1017803-19-8Relevant articles and documents
Convenient preparation of optically pure 3-aryloxy-pyrrolidines
Benard, Christophe,Mohammad, Rahim,Saraswat, Neerja,Shan, Rudong,Maiti, Samarendra N.,Wuts, Peter G. M.,Stier, Michael,Lints, Teresa,Bradow, James,Schwarz, Jacob B.
, p. 517 - 524 (2008)
Chiral 3-methanesulfonyl-1-Boc-pyrrolidine and piperidine were reacted with sodium phenolates, resulting in a mixture of displacement and elimination products. Following carbamate deprotection and pH adjustment, the 3-pyrroline and tetrahydropyridine by-products resulting from elimination were easily removed through aqueous partitioning and/or concentration. Although the pyrrolidines were formed with a high degree of optical purity, slight racemization was observed for the piperidine case because elevated temperatures were required to effect displacement. Copyright Taylor & Francis Group, LLC.
PYRIDINE AMIDE DERIVATIVES AS EP4 RECEPTOR ANTAGONISTS
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Page/Page column 63-64, (2012/06/30)
The invention relates pyridine amide derivative of Formula (I) or a pharmaceutically acceptable salt thereof, wherein R1 and R2 are independently hydrogen, linear o branched (C1-C3)alkyl or joined together they form a cyclopropyl ring; R is independently selected from the group consisting of halogens and trifluoromethyl and p is 1, 2 or 3; A is C or N; E is a group of formula (B) or (C), wherein B is C(O)OH, C(O)O(C1-C3)alkyl, and C is selected from the group consisting of formula (I) m is 1,2 or 3, n is 0 or 1, W is -O-, -O(C1-C3 alkyl)-; -(C1-C3 alkyl)O-; -C(O)-; -C(=N-O(C1-C3 alkyl))-; -NH- or -NH(C1-C3alkyl)-; Ar is phenyl, optionally substituted with one or more substituents selected from the group consisting of halogen, trifluoromethyl, trifluoromethoxy, methyl, -NH(C1-C3alkyl)-; -N(C1-C3alkyl)(C1-C3alkyl)-, a from 5 to 7 membered heterocyclic ring containing one nitrogen atom which is convalently bonded to Ar and optionally containing one or two heteroatoms selected from N, O and S; and a 5- or 6-membered heteroaromatic ring containing 1 to 3 heteroatoms selected from S, O e N, such heteroaromatic ring being substituted with one or two substituents selected from the group consisting of (C1-C3)alkyl, (C3-C5)cycloalkyloxy, (C1-C3)alkylcarbonyl. The compounds of the invention could be used for manufacturing a medicament for the treatment of pathologies which require the use of an antagonist of the EP4 receptor, such as the treatment of acute and chronic pain, inflammatory pain, osteoarthritis, inflammation-associated disorder as arthritis, rheumatoid artrhritis, cancer, endometriosis and migraine.
