NL8003054A - Alfa-beschermde oxyimino beta-oxo gamma-halogeen- boterzuurderivaten. - Google Patents

Alfa-beschermde oxyimino beta-oxo gamma-halogeen- boterzuurderivaten. Download PDF

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Publication number
NL8003054A
NL8003054A NL8003054A NL8003054A NL8003054A NL 8003054 A NL8003054 A NL 8003054A NL 8003054 A NL8003054 A NL 8003054A NL 8003054 A NL8003054 A NL 8003054A NL 8003054 A NL8003054 A NL 8003054A
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Prior art keywords
compound according
οχο
methoxyimino
ethyl
ester
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NL8003054A
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English (en)
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Takeda Chemical Industries Ltd
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Priority claimed from JP49146567A external-priority patent/JPS5760345B2/ja
Priority claimed from GB24611/75A external-priority patent/GB1536281A/en
Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd
Publication of NL8003054A publication Critical patent/NL8003054A/nl

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    • 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
    • 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
    • C07D277/34—Oxygen atoms
    • 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
    • C07D277/44—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
    • 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
    • C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

_ 1 „ p & c *> ψ*
Takeda Chemical Industries, Ltd- te Osaka, Japan. j ; α-Beschermde oxyiaino β-οχο i-halogeenboterzuurderivaten. ' ; Afsplitsing van octrooiaanvrage 7514811. ! i j ! i De uitvinding heeft betrekking op een verbinding met de formule ! i (1), waarin X een halogeenatoom en Y en Z samen een groep met de formulé
5 5 I
= NR voorstellen, waarin R een beschermde hydroxylgroep voorstelt, j ' ' i benevens zouten en esters daarvan. ! i !.
5 j De verbinding (1) is een waardevol tussenprodukt voor de bereiding I van een verbinding met de formule (2), waarin R* een eventueel bescherm-f I j ( de amino- of hydroxylgroep voorstelt en de overige symbolen de hieronder I gegeven betekenissen hebben, benevens zouten of esters daarvan. De ver-: i ! ; bindingen volgens formule (2) kunnen bereid worden door de verbindingen ; 10 : volgens formule (1) om te zetten met een verbinding met de formule (3), !
12 I
jwaarin R een lage alkoxygroep of een eventueel beschermde aminogroep 1 I voorstelt, zonodig gevolgd door verwijdering van de beschermende groep, j
De verbinding (3) is op zijn beurt weer waardevol voor de bereiding van
15 I
: cefemverbindingen met de formule (4), waarin R en R de bovengegeven 3 4 ' 15 betekenissen hebben, R waterstof of methoxygroep voorstelt en R watery stof of de rest van een nucleofiele verbinding voorstelt, benevens t ' zouten en esters daarvan, in het bijzonder farmaceutisch aanvaardbare ;
# I
\ zouten en esters. Deze verbindingen (4) worden bereid door een verbin- >
O
• ding (2) om te zetten met een verbinding met de formule (5), waarin R
1 4 - : 20 ; en R de bovengegeven betekenissen hebben, of een zout of ester daarvan.
