COOH wherein m 1 is as defined in claim 1, ##STR106## or --CH═CH--COOH; Y is hydrogen, halogen, hydroxy, methoxy, methyl, ##STR107## or CH 2 --S--Het, wherein Het is (1) tetrazolyl unsubstituted or substituted by C 1 -C 3 alkyl, C 2 -C 4 alkenyl, --(CH 2 )m 1 --COOH, --(CH 2 )m 1 --CN or ##STR108## wherein m 1 is as defined above and R 5 and R 6 are independently hydrogen, C 1 -C 6 alkyl or C 2 -C 6 alkanoyl (2) a thiadiazolyl radical, unsubstituted or substituted by methyl, C 2 -C 4 alkenyl; --SH; --SCH 3 ; --SCH 2 COOH; --(CH 2 ) m --COOH; ##STR109## wherein R' 5 and R' 6 are independently hydrogen or C 1 -C 3 alkyl and m is as defined in claim 1; (3) tetrazolopyridazinyl, optionally substituted by hydroxy, --SH, ##STR110## wherein R' 5 and R' 6 are as defined above; --COOR 4 wherein R 4 is as defined in claim 15; C 1 -C 3 alkyl; C 2 -C 4 alkenyl; --CH 2 COOR 4 or --CH═CH--COOR 4 , wherein R 4 is as defined above or ##STR111## wherein R' 5 and R' 6 are as defined above; n is zero; X is a free carboxy group, and the pharmaceutically and veterinarily acceptable salts thereof.
Claim 5
Dependent Claim
237 words
Syn-isomer of the compound of claim 1, wherein R 1 is hydrogen; R is hydroxy; R 3 is hydrogen, C 1 -C 6 alkyl, C 2 -C 4 alkenyl, --(CH 2 )m 1 --COOH wherein m 1 is 1, 2 or 3, ##STR112## or --CH═CH--COOH; Y is hydrogen, halogen, hydroxy, methoxy, ##STR113## or --CH 2 --S--Het, wherein Het is (1) tetrazolyl unsubstituted or substituted by C 1 -C 3 alkyl, C 2 -C 4 alkenyl, --(CH 2 )m 1 --COOH, --(CH 2 )m 1 --CN or ##STR114## wherein m 1 is as defined above and R 5 and R 6 are independently hydrogen, C 1 -C 6 alkyl or C 2 -C 4 alkanoyl; (2) a thiadiazolyl radical, unsubstituted or substituted by methyl, C 2 -C 4 alkenyl; --SH; --SCH 3 ; --SCH 2 COOH; --(CH 2 ) m --COOH; ##STR115## wherein m, R' 5 and R' 6 are as defined in claim 1; (3) tetrazolopyridazinyl, optionally substituted by hydroxy, --SH, ##STR116## wherein R' 5 and R' 6 are as defined above; --COOR 4 wherein R 4 is as defined in claim 15; C 1 -C 3 alkyl; C 2 -C 4 alkenyl, --CH 2 COOR 4 or --CH═CH--COOR 4 , wherein R 4 is as defined above or ##STR117## wherein R' 5 and R' 6 are as defined above n is zero; X is a free carboxy group, and the pharmaceutically and veterinarily acceptable salts thereof.
Claim 6
Dependent Claim
11 words
7β-[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 and its pharmaceutically and veterinarily acceptable salts and esters.
Claim 7
Dependent Claim
11 words
7β-[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 and its pharmaceutically and veterinarily acceptable salts and esters.
Claim 8
Dependent Claim
12 words
7β-[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.
Claim 9
Dependent Claim
12 words
7β-[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.
Claim 10
Dependent Claim
119 words
A compound selected from 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-hydroxy-imino-acetamido]-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-cephem-4-carboxylic acid (syn-isomer); β -[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(R)-sulphoxide-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(S)-sulphoxide-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-chloro-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-hydroxy-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-methoxy-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-acetoxy-methyl-3-cephem-4-carboxylic acid; (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(R)-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(S)-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn-isomer); 7β-[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); 7β-[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); 7β-[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); 7β-[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); 7β-[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); 7β-[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); β -[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); 7β-[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-carboxylic acid (syn isomer); 7β-[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-carboxylic acid (syn isomer); 7β-[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)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetamido]-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetamido]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetamido]-3-[(8-amino-tetrazolo[1,5-b]pyridazin-6-yl) -thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-(β-carboxyvinyleneoxy-imino)-acetamido]-3-[(8-amino-tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1-sulphone-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1-sulphone-3-acetoxy methyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-(α-methyl-α-carboxy-ethoxyimino)-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxyimino-acetamido]-3-[8-aminocarbonyl-tetrazolo[1,5-b]pyridazin-6-yl-]thiomethyl]-3-cephem-4-carboxylic acid (syn-isomer); and the pharmaceutically and veterinarily acceptable salts and esters thereof.
