Heterocyclic chemical compound

Details Heterocyclic chemical compound Heterocyclic chemical compound

1998-05-13

2000-04-04

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548413, 514 89, C07F 959, C07F 9572, A61K 31675

Patent

active

060463341

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to a heterocyclic chemical compound containing boron, silicon, nitrogen, phosphorous, sulphur, or selenium in the ring structure. In addition the compound is substituted with stereochemically well defined groups. Such compounds are very difficult to bring about.
According to the present invention, it has quite unexpectedly been possible to prepare novel heterocyclic derivatives possessing unexpected physiological properties. The invention relates to a heterocyclic compound of formula 1 or 2 ##STR2## or a neutral or acidic salt thereof where the counter ion is Li.sup.+, Na.sup.+, K.sup.+, Mg.sup.2+, Ca.sup.2+, NH.sub.4.sup.+ or another pharmacologically acceptable positively charged inorganic or organic ion or any combination thereof, ##STR3## and where the remaining R.sup.1 -R.sup.12 can be selected from H, HY.sup.22, halogen, R.sup.25 , or R.sup.26 Y.sup.23 ; ((Y.sup.24).sub.p R.sup.30) and (V.sup.1).sub.m ((Y.sup.24).sub.p R.sup.30) or R.sup.30)C(R.sup.31).sub.2-q (V.sup.2).sub.q ((Y.sup.25).sub.r R.sup.32); to i), PY.sup.26 Y.sup.27 R.sup.33, S, SO, SO.sub.2, or Se, containing 1-22 carbon atoms, heterocyclic residue containing 3-22 carbon atoms and 0-5 heteroatoms consisting of nitrogen, oxygen, or sulfur, containing 1-22 carbon atoms substituted with a saturated or unsaturated aromatic or non-aromatic homo- or heterocyclic residue containing 3-22 carbon atoms and 0-5 heteroatoms consisting of nitrogen, oxygen, or sulfur, heterocyclic residue containing 3-22 carbon atoms and 0-5 heteroatoms consisting of nitrogen, oxygen, or sulfur, substituted with a straight or branched saturated or unsaturated alkyl residue containing 1-22 carbon atoms, unsubstituted or substituted with 0-6 of the following groups: hydroxy, alkoxy, aryloxy, acyloxy, carboxy, alkoxycarbonyl, alkoxycarbonyloxy, aryloxycarbonyl, karbamoyl, fluoro, chloro, bromo, azido, cyano, oxo, oxa, amino, imino, alkylamino, arylamino, acylamino, nitro, alkylthio, alkylsulfonyl.
Thus, the chemical compound according to the invention may be a derivative of piperidin, tetrahydrothiopyran, S-oxotetrahydrothiopyran, S,S-dioxotetrahydrothiopyran, tetrahydroselenopyran, tetrahydrofuran, pyrrolidine, tetrahydro-thiophene, S-oxotetrahydrothiophene, S,S-dioxotetrahydrothiophene, or tetra-hydroselenophene.
The acidic or negatively charged groups consists of, or derive from, a carboxylic acid, thiocarboxylic acid, carboxamide, sulfonic acid, sulfonamide, phosphate, thiophosphate, phosphonate.
The straight or branched saturated or unsaturated alkyl residue in groups 2-6 above can be exemplified by: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, doeicosyl, isopropyl, isobutyl, isopentyl, isohexyl, isoheptyl, isooctyl, isononyl, isodecyl, isodoecosyl, 2-butyl, 2-pentyl, 2-hexyl, 2-heptyl, 2-octyl, 2-nonyl, 2-decyl, 2-doeicosyl, 2-methylbutyl, 2-methylpentyl, 2-methylhexyl, 2-methylheptyl, 2-methyloctyl, 2-methylnonyl, 2-methyldecyl, 2-methyleicosyl, 2-ethylbutyl, 2-ethylpentyl, 2-ethylhexyl, 2-ethylheptyl, 2-ethyloctyl, 2-ethylnonyl, 2-ethyldecyl, 2-ethyleicosyl, tertbutyl, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, heneicosenyl, doeicosenyl, butadienyl, pentadienyl, hexadienyl, heptadienyl, octadienyl, nonadienyl, decadienyl, doeicodienyl, ethynyl, propynyl, doeicosynyl.
The saturated or unsaturated aromatic or non-aromatic homo- or heterocyclic residue in groups 2-6 above can be exemplified by: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, cyclopentadecyl, cyclohexadecyl, cycloheptadecyl, cyclooctadecyl, cyclononadecyl, cycloeicosyl, cycloheneicosyl, cyclodoeicosyl, adamantyl, cyclopropenyl, cyclobutenyl, cyclopenten

REFERENCES:
Mats Malmberg et al., "A Facile Synthesis of N-Substituted D-Arabino-Piperidinol Phosphates from the Inositol Phosphate .alpha.-Trinositol", Synlett (Apr. 1996), pp. 361-362.

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