Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1991-05-07
1993-08-10
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
5142335, 514374, 514307, 514314, 514320, 514397, 544147, 544187, 546139, 546146, 546152, 546269, 549422, 549462, 549463, 549465, C07D30700, C07D40500, C07D40700, C07D41300, C07F 718, C07C40500, A61K 3134, A61K 31557
Patent
active
052350720
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
The invention relates to 2-oxabicyclo[2.2.1]heptane derivatives of formula I ##STR4## as well as their enantiomers, in which A means --(CH.sub.2).sub.n --, (E)-- or (Z)--CH.dbd.CH--, --C.tbd.C, --O-- or --S--, --N.sub.3, --COOR.sup.3, ##STR5## a 5- or 6-member heterocyclic radical with at least one N, O or S atom, R.sup.1 means oxygen or a --CH.sub.2 group, substituted by X or C.sub.7 -C.sub.16 aralkyl substituted by X, cycloalkyl, C.sub.6 -C.sub.12 aryl or C.sub.7 -C.sub.16 aralkyl, ##STR6## --OR.sup.2, halogen, `C.tbd.N, --N.sub.3, --NO.sub.2, --COOR.sup.3, trifluoromethyl, or phenyl; ##STR7## --COOR.sup.5, in which R.sup.5 can means hydrogen or C.sub.1 -C.sub.10 alkyl optionally substituted by halogen, phenyl, C.sub.1 -C.sub.4 alkoxy or di-(C.sub.1 -C.sub.4)-alkylamino, C.sub.5 -C.sub.6 cycloalkyl, C.sub.7 -C.sub.16 aralkyl, phenacyl or C.sub.6 -C.sub.16 aryl substituted by X or a 5- or 6-member heterocyclic radical with at least one N, O or S atom, or --CONHR.sup.6, with R.sup.6 meaning hydrogen, can be C.sub.1 -C.sub.10 alkanoyl or C.sub.1 -C.sub.10 alkanesulfonyl or --CONR.sup.2 R.sup.3 or the radical --CON (CH.sub.2).sub.t or the radical ##STR8## t means 2 or 3, Z means --(CH.sub.2).sub.p --, (E)--CH.dbd.CH. --CH.dbd.CR.sup.7 --, --C.tbd.C--, ##STR9## a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR10## group, in which the OH group can be respectively in alpha- or beta-position ##STR11## a straight-chain saturated alkylene group with 1-5 C atoms, a branched saturated or a straight-chain or branched unsaturated alkylene group with 2-5 C atoms, which optionally can be substituted by fluorine atoms, trifluoromethyl, cycloalkyl, C.sub.7 -C.sub.16 aralkyl optionally substituted by X, C.sub.6 -C.sub.12 aryl optionally substituted by X or a 5- or 6-membered heterocyclic radical with at least one N, O or S atom or, if E represents a direct bond. ##STR12## --O--(CH.sub.26 l).sub.S --L--(CH.sub.2).sub.o --X, in which X can be the same or different in radicals --(X).sub.p, if p=2 or 3, substituted by X or C.sub.7 -C.sub.16 aralkyl substituted by X, cycloalkyl, C.sub.6 -C.sub.12 aryl or C.sub.7 -C.sub.16 aralkyl, ##STR13## --OR.sup.2, halogen, --C.tbd.N, --N.sub.3, --NO.sub.2, --COOR.sup.3 or trifluoromethyl ##STR14## in which R.sup.5 can means hydrogen or C.sub.1 -C.sub.10 alkyl optionally substituted by halogen, phenyl, C.sub.1 -C.sub.4 alkoxy or di-(C.sub.1 -C.sub.4)-alkylamino, C.sub.5 -C.sub.6 cycloalkyl, C.sub.7 -C.sub.16 aralkyl, phenacyl or C.sub.6 -C.sub.12 aryl substituted by X or a 5- or 6-member heterocyclic radical with at least one N, O or S atom, or --CONHR.sup.6, with R.sup.6 meaning hydrogen, can be C.sub.1 -C.sub.10 alkanoyl or C.sub.1 -C.sub.10 alkanesulfonyl or CONR.sup.2 R.sup.3 or the radical. ##STR15## t means 2 or 3, Z means --(CH.sub.2)p--, (E)--CH.dbd.CH, --CH.dbd.CR.sup.7 --, --C.tbd.C, ##STR16## a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR17## group, in which the OH group can be respectively in alpha- or beta-position, B, and B.sup.3 are the same or different and mean C.sub.1 -C.sub.4 alkyl, phenyl or C.sub.7 -C.sub.16 aralkyl, physiologically compatible bases, as well as the alpha-, beta- or gamma-cyclodextrin clathrates, as well as the compounds of formula I encapsulated with liposomes.
The definition "5- or 6-member heterocyclic radicals" relates to heterocycles, which contain at least 1 heteroatom, preferably nitrogen, oxygen or sulfur and are monocyclic or bicyclic. For example, there can be mentioned 2-furyl, 3-furyl, 2-thienyl, 3-thenyl, 2-pyridyl, 4-pyridyl, quinolyl, isoquinolyl.
As alkyl groups R.sup.2, R.sup.3, R.sup.5, R.sup.8 and B, straight-chain or branched-chain alkyl groups with 1-10 C atoms, such as, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, neopentyl, heptyl, hexyl, decyl, are suitable.
Alkyl groups R.sup.2, R.sup.3, R.sup.5, R.sup.8 and B can be substituted by halogen atoms, hydroxy groups. C.sub.1 -C.s
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Klar Ulrich
Rehwinkel Hartmut
Sturzebecher Claus S.
Thierauch Karl H.
Vorbruggen Helmut
Higel Floyd D.
Schering Aktiengsellschaft
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