Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1987-12-08
1989-09-12
Rizzo, Nicholas S.
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
C07D48704, A61K 3140
Patent
active
048661716
ABSTRACT:
(1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(1,2-diiminomethyl)-4-pyrazol idinyl]-thio-carbapenum-3-carboxylic acid is provided as an intermediate, which is converted into (1R,5S,6S)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl)]thio- 6-[R-1-hydroxyethyl]-1-methyl-carbapenum-3-carboxylate. This compound is an antibacterial agent, which also may be in the form of the corresponding acid or pharmaceutically acceptable salt, in which case there is included an anionic group balancing the traizolinium positive charge. As such an anionic group may be mentioned, for example, the chloride, acatate or carbonate. As the salt may be mentioned the alkali metal salts, for example, sodium. Also provided in a method for the preparation of (1R,5S,6S)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl)]thio- 6-[R-1-hydroxyethyl]-1-methyl-carbapenem-3-carboxylate, which comprises contacting (1R,5S,6S)-2-[4-pyrazolidinyl]thio-6-[R-1-hydroxyethyl]-1-methyl-carbapene m-3-carboxylic acid with ethyl formimidate hydrohalide under conditions to introduce iminomethyl substitution at each of the free hydrogen positions of the nitrogen atoms of the pyrazolidinyl nucleus and recovering the in situ formed (1R,5S,6S)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl)]thio- 6-[R-1-hydroxyethyl]-1-methyl-carbapenem-3-carboxylate.
REFERENCES:
patent: 4644061 (1987-02-01), Kim
patent: 4680292 (1987-07-01), Christensen et al.
Hikida Muneo
Kumagai Toshio
Machida Yoshisuke
Matsunaga Hiroshi
Nagao Yoshimitsu
Lederle (Japan) Ltd.
Rizzo Nicholas S.
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