CH617662A5 - Process for the preparation of novel benzylamines - Google Patents

Abstract

Preparation of novel benzylamines of the formula I <IMAGE> in which the symbols R1 to R5 have the meaning given in Patent Claim 1, and of their hydrolysis products in which R1 denotes hydrogen, and their physiologically tolerable acid addition salts with inorganic or organic acids. The compounds of the formula I have useful pharmacological properties, in particular an anti-ulcer action, a secretolytic, cough-relieving and heightening action on the production of the surfactant or anti-atelectasis factor of the alveoli. The compounds of the formula I are prepared by reaction of a compound of the formula II <IMAGE> in which R9 denotes a hydrogen atom or an aliphatic or aromatic group corresponding to R1 with a nitrogen compound of the formula HNR4R5 and, if appropriate, subsequent hydrolysis of the reaction product.

Description

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PATENT CLAIMS 1. Process for the preparation of new benzylamines of the formula (I)

5 (I),

wherein

R.! an aliphatic or aromatic acyl radical;

R2 is a hydrogen, chlorine or bromine atom;

R3 is a methyl or alkoxy group in the 3-, 4- or 5-position of the phenyl nucleus, a straight-chain or branched alkyl group with 2 to 4 carbon atoms, a fluorine atom, a trifluoromethyl, cyano, carbamoyl, carboxyl, Carbalkoxy, acetyl or 1-hydroxyethyl group or the aminomethyl group of the formula

/ R6

-ch2-Nx where R6 and R7, which are the same or different, each represent an alkyl, cycloalkyl or hydroxycycloalkyl group or both together with the nitrogen atom to which they are attached represent a pyrrolidine, piperidine or morpholine ring and

R4 and Rs, which are the same or different, each have a straight-chain or branched alkyl radical with 1 to 5 carbon atoms, which can be substituted by 1 or 2 hydroxyl groups, an alkenyl radical with 2 to 4 carbon atoms, a cycloalkyl radical optionally substituted by one or two hydroxyl groups 5 to 7 carbon atoms, a benzyl or morpholinocarbonylmethyl group or both together with the nitrogen atom to which they are attached, a pyrrolidine, piperidine, hexamethyleneamine, morpholine, N-methylpiperazine or camphidine ring, and R4 also a hydrogen atom mean, as well as their physiologically compatible acid addition salts with inorganic or organic acids, characterized in that a compound of the formula (II)

(II),

wherein

R9 represents a hydrogen atom or an aliphatic or aromatic group corresponding to Rt, with a nitrogen compound of the formula (III)

H-N

• I

\

R,

(III)

implemented and the process products optionally subsequently converted into their physiologically tolerable salts with inorganic or organic acids.

2. The method according to claim 1, characterized in

5 shows that the reaction is carried out in a solvent.

3. The method according to claim 1 or 2, characterized in that the reaction at temperatures from 100 to 200 ° C, preferably at temperatures from 120 to

10 180 ° C.

4. The method according to claim 1, characterized in that a compound of the formula (I) obtained, in which R3 represents a cyano group, is converted into the corresponding carbamoyl compound by partial hydrolysis.

15 5. Process for the preparation of a compound of formula (I ')

20th

25th

(11) 3

wherein the symbols R2 to Rs have the meaning given in claim 1, characterized in that

30 by the process according to claim 1, a compound of formula (I) is prepared and then hydrolyzed, the hydrolysis being carried out in the presence of an acid or in the presence of a base at temperatures up to the boiling point of the solvent used.

6. The method according to claim 5, characterized in that a compound of the formula (I ') in which R3 represents a cyano group is converted into the corresponding carbamoyl compound by partial hydrolysis.

40

45 The invention relates to a process for the preparation of new benzylamines of the formula (I)

50

55

(I),

Rr

60 in which

Ri is an aliphatic or aromatic acyl radical;

R2 is a hydrogen, chlorine or bromine atom;

R3 is a methyl or alkoxy group in the 3-, 4- or 5-position of the phenyl nucleus, a straight-chain or branched Al-65 kyl group with 2 to 4 carbon atoms, a fluorine atom, a trifluoromethyl, cyano, carbamoyl, carboxyl , Carbalkoxy, acetyl or 1-hydroxyethyl group or the aminomethyl group of the formula

