Substituted 2-dialkylaminoalkylbiphenyl derivatives

Details Substituted 2-dialkylaminoalkylbiphenyl derivatives Substituted 2-dialkylaminoalkylbiphenyl derivatives

2002-02-11

2004-03-23

McKane, Joseph K. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C514S650000, C558S422000, C564S337000

Reexamination Certificate

active

06710080

ABSTRACT:

BACKGROUND AND SUMMARY OF THE INVENTION
The invention relates to substituted 2-dialkylaminoalkylbiphenyl derivatives, processes for their preparation, medicaments comprising these compounds and the use of these compounds for the preparation of medicaments and methods of treatment using these components.
The treatment of chronic and non-chronic states of pain is of great importance in medicine. There is a worldwide demand for pain treatments which have a good efficacy. The urgent need for action in respect of patient-relevant and target-orientated treatment of chronic and non-chronic states of pain, this being understood as meaning successful and satisfactory pain treatment for the patient, is documented in the large number of scientific works which have recently appeared in the field of applied analgesia and fundamental research into nociception.
Conventional opioids, such as morphine, have a good action in the treatment of severe to very severe pain. However, their use is limited due to the known side effects, e.g. respiratory depressions, vomiting, sedation, constipation, addiction, dependency and development of tolerance. They can therefore be administered over a relatively long period of time or in relatively high dosages only with particular safety precautions, such as specific prescription instructions (Goodman, Gilman, The Pharmacological Basis of Therapeutics, Pergamon Press, New York 1990). Furthermore, they have a relatively low efficacy for some states of pain, in particular neuropathic pain.
An object of the instant invention was to provide analgesically active substances which are suitable for treatment of pain. Furthermore, these substances should have as few as possible of the side effects of opioid analgesics, such as nausea, vomiting, dependency, respiratory depression or constipation. Further objects are to provide active compounds for treatment of inflammatory and allergic reactions, depressions, drug and/or alcohol abuse, gastritis, diarrhoea, urinary incontinence, cardiovascular diseases, respiratory tract diseases, coughing, mental illnesses and/or epilepsy.
According to the invention, this is achieved by provision of new substituted 2-dialkylaminoalkylbiphenyl derivatives which are suitable for treatment of inflammatory and allergic reactions, depressions, drug and/or alcohol abuse, gastritis, diarrhoea, urinary incontinence, cardiovascular diseases, respiratory tract diseases, coughing, mental illnesses and/or epilepsy and which moreover have a pronounced analgesic action.
DETAILED DESCRIPTION OF THE INVENTION
The invention therefore provides substituted 2-dialkylaminoalkylbiphenyl derivatives of the general formula I
Wherein
n is 1 or 2,
the radicals R
1
, R
2
, R
3
, which are identical or different, represent H, F, Cl, Br, CN, NO
2
, CHO, SO
2
CH
3
, SO
2
CF
3
, OR
6
, NR
6
R
7
, a C
1-6
-alkyl, preferably a C
1-3
-alkyl, an aryl, an acetyl, an acetamidyl or a benzoyl radical, or represent an aryl radical bonded via a C
1-6
-alkylene group, preferably an aryl radical bonded via a C
1-3
-alkylene group;
or R
1
and R
2
together in each case denote the group OCH
2
O, OCH
2
CH
2
O , CH═CHO, CH═C(CH
3
)O or CH═CHNH;
the radicals R
4
, R
5
, which are identical or different, represent H, or represent a C
1-6
-alkyl radical, preferably a C
1-3
-alkyl radical;
the radicals R
6
, R
7
, which are identical or different, represent H, a C
1-6
-alkyl, preferably a C
1-3
-alkyl, or an aryl radical, or represent an aryl radical bonded via a C
1-6
-alkylene group, preferably an aryl radical bonded via a C
1-3
