IP Library › Granted Patent US 6,967,215

Granted Patent B2

US 6,967,215 · App. 10/380,573 · Granted Nov 22, 2005

Tetrahydrocarbazoles, a process for the preparation of those compounds, and the use thereof

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Quick Facts

Patent No.: US 6,967,215
App. No.: 10/380,573
Granted: Nov 22, 2005
Kind: B2

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Abstract

Tetrahydrocarbazoles of formula where Q is —SO 2 —; —O—; or —(CO)—; X is —(CH)—; or —N—; m is from 1 to 3; t is 0 or 1 and the remaining substituents are as defined herein, are useful as antimicrobial active ingredients.

Claims (130)

1. A compound of formula

wherein

R 1 is hydrogen; C 1 -C 20 alkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 -alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C 1 -C 7 alkylcarbonyl, C 1 -C 7 alkoxycarbonyl, C 3 -C 12 cycloalkylcarbonyl, C 3 -C 12 -cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono or di-C 1 -C 20 alkylamino or by nitro,

R 2 is hydrogen; hydroxy; C 1 -C 20 alkyl; C 3 -C 12 cycloalkyl; C 1 -C 20 hydroxyalkyl; C 1 -C 20 hydroxy-alkoxy; C 1 -C 20 aminoalkyl; N—C 1 -C 20 monoalkylamino-C 1 -C 20 alkyl; N—C 1 -C 20 monoalkyl-aminohydroxy-C 1 -C 20 alkoxy; N,N—C 1 -C 20 dialkylamino-C 1 -C 20 alkyl; N,N—C 1 -C 20 dialkylaminohydroxy-C 1 -C 20 alkoxy; carboxy; carboxy-C 1 -C 20 alkyl ester; C 1 -C 20 haloalkyl; C 1 -C 20 -haloalkoxy; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 alkynyl; C 4 -C 12 cycloalkynyl; C 1 -C 20 -alkoxy; C 2 -C 20 alkenyloxy; C 2 -C 20 alkynyloxy; halogen; cyano; C 1 -C 7 alkylcarbonyl; nitro; trifluoromethyl; or pentafluoroethyl;

R 3 and R 4 together denote a —(CH 2 ) 10 — radical; a C 2 -C 20 alkenylene radical; a C 4 -C 20 -alkynylene radical; or a C 3 -C 20 alkylene radical interrupted by —N(R 6 )—, it being possible for such bivalent radicals to be further substituted by one or more C 1 -C 20 alkyl, C 3 -C 12 -cycloalkyl, C 2 -C 20 alkenyl, C 4 -C 12 cycloalkenyl, C 3 -C 20 alkynyl, CC 12 cycloalkynyl, C 1 -C 7 alkoxycarbonyl, or phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C 1 -C 7 -alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N-mono- or N,N-di-C 1 -C 20 alkylamino or by nitro; or R 3 and R 4 together denote a bicyclo[x.y.z.]C 4 -C 20 alkylene or bicyclo[x.y.z.]C 4 -C 20 alkylene interrupted by —N(R 6 )—, wherein x and y are each independently of the other from 1 to 10 and z is from 0 to 10;

R 5 is hydrogen; hydroxy; C 1 -C 20 alkyl; C 1 -C 20 alkoxy; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C 1 C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N-mono- or N,N-di-C 1 -C 20 alkylamino or by nitro;

R 6 is hydrogen; C 1 -C 20 alkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 -alkynyl; C 4 -C 12 cycloalkynyl; C 1 -C 7 alkoxycarbonyl; phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C 1 -C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N-mono- or N,N-di-C 1 -C 20 alkylamino or by nitro;

Q is —SO 2 —; —O—; or —(CO)—;

X is —CH—; or —N—;

m is from 1 to 3; and

t is 0 or 1,

a compound of formula (2)

wherein

R 1 , R 2 , R 6 , X, Q, t and m are as defined for the compound of formula (1);