3rd

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/ R6

■ ° v \

R,

wherein R6 and R7, which are the same or different, each represent an alkyl, cycloalkyl or hydroxycycloalkyl group or both together with the nitrogen atom to which they are attached represent a pyrrolidine, piperidine or morpholine ring; and

R4 and R5, which are the same or different, each have a straight-chain or branched alkyl radical having 1 to 5 carbon atoms, which can be substituted by 1 or 2 hydroxyl groups, an alkenyl radical having 2 to 4 carbon atoms, a cycloalkyl radical optionally substituted by one or two hydroxyl groups 5 to 7 carbon atoms, a benzyl or morpholinocarbonylmethyl group or both together with the nitrogen atom to which they are attached, a pyrrolidine, piperidine, hexamethyleneamine, morpholine, N-methylpiperazine or camphidine ring, and R4 also denotes a hydrogen atom, and of their hydrolysis products, in which Rt is hydrogen, and their physiologically tolerable acid addition salts with inorganic or organic acids.

The compounds of the formula (I) or (I ') have valuable pharmacological properties, in particular an anti-ulcer effect, a secretolytic, antitussive and an increasing effect on the production of the surfactant or antiatelectase factor of the alveoli.

Similar benzylamines are described in AU-PS 401 015 (C.A. 121.101d [1970]) and in Helv. Chim. Acta 48 (1965) 259-274; these compounds differ fundamentally in their action from those obtainable according to the invention. Those mentioned in the AU-PS are used as supplementary feed for the prevention of coccidosis, while those described in the last-mentioned publication can be used as X-ray contrast agents.

The new compounds are prepared according to the invention by using a compound of the formula (II)

HÛCL,

(II),

wherein

R9 represents a hydrogen atom or an aliphatic or aromatic group corresponding to Rx, with a nitrogen compound of the formula (III)

H-N

/ R4

\

(III)

Rr converts a reaction product of the formula (I) in which R i is aliphatic or aromatic acyl, optionally subsequently to the preparation of the corresponding compounds of the formula (I ') in which R i is hydrogen, and the process products are then optionally hydrolysed into their physiologically tolerable salts transferred.

The reaction is expediently carried out in a suitable solvent, such as tetralin, or an excess of the compound of the formula (III) at temperatures from 100 to 200 ° C., but preferably at temperatures between 120 and 180 ° C. However, the reaction can also be carried out without a solvent.

The hydrolysis of the reaction product to be carried out is preferably carried out in the presence of an acid, such as hydrochloric acid or sulfuric acid, or in the presence of a base, such as sodium hydroxide solution, in a polar solvent, such as water, ethanol / water or dioxane / water, and at temperatures up to the boiling point performed the solvent used.

For the groups mentioned above in the definition of the radical R9, the meaning of the methyl, 15 ethyl or phenyl radical is particularly suitable.

If a compound of the formula (I) or (I ') is obtained,

in which R3 represents a cyano group, this can be achieved by means of partial hydrolysis, e.g. B. by means of aqueous alcoholic sodium hydroxide solution, into the corresponding carbamoyl compound of For-20 mei (I) or (I '). A compound of formula (I ') obtained, provided that the radicals R2, R3, R4 and Rs do not contain a reactive hydrogen atom, can, if desired, be subsequently acylated with an aliphatic or aromatic acylating agent. This reaction 25 is conveniently carried out with a reactive acid derivative, such as an acid halide, acid anhydride or mixed acid anhydride, or in the presence of a dehydrating agent, such as N, N'-dicyclohexyl-carbodiimide.

The compounds of formula (I) or (I ') obtained can, if desired, be converted with inorganic or organic acids into their physiologically compatible acid addition salts with one, two or three equivalents of the acid in question. As acids, 35 hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, lactic acid, citric acid, tartaric acid, maleic acid or fumaric acid have proven to be suitable.

A compound of formula (II) used as a starting material is obtained, for example, by halogenation of a corresponding benzoxazine derivative or by elimination of water from a 2-acylamino-benzyl alcohol.

As already mentioned at the beginning, the new compounds of the formula (I) or (I ') have valuable pharmacological properties, in particular an anti-ulcer effect, a 45 secretolytic, antitussive and an increasing effect on the production of the surfactant or anti-electectase. Factor of the alveoli.

