76272-36-1

Usage

Uses

Used in Pharmaceutical Industry:
3-AMINO-8-BENZYL-8-AZABICYCLO[3.2.1]OCTANE (3-EXO)is used as an intermediate in the preparation of CCR5 receptor antagonists for the treatment of HIV infection and other diseases. It plays a significant role in modulating the immune response and preventing viral entry into host cells.
Used in Antibacterial Applications:
3-AMINO-8-BENZYL-8-AZABICYCLO[3.2.1]OCTANE (3-EXO)is used as a key component in the development of antibacterial agents, targeting various bacterial pathogens and contributing to the discovery of novel antibiotics to combat drug-resistant infections.
Used in Dopamine Antagonist Development:
3-AMINO-8-BENZYL-8-AZABICYCLO[3.2.1]OCTANE (3-EXO)is utilized as an intermediate in the synthesis of dopamine antagonists, which are essential for the treatment of various neurological and psychiatric disorders, such as schizophrenia, bipolar disorder, and Parkinson's disease. These antagonists help regulate dopamine levels in the brain, providing therapeutic benefits for patients.

InChI:InChI=1/C14H20N2/c15-12-8-13-6-7-14(9-12)16(13)10-11-4-2-1-3-5-11/h1-5,12-14H,6-10,15H2/t12-,13-,14+

Upstream product

• 1515-26-0 (1R,5S)-8-Methyl-8-aza-bicyclo[3.2.1]octan-3-one oxime 
• 28957-72-4 N-benzylnortropinone 
• 532-24-1 tropinone 
• 542-05-2 acetonedicarboxylic acid 
• 76272-34-9 8-Benzyl-1αH,5αH-nortropan-3-one Oxime 
• 100-44-7 benzyl chloride 
• 132259-54-2 exo-(8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-carbamic acid tert-butyl ester 
• 28957-72-4 N-benzyltropinone 
• 100-46-9 benzylamine 
• 76272-34-9 8-benzyl-8-azabicyclo[3.2.1] octan-3-one oxime 
• 850847-96-0 N-benzyl-3-α-(4-dimethylaminobenzylideneamino)nortropane 
• 1415560-32-5 endo-8-benzyl-8-azabicyclo[3.2.1]oct-3-ylamine dihydrochloride 

Downstream Products

• 132259-54-2 exo-(8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-carbamic acid tert-butyl ester 
• 84923-00-2 4-Methoxy-pyrimidine-5-carboxylic acid ((1R,3S,5S)-8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide 
• 84923-02-4 4-Methoxy-2-methyl-pyrimidine-5-carboxylic acid ((1R,3S,5S)-8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide 
• 76352-24-4 2-Amino-4-methoxy-pyrimidine-5-carboxylic acid ((1R,3S,5S)-8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide 
• 84923-06-8 2-Ethyl-4-methoxy-pyrimidine-5-carboxylic acid ((1R,3S,5S)-8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide 
• 76351-82-1 2-Amino-4-ethoxy-pyrimidine-5-carboxylic acid ((1R,3S,5S)-8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide 
• 84936-77-6 2-Dimethylamino-4-methoxy-pyrimidine-5-carboxylic acid ((1R,3S,5S)-8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide 
• 84923-08-0 2-Dimethylamino-4-ethoxy-pyrimidine-5-carboxylic acid ((1R,3S,5S)-8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide 
• 376348-67-3 exo-N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)-2-methylpropanamide 
• 1221446-23-6 N-(8-benzyl-3-exo-8-azabicyclo[3.2.1]oct-3-yl)-4-tolylsulfonamide 
• 423165-13-3 exo-8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane 
• 423165-07-5 UK-408027 
• 1221446-17-8 tert-butyl 8-(3-(1-acetyl-N-(3-chloro-4-methylphenyl)-4-piperidineformamide)propyl)-3-exo-8-azabicyclo[3.2.1]octan-3-carbamate 
• 1221446-18-9 1-acetyl-N-(3-(3-exo-amino-8-azabicyclo[3.2.1]oct-8-yl)propyl)-N-(3-chloro-4-methylphenyl)-4-piperidinylcarboxamide 

Relevant academic research and scientific papers

CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

METHOD FOR PREPARING MARAVIROC

Provided is a method for preparing a tropane derivative, maraviroc, including reacting a compound of formula (II) with a compound of formula (I), wherein the compound of formula (II) is prepared by the steps of acetylation of a compound of formula (III), activation and substitution of a compound of formula (IV) by a chlorination agent, cyclization of a compound of formula (V), and debenzylation of a compound of formula (VI) by hydrogenation. Hence, the present disclosure provides a method for preparing maraviroc with good yield and simple operation.

