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2, 6-diamino- pyrimidin- 5-yl-carboxamides as SYK or JAK kinases inhibitors
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A compound, amino technology, applied in the preparation of the compound described in this article, the treatment of the disease field characterized by other indications, can solve problems such as Src kinase inactivity
Active Publication Date: 2011-05-18
PORTOLA PHARMA INC
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Interestingly, this ATP-competitive inhibitor of Syk is also active against Flt3, cKit and JAK kinases, but not against Src kinase (Braselmann, Taylor et al., 2006)
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[0309] a. Compound
[0310] In one group of embodiments, the present invention provides a compound having formula (I), a tautomer or a pharmaceutically acceptable salt thereof:
[0311]
[0312] in:
[0313] Y 1 selected from:
[0314]
[0315] Z is O or S;
[0316] D. 1 selected from:
[0317] (a) By group R 5 Substituted phenyl, wherein phenyl is also optionally substituted by 1-2 substituents R 7a replace, R 7a Independently selected from C 1-8 Alkyl, C 1-8 Alkoxy, halo, C 1-8 Alkylsulfonyl and heterocyclyl;
[0327] L is selected from -CO-, -O-, -SO 2 -, -CONH- and -CONHCH 2 -;
[0328] Each R 5 is optionally further substituted with 1-2 substituents independently selected ...
Embodiment 1
[0640] Example 1: 4-(4-(4-acetylpiperazin-1-yl)anilino)-2-((1R,2S)-2-aminocyclohexylamino)pyrimidine-5-carboxamide
[0641]
[0642] Step 1: To a solution of carboxylic acid 72.1 (85 g, 540 mmol) in thionylchloride (425 mL) was slowly added pyridine (8.5 mL, 0.11 mmol) with stirring. The reaction was stirred overnight at 75 °C, then concentrated and dried in vacuo to a pale yellow powder. The yellow solid was slowly diluted with 750 mL of ethanol and refluxed overnight. The next day, the reaction was determined to be complete by HPLC, then cooled in an ice bath, and the solid was filtered and washed with ether to afford the ethyl ester 72.2 as an off-white powder (91 g, 87% for two steps). C 7 h 8 N 2 o 4 The MS measured value is (M+H) + 185.0.
[0643] Step 2: Ester 72.2 (22 g, 120 mmol) was dissolved in phosphorus oxychloride (60 mL, 600 mmol), the mixture was treated with N,N-diethylaniline (27 mL, 167 mmol), the mixture was heated to 105 °C until the reaction wa...
Embodiment 2
[0648] Example 2: 2-((1R,2S)-2-aminocyclohexylamino)-4-(4-(1,1-dioxo)thiomorpholineanilino)pyrimidine-5-carboxamide
[0649]
[0650] Using the same synthetic scheme shown in Example 1, substituting 4-(1,1-dioxo)thiomorpholineaniline for aniline 72.4, the above racemic compound was prepared. C 21 h 29 N 7 o 3 The MS measured value of S is (M+H) + 460.2. UVλ=236, 312nm.
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Abstract
The present invention is directed to compounds of formula I-V and tautomers thereof or pharmaceutically acceptable salts, esters, and prodrugs thereof which are inhibitors of sykkinase. The present invention is also directed to intermediates used in making such compounds, the preparation of such a compound, pharmaceutical compositions containing such a compound, methods of inhibition sykkinase activity, methods ofinhibilion the platelet aggregation, and methods to prevent or treat a number of conditions mediated at least in part by sykkinase activity, such as cardiovascular disease, inflammatory disease and autoimmune disease and cell proliferative disorder. Formula (I) Y1 is selected from the group consisting of: (a) and (b); Z is O or S; D1 is selected from the group consisting of: (a) phenyl substituted with a group, R5 (b) naphthyl (c) C3-8cycloalkyl (d) heteroaryl (e) heterocyclyl.
Description
[0001] Cross References to Related Applications [0002] This application claims U.S. Provisional Patent Application No. 61 / 120,348, filed December 5, 2008, U.S. Provisional Patent Application No. 61 / 120,346, filed December 5, 2008, U.S. Provisional Patent Application No. Patent Application No. 61 / 045,406 and the benefit of US Provisional Patent Application No. 61 / 045,499, filed April 16, 2008, the entire contents of which are incorporated herein by reference. technical field [0003] The present invention relates to pyrimidine-5-carboxamide compounds useful as spleentyrosine kinase (syk) and / or JAK kinase inhibitors. The present invention also relates to pharmaceutical compositions comprising pyrimidine-5-carboxamide compounds, and methods of using the compounds or compositions to treat conditions characterized by other indications. The present invention also relates to methods of preparing the compounds described herein. Background technique [0004] Protein kinases con...
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