CH631437A5 - Verfahren zur herstellung neuer buttersaeurederivate. - Google Patents
Verfahren zur herstellung neuer buttersaeurederivate. Download PDFInfo
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- CH631437A5 CH631437A5 CH1451477A CH1451477A CH631437A5 CH 631437 A5 CH631437 A5 CH 631437A5 CH 1451477 A CH1451477 A CH 1451477A CH 1451477 A CH1451477 A CH 1451477A CH 631437 A5 CH631437 A5 CH 631437A5
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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
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung neuer Buttersäurederivate der Formel:
XCH,
•C' &
-C COOH
/ \
Y Z
(XII)
in der X ein Halogenatom ist und Y und Z gemeinsam eine Gruppe der Formel:
NR-
worin R5 eine geschützte Hydroxylgruppe ist, bilden, und von Salzen und Estern dieser Verbindungen.
Die Verbindungen der Formel XII sind wertvolle Zwischenprodukte bei der Herstellung von Thiazolderivaten der Formel:
R1-
T |i
N U C
Y Z
COOH
(XIV)
in der R1 eine gegebenenfalls geschützte Aminogruppe oder Hydroxylgruppe ist und die übrigen Symbole die obgenann-ten Bedeutungen haben, und von Salzen und Estern dieser Verbindungen. Zu diesem Zweck werden die Verbindungen der Formel XII mit Verbindungen der Formel:
R12-C-NH,
(XIII)
s in der R12 ein niederer Alkoxyrest oder eine gegebenenfalls geschützte Aminogruppe ist, umgesetzt und anschliessend gegebenenfalls die Schutzgruppe entfernt.
Ihrerseits können die Thiazolderivate der Formel XIV durch Reaktion mit Cephemverbindungen der Formel:
10
>3
R'
h2n.
0
//
ïl^-OH2R4
COOH
20 in der R3 Wasserstoff oder einen Methoxyrest und R4 Wasserstoff oder den Rest einer nukleophilen Verbindung bedeuten, oder mit Salzen oder Estern derselben zur Herstellung von Cephemverbindungen der Formel:
Nv^*-CH2R COOH
in der R1, R3, R4 und R5 die obengenannten Bedeutungen 35 haben, und von pharmazeutisch unbedenklichen Salzen und von Estern derselben verwendet werden.
In den Buttersäurederivaten der Formel XII bedeuten Y und Z zusammen eine Gruppe der Formel = NRS, worin R5 eine geschützte Hydroxylgruppe darstellt. Als Schutz-40 gruppen der Hydroxylgruppe eignen sich beliebige übliche Schutzgruppen, soweit sie die Reaktion gemäss der Erfindung nicht stören. Geeignet sind im allgemeinen beispielsweise niedere Alkylreste, z.B. Methyl und Äthyl, Arylreste, z.B. Phenyl und Thienyl, und Acylreste, z.B. Acetyl und 45 Bènzoyl.
In den Verbindungen der Formel XII ist X ein Halogenatom, z.B. Chlor, Brom, Jod und Fluor. Die Carboxyl-gruppe kann durch eine aus einem Salze oder einem Ester bestehende Schutzgruppe, die unter milden Bedingungen, so z.B. unter sauren oder alkalischen Bedingungen, durch Reduktion usw., entfernbar ist, geschützt sein. Als Schutzgruppen eignen sich hierzu die in der Peptidsynthese allgemein verwendeten Schutzgruppen der Carboxylgruppe, z.B. Alkalimetalle wie Natrium und Kalium, Alkylreste, z.B. Mess thyl, Äthyl, Propyl, Butyl, sek.-Butyl, Isobutyl und tert.-Bu-tyl, substituierte Alkylreste, z.B. ß-Methylsulfonyläthyl, Tri-chloräthyl und Diphenylmethyl, Arylreste, z.B. Phenyl und Tolyl, substituierte Arylreste, z.B. p-tert.-Butylphenyl und p-Nitrophenyl, Aralkylreste, z. B. Benzyl, Phenäthyl und 60 Tolubenzyl, substituierte Aralkylreste, z.B. p-Methoxyben-zyl und p-Nitrobenzyl.
Die Verbindungen der Formel XII können theoretisch als syn- und anti-Isomere zur Oxyiminogruppe vorliegen, jedoch eignen sich beide Isomere gleich gut zur Verwendung 65 als Zwischenprodukte.
Das erfindungsgemässe Verfahren besteht darin, dass man entsprechende abgeschätzte Oxyimino)-ß-oxo-buttersäurederivate, d.h. Buttersäuren der Formel:
CH, C C COOH
3 II / \
0 Y Z
oder ihre Salze und Ester, halogeniert.
Beispiel 1
Zu einer Losung von 18,7 g Äthyl alpha-Äthoxyimino-ß-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 Natriumbicarbonatlösung und dann mit Wasser in dieser Reihenfolge gewaschen, worauf über wasserfreiem Ma-
3 631437
gnesiumsulfat getrocknet wird. Die getrocknete Lösung wird zur Entfernung des Lösungsmittels eingedampft; der Rückstand besteht aus rohem Äthyl a-Äthoxyimino-ß-oxo-y-brombutyrat.
s Beispiel 2
Zu einer Lösung von 27,3 g Äthyl alpha-methoxyimino-ß-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 io 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-ß-oxo-y-brombuty-i5 rat erhalten wird.
Claims (4)
- 631 437
- 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass das Halogenierungsmittel Brom ist.2PATENTANSPRÜCHE 1. Verfahren zur Herstellung neuer Buttersäurederivate der Formel:XCH,&-C-/ \y zCOOH(XII)in der X ein Halogenatom ist und Y und Z gemeinsam eine Gruppe der Formel:NR-worin R5 eine geschützte Hydroxylgruppe ist, bilden, und von Salzen und Estern dieser Verbindungen, dadurch gekennzeichnet, dass man Buttersäurederivate der Formel:CH.■C-«-C-/ \Y Z■COOHin der Y und Z die obengenannten Bedeutungen haben, oder Salze oder Ester derselben halogeniert.
- 3. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass man Äthyl-a-äthoxyimino-ß-oxo-y-brombuty-rat herstellt.
- 4. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass man Äthyl-a-methoxyimino-ß-oxo-y-brom-butyrat herstellt.
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 |
---|---|
CH631437A5 true CH631437A5 (de) | 1982-08-13 |
Family
ID=26257200
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1655675A CH624119A5 (de) | 1974-12-19 | 1975-12-19 | |
CH1451477A CH631437A5 (de) | 1974-12-19 | 1977-11-28 | Verfahren zur herstellung neuer buttersaeurederivate. |
CH407580A CH628058A5 (de) | 1974-12-19 | 1980-05-23 | Verfahren zur herstellung von cephemverbindungen. |
CH407680A CH633544A5 (de) | 1974-12-19 | 1980-05-23 | Verfahren zur herstellung von thiazolessigsaeureverbindungen. |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1655675A CH624119A5 (de) | 1974-12-19 | 1975-12-19 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH407580A CH628058A5 (de) | 1974-12-19 | 1980-05-23 | Verfahren zur herstellung von cephemverbindungen. |
CH407680A CH633544A5 (de) | 1974-12-19 | 1980-05-23 | Verfahren zur herstellung von thiazolessigsaeureverbindungen. |
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) |
Families Citing this family (166)
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 |
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 |
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 |
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- 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
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PFA | Name/firm changed |
Owner name: TAKEDA CHEMICAL INDUSTRIES, LTD |
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PL | Patent ceased |