US 2006/0189614 A1 · Substituted diamino-1,3,5-triazine derivatives

Abstract

This invention concerns the compounds of formula the pharmaceutically acceptable acid addition salts and the stereochemically isomeric forms thereof, wherein R1 and R2 are each independently selected from hydrogen; hydroxy; amino; optionally substituted C1-6alkyl; C1-6alkyloxy; C1-6alkylcarbonyl; C1-6alkyloxycarbonyl; Ar1; mono- or di(C1-6alkyl)amino; mono- or di(C1-6alkyl)-aminocarbonyl; dihydro-2(3H)-furanone; or R1 and R2 taken together may form pyrrolidinyl, piperidinyl, morpholinyl, azido or mono- or di(C1-6alkyl)amino-C1-4alkylidene; R3 is hydrogen, Ar1, C1-6alkylcarbonyl, C1-6alkyl, C1-6alkyloxy-carbonyl, C1-6alkyl substituted with C1-6alkyloxycarbonyl; and R4, R5, R6, R7 and R8 are each independently selected from hydrogen, halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl or trihalomethyloxy; L is optionally substituted C1-10alkyl; C3-10alkenyl; C3-10alkynyl; C3-7cycloalkyl; Ar1 is optionally substituted phenyl; for the manufacture of a medicine for the treatment of subjects suffering from HIV (Human Immunodeficiency Virus) infection. It further relates to new compounds being a subgroup of the compounds of formula (I), their preparation and compositions comprising them.

Claims8

Dependent claims

1-17. (canceled)

A method for preparing a compound of formula (I-a),

wherein
R3 is hydrogen, Ar1, C1-6alkylcarbonyl, C1-6alkyl, C1-6alkyloxycarbonyl, C1-6alkyl substituted with C1-6alkyloxycarbonyl;
and
R4, R5, R6, R7 and R8 are each independently selected from hydrogen, hydroxy, halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl or trihalomethyloxy;
L is C1-10alkyl;
C3-10alkenyl;
C3-10alkynyl;
C3-7cycloalkyl;
or
L is C1-10alkyl substituted with one or two substituents independently selected from C3-7cycloalkyl;
indolyl or indolyl substituted with one, two, three or four substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
phenyl or phenyl substituted with one, two, three, four or five substituents each independently selected from halo, hydroxy, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
and,
Ar1 is phenyl, or phenyl substituted with one, two or three substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, nitro or trifluoromethyl;
with the proviso that the following compounds
Co.
No.
Alk
R1/R2
R3
R4
R5
R6
R7
R8
a
1-(4-(2-methylpropyl)phenyl)ethyl
H/H
H
CH3
H
H
H
H
b
1-(4-(2-methylpropyl)phenyl)ethyl
H/H
H
H
H
NO2
H
H
c
1-(4-(2-methylpropyl)phenyl)ethyl
H/H
C6H5
H
H
H
H
H
d
1-(4-(2-methylpropyl)phenyl)ethyl
H/H
H
NO2
H
CH3
H
H
e
1-(4-(2-methylpropyl)phenyl)ethyl
H/H
H
H
H
NH2
H
H
f
4-(2-methylpropyl)phenylmethyl
H/H
H
H
CF3
H
H
H
g
1-(4-(2-methylpropyl)phenyl)ethyl
H/H
H
H
H
Cl
H
H
h
4-(2-methylpropyl)phenylmethyl
H/H
H
H
H
H
H
H
i
3,4-dimethoxyphenylmethyl
H/H
H
H
H
H
H
H
j
2,3-dimethoxyphenylmethyl
H/H
H
H
H
H
H
H
k
3,4-diethoxyphenylmethyl
H/H
H
H
H
H
H
H
l
2-(3,5-(1,1-dimethylethyl)-4-
H/H
H
H
H
H
H
H
hydroxy-phenyl)ethyl
m
2-(3,5-(1,1-dimethylethyl)-4-
H/H
H
H
t-Bu
OH
t-Bu
H
hydroxy-phenyl)ethyl
n
phenylmethyl
H/H
H
CH3
H
H
H
H
o
phenylmethyl
H/H
H
H
H
H
H
H
are not included,
comprising the step of reacting an intermediate of formula (II),
wherein
L is C1-10alkyl;
C3-10alkenyl;
C3-10alkynyl;
C3-7cycloalkyl;
or
L is C1-10alkyl substituted with one or two substituents independently selected from C3-7cycloalkyl;
indolyl or indolyl substituted with one, two, three or four substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
phenyl or phenyl substituted with one, two, three, four or five substituents each independently selected from halo, hydroxy, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
with an intermediate of formula (III),
wherein
R3 is hydrogen, Ar1, C1-6alkylcarbonyl, C1-6alkyl, C1-6alkyloxycarbonyl, C1-6alkyl substituted with C1-6alkyloxycarbonyl;
and
R4, R5, R6, R7 and R8 are each independently selected from hydrogen, hydroxy, halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl or trihalomethyloxy;
and,
Ar1 is phenyl, or phenyl substituted with one, two or three substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, nitro or trifluoromethyl;
in a reaction-inert solvent.

