130497-40-4

Upstream product

• 115642-92-7 (2S)-2-(1-pyrrolidinylcarbonyl) piperidine 
• 136598-30-6 (S)-1-(ethoxycarbonyl)pipecolic acid 
• 3105-95-1 pipecolinic acid 
• 741633-48-7 (S)-Piperidine-2-carbonyl chloride 
• 32857-62-8 4-Trifluoromethylphenylacetic acid 
• 74426-51-0 4-(trifluoromethyl)phenylacetyl chloride 
• 112419-06-4 (2S)-2-(1-pyrrolidinylmethyl)-piperidine 

Relevant academic research and scientific papers

Method for the treatment of a hyponatremic disease

Compounds of formula (Ia), or pharmaceutically acceptable salts or solvates thereof, STR1 in which A, together with the nitrogen atom, represents --(CH2)p--, where p is an integer from 3 to 6, or an optionally substituted tetrahydroisoquinoline ring system; each of R1 and R2 are independently hydrogen, C1-6 alkyl, C2-6 alkenyl C3-6 cycloalkyl or C4-12 cycloalkylalkyl, or together form a C2-6 polymethylene or C2-6 alkenylene group, optionally substituted with a hetero-atom, Rx is hydrogen, C1-6 alkyl or phenyl, or together with R1 forms a --(CH2)3 -- or --(CH2)4 -- group; and R comprises a substituted or unsubstituted carbocyclic or heterocyclic aromatic group; and compounds of formula (Ib) STR2 in which: R, R1, R2 and X are as defined in formula (Ia) Ra is C1-6 alkyl or phenyl; Rb is hydrogen or together with Ra forms a --(CH2)n -- group in which n=1, 2 or 3; and `Het` is an optionally substituted single or fused ring heterocyclic group containing from 5 to 12 ring atoms and comprising up to four hetero-atoms in the or each ring, selected from oxygen, nitrogen and sulphur, are useful as diuretic agents.

(2S)-1-(arylacetyl)-2-(aminomethyl)piperidine derivatives: Novel, highly selective κ opioid analgesics

This paper describes the synthesis and structure-activity relationships as κ opioid analgesics of a novel class of 1-(arylacetyl)-2-(aminomethyl)piperidine derivatives (8). The active conformation of the pharmacophore, with a torsional angle (N1C2C7N8) of 60°, was defined with computational studies and 1H NMR. A quantitative structure-activity relationship study of the arylacetic moiety substitution indicated that the presence of an electron-withdrawing and lipophilic substituent in para and/or meta positions is required for good analgesic activity and κ affinity. The lead compounds (2S)-1-[(3,4-dichlorophenyl)acetyl]-2-(pyrrolidin-1-ylmethyl) piperidine hydrochloride (14) and (2S)-1-[[4-(trifluoromethyl)phenyl]acetyl]-2-(pyrrolidin-1- ylmethyl)piperidine hydrochloride (21) are the most κ/μ selective (respectively 6500:1 and 4100:1) and among the most potent (K(i) κ 0.24 and 0.57 nM, respectively) κ ligands identified so far. In the mouse tail flick model of antinociception, compound 14 (ED50 = 0.05 mg/kg sc) was 25 times more potent than morphine and 16 times more potent than the standard κ ligand U-50488.