CH631437A5 - Verfahren zur herstellung neuer buttersaeurederivate. - Google Patents

Verfahren zur herstellung neuer buttersaeurederivate. Download PDF

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Publication number
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
Authority
CH
Switzerland
Prior art keywords
formula
acid derivatives
cooh
compounds
group
Prior art date
Application number
CH1451477A
Other languages
English (en)
Inventor
Michihiko Ochiai
Osami Aki
Akira Morimoto
Taiichi Okada
Kenji Kawakita
Yoshihiro Matsushita
Original Assignee
Takeda Chemical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26257200&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CH631437(A5) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
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 CH631437A5 publication Critical patent/CH631437A5/de

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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

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  • 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)

  1. 631 437
  2. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass das Halogenierungsmittel Brom ist.
    2
    PATENTANSPRÜCHE 1. Verfahren zur Herstellung neuer Buttersäurederivate der Formel:
    XCH,
    &
    -C-/ \
    y z
    COOH
    (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
    ■COOH
    in der Y und Z die obengenannten Bedeutungen haben, oder Salze oder Ester derselben halogeniert.
  3. 3. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass man Äthyl-a-äthoxyimino-ß-oxo-y-brombuty-rat herstellt.
  4. 4. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass man Äthyl-a-methoxyimino-ß-oxo-y-brom-butyrat herstellt.
CH1451477A 1974-12-19 1977-11-28 Verfahren zur herstellung neuer buttersaeurederivate. CH631437A5 (de)

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) DE2556736C2 (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 (168)

* Cited by examiner, † Cited by third party
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US4493833A (en) * 1976-04-12 1985-01-15 Fujisawa Pharmaceutical Co., Ltd. Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds
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
DE2760484C2 (de) * 1976-04-14 1992-12-03 Takeda Chemical Industries, Ltd., Osaka, Jp
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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
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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
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PH17188A (en) * 1977-03-14 1984-06-14 Fujisawa Pharmaceutical Co New cephem and cepham compounds and their pharmaceutical compositions and method of use
SE439312B (sv) * 1977-03-25 1985-06-10 Roussel Uclaf Sett att framstella nya oximderivat av 3-acetoximetyl-7-aminotiazolylacetamido cefalosporansyra
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JPS5936891B2 (ja) 1977-12-09 1984-09-06 武田薬品工業株式会社 保護基の脱離方法
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NL183703C (nl) 1989-01-02
NO754296L (de) 1976-06-22
FR2468599A1 (fr) 1981-05-08
ATA517277A (de) 1979-12-15
ES464772A1 (es) 1979-01-01
DE2556736C2 (de) 1982-02-11
NL7800731A (nl) 1978-05-31
NO157933C (no) 1988-06-15
FR2294690A1 (fr) 1976-07-16
MX5097E (es) 1983-03-16
BE836813A (fr) 1976-06-18
AU8766775A (en) 1977-06-23
SE442202B (sv) 1985-12-09
DE2559942C2 (de) 1985-02-28
DK548875A (da) 1976-06-20
ES464771A1 (es) 1978-09-01
NL950016I1 (nl) 1996-03-01
FR2434146B1 (de) 1984-02-10
NO157933B (no) 1988-03-07
DK155086B (da) 1989-02-06
US4098888A (en) 1978-07-04
US4205180A (en) 1980-05-27
CA1216284A (en) 1987-01-06
AT357521B (de) 1980-07-10
NL7514811A (nl) 1976-06-22
AU500104B2 (en) 1979-05-10
ES457891A1 (es) 1978-08-01
FR2468599B1 (fr) 1986-03-21
US5583216A (en) 1996-12-10
HU179798B (en) 1982-12-28
ES443627A1 (es) 1977-10-16
DK155086C (da) 1989-06-19
DE2560398C2 (de) 1983-09-29
SE445454B (sv) 1986-06-23
DE2556736A1 (de) 1976-06-24
DK552377A (da) 1977-12-09
CH633544A5 (de) 1982-12-15
SE7902954L (sv) 1979-04-03
SE7514286L (sv) 1976-06-21
CA1128957A (en) 1982-08-03
NL183703B (nl) 1988-08-01
PH14161A (en) 1981-03-19
FR2357552A1 (fr) 1978-02-03
CH628058A5 (de) 1982-02-15
GB1536283A (en) 1978-12-20
DK154939C (da) 1989-06-12
NL8003054A (nl) 1980-08-29
BG60437B2 (bg) 1995-03-31
US4912212A (en) 1990-03-27
US4514565A (en) 1985-04-30
PH13731A (en) 1980-09-09
CA1137492A (en) 1982-12-14
FR2294690B1 (de) 1982-01-29
US4973684A (en) 1990-11-27
FR2434146A1 (fr) 1980-03-21
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DK154939B (da) 1989-01-09

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