21472-89-9

Usage

Uses

1. Used in Pharmaceutical Synthesis:
1-Aza-bicyclo[2.2.1]heptan-3-one is used as a synthetic intermediate for the preparation of spirocyclic quinuclidinyl-Δ2-isoxazolines. These compounds act as neuronal nicotinic acetylcholine receptor agonists, which can be beneficial in the treatment of neurological disorders related to the cholinergic system.
2. Used in Progranulin Modulation:
In the field of neurodegenerative diseases, 1-Aza-bicyclo[2.2.1]heptan-3-one is used as a precursor in the synthesis of isoquinoline derivatives. These derivatives serve as progranulin modulators, which are useful in the treatment of progranulin-associated disorders, such as frontotemporal lobar degeneration and neuroinflammatory conditions.
3. Used in Cancer Treatment:
1-Aza-bicyclo[2.2.1]heptan-3-one is also utilized in the preparation of N-pyridinyl carboxamides, which are cyclin-dependent kinase inhibitors. These inhibitors play a crucial role in regulating cell cycle progression and have potential applications in the treatment of various types of cancer.
4. Used in Metabolic Disease Treatment:
In the realm of metabolic diseases, 1-Aza-bicyclo[2.2.1]heptan-3-one is employed in the synthesis of glucosylceramide synthase inhibitors. These inhibitors are essential for the treatment of lysosomal storage diseases, which are a group of inherited metabolic disorders characterized by the accumulation of substances within lysosomes due to enzyme deficiencies.
Overall, 1-Aza-bicyclo[2.2.1]heptan-3-one is a valuable compound in the pharmaceutical industry, with applications spanning across various therapeutic areas, including neurology, oncology, and metabolic disorders. Its versatility as a synthetic intermediate makes it a promising candidate for the development of innovative treatments and therapies.

InChI:InChI=1/C6H9NO/c8-6-4-7-2-1-5(6)3-7/h5H,1-4H2

Upstream product

• 121564-87-2 methyl 1-(2-methoxy-2-oxoethyl)pyrrolidine-3-carboxylate 
• 121564-86-1 methyl 1-(2-methoxy-2-oxoethyl)-5-oxopyrrolidine-3-carboxylate 
• 142483-57-6 1-<(ethoxycarbonyl)methyl>-3-(methoxycarbonyl)pyrrolidine 

Downstream Products

• 122755-14-0 exo-3-hydroxy-endo-3-methoxycarbonyl-1-azabicyclo<2.2.1>heptane 
• 122755-14-0 endo-3-hydroxy-exo-3-methoxycarbonyl-1-azabicyclo<2.2.1>heptane 
• 125059-70-3 (3S,4S)-3-(6-Methyl-pyrazin-2-yl)-1-aza-bicyclo[2.2.1]heptan-3-ol 
• 125060-84-6 (3R,4R)-3-(3,5,6-Trimethyl-pyrazin-2-yl)-1-aza-bicyclo[2.2.1]heptan-3-ol 
• 125060-64-2 (3S,4S)-3-(6-Methoxy-pyrazin-2-yl)-1-aza-bicyclo[2.2.1]heptan-3-ol 
• 125059-75-8 (3S,4S)-3-(6-Ethoxy-pyrazin-2-yl)-1-aza-bicyclo[2.2.1]heptan-3-ol 
• 125059-73-6 (3S,4S)-3-(6-Dimethylamino-pyrazin-2-yl)-1-aza-bicyclo[2.2.1]heptan-3-ol 
• 125060-72-2 (3S,4S)-3-(6-Isopropoxy-pyrazin-2-yl)-1-aza-bicyclo[2.2.1]heptan-3-ol 
• 125060-76-6 (3S,4S)-3-(6-Allyloxy-pyrazin-2-yl)-1-aza-bicyclo[2.2.1]heptan-3-ol 
• 21473-16-5 endo-3-hydroxy-1-azabicyclo<2.2.1>heptane 
• 103660-35-1 2-(2-Chlorobenzylidene)-1-azabicyclo[2.2.2]octan-3-one 
• 24123-91-9 2-(1-naphthylmethylene)-3-quinuclidinone 
• 103660-32-8 2-(3,4-dimethoxyphenylmethylene)-3-oxoquinuclidine 
• 125059-55-4 (1R,3S,4S)-3-Pyrazin-2-yl-1-aza-bicyclo[2.2.1]heptan-3-ol 

Relevant academic research and scientific papers

PROGRANULIN MODULATORS AND METHODS OF USING THE SAME

Provided herein are compounds that modulate progranulin and methods of using the compounds in progranulin-associated disorders, such as Frontotemporal dementia (FTD).

GLUCOSYLCERAMIDE SYNTHASE INHIBITORS

The invention relates to inhibitors of glucosylceramide synthase (GCS) useful for the treatment metabolic diseases, such as lysosomal storage diseases, either alone or in combination with enzyme replacement therapy.

