Methods of synthesizing 2-(1H-indole-3-carbonyl)-thiazole-4-carboxylic acid methyl ester (ITE) and structural analogs thereof. The methods include condensation reactions or condensation and oxidation reactions to form the thiazoline or thiazole moiety of ITE or its structural analogs.

Methods of synthesizing 2-(1H-indole-3-carbonyl)-thiazole-4-carboxylic acid methyl ester (ITE) and structural analogs thereof. The methods include condensation reactions or condensation and oxidation reactions to form the thiazoline or thiazole moiety of ITE or its structural analogs.

[Problem] Provided is a novel 1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine derivative or a pharmaceutically acceptable salt thereof, or a solvate thereof, which is useful as an anti-HIV agent. [Solving Means] The present invention provides a compound represented by the following formula [I] ##STR00001##
wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof, or a solvate thereof.

The present invention relates to a compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt thereof. The compound according to the present invention can be usefully used for the prevention or treatment of autophagy-related diseases.

Provided herein are small molecule active metabotropic glutamate subtype-2 and -3 receptor negative allosteric modulators (NAMs), compositions comprising the compounds, and methods of using the compounds and compositions.

The present invention provides a process that enables a substituted methylamine compound which is useful as an intermediate for the production of agricultural chemicals and medicines, to be produced easily, with good yield, and at low cost, and also provides a production intermediate thereof. The process comprises a step of reacting a hexamethylenetetraammonium salt compound represented by a formula (I) with a base to obtain an N-methylidene-substituted methylamine oligomer represented by a formula (II) or a mixture of two or more of the oligomers, and a step of hydrolyzing the N-methylidene-substituted methylamine oligomer represented by formula (II) or the mixture of two or more of the oligomers in the presence of an acid. ##STR00001##
(wherein A represents an organic group, R represents a hydrogen atom, or an organic group, L represents a halogen atom and the like, and n represents an integer of 2 to 20).

The present invention provides a process that enables a substituted methylamine compound which is useful as an intermediate for the production of agricultural chemicals and medicines, to be produced easily, with good yield, and at low cost, and also provides a production intermediate thereof. The process comprises a step of reacting a hexamethylenetetraammonium salt compound represented by a formula (I) with a base to obtain an N-methylidene-substituted methylamine oligomer represented by a formula (II) or a mixture of two or more of the oligomers, and a step of hydrolyzing the N-methylidene-substituted methylamine oligomer represented by formula (II) or the mixture of two or more of the oligomers in the presence of an acid. ##STR00001##
(wherein A represents an organic group, R represents a hydrogen atom, or an organic group, L represents a halogen atom and the like, and n represents an integer of 2 to 20).

The present invention provides a compound having a lysine-specific demethylase 1 inhibitory action, and useful as a medicament such as a prophylactic or therapeutic agent for cancer, and central nervous system diseases, and the like. The present invention relates to a compound represented by the formula ##STR00001##
wherein A is a hydrocarbon group or heterocyclic group optionally having substituent(s); R is H, a hydrocarbon group or heterocyclic group optionally having substituent(s); A and R are optionally bonded to each other to form a ring optionally having substituent(s); Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 are each a hydrogen atom or a substituent; Q.sup.1 and Q.sup.2, and Q.sup.3 and Q.sup.4, are each optionally bonded to each other to form a ring optionally having substituent(s); X is H, an acyclic hydrocarbon group or saturated cyclic group optionally having substituent(s); Y.sup.1, Y.sup.2 and Y.sup.3 are each H, a hydrocarbon group or heterocyclic group optionally having substituent(s); X and Y.sup.1, and Y.sup.1 and Y.sup.2, are each optionally bonded to each other to form a ring optionally having substituent(s); and Z.sup.1, Z.sup.2 and Z.sup.3 are each H or a substituent, or a salt thereof.

The present invention provides a compound having a lysine-specific demethylase 1 inhibitory action, and useful as a medicament such as a prophylactic or therapeutic agent for cancer, and central nervous system diseases, and the like. The present invention relates to a compound represented by the formula ##STR00001##
wherein A is a hydrocarbon group or heterocyclic group optionally having substituent(s); R is H, a hydrocarbon group or heterocyclic group optionally having substituent(s); A and R are optionally bonded to each other to form a ring optionally having substituent(s); Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 are each a hydrogen atom or a substituent; Q.sup.1 and Q.sup.2, and Q.sup.3 and Q.sup.4, are each optionally bonded to each other to form a ring optionally having substituent(s); X is H, an acyclic hydrocarbon group or saturated cyclic group optionally having substituent(s); Y.sup.1, Y.sup.2 and Y.sup.3 are each H, a hydrocarbon group or heterocyclic group optionally having substituent(s); X and Y.sup.1, and Y.sup.1 and Y.sup.2, are each optionally bonded to each other to form a ring optionally having substituent(s); and Z.sup.1, Z.sup.2 and Z.sup.3 are each H or a substituent, or a salt thereof.

A compound that can be a therapeutic agent for underactive bladder which has low risk of side effects and can be administered orally is provided. Furthermore, a crystal which is advantageous in view of the stability, long-term storage, handleability, easiness of the drug preparation or the like as a drug substance of medicaments is provided. Since a salt of 2-[(2-{(1R,5R)-2-oxo-5-[(1E,4S)-7,8,8-trifluoro-4-hydroxy-4-methyl-1,7-octadien-1-yl]cyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxylic acid or a diastereomeric mixture thereof and 4-piperidinemethanol is a chemically very stable crystal, it can be stored for a long time, and is very useful as a drug substance of medicaments.