For example, the following substances were examined for their biological effects:

50

A = 2-amino-3-bromo-5-carbäthoxy-N, N-diethyl-benzylamine hydrochloride,

B = N-ethyl-2-amino-3-bromo-5-carboxy-N-cyclohexyl-benzylamine hydrochloride, 55 C = N-ethyl-2-amino-5-bromo-N-cyclohexyl-3-fluoro-benzyl amine hydrochloride, D = N- (2-amino-5-bromo-3-methyl-benzyl) -hexamethylene-

amine dihydrochloride, E = N- (2-amino-5-bromo-4-tert-butyl-benzyl) -morpholine-60 dihydrochloride,

F = 5-acetyi-2-amino-3-bromo-N, N-dimethyl-benzylamine and G = 2-amino-3-bromo-N, N-dimethyl-5-fluorine-benzylamine hydrochloride.

65 1. Secretolytic effect:

The expectoration experiments were carried out on anesthetized guinea pigs or on anesthetized rabbits (see Perry and Boyd, Pharmacol. Exp. Therap. 73, 65 [1941])

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carried out. The substances were in each case 6 to 8 animals in a dose of 8 mg / kg p.o. applied. The increase in secretion (2-hour values) was calculated by comparing the amount of secretion on and before substance administration.

The circulatory tests were carried out on 3 cats each with chloralose-urethane anesthesia after intravenous administration of 2, 4 and 8 mg / kg of the substance to be examined:

Experiments on guinea pigs:

Substance secretion-circulatory effect increase

A + 90% 274 and 8 mg / kg: none

change

B + 81% 2, 4 and 8 mg / kg: none

change

C + 100%

G + 84%

Tests on rabbits:

Substance secretion increase

D + 72%

E + 77%

F + 75%

2. Anti-ulcer effect:

The effect of the substance to be examined on ulcers was determined by the method of K. Takagi et al. (Jap. J. Pharmac. 19, 418 [1969]). For this purpose, female rats with a body weight between 220 to 250 g were opened under ether anesthesia and the stomach was removed. Thereafter, 0.05 ml of a 5% acetic acid solution was injected at one point between the muscularis mucosae and the submucosa of the stomach. The abdominal cavity was closed again after the injection. The ulcers that formed in the mucous membrane after 3 to 5 days at the application site were treated for 3 weeks by adding the substance to be examined in doses of 50 and 100 mg / kg to the feed (6 animals / dose). The control animals received only the powdered feed.

After 3 weeks of treatment, the animals were sacrificed, the stomach removed and the ulcers determined by measuring the ulcer length and ulcer width. The substance effect compared to controls (100%) was determined:

With a dosage of substance A of 50 mg / kg p.p. there was a 52% reduction in ulcers and a dose of 100 mg / kg p. o. A 79% reduction in ulcers compared to controls was found.

3. Acute toxicity:

The acute toxicity of the substances to be examined was determined in groups of 5 white mice after a single dose of 1000 or 2000 mg / kg p. os orientated:

Substance acute toxicity

A> 2000 mg / kg p.o. (0 out of 5 animals died):

B> 1000 mg / kg p.o. (0 out of 5 animals died)

C> 1000 mg / kg p.o. (0 of 5 animals died)

D> 1000 mg / kg p.o. (0 of 5 animals died)

E> 1000 mg / kg p.o. (0 out of 5 animals died)

F ~ 1000 mg / kg p.o. (2 out of 5 animals died)

G> 1000 mg / kg p.o. (0 out of 5 animals died)

The new compounds of the formula (I) or (I ') can be incorporated for pharmaceutical use into the customary pharmaceutical preparation forms, such as tablets, dragées, capsules, suppositories, ampoules and solutions, if appropriate in combination with other active substances. The single dose is 1 to 100 mg, preferably 4 to 60 mg, and the daily dose is 2 to 300 mg, preferably 4 to 200 mg. For compounds with secretolytic activity, the single dose is 1 to 20 mg, but preferably 4 to 15 mg, and with an antiulcus effect 25 to 100 mg, but preferably 30 to 60 mg.

The following examples are intended to explain the invention in more detail:

example 1

2-benzoylamino-3-bromo-5-carbethoxy-N, N-diethyl-benzylamine

3.6 g of 8-bromo-6-carbäthoxy-2-phenyl-4H-3, l-benzoxazine hydrobromide are heated with 4.4 g of diethylamine in an autoclave at 150 to 160 ° C for 2 hours, then concentrated to dryness in vacuo . The residue is partitioned between chloroform and dilute ammonia, the chloroform phase is concentrated, the residue is dissolved in ethanol and the hydrochloride with a melting point of 220 to 222 ° C. is precipitated with ethereal hydrochloric acid.

