GB2083820A - Aminothiazole oxime derivatives - Google Patents

Aminothiazole oxime derivatives Download PDF

Info

Publication number
GB2083820A
GB2083820A GB8131634A GB8131634A GB2083820A GB 2083820 A GB2083820 A GB 2083820A GB 8131634 A GB8131634 A GB 8131634A GB 8131634 A GB8131634 A GB 8131634A GB 2083820 A GB2083820 A GB 2083820A
Authority
GB
United Kingdom
Prior art keywords
ester
syn isomer
formula
ethyl
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
GB8131634A
Other versions
GB2083820B (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fujisawa Pharmaceutical Co Ltd
Original Assignee
Fujisawa Pharmaceutical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd
Publication of GB2083820A publication Critical patent/GB2083820A/en
Application granted granted Critical
Publication of GB2083820B publication Critical patent/GB2083820B/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Compounds of the formula <IMAGE> wherein R<1> is amino or protected amino group and R<2> is cyclopentyl or 3,4-dichlorobenzyl are useful as starting compounds in the synthesis of novel 3,7-di-substituted-3-cephem -4-carboxylic acid antibacterial agents.

Description

SPECIFICATION Aminothiazole oxime derivatives The present invention relates to new compounds having the general formula
wherein R' is amino or protected amino group and R2 is cyclopentyl or 3,4-dichlorobenzyi.
The compounds of the present invention are useful as starting compounds in the synthesis of novel 3,7-disubstituted-3-cephem-4-carboxylic acid antibacterial agents which form the subject of our copending British Patent Application published under the No. 2031411.
Wherein R1, Ria is protected amino and R2 are each as defined above Z is a protected carboxy, and Y is halogen Regarding the compounds of the invention it is to be understood that these compounds include tautomeric isomers relating to their thiazole groups. That is, in case that the group represented by the formula:
(wherein R' is as defined above) in the formula of said object and starting compounds take the formula:
(R' is as defined above), said group of the formula:
can be also alternatively represented by its tautomeric formula:
(wherein Rib is imino or a protected imino).That is, both of the said groups (A) and (B) are in the state of equilibrium as so-called tautomeric forms which can be represented by the following equilibrium:
(wherein R' and Rib are each as defined above).
These types of tautomerism between 2-aminothiazole compounds and 2-iminothiazoline compounds as stated above have been well known in the literature, and it is obvious to a person skilled in the art that both of the tautomeric isomers are equilibrated and easily convertible reciprocally, and accordingly it is to be understood that such isomers are included within the same category of the compound per se. Accordingly, the both of the tautomeric forms of the object compounds and the starting compounds are clearly included within the scope of the present invention. In the present specification and examples, the object and starting compounds including the group of such tautomeric isomers are represented by using one of the expressions therefor, that is the formula:
only for the convenient sake.
Furthermore, it is to be understood that these compounds include the syn isomer, the anti isomer and a mixture thereof. For example, regarding the object compound, the syn-isomer can be represented by the partial structure of the formula:
in its molecule, while the corresponding anti-isomer is represented by the partial structure of the formula:
in its molecule, and in case that it is convenient for the explanation of this invention to express both of the syn isomer and anti-isomer by one general formula, it is represented by the partial structure of the formula:
Suitable protected amino may include an acylamino and amino group substituted by a conventional protective group other than the acyl group such as ar(lower)alkyl (e.g., benzyl and trityl).
Suitable protected imino may include an acylimino and imino group substituted by a conventional protective group other than the acyl group such as ar(lower)alkyl (e.g., benzyl and trityl).
