Pyrrolophenylalkanolamines as animal yield promoters

Pyrrolophenylalkanolamines of the formula ##STR1## R.sup.1 and R.sup.2 represent hydrogen or various radicals, R.sup.3 represents hydrogen, acyl or trialkylsilyl, PA1 R.sup.4 represents hydrogen or alkyl, PA1 R.sup.5 represents hydrogen, or, together with R.sup.3, represents ##STR2## wherein R.sup.7 represents hydrogen or alkyl, and PA1 R.sup.6 represents branched or cyfclic alkyl, which is optionally substituted, and salts thereof promote the yield of animals. Many new intermediates are also shown.

The present invention relates to new pyrrolophenylalkanolamines, their 
derivatives, processes for their preparation and their use as yield 
promoters for animals. 
It is known that substituted phenylethanolamines have properties which 
promote the growth of animals (European Published Specification 26,298 and 
European Published Specification 49,728). However, the yield-promoting 
properties of the known compounds are not always completely satisfactory. 
The present invention relates to 
1. the new pyrrolophenylalkanolamines of the formula I and their 
derivatives 
##STR3## 
in which R.sup.1 represents one or more identical or different radicals 
from the group comprising hydrogen, halogen, cyano, formyl, nitro, 
carboxyl, carbalkoxyalkyl, alkoxycarboxyalkyl, alkylcarbonyl, 
alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, 
alkyl, alkoxy, alkenoxy, halogenoalkyl, halogenoalkoxy, alkylthio, 
halogenoalkylthio, hydroxyalkyl, cyanoalkyl, alkoxyalkyl, alkylthioalkyl 
and alkylcarbonylalkoxy, 
R.sup.2 represents one or more identical or different radicals from the 
group comprising hydrogen, hydroxyl, halogen, cyano, nitro, alkyl, alkoxy, 
alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, cyanoalkyl, 
alkoxyalkyl, hydroxyalkyl, alkoxycarbonyl, aminocarbonyl and mono-and 
dialkylaminocarbonyl, 
R.sup.3 represents hydrogen, acyl or trialkylsilyl, 
R.sup.4 represents hydrogen or alkyl, 
R.sup.5 represents hydrogen, or, together with R.sup.3, represents the 
following radicals 
##STR4## 
wherein R.sup.7 represents hydrogen or alkyl, and 
R.sup.6 represents branched or cyclic alkyl, which are optionally 
substituted. 
2. Process for the preparation of the new pyrrolophenylalkanolamines of the 
formula I and their derivatives 
##STR5## 
in which R.sup.1 represents one or more identical or different radicals 
from the group comprising hydrogen, halogen, cyano, formyl, nitro, 
carboxyl, carbalkoxyalkyl, alkoxycarboxyalkyl, alkylcarbonyl, 
alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, 
alkyl, alkoxy, alkenoxy, halogenoalkyl, halogenoalkoxy, alkylthio, 
halogenoalkylthio, hydroxyalkyl, cyanoalkyl, alkoxyalkyl, alkylthioalkyl 
and alkylcarbonylalkoxy, 
R.sup.2 represents one or more identical or different radicals from the 
group comprising hydrogen, hydroxyl, halogen, cyano, nitro, alkyl, alkoxy, 
alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, cyanoalkyl, 
alkoxyalkyl, hydroxyalkyl, alkoxycarbonyl, aminocarbonyl and mono-and 
dialkylaminocarbonyl, 
R.sup.3 represents hydrogen, acyl or trialkylsilyl, 
R.sup.4 represents hydrogen or alkyl, 
R.sup.5 represents hydrogen, or, together with R.sup.3, represents the 
following radicals 
##STR6## 
wherein R.sup.7 represents hydrogen or alkyl, and 
R.sup.6 represents branched or cyclic alkyl, which are optionally 
substituted, 
characterized in that compounds of the formula II 
##STR7## 
in which R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have the 
abovementioned meaning, 
(a) are reacted with 1,4-dicarbonyl compounds of the formula III 
##STR8## 
or monoacetals, diacetals or cyclic acetals thereof of the formula IIa, 
IIIb or IIIc 
##STR9## 
in which R.sup.1 has the abovementioned meaning and 
R.sup.8 represents hydrogen, alkyl or aryl, or 
(b) are reacted with dihalogenoallenes of the formula IV 
EQU Hal--CH.dbd.C.dbd.CH--CH.sub.2 --Hal IV 
in which Hal represents halogen, or 
(c) are reacted with epoxybutanes of the formula V 
##STR10## 
in which R.sup.1 has the abovementioned meaning, 
R.sup.10 represents hydrogen or bromine, 
R.sup.11 represents hydrogen and 
R.sup.12 represents bromine, or 
R.sup.11 and R.sup.12 represent alkoxy or aryloxy, or 
(d) are reacted with halogenocrotonaldehyde of the formula VI 
##STR11## 
in which Hal represents halogen, or 
(e) in which compounds of the formula VII 
##STR12## 
in which R.sup.1, R.sup.2, R.sup.4, R.sup.5 and R.sup.6 have the 
abovementioned meaning, are reduced, or 
(f) in which compounds of the formula VIII 
##STR13## 
in which R.sup.1, R.sup.2 and R.sup.4 have the abovementioned meaning, are 
reacted with amines of the formula IX 
EQU HNR.sup.5 R.sup.6 IX 
in which R.sup.5 and R.sup.6 have the abovementioned meaning, or 
(g) in which compounds of the formula X 
##STR14## 
in which R.sup.1 and R.sup.2 have the abovementioned meaning and Hal 
represents halogen, are reduced with amines of the formula IX and the 
carbonyl group is then reduced, or 
(h) in which compounds of the formula XI 
##STR15## 
in which R.sup.1, R.sup.2 and R.sup.4 have the abovementioned meaning and 
Hal represents halogen, are reacted with amines of the formula IX, or 
(i) in which, in the case where the radical R.sup.5 in formula I represents 
hydrogen, compounds of the formula XII 
##STR16## 
in which R.sup.1 to R.sup.4 have the abovementioned meaning, are reacted 
with ketones of the formula XIII 
##STR17## 
in which R.sup.13 represents optionally substituted alkyl or cycloalkyl 
and 
R.sup.14 represents optionally substituted alkyl, cycloalkyl or 
heterocyclyl, or 
R.sup.13 and R.sup.14, together with the adjacent C atom, represent an 
optionally substituted aliphatic ring, 
under reducing conditions, or 
(j) in which compounds of the formula XIV 
##STR18## 
in which R.sup.1 and R.sup.2 have the abovementioned meanings, are reacted 
with amines of the formula IX under reducing conditions, or 
(k) in which, in the case where R.sup.3 and R.sup.4 in formula I represent 
hydrogen, compounds of the formula XV 
##STR19## 
in which R.sup.1, R.sup.2, R.sup.5 and R.sup.6 have the abovementioned 
meanings are reduced, or 
(l) in which, in the case where R.sup.3 represents acyl, compounds of the 
formula I in which R.sup.3 represents hydrogen are reacted with acylating 
agents in the presence of bases, or 
(m) in which, in the case where R.sup.3 represents trialkylsilyl, compounds 
of the formula I in which R.sup.3 represents hydrogen are reacted with 
silylating agents of the formula XVI 
EQU Z-Si(R.sup.15).sub.3 XVI 
in which 
Z represents halogen, CN, OSO.sub.2 -CF.sub.3, O-Si(alkyl).sub.3 or 
O-SO.sub.2 -OSi(alkyl).sub.3 and 
R.sup.15 represents identical or different alkyl radicals, or 
(n) in which, in the case where R.sup.3 and R.sup.5 together represent the 
radical 
##STR20## 
compounds of the formula I in which R.sup.3 and R.sup.5 represent hydrogen 
are reacted with phosgene or agents which split off phosgene, or 
(o) in which, in the case where R.sup.3 and R.sup.5 together represent the 
radical 
##STR21## 
compounds of the formula I in which R.sup.3 and R.sup.5 represent hydrogen 
are reacted with aldehydes of the formula XVII 
##STR22## 
in which R.sup.7 has the abovementioned meaning, in the presence of 
dehydrating agents or under dehydrating reaction conditions, or 
(p) in which compounds of the formula XII in which R.sup.1 -R.sup.4 have 
the abovementioned meaning are reacted with halogen compounds of the 
formula XXXVIII 
##STR23## 
in which R.sup.13 and R.sup.14 have the meanings given in the case of the 
compounds of the formula XIII in process 2i and 
Hal represents chlorine or bromine. 
3. New compounds of the formula VII 
##STR24## 
in which R.sup.1, R.sup.2 and R.sup.4 to R.sup.6 have the meanings given 
in the case of the compounds of the formula I. 
4. Process for the preparation of the compounds of the formula VII, 
characterized in that, as described for process 2(g) in the first stage, 
halogenoacetophenones of the formula X 
##STR25## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I and Hal represents halogen, are reacted with 
amines of the formula IX, or in which compounds of the formula XX 
##STR26## 
in which R.sup.2 and R.sup.4 to R.sup.6 have the meaning given in the case 
of the compounds of the formula I and R.sup.5 and R.sup.6 do not both 
represent hydrogen, are reacted analogously to the reactions described for 
processes 2(a-d). 
5. New compounds of the formula VIII 
##STR27## 
in which R.sup.1, R.sup.2 and R.sup.4 have the meanings given in the case 
of the compounds of the formula I. 
6. Process for the preparation of the compounds of the formula VIII, 
characterized in that compounds of the formula XI 
##STR28## 
in which R.sup.1, R.sup.2 and R.sup.4 have the meanings given in the case 
of the compounds of the formula I and Hal represents halogen, are reacted 
with bases, or in that compounds of the formula XVIII 
##STR29## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I, are reacted in the presence of bases with 
reagents which transfer methylene groups, or in which compounds of the 
formula XXI 
##STR30## 
in which R.sup.2 and R.sup.4 have the meanings given in the case of the 
compounds of the formula I and Hal represents halogen, are reacted 
analogously to the reactions described for processes 2(a-d). 
7. New compounds of the formula X 
##STR31## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I and Hal represents halogen. 
8. Process for the preparation of the compounds of the formula X, 
characterized in that acetophenones of the formula XIX 
##STR32## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I, are reacted with halogen or copper halides 
Cu(halogen).sub.2 or N-halogenosuccinimides, or in which compounds of the 
formula XXII 
##STR33## 
in which R.sup.2 has the meanings given in the case of the compounds of 
the formula I and Hal represents halogen, are reacted analogously to the 
reactions described for processes 2(a-d). 
9. New compounds of the formula XI 
##STR34## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I, Hal represents halogen and 
R.sup.4 represents hydrogen. 
10. Process for the preparation of the compounds of the formula XI, 
characterized in that compounds of the formula X 
##STR35## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I and Hal represents halogen, are reduced, or in 
which compounds of the formula XXIII 
##STR36## 
in which R.sup.2 and R.sup.4 have the meaning given in the case of the 
compounds of the formula I and Hal represents halogen, are reacted 
analogously to the reactions described for processes 2(a-d). 
11. New compounds of the formula XII 
##STR37## 
in which R.sup.1 to R.sup.4 have the meanings given in the case of the 
compounds of the formula I. 
12. Process for the preparation of the compounds of the formula XII, 
characterized in that nitro compounds of the formula XXIV 
##STR38## 
in which R.sup.1 to R.sup.4 have the meanings given in the case of the 
compounds of the formula I, are reduced, or in that compounds of the 
formula XXV 
##STR39## 
in which R.sup.2 to R.sup.4 have the meanings given in the case of the 
compounds of the formula I, are reacted analogously to the reactions 
described for processes 2(a-d) and the products are then reduced. 
13. New compounds of the formula XIV 
##STR40## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I. 
14. Process for the preparation of the compounds of the formula XIV, 
characterized in that compounds of the formula X 
##STR41## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I and Hal represents halogen, are oxidized, or in 
that compounds of the formula XXII 
##STR42## 
in which R.sup.2 has the meaning given in the case of the compounds of the 
formula I, are reacted analogously to the reactions described for 
processes 2(a-d). 
15. New compounds of the formula XV 
##STR43## 
in which R.sup.1, R.sup.2, R.sup.5 and R.sup.6 have the meanings given in 
the case of the compounds of the formula I. 
16. Process for the preparation of the compounds of the formula XV in which 
R.sup.5 represents hydrogen, characterized in that compounds of the 
formula XVIII 
##STR44## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I, are reacted with isonitriles of the formula 
XXVI 
EQU CN-R.sup.6 XXVI 
in which R.sup.6 has the meaning given in the case of the compounds of the 
formula I, in the presence of acetic acid and the O-acetyl compounds 
formed are hydrolyzed, or in which compounds of the formula XXX 
##STR45## 
in which R.sup.2, R.sup.5 and R.sup.6 have the meanings given in the case 
of the compounds of the formula I and R.sup.5 and R.sup.6 may not both 
simultaneously represent hydrogen, are reacted analogously to the 
reactions described for process 2(a-d). 
