IP Library › Granted Patent US 7,417,066
Granted Patent B2
US 7,417,066 · App. 11/448,140 · Granted Aug 26, 2008

Inhibitors of soluble adenylate cyclase

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Quick Facts
Patent No.
US 7,417,066
App. No.
11/448,140
Granted
Aug 26, 2008
Kind
B2
Abstract

The invention relates to compounds of general Formula I, the production thereof, and the use thereof as a medicinal product.

Claims (178)

1. A compound of Formula 1

wherein

R 1 is hydrogen, halogen, CF 3 , sulfonyl-C 1 -C 6 -alkyl, sulfonamide, cyano, C 3 -C 6 -cycloalkyl,

which C 3 -C 6 -cycloalkyl is optionally multiply saturated and optionally multiply substituted, or

 C 1 -C 6 -alkyl, C 1 -C 6 -aryl, C 1 -C 6 -acyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -acyl, C 1 -C 6 -acyl-C 1 -C 6 -acyl, C 1 -C 6 -alkyl-C 1 -C 6 -aryl, or C 1 -C 6 -aryl-C 1 -C 6 -alkyl,

which C 1 -C 6 -alkyl, C 1 -C 6 -aryl, C 1 -C 6 -acyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -acyl, C 1 -C 6 -acyl-C 1 -C 6 -acyl, C 1 -C 6 -alkyl-C 1 -C 6 -aryl or C 1 -C 6 -aryl-C 1 -C 6 -alkyl is optionally be interrupted singly or more than once, identically or differently by oxygen, sulfur or nitrogen,

R 2 is halogen, CF 3 , sulfonyl-C 1 -C 6 -alkyl, sulfonamide, cyano,

 C 3 -C 6 -cycloalkyl,

which C 3 -C 6 -cycloalkyl is optionally multiply saturated and optionally multiply substituted, or

 C 1 -C 6 -alkyl, C 1 -C 6 -aryl, C 1 -C 6 -acyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -alkyl,C 1 -C 6 -alkyl-C 1 -C 6 -acyl, C 1 -C 6 -acyl-C 1 -C 6 -acyl, C 1 -C 6 -alkyl-C 1 -C 6 -aryl, or C 1 -C 6 -aryl-C 1 -C 6 -alkyl,

which C 1 -C 6 -alkyl, C 1 -C 6 -aryl, C 1 -C 6 -acyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -acyl, C 1 -C 6 -acyl-C 1 -C 6 -acyl, C 1 -C 6 -alkyl-C 1 -C 6 -aryl or C 1 -C 6 -aryl-C 1 -C 6 -alkyl is optionally interrupted singly or more than once, identically or differently by oxygen, sulfur or nitrogen,

R 3 is C 6 -C 12 -aryl,

which C 6 -C 12 -aryl is optionally substituted singly or more than once, identically or differently with halogen, C 1 -C 6 -alkoxy, hydroxy, cyano, CO 2 —(C 1 -C 6 -alkyl), N—(C 1 -C 6 -alkyl) 2 , CO—NR 4 R 5 , CF 3 ,C 1 -C 6 -alkyl or C 1 -C 6 -acyl,

which C 1 -C 6 -alkyl or C 1 -C 6 -acyl is optionally singly or more than once substituted,

 C 5 -C 12 -heteroaryl,

which C 5 -C 12 -heteroaryl is optionally substituted singly or more than once, identically or differently with halogen, C 1 -C 6 -alkyl, C 1 -C 6 -acyl, C 1 -C 6 -alkoxy, hydroxy, cyano, CO 2 —(C 1 -C 6 -alkyl), N—(C 1 -C 6 -alkyl) 2 , CO—NR 4 R 5 or CF 3 , or

 C 3 -C 6 -cycloalkyl,

which C 3 -C 6 -cycloalkyl is optionally substituted singly or more than once, identically or differently with halogen, CF 3 hydroxy, cyano, CO 2 —(C 1 -C 6 -alkyl), C 1 -C 6 -alkyl, C 1 -C 6 -acyl, N—(C 1 -C 6 -alkyl) 2 , CO—NR 4 R 5 or C 1 -C 6 -alkoxy,

R 4 is hydrogen,

 C 3 -C 6 -cycloalkyl,

which C 3 -C 6 -cycloalkyl is optionally substituted singly or more than once, identically or differently with C 1 -C 6 -alkyl, C 1 -C 6 -acyl, C 1 -C 6 -alkoxy or CF 3 ,