t ; j · In de verbindingen(1) stellen Y en Z samen een groep met de 5 5 i 1 formule = NR voor, waarbij het symbool R een beschermde hydroxylgroep I ; | voorstelt. Als beschermende groepen voor de hydroxylgroep kan men elk van de gebruikelijke groepen toepassen, mits zij de reacties van de j * j 25 uitvinding niet storen en in het algemeen gebruikt men een lage alkyl- j groep, bijvoorbeeld methyl, ethyl, enz.; een arylgroep, bijvoorbeeld -fenyl, thienyl enz.; een acylgroep, bijvoorbeeld acetyl, benzoyl enz. ; In de verbindingen (1) stelt het symbool X een halogeenatoom | voor, zoals chloor, broom, jodium, fluor enz. De carboxylgroep van de ; ί 30 verbindingen (1) kan beschermd zijn met een beschermende groep, die onder milde omstandigheden te verwijderen is, bijvoorbeeld door zure of alka- · -lische omstandigheden, reductie, enz. Derhalve kan men dergelijke be- 80 0 30 5 4................ ........
1« 4* ; schermende groepen kiezen uit beschermende groepen voor de carboxylgroep, _ » ; die gewoonlijk worden toegepast bij de peptidesynthese. Voorbeelden hiervan zijn alkalimetalen, zoals natrium, kalium, enz.; alkylgroepen, ; , bijvoorbeeld methyl, ethyl, propyl, isopropyl, butyl, sec.butyl, iso- j 5 butyl, tert.butyl, enz.; gesubstitueerde alkylgroepen, bijvoorbeeld j : β-methylsulfonylethyl, trichloorethyl, difenylmethyl enz.; arylgroepen, \ i i : bijvoorbeeld fenyl, tolyl, enz.; gesubstitueerde arylgroepen, bijvoor- j beeld p.tert.butylfenyl, p.nitrofenyl enz.; aralkylgroepen, bijvoorbeeld ! * j I benzyl, fenetyl, tolubenzyl enz.; gesubstitueerde aralkylgroepen, bij- i j 10 j voorbeeld p.methoxybenzyl, p.nitrobenzyl enz. j j Hoewel de verbindingen (1) theoretisch kunnen voorkomen als j I i - . syn- en anti-isomeren voor wat betreft de beschermde oxyiminogroep, | ; kem men elk van deze isomeren op gelijke wijze als waardevol tussenpro- ; ! dukt toepassen. i ; i t » 15 | De verbinding (1) kan bereid worden door de overeenkomstige a- | ; (beschermd oxyimino) β-oxoboterzuurderivaten volgens op zichzelf bekende i ! methoden te halogeneren. | ; VOORBEELD I |
Bij een oplossing van 18,7 g ethyl α-ethoxyimino 6-oxobutyraat 20 ; in 100 ml chloroform voegt men druppelsgewijs en onder koelen met ijs geleidelijk een oplossing van 15,9 g broom in 20 ml chloroform. Men i roert de oplossing 30 min. bij dezelfde temperatuur en nog 1½ uur bij .
: kamertemperatuur. Het reactiemengsel wordt achtereenvolgens met water, : waterige natriumbicarbonaatoplossing en water gewassen en vervolgens 25 ; boven watervrij magnesiumsulfaat gedroogd. De gedroogde oplossing wordt vervolgens door verdamping van het oplosmiddel bevrijd. ' j VOORBEELD IX j
Bij een oplossing van 27,3 g ethyl a-methoxyimino β-oxobutyraat : ' in 120 ml chloroform voegt men druppelsgewijs in verloop van 30. min. ! i 30 een oplossing van 25,3 g broom in 30 ml chloroform. Men roert de oplos- j sing 1 uur bij kamertemperatuur, wast met verdunde waterige natriumbi- | carbonaatoplossing en met water en droogt. Na afdestilleren van het oplosmiddel uit de gedroogde oplossing verkrijgt men als olieachtig ruw pro- ! . i dukt ethyl α-methoxyimino 6-oxo /-broombutyraat. ! - Conclusies - 8003054