17. New compounds of the formula XVIII 
##STR46## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I. 
18. Process for the preparation of the compounds of the formula XVIII, 
characterized in that compounds of the formula XXVII 
##STR47## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I, are oxidized, or in which acid chlorides of 
the formula XXVIII 
##STR48## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I, are reduced, or in which compounds of the 
formula XXXI 
##STR49## 
in which R.sup.2 has the meaning given in the case of the compounds of the 
formula I, are reacted analogously to the reactions described for 
processes 2(a-d). 
19. New compounds of the formula XIX 
##STR50## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I. 
20. Process for the preparation of the compounds of the formula XIX, 
characterized in that compounds of the formula XXIX 
##STR51## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I and Alk represents C.sub.1-4 -alkyl, are 
hydrolyzed and decarboxylated, or in which compounds of the formula XXXII 
##STR52## 
in which R.sup.2 has the meaning given in the case of the compounds of the 
formula I, are reacted analogously to the reactions described for 
processes 2(a-d). 
21. New compounds of the formula XXIV 
##STR53## 
in which R.sup.1 and R.sup.4 have the meanings given in the case of the 
compounds of the formula I. 
22. Process for the preparation of the compounds of the formula XXIV, 
characterized in that aldehydes of the formula XVIII 
##STR54## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I, are reacted with nitromethane. 
23. New compounds of the formula XVII 
##STR55## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I. 
24. Process for the preparation of the compounds of the formula XVII, 
characterized in that compounds of the formula XXXIII 
##STR56## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I and 
R.sup.9 represents hydrogen or C.sub.1-4 -alkyl, 
are reduced, or in which compounds of the formula XXXIV 
##STR57## 
in which R.sup.2 has the meaning given in the case of the compounds of the 
formula I, are reacted analogously to the reactions described for 
processes 2(a-d). 
25. New compounds of the formula XXVIII 
##STR58## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I. 
26. Process for the preparation of the compounds of the formula XXVIII, 
characterized in that compounds of the formula XXXIII 
##STR59## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I and 
R.sup.9 represents hydrogen, 
are reacted with halogenating agents, or in which compounds of the formula 
XXXV 
##STR60## 
in which R.sup.2 has the meaning given in the case of the compounds of the 
formula I, are reacted analogously to the reactions described for 
processes 2(a-d). 
27. New compounds of the formula XXIX 
##STR61## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I and Alk represents C.sub.1-4 -alkyl. 
28. Process for the preparation of the compounds of the formula XXIX, 
characterized in that compounds of the formula XXXIII 
##STR62## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I and 
R.sup.9 represents C.sub.1-4 -alkyl, 
are reacted with acetic acid esters of the formula XXXVI 
EQU CH.sub.3 -COOAlk XXXVI 
in which Alk represents C.sub.1-4 -alkyl, or in which compounds of the 
formula XXXVII 
##STR63## 
in which R.sup.2 represents the radicals given in the case of the 
compounds of the formula I, are reacted analogously to the reactions 
described for processes 2(a-d). 
29. New compounds of the formula XXXIII 
##STR64## 
in which R.sup.1 and R.sup.2 have the meanings given in the case of the 
compounds of the formula I and 
R.sup.9 represents hydrogen or C.sub.1-4 -alkyl. 
30. Process for the preparation of the compounds of the formula XXXIII, 
characterized in that compounds of the formula XXXVII 
##STR65## 
in which R.sup.2 has the meaning given in the case of the compounds of the 
formula I and 
R.sup.9 represents C.sub.1-4 -alkyl or hydrogen, 
are reacted analogously to the reactions described for processes 2(a-d). 
It has furthermore been found that the compounds of the formula I and their 
physiologically tolerated salts have a yield-promoting action on animals, 
in particular an action to shift the meat/fat ratio in favor of meat. The 
invention relates to the use of the compounds of the formula I in animal 
breeding and animal nutrition. 
The compounds of the formula I can also exist in the form of their 
diastereomers, racemates or enantiomeric forms. 
Physiologically tolerated salts of the compounds of the formula I can be 
formed with the following acids: hydrochloric acid, sulphuric acid, 
phosphoric acid, perchloric acid, hydrobromic and hydriodic acid, nitric 
acid, acetic acid, oxalic acid, malonic acid, succinic acid, ascorbic 
acid, malic acid, tartaric acid, maleic acid, fumaric acid, 
methanesulphonic acid, benzoic acid, substituted benzoic acids, formic 
acid, toluenesulphonic acid, benzenesulphonic acid, phthalic acid, 
naphthalenesulphonic acid, nicotinic acid, palmitic acid and embonic acid. 
Preferred compounds of the formula I are those in which 
R.sup.1 represents one or more identical or different radicals from the 
group comprising hydrogen, halogen, cyano, nitro, formyl(CHO), 
carboxyl(COOH), carbalkoxyalkyl, alkoxycarboxyalkyl, C.sub.1-4 
-alkylcarbonyl(Alk-CO-), C.sub.1-4 -alkoxycarbonyl(Alk-O-CO-), 
aminocarbonyl(H.sub.2 N-CO-), C.sub.1-4 -alkylaminocarbonyl, di-C.sub.1-4 
-alkylaminocarbonyl, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.2-6 
-alkenoxy, C.sub.1-4 -halogenoalkyl, C.sub.1-4 -halogenoalkoxy, C.sub.1-4 
-alkylthio, C.sub.1-4 -halogenoalkylthio, C.sub.1-4 -hydroxyalkyl, 
C.sub.1-4 -cyanoalkyl, C.sub.2-8 -alkoxyalkyl, C.sub.2-8 -alkylthioalkyl 
and C.sub.1-4 -alkylcarbonyl-C.sub.1-4 -alkoxy, 
R.sup.2 represents one or more identical or different radicals from the 
group comprising hydrogen, halogen, hydroxyl, cyano, nitro, C.sub.1-4 
-alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylthio, C.sub.1-4 -halogenoalkyl, 
C.sub.1-4 -halogenoalkoxy, C.sub.1-4 -halogenoalkylthio, C.sub.1-4 
-cyanoalkyl, C.sub.2-8 -alkoxyalkyl, C.sub.1-4 -hydroxyalkyl, C.sub.1-4 
-alkoxycarbonyl, aminocarbonyl and mono- and di-C.sub.1-4 
-alkylaminocarbonyl, 
R.sup.3 represents hydrogen C.sub.1-6 -alkylcarbonyl, optionally 
substituted benzoyl, C.sub.1-6 -alkylsulphonyl, optionally substituted 
phenylsulphonyl or tri-C.sub.1-6 -alkyl-silyl, 
R.sup.4 represents hydrogen or methyl, 
R.sup.5 represents hydrogen and 
R.sup.6 represents straight-chain, branched or cyclic alkyl which has up to 
12 C atoms and is optionally substituted by heterocyclyl with 4 to 6 ring 
atoms and 1 or 2 hetero atoms, C.sub.1-6 -alkoxy, C.sub.1-4 -alkylthio or 
halogen, or represents cycloalkyl-alkyl which has up to 12 C atoms and is 
optionally substituted by halogen, C.sub.1-4 -alkoxy or C.sub.1-4 
-alkylthio. 
Particularly preferred compounds of the formula I are those in which 
R.sup.1 represents one or more identical or different radicals from the 
group comprising hydrogen, C.sub.1-4 -alkyl, formyl, C.sub.1-4 
-alkoxycarbonyl and C.sub.1-4 -alkylcarbonyl, 
R.sup.2 represents one or more identical or different radicals from the 
group comprising hydrogen, hydroxyl, cyano, halogen, in particular 
chlorine, fluorine or bromine, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, 
C.sub.1-4 -alkylthio, C.sub.1-4 -halogenoalkyl in particular 
trihalogenomethyl and C.sub.1-4 -halogenoalkoxy, 
R.sup.3 represents hydrogen, C.sub.1-6 -alkylcarbonyl, in particular 
acetyl, or dimethyl(C.sub.4-8 -alkyl)silyl, 
R.sup.4 represents hydrogen or methyl, 
R.sup.5 represents hydrogen and 
R.sup.6 represents t-butyl, i-propyl, C.sub.3-7 -cycloalkyl or 
dicyclopropylmethyl, which can optionally be substituted by one or more 
substituents from the group comprising halogen, C.sub.1-4 -alkoxy and 
C.sub.1-4 -alkylthio, or R.sup.6 furthermore represents the radical 
##STR66## 
wherein A represents C.sub.3-6 -cycloalkyl or C.sub.4-6 -heterocyclyl with 
O or S as the hetero atom, which can optionally be substituted by 
C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.1-4 -alkylthio. 
Radicals R.sup.6 which may be mentioned in particular are t-butyl, 
i-propyl, C.sub.1-4 -alkoxy-C.sub.2-4 -alkyl, C.sub.1-4 
-alkylthio-C.sub.2-4 -alkyl, C.sub.3-6 -cycloalkyl-C.sub.2-4 -alkyl, 
C.sub.2-4 -halogenoalkyl, tetrahydropyranyl-C.sub.2-4 -alkyl, 
tetrahydrofuryl-C.sub.2-4 -alkyl, furyl-C.sub.2-4 -alkyl and 
pyranyl-C.sub.2-4 -alkyl. 
The following compounds of the formula I may be mentioned specifically: 
______________________________________ 
##STR67## 
R.sup.1 R.sup.2 R.sup.2' 
R.sup.4 
R.sup.6 
______________________________________ 
2,4-(CH.sub.3).sub.2 
Cl Cl H i-Prop 
3-CH.sub.3 
Cl Cl H C(CH.sub.3).sub.3 
3-C.sub.2 H.sub.5 
Cl Cl H C(CH.sub.3).sub.3 
3-CHO Cl Cl H C(CH.sub.3).sub.3 
3-COOH Cl Cl H C(CH.sub.3).sub.3 
3-CH.sub.2 COOH 
Cl Cl H C(CH.sub.3).sub.3 
2-CH.sub.3 
Cl Cl H C(CH.sub.3).sub.3 
H Cl Cl H 
##STR68## 
H Cl Cl H 
##STR69## 
H Cl Cl H 
##STR70## 
H Cl Cl H 
##STR71## 
H Cl Cl H CH(CH.sub.3)CH.sub.2 OC.sub.2 H.sub.5 
H Cl Cl H 
##STR72## 
H Cl Cl H 
##STR73## 
H Cl Cl H 
##STR74## 
H Cl CH.sub.3 
H C(CH.sub.3).sub.3 
H Cl H H C(CH.sub.3).sub.3 
H CH.sub.3 
H H C(CH.sub.3).sub.3 
H SCH.sub.3 
H H C(CH.sub.3).sub.3 
H Cl F H C(CH.sub.3).sub.3 
H F F H C(CH.sub.3).sub.3 
H Cl CF.sub.3 
H C(CH.sub.3).sub.3 
H Cl C.sub.2 H.sub.5 
H C(CH.sub.3).sub.3 
H CN H H C(CH.sub.3).sub.3 
H Cl Cl CH.sub.3 
C(CH.sub.3).sub.3 
H Cl H CH.sub.3 
C(CH.sub.3).sub.3 
H Cl Cl CH.sub.3 
CH(CH.sub.3)CH.sub.2 OCH.sub.3 
2,5(CH.sub.3).sub.2 
Cl Cl CH.sub.3 
CH(CH.sub.3)CH.sub.2 OCH.sub.3 
H Cl Cl H CH(CH.sub.3).sub.2 CH.sub.2 F 
2,5(CH.sub.3).sub.2 
Cl Cl H CH(CH.sub.3).sub.2 CH.sub.2 F 
2,5(CH.sub.3).sub.2 
Cl Cl H 
##STR75## 
H Cl H H 
##STR76## 
2,5(CH.sub.3).sub.2 
Cl Cl H 
##STR77## 
H Cl Cl H 
##STR78## 
2,5(CH.sub.3).sub.2 
Cl Cl H 
##STR79## 
H Cl Cl H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
2,5(CH.sub.3).sub.2 
Cl Cl H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
2-CH.sub.3 
Cl Cl H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
3-CH.sub.3 
Cl Cl H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
3-CHO Cl Cl H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
3-COOH Cl Cl H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
3-CH.sub.2COOH 
Cl Cl H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
H Cl CH.sub.3 
H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
H Cl H H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
H CH.sub.3 
H H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
H CF.sub.3 
H H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
H Cl CF.sub.3 
H CH(CH.sub.3 )CH.sub.2 OCH.sub.3 
H CN H H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
2,5(CH.sub.3).sub.2 
Cl CH.sub.3 
H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
2,5(CH.sub.3).sub.2 
Cl H H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
H Cl Cl H CH(CH.sub.3)CH.sub.2 SCH.sub.3 
H Cl Cl H 
##STR80## 
H Cl Cl H 
##STR81## 
2,5(CH.sub.3).sub.2 
Cl Cl H CH(CH.sub.3)CH.sub.2 SCH.sub.3 
______________________________________ 
______________________________________ 
ArCHOHCH.sub.2NHR.sup.6 
Ar R.sup.6 
______________________________________ 
##STR82## C(CH.sub.3).sub.3 
##STR83## C(CH.sub.3).sub.3 
##STR84## C(CH.sub.3).sub.3 
##STR85## CH(CH.sub.3)CH.sub.2 OCH.sub.3 
##STR86## CH(CH.sub.3)CH.sub.2 OCH.sub.3 
##STR87## CH(CH.sub.3)CH.sub.2 OCH.sub.3 
##STR88## CH(CH.sub.3)CH.sub.2 OCH.sub.3 
##STR89## CH(CH.sub.3)CH.sub.2 OCH.sub.3 
______________________________________ 
The salts of the compounds of the formula I with hydrochloric acid, 
sulphuric acid, phosphoric acid, oxalic acid, maleic acid, fumaric acid 
and malonic acid may be mentioned as preferred. 
