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US 7,375,237 B2Granted
Pyrrolizine compounds useful as anti-inflammatory agents
AssigneesBristol-Myers Squibb Company, Cerep SA
InventorsT. G. Murali Dhar, Dharmpal S. Dodd, Dominique Potin, Michele Launay
Life of this patent
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Abstract
Pyrrolizine compounds having the formula (I), or pharmaceutically-acceptable salts thereof, are effective in treating inflammatory or immune diseases, where A is a four- to seven-membered saturated ring, K is O or S, and R1, R2, R3 n, and M are defined in the specification.
Claims5
A compound having the structure of formula (Ic):
- or a pharmaceutically-acceptable salt, enantiomer, or diastereomer, thereof wherein:
- M is methyl, ethyl, propyl, cyclopropyl, or CF3;
- R3 is hydroxy or —OC(═O)phenyl;
- R10 is chloro, fluoro, bromo, or cyano;
- and
- R11 independently at each occurrence is chloro, fluoro, or bromo.
3 more elements
A compound selected from
- (i)
- 7a-(4-Bromobenzyl)-2-(3,5-dichlorophenyl)-1-ethyl-5,6,7,7a-tetrahydro-3H-pyrrolizin-3-one;
- 7a-(4-Bromobenzyl)-1-cyclopropyl-2-(3,5-dichlorophenyl)-5,6,7,7a-tetrahydro-3H-pyrrolizin-3-one;
- (6R)-7a-(4-Bromobenzyl)-2-(3,5-dichlorophenyl)-1-ethyl-6-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-3-one;
- (6R)-7a-(4-Bromobenzyl)-2-(3,5-dichlorophenyl)-1-ethyl-6-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-3-one;
- 4-{[6-(3,5-Dichlorophenyl)-7-ethyl-5-oxo-2,3-dihydro-1H-pyrrolizin-7a(5H)-yl]methyl}benzonitrile;
- 4-{[(2R)-6-(3,5-Dichlorophenyl)-7-ethyl-2-hydroxy-5-oxo-2,3-dihydro-1H-pyrrolizin-7a(5H)-yl]methyl}benzonitrile;
- (2S,7aR)-7a-(4-bromobenzyl)-6-(3,5-dichlorophenyl)-7-ethyl-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizin-2-yl benzoate;
- (2S,7aS)-7a-(4-Bromobenzyl)-6-(3,5-dichlorophenyl)-7-ethyl-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizin-2-yl benzoate;
- (6S, 7aS)-7a-(4-Bromobenzyl)-2-(3,5-dichlorophenyl)-1-ethyl-6-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-3-one;
- 4-{[6-(3,5-Dichlorophenyl)-7-methyl-5-oxo-2,3-dihydro-1H-pyrrolizin-7a(5H)-yl]methyl}benzonitrile;
- 4-{[6-(3,5-Dichlorophenyl)-7-methyl-5-oxo-2,3-dihydro-1H-pyrrolizin-7a(5H)-yl]methyl}benzonitrile;
- 7a-(4-Cyanobenzyl)-6-(3,5-dichlorophenyl)-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizine-7-carbonitrile;
- 7a-(4-Cyanobenzyl)-6-(3,5-dichlorophenyl)-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizine-7-carbonitrile;
- (2R)-7a-(4-cyanobenzyl)-6-(3,5-dichlorophenyl)-2-hydroxy-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizine-7-carbonitrile;
- and
- 4-[6-(3,5-Dichloro-phenyl)-7-methoxy-5-oxo-2,3-dihydro-1H,5H-pyrrolizin-7a-ylmethyl]-benzonitrile;
- or
- (ii) a pharmaceutically-acceptable salt, enantiomer, or diastereomer of (i), thereof.
16 more elements
Dependencies are inferred from the claim text.