 C 6 -C 12 -aryl,

which C 6 -C 12 -aryl is optionally substituted singly or more than once, identically or differently with halogen, C 1 -C 6 -alkyl, C 1 -C 6 -acyl, C 1 -C 6 -alkoxy, N—C 1 -C 6 -alkyl-C 1 -C 6 -alkyl, CF 3 or cyano,

 C 5 -C 12 -heteroaryl,

which C 5 -C 12 -heteroaryl is optionally substituted singly or more than once, identically or differently with halogen, C 1 -C 6 -alkyl, C 1 -C 6 -acyl, C 1 -C 6 -alkoxy, N—C 1 -C 6 -alkyl-C 1 -C 6 -alkyl, CF 3 or cyano, or

 C 1 -C 6 -alkyl,

which C 1 -C 6 -alkyl is optionally substituted,

R 5 is hydrogen,

 C 3 -C 6 -cycloalkyl,

which C 3 -C 6 -cycloalkyl is optionally substituted singly or more than once, identically or differently with C 1 -C 6 -alkyl, C 1 -C 6 -acyl, C 1 -C 6 -alkoxy or CF 3 ,

 C 6 -C 12 -aryl,

which C 5 -C 12 -heteroaryl is optionally substituted singly or more than once, identically or differently with halogen, with C 1 -C 6 -alkyl, C 1 -C 6 -acyl, C 1 -C 6 -alkoxy, N—C 1 -C 6 -alkyl-C 1 -C 6 -alkyl, CF 3 or cyano, or

 C 5 -C 12 -heteroaryl,

which C 5 -C 12 -heteroaryl is optionally substituted singly or more than once, identically or differently with halogen, C 1 -C 6 -alkyl, C 1 -C 6 -acyl, C 1 -C 6 -alkoxy, N—C 1 -C 6 -alkyl-C 1 -C 6 -alkyl, CF 3 or cyano, or

 C 1 -C 6 -alkyl,

which C 1 -C 6 -alkyl is optionally ean-be substituted,

or alternatively

R 4 and R 5 together form a 5-8-membered ring, which optionally further contains one or more heteroatoms,

X is sulfonyl, (CH 2 ) n or carbonyl,

Y is —(CH 2 ) n — or carbonyl,

Z is nitrogen,

A is oxygen or sulfur, and

n is 0-4,

or a diastereomer, enantiomer or salt thereof.

2. A compound of claim 1 , wherein:

R 1 is hydrogen, halogen, CF 3 , a C 3 -C 6 -cycloalkyl, sulfonyl-C 1 -C 6 -alkyl, sulfonamide, or cyano, C 1 -C 6 -alkyl, C 1 -C 6 -aryl, C 1 -C 6 -acyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl -C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -acyl, C 1 -C 6 -acyl-C 1 -C 6 -acyl, C 1 -C 6 -alkyl-C 1 -C 6 -aryl, or C 1 -C 6 -aryl-C 1 -C 6 -alkyl,

which C 1 -C 6 -alkyl, C 1 -C 6 -aryl, C 1 -C 6 -acyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -acyl, C 1 -C 6 -acyl-C 1 -C 6 -acyl, C 1 -C 6 -alkyl-C 1 -C 6 -aryl or C 1 -C 6 -aryl-C 1 -C 6 -alkyl is optionally interrupted singly or more than once, identically or differently by oxygen, sulfur or nitrogen,

R 2 is halogen, CF 3 , C 3 -C 6 -cycloalkyl, sulfonyl-C 1 -C 6 -alkyl, sulfonamide, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -aryl, C 1 -C 6 -acyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -acyl, C 1 -C 6 -acyl-C 1 -C 6 -acyl, C 1 -C 6 -alkyl-C 1 -C 6 -aryl, or C 1 -C 6 -aryl-C 1

 -C 6 -alkyl,

which C 1 -C 6 -alkyl, C 1 -C 6 -aryl, C 1 -C 6 -acyl, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-C 1 -C 6 -acyl, C 1 -C 6 -acyl-C 1 -C 6 -acyl, C 1 -C 6 -alkyl-C 1 -C 1 -C 6 -aryl or C 1 -C 6 -aryl-C 1 -C 6 -alkyl is optionally interrupted singly or more than once, identically or differently by oxygen, sulfur or nitrogen,

R 3 is C 6 -C 12 -aryl,

which C 6 -C 12 -aryl is optionally substituted singly or more than once, identically or differently with halogen, C 1 -C 6 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy, cyano, hydroxy, N—(CH 3 ) 2 , CO 2 —(C 1 -C 3 -alkyl), CO—NR 4 R 5 or CF 3 , C 5 -C 12 -heteroaryl,

which C 5 C 12 -heteroaryl is optionally substituted singly or more than once, identically or differently with chlorine fluorine, C 1 -C 6 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy, cyano, hydroxy, N—(CH 3 ) 2 , CO 2 —(C 1 -C 3 -alkyl), CO—NR 4 R 5 or CF 3 , or

