Process for the preparation of N-amino substituted...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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Reexamination Certificate

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07112682

ABSTRACT:
An improved process for the preparation of N-amino nitrogen heterocyclic compounds is disclosed and claimed. In an embodiment of this invention, a compound of the formula (VI) is prepared starting from the corresponding indole derivative by way of N-amination and subsequently forming an hydrazone by the reaction with a keto compound in a single step. Further reduction of the hydrazone and subsequent coupling with a pyridine compound affords the compound of formula VI or a suitable salt thereof.

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A. E. Arbuzov et al., Syntheses Of Heterocyclic Compounds Based On The Fischer Reaction, Journal Of General Chemistry of the USSR (1957, pp. 2401-2412, vol. 27).
Joseph T. Klein et al., Synthesis And Structure- Activity Relationships of N-Propyl-N-(4-Pyridinyl)-1H-Indol-1-Amine (Besipirdine) and Related Analogs as Potential Therapeutic Agents for Alzheimer's Disease, J. Med. Chem. (1996, pp. 570-581, vol. 39).
Kim Andersen et al., Selective, Centrally Acting Serotonin 5-HT2 Antagonists. 2. Substituted 3-(4-Fluorophenyl)-1H-Indoles, J. Med. Chem. (1992, pp. 4823-4831, vol. 35).
Masanori Somei et al., Preparation Of N-Aminoheterocycles And Their Reactions, Pharm. Inst. Tohoku Univ., Sendai Japan (1975, pp. 219-223) abstract.
Masanori Somei et al., The Chemistry Of Indoles, Tetrahedron Letters No. (1974, pp. 3605-3608, vol. 41).

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