178 more elements

A method for preparing a compound of formula (I-b),

wherein R1 and R2 are each independently selected from hydrogen;
hydroxy;
amino;
C1-6alkyl;
C1-6alkyloxy;
C1-6alkylcarbonyl;
C1-6alkyloxycarbonyl;
Ar1;
mono- or di(C1-6alkyl)amino;
mono- or di(C1-6alkyl)aminocarbonyl;
dihydro-2(3H)-furanone;
C1-6alkyl substituted with one or two substituents each independently selected from amino, imino, aminocarbonyl, aminocarbonylamino, hydroxy, hydroxyC1-6alkyloxy, carboxyl, mono- or di(C1-6alkyl)amino, C1-6alkyloxycarbonyl and thienyl;
or
R1 and R2 taken together may form pyrrolidinyl, piperidinyl, morpholinyl, azido or mono- or di(C1-6alkyl)aminoC1-4alkylidene;
R4, R5, R6, R7 and R8 are each independently selected from hydrogen, hydroxy, halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl or trihalomethyloxy;
L is C1-10alkyl;
C3-10alkenyl;
C3-10alkynyl;
C3-7cycloalkyl;
or
L is C1-10alkyl substituted with one or two substituents independently selected from C3-7cycloalkyl;
indolyl or indolyl substituted with one, two, three or four substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
phenyl or phenyl substituted with one, two, three, four or five substituents each independently selected from halo, hydroxy, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
and,
Ar1 is phenyl, or phenyl substituted with one, two or three substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, nitro or trifluoromethyl;
with the proviso that the following compounds
Co.
No.
Alk
R1/R2
R3
R4
R5
R6
R7
R8
a
1-(4-(2-methylpropyl)phenyl)ethyl
H/H
H
CH3
H
H
H
H
b
1-(4-(2-methylpropyl)phenyl)ethyl
H/H
H
H
H
NO2
H
H
d
1-(4-(2-methylpropyl)phenyl)ethyl
H/H
H
NO2
H
CH3
H
H
e
1-(4-(2-methylpropyl)phenyl)ethyl
H/H
H
H
H
NH2
H
H
f
4-(2-methylpropyl)phenylmethyl
H/H
H
H
CF3
H
H
H
g
1-(4-(2-methylpropyl)phenyl)ethyl
H/H
H
H
H
Cl
H
H
h
4-(2-methylpropyl)phenylmethyl
H/H
H
H
H
H
H
H
i
3,4-dimethoxyphenylmethyl
H/H
H
H
H
H
H
H
j
2,3-dimethoxyphenylmethyl
H/H
H
H
H
H
H
H
k
3,4-diethoxyphenylmethyl
H/H
H
H
H
H
H
H
l
2-(3,5-(1,1-dimethylethyl)-4-
H/H
H
H
H
H
H
H
hydroxy-phenyl)ethyl
m
2-(3,5-(1,1-dimethylethyl)-4-
H/H
H
H
t-Bu
OH
t-Bu
H
hydroxy-phenyl)ethyl
n
phenylmethyl
H/H
H
CH3
H
H
H
H
o
phenylmethyl
H/H
H
H
H
H
H
H
are not included,
comprising the step of reacting an intermediate of formula (IV),
wherein R1 and R2 are each independently selected from hydrogen;
hydroxy;
amino;
C1-6alkyl;
C1-6alkyloxy;
C1-6alkylcarbonyl;
C1-6alkyloxycarbonyl;
Ar1;
mono- or di(C1-6alkyl)amino;
mono- or di(C1-6alkyl)aminocarbonyl;
dihydro-2(3H)-furanone;
C1-6alkyl substituted with one or two substituents each independently selected from amino, imino, aminocarbonyl, aminocarbonylamino, hydroxy, hydroxyC1-6alkyloxy, carboxyl, mono- or di(C1-6alkyl)amino, C1-6alkyloxycarbonyl and thienyl;
or
R1 and R2 taken together may form pyrrolidinyl, piperidinyl, morpholinyl, azido or mono- or di(C1-6alkyl)aminoC1-4alkylidene;
L is C1-10alkyl;
C3-10alkenyl;
C3-10alkynyl;
C3-7cycloalkyl;
or
L is C1-10alkyl substituted with one or two substituents independently selected from C3-7cycloalkyl;
indolyl or indolyl substituted with one, two, three or four substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
phenyl or phenyl substituted with one, two, three, four or five substituents each independently selected from halo, hydroxy, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
and Ar1 is phenyl, or phenyl substituted with one, two or three substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, nitro or trifluoromethyl;
with an intermediate of formula (V),
herein
R4, R5, R6, R7 and R8 are each independently selected from hydrogen, hydroxy, halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl or trihalomethyloxy;
in a reaction-inert solvent.