Claims (13)

  1. 2. Verbinding volgens conclusie 1, met het kenmerk, dat X broom is. i 5 j 3. Verbinding volgens conclusie 1, met het kenmerk, dat X chloor is. j 1- 4.' Verbinding volgens conclusie 1-3, met het kenmerk, dat de ester j ; een alkyl-, gesubstitueerde alkyl-, aryl-, gesubstitueerde aryl-, ί aralkyl- of gesubstitueerde aralkylester is. j ! j
  2. 5. Verbinding volgens conclusie 4, met het kenmerk, dat de ester : } ï 10. een alkylester is. !
  3. 1 I
  4. 6. Verbinding volgens conclusie 5, met het kenmerk, dat de alkyl- i ! \ ester een methyl- of ethylester is. ! i et
  5. 7. Verbinding volgens conclusies 1-6, met het kenmerk, dat R een lage j f j alkoxygroep is. ; /15 | 8. Verbinding volgens conclusie 7, met het kenmerk, dat de lage alkoxy-; ; groep een methoxygroep is. j
  6. 9. Verbinding volgens conclusie 2, met het kenmerk, dat hij methyl ! ί α-methoxyimino β-οχο ^-broombutyraat is. |
  7. 10. Verbinding volgens conclusie 2, met het kenmerk, dat hij ethyl j 20 cc-methoxyimino β-οχο jf-broombutyraat is. |
  8. 11. Verbinding volgens conclusie 2, met het kenmerk, dat hij a-methoxy-! i ; imino β-οχο £-broomboterzuur is. | i j
  9. 12. Verbinding volgens conclusie 2, met het lenmerk, dat hij ethyl et-! | j ethoxyimino β-οχο -broombutyraat is. {
  10. 13. Verbinding volgens conclusie 3, met het kenmerk, dat hij methyl j j j j cc-methoxyimino β-οχο Jf-chloorbutyraat is. \ 1 j
  11. 14. Verbinding volgens conclusie 3, met het kenmerk, dat hij ethyl j α-methoxyimino β-οχο ^-chloorbutyraat is. | i ’ 15. Verbinding volgens conclusie 3, met het kenmerk, dat hij cc-methoxy-: j 30. imino β-οχο ï-chloorboterzuur is. · i • 16. Werkwijze ter bereiding van een verbinding met de formule (1), ! waarin de verschillende symbolen de in conclusie 1 gegeven betekenissen ' hebben, benevens zouten en esters daarvan, met het kenmerk, dat men deze . verbindingen volgens een op zichzelf bekende werkwijze bereidt. 35 ~17. Werkwijze ter bereiding van een verbinding met de formule Cl), 80,0 3 0 5 4 ! waarin de verschillende symbolen de in conclusie 1 gegeven betekenissen j i hebben, of zouten of esters daarvan, met het kenmerk, dat men een ver- | binding met de formule (6) of een zout of ester daarvan halogeneert. ; : 18. Werkwijze volgens conclusie 17, met het kenmerk, dat men als halo- ; 5 generingsmiddel broom of chloor kiest. ; i ί 19. Werkwijze volgens conclusie 17 of 18, met het kenmerk, dat men I ethyl α-methoxyimino β-οχο ^-broombutyraat bereidt. j ' i : 20. Werkwijze volgens conclusie 17 of 18, met het kenmerk, dat men i. I j i methyl α-methoxyimino β-οχο ^-broombutyraat bereidt. j ί ' ! 10 j 21. Werkwijze volgens conclusie 17 of 18, met het kenmerk, dat men j | methyl cc-methoxyimino β-οχο tf'-chloorbutyraat bereidt. j
  12. 22. Werkwijze volgens conclusie 17 of 18, met het kenmerk, dat men | ί y * « j ethyl α-methoxyimino β-οχο ï-chloorbutyraat bereidt. j I · i ; I s ! ——— ί I » » . I t ! I f I i i } ! j | i i f ! ; ί I i . 1 : I I ί s ! ! ! ' 1 i ; i · ; i . > } I ; ί
  13. 1 I i : ί r ! ί ί ί : ί ; j I j 8”(T0 3 0 5 4 ........... ......................
NL8003054A 1974-12-19 1980-05-27 Alfa-beschermde oxyimino beta-oxo gamma-halogeen- boterzuurderivaten. NL8003054A (nl)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP49146567A JPS5760345B2 (nl) 1974-12-19 1974-12-19
JP14656774 1974-12-19
GB24611/75A GB1536281A (en) 1975-06-09 1975-06-09 Cephem compounds
GB2461175 1975-06-09

Publications (1)

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NL8003054A true NL8003054A (nl) 1980-08-29

Family

ID=26257200

Family Applications (4)

Application Number Title Priority Date Filing Date
NLAANVRAGE7514811,A NL183703C (nl) 1974-12-19 1975-12-18 Werkwijze ter bereiding van farmaceutische preparaten met antibiotische werkzaamheid, alsmede werkwijze ter bereiding van antibiotische werkzame cefemverbindingen.
NL7800731A NL7800731A (nl) 1974-12-19 1978-01-20 (alpha)-beschermde oxyimino (beta)-oxo gamma-halogeenboter- zuurderivaten.
NL8003054A NL8003054A (nl) 1974-12-19 1980-05-27 Alfa-beschermde oxyimino beta-oxo gamma-halogeen- boterzuurderivaten.
NL950016C NL950016I1 (nl) 1974-12-19 1995-08-22 Werkwijze ter bereiding van farmaceutische preparaten met antibiotische werkzaamheid, alsmede werkwijze ter bereiding van antibiotische werkzame cefemverbindingen.

Family Applications Before (2)

Application Number Title Priority Date Filing Date
NLAANVRAGE7514811,A NL183703C (nl) 1974-12-19 1975-12-18 Werkwijze ter bereiding van farmaceutische preparaten met antibiotische werkzaamheid, alsmede werkwijze ter bereiding van antibiotische werkzame cefemverbindingen.
NL7800731A NL7800731A (nl) 1974-12-19 1978-01-20 (alpha)-beschermde oxyimino (beta)-oxo gamma-halogeenboter- zuurderivaten.

