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New process for the production of cephalosporines and novel intermediates in this process

Assignee: Sandoz GmbH
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Filing: 1992-08-12
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Granted: —
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Expires: 2012-08-12
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Abstract

Abstract The invention relates to a new economical and simple process, using a new intermediate compound, for the production of 3'-substituted 7-amino-3-propenyl-4-cephem-carboxylic acid derivatives of formula <CHEM> wherein R is hydrogen, a negative charge or a silyl protecting group, R0 is hydrogen or methoxy, R1 is hydrogen or a silyl protecting group and X is the radical of a nucleophile, and their acid addition salts.

Inventors

  • 👤 Johannes Ludescher
  • 👤 Hubert Sturm
  • 👤 Josef Wieser

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-07 13:19
CPC Classifications
C; C07; C07D; C07D501/00; C07D501/14; C07D501/16; C07D501/20; C07D501/24; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/10; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 88 words
A process for the production of 3'-substituted 7-amino-3-propenyl-4-cephem-carboxylic acid derivatives of formula I wherein R₁ is hydrogen or a silyl protecting group, R₀ is hydrogen or methoxy, X is the radical of a nucleophile, R is hydrogen, a silyl protecting group or a negative charge, and their acid addition salts, which comprises the step of i) subjecting a compound of formula IX wherein R₀ is defined as above and R₆ is a silyl protecting group, to a nucleophilic exchange in 3'-position, and optionally splitting off silyl protecting groups.
Claim 2
Dependent Claim 59 words
A process according to claim 1 wherein the compound of formula IX is produced by the step ii) reacting a compound of formula VIII wherein R₀ and R₆ are defined as above, and R₁₀ is a silyl protecting group, an optionally substituted straight or branched alkyl radical, an optionally substituted aryl radical or acyl radical, with an iodinating agent.
Claim 3
Dependent Claim 51 words
A process according to claim 2 wherein the compound of formula VIII is produced by the step iii) silylating a compound of formula VII wherein R₀ is defined as above and R₉ is hydrogen, an optionally substituted straight or branched alkyl radical, an optionally substituted aryl radical or an acyl radical.
Claim 4
Dependent Claim 30 words
A process according to claim 2 or 3 in which steps i), ii) and iii) as defined in claims 1, 2 and 3 are effected in the same reaction vessel.
Claim 5
Dependent Claim 17 words
Compounds of formula IX wherein R₀ is hydrogen or methoxy and R₆ is a silyl protecting group.
Claim 6
Dependent Claim 4 words
7-Trimethylsilylamino-3-(3-iodo-1-propen-1-yl)-3-cephem-4-carboxylic acid trimethylsilyl ester.
Claim 7
Dependent Claim 71 words
A process for the production of a compound of formula IX wherein R₆ is a silyl protecting group and R₀ is hydrogen or methoxy, which comprises the step of ii) reacting a compound of formula VIII wherein R₀ and R₆ are defined as above, and R₁₀ is a silyl protecting group, an optionally substituted straight or branched alkyl radical, an optionally substituted aryl radical or acyl radical, with an iodinating agent.
Claim 8
Dependent Claim 14 words
Use of a compound of formula IX for the production of a 7-acylamino-1-propen-1-yl-3-cephem-4-carboxylic acid.

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