Claims
- 1. A heterocyclic compound of the formula (I) ##STR43## wherein one of R.sup.2 and R.sup.4 is NHCO--R.sup.6 and the other is hydrogen;
- R.sup.1 and R.sup.3 are both C.sub.1 -C.sub.4 alkyl or both C.sub.1 -C.sub.4 alkoxy; when R.sup.5 is unsubstituted C.sub.1 -C.sub.12 alkyl, R.sup.6 is C.sub.1 -C.sub.2 alkyl (which is optionally substituted with hydroxy, C.sub.2 -C.sub.5 acyloxy, or C.sub.1 -C.sub.4 alkoxy), pyrrolidinyl, piperidyl, piperidino, morpholinyl, morpholino, piperazinyl, pyrrolyl, imidazolyl, pyridyl, pyrrolidinyl C.sub.1 -C.sub.8 alkyl, piperidyl C.sub.1 -C.sub.8 alkyl, piperidino C.sub.1 -C.sub.8 alkyl, morpholinyl C.sub.1 -C.sub.8 alkyl, morpholino C.sub.1 -C.sub.8 alkyl, piperazinyl C.sub.1 -C.sub.8 alkyl, pyrrolyl C.sub.1 -C.sub.8 alkyl, imidazolyl C.sub.1 -C.sub.8 alkyl, pyridyl C.sub.1 -C.sub.8 alkyl, --NR.sup.7 R.sup.8 (wherein R.sup.7 is hydrogen, and R.sup.8 is C.sub.1 -C.sub.12 alkyl), or --R.sup.9 --OCOR.sup.10 (wherein R.sup.9 is C.sub.1 -C.sub.8 alkylene and R.sup.10 is pyrrolidinyl, piperidyl, piperidino, morpholinyl, morpholino, piperazinyl, pyrrolyl, imidazolyl, or pyridyl and m is 1, and when R.sup.5 is C.sub.1 -C.sub.12 alkyl, which is substituted by C.sub.2 -C.sub.5 acyloxy or C.sub.1 -C.sub.4 alkoxy, R.sup.6 is unsubstituted C.sub.1 -C.sub.2 alkyl and m is 1,
- or a pharmaceutically acceptable salt thereof.
- 2. The compound of claim 1, which is a member selected from the group consisting of:
- 1-butyl-3-(1-hexyl-4,6-dimethylindolin-5-yl)urea,
- N-(1-hexyl-4,6-dimethylindolin-5-yl)-2,2-dimethylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- 1-butyl-3-(1-hexyl-4,6-dimethylindolin-7-yl)urea,
- N-(1-ethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylundecanamide,
- N-(1-hexyl-4,6-dimethoxylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-butyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-butyl-4,6-dimethylindolin-7-yl)-2,2-dimethylhexanamide,
- N-(1-butyl-4,6-dimethylindolin-7-yl)-2,2-dimethyloctanamide,
- N-(4,6-dimethyl-1-octylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-ethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-ethyl-4,6-dimethylindolin-7-yl)-2,2-dimethyloctanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2,2-dimethylhexanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2,2-dimethyloctanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2-methylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)pentanamide,
- N-[1-(2-acetoxyethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide,
- N-[1-(2-methoxyethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide,
- N-[1-(2-ethoxyethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide,
- N-(4,6-dimethyl-1-pentylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-heptyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-3-hydroxy-2,2-dimethylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-3-acetoxy-2,2-dimethylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)nicotinamide,
- N-(1-isopentyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-isobutyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-3-nicotinoyloxypropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-3-ethoxypropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-3-(2,6-dimethylpiperidino)propanamide, and
- N-(4,6-dimethyl-1-propylindolin-7-yl)-2,2-dimethylpropanamide, or pharmaceutically acceptable salts thereof.
- 3. The compound of claim 1, which is a member selected from the group consisting of:
- 1-butyl-3-(1-hexyl-4,6-dimethylindolin-5-yl)urea,
- N-(1-hexyl-4,6-dimethylindolin-5-yl)-2,2-dimethylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- 1-butyl-3-(1-hexyl-4,6-dimethylindolin-7-yl)urea,
- N-(4,6-dimethyl-1-pentylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-isobutyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-3-ethoxypropanamide, and
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-3-(2,6-dimethylpiperidino)propanamide, or pharmaceutically acceptable salts thereof.
