186347-31-9

Usage

Chemical structure

Piperidine derivative with a BOC protective group, a cyano group at the 4-position, and a 2-chlorophenyl moiety

Functional groups

BOC (tert-butoxycarbonyl), cyano (-CN), and 2-chlorophenyl

Application

Intermediate in the synthesis of pharmaceuticals, particularly CNS drugs

Investigation

Potential antipsychotic and analgesic properties

Importance

Versatile and important building block in medicinal chemistry

Upstream product

• 2856-63-5 2-Chlorophenylacetonitrile 
• 118753-70-1 N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 191328-21-9 4-(2-chlorophenyl)-4-cyano-piperidine 
• 553635-34-0 (S)-4-(2-chlorophenyl)-1-[4-(2,3-dihydroxypropylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]piperidine-4-carbonitrile 
• 553635-33-9 (S)-1-[7-benzenesulfonyl-4-(2,3-dihydroxypropylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-4-(2-chlorophenyl)piperidine-4-carbonitrile 
• 186347-33-1 4-(2-chlorophenyl)-piperidine-4-carbonitrile hydrochloride 
• 186347-35-3 4-(2-Chlorophenyl)-4-cyano-N-(3-[N-{1,1-dimethylethoxycarbonyl}]amino)propylpiperidine 
• 766488-36-2 1-(3-amino-propyl)-4-(2-chloro-phenyl)-piperidine-4-carbonitrile 

Relevant academic research and scientific papers

(4-PHENYL-PIPERIDIN-1-YL)-[5-1H-PYRAZOL-4YL)-THIOPHEN-3-YL]-METHANONE COMPOUNDS AND THEIR USE

The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain (4-phenyl-piperidin-1-yl)- [5-(1 H-pyrazol-4-yl)-thiophen-3-yl]-methanone compounds that, inter alia, inhibit 11 β-hydroxysteroid dehydrogenase type 1 (11 β-HSD1 ). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit 1 1 β-hydroxysteroid dehydrogenase type 1; to treat disorders that are ameliorated by the inhibition of 11 β-hydroxysteroid dehydrogenase type 1; to treat the metabolic syndrome, which includes disorders such as type 2 diabetes and obesity, and associated disorders including insulin resistance, hypertension, lipid disorders and cardiovascular disorders such as ischaemic (coronary) heart disease; to treat CNS disorders such as mild cognitive impairment and early dementia, including Alzheimer's disease; etc.

Pyrrolopyrimidine A2b selective antagonist compounds, their synthesis and use

The subject invention provides compounds having the structure: 1 wherein,R1 is a substituted or unsubstituted alkyl, wherein the substituent is hydroxyl, dihydroxy, carboxyl, —C(═O)NRaRb, —NRaRb, —NRaC(═O)NRaRb, —NRaC(═O)ORa, —OC(═O)NRaRb, or —NHC(═O)Ra;R2 is hydrogen or a substituted or unsubstituted alkyl, wherein the substituent is hydroxyl, dihydroxy, carboxyl, —C(═O)NRaRb, —NRaRb, —NRaC(═O)NRaRb, —NRaC(═O)ORa, —OC(═O)NRaRb, or —NHC(═O)Ra, orR1, R2 and N together form a substituted piperazine, substituted azetidine ring, or a pyrrolidine ring substituted with —(CH2)2OH or —CH2C(═O)OH;R3 is a substituted or unsubstituted phenyl or a 5-6 membered heteroaryl ring, wherein the substituent is halogen, hydroxyl, cyano, (C1-C15)alkyl, (C1-C15)alkoxy, or —NRaRb;R4 is hydrogen or substituted or unsubstituted (C1-C15)alkyl;R5 is —(CH2)mOR6, —CHNOR7, —C(═O)NR8R9, —(CH2)mC(═O)OR10, —(CH2)kC(═O)NR11R12;wherein R6 is a substituted or unsubstituted (C1-C30)alkyl, (C3-C10)cycloalkyl, or an aryl, heteroaryl or 4-8 membered heterocyclic ring;R7 is hydrogen, or a substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkylaryl;R8 and R9 are each independently hydrogen, or a substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkylaryl, (C1-C30)alkylamino, (C1-C30)alkoxy, or a saturated or unsaturated, monocyclic or bicyclic, carbocyclic or heterocyclic ring, orR8, N, and R9 together form a substituted or unsubstituted 4-8 membered heterocyclic ring;R10 is hydrogen or a substituted or unsubstituted (C1-C30)alkyl, (C3-C10)cycloalkyl, or an aryl, heteroaryl or heterocyclic ring;R11, N and R12 together form a 4-8 membered heterocyclic ring;Ra and Rb are each independently hydrogen or alkyl;m is 0, 1, 2 or 3; andk is 1, 2 or 3,or a specific enantiomer thereof, or a specific tautomer thereof, or a pharmaceutically acceptable salt thereof, and a method for treating a disease associated with the A2b adenosine receptor in a subject in need of such treatment comprising administering to the subject a therapeutically effective amount of the compounds of the invention.

Phenylacetamides as selective α-1A adrenergic receptor antagonists

A novel class of potent and selective α-1a receptor antagonists has been identified. The structures of these antagonists were derived from truncating the 4-aryl dihydropyridine subunit present in known α-1a antagonists. The design principles which led to the discovery of substituted phenylacetamides, the synthesis and SAR of key analogues, and the results of select in vitro and in vivo studies are described. (C) 2000 Elsevier Science Ltd. All rights reserved.

Alpha 1a adrenergic receptor antagonists

This invention relates to certain novel compounds and derivatives thereof, their synthesis, and their use as selective alpha 1a adrenergic receptor antagonists. One application of these compounds is in the treatment of benign prostatic hyperplasia. These componds are selective in their ability to relax smooth muscle tissue enriched in the alpha 1a receptor subtype without at the same time inducing hypotension. One such tissue is found surrounding the urethral lining. Therefore, one utility of the instant compounds is to provide acute relief to males suffering from benign prostatic hyperplasia, by permitting less hindered urine flow. Another utility of the instant compounds is provided by combination with a human 5-alpha reductase inhibitory compound, such that both acute and chronic relief from the effects of benign prostatic hyperplasia are achieved.

ALPHA-1A ADRENERGIC RECEPTOR ANTAGONISTS

This invention relates to certain novel compounds and derivatives thereof, their synthesis, and their use as selective alpha-1a adrenergic receptor antagonists. One application of these compounds is in the treatment of benign prostatic hyperplasia. These compounds are selective in their ability to relax smooth muscle tissue enriched in the alpha 1a receptor subtype without at the same time inducing orthostatic hypotension. One such tissue is found surrounding the urethral lining. Therefore, one utility of the instant compounds is to provide acute relief to males suffering from benign prostatic hyperplasia, by permitting less hindered urine flow. Another utility of the instant compounds is provided by combination with a human 5-alpha reductase inhibitory compound, such that both acute and chronic relief from the effects of benign prostatic hyperplasia are achieved.