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US 6,187,780 B1Granted
Assymetrically substituted xanthine derivatives having adenosine A1 antagonistic activity
AssigneeBoehringer Ingelheim Pharma GmbH & Co. KG
InventorsStefan Blech, Adrian Carter, Wolfram Gaida, Ursula Gath, Matthias Hoffmann, Ulrike Kuefner-Muehl, Erich Lehr, Joachim Mierau, Gerald Pohl, Thomas Weiser
Life of this patent
Estimating the term…
Abstract
Asymmetrically substituted xanthine derivatives having adenosine A1 antagonistic activity. These are useful as pharmaceuticals. Exemplary are: (a) 3-(2-(2-acetyloxyethyl)sulphonylethyl)-8-(1-noradamantyl)-1-n-propyl-xanthine; (b) 3-(2-(hydroxyethyl)sulphonylethyl)-8-(1-noradamantyl)-1-n-propyl-xanthine; and, (c) 3-(2-(carbamoylethyl)-8-(1-noradanantyl)-1-n-propyl-xanthine.
Claims9
A compound of the formula (I)
- in which the dotted line between the nitrogen atoms in formula (I) indicates the existence of a double bond in one of two possible positions, with the result that the groups R4 and R5 cannot both be present at the same time and wherein:
- R1 denotes propyl;
- R2 denotes a methyl, ethyl or propyl group substituted by —SO2—CH2—CH2—OR9, —SO2—CH2—CH2—OCOR9, —SO2—CH2—CH2—CH2—OR9, —SO2—CH2—CH2—CH2—OCOR9, —NR7R8, —CONR7R8, pyridyl or pyrimidyl;
- R3 denotes tert.-butyl, norborranyl, norboimenyl, or noradamantyl;
- R4 or R5 denotes hydrogen;
- R7 denotes hydrogen, methyl, ethyl, propyl or —COR9;
- R8 denotes hydrogen, methyl, ethyl, propyl or —COR9;
- or,
- R7 and R8 together with the nitrogen form a pipeiidinyl, morpholinyl, pyrrolyl, pyrrolidinyl or piperazinyl ring which may optionally be substituted by methyl or benzyl;
- and,
- R9 denotes hydrogen, methyl, ethyl or propyl,
- or a pharmaceutically acceptable acid addition salt thereof.
9 more elements
A compound selected from the group consisting of:
- (a) 3-(2-(2-acetyloxyethyl)sulphonylethyl)-8-(1-noradamantyl-1-n-propyl-xanthine;
- (b) 3-(2-(hydroxyethyl)sulphonylethyl)-8-(1-noradamantyl)-1-n-propyl-xanthine;
- (c) 3-(2-(carbamoylethyl)-8-(1-noradamantyl)-1-n-propyl-xanthine;
- (d) 3-(2-(acetamidoethyl)-8-(1-noradamantyl)-1-n-propyl-xanthine;
- (e) 3-(3-(N-morpholino)propyl)-8-(1-noradamantyl)-1-n-propyl-xanthine;
- (f) 3-(3-(4-methylpiperazin-1-yl)propyl)-8-(1-noradamantyl)-1-n-propyl-xanthine;
- (g) 3-(2-(2-acetyloxyethyl)sulphonylethyl)-8-(tert.-butyl)-1-n-propyl-xanthine;
- (h) 8-(tert.-butyl)-3-(2-(2-hydroxyethyl)sulphonylethyl)-1-n-propyl-xanthine;
- (i) 8-(tert.-butyl)-3-(2-carbamoylethyl)-1-n-propyl-xanthine;
- (j) 3-(2-acetamidoethyl)-8-(tert.-butyl)-1-n-propyl-xanthine;
- (k) 8-(tert.-butyl)-3-(3-(N-morphohino)propyl)-1-n-propyl-xanthine;
- (l) 8-(tert.-butyl)-3-(2-(N-methyl-acetamido)ethyl)-1-n-propyl-xanthine;
- (m) 8-(tert.-butyl)-3-(2-N-isopropionyl-N-methyl-anino)ethyl)1-n-propyl-xanthine;
- (n) 8-(tert.-butyl)-3-(2-(N-isopropionyl-amino)ethyl)-1-n-propyl-xanthine;
- (o) 8-(tert.-butyl)-3-(2-(N-morphoiocarbonyl)ethyl)-1-n-propyl-xanthine;
- (p) 8-(tert.-butyl)-3-(2-(4-methylpiperazin-1-yl-carbonyl)ethyl)-1-n-propyl-xanthine;
- (q) 8-(tert.-butyl)-3-(2-(N,N-dimethylaminocarbonyl)ethyl)-1-n-propyl-xanthine;
- (r) 8-(tert.-butyl)-1-n-propyl-3-(2-(4-pyridyl)ethyl)-xanthine;
- (s) 8-(tert.-butyl)-3-(3-(4-methylpiperazin-1-yl)-propyl)-1-n-propyl-xanthine;
- (t) 3-(2-(2-acetyloxyethyl)sulphonylethyl)-8-(1(R)-2-endo-norboman-2-y)-1-n-propyl-xanthine;
- (u) 3-(2-(2-hydroxyethyl)sulphonylethyl)-8-(1(R)-2-endo-norbornan-2-yl)-1-n-propyl-xanthine;
- (v) 3-(2-carbamoylethyl)-8-(1(R-2-endnorbornan-2-yl)-1-n-propyl-xanthine;
- and
- (w) 3-(3-(4-methylpiperazin-1-yl)propyl)-8-(1(R)2-endonorbornan-2-yl)-1-n-propyl-xanthine.
21 more elements
Dependencies are inferred from the claim text.