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Pyrrolo [2,3-d] pyrimidine compounds as immunosuppressive agents

A compound, C2-C6 technology, applied in anti-inflammatory agents, drug combinations, organic chemistry, etc., can solve the problem of JAK3 being limited to hematopoietic cells

Inactive Publication Date: 2003-08-27
PFIZER PRODS ETAT DE CONNECTICUT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

While essentially all tissues express other members of this family, JAK3 expression is restricted to hematopoietic cells

Method used

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  • Pyrrolo [2,3-d] pyrimidine compounds as immunosuppressive agents

Examples

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preparation example Construction

[0081] The following reaction scheme explains the preparation process of the compounds of this invention. In this reaction scheme and the subsequent discussion of R 2 , R 3 , R 4 And R 5 The definition is as above, unless otherwise stated.

[0082] Preparation A Preparation B Preparation C Reaction scheme 1 Reaction scheme 2 Reaction scheme 3

[0083] In reaction 1 of preparation A, R is hydrogen or a 4-chloropyrrolo[2,3-d]pyrimidine compound of formula XXI with a protecting group such as benzenesulfonyl or tolyl, by combining the compound of formula XXI with N-chlorosuccinate The reaction of acid imine, N-bromosuccinic acid imine or N-iodosuccinic acid imine is converted into 4-chloro-5-halopyrrolo of formula XX in which Y is chlorine, bromine, or iodine [2 ,3-d] pyrimidine compounds. The reaction mixture is heated to reflux in chloroform for about 1 hour to about 3 hours, preferably about 1 hour. Alternatively, in the reaction 1 of preparation A, the 4-chloropy...

Embodiment 1

[0122] Furan-2-yl-{4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-

[0123] Piperidin-1-yl}-methanone Method A1-Benzyl-4-methyl-pyridinium chloride

[0124] To a stirred solution of 4-picoline (26ml / 0.268mol) in 70ml acetone was added 31ml (0.286mol) benzyl chloride. The resulting mixture was stirred at 50°C for 18 hours. After cooling to room temperature, it was filtered, washed with acetone and dried under reduced pressure to obtain 38 g of the title compound. The filtrate was concentrated under reduced pressure to yield an additional 5.6 g of the title compound (74% combined yield).

[0125] LRMS: 184. Method B1-Benzyl-4-methyl-1,2,3,6-tetrahydro-pyridine

[0126] To a stirred solution of the product of Method A (38 g / 0.171 mol) dissolved in 140 mL of 10:1 ethanol / water at 0°C was added 16 g (0.427 mol) of sodium borohydride in 25 minutes. The resulting mixture was stirred at room temperature for 18 hours, during which time 100 mL of water was added to quench th...

Embodiment 2

[0147] [1-(4-Methoxy-benzenesulfonyl)-4-methyl-piperidin-3-yl]-methyl-(7H-

[0148] Pyrrolo[2,3-d]pyrimidin-4-yl)-amine

[0149] LRMS: 416.

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PUM

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Abstract

A compound of Formula (I), wherein R1, R2 and R3 are as defined herein, useful as inhibitors of protein kinases, such as the enzyme Janus Kinase 3.

Description

Background of the invention [0001] The present invention relates to pyrrolo[2,3-d]pyrimidine compounds, which are inhibitors of protein kinases such as the enzyme JanusKinase 3 (hereinafter referred to as JAK3), and therefore can be used as immunosuppressive agents for the treatment of organ transplantation, transplant rejection, and lupus , Multiple sclerosis, rheumatoid arthritis, psoriasis, type I diabetes and diabetic complications, cancer, asthma, atopic skin disease, autoimmune thyroid disease, ulcerative colitis, Crohn disease, Alzheimer's disease, Leukemia and other immunosuppressive indications. [0002] The present invention also relates to a method for treating the aforementioned conditions in mammals, especially humans, with such compounds. [0003] JAK3 is a member of the Janus family of protein kinases. Although almost all tissues express other members of this family, the expression of JAK3 is limited to hematopoietic cells. This is related to the non-covalent bindin...

Claims

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Application Information

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IPC IPC(8): A61KA61K31/407A61K31/505A61K31/519A61K31/5377A61K45/00A61PA61P1/04A61P3/00A61P3/10A61P5/00A61P7/06A61P9/02A61P11/06A61P17/00A61P17/06A61P19/02A61P21/00A61P25/00A61P25/28A61P29/00A61P35/00A61P35/02A61P37/02A61P37/06A61P43/00C07DC07D207/00C07D237/00C07D487/04
CPCA61K31/505C07D487/04A61P1/04A61P11/06A61P17/00A61P17/06A61P19/00A61P19/02A61P21/00A61P25/00A61P25/28A61P29/00A61P3/00A61P35/00A61P35/02A61P37/00A61P37/02A61P37/06A61P43/00A61P5/00A61P7/06A61P9/02A61P3/10
Inventor 托德·A·布卢门科普夫马克·E·弗拉纳根迈克尔·J·芒奇霍夫
Owner PFIZER PRODS ETAT DE CONNECTICUT
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