FR2399418A1 - Heterocyclyl-imino-acetamido-cephalosporin derivs. - Google Patents

Heterocyclyl-imino-acetamido-cephalosporin derivs.

Info

Publication number
FR2399418A1
FR2399418A1 FR7830108A FR7830108A FR2399418A1 FR 2399418 A1 FR2399418 A1 FR 2399418A1 FR 7830108 A FR7830108 A FR 7830108A FR 7830108 A FR7830108 A FR 7830108A FR 2399418 A1 FR2399418 A1 FR 2399418A1
Authority
FR
France
Prior art keywords
lower alkyl
haloacetyl
halo
opt
cooh
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
FR7830108A
Other languages
French (fr)
Other versions
FR2399418B1 (en
Inventor
Takao Takaya
Hisashi Takasugi
Kiyoshi Tsuji
Toshiyuki Chiba
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
Priority claimed from GB10699/77A external-priority patent/GB1600735A/en
Priority claimed from FR7807360A external-priority patent/FR2383951A1/en
Priority claimed from KR7802782A external-priority patent/KR820001285B1/en
Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd
Priority to FR7830108A priority Critical patent/FR2399418A1/en
Publication of FR2399418A1 publication Critical patent/FR2399418A1/en
Priority claimed from KR1019820000231A external-priority patent/KR830000455B1/en
Application granted granted Critical
Publication of FR2399418B1 publication Critical patent/FR2399418B1/fr
Granted 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
    • 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
    • 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
    • C07D277/32—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 hetero atoms or with 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
    • C07D277/38—Nitrogen atoms
    • C07D277/40—Unsubstituted amino or imino radicals
    • 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
    • C07D277/32—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 hetero atoms or with 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
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • C07D277/32—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 hetero atoms or with 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Cephalosporins of formula (I), and their pharmaceutically acceptable salts and bio-precursors are new:- (R1=thiadiazolyl, 2-R6-thiazoyl (R6=opt. protected amino) or haloacetyl. A is CH2 or -C(=N is approx.OR2). R2=H or aliphatic hydrocarbyl opt. substd. by halo, COOH or esterified COOH. R3=H or lower alkyl. R4=H, halo, lower alkyl or OR7.R7=H, lower alkyl or acyl. R5=opt. modified COOH. The dotted line is a single or double bond).- R4 is not lower alkyl, when R3 is H; R4 is lower alkyl when R3 is lower alkyl; A is not CH2 unless R1 is haloacetyl; DELTA 3 is present and R4 is H, halo, lower alkyl, or lower alkoxy, when R1 is haloacetyl. When R2=ethyl, isopropyl or allyl, R'6 is amino or non-substd. alkanamido, and R8 is H.- (I) where A is -C(=N is approx. Or2) and R1 i heterocyclic are antibacterials for therapeutic or prophylactic treatment of human or animal infections; the syn isomers are the more active. The other (I) are intermediates. The cpd. syn-7- 2-(2-amino-4-thiazolyl)-2-methoxyi minoacetamido -3-cephem-- 4-carboxylic acid has sub-cutaneous LD50
FR7830108A 1977-03-14 1978-10-23 Heterocyclyl-imino-acetamido-cephalosporin derivs. Granted FR2399418A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7830108A FR2399418A1 (en) 1977-03-14 1978-10-23 Heterocyclyl-imino-acetamido-cephalosporin derivs.

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
GB10699/77A GB1600735A (en) 1977-03-14 1977-03-14 Cephem and cephem compounds and processes for preparation thereof
GB2924577 1977-07-12
GB4231577 1977-10-11
GB7578 1978-01-03
FR7807360A FR2383951A1 (en) 1977-03-14 1978-03-14 PROCESS FOR PREPARING 7-SUBSTITUE-3-CEPHEM (OR CEPHAM) -4-CARBOXYLIC ACIDS, THEIR SALTS AND THEIR BIOPRECURSORS, AND NEW PRODUCTS THUS OBTAINED, WITH ANTIMICROBIAL ACTIVITY
KR7802782A KR820001285B1 (en) 1977-03-14 1978-09-13 Process for preparing cephem compounds
FR7830108A FR2399418A1 (en) 1977-03-14 1978-10-23 Heterocyclyl-imino-acetamido-cephalosporin derivs.
KR1019820000231A KR830000455B1 (en) 1977-03-14 1982-01-18 Process for preparing cefem compound

Publications (2)

Publication Number Publication Date
FR2399418A1 true FR2399418A1 (en) 1979-03-02
FR2399418B1 FR2399418B1 (en) 1983-02-18

Family

ID=27571085

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7830108A Granted FR2399418A1 (en) 1977-03-14 1978-10-23 Heterocyclyl-imino-acetamido-cephalosporin derivs.

Country Status (1)

