157286-86-7

Basic information

• Product Name: CP-154,526
• Synonyms: CP-154,526;N-Butyl-N-ethyl-2,5-dimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-aminehydrochloride;N-Butyl-N-ethyl-2,5-dimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine;7H-Pyrrolo[2,3-d]pyrimidin-4-amine,N-butyl-N-ethyl-2,5-dimethyl-7-(2,4,6-trimethylphenyl)-;N-butyl-N-ethyl-2,5-dimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-amine
• CAS NO: 157286-86-7
• Molecular Formula: C23H32N4
• Molecular Weight: 364.53
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Neurochemicals;Pfizer Compounds;Pharmaceuticals
• Mol File: 157286-86-7.mol

Chemical Properties

• Boiling Point: 423.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.06
• Storage Temp.: Desiccate at +4°C
• PKA: 6.97±0.30(Predicted)
• CAS DataBase Reference: CP-154,526(CAS DataBase Reference)
• NIST Chemistry Reference: CP-154,526(157286-86-7)
• EPA Substance Registry System: CP-154,526(157286-86-7)

Safety Data

• Hazardous Substances Data: 157286-86-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
CP-154,526 is used as a therapeutic agent for the treatment of anxiety disorders due to its anxiolytic-like activity and ability to modulate the HPA axis.
Used in Research Applications:
CP-154,526 is used as a research tool for studying the role of CRF1 receptors in various physiological and pathological processes, including stress response, anxiety, and other related conditions.
Used in Drug Development:
CP-154,526 serves as a lead compound in the development of new drugs targeting CRF1 receptors for the treatment of anxiety and stress-related disorders, as well as other conditions where CRF1 receptor modulation may be beneficial.

Biological Activity

Selective, non-peptide CRF 1 receptor antagonist (K i values are 2.7 and > 10000 nM for CRF 1 and CRF 2 receptors respectively). Blocks CRF-induced adenylate cyclase activation (K i = 3.7 nM) and attenuates activation of the HPA axis by CRF. Displays anxiolytic-like activity in the rat elevated plus-maze test; brain penetrant.

Upstream product

• 13360-63-9 N-ethylbutylamine 
• 157286-81-2 4-chloro-2,5-dimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo-[2,3-d]pyrimidine 
• 157286-78-7 2-amino-4-methyl-1-(2,4,6-trimethylphenyl)pyrrole-3-carbonitrile 
• 157286-79-8 N-[3-cyano-4-methyl-1-(2,4,6-trimethylphenyl)-1H-pyrrol-2-yl]-acetamide 
• 157286-80-1 2,5-dimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ol 
• 13166-10-4 isopropylidenemalonodinitrile 

Relevant articles and documents

Pyrrolopyrimidines as CRF antagonists

The compounds of the formula wherein R1, R2, R3, R4, R5and R6are as defined herein, are useful in the treatment of stress-related and other diseases. These compounds have corticotropin-releasing factor antagonist activity and as such are of use in the treatment of stress and anxiety related, and other disorders.

Use of CRF antagonists and renin-angiotensin system inhibitors

The present invention relates to compositions and methods of achieving a therapeutic effect including, but not limited to, the treatment of congestive heart failure or hypertension in an animal, preferably a mammal including a human subject or a companion animal, using a corticotropin releasing factor (CRF) antagonist and a renin-angiotensin system (RAS) inhibitor.

QT dispersion and heart rate variability improvement with CRF antagonists to prevent sudden death

A method of preventing sudden death which comprises administering to a mammal, including a human, a therapeutically effective amount of a corticotropin releasing factor antagonist.

New uses for corticotropin releasing factor antagonists

A method of treating, preventing or inhibiting a disorder selected from the group consisting of cardiovascular or heart related diseases such as stroke, hypertension, tachycardia, and congestive heart failure, osteoporosis, premature birth, psychosocial dwarfism, stress-induced fever, ulcer, diarrhea, post-operative ileus, and colonic hypersensitivity associated with psychopathological disturbance and stress, comprising administering to a mammal, including a human, in need of such treatment a therapeutically effective amount of a compound of the formula or pharmaceutically acceptable salt thereof, wherein A, B, D, E, Y, Z, R3, R4, and R5 are as defined herein.

PYRAZOLOPYRIMIDINES FOR TREATMENT OF CNS DISORDERS

This invention relates to the use of pyrazolopyrimidines and pyrrolopyrimidine of, respectively, the general formula STR1 wherein A, X, R 3, R 4 and R 5 are as defined below, and the pharmaceutically acceptable salts of such compounds, to treat, prevent or inhibit certain neuronal and other disorders.

Synthesis, corticotropin-releasing factor receptor binding affinity, and pharmacokinetic properties of triazolo-, imidazo-, and pyrrolopyrimidines and -pyridines

The synthesis and CRF receptor binding affinities of several new series of N-aryltriazolo- and -imidazopyrimidines and -pyridines are described. These cyclized systems were prepared from appropriately substituted diaminopyrimidines or -pyridines by nitrous acid, orthoester, or acyl halide treatment. Variations of amino (ether) pendants and aromatic substituents have defined the structure-activity relationships of these series and resulted in the identification of a variety of high-affinity agents (K(i)'s 1 has been selected for further pharmacological studies that will be reported in due course.

Methods of administering CRF antagonists

Compounds of the formula STR1 wherein B, R3, R4, R5 and R6 are as defined herein with reference to formula IX have corticotropin-releasing factor antagonist activity and as such are of use in the treatment of panics, phobias and other stress-related disorders.

Synthesis and oral efficacy of a 4-(butylethylamino)pyrrolo[2,3- d]pyrimidine: A centrally active corticotropin-releasing factor1 receptor antagonist

The syntheses of a centrally active nonpeptide CRF1 receptor antagonist 2, butylethyl[2,5-dimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3- d]pyrimidin-4-yl]amine (CP-154,526), and its analogs 11-14 and [3H]-2 are reported. The in v