851048-48-1

Upstream product

• 1191-95-3 cyclobutanone 
• 112275-50-0 tert-butyl 1,4-diazepine-1-carboxylate 

Relevant academic research and scientific papers

First, second, and third generation scalable syntheses of two potent H 3 antagonists

Our teams have recently completed scale-up campaigns for two structurally similar H3 receptor antagonists. The first and second generation processes were developed for the synthesis of 107 and 125 g batches of (4-cyclobutyl-1,4-diazepan-1-yl)(6

Synthesis of a histamine H3 receptor antagonist - Manipulation of hydroxyproline stereochemistry, desymmetrization of homopiperazine, and nonextractive sodium triacetoxyborohydride reaction workup

(Figure presented) We have recently completed the synthesis of 1-[2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-(3-fluoro-phenoxy) -pyrrolidin-1-yl]-ethanone, a hydroxyproline-based H3 receptor antagonist, on 100 g scale. The synthesis proceeds through four steps and route selection was driven by a desire to minimize the cost-of-goods. Naturally occurring trans-4-hydroxy-L-proline was chosen as the precursor to the targets core, which necessitated an inversion at both stereogenic centers. The inversions were accomplished through strategic employment of La Rosas lactone and a late-stage Mitsunobu reaction. A first generation synthesis that employed N-Boc-homopiperazine was improved in a second generation approach wherein homopiperazine was directly desymmetrized. Finally, the water solubility of a key intermediate necessitated the development of a nonextractive workup for the sodium triacetoxyborohydride reduction.

AZETIDINES AS HISTAMINE H3 RECEPTOR ANTAGONISTS

The invention relates to compounds of formula (I), wherein R, R1, m, n and X1to X3 have the meaning as cited in the description and the claims. Said compounds are useful as Histamine H3 receptor antagonists. The invention

Spirocyclobutyl Piperidine Derivatives

Disclosed herein is at least one spirocyclobutyl piperidine derivative, at least one pharmaceutical composition comprising at least one spirocyclobutyl piperidine derivative disclosed herein, and at least one method of using at least one spirocyclobutyl piperidine derivative disclosed herein for treating at least one histamine H3 receptor associated condition therewith.

DIAZEPANES AS HISTAMINE H3 RECEPTOR ANTAGONISTS

The invention relates to compounds of formula (I) wherein R1 to R8 and X1, X2 have the meaning as cited in the description and the claims. Said compounds are useful as Histamine H3 receptor antagonists. The invention also relates to pharmaceutical compositions, the preparation of such compounds as well as the production and use as medicament.

AZETIDINES AND CYCLOBUTANES AS HISTAMINE H3 RECEPTOR ANTAGONISTS

The invention relates to compounds of formula (I) wherein R, R0, R1, m, n and X1 to X4 have the meaning as cited in the description and the claims. Said compounds are useful as Histamine H3 receptor antagonists. The invention also relates to pharmaceutical compositions, the preparation of such compounds as well as the production and use as medicament.

SUBSTITUTED BENZAMIDE MODULATORS OF THE HISTAMINE H3 RECEPTOR

Certain substituted benzamide compounds are histamine H3receptor modulators useful in the treatment of histamine H3 receptor-mediated diseases.

SUBSTITUTED PYRIDYL AMIDE COMPOUNDS AS MODULATORS OF THE HISTAMINE H3 RECEPTOR

Certain substituted pyridyl amide compounds are histamine H3 receptor modulators useful in the treatment of histamine H3 receptor-mediated diseases.

PYRROLIDINE DERIVATIVES AS HISTAMINE RECEPTORS LIGANDS

The present invention relates to pyrrolidine derivatives of formula (I) having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of neurological and psychiatric disorders.

NOVEL COMPOUNDS

The present invention relates to novel diazepanyl derivatives of formula (I) having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of neurological and psychiatric disorders.