Suitable acyl moiety in the terms "acylamino" and "acylimino" may include carbomyl, aliphatic acyl group and acyl group containing an aromatic or heterocyclic ring. And, suitable examples of the said acyl may be lower alkanoyl (e.g., formyl, acetyl propionyl, butyryl, isobutyryi, valeryl, isovaleryl, oxalyl, succinyl, pivaloyl, etc.), preferably one having 1 to 4 carbon atoms(s), more preferably one having 1 to 2 carbon atom(s); lower alkoxycarbonyl having 2 to 7 carbon atoms (e.g., methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-cyclopropyle thoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, t-butoxycarbonyl,pentyloxycarbonyl, t-pentyloxycarbonyl, hexyloxycarbonyl, etc.); lower alkanesulfonyl (e.g.,mesyl, ethansulfonyl, propanesulfonyl, isopropanesulfonyl, butanesulfonyl,); arenesulfonyl (e.g., benzensulfonyl, tosyl, etc.); aroyl (e.g., benzoyl, toluoyl, naphthoyl, phthaloyl, indancarbonyl); ar(lower)alkanoyl (e.g., phenylacetyl, phenylpropionyl); and ar(lower)alkoxycarbonyl (e.g., benzyloxycarbonyl, phenethyloxycarbonyl).
The acyl moiety as stated above may have 1 to 3 suitable substituent(s) such as halogen (e.g., chlorine, bromine, iodine or fluorine), hydroxy, cyano, nitro, lower alkoxy, (e.g., methoxy, ethoxy, propoxy, isopropoxy), lower alkyl (e.g., methyl, ethyl, propyi, isopropyl, butyl), lower alkenyl (e.g., vinyl, allyl) or aryl (e.g., phenyl, tolyl).
Preferable example of acylamino may be lower alkanoylamino or halo(lower)alkanoylamino(more preferably trihalo(lower)alkanoylamino).
Suitable protected carboxy includes esterified carboxy in which said ester moiety may be the ones such as lower alkyl ester (e.g., methyl ester, ethyl ester, propyl ester, isopropyl ester, butyl ester, isobutyl ester, t-butyl ester, pentyl ester, t-pentyl ester, hexyl ester, 1-cyclo-propylethyl ester), wherein lower alkyl moiety may be preferably one having 1 to 4 carbon atom(s), lower alkenyl ester (e.g., vinyl ester, allyl ester etc.); lower alkynyl ester (e.g., ethynyl ester, propynyl ester, etc.); mono(or di or tri)-halo(lower)alkyl ester (e.g., 2-iodethyl ester, 2,2,2-trichloroethyl ester, etc.); lower alkanoyloxy(lower)alkyl ester (e.g., acetoxymethyl ester, propionyloxymethyl ester, butyryloxymethyl ester, valeryloxymethyl ester, pivaloxymethyl ester, hexanoyloxymethyl ester, 2acetoxymethyl ester, 2-propionyloxyethyl ester, etc.); lower alkanesulfonyl(lower)alkyl ester (e.g., mesylmethyl ester, 2-mesyletheyl ester etc.); ar(lower)alkyl ester, for example, phenyl(lower)alkyl ester which may have one or more suitable substituent(s) (e.g., benzyl ester, 4-methoxybenzyl ester, 4-nitrobenzyl ester, phenethyl ester, trityl ester, diphenylmethyl ester, bis(methoxyphenyl)methyl ester, 3,4-dimethoxybenzyl ester, 4hydroxy-3 ,5-ditertiarybutyl benzyl ester, etc.); aryl ester which may have one or more suitable substituent(s) (e.g., phenyl ester, tolyl ester, tertiary butylphenyl ester, xylyl ester, mesityl ester, cumenyl ester, etc.), and the like. Preferable example of protected carboxy may be lower alkoxycarbonyl(e.g., methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, t-butoxycarbonyl, t-pentyloxycarbonyl, hexyloxycarbonyl, etc.) having 2 to 7 carbon atoms, preferably one having 2 to 5 carbon atoms.
By the term "halogen" we mean one of fluorine, chlorine, bromine and iodine.
EXAMPLE 1 (i) Ethyl 2-cyclopentyloxyimino-3-oxobutyrate (syn isomer) was obtained by reacting ethyl 2hydroxyimino-3-oxobutyrate (syn isomer) with cyclopentyl bromide in a conventional manner.
Ethyl 2-cyclopentyloxyimino-3-oxobutyrate (syn isomer), oil.
I.R. (Film :1740,1670, 1495, 1430 cm-t NMR 1CC14,8): 1.32 (eH, t,J = 7Hz), 1.4-2.2 (8H, m) 2.33 (3H, s), 4.27 (2H, q,J = 7Hz), 4.87 (1H, m) (ii) Sulfuryl chloride was added, all at once to a stirred solution of ethyl 2-cyclopentyloxyimino-3oxobutyrate (syn isomer) in acetic acid at room temperature, and stirred at the same temperature for an hour. After adding the resultant solution to water (200 ml), the solution was extracted with methylene chloride. The extract was washed with a saturated aqueous solution of sodium chloride, neutralized with an aqueous solution of sodium bicarbonate and washed with water.