 C 3 -C 6 -cycloalkyl,

which C 3 -C 6 -cycloalkyl is optionally substituted singly or more than once, identically or differently with chlorine, fluorine, CF 3 cyano, C 1 -C 3 -alkyl, C 1 -C 3 -acyl, hydroxy, N—(CH 3 ) 2 , CO 2 —(C 1 -C 3 -alkyl), CO—NR 4 R 5 or C 1 -C 3 -alkoxy,

R 1 is hydrogen,

 C 3 -C 6 -cycloalkyl,

which C 3 -C 6 -cycloalkyl is optionally substituted singly or more than once, identically or differently with C 1 -C 3 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy or CF 3 ,

 C 6 -C 12 -aryl,

which C 6 -C 12 -aryl is optionally substituted singly or more than once, identically or differently with halogen, C 1 -C 3 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy, N—C 1 -C 3 -alkyl-C 1 -C 3 -alkyl, CF 3 or cyano, or

 C 1 -C 6 -alkyl,

which C 1 -C 6 -alkyl is optionally substituted,

R 5 is hydrogen,

 C 3 -C 6 -cycloalkyl,

which C 3 -C 6 -cycloalkyl is optionally substituted singly or more than once, identically or differently with C 1 -C 3 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy or CF 3 ,

 C 6 -C 12 -aryl,

which C 6 -C 12 -aryl is optionally substituted singly or more than once, identically or differently with halogen, C 1 -C 3 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy, N—C 1 -C 3 -alkyl-C 1 -C 3 -alkyl, CF 3 or cyano,

 C 5 -C 12 -heteroaryl,

which C 5 C 12 -heteroaryl is optionally substituted singly or more than once, identically or differently with halogen, C 1 -C 3 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy, N—C 1 -C 3 -alkyl-C 1 -C 3 -alkyl, CF 3 or cyano, or

 C 1 -C 6 -alkyl,

which C 1 -C 6 -alkyl is optionally substituted,

or alternatively

R 4 and R 5 together form a 5-8-membered ring, which optionally further contains one or more heteroatoms,

X is sulfonyl, (CH 2 ) n or carbonyl,

Y is —(CH 2 )—°or carbonyl,

Z is nitrogen,

A is oxygen or sulfur, and

n stands for 0-2,

or a diastereomer, enantiomer or salt thereof.

3. A compound of claim 1 , wherein:

R 1 is hydrogen,

R 2 is C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkyl, CF 3 , cyano, bromine, —OCF 3 , —S 0 2 —CH 3 ,

R 3 is C 6 -C 12 -aryl,

which C 6 -C 12 -aryl is optionally substituted singly or more than once, identically or differently with halogen, C 1 -C 6 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy, cyano, hydroxy, N—(CH 3 ) 2 , CO 2 —(C 1 -C 3 -alkyl), CO—NR 4 R 5 or CF 3 ,

 C 5 -C 12 -heteroaryl,

which C 5 -C 12 -heteroaryl is optionally substituted singly or more than once, identically or differently with chlorine, fluorine, C 1 -C 6 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy, cyano, hydroxy, N—(CH 3 ) 2 , CO 2 —(C 1 -C 3 -alkyl), CO —NR 4 R 5 or CF 3 ,

 C 3 -C 6 -cycloalkyl,

which C 3 C 6 -cycloalkyl is optionally substituted singly or more than once, identically or differently with chlorine, fluorine, CF 3 cyano, C 1 -C 3 -alkyl, C 1 -C 3 -acyl, hydroxy, N—(CH 3 ) 2 , CO 2 —(C 1 -C 3 -alkyl), CO—NR 4 R 5 or C 1 -C 3 -alkoxy,

R 4 is hydrogen,

 C 3 -C 6 -cycloalkyl,

which C 3 -C 6 -cycloalkyl is optionally substituted singly or more than once, identically or differently with C 1 -C 3 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy or CF 3 ,

 C 6 -C 12 -aryl,

which C 6 -C 12 -aryl is optionally substituted singly or more than once, identically or differently with halogen, C 1 -C 3 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy, N—C 1 -C 3 -alkyl-C 1 -C 3 -alkyl, CF 3 or cyano,

 C 5 -C 12 -heteroaryl,

which C 5 -C 12 -heteroaryl is optionally substituted singly or more than once, identically or differently with halogen, C 1 -C 3 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy, N—C 1 -C 3 -alkyl-C 1 -C 3 -alkyl, CF 3 or cyano, or

 C 1 -C 6 -alkyl,

which C 1 -C 6 -alkyl is optionally substituted,

R 5 is hydrogen,

X is sulfonyl, carbonyl or —(CH 2 ) n ,

Y is —(CH 2 ) n — or carbonyl,

Z is nitrogen,

A is oxygen or sulfur, and

n is 0-2,

or a diastereomer, enantiomer or salt thereof.

