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US 7,071,207 B2Granted
Preparation and use of 1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine derivatives for treatment of obesity
AssigneeBayer Pharmaceuticals Corporation
InventorsRoger A. Smith, Stephen J. O'Connor, Wai C. Wong, Soongyu Choi, Harold C. Kluender, Jianmei Fan, Zhonghua Zhang, Rico C. Lavoie, Brent L. Podlogar
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Abstract
This invention relates to 1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine derivatives which have been found to suppress appetite and induce weight loss. The invention also provides methods for synthesis of the compounds, pharmaceutical compositions comprising the compounds, and methods of using such compositions for inducing weight loss and treating obesity and obesity-related disorders.
Claims27
A compound of Formula (I)
- wherein
- R1 is phenyl optionally substituted with one or more halogen, (C1–C6)alkyl, (C1–C6)alkoxy, (C 1–C6)alkylthio, trifluoromethyl, trifluoromethoxy, carboxyl, amino, cyano, nitro, (C1–C6)alkyl-carbonyl-amino, (C1–C6)alkyl-amino-carbonyl-amino, or phenyl optionally substituted with one or more halogen;
- R2 is a hydrogen,
- halogen,
- (C1–C9)alkyl optionally substituted with (C1–C6)alkoxy, trifluoromethyl, or with one or more fluorine,
- phenyl optionally substituted with one or more halogen, (C1–C6)alkyl, (C2–C8)alkenyl, (C2–C8)alkynyl, (C1–C6)alkoxy, (C1–C6)alkyl-thio, trifluoromethyl, trifluoromethoxy, carboxyl, amino, cyano, nitro, (C1–C6)alkyl-carbonyl-amino, (C1–C6)alkyl-amino-carbonyl-amino, or phenyl,
- or
- a 5- to 10-membered aromatic monocyclic or bicyclic heterocyclic radical optionally substituted with one or more halogen, (C1–C6)alkyl, (C1–C6)alkoxy, trifluoromethyl, trifluoromethoxy, cyano, or nitro;
- R3 is hydrogen, (C1–C6)alkyl, or benzyl;
- X is —C(═O)—;
- R4 is
- hydrogen,
- (C1–C9)alkyl optionally substituted with one or more hydroxy, benzyloxy, (C1–C6)alkoxy, trifluoromethyl, cyano, or fluorine,
- benzyl or phenyl, optionally substituted on the phenyl ring with one or more (C1–C6)alkyl, hydroxy, (C1–C6)alkoxy, trifluoromethyl, cyano, nitro, or halogen,
- piperidin-4-yl, piperidin-3-yl, or pyrrolidin-3-yl, each of which may be optionally substituted on the nitrogen atom of the piperidine or pyrrolidine ring with (C1–C6)alkyl, (C1–C6)hydroxyalkyl, benzyl, or phenyl, in which the benzyl or phenyl group may optionally be substituted on the phenyl ring with one or more halogen, (C1–C6)alkyl, (C1–C6)alkoxy, or trifluoromethyl,
- —NR5R6 in which R5 and R6, taken together with the nitrogen atom to which they are attached, form a 5- to 10-membered saturated or unsaturated heterocyclic radical which is optionally substituted with one or more (C1–C6)alkyl, (C1–C6)alkoxy, hydroxy-substituted (C1–C3)alkyl, (C1–C3)alkoxy-substituted (C1–C3)alkyl, benzyl, phenyl, hydroxy, or fluorine,
- or
- a 5- to 10-membered aromatic monocyclic or bicyclic heterocyclic radical optionally substituted with one or more halogen, (C1–C6)alkyl, (C1–C6)alkoxy, trifluoromethyl, cyano, or nitro;
- and pharmaceutical salts and esters thereof.
16 more elements
Dependencies are inferred from the claim text.