D-proline derivatives

Details D-proline derivatives D-proline derivatives

C - Chemistry, Metallurgy

07

D

C07D 207/16 (2006.01) A61K 31/40 (2006.01) A61K 31/41 (2006.01) A61K 31/44 (2006.01) A61K 38/05 (2006.01) C07D 207/22 (2006.01) C07D 401/14 (2006.01) C07D 403/06 (2006.01) C07D 403/14 (2006.01) C07D 405/14 (2006.01) C07D 409/14 (2006.01) C07D 413/14 (2006.01) C07D 417/14 (2006.01) C07D 419/14 (2006.01) C07D 521/00 (2006.01) C07K 5/06 (2006.01)

Patent

CA 2252163

The invention relates to D-prolines of the formula Image wherein R is SH, benzyl or phenyl, optionally substituted by hydroxy or lower alkoxy or the group Image ~; R1 is hydrogen or halogen; X is -(CH2)n-; -CH(R2)(CH2)n-; -CH2O(CH2)n-; -CH2NH-; benzyl, -C(R2)=CH-; -CH2CH(OH)-; or thiazol-2,5-diyl; Y is -S-S-; -(CH2)n-; -O-; -NH-; -N(R2)-; -CH=CH-; -NHC(O)NH-; - N(R2)C(O)N(R2)-; -N[CH2C6H3(OCH3)2]-; -N(CH2C6H5)-; -N(CH2C6H5)C(O)N(CH2C6H5)-; -N(alkoxyalkyl)-; -N(cycloalkyl-methyl)-; 2,6- pyridyl; 2,5-furanyl; 2,5-thienyl; 1,2-cyclohexyl; 1,3-cyclohexyl; 1,4- cyclohexyl; 1,2-naphthyl; 1,4-naphthyl; 1,5-naphthyl; 1,6-naphthyl; biphenylen; or 1,2-phenylen,1,3-phenylen and 1,4-phenylen, wherein the phenylen groups are optionally substituted by 1 - 4 substituents, selected from halogen, lower alkyl, lower alkoxy, hydroxy, carboxy, -COO-lower alkyl, nitrilo, 5-tetrazol, (2-carboxylic acid-pyrrolidin-1-yl)-2-oxo-ethoxy, N- hydroxycarbamimidoyl, 5-oxo-[1,2,4]oxadiazolyl, 2-oxo- [1,2,3,5]oxathiadiazolyl, 5-thioxo-[1,2,4]oxadiazolyl and 5-tert-butylsulfanyl- [1,2,4]oxadiazolyl; X' is -(CH2)n-; -(CH2)n CH(R2)-; -(CH2)n OCH2-; -NHCH2-; benzyl, -CH=C(R2)-; -CH(OH)CH2; or thiazol-2,5-diyl; R2 is lower alkyl, lower alkoxy or benzyl and n is 0-3, and to pharmaceutically acceptable salts and mono- and diesters thereof. The D-prolines of formula I-A and I-B can be used in the treatment or prevention of all forms of central and systemic amyloidosis.

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