DE2559942C2 - In α-Stellung geschützte Oxyimino-β-oxo-γ-halogenbuttersäurederivate und ihre Verwendung zur Herstellung entsprechender 2-Amino-thiazol-4-yl-essigsäurederivate - Google Patents
In α-Stellung geschützte Oxyimino-β-oxo-γ-halogenbuttersäurederivate und ihre Verwendung zur Herstellung entsprechender 2-Amino-thiazol-4-yl-essigsäurederivateInfo
- Publication number
- DE2559942C2 DE2559942C2 DE2559942A DE2559942A DE2559942C2 DE 2559942 C2 DE2559942 C2 DE 2559942C2 DE 2559942 A DE2559942 A DE 2559942A DE 2559942 A DE2559942 A DE 2559942A DE 2559942 C2 DE2559942 C2 DE 2559942C2
- Authority
- DE
- Germany
- Prior art keywords
- acid derivatives
- compounds
- preparation
- amino
- thiazol
- 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.)
- Expired
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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
In ^-Stellung geschützte Oxyimino-^-oxo-y-halogenbuttersäurederivate
und ihre Verwendung zur Herstellung entsprechender 2-Amino-thiazol-4-yl-essigsäurederivate.
Die vorliegende Erfindung betrifft Verbindungen der Formel
XCH—C —C-COOH
Il I!
O NR3
in der X ein Halogenatom und Rs eine niedere Alkoxygruppe
sind, saure Salze und Ester dieser Verbindungen und ihre Verwendung zur Herstellung entsprechender
2-Amino-thiazol-4-yl-essigsäure-Derivaten. Die Verbindungen (XII) sind wertvolle Zwischenprodukte
für die Herstellung von Verbindungen der Formel -w
(XIV)
C — COOH
NR5
in der R' eine gegebenenfalls geschützte Aminogruppe ist und die übrigen Symbole die obengenannten Bedeutungen
haben oder von Salzen oder Estern dieser Verbindungen durch Umsetzen mit einer Verbindung
der Formel
(xm)
R1 —C-NH2
CCONH
NR5
CH2R4
COOH
(D
in der R1 und Rs die oben angegebene Bedeutung haben
und R4 Wasserstoff, einen Acetoxyrest, eine Thiadiazolylthiogruppe,
eine Triazolylthiogruppe, eine Tetrazolylthiogruppen
die durch niederes Aethyl substituiert sein können oder Carbamoyoxy bedeuten und pharmazeutisch
unbedenkliche Salze oder Ester dieser Verbindungen, durch Umsetzung mit Verbindungen der Formel
CH2R4
(VI)
COOH
in der R1 die vorstehende Bedeutung hat und gegebenenfalls
anschließender Entfernung der Schutzgruppe.
Die Verbindungen (XIV) sind wertvoll für die Herstellung von Cephemverbindungen der Formel
in der R4 die oben genannte Bedeutung hat, oder von Salzen oder Estern dieser Verbindungen.
In den Ausgangsverbindungen (XII) besitzt Rs die
vorstehende Bedeutung.
In den Verbindungen (XII) ist X ein Halogenatom, z. B. Chlor, Brom, Jod und Fluor. Die Carboxylgruppe
der Verbindungen (XII) kann ein Salz oder einen Ester bilden, die unter milden Bedingungen, z. B. unter
sauren oder alkalischen Bedingungen, durch Reduktion usw. wieder die Carboxylgruppe freisetzen. Als Salze
kommen z. B. Alkallsalze wie Natrium- und Kallumsalze,
als Ester, Alkylester, z. B. Methyl-, Äthyl-, Propyl-, Isopropyl-, Butyl-, sek.-Butyl-, Isobutyl- und
tert.-Butyl-, sowie substituierte Alkylester 'in Frage,
z. B. ^-Methylsulfonyläthyl-, Trlchloräihyl- und
Diphenylmethylester, Arylester, ζ. Β. Phenyl- und Tolylester, substituierte Arylester, ζ. B. p-tert.-Butylphenyl-
und p-Nitrophenylester, Aralkylester, z. B. Benzyl-, Phenäthyl- und Tolubenzylester, substituierte
Araikylester, z. B. p-Methoxybenzyl- und p-Nltrobenzylester
kommen gleichfalls in Frage.
Die Verbindungen (XII) können theoretisch als syn- und anti-Isomere zur geschützten Oximlnogruppe
vorliegen, jedoch eignen sich beide Isomere gleich gut als Zwischenprodukte.
Die Verbindungen (XII) können nach an sich bekannten Verfahren durch Halogenierung der entsprechenden
jr-geschützten Oxlmino-ß-oxobuttersäurederivate
herstellt werden.
Zu einer Lösung von 18,7g Äthyl alpha-Äthoxylmino-/?-oxobutyrat
in 100 ml Chloroform wird tropfenweise eine Lösung von 15,9 g Brom In 20 ml Chloroform
unter Eiskühlung gegeben. Die Lösung wird 30 Minuten bei derselben Temperatur und weitere 1,5
Stunden bei Raumtemperatur gerührt. Das Reaktionsgemisch wird mit Wasser, wäßriger Natriumblcarbonatlösung
und dann mit Wasser in dieser Reihenfolge gewaschen, worauf über wasserfreiem Magnesiumsulfat
getrocknet wird. Die gegrocknete Lösung wird zur Entfernung des Lösungsmittels eingedampft.
