DE1909038A1 - New heterocyclic derivatives - Google Patents

Description

14.82.06

IJCB (UIiIOF OHIMIQUE-OHEMISCHE. BEDRIJVM-) S, A.

Saint-G-illes-lez-rBruxelles / Belgium, 4 jί ehaussee de Charleroi

New heterocyclic derivatives

Priority: British patent application n ° 8841/68 dated February 23, 1968

The invention relates to new heterocyclic derivatives mit.pharmakolqgischen properties, to their addition salts with pharmaceutically acceptable inorganic and organic acids and also on processes for their production

The new heterocyclic derivatives according to the invention correspond to the general formula ^

where mean:

A a. Hydrogen atiom. _{r is} a halogen atom, an alkyl, haloalkyl or oyanoradical,

B is a hydrogen atom or an alkyl radical,

909836/1678

-Z-

X.a methylene group or a heteroatom, ζ.B ₀ sulfur, a group -CH (CH ₅ ) -CH ₂ -, -CH (CH ₅ ) -CÖ- or - ■; _ -CH ₂ -CH (CH ₅ ) -, '": ■■ -' ■ .. ...: ■;, ■ '.- ■

R and R 'each represent a hydrogen atom or an alkyl radical with a straight or branched chain, or they form ^ together with the nitrogen atom. a heterocyclic one

. Radical with a maximum of seven chain links, selected from the 'alkylenimine (e.g. pyrrolidine,

Piperidine- or iron-hexylenimine-), oxaalkylenimine- (for example Morpholines), Tii-j-aalkylenimine- (at- ' for example thiamorpholine-), azaalkylenimine- (for example Piperazine-), ¥ -alkyl-aza-alkylenimine- (for example N-alkylpiperazine-), ir-Hydrpxyalkyl-aza-alkylenimin-, N-alkoxyalkyl-aza-alkyleniiiiin- and F-aryl-aza- " alkyleneimine radicalsβ

The heterocyclic derivatives of the present invention are obtained by known synthetic methods, from which \ the following are mentioned:

a) Condensation of a benzazocine of the formula I with a; ■ N-R-Ii-R'-2-Hal-propionamide of the formula II according to föl- ' The following scheme: -. ;

of

NH + Wal -CH- CO-U I - ' ^N

CH

A r

N-CH-CO-N ^ .-

(D

(H)

b) Reduction of an IT- (IT- ¹ -R-IT'-R'-Amino-Zj-benzazocina of the formula IV in the presence of an aluminum hydride, ._. ^::

(For example, lithium aluminum hydride) according to the following Scheme:. ~

909836/1578

B.
(IV)

_R reduction

NZN ^ ~~ ~~ * X

^X R 'LiAlH,

N-CH-CH ₀ -N 'i' CH,

.or

N-GH ₇ -CH-N CH,

c) Condensation of an alkali derivative of a benzazocine of Formula VII with a UT-R-U-R'-2-halopropylamine of the formula VIII, if necessary, with a mixture of two diamines (V) and VI):. :

N-Me

Hai-CM-CH., - ^ -> (V) + (VI)

R ¹

(VII) (viii) =. ■ ;.

In, the above equations, A, X, B, R and R have ^f . while Z under the radicalization the meaning already ^indicated: len - · is selected and Hal is a halogen atom and Me is a - CH (CH ₅₎ -CO and -CO-CH (CH _3). Alkali metal mean: .-; ·. .

The products according to the invention are pharmacological substances with strong antidepressant Sigenso juices. They are equal-' if stimulants for the central nervous system, anorexigenic, antxhistaminic, antispasmotic, sedative or hypnotic

9098 36/1578

Γ909038

cal means.

