6238-30-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxyquinuclidine-3-carbonitrile is used as a key intermediate for the synthesis of various organic compounds, specifically in the production of pharmaceutical drugs. Its role is pivotal in creating molecules that address central nervous system disorders, leveraging its unique structural attributes to facilitate the development of effective treatments.
Used in Drug Discovery and Development:
In the realm of drug discovery and development, 3-Hydroxyquinuclidine-3-carbonitrile is utilized as a building block to create a wide range of biologically active molecules. Its chemical properties allow for the design and synthesis of new pharmaceutical agents, contributing to the advancement of medicinal chemistry and the treatment of various conditions related to the central nervous system.

InChI:InChI=1/C19H16N4O4S2/c24-8-6-20-16-13(17(25)22-7-2-1-5-15(22)21-16)10-14-18(26)23(19(28)29-14)11-12-4-3-9-27-12/h1-5,7,9-10,20,24H,6,8,11H2

Upstream product

• 151-50-8 potassium cyanide 
• 1193-65-3 3-quinuclidinone hydrochloride 
• 143-33-9 sodium cyanide 
• 3731-38-2 3-Quinuclidinone 
• 39896-06-5 quinuclidine hydrochloride 

Downstream Products

• 26630-16-0 3-morpholino-3-cyanoquinuclidine 
• 81547-25-3 quinuclidine-3-spiro-5'-oxazolidine-2',4'-dione 
• 6238-31-9 (+/-)-ethyl 3-hydroxy-1-azabicyclo[2.2.2]octane-3-carboxylate 
• 128223-36-9 2'-(1H-indol-3-yl)spiro(1-azabicyclo<2.2.2>octane-3,5'(4'H)-oxazole) dihydrochloride 
• 128199-67-7 2'-(1-methyl-1H-indol-3-yl)spiro(1-azabicyclo<2.2.2>octane-3,5'(4'H)-oxazole) dihydrochloride 
• 138982-76-0 C₁₆H₂₀N₂O₂*2ClH 
• 128199-81-5 C₁₇H₁₈N₂OS*2ClH 
• 128199-86-0 C₁₆H₁₈N₄O*3ClH 
• 128199-90-6 C₁₉H₂₃N₃O*2ClH 
• 128199-91-7 C₁₉H₂₃N₃O*2ClH 
• 128199-70-2 [2'-(5-fluoro-1-methyl-1H-indol-3-yl)]spiro(1-azabicyclo[2.2.2]octane-3,5'(4'H)-oxazole) 
• 128199-88-2 C₁₉H₂₃N₃O₂*2ClH 
• 128199-84-8 2'-(5-amino-1-methyl-1H-indol-3-yl)spiro(1-azabicyclo<2.2.2>octane-3,5'(4'H)-oxazole) trihydrochloride 
• 128199-87-1 C₁₈H₂₀N₄O₃*2ClH 

Relevant academic research and scientific papers

NOVEL SPIRO-QUINUCLIDINYL DERIVATIVES FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS

The present invention is directed to novel spiro-quinuclidinyl derivatives, pharmaceutical compositions containing them and their use in the treatment of central nervous system disorders.

Novel spiro-quinuclidinyl derivatives for the treatment of central nervous system disorders

The present invention is directed to novel spiro-quinuclidinyl derivatives, pharmaceutical compositions containing them and their use in the treatment of central nervous system disorders.

Novel spiro-quinuclidinyl derivatives for the treatment of central nervous system disorders

The present invention is directed to novel spiro-quinuclidinyl derivatives, pharmaceutical compositions containing them and their use in the treatment of central nervous system disorders.

Novel 5-HT3 antagonists: Indol-3-ylspiro(azabicycloalkane-3,5'(4'H)- oxazoles)

The synthesis and biochemical evaluation of a series of spirofused indole oxazoline 5-HT3 antagonists is described in which the oxazoline ring acts as a bioisosteric replacement for esters and amides. The effect of substitution about the indole ring has shown the steric limitations of the aromatic binding site. Incorporation of a variety of azabicyclic systems within the rigid spirofused framework has allowed the definition of a binding model which incorporates a number of known antagonists and agonists. In this model steric constraints limit substitution around the indole ring although there is some bulk tolerance at the 1- and 2-positions. The importance of constraining the basic nitrogen within an azabicyclic system is underlined by comparison with the monocyclic piperidine. The highest affinity was observed for those compounds in which the basic nitrogen occupies a bridgehead position, the most potent analogue in this group being the azabicyclic [3.3.1] system (pIC50 = 8.95), suggesting lipophilic interactions may play a role in increasing affinity. A suggested model for agonist binding is included in which the basic nitrogens are superimposed and the 5-hydroxyl group of 5-HT is superimposed on the H-bond-accepting atom of the heterocyclic linking group.

