IP Library › Patent Application 13009951

Patent Application

App. No. 13/009,951

CARBAMOYLBENZOTRIAZOLE DERIVATIVES AS INHIBITORS OF LIPASES AND PHOSPHOLIPASES

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App. No.: 13/009,951

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Abstract

The invention relates to carbamoylbenzotriazole derivatives of general formula (I), which are defined as cited in the description, to their pharmaceutically applicable salts and to their use as medicaments.

Claims (102)

1 .- 11 . (canceled)

12 . A method for the treatment of disorders of fatty acid metabolism and glucose utilization disorders comprising administering to a patient in need of said treatment a therapeutically effective amount of a compound of the formula I

wherein:

W is —(C═O)—, —SO— or —SO 2 —;

R1 is (C 5 -C 16 )-alkyl, (C 5 -C 12 )-cycloalkyl, X-aryl, X-heteroaryl, X—(C 5 -C 12 )-cycloalkyl or (C 8 -C 14 )-bicycle, where aryl, heteroaryl, cycloalkyl or bicycle may be substituted one or more times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 ) alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 1 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl, or aminosulfonyl, and may be substituted once by Y-aryl, Y-heteroaryl or Y—(C 3 -C 12 )-cycloalkyl, in which aryl, heteroaryl or cycloalkyl may be substituted one to three times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 ) alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl or aminosulfonyl;

X is (C 1 -C 3 )-alkylene, which may be substituted one or more times by halogen, (C 1 -C 3 )-alkyl, hydroxy or trifluoromethyl;

Y is a bond, (C 1 -C 3 )-alkylene, —O— or —NH—;

R2, R3, R4, R5 are identically or differently hydrogen, halogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkyloxy-(C 1 -C 3 )-alkylene, hydroxy, phenoxy, NR6R7, cyano, nitro, COOR6, CO—NR6R7, —S—R6, —SO—R6, —SO 2 —R6, aminosulfonyl, pentafluorosulfanyl, aryl, heteroaryl, O-heteroaryl, (C 3 -C 12 )-cycloalkyl, CO—R6, CO—NR6R7, O—CO—NR6R7, O—CO—(C 1 -C 6 )-alkylene-CO—O—(C 1 -C 6 )-alkyl, O—CO—(C 1 -C 6 )-alkylene-CO—OH, O—CO—(C 1 -C 6 )-alkylene-CO—NR6R7 or unsubstituted or mono- or poly-F-substituted (C 1 -C 6 )-alkyloxy; and

R6, R7 are identically or differently hydrogen, (C 1 -C 6 )-alkyl or benzyl; or

a pharmaceutically acceptable salt thereof.

13 . A method for the treatment of disorders in which insulin resistance is involved comprising administering to a patient in need of said treatment a therapeutically effective amount of a compound of the formula I

wherein:

W is —(C═O)—, —SO— or

R1 is (C 5 -C 16 )-alkyl, (C 5 -C 12 )-cycloalkyl, X-aryl, X-heteroaryl, X—(C 5 -C 12 )-cycloalkyl or (C 8 -C 14 )-bicycle, where aryl, heteroaryl, cycloalkyl or bicycle may be substituted one or more times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl, or aminosulfonyl, and may be substituted once by Y-aryl, Y-heteroaryl or Y—(C 3 -C 12 )-cycloalkyl, in which aryl, heteroaryl or cycloalkyl may be substituted one to three times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl or aminosulfonyl;

X is (C 1 -C 3 )-alkylene, which may be substituted one or more times by halogen, (C 1 -C 3 )-alkyl, hydroxy or trifluoromethyl;

Y is a bond, (C 1 -C 3 )-alkylene, —O— or —NH—;

R6, R7 are identically or differently hydrogen, (C 1 -C 6 )-alkyl or benzyl; or

a pharmaceutically acceptable salt thereof.