Ausbeute 24,2 g (91,6%)
NMR-Spektrum (CDCl3): <5 1,20-1,60 (m, · <
6H, CH3X2) 4,10-4,60 (m, 4H, CH2X2), 4,32 (s,
2H, BrCH2)
In
Zu einer Lösung von 27,3 g Äthyl alpha-methoxyimino-/!-oxobutyrat
in 120 ml Chloroform wird tropfenweise eine Lösung von 25,3 g Brom in 30 ml Chloroform
über eine Zeit von 30 Minuten gegeben. Die Lösung wird 1 Stunde bei Raumtemperatur gerührt und
dann mit verdünnter wäßriger Natriumbicarbonatlösung und mit Wasser gewaschen und getrocknet. Die
getrocknete Lösung wird zur Entfernung des Lösungsmittels destilliert, wobei ein öliges rohes Produkt von
Äthyl alpha-methoxyimino-/?-oxo-5'-brombutyrat erhal- .2«
ten wird.
Ausbeute 36,7 g (92,8%)
NMR-Spektrum (CDCl3): δ 1,30 (A, 3H, CH3),
4,12 (s, 3H, OCH3), 4,32 (s, 2H, BrCH2), 4,33 (q,
2H, CH2)
40
45
60
65
Claims (2)
1. Verbindungen der Formel
NR-
Il
XCH3-C-C-COOH
XCH3-C-C-COOH
in der X ein Halogenatom und R5 eine niedere Alkoxylgruppe sind, sowie Salze oder Ester dieser
Verbindungen.
2. Verwendung der Verbindungen gemäß Anspruch 1 zur Herstellung entsprechender 2-Amino-thiazol-4-yl-essigsäure-Derivate
durch an sich bekannte Umsetzung mit entsprechenden Thioharnstoffen.
R1
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP49146567A JPS5760345B2 (de) | 1974-12-19 | 1974-12-19 | |
GB24611/75A GB1536281A (en) | 1975-06-09 | 1975-06-09 | Cephem compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2559942C2 true DE2559942C2 (de) | 1985-02-28 |
Family
ID=26257200
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2559942A Expired DE2559942C2 (de) | 1974-12-19 | 1975-12-17 | In α-Stellung geschützte Oxyimino-β-oxo-γ-halogenbuttersäurederivate und ihre Verwendung zur Herstellung entsprechender 2-Amino-thiazol-4-yl-essigsäurederivate |
DE2556736A Expired DE2556736C2 (de) | 1974-12-19 | 1975-12-17 | Cephemverbindungen und sie enthaltende Arzneimittel |
DE2560398A Expired DE2560398C2 (de) | 1974-12-19 | 1975-12-17 | 2-Amino-thiazol-4-yl-essigsäure-Derivate und Verfahren zu deren Herstellung |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2556736A Expired DE2556736C2 (de) | 1974-12-19 | 1975-12-17 | Cephemverbindungen und sie enthaltende Arzneimittel |
DE2560398A Expired DE2560398C2 (de) | 1974-12-19 | 1975-12-17 | 2-Amino-thiazol-4-yl-essigsäure-Derivate und Verfahren zu deren Herstellung |
Country Status (18)
Country | Link |
---|---|
US (6) | US4098888A (de) |
AT (1) | AT357521B (de) |
AU (1) | AU500104B2 (de) |
BE (1) | BE836813A (de) |
BG (1) | BG60437B2 (de) |
CA (3) | CA1216284A (de) |
CH (4) | CH624119A5 (de) |
DE (3) | DE2559942C2 (de) |
DK (2) | DK154939C (de) |
ES (4) | ES443627A1 (de) |
FR (4) | FR2294690A1 (de) |
GB (1) | GB1536283A (de) |
HU (1) | HU179798B (de) |
MX (1) | MX5097E (de) |
NL (4) | NL183703C (de) |
NO (1) | NO157933C (de) |
PH (2) | PH13731A (de) |
SE (2) | SE442202B (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2710282A1 (de) | 1976-03-09 | 1977-09-15 | Fujisawa Pharmaceutical Co | 3,7-disubstituierte-3-cephem-4- carbonsaeureverbindungen, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel |
DE2760288A1 (de) * | 1976-03-09 | 1985-05-09 |
Families Citing this family (164)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
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 |
JPS5760345B2 (de) * | 1974-12-19 | 1982-12-18 | Takeda Chemical Industries Ltd | |
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 |
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 |
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 |
US4202893A (en) | 1976-03-25 | 1980-05-13 | Roussel Uclaf | Alkyloximes of 7-amino-thiazolyl-acetamido-cephalosporanic acids |
US4166115A (en) * | 1976-04-12 | 1979-08-28 | Fujisawa Pharmaceutical Co., Ltd. | Syn 7-oxoimino substituted derivatives of cephalosporanic acid |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
GR63088B (en) * | 1976-04-14 | 1979-08-09 | Takeda Chemical Industries Ltd | Preparation process of novel cephalosporins |
FI771866A (de) * | 1976-06-28 | 1977-12-29 | Fujisawa Pharmaceutical Co | |
US4963542A (en) * | 1976-09-08 | 1990-10-16 | Takeda Chemical Industries, Ltd. | Cephalosporin derivatives |
JPS6011713B2 (ja) * | 1976-09-08 | 1985-03-27 | 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 |
GB1592149A (en) * | 1976-10-08 | 1981-07-01 | Fujisawa Pharmaceutical Co | 3 7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for preparation thereof |
GB1597848A (en) * | 1976-12-27 | 1981-09-09 | Fujisawa Pharmaceutical Co | Cephalosporin compounds and processes for the preparation thereof |
JPS53144594A (en) * | 1976-12-27 | 1978-12-15 | Fujisawa Pharmaceut Co Ltd | 3,7-di-substitued-3-cephem-4-carboxylic acid derivatives |