The compounds of the formula I can be prepared by the abovementioned 
processes 2(a) to (p). 
If, in process 2(a), 2-(4-amino-3-chlorophenyl)N-cyclohexyl-ethanolamine is 
used as the compound of the formula II and 2,5-hexanedione is used as the 
compound of the formula III, process (a) can be represented by the 
following equation: 
##STR90## 
The compounds of the formula II are known in some cases (Arzneim.-Forsch. 
34, 1625 (1984); 22, 861/1972). New compounds of the formula II are the 
subject matter of a Patent Application simultaneously filed by the 
Applicant Company. They are prepared in a manner which is known per se, 
for example analogously to the reactions described for processes 2(e) to 
(p). 
Compounds of the formula II in which the radicals R.sup.2 to R.sup.6 have 
the meanings given as preferred and particularly preferred in the case of 
the compounds of the formula I are preferably used. The following 
compounds of the formula II may be mentioned specifically: 
______________________________________ 
##STR91## 
R.sup.2 R.sup.6 
______________________________________ 
3,5-Cl.sub.2 C(CH.sub.3).sub.3 
3-Cl C(CH.sub.3).sub.3 
3-CH.sub.3 C(CH.sub.3).sub.3 
3-CF.sub.3 C(CH.sub.3).sub.3 
3-CF.sub.3, 5-Cl C(CH.sub.3).sub.3 
3-CN C(CH.sub.3).sub.3 
3,5-Cl.sub.2 CH(CH.sub.3).sub.2 
3,5-Cl.sub.2 CH(CH.sub.3)CH.sub.2 OCH.sub.3 
3,5-Cl.sub.3 
##STR92## 
3-Cl CH(CH.sub.3)CH.sub.2 OCH.sub.3 
3-CN CH(CH.sub.3)CH.sub.2 OCH.sub.3 
3,5-Cl.sub.2 
##STR93## 
3,5-Cl.sub.2 
##STR94## 
______________________________________ 
The compounds of the formula III are known or can be prepared analogously 
to known processes (compare Houben-Weyl Methoden der Organischen Chemie 
(Methods of Organic Chemistry) Volume 7/2b page 1876 et seq.; Volume 6/3 
page 707 et seq.; and Volume 7/1 page 255 et seq.). Like the compounds of 
the formula III, their monoacetals, diacetals or cyclic acetals of the 
formulae IIIa, b and c can also be used. 
Compounds of the formula III in which R.sup.1 has the meanings given as 
preferred and particularly preferred in the case of the compounds of the 
formula I are preferably used. The following compounds of the formula III 
may be mentioned specifically: 
______________________________________ 
##STR95## 
##STR96## 
R R.sup.1 R.sup.2 
______________________________________ 
H CH.sub.3 CH.sub.3 
H CH.sub.3 C.sub.2 H.sub.5 
2-CH.sub.3 CH.sub.3 CH.sub.3 
H H CH.sub.3 
H H H 
______________________________________ 
The methyl or ethyl acetals may be mentioned as preferred, such as, for 
example: 
##STR97## 
The cyclic acetals may be mentioned as preferred, such as, for example: 
##STR98## 
The reaction is carried out under conditions analogous to those known for 
the Knorr-Paal synthesis (Synthesis 1976 page 295; and The Chemistry of 
Pyrroles, page 77 et seq.). 
It is preferably carried out in the following solvents: hydrocarbons, such 
as toluene, acids, such as glacial acetic acid, nitriles, such as 
acetonitrile, or esters, such as ethyl acetate. 
It is advantageously carried out in the presence of acid catalysts. Acid 
catalysts which may be mentioned are: acetic acid, p-toluenesulphonic 
acid, hydrochloric acid and methanesulphonic acid. 
It is carried out at temperatures of 0.degree.-150.degree. C., preferably 
between 20.degree. and 100.degree. C., advantageously using a water 
separator. 
The starting substances are used in an approximately equimolar ratio to one 
another. 
Working up is carried out by a procedure in which the reaction mixture is 
poured onto water, rendered alkaline and extracted with solvents such as 
ethyl acetate, ether or methylene chloride, the organic phase is 
evaporated and the residue is chromatographed or redissolved or distilled. 
If cyclic acetals of the formula IIIc are used as starting substances, the 
reaction is advantageously carried out in the presence of acid catalysts. 
Acid catalysts which may be mentioned are: acetic acid, p-toluenesulphonic 
acid and methanesulphonic acid. 
The reaction of compounds of the formula II with dihalogenoketones of the 
formula IV in process 2(b) can be represented, in the case of 
2-[4-amino-5-trifluoromethylthiophenyl]-N-cyclobutylaminoethanol and 
dibromoallene, by the following equation: 
##STR99## 
The process is carried out in a manner which is known per se. Compounds of 
the formula IV are known or can be prepared analogously to known 
processes. 
The reaction of compounds of the formula II with epoxybutanes of the 
formula V in process 2(c) can be represented, in the case of 
2-(4-amino-5-cyanophenyl)-N-1-ethyltetrahydrofurylamino-propan-2-ol and 
3,4-epoxybutyraldehyde diethylacetal, by the following equation: 
##STR100## 
The process is carried out in a manner which is known per se. The 
epoxybutanes of the formula V are known or can be prepared analogously to 
known processes. 
The reaction of compounds of the formula II with halogenocrotonaldehyde in 
process 2(d) can be represented, in the case of 
4-amino-3-fluoro-5-ethyl-phenyl-t-butylaminoethanol and 
2-chlorocrotonaldehyde, by the following equation: 
##STR101## 
The reaction is carried out in a manner which is known per se. The 
halogenocrotonaldehydes of the formula VI are known or can be prepared 
analogously to known processes. 
If, in process 2(e), 
2-(3-pyrrolo-5-methoxyphenyl-)-2-oxocyclohexylethylamine is used as the 
compound of the formula VII, process 2(e) can be represented by the 
following equation: 
##STR102## 
The compounds of the formula VII are new. They are prepared by the process 
described below under (4). 
The substituents R.sup.1, R.sup.2, R.sup.4, R.sup.5 and R.sup.6 in formula 
VII preferably have the meanings given as preferred and particularly 
preferred in the case of the compounds of the formula I. The following 
compounds of the formula VII may be mentioned specifically: 
______________________________________ 
R.sup.1 
R.sup.2 R.sup.4 
R.sup.5 
R.sup.6 
______________________________________ 
H 3,5-Cl.sub.2 
H H CMe.sub.3 
H 3,5-Cl.sub.2 
H H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
H 3-Cl H H CH(CH.sub.3)CH.sub.2 OCH.sub.3 
H 3,5-Cl.sub.2 
H H 
##STR103## 
______________________________________ 
The following reducing agents may be mentioned as reducing agents for 
carrying out the process: H.sub.2 /catalyst, examples of the catalyst 
which may be mentioned being: PtO.sub.2 and Pd-active charcoal; and 
complex metal hydrides, such as, for example, LiAlH.sub.4, NaBH.sub.4 and 
NaBH.sub.3 CN. 
The following reducing agents are particularly preferably used: NaBH.sub.4 
and NaBH.sub.3 CN. 
The reaction is carried out at temperatures from -20.degree. C. to 
+100.degree. C., preferably between 0.degree. and 50.degree. C. 
The reaction is preferably carried out at atmospheric pressure. 
All the inert organic solvents are used as diluents. These include, in 
particular, aliphatic and aromatic hydrocarbons, such as pentane, hexane, 
cyclohexane, petroleum ether, ligroin, benzene and toluene; chlorinated 
hydrocarbons, such as methylene chloride, ethylene chloride and 
chloroform; ethers, such as diethyl ether and glycol dimethyl ether; 
nitriles, such as acetonitrile, propionitrile and benzonitrile; and 
alcohols, such as methanol, ethanol and n- and i-propanol. Alcohols are 
preferred. 
If, in process 2(f), 3-methyl-4-pyrrolophenyl epoxide is used as the 
epoxide of the formula VII and t-butylamine is used as the amine of the 
formula IX, process 2(f) can be represented by the following equation: 
##STR104## 
Epoxides of the formula VII are new. They are prepared by the process 
described under (6). Epoxides of the formula VIII in which R, R.sup.2 and 
R.sup.4 have the meanings given as preferred and particularly preferred in 
the case of the compounds of the formula I are preferably used. 
The following epoxides may be mentioned specifically: 
4-pyrrolo-3-chlorophenyl epoxide, 4-pyrrolo-3-cyanophenyl epoxide, 
3,5-dichloro-4-pyrrolophenyl epoxide, 3-chloro-4-pyrrolo-5-cyanophenyl 
epoxide, 3-cyano-4-pyrrolo-5-chlorophenyl epoxide, 
3-cyano-4-pyrrolo-phenyl epoxide, 
3-chloro-4-pyrrolo-5-trifluoromethylphenyl epoxide and 
3-bromo-4-pyrrolo-5-cyanophenyl epoxide. 
Amines of the formula IX in which R.sup.5 and R.sup.6 have the meanings 
given as preferred and particularly preferred in the case of the compounds 
of the formula I are preferably used. 
Amines of the formula IX which may be mentioned are, for example, 
tert.-butylamine, isopropylamine, 2-methoxymethyl-ethylamine, 
2-tetrahydropyranylethylamine, 2-cyclohexylethylamine, 
2-cyclobutylethylamine and 2-cyclopropyl-ethylamine. 
Process 2(f) is carried out by reacting approximately equimolar amounts of 
the epoxide of the formula VIII and the amine of the formula IX in a 
diluent. 
An excess of amine (1-3 molar, preferably 1-1.5 molar) relative to the 
epoxide of the formula VIII is in general used. 
The reaction is carried out at temperatures from +20.degree. to 
+150.degree. C. 
The reaction is preferably carried out at atmospheric pressure. 
All the inert organic solvents are used as diluents. These include, in 
particular, aliphatic and aromatic, optionally halogenated hydrocarbons, 
such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, 
ligroin, benzene, toluene, methylene chloride, ethylene chloride, 
chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, and 
furthermore ethers, such as diethyl ether, dibutyl ether, glycol dimethyl 
ether, diglycol dimethyl ether, tetrahydrofuran and dioxane, and 
furthermore nitriles, such as acetonitrile and benzonitrile, amides, such 
as dimethylformamide, and alcohols, such as methanol, ethanol and n- and 
i-propanol. 
Alcohols are preferred. 
If, in process 2(g), 
3-chloro-4-(2-ethoxycarbonylpyrrolo)-chloroacetophenone is used as the 
2-halogenoketone of the formula X and 1-cyclohexylethylamine is used as 
the amine of the formula IX, process 2(g) can be represented by the 
following equation: 
##STR105## 
The 2-halogenoketones of the formula X are new. They are prepared by the 
process described under (8). Compounds of the formula X in which R.sup.1 
and R.sup.2 have the meanings given as preferred and particularly 
preferred in the case of the compounds of the formula I and halogen 
represents chlorine or bromine are preferably used. 
The amines mentioned in the case of process 2(f) are preferably used. 
The following compounds of the formula X may be mentioned specifically: 
(2-pyrrolo-3-chlorophenyl-5-chloromethyl ketone, 
(2-pyrrolo-3-cyanophenyl-5-chloromethyl ketone, 
(2,4-dichloro-3-pyrrolophenyl-6-bromomethyl ketone, 
(2-cyano-3-pyrrolophenyl-6-bromomethyl ketone, 
(3-pyrrolo-4-cyanophenyl-6-bromomethyl ketone, 
(2-pyrrolo-3-cyanophenyl-5-bromomethyl ketone, 
(2-cyano-3-pyrrolo-4-chlorophenyl-bromomethyl ketone, 
(2-cyano-3-pyrrolo-4-chlorophenyl-6-chloromethyl ketone, 
(2-chloro-3-pyrrolo-4-trifluoromethylphenyl-6-bromomethyl ketone, 
(2-trifluoromethyl-3-pyrrolo-4-cyanophenyl-6-bromomethyl ketone and 
(2-fluoro-3-pyrrolo-4-cyanophenyl-6-chloromethyl ketone. 