Family Applications After (1)

Application Number Title Priority Date Filing Date
NL950016C NL950016I1 (nl) 1974-12-19 1995-08-22 Werkwijze ter bereiding van farmaceutische preparaten met antibiotische werkzaamheid, alsmede werkwijze ter bereiding van antibiotische werkzame cefemverbindingen.

Country Status (18)

Country Link
US (6) US4098888A (nl)
AT (1) AT357521B (nl)
AU (1) AU500104B2 (nl)
BE (1) BE836813A (nl)
BG (1) BG60437B2 (nl)
CA (3) CA1216284A (nl)
CH (4) CH624119A5 (nl)
DE (3) DE2556736C2 (nl)
DK (2) DK154939C (nl)
ES (4) ES443627A1 (nl)
FR (4) FR2294690A1 (nl)
GB (1) GB1536283A (nl)
HU (1) HU179798B (nl)
MX (1) MX5097E (nl)
NL (4) NL183703C (nl)
NO (1) NO157933C (nl)
PH (2) PH13731A (nl)
SE (2) SE442202B (nl)

Families Citing this family (166)

* Cited by examiner, † Cited by third party
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US4191762A (en) 1974-03-14 1980-03-04 Fujisawa Pharmaceutical Co., Ltd. 2-Lower alkyl-7-substituted amino-2 or 3-cephem-4-carboxylic acid compounds
US4297489A (en) * 1974-09-03 1981-10-27 Bristol-Myers Company 7-α-Amino-substituted acylamino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acids
US4182868A (en) * 1974-10-29 1980-01-08 Takeda Chemical Industries, Ltd. 7-Methoxycephalosporin derivatives
JPS5760345B2 (nl) * 1974-12-19 1982-12-18 Takeda Chemical Industries Ltd
DK154939C (da) * 1974-12-19 1989-06-12 Takeda Chemical Industries Ltd Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf
US4196205A (en) * 1976-01-23 1980-04-01 Roussel Uclaf 3-Acetoxymethyl-7-(iminoacetamido)-cephalosporanic acid derivatives
DE2760123C2 (de) * 1976-01-23 1986-04-30 Roussel-Uclaf, Paris 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
SE440655B (sv) * 1976-01-23 1985-08-12 Roussel Uclaf Sett att framstella nya oximderivat av 7-amino-tiazolyl-acetamido-cefalosporansyra
IE44888B1 (en) * 1976-03-09 1982-05-05 Fujisawa Pharmaceutical Co 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation theroef
GB1575803A (en) * 1976-03-09 1980-10-01 Fujisawa Pharmaceutical Co 3,7 disubstituted 3 cephem 4 carboxylic acid compounds andprocesses for the preparation thereof
US4299829A (en) 1976-03-12 1981-11-10 Fujisawa Pharmaceutical Co., Ltd. 2-Lower alkyl-7-substituted-2 or 3-cephem 4-carboxylic acid compounds
US4202893A (en) 1976-03-25 1980-05-13 Roussel Uclaf Alkyloximes of 7-amino-thiazolyl-acetamido-cephalosporanic acids
FR2345153A1 (fr) * 1976-03-25 1977-10-21 Roussel Uclaf Nouvelles alcoyloximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments
JPS5946237B2 (ja) * 1976-04-02 1984-11-10 武田薬品工業株式会社 セフアロスポリン誘導体およびその製造法
US4166115A (en) * 1976-04-12 1979-08-28 Fujisawa Pharmaceutical Co., Ltd. Syn 7-oxoimino substituted derivatives of cephalosporanic acid
DK162391C (da) * 1976-04-12 1992-03-09 Fujisawa Pharmaceutical Co Analogifremgangsmaade til fremstilling af syn-isomerer af 3,7-disubstituerede 3-cephem-4-carboxylsyreforbindelser
US4431643A (en) * 1976-04-12 1984-02-14 Fujisawa Pharmaceutical Co., Ltd. Syn-isomer of 3-substituted-7-[2-cyclopentyloxyimino-2-(2-aminothiazol-4-yl)-acetamido]-3
FR2367756B1 (fr) * 1976-04-12 1985-07-05 Fujisawa Pharmaceutical Co Derives 2-alcoxyamino-2-(amino-1,3-thiazolyl) acetiques et leur utilisation
