282547-38-0

Upstream product

• 1310-73-2 sodium hydroxide 
• 90-52-8 6-methoxyquinolin-8-amine 
• 52671-64-4 4-Amino-3-chlorophenol hydrochloride 
• 796851-15-5 8-chloro-6-methoxyquinoline 
• 18119-24-9 8-Chlor-6-hydroxychinolin 
• 282547-70-0 8-(4-benzyl-piperazin-1-yl)-6-methoxy-quinoline 
• 796851-18-8 6-methoxy-8-[1-(tert-butoxycarbonyl)-4-piperazino]quinoline 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 

Downstream Products

• 917251-89-9 8-[4-(1-benzylpiperidin-4-yl)piperazin-1-yl]-6-methoxyquinoline 

Relevant academic research and scientific papers

The synthesis and biological evaluation of quinolyl-piperazinyl piperidines as potent serotonin 5-HT1A antagonists

As part of an effort to identify 5-HT1A antagonists that did not possess typical arylalkylamine or keto/amido-alkyl aryl piperazine scaffolds, prototype compound 10a was identified from earlier work in a combined 5-HT 1A antagonist/SSRI program. This quinolyl-piperazinyl piperidine analogue displayed potent, selective 5-HT1A antagonism but suffered from poor oxidative metabolic stability, resulting in low exposure following oral administration. SAR studies, driven primarily by in vitro liver microsomal stability assessment, identified compound 10b, which displayed improved oral bioavailability and lower intrinsic clearance. Further changes to the scaffold (e.g., 10r) resulted in a loss in potency. Compound 10b displayed cognitive enhancing effects in a number of animal models of learning and memory, enhanced the antidepressant-like effects of the SSRI fluoxetine, and reversed the sexual dysfunction induced by chronic fluoxetine treatment.

BENZOFURANYL- AND BENZOTHIENYL- PIPERAZINYL QUINOLINES AND METHODS OF THEIR USE

Benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such compounds are disclosed. Methods of using benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such composition in the treatment and/or prevention of serotonin-related disorders, such as depression and anxiety, are also disclosed. In addition, processes for the preparation of benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives are disclosed.

METABOLITES OF 5-FLUORO-8-{4-[4-(6-METHOXYQUINOLIN-8-YL)PIPERAZIN-1-YL]PIPERIDIN-1-YL} QUINOLINE AND METHODS OF PREPARATION AND USES THEREOF

The present invention relates to novel metabolites of 5-Fluoro-8-{4-[4-(6- methoxyquinolin-8-yl)piperazin-l-yl]piperidin-l -yl}quinoline, which can be useful in treating CNS disorders. The present invention further relates to processes for their preparation, to pharmaceutical compositions comprising them, and to methods of using them.

Piperazine-piperidine antagonists and agonists of the 5-HT1A receptor

The present invention relates to novel piperazine-piperidine compounds. The compounds are useful as 5-HT1A binding agents, particularly as 5-HT1A receptor antagonists and agonists. These compounds are useful in treating central nervous system disorders, such as cognition disorders, anxiety disorders, depression and sexual dysfunction.

PROCESS FOR SYNTHESIZING PIPERAZINE-PIPERIDINE COMPOUNDS

The present invention relates to processes for synthesizing piperazine-piperidine compounds, and compounds useful as 5-HT1A binding agents, particularly as 5-HT1A receptor antagonists and agonists. The processes also allow for safer

6-Methoxy-8-[4-(1-(5-fluoro)-quinolin-8-yl-piperidin-4-yl)-piperazin-1-yl]-quinoline hydrochloric acid salts

The present invention relates to hydrochloric acid salt and crystalline forms of the 5-HT1A binding agent 6-methoxy-8-[4-(1-(5-fluoro)-quinolin-8-yl-piperidin-4-yl)-piperazin-1-yl]-quinoline, as well as pharmaceutical compositions thereof, and methods of use thereof.

SUCCINATE SALTS OF 6-METHOXY-8-[4-(1-(5-FLUORO)-QUINOLIN-8-YL-PIPERIDIN-4-YL)-PIPERAZIN-1-YL]-QUINOLINE AND CRYSTALLINE FORMS THEREOF

The present invention relates to succinic acid salt forms of the 5-HT1A binding agent 6-methoxy-8-[4-(1-(5-fluoro)-quinolin-8-yl-piperidin-4-yl)-piperazin-1-yl]-quinoline, as well as crystalline forms thereof, pharmaceutical compositions thereof, and methods of use thereof.

CRYSTALLINE FORMS OF 6-METHOXY-8-[4-(1-(5-FLUORO)-QUINOLIN-8-YL-PIPERIDIN-4-YL)-PIPERAZIN-1-YL]-QUINOLINE

The present invention relates to crystalline forms of the 5-HT1A binding agent 6-methoxy-8-[4-(1-(5-fluoro)-quinolin-8-yl-piperidin-4-yl)-piperazin-1-yl]-quinoline, as well as pharmaceutical compositions thereof, and methods of use thereof.

ARYLPIPERAZINYL-CYCLOHEXYL INDOLE DERIVATIVES FOR THE TREATMENT OF DEPRESSION

Compounds are provided which are useful for the treatment of serotonin-affected neurological disorders which comprise (I) wherein: Ra, R1, R2 and R3 are each, independently, hydrogen, or a substituent selected from halogen, CF3, alkyl, alkoxy, MeSO2, amino or aminocarbonyl (each optionally substituted by one or two groups selected from alkyl and benzyl) carboxy, or alkoxycarbonyl; or two adjacent of Ra and R1-4 together can form a 5-7 membered carbocyclic or heterocyclic ring which is optionally substituted by a substituent defined above; R4 is hydrogen, halogen, or alkyl; R5 is hydrogen, alkyl, arylalkyl, or aryl; R6 is hydrogen, halogen, CF3, CN, carbamide, alkoxy or benzyloxy; X1, X2 and X3 are each carbon or one of X1, X2 or X3 may be nitrogen; Y is CH or nitrogen; and Z is carbon or nitrogen; or pharmaceutically acceptable salts thereof.

BENZOFURANYL-AND BENZOTHIENYL-PIPERAZINYL QUINOLINES AND METHODS OF THEIR USE

Benzofuranyl-and benzothienyl-piperzinyl quinoline derivatives and compositions containing such compounds are disclosed. Methods of using benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such composition in the treatment and/or prevention of serotonin-related disorders, such as depression and anxiety, are also disclosed. In addition, processes for the preparation of benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives are disclosed.