JPS6011714B2 (ja) | 1977-02-17 | 1985-03-27 | 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 |
JPS53101393A (en) | 1977-02-17 | 1978-09-04 | Takeda Chem Ind Ltd | Cephalosporin derivatives and process for their preparation |
JPS53103493A (en) | 1977-02-18 | 1978-09-08 | Takeda Chem Ind Ltd | Cephalosporin derivatives and process for their preparation |
FR2381053A1 (fr) * | 1977-02-18 | 1978-09-15 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-thiadiazolyl thiomethyl 7-aminothiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
DE2710902A1 (de) * | 1977-03-12 | 1978-09-21 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
PH17188A (en) * | 1977-03-14 | 1984-06-14 | Fujisawa Pharmaceutical Co | New cephem and cepham compounds and their pharmaceutical compositions and method of use |
US4841062A (en) * | 1977-03-14 | 1989-06-20 | Fujisawa Pharmaceutical Company, Limited | New cephem and cepham compounds and processes for preparation thereof |
SE439312B (sv) * | 1977-03-25 | 1985-06-10 | Roussel Uclaf | Sett att framstella nya oximderivat av 3-acetoximetyl-7-aminotiazolylacetamido cefalosporansyra |
GB1579533A (en) * | 1977-03-26 | 1980-11-19 | Farmaceutici Italia | Cephalosporins and their preparation |
DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
DE2716677C2 (de) * | 1977-04-15 | 1985-10-10 | Hoechst Ag, 6230 Frankfurt | Cephemderivate und Verfahren zu ihrer Herstellung |
US5089490A (en) * | 1977-04-02 | 1992-02-18 | Hoechst Aktiengesellschaft | Cephem derivatives |
DE2831568C2 (de) * | 1977-07-23 | 1985-01-10 | Toyama Chemical Co. Ltd., Tokio / Tokyo | 7α-Methoxycephalosporine und Verfahren zur Herstellung derselben |
JPS609719B2 (ja) * | 1977-08-06 | 1985-03-12 | 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 |
FR2400519A1 (fr) * | 1977-08-17 | 1979-03-16 | Roussel Uclaf | Forme cristalline du sel de sodium d'un derive oximine de l'acide 7-amino-thiazolyl acetamido cephalosporanique, son procede de preparation et son application comme medicament |
US4370326A (en) * | 1977-09-13 | 1983-01-25 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds and composition |
IT1192287B (it) * | 1977-11-14 | 1988-03-31 | Fujisawa Pharmaceutical Co | Derivati di acido cefalosporanico ad azione farmaceutica e relativo procedimento di preparazione |
FR2410655A1 (fr) * | 1977-12-05 | 1979-06-29 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-substitue 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
DE2758001A1 (de) * | 1977-12-24 | 1979-07-12 | Hoechst Ag | Cephalosporinderivate und verfahren zu ihrer herstellung |
FR2387235A1 (fr) * | 1978-01-23 | 1978-11-10 | Fujisawa Pharmaceutical Co | Procede de preparation de composes d'acide 3,7-disubstitue-3-cephem-4-carboxylique et nouveaux produits ainsi obtenus, ayant une forte activite antibacterienne |
JPS54112892A (en) * | 1978-02-23 | 1979-09-04 | Shionogi & Co Ltd | Substituted imidazolidinyl-3-chloro-3-cephem-4-carboxylic acid |
US4180658A (en) * | 1978-02-24 | 1979-12-25 | Bristol-Myers Company | 7[-2-Alkoxyamino(acetamido)]cephalosporin derivatives |
JPS54117494A (en) * | 1978-03-03 | 1979-09-12 | Takeda Chem Ind Ltd | Cephalosporin compound and its preparation |
FR2421907A1 (fr) * | 1978-04-07 | 1979-11-02 | Roussel Uclaf | Nouvelles cephalosporines derivees de l'acide 7-/2-(2-amino 4-thiazolyl)2-(carboxymethoxyimino/acetamido 3-substitue cephalosporanique, leur procede de preparation et leur application comme medicaments |
SE445350B (sv) * | 1978-04-14 | 1986-06-16 | Roussel Uclaf | Oximderivat av 3-azidometyl-7-amino-tiazolyl-acetamido-cefalosporansyra och dess anvendning som antibiotika |
DE2818263A1 (de) * | 1978-04-26 | 1979-11-08 | Bayer Ag | Beta-lactamantibiotika |
AR229883A1 (es) * | 1978-05-26 | 1983-12-30 | Glaxo Group Ltd | Procedimiento para la preparacion de antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)-acetamido)-3-(1-piridinometil)-cef-3-em-4-carboxilato |
CH641468A5 (de) * | 1978-05-30 | 1984-02-29 | Hoffmann La Roche | Cephemderivate. |
JPS54160392A (en) * | 1978-06-02 | 1979-12-19 | Takeda Chem Ind Ltd | Cephalosporin derivative and its preparation |
US4501743A (en) * | 1978-06-16 | 1985-02-26 | E. R. Squibb & Sons, Inc. | Iminothiazolyl ureido cephalosporins |
US4461767A (en) * | 1978-06-16 | 1984-07-24 | E. R. Squibb & Sons, Inc. | Iminothiazolyl ureido cephalosporins |
US4268509A (en) * | 1978-07-10 | 1981-05-19 | Fujisawa Pharmaceutical Co., Ltd. | New cephem compounds and processes for preparation thereof |
DE2967356D1 (en) * | 1978-07-17 | 1985-02-28 | Fujisawa Pharmaceutical Co | Cephalosporin derivatives, process for their preparation and pharmaceutical compositions containing them |