Process 2(g) is carried out by reacting approximately equimolar amounts of 
the 2-halogenoketone of the formula X and the amine of the formula IX in a 
diluent. An excess of amine (1-3 molar, preferably 1-1.5 molar) relative 
to the 2-halogenoketone of the formula X is in general used. 
The reaction is carried out at temperatures from 20.degree. to 150.degree. 
C., preferably 50.degree. to 120.degree. C. 
The diluents mentioned for process 2(f) may be mentioned as preferred 
diluents. 
If, in process 2(h), 1-(3-pyrrolo-phenyl)-2-chloroethanol is used as the 
beta-halogenomethyl compound of the formula XI and t-butylamine is used as 
the amine of the formula IX, process 2(h) can be represented by the 
following equation: 
##STR106## 
Beta-halogenomethyl compounds of the formula XI are new. They are prepared 
by the process described under (10). Compounds of the formula IX in which 
R.sup.1, R.sup.2 and R.sup.4 have the meanings given as preferred in the 
case of the compounds of the formula I and Hal represents chlorine or 
bromine are preferred. 
The following compounds of the formula XI may be mentioned specifically: 
1-(2-pyrrolo-3-chloro-phenyl)-2-chloroethanol, 
1-(2-pyrrolo-3-cyano-phenyl)-2-chloroethanol, 
1-(2,4-dichloro-3-pyrrolophenyl)-2-chloroethanol, 
1-(2-chloro-3-pyrrolo-4-cyano-phenyl)-2-chloroethanol, 
1-(2-cyano-3-pyrrolo-4-chloro-phenyl)-2-bromoethanol, 
1-(2-cyano-3-pyrrolophenyl)-2-chloroethanol, 
1-(3-pyrrolo-4-cyano-phenyl)-2-bromoethanol, 
1-(2-chloro-3-pyrrolo-4-trifluoromethyl-phenyl)-2-chloroethanol and 
1-(2-cyano-3-pyrrolo-4-fluoro-phenyl)-2-bromoethanol. 
Process 2(h) is carried out by reacting the betahalogenomethyl compound of 
the formula XI with excess amine of the formula IX, if appropriate in the 
presence of a diluent. 
The reaction is carried out at temperatures from +20.degree. to 
+150.degree. C. 
The reaction is carried out at atmospheric pressure or under increased 
pressure. 
All the inert organic solvents are used as diluents. These include, in 
particular, aliphatic and aromatic, optionally halogenated hydrocarbons, 
such as pentane, hexane, cyclohexane, benzene, toluene, methylene chloride 
and chloroform, and furthermore ethers, such as diethyl ether, 
tetrahydrofuran and dioxane, and moreover nitriles, such as acetonitrile 
and benzonitrile, and furthermore amides, such as dimethylformamide, and 
furthermore alcohols, such as methanol, ethanol and n- and i-propanol. 
Alcohols are preferably used. 
If, in process 2(i), 3-fluoro-4-pyrrolo-(1-hydroxy-2-aminoethyl)-benzene is 
used as the compound of the formula XII and acetophenone is used as the 
compound of the formula XIII, process 2(i) can be represented by the 
following equation: 
##STR107## 
Compounds of the formulae XII are new. They are prepared by the process 
described under (12). Compounds of the formula XII in which R.sup.1, 
R.sup.2, R.sup.3 and R.sup.4 have the meanings given as preferred and 
particularly preferred in the case of the compounds of the formula I are 
preferably used. 
The following compounds of the formula XII may be mentioned specifically: 
1-(2-pyrrolo-3-chloro-phenyl)-2-aminoethanol, 
1-(2-pyrrolo-3-cyano-phenyl)-2-aminoethanol, 
1-(2,4-dichloro-3-pyrrolophenyl)-2-aminoethanol, 
1-(2-chloro-3-pyrrolo-4-cyano-phenyl)-2-aminoethanol, 
1-(2-cyano-3-pyrrolophenyl)-2-aminoethanol and 
1-(2-chloro-3-pyrrolo-4-trifluoromethyl-phenyl)-2-aminoethanol. 
Compounds of the formula XIII are known or can be prepared analogously to 
known processes. 
R.sup.13 preferably represents C.sub.1-4 -alkyl, in particular methyl, or 
C.sub.3-6 -cycloalkyl, in particular cyclopropyl, and 
R.sup.14 preferably represents C.sub.1-4 -alkyl, which is optionally 
substituted by halogen, in particular fluorine, C.sub.1-4 -alkoxy, in 
particular methoxy, or C.sub.1-4 -alkylthio, in particular methylthio, or 
furthermore represents C.sub.3-6 -cycloalkyl, which is optionally 
substituted by C.sub.1-4 -alkyl, in particular methyl, or C.sub.1-4 
-alkoxy, in particular methoxy, or furthermore represents heterocyclyl 
which has 4-6 ring atoms and O as the hetero atom and is optionally 
substituted by C.sub.1-4 -alkyl, in particular methyl, such as, for 
example, tetrahydrofuranyl, furanyl, pyranyl or tetrahydropyranyl, or 
R.sup.13 and R.sup.14, together with the C atom to which they are bonded, 
furthermore represent an aliphatic ring with 3-7 ring atoms, such as 
cyclopropyl, cyclopentyl, cyclohexyl or cyclohexenyl. 
The following compounds of the formula XIII may be mentioned specifically: 
acetone, methyl ethyl ketone, methyl isopropyl ketone, diethyl ketone, 
ethyl propyl ketone, methyl cyclohexyl ketone and cyclohexanone. 
Process 2(i) is carried out by taking approximately equimolar amounts of 
the compounds of the formulae XII and XIII in a diluent and reducing the 
mixture. 
The reaction is carried out at temperatures from 0.degree. C. to 
150.degree. C. 
The reaction is preferably carried out at atmospheric pressure. 
All the inert organic solvents are used as diluents. These include 
aliphatic and aromatic, optionally halogenated hydrocarbons, such as 
pentane, hexane, cyclohexane, benzene, toluene, methylene chloride, 
ethylene chloride, chloroform and chlorobenzene, and furthermore ethers, 
such as diethyl ether, tetrahydrofuran and dioxane, and moreover nitriles, 
such as acetonitrile and benzonitrile, amides, such as dimethylformamide, 
and alcohols, such as methanol and ethanol. 
The reducing agents used are: H.sub.2 /catalyst, PtO.sub.2 being mentioned 
as an example of a catalyst; complex metal hydrides, such as, for example, 
LiAlH.sub.4, NaBH.sub.4 and NaBH.sub.3 CN; and Raney nickel. 
If, in process 2(j), 3-methyl-4-pyrrolophenylglyoxal is used as the 
compound of the formula XIV and t-butylamine is used as the amine of the 
formula III, process 2(j) can be represented by the following equation. 
##STR108## 
The compounds of the formula XIV are new. They are prepared by the process 
described below under (14). 
The substituents R.sup.1 and R.sup.2 in formula XIV preferably have the 
meanings given above as preferred in the case of the compounds of the 
formula I. The following compounds of the formula XIV may be mentioned 
specifically: 4-pyrrolo-3-chloro-phenylglyoxal, 
4-pyrrolo-3-cyano-phenylglyoxal, 3,5-dichloro-4-pyrrolophenylglyoxal, 
3-cyano-4-pyrrolophenyglyoxal and 
3-chloro-4-pyrrolo-5-trifluoromethyl-phenylglyoxal. 
Process 2(j) is carried out by adding about the equivalent amount of the 
amine of the formula IX to the compound of the formula XIV in a diluent 
and then reducing the mixture. 
The reaction is carried out at temperatures from 0.degree. C. to 
100.degree. C. 
The reaction is preferably carried out at atmospheric pressure. 
All the inert organic solvents are used as diluents. These include, in 
particular, aliphatic and aromatic, optionally halogenated hydrocarbons, 
such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, 
ligroin, benzene, toluene, methylene chloride, ethylene chloride, 
chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, and 
furthermore ethers, such as diethyl ether, dibutyl ether, glycol dimethyl 
ether, diglycol dimethyl ether, tetrahydrofuran and dioxane, and in 
addition esters, such as methyl and ethyl acetate, and furthermore 
nitriles, such as, for example, acetonitrile, propionitrile, benzonitrile 
and glutaric acid dinitrile, and moreover amides, such as, for example, 
dimethylformamide, dimethylacetamide and N-methylpyrrolidone, as well as 
tetramethylene sulphone and hexamethylphosphoric acid triamide, and 
furthermore alcohols, such as methanol, ethanol and n- and i-propanol. 
The reducing agents used are H.sub.2 /catalyst (PtO.sub.2 and Pd-charcoal 
may be mentioned as the catalyst) and furthermore complex metal hydrides, 
such as LiAlH.sub.4 and NabH.sub.4. 
If, in process 2(k), (5-chloro-4-pyrrolophenyl)hydroxyacetic acid 
isopropylamide is used as the compound of the formula XV, process 2(k) can 
be represented by the following equation: 
##STR109## 
Compounds of the formula XV are new. They are prepared by the process 
described under (16). Compounds of the formula XV in which R.sup.1, 
R.sup.2, R.sup.5 and R.sup.6 have the meanings given as preferred and 
particularly preferred in the case of the compounds of the formula I are 
preferably used. 
The following compounds of the formula XV may be mentioned specifically: 
(3-chloro-4-pyrrolophenyl)hydroxyacetic acid isopropylamide, 
(3-cyano-4-pyrrolophenyl)hydroxyacetic acid isopropylamide, 
(3-chloro-4-pyrrolopphenyl)hydroxyacetic acid tert.-butylamide, 
(3-chloro-4-pyrrolo-5-amino-cyano-phenyl)hydroxyacetic acid 
isopropylamide, (3-cyano-4-pyrrolo-5-chloro-phenyl)hydroxyacetic acid 
tert.-butylamide, (3-cyano-4-pyrrolo-5-chloro-phenyl)hydroxyacetic acid 
isopropylamide, (3,5-dichloro-4-pyrrolophenyl)hydroxyacetic acid 
tert.-butylamide, (3,5-dichloro-4-pyrrolophenyl)hydroxyacetic acid 
isopropylamide and (3,5-dichloro-4-pyrrolophenyl)hydroxyacetic acid 
tert.-butylamide. 
Process 2(k) is carried out by reacting the compound of the formula XV with 
excess reducing agent in a diluent. 
The reaction is carried out at temperatures from 0.degree. C. to 
+150.degree. C. 
The reaction is preferably carried out at atmospheric pressure. 
All the inert organic solvents are used as diluents. These include, in 
particular, aliphatic and aromatic, optionally halogenated hydrocarbons, 
such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, 
ligroin, benzene, toluene, methylene chloride, ethylene chloride, 
chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, and 
furthermore ethers, such as diethyl ether, dibutyl ether, glycol dimethyl 
ether, diglycol dimethyl ether, tetrahydrofuran and dioxane. 
The reducing agents used are complex metal hydrides, such as LiAlH.sub.4, 
and boranes, such as diborane. 
If, in process 2(l), 
4-(2-ethylpyrrolo)-3,5-difluorophenylethanol-dicyclopropylmethylamine is 
used as the compound of the formula I and benzoyl chloride is used as the 
acylating agent, process 2(l) can be represented by the following 
equation: 
##STR110## 
The acylation reaction is carried out analogously to known acylation 
reactions. 
Acylating agents which may be mentioned as preferred are: acetyl chloride, 
acetic anhydride, propionic anhydride and methoxyacetyl chloride. 
Compounds of the formula I and the acylating agents are preferably reacted 
in the presence of diluents and in the presence of acid-binding agents. 
Possible diluents are all the inert organic solvents. These include, in 
particular, aliphatic and aromatic, optionally halogenated hydrocarbons, 
such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, 
ligroin, benzene, toluene, methylene chloride, ethylene chloride, 
chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, and 
furthermore ethers, such as diethyl ether, dibutyl ether, glycol dimethyl 
ether, diglycol dimethyl ether, tetrahydrofuran and dioxane, and moreover 
ketones, such as acetone, methyl ethyl ketone, methyl isopropyl ketone and 
methyl isobutyl ketone, and in addition esters, such as methyl and ethyl 
acetate, and furthermore nitriles, such as, for example, acetonitrile, 
propionitrile, benzonitrile and glutaric acid dinitrile, and moreover 
amides, such as, for example, dimethylformamide, dimethylacetamide and 
N-methylpyrrolidone, as well as dimethyl sulphoxide, tetramethylene 
sulphone and hexamethylphosphoric acid triamide. 
