Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Patent
1985-02-11
1987-10-13
Gerstl, Robert
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
549415, 549422, 549473, 549475, 560106, 560107, 560118, 560121, 560231, 562500, 562503, C07C17700
Patent
active
046999892
DESCRIPTION:
BRIEF SUMMARY
FIELD OF TECHNOLOGY
The present invention relates to novel 7-fluoroprostaglandins and a process for their production.
Further, the present invention relates to a novel process for producing 7-fluoroprostaglandins I.sub.2 by using the novel 7-fluoroprostaglandins.
BACKGROUND OF TECHNOLOGY
7-Fluoroprostaglandins I.sub.2 represented by the following formula (III') and having an alternative name of 7-fluoroprostacyclines (or their non-toxic salts when R.sup.10 is a hydrogen atom), are known, and disclosed in e.g. Japanese Unexamined Patent Publication No. 99580/1982 (GB No. 2088856), Japanese Unexamined Patient Publication No. 165382/1982 (EP No. 54795) or Japanese Unexamined Patent Publication No. 171988/1982 (GB No. 2094310). ##STR2##
In the formula, R.sup.10 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, R.sup.11 and R.sup.12 are hydrogen atoms or the same or different protective groups, respectively, and R.sup.5' is a straight chained or branched alkyl group.
In the above formula (III'), numerals 1 to 15 alloted to the carbon atoms, designate the positions of the carbon atoms.
Natural prostaglandin I.sub.2 (hereinafter referred to as "PGI.sub.2 " including synthesized products) is chemically unstable, and it is difficult to handle it in a neutral or weakly acidic condition. Whereas, 7-fluoroprostaglandins I.sub.2 represented by the above formula (III') are extremely stable under the above condition, and believed to be useful from the aspect of the improvement of the selectivity for pharmacological activities. These 7-fluoroprostaglandins I.sub.2 are prepared by the fluorination of 7-hydroxy PGI.sub.2 (see the abovementioned Japanese Unexamined Patent Publication No. 165382/1982) or by a process disclosed in the abovementioned Japanese Unexamined Patent Publication No. 171988/1982. However, these processes have various problems such as poor yield and selectivity, or the complexity of the reaction steps. Therefore, it has been desired to solve these problems.
SUMMARY OF THE INVENTION
The present invention provides fluorinated novel prostaglandins useful as intermediates for the production of 7-fluoroprostaglandins I.sub.2, and a process for their production.
Further, the present invention relates to a process for producing 7-fluoroprostaglandins I.sub.2 which are basically known as mentioned above, which is characterized in that the novel 7-fluoroprostaglandins are used as intermediates.
Novel 7-fluoroprostaglandins (hereinafter referred to as 7-FPGF) of the present invention are compounds represented by the following formula (I): ##STR3##
In the formula (I), R.sup.1 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, R.sup.2, R.sup.3 and R.sup.4 are hydrogen atoms or the same or different protective groups, respectively, and R.sup.5 is a straight chained, branched or cyclic alkyl group having from 3 to 7 carbon atoms.
In the above formula (I), numerals 1 to 15 alloted to the carbon atoms designate the positions of the carbon atoms.
The present invention also relates to a process for producing 7-FPGF represented by the above formula (I) by fluorinating 7-hydroxy- (or trimethylsiloxy-) prostaglandins (hereinafter referred to as 7-XPGF) represented by the folowing formula (II), optionally followed by the removal of the protective groups and/or hydrolysis. ##STR4##
In the formula (II), X is a hydrogen atom or a trimethylsilyl group, R.sup.6 is an alkyl group having from 1 to 10 carbon atoms, R.sup.7, R.sup.8, R.sup.9 are the same or different protective groups, respectively, and R.sup.5 is the same alkyl group as R.sup.5 in the above (I).
Furthermore, the present invention relates to a novel process for the production of 7-fluoroprostaglandins I.sub.2, where 7-fluoroprostaglandins I.sub.2 represented by the following formula (III) (or their non-toxic salts when R.sup.10 is a hydrogen atom) are produced via a cyclization reaction characterized by the use of 7-FPGF represented by the above formula (I). ##STR5##
In the formula (III), R.sup.10 is a hydrogen atom or
REFERENCES:
patent: 4634782 (1987-01-01), Holland
Arata Yasuda
Keiichi Uchida
Masaaki Yamabe
Masao Kato
Asahi Glass Company Ltd.
Gerstl Robert
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