147249-42-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Aminomethyl-3,4-Dichloro-Phenylamine is used as a synthetic reagent for the production of 3-Hydroxyanagrelide, a derivative of Anagrelide (A637300). Anagrelide is a medication prescribed for the treatment of thrombocythemia, a condition characterized by an abnormally high platelet count in the blood. The compound plays a crucial role in the synthesis process, enabling the development of effective treatments for this medical condition.

InChI:InChI=1/C7H8Cl2N2/c8-5-1-2-6(11)4(3-10)7(5)9/h1-2H,3,10-11H2

Upstream product

• 2112-22-3 2,3-dichloro-6-nitrobenzonitrile 
• 147249-41-0 2,3-dichloro-6-aminobenzonitrile 

Downstream Products

• 875467-37-1 C₁₄H₁₅Cl₂N₃O₃ 
• 327602-34-6 2-amino-5,6-dichloro-3,4-dihydroquinazoline hydrogen bromide 
• 444904-63-6 RL 603 

Relevant academic research and scientific papers

Synthesis and stability of 3-hydroxyanagrelide, a biologically potent metabolite of anagrelide

Metabolism of 6,7-dichloro-1,5-dihydroimidazo[2,1-b]quinazolin- 2-one (anagrelide), a drug for treating essential thrombocythemia, gives 6,7-dichloro-3-hydroxy-1,5-dihydroimidazo[2,1-b]quinazolin-2-one (3-hydroxyanagrelide) and 2-amino-5,6-dichloro-3,4-dihydroquinazoline. To enable the properties of 3-hydroxyanagrelide to be fully evaluated, the racemic compound has been synthesized. In pH 7.4 aqueous buffer 3-hydroxyanagrelide readily equilibrates with an isomer, 6,7-dichloro-1-hydroxy-3,5- dihydroimidazo[1,2-a]- quinazolin-2-one, and is also hydrolyzed to 2-amino-5,6-dichloro-3,4-dihydroquinazoline. 3-Hydroxyanagrelide (half-life 40 hours) was the dominant species at equilibrium and it was concluded that the equilibration and decomposition are sufficiently slow that published assays of 3-hydroxyanagrelide are reliable.

Cyclic guanidines as dual 5-HT5A/5-HT7 receptor ligands: Structure-activity relationship elucidation

The optimisation of affinity and selectivity in a novel series of dual 5-HT5A/5-HT7 receptor ligands is described. Brain penetrant 2-aminodihydroquinazolines with low nanomolar affinities were identified.

2-amino-5,6-dichloro-3,4-dihydroquinazoline, its method of making and using and pharmaceutical compositions thereof

The compound 2-amino-5,6-dichloro-3,4-dihydroquinazoline has been found to have enhanced platelet count reducing properties. Also provided are methods for synthetically making the compound and a method of reducing the platelet count in a patient by administering to the patient a platelet reducing effective amount of the compound preferably together with a pharmaceutically acceptable carrier. A pharmaceutical composition is also provided which contains the above compound as the active ingredient together with pharmaceutically acceptable excipients.