The solution was dried over magnesium sulfate and concentrated under reduced pressure to give ethyl 2-cyclopentyloxyimino-3-oxo-4-chlorobutyrate (syn isomer), oil l.R. (Film): 1750, 1735, 1465, 1435 cam~1 NMR (CCI4,8): 1.33 (3H, t, J = 7Hz), 1.3-2.4 (8H,m), 4.28 (2H, q, J = 7Hz), 4.46 (2H,s), 4.86 (1H,m).
(iii) A mixture of ethyl 2-cyclopentyloxyimino-3-oxo-4-chlorobutyrate (syn isomer), thiourea, sodium acetate, methanol and water was stirred at 48"C for 40 minutes. After the resultant solution was adjusted to pH 6.5 with an aqueous solution of sodium bicarbonate, the precipitate was collected by filtration and washed with diisopropylether to give ethyl 2-cyclopentyloxyimino2-(2'-aminothiazole-4'-yl)acetate (syn isomer), mp 134-136"C l.R. (NUJOL(Registered Trade Mark) : 3490, 3450, 3250, 3120, 1735, 1540, 1460 cm- N.M.R. (DMSO-d6,6):: 1.25 (3H, t,J = 7Hz), 1.62 (8H, broad s), 4.27 (2H, q,J = 7Hz), 4.70 (1H,m), 6.85 (1 H,s), 7.20(2H,s) (iv) Ethyl 2-cyclopentyloxyimino-2-(2'-aminothiazol-4'-yl)acetate (syn isomer) was added to a mixture of IN sodium hydroxide and ethanol and stirred at room temperature for 5 hours. After removing ethanol from the resultant solution under reduced pressure, the residue was dissolved in water (60 ml) and adjusted to pH 2.0 with 10% hydrochloric acid. The precipitate was collected by filtration and dried to give 2-cyclopentyloxyimino-2-(2'-aminothiazol-4'-yl)acetic acid (syn isomer), mp 186"C (dec.).
I.R. (NUJOL) : 3330, 3120,1635,1450 cm-' N.M.R. (DMSO-d6,8): 1.1-2.2 (8H, m), 4.68 (1H,m), 6.81 (1H,s), 7.18 (2H,broad s).
(v) Trifluoroacetic acid was added to acetic anhydride under ice-cooling, and the mixture was stirred for 1 hour at 50"C and then cooled to 20"C. To this mixture was added 2cyclopentyloxyimino-2(2-aminothiazol-4'-yl)acetic acid (syn isomer), and the mixture was stirred for 3 hours at ambient temperature. To the mixture was added diisopropyl ether (400 ml) and then the precipitated crystals were collected by filtration, washed with diisopropyl ether and then dried to give 2-cyclopentyloxyimino-2-(2'-trifluoroacetamido thiazol-4'-yl)acetic acid (syn isomer I.R. (NUJOL) : 3200, 3130, 1720, 1590, 1580 cm-1 NMR(DMSO-d6,8): 1.34-2.22(8H,m),4.81(1 H,m), 7.71(1 H,s).
EXAMPLE 2 (i) Ethyl 2-(3", 4"-dichlorobenzyloxyimino)-3-oxobutyrate (syn isomer) was obtained by reacting ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer) with 3,4-diclorobenzyl chloride in a conven fional manner.
Ethyl 2-(3",4"-dichlorobenzyloxyimino)-3-oxobutyrate (syn isomer), oil.
I.R. (Film) 1730, 1690, 1600, 1470, 1400, 1370, 1310, 1240, 1130, 1080, 1010 cm - N.M.R. (CCI4,S): 1.30 (3H,t,J = 6Hz), 2.30 (3H,s), 4.30 (2H,q,J = 6Hz), 4.47(2H,s), 7.00-7.53(3H,m) (ii) Ethyl 2-(3",4"-dichlorobenzyloxyimino)-3-oxo-4-chlorobutyrate (syn isomer), oil, was prepared in a similar manner to that described above in Example 1 (ii) I.R. (Film) 1740, 1710, 1590, 1470, 1400, 1370, 1320, 1260, 1200, 1130, 1010 cm - NMR (CCI4,6):1.37(3H,t,J = 6Hz),4.23(2H,q,J = 6HZ),4.43(2H,s),5.27(2H, s),7.10-7.60(3H,m).
(iii) Ethyl 2-(3",4"-dichlorobenzyloxyimino)-2-(2'-aminothiazol-4'-yl)acetate (syn isomer)was prepared in a manner similar to that described in Example 1 (iii).
I.R. (NUJOL): 3460,1720,1600,1540,1460,1390,1260,1180,1020,1010,,880, 810 cm - NMR (DMSO-d6,8): 1.25(3H,t,J = 7Hz),4.30 (2H,q,J = 7Hz),5.17 (2H,s), 6.93 (1H,s), 7.27-7.73(3H,m).
(iv) 2-(3",4"-dichlorobenzyíoxyimino)-2-(2'-aminothiazol-4'-yl)acetic acid (syn isomer) was obtained in a manner similar to that as described in Example 1 (iv).
I.R. (NUJOL) 3430, 1660, 1590, 1400, 1010cm NMR (DMsO-d6,8): 5.23 (2H,s), 6.93(1H,s) 7.30-7.77 (3H,m).
(v) 2-(3",4"-dichlorobenzyloxyimino)-2-(2'-trifluoro-acetamidothiazol-4'-yl)acetic acid(syn isomer) was prepared in a manner similar to that described in Example 1 (v) above.
I.R. (NUJOL) : 1720,1580,1300,1260, 1200, 1160, 1150cm-'.
NMR(DMSO-d6,8): 5.40(2H,s), 7.47-7.93(4H,m)

