JPS5598189A - Syn-isomer of 3, 7-di-substituted-3-cephem-4-carboxylic acid compound, its salt, and their preparation - Google Patents

Syn-isomer of 3, 7-di-substituted-3-cephem-4-carboxylic acid compound, its salt, and their preparation

Info

Publication number
JPS5598189A
JPS5598189A JP15697479A JP15697479A JPS5598189A JP S5598189 A JPS5598189 A JP S5598189A JP 15697479 A JP15697479 A JP 15697479A JP 15697479 A JP15697479 A JP 15697479A JP S5598189 A JPS5598189 A JP S5598189A
Authority
JP
Japan
Prior art keywords
formula
group
isomer
syn
salt
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
JP15697479A
Other languages
Japanese (ja)
Other versions
JPS6141516B2 (en
Inventor
Takao Takatani
Takashi Masugi
Hisashi Takasugi
Hiromu Kawachi
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 JPS5598189A publication Critical patent/JPS5598189A/en
Publication of JPS6141516B2 publication Critical patent/JPS6141516B2/ja
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
    • 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
    • C07D277/32—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
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms

Abstract

NEW MATERIAL:The title compound of formula I {R1 is formula II (R5 is H, halogen, nitro, OH, alkoxy group, etc.; R6 is OH, alkoxy, acyloxy group, etc.), formula III (R7 is amino, OH, alkyl group, etc.), formula IV [R8 is alkyl group; R9 is (protected) imino, or oxo group]; R2 is alkyl group; R3 is (protected) carboxy group; R4 is acyloxymethyl group, etc.}.
EXAMPLE: 7-[ 2-Methoxyimino-2-( 2-amino-1,3-thiazol-4-yl )acetamide ]cephalosporanic acid (syn-isomer).
USE: Antibacterials having greater activities than the anti-isomer.
PROCESS: A compound of formula V or its reactive derivative at the amino group or their salt is reacted with a substituted acetic acid of formula VI to give the compound of formula I.
COPYRIGHT: (C)1980,JPO&Japio
JP15697479A 1976-04-12 1979-12-03 Syn-isomer of 3, 7-di-substituted-3-cephem-4-carboxylic acid compound, its salt, and their preparation Granted JPS5598189A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB14916/76A GB1576625A (en) 1976-04-12 1976-04-12 Syn isomer 3,7 disubstituted 3 cephem 4 carboxylic acid compounds and processes for the preparation thereof
GB2349076 1976-06-07

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
JP51125826A Division JPS5941995B2 (en) 1976-04-02 1976-10-19 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and salts thereof and methods for producing them

Publications (2)

Publication Number Publication Date
JPS5598189A true JPS5598189A (en) 1980-07-25
JPS6141516B2 JPS6141516B2 (en) 1986-09-16

Family

ID=26250890

Family Applications (6)

Application Number Title Priority Date Filing Date
JP51125826A Expired JPS5941995B2 (en) 1976-04-02 1976-10-19 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and salts thereof and methods for producing them
JP8249077A Granted JPS5368796A (en) 1976-04-12 1977-07-08 Syn-isomer of 3,7-disubstd.-3-cephem-4-carboxylic acids, and their preventingor treating agents containing their salts as active constituent againstdiseases caused by bacterial infection
JP8248977A Pending JPS5368795A (en) 1976-04-12 1977-07-08 Syn-isomer of 7-substd.-3-methyl-3-cephem-4-carboxylic acids, their salts,and their preparation
JP15697479A Granted JPS5598189A (en) 1976-04-12 1979-12-03 Syn-isomer of 3, 7-di-substituted-3-cephem-4-carboxylic acid compound, its salt, and their preparation
JP58128676A Granted JPS5962597A (en) 1976-04-12 1983-07-13 Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compound, its salt and their preparation
JP2261173A Expired - Lifetime JPH0684338B2 (en) 1976-04-12 1990-09-28 Substituted acetic acid derivative