14 . A method for the treatment of diabetes mellitus and the sequelae associated therewith comprising administering to a patient in need of said treatment a therapeutically effective amount of a compound of the formula I

wherein:

W is —(C═O)—, —SO— or

R1 is (C 5 -C 16 )-alkyl, (C 5 -C 12 )-cycloalkyl, X-aryl, X-heteroaryl, X—(C 5 -C 12 )-cycloalkyl or (C 8 -C 14 )-bicycle, where aryl, heteroaryl cycloalkyl or bicycle may be substituted one or more times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl, or aminosulfonyl, and may be substituted once by Y-aryl, Y-heteroaryl or Y—(C 3 -C 12 )-cycloalkyl, in which aryl, heteroaryl or cycloalkyl may be substituted one to three times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 1 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl or aminosulfonyl;

X is (C 1 -C 3 )-alkylene, which may be substituted one or more times by halogen, (C 1 -C 3 )-alkyl, hydroxy or trifluoromethyl;

Y is a bond, (C 1 -C 3 )-alkylene, —O— or —NH—;

R6, R7 are identically or differently hydrogen, (C 1 -C 6 )-alkyl or benzyl; or

a pharmaceutically acceptable salt thereof.

15 . A method for the treatment of dyslipidemia and its sequelae comprising administering to a patient in need of said treatment a therapeutically effective amount of a compound of the formula I

wherein:

W is —(C═O)—, —SO— or —SO 2 ;

R1 is (C 5 -C 16 )-alkyl, (C 5 -C 12 )-cycloalkyl, X-aryl, X-heteroaryl, cycloalkyl or (C 8 -C 14 )-bicycle, where aryl, heteroaryl, cycloalkyl or bicycle may be substituted one or more times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-allylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 ) -alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl, or aminosulfonyl, and may be substituted once by Y-aryl, Y-heteroaryl or Y—(C 3 -C 12 )-cycloalkyl, in which aryl, heteroaryl or cycloalkyl may be substituted one to three times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl or aminosulfonyl;

X is (C 1 -C 3 )-alkylene, which may be substituted one or more times by halogen, (C 1 -C 3 )-alkyl, hydroxy or trifluoromethyl;

Y is a bond, (C 1 -C 3 )-alkylene, —O— or —NH—;

R2, R3, R4, R5 are identically or differently hydrogen, halogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkyloxy-(C 1 -C 3 )-alkylene, hydroxy, phenoxy, NR6R7, cyano, nitro, COOR6, CO—NR6R7, —S—R6, —SO—R6, —SO 2 —R6, aminosulfonyl, pentafluorosulfanyl, aryl, heteroaryl, O-heteroaryl, (C 3 -C 12 )-cycloalkyl, CO—R6, CO—NR6R7, O—CO—NR6R7, O—CO—(C 1 -C 6 )-alkylene-CO—O—CO—(C 1 -C 6 )-alkyl, O—CO—(C 1 -C 6 )-alkylene-CO—OH, O—CO—(C 1 -C 6 )-alkylene-CO—NR6R7 or unsubstituted or mono- or poly-F-substituted (C 1 -C 6 )-alkyloxy and

R6, R7 are identically or differently hydrogen, (C 1 -C 6 )-alkyl or benzyl; or

a pharmaceutically acceptable salt thereof.

16 . A method for the treatment of conditions associated with the metabolic syndrome comprising administering to a patient in need of said treatment a therapeutically effective amount of a compound of the formula I

wherein:

W is —(C═O)—, —SO— or —SO 2 —;

R1 is (C 5 -C 16 )-alkyl, (C 5 -C 12 )-cycloalkyl, X-aryl, X-heteroaryl, X—(C 5 -C 12 )-cycloalkyl or (C 8 -C 14 )-bicycle, where aryl, heteroaryl, cycloalkyl or bicycle may be substituted one or more times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl, or aminosulfonyl, and may be substituted once by Y-aryl, Y-heteroaryl or Y—(C 3 -C 12 )-cycloalkyl, in which aryl, heteroaryl or cycloalkyl may be substituted one to three times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 ) alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl or aminosulfonyl;

X is (C 1 -C 3 )-alkylene, which may be substituted one or more times by halogen, (C 1 -C 3 )-alkyl, hydroxy or trifluoromethyl;

Y is a bond, (C 1 -C 3 )-alkylene, —O— or —NH—;

R6, R7 are identically or differently hydrogen, (C 1 -C 6 )-alkyl or benzyl; or

a pharmaceutically acceptable salt thereof.

