IP Library Granted Patent US 7,674,788
Granted Patent B2
US 7,674,788 · App. 11/751,917 · Granted Mar 9, 2010

Substituted pteridines

Assignee: Boehringer Ingelheim International GmbH
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Quick Facts
Patent No.
US 7,674,788
App. No.
11/751,917
Granted
Mar 9, 2010
Kind
B2
Abstract

The invention relates to new pteridines which are suitable for treating respiratory or gastrointestinal complaints or diseases, inflammatory diseases of the joints, skin or eyes, diseases of the peripheral or central nervous system and cancers. This invention also relates to pharmaceutical compositions containing these compounds.

Claims (42)

1. A compound of formula 1,

wherein

R 1 denotes pyrrolidinyl;

and

R 2 denotes piperazinyl;

and wherein

R 3 denotes NHR 3.1 or OR 3.1 , wherein

R 3.1 denotes H or a group selected from among branched or unbranched alkyl with 1 to 6 carbon atoms substituted by one or more hydroxyl groups, C 1-6 -haloalkyl, C 1-6 -alkylene-O—C 1-2 -alkyl, a mono- or bicyclic, saturated or partially unsaturated C 3-10 -cycloalkyl, mono- or bicyclic, saturated or partially saturated, four- to ten-membered heterocyclic group with 1 to 3 heteroatoms selected from S, N or O, and a mono- or bicyclic, five- to ten-membered heteroaromatic group with 1 to 4 heteroatoms selected from S, N or O, which may optionally be substituted by one or more groups selected from among OH, halogen, C 1-6 -alkyl, branched or unbranched alkyl with 1 to 6 carbon atoms substituted by one or more hydroxyl groups, C 1-6 -haloalkyl, COOR 3.3 , O—C 1-6 -alkyl, C 6-10 -aryl, C 3-10 -cycloalkyl, four- to ten-membered heterocyclic group, five- to ten-membered heteroaromatic group and O—C 1-4 -alkyl-phenyl, while this group may in turn optionally be substituted by at least one group selected from among halogen, OH, C 1-3 -alkyl, and C 1-3 -haloalkyl,

and wherein

R 3.3 denotes H, C 1-6 -alkyl or branched or unbranched alkyl with 1 to 6 carbon atoms substituted by one or more hydroxyl groups,

or wherein

R 3 denotes a saturated or partially saturated, bi- or polycyclic seven-, eight-, nine- or ten-membered heterocyclic group, which contains a nitrogen atom and may optionally contain one, two or three other atoms selected from among nitrogen, sulphur and oxygen and

which may optionally be substituted by one or more groups selected from among OH, halogen, C 1-6 -alkyl, branched or unbranched alkyl with 1 to 6 carbon atoms substituted by one or more hydroxyl groups, C 1-4 -alkyl-O—C 1-3 -alkyl, C 6-10 -aryl, C 3-10 -cycloalkyl, five- to ten-membered heteroaryl, four- to ten-membered heterocyclic group, C 1-2 -alkylene-C 5-10 -heteroaryl and C 1-2 -alkylene-C 4-10 heterocycle, which may in turn optionally be substituted by one or more groups selected from among methyl, ethyl, O-methyl, Cl, F and OH,

and the pharmacologically acceptable salts, diastereomers, enantiomers or racemates thereof.

2. The compound according to claim 1 , wherein

R 1 pyrrolidinyl;

and

R 2 piperazinyl;

and wherein

R 3 denotes NHR 3.1 or OR 3.1 , wherein

R 3.1 denotes H or a group selected from among branched or unbranched alkyl with 1 to 6 carbon atoms substituted by one or more hydroxyl groups, C 1-6 -haloalkyl, C 1-6 -alkylene-O—C 1-2 -alkyl, mono- or bicyclic, saturated or partially unsaturated C 3-10 -cycloalkyl, mono- or bicyclic, saturated or partially saturated, four- to ten-membered heterocyclic group with 1 or 2 heteroatoms selected from S, N or O, and a mono- or bicyclic, five- to ten-membered heteroaromatic group with 1, 2 or 3 heteroatoms selected from S, N or O, which may optionally be substituted by one or more groups selected from among OH, C 1-6 -alkyl, branched or unbranched alkyl with 1 to 6 carbon atoms substituted by one or more hydroxyl groups, COO—C 1-3 -alkyl, O—C 1-3 -alkyl, phenyl, C 3-10 -cycloalkyl, four- to ten-membered heterocyclic group, five- to ten-membered heteroaromatic group and O—CH 2 -phenyl, while this group may in turn optionally be substituted by at least one group selected from among halogen, OH, C 1-3 -alkyl, C 1-3 -haloalkyl,