J ¹ The following products according to the invention were used for the activity tests given below:

A: 9-chloro-1- (2-aminopropyl) -1,2,3,4,5,6-hexahydro-1-benzazocine,

B: 9-Fluor-I- (2-aminopropyl) -1,2,3,4,5 »6-hexahydro-1 benzazocine (31.2),

Ci 1- (2-methylamino-propyl) -1,2,3,4,5,6-hexahydro-1 » benzazocine (70),

Di1- (2-amino-propyl) -1,2,3,4 »5,6-hexahydro-i-benzazocine (45.5)

E: S-chloro-6- (2-amino-1-methyl-ethyl) -2,3 * 4,5-tetrahydro-1,6-benzothiazocine,

F: i- (2-Amino-1-methyl-ethyl) -1,2,3> 4!> 5,6-hexahydrobenzazocine (58.9)

Gi 8-chloro-6- (2-amino-propyl) -2.3 »4» 5-tetrahydro-1,6-benzothiazocine (45)

Hi 2- (1,2,3,4,5,6-hexahydro-1-benzasocin-1-yl) propionamide

Is 1- (2-pyrrolidino-propyl) -1,2,3,4 »5,6-hexahydro-1-benzassocin (41) ·

The numerical values given in brackets are those of the lethal dose (Dl ₅₀ ) obtained in the rat by intravenous route and expressed in mg of the free base per kg of animal »

Antidepressant activity

a) Potentialization of the amph @ taminic stereotype at the rat

The method of (J. HAI1LIWELL et al. (Brit. J. Pharmacol.; 23_ (1964) 330) aa ₉ and the dose DE 200? Ί (dose in mg base / kg! Animal) on intraperitoneal The way to determine what a double duration of the amphetaminic stereotype, based on that secures what the experimental animals show. The ones with the inventions

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The results obtained with the compounds are compared in the following table with those obtained with two very well-known antidepressant substances, namely desipramine (10, t1-dihydro-5 - ^ - (methylamino) -propyl7 ^ 5H - dibenzo / SjfJ-azepin) and the Ämitryptilin (10,11-dihydro-5 - (^^ 3-dimethylamino-propylideh) ^ 5H ^ dibenzO / ä, d-cyclohepten) were obtained. ; ■ ^: Λ. /

Product - ■ ". ■ DE · 200 ^;:

: Desipramine 3.8 ^: - -.; "". - .- ■; "-. · '"

.. -; Amitryptiline; i 25. ^v VV; /

b) Effect on the rotating tibia. -;

In this test by HWDUNHAM and TS MlYA (tr.Amer.Pharm As s o c.46 (1957), 208) the following results were obtained for the effective dose (Dl ₁ -Q) in the rat atif intraperitoneally obtained, expressed in mg / kg animal.

Product - -

Dexamphetamine 9 »8,

Desipramine 35

Ämitryptilin 34

Ketipramine, 88

It will be noted that in this ^ 'est the inventive Compounds are on average far more effective than their counterparts used clinically as antidepressants (Dexaamphetamine = d-1-phenylr2-aminopropane; Ketipramine = 5Z5- (dimethylamino) propy] ^ - 5i11-dihydro 10H-dibenz / b, f7azepin-10-one)

o) antitetrabenazine activity,

In this test (M. GIURGIA et al. Med.Exp, £, (1963), 249)

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the antidepressant activity is expressed by the effective 'dose DE, -' in mg of base per kg of animal administered by subcutaneous route in rats · The following table gives the results obtained again

t , ■ _: ^DE 50

DesipramiT! 16

The three previous tests show that the Products according to the invention have a considerable antidepressant effect Have an effect

Hypnotic activity

Man. uses the general mouse behavior test by 3rd IRWIIi (Gordon Research Conference on Medicinal Chemistry, at 3-7, 1959 at Colby Junior College, New London) In this test, the pharmaceutical product under test is administered by the intraperitoneal route. The administered Dose is expressed in mg free base per kg animal. The following behavior with the product H of the invention was found ^

Dose Cmg / kg) behavior

23 normal

70 the mouths are calm

139 Prevention of the reflex of the. Recovery

. direction for 40 minutes

232 Prevention of the reflex of the rebound

direction for 60 minutes

464 Prevention of the reflex of recovery

direction for 90 minutes.