Acid-binding agents which may be mentioned are: alkali metal and alkaline 
earth metal alcoholates and tertiary amines. The following bases may be 
mentioned as particularly preferred: triethylamine, pyridine, picolines, 
trimethylamine, N-methyl-morpholine, N-ethylpyrrolidone, 
diazabicyclo(4,3,0)undecene (DBU), 1,4-diazabicyclo-2,2,2-octane (DABCO) 
and diazabicyclo(3,2,0)nonene (DBN). 
The reaction is carried out at 0.degree.-150.degree. C., preferably at 
20.degree.-100.degree. C. and preferably at atmospheric pressure. 
The reaction is preferably carried out under an inert gas atmosphere. 
The compounds of the formula I and the acylating agents are preferably 
employed in an equimolar ratio to one another. An excess of either of the 
compounds provides no substantial advantage. The acid-binding agents are 
preferably used in an equimolar amount or in an excess of up to 10 mols in 
relation to the compounds of the formula I. If tertiary amines are used as 
the acid-binding agents, these can also serve as the reaction medium. 
Working up is carried out in a manner which is known per se by a procedure 
in which the salt which has separated out is filtered off and the organic 
phase is concentrated, or in which the reaction mixture is poured into 
water and the organic phase is separated off and concentrated. 
If, in process 2(m), 
3-cyano-4-(2-methoxypyrrolo)phenyl-2-cyclohexylamino-propanol is used as 
the compound of the formula I and dimethyl-(1,3-dimethyl-butyl)-silyl 
chloride is used as the silylating agent of the formula XVI, process 2(m) 
can be represented by the following equation: 
##STR111## 
The compounds of the formula I can be prepared by one of the abovementioned 
processes 2(a)-(e). The compounds of the formula XVI are known. 
The process is carried out by methods analogous to known methods of organic 
chemistry. 
The process can be carried out in the presence of diluents. Possible 
diluents are all the inert organic solvents. These include, in particular, 
aliphatic and aromatic, optionally halogenated hydrocarbons, such as 
pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, 
benzene, toluene, methylene chloride, ethylene chloride, chloroform, 
carbon tetrachloride, chlorobenzene and o-dichlorobenzene, and furthermore 
ethers such as diethyl ether, dibutyl ether, glycol dimethyl ether, 
diglycol dimethyl ether, tetrahydrofuran and dioxane, and furthermore 
ketones, such as acetone, methyl ethyl ketone, methyl isopropyl ketone and 
methyl isobutyl ketone, and in addition esters, such as methyl and ethyl 
acetate, and furthermore nitriles, such as, for example, acetonitrile, 
propionitrile, benzonitrile and glutaric acid dinitrile, and moreover 
amides, such as, for example, dimethylformamide, dimethylacetamide and 
N-methylpyrrolidone, as well as dimethyl sulphoxide, tetramethylene 
sulphone and hexamethylphosphoric acid triamide. 
The process can be carried out in the presence of catalysts. Catalysts 
which can preferably be used are: imidazole, triazole or 
diisopropylethylamine. 
The reaction temperature is kept between about 0.degree. C. and 130.degree. 
C., preferably between about 20.degree. C. and 60.degree. C. The process 
is preferably carried out at atmospheric pressure. 
The starting compounds are in general used in an approximately equimolar 
ratio. 
If, in process 2(n), 
4-pyrrolo-3-trifluoromethyl-5-chlorophenyl-ethanolmethoxyisopropylamine is 
used as the compound of the formula I and phosgene is used, process 2(n) 
can be represented by the following equation: 
##STR112## 
The process is carried out by reacting phenylethanolamines of the formula I 
with phosgene or agents which split off phosgene, if appropriate in the 
presence of bases, such as, for example, tertiary amines, preferably 
triethylamine or imidazole, at between 0.degree. and 100.degree. C. in 
inert diluents, such as, for example, optionally halogenated hydrocarbons, 
preferably methylene chloride or toluene. 
If, in process 2(o), 
4-(3,4-dimethylpyrrolo)-3-methoxyphenyl-ethanol-monofluoro tertiary 
butylamine is used as the compound of the formula I and acetaldehyde is 
used as the aldehyde of the formula XVII, process 2(o) can be represented 
by the following equation: 
##STR113## 
The process is carried out by reacting phenylethanolamines of the formula I 
with aldehydes or ketones, preferably formaldehyde or acetone, if 
appropriate in the presence of acid catalysts, such as, for example, 
p-toluenesulphonic acid, or in the presence of molecular sieves, if 
appropriate in inert diluents, such as, for example, optionally 
halogen-substituted hydrocarbons, at between 0.degree. and 100.degree. C. 
Process 2(p) is carried out under the conditions customary for alkylation 
of amines with alkyl halides. It is preferably carried out in inert 
diluents, such as hydrocarbons, for example toluene or xylene, ethers, 
such as dioxane or tetrahydrofuran, or ketones, such as acetone, at 
temperatures of 20.degree.-180.degree. C., preferably between 60.degree. 
and 150.degree. C. If appropriate, the reaction is carried out with the 
addition of bases, such as inorganic bases, for example alkali metal and 
alkaline earth metal hydroxides, carbonates or bicarbonates, or organic 
bases, such as tertiary amines, for example triethylamine. 
The compounds of the formula XXXVIII are usually employed in an equimolar 
amount in relation to the compounds of the formula XII. It may be 
advantageous to add a 1- to 3-fold excess of compounds of the formula 
XXXVIII. 
The compounds of the formula XXXVIII are known or can be prepared by 
processes which are known per se. R.sup.13 and R.sup.14 preferably have 
the meanings given above as preferred and particularly preferred in the 
case of the compounds of the formula XIII. 
The compounds of the formula XII preferably used above in process 2(i) are 
preferably used as the compounds of the formula XII. 
As already mentioned, the new compounds of the formula VII can be prepared 
by the process described under 4. 
Process 4 is carried out as described for process 2(f) in the first stage. 
The compounds of the formula X and amines of the formula IX mentioned for 
process 2(g) are preferably used. 
As already mentioned, the new compounds of the formula VIII can be prepared 
by the process described under (6). 
Process 6 is carried out by reacting a compound of the formula XI with 2-5 
times the molar amount, preferably 2-4 times the molar amount, of a base 
in a diluent. If 1-(3-chloro-4-pyrrolophenyl)-2-bromoethanol is used as 
the compound of the formula XI and NaOH is used as the base, the reaction 
can be represented by the following equation: 
##STR114## 
Compounds of the formula XI are new. They are prepared by the process 
described under (10). 
Compounds of the formula XI in which R.sup.1, R2 and R.sup.4 have the 
meanings given as preferred in the case of the compounds of the formula I 
and Hal represents chlorine or bromine are preferably used. 
The following compounds of the formula XI may be mentioned specifically: 
______________________________________ 
##STR115## 
R.sup.1 R.sup.2 Hal 
______________________________________ 
H 3,5-Cl.sub.2 
Cl 
H 3,5-Cl.sub.2 
Br 
2,5(CH.sub.3).sub.2 
3,5-Cl.sub.2 
Cl 
H 3-Cl Cl 
2,5(CH.sub.3).sub.2 
3-Cl Br 
______________________________________ 
Bases which may be mentioned are: alkali metal and alkaline earth metal 
hydroxides, such as sodium hydroxide and potassium hydroxide; and 
carbonates and bicarbonates, such as sodium carbonate, sodium bicarbonate 
and barium carbonate; and alcoholates, such as sodium methylate and sodium 
ethylate. 
Diluents which may be mentioned are: alcohols, such as methanol and 
ethanol, water, and mixtures of alcohols with water. 
The reaction is carried out at temperatures from 0.degree. C. to 
+100.degree. C., and it is preferably carried out at atmospheric pressure. 
If, in process 6, 3-methyl-4-pyrrolobenzaldehyde is used as the compound of 
the formula XVIII, trimethylsulphonium iodide is used as the reagent which 
transfers methylene groups and sodium hydride is used as the base, the 
reaction can be represented by the following equation: 
##STR116## 
Compounds of the formula XVIII are new. They are prepared by the process 
described under (18). Compounds of the formula XVIII in which R.sup.1 and 
R.sup.2 have the meanings given as preferred in the case of the compounds 
of the formula I are preferably used. 
The following compounds of the formula XVIII may be mentioned specifically: 
______________________________________ 
##STR117## 
R.sup.1 R.sup.2 R.sup.1 R.sup.2 
______________________________________ 
H 3,5-Cl.sub.2 
2,5(CH.sub.3).sub.2 
3,5-Cl.sub.2 
H 3-Cl 2,5(CH.sub.3).sub.2 
3-Cl 
H 3-CF.sub.3 5-Cl 
2,5(CH.sub.3).sub.2 
3-CF.sub.3 5-Cl 
H 3-CH.sub.3 2,5(CH.sub.3).sub.2 
3-CN 
H 3-CN 
______________________________________ 
Reagents which may be mentioned which transfer methylene groups are: 
trimethylsulphonium halides, such as trimethylsulphonium chloride, bromide 
and iodide, and trimethylsulphoxonium halides, such as 
trimethylsulphoxonium chloride, bromide and iodide. 
The bases used are: alkali metal and alkaline earth metal hydrides, such as 
sodium hydride, and alkali metal and alkaline earth metal alcoholates, 
such as potassium tert.-butylate. 
The process is carried out by taking 1.1 equivalents of the base, for 
example in dimethylsulphoxide, and then adding the agent which transfers 
methylene groups (1.1 equivalents) and finally adding 1 equivalent of the 
compound of the formula XVIII. 
The reaction is carried out at temperatures from 0.degree. C. to 
100.degree. C., preferably at 50.degree.-70.degree. C., and it is 
preferably carried out at atmopheric pressure. 
The diluents used are dimethylsulphoxide or mixtures of dimethylsulphoxide 
with inert organic solvents. 
Inert organic solvents which may be mentioned are: ethers, such as diethyl 
ether, tetrahydrofuran and dioxane. 
The new halogenomethylketones of the formula X can be prepared by the 
processes described under (8). 
The compounds of the formula XIX are new. They can be prepared by the 
process described under (20). Compounds of the formula XIX in which 
R.sup.1 and R.sup.2 have the meanings given as preferred and particularly 
preferred in the case of the compounds of the formula I are preferably 
used. 
The following compounds of the formula XIX may be mentioned specifically: 
______________________________________ 
##STR118## 
R.sup.1 R.sup.2 R.sup.1 R.sup.2 
______________________________________ 
H 3,5-Cl.sub.2 
2,5(CH.sub.3).sub.2 
3,5-Cl.sub.2 
H 3-Cl 2,5(CH.sub.3).sub.2 
3-Cl 
H 3-CF.sub.3 5-Cl 
2,5(CH.sub.3).sub.2 
3-CF.sub.3 5-Cl 
H 3-CH.sub.3 2,5(CH.sub.3).sub.2 
3-CH.sub.3 
H 3-CN 2,5(CH.sub.3).sub.2 
3-CN 
H 3-CF.sub.3 2,5(CH.sub.3).sub.2 
3-CF.sub.3 
______________________________________ 
If, in process 8, 4-fluoro-8-pyrroloacetophenone is used as the compound of 
the formula XIX and bromine is used as the halogen Hal, the reaction can 
be represented by the following equation: 
##STR119## 
Process 8 is carried out by adding the equivalent amount of halogen, if 
appropriate dissolved in a diluent, to the compound XIX in a diluent. 
The reaction is carried out at +20.degree. C. to +150.degree. C., 
preferably at the boiling point of the diluent used. 
The reaction is preferably carried out at atmopheric pressure. 
Diluents which may be mentioned are: aliphatic, optionally halogenated 
hydrocarbons, such as pentane, hexane, heptane, cyclohexane, methylene 
chloride, ethylene chloride, chloroform and carbon tetrachloride, 
alcohols, such as methanol and ethanol, esters, such as ethyl acetate, and 
mixtures of these diluents. 
If, in process 8, 3-chloro-4-pyrroloacetophenone is used as the compound of 
the formula XIX and copper(II) bromide is used as the copper halide, the 
reaction can be represented by the following equation: 
##STR120## 
The process is carried out by heating equivalent amounts of the compound of 
the formula XIX and copper halide under reflux in the dilunet for 1-24 
hours, preferably 6-12 hours. 
The reaction parameters and diluents are as described above. 
As already mentioned, the new compounds of the formula XI can be prepared 
by the process described under (10). 
If, in process 10, 3-cyano-4-pyrrolochloroacetophenone is used as the 
compound of the formula X, process 10 can be represented by the following 
equation: 
##STR121## 
The substituents R.sup.1 and R.sup.2 in the compounds of the formula X have 
the meanings given as preferred in the case of the compounds of the 
formula I. Hal preferably represents chlorine or bromine. 