JPS6058239B2 (ja) * | 1978-07-20 | 1985-12-19 | 山之内製薬株式会社 | 新規セフアロスポリン誘導体 |
US4284631A (en) * | 1978-07-31 | 1981-08-18 | Fujisawa Pharmaceutical Co., Ltd. | 7-Substituted cephem compounds and pharmaceutical antibacterial compositions containing them |
US4372952A (en) * | 1978-07-31 | 1983-02-08 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
US4305937A (en) * | 1978-08-17 | 1981-12-15 | Fujisawa Pharmaceutical Co., Ltd. | 2-Lower alkyl-7-substituted-2 or 3-cephem-4-carboxylic acid compounds and antibacterial pharmaceutical compositions containing them |
US4703046A (en) * | 1978-09-08 | 1987-10-27 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds and processes for preparation thereof |
US4341775A (en) * | 1978-09-11 | 1982-07-27 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
US4220761A (en) * | 1978-09-12 | 1980-09-02 | Fujisawa Pharmaceutical Co., Ltd. | 7-[Substituted oximinoacetamido]-3-[hydroxy alkyltetrazolo]cephalosporin derivatives |
EP0048504B1 (de) * | 1978-09-12 | 1988-08-17 | Fujisawa Pharmaceutical Co., Ltd. | Cephalosporinzwischenprodukte, Verfahren zu ihrer Herstellung und Verfahren zur Herstellung von Cephalosporinderivaten |
US4327093A (en) * | 1978-10-24 | 1982-04-27 | Fujisawa Pharmaceutical Co., Ltd. | 3,7-Disubstituted-2 or 3-cephem-4-carboxylic acid compounds |
CA1130280A (en) * | 1978-10-27 | 1982-08-24 | Cynthia H. O'callaghan | Cephalosporin compounds |
IL58717A (en) * | 1978-11-15 | 1983-05-15 | Glaxo Group Ltd | Derivatives of(6r,7r)-7-((z)-2-(2-aminothiazol-4-yl)-2-(carboxy-(lower alkyl or cycloalkyl)oxyimino)acetamido)-3-(2-alkyl-pyrazolium-1-ylmethyl)ceph-3-em-4-carboxylate,process for their preparation and pharmaceutical compositions comprising them |
US4313945A (en) * | 1978-11-23 | 1982-02-02 | Ciba-Geigy Corporation | 7-Thiazolyl-acetamido-cephem derivatives with terminal aminocarboxylic acid grouping |
JPS5579393A (en) * | 1978-12-11 | 1980-06-14 | Takeda Chem Ind Ltd | Cephalosporin derivative and its preparation |
US4332798A (en) * | 1978-12-29 | 1982-06-01 | Fujisawa Pharmaceutical Co., Ltd. | 7-Amino-thia-diazole oxyimino derivatives of cephem and cephem compounds |
AU536842B2 (en) * | 1978-12-29 | 1984-05-24 | Fujisawa Pharmaceutical Co., Ltd. | Cephalosporin antibiotics |
FR2445830A1 (fr) * | 1979-01-05 | 1980-08-01 | Roussel Uclaf | Nouveaux derives de l'acide (4-thiazolyl) acetique procede de preparation |
ES8103101A1 (es) * | 1979-03-22 | 1981-02-16 | Glaxo Group Ltd | Un procedimiento para la preparacion de antibioticos de ce- falosporina |
US4237128A (en) * | 1979-04-12 | 1980-12-02 | E. R. Squibb & Sons, Inc. | 7-[2-(2-Amino-4-thiazolyl)-2-[(1-carboxy-1,1-dialkyl)alkoxyimino]acetamido]cephem sulfoxides |
FR2457296A1 (fr) * | 1979-05-23 | 1980-12-19 | Rhone Poulenc Ind | Nouveaux derives de vinyl-3 cephalosporines et leur preparation |
NO801501L (no) * | 1979-05-23 | 1980-11-24 | Rhone Poulenc Ind | Fremgangsmaate for fremstilling av 3-tiovinylcefalosporiner |
EP0021688B1 (de) * | 1979-06-07 | 1983-07-13 | Yamanouchi Pharmaceutical Co., Ltd. | 7-(Thiazolylpropionamido)-cephalosporine, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
US4275062A (en) * | 1979-09-19 | 1981-06-23 | E. R. Squibb & Sons, Inc. | Aminothiazolyl ureido sulfoxide cephalosporins |
US4252951A (en) * | 1979-10-09 | 1981-02-24 | Eli Lilly And Company | Isolation of syn-7-(2-amino-4-thiazolyl)-(methoxyimino)acetamido-3-acetoxymethyl-3-cephem-4-carboxylic acid |
US4332800A (en) * | 1979-10-12 | 1982-06-01 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
US4381299A (en) * | 1980-03-07 | 1983-04-26 | Fujisawa Pharmaceutical Co., Ltd. | 7-Amino-thiadiazole oxyimino derivatives of cephem and cepham compounds |
US4338313A (en) * | 1979-10-12 | 1982-07-06 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
US4271157A (en) * | 1980-02-28 | 1981-06-02 | E. R. Squibb & Sons, Inc. | Imidazole derivatives of 7-[(2-amino-4-thiazolyl)-oximino] cephalosporins |
US4409214A (en) * | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical, Co., Ltd. | 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof |
US4409215A (en) * | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical Co., Ltd. | 7-Acylamino-3-substituted cephalosporanic acid derivatives and processes for the preparation thereof |
US5243043A (en) * | 1980-02-18 | 1993-09-07 | Roussel Uclaf | Cephalosporins |
DE3006888A1 (de) * | 1980-02-23 | 1981-09-10 | Hoechst Ag, 6000 Frankfurt | Cephalosporinderivate und verfahren zu ihrer herstellung |
