The present application relates to psilocin derivatives of Formula (I), to processes for their preparation, to compositions comprising them and to their use in activation of a serotonin receptor in a cell, as well as to treating diseases, disorders or conditions by activation of a serotonin receptor in a cell.

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This invention relates to the large-scale production of psilocybin for use in medicine. More particularly, it relates to a method of obtaining high purity crystalline psilocybin, particularly, in the form of Polymorph A. It further relates to a method for the manufacture of psilocybin and intermediates in the production thereof and formulations containing psilocybin.

The disclosure provides methods for treating a subject in need thereof comprising administering to the subject a therapeutically-effective dose of psilocybin. The methods described herein may be used to treat a variety of diseases, disorders, and conditions. For example, the methods may be used to treat depression, neurocognitive disorders, autism spectrum disorder, and/or attention-deficit/hyperactivity disorder.

The disclosure relates to compounds of Formula (I), which are formyl peptide 2 (FPR2) receptor agonists and/or formyl peptide 1 (FPR1) receptor agonists. The disclosure also provides compositions and methods of using the compounds, for example, for the treatment of atherosclerosis, heart failure, chronic obstructive pulmonary disease (COPD), and related diseases.

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The disclosure relates to compounds of Formula (I), which are formyl peptide 2 (FPR2) receptor agonists and/or formyl peptide 1 (FPR1) receptor agonists. The disclosure also provides compositions and methods of using the compounds, for example, for the treatment of atherosclerosis, heart failure, chronic obstructive pulmonary disease (COPD), and related diseases.

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The present disclosure is directed to chemical compounds and to the use of such compounds in the treatment of diseases associated with a serotonin 5-HT.sub.2 receptor.

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The invention relates to compounds of formula (I)

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where R.sup.1, R.sup.2, R.sup.3, R.sup.4 are each independently selected from —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —(C.sub.6-C.sub.20)-aryl, —(C.sub.3-C.sub.20)-heteroaryl; at least one of the R.sup.1, R.sup.2, R.sup.3, R.sup.4 radicals is a —(C.sub.3-C.sub.20)-heteroaryl radical; and R.sup.1, R.sup.2, R.sup.3, R.sup.4, if they are —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —(C.sub.6-C.sub.20)-aryl or —(C.sub.3-C.sub.20)-heteroaryl, may each independently be substituted by one or more substituents selected from —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —O—(C.sub.1-C.sub.12)-alkyl, —O—(C.sub.1-C.sub.12)-alkyl-(C.sub.6-C.sub.20)-aryl, —O—(C.sub.3-C.sub.12)-cycloalkyl, —S—(C.sub.1-C.sub.12)-alkyl, —S—(C.sub.3-C.sub.12)-cycloalkyl, —COO—(C.sub.1-C.sub.12)-alkyl, —COO—(C.sub.3-C.sub.12)-cycloalkyl, —CONH—(C.sub.1-C.sub.12)-alkyl, —CONH—(C.sub.3-C.sub.12)-cycloalkyl, —CO—(C.sub.1-C.sub.12)-alkyl, —CO—(C.sub.3-C.sub.12)-cycloalkyl, —N—[(C.sub.1-C.sub.12)-alkyl].sub.2, —(C.sub.6-C.sub.20)-aryl, —(C.sub.6-C.sub.20)-aryl-(C.sub.1-C.sub.12)-alkyl, —(C.sub.6-C.sub.20)-aryl-O—(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.20)-heteroaryl, —(C.sub.3-C.sub.20)-heteroaryl-(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.20)-heteroaryl-O—(C.sub.1-C.sub.12)-alkyl, —COOH, —OH, —SO.sub.3H, —NH.sub.2, halogen; and to the use thereof as ligands in alkoxycarbonylation.

The invention relates to compounds of formula (I)

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where R.sup.1, R.sup.2, R.sup.3, R.sup.4 are each independently selected from —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —(C.sub.6-C.sub.20)-aryl, —(C.sub.3-C.sub.20)-heteroaryl; at least one of the R.sup.1, R.sup.2, R.sup.3, R.sup.4 radicals is a —(C.sub.3-C.sub.20)-heteroaryl radical; and R.sup.1, R.sup.2, R.sup.3, R.sup.4, if they are —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —(C.sub.6-C.sub.20)-aryl or —(C.sub.3-C.sub.20)-heteroaryl, may each independently be substituted by one or more substituents selected from —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —O—(C.sub.1-C.sub.12)-alkyl, —O—(C.sub.1-C.sub.12)-alkyl-(C.sub.6-C.sub.20)-aryl, —O—(C.sub.3-C.sub.12)-cycloalkyl, —S—(C.sub.1-C.sub.12)-alkyl, —S—(C.sub.3-C.sub.12)-cycloalkyl, —COO—(C.sub.1-C.sub.12)-alkyl, —COO—(C.sub.3-C.sub.12)-cycloalkyl, —CONH—(C.sub.1-C.sub.12)-alkyl, —CONH—(C.sub.3-C.sub.12)-cycloalkyl, —CO—(C.sub.1-C.sub.12)-alkyl, —CO—(C.sub.3-C.sub.12)-cycloalkyl, —N—[(C.sub.1-C.sub.12)-alkyl].sub.2, —(C.sub.6-C.sub.20)-aryl, —(C.sub.6-C.sub.20)-aryl-(C.sub.1-C.sub.12)-alkyl, —(C.sub.6-C.sub.20)-aryl-O—(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.20)-heteroaryl, —(C.sub.3-C.sub.20)-heteroaryl-(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.20)-heteroaryl-O—(C.sub.1-C.sub.12)-alkyl, —COOH, —OH, —SO.sub.3H, —NH.sub.2, halogen; and to the use thereof as ligands in alkoxycarbonylation.

Provided herein are compounds of Formula (I), or pharmaceutically acceptable salt thereof, wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.8, R.sub.9, X, Y, Z, W, and m are defined herein. Also provided herein are pharmaceutical compositions comprising a compound of Formula (I) or pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient.

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Compounds useful as fluorescent or colored dyes are disclosed. The compounds have the following structure (I): or a stereoisomer, tautomer or salt thereof, wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, L.sup.1, L.sup.3, L.sup.4, L.sup.6, L.sup.7, L.sup.8, M.sup.1, M.sup.2, q, w and n are as defined herein. Methods associated with preparation and use of such compounds are also provided. ##STR00001##