Family Applications Before (3)

Application Number Title Priority Date Filing Date
JP51125826A Expired JPS5941995B2 (en) 1976-04-02 1976-10-19 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and salts thereof and methods for producing them
JP8249077A Granted JPS5368796A (en) 1976-04-12 1977-07-08 Syn-isomer of 3,7-disubstd.-3-cephem-4-carboxylic acids, and their preventingor treating agents containing their salts as active constituent againstdiseases caused by bacterial infection
JP8248977A Pending JPS5368795A (en) 1976-04-12 1977-07-08 Syn-isomer of 7-substd.-3-methyl-3-cephem-4-carboxylic acids, their salts,and their preparation

Family Applications After (2)

Application Number Title Priority Date Filing Date
JP58128676A Granted JPS5962597A (en) 1976-04-12 1983-07-13 Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compound, its salt and their preparation
JP2261173A Expired - Lifetime JPH0684338B2 (en) 1976-04-12 1990-09-28 Substituted acetic acid derivative

Country Status (3)

Country Link
JP (6) JPS5941995B2 (en)
GB (1) GB1576625A (en)
HU (1) HU183009B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1984002703A1 (en) * 1983-01-07 1984-07-19 Takeda Chemical Industries Ltd Process for preparing aminothiazolylacetic acid derivatives
WO1984004305A1 (en) * 1983-05-02 1984-11-08 Takeda Chemical Industries Ltd Process for preparing aminothiazoleacetic acid derivatives
US4695639A (en) * 1983-01-07 1987-09-22 Takeda Chemical Industries, Ltd. Thiazole derivatives