Preparation of quinuclidine-3-methanol

A process for the preparation of quinuclidine-3-methanol comprising reacting quinuclidine-3-one acid addition salt with an alkali metal cyanide in an aqueous media to obtain 3-cyano-3-hydroxy-quinuclidine, reacting the latter with anhydrous methanol in the presence of hydrogen chloride gas followed by treatment with aqueous alkali to obtain methyl 3-hydroxy-quinuclidine-3-carboxylate, reacting the latter with thionyl chloride to form methyl 1-azabicyclo(2,2,2)oct-2-ene-3-carboxylate, hydrogenating the latter with Raney nickel to obtain methyl 1-azabicyclo(2,2,2)octane-3-carboxylate and reducing the latter to obtain quinuclidine-3-methanol which is an intermediate for mequitazine which is useful as an antihistaminic.

Spirocyclic compounds incorporating five-membered rings with two heteroatoms for treating psychotic disorders, etc.

The present invention provides a compound of formula I or a salt or prodrug thereof: STR1 wherein the dotted line represents an optional chemical bond in one of the two possible positions; A represents a group of formula II: STR2 in which R1 represents hydrogen, hydroxy, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, benzyloxy, hydroxy (C1-6)alkyl, halogen, amino, cyano, nitro, --CONR6 R7 or --SO2 NR6 R7, in which R6 and R7 independently represent hydrogen, halogen, C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl; R2 represents hydrogen, halogen, C1-6 alkyl, C1-6 alkoxy or C1-6 alkylcarbonyl; V represents nitrogen, --CH or --C--; and W represents oxygen, sulphur or --NR8, in which R8 represents hydrogen, C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl; two of X, Y and Z are the same or different and each represents oxygen, sulphur or nitrogen; and the remaining group X, Y or Z is carbon, or Y is carbonyl (C=O); and Q is the residue of an azacyclic or azabicyclic ring system; which compounds are useful in the treatment of psychotic disorders (e.g. schizophrenia and mania); anxiety; alcohol or drug withdrawal or dependence; pain; gastric stasis; gastric dysfunction (such as occurs with dyspepsia, peptic ulcer, reflux oesophagitis and flatulence); migraine, nausea and vomiting; movement disorders; and presenile and senile dementia.

Imidazole derivatives and salts thereof and pharmaceutical formulations useful in thrombo-embolic disorders

Imidazoles of formula (I) STR1 wherein A is a chemical bond or a straight or branched, saturated or unsaturated, aliphatic residue having from 1 to 6 carbon atoms wherein 1, 2 or 3 of such carbon atoms may be replaced by a corresponding number of heteroatoms selected from oxygen, sulphur and nitrogen providing (in the case of 2 or 3 heteroatoms) that any such heteroatom is not located adjacent to a further such heteroatoms or heteroatoms R is a fused, saturated or unsaturated, non-aromatic carbocyclic, polycyclic ring system; a saturated or unsaturated, carbocyclic spirocyclic ring system, optionally containing one or more ring heteroatoms selected from oxygen, sulphur and nitrogen; or a saturated or unsaturated, carbocyclic bridged-polycyclic ring system, optionally containing one or more ring heteroatoms selected from oxygen, sulphur and nitrogen and having one or more bridges; or AR together represent a straight or branched, saturated or unsaturated, aliphatic residue having 3 to 6 carbon atoms, wherein 1, 2 or 3 of such carbon atoms may be replaced by a corresponding number of heteroatoms selected from oxygen, sulphur and nitrogen providing (in the case of 2 or 3 heteroatoms) that any such heteroatom is not located adjacent to a further such heteroatom or heteroatoms; which aliphatic residue is substituted by at least two groups, which may be the same or different, selected from the groups specified for R above. and acid addition salts and pharmaceutically acceptable bioprecursors thereof. Methods of preparing the imidazoles are disclosed. The imidazoles and their acid addition salts and bioprecursors are useful in the treatment or prophylaxis of thrombo-embolic conditions.

Synthesis and Structural Study of Quinuclidine Spiro Derivatives

The synthesis of quinuclidine-3-spiro-5'-oxazolidine-2',4'-dione, quinuclidine-3-spiro-5'-hydantoin, and some 3'-derivatives is described.Based on the data from 1H and 13C-nmr spectra the structure of the above mentioned compounds is established.A relationship between second order effects in 13C-nmr spectra and H-C-C-H dihedral angles is deduced.