DE3007685A1 (de) | 1980-02-29 | 1981-10-01 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue cephylosporine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
US4252802A (en) * | 1980-03-13 | 1981-02-24 | E. R. Squibb & Sons, Inc. | Hydroxamic acid derivatives of 7-[(2-amino-4-thiazolyl)-oximino] cephalosporins |
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 |
US4399132A (en) * | 1980-08-11 | 1983-08-16 | American Cyanamid Company | 7-Beta-[alpha-syn-methoxyimino-alpha-(2-aminothiazol-4-yl)-acetamido]-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-3-cephem-4-carboxylic acid and C1 -C6 alkyl derivatives thereof |
US4486425A (en) * | 1980-09-30 | 1984-12-04 | Sankyo Company Limited | 7-[2-(2-Aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylates |
US4367228A (en) * | 1980-10-29 | 1983-01-04 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compound and composition |
US4431642A (en) * | 1980-12-01 | 1984-02-14 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
DE3177090D1 (en) * | 1980-12-31 | 1989-09-28 | Fujisawa Pharmaceutical Co | 7-acylaminocephalosporanic acid derivatives and processes for the preparation thereof |
US4427677A (en) * | 1980-12-31 | 1984-01-24 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
JPS57154175A (en) * | 1981-03-16 | 1982-09-22 | Mitsui Toatsu Chem Inc | 2-thiazoleamine derivative, its preparation, and drug composition comprising it |
JPS6011917B2 (ja) * | 1981-04-09 | 1985-03-28 | 山之内製薬株式会社 | 新規なセファロスポリン化合物 |
DE3117438A1 (de) * | 1981-05-02 | 1982-11-18 | Hoechst Ag, 6000 Frankfurt | Cephemderivate und verfahren zu ihrer herstellung |
DE3118732A1 (de) * | 1981-05-12 | 1982-12-02 | Hoechst Ag, 6000 Frankfurt | Cephalosporinderivate und verfahren zu ihrer herstellung |
US4396619A (en) * | 1981-09-08 | 1983-08-02 | Eli Lilly And Company | Cephalosporin betaines |
US4396620A (en) * | 1981-09-08 | 1983-08-02 | Eli Lilly And Company | Cephalosporin quinolinium betaines |
US4594417A (en) * | 1981-10-30 | 1986-06-10 | Eli Lilly Company | Crystalline antibiotic salt |
US4400503A (en) * | 1981-10-30 | 1983-08-23 | Eli Lilly And Company | Purification of syn-7-[[(2-amino-4-thiazolyl)(methoxyimino) acetyl]amino]-3-methyl-3-cephem-4-carboxylic acid |
EP0088847B1 (de) * | 1981-11-13 | 1986-02-26 | Glaxo Group Limited | Thiazol-Derivate und ihre Verwendung bei der Herstellung von Beta-Lactam-Antibiotika |
ATE30724T1 (de) | 1982-06-28 | 1987-11-15 | Bristol Myers Co | Cephalosporinderivate, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen die sie enthalten. |
US4560683A (en) * | 1982-06-30 | 1985-12-24 | Glaxo Group Limited | Cephalosporin antibiotics |
DE3239365A1 (de) * | 1982-10-23 | 1984-04-26 | Bayer Ag, 5090 Leverkusen | Neue cephalosporine und verfahren zu ihrer herstellung |
US4480120A (en) * | 1983-03-24 | 1984-10-30 | Eastman Kodak Company | Process for the preparation of alkyl-2-alkoxyimino-3-oxo-4-chlorobutyrates |
DE3485860T2 (de) * | 1983-12-29 | 1993-01-14 | Mochida Pharm Co Ltd | Cephalosporinverbindungen, verfahren zu ihrer herstellung und pharmazeutishe praeparate. |
US4788185A (en) * | 1984-04-23 | 1988-11-29 | Takeda Chemical Industries, Ltd. | Cephalosporin compounds |
PH22107A (en) * | 1984-06-07 | 1988-06-01 | Takeda Chemical Industries Ltd | 3-pyrazolo(1,5-a)pyrdinium cephem compounds |
DE3585434D1 (de) * | 1984-12-27 | 1992-04-02 | Banyu Pharma Co Ltd | Cephalosporinverbindungen. |
ATE89826T1 (de) * | 1985-03-01 | 1993-06-15 | Takeda Chemical Industries Ltd | Antibakterielle verbindungen, ihre herstellung und verwendung. |
US4840945A (en) * | 1985-04-01 | 1989-06-20 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
US4698338A (en) * | 1986-02-19 | 1987-10-06 | Eli Lilly And Company | 7[2-(2-aminothiazol-4-yl)-2-benzyloximino]acetamido-3[4-alkyl-5-oxo-6-hydroxy-3,4-dihydro-1,2,4-triazin-3-yl]thiomethyl cephalosporins |
US4814328A (en) * | 1986-03-19 | 1989-03-21 | Banyu Pharmaceutical Co., Ltd. | Cephalosporin derivatives, and antibacterial agents |
JPS6310795A (ja) * | 1986-03-25 | 1988-01-18 | Takeda Chem Ind Ltd | 選択性除草化合物 |
JPS635091A (ja) * | 1986-06-26 | 1988-01-11 | Senjiyu Seiyaku Kk | 着色防止方法 |
US5066799A (en) * | 1986-07-28 | 1991-11-19 | American Cyanamid Company | Intermediates for the preparation of aminothiazoloximino cephalosporins |
US4959495A (en) * | 1986-07-28 | 1990-09-25 | American Cyanamid Company | Process for the preparation of intermediates used to produce aminothiazoloximino cephalosporins |
FR2621589B1 (fr) * | 1987-10-08 | 1990-03-02 | Sanofi Sa | Derives des cephalosporines a pharmacocinetique amelioree, procede pour leur preparation et compositions pharmaceutiques les contenant |
