Claims
- 1. A compound of Formula I or a pharmaceutically acceptable acid addition salt and/or solvate thereof ##STR8## wherein R.sup.1 is selected from hydrogen, halogen, lower alkyl, lower alkoxy and lower alkylthio;
- R.sup.2 and R.sup.3 are independently selected from hydrogen and lower alkyl;
- R.sup.4 is selected from hydrogen and lower alkoxy;
- W is either a single covalent bond or --NR.sup.5 --, wherein R.sup.5 is selected from hydrogen, lower alkyl, lower acyl, and lower alkylsulfonyl;
- X is selected from --NR.sup.2 R.sup.3, --OR.sup.2, and R.sup.6, wherein R.sup.6 can be hydrogen, lower alkyl, C.sub.5-7 cycloalkyl, phenyl, and phenyl-lower alkyl;
- Y and Z are independently selected from N and CH with the proviso that both Y and Z cannot be CH simultaneously;
- m is selected from zero and the integers 1 to 3; and
- n is selected from the integers 1 to 5.
- 2. A compound of claim 1 wherein W is a single covalent carbon-carbon bond.
- 3. A compound of claim 1 wherein W is --NR.sup.5 --.
- 4. A compound of claim 1 wherein m is zero and n is 3.
- 5. A compound of claim 2 selected from the group consisting of 3-[3-[4-(5-methoxy-4-pyrimidinyl)-1-piperazinyl)propyl]-5-(1,2-dioxo-4-methylamino-3-cyclobuten-3-yl)indole; 3-[3-[4-(5-methoxy-4-pyrimidinyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-4-amino-3-cyclobuten-3-yl)indole; 3-[3-[4-(5-methoxy-4-pyrimidinyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-4-isopropylamino-3-cyclobuten-3-yl)indole; 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl-5-(1,2-dioxo-4-t-butylamino-3-cyclobuten-3-yl)indole.
- 6. A compound of claim 3 selected from the group consisting of 3-[3-[4-(5-methoxy-4-pyrimidinyl)-1-piperazinyl]propyl]-5-[(1,2-dioxo-4-methyl-3-cyclobuten-3-yl)aminomethyl]indole; 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-4-methyl-3-cyclobuten-3-yl)amino-1H-indole; 3-[[3-[3-[4-(3-methoxy-4-pyridinyl)-1-piperazinyl]propyl]-1H-indol-5-yl]amino]-4-methyl-3-cyclobutene-1,2-dione; 3-[[3-[3-(2-pyridinyl)-1-piperazinyl]propyl]-1H-indol-5-yl]amino]-4-methyl-3-cyclobutene-1,2-dione; 3-[[3-[3-[3-2-pyridinyl)-1-piperazinyl]propyl]-1H-indol-5-yl]amino]-4-methyl-3-cyclobutene-1,2-dione; 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-3-cyclobuten-3-yl)amino-1H-indole; 3-[3-[4-(5-methoxy-4-pyrimidyl)-3-methyl-1-piperazinyl]propyl]-5-(1,2-dioxo-3-cyclobuten-3-yl)amino-1H-indole; 3-[3-[4-(5-methoxy-4-pyrimidyl)-2-methyl-1-piperazinyl]propyl]-5-(1,2-dioxo-3-cyclobuten-3-yl)amino-1H-indole; 3-[3-[4-(5-methoxy-4-pyrimidyl)-3-methyl-1-piperazinyl]propyl]-5-(1,2-dioxo-4-methyl-3-cyclobuten-3-yl)amino-1H-indole; 3-[3-[4-(5-methoxy-4-pyrimidyl)-2-methyl-1piperazinyl]propyl]-5-(1,2-dioxo-4-methyl-3-cyclobuten-3-yl)amino-1H-indole; 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-4-butyl-3-cyclobuten-3-yl)amino-1H-indole; 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-3-cyclobuten-3-yl)methylamino-1H-indole; 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-[1,2-dioxo-4-(1-methylethoxy)-3-cyclobuten-3-yl]amino-1H-indole; 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-4-hydroxy-3-cyclobuten-3-yl)amino-1H-indole; 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-4-methylamino-3-cyclobuten-3-yl)amino-1H-indole; 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-4-amino-3-cyclobuten-3-yl)amino-1H-indole; 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-4-dimethylamino-3-cyclobuten-3-yl)amino-1H-indole; 3-[3-[4-(5-methoxy-4-pyrimidinyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-4-methyl-3-cyclobuten-3-yl)amino-1H-indole; 4-ethylthio-3-[3-[4-(5-methoxy-4-pyrimidinyl)-1-piperazinyl]propyl] -5-(1,2-dioxo-4-methyl-3-cyclobuten-3-yl)amino-1H-indole.
- 7. The compound of claim 6, 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-4-methyl-3-cyclobuten-3-yl)amino-1H-indole.
- 8. A method for treating vascular headaches, consisting of migraine and cluster headaches, by administering a therapeutically effective amount of a compound claimed in claim 1 to a person suffering from a vascular headache.
- 9. A method for preventing vascular headaches, consisting of migraine and cluster headaches, by administering a prophylactically effective amount of a compound claimed in claim 1 to a person suffering the onset of a vascular headache.
- 10. A pharmaceutical composition in unit dosage form suitable for systemic administration to a person at risk of or suffering a vascular headache, the composition comprising a pharmaceutical carrier and from about 1 to 500 mg of a compound claimed in claim 1.
CROSS REFERENCE TO RELATED APPLICATION
This application is a continuation-in-part of our application, Ser. No. 08/122,266 filed Sep. 16, 1993, now abandoned.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
5077293 |
Smith et al. |
Dec 1991 |
|
5300506 |
Smith et al. |
Apr 1994 |
|
5434154 |
Smith et al. |
Jul 1995 |
|
Foreign Referenced Citations (5)
Number |
Date |
Country |
0426379 |
May 1991 |
EPX |
0464558 |
Jan 1992 |
EPX |
0548813 |
Jun 1993 |
EPX |
1551082 |
Dec 1968 |
FRX |
WO9401436 |
Jan 1994 |
WOX |
Non-Patent Literature Citations (1)
Entry |
Edmeads, J. Internal Medicine, ed. by Stein, J. H. et al. (Mosby, St. Louis), pp. 1029, 1032 (1994). |
Continuation in Parts (1)
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Number |
Date |
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Parent |
122266 |
Sep 1993 |
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