Bifunctional Chimera That Coordinately Targets Human Immunodeficiency Virus 1 Envelope gp120 and the Host-Cell CCR5 Coreceptor at the Virus-Cell Interface

To address the urgent need for new agents to reduce the global occurrence and spread of AIDS, we investigated the underlying hypothesis that antagonists of the HIV-1 envelope (Env) gp120 protein and the host-cell coreceptor (CoR) protein can be covalently joined into bifunctional synergistic combinations with improved antiviral capabilities. A synthetic protocol was established to covalently combine a CCR5 small-molecule antagonist and a gp120 peptide triazole antagonist to form the bifunctional chimera. Importantly, the chimeric inhibitor preserved the specific targeting properties of the two separate chimera components and, at the same time, exhibited low to subnanomolar potencies in inhibiting cell infection by different pseudoviruses, which were substantially greater than those of a noncovalent mixture of the individual components. The results demonstrate that targeting the virus-cell interface with a single molecule can result in improved potencies and also the introduction of new phenotypes to the chimeric inhibitor, such as the irreversible inactivation of HIV-1.

Synthesis and biological investigations of 3β-aminotropane arylamide derivatives with atypical antipsychotic profile

This work is a continuation of our previous research, concentrating this time on lead structure modification to increase the 5-HT1A receptor affinity and water solubility of designed compounds. Therefore, the compounds synthesised within the present project included structural analogues of 3β-acylamine derivatives of tropane with the introduction of a methyl substituent in the benzyl ring and a 2-quinoline, 3-quinoline, or 6-quinoline moiety. A series of novel 3β-aminotropane derivatives was evaluated for their affinity for 5-HT1A, 5-HT2A, and D2 receptors, which allowed for the identification of compounds 12e, 12i, and 19a as ligands with highest affinity for the tested receptors; they were then subjected to further evaluation in preliminary in vivo studies. Selected compounds 12i and 19a displayed antipsychotic properties in the d-amphetamine-induced and MK-801-induced hyperlocomotor activity test in mice. Moreover, compound 19a showed significant antidepressant-like activity in the forced swim test in mice.

Preparation and activities of macromolecule conjugates of the CCR5 antagonist maraviroc

CCR5 antagonists are among the most advanced approaches in HIV therapy and may also be relevant to treatment of graft-versus-host disease and Staphylococcus aureus infection. To expand the potential of the only approved CCR5 antagonist, Maraviroc, we studied derivatives that would enable functional linkage of Maraviroc to long-lived carriers. Through targeted synthesis, we discovered an effective linkage site on Maraviroc and demonstrate the potential of these derivatives to prepare potent chemically programmed antibodies and PEGylated derivatives. The resulting compounds effectively neutralized a variety of HIV-1 isolates. Both chemically programmed antibody and PEGylation approaches extend the neutralization activity of serum circulating Maraviroc. Derivation of a successful conjugation strategy for Maraviroc should further enable its use in chemically programmed vaccines, novel bispecific antibodies, and topical microbicides.

1,4 DI SUBSTITUTED PYRROLIDINE - 3 - YL -AMINE DERIVATIVES AND THEIR USE FOR THE TREATMENT OF METABOLIC DISORDERS

Therapeutic compounds are disclosed having the general formula (1) that are useful for the treatment of metabolic disorders, including type II diabetes.The compounds have activity as agonists of GPR1 19. Compounds having the stereochemistry of formula (la) may also demonstrate DPP-IV inhibitory activity.

AMIDE COMPOUNDS, THEIR PHARMACEUTICAL COMPOSITIONS, THEIR PREPARATION METHOD AND THEIR USES

The present invention pertains to the field of pharmaceutical chemistry and discloses 8-(3-aminopropyl)-3-exo-8-azabicyclo[3.2.1]octane-3-amino amide compounds represented by formula I, the pharmaceutical compositions, the preparation method and the use thereof. Such compounds or pharmaceutically acceptable salts thereof can be used as an antagonist of CCR5 in preparing medicaments for treating diseases mediated by CCR5, particularly HIV infection, asthma, rheumatoid arthritis, autoimmune diseases and chronic obstructive pulmonary diseases (COPD).

Discovery of bioavailable 4,4-disubstituted piperidines as potent ligands of the chemokine receptor 5 and inhibitors of the human immunodeficiency virus-1

We describe robust chemical approaches toward putative CCR5 scaffolds designed in our laboratories. Evaluation of analogues in the 125I-[MIP-1β] binding and Ba-L-HOS antiviral assays resulted in the discovery of 64 and 68 in the 4,4-disubstitited piperidine class H, both potent CCR5 ligands (pIC50 = 8.30 and 9.00, respectively) and HIV-1 inhibitors (pIC50 = 7.80 and 7.84, respectively, in Ba-L-HOS assay). In addition, 64 and 68 were bioavailable in rodents, establishing them as lead molecules for further optimization toward CCR5 clinical candidates.

PREPARATION AND UTILITY OF CCR5 INHIBITORS

Disclosed herein are substituted 8-azabicyclo[3.2.1]octane-based anti-infective agents of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.

TRIAZOLYL TROPANE DERIVATIVES

This invention relates to novel triazolyl tropane derivatives, their acceptable acid addition salts, solvates, hydrates and polymorphs thereof. The invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions beneficially treated by blocking or reducing the binding ability of the CCR5 receptor.