Claims
- 1. Benzophenone derivative having the structural formula ##SPC7##
- and the acid addition salts thereof, wherein
- R.sub.1 and R.sub.2 are substituents selected from the group consisting of hydrogen, saturated and unsaturated alkyl groups having 1 - 4 carbon atoms;
- R.sub.3 is a substituent selected from the group consisting of --COOH and --COOMe, Me signifying a pharmacologically acceptable metallic cation;
- n is an integer selected from 1 and 2; and
- m is an integer selected from 1, 2 and 3, and wherein the ring A may be substituted with a substituent selected from the group consisting of halogen, nitro, trifluoromethyl, methyl, methoxy and methylmercapto and the ring B may be substituted with a substituent selected from the group consisting of fluorine and chlorine.
- 2. Benzophenone derivative according to claim 1, wherein the ring A is substituted at the 5-position and the ring B is substituted at the 2' position.
- 3. Benzophenone derivative according to claim 1, wherein R.sub.1 is a substituent selected from the group consisting of hydrogen and methyl and R.sub.2 is a substituent selected from the group consisting of hydrogen, methyl and butyl.
Priority Claims (1)
| Number |
Date |
Country |
Kind |
| 65340 |
May 1972 |
LU |
|
Parent Case Info
The present application is a division of our U.S. Ser. No. 358,455, filed May 8, 1973, now U.S. Pat. No. 3,888,899.
The invention relates to pharmacologically valuable new benzophenone derivatives of the general formula I ##SPC2##
Preferred substituents for the ring A are halogen, especially chlorine, nitro, trifluoromethyl, methyl, methoxy or methylmercapto, and substitution is preferably in the 5 position, and preferred substituents for the ring B are fluorine or chlorine, substitution preferably being at the 2' position. The radicals R.sub.1 and R.sub.2 preferably signify hydrogen or a methyl group, or an n-butyl group in the case of R.sub.2.
The metal cation Me is preferably a pharmacologically acceptable metal cation, for example the sodium, potassium, ammonium or calcium.
The invention also extends to processes for the production of compounds of the general formula I.
Compounds of the general formula I may be produced by reacting a benzophenone derivative of the general formula II ##SPC3##
Starting compounds of the general formula II, in which X signifies a halogen atom, can easily be produced from aminobenzophenones of the general formula IV ##SPC4##
The initial compounds of the general formula II, in which X signifies the radical R.sub.2 -- NH-- , can be obtained by reacting a compound of the general formula IIa ##SPC5##
The reaction is preferably carried out at a temperature between 5.degree. and 50.degree. with a reaction time of from a few hours up to several days, advantageously in a suitable solvent.
Those compounds of the general formula I, in which m signifies 2 or 3 and R.sub.1, R.sub.2, R.sub.3 and n are as defined above, may be produced by an addition reaction between a benzophenone derivative of the general formula II, in which X signifies R.sub.2 -- NH --, and a compound containing an aliphatic double bond and of the general formula VII
Those compounds of the general formula I in which R.sub.3 is CN and is in the .alpha. position in relation to the amino group of the side chain can also be prepared by reacting a compound of the general formula II, in which X signifies the radical R.sub.2 -- NH --, with am aldehyde or ketone of the general formula VIII
Compounds according to the invention in which R.sub.3 signifies a carbmethoxy or carbethoxy group can be converted by saponification into compounds according to the invention in which R.sub.3 is --COOH or by ammonolysis into compounds according to the invention in which R.sub.3 is --CONH.sub.2.
Compounds according to the invention in which R.sub.3 is --COOH may be used to prepare the corresponding salts --COOMe.
Normally compounds according to the invention are oily substances which provide crystalline acid addition salts.
The compounds of the general formula I and their pharmaceutically acceptable salts are characterised by valuable pharmacological properties, especially a pronounced sedative action on the central nervous system. Some of these compounds also possess muscle-relaxing and aggression-inhibiting properties. The compounds of the general formula I and their pharmaceutically acceptable salts are therefore valuable pharmaceutical products which can be used as medicaments in the form of pharmaceutical preparations. The pharmaceutical preparations can be put up, for example, as tablets, suppositories, capsules, emulsions or suspensions in a known manner by the use of pharmaceutically acceptable diluents or carriers which do not react with the compounds. As diluents or carriers it is possible to use any substance which is suitable for the purpose in mind, for example talcum, starch, vegetable oils or petroleum jellies. If desired the pharmaceutical preparations may also contain other therapeutically active substances.
The pharmacological investigation of the sedative action on the central nervous system was carried out using the climbing tests on albino mice described by P. K. KNEIP: Arch. int. pharmacodyn 126, 238 (1960) and R. DOMENJOZ and W. THEOBALD: Arch. int. pharmacodyn 120, 450 (1959).
In the table which follows, the results of the pharmacological investigations carried out are summarised. In the last table under the heading "Sedative action %" there is given the percentage of the experimental animals which no longer take up the normally readily assumed climbing work.
US Referenced Citations (1)
| Number |
Name |
Date |
Kind |
|
3741988 |
Allais et al. |
Jun 1973 |
|
Divisions (1)
|
Number |
Date |
Country |
| Parent |
358455 |
May 1973 |
|
Patent Grant
3931301
