US 7,550,455 B2
8-(piperazin-1yl)- and 8-([1,4]diazepan-1yl)-xanthines, the preparation thereof and their use as pharmaceutical composition
Frank Himmelsbach, Mittelbiberach (Germany); Elke Langkopf, Warthausen (Germany); Matthias Eckhardt, Biberach (Germany); Mohammad Tadayyon, Ulm (Germany); and Leo Thomas, Biberach (Germany)
Assigned to Boehringer Ingelheim International GmbH, Ingelheim (Germany)
Filed on Nov. 02, 2004, as Appl. No. 10/979,468.
Claims priority of provisional application 60/530560, filed on Dec. 18, 2003.
Claims priority of application No. 103 55 304 (DE), filed on Nov. 27, 2003.
Prior Publication US 2005/0130985 A1, Jun. 16, 2005
Int. Cl. C07D 473/06 (2006.01); C07D 519/00 (2006.01); A61K 31/522 (2006.01); A61P 3/10 (2006.01); A61P 3/04 (2006.01)
U.S. Cl. 514—218  [514/234.2; 514/263.2; 514/263.21; 514/263.22; 514/263.34; 544/118; 544/268; 544/270; 544/272; 540/575] 16 Claims
 
1. A compound of formula

OG Complex Work Unit Drawing
wherein
R1 is
(a) a heteroaryl-C1-3-alkyl group,
wherein heteroaryl is selected from the group consisting of phenylpyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl and phenanthridinyl which may be optionally substituted by R10, R11 and R12,
where R10 is selected from hydrogen, fluorine, chlorine, bromine, methyl, difluoromethyl, trifluoromethyl, phenyl, cyano, methoxy, difluoromethoxy, trifluoromethoxy, amino, methylamino, dimethylamino, pyrrolidin-1-yl, piperidin-1-yl or morpholin-4-yl group;
R11 is selected from hydrogen, methyl, methoxy or cyano; and
R12 is hydrogen or methyl,
or
(b) a naphthyl-C1-3-alkyl group, which may be substituted by R13 and R14,
where R13 is selected from hydrogen, fluorine, chlorine, bromine methyl, difluoromethyl,
trifluoromethyl, cyano, methoxy, difluoromethoxy or trifluoromethoxy; and
R14 is selected from hydrogen, methyl, methoxy or cyano;
R2 is selected from methyl, ethyl, propyl, isopropyl, cyclopropyl or phenyl;
R3 is selected from 2-butyn-1-yl, 1-buten-1-yl, 2-buten-1-yl or 3-methyl-2-buten-1-yl and
n is 1 or 2;
or a tautomer, enantiomer, diastereomer, mixture, prodrug or salt thereof.