- 4. The compound of claim 1, wherein the compound is N-(4,6-dimethyl-1-pentylindolin-7-yl)-2,2-dimethylpropanamide or a pharmaceutically acceptable salt thereof.
- 5. A pharmaceutical composition comprising the heterocyclic compound of claim 1, or a pharmaceutically acceptable salt thereof, in admixture with a pharmaceutically acceptable diluent or carrier.
- 6. The pharmaceutical composition of claim 5, wherein the compound is selected from the group consisting of:
- 1-butyl-3-(1-hexyl-4,6-dimethylindolin-5-yl)urea,
- N-(1-hexyl-4,6-dimethylindolin-5-yl)-2,2-dimethylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- 1-butyl-3-(1-hexyl-4,6-dimethylindolin-7-yl)urea,
- N-(1-ethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylundecanamide,
- N-(1-hexyl-4,6-dimethoxylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-butyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-butyl-4,6-dimethylindolin-7-yl)-2,2-dimethylhexanamide,
- N-(1-butyl-4,6-dimethylindolin-7-yl)-2,2-dimethyloctanamide,
- N-(4,6-dimethyl-1-octylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-ethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-ethyl-4,6-dimethylindolin-7-yl)-2,2-dimethyloctanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2,2-dimethylhexanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2,2-dimethyloctanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2-methylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)pentanamide,
- N-[1-(2-acetoxyethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide,
- N-[1-(2-methoxyethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide,
- N-[1-(2-ethoxyethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide,
- N-(4,6-dimethyl-1-pentylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-heptyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-3-hydroxy-2,2-dimethylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-3-acetoxy-2,2-dimethylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)nicotinamide,
- N-(1-isopentyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-isobutyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-3 nicotinoyloxypropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-3-ethoxypropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-3-(2,6-dimethylpiperidino)propanamide, and
- N-(4,6-dimethyl-1-propylindolin-7-yl)-2,2-dimethylpropanamide, or pharmaceutically acceptable salts thereof.
- 7. The pharmaceutical composition of claim 5, wherein the compound is selected from the group consisting of:
- 1-butyl-3-(1-hexyl-4,6-dimethylindolin-5-yl)urea,
- N-(1-hexyl-4,6-dimethylindolin-5-yl)-2,2-dimethylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- 1-butyl-3-(1-hexyl-4,6-dimethylindolin-7-yl)urea,
- N-(4,6-dimethyl-1-pentylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-isobutyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide,
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-3-ethoxypropanamide, and
- N-(1-hexyl-4,6-dimethylindolin-7-yl)-3-(2,6-dimethylpiperidino)propanamide, or pharmaceutically acceptable salts thereof.
- 8. The pharmaceutical composition of claim 5, wherein the compound is N-(4,6-dimethyl-1-pentylindolin-7-yl)-2,2-dimethylpropanamide or a pharmaceutically acceptable salt thereof.
Priority Claims (1)
Number |
Date |
Country |
Kind |
6-225166 |
Sep 1994 |
JPX |
|
Parent Case Info
This application is a 371 of PCT/JP95/01873 filed Sep. 20, 1995
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/JP95/01873 |
9/20/1995 |
|
|
3/19/1997 |
3/19/1997 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO96/09287 |
3/28/1996 |
|
|
US Referenced Citations (4)
Number |
Name |
Date |
Kind |
3824230 |
Hester, Jr. |
Jul 1974 |
|
5143919 |
Meguro et al. |
Sep 1992 |
|
5254590 |
Malen et al. |
Oct 1993 |
|
5256782 |
Meguro et al. |
Oct 1993 |
|
Foreign Referenced Citations (5)
Number |
Date |
Country |
2-117651 |
May 1990 |
JPX |
3-7259 |
Jan 1991 |
JPX |
04066568 |
Mar 1992 |
JPX |
WO 9414801 |
Jul 1994 |
WOX |
9712860 |
Apr 1997 |
WOX |
Non-Patent Literature Citations (1)
Entry |
De Vries et al., "Potential Antiatherosclerotic Agents. 5..sup.1 An Acyl-CoA:Cholesterol O-Acyltransferase Inhibitor with Hypocholesterolemic Activity," J. Med. Chem., 29, pp. 1131-1133 (1986). |