Claims
- 1. A compound selected from the group consisting of a compound of the formula wherein A is selected from the group consisting of R1 and R2 are individually selected from the group consisting of hydrogen, halogen, —OH and alkyl and alkoxy of 1 to 6 carbon atoms, R3 is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms and —COR4, R4 is alkyl of 1 to 6 atoms, R5 is selected from the group consisting of hydrogen, —OH and alkyl and alkoxy of 1 to 6 carbon atoms, X is selected from the group consisting of —Z1—, —Z1—CO—, —CH═, —CH═CH—CO—, —Z1—NR3—CO—Z′1—, —CO—NR3—Z′1—, —Z1—NR3—CS—, —Z1—NR3—SO2— and a single bond, Het is piperazine or 1,4-diazepine unsubstituted or substituted by at least one member of the group consisting of —X1—OR3, —X1—NR3 and —X1—S—R3, Y is selected from the group consisting of —Z2—Q—, —Z2—CO—, —Z2—NH—CO—, —Z2—CH2—NR3—CO—, —NR3—Z2—Q—, —NR3—CO—Z2—Q—, —NR3—NH—CO—Z2, —NH—NH—Z2—, —NR3—O—Z2—, NR3—SO2—NR3—Z2—, —O—Z2—Q, —O—CO—Z2—Q and —S—Z2—Q—, Q is selected from the group consisting of —S—Z3 and a single bond, and X1 is —(CH2)n—, n is an integer from 0 to 6, Z1, Z′1, Z2 and Z3 are individually a single bond or alkyl of 1 to 6 carbon atoms, R6 is hydrogen or —OH, W is —NH2 or —NO2 and a salt thereof.
- 2. A compound of claim 1 wherein Het is selected from the group consisting of. piperazine, 2-methylpiperazine, 2,5-dimethyl-piperazine and 4-aminopiperidine.
- 3. A compound of claim 1 wherein Z1, Z1, Z2 and Z3 are individually —(CH2)m— and m is an integer from 0 to 6.
- 4. A compound of claim 1 selected from the group consisting of:1-{[3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl]carbonyl}-4-(4-nitrophenyl)piperazine; 1-{[3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl]carbonyl}-4-(4-aminophenyl)piperazine; hexahydro-4-(4-nitrophenyl)-1H-1,4-diazepine; 1-[(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)carbonyl]hexahydro-4-(4-nitrophenyl)-1H-1,4-diazepine; 1-(4-aminophenyl)-4-[(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)carbonyl]hexahydro-1H-1,4-diazepine; N-[4-{4-[(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)carbonyl]-1H-1,4-diazepin-1-yl}phenyl]-2-thiophenecarboximidamide hydrochloride; (R)-3,4-dihydro-2,5,7,8-tetramethyl-2-{4-[(4-nitrophenyl)-1-piperazinyl]-carbonyl}-2H-1-benzopyran-6-ol; (R)-3,4-dihydro-2,5,7,8-tetramethyl-2-{4-[(4-aminophenyl)-1-piperazinyl]-carbonyl}-2H-1-benzopyran-6-ol; (S)-3,4-dihydro-2,5,7,8-tetramethyl-2-{4-[(4-nitrophenyl)-1-piperazinyl]-carbonyl}-2H-1-benzopyran-6-ol; (S)-3,4-dihydro-2,5,7,8-tetramethyl-2-{4-[(4-aminophenyl)-1-piperazinyl]-carbonyl}-2H-1-benzopyran-6-ol; and a salt thereof.
Priority Claims (2)
| Number |
Date |
Country |
Kind |
| 97 03528 |
Mar 1997 |
FR |
|
| 97 07701 |
Jun 1997 |
FR |
|
Parent Case Info
This application is a division of U.S. patent application Ser. No. 09/882,264 filed Jun. 15, 2001 which is a division of U.S. patent application Ser. No. 09/456,205 filed Dec. 7, 1999, now U.S. Pat. No. 6,335,445 which is a continuation-in-part of U.S. patent application Ser. No. 09/381,749 filed Sep. 22, 1999, now U.S. Pat. No. 6,340,700 which is a 371 of PCT/FR98/00288 filed Feb. 16, 1998 and PCT/FR98/01250 filed Jun. 15, 1998.
US Referenced Citations (3)
| Number |
Name |
Date |
Kind |
|
3652645 |
Dietrich et al. |
Mar 1972 |
A |
|
6335445 |
De Lassauniere et al. |
Jan 2002 |
B1 |
|
6340700 |
De Lassauniere et al. |
Jan 2002 |
B1 |
Foreign Referenced Citations (2)
| Number |
Date |
Country |
| 1912847 |
Oct 1969 |
DE |
| 9505363 |
Feb 1995 |
WO |
Continuation in Parts (1)
|
Number |
Date |
Country |
| Parent |
09/381749 |
|
US |
| Child |
09/456205 |
|
US |
Patent Grant
6599903