The erfindungagemässen products are buccal and parenterally administered in the Porm of solid or liquid, 'the usual excipients containing "MischunV gen" The unit dosage varies preferably between 50 and 150 mg "

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Br onchOspaBiaoly table assets;

In this 3? Est by J "JULLIW u" ä "(Arzneimittel-Porschung, 18, (1968) 995), the product I according to the invention was compared with theophylline in its anti-bronchospasm, caused in guinea pigs by acetylcholine and serotonin Histamine The effective dose (DEcq in mg / kg by intravenous route) for these two substances is also determined. :

Product 50 in mg / kg \ ge% caused a spasm

Aetylcholine by.. histamine OjTO
. 8 \: ^ ^: - ^:: \ Serotonin 0.35
4 ■: ■ ·. I.
Iheophylline. 0.60
A- - ■ .- ■■■

It can be seen that the compound I according to the invention is a has considerable bronenospasmolytic activity.

The following examples explain the invention without restricting it · ■ - ■ "". ". ^V. Ν - -

Example 1 I, ^ "■.;" _ -. , "■" .. ' \ _:. . -J \; .'_ \ -. ; -, _ ■■ - ";.. ■ '- ■ .'- 2- (1,2,3,4,5» 6-Hexa ^ ydto ^ f-benzazö.oin- ^; 1. * « ^; yl) - propionamicL ..

A mixture of 23.2 g 1 _for 2 _r 3.4 _? 5-6-Hexahydro-1-benzazocine, 30 g of 2-bromopropionamide and 18 g of anhydrous sodium carbonate in 30 ml of i ^ Bserfre ± em '-' ^ Xoi- ^{: i} vi! ± ^ ä ^^ ähr.e _i n.ä "--- ^{heated to 115 0} O for 2 hours with mechanical stirring.:

50 ml of benzene are added and the mixture is then filtered after cooling, the base filtrate, washed with water and dried over anhydrous sodium sulphate, is evaporated to dryness under reduced pressure on the water bath. Melting point of the base 125-t26 ° C isopropanol)

Melting point of the oil hydrate B 223-225 ° C (currently at 237-23800) (laöptopanol)

Calculated for ^ 4H ₂₀ NgO Ji Ii 12.5

found «n. ^ 11 ^ 88

Calculated for G ₁₄ H ₂₀ ^ O * Höii> 01 ~ 13.19 # ff .10.42

. found ^ 12.98 10.21

The following products were produced in an analogous manner

a) 2 ~ (8-chloro-2,3,4,5-tetrahydro-1 ₅ 6-1 amide ■ "

The condensation product * (sparingly soluble in benzene) ^ precipitates out, The reaction mixture is filtered and filtered after cooling the precipitate rubbed in water »- The FÜtrati as above ' treated, provides a second attack of the same. Prod \ ikt8 <

Melting point 153-154 ⁰ O (ethanol) / ■ ...-. ';·; ^: <^{; c} : _ ^: -.J: -

Calculated for 0 ^ H ₁ found

6-yl) propionamide

01 total 12> 44

1, ■■■■ -. "; ^: 12ρ05 '

»Bensa ^ ocin-

^ η. Melting? ■ Boiling point 150-155 0 / 0.001 mm Hg. -Γ. .; £ point "^

'■; - ether 40-6Ö ^D G) ^ - \; Calculated for C ₁₅ H ₂₁ ClIi ₂ OS $ 01 t.ly3 _L 3? Έ; H f ₉ 95; ; V 1V.,; ; ^: found '. ^:.:; 11> 27 8.95' ^ V;

c) "Si N-DiMethyl-2- (1,2,3,4,5, e-hexahydro-i-bengazocin ^ i-yl _:) propionamide... ■ ^ / ^

Boiling point 127-129 ° C / 0.001 mm Hg.