17 . A method for the treatment of conditions associated with a reduced HDL level comprising administering to a patient in need of said treatment a therapeutically effective amount of a compound of the formula I

wherein:

W is —(C═O)—, —SO— or

R1 is (C 5 -C 16 )-alkyl, (C 5 -C 12 )-cycloalkyl, X-aryl, X-heteroaryl, X—(C 5 -C 12 )-cycloalkyl or (C 8 -C 14 )-bicycle, where aryl, heteroaryl, cycloalkyl or bicycle may be substituted one or more times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl, or aminosulfonyl, and may be substituted once by Y-aryl, Y-heteroaryl or Y—(C 3 -C 12 )-cycloalkyl, in which aryl, heteroaryl or cycloalkyl may be substituted one to three times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl or aminosulfonyl;

X is (C 1 -C 3 )-alkylene, which may be substituted one or more times by halogen, (C 1 -C 3 )-alkyl, hydroxy or trifluoromethyl;

Y is a bond, (C 1 -C 3 )-alkylene, —O— or —NH—;

R2, R3, R4, R5 are identically or differently hydrogen, halogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-halo alkyl, (C 1 -C 3 )-alkyloxy-(C 1 -C 3 )-alkylene, hydroxy, phenoxy, NR6R7, cyano, nitro, COOR6, CO—NR6R7, —S—R6, —SO—R6, —SO 2 —R6, aminosulfonyl, pentafluorosulfanyl, aryl, heteroaryl, O-heteroaryl, (C 3 -C 12 ) cycloalkyl, CO—R6, CO—NR6R7, O—CO—NR6R7, O—CO—(C 1 -C 6 )-alkylene-CO—O—(C 1 -C 6 )-alkyl, O—CO—(C 1 -C 6 )-alkylene-CO—OH, O—CO—(C 1 -C 6 )-alkylene-CO—NR6R7 or unsubstituted or mono- or poly-F-substituted (C 1 -C 6 )-alkyloxy; and

R6, R7 are identically or differently hydrogen, (C 1 -C 6 )-alkyl or benzyl; or

a pharmaceutically acceptable salt thereof.

18 . A method for the treatment of atherosclerotic disorders comprising administering to a patient in need of said treatment a therapeutically effective amount of a compound of the formula I

wherein:

W is —(C═O)—, —SO— or —SO 2 ;

R1 is (C 5 -C 16 )-alkyl, (C 5 -C 12 )-cycloalkyl, X-aryl, X-heteroaryl, X—(C 5 -C 12 )-cycloalkyl or (C 8 -C 14 )-bicycle, where aryl, heteroaryl, cycloalkyl or bicycle may be substituted one or more times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl, or aminosulfonyl, and may be substituted once by Y-aryl, Y-heteroaryl or Y—(C 3 -C 12 )-cycloalkyl, in which aryl, heteroaryl or cycloalkyl may be substituted one to three times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl or aminosulfonyl

X is (C 1 -C 3 )-alkylene, which may be substituted one or more times by halogen, (C 1 -C 3 )-hydroxy or trifluoromethyl;

Y is a bond, (C 1 -C 3 )-alkylene, —O— or —NH—;

R6, R7 are identically or differently hydrogen, (C 1 -C 6 )-alkyl or benzyl; or

a pharmaceutically acceptable salt thereof.

19 . A method for the treatment of disorders in which insulin resistance is involved comprising administering to a patient in need of said treatment a therapeutically effective amount of a compound of the formula I

wherein:

W is —(C═O)—, —SO— or —SO 2 —;

R1 is (C 5 -C 16 )-alkyl, (C 5 -C 12 )-cycloalkyl, X-aryl, X-heteroaryl, X—(C 5 -C 12 )-cycloalkyl or (C 8 -C 14 )-bicycle, where aryl, heteroaryl, cycloalkyl or bicycle may be substituted one or more times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 ) -alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl, or aminosulfonyl, and may be substituted once by Y-aryl, Y-heteroaryl or Y—(C 3 -C 12 )-cycloalkyl, in which aryl, heteroaryl or cycloalkyl may be substituted one to three times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl or aminosulfonyl;

X is (C 1 -C 3 )-alkylene, which may be substituted one or more times by halogen, hydroxy or trifluoromethyl;

Y is a bond, (C 1 -C 3 )-alkylene, —O— or —NH—;

R6, R7 are identically or differently hydrogen, (C 1 -C 6 )-alkyl or benzyl; or

a pharmaceutically acceptable salt thereof

in combination with at least one other active ingredient.