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE878514A (en) * 1978-09-04 1980-02-29 Fujisawa Pharmaceutical Co PROCESS FOR THE PREPARATION OF 3-CEPHEM-4-CARBOXYLIC ACID COMPOUNDS WITH DISUBSTITUTION IN POSITIONS 3 AND 7, NOVEL PRODUCTS THUS OBTAINED AND THEIR USE FOR THEIR ANTIBACTERIAL ACTIVITY
BE878433A (en) * 1978-08-31 1980-02-25 Fujisawa Pharmaceutical Co PROCESS FOR THE PREPARATION OF 3-CEPHEM-4-CARBOXYLIC ACID DERIVATIVES 3,7-DISUBSTITUTED, NOVEL PRODUCTS THUS OBTAINED AND THEIR USE FOR THEIR ANTIBACTERIAL ACTIVITY
SE439312B (en) * 1977-03-25 1985-06-10 Roussel Uclaf SET TO MAKE NEW OXIME DERIVATIVES OF 3-ACETOXIMETHYL-7-AMINOTIAZOLYLACETAMIDO CEPHALOSPORANIC ACID
DE2714880A1 (en) * 1977-04-02 1978-10-26 Hoechst Ag CEPHEMDER DERIVATIVES AND PROCESS FOR THEIR PRODUCTION
NL7805715A (en) * 1977-06-03 1978-12-05 Hoffmann La Roche METHOD FOR PREPARING ACYL DERIVATIVES.
FR2410655A1 (en) * 1977-12-05 1979-06-29 Roussel Uclaf NEW OXIMES DERIVED FROM 3-SUBSTITUTE 7-AMINO THIAZOLYL ACETAMIDO CEPHALOSPORANIC, THEIR METHOD OF PREPARATION AND THEIR APPLICATION AS MEDICINAL PRODUCTS
JPS5498795A (en) * 1978-01-13 1979-08-03 Takeda Chem Ind Ltd Cephalosporin derivative and its preparation
JPS54128594A (en) * 1978-03-27 1979-10-05 Fujisawa Pharmaceut Co Ltd 3,7-disubstituted-3-cephem-4-carboxylic acid derivative
FR2432521A1 (en) * 1978-03-31 1980-02-29 Roussel Uclaf NOVEL O-SUBSTITUTED OXIMES DERIVED FROM 7-AMINO THIAZOLYL ACETAMIDO CEPHALOSPORANIC ACID, THEIR PREPARATION PROCESS AND THEIR USE AS MEDICAMENTS
FR2421907A1 (en) * 1978-04-07 1979-11-02 Roussel Uclaf NEW CEPHALOSPORINS DERIVED FROM 7- / 2- (2-AMINO 4-THIAZOLYL) 2- (CARBOXYMETHOXYIMINO / ACETAMIDO 3-SUBSTITUTE CEPHALOSPORANIC ACID, THEIR METHOD OF PREPARATION AND THEIR APPLICATION AS MEDICINAL PRODUCTS
GB1604722A (en) * 1978-05-26 1981-12-16 Glaxo Operations Ltd 7-(2-(2-amino-4-thiozolyl)-2-oxymino-acetamido)-cephem derivatives
GB1604723A (en) * 1978-05-26 1981-12-16 Glaxo Operations Ltd 7-(2-aminothiazol-4-yl)-2-oxyimino-acetamido)-cephem derivatives
ATE15897T1 (en) * 1978-07-17 1985-10-15 Fujisawa Pharmaceutical Co STARTING PRODUCTS FOR THE MANUFACTURE OF CEPHALOSPORINS AND PROCESS FOR THEIR MANUFACTURE.
US4703046A (en) * 1978-09-08 1987-10-27 Fujisawa Pharmaceutical Co., Ltd. Cephem compounds and processes for preparation thereof
BE878637A (en) * 1978-09-11 1980-03-06 Fujisawa Pharmaceutical Co PROCESS FOR THE PREPARATION OF 3,7-DISUBSTITUTED 3-CEPHEM-4-CARBOXYLIC ACID COMPOUNDS AND THEIR PHARMACEUTICALLY ACCEPTABLE SALTS, NOVEL PRODUCTS THUS OBTAINED AND THEIR USE FOR THEIR ANTIMICROBIAL ACTIVITIES
JPH02111750A (en) * 1978-09-12 1990-04-24 Fujisawa Pharmaceut Co Ltd Butyric acid derivative
JPS5585594A (en) * 1978-11-13 1980-06-27 Fujisawa Pharmaceut Co Ltd Cephem compound and their preparation
JPS5579393A (en) * 1978-12-11 1980-06-14 Takeda Chem Ind Ltd Cephalosporin derivative and its preparation
JPS5616490A (en) * 1979-07-18 1981-02-17 Hoechst Ag Cephem compound manufacture
IL61458A0 (en) * 1979-12-07 1980-12-31 Erba Farmitalia N-substituted thiazolyl derivatives of oximino-substituted cephalosporins, their preparation and pharmalceutical compositions containing them
EP0037380B1 (en) * 1980-03-28 1984-09-12 BIOCHEMIE Gesellschaft m.b.H. New process for the production of cephalosporin antibiotics, and novel intermediates used in such process and their production
IL63207A (en) * 1980-07-24 1985-09-29 Lonza Ag Process for the preparation of 2-(2-aminothiazole-4-yl)-2-(syn)-methoxyiminoacetic acid esters
JPS57154175A (en) * 1981-03-16 1982-09-22 Mitsui Toatsu Chem Inc 2-thiazoleamine derivative, its preparation, and drug composition comprising it
JPS57157594U (en) * 1981-03-31 1982-10-04
GB8318846D0 (en) * 1983-07-12 1983-08-10 Fujisawa Pharmaceutical Co Prophylactic/therapeutic agent against fish diseases
JPS60142987A (en) * 1983-12-29 1985-07-29 Mochida Pharmaceut Co Ltd Cephalosporin derivative
DE150507T1 (en) * 1983-12-29 1987-02-26 Mochida Pharmaceutical Co., Ltd., Tokio/Tokyo, Jp CEPHALOSPORINE COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL PREPARATIONS.
JPS60178891A (en) * 1984-02-24 1985-09-12 Kureha Chem Ind Co Ltd Cephalosporin derivative, preparation thereof and medicine containing said derivative
JPS60155167A (en) * 1984-07-31 1985-08-15 Fujisawa Pharmaceut Co Ltd Substituted iminoacetic acid derivative and its salt
US4840945A (en) * 1985-04-01 1989-06-20 Mochida Pharmaceutical Co., Ltd. Cephalosporin derivatives
AU579469B2 (en) * 1985-05-30 1988-11-24 Shionogi & Co., Ltd. A process for preparing hydroxymethylcephem compounds
JPS6236386A (en) * 1985-08-09 1987-02-17 Kureha Chem Ind Co Ltd Cephalosporin derivative, production thereof and drug containing said derivative
JPS6332235A (en) * 1986-07-25 1988-02-10 アトラス・エア・（オ−ストラリア）・ピ−テイ−ワイ・リミテツド Zone air-conditioning method and device
JPS63132893A (en) * 1986-11-25 1988-06-04 Mochida Pharmaceut Co Ltd Novel cephalosporin derivative, production thereof and antibacterial agent containing said derivative as active ingredient
US4880798A (en) * 1986-11-25 1989-11-14 Mochida Pharmaceutical Co., Ltd. Cephalosporin derivatives
US5189157A (en) * 1987-06-16 1993-02-23 Hoffmann La Roche Inc. Antibacterial cephalosporin compounds
CA2216259A1 (en) * 1996-09-25 1998-03-25 Eisai Chemical Co., Ltd. Production process of cephem compound
CN112480024A (en) * 2020-12-11 2021-03-12 山东金城医药化工有限公司 Method for producing trans isomer of aminothiazoly loximate