Sehmelzpunfct 79-80 ⁰ O (petroleum ether 40-60 ^Q C)

Calculated for 0

found

Example 2
8-0hlor-6- (2-

Ή 10.76
10.92

'-2 "3.4" 5-tetrahydro ° -t

One warms at the reflux © for 18 hours a ^; Mixture of 20 g of 6- (2-aittino-propiOnyl) -6-ciilor- "2.3 _s 4,5-tetrahydroM _s 6-> ^ benzothiasocih and 6.2 g of Mthiumaluininiumhydrid in anhydrous ether in nitrogen gasoline. The in Ice-salt mixture of cooled reaction mixture is then treated with 6.2 ml of water, 6.2 ml of aqueous sodium hydroxide solution of 20% and 18.5 ml of water, filtering off and washing the ethereal precipitate is dried over anhydrous potassium carbonate iand solvent under vacuum on the water bath from ₉

243-244 ⁰ C 19QyUd8 causes » 3,4,5-tetrahydro- 96 S 10.43 208-209 ⁰ C 151-153 ° C (Isopropane pl) Jt ₁ ? 9.90 "■■ ·" ■ -9- 23.07 # -oil " -9.80 '$> N 8.35 $ C1 "13.91 # N 10.99 9.94 Melting point of the hydrochloride 23.35 " (Isopropanol) by heating on , 5.6-hexahydro-i-benzazoBine. 8.29 13.94 10.72 ■■ "■■■ Calculated for
.C ₁ ^ H ₁ QClH ₂ S- * HCl $> Gl total '11, 53 1 » N 9ViI ^ S10,4: 170-172 ⁰ C d) 1-C2-amino-1-methyl-ethyl) -1,2,3,4,5,
; - a ..''- ·, '■■ "-.'" ■ '; '-..- e) 1 ~ (2> -Dimetliylamino-1-methyl-ethyl) -1, 3.4 t 5-tetrahydro- found 12.28 / 8.86 10.5 213-215 ⁰ C (isopropanol) ' Gl "13.91 Melting point of the hydrochloride 1-benzazocine. The following products were made produced in an analogous way: 96 N 9.12 - 14.16 Calculate for -C ₁ ^ H ₂₂ N ₂ .HGl J Melting point of chlorohydrates (Isopropanol) a) 8-chloro ^ 6- (2-amino-1-methyl-ethyl) -2, 8.88 c) 8-chloro-6- (2-dimethylaminopropyl) -2, ' found Calculated ^ ir'GI ₆ H ₂₆ I ₂ .HCl \ $> S 9.56 1,6-benzothiazocine 1,6-benzothiazocine .. ; ^ '^ - v. found 9.69 Melting point of the hydrochloride 6 «* hexahydr o ~ 1 -benzazo- The reduction is in tetrahydrofuran calculated for
C ₁₅ H ₂₃ GlN ₂ SvHCl. i " Cl" 10.57 (Isopropanol) Reflux for 10 hours found '"10.78 9έ Ν 10.99 Melting point of the hydrochloride 10.85 Calculated for
C ₁₃ H ₁ QClN ₂ S.HCl # 01 "1-1., - 03 2,3,5,5,6-hexahydro- found - 11.96 b) 1- (2-amino-propyl) -1,2,3.4 178-180 ⁰ C (isopropanol) Melting point of the hydrochloride υ Gl "* 12.54 calculated for C ₁ .H ₂₂ N ₂ -HCl 96 12.58 " ^: " found

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:. ' V ■ ■■■: / V -10-. V: '. _ ^■': ..: V ■■ ■ - ■■ _ ■.

f) 1 - (2-methylamino-propyl) 1 »2,3» 4 «5,6-hexahydro-i

Boiling point 96-98 ° 0 / Ο.001 mm Hg.

