Albany Molecular Research, Inc.

Bristol-myers Squibb Compnay

Min Hu

Shuang Liu

Matthew L Isherwood

Wenge Cui

Richard Eric Olson

Peter Guzzo

Bruce Francis Molino

David Douglas Manning

Kassoum Nacro

Aruna Sambandam

Congxiang Zha

Rasidul Amin

Qi Gao

Jun Qiu

Kristen N Fleming

Yuh-Lin Allen Yang

Bang-Chi Chen

Rulin Zhao

Bei Wang

Paul C Lobben

Kristen N Ryan

Yuh-lin Allen Yang

Peter R Guzzo

Matthew Isherwood

The present disclosure generally relates to a crystalline form of 6-[(4S)-2-methyl-4-(naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine. The present disclosure also generally relates to pharmaceutical compositions comprising the crystalline form, as well of methods of using a crystalline form in the treatment of depression and other conditions and methods for obtaining such crystalline form.

Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine

The compounds of the present invention are represented by the following aryl- and heteroaryl-substituted tetrahydrobenzazepine and dihydrobenzazapine derivatives having formulae I(A-E) and formula (II): where the carbon atom designated * is in the R or S configuration, and the substituents X and R-Rare as defined herein.

Aryl- and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin

Disclosed are processes for preparing tetrahydroisoquinolines, intermediates useful in the preparation of tetrahydroisoquinolines, processes for preparing such intermediates, and a crystalline form of 6-[(4S)-2-methyl-4-(naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine. Also disclosed are pharmaceutical compositions comprising tetrahydroisoquinolines, methods of using tetrahydroisoquinolines in the treatment of depression and other conditions and methods for obtaining the crystalline form. One such intermediate has the following structure: 

Tetrahydroisoquinolines and intermediates therefor

The compounds of the present invention are represented by the following aryl- and heteroaryl-substituted tetrahydrobenzazepine and dihydrobenzazapine derivatives having formulae I(A-E) and formula (II):  where the carbon atom designated * is in the R or S configuration, and the substituents X and R-Rare as defined herein.

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Schenectady, NY, United States of America

Min Hu