120570-05-0

Basic information

• Product Name: (S)-quinuclidin-3-aMine
• Synonyms: (S)-quinuclidin-3-aMine;(S)-1-Aza-bicyclo[2.2.2]oct-3-ylamine;(3S)-1-azabicyclo[2.2.2]octan-3-amine;1-Azabicyclo[2.2.2]octan-3-amine, (S)-
• CAS NO: 120570-05-0
• Molecular Formula: C₇H₁₄N₂
• Molecular Weight: 126.19946
• Mol File: 120570-05-0.mol

Chemical Properties

• Boiling Point: 165.9°C at 760 mmHg
• Flash Point: 51.1°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 1.83mmHg at 25°C
• Refractive Index: 1.551
• Storage Temp.: 2-8°C(protect from light)
• PKA: 10.58±0.33(Predicted)
• CAS DataBase Reference: (S)-quinuclidin-3-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-quinuclidin-3-aMine(120570-05-0)
• EPA Substance Registry System: (S)-quinuclidin-3-aMine(120570-05-0)

Safety Data

• Hazardous Substances Data: 120570-05-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-Quinuclidin-3-aMine is used as an intermediate in the synthesis of Palonosetron-3-ene Hydrochloride (P165825), which is an impurity of Palonosetron (P165800). Palonosetron is a serotonin 5-HT3 receptor antagonist that is utilized in the prevention and treatment of chemotherapy-induced nausea and vomiting (CINV). As an antiemetic, (S)-Quinuclidin-3-aMine contributes to the development of medications that help alleviate the distressing side effects of chemotherapy, improving the quality of life for cancer patients.

InChI:InChI=1/C7H14N2/c8-7-5-9-3-1-6(7)2-4-9/h6-7H,1-5,8H2/t7-/m1/s1

Upstream product

• 123194-01-4 3-amino-1-azabicyclo<2.2.2>octane-3-carbonitrile 
• 16205-47-3 7-methyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid 
• 6530-09-2 (S)-1-azabicyclo[2.2.2]oct-3-ylamine dihydrochloride 

Downstream Products

• 193882-52-9 5-chloro-2-methoxy-N-(1-azabicyclo<2.2.2>oct-3-yl)benzamide 
• 124808-64-6 N-[[[1-Azabicyclo[2.2.2]octan-3-yl] amino]carbonyl]-2-methylbenzamide 
• 124808-59-9 N-[[[1-azabicyclo[2.2.2]octan-3-yl]amino]carbonyl]-2-fluorobenzamide 
• 124808-43-1 N-[[[1-azabicyclo[2.2.2]octan-3-yl]amino]carbonyl]-2-methoxybenzamide 
• 138572-71-1 5-chloro-3-cyclohexyl-2-isobutoxy-N-(1-azabicyclo<2.2.2>oct-3-yl)benzamide 
• 138572-73-3 N-(1-Aza-bicyclo[2.2.2]oct-3-yl)-5-chloro-3-cyclohexyl-2-(1-methyl-allyloxy)-benzamide 
• 138572-72-2 5-chloro-3-cyclohexyl-2-(2'-oxo-1'-methylpropoxy)-N-(1-azabicyclo<2.2.2>oct-3-yl)benzamide 
• 176088-67-8 N-(1-azabicyclo[2.2.2]oct-3-yl)-2-methylbenzamide 
• 123040-69-7 azasetron 
• 141762-13-2 4-Benzyl-6-chloro-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide 
• 142843-11-6 3-<2-<<(2R,3S)-3-<(tert-butoxycarbonyl)amino>-4-cyclohexyl-2-hydroxy-1-butyl>thio>acetamido>quinuclidine 
• 141762-14-3 6-Chloro-3-oxo-4-phenethyl-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide 
• 143396-49-0 {(S)-1-[(S)-1-{(1S,2R)-3-[(1-Aza-bicyclo[2.2.2]oct-3-ylcarbamoyl)-methylsulfanyl]-1-cyclohexylmethyl-2-hydroxy-propylcarbamoyl}-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester 
• 176088-63-4 (RS)-N-(1-azabicyclo[2.2.2]oct-3-yl)-2-ethyl-3-methylbenzamide 