Melting point of the hydrochloride 187-190? C (isoprö ^ paiiol)

Calculated for C ₁₅ H ₂₄ ] J ₂ ^ HCl f Cl "13.19""^""K 10.42 / V found 13.32 -; ί" 0, "41" ■, /

g) 8-rßnlpr-6 ~ (2-dimethylamino-1 -methylr-ethyl) -2-, 3 » ^ ■ ^ hydro-lye-benzothiazoein - ■ :: '. - 'ί

Melting point of; Chlorohydrates 186-188 ⁰ C; (isopropane blX .-

Calculated for C ₁₅ H ₂₃ ClN ₂ S 1 HCl i> Cl 1 10.57 ^ -JF8.35; ^; S 9.56 found - "." .-: 10.85; 8.30,. "-; ■ -J 9 ₅ 20

h) 1 ~ (2-dimethylamino-propyl-i _f 2,3 _a 4 »5,6-

Melting point of the chlorohydrate 175-176 ⁰ G (isopropanol) V Calculated for G ₁₆ H ₂₆ N ₂ .HCl <fi Gl "12.54 -.- ■ £ N 9> 9O '■ found. 12.96 tOj15 -

i) 9-chloro-1 - (2-aminopropyl) -1,2,3 ₉ 4? 5,6-hexahydro- 1 ^ -benzazo-

Melting point of the chlorohydrate 210-21.1 ⁰ C (ithanol)

Calculated for- " ^: ■ - ^ - : ■ - ': -

C ₁₄ H ₂₁ ClN ₂ ^ Cl $> Cl total $ 24.50> Gl " 12.25 % Έ 9.68:; ■ ^

found 24.25 12.28 9.65

j ), 9-I ¹ IuOr-1 -C2-aminopropyl) -1,2,3,4,5, δ-hexahydro-i-benzazocine

Low temperature of the hydrochloride 187-189 ° C (isopropanol) Calculated for C ₁₄ H ₂₁ IN ₂ .HCl ^ F 6.96 # Cl "12.99 $> N 10.26 - found 6.89 13.4 10.40

kj [8-Ghlor-6- (2-methylamino-propyl) 2,3,4,5rtetraliydro-1 ₉ 6-benzo

Sohmelzpünkt the base 6i-62 ° C (petroleum ether b.p. 40-60 ⁰ C) Calculated for G ₁₄ H ₂₁ ClN ₂ S Cl 12.44 # N 9.83% S 11.25. ■ -V "found 12.14 9.80 11.56,

rS * - iZydlMQ thylamino-propyl) -3-methyl-2,3,4,5-te trkhydr 0-1 ^ 6τΐ? βηζ ο thiaz ο a

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ΐ entered T3TB

Melting point of the chlorohydrate 225'-226 ⁰ C (isopropanol)

Calculated for CIgH ₂₅ OlIi ₂ S.Hol found ^

m) -. 1 - (2

> Cl 10.15> I8, 01 f> S 9 » 17th 10.38 Ο '7, 90 9, 13th .-3, , 4 * 5, 6-h @ xahvdro-1 -fcenzazocin

-Melting point of the chlorohydrate 204-205 ° C (isopropanol)

Calculated for O ₁₈ H ₂₈ ^ ₂₉ HeI # Cl "11.47? Έ Ε 9.06 geftmdezi.;: 11.56 9> 02

n) 1 ~ (2 ~ Piperxd.iii-propyl) -.1 i ^ 2.13 »4 .5» 6-hexahydro- 1- ^ beiizazociil ·

Melting point of 187-188 ° öhlorhydrats · 0 (isopropanol) Calculated for G ^^ H ₅₀ H ₂ "HO 1 ^ Cl '" 10.98 $> 8.68 Έ _found: 7 11.28 8.88

Find out what the Mischuag Ton positional is omers provide (Terfahren c). > V '

