Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-12-20
2004-03-09
Davis, Zinna Northington (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S139000
Reexamination Certificate
active
06703405
ABSTRACT:
DESCRIPTION
Substituted 4-phenyltetrahydroisoquinolinium salts, process for their preparation, their use as medicament, and medicament containing them
The invention relates to compounds of the formula I
wherein
R1, R2, R3 and R4 are independently of one another H, F, Cl, Br, I, CN, NO
2
, OH, NH
2
, C
a
H
2a+1
, C
qq
H
2qq−1
, OC
b
H
2b+1
, COOR50, OCOR50, COR50 or O
x
—(CH
2
)
y
— phenyl; wherein
a and b are independently of one another 1, 2, 3, 4, 5, 6, 7 or 8, wherein the groups C
a
H
2a+1
and OC
b
H
2b+1
independently of one another are unsubstituted or substituted where one or more H atoms are replaced by F atoms;
qq is 3, 4, 5, 6, 7 or 8, wherein the group C
qq
H
2qq−1
is unsubstituted or substituted where one or more H atoms are replaced by F atoms;
R50 is H or C
c
H
2c+1
,
c is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the group C
c
H
2c+1
is unsubstituted or substituted where one or more H atoms are replaced by F atoms;
x is zero or 1;
y is zero, 1, 2, 3 or 4, where the phenyl ring in the group O
x
—(CH
2
)
y
— phenyl is unsubstituted or substituted by 1-3 independently chosen from F, Cl, Br, CN, NO
2
, OH, NH
2
and C
d
H
2d+1
,
d is 1, 2, 3 or 4, wherein the group C
d
H
2d+1
is unsubstituted or substituted where one or more H atoms are replaced by F atoms; or
R1, R2, R3 and R4 are independently of one another chosen from a heteroaryl with at least one heteroatom chosen from 1, 2, 3 or 4 N atoms, 1 oxygen atom and 1 S atom, present as ring atoms; or
R1, R2, R3 and R4 are independently of one another CONR11R12 or NR11R12;
wherein
R11 and R12 are independently of one another H, C
e
H
2e+1
, or C
rr
H
2rr−1
,
e is 1, 2, 3, 4, 5, 6, 7 or 8;
rr is 3, 4, 5, 6, 7, or 8, wherein the groups C
e
H
2e+1
and C
rr
H
2rr−1
independently of one another are unsubstituted or substituted where one or more H atoms are replaced by F atoms and/or one or more CH
2
groups are replaced by O or NR13;
R13 is H or C
f
H
2f+1
;
f is 1, 2, 3 or 4, wherein the group C
f
H
2f+1
is unsubsitituted or substituted where one or
more H atoms are replaced by F atoms; or
R13 and a CH
2
group of R11 or R12 together with the N atom to which they are bonded form a 5- or 6-membered ring; or
R11 and R12 together with the N atom to which they are bonded form a 5-, 6- or 7-membered ring; or
R11 and R12 are independently of one another COR14, CSR14 or SO
2
R14; wherein
R14 is C
g
H
2g+1
;
g is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the group C
g
H
2g+1
is unsubsitituted or substituted where one or more H atoms are replaced by F atoms, and/or one or more CH
2
groups are replaced by O or NR13; or
R1, R2, R3 and R4 are independently of one another —O
h
—SO
j
—R15; wherein
h is zero or 1;
j is zero, 1 or 2;
R15 is C
k
H
2k+1
, OH, OC
l
H
2l+1
or NR17R18;
k is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the group C
k
H
2k+1
is unsubsitituted or substituted where one or more H atoms are replaced by F atoms;
l is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the group OC
l
H
2l+1
is unsubsitituted or substituted where one or more H atoms are replaced by F atoms;
R17 and R18 are independently of one another H or C
m
H
2m+1
;
m is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the group C
m
H
2m+1
is unsubstituted or substituted where one or more H atoms is replaced by F atoms and/or one or more CH
2
groups are replaced by O, CO, CS or NR19; R19 is H or C
n
H
2n+1
;
n is 1, 2, 3 or 4, wherein the group C
n
H
2n+1
is unsubstituted or substituted where one or more H atoms are replaced by F atoms; or
R17 and R18 together with the N atom to which they are bonded form a 5-, 6- or 7-membered ring; or
R19 and a CH
2
group of R17 or R18 together with the N atom to which they are bonded form a 5- or 6-membered ring;
R5 and R6 are independently of one another C
p
H
2p+1
, C
ss
H
2ss−1
, COR20 or SO
2
R20; wherein
p is 1, 2, 3, 4, 5, 6, 7 or 8;
ss is 3, 4, 5, 6, 7 or 8;
R20 is C