R 3 and R 4 are each independently of the other hydrogen; or C 1 -C 20 alkyl; or R 3 and R 4 together denote a C 2 -C 20 alkylene radical; a C 2 -C 20 alkenylene radical; a C 4 -C 20 -alkynylene radical; or a C 3 -C 20 alkylene radical interrupted by —N(R 6 )—, it being possible for such bivalent radicals to be further substituted by one or more C 1 -C 20 alkyl, C 3 -C 12 -cycloalkyl, C 2 -C 20 alkenyl, C 4 -C 12 cycloalkenyl, C 3 -C 20 alkynyl, C 4 -C 12 cycloalkynyl, C 1 -C 7 -alkoxycarbonyl, or phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C 1 -C 7 -alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N-mono- or N,N-di-C 1 -C 20 alkylamino or by nitro; or R 3 and R 4 together denote a bicyclo[x.y.z.]C 4 -C 20 alkylene; or bicyclo[x.y.z.]C 4 -C 20 alkylene interrupted by —N(R 6 )—, wherein x and y are each independently of the other from 1 to 10 and z is from 0 to 10;

R 5 is hydrogen; C 1 -C 20 alkyl; phenyl or phenyl-C 1 -C 5 alkyl.

2. A compound of formula (1) according to claim 1 , wherein

R 2 is hydrogen; hydroxy; C 1 -C 20 alkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 alkynyl; C 4 -C 12 cycloalkynyl; C 1 -C 20 alkoxy; C 2 -C 20 alkenyloxy; C 2 -C 20 alkynyloxy; halogen; cyano; C 1 -C 7 alkylcarbonyl; nitro; trifluoromethyl; or pentafluoroethyl;

R 3 and R 4 together denote a —(CH 2 ) 10 — radical; a C 2 -C 20 alkenylene radical; a C 4 -C 20 alkynylene radical; or a C 3 -C 20 alkylene radical interrupted by —N(R 6 )—, it being possible for such bivalent radicals to be further substituted by one or more C 1 -C 20 alkyl, C 3 -C 12 cycloalkyl, C 2 -C 20 -alkenyl, C 4 -C 12 cycloalkenyl, C 3 -C 20 alkynyl, C 4 -C 12 cycloalkynyl, C 1 -C 7 alkoxycarbonyl, or phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 3 -C 12 -cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C 1 -C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N-mono- or N,N-di-C 1 -C 20 alkylamino or by nitro;

R 5 is hydrogen; hydroxy; C 1 -C 20 alkyl; C 1 -C 20 alkoxy; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 12 cyclo-alkoxy, halogen, carboxy, C 1 -C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N-mono- or N,N-di-C 1 -C 20 alkylamino or by nitro;

R 6 is hydrogen; C 1 -C 20 alkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 -alkynyl; C 4 -C 12 cycloalkynyl; C 1 -C 7 alkoxycarbonyl; phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 12 cyclo-alkoxy, halogen, carboxy, C 1 -C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N-mono- or N,N-di-C 1 -C 20 alkylamino or by nitro;

Q is —SO 2 —; —O—; or —(CO)—;

X is —CH—; or —N—;

m is from 1 to 3; and

t is 0 or 1, or

a compound of formula (2) according to claim 1 , wherein

R 1 , R 2 , R 2 , X, Q, t and mare as defined above for the compound of formula (1) and

R 3 and R 4 are each independently of the other hydrogen; or C 1 -C 20 alkyl; or R 3 and R 4 denote a C 2 -C 20 alkylene radical; a C 2 -C 20 alkenylene radical; a C 4 -C 20 alkynylene radical; or a C 3 -C 20 alkylene radical interrupted by —N(R 6 )—, it being possible for such bivalent radicals to be further substituted by one or more C 1 -C 20 alkyl, C 3 -C 12 cycloalkyl, C 2 -C 20 -alkenyl, C 4 -C 12 cycloalkenyl, C 3 -C 20 alkynyl, C 4 -C 12 cycloalkynyl, C 1 -C 7 alkoxycarbonyl, or phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 3 -C 12 -cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C 1 -C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N-mono- or N,N-di-C 1 -C 20 alkylamino or by nitro;

R 5 is hydrogen; C 1 -C 20 alkyl; phenyl or phenyl-C 1 -C 5 alkyl.

