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Title:
INTERLEUKIN-1 AND TUMOR NECROSIS FACTOR-ALPHA MODULATORS AND THEIR ENANTIOMERS, THEIR SYNTHESIS AND USE
Document Type and Number:
WIPO Patent Application WO2002079137
Kind Code:
A9
Abstract:
Novel compounds are disclosed that have specific chemical structures, and prodrug esters and acid-addition salts thereof, that are useful as Interleukin-1 and Tumor Necrosis Factor-a modulators, and thus are useful in the treatment of various diseases. Wherein the R groups are defined as follows: if any R3-R5, R7, R8, R11-R13 is not hydrogen, R2 or R6 or R9 is not methyl, or R10 is not CH2, then R1 is selected from the group consisting of hydrogen, a halogen, COOH, C1-C12 carboxylic acids, C1-C12 acyl halides, C1-C12 acyl residues, C1-C12 esters, C1-C12 secondary amides, (C1-C12)(C1-C12) tertiary amides, (C1-C12)(C1-C12) cyclic amides, (C1-C12) amines, C1-C12 alcohols, (C1-C12)(C1-C12) ethers, C1-C12 alkyls, C1-C12 substituted alkyls, C2-C12 alkenyls, C2-C12 substituted alkenyls, and C5-C12 aryls. If all R3-R5, R7, R8, R11-R13 are hydrogen, R2, R6, and R9 are each methyl, and R10 is CH2, then R1 is selected from hydrogen, a halogen, C1-C12 carboxylic acids, C1-C12 acyl halides, C1-C12 acyl residues, C2-C12 esters, C2-C12 secondary amides, (C1-C12)(C1-C12) tertiary amides, C2-C12 alcohols, (C1-C12)(C1-C12) ethers other than methyl-acetyl ether, C2-C12 alkyls, C1-C12 substituted alkyls, C2-C12 alkenyls, C2-C12 substituted alkenyls, and C2-C12 aryls. R2 and R9 are each separately selected from hydrogen, a halogen, C1-C12 alkyl, C1-C12 substituted alkyls, C2-C12 alkenyl, C2-C12 substituted alkenyl, C2 - C12 alkynyl, C1-C12 acyl, C1-C12 alcohol, and C5-C12 aryl. R3-R5, R7, R8, and R11-R13 are each separately selected from hydrogen, a halogen, C1-C12 alkyl, C1-C12 substituted alkyls, C2-C12 alkenyl, C2-C12 substituted alkenyl, C2-C12 alkynyl, and C5-C12 aryl. R6 is selected from hydrogen, a halogen, C1-C12 alkyl, C1-C12 substituted alkyls, C2-C12 alkenyl, C2-C12 substituted alkenyl, and C2-C12 alkynyl. R10 is selected from hydrogen, a halogen, CH2, C1-C6 alkyl, C1-C6 substituted alkyl, C2-C6 alkenyl, C2-C6 substituted alkenyl, C1-C12 alcohol, and C5-C12 aryl. Pharmaceutical compositions comprising, and uses of, therapeutically effective amounts of the aove compounds and their prodrug esters, and a pharmaceutically acceptable carrier, are also disclosed, and are useful as, for example, anti-inflammatory analgesics, in treating immune disorders, as anti-cancer and anti-tumor agents, and in the treatment of cardiovascular disease, skin redness, and viral infection. Completely synthetic and semi-synthetic methods of making these compounds and their analogs, are also disclosed.

Inventors:
PALLADINO MICHAEL
THEODORAKIS EMMANUEL
Application Number:
US0209591W
Publication Date:
May 27, 2004
Filing Date:
March 27, 2002
Export Citation:
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Assignee:
NEREUS PHARMACEUTICALS, INC.
THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
International Classes:
A61P37/02; C07C33/14; C07C61/35; C07C69/00; C07C233/58; C07D295/15; C07D295/185; C07D295/26; (IPC1-7): C07C61/35; C07C61/29; C07C69/753; C07C69/757; C07D295/185; C07C233/58; C07C233/62; C07C233/60; C07C33/14; C07C69/38; A61P37/02; A61K31/19; A61K31/215
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