20 . A process for producing a medicament comprising one or more of the compounds of the formula I

wherein:

W is —(C═O)—, —SO— or —SO 2 —;

R1 is (C 5 -C 16 )-alkyl, (C 5 -C 12 )-cycloalkyl, X-aryl, X-heteroaryl, X—(C 5 -C 12 )-cycloalkyl or (C 8 -C 14 )-bicycle, where aryl, heteroaryl, cycloalkyl or bicycle may be substituted one or more times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 1 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 ) alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl, or aminosulfonyl, and may be substituted once by Y-aryl, Y-heteroaryl or Y—(C 3 -C 12 )-cycloalkyl, in which aryl, heteroaryl or cycloalkyl may be substituted one to three times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl or aminosulfonyl;

X is (C 1 -C 3 )-alkylene, which may be substituted one or more times by halogen, (C 1 -C 3 )-alkyl, hydroxy or trifluoromethyl;

Y is a bond, (C 1 -C 3 )-alkylene, —O— or —NH—;

R2, R3, R4, R5 are identically or differently hydrogen, halogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkyloxy-(C 1 -C 3 )-alkylene, hydroxy, phenoxy, NR6R7, cyano, nitro, COOR6, CO—NR6R7, —S—R6, —SO—R6, —SO 2 —R6, aminosulfonyl, pentafluorosulfanyl, aryl, heteroaryl, O-heteroaryl, (C 3 -C 12 )-cycloalkyl, CO—NR6R7, O—CO—NR6R7, O—CO—(C 1 -C 6 )-alkylene-CO—O—(C 1 -C 6 )-alkyl, O—CO—(C 1 -C 6 )-alkylene-CO—OH, O—CO—(C 1 -C 6 )-alkylene-CO—NR6R7 or unsubstituted or mono- or poly-F-substituted (C 1 -C 6 )-alkyloxy; and

R6, R7 are identically or differently hydrogen, (C 1 -C 6 )-alkyl or benzyl; or

a pharmaceutically acceptable salt thereof;

which process comprises mixing said one or more compounds with a pharmaceutically suitable carrier to form a mixture, and converting said mixture into a form suitable for administration.

21 . A process for preparing a compound of the formula I

wherein:

W is —(C═O)—, —SO— or —SO 2 —;

R1 is (C 5 -C 16 )-alkyl, (C 5 -C 12 )-cycloalkyl, X-aryl, X-heteroaryl, X—(C 5 -C 12 )-cycloalkyl or (C 8 -C 14 )-bicycle, where aryl, heteroaryl, cycloalkyl or bicycle may be substituted one or more times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 ) -alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 2 -C 12 )-alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 ) -alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl, or aminosulfonyl, and may be substituted once by Y-aryl, Y-heteroaryl or Y—(C 3 -C 12 )cycloalkyl in which aryl, heteroaryl or cycloalkyl may be substituted one to three times by halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyloxy, hydroxy, (C 1 -C 6 )-alkylmercapto, amino, (C 1 -C 6 )-alkylamino, di-(C 1 -C 12 -alkylamino, mono-(C 1 -C 6 )-alkylaminocarbonyl, di-(C 2 -C 8 )-alkylaminocarbonyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylcarbonyl, cyano, nitro, trifluoromethyl, trifluoromethyloxy, (C 1 -C 6 )-alkylsulfonyl or aminosulfonyl;

X is (C 1 -C 3 )-alkylene, which may be substituted one or more times by halogen, (C 1 -C 3 )-alkyl, hydroxy or trifluoromethyl;

Y is a bond, (C 1 -C 3 )-alkylene, —O— or —NH—;

R6, R7 are identically or differently hydrogen, (C 1 -C 6 )-alkyl or benzyl; or

a pharmaceutically acceptable salt thereof

which process comprises:

a) acylating benzotriazole of the formula II with a carbamoyl chloride of the formula III;

b) reacting benzotriazole of the formula II in two stages first with phosgene or its equivalents chosen from trichloromethyl chloro carbonate, ditrichloromethyl carbonate or 4-nitrophenyl chloroformate and in a second step with an amine of the formula IV:

c) reacting benzotriazole of the formula II with an isocyanate of the formula V:

O═C═N—R1;

and

where appropriate separating the resulting regioisomers by a chromatographic method.

Assignments (2)

CHANGE OF NAME Recorded Jun 20, 2012

From: SANOFI-AVENTIS

To: SANOFI

Reel/Frame 028413/0927 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 30, 2012

From: PETRY, STEFAN, DR.; ZOLLER, GERHARD, DR.; TENNAGELS, NORBERT, DR.; MULLER, GUNTER, DR.

To: SANOFI-AVENTIS

Reel/Frame 027962/0059 →