or wherein R 3 denotes a saturated or partially saturated , bi- or polycyclic seven-, eight-, nine- or ten-membered heterocyclic group, which contains a nitrogen atom and which may optionally contain one, two or three other atoms selected from among nitrogen, sulphur and oxygen and

which may optionally be substituted by one or more groups selected from among OH, C 1-6 -alkyl, branched or unbranched alkyl with 1 to 6 carbon atoms substituted by one or more hydroxyl groups, CH 2 —O—CH 3 , phenyl, C 3-10 -cycloalkyl, five- to ten-membered heteroaryl, four- to ten-membered heterocyclic group, CH 2 —C 5 -10 -heteroaryl and CH 2 —C 4-10 heterocycle,

which may in turn optionally be substituted by one or more groups selected from among methyl, O-methyl, Cl and OH,

and the pharmacologically acceptable salts, diastereomers, or racemates thereof.

3. The compound according to claim 1 , wherein

R 3 denotes a saturated or partially saturated, bi- or polycyclic seven-, eight-, nine- or ten-membered heterocyclic group, which contains a nitrogen atom and is linked to the rest of the molecule via this nitrogen atom and which may optionally contain one, two or three other atoms selected from among nitrogen, sulphur and oxygen and which may optionally be substituted by one or more groups selected from among OH, (halogen), C 1-6 -alkyl, branched or unbranched alkyl with 1 to 6 carbon atoms substituted by one or more hydroxyl groups, C 1-4 -alkyl-O—C 1-3 -alkyl, C 6-10 -aryl, C 3-10 -cycloalkyl, five- to ten-membered heteroaryl, four- to ten-membered heterocyclic group, C 1-2 -alkylene-C 5-10 -heteroaryl and C 1-2 -alkylene-C 4-10 heterocycle, which may in turn optionally be substituted by one or more groups selected from among methyl, ethyl, O-methyl, Cl, F and OH,

and the pharmacologically acceptable salts, diastereomers, enantiomers or racemates thereof.

4. The compound according to claim 1 , wherein

R 3.1 denotes a branched or unbranched, alkyl with 1 to 6 carbon atoms substituted by one or more hydroxyl groups or a C 3-6 -cycloalkyl

and the pharmacologically acceptable salts, diastereomers, enantiomers or racemates thereof.

5. The compound according to claim 1 , wherein

R 3 denotes NHR 3.1 or OR 3.1 , and

R 3.1 denotes a saturated or unsaturated, five- or six-membered heterocyclic group with 1 or 2 heteroatoms selected independently of one another from among O, S and N,

which may optionally be substituted by at least one of the groups selected from among OH, methyl, ethyl, a branched or unbranched C 1-4 -alkanol, phenyl and C 3-10 -cycloalkyl.

6. The compound according to claim 5 , wherein

R 3 denotes NHR 3.1 or OR 3.1 and

R 3.1 is tetrahydrofuryl or tetrahydropyranyl, which may optionally be substituted by at least one of the groups selected from among OH, methyl, ethyl, a branched or unbranched alkyl with 1 to 4 carbon atoms substituted by one or more hydroxyl groups, phenyl and C 3-10 -cycloalkyl.

7. The compound according to claim 1 , wherein

R 3 denotes a bicyclic saturated or partially saturated eight-, nine- or ten-membered heterocyclic group which contains a nitrogen atom and is linked to the rest of the molecule via this nitrogen atom and which may optionally contain another atom selected from among nitrogen, sulphur and oxygen and which may optionally be substituted by one or more groups selected from among OH, methyl, ethyl, a branched or unbranched alkyl with 1 to 4 carbon atoms substituted by one or more hydroxyl groups, phenyl, C 3-10 -cycloalkyl, a five- to ten-membered heteroaryl and a four- to ten-membered heterocyclic group,

and the pharmacologically acceptable salts, diastereomers, enantiomers or racemates thereof.

8. A pharmaceutical composition comprising one or more compounds according to claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 12, 2010
From: DOLLINGER, HORST; MARTYRES, DOMNIC; MACK, JUERGEN; GOEGGEL, ROLF; JUNG, BIRGIT; NICKOLAUS, PETER
To: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
Reel/Frame 023767/0296 →
Priority Claims (1)
EP 06114538 · May 24, 2006 · regional
Continuity (1)
Related Publication 20070287704A1 · Dec 13, 2007