4. A compound of claim 1 , wherein:

R 1 is hydrogen,

R 2 is C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkyl, CF 3 , cyano, bromine, or —OCF 3 , —SO 2 —CH 3 in the para-position,

R 3 is C 6 -C 12 -aryl,

which C 6 -C 12 -aryl is optionally substituted singly or twice, identically or differently with halogen, C 1 -C 3 -alkyl, acetyl, methoxy, ethoxy, cyano, hydroxy, N—(CH 3 ) 2 , CO 2 —(C 1 -C 3 -alkyl), CO—NHR 5 or CF 3 ,

 C 5 -C 12 -heteroaryl,

which C 5 -C 12 -heteroaryl is optionally substituted singly or twice, identically or differently with chlorine, fluorine, C 1 -C 3 -alkyl, acetyl, methoxy, ethoxy, cyano, hydroxy, N—(CH 3 ) 2 , CO 2 —(C 1 -C 3 -alkyl), CO—NHR 5 or CF 3 ,

 C 3 -C 6 -cycloalkyl,

is hydrogen,

 C 3 -C 6 -cycloalkyl,

Which C 3 -C 6 -cycloalkyl is optionally substituted singly or more than once, identically or differently with C 1 -C 3 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy or CF 3 ,

 C 6 -C 12 -aryl,

which C 6 -C 12 -aryl is optionally substituted singly or more than once, identically or differently with halogen, C 1 -C 3 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy, N—C 1 -C 3 -alkyl-C 1 -C 3 -alkyl, CF 3 or cyano,

 C 5 -C 12 -heteroaryl,

which C 5 -C 12 -heteroaryl is optionally substituted singly or more than once, identically or differently with halogen, C 1 -C 3 -alkyl, C 1 -C 3 -acyl, C 1 -C 3 -alkoxy, N—C 1 -C 3 -alkyl-C 1 -C 3 -alkyl, CF 3 or cyano, or

 C 1 -C 6 -alkyl,

which C 1 -C 6 -alkyl is optionally substituted

R 5 is hydrogen,

X is sulfonyh carbonyl or —CH 2 ) n ,

Y is —(CH 2 ) n — or carbonyl,

Z is nitrogen,

A is oxygen or sulfur and

n is 1−2

or a diastereomer, enantiomer or salt thereof.

5. A compound of claim 1 , wherein:

R 1 is hydrogen,

R 2 is tertiary butyl, iso-propyl, iso-butyl, sec. butyl, cyano, bromine, or — 0 —CF 3 , —SO 2 -CH 3 in the para-position,

R 3 is one of the following groups

R 4 is hydrogen or —(CH 2 ) n —N—(CH 3 ) 2 , —(CH 2 ) 2 —CH 3 , —(CH 2 ) 2 —NH—COCH 3 ,—(CH 2 )—CHCH 3 —OH, —(CH 2 ) 2 —O—CH 3 , —(CH 2 ) 2 —OH, —CHCH 3 —CH 2 —OH, —(CH 2 ) 3 —CH(CH 3 ) 2 —CH 2 —OH or CH 2 —CN, or one of the following groups

R 5 is hydrogen,

X is sulfonyh carbonyl or —(CH 2 ) n ,

Y is —(CH 2 ) n — or carbonyl,

Z is nitrogen,

A is oxygen or sulfur, and

n is 1−2

or a diastereomer, enantiomer or salt thereof.

6. A compound of claim 1 , wherein:

R 1 is hydrogen,

R 2 is tertiary butyl, iso-propyl, iso-butyl, sec. butyl, cyano, bromine, or —O —CF 3 , or —SO 2 —CH 3 in the para-position,

R 3 is one of the following groups

R 4 is hydrogen or the group, —(CH 2 )—CHCH 3 —OH, —(CH 2 ) 2 —O—CH 3 , —CHCH 3 —CH 2 —OH, , (CH 2 ) 3 —CH(CH 3 ) 2 —CH 2 —OH or CH 2 —CN, or one of the following groups

R 5 is hydrogen,

X is sulfony, carbonyl or —(CH 2 ) n ,

Y is —(CH 2 ) n — or carbony,

Z is nitrogen,

A is oxygen or sulfur, and

n is 1−2.

or a diastereomer, enantiomer or salt thereof.