190 more elements

A method for preparing a compound of formula (I-c),

wherein R1 and R2 are each independently selected from hydrogen;
hydroxy;
amino;
C1-6alkyl;
C1-6alkyloxy;
C1-6alkylcarbonyl;
C1-6alkyloxycarbonyl;
Ar1;
mono- or di(C1-6alkyl)amino;
mono- or di(C1-6alkyl)aminocarbonyl;
dihydro-2(3H)-furanone;
C1-6alkyl substituted with one or two substituents each independently selected from amino, imino, aminocarbonyl, anocarbonylamino, hydroxy, hydroxyC1-6alkyloxy, carboxyl, mono- or di(C1-6alkyl)amino, C1-6alkyloxycarbonyl and thienyl;
or
R1 and R2 taken together may form pyrrolidinyl, piperidinyl, morpholinyl, azido or mono- or di(C1-6alkyl)aminoC1-4alkylidene;
R3 is hydrogen, Ar1, C1-6alkylcarbonyl, C1-6alkyl, C1-6alkyloxycarbonyl, C1-6alkyl substituted with C1-6alkyloxycarbonyl;
and
R4, R5, R6, R7 and R8 are each independently selected from hydrogen, hydroxy, halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl or trihalomethyloxy;
Ar1 is phenyl, or phenyl substituted with one, two or three substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, nitro or trifluoromethyl;
wherein n is 1 to 4 and each R′ is independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
comprising the step of deprotecting an intermediate of formula (VI),
wherein R1 and R2 are each independently selected from hydrogen;
hydroxy;
amino;
C1-6alkyl;
C1-6alkyloxy;
C1-6alkylcarbonyl;
C1-6alkyloxycarbonyl;
Ar1;
mono- or di(C1-6alkyl)amino;
mono- or di(C1-6alkyl)aminocarbonyl;
dihydro-2(3H)-furanone;
C1-6alkyl substituted with one or two substituents each independently selected from amino, imino, aminocarbonyl, aminocarbonylamino, hydroxy, hydroxyC1-6alkyloxy, carboxyl, mono- or di(C1-6alkyl)amino, C1-6alkyloxycarbonyl and thienyl;
or
R1 and R2 taken together may form pyrrolidinyl, piperidinyl, morpholinyl, azido or mono- or di(C1-6alkyl)aminoC1-4alkylidene;
R3 is hydrogen, Ar1, C1-6alkylcarbonyl, C1-6alkyl, C1-6alkyloxycarbonyl, C1-6alkyl substituted with C1-6alkyloxycarbonyl;
and
R4, R5, R6, R7 and R8 are each independently selected from hydrogen, hydroxy, halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl or trihalomethyloxy;
Ar1 is phenyl, or phenyl substituted with one, two or three substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, nitro or trifluoromethyl;
wherein n is 1 to 4 and each R′ is independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
and wherein P is a suitable protective group;
according to art-known deprotection techniques.