q
H
2q+1
;
q is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the groups C
p
H
2p+1
, C
ss
H
2ss−1
and C
q
H
2q+1
independently of one another are unsubstituted or substituted where one or more H atoms are replaced by F atoms and/or one or more CH
2
groups are replaced by O or NR21;
R21 is H or C
r
H
2r+1
;
r is 1, 2, 3 or 4; wherein the group C
r
H
2r+1
is unsubstituted or substituted where one or more H atoms are replaced by F atoms;
R7 is H, F, Cl, Br, I, C
s
H
2s+1
, C
dd
H
2dd−1
, OH, OC
t
H
2t+1
or OCOR22; wherein s and t are independently of one another 1, 2, 3, 4, 5, 6, 7 or 8;
dd is 3, 4, 5, 6, 7 or 8, wherein the groups C
s
H
2s+1
, C
dd
H
2dd−1
and OC
t
H
2t+1
independently of one another are unsubstituted or substituted where one or more H atoms are replaced by F atoms;
R22 is C
u
H
2u+1
;
u 1, 2, 3 or 4, wherein the group C
u
H
2u+1
is unsubstituted or substituted where one or more H atoms are replaced by F atoms;
R8, R9 and R10 are independently of one another —O
v
—SO
w
—R
23
; wherein
v is zero or 1;
w is zero, 1 or 2;
R23 is C
nn
H
2nn+1
, C
mm
H
2mm−1
, OH, OC
pp
H
2pp+1
or NR25R26; nn and pp are independently of one another 1, 2, 3, 4, 5, 6, 7 or 8, mm is 3, 4, 5, 6, 7 or 8, wherein the groups C
nn
H
2nn+1
, C
mm
H
2mm−1
and OC
pp
H
2pp+1
independently of one another are unsubstituted or substituted where one or more H atoms are replaced by F atoms;
R25 and R26 are independently of one another H, CN, C
z
H
2z+1
, or C
zz
H
2zz−1
;
z is 1, 2, 3, 4, 5, 6, 7 or 8;
zz is 3, 4, 5, 6, 7 or 8, wherein the group C
z
H
2z+1
is unsubstituted or substituted where one or more H atoms are replaced by F atoms and,
wherein the group C
z
H
2z+1
, is unsubstituted or substituted where one or more H atoms are replaced by F atoms and/or one or more CH
2
groups are replaced by O, CO, CS or NR27;
R27 is H or C
aa
H
2aa+1
;
aa is 1, 2, 3 or 4, wherein the group C
aa
H
2aa+1
is unsubstituted or substituted where one or more H atoms are replaced by F atoms; or
R27 and a CH
2
group of R25 or R26 together with the N atom to which they are bonded form a 5- or 6-membered ring; or
R25 and R26 together with the N atom to which they are bonded form a 5-, 6- or 7-membered ring, or
R8, R9 and R10 are independently of one another NR32COR30, NR32CSR30 or NR32SO
bb
R30; wherein
R30 is H, C
cc
H
2cc+1
, C
yy
H
2yy−1
, pyrrolidinyl or piperidinyl, wherein the pyrrolidinyl or piperidinyl is unsubstituted or substituted where a CH
2
group is replaced by O or NR33;
R32 and R33 are independently of one another H or C
h
H
2h+1
;
bb is 2 or 3;
cc is 1, 2, 3, 4, 5, 6, 7 or 8;
yy is 3, 4, 5, 6, 7 or 8;
h is 1, 2, 3, 4, 5, 6, 7 or 8,
wherein the group C
h
H
2h+1
is unsubstituted or substituted where one or more H atoms are replaced by F atoms, and wherein the groups C
cc
H
2cc+1
and C
yy
H
2yy−1
independently of one another are unsubstituted or substituted where one or more H atoms are replaced by F atoms and/or one or more CH
2
groups are replaced by O or NR31;
R31 is H, C
kk
H
2kk+1
, or COR65;
kk is 1, 2, 3, or 4; wherein the group C
kk
H
2kk+1
is unsubstituted or substituted where one or more H atoms are replaced by F atoms, R65 is H, or C
xx
H
2xx+1
;
xx is 1, 2, 3 or 4, wherein the group C
xx
H
2xx+1
is unsubstituted or substituted where one or more H atoms are replaced by F atoms; or
R31 together with a CH
2
group of R30 and the N atom to which they are jointly bonded forms a 5-, 6- or 7-membered ring; or
R30 is a 5- or 6-membered heteroaryl with at least one hetero atom chosen from 1, 2, 3 or 4 N atoms, 1 S atoms and 1 O atoms which is unsubstituted or substituted by up to three substituents chosen from F, Cl, Br, I, C
oo
H
2oo+1
, and NR70R71;
R70 and R71 are independently of one another H, C
uu
H
2uu+1
or COR72;
R72 is H, or C
vv
H
2vv+1
;
oo, uu and vv are independently of one another 1, 2, 3, 4, 5, 6, 7 or 8, wherein the groups C
oo
H
2oo+1
,
Bleich Markus
Heinelt Uwe
Hofmeister Armin
Lang Hans-Jochen
Wirth Klaus
Aventis Pharma Deutschland GmbH
Davis Zinna Northington
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
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