Example 2

2-amino-3-bromo-5-carbamoyl-N, N-diethyl-benzylamine

11 g of 2-amino-3-bromo-5-cyan-N, N-diethyl-benzylamine are refluxed with 70 ml of ethanol and 100 ml of 5N sodium hydroxide solution. After cooling, it is diluted with 100 ml of water and extracted with chloroform. The chloroform extract is dried over sodium sulfate, concentrated and the residue is recrystallized from isopropanol. 2-Amino-3-bromo-5-carbamoyl-N, N-diethyl-benzylamine of melting point 140 to 142 ° C. is obtained.

Example 3

2-acetamino-3-bromo-5-carbethoxy-N, N-diethyl-benzylamine

1 g of 2-amino-3-bromo-5-carbäthoxy-N, N-diethyl-benzyl-amine is dissolved in 2 ml of acetyl chloride and heated to 50 ° C for 1 hour. The acetyl chloride is evaporated off in vacuo, the residue is partitioned between cold dilute ammonia and chloroform, the chloroform solution is evaporated, the product is purified by chromatography on silica gel (eluent: ethyl acetate), the evaporation residue from the eluate is dissolved in isopropanol and brought about by the addition of isopropanol Hydrochloric acid and ether the 2-acetamino-3-bromo-5-carbäthoxy-N, N-diethyl-benzylamine hydrochloride for crystallization. Melting point: 190 to 194 ° C.

Example 4

2-acetamino-3-bromo-N, N-diethyl-5-methyl-benzylamine

1.53 g of 2-amino-3-bromo-N, N-diethyl-5-methyl-benzyl-amine hydrochloride are dissolved in 50 ml of acetic anhydride at 75 ° C. It is evaporated to the dry state in a vacuum and the residue is recrystallized from ethanol. The 2-acetamino-3-bromo-N, N-diethyl-5-methyl-benzylamine hydrochloride obtained melts at 170 to 172 ° C.

Example 5

2-acetamino-3-bromo-N, 5-dimethyl-N- (trans-4-hydroxy-cyclohexyl) benzylamine

2.2 g of 2-amino-3-bromo-N, 5-dimethyl-N- (trans-4-hydroxy-cyclohexyl) benzylamine are dissolved in 100 ml of methanol and heated to boiling. 75 ml of acetic anhydride are added in the course of 2 hours and the methyl acetate formed is distilled off in the process. It is evaporated to the dry state in a vacuum and, after the addition of further methanol, the evaporation is repeated. The residue obtained is dissolved in ethanol

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and converted into the 2-acetamino-3-bromo-N, 5-dimethyl-N- (trans-4-hydroxycyclohexyl) benzylamine hydrochloride with ethanolic hydrochloric acid.

Melting point: 246 to 248 ° C.

Example 6

3-bromo-2-butyrylamino-5-carbethoxy-N, N-diethyl-benzylamine

3 g of 2-amino-3-bromo-5-carbäthoxy-N, N-diethyl-benzyl-amine are dissolved in 30 ml of benzene and heated to 50 ° C. with 3 ml of butyric acid chloride for 30 minutes. It is evaporated to the dry state in a vacuum and the residue is purified by chromatography on silica gel (mobile phase: benzene: ethyl acetate = 6: 1); This gives 3-bromo-2-butyrylamino-5-carbäthoxy-N, N-di-ethyl-benzylamine, which is converted into the hydrochloride with a melting point of 134 ° C. using ethanolic hydrochloric acid.

Example 7

2-acetamino-3-bromo-5-carbethoxy-N-cyclohexyl-N-methyl-benzylamine

Melting point of the hydrochloride: 220 to 223 ° C. Prepared from 2-amino-3-bromo-5-carbäthoxy-N-cyclo-hexyl-N-methyl-benzylamine and acetyl chloride analogously to Example 6.

The following compounds were prepared analogously to Examples 1 to 7:

4-bromo-2,6-bis (pyrrolidino-methyl) acetanilide dihydrochloride

Melting point: 319 ° C (dec.) 4-bromo-2,6-bis (morpholino-methyl) aniline dihydrochloride Melting point: 251 to 257 ° C (dec.)