7. A compound of claim 1 , which:

(+/−)-5-(4-tert-Butylbenzenesulfonylamino)-3-phenyl-1-benzothiophene-2-carboxylic acid-(2-hydroxypropyl)amide

(+/−)-5-(4-tert-Butylbenzenesulfonylamino)-3-phenyl-1-benzothiophene-2-carboxylic acid-(2-hydroxymethylethyl)amide

5-(4-tert-Butylbenzenesulfonylamino)-3-phenyl-1-benzothiophene-2-carboxylic acid -(tetrahydropyran-4-yl)amide

5-(4-tert-Butylbenzenesulfonylamino)-3-phenyl-1-benzothiophene-2-carboxylic acid-(2-morpholin-4-yl-ethyl)amide

5-(4-tert-Butylbenzenesulfonylamino)-3-phenyl-1-benzofuran-2-carboxylic acid -(tetrahydropyran-4-yl)amide

5-(4-tert-Butylbenzenesulfonylamino)-3-phenyl-1-benzofuran-2-carboxylic acid-(2-morpholin-4-yl-ethyl)amide

5-(4-tert-Butyl-phenylsulfonylamino)-3-phenyl-benzo[b]thiophene-2-carboxylic acid-(3-morpholin-4-yl-propyl)-amide

5-(4-tert-Butyl-phenylsulfonylamino)-3-phenyl-benzo[b]thiophene-2-carboxylic acid -cyclopentyl-amide

5-(4-tert-Butyl-phenylsulfonylamino)-3-phenyl-benzo[b]thiophene-2-carboxylic acid-(4-pyridyl)-amide

5-(4-tert-Butyl-phenylsulfonylamino)-3-phenyl-benzo[b]thiophene-2-carboxylic acid-(2-methoxy-ethyl)-amide

5-(4-tert-Butyl-phenylsulfonylamino)-3-phenyl-benzo[b]thiophene-2-carboxylic acid -cyclohexyl-amide -

5-(4-tert-Butyl-phenylsulfonylamino)-3-phenyl-benzo[b]thiophene-2-carboxylic acid-(2-hyxdroxy-ethyl)-amide

5-(4-tert-Butyl-phenylsulfonylamino)-3-phenyl-benzo[b]thiophene-2-carboxylic acid-(2-propen-1-yl)-amide

5-(4-tert-Butyl-phenylsulfonylamino)-3-phenyl-benzo[b]thiophene-2-carboxylic acid-(2-acetylamino-ethyl)-amide

5-(4-tert-Butyl-phenylsulfonylamino)-3-phenyl-benzo[b]thiophene-2-carboxylic acid-(5-hydroxy-4,4-dimethyl-pentyl)-amide

(+/−)-5-(4-tert-Butylphenylsulfonylamino)-3-phenyl-1-benzofuran-2-carboxylic acid-(2-hydroxypropyl)amide or

(+/−)-5-(4-tert-Butylbenzenesulfonylamino)-3-phenyl-1-benzofuran-2-carboxylic acid-(2-hydroxy-1-methylethyl)amide.

8. A method for contraception. comphsing administering an effective amount of a compound of claim 1 to a subject in need thereof.

9. A method for the inhibition of soluble adenylate cyclase. comprising administering an effective amount of a compound of claim 1 to a subject in need thereof.

10. A pharmaceutical composition, compnsing a compound of claim 1 and a pharmaceutically acceptable carrier.

11. A pharmaceutical composition according to claim 10 , which is suitable for enteral, parenteral or oral administration.

12. A method for contraception, comprising administering an effective amount of a compound of claim 7 to a subject in need thereof.

13. A method for the inhibition of soluble adenylate cyclase, comprising administering an effective amount of a compound of claim 7 to a subject in need thereof.

14. A pharmaceutical composition, comprising a compound of claim 7 and a pharmaceutically acceptable carrier.

15. A pharmaceutical composition according to claim 14 , which is suitable for enteral, parenteral or oral administration.

Assignments (2)
CHANGE OF NAME Recorded Nov 14, 2007
From: SCHERING AKTIENGESELLSCHAFT
To: BAYER SCHERING PHARMA AKTIENGESELLSCHAFT
Reel/Frame 020110/0334 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 16, 2006
From: BUCHMANN, BERND; FRITSCH, MARTIN; NGUYEN, DUY; MENZENBACH, BERND; BOEHMER, ULF
To: SCHERING AG
Reel/Frame 018204/0911 →