Claims (2)

1. A compound of the formula
wherein R1 is amino or protected amino group and R2 is cyclopentyl or 3,4-dichlorobenzyl
2. A process for preparing a compound of the formula:
wherein R1a is a protected amino and R2 is cyclopentyl or 3,4-dichlorobenzyl or salts thereof which process comprises reacting a compound of the formula
wherein R2 is as defined above or salts thereof with an amino-protecting agent.
GB8131634A 1978-08-31 1979-08-28 Aminothiazole oxime derivatives Expired GB2083820B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB7835195 1978-08-31

Publications (2)

Publication Number Publication Date
GB2083820A true GB2083820A (en) 1982-03-31
GB2083820B GB2083820B (en) 1983-02-16

Family

ID=10499378

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8131634A Expired GB2083820B (en) 1978-08-31 1979-08-28 Aminothiazole oxime derivatives

Country Status (9)

Country Link
JP (1) JPS5533500A (en)
BE (1) BE878433A (en)
CH (1) CH642663A5 (en)
DE (1) DE2934682A1 (en)
ES (3) ES483676A1 (en)
FR (1) FR2434812A1 (en)
GB (1) GB2083820B (en)
NL (1) NL7906497A (en)
SE (1) SE7907159L (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0075805A1 (en) * 1981-09-18 1983-04-06 Kyowa Hakko Kogyo Co., Ltd Beta-lactam compound and a pharmaceutical composition containing the same

