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US 10,377,698 B2Granted
Diphenethylamine derivatives which are inter alia useful as analgesics and method for their production
AssigneeUniversity of Innsbruck
InventorsHelmut Schmidhammer, Mariana Spetea, Elena Guerrieri
Life of this patent
Estimating the term…
Abstract
Diphenethylamine derivatives for use as highly active analgesics, diuretics, anxiolytics, for the treatment of neurodegenerative, psychiatric and neuropsychiatric disorders, and also as anti-itch, anti-addiction, anti-inflammatory, anti-obesity, anti-epileptic, anti-convulsant, anti-seizure, anti-stress, anti-psychotic and anti-depressant medications and their pharmaceutically acceptable salts and easily accessible derivatives thereof (e.g. esters, ethers, amides), processes for their preparation and their application in the manufacture of pharmaceutical products.
Claims13
A compound of formula (I),
- in which
- R1 is selected from C2-C30-alkynyl;
- C1-C30-monohydroxyalkyl;
- C2-C30-dihydroxyalkyl;
- C3-C30-trihydroxyalkyl;
- C3-C12-cycloalkyl;
- C4-C30-cycloalkylalkyl;
- C5-C30-cycloalkylalkenyl;
- C5-C30-cycloalkylalkynyl;
- C7-C30-arylalkyl;
- C8-C30-arylalkenyl;
- C8-C30-arylalkynyl;
- R2 is hydrogen;
- F;
- Cl;
- I;
- NO2;
- CN;
- SH;
- CO2H;
- CONH2;
- SO3H;
- SO2NH2;
- CONHSO3H;
- NHCONHSO2H;
- PO3H;
- PO2H;
- CF3;
- R3 is hydroxy;
- OCOA, wherein A is selected from C1-C6-alkyl, C6-C14-aryl, C7-C16-aryalkyl;
- F;
- Cl;
- Br;
- I;
- NO2;
- CN;
- SH;
- CO2H;
- CONH2;
- SO3H;
- SO2NH2;
- CONHSO3H;
- NHCONHSO2H;
- PO3H;
- PO2H;
- CF3;
- R4 is hydrogen;
- F;
- Cl;
- I;
- NO2;
- CN;
- SH;
- CO2H;
- CONH2;
- SO3H;
- SO2NH2;
- CONHSO3H;
- NHCONHSO2H;
- PO3H;
- PO2H;
- CF3;
- R5 is hydrogen;
- hydroxy;
- R6 is hydrogen;
- hydroxy;
- with the proviso that R1 cannot be cyclobutylmethyl (CBM) or cyclopropylmethyl (CPM) if R3 is hydroxy and R2, R4, R5 and R6 is hydrogen;
- and pharmaceutically acceptable acid addition salts and base addition salts.
65 more elements
A compound selected from:
- 3-[2-[Allyl(phenethyl)amino]ethyl]phenol
- 3-[2-[(Cyclopentylmethyl)(phenethyl)amino]ethyl]phenol
- 3-[2-[(Cyclohexylmethyl)(phenethyl)amino]ethyl]phenol
- 3-[2-[Benzyl(phenethyl)amino]ethyl]phenol
- 3-[2-[Propargyl(phenethyl)amino]ethyl]phenol
- 3-[2-[Isopropyl(phenethyl)amino]ethyl]phenol
- 3-[2-[Isoamyl(phenethyl)amino]ethyl]phenol
- 3-[2-[(Cyclobutyl)(phenethyl)amino]ethyl]phenol
- N-(Cyclobutylmethyl)-N-(3-methoxyphenethyl)-2-(3-methoxyphenyl)ethanamine
- N-(Cyclopropylmethyl)-N-(3-methoxyphenethyl)-2-(3-methoxyphenyl)ethanamine
- N-Allyl-N-(3-methoxyphenethyl)-2-(3-methoxyphenyl)ethanamine
- 3,3′-[2,2′-(Cyclobutylmethylazanediyl)bis(ethane-2,1-diyl)]diphenol
- 3,3′-[2,2′-(Cyclopropylmethylazanediyl)bis(ethane-2,1-diyl)]diphenol
- 3,3′-[2,2′-(Allylazanediyl)bis(ethane-2,1-diyl)]diphenol
- 3-[2-(3-Methoxyphenethylamino)ethyl]phenol
- 4-[2-(3-Methoxyphenethylamino)ethyl]phenol
