Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-06-16
2002-02-12
Berch, Mark L (Department: 1611)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
06346617
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to intermediate compounds useful in the synthesis of carbapenem antibiotics. The carbapenems derived from the present invention are useful against gram positive microorganisms, especially methicillin resistant
Staphylococcus aureus
(MRSA), methicillin resistant
Staphylococcus epidermidis
(MRSE), and methicillin resistant coagulase negative Staphylococci (MRCNS). There is an increasing need for carbapenems effective against such pathogens, as well as intermediates which facilitate their production. The intermediates of the present invention thus facilitate an important contribution to therapy for treating infections caused by these difficult to control pathogens.
Prior syntheses of similar intermediate compounds have relied on time-consuming, multi-step reaction protocols, and have generated the intermediate as an unstable oil. See, e.g., U.S. Pat. No. 4,960,879, Shionogi & Co. Ltd. The present invention responds to the need for a more facile synthesis yielding novel, more stable carbapenem intermediates.
SUMMARY OF THE INVENTION
The present invention relates to a process for preparation of a compound of formula I:
wherein:
R
1
represents CH
3
or H; and P represents a protecting group;
comprising reacting a compound of formula IV:
wherein R
1
and P and are defined above and R
4
represents triflate or SO
2
F;
in the presence of a catalyst and (R
3
)
3
SnCH
2
OP″, wherein: each R
3
represents C
1-4
lower alkyl, and P″ represents H or a protecting group, to yield the compound of formula I.
This one-vessel process is a more efficient and facile pathway than the traditional multi-step synthesis for preparation of carbapenem intermediates.
The present invention also relates to the compound of formula I:
wherein:
R
1
represents CH
3
or H; and P and P′ independently represent H or a protecting group. This novel compound is a stable and storable crystalline solid.
REFERENCES:
patent: 4960879 (1990-10-01), Kyoto
patent: 0 476 649 (1992-03-01), None
Y. Nagao et al.,J. Org. Chem,57, p 4243-4349 (1992).
S. M. Schmitt et al. J. Antibiotic, 41(6), p. 780-787 (1988).
Chung John Y.
Jensen Mark S.
Leazer, Jr. Johnnie L.
Wells Kenneth M.
Yang Chunhua
Ayler Sylvia A.
Berch Mark L
Daniel Mark R.
Merck & Co. , Inc.
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