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NNO. Muscular Genesis

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NNO. Muscular Genesis 3,772,348 United States Patent Office Patented Nov. 13, 1973 2 and the pharmaceutically acceptable acid addition salts 3,772,348 thereof. DERIVATIVES OF DEBENZObf)PYRROLO(3,4-d Compounds of the Formula I and the pharmaceutically AZEPINE AS CNS-DEPRESSANTS acceptable acid addition salts thereof have valuable phar Hans Blattner, Riehen, Switzerland, and Walter Schindler, deceased, late of Basel, Switzerland, by Leonhard Gysin, macological properties. They exert in particular after oral, executor, Basel, Switzerland, assignors to Ciba-Geigy rectal and parenteral administration a central depressant Corporation, Ardsley, N.Y. action on the central nervous system. For example they No Drawing. Filed May 11, 1971, Ser. No. 142,390 reduce motility, potentiate the action of anaesthetics, and Claims priority, application Switzerland, May 13, 1970, counteract the effect of amphetamine. Moreover, they 7,069/70 10 have an adrenolytic and histamineantagonistic action. Int, C. C07d 27/36 These properties are determined by selected standard tests U.S. C. 260-326.9 15 Claims (cp. R. Domenjoz and W. Theobald, Arch. Int. Pharma codyn. 120, 450 (1959), W. Theobald et al., Arzneimit ABSTRACT OF THE DISCLOSURE telforsch. 17, 561 (1967) and W. Theobald and R. Compounds of the class of 1,2,3,8-tetrahydrodibenzo 15 Domenjoz, Arzneimittelforsch. 8, 19 (1958). (b,f pyrrolo 3,4-diazepines which may be substituted in Thus, merely by illustration, it is demonstrated that 2 the 5- or 6- and/or 8-position by chlorine, the trifluoro methyl-5-chloro-1,2,3,8-tetrahydro - dibenzo[b,flpyrrolo methyl group or alkyl groups respectively or the allyl 3,4-diazepine in the form of the hydrochloride salt ef group respectively and pharmaceutically acceptable addi fects a 50%. decrease of orientation motility after intra 20 peritoneal administration on mice in an amount of 0.77 tion salts thereof have a depressant effect on the central mg./kg. nervous system; they can be prepared from the corre The same compound subcutaneously administered in an sponding N-substituted 10,11-bis-bromomethyl - 5H - di amount of 10 mg./kg. to mice, which had been anaesthe benzbfazepines and a primary amine; the compounds tised by intraperitoneal administration of 40 mg./kg. of are active ingredients of pharmaceutical compositions. 25 the short-acting anaesthetic N,N-diethyl-2 - methoxy-4- allyl-phenoxyacetic acid amide potentiates, i.e. prolongs the effect of the anaesthetic to a significant extent. DETAILED DESCRIPTION The same compound exerts an adrenolytic effectiveness The present invention relates to new azepine deriva which is found equal to the activity of Regitin. tives, processes for their production, medicaments con 30 The same compound effects an antagonism against taining the new compounds, and their use. histamine which is found equal to the activity of More particularly, the present invention relates to com Antergan. pounds of the formula Similar results are found with 2-ethyl-6-chloro-1,2,3,8- tetrahydro - dibenzo[b,fpyrrolo[3,4 - diazepine, the 2 35 ethyl- 6 - chloro - 8 - methyl-1,2,3,8-tetrahydro-dibenzo Ib,fpyrrolo[3,4-diazepine and the 2-methyl-5-chloro-8- methyl - 1,2,3,8-tetrahydro - dibenzobf)pyrrolo2,4-d R azepine. Although the hydrochloride salts are preferred, also 40 other pharmaceutically acceptable acid addition salts can c be used. / X The pharmacological properties of the compounds of the present invention render them suitable for the treat ment of states of tension and agitation of psychic and NNO. muscular genesis. The compounds of the Formula I are produced ac (I) cording to the invention by reacting a compound of Formula II 50 wherein R and Ra are hydrogen, alkyl groups having at most 4 carbon atoms, or the allyl group, X is hydrogen, chlorine, or the trifluoromethyl group, and HBr, H X is chlorine if X is hydrogen, or hydrogen if X1 is chlorine or the trifluoromethyl group. H 3. K Cas and the pharmaceutically acceptable addition salts thereof. / N -Xa In the compounds of Formula I R1 and R2 as alkyl groups having at most four carbon atoms are e.g., the methyl, ethyl, propyl, isopropyl, butyl, isobutyl or the 60 - X sec.butyl group. N Preferred members of this class are: R (II) 2-ethyl-6-chloro-1,2,3,8-tetrahydro - dibenzo[b,f)pyrrolo 3,4-diazepine 65 2-methyl - 5 - chloro - 1,2,3,8-tetrahydro - dibenzo Ib,f pyrroloI3,4-diazepine wherein: 2-ethyl-6-chloro - 8 - methyl-1,2,3,8-tetrahydrodibenzo R1 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl or b.fpyrrolo 3,4-diazepine sec.butyl or a group which by means of hydrolysis can 2-methyl-5-chloro-8-methyl-1,2,3,8-tetrahydro - dibenzo 70 be replaced by hydrogen, and b,flpyrrolo[3,4-diazepine X and X have the meaning given under Formula I, 3,772,348 3 4. with an amine of the General Formula III: by way of the intermediates: methyl-(2-chloro-9,10-di methyl-acridan-9-yl)-ketone, 2-chloro-a,9,10 - trimethyl 9-acridanmethanol, and 