Claims
- 1. A compound of formula ##STR15## or a pharmaceutically acceptable salt thereof wherein R.sup.1 and R.sup.2 are taken together with the nitrogen to which they are attached to form a heterocyclic ring selected from pyrrolidinyl, morpholino, and piperidino;
- R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, and R.sup.10 are each independently hydrogen, halogen, alkyl of from one to four carbon atoms, alkoxy of from one to four carbon atoms, acyloxy of from one to four carbon atoms, nitro, amino which is unsubstituted or mono- or disubstituted by benzyl, alkyl of from one to four carbon atoms, benzyloxy, hydroxy, aminoalkoxy of from one to twelve carbon atoms and which nitrogen can be unsubstituted or mono- or disubstituted by benzyl or by alkyl of from one to four carbon atoms or the substituents together with the nitrogen to which they are attached form a heterocyclic ring containing from three to six atoms or the alkyl is unsubstituted or substituted by alkyl of from one to four carbon atoms, hydroxy, alkoxy of from one to four carbon atoms, trifluoromethyl or two neighboring substituents form methylene, with the proviso that not all of R.sup.1 to R.sup.10 are hydrogen and R.sup.10 can also be cyanoalkyl or when R.sup.4 or R.sup.4 and R.sup.9 are hydroxy, the others of R.sup.1 to R.sup.10 are not hydrogen.
- 2. A compound according to claim 1 wherein R.sup.1 and R.sup.2 are taken together with the nitrogen to which they are attached, to form a heterocyclic ring selected from pyrrolidinyl, morpholino, and piperidino;
- R.sup.3, R.sup.6, R.sup.7, and R.sup.10 are each hydrogen and R.sup.4, R.sup.5, R.sup.8, and R.sup.9 are each independently hydrogen, halogen, alkyl of from one to four carbon atoms, alkoxy of from one to four carbon atom, benzyloxy, hydroxy, aminoalkoxy of from one to four carbon atoms, the alkyl portion of which is unsubstituted or substituted by alkoxy of from one to four carbon atoms and the nitrogen portion of which is unsubstituted, mono- or disubstituted by alkyl of from one to four carbon atoms and two substituents of R.sup.4, R.sup.5, R.sup.8, and R.sup.9 together with the nitrogen to which they are attached form a heterocyclic ring containing from three to six atoms, wherein the alkyl chain is unsubstituted or substituted by an alkyl of from one to four carbon atoms.
- 3. A compound of formula ##STR16## or a pharmaceutically acceptable salt thereof wherein R.sup.1 and R.sup.2 are each independently 2-piperidinoethyl, 3-piperidinopropyl, 2-pyrrolidinyoethyl, 3-pyrrolidinopropyl, 2-morpholinoethyl, 3-morpholinopropyl, pyrrolidin-2-ylmethyl, N-methylpyrrolidin-2-yl-methyl, and R.sup.5 and R.sup.8 are each independently 2-piperidinoethoxy, 3-piperidinopropoxy, 2-pyrrolidinoethoxy, 3-pyrrolidinopropoxy, 2-morpholinoethoxy, 3-morpholinopropoxy, 2-piperazinoethyl, 3-piperazinopropyl, pyrrolidin-2-ylmethoxy or N-methylpyrrolidin-2-ylmethoxy;
- R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, and R.sup.10 are each independently hydrogen, halogen, alkyl of from one to four carbon atoms, alkoxy of from one to four carbon atoms, acyloxy of from one to four carbon atoms, nitro, amino which is unsubstituted or mono- or disubstituted by benzyl, alkyl of from one to four carbon atoms, benzyloxy, hydroxy, aminoalkoxy of from one to twelve carbon atoms and which nitrogen can be unsubstituted or mono- or disubstituted by benzyl or by alkyl of from one to four carbon atoms or the substituents together with the nitrogen to which they are attached form a heterocyclic ring containing from three to six atoms or the alkyl is unsubstituted or substituted by alkyl of from one to four carbon atoms, hydroxy, alkoxy of from one to four carbon atoms, trifluoromethyl or two neighboring substituents form methylene, with the proviso that not all of R.sup.1 to R.sup.10 are hydrogen and R.sup.10 can also be cyanoalkyl or when R.sup.4 or R.sup.4 and R.sup.9 are hydroxy, the others of R.sup.1 to R.sup.10 are not hydrogen.
- 4. A compound selected from the group consisting of:
- 2-(1H-indol-3-yl)-3-[1-(3-(1-piperidino)propyl)-1H-indol-3-yl]maleinimide,
- 2-(1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-1H-indol-3-yl]maleinimide,
- 2-(5-methoxy-1H-indol-3-yl)-3-[1-(3-(4-morpholino)propyl)-1H-indol-3-yl]maleinimide,
- 2-(1H-indol-3-yl)-3-[5-methoxy-1-(3-(4-morpholino)propyl)-1H-indol-3-yl]maleinimide,
- 2-(1H-indol-3-yl)-3-[5-methoxy-1-(3-(1-piperidino)propyl)-1H-indol-3-yl]maleinimide,
- 2-(5- methoxy-1H-indol-3-yl)-3-[1-(3-(1-piperidino)propyl)-1H-indol-3-yl]maleinimide.
- 5. A compound selected from the group consisting of the named compound and the (+) and (-) and (.+-.) mixtures thereof:
- (.+-.)-2-[1-(2-hydroxy-3-(1-piperidino)-propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)maleinimide,
- (+)-2-[1-(2-hydroxy-3-(1-piperidino)-propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)maleinimide, and
- (-)-2-[1-(2-hydroxy-3-(1-piperidino)-propyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)maleinimide.
Priority Claims (2)
| Number |
Date |
Country |
Kind |
| 39 42 991.1 |
Dec 1989 |
DEX |
|
| 39 14 764.9 |
Mar 1990 |
DEX |
|
Parent Case Info
This is a Divisional application of U.S. Ser. No. 08/028,528 filed Mar. 9, 1993, now U.S. Pat. No. 5,380,746; which is a File-Wrapper-Continuation application of U.S. Ser. No. 07/715,064, filed Jun. 11, 1991, now abandoned; which is a Continuation-in-Part of U.S. Ser. No. 07/515,795 filed Apr. 27, 1990, now abandoned.
US Referenced Citations (1)
| Number |
Name |
Date |
Kind |
|
4912107 |
Kleinschroth et al. |
Mar 1990 |
|
Foreign Referenced Citations (1)
| Number |
Date |
Country |
| 328026 |
Aug 1989 |
EPX |
Non-Patent Literature Citations (2)
| Entry |
| Tetrahedron Letters, 28(38):4441-4444 (1987), J. Bergman et al., "Coupling of Indoleacetic Acid Trianion . . . ". |
| Febs Lett., 259(1):61-63 (1989), P. D. Davis et al., "Potent Selective Inhibitors of Protein Kinase-C". |
Divisions (1)
|
Number |
Date |
Country |
| Parent |
28528 |
Mar 1993 |
|
Continuation in Parts (2)
|
Number |
Date |
Country |
| Parent |
715064 |
Jun 1991 |
|
| Parent |
515795 |
Apr 1990 |
|
Patent Grant
5516915
