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Details for Patent: 7,674,887

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Details for Patent: 7,674,887

Title:Thrombopoietin mimetics
Abstract: Invented are non-peptide TPO mimetics. Also invented are novel processes and intermediates used in the preparation of the presently invented compounds. Also invented is a method of treating thrombocytopenia, in a mammal, including a human, in need thereof which comprises administering to such mammal an effective amount of a selected hydroxy-1-azobenzene derivative.
Inventor(s): Duffy; Kevin J. (Collegeville, PA), Luengo; Juan I. (Collegeville, PA), Shaw; Antony N. (Collegeville, PA), Wiggall; Kenneth (Collegeville, PA)
Assignee: GlaxoSmithKline LLC (Philadelphia, PA)
Filing Date:Jun 18, 2008
Application Number:12/141,379
Claims:1. A process for preparing a compound of the Formula: ##STR00015## by reaction of a compound of the formula or a salt thereof: ##STR00016## or a protected form thereof with a compound of Formula (VIII) or tautomeric equivalent (IX) ##STR00017## wherein either: R is a phenyl or pyridinyl ring substituted by one or more of the following: --(CH.sub.2).sub.gC(O)OR.sup.8, tetrazole, phosphonic acid, sulfonic acid, hydroxy, methyl, fluoro, NHSO.sub.2CF.sub.3, and C(O)NHSO.sub.2CH.sub.3, and R.sup.1 is hydrogen, where g is 0 to 6 and R.sup.8 is hydrogen or alkyl, or: R is hydrogen; and R.sup.1 is a phenyl or pyridinyl ring substituted by one or more of the following: --(CH.sub.2).sub.gC(O)OR.sup.8, tetrazole, phosphonic acid, sulfonic acid, hydroxy, methyl, fluoro, NHSO.sub.2CF.sub.3, and C(O)NHSO.sub.2CH.sub.3, where g is 0 to 6 and R.sup.8 is hydrogen or alkyl, and in either case: R.sup.2 and R.sup.3 are independently selected from: hydrogen, C.sub.1-6alkyl and halogen; R.sup.15 is selected from the group consisting: of C.sub.1-4alkyl, C.sub.1-4alkoxy, trifluoromethyl and halogen; Y is phenyl that is optionally substituted with from one to five substituents selected from the group consisting of: alkyl, substituted alkyl, trifluoromethyl and halogen; and m is 0 optionally followed by salt formation.

2. A process for preparing a compound of the Formula: ##STR00018## by reaction of a compound of the formula or a salt thereof: ##STR00019## or a protected form thereof with a compound of Formula (VIII) or tautomeric equivalent (IX) ##STR00020## wherein either: R is a phenyl or pyridinyl ring substituted by one or more of the following: --C(O)OH, tetrazole, phosphonic acid, sulfonic acid, hydroxy, methyl, fluoro, NHSO.sub.2CF.sub.3, and C(O)NHSO.sub.2CH.sub.3, and R.sup.1 is hydrogen, or: R is hydrogen; and R.sup.1 is a phenyl or pyridinyl ring substituted by one or more of the following: --C(O)OH, tetrazole, phosphonic acid, sulfonic acid, hydroxy, methyl, fluoro, NHSO.sub.2CF.sub.3, and C(O)NHSO.sub.2CH.sub.3, and in either case: R.sup.2 and R.sup.3 are independently selected from: hydrogen, C.sub.1-6alkyl and halogen; R.sup.15 is selected from the group consisting: of C.sub.1-4alkyl, C.sub.1-4alkoxy, trifluoromethyl and halogen; Y is phenyl that is optionally substituted with from one to five substituents selected from the group consisting of: alkyl, substituted alkyl, trifluoromethyl and halogen; and m is 0 optionally followed by salt formation.

3. The compound 3'-Amino-2'-hydroxybiphenyl-3-carboxylic acid.

4. A process for preparing the compound 3'-{N'-[1-(3,4-Dimethylphenyl)-3-methyl-5-oxo-1,5-dihydropyrazol-4-yliden- e]hydrazino}-2'-hydroxybiphenyl-3-carboxylic acid, which process comprises converting the compound 3'-Amino-2'-hydroxybiphenyl-3-carboxylic acid into 3'-{N'-[1-(3,4-Dimethylphenyl)-3-methyl-5-oxo-1,5-dihydropyrazol-4-y- lidene]hydrazino}-2'-hydroxybiphenyl-3-carboxylic acid.
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