3. A compound according to claim 1 , wherein

R 1 is hydrogen; C 1 -C 20 alkyl; phenyl or phenyl-C 1 -C 5 alkyl.

4. A compound according to claim 1 , wherein

R 1 is hydrogen; or C 1 -C 5 alkyl.

5. A compound according to claim 1 , wherein

R 2 is hydrogen; C 1 -C 20 alkyl; C 1 -C 20 alkoxy; or halogen.

6. A compound according claim 1 , wherein

R 2 is hydrogen; C 1 -C 5 alkyl; C 1 -C 5 alkoxy; or halogen.

7. A compound according to claim 1 that corresponds to formula

wherein

R 5 is hydrogen; hydroxy; C 1 -C 20 alkyl; C 1 -C 20 alkoxy; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 12 cyclo-alkoxy, halogen, carboxy, C 1 -C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N-mono- or N,N-di-C 1 -C 20 alkylamino or by nitro;

R 6 is hydrogen; C 1 -C 20 alkyl; C 3 -C 12 cycloalkyl; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 -alkynyl; C 4 -C 12 cycloalkynyl; C 1 -C 7 alkoxycarbonyl; phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 12 cyclo-alkoxy, halogen, carboxy, C 1 -C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N-mono- N,N-or di-C 1 -C 20 alkylamino or by nitro;

Q is —SO 2 —; —O—; or —(CO)—;

T 1 is C 2 -C 20 alkenylene; C 4 -C 20 alkynylene; or C 3 -C 20 alkylene interrupted by

X is —CH—; or —N—;

s is from 1 to 4; and

t is 0 or 1, or

a compound according to claim 1 that corresponds to formula

wherein

R 1 , R 2 , R 6 , X, Q, t and s have the same definitions as above for the compound of formula (3); and

T 1 is C 2 -C 20 alkylene; C 2 -C 20 alkenylene; C 4 -C 20 alkynylene; or C 3 -C 20 alkylene interrupted by

8. A compound of formula (4) according to claim 7 , wherein

T 1 is a —(CH 2 ) 10 — radical; and

R 6 is hydrogen; or C 1 -C 5 alkyl.

9. A compound according to claim 1 , wherein

R 5 is hydrogen; C 1 -C 20 alkyl; phenyl or phenyl-C 1 -C 5 alkyl.

10. A compound according to claim 1 , wherein

R 5 is hydrogen; C 1 -C 5 alkyl; or phenyl.

11. A compound of formula

wherein

R 6 ′ and R 6 ″ are each independently of the other hydrogen; C 1 -C 20 alkyl; C 1 -C 7 alkoxy-carbonyl; phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 1 -C 7 alkoxycarbonyl, N-mono- or N,N-di-C 1 -C 20 alkylamino or by nitro;

T 1 is —(CH 2 ) 7 — or

and

R 1 , R 2 , R 5 , R 6 and X are as defined in claim 7 , or

a compound of formula

wherein

T 1 is

and

R 1 , R 2 , R 5 , R 6 and X are as defined in claim 7 .

12. A compound according to claim 11 , wherein

R 6 ′, R 6 ″ and R 6 are each independently of the others hydrogen; C 1 -C 20 alkyl; C 1 -C 7 -alkoxycarbonyl; phenyl; or phenyl-C 1 -C 5 alkyl.

13. A compound according to claim 12 , wherein

R 6 ′, R 6 ″ and R 6 are each independently of the others hydrogen; C 1 -C 5 alkyl; C 1 -C 7 alkoxycarbonyl; phenyl or benzyl.