US5242913A (en) * | 1987-03-11 | 1993-09-07 | Pfizer Inc. | Substituted 3-cephem compounds as antibacterial agents |
WO1993013108A1 (en) * | 1987-03-11 | 1993-07-08 | Susumu Nakanishi | Substituted 3-cephem compounds as antibacterial agents |
US5223496A (en) * | 1987-11-10 | 1993-06-29 | The Upjohn Company | Cephalosporin antibiotics |
DE3804841A1 (de) * | 1988-02-17 | 1989-08-31 | Hoechst Ag | Cephalosporinderivate und verfahren zu ihrer herstellung |
EP0333082A3 (de) * | 1988-03-15 | 1991-05-02 | Takeda Chemical Industries, Ltd. | Cephemverbindungen, ihre Herstellung und Anwendung |
DE3809845A1 (de) * | 1988-03-24 | 1989-10-12 | Hoechst Ag | Verfahren zur herstellung von 4-halo-3-oxo-2-alkoxyiminobuttersaeureestern |
NO175152C (no) * | 1988-10-07 | 1994-09-07 | Sankyo Co | Analogifremgangsmåte for fremstilling av terapeutisk aktive 3-aryloksymetyl-cefalosporinderivater |
DE3919259A1 (de) * | 1989-06-13 | 1990-12-20 | Hoechst Ag | Kristalline cephem-saeureadditionssalze und verfahren zu ihrer herstellung |
KR940000112B1 (ko) * | 1990-07-05 | 1994-01-05 | 주식회사 대웅제약 | 신규의 3-치환 세펨화합물 및 그의 제조방법 |
IL113744A (en) * | 1990-11-09 | 1998-06-15 | Eisai Co Ltd | History of 3-tufts and their preparation |
YU48484B (sh) * | 1991-05-24 | 1998-09-18 | Hoechst Aktiengesellschaft | Kristalne kiselinske adicione soli diastereomerno čistih 1-(2,2-dimetilpropioniloksi)-etilestara 3-cefem-4-karbonske kiseline |
US5281589A (en) * | 1991-06-15 | 1994-01-25 | Cheil Foods & Chemicals, Inc. | 3-fused pyridiniummethyl cephalosporins |
AT396108B (de) * | 1991-08-21 | 1993-06-25 | Biochemie Gmbh | Neues verfahren und neue zwischenprodukte zur herstellung von 7-aminocephalosporansaeurederivaten |
ES2215161T3 (es) * | 1991-09-07 | 2004-10-01 | Aventis Pharma Deutschland Gmbh | Diastereoisomero del ester 1-(isopropoxicarboniloxi)-etilico del acido 3-cefem-4-carboxilico y procedimiento para su preparacion. |
TW212181B (de) * | 1992-02-14 | 1993-09-01 | Hoechst Ag | |
ES2117066T3 (es) * | 1992-05-21 | 1998-08-01 | Hoechst Ag | Procedimiento para la disociacion de esteres profarmacos de cefalosporina para dar acido 7-amino-3-metoximetil-cef-3-em-4-carboxilico. |
DK0690864T3 (da) * | 1993-03-12 | 2001-09-17 | Upjohn Co | Krystallinsk ceftiofur på fri syreform |
KR100194994B1 (ko) * | 1993-06-05 | 1999-06-15 | 손경식 | 새로운 세펨 화합물 |
TW369530B (en) * | 1993-06-10 | 1999-09-11 | Lucky Ltd | Process for preparing cephalosporin compounds from reactive organic acid derivatives |
US6468995B1 (en) * | 1993-09-09 | 2002-10-22 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
US5661144A (en) * | 1994-08-16 | 1997-08-26 | Meiji Seika Kabushiki Kaisha | Cephem derivatives with 3-substituted bis heterocycles |
US5574154A (en) * | 1994-09-29 | 1996-11-12 | Alnejma Bulk Pharmaceutical Co. A.B.P.C. | Process for the preparation of cephalosporanic compounds |
GB9423459D0 (en) * | 1994-11-21 | 1995-01-11 | Biochemie Gmbh | Silylation process |
AT402928B (de) * | 1994-12-23 | 1997-09-25 | Biochemie Gmbh | Neues verfahren zur herstellung von cefotaxim |
KR0164458B1 (ko) * | 1995-04-04 | 1999-01-15 | 김은영 | 암모니오세팔로스포린 계열 항생제 및 그의 제조방법 |
US5872249A (en) * | 1995-09-01 | 1999-02-16 | Korea Institute Of Science And Technology | 3-ammoniopropenyl cephalosporin compounds as antibacterial agents and process for preparing the same |
AU690482B2 (en) * | 1996-03-18 | 1998-04-23 | Ranbaxy Laboratories Limited | Process for producing cephalosporin antibiotics |
IN184690B (de) * | 1996-03-18 | 2000-09-23 | Ranbaxy Lab Ltd | |
US7842791B2 (en) * | 2002-12-19 | 2010-11-30 | Nancy Jean Britten | Dispersible pharmaceutical compositions |
EP1618114B1 (de) | 2003-04-16 | 2010-07-14 | Sandoz AG | Verfahren zur herstellung von cefepim |
US7847093B2 (en) * | 2003-04-16 | 2010-12-07 | Sandoz Ag | Processes for the preparations of cefepime |
US20050119244A1 (en) * | 2003-12-02 | 2005-06-02 | Acs Dobfar S.P.A. | Process for preparing cephalosporins with salified intermediate |
EP1704153A2 (de) * | 2004-01-16 | 2006-09-27 | Wockhardt Limited | Verbessertes verfahren zur herstellung von cefotaxim-natrium |
CN105153197B (zh) * | 2015-07-28 | 2017-05-31 | 齐鲁安替制药有限公司 | 一种头孢中间体的制备方法 |
Family Cites Families (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2470083A (en) * | 1946-04-03 | 1949-05-17 | Walter H Hartung | Ethers of oximino acid chlorides |
US2542812A (en) * | 1946-04-03 | 1951-02-20 | Walter H Hartung | Preparation of aminoacidamides |
US3038007A (en) * | 1958-05-23 | 1962-06-05 | Reeve Edward Wilkins | Process for the preparation of dl-threonine |
US3104258A (en) * | 1958-09-25 | 1963-09-17 | Fmc Corp | Novel synthesis of amino acids |