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5585594A (en) * 1978-11-13 1980-06-27 Fujisawa Pharmaceut Co Ltd Cephem compound and their preparation
DE2945248A1 (en) * 1978-11-13 1980-05-22 Fujisawa Pharmaceutical Co CEPHEM COMPOUNDS, METHOD FOR THEIR PRODUCTION AND ANTIBACTERIAL PHARMACEUTICAL AGENTS CONTAINING THE SAME
JPS6011917B2 (en) * 1981-04-09 1985-03-28 山之内製薬株式会社 Novel cephalosporin compounds
JPS58986A (en) * 1981-05-07 1983-01-06 Fujisawa Pharmaceut Co Ltd 7-acylamino-3-vinylcephalosporanic acid derivative and its preparation
JPS58135894A (en) * 1982-01-22 1983-08-12 Fujisawa Pharmaceut Co Ltd 7-acylamino-3-vinylcephalosporanic acid derivative and its preparation
JPS5973610A (en) * 1982-10-20 1984-04-25 Tokico Ltd Hydraulic shock absorber
GB8432295D0 (en) * 1984-12-20 1985-01-30 Fujisawa Pharmaceutical Co Cephem compounds

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK159154C (en) * 1975-02-24 1991-02-11 Takeda Chemical Industries Ltd PROCEDURE FOR THE PRODUCTION OF CEPHALOSPORIN DERIVATIVES OR SALTS THEREOF
GB1576625A (en) * 1976-04-12 1980-10-08 Fujisawa Pharmaceutical Co Syn isomer 3,7 disubstituted 3 cephem 4 carboxylic acid compounds and processes for the preparation thereof
GR63088B (en) * 1976-04-14 1979-08-09 Takeda Chemical Industries Ltd Preparation process of novel cephalosporins
FR2381053A1 (en) * 1977-02-18 1978-09-15 Roussel Uclaf NEW OXIMES DERIVED FROM 3-THIADIAZOLYL THIOMETHYL 7-AMINOTHIAZOLYL ACETAMIDO CEPHALOSPORANIC, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICINAL PRODUCTS
PH17188A (en) * 1977-03-14 1984-06-14 Fujisawa Pharmaceutical Co New cephem and cepham compounds and their pharmaceutical compositions and method of use
DE2716677C2 (en) * 1977-04-15 1985-10-10 Hoechst Ag, 6230 Frankfurt Cephem derivatives and processes for their preparation
DE2714880A1 (en) * 1977-04-02 1978-10-26 Hoechst Ag CEPHEMDER DERIVATIVES AND PROCESS FOR THEIR PRODUCTION
FR2387235A1 (en) * 1978-01-23 1978-11-10 Fujisawa Pharmaceutical Co PROCESS FOR THE PREPARATION OF COMPOUNDS OF 3,7-DISUBSTITUE-3-CEPHEM-4-CARBOXYLIC ACID AND NEW PRODUCTS THUS OBTAINED, HAVING A STRONG ANTIBACTERIAL ACTIVITY
DE2804040C3 (en) * 1978-01-31 1981-03-19 Hoechst Ag, 6000 Frankfurt Process for the preparation of cephem compounds
SE7901262L (en) * 1978-02-15 1979-08-16 Fujisawa Pharmaceutical Co 3,7-DISUBSTITUTED 3-CEFEM-4-CARBOXYLIC ACID COMPOUNDS AND PROCEDURES FOR THEIR PREPARATION
US4341775A (en) * 1978-09-11 1982-07-27 Fujisawa Pharmaceutical Co., Ltd. Cephem compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0075805A1 (en) * 1981-09-18 1983-04-06 Kyowa Hakko Kogyo Co., Ltd Beta-lactam compound and a pharmaceutical composition containing the same