14. A compound according to claim 11 that corresponds to formula

wherein

R 1 is hydrogen; or C 1 -C 5 alkyl;

R 2 is hydrogen; C 1 -C 4 alkyl; Cl or Br;

R 5 is hydrogen; C 1 -C 5 alkyl; or phenyl

R 6 ′ and R 6 ″ are each independently of the other hydrogen; C 1 -C 5 alkyl; or C 1 -C 7 alkoxy-carbonyl;

R 6 is hydrogen, C 1 -C 5 alkyl; C 1 -C 7 alkylcarbonyl; or phenyl-C 1 -C 5 alkyl;

T 1 is

and

X is —CH—, or

a compound according to claim 11 that corresponds to formula

wherein

R 1 is hydrogen; or C 1 -C 5 alkyl;

R 2 is hydrogen; C 1 -C 4 alkyl; Cl or Br;

R 5 is hydrogen; C 1 -C 5 alkyl; or phenyl

R 6 ′ and R 6 ″ are each independently of the other hydrogen; C 1 -C 5 alkyl; or C 1 -C 7 alkoxy-carbonyl;

R 6 is hydrogen, C 1 -C 5 alkyl; C 1 -C 7 alkylcarbonyl; or phenyl-C 1 -C 5 alkyl;

T 1 is

and

X is —CH—.

15. A personal care method for antimicrobial treatment, deodorisation and disinfection of skin, mucosa or hair, which comprises contacting the skin, mucosa or hair with an effective amount of a compound of formula (1) or (2)

wherein

R 2 is hydrogen; hydroxy; C 1 -C 20 alkyl; C 3 -C 12 cycloalkyl; C 1 -C 20 hydroxyalkyl; C 1 -C 20 -hydroxy-alkoxy; C 1 -C 20 aminoalkyl; N—C 1 -C 20 monoalkylamino-C 1 -C 20 alkyl; N—C 1 -C 20 -monoalkyl-aminohydroxy-C 1 -C 20 alkoxy; N,N—C 1 -C 20 dialkylamino-C 1 -C 20 alkyl; N,N—C 1 -C 20 dialkyl-aminohydroxy-C 1 -C 20 alkoxy; carboxy; carboxy-C 1 -C 20 alkyl ester; C 1 -C 20 haloalkyl; C 1 -C 20 haloalkoxy; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 alkynyl; C 4 -C 12 cycloalkynyl; C 1 -C 20 alkoxy; C 2 -C 20 alkenyloxy; C 2 -C 20 alkynyloxy; halogen; cyano; C 1 -C 7 alkylcarbonyl; nitro; trifluoromethyl; or pentafluoroethyl;

R 3 is hydrogen and R 4 is C 1 -C 20 alkyl; or R 4 is hydrogen and R 3 is C 1 -C 20 alkyl; or R 3 and R 4 together denote a C 2 -C 20 alkylene radical; a C 2 -C 20 alkenylene radical; a C 4 -C 20 -alkynylene radical; or a C 3 -C 20 alkylene radical interrupted by —N(R 6 )—, it being possible for such bivalent radicals to be further substituted by one or more C 1 - C 1 -C 20 alkyl, C 3 -C 12 -cycloalkyl, C 2 -C 20 alkenyl, C 4 -C 12 cycloalkenyl, C 3 -C 20 alkynyl, C 4 -C 12 cycloalkynyl, C 1 -C 7 -alkoxycarbonyl, or phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C 1 -C 7 -alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-C 1 -C 20 alkylamino or by nitro; or R 3 and R 4 together denote a bicyclo[x.y.z]C 4 -C 20 alkylene; or bicyclo[x.y.z.]C 4 -C 20 alkylene interrupted by —N(R 6 )—, wherein x, y and z are each independently of the others from 0 to 10;

R 5 is hydrogen; hydroxy: C 1 -C 20 alkyl; C 1 -C 20 alkoxy; C 3 -C 12 cycloalkyl; C 3 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 alkynyl; C 4 -C 12 cycloalkynyl; phenyl or phenyl-C 1 -C 5 alkyl each unsubstituted or substituted by C 1 -C 5 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 5 alkoxy, C 3 -C 12 cycloalkoxy, halogen, carboxy, C 1 C 7 alkoxycarbonyl, C 3 -C 12 cycloalkoxycarbonyl, cyano, trifluoromethyl, pentafluoroethyl, amino, N,N-mono- or di-C 1 -C 20 alkylamino or by nitro;

Q is —SO 2 —; —O—; or —(CO)—;

X is —CH—; or —N—;

m is from 1 to 3; and

t is 0 or 1.