2u of a suspension of clay ₅ % sodium amide, starting with 2 * 53; A solution of 16.2 g of sodium in 80 ml of liquid ammonia is added 1 _? 2 _s 3 _{g 4 s} 5 »6-Hexahydro-1 -" benZaaoWin in 100 ml of anhydrous xylene, after the "evaporation of the ammonia one warms to 12O-125 ° Ö for 2 hours" then one sets hot about Sa ⁰ O 15 g E- Ghlor-I-Cdimethylamizio) propane, dissolved in 15 TQl. anhydrous xylene hinsuο Hach 4 hours heating at 120-125 ⁰ O cooled ah ₉ adds slowly 150 ml ¥ ater added, filtered and the organic layer separated afc. The organic solution is then washed 3 times with 100 ml of water and then with

dilute hydrochloric acid (20 kl concentrated HGl, + 60 ml water) extracted. The acid; Solution becomes / a concentrated sodium. The hydroxide solution is made alkaline and the free bases are extracted with benzene. The solution in henzene, washed with water and dried over anhydrous Matriura sulfate, is evaporated under reduced pressure for irookne. The evaporation residue shows according to the Ehromatographic Eethode in a thin layer (CHaOH) the presence of two isomers 1- (2-dimethylamino-1-metii ^^ äthyl :) ~ 1,2,3,4 »5, e-hexahydro-i- henzazocin and 1- (2-Dimethylaffiino-propjl) 1 , 2, J, 4,5 »6-hexahydro-1-henzazocin in Yergleicit with -den, samples, of the products :, produced by the i

BfB

19U9Ü38

Processes which have no possibilities for isomer formation (Examples 2 e and 2h).

The chlorohydrate of the isomer mixture is formed in a mixture of isopropanol-ether and crystallization is initiated with a seed of the chlorohydrate of 1- (2-dimethyiamino-propyl) 1 »2» 3,4i5,6-hexahydro-1-benzazx) cin. .

After two recrystallizations from isopropanol, the product obtained melts at 174-175 ⁰ C and is no degradation in the determination of the melting point in mixture with the hydrochloride of 1- (2-dimethyl-amino-propyl} -1,2,3,4, 5,6-hexahydro-1-benzazocine, prepared according to Example 2 h.

Calculated for C-JgH ₂₆ Ii ₂ .HCl ji -. ' Oi "" 12.54 # Έ Ϊ 9.90 found 12.86 10.11

All of the end products of Example 2 can be based on the same Way to be made. -;

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Claims (1)

