A new synthetic method of JAK inhibitor baricitinib and its intermediate

A technology for baricitinib and a synthesis method, applied in the field of medicine and chemical industry, can solve the problems of expensive 3-hydroxyazetidine starting material, unsatisfactory product yield and purity, poor acetonitrile stability, etc. Route efficiency and atom economy, simplified separation and purification process, simple operation effect
CN106946917BActive Publication Date: 2019-06-11HANGZHOU CHEMINSPIRE TECH CO LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
HANGZHOU CHEMINSPIRE TECH CO LTD
Publication Date
2019-06-11

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Abstract

The present invention provides a new synthesis method of a baricitinib compound 11. According to the present invention, by using a compound 1 as a staring raw material, the amino group is protected by directly using ethanesulfonyl chloride, and direct cyclization is directly performed by using the effect of an alkali to obtain a key intermediate compound 3 so as to avoid the use of other protection groups and substantially improve the route efficiency and the atomic economy; during the compound 5 preparation, a Wittig reaction is performed by using triphenylphosphine acetonitrile so as to avoid the use of strong alkali and improve the reaction yield; the completely-new neopentyl glycol borate derivative compound 8 has good stability and good crystallinity so as to simplify the separation and purification process; and the route is simple to operate and has the high yield, the purity of the obtained product is high, and the synthesis method is suitable for amplification production. The formulas 1-11 are defined in the specification.
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Description

Technical field

[0001] The invention belongs to the field of medicine and chemical industry, and specifically relates to a new intermediate for rheumatoid arthritis drug baritinib, a method for synthesizing the same, and a method for preparing baritinib by using the intermediate. Background technique

[0002] Baricitinib is a selective oral JAK1 / JAK2 inhibitor jointly developed by Eli Lilly and Incyte Pharmaceuticals. It can inhibit the intracellular signal transduction of a variety of inflammatory cytokines such as IL-6 and IL-23. , Used to treat autoimmune diseases and related inflammations, such as rheumatoid arthritis, psoriasis and diabetic nephropathy. EMA has approved baricitinib as a single agent or in combination with methotrexate on February 13, 2017 for the treatment of one or more disease-modifying anti-rheumatic drugs (DMARD) to relieve inadequate or intolerant moderate to severe activities Treatment of adult patients with rheumatoid arthritis (RA).

[0003] The chem...

Claims

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