Carbamate-substituted pyrazolopyridine-derivatives

1. A compound of the formula (I)

in which

R 1 is hydrogen or a di-C 1-6 -alkylaminocarbonyl radical,

R 2 is a radical of the formula —O—CX—NR 3 R 4 ,

where

X is O or S;

R 3 and R 4 may be identical or different from one another and each is a radical chosen from H, optionally substituted C 1-6 -alkyl, optionally substituted C 1-6 -alkoxy-C 1-6 -alkyl, optionally substituted hydroxy-C 1-6 -alkyl, optionally substituted C 2-6 -alkenyl, optionally substituted C 1-6 -alkylcarbonyloxy-C 1-6 -alkyl, optionally substituted C 1-6 -alkoxycarbonyl-C 1-6 -alkyl, optionally substituted hydroxycarbonyl-C 1-6 -alkyl, phenyl which is optionally substituted by a C 1-6 -alkyl radical, a saturated five- to seven-membered heterocycle which is optionally linked via a C 1-6 -alkyl radical to the nitrogen atom, and optionally substituted C 3-8 -cycloalkyl, where R 3 and R 4 cannot simultaneously be H;

or

R 3 and R 4 together with the nitrogen atom to which they are bonded form a five- to seven-membered saturated heterocycle which may optionally contain a further heteroatom chosen from N, O, and S and/or may optionally be substituted or fused to a phenyl ring;

or a salt, stereoisomer, tautomer, or hydrate thereof.

2. The compound of claim 1 , in which

R 1 is hydrogen or a di-C 1-6 -alkylaminocarbonyl radical,

R 2 is a radical of the formula —O—CX—NR 3 R 4 ,

where

X is O or S;

R 3 and R 4 may be identical or different and is a radical chosen from H, C 1-6 -alkyl which optionally has a CN or a halogen substituent, C 1-6 -alkoxy-C 1-6 -alkyl, hydroxy-C 1-6 -alkyl, C 2-6 -alkenyl, C 1-6 -alkylcarbonyloxy-C 1-6 -alkyl, C 1-6 -alkoxycarbonyl-C 1-6 -alkyl, hydroxycarbonyl-C 1-6 -alkyl, phenyl, p-tolyl, a saturated five- to seven-membered heterocycle which is linked via a C 1-6 -alkanediyl radical to the nitrogen atom and has up to 2 oxygen atoms, and optionally substituted C 3-8 -cycloalkyl, where R 3 and R 4 cannot simultaneously be H;

or

R 3 and R 4 together with the nitrogen atom to which they are bonded form a five- or six-membered saturated heterocycle which may optionally contain a further heteroatom chosen from N, O, and S and/or optionally an alkylcarbonyl or alkoxycarbonyl substituent;

or a salt, stereoisomer, tautomer, or hydrate thereof.

3. The compound of claim 1 , in which

R 1 is hydrogen or a diethylaminocarbonyl radical,

R 2 is a radical of the formula —O—CX—NR 3 R 4 ,

where

X is O or S;

R 3 and R 4 may be identical or different and each is a radical chosen from H, methyl, ethyl, isopropyl, butan-2-yl, methoxyethyl, 2-methoxy-1-methylethyl, 1-cyano-1-methylethyl, 2-cyanoethyl, 2-chloroethyl, ethoxycarbonylmethyl, hydroxycarbonylmethyl 2-propenyl, phenyl, p-tolyl, 1,3-dioxolan-2-methyl, cyclohexyl and cyclopentyl, where R 3 and R 4 cannot simultaneously be H;

or

R 3 and R 4 together with the nitrogen atom to which they are bonded form a five- or six-membered saturated heterocycle which may optionally contain a further heteroatom chosen from N and O and/or may optionally have a substituent chosen from methylcarbonyl, ethoxycarbonyl and t-butoxycarbonyl, or together are 1,2,3,4-tetrahydroquinolin-N-yl;

or a salt, stereoisomer, tautomer, or hydrate thereof.

4. A process for preparing compounds of formula (I), comprising reaction of a compound of the formula (II)

with a compound of the formula (III)

in an organic solvent in the presence of a base with heating and subsequent conversion of the ether group into the free hydroxyl group to give a compound of the formula (IV)

and subsequent reaction of (IV) with a compound of the formula X—CO—NR 3 R 4 in which

X is a halogen radical or alkoxy radical, and

R 3 and R 4 have the meaning indicated in claim 1 ;

in an organic solvent, where appropriate in the presence of a base, and where appropriate with subsequent removal of protective groups to give a compound of the formula (I).

5. A pharmaceutical composition comprising at least one compound of the formula (I) as defined in claim 1 .

6. A pharmaceutical composition comprising at least one compound of the formula (I) as defined in claim 1 in combination with at least one organic nitrate or NO donor.

7. A pharmaceutical composition comprising at least one compound of the formula (I) as defined in claim 1 in combination with at least one compound which inhibits the breakdown of cyclic guanosine monophosphate (cGMP).

8. A method for the treatment of hypertension, comprising administering an effective amount of a compound of formula (I) as defined in claim 1 .

9. The method as claimed in claim 8 , wherein the compound of the formula (I) as defined in claim 1 is employed in combination with at least one organic nitrate or NO donor or in combination with at least one compound which inhibits the breakdown of cyclic guanosine monophosphate (cGMP).