-alkylene group,
in the form of their bases and/or salts of physiologically tolerated acids.
However, the compounds
2′-dimethylaminomethylbiphenyl-2-carbaldehyde;
biphenyl-2-ylmethyldimethylamine;
2′-dimethylaminomethylbiphenyl-2-ol, and the corresponding hydrochloride;
(2′,3′-dimethoxybiphenyl-2-ylmethyl)dimethylamine, and the corresponding hydrochloride and the corresponding hydrobromide;
(4′-methylbiphenyl-2-ylmethyl)-dimethylamine;
(2′-methylbiphenyl-2-ylmethyl)-dimethylamine;
4-chloro-2′-dimethylaminomethylbiphenyl-2-carbonitrile;
(2′-dimethylaminomethylbiphenyl-2-yl)methanol;
2′-dimethylaminomethylbiphenyl-2,3-diol, and the corresponding hydrobromide;
[2-(3′,4′-dimethoxybiphenyl-2-yl)ethyl)]-dimethylamine, and the corresponding hydrochloride;
[2-(2′,3′-dimethoxy-6′-methylbiphenyl-2-yl)ethyl)]-dimethylamine, and the corresponding hydrobromide; and
biphenyl-2-ylethyldimethylamine are excluded.
Alkyl radicals are understood as meaning hydrocarbons which may be substituted, preferably by halogen and/or a hydroxyl group, particularly preferably by fluorine and/or a hydroxyl group. If there are more than one substituent, the substituents can be identical or different. The alkyl radicals methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, hexyl, 1-methylpentyl, CHF
2
, CF
3
or CH
2
OH are preferred.
An aryl radical is understood as meaning phenyls or naphthyl radicals which may be substituted by an OH, a halogen, preferably F and/or Cl, a CF
3
, a C
1-6
-alkyl, a C
1-6
-alkoxy, a C
1-7
-cycloalkoxy, a C
3-7
-cycloalkyl, a C
2-6
-alkylene or a phenyl radical. The phenyl radicals can also be condensed with further rings.
The following substituted 2-dimethylaminoalkylbiphenyl derivatives are particularly preferred:
(3′-methoxybiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
(4′-chlorobiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
2′-dimethylaminomethylbiphenyl-3-ol and the corresponding hydrochloride;
(2′-methoxybiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
(3′-chlorobiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
(2′-fluorobiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
(3′-fluorobiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
(4′-fluorobiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
(3′-chloro-4′-fluorobiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
(3′-methoxybiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
dimethyl-[2-(2-methylbenzofuran-4-yl)benzyl]amine and the corresponding hydrochloride;
2′-dimethylaminomethylbiphenyl-2-carbaldehyde and the corresponding hydrochloride;
(3′-difluoromethylbiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
2′-dimethylaminomethylbiphenyl-3-carbaldehyde and the corresponding hydrochloride;
biphenyl-2-ylmethyldimethylamine and the corresponding hydrochloride;
(3′,4′-dichlorobiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
(3′,5′-dichlorobiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
dimethyl-(4′-nitro-3′-trifluoromethylbiphenyl-2-ylmethyl)-amine and the corresponding hydrochloride;
(3′,4′-difluorobiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
(4′-fluoro-3′-trifluoromethylbiphenyl-2-ylmethyl)dimethyl-amine and the corresponding hydrochloride;
(4′-chloro-3′-methoxybiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
N-(2′-dimethylaminomethyl-3-trifluoromethoxybiphenyl-4-yl)acetamide and the corresponding hydrochloride;
(3′-isopropoxybiphenyl-2-ylmethyl)dimethylamine and the corresponding and the corresponding hydrochloride;
2′-(2-dimethylaminoethyl)biphenyl-3-ol and the corresponding hydrochloride;
4-chloro-2′-dimethylaminomethylbiphenyl-3-ol and the corresponding hydrochloride;
[2-(1H-indol-5-yl)benzyl]dimethylamine and the corresponding hydrochloride;
(4′-methanesulfonylbiphenyl-2-ylmethyl)dimethylamine and the corresponding hydrochloride;
(2′,4′-dichlorobiphenyl-2-ylmethyl)

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