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

A compound, pyrimidine technology, which can be used in fields such as transplant rejection and autoimmunity to solve the problem that JAK3 is limited to hematopoietic cells

Inactive Publication Date: 2007-11-28
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
  • Pyrrolo [2,3-d] pyrimidine compounds as immunosuppressive agents
  • Pyrrolo [2,3-d] pyrimidine compounds as immunosuppressive agents

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Experimental program
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preparation example Construction

[0092] The following reaction schemes illustrate the preparation of compounds of the present invention. R in this reaction scheme and subsequent discussion 2 , R 3 , R 4 and R 5 As defined above, unless otherwise stated.

[0093] Preparation A

[0094]

[0095] Preparation B

[0096]

[0097] Preparation C

[0098]

[0099] Reaction scheme 1

[0100]

[0101] Reaction scheme 2

[0102]

[0103] Reaction scheme 3

[0104]

[0105] In reaction 1 of Preparation A, R is hydrogen or a 4-chloropyrrolo[2,3-d]pyrimidine compound of formula XXI such as benzenesulfonyl or tolyl protecting group, by combining the compound of formula XXI with N-chlorosuccinate acid imide, N-bromosuccinimide, or N-iodosuccinimide, into 4-chloro-5-halopyrrolo[2 of formula XX where Y is chlorine, bromine, or iodine , 3-d] pyrimidine compounds. The re...

Embodiment 1

[0144] Furan-2-yl-{4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-

[0145] Piperidin-1-yl}-methanone

[0146] Method A

[0147] 1-Benzyl-4-methyl-pyridinium chloride

[0148] To a stirred solution of 4-picoline (26ml / 0.268mol) in 70ml of acetone was added 31ml (0.286mol) of benzyl chloride. The resulting mixture was stirred at 50°C for 18 hours. After cooling to room temperature, filtration, washing with acetone and drying under reduced pressure afforded 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).

[0149] LRMS: 184.

[0150] Method B

[0151] 1-Benzyl-4-methyl-1,2,3,6-tetrahydro-pyridine

[0152] To a stirred solution of the Method A product (38 g / 0.171 mol) dissolved in 140 mL of 10:1 ethanol / water at 0°C was added 16 g (0.427 mol) sodium borohydride in portions over 25 minutes. The resulting mixture was stirred at room tem...

Embodiment 2

[0187] [1-(4-Methoxy-benzenesulfonyl)-4-methyl-piperidin-3-yl]-methyl-(7H-

[0188] Pyrrolo[2,3-d]pyrimidin-4-yl)-amine

[0189] LRMS: 416.

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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 enzyme JanusKinase 3 (hereinafter referred to as JAK3), and thus can be used as immunosuppressants for the treatment of organ transplantation, transplant rejection, lupus , multiple sclerosis, rheumatoid arthritis, psoriasis, type 1 diabetes and diabetic complications, cancer, asthma, atopic skin disease, autoimmune thyroid disease, ulcerative conjunctivitis, Crohn's disease, Alzheimer's disease, Leukemia and other immunosuppressive indications. [0002] The invention also relates to methods of using such compounds for the treatment of the aforementioned conditions in mammals, especially humans. [0003] JAK3 is a member of the Janus family of protein kinases. While other members of this family are expressed in essentially all tissues, expression of JAK3 is restricted to hematopoietic cells. This is consistent with signaling...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K31/505A61P17/06A61P19/02A61P37/06A61KA61K31/407A61K31/519A61K31/5377A61K45/00A61PA61P1/04A61P3/00A61P3/10A61P5/00A61P7/06A61P9/02A61P11/06A61P17/00A61P21/00A61P25/00A61P25/28A61P29/00A61P35/00A61P35/02A61P37/02A61P43/00C07DC07D207/00C07D237/00
CPCC07D487/04A61K31/505A61P1/04A61P11/06A61P17/00A61P17/06A61P19/00A61P19/02A61P21/00A61P25/00A61P25/28A61P29/00A61P3/00A61P35/00A61P35/02A61P37/00A61P37/02A61P37/06A61P43/00A61P5/00A61P7/06A61P9/02A61P3/10
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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