4-bromo-2,6-bis (piperidino-methyl) acetanilide dihydrochloride

Melting point: 308 to 312 ° C (dec.) N- (2-amino-5-methoxy-benzyl) -piperidine

Oil, structural evidence by IR, UV and NMR spectra

5-Acetyl-2-acetylamino-N, N-diethyl-benzylamine Melting point: 102 to 103 ° C

5-acetyl-2-amino-3-bromo-N-cyclohexyl-N-methyl-benzyl-amine hydrochloride Melting point: 229 to 231 ° C 2-amino-3-bromo-N, N-dimethyl-5- (l -hydroxy-ethyl) -benzylamine

Melting point: 69 to 72 ° C 2-amino-5-bromo-3-dimethylaminomethyl-N, N-dimethyl-benzylamine-dihydrochloride Melting point: 284 to 287 ° C (dec.) 2-Acetylamino-5-bromo-N, N -Diethyl-3-methyl-benzylamine hydrochloride

Melting point: 192.5 to 194 ° C 2-amino-5-bromo-N-cyclohexyl-N, 3-dimethyl-benzylamine hydrochloride

Melting point: 206.5 to 207.5 ° C (dec.) N- (2-acetylamino-5-bromo-3-methyl-benzyl) morpholine

Melting point: 105 to 110 ° C 2-amino-5-bromo-N, 3-dimethyl-N- (trans-4-hydroxy-cyclo-hexyl) -benzylamine Melting point: 122 to 123.5 ° C 2-acetylamino-5 -bromo-N, 3-dimethyl-N- (trans-4-hydroxy-cyclohexyl) -benzylamine Melting point: 136.5 to 138 ° C 2-acetylamino-N, N, 3-trimethyl-benzylamine hydrochloride

Melting point: 162 to 164 ° C N - '(2-amino-5-bromo-3-methyl-benzyl) piperidine dihydrochloride

Melting point: 176 to 179 ° C (dec.) 4-amino-5-bromo-3-tert-butyl-N, N-diethyl-benzylamine-dihydrochloride

Melting point: 201 to 204 ° C (decomp.)

2-acetylamino-5-bromo-3-tert-butyl-N-cyclohexyl-N-methyl-benzylamine hydrochloride Melting point: 231 to 234 ° C 2-amino-3-bromo-5-tert-butyl-N- cyclohexyl-N-methyl-benzylamine hydrochloride Melting point: 214 to 215 ° C (dec.) N- (2-amino-5-bromo-4-tert-butyl-benzyl) pyrrolidine hydrochloride

Melting point: from 190 ° C (decomp.) N- (2-acetylamino-5-bromo-4-tert-butyl-benzyl) -piperidine

Melting point: 132 to 134 ° C 2-acetylamino-5-bromo-N-cyclohexyl-N-methyl-3- (N-methyl-cyclohexylaminomethyl) benzylamine Melting point: 194 to 199 ° C 2-acetylamino-5-bromo-4 -tert.-butyl-N, N-diethyl-benzylamine

Melting point: 88 to 91 ° C 2-amino-5-bromo-4-tert-butyl-N-cyclohexyl-N-methyl-benzylamine hydrochloride Melting point: 202 to 202.5 ° C (dec.) N- (2nd -Amino-5-bromo-4-tert-butyl-benzyl) -morpholine-dihydrochloride

Melting point: 194 to 198 ° C (dec.) N- (2-acetylamino-5-bromo-4-tert-butyl-benzyl) -N'-methyl-piperazine dihydrochloride Melting point: from 250 ° C (dec.) 2-amino-5-bromo-N- (trans-4-hydroxy-cyclohexyl) -N-methyl-3- [N-methyl- (trans-4-hydroxy-cyclohexylamino) methyll-benzylamine

Melting point: 179 to 180 ° C 2-amino-3-bromo-N, N-dimethyl-5-methoxy-benzylamine Structural evidence by IR, UV and NMR spectra 2-amino-N, N-dimethyl-5-methoxy -benzylamine

Structural evidence by IR, UV and NMR spectra N- (5-acetyl-2-amino-benzyl) -hexamethyleneamine hydrochloride

Melting point: 205 to 207 ° C (dec.) 5-acetyl-2-amino-3-bromo-N, N-dimethyl-benzylamine

Melting point: 92 to 95 ° C 5-acetyl-2-amino-N, N-dimethyl-benzylamine hydrochloride