- 3-[2-[(Cyclohexylmethyl)(3-methoxyphenethyl)amino]ethyl]phenol
- 3-[2-[(Isoamyl)(3-methoxyphenethyl)amino]ethyl]phenol
- 3-[2-[(n-Butyl)(3-methoxyphenethyl)amino]ethyl]phenol
- 3-[2-[(n-Pentyl)(3-methoxyphenethyl)amino]ethyl]phenol
- 3-[2-[(n-Hexyl)(3-methoxyphenethyl)amino]ethyl]phenol
- 4-[2-[(Cyclobutylmethyl)(3-methoxyphenethyl)amino]ethyl]phenol
- 4-[2-[(Cyclohexylmethyl)(3-methoxyphenethyl)amino]ethyl]phenol
- 4-[2-[Allyl(3-methoxyphenethyl)amino]ethyl]phenol
- 4-[2-[n-Butyl(3-methoxyphenethyl)amino]ethyl]phenol
- 4-[2-[(Cyclopropylmethyl)(3-methoxyphenethyl)amino]ethyl]phenol
- 4-[2-[(Cyclopentylmethyl)(3-methoxyphenethyl)amino]ethyl]phenol
- 3-[2-[(Cyclopentylmethyl)(3-methoxyphenethyl)amino]ethyl]phenol
- 3,3′-[2,2′-(Cyclohexylmethylazanediyl)bis(ethane-2,1-diyl)]diphenol
- 3,3′-[2,2′-(Isoamylazanediyl)bis(ethane-2,1-diyl)]diphenol
- 3,3′-[2,2′-(n-Pentylazanediyl)bis(ethane-2,1-diyl)]diphenol
- 3,3′-[2,2′-(n-Hexylazanediyl)bis(ethane-2,1-diyl)]diphenol
- 3,3′-[2,2′-(Cyclopentylmethylazanediyl)bis(ethane-2,1-diyl)]diphenol
- 3-[2-[(Cyclobutylmethyl)(4-hydroxyphenethyl)amino]ethyl]phenol
- 3-[2-[(Cyclopropylmethyl)(4-hydroxyphenethyl)amino]ethyl]phenol
- 3-[2-[(Cyclohexylmethyl)(4-hydroxyphenethyl)amino]ethyl]phenol
- 3-[2-[Allyl(4-hydroxyphenethyl)amino]ethyl]phenol
- 3-[2-[n-Butyl(4-hydroxyphenethyl)amino]ethyl]phenol
- 1-(2-Fluoro-3-methoxyphenethyl)-2-phenethylamine
- N-(2-Fluoro-3-methoxyphenethyl)-2-(3-methoxyphenyl)ethanamine
- N-(Cyclopropylmethyl)-N-(2-fluoro-3-methoxyphenethyl)-2-phenylethanamine
- N-(Cyclobutylmethyl)-N-(2-fluoro-3-methoxyphenethyl)-2-phenylethanamine
- 4-[2-(2-Fluoro-3-methoxyphenethylamino)ethyl]phenol
- N-(Cyclohexylmethyl)-N-(2-fluoro-3-methoxyphenethyl)-2-phenylethanamine
- N-Benzyl-N-(2-fluoro-3-methoxyphenethyl)-2-phenylethanamine
- N-(Cyclobutylmethyl)-N-(2-fluoro-3-methoxyphenethyl)-2-(3-methoxyphenyl)ethanamine
- 4-[2-[(Cyclobutylmethyl)(2-fluoro-3-methoxyphenethyl)amino]ethyl]phenol
- 3-[2-[(Cyclobutylmethyl)(phenethyl)amino]ethyl]-2-fluorophenol
- 3-[2-[(Cyclopropylmethyl)(phenethyl)amino]ethyl]-2-fluorophenol
- 3-[2-[(Cyclohexylmethyl)(phenethyl)amino]ethyl]-2-fluorophenol
- 3-[2-[(Benzyl)(phenethyl)amino]ethyl]-2-fluorophenol
- 3-[2-[(Cyclobutylmethyl)(3-hydroxyphenethyl)amino]ethyl]-2-fluorophenol
- 3-[2-[(Cyclobutylmethyl)(4-hydroxyphenethyl)amino]ethyl]-2-fluorophenol
- 3-[2-[(Cyclobutylmethyl)(phenethyl)amino]ethyl]benzonitrile
- 3-[2-[(Cyclobutylmethyl)(phenethyl)amino]ethyl]benzamide
- N-(Cyclobutylmethyl)-N-phenethyl-2-phenylethanamine
- N-(Cyclobutylmethyl)-N-(3-nitrophenethyl)-2-phenylethanamine
- 3-[2-[(Cyclobutylmethyl)(phenethyl)amino]ethyl]aniline
- 4-[2-[(Cyclopentylmethyl)(phenethyl)amino]ethyl]phenol
- 4-[2-[(Cyclobutylmethyl)(phenethyl)amino]ethyl]phenol
- and pharmaceutically acceptable acid addition salts and base addition salts, esters.
58 more elements
Dependencies are inferred from the claim text.