Reducing agents which may be mentioned for carrying out the process are: 
H.sub.2 /catalyst (catalysts which may be mentioned are: PtO.sub.2 and 
Pd/charcoal) and complex metal hydrides, such as, for example, 
LiAlH.sub.4, NaBH.sub.4 and NaBH.sub.3 CN. NaBH.sub.4 and NaBH.sub.3 CN 
are preferably used. 
Process 10 is carried out by reacting the compound X with the reducing 
agent in a diluent. 
The reaction is carried out at temperatures from -20.degree. C. to 
+100.degree. C. 
The reaction is preferably carried out at atmospheric pressure. 
All the inert organic solvents are used as diluents. These include, in 
particular, optionally halogenated aliphatic and aromatic hydrocarbons, 
such as pentane, hexane, cyclohexane, benzene, toluene, methylene 
chloride, chloroform and chlorobenzene; ethers, such as diethyl ether and 
tetrahydrofuran; nitriles, such as acetonitrile and benzonitrile; and 
alcohols, such as methanol, ethanol and n- and i-propanol. Alcohols are 
preferably used. 
As already mentioned, the compounds of the formula XII can be prepared by 
the process described under 12. 
If 1-(3-bromo-4-pyrrolophenyl)-2-nitroethanol is used as the nitro compound 
of the formula XXIV in process 12, the reaction can be represented by the 
following equation: 
##STR122## 
The compounds of the formula XXIV are new. They can be prepared by the 
process described under (22). The substituents R.sup.1, R.sup.2, R.sup.3 
and R.sup.4 in formula XXIV preferably have the meanings given above as 
preferred in the case of the compounds of the formula I. 
The following compounds of the formula XXIV may be mentioned specifically: 
______________________________________ 
##STR123## 
R.sup.1 R.sup.2 R.sup.1 R.sup.2 
______________________________________ 
H 3,5-Cl.sub.2 
2,5(CH.sub.3).sub.2 
3,5-Cl.sub.2 
H 3-Cl 2,5(CH.sub.3).sub.2 
3-Cl 
H 3-CF.sub.3 2,5(CH.sub.3).sub.2 
3-CF.sub.3 
H 3-CN 2,5(CH.sub.3).sub.2 
3-CH.sub.3 
H 3-CF.sub.3 5-Cl 
2,5(CH.sub.3).sub.2 
3-CN 
2,5(CH.sub.3).sub.2 
3-CF.sub.3 5-Cl 
______________________________________ 
Hydrogen/catalyst is used as the reducing agent for the process. Examples 
of catalysts which may be mentioned are: Raney nickel, PtO.sub.2 and 
Pd/charcoal. 
The process is carried out by subjecting the compound XXI to catalytic 
hydrogenation in a diluent with the addition of an acid. 
The reaction is carried out at temperatures from +.degree. C. to 
+150.degree. C. 
The reaction is carried out at atmospheric pressure or increased pressure. 
All the inert organic solvents are used as diluents. These include, in 
particular, aliphatic and aromatic hydrocarbons, such as pentane, hexane, 
cyclohexane, benzene and toluene; ethers, such as diethyl ether and 
tetrahydrofuran; and alcohols, such as methanol and ethanol. 
The acids used are: inorganic acids, such as carbonic acid; hydrogen halide 
acids, such as hydrochloric acid, and sulphuric acid, and organic acids, 
such as acetic acid and propionic acid. 
As already mentioned, the new compounds of the formula XIV can be prepared 
by the process described under (14). 
If, in the process, 3-cyano-4-tetramethylpyrrolobromacetophenone is used as 
the halogenomethyl ketone of the formula X, the process can be represented 
by the following equation: 
##STR124## 
The compounds mentioned above are preferably used as the halogenomethyl 
ketones of the formula X. 
The process is carried out by oxidizing the compound X, if appropriate in 
the presence of a diluent. 
The reaction is carried out at temperatures from +20.degree. C. to 
+100.degree. C. 
The reaction is preferably carried out at atmospheric pressure. 
Dimethylsulphoxide is preferably used as the oxidizing agent (N. Kornblum 
et al., JACS 79, 6562 (1957). 
If the reaction is carried out in the presence of a diluent, all the inert 
organic solvents can be used. These include, in particular, aliphatic and 
aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, 
cyclohexane, benzene, toluene, methylene chloride, chloroform and 
chlorobenzene; ethers, such as diethyl ether and tetrahydrofuran; and 
nitriles, such as acetonitrile and benzonitrile. The reaction is 
preferably carried out in dimethylsulphoxide without a further solvent. 
As already mentioned, the new compounds of the formula XV can be prepared 
by the process described under 16. 
If, in process 16, 3-fluoro-4-pyrrolobenzaldehyde is used as the aldehyde 
of the formula XVIII and isopropylisonitrile is used as the isonitrile of 
the formula XXVI, the process can be represented by the following 
equation: 
##STR125## 
Aldehydes of the formula XVIII in which R.sup.1 and R.sup.2 have the 
meanings given as preferred in the case of the compounds of the formula I 
are preferably used. The aldehydes of the formula XVIII are new. They can 
be prepared by the process described under (18). 
Isonitriles of the formula XXVI are new or can be prepared analogously to 
known processes. The substituent R.sup.6 preferably has the meanings given 
above as preferred in the case of the compounds of the formula I. The 
following compounds of the formula XXVI may be mentioned specifically: 
methylisonitrile, ethylisonitrile, n-propylisonitrile, 
isopropylisonitrile, n-butylisonitrile, sec.-butylisonitrile, 
isobutylisonitrile and tert.-butylisonitrile. 
The process is carried out by bringing the compound XVIII together with 
twice the molar amount of isonitrile of the formula XXVI and acetic acid 
in a diluent. 
The reaction is carried out at temperatures from +20.degree. C. to 
+150.degree. C. 
The reaction is preferably carried out at atmospheric pressure. 
All the inert organic solvents are used as diluents. These include, in 
particular, optionally halogenated aliphatic and aromatic hydrocarbons, 
such as pentane, hexane, cyclohexane, benzene, toluene, methylene 
chloride, chloroform and chlorobenzene; ethers, such as diethyl ether and 
tetrahydrofuran; and nitriles, such as acetonitrile and benzonitrile. 
Inorganic acids are used to split off the acetyl group. These acids include 
hydrogen halide acids, such as hydrochloric acid; sulphuric acid and 
phosphoric acid. The acetyl group can also be split off in the presence of 
inorganic bases, such as alkali metal or alkaline earth metal hydroxides, 
or carbonates or bicarbonates. 
The process is carried out by treating the acetylated compound directly, or 
after prior isolation, with an excess aqueous solution of the inorganic 
acid or base in a diluent as a solubilizing agent. 
The reaction is carried out at temperatures from +20.degree. C. to 
+150.degree. C. 
The reaction is preferably carried out at atmospheric pressure. 
All the inert organic solvents which are miscible with water can be used as 
diluents. These include ethers, such as tetrahydrofuran and dioxane; 
nitriles, such as acetonitrile; amides, such as dimethylformamide; 
alcohols, such as methanol and ethanol; and dimethyl sulphoxide. 
As already mentioned, the new compounds of the formula XVIII can be 
prepared by the process described under (18). 
If, in process (18), 3-trifluoromethyl-4-pyrrolobenzyl alcohol is used as 
the alcohol of the formula XXVII, the reaction can be represented by the 
following equation: 
##STR126## 
The compounds of the formula XXVII are new. They can be prepared by the 
process described under (24). Compounds of the formula XXVII in which 
R.sup.1 and R.sup.2 have the meanings given as preferred in the case of 
the compounds of the formula I are preferred. 
The following compounds of the formula XXVII may be mentioned specifically: 
______________________________________ 
##STR127## 
R.sup.1 R.sup.2 
______________________________________ 
H 3,5-Cl.sub.2 
2,5(CH.sub.3).sub.2 3,5-Cl.sub.2 
H 3-Cl 
2,5(CH.sub.3).sub.2 3-Cl 
H 3-Cl 5-CF.sub.3 
H 3-CN 
2,5(CH.sub.3).sub.2 3-Cl 5-CF.sub.3 
______________________________________ 
Oxidizing agents which may be mentioned for carrying out the process are: 
(a) activated dimethyl sulphoxide, such as dimethyl sulphoxide/acetic 
anhydride, dimethyl sulphoxide/thionyl chloride and dimethyl 
sulphoxide/oxalyl chloride, and (b) manganese dioxide. 
Process (a) is carried out by reacting the alcohol of the formula XIII with 
1-1.5 equivalents of the oxidizing agent. 
The reaction is carried out at temperatures from -70.degree. C. to 
+25.degree. C. 
The reaction is preferably carried out at atmospheric pressure. 
Inert organic solvents are used as the diluents, and examples which may be 
mentioned are: optionally chlorinated hydrocarbons, such as methylene 
chloride and chloroform, and ethers, such as diethyl ether and 
tetrahydrofuran. 
Process (b) is carried out by reacting the alcohol of the formula XXVII 
with excess manganese dioxide. 
The reaction is carried out at temperatures from +20.degree. C. to 
+150.degree. C., and it is preferably carried out at atmospheric pressure. 
The diluents used are: inert organic solvents, in particular aliphatic and 
aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, 
cyclohexane, benzene, toluene, methylene chloride and chloroform, ethers, 
such as diethyl ether and tetrahydrofuran, and ketones, such as acetone 
and methyl ethyl ketone. 
If, in process 18, 3-chloro-4-pyrrolobenzoylchloride is used as the 
compound of the formula XXVIII, the reaction can be represented by the 
following equation: 
##STR128## 
Compounds of the formula XXVIII are new. They can be prepared by the 
process described under (26). Compounds of the formula XVIII in which 
R.sup.1 and R.sup.2 have the meanings given as preferred in the case of 
the compounds of the formula I may be mentioned as preferred. 
The following compounds of the formula XXVIII may be mentioned 
specifically: 
______________________________________ 
##STR129## 
R.sup.1 R.sup.2 
______________________________________ 
H 3,5-Cl.sub.2 
2,5(CH.sub.3).sub.2 3,5-Cl.sub.2 
H 3-Cl 
2,5(CH.sub.3).sub.2 3-Cl 
H 3-Cl 5-CF.sub.3 
H 3-CN 
2,5(CH.sub.3).sub.2 3-Cl 5-CF.sub.3 
______________________________________ 
The reducing agent used is H.sub.2 /catalyst, and palladium-on-barium 
sulphate may be mentioned as an example of the catalyst. 
The process is carried out by passing a stream of hydrogen through a 
solution of the compound XXVIII in a boiling diluent, after addition of 
5-10 mol % of catalyst. 
The reaction is carried out at temperatures of 100.degree.-200.degree. C., 
and it is preferably carried out at atmospheric pressure. 
The diluents used are aliphatic and aromatic hydrocarbons. Examples which 
may be mentioned are: hexane, heptane, cyclohexane, benzene, toluene and 
the xylenes. 
As already mentioned, the new compounds of the formula XIX can be prepared 
by the process described under 20. 
If, in process (20), 3-chloro-4-pyrrolocarbethoxyacetophenone is used as 
the compound of the formula XXIX, the process can be represented by the 
following equation: 
##STR130## 
The compounds of the formula XXIX are new. They can be prepared by the 
process described below under (28). Compounds of the formula XIX in which 
R.sup.1 and R.sup.2 have the meanings given as preferred in the case of 
the compounds of the formula I and Alk represents methyl or ethyl are 
preferably used. 
The following compounds may be mentioned specifically: 
______________________________________ 
##STR131## 
R.sup.1 R.sup.2 
______________________________________ 
H 3,5-Cl.sub.2 
2,5(CH.sub.3).sub.2 3,5-Cl.sub.2 
H 3-Cl 
2,5(CH.sub.3).sub.2 3-Cl 
H 3-Cl 5-CF.sub.3 
H 3-CN 
2,5(CH.sub.3).sub.2 3-Cl 5-CF.sub.3 
______________________________________ 
The process is carried out by reacting the compound of the formula XXIX in 
a diluent in the presence of an excess of an acid or base. 
The reaction is carried out at temperatures from +20.degree. C. to 
+150.degree. C. 
The reaction is preferably carried out at atmospheric pressure. 
All the inert organic solvents are used as diluents. These include, in 
particular, aliphatic and aromatic, optionally halogenated hydrocarbons, 
such as pentane, hexane, cyclohexane, benzene, toluene, methylene 
chloride, chloroform and chlorobenzene; ethers, such as diethyl ether, 
tetrahydrofuran, ethylene glycol mono- methyl ether and ethylene glycol 
dimethyl ether; alcohols such as methanol and ethanol, and water. The 
reaction is preferably carried out in alcohol or in water. 
All the inorganic acids can be used as acids. These include, in particular, 
hydrogen halide acids, such as hydrochloric acid, and furthermore 
sulphuric acid and phosphoric acid. 
All the inorganic bases can be used as bases. These include alkali metal 
and alkaline earth metal carbonates, such as sodium carbonate and 
potassium carbonate, and hydroxides, such as sodium hydroxide and 
potassium hydroxide. 