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1453049A (en) * 1973-08-21 1976-10-20 Glaxo Lab Ltd Cephalosporing antibiotics
GB1445979A (en) * 1972-10-25 1976-08-11 Glaxo Lab Ltd Cephalosporin derivatives
JPS4849789A (en) * 1971-10-25 1973-07-13
JPS50111093A (en) * 1974-02-20 1975-09-01
GB1536281A (en) * 1975-06-09 1978-12-20 Takeda Chemical Industries Ltd Cephem compounds
SE440655B (en) * 1976-01-23 1985-08-12 Roussel Uclaf SET TO MAKE NEW OXIME DERIVATIVES OF 7-AMINO-THIAZOLYL-ACETAMIDO-CEPHALOSPORANIC ACID
FR2345153A1 (en) * 1976-03-25 1977-10-21 Roussel Uclaf NEW ALCOYLOXIMES DERIVED FROM 7-AMINO THIAZOLYL ACETAMIDO CEPHALOSPORANIC ACID, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICINAL PRODUCTS

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1984002703A1 (en) * 1983-01-07 1984-07-19 Takeda Chemical Industries Ltd Process for preparing aminothiazolylacetic acid derivatives
US4695639A (en) * 1983-01-07 1987-09-22 Takeda Chemical Industries, Ltd. Thiazole derivatives
WO1984004305A1 (en) * 1983-05-02 1984-11-08 Takeda Chemical Industries Ltd Process for preparing aminothiazoleacetic acid derivatives

Also Published As

Publication number Publication date
JPH0373553B2 (en) 1991-11-22
GB1576625A (en) 1980-10-08
HU183009B (en) 1984-04-28
JPS5962597A (en) 1984-04-10
JPS5941995B2 (en) 1984-10-11
JPS6141516B2 (en) 1986-09-16
JPH0684338B2 (en) 1994-10-26
JPH03135946A (en) 1991-06-10
JPS52125190A (en) 1977-10-20
JPS5368796A (en) 1978-06-19
JPS5368795A (en) 1978-06-19
JPS6137250B2 (en) 1986-08-22

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