Glucosylceramide synthase inhibitors

The invention relates to inhibitors of glucosylceramide synthase (GCS) useful for the treatment metabolic diseases, such as lysosomal storage diseases, either alone or in combination with enzyme replacement therapy, and for the treatment of cancer.

Inhibitors of protein kinases

Compounds of general Formula (I): wherein R1, R2, R3, Ra, A, B and x are as defined herein are inhibitors of protein kinases in particular members of the cyclin-dependent kinase family and/or the glycogen synthase kinase 3 family and are useful in preventing and/or treating any type of pain, inflammatory disorders, cancer, immunological diseases, proliferative diseases, infectious diseases, cardiovascular diseases, metabolic disorders, renal diseases, neurologic and neuropsychiatric diseases and neurodegenerative diseases.

Oxadiazoles useful in the treatment of senile dementia

A class of novel oxadiazoles, substituted on one of the ring carbon atoms with a non-aromatic azacyclic or azabicyclic ring, and substituted on the other ring carbon atom with a substituent of low lipophilicity; are potent muscarinic agonists, and have good CNS penetrability. The compounds are therefore useful in the treatment of neurological and mental illnesses.

THIADIAZOLES USEFUL IN THE TREATMENT OF SENILE DEMENTIA

A class of novel thiadiazoles, substituted on one of the ring carbon atoms with a non-aromatic azacyclic or azabicyclic ring system, and substituted on the other ring carbon atom with a substituent of low lipophilicity, or a hydrocarbon substituent; are potent muscarinic agonists, and have good CNS penetrability. The compounds are therefore useful in the treatment of neurological and mental illnesses, and are also of benefit in the treatment of severe painful conditions.

Substituent variation in azabicyclic triazole- and tetrazole-based muscarinic receptor ligands

The effect of variation of the 1-azabicyclic substituent on the novel 1,2,3-triazol-4-yl-, 1,2,4-triazol-1-yl-, tetrazol-5-yl-, and tetrazol-2-yl- based muscarinic receptor ligands has been studied, and the exo- azabicyclic[2.2.1]hept-3-yl substituent was found to give the most potent and efficacious compounds. In addition, variation of the second substituent on 1,2,4-triazol-1-yl- and tetrazol-2-yl-based muscarinic receptor ligands has yielded a series of novel compounds with high potencies and efficacies, ranging from full agonists to antagonists. Small lipophilic electron withdrawing substituents give potent but low efficacy compounds, while small polar electron donating substituents give potent and efficacious compounds. The activity of these compounds is described in terms of a model of the receptor involving lipophilic and hydrogen bonding interactions. These compounds provide muscarinic ligands with high potency and a range of efficacies suitable for testing as candidate drugs in the treatment of Alzheimer's disease.

Synthesis and biological activity of 1,2,4-oxadiazole derivatives: Highly potent and efficacious agonists for cortical muscarinic receptors

The synthesis and biochemical evaluation of novel 1,2,4-oxadiazole-based muscarinic agonists which can readily penetrate into the CNS is reported. Efficacy and binding of these compounds are markedly influenced by the structure and physicochemical properties of the cationic head group. In a series of azabicyclic ligands efficacy and affinity are influenced by the size of the surface area presented to the receptor, at the active site, and the degree of conformational flexibility. The exo-1-azanorbornane 16a represents the optimum arrangement, and this compound is one of the most efficacious and potent muscarinic agonists known. In a series of isoquinuclidine based muscarinic agonists efficacy and are influenced by the geometry between the cationic head group and hydrogen bond acceptor pharmacophore and steric bulk in the vicinity of the base. The anti configuration represented by 22a is optimal for muscarinic activity. Ligands with pK(a) below 6.5 show poor binding to the muscarinic receptor as exemplified by the diazabicyclic derivative 42.

Oxadiazolyl-azabicyloheptanes for the treatment of senile dementia

Oxadiazoles represented by structural formula I: or a salt or prodrug thereof; wherein one of X, Y or Z is an oxygen atom and the other two are nitrogen atoms, and the dotted circle represents aromaticity (two double bonds); R2 represents a substituent of low lipophilicity; the broken line represents an optional chemical bond; and the substituents R3 and R? may be present at any position, including the point of attachment to the oxadiazole ring, and R3 represents halo, C??? alkoxy, carboxy,-NR?R?, C??? alkyl, C?? ? alkyl substituted with hydroxy or C??? alkoxy, or methyl or hydroxy in the 3-, 4-or 5-position; and R? represents hydrogen, halo, C??? alkoxy, hydroxy, carboxy,-NR? R?, C??? alkyl, or C??? alkyl substituted with hydroxy or C??? alkoxy; or R3 and R? together represent carbonyl; and R? and R? independently represent hydrogen or C??? alkyl are potent muscarinic agonists with good CNS penetrability, and are therefore useful in the treatment of neurological and mental illnesses; the compounds are also of benefit in the treatment of severe painful conditions. Processes for preparing these compounds are described, as also are pharmaceutical compositions containing them.