444904-17-0

Upstream product

• 444904-02-3 (S)-1,2,3,6-tetrahydro-1,3-dimethyl-4-[3-(1-methylethoxy)phenyl]pyridine 
• 104-53-0 3-phenyl-propionaldehyde 
• 444904-04-5 (-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-2,4-dimethyl-2-azabicyclo[3.3.1]nonan-7-one 
• 881686-00-6 2-[(1R,4S,5R,7R)-5-(3-isopropoxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]non-7-yl]-1H-isoindole-1,3(2H)-dione 
• 881686-01-7 2-[(1R,4S,5R,7R)-5-(3-isopropoxyphenyl)-4-methyl-2-azabicyclo[3.3.1]non-7-yl]-1H-isoindole-1,3(2H)-dione 
• 881685-98-9 (1R,4S,5R)-5-(3-isopropoxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]nonan-7-one oxime 
• 881685-99-0 (1R,4S,5S,7R)-5-(3-isopropoxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]nonan-7-amine 
• 881686-02-8 2-[(1R,4S,5R,7R)-5-(3-isopropoxyphenyl)-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]non-7-yl]-1H-isoindole-1,3(2H)-dione 
• 444904-14-7 (-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonan-7-one oxime 
• 444904-08-9 (1R,4S,5R)-5-(3-Isopropoxy-phenyl)-4-methyl-2-aza-bicyclo[3.3.1]nonan-7-ol 
• 444904-09-0 (-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonan-7-ol 
• 444904-11-4 (1R,4S,5R)-5-(3-Isopropoxy-phenyl)-4-methyl-2-(3-phenyl-propyl)-2-aza-bicyclo[3.3.1]nonan-7-one 
• 444904-25-0 Benzoic acid (1R,4S,5R)-5-(3-isopropoxy-phenyl)-2,4-dimethyl-2-aza-bicyclo[3.3.1]non-7-yl ester 
• 444904-06-7 (-)-(1R,4S,5S)-5-[3-(1-methylethoxy)phenyl]-2,4-dimethyl-2-azabicyclo[3.3.1]nonan-7-ol 

Downstream Products

• 444904-20-5 (1R,4S,5S,7R)-(-)-5-(3-hydroxyphenyl)-4-methyl-2-(3-phenylpropyl)-2-azabicylo-[3.3.1]nonan-7-amine 
• 881686-31-3 N-[(1R,4S,5S,7R)-5-(3-isopropoxyphenyl)-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]non-7-yl]-3-(5-methoxy-3,4-dihydroisoquinolin-2(1H)-yl)propionamide 
• 913366-37-7 7-formylamino-5-(3-isopropoxyphenyl)-4-methyl-2-(3-phenprop-1-yl)-2-aza-bicyclo[3.3.1]nononane 

Relevant academic research and scientific papers

N-substituted 4β-methyl-5-(3-hydroxyphenyl)-7α-amidomorphans are potent, selective κ opioid receptor antagonists

In a previous study, we identified (-)-N-[(1R,4S,5S,7R)-5-(3-hydroxyphenyl) -4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]non-7-yl]-3-(1-piperidinyl) propanamide (5a, KAA-1) as the first potent and selective κ opioid receptor antagonist from the 5-(3-hydroxyphenyl)morphan class of opioids. In this study we report an improved synthesis of this class of compounds. The new synthetic method was used to prepare analogues 5b-r where the morphan N-substituent and 7α-amido group were varied. Most of the analogues showed sub-nanomolar potency for the κ opioid receptor and were highly selective relative to the μ and δ opioid receptors. (-)-3-(3,4- Dihydroisoquinolin-2(1H)-yl)-N-{(1R,4S,5S,7R)-5-(3-hydroxyphenyl) -4-methyl-2-[2-(2-methylphenyl)ethyl]-2-azabicyclo[3.3.1]non-7-yl}propanamide (5n, MTHQ) is at least as potent and selective as nor-BNI as a κ opioid receptor antagonist in the [35S]GTP-γ-S in vitro functional test.

Opiod receptor agonist compounds and their use in treatment of pain

Structurally novel opioid receptor agonists are provided, and the use of these agonists in treatment of chronic and/or acute pain.

Discovery of an opioid κ receptor selective pure antagonist from a library of N-substituted 4β-methyl-5-(3-hydroxyphenyl)morphans

A library of compounds biased toward opioid receptor antagonist activity was prepared by incorporating N-phenylpropyl-4β-methyl-5-(3-hydroxyphenyl)morphans as the core scaffold using simultaneous solution phase synthetic methodology. From this library, N-