Melting point: 209 to 215 ° C (dec.) N-ethyl-2-amino-3-bromo-N-cyclohexyl-5- (l-hydroxyethyl) benzylamine Melting point: 117 to 121 ° C N-ethyl-2 -amino-3-bromo-N-cyclohexyl-5-fluoro-benzylamine hydrochloride

Melting point: 176 to 178 ° C N-ethyl-2-amino-5-bromo-N-cyclohexyl-3-fluoro-benzylamine hydrochloride

Melting point: 193 to 195 ° C 2-amino-5-bromo-N-cyclohexyl-3-fluoro-N-methyl-benzylamine hydrochloride

Melting point: 226 to 228 ° C (dec.) 2-Amino-5-bromo-3-fluoro-N- (trans-4-hydroxy-cyclohexyl) benzylamine hydrochloride Melting point: 231 to 233 ° C (dec.) N - (2-Amino-3-bromo-5-fluorobenzyl) morpholine hydrochloride

Melting point: 230 to 232 ° C 2-amino-3-bromo-N, N-dimethyl-5-fluorobenzylamine hydrochloride

Melting point: 241 to 243 ° C

2-amino-5-bromo-N, N-dimethyl-3-fluoro-benzylamine hydrochloride

Melting point: 263 to 265 ° C (decomp.)

2-amino-5-bromo-N, N-diethyl-3-methyl-benzylamine hydrochloride

Melting point: 177 to 179 ° C (dec.)

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N-ethyl-2-amino-5-bromo-N-cyclohexyl-3-methyl-benzyl-amine dihydrochloride Melting point: 183 to 187 ° C (dec.) 2-acetylamino-5-bromo-N-cyclohexyl-N, 3-dimethyl-benzyl-amine

Melting point: 102 to 104 ° C N- (2-acetylamino-5-bromo-3-methyl-benzyl) pyrrolidine

Melting point: 123 to 127 ° C N- (2-amino-5-bromo-3-methyl) -hexamethyleneamine dihydrochloride

Melting point: 159 to 164 ° C (dec.) N- (2-acetylamino-5-bromo-3-methyl-benzyl) piperidine

Melting point: 119 to 124 ° C 2-amino-3-bromo-5-carbäthoxy-N, N-diethyl-benzylamine hydrochloride

Melting point: 165 to 168 ° C N-ethyl-2-amino-3-bromo-5-carboxy-N-cyclohexyl-benzyl-amine hydrochloride

Melting point: 227 to 229 ° C (dec.) 2-amino-5-carboxy-N-cyclohexyl-N-methyl-benzylamine

Melting point: 200 to 205 ° C N- (2-amino-5-carboxy-benzyl) hexamethylene amine dihydrochloride

Melting point: from 121 ° C (decomp.) 2-amino-5-carboxy-N, N-diethyl-benzylamine hydrochloride

Melting point: 194 to 198 ° C N- (2-amino-3-bromo-5-carbäthoxy-benzyl) pyrrolidine hydrochloride

Melting point: 204 to 205 ° C

2-amino-3-bromo-5-carbäthoxy-N- (trans-4-hydroxy-cyclo-hexyl) -benzylamine hydrochloride Melting point: 137 ° C (dec.) N- (2-amino-3-bromo-5 -carbäthoxy-benzyl) -hexamethylene-5 amine hydrochloride

Melting point: 219 to 221 ° C N-ethyl-2-amino-N-cyclohexyl-5-methyl-benzylamine hydrochloride

Melting point: 189 to 191 ° C (dec.) Io 2-amino-3-bromo-5-cyan-N-cyclohexyl-N-methyl-benzylamine hydrochloride

Melting point: 236 to 240 ° C

2-amino-3-bromo-5-carbäthoxy-N-cyclohexyl-N-methyl-benzylamine hydrochloride 15 Melting point: 212 to 215 ° C

2-amino-5-bromo-N, N-diethyl-3-trifluoromethyl-benzylamine hydrochloride

Melting point: 198 to 200 ° C

20 2-Amino-3-bromo-N, N-diethyl-5-fluoro-benzylamine hydrochloride

Melting point: 182 to 184 ° C

N-ethyl-2-amino-3-carboxy-N-cyclohexyl-benzylamine-25 hydrochloride

Melting point: 193 to 197 ° C

N-ethyl-2-amino-5-bromo-3-carboxy-N-cyclohexyl-benzyl-amine hydrochloride melting point: 130 to 140 ° C.