US4331664A (en) * 1976-04-12 1982-05-25 Fujisawa Pharmaceutical Co., Ltd. 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
US4804752A (en) * 1976-04-12 1989-02-14 Fujisawa Pharmaceutical Co., Ltd. Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof
US4304770A (en) * 1976-04-12 1981-12-08 Fujisawa Pharmaceutical Co., Ltd. Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof
US4493833A (en) * 1976-04-12 1985-01-15 Fujisawa Pharmaceutical Co., Ltd. Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds
US4364943A (en) * 1976-04-12 1982-12-21 Fujisawa Pharmaceutical Co., Ltd. Syn-isomer of 7-[2-alkoxyimino-2-(2-amino-alkanoylamino-or haloalkanoylamino-thiazol-4-yl) acetamids]-3-[hexanoyl-, or phenylalkanoyl-oxymethyl or benzothiazolylthiomethyl]-3-cephem-4-carboxylic acid
DE2760491C2 (de) * 1976-09-08 1995-04-20 Takeda Chemical Industries Ltd Pharmazeutische Zubereitungen enthaltend Pivaloyloxymethyl 7- 2-(2-aminothiazol-4-yl)-2-(syn)mehtoxyiminoacetamido desacetoxycephalosporanat und dessen Salze
DE2760488C2 (de) * 1976-04-14 1994-04-07 Takeda Chemical Industries Ltd Cephalosporinderivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE2760482C2 (de) * 1976-04-14 1995-02-09 Takeda Chemical Industries Ltd Pharmazeutische Zubereitungen, enthaltend ein 7-[2-(2-aminothiazol-4yl)-2-(syn)-methoxyiminoacetamido]cephalosporinderivat
DE2760484C2 (nl) * 1976-04-14 1992-12-03 Takeda Chemical Industries, Ltd., Osaka, Jp
FI771866A (nl) * 1976-06-28 1977-12-29 Fujisawa Pharmaceutical Co
US4963542A (en) * 1976-09-08 1990-10-16 Takeda Chemical Industries, Ltd. Cephalosporin derivatives
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ES457891A1 (es) 1978-08-01
DE2556736C2 (de) 1982-02-11
ATA517277A (de) 1979-12-15
FR2434146A1 (fr) 1980-03-21
DK155086B (da) 1989-02-06
ES464771A1 (es) 1978-09-01
US4514565A (en) 1985-04-30
GB1536283A (en) 1978-12-20
HU179798B (en) 1982-12-28
US5583216A (en) 1996-12-10
DE2559942C2 (de) 1985-02-28
US4973684A (en) 1990-11-27
US4098888A (en) 1978-07-04
FR2434146B1 (nl) 1984-02-10
CH631437A5 (de) 1982-08-13
ES443627A1 (es) 1977-10-16
PH14161A (en) 1981-03-19
NL183703C (nl) 1989-01-02
AU8766775A (en) 1977-06-23
FR2294690A1 (fr) 1976-07-16
FR2357552A1 (fr) 1978-02-03
US4205180A (en) 1980-05-27
MX5097E (es) 1983-03-16
DK154939B (da) 1989-01-09
BG60437B2 (bg) 1995-03-31
DE2560398C2 (de) 1983-09-29
SE445454B (sv) 1986-06-23
CH624119A5 (nl) 1981-07-15
SE7902954L (sv) 1979-04-03
CA1128957A (en) 1982-08-03
DE2556736A1 (de) 1976-06-24
DK552377A (da) 1977-12-09
NL7800731A (nl) 1978-05-31
NO157933B (no) 1988-03-07
CA1216284A (en) 1987-01-06
NO157933C (no) 1988-06-15
NL183703B (nl) 1988-08-01
SE442202B (sv) 1985-12-09
NL7514811A (nl) 1976-06-22
DK548875A (da) 1976-06-20
PH13731A (en) 1980-09-09
CH628058A5 (de) 1982-02-15
SE7514286L (sv) 1976-06-21
NL950016I1 (nl) 1996-03-01
CA1137492A (en) 1982-12-14
FR2294690B1 (nl) 1982-01-29
FR2468599B1 (fr) 1986-03-21
CH633544A5 (de) 1982-12-15
AT357521B (de) 1980-07-10
FR2468599A1 (fr) 1981-05-08
BE836813A (fr) 1976-06-18
DK155086C (da) 1989-06-19
AU500104B2 (en) 1979-05-10
ES464772A1 (es) 1979-01-01
DK154939C (da) 1989-06-12
US4912212A (en) 1990-03-27
NO754296L (nl) 1976-06-22

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