Country Link
FR (1) FR2399418A1 (en)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2346014A1 (en) * 1976-01-23 1977-10-28 Roussel Uclaf Amino-thiazolyl-hydroxyimino-acetamido-cephalosporanic acids - with antibacterial activity
FR2348219A1 (en) * 1976-04-12 1977-11-10 Fujisawa Pharmaceutical Co PROCESS FOR PREPARING SYN ISOMERS OF 3,7-CEPHEM-4-CARBOXYLIC 3,7-DISUBSTITUTED ACID COMPOUNDS AND NEW PRODUCTS THUS OBTAINED, WITH ANTIBACTERIAL ACTIVITY
FR2381051A1 (en) * 1977-02-17 1978-09-15 Takeda Chemical Industries Ltd CEPHALOSPORANIC ACID DERIVATIVES AND THEIR PREPARATION PROCESS
FR2383951A1 (en) * 1977-03-14 1978-10-13 Fujisawa Pharmaceutical Co PROCESS FOR PREPARING 7-SUBSTITUE-3-CEPHEM (OR CEPHAM) -4-CARBOXYLIC ACIDS, THEIR SALTS AND THEIR BIOPRECURSORS, AND NEW PRODUCTS THUS OBTAINED, WITH ANTIMICROBIAL ACTIVITY
FR2384782A1 (en) * 1977-03-25 1978-10-20 Roussel Uclaf 7-Amino-thiazolyl-acetamido-cephalosporin oxime derivs. - are broad spectrum antibacterials useful against penicillin resistant Staphylococci (BE 25.9.78)
FR2385722A1 (en) * 1977-04-02 1978-10-27 Hoechst Ag NEW CEPHALOSPORIN DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR THERAPEUTIC APPLICATION
FR2390442A1 (en) * 1977-05-13 1978-12-08 Roussel Uclaf Amino-thiazolyl hydroxy-imino acetic acid derivs. - intermediates for bactericidal cephalosporanic acid derivs.
FR2408613A2 (en) * 1977-07-19 1979-06-08 Roussel Uclaf NEW OXIMES DERIVED FROM 7-AMINO THIAZOLYL ACETAMIDO CEPHALOSPORANIC ACID, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICINAL PRODUCTS

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2346014A1 (en) * 1976-01-23 1977-10-28 Roussel Uclaf Amino-thiazolyl-hydroxyimino-acetamido-cephalosporanic acids - with antibacterial activity
FR2348219A1 (en) * 1976-04-12 1977-11-10 Fujisawa Pharmaceutical Co PROCESS FOR PREPARING SYN ISOMERS OF 3,7-CEPHEM-4-CARBOXYLIC 3,7-DISUBSTITUTED ACID COMPOUNDS AND NEW PRODUCTS THUS OBTAINED, WITH ANTIBACTERIAL ACTIVITY
FR2381051A1 (en) * 1977-02-17 1978-09-15 Takeda Chemical Industries Ltd CEPHALOSPORANIC ACID DERIVATIVES AND THEIR PREPARATION PROCESS
FR2383951A1 (en) * 1977-03-14 1978-10-13 Fujisawa Pharmaceutical Co PROCESS FOR PREPARING 7-SUBSTITUE-3-CEPHEM (OR CEPHAM) -4-CARBOXYLIC ACIDS, THEIR SALTS AND THEIR BIOPRECURSORS, AND NEW PRODUCTS THUS OBTAINED, WITH ANTIMICROBIAL ACTIVITY
FR2384782A1 (en) * 1977-03-25 1978-10-20 Roussel Uclaf 7-Amino-thiazolyl-acetamido-cephalosporin oxime derivs. - are broad spectrum antibacterials useful against penicillin resistant Staphylococci (BE 25.9.78)
FR2385722A1 (en) * 1977-04-02 1978-10-27 Hoechst Ag NEW CEPHALOSPORIN DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR THERAPEUTIC APPLICATION
FR2390442A1 (en) * 1977-05-13 1978-12-08 Roussel Uclaf Amino-thiazolyl hydroxy-imino acetic acid derivs. - intermediates for bactericidal cephalosporanic acid derivs.
FR2408613A2 (en) * 1977-07-19 1979-06-08 Roussel Uclaf NEW OXIMES DERIVED FROM 7-AMINO THIAZOLYL ACETAMIDO CEPHALOSPORANIC ACID, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICINAL PRODUCTS

Also Published As

Publication number Publication date
FR2399418B1 (en) 1983-02-18

Similar Documents

Publication Publication Date Title
NO159017C (en) ANALOGUE PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE 1,2,3,4-TETRAHYDROISOKINOLIN-3-CARBOXYLIC ACID DERIVATIVES.
ES485188A1 (en) Diphenylbutyl-piperzinecarboxamides
GR3032220T3 (en) Use of 2-(N-(2-aminoethyl)amino)acetic acid derivatives for the treatment of diseases which are mediated by non-enzymatical glycosylation
NO911041D0 (en) PROCEDURE FOR THE PREPARATION OF 3-TETRAZOLYLTYOMETHYL-CEPHALOSPORIN ANTIBIOTICS.
HUT63615A (en) Process for producing new imidazole derivatives and pharmaceutical compositions comprising same as active ingredient
FR2358384A1 (en) PSYCHOPHARMACOLOGICALLY ACTIVE PEPTIDES AND DERIVATIVES FROM THESE PEPTIDES
FR2399418A1 (en) Heterocyclyl-imino-acetamido-cephalosporin derivs.
IT1192174B (en) Heterocyclyl-imino-acetamido-cephalosporin derivs. - useful as antibacterials and their precursors
GR871549B (en) Amino acid derivative anticonvulsant
ES8502118A1 (en) Penicillin derivatives and process for preparation of the same.
ATE131055T1 (en) TREATMENT OF COGNITIVE DISORDERS.
ES483676A1 (en) Aminothiazole oxime derivatives
IL129088A0 (en) Subepithelial turbidity inhibitor
ES2001031A6 (en) 6-Beta-(alpha-etherified oxyimino)-acylamino penicillanic-acid derivatives, their preparation and use.
ES2062340T3 (en) DERIVATIVES OF 2-CARBAPENEMO ANTIBACTERIALS.
ES8101076A1 (en) Novel penicillins
ZA961795B (en) Pharmaceuticals
GB2011887A (en) Antiallergic agent
AU2013888A (en) Uricosuric composition
DK0674645T3 (en) Cephem compounds with antimicrobial action
NL7205885A (en) Benzocyclobutenyl-cephalosporins - useful as antibiotics
FI962714A (en) Process for the preparation of therapeutically useful naphthyridine derivatives