Claim 11
Dependent Claim
119 words
A compound selected from 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-hydroxy-imino-acetamido]-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-cephem-4-carboxylic acid (syn-isomer); β -[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(R)-sulphoxide-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(S)-sulphoxide-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-chloro-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-hydroxy-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-methoxy-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-acetoxy-methyl-3-cephem-4-carboxylic acid; (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(R)-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(S)-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn-isomer); 7β-[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); 7β-[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); 7β-[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); 7β-[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); 7β-[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); 7β-[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); β -[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); 7β-[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-carboxylic acid (syn isomer); 7β-[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-carboxylic acid (syn isomer); 7β-[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)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetamido]-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetamido]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetamido]-3-[(8-amino-tetrazolo[1,5-b]pyridazin-6-yl) -thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-(β-carboxyvinyleneoxy-imino)-acetamido]-3-[(8-amino-tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1-sulphone-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1-sulphone-3-acetoxy methyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-(α-methyl-α-carboxy-ethoxyimino)-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-hydroxy-4-thiazolinyl)-2-methoxyimino-acetamido]-3-[8-aminocarbonyl-tetrazolo[1,5-b]pyridazin-6-yl-]thiomethyl]-3-cephem-4-carboxylic acid (syn-isomer); and the pharmaceutically and veterinarily acceptable salts and esters thereof.
Claim 12
Dependent Claim
78 words
A compound selected from 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(R)-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(S)-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[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); 7β-[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); 7β-[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); 7β-[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); 7β-[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); 7β-[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); 7β-[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-carboxylic acid (syn-isomer); 7β-[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-carboxylic acid (syn-isomer); β -[2-(2-imino-3-methoxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetamido]-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetamido]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetamido]-3-[(8-amino-tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1-sulphone-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-(α-methyl-α-carboxy-ethoxy-imino)-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[8-aminocarbonyl-tetrazolo[1,5-b]pyridazin-6-ylthiomethyl]-3-cephem-4-carboxylic acid (syn-isomer); and the pharmaceutically and veterinarily acceptable salts and esters thereof.
Claim 13
Dependent Claim
78 words
A compound selected from 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(R)-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(S)-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[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); 7β-[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); 7β-[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); 7β-[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); 7β-[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); 7β-[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); 7β-[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-carboxylic acid (syn-isomer); 7β-[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-carboxylic acid (syn-isomer); β -[2-(2-imino-3-methoxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetamido]-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetamido]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-carboxymethoxy-imino-acetamido]-3-[(8-amino-tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-1-sulphone-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-(α-methyl-α-carboxy-ethoxy-imino)-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-methoxy-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[8-aminocarbonyl-tetrazolo[1,5-b]pyridazin-6-ylthiomethyl]-3-cephem-4-carboxylic acid (syn-isomer); and the pharmaceutically and veterinarily acceptable salts and esters thereof.
Claim 14
Dependent Claim
62 words
A compound selected from 7β-[2-(2-imino-3-amino-4-thiazolinyl)2-methoxy-imino-acetamido]-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(R)-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(S)-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn-isomer); 7β-[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); 7β-[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); β -[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[(tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[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); 7β-[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); 7β-[2-(2-imino-3-amino-4-thiazolinyl)-2-(β-carboxyvinyleneoxy-imino)-acetamido]-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-1-sulphone-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-amino-4-thiazolinyl)-2-(β-methyl-α-carboxyethoxyimino)-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxyimino-acetamido]-3-[8-aminocarbonyl-tetrazolo[1,5-b]pyridazin-6-ylthiomethyl]-3-cephem-4-carboxylic acid (syn-isomer), and the pharmaceutically and veterinarily acceptable salts and esters thereof.
Claim 15
Dependent Claim
62 words
A compound selected from 7β-[2-(2-imino-3-amino-4-thiazolinyl)2-methoxy-imino-acetamido]-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(R)-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-1(S)-sulphoxide-3-acetoxy-methyl-3-cephem-4-carboxylic acid (syn-isomer); 7β-[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); 7β-[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); β -[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-3-[(tetrazolo[1,5-b]pyridazin-6-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[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); 7β-[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); 7β-[2-(2-imino-3-amino-4-thiazolinyl)-2-(β-carboxyvinyleneoxy-imino)-acetamido]-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxy-imino-acetamido]-1-sulphone-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn isomer); 7β-[2-(2-imino-3-amino-4-thiazolinyl)-2-(β-methyl-α-carboxyethoxyimino)-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn-isomer); 7β-[2-(2-imino-3-amino-4-thiazolinyl)-2-methoxyimino-acetamido]-3-[8-aminocarbonyl-tetrazolo[1,5-b]pyridazin-6-ylthiomethyl]-3-cephem-4-carboxylic acid (syn-isomer), and the pharmaceutically and veterinarily acceptable salts and esters thereof.
Claim 16
Dependent Claim
34 words
An anti-bacterial pharmaceutical or veterinary composition containing an effective amount of a compound of any one of claims 5 to 9, or 1 to 4 and a pharmaceutically or veterinarily acceptable carrier or diluent.
Claim 17
Independent Claim
39 words
A method of treating bacterial infection in a patient in need of such treatment, said method comprising administering to said patient an anti-bacterial amount of a compound of any one of claims 5 to 9 or 1 to 4.
References Cited (Backward Citations)
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