As already mentioned, the new compounds of the formula XXIV can be prepared 
by the process described under (22). 
If, in process (22), 3-methyl-4-pyrrolobenzaldehyde is used as the aldehyde 
of the formula XVIII, process 20 can be represented by the following 
equation: 
##STR132## 
The compounds mentioned above are preferably used as the aldehydes of the 
formula XVIII. 
The process is carried out by reacting equivalent amounts of the compound 
XVIII and nitromethane in a diluent in the presence of a base. 
The reaction is carried out at temperatures from -20.degree. C. to 
+50.degree. C. 
The reaction is preferably carried out at atmospheric pressure. 
All the inert organic solvents are used as diluents. These include, in 
particular, ethers, such as diethyl ether and tetrahydrofuran; and 
alcohols, such as methanol and ethanol. 
The bases used are: alkali metal and alkaline earth metal hydroxides, such 
as sodium hydroxide and potassium hydroxide, and alcoholates, such as 
sodium methylate, potassium methylate, sodium ethylate and potassium 
ethylate. 
As already mentioned, the new compounds of the formula XVII can be prepared 
by the process described under (24) by reducing correspondingly 
substituted benzoic acids or benzoic acid esters of the formula XXXIII. 
The compounds of the formula XXXIII are new. They can be prepared by 
process (30) described below. Compounds of the formula XXXIII in which 
R.sup.1 and R.sup.2 have the meanings given as preferred in the case of 
the compounds of the formula I and R.sup.9 represents hydrogen, methyl or 
ethyl are preferably used. 
The following compounds of the formula XXXIII may be mentioned 
specifically: 
______________________________________ 
##STR133## 
R.sup.1 R.sup.2 
______________________________________ 
H 3,5-Cl.sub.2 
2,5(CH.sub.3).sub.2 3,5-Cl.sub.2 
H 3-Cl 
2,5(CH.sub.3).sub.2 3-Cl 
H 3-Cl 5-CF.sub.3 
H 3-CN 
2,5(CH.sub.3).sub.2 3-Cl 5-CF.sub.3 
______________________________________ 
The reducing agents used are: for esters of the formula XXXIII, complex 
metal hydrides, such as, for example, LAlH.sub.4, and for acids of the 
formula XXXIII, boranes, such as, for example, diborane, and complex metal 
hydrides, such as, for example, LiAlH.sub.4. 
The process is carried out by reacting the compounds of the formula XXXIII 
with 1-4 times the molar amount of reducing agent in a diluent. 
The reaction is carried out at temperatures from -50.degree. C. to 
+100.degree. C., and it is preferably carried out at atmospheric pressure. 
The diluents used are: ethers, such as diethyl ether, tetrahydrofuran and 
dioxane. 
As already mentioned, the new compounds of the formula XXXIII can be 
prepared by the process described under (26). 
If, in process (26), 3-bromo-4-pyrrolobenzoic acid is used as the 
carboxylic acid of the formula XXXIII, the reaction can be represented by 
the following equation: 
##STR134## 
The compounds of the formula XXXIII are new. They can be prepared by the 
process described under (30). The compounds of the formula XXXIII 
described above are preferably used. 
Inorganic acid chlorides can be used as the halogenating agents. Examples 
which may be mentioned are: phosphorus oxychloride, phosphorus 
pentachloride and thionyl chloride. 
The reaction is carried out by treating a compound of the formula XXXIII 
with 0.5-1.5 equivalents of the inorganic acid chloride, if appropriate in 
a diluent. 
The reaction is carried out at temperatures from 20.degree. C. to 
100.degree. C. and it is preferably carried out at atmospheric pressure. 
All the inert organic solvents can be used as diluents. These include, in 
particular, aliphatic and aromatic, optionally halogenated hydrocarbons, 
such as pentane, hexane, cylcohexane, benzene, toluene, methylene 
chloride, chloroform and chlorobenzene; ethers, such as diethyl ether, 
tetrahydrofuran and dioxane, and phosphorus oxychloride. 
The reaction is preferably carried out without a diluent. 
As already mentioned, the new compounds of the formula XXIX can be prepared 
by the process described under (28). 
If, in process 28, isopropyl 4-pyrrolobenzoate is used as the compound of 
the formula XXXIII and methyl acetate is used as the compound of the 
formula XXXVI, process 28 can be represented by the following equation: 
##STR135## 
The compounds mentioned above are preferably used as the compounds of the 
formula XXXVI. 
Compounds of the formula XXXVI are known or can be prepared analogously to 
known processes. 
The following compounds of the formula XXXVI may be mentioned specifically: 
methyl acetate and ethyl acetate. 
The process is carried out by reacting equivalent amounts of the compounds 
XXXIII and XXXVI and a base in a diluent. 
The reaction is carried out at temperatures from 0.degree. c. to 
+150.degree. C. 
The reaction is preferably carried out at atmospheric pressure. 
All the inert organic solvents are used as diluents. These include, in 
particular, aliphatic and aromatic hydrocarbons, such as pentane, hexane, 
heptane, cyclohexane, benzene and toluene; ethers, such as diethyl ether 
and tetrahydrofuran; and alcohols, such as methanol and ethanol. 
The bases used are alkali metal and alkaline earth metal hydrides, such as 
sodium hydride and calcium hydride, and alkaline metal alcoholates, such 
as sodium methylate, potassium methylate, sodium ethylate and potassium 
ethylate. 
As already mentioned, the new compounds of the formula XXXIII can be 
prepared by the process described under (30). 
The compounds of the formula XXXVII used as starting substances for process 
(30) are known or can be prepared analogously to known processes. 
Compounds of the formula XXXVII in which R.sup.2 has the meanings given as 
preferred in the case of the compounds of the formula I and R.sup.9 
represents methyl, ethyl, propyl or hydrogen are preferred. 
The following compounds of the formula XXXVII may be mentioned 
specifically: 
______________________________________ 
##STR136## 
R.sup.1 R.sup.2 
______________________________________ 
H 3,5-Cl.sub.2 
2,5(CH.sub.3).sub.2 3,5-Cl.sub.2 
H 3-Cl 
2,5(CH.sub.3).sub.2 3-Cl 
H 3-Cl 5-CF.sub.3 
H 3-CN 
2,5(CH.sub.3).sub.2 3-Cl 5-CF.sub.3 
______________________________________ 
The active compounds have a favorable toxicity towards warm-blooded animals 
and are suitable as agents for promoting yield in animals for breeding and 
stock animals. They are used here for promoting and accelerating growth 
and milk and wool production, as well as for improving the feed 
utilization and the meat quality and for shifting the meat/fat ratio in 
favor of meat. 
The compounds according to the invention moreover exhibit a good 
anti-inflammatory action in the carrageenan induced paw oedema test in 
rats. 
They can therefore be used as anti-inflammatories and antirheumatics and 
for the treatment of inflammation and oedemas. 
The stock animals and animals for breeding include mammals, such as, for 
example, cattle, horses, sheep, pigs, goats, camels, water buffalo, asses, 
rabbits, fallow deer and reindeer, fur-bearing animals, such as, for 
example, mink, chinchillas and racoons, birds, such as, for example, 
chickens, geese, turkeys and ducks, fresh and saltwater fish, such as, for 
example, trout, carp and eels, and reptiles. 
The active compounds are used in all the growth and yield phases of the 
animals regardless of the strain and sex of the animals. The active 
compounds are preferably used in the intensive growth and yield phase. The 
intensive growth and yield phase lasts from one month to 10 years, 
depending on the animal species. The active compounds have proved to be 
particularly useful in the rearing and husbandry of young animals and 
animals for fattening. 
The active compounds are used enterally or parenterally, directly or in the 
form of formulations suitable for animals. Enteral use of the active 
compounds is carried out, for example, orally in the form of powders, 
tablets, capsules, pastes, drinks or granules, solutions, emulsions or 
suspensions for oral administration, boli and via the feed or via the 
drinking water. Parenteral use is carried out, for example, in the form of 
injection (intramuscular, subcutaneous or intravenous or by implants). 
Formulations for administration via the feed or the drinking water are to 
be particularly singled out. The active compounds can thereby be added to 
the feed directly or in the form of premixes or feed concentrates. 
The feed includes individual feedstuffs of vegetable origin, such as hay, 
beet, cereals and cereal byproducts, molasses and silage, individual 
feedstuffs of animal origin, such as meat, fats, milk products, bonemeal 
and fish products, and the individual feedstuffs, such as vitamins, 
proteins, sugars, starches, flours, amino acids, for example 
DL-methionine, and salts, such as lime and sodium chloride. The feed also 
includes supplement, ready-to-use and mixed feedstuffs. These contain 
individual feedstuffs in a composition which guarantees a balanced 
nutrition in respect of energy and protein supply and the supply of 
vitamins, mineral salts and trace elements. 
Premixes and feed concentrates are mixtures of the active compound with 
carriers and, if appropriate, other auxiliaries. The carriers include all 
the individual feedstuffs or mixtures thereof. 
The active compounds can be present in the formulations by themselves or as 
a mixture with other yield-promoting active compounds, mineral feedstuffs, 
trace element compounds, vitamins, nitrogen-containing non-protein 
compounds, dyestuffs, antioxidants, aroma substances, emulsifiers, flow 
control auxiliaries, preservatives and pressing auxiliaries. 
Other yield-promoting active compounds are, for example, antibiotics, such 
as tylosin and virginamycin. 
Mineral feedstuffs are, for example, dicalcium phosphate, magnesium oxide 
and sodium chloride. 
Trace element compounds are, for example, iron fumarate, sodium iodide, 
cobalt chloride, copper sulphate, zinc oxide and selenium compounds. 
Vitamins are, for example, vitamin A, vitamin D.sub.3 and vitamin E. 
Nitrogen-containing non-protein compounds are, for example, biuret and 
urea. 
Dyestuffs are, for example, carotinoids, such as canthaxidine, zeaxanthine 
or capsanthine, or all the dyestuffs which are permitted for coloring 
foodstuffs. 
Antioxidants are, for example ethoxyquin, butylhydroxy-toluene and ascorbic 
acid. 
Aroma substances are, for example, vanillin. 
Emulsifiers are, for example, esters of lactic acid and lecithin. 
Flow control auxiliaries are, for example, sodium stearate, calcium 
stearate, silicic acids, bentonites and ligninsulphonates. 
Preservatives are, for example, propionic acid, calcium propionate, sorbic 
acid and ascorbic acid. 
Pressing auxiliaries are, for example, ligninsulphonates and cellulose 
ethers. 
The concentration of the active compounds in the feed is usually about 
0.001-500 ppm, preferably 0.1-50 ppm. 
The concentration of the active compounds in the premixes or feed 
concentrates is about 0.5 to 50 per cent by weight, preferably 1 to 20 per 
cent by weight. 
The amount of active compounds administered to the animals to achieve the 
desired effect can be varied widely because of the favorable properties of 
the active compounds. It is preferably about 0.001 to 50 mg/kg, in 
particular 0.01 to 5 mg/kg of body weight per day. The appropriate amount 
of the active compound and the appropriate duration of the administration 
depend, in particular, on the species, the age, the sex, the state of 
health and the type of housing and feeding of the animals and can easily 
be determined by any expert. 
The active compounds are administered to the animals by customary methods. 
The nature of the administration depends, in particular, on the species, 
the behaviour and the state of health of the animals. 
The active compounds can be administered a single time. However, the active 
compounds can also be administered temporarily or continuously throughout 
the entire or throughout part of the growth and yield phase. In the case 
of continuous administration, they can be used once or several times daily 
at regular or irregular intervals. 
An example of the composition of a chick-rearing feed containing active 
compound according to the invention: 200 g of wheat, 340 g of corn, 361 g 
of shredded soy beans, 60 g of beef tallow, 15 g of dicalcium phosphate, 
10 g of calcium carbonate, 4 g of iodinated sodium chloride, 7.5 g of a 
vitamin-mineral mixture of the composition shown below and 2.5 g of an 
active compound premix of the composition shown below give, after thorough 
mixing, 1 kg of feed. 
1 kg of vitamin-mineral mixture contains: 600 I.U. of vitamin A, 100 I.U. 
of vitamin D.sub.3, 10 mg of vitamin E, 1 mg of vitamin K.sub.3, 3 mg of 
riboflavin, 2 mg of pyridoxine, 20 mcg of vitamin B.sub.12, 5 mg of 
calcium pantothenate, 30 mg of nicotinic acid, 200 mg of choline chloride, 
200 mg of MnSO.sub.4 .times.H.sub.2 O, 140 mg of ZnSO.sub.4 .times.7 
H.sub.2 O, 100 mg of FeSO.sub.4 .times.7 H.sub.2 O and 20 mg of CuSO.sub.4 
.times.5 H.sub.2 O in cereal flour as a carrier. 
