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Substituted 2-dialkylaminoalkylbiphenyl derivatives

A technology of alkylaminoalkylbiphenyl and derivatives, which is applied in the field of preparation of medicines and can solve problems such as drug resistance, dependence, and addiction

Inactive Publication Date: 2009-12-30
GRUNENTHAL GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, their use is limited by their well-known side effects, such as depression of respiration, vomiting, sedation, constipation, addiction, dependence and development of drug resistance

Method used

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  • Substituted 2-dialkylaminoalkylbiphenyl derivatives
  • Substituted 2-dialkylaminoalkylbiphenyl derivatives
  • Substituted 2-dialkylaminoalkylbiphenyl derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] (3′-Methoxybiphenyl-2-ylmethyl)dimethylamine hydrochloride

[0106] first step

[0107] 3-Methoxyphenylboronic acid

[0108]41.3g (220mmol) of 3-bromoanisole was dissolved in 880ml of tetrahydrofuran, and the resulting solution was cooled to -70°C in a cold bath (ethanol / dry ice). 160ml (250mmol) of butyl lithium solution (1.6M in hexane) was added dropwise under nitrogen and the temperature was not higher than -60°C. After stirring at -70°C for 1.5 hours, 75 ml (660 mmol) of trimethyl borate was added dropwise and the temperature was not higher than -60°C. After stirring was continued for one hour in the cold bath, the temperature of the mixture was raised to 25°C over a period of two hours, 720 ml (1M) of hydrochloric acid were added and the resulting mixture was stirred at 25°C for 15 hours. For further completion of the reaction, the mixture was extracted three times with 300ml ether each time, the organic phases were combined, washed with 100ml each of water and...

Embodiment 2

[0116] (4'-Chlorobiphenyl-2-ylmethyl)dimethylamine hydrochloride

[0117] 0.88g (5.65mmol) 4-chlorophenylboronic acid, 1.27g (5.93mmol) (2-bromobenzyl) dimethylamine and 2.00g (18.8mmol) sodium carbonate obtained according to the method of embodiment 1 (the 2nd step) Dissolved in a mixture of 39ml toluene, 16ml water and 8ml ethanol. Under a nitrogen atmosphere, 133 mg of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was heated under reflux (bath temperature: 110° C.) for 16 hours. To further complete the reaction, 65 ml of ether were added and the mixture was extracted three times with 65 ml of potassium hydroxide solution (0.5M). The combined aqueous solution was re-extracted with 20 ml of ether, the resulting organic phases were combined, dried over anhydrous magnesium sulfate, then filtered, and the filtrate was concentrated using a rotary evaporator (500-10 mbar). This gave 1.30 g of crude base (93.8% of theory), which was transferred to a 3 x 25 c...

Embodiment 3

[0119] 2′-Dimethylaminomethylbiphenyl-3-ol hydrochloride

[0120] 0.70 (2.52 mmol) (3'-methoxybiphenyl-2-ylmethyl) dimethylamine hydrochloride prepared according to the method of Example 1 (the third step) was dissolved in 10 ml of water, and was oxidized with 10 ml of water and 2 ml of hydroxide Sodium solution (32 wt.%) liberates the base, the mixture is extracted three times with 20 ml of ether each time, the combined organic phases are dried over anhydrous magnesium sulfate, then filtered, and the filtrate is concentrated on a rotary evaporator (500-10 mbar). 0.59 g (2.44 mmol) of this base and 55 ml of hydrobromic acid solution (48 wt % aqueous solution) were heated under reflux (bath temperature 145° C.) for two hours. For further completing the reaction, the mixture is poured into 600ml sodium bicarbonate solution (1M) (pH7-8), the mixture is extracted three times with 100ml ethyl acetate each time, the organic phases are combined, dried with anhydrous magnesium sulfate...

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Abstract

The invention relates to substituted 2-dialkylaminoalkylbiphenyl derivatives, a method for the preparation thereof, drugs containing them and the use thereof for the production of drugs.

Description

[0001] This application is a divisional application based on the application number 00813734.X filed on July 25, 2000. technical field [0002] The present invention relates to substituted 2-dialkylaminoalkylbiphenyl derivatives, processes for their preparation, pharmaceuticals containing these compounds and the use of these compounds in the preparation of pharmaceuticals. Background technique [0003] The treatment of pain in both persistent and non-persistent states is important to medicine. There is a worldwide need for highly effective pain treatments. The urgent need for treatment of pain involving patient-specific and goal-directed persistent and discontinuous states, which can be understood as a successful and satisfactory treatment of a patient's pain, is documented in a large body of scientific literature, recently appearing in Applied Pain Relief Law and basic research on nociceptive perception. [0004] Traditional opioids such as morphine are effective for seve...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/01C07C209/24C07C209/68C07C211/27C07C213/02C07C215/50C07C217/58C07D307/79C07D317/58A61K31/135C07D319/08A61K31/137A61K31/167A61K31/343A61K31/357A61K31/404A61P1/04A61P1/12A61P7/12A61P9/00A61P11/00A61P11/14A61P25/04A61P25/08A61P25/18A61P25/24A61P25/30A61P29/00A61P37/08C07B61/00C07C209/66C07C211/29C07C213/08C07C215/46C07C215/52C07C217/54C07C217/60C07C221/00C07C223/02C07C225/16C07C233/25C07C233/43C07C315/04C07C317/32C07D209/08
CPCC07C217/58C07C215/52C07C317/32C07C233/43C07C215/46C07D317/58C07C223/02C07C217/54C07C215/50C07C225/16C07C217/60C07C211/29C07D307/79A61P1/04A61P1/12A61P11/00A61P11/14A61P25/04A61P25/08A61P25/18A61P25/24A61P25/30A61P29/00A61P37/08A61P7/12A61P9/00C07C211/00
Inventor B·松德曼B·-Y·科格尔H·布施曼
Owner GRUNENTHAL GMBH
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