US3167549A (en) * | 1961-05-18 | 1965-01-26 | Smith Kline French Lab | Derivatives of 7-aminocephalosporanic acid |
US3360515A (en) * | 1964-07-24 | 1967-12-26 | Fujisawa Pharmaceutical Co | 7-(condensed n-containing heterocyclic carbonamido) cephalosporanic acid and derivatives thereof |
US3338897A (en) * | 1965-03-10 | 1967-08-29 | Fujisawa Pharmacentical Co Ltd | 7-(alpha-substituted acyl amino) cephalosporanic acid and derivatives thereof |
US3661977A (en) * | 1968-04-25 | 1972-05-09 | Shionogi & Co | Novel dioximes and processes for preparing the same |
GB1364453A (en) * | 1970-11-06 | 1974-08-21 | Gist Brocades Nv | Penicillanic and cepholosporanic acid derivatives |
US3855213A (en) * | 1971-02-18 | 1974-12-17 | Smith Kline French Lab | 3-heterocyclic thiomethyl-cephalosporins |
US4024134A (en) * | 1971-01-29 | 1977-05-17 | Glaxo Laboratories Limited | Syn isomers of cephalosporins having α-hydroximino- or α-acyloxyiminoacylamido groups at position-7 |
US3971778A (en) * | 1972-05-12 | 1976-07-27 | Glaxo Laboratories Limited | Cephalosporins having (α-etherified oximino)acylamido groups at the 7-position |
US3974153A (en) * | 1971-05-14 | 1976-08-10 | Glaxo Laboratories Limited | 7-Hydrocarbonoxy imino-acetamido-3-carbamoyloxy methylceph-3-em-4 carboxylic acids |
GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
US4024137A (en) * | 1971-05-14 | 1977-05-17 | Glaxo Laboratories Limited | 7β-[2-Etherified oximino-2-(phenyl- or naphthylacetamido)] cephalosporins |
US4024133A (en) * | 1971-05-14 | 1977-05-17 | Glaxo Laboratories Limited | 7β-[2-Etherified oximino-2-(thienyl-,furyl- or pyridylacetamido)]cephalosporins |
US3966717A (en) * | 1971-05-14 | 1976-06-29 | Glaxo Laboratories Limited | 7-β-Acylamido-3-carbamoyloxymethylceph-3-em-4-carboxylic acids and salts thereof |
US3821207A (en) * | 1971-06-21 | 1974-06-28 | Smithkline Corp | 7-heterocyclic substituted cephalosporins |
YU36181B (en) * | 1971-11-29 | 1982-02-25 | Merck & Co Inc | Process for obtaining 7-(2-thienylacetamido)-7-methoxy-3-carbamoyloxymethyl-3-cephem-4-carboxylates |
US4032521A (en) * | 1972-12-29 | 1977-06-28 | Merck & Co., Inc. | Cephalosporin phosphonic acid, sulfonic acid and sulfonamide compounds |
US4308380A (en) * | 1973-03-15 | 1981-12-29 | Fujisawa Pharmaceutical Co., Ltd. | 2-Lower alkyl-2 or 3-cephem-4-carboxylic acid derivatives |
DE2512284A1 (de) * | 1974-03-28 | 1975-10-09 | Fujisawa Pharmaceutical Co | Cephalosporansaeurederivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel |
IE41697B1 (en) * | 1974-09-27 | 1980-02-27 | Rhone Poulenc Ind | New cephalosporin derivatives their preparation and compositions containing them |
US4668783A (en) * | 1974-12-19 | 1987-05-26 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido cephalosporin compounds |
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 |
GB1536281A (en) * | 1975-06-09 | 1978-12-20 | Takeda Chemical Industries Ltd | Cephem compounds |
US4011216A (en) * | 1975-04-11 | 1977-03-08 | Bristol-Myers Company | Δ2,3-0-2-Isocephem-4-carboxylic acid and derivatives thereof as antibacterial agents |
-
1975
- 1975-12-04 DK DK548875A patent/DK154939C/da not_active IP Right Cessation
- 1975-12-15 PH PH17868A patent/PH13731A/en unknown
- 1975-12-17 SE SE7514286A patent/SE442202B/xx not_active IP Right Cessation
- 1975-12-17 FR FR7538703A patent/FR2294690A1/fr active Granted
- 1975-12-17 NO NO754296A patent/NO157933C/no unknown
- 1975-12-17 MX MX752873U patent/MX5097E/es unknown
- 1975-12-17 DE DE2559942A patent/DE2559942C2/de not_active Expired
- 1975-12-17 DE DE2556736A patent/DE2556736C2/de not_active Expired
- 1975-12-17 GB GB28892/78A patent/GB1536283A/en not_active Expired
- 1975-12-17 DE DE2560398A patent/DE2560398C2/de not_active Expired
- 1975-12-17 HU HU75TA1464A patent/HU179798B/hu unknown
- 1975-12-18 CA CA000242004A patent/CA1216284A/en not_active Expired
- 1975-12-18 BE BE162887A patent/BE836813A/xx not_active IP Right Cessation
- 1975-12-18 NL NLAANVRAGE7514811,A patent/NL183703C/xx active Protection Beyond IP Right Term
- 1975-12-18 ES ES443627A patent/ES443627A1/es not_active Expired
- 1975-12-18 AU AU87667/75A patent/AU500104B2/en not_active Expired
- 1975-12-19 CH CH1655675A patent/CH624119A5/de not_active IP Right Cessation
- 1975-12-19 US US05/642,356 patent/US4098888A/en not_active Expired - Lifetime
-
1976
- 1976-11-29 FR FR7635966A patent/FR2357552A1/fr not_active Withdrawn
-
1977
- 1977-04-16 ES ES457891A patent/ES457891A1/es not_active Expired
- 1977-07-12 PH PH19987A patent/PH14161A/en unknown
- 1977-07-18 AT AT517277A patent/AT357521B/de not_active IP Right Cessation
- 1977-11-28 CH CH1451477A patent/CH631437A5/de not_active IP Right Cessation