2-chloro-5,10,11-trimethyl-5H-di N4: benzIb,fazepine. N A second process according to the invention for the H (III) production of compounds of Formula I comprises alkylat wherein R has the meaning given under Formula I, hy ing a compound of the Formula IV: drolysing, the reaction product if R1 is a group which can be replaced by hydrogen by means of hydrolysis, and, R optionally, converting an obtained compound of the gen O N eral Formula I with an inorganic or organic acid into an Ho? Yoit, addition salt. The bisbromomethyl compounds of the General C-5 Formula II are reacted with the free bases of the General / YN x, Formula III in the presence of a solvent. Suitable sol vents are those which are inert under the reaction condi NN-1 -X tions, e.g. hydrocarbons such as benzene or toluene, halogenated hydrocarbons such as chloroform, lower h (IV) alkanols such as methanol or ethanol, ethereal liquids wherein R2, X1 and X have the meaning given under such as ether or dioxane, as well as lower alkanones such 20 Formula I, preferably in the presence of solvents and as acetone, methyl ethyl ketone, or diethyl ketone. The basic condensation agents, by means of a reactive ester reaction temperature is preferably between 20° and 100 of an alkanol of Formula V: C. For the bonding of the hydrogen bromide eliminated in the reaction according to the invention, an appreciable excess of base of the General Formula III is preferably 25 in which R1 has the meaning given under Formula I for used. R1 with the exception of hydrogen; and, if desired, con Croups R convertible by hydrolysis into the hydrogen verting the obtained compounds with inorganic or organic atom are, e.g. acyl radicals, e.g. lower alkanoyl groups acids into their addition salts. having preferably 1-4 carbon atoms, such as, e.g. the Starting materials of the General Formula IV can be acetyl group, arenecarbonyl groups such as the benzoyl 30 produced analogously to the first process by reaction of group, radicals of monofunctional derivatives of carbonic 5-acyl-10, 11-bisbromomethyl-5H-dibenzb,fazepine de acid such as, e.g. the methoxycarbonyl, ethoxycarbonyl, rivatives of the General Formula II with an amine of or the phenoxycarbonyl group. Hydrolysis can be per the General Formula III, and hydrolysing the obtained formed with the aid of an alkali metal hydroxide, e.g. acyl compound. potassium or sodium hydroxide, preferably at the boiling Used as the second reaction component are reactive temperature of the reaction mixture, either in a higher esters of alkanols of the General Formula V. As reactive boiling organic solvent containing hydroxyl groups, such esters it is possible to use, e.g. halides usch as chlorides, as, e.g. ethylene glycol or diethylene glycol, or in a bromides or iodides, Sulphonic acid esters such as meth lower monoalkyl ether of such a glycol, and, in particular, anesulphonic acid ester, benzenesulphonic acid ester, o in a lower alkanol, e.g. methanol or ethanol. Further 40 and p-toluenesulphonic acid ester or 2,4-dinitrobenzene more, hydrolysis may by performed, e.g. also in acid sulphonic acid ester, as well as sulphuric acid ester such medium, e.g. in alkanolic hydrochloric acid, or with the as dimethyl or diethyl sulphate. aid of hydrogen bromide in water or glacial acetic acid. The reaction according to the invention can be per A group of starting materials of the General Formula formed in the presence or absence of an inert organic II are compounds which are substituted in the 5-position Solvent. Suitable inert solvents are, e.g. hydrocarbons by an acyl radical. A compound falling into this group Such as benzene, toluene, xylene, cumol or Tetralin, is 2 - chloro - 5-acetyl-10,11-bisbromomethyl-5H-dibenz ethereal liquids such as dioxane, alkanones such as Eb,flazepine. This compound can, for example, be acetone or methyl ethyl ketone, carboxlyic acid amides produced as follows: Starting with 2-chloro-9-methyl such as dimethylformamide, phosphoric acid amides such acridine Icp. A. Campbell et al., J. Chem. Soc. (London) 50 as hexamethylphosphoric acid triamide, or sulphoxides 1958, 1145), this yields with acetaldehyde, in the presence such as dimethyl- or diethylsulphoxide. Suitable basic of tert-butyl hydroperoxide and ferrosulphate-heptahy condensation agents are, e.g. alkali metals such as sodium, drate: methyl-(2-chloro-9 - methyl - acridan - 9 - yl)- potassium or lithium, alkali hydroxides such as sodium ketone; this ketone is reduced, with the aid of sodium or potassium hydroxide, alkali metal carbonate such as borohydride, to 2-chloro-O,9-dimethyl-9-acridanmethanol; potassium carbonate, alkali metal amides such as sodium-, the obtained reduction product is rearranged in dilute potassium- or lithiumamide, alkali metal hydrides such Sulphuric acid according to Wagner-Meerwein to give 2 as sodium or lithium hydride, alkali metal alkanolates chloro-10,11-dimethyl-5H-dibenz(b,flazepine, and dehy Such as sodium methylate, sodium ethylate, or sodium drated.
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