Also Published As

Publication number Publication date
CH642663A5 (en) 1984-04-30
JPS5533500A (en) 1980-03-08
ES483676A1 (en) 1980-09-01
SE7907159L (en) 1980-03-01
FR2434812B1 (en) 1983-05-13
ES490891A0 (en) 1980-12-16
JPS6361954B2 (en) 1988-11-30
NL7906497A (en) 1980-03-04
GB2083820B (en) 1983-02-16
ES8102143A1 (en) 1980-12-16
DE2934682A1 (en) 1980-03-13
ES490890A0 (en) 1980-12-16
FR2434812A1 (en) 1980-03-28
BE878433A (en) 1980-02-25
ES8102109A1 (en) 1980-12-16

Similar Documents

Publication Publication Date Title
CA1128957A (en) .alpha.-PROTECTED OXYIMINO-.beta.-OXO-.gamma.-HALOGENOBUTYRIC ACID DERIVATIVES
US4877873A (en) Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof
EP0191507B1 (en) New 2-oxyimino-3-oxobutyric acid derivatives and process for preparation thereof
SE456909B (en) NEW 2- (2-EV SUB AMINO-TIAZOL-4-YL) 2-IMINO-ACETIC ACID DERIVATIVES FOR USE AS INTERMEDIATE IN THE PREPARATION OF 7-SUBSTITUTED-3-CEFEM-4-CARBOXYL ACID
CA1175416A (en) Process for preparing 7-/(2-aryl) 2- hydroxyimino acetamido/cephalosporanic acid derivatives
HU177441B (en) Process for preparing syn isomers of 3,7-disubstituted 3-cephem-4-carboxylic acid derivatives
HU183009B (en) Process for producing 2-oximino-acetic acid derivatives substituted with thiazolyl-4-ring at the 2 position
US4411898A (en) 7-[2-Oxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1-carboxyalkyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid compounds
CA1224784A (en) Amide derivatives of 2-oxo-1-azetidinesulphonic acids
CA1276929C (en) Cephalosporin antibacterial agents
EP0008442B1 (en) 2-lower alkyl-7-substituted-2 or 3-cephem-4-carboxylic acid compounds, processes for their preparation and pharmaceutical compositions containing them
GB2083820A (en) Aminothiazole oxime derivatives
GB2110688A (en) A process for preparing 3-alkoxymethylcephalosporin derivatives
US3962272A (en) 1h-tetrazole-1-acetate esters and acids and process therefor
CA1225391A (en) Process for producing a cephalosporin, an intermediate for the cephalosporin and a process for producing the intermediate
US4331664A (en) Syn isomer of 7-[2-cyclo(lower) alkoxyimino-2-(2-amino-or substituted aminothiazol-4-yl)acetamido]-3-lower alkanoyloxymethyl or heterocyclicthiomethyl-3-cephem-4-carboxylic acid compounds
GB2033390A (en) Process for the Preparation of 7-aminothiazolylacetamido- cephalosporanic Acid Derivatives
US4804752A (en) Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof
US5079369A (en) Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof
US4871860A (en) Syn-isomer of 3,7-disubstituted-3-cephem-4-caroxylic acid compounds and processes for the preparation thereof
FR2528839A1 (en) NOVEL PROCESS FOR THE PRODUCTION OF 2- (2-AMINOTHIAZOL-4-YL) GLYOXYLIC ACID DERIVATIVES OR ONE OF ITS SALTS, THE INTERMEDIATES NECESSARY FOR THE SYNTHESIS THEREOF, AND THE PROCESS FOR THE PRODUCTION OF SAID INTERMEDIATES
US5631378A (en) Protected aminothiazolylacetic acid derivatives
GB2104505A (en) Thiazolyloxime carboxylic acids
KR900003407B1 (en) Silyl compound and preparation method thereof
US4431643A (en) Syn-isomer of 3-substituted-7-[2-cyclopentyloxyimino-2-(2-aminothiazol-4-yl)-acetamido]-3

Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19950828