- 1977-12-06 ES ES464772A patent/ES464772A1/es not_active Expired
- 1977-12-06 ES ES464771A patent/ES464771A1/es not_active Expired
- 1977-12-09 DK DK552377A patent/DK155086C/da active
-
1978
- 1978-01-18 US US05/870,932 patent/US4205180A/en not_active Expired - Lifetime
- 1978-01-20 NL NL7800731A patent/NL7800731A/xx not_active Application Discontinuation
- 1978-10-31 CA CA000315026A patent/CA1137492A/en not_active Expired
- 1978-10-31 CA CA315,025A patent/CA1128957A/en not_active Expired
-
1979
- 1979-04-03 SE SE7902954A patent/SE445454B/sv not_active IP Right Cessation
- 1979-05-11 FR FR7912111A patent/FR2434146A1/fr active Granted
- 1979-09-28 FR FR7924297A patent/FR2468599B1/fr not_active Expired
-
1980
- 1980-05-23 CH CH407580A patent/CH628058A5/de not_active IP Right Cessation
- 1980-05-23 CH CH407680A patent/CH633544A5/de not_active IP Right Cessation
- 1980-05-27 NL NL8003054A patent/NL8003054A/nl active Search and Examination
-
1983
- 1983-06-24 US US06/525,663 patent/US4514565A/en not_active Expired - Lifetime
-
1988
- 1988-06-07 US US07/203,409 patent/US4912212A/en not_active Expired - Fee Related
- 1988-06-07 US US07/203,410 patent/US4973684A/en not_active Expired - Fee Related
-
1990
- 1990-01-08 US US07/462,492 patent/US5583216A/en not_active Expired - Lifetime
-
1994
- 1994-02-11 BG BG98461A patent/BG60437B2/bg unknown
-
1995
- 1995-08-22 NL NL950016C patent/NL950016I1/nl unknown
Non-Patent Citations (1)
Title |
---|
NICHTS-ERMITTELT * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2710282A1 (de) | 1976-03-09 | 1977-09-15 | Fujisawa Pharmaceutical Co | 3,7-disubstituierte-3-cephem-4- carbonsaeureverbindungen, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel |
DE2760288A1 (de) * | 1976-03-09 | 1985-05-09 |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE2559942C2 (de) | In &alpha;-Stellung geschützte Oxyimino-&beta;-oxo-&gamma;-halogenbuttersäurederivate und ihre Verwendung zur Herstellung entsprechender 2-Amino-thiazol-4-yl-essigsäurederivate | |
EP0081674B1 (de) | Zwischenprodukte, Verfahren zu deren Herstellung und Verfahren zur Herstellung von Cephalosporinen | |
EP0002735A2 (de) | Verfahren zur Herstellung von Piperonylidencrotonsäureamiden | |
DE3881836T2 (de) | N-(Biphenylmethyl)-3-hydroxyglutaraminsäure und -derivate als hypocholesterolemische Agenzien. | |
DD263055A1 (de) | Verfahren zur herstellung substituierter 3-amino-5-phenyl-thiophene | |
EP0089485A2 (de) | Verfahren zur Herstellung von 5-Chlor-1H-tetrazol-1-carbonsäureestern sowie Verfahren zur Herstellung der erforderlichen Dichlorisonitril-carbonsäureester | |
DE2055796C2 (de) | Verfahren zur Herstellung von 7-Aminocephalosporansäure-Derivaten | |
CH513849A (de) | Verfahren zur Herstellung von Pyrrolinverbindungen | |
CH621351A5 (de) | ||
DE912693C (de) | Verfahren zur Herstellung von 3-Oxy-4-carboxyphenylisothiocyanaten | |
EP0261668B1 (de) | Verfahren zur Herstellung von 4-Alkoxy-2(5H)-thiophenonen | |
DE2129887A1 (de) | 2,4,6-trijodbenzoesaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung als roentgenkontrastmittel | |
DE1141634B (de) | Verfahren zur Herstellung von Dithiolphosphorsaeureestern | |
AT331237B (de) | Verfahren zur herstellung von monoacetalen aromatischer 1,2-diketone | |
EP0012868A1 (de) | 1,2,3-Thiadiazol-5-yl-thioglycolsäure, deren Derivate sowie Verfahren zu deren Herstellung | |
AT331804B (de) | Verfahren zur herstellung von neuen 6-aza-3h-1,4-benzodiazepinen, deren optischen isomeren und deren salzen | |
SU455084A1 (ru) | Способ получени полифторированных 1,3-диоксинафталинов или 1,3-диоксибензолов | |
DE942994C (de) | Verfahren zur Herstellung von 5-Nitrothiophenderivaten | |
EP0396014A2 (de) | Substituierte Biphenylcarbonsäuren, Verfahren zu ihrer Herstellung und neue Zwischenprodukte | |
JP3214139B2 (ja) | パントテン酸誘導体の製造方法 | |
AT358563B (de) | Verfahren zur herstellung von neuen hydroxy- aethyliden-cyanessigsaeure-aniliden sowie von deren physiologisch vertraeglichen salzen | |
AT367394B (de) | Verfahren zur herstellung neuer indanderivate | |
DE701901C (de) | Verfahren zur Herstellung von Thioformamidverbindungen | |
DE2627709A1 (de) | Verfahren zur herstellung von pentahalogenphenyl-malonsaeureestern | |
EP0057827A1 (de) | Verfahren zur Herstellung von 2-Aminopyridinderivaten |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
OI | Miscellaneous see part 1 | ||
OI | Miscellaneous see part 1 | ||
8110 | Request for examination paragraph 44 | ||
AC | Divided out of |
Ref country code: DE Ref document number: 2556736 Format of ref document f/p: P |
|
D2 | Grant after examination | ||
8364 | No opposition during term of opposition |