38 more elements

A method of preparing a compound of formula (I-d),

wherein each R2 is independently selected from hydrogen;
hydroxy;
amino;
C1-6alkyl;
C1-6alkyloxy;
C1-6alkylcarbonyl;
C1-6alkyloxycarbonyl;
Ar1;
mono- or di(C1-6alkyl)amino;
mono- or di(C1-6alkyl)aminocarbonyl;
dihydro-2(3H)-furanone;
C1-6alkyl substituted with one or two substituents each independently selected from amino, imino, aminocarbonyl, aminocarbonylamino, hydroxy, hydroxyC1-6alkyloxy, carboxyl, mono- or di(C1-6alkyl)amino, C1-6alkyloxycarbonyl and thienyl;
R3 is hydrogen, Ar1, C1-6alkylcarbonyl, C1-6alkyl, C1-6alkyloxycarbonyl, C1-6alkyl substituted with C1-6alkyloxycarbonyl;
and
R4, R5, R6, R7 and R8 are each independently selected from hydrogen, hydroxy, halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl or trihalomethyloxy;
L is C1-10alkyl;
C3-10alkenyl;
C3-10alkynyl;
C3-7cycloalkyl;
or
L is C1-10alkyl substituted with one or two substituents independently selected from C3-7cycloalkyl;
indolyl or indolyl substituted with one, two, three or four substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
phenyl or phenyl substituted with one, two, three, four or five substituents each independently selected from halo, hydroxy, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
and,
Ar1 is phenyl, or phenyl substituted with one, two or three substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, nitro or trifluoromethyl;
comprising the step of reacting an intermediate of formula (VII)
wherein R3 is hydrogen, Ar1, C1-6alkylcarbonyl, C1-6alkyl, C1-6alkyloxycarbonyl, C1-6alkyl substituted with C1-6alkyloxycarbonyl;
and
R4, R5, R6, R7 and R8 are each independently selected from hydrogen, hydroxy, halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl or trihalomethyloxy;
L is C1-10alkyl;
C3-10alkenyl;
C3-10alkynyl;
C3-7cycloalkyl;
or
L is C1-10alkyl substituted with one or two substituents independently selected from C3-7cycloalkyl;
indolyl or indolyl substituted with one, two, three or four substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
phenyl or phenyl substituted with one, two, three, four or five substituents each independently selected from halo, hydroxy, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
and,
Ar1 is phenyl, or phenyl substituted with one, two or three substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, nitro or trifluoromethyl;
and wherein W1 is a suitable leaving group;
with an amino derivative of formula (VIII),
wherein each R2 is independently selected from hydrogen;
hydroxy;
amino;
C1-6alkyl;
C1-6alkyloxy;
C1-6alkylcarbonyl;
C1-6alkyloxycarbonyl;
Ar1;
mono- or di(C1-6alkyl)amino;
mono- or di(C1-6alkyl)aminocarbonyl;
dihydro-2(3H)-furanone;
C1-6alkyl substituted with one or two substituents each independently selected from amino, imino, aminocarbonyl, aminocarbonylamino, hydroxy, hydroxyC1-6alkyloxy, carboxyl, mono- or di(C1-6alkyl)amino, C1-6alkyloxycarbonyl and thienyl;
in a reaction inert and in the presence of a suitable base.

51 more elements

A method of preparing a compound of formula (I-f-1)

wherein R1′ and R2′ are each independently selected from hydroxy;
amino;
C1-6alkyl;
C1-6alkyloxy;
C1-6alkylcarbonyl;
C1-6alkyloxycarbonyl;
Ar1;
mono- or di(C1-6alkyl)amino;
mono- or di(C1-6alkyl)aminocarbonyl;
dihydro-2(3H)-furanone;
C1-6alkyl substituted with one or two substituents each independently selected from amino, imino, aminocarbonyl, aminocarbonylamino, hydroxy, hydroxyC1-6alkyloxy, carboxyl, mono- or di(C1-6alkyl)amino, C1-6alkyloxycarbonyl and thienyl;
or
R1′ and R2′ taken together may form pyrrolidinyl, piperidinyl, morpholinyl, azido or mono- or di(C1-6alkyl)aminoC1-4alkylidene
R4, R5, R6, R7 and R8 are each independently selected from hydrogen, hydroxy, halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl or trihalomethyloxy;
L is C1-10alkyl;
C3-10alkenyl;
C3-10alkynyl;
C3-7cycloalkyl;
or
L is C1-10alkyl substituted with one or two substituents independently selected from C3-7cycloalkyl;
indolyl or indolyl substituted with one, two, three or four substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
phenyl or phenyl substituted with one, two, three, four or five substituents each independently selected from halo, hydroxy, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
Ar1 is phenyl, or phenyl substituted with one, two or three substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, nitro or trifluoromethyl;
comprising the step of reacting an intermediate of formula (XI)
wherein R1′ and R2′ are each independently selected from hydroxy;
amino;
C1-6alkyl;
C1-6alkyloxy;
C1-6alkylcarbonyl;
C1-6alkyloxycarbonyl;
Ar1;
mono- or di(C1-6alkyl)amino;
mono- or di(C1-6alkyl)aminocarbonyl;
dihydro-2(3H)-furanone;
C1-6alkyl substituted with one or two substituents each independently selected from amino, imino, aminocarbonyl, aminocarbonylamino, hydroxy, hydroxyC1-6alkyloxy, carboxyl, mono- or di(C1-6alkyl)amino, C1-6alkyloxycarbonyl and thienyl;
or
R1′ and R2′ taken together may form pyrrolidinyl, piperidinyl, morpholinyl, azido or mono- or di(C1-6alkyl)aminoC1-4alkylidene;
with an intermediate of formula (XII),
wherein R4, R5, R6, R7 and R8 are each independently selected from hydrogen, hydroxy, halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl or trihalomethyloxy and wherein W3 is a suitable leaving group;
in a reaction-inert solvent and in the presence of a suitable base.