Relevant articles and documents

A hydrochloric acid palonosetron production method

The invention belongs to the field of organic synthesis, and particularly relates to a production method of high-purity and high-yield palonosetron hydrochloride. Chiral compounds, namely, (S)-(-)-1,2,3,4-tetrahedro-naphthoic acid and S-3-aminoquinuclidine, are taken as raw materials, and an intermediate is obtained; the intermediate has a reduction reaction in the presence of NaBH4 and BF3*CH3OH, a product is added to a hydrochloric acid aqueous solution for a reflux reaction after the reaction, and a transparent oily substance is obtained through extraction after the reflux reaction; toluene is added to the substance, a toluene solution of triphosgene is dropwise added again at the temperature ranging from 10 DEG C to 15 DEG C, white solids are separated out, a reaction is performed under the condition of heating reflux, and the toluene solution of the triphosgene is dropwise added again under the reflux condition; then a system is cooled to the temperature ranging from 10 DEG C to 15 DEG C, BF3*CH3OH is added, the system is added to water and the hydrochloric acid aqueous solution at the reflux temperature after addition, then a reflux reaction is performed at the heating reflux temperature, and then a crude product is obtained through washing, extraction and crystallization; the crude product is dissolved in acetone, repeated crystallization is performed after dissolution, and the refined palonosetron hydrochloride is obtained. Steps are simple and convenient, reaction conditions are mild, and the production method is easy to operate and suitable for industrial production.

PROCESSES FOR THE PREPARATION OF PALONOSETRON

The present invention relates to novel processes for the preparation of N-[(3S)-1- azabicyclo[2.2.2]oct-3-yl]-5,6,7,8-tetrahydronaphthalene-1-carboxamide of Formula I. The present invention further relates to processes for the preparation of palonosetron or its salts thereof using N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-5,6,7,8- tetrahydronaphthalene-1-carboxamide of Formula I as an intermediate.

PREPARATION OF CRYSTALLINE PALONOSETRON HYDROCHLORIDE

Processes for the preparation of palonosetron hydrochloride and its crystalline forms.

Processes for preparing palonosetron salts

The present invention provides processes for preparing Palonosetron salts, especially, the hydrochloride salt and intermediates used to prepare Palonosetron salts.

Synthesis of 2'-arylazabicyclo-3-spiro-4'(5')-imidazolines

A method is described for the synthesis of a series of 2'-aryl-3-azabicyclospiro-4'(5')-imidazolines via the reaction of azabicyclic 1,2-diamines with aryl imidate salts. Competing reactions in the synthesis of the diamines such as the reduction of amino nitriles with LiAlH4 lead to some anomalous products. In the Pinner synthesis, unstable pyridine-type imidates were stabilized as their N-oxide derivatives.

Pyrazolo[1,5-a]pyridine-3-carboxylic acid derivatives and their pharmaceutical use

Described herein are pyrazolo[1,5-a]pyridine-3-carboxylic acid derivatives represented by the following formula (I): STR1 wherein R 1 and R 2 individually mean a hydrogen atom or a lower alkyl group, R 3 denotes an azabicyclo group containing a tertiary nitrogen atom, and Y stands for --O-- or --NH--, or salts thereof. Their preparation process and serotonin receptor antagonists containing them as active ingredients are also described.

Enantiomers of absolute configuration S of amide derivatives of 3-aminoquinuclidine, the process for preparing them and their application in therapy

Enantiomer of absolute configuration S of formula: STR1 where: X=O or S; and Ar denotes a: * phenyl ring substituted with one, two or three C1 -C4 alkoxy groups; * phenyl ring substituted at the 2-position with a OCH3 group and at the 5-position with a halogen atom or a lower alkylcarbonyl group; * phenyl ring substituted at the 2-position with OCH3, at the 4-position with NH2 or alkylcarbonyl-NH and at the 5-position with a halogen; * 3-fluoro-2-methoxyphenyl group; * 5-pyrimidinyl group substituted at the 2-position with NH2 and in the 4-position with alkoxy or phenyloxy. These compounds are useful as medicinal products having activity in respect of gastric movements and antiemetic activity.

Heterocyclic compounds useful as 5-HT3 antagonists

Aroyl ureas and carbamic acid derivatives of formula and pharmaceutically acceptable salts thereof wherein A is a specified aromatic radical including optionally substituted phenyl W is O or S Y is NH or S and B is a specified saturated azacyclic ring, eg tropan-3-yl or quinuclidin-3-yl, possess 5-HT3 -antagonistic activity and are, for example, useful in treatment of migraine, emesis, anxiety, gastro-intestinal disorders and as anti-psychotics.

Fused imidazoheterocyclic compounds and pharmaceutical compositions

Imidazoheterocyclic compounds having the formula: STR1 wherein the A ring is pyridine in any of its four positions; B is carbonyl, thioxomethyl or hydroxymethylene; Z is hydrogen, halogen, loweralkyl, hydroxy, loweralkoxy, diloweralkylamino or nitro; Ar i