1 kg of active compound premix contain 100 g of active compound and 900 g 
of wheat flour. 
An example of the composition of a pig-rearing feed containing active 
compound according to the invention: 630 g of shredded cereal feed 
(composed of 200 g of corn, 150 g of shredded barley, 150 g of shredded 
oats and 130 g of shredded wheat), 80 g of fishmeal, 60 g of shredded soy 
beans, 60 g of tapioca flour, 38 g of brewer's yeast, 50 g of a 
vitamin-mineral mixture (composition as for the chick feed) 30 g of 
linseed cake, 30 g of corn gluten feed, 10 g of soy bean oil, 10 g of 
sugarcane molasses and 2 g of an active compound premix of the composition 
shown below give, after thorough mixing, 1 kg of feed. 
1 kg of active compound premix contains 200 g of active compound, 20 g of 
vegetable oil and 780 g of calcium carbonate powder. 
An example of the composition of a cattle feed containing the active 
compound according to the invention: 69.95% of shredded cereal feed, 10% 
of ground corn cobs, 8% of soy bean flour, 5% of lucerne flour, 5% of 
molasses, 0.6% of urea, 0.5% of calcium phosphate, 0.5% of calcium 
carbonate, 0.3% of sodium chloride and 0.15% of a vitamin-mineral mixture. 
The vitamin-mineral mixture contains, per kg, 70,000 I.U. of vitamin A, 
70,000 I.U. of vitamin D.sub.3, 100 mg of vitamin E, 50 mg of MnSO.sub.4 
.times.H.sub.2 O and 30 mg of ZnSO.sub.4 .times.7H.sub.2 O in cereal flour 
as the carrier. 
The active compound is admixed with the vitamin-mineral mixture in the 
required amount and this mixture is then mixed thoroughly with the other 
constituents.

EXAMPLE A 
Rat feeding test 
Female laboratory rats weighing 90-110 g of the SPF Wistar type (Zuchtung 
Hagemann) are fed ad libitum with standard rat food to which the desired 
amount of active compound has been added. Each experimental set-up is 
carried out with food of an identical batch, so that differences in the 
composition of the food cannot impair the comparability of the results. 
The rats are given water ad libitum. 
Each test group is formed from 12 rats and the rats are fed with food to 
which the desired amount of active compound has been added. A control 
group is given food with no active compound. The average body weight and 
the scatter in the body weights of the rats is the same in each test 
group, so that comparability of the test groups with one another is 
guaranteed. 
The weight increase during the 13-day test is determined. 
The results which can be seen from the table are obtained: 
TABLE 
______________________________________ 
Rat feeding test 
Active compound Dose Weight increase 
Example No. 25 ppm after 13 days 
______________________________________ 
Control 100 
without active compound 
1 135 
2 130 
10 131 
12 131 
12.7 137 
12.9 129 
11.1 120 
8 125 
12.8 137 
12.14 115 
12.12 122 
13 125 
13.1 145 
______________________________________ 
PREATION EXAMPLES 
EXAMPLE 1 
2-(3,5-Dichloro-4-pyrrolophenyl)-2-hydroxy-N-tert.-butyl-1-ethylamine 
10 g of 
2-(3,5-dichloro-4-amino-phenyl)-2-hydroxy-N-tert.-butyl-1-ethylamine are 
heated under reflux with 5.3 g of 2,5-dimethoxytetrahydrofuran in 50 ml of 
acetic acid for 1 hour. After cooling, the mixture is poured onto 500 ml 
of water, rendered alkaline with concentrated ammonia solution and 
extracted twice with 50 ml of ethyl acetate each time and the organic 
phases are separated off and dried over sodium sulphate. Evaporation is 
carried out and the residue is purified by chromatography/silica gel 
column (HCCl.sub.3 :CH.sub.3 OH:NH.sub.3 =20:3:0.3), 10 g of melting 
point: 125.degree. C. 
EXAMPLE 2 
2-[3,5-Dichloro-4-(2',5'-dimethylpyrrolo)-phenyl]-2-hydroxy-N-tert.-butyl-1 
-ethylamine 
A solution of 15 g of 
2-(3,5-dichloro-4-amino-phenyl)-2-hydroxy-N-tert.-butyl-1-ethylamine and 
10.3 g of 2,5-hexanedione in 75 ml of acetic acid was heated under reflux 
for 12 hours. After the working up described in Example 1, 10.2 g of 
melting point: 95.degree. C. are obtained. 
Instead of 2,5-hexanedione, 2,5-dimethyl-2,5-dimethoxy-tetrahydrofuran can 
be used to give the abovementioned compound in a yield of 13 g. Melting 
point: 95.degree. C. 
EXAMPLE 2a 
The following compounds were obtained by the reaction described in Example 
1 and 2 and were characterized by .sup.1 H-NMR. 
__________________________________________________________________________ 
##STR137## 
Example 
No. Ar R.sup.1 m.p. .degree.C. 
__________________________________________________________________________ 
##STR138## CH(CH.sub.3).sub.2 120 
4 
##STR139## 
##STR140## Oil 
5 
##STR141## 
##STR142## 100 
6 
##STR143## 
##STR144## 120-125 
7 
##STR145## 
##STR146## Isomer A Oil Isomer B Oil 
8 
##STR147## 
##STR148## 110 
9 
##STR149## 
##STR150## Oil 
10 
##STR151## 86-90 
11.1 
##STR152## 114 
11.2 
##STR153## 
12 
##STR154## 
##STR155## Oil 
12.1 
##STR156## CH(CH.sub.3).sub.2 98-100 
12.2 
##STR157## CH(CH.sub.3).sub.2 Oil 
12.3 
##STR158## C(CH.sub.3).sub.3 260 
12.4 
##STR159## 
##STR160## 97 
12.5 
##STR161## 
##STR162## Oil 
12.6 
##STR163## 
##STR164## 65 
12.7 
##STR165## CH(CH.sub.3)CH.sub.2 OCH.sub.3 
75 
12.7.1 
##STR166## CH(CH.sub.3)CH.sub.2OCH.sub.3 
72 
12.8 
##STR167## CH(CH.sub.3)CH.sub.2OCH.sub.3 
Oil 
12.9 
##STR168## 
##STR169## Oil 
12.10 
##STR170## CH(CH.sub.3)C(CH.sub.3).sub.2OCH.sub.3 
75 
12.11 
##STR171## CH(CH.sub.3).sub.2OCH.sub.3 
Oil 
12.12 
##STR172## C(CH.sub.3).sub.3 74-76 
12.13 
##STR173## C(CH.sub.3).sub. 3 Oil 
12.14 
##STR174## CH(CH.sub.3).sub.2 115-118 
12.15 
##STR175## C(CH.sub.3).sub.3 102 
12.16 
##STR176## C(CH.sub.3).sub.3 Oil 
12.17 
##STR177## C(CH.sub.3).sub.3 113 
__________________________________________________________________________ 
EXAMPLE 13 
2-(3,5-Dichloro-4-pyrrolo-phenyl)-2-(1,2-dimethylpropyldimethyl-silyloxy)-N 
-tert.-butyl-ethylamine 
##STR178## 
3.27 g (0.01 mol) of 
2-(3,5-dichloro-4-pyrrolo-phenyl)-2-hydroxy-N-tert.-butyl-ethylamine 
(Example 1) are added to 1.38 g (0.02 mol) of imidazole in 15 ml of 
absolute dimethylformamide. 1.8 g of dimethyl-1,2-dimethyl-propylsilyl 
chloride are now added at 0.degree. to 5.degree. C. The mixture is stirred 
for 2 hours, while cooling with ice, and is concentrated, the residue is 
taken up in toluene/water, the phases are separated, the toluene phase is 
washed 4 times with water, dried and concentrated and the residue is freed 
from solvent residues using an oil pump. 4.8 g of an almost colorless oil 
are obtained. 
##STR179## 
is obtained as a colorless oil in a corresponding procedure with 
dimethyl-tert.-butyl-silyl chloride. 
EXAMPLE 14 
5-(3,5-Dichloro-4-pyrrolo-phenyl)-3-tert.-butyl-2-oxazolidinone 
##STR180## 
A solution of 1 g of COCl.sub.2 in 20 ml of methylene chloride is added 
dropwise to 3.27 g (0.01 mol) of 
2-(3,5-dichloro-4-pyrrolo-phenyl)-2-hydroxy-N-tert.-butyl-ethylamine, 
dissolved in 30 ml of methylene chloride and 3 g of triethylamine, at 
-5.degree. C. in the course of 20 minutes. The mixture is stirred at 
-5.degree. C. for 30 minutes and at room temperature for 1 hour and 
evaporated in vacuo and the residue is chromatographed over a silica gel 
column using n-heptane-CH.sub.2 Cl.sub.2 =1:1. Yield 1.5 g. 
EXAMPLE 15 
5-(3,5-Dichloro-4-pyrrolo-phenyl)-3-tert.-butyl-oxazolidine 
##STR181## 
3.27 g (0.01 mol) of 
2-(3,5-dichloro-4-pyrrolo-phenyl)-2-hydroxy-N-tert.-butyl-ethylamine, 
dissolved in 60 ml of toluene, are heated with 18 ml of formaldehyde (38% 
strength) with the addition of 2 mg of p-toluene-sulphonic acid, using a 
water separator. When no further water has separated out (after about 1 
hour), the mixture is cooled, washed twice with 10% strength sodium 
hydroxide solution and then with water and dried over Na.sub.2 SO.sub.4. 
After evaporation, the residue is chromatographed through a silica gel 
column (hexane, methylene chloride=1:1) to give 2.5 g of an oil. 
EXAMPLE 16 
2-(3,5-Dichloro-4-pyrrolo-phenyl)-2-acetoxy-N-tert.-butyl-ethylamine 
3 g of triethylamine are added to 3.27 g (0.01 mol) of 
2-(3,5-dichloro-4-pyrrolo-phenyl)-2-hydroxy-N-tert.-butyl-ethylamine, 
dissolved in 50 ml of CHCl.sub.3, 1.1 g (0.011 mol) of acetic anhydride 
are added dropwise at -5.degree. C. and the mixture is warmed at room 
temperature for 2 hours. When the reaction has ended (control by thin 
layer chromatography), the mixture is evaporated in vacuo, the residue is 
taken up in ethyl acetate, the mixture is washed with sodium bicarbonate 
solution and then with saturated sodium chloride solution, the organic 
phase is evaporated and the residue is chromatographed through a silica 
gel column (hexane-ethyl acetate=2:1). Yield: 2.8 g. 
The starting compounds used for Examples 11.1 and 11.2 were obtained by the 
following route: 
10.9 g (29.8 mmol) of 
4-amino-3,5-dichloro-.omega.-[(R)-1-cyclohexyl-ethylamino]-acetophenone 
hydrochloride, melting point 226.degree. C. (obtained from 
4-amino-3,5-dichloro-.omega.-bromo-acetophenone by reaction with 
(R)-1-cyclohexyl-ethylamine) are dissolved in 75 ml of methanol and 18 ml 
of water, and a solution of 2.5 g of sodium borohydride in 18 ml of water 
is added dropwise at a pH of between 2 and 7. The pH is brought to 9, the 
mixture is concentrated and the residue is extracted with ethyl acetate. 
The ethyl acetate phase is washed with water, dried and concentrated. The 
crystalline product is stirred with heptane, filtered off with suction and 
washed with heptane. 6.5 g of 
2-(3,5-dichloro-4-amino-phenyl)-2-hydroxy-N-[(R)-1-cyclohexyl-ethyl]-ethyl 
amine, melting point 110.degree. to 116.degree. C., are obtained. The two 
diastereomers are resolved by fractional recrystallization from 
acetonitrile: 
______________________________________ 
Physical data: 
______________________________________ 
Diastereomer 11.1: 
Melting point: 142.degree. C. 
[.alpha.].sup.20 = -22 
(c = 0.69, methanol) 
589 
Diastereomer 11.2: 
Melting point: 108-111.degree. C. 
[.alpha.].sup.20 = -27.26 
(c = 0.8576, methanol) 
______________________________________ 
2-(3,5-Dichloro-4-amino-phenyl)-2-hydroxy-N-[(S)-1-cyclohexyl-ethyl]-ethyla 
mine is obtained in a corresponding manner from 
4-amino-3,5-dichloro-.omega.[(S)-1-cyclohexyl-ethylamino]-acetophenone and 
is resolved into the diastereomers C and D by fractional crystallization. 
A diastereomer mixture of 
2-(3,5-dichloro-4-aminophenyl)-2-hydroxy-N-(1-cyclohexyl-ethyl)-ethylamine 
is obtained in a corresponding manner from 
4-amino-3,5-dichloro-.omega.-(1-cyclohexyl-ethylamino)-acetophenone. 
It will be understood that the specification and examples are illustrative 
but not limitative of the present invention and that other embodiments 
within the spirit and scope of the invention will suggest themselves to 
those skilled in the art.