34617-65-7

Usage

Uses

Used in Pharmaceutical Industry:
5-AMINO-3-CHLOROPYRAZINE-2-CARBONITRILE is used as a reagent for the synthesis of orally bioavailable CHK1 inhibitors. These inhibitors play a significant role in the treatment of cancer, as they target the checkpoint kinase 1 (CHK1) enzyme, which is involved in the regulation of cell cycle progression and DNA repair. By inhibiting CHK1, these compounds can potentially enhance the effectiveness of DNA-damaging anticancer therapies and overcome drug resistance in cancer cells.

Upstream product

• 173253-42-4 2-chloro-3-bromo-6-aminopyrazine 
• 925678-00-8 6-chloro-5-iodo-pyrazin-2-ylamine 
• 557-21-1 zinc(II) cyanide 
• 34617-64-6 5-amino-3-chloro-pyrazine-2-carbaldehyde O-acetyl-oxime 

Downstream Products

• 1430840-87-1 3-(4-fluorophenyl)-6-((3-(pyridin-4-yloxy)azetidin-1-yl)methyl)imidazo[1,5-a]pyrazin-8(7H)-one 
• 1430840-13-3 6-[1-(3-methoxyazetidin-1-yl)-ethyl]-3-phenyl-7H-imidazo[1,5-a]pyrazin-8-one 
• 1430840-01-9 3-phenyl-6-(3-phenylazetidin-1-ylmethyl)-7H-imidazo-[1,5-a]pyrazin-8-one 
• 1430841-42-1 6-acetyl-3-phenyl-7H-imidazo[1,5-a]pyrazin-8-one 
• 1430841-41-0 1-(8-methoxy-3-phenyl-imidazo[1,5-a]pyrazin-6-yl)-ethanone 
• 1430841-40-9 8-methoxy-3-phenylimidazo[1,5-a]pyrazine-6-carboxylic acid methoxy-methyl-amide 
• 1430841-39-6 6-chloromethyl-3-phenyl-7H-imidazo[1,5-a]pyrazin-8-one 
• 1430841-38-5 6-(chloromethyl)-8-methoxy-3-phenylimidazo[1,5-a]pyrazine 
• 1430841-37-4 (8-methoxy-3-phenylimidazo[1,5-a]pyrazin-6-yl)methanol 
• 1430841-36-3 methyl 8-methoxy-3-phenylimidazo[1,5-a]pyrazine-6-carboxylate 
• 1430841-35-2 6-iodo-8-methoxy-3-phenylimidazo[1,5-a]pyrazine 
• 1430841-34-1 N-((5-iodo-3-methoxypyrazin-2-yl)methyl)benzamide 

Relevant academic research and scientific papers

PDE9 INHIBITORS FOR TREATMENT OF PERIPHERAL DISEASES

The present invention relates to PDE9 inhibitors, their synthesis, and their use for treatment of benign prostate hyperplasia, beta thalassemia, and sickle cell disease.

PDE9 INHIBITORS WITH IMIDAZO TRIAZINONE BACKBONE AND IMIDAZO PYRAZINONE BACKBONE FOR TREATMENT OF PERIPHERAL DISEASES

The present invention relates to PDE9 inhibitors and their use for treatment of benign prostate hyperplasia and sickle cell disease.

NEW SUBSTITUTED BIPHENYL ANALOGUES AS DUAL INHIBITORS OF AROMATASE AND SULFATASE

Provided are new biphenyl derivatives of formula (Ia). These compounds act as aromatase and sulfatase inhibitors. They are particularly useful for treating pathological conditions or diseases in which aromatase and sulfatase are involved. Moreover, provided are processes for the preparation of these compounds and pharmaceutical compositions containing said products and their use for the preparation of a medicament, in particular for the treatment of diseases characterized by aromatase and sulfatase activity such as hormone-dependent cancers.

5-(PYRIDIN-2-YL-AMINO)-PYRAZINE-2-CARBONITRILE COMPOUNDS AND THEIR THERAPEUTIC USE

The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain pyridyl-amino-pyrazine carbonitrile compounds that, inter alia, inhibit Checkpoint Kinase 1 (CHK1) kinase function. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit CHK1 kinase function, and in the treatment of diseases and conditions that are mediated by CHK1, that are ameliorated by the inhibition of CHK1 kinase function, etc., including proliferative conditions such as cancer, etc., optionally in combination with another agent, for example, (a) a DNA topoisomerase I or II inhibitor; (b) aDNA damaging agent; (c) an antimetabolite or thymidylate synthase (TS) inhibitor; (d) a microtubule targeted agent; and (e) ionisin g radiation.

Structure-guided evolution of potent and selective CHK1 inhibitors through scaffold morphing

Pyrazolopyridine inhibitors with low micromolar potency for CHK1 and good selectivity against CHK2 were previously identified by fragment-based screening. The optimization of the pyrazolopyridines to a series of potent and CHK1-selective isoquinolines demonstrates how fragment-growing and scaffold morphing strategies arising from a structure-based understanding of CHK1 inhibitor binding can be combined to successfully progress fragment-derived hit matter to compounds with activity in vivo. The challenges of improving CHK1 potency and selectivity, addressing synthetic tractability, and achieving novelty in the crowded kinase inhibitor chemical space were tackled by multiple scaffold morphing steps, which progressed through tricyclic pyrimido[2,3-b] azaindoles to N-(pyrazin-2-yl)pyrimidin-4-amines and ultimately to imidazo[4,5-c]pyridines and isoquinolines. A potent and highly selective isoquinoline CHK1 inhibitor (SAR-020106) was identified, which potentiated the efficacies of irinotecan and gemcitabine in SW620 human colon carcinoma xenografts in nude mice. (Figure presented)

BICYCLYLARYL-ARYL-AMINE COMPOUNDS AND THEIR USE

The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain bicyclylaryl-aryl-amines compounds of the following formula (referred to herein as BCAA compounds), which, inter alia, inhibit Checkpoint Kinase 1 (CHK1) kinase function. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit CHK1 kinase function, and in the treatment of diseases and conditions that are mediated by CHK1, that are ameliorated by the inhibition of CHK1 kinase function, etc., including proliferative conditions such as cancer, etc., optionally in combination with another agent, for example, (a) a DNA topoisomerase I or II inhibitor; (b) a DNA damaging agent; (c) an antimetabolite or TS inhibitor; (d) a microtubule targeted agent; and (e) ionising radiation: (I).

Synthesis of macrocyclic urea kinase inhibitors

An efficient and convergent route was developed for the synthesis of a novel class of urea-based macrocyclic kinase inhibitors. The synthesis is featured with an efficient urea formation by using a key carbamate intermediate and with a smooth ring-closure olefin metathesis. Furthermore, the hydrogenations of the resulting olefins were investigated in this complex macrocyclic ring system. Georg Thieme Verlag Stuttgart.

Macrocyclic kinase inhibitors

Compounds having the formula are useful for inhibiting protein kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

Macrocyclic kinase inhibitors

Compounds having the formula are useful for inhibiting protein kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.