16. A method according to claim 15 , wherein the compound of formula (1) or (2) is used for disinfection and deodorisation.

17. A method for preserving textile fibre materials, which comprises contacting the textile fibre materials with an effective amount of a compound of formula (1) or (2) according to claim 15 .

18. A method of preparing and preserving washing and cleaning formulations, which comprises incorporating therein an effective amount of a compound of formula (1) or (2) according to claim 15 .

19. A method of imparting antimicrobial properties to and preserving plastics, paper, nonwovens, wood or leather, which comprises contacting the plastics, paper, nonwovens, wood or leather with an effective amount of a compound of formula (1) or (2) according to claim 15 .

20. A method of imparting antimicrobial properties to and preserving technical products selected from the group consisting of print thickeners of starch or of cellulose derivatives, surface coatings and paints, which comprises contacting said technical products with an effective amount of a compound of formula (1) or (2) according to claim 15 .

21. A method for biocidal treatment of paper, which comprises contacting said paper with a biocidally effective amount of a compound of formula (1) or (2) according to claim 15 .

22. An anitimicrobial personal care preparation comprising from 0.01 to 15% by weight, based on the total weight of the composition, of a compound of formula (1) or (2)

wherein

R 2 is hydrogen; hydroxy; C 1 -C 20 alkyl; C 3 -C 12 cycloalkyl; C 1 -C 20 hydroxyalkyl; C 1 -C 20 hydroxy-alkoxy; C 1 -C 20 aminoalkyl; N—C 1 -C 20 monoalkylamino-C 1 -C 20 alkyl; N—C 1 -C 20 -monoalkyl-aminohydroxy-C 1 -C 20 alkoxy; N,N—C 1 -C 20 dialkylamino-C 1 -C 20 alkyl; N,N—C 1 -C 20 dialkyl-aminohydroxy-C 1 -C 20 alkoxy; carboxy; carboxy-C 1 -C 20 alkyl ester; C 1 -C 20 haloalkyl; C 1 -C 20 -haloalkoxy; C 2 -C 20 alkenyl; C 4 -C 12 cycloalkenyl; C 3 -C 20 alkynyl; C 4 -C 12 cycloalkynyl; C 1 -C 20 -alkoxy; C 2 -C 20 alkenyloxy; C 2 -C 20 alkynyloxy; halogen; cyano; C 1 -C 7 alkylcarbonyl; nitro; trifluoromethyl; or pentafluoroethyl;

Q is —SO 2 —; —O—; or —(CO)—;

X is —CH—; or —N—;

m is from 1 to 3; and

t is 0 or 1;

and a cosmetically tolerable adjuvant.

23. An antimicrobial oral composition comprising from 0.01 to 15% by weight, based on the total weight of the composition, of a compound of formula (1) or (2) according to claim 22 and an orally tolerable adjuvant.

24. A pharmaceutical composition for the treatment of bacterial infections, comprising an antibacterially effective amount of a compound of formula (1) or (2) according to claim 22 and a therapeutically tolerable adjuvant.

25. A process for the preparation of a compound of formula (1) or (2) according to claim 1 , wherein an indole compound (I), a keto or aldehyde compound of formula (II) and a dienophile of formula (IV) or (V), respectively, are reacted in a suitable solvent using an acid catalyst at a temperature of from 50° C. to 140° C. to form a compound of formula (1) or (2), respectively, in accordance with the following scheme:

wherein R 1 , R 2 , R 5 , R 6 , m, Q, t and X are as defined in claim 1 .

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2007

From: CIBA SPECIALTY CHEMICALS CORPORATION

To: HUNTSMAN INTERNATIONAL LLC

Reel/Frame 019140/0871 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 1, 2005

From: HAAP, WOLFGANG; MEHLIN, ANDREAS; PETZOLD, KARIN; OCHS, DIETMAR; HOLZL, WERNER

To: CIBA SPECIALTY CHEMICALS CORP.

Reel/Frame 016746/0834 →