37 more elements

A method for preparing a compound of formula (I-f-2),

wherein R1′ and R2′ are each independently selected from hydroxy;
amino;
C1-6alkyl;
C1-6alkyloxy;
C1alkylcarbonyl;
C1-6alkyloxycarbonyl;
Ar1;
mono- or di(C1-6alkyl)amino;
mono- or di(C1-6alkyl)aminocarbonyl;
dihydro-2(3H)-furanone;
C1-6alkyl substituted with one or two substituents each independently selected from amino, imino, aminocarbonyl, aminocarbonylamino, hydroxy, hydroxyC1-6alkyloxy, carboxyl, mono- or di(C1-6alkyl)amino, C1-6alkyloxycarbonyl and thienyl;
or
R1′ and R2′ taken together may form pyrrolidinyl, piperidinyl, morpholinyl, azido or mono- or di(C1-6alkyl)aminoC1-4alkylidene;
L is C1-10alkyl;
C3-10alkenyl;
C3-10alkynyl;
C3-7cycloalkyl;
or
L is C1-10alkyl substituted with one or two substituents independently selected from C3-7cycloalkyl;
indolyl or indolyl substituted with one, two, three or four substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
phenyl or phenyl substituted with one, two, three, four or five substituents each independently selected from halo, hydroxy, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
Ar1 is phenyl, or phenyl substituted with one, two or three substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, nitro or trifluoromethyl;
comprising the step of reacting an intermediate of formula (XI-b);
wherein R1′ and R2′ are each independently selected from hydroxy;
amino;
C1-6alkyl;
C1-6alkyloxy;
C1-6alkylcarbonyl;
C1-6alkyloxycarbonyl;
Ar1;
mono- or di(C1-6alkyl)amino;
mono- or di(C1-6alkyl)aminocarbonyl;
dihydro-2(3H)-furanone;
C1-6alkyl substituted with one or two substituents each independently selected from amino, imino, aminocarbonyl, aminocarbonylamino, hydroxy, hydroxyC1-6alkyloxy, carboxyl, mono- or di(C1-6alkyl)amino, C1-6alkyloxycarbonyl and thienyl;
or
R1′ and R2′ taken together may form pyrrolidinyl, piperidinyl, morpholinyl, azido or mono- or di(C1-6alkyl)aminoC1-4alkylidene;
L is C1-10alkyl;
C3-10alkenyl;
C3-10alkynyl;
C3-7cycloalkyl;
or
L is C1-10alkyl substituted with one or two substituents independently selected from C3-7cycloalkyl;
indolyl or indolyl substituted with one, two, three or four substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
phenyl or phenyl substituted with one, two, three, four or five substituents each independently selected from halo, hydroxy, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy, C1-6alkylcarbonyl;
with an intermediate of formula (XII-b),
W3—Ar1 (XII-b)
wherein W3 is a suitable leaving group and
Ar1 is phenyl, or phenyl substituted with one, two or three substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, nitro or trifluoromethyl;
a reaction-inert solvent and in the presence of a suitable base.

46 more elements

Dependencies are inferred from the claim text.

Substituted diamino-1,3,5-triazine derivatives

Life of this patent

Substituted diamino-1,3,5-triazine derivatives

Life of this patent

Abstract

Claims8