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US 2013/0158004 A1Published application
Azetidine Derivatives
AssigneeBoehringer Ingelheim International GmbH
InventorsMartin FLECK, Bernd NOSSE, Niklas HEINE, Gerald Juergen ROTH
Life of this patent
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Abstract
Azetidine derivatives of which the following is exemplary and their use in the treatment of obesity, diabetes or dyslipidemia.
Claims11
A compound of the formula I
- wherein
- Ar1 is selected from the group Ar1-G1 consisting of:
- 6- to 10-membered aryl and 5- to 10-membered heteroaryl, which may each be substituted with one or more substituents R1,
- wherein two substituents R1 linked to adjacent C-atoms of Ar1 together may form a C3-5-alkylene bridge in which 1, 2 or 3 CH2-groups may be replaced independently of each other by O, C(═O), S, S(═O), S(═O)2, NH or N(C1-4-alkyl)-, wherein the alkylene bridge may optionally be substituted by one or two F atoms or one or two C1-3-alkyl groups;
- and
- R1 is selected from the group R1-G1 consisting of:
- H, F, Cl, Br, I, CN, OH, —NO2, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-10-carbocyclyl, C3-10-carbocyclyl-C1-3-alkyl, C1-6-alkyl-O—, C3-6-alkenyl-O—, C3-6-alkynyl-O—, C3-10-carbocyclyl-O—, C3-10-carbocyclyl-C1-3-alkyl-O—, C1-6-alkyl-S—, C1-6-alkyl-S(═O)—, C1-6-alkyl-S(═O)2—, C3-10-carbocyclyl-S—, C3-10-carbocyclyl-C—1-3-alkyl-S—, C1-4-alkyl-C(═O)—, C3-10-carbocyclyl-C(═O)—, RN1RN2N—, RN1RN2N—C2-3-alkyl-O—, RN1RN2N—C(═O)—, RN1RN2N—S(═O)2—, C1-6-alkyl-C(═O)—NRN1—, C1-6-alkyl-S(═O)2—NRN1—, C1-6-alkyl-C(═O)—NRN1—C1-3-alkyl-, HO—C(═O)—, C1-6-alkyl-O—C(═O)—, heterocyclyl, heterocyclyl-O—, heterocyclyl-C1-3-alkyl, heterocyclyl-C1-3-alkyl-O—, heterocyclyl-C(═O)—, aryl, aryl-C1-3-alkyl, aryl-O—, aryl-C1-3-alkyl-O—, heteroaryl, heteroaryl-C1-3-alkyl, heteroaryl-O— and heteroaryl-C1-3-alkyl-O—,
- wherein in each carbocyclyl and heterocyclyl a CH2-group may optionally be replaced by —C(═O)— or —C(═CRN22)—, and
- wherein each carbocyclyl and heterocyclyl may be optionally substituted with one or more C1-4-alkyl, which may be optionally substituted with one or more substituents RC, and
- wherein each alkyl, carbocyclyl and heterocyclyl may be optionally substituted with one or more substituents RC, and
- wherein each heterocyclyl may be optionally substituted with aryl or heteroaryl, and
- wherein each aryl and heteroaryl group may be optionally substituted with one or more substituents R2,
- RC is selected from the group RC-G1 consisting of:
- F, Cl, Br, CN, OH, C1-4-alkyl-O—, C3-7-cycloalkyl-O—, C3-7-cycloalkyl-C1-3-alkyl-O—, H2N—, (C1-4-alkyl)NH—, (C1-4-alkyl)2N—, C1-4-alkyl-C(═O)—, C1-4-alkyl-S(═O)2—, HO—C(═O)— and C1-4-alkyl-O—C(═O)—, wherein each alkyl or cycloalkyl may be optionally substituted with one or more substituents selected from F and OH, and
- RN1 is selected from the group RN1-G1 consisting of:
- H, C1-6-alkyl, C3-10-carbocyclyl, C3-10-carbocyclyl-C1-3-alkyl, C3-6-alkenyl, C3-6-alkynyl, heterocyclyl, heterocyclyl-C1-3-alkyl, aryl, aryl-C1-3-alkyl, heteroaryl and heteroaryl-C1-3-alkyl,
- wherein each carbocyclyl and heterocyclyl may be optionally substituted with one or more C1-4-alkyl, and
- wherein in each carbocyclyl and heterocyclyl a CH2-group may optionally be replaced by —C(═O)—, and
- wherein each alkyl, carbocyclyl and heterocyclyl may be optionally substituted with one or more substituents RC, and
- wherein each aryl and heteroaryl group may be optionally substituted with one or more substituents R2,
- RN2 is selected from the group RN2-G1 consisting of:
- H and C1-6-alkyl, and
- Ar2 is selected from the group Ar2-G1 consisting of:
- phenylene and a 5- or 6-membered monocyclic heteroaryl group containing 1, 2 or 3 heteroatoms selected from N, O, or S, wherein all of the before mentioned groups may be optionally substituted with one or more substituents R2, and
- R2 is selected from the group R2-G1 consisting of:
- F, Cl, Br, CN, OH, C1-4-alkyl-, C1-4-alkyl-O—, C1-4-alkyl-S—, C1-4-alkyl-S(═O)2—, H2N—, (C1-4-alkyl)NH—, (C1-4-alkyl)2N—, C1-4-alkyl-C(═O)—NH— and heterocyclyl,
- wherein each alkyl may be optionally substituted with one or more F-atoms and/or with a substituent selected from OH, C1-3-alkyl-O— and CN;
- and
- wherein two substituents R2 attached to an aryl or heteroaryl group may be linked to each other and form a C2-5-alkylene bridging group in which 1 or 2-CH2-groups may be replaced by a group independently of each other selected from O, S, NH and N(C1-4-alkyl)-, wherein the C2-5-alkylene bridging group is optionally be substituted by 1 or 2 C1-3-alkyl groups;
- L is selected from the group L-G1 consisting of:
- a C1-4-alkylene group that is optionally substituted by one or two CH3;
- X is selected from the group X-G1 consisting of:
- O and S;
- R is selected from the group R-G1 consisting of:
- H and C1-3-alkyl;
- and
- T is selected from the group T-G1 consisting of:
- C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-10-carbocyclyl, C3-10-carbocyclyl-C1-3-alkyl, C1-6-alkyl-O—, C3-10-carbocyclyl-O—, C3-10-carbocyclyl-C1-3-alkyl-O—, C1-6-alkyl-S—, C3-10-carbocyclyl-S—, C3-10-carbocyclyl-C1-3-alkyl-S—, C1-4-alkyl-C(═O)—, C1-4-alkyl-S(═O)2—, RN1RN2—N—, RN1RN2—N—C1-3-alkyl-, RN1RN2—N—CO—, C1-4-alkyl-C(═O)—RN2N—C1-3-alkyl, heterocyclyl, aryl and heteroaryl,
- wherein in each carbocyclyl and heterocyclyl a CH2-group may optionally be replaced by —C(═O)—, and
- wherein each carbocyclyl and heterocyclyl may be optionally substituted with one or more C1-4-alkyl, which may be optionally substituted with one or more substituents RC, and
- wherein each alkyl, carbocyclyl and heterocyclyl may be optionally substituted with one or more substituents RC, and
- wherein each alkyl may optionally be substituted with a heteroaryl group;
- and
- wherein each aryl and heteroaryl group may be optionally substituted with one or more substituents R2;
- or a tautomer or pharmaceutically acceptable salt thereof.
42 more elements
Dependencies are inferred from the claim text.