42281-31-2

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dihydro-7-methoxyspiro(cyclopentane-1,2(1H)-naphthalene)-1-one is used as an intermediate in the synthesis of rac-14-epi-Dextromethorphan (D299440), which is an analog of Dextromethorphan (D299445). Dextromethorphan is an antitussive compound with analgesic properties, commonly used in cough medication formulations to suppress coughing.
In the synthesis process, 3,4-Dihydro-7-methoxyspiro(cyclopentane-1,2(1H)-naphthalene)-1-one plays a vital role in creating the desired pharmacological effects of the final product, rac-14-epi-Dextromethorphan. This intermediate compound is essential for the development of new and improved antitussive and analgesic medications, potentially offering better efficacy and reduced side effects for patients suffering from cough and pain.

Upstream product

• 110-52-1 1,4-dibromo-butane 
• 6836-19-7 7-Methoxy-1-tetralone 

Relevant academic research and scientific papers

OCTAHYDROPHENANTHRENE DERIVATIVES

Compounds of the formula: STR1 wherein R 1 and R 2 each individually are hydrogen or lower alkyl optionally substituted by aryl or C 3-6-cycloalkyl;R 4 and R 5 either both are hydrogen or both are halogen or one is hydrogen and the other is halogen, hydroxy, lower alkoxy, aryloxy or amino; and R. sup.3 is hydrogen or, where no primary or secondary amino group is present, alkanoyl;with the proviso that all the groups R 1 through R 5 cannot simultaneously be hydrogen; as well as pharmaceutically acceptable salts of compounds of formula I with acids have valuable pharmacodynamic properties as non-competitive NMDA antagonists and can accordingly be used as neuroprotectives.

Process for the preparation of 14-hydroxymorphinans

N-substituted-14-hydroxy-3-substituted-morphinan derivatives have been found to possess potent narcotic agonist or antagonist activity. In particular, the compound 3,14-dihydroxy-N-cyclopropylmethylmorphinan has been found to possess potent agonist-antagonist activity. A new and more efficient total synthesis for the preparation of these compounds is described herein, which improvement comprises using a Schiff base of 4a-(2-aminoethyl)-1,2,3,4,4a,9-hexahydro-6-methoxyphenanthrene to produce 3-methoxy-9-bromo-norhasubanan hydrobromide in substantially improved yields through the intermediate of the formula SPC1