| US 7,557,136 B2 | ||
| Pyrrolidine derivatives as oxytocin antagonists | ||
| Matthias Schwarz, Geneve (Switzerland); Catherine Jorand-Lebrun, Contamine-Sarzin (France); and Delphine Valognes, Asson (France) | ||
| Assigned to Laboratoires Serono SA, Coinsins (Switzerland) | ||
| Appl. No. 10/547,032 PCT Filed Feb. 16, 2004, PCT No. PCT/EP2004/050142 § 371(c)(1), (2), (4) Date Sep. 27, 2006, PCT Pub. No. WO2004/076407, PCT Pub. Date Sep. 10, 2004. |
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| Claims priority of application No. 03100477 (EP), filed on Feb. 27, 2003. | ||
| Prior Publication US 2007/0037806 A1, Feb. 15, 2007 | ||
| Int. Cl. A61K 31/40 (2006.01); A61K 31/4245 (2006.01); A61K 31/4184 (2006.01); C07D 207/14 (2006.01); C07D 271/06 (2006.01); C07D 403/06 (2006.01) | ||
| U.S. Cl. 514—423 [514/364; 514/385; 548/539; 548/131; 548/306.1] | 15 Claims |
1. A pyrrolidine derivative of Formula I:
 its optically active forms as enantiomers, diastereomers, mixtures of these and its racemate forms, as well as salts thereof,
wherein:
R1 is selected from the group consisting of H and C1-C6-alkyl;
B is selected from the group consisting of —COO, —CONR4, oxadiazole, thiadiazole or benzimidazole;
R2 is selected from the group consisting of hydrogen, C1-C6-alkyl, aryl, C1-C6-alkyl aryl, heteroaryl, C1-C6-alkyl heteroaryl, C2-C6-alkenyl, C2-C6-alkenyl aryl, C2-C6-alkenyl heteroaryl, C2-C6-alkynyl, C2-C6-alkynyl aryl, C2-C6-alkynyl heteroaryl, C3-C8-cycloalkyl, heterocycloalkyl, C1-C6-alkyl cycloalkyl, C1-C6-alkyl heterocycloalkyl, C1-C6-alkyl carboxy, acyl, C1-C6-alkyl acyl, C1-C6-alkyl acyloxy, C1-C6-alkyl alkoxy, alkoxycarbonyl, C1-C6-alkyl alkoxycarbonyl, aminocarbonyl, C1-C6-alkyl aminocarbonyl, C1-C6-alkyl acylamino, C1-C6-alkyl ureido, amino, C1-C6-alkyl amino, sulfonyloxy, C1-C6-alkyl sulfonyloxy, sulfonyl, C1-C6-alkyl sulfonyl, sulfinyl, C1-C6-alkyl sulfinyl, C1-C6-alkyl sulfanyl, and C1-C6-alkyl sulfonylamino;
R3 is selected from the group consisting of aryl and heteroaryl;
R4 is selected from the group consisting of H, C1-C6-alkyl, C1-C6-alkyl aryl, C1-C6-alkyl heteroaryl, aryl, and heteroaryl; or
R2 and R4 can form together with the N atom to which they are linked to, a 5-8 membered saturated or unsaturated heterocycloalkyl ring;
and
n is an integer from 1 to 3.
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