- - - -. lyuyuj « P at e η "t a η s ρ r ii c h e 1. Heterocycles ch.e compounds of the general formula a '■■. "■■". -: N-Y-N. where mean: A is a hydrogen atom, a halogen atom, an alkyl, alkoxy, Haloalkyl or cyano radical, B is a hydrogen atom or an alkyl radical, X is a methylene group or a heteroatom, for example sulfur, Y is a group -CH (CH ₅ ) -CH ₂ -, -CH (CH ₅ ) -CO- or -CH ₂ -CH (CH ₅ V, R and R ¹ each a hydrogen atom or an alkyl radical with a straight or branched chain, or together with the nitrogen atom they form a heteroeyclic radical with a maximum of seven chain members, selected from alkylenimine (for example pyrrolidine, piperidine or ^: 1.6 -Hexylenimine-), oxaalkylenimine- (for example: Mor.ph.olin-), thiaalkylenimine- (for example iDhiamorpho- - Hn-), azaalkyleniffiin- (for example piperazine-), N-alkyl-aza-alkylenimine- (for example N- Alkylpiperazine-) li-hydroxyalkyl-aza-alkylenimine, H-alkoxyalkyl-aza-alkyleiBrimin ^ and N-aryl-aza-alkylenimine radicals, and their addition salts with pharmaceutically acceptable acids. 2. iieuB.Verbindungen according to claim 1:. - ? r- i- (2-amino-propyl) -1,2,3,4,5,6-nexahydr · o-1 -benzazo ? - 1 - (^ - ataino-propyl) -1,2,3,4 $ 5 , 6-hexahydr o-1 -benzazö a, I- (2 - Meithylamino ^ propyl) - ί, 2:, · 3 \ _i 4, 5 ■> 6 * hexahydro-1 ^ benzazowin, T-- (2-Amiiio-pr op-yl) "1, 2, 3.4" 5.6-hexaiiydrb - 1 ^ ^-; ben; za2ooin, 8-Cnl qr-6 ^) C2 - ämino- l ^ methyl-äthiyl ·) ^, .5,4,5- tetrahydro-1,6-benzo thiazQ a; _{_:;.} '.-. - ''"- .. ■,;, .- '- "■■.; ■ '"-. 1- (2-Amino-1-methyl-ethyl) -1, 2, 3 ' ,, 4,5, e-8-chloro-6- (2-aminopropyl) -2,3,4, .5 -tetrahydro-i ^ 6-henzotnia 2- (1,2,3 f 4 »5» 6-hexahydro-1-benzazocin-1- yl) -prop ± onaiEJui * _; 3. β process for the preparation of the heterocyclic gen. according to i-nspruch 1, .. wherein Y is -CH (GH -,) - CO-, thereby g e-k.e η n.z e i c. h η e t, d a s s m ä ~ η a ■ Benzazocine of the formula I with a li-R-ir-Ri-S-der Formulas according to the following scheme. + Ha I ~ CH-CO-f - ■ * x H-CH-CO-H ' CH, (I) (II) (HI) ^; condensed, where A, B »X» R and E ^! those in the claim. 1 given; ne · have meaning and Hai denoted a halogen atom T 4. Process for the preparation of the heterocyclic compounds of claim 1, wherein Y -CH (GH ^) - CH ₂ - or -CHp-CH (CH ^) - XSt, characterized in that in the presence of an aluminum hydride a Ii- (JJ * -E-Ii'-R amino-Z) benzazocine of the formula _. X N-Z-N "■ v, - R ¹ reduced, wherein _: A, B, X, R and r 'have the meaning given in claim 1 and Z is selected from the radicals -CH (CH-Z) CH- and -CO-CH (CH ^) - 09 8: 36/1 5 78 . "" "~ ~~~ 1 y ύ 9 U j ö 5. A process for the preparation of the heterocyclic compounds of, claim 1, wherein X is -CH (CH, J-GR ₉ or -CH ₉ -CH (CH,), characterized geke η η ζ calibrated that an alkali derivative of a benzazocine is the Formula VII with an NRFR ¹ -2-halopropylamide of the formula VIII, optionally with obtaining a mixture of two diamines (V) and VI) according to the following scheme Hal-CH-CM.-tr -—> X N-CH-CH ₉ -N ^ ι - ^{L x} Di I ι ι ■ ■ ^ CH. (VII) (VIII) ^ö (V) N-CH ₉ -CH-N condensed, wherein Α.Β, Σ, R and R ^{r have} the meaning given in claim 1, Hal is a halogen atom and Me is an alkali metal 6. Compounds useful as antidepressants, Central nervous system stimulants, anorexigenic, antihistamic, anti-epasmotic, sedative and hypnotic Means of the general formula \ _o i where mean: 90983 6/15 78 A is a hydrogen atom, a Halpgen atom, an alkyl, alkoxy, Halogezialkyl or cyano radical, / B a hydrogen atom or an alkyl radical: X is a methylene group or a heteroatom, e.g. sulfur, Y is a group -CH (CH ₅ ) -CH ₂ -, -CH (CH ₅ ) -C0- or -CH ₂ r-CH (GH ₅ ) R and R * each represent a hydrogen atom or an alkyl radical with a straight or branched chain, or they form, together with the nitrogen atom, a heteronylic radical with a maximum of seven chain links selected from the alkyleneimine (for example pyrrolidine, biperldine or 1,6-hexyleneimine) . ^; . .N-alkyl-aza-alkyleneimine (for example H-alkylpiperazine-F-hydroxyalkyl-aza-alkyleneimine, N-alkoxyalkyl- ^ az & -alkylene imine and H-aryl-aza-alkyleneimine radicals,> and their addition salts with pharmaceutically acceptable "' acids *. ^. ^; ."";"";;'." . '.' ■ '.- ;. -. W. "■", \ _{: i ::} . ; -: 7 solid and liquid medicinal products for ^ use on ^ ' oral and parenteral route, which at least one binding according to claim 6 contain * "-: 909836/15 78