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US 4,309,348 AGranted
Tricyclic indole derivatives
AssigneeAmerican Home Products Corporation
InventorsAndre A. Asselin, Leslie G. Humber, Gervais Dionne, Clara Revesz, Amedeo Failli
Life of this patent
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Abstract
Indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole or 1,3,4,9-tetrahydrothiopyrano[3,4-b]indole nucleus with a hydroxyalkanamine or lower alkoxyalkanamine substituent and a lower alkyl group at position 1 are disclosed. The nucelus is optionally further substituted at position 9 and on the aromatic ring. The derivatives are useful diuretic agents, and methods for their preparation and use are also disclosed.
Claims7
A compund selected from the group of those of formula VIa ##STR10## in which R.sup.1 is lower alkyl;
- R.sup.2 is hydrogen or lower alkyl;
- R.sup.3 and R.sup.4 each independently is hydrogen, lower alkyl, halo, nitro, trifluoromethyl or lower alkoxy;
- and X is oxa or thia and those of formula IV ##STR11## in which R.sup.1 is lower alkyl;
- R.sup.2 is hydrogen or lower alkyl;
- R.sup.3 and R.sup.4 each independently is hydrogen, lower alkyl, halo, nitro, trifluoromethyl or lower alkoxy;
- X is oxa or thia;
- Y is selected from the group consisting of:
- a. COOR.sup.8 wherein R.sup.8 is hydrogen or lower alkyl, or a radical of formula Alk.sup.3 -COOR.sup.8 wherein Alk.sup.3 is a straight or branched chain lower alkylene having one to five carbon atoms and R.sup.8 is as defined herein;
- b. CONR.sup.5 R.sup.6 wherein R.sup.5 and R.sup.6 each is hydrogen or lower alkyl, or a radical of formula Alk.sup.3 -CONR.sup.5 R.sup.6 wherein Alk.sup.3, R.sup.5 and R.sup.6 are as defined herein;
- c. a radical of formula Alk.sup.1 -NR.sup.5 -COR.sup.9 wherein Alk.sup.1 is a straight or branched chain lower alkylene having one to six carbon atoms, R.sup.5 is as defined herein and R.sup.9 is hydrogen or lower alkyl;
- d. a radical of formula Alk.sup.1 -halo wherein Alk.sup.1 is as defined herein and halo is chloro, bromo or iodo;
- e. a radical of formula Alk.sup.1 -NO.sub.2 wherein Alk.sup.1 is as defined herein;
- and
- f. a radical of formula Alk.sup.1 -NR.sup.5 R.sup.6 wherein Alk.sup.1, R.sup.5 and R.sup.6 are as defined herein;
- and Z is selected from the group consisting of:
- a. COOR.sup.10 wherein R.sup.10 is hydrogen or lower alkyl, or a radical of formula Alk.sup.4 -COOR.sup.10 wherein Alk.sup.4 is a straight or branched chain lower alkylene having one to five carbon atoms and R.sup.10 is as defined herein;
- b. a radical of formula Alk.sup.2 -OCOR.sup.11 wherein Alk.sup.2 is a straight or branched chain lower alkylene having one to six carbon atoms and R.sup.11 is lower alkyl;
- and
- c. a radical of formula Alk.sup.2 -OR.sup.7 wherein Alk.sup.2 is as defined herein and R.sup.7 is hydrogen or lower alkyl with the proviso that when Y is a radical of formula Alk.sup.1 -NR.sup.5 R.sup.6 then Z is selected from the group consisting of COOR.sup.10, and Alk.sup.2 -OCOR.sup.11.
16 more elements
A compound of formula VIa ##STR12## in which R.sup.1 is lower alkyl;
- R.sup.2 is hydrogen or lower alkyl;
- R.sup.3 and R.sup.4 each independently is hydrogen, lower alkyl, halo, nitro, trifluoromethyl or lower alkoxy;
- and X is oxa or thia.
A compound of formula VIa ##STR13## in which R.sup.1 is lower alkyl;
- R.sup.2 is hydrogen;
- R.sup.3 and R.sup.4 each is hydrogen, lower alkyl or halo;
- and X is oxa or thia.
A compound of formula IV ##STR14## in which R.sup.1 is lower alkyl;
- R.sup.2 is hydrogen or lower alkyl;
- R.sup.3 and R.sup.4 each independently is hydrogen, lower alkyl, halo, nitro, trifluoromethyl or lower alkoxy;
- X is oxa or thia;
- Y is selected from the group consisting of:
- a. COOR.sup.8 wherein R.sup.8 is hydrogen or lower alkyl, or a radical of formula Alk.sup.3 -COOR.sup.8 wherein Alk.sup.3 is a straight or branched chain lower alkylene having one to five carbon atoms and R.sup.8 is as defined herein;
- b. CONR.sup.5 R.sup.6 wherein R.sup.5 and R.sup.6 each is hydrogen or lower alkyl, or a radical of formula Alk.sup.3 -CONR.sup.5 R.sup.6 wherein Alk.sup.3, R.sup.5 and R.sup.6 are as defined herein;
- c. a radical of formula Alk.sup.1 -NR.sup.5 -COR.sup.9 wherein Alk.sup.1 is a straight or branched chain lower alkylene having one to six carbon atoms, R.sup.5 is as defined herein and R.sup.9 is hydrogen or lower alkyl;
- d. a radical of formula Alk.sup.1 -halo wherein Alk.sup.1 is as defined herein and halo is chloro, bromo or iodo;
- e. a radical of formula Alk.sup.1 -NO.sub.2 wherein Alk.sup.1 is as defined herein;
- and
- f. a radical of formula Alk.sup.1 -NR.sup.5 R.sup.6 wherein Alk.sup.1, R.sup.5 and R.sup.6 are as defined herein;
- and Z is selected from the group consisting of:
- a. COOR.sup.10 wherein R.sup.10 is hydrogen or lower alkyl, or a radical of formula Alk.sup.4 -COOR.sup.10 wherein Alk.sup.4 is a straight or branched chain lower alkylene having one to five carbon atoms and R.sup.10 is as defined herein;
- b. a radical of formula Alk.sup.2 -OCOR.sup.11 wherein Alk.sup.2 is a straight or branched chain lower alkylene having one to six carbon atoms and R.sup.11 is lower alkyl;
- and
- c. a radical of formula Alk.sup.2 -OR.sup.7 wherein Alk.sup.2 is as defined herein and R.sup.7 is hydrogen or lower alkyl with the proviso that when Y is a radical of formula Alk.sup.1 -NR.sup.5 R.sup.6 then Z is selected from the group consisting of COOR.sup.10, and Alk.sup.2 -OCOR.sup.11.
13 more elements
A compound of formula IVa ##STR15## in which R.sup.1 is lower alkyl;
- R.sup.2 is hydrogen or lower alkyl;
- R.sup.3 and R.sup.4 each independently is hydrogen, lower alkyl, halo, nitro, trifluoromethyl or lower alkoxy;
- R.sup.7 is hydrogen;
- Alk.sup.2 is a straight or branched chain lower alkylene having one to six carbon atoms;
- X is oxa or thia, and Y is CONR.sup.5 R.sup.6 wherein R.sup.5 and R.sup.6 each is hydrogen or lower alkyl or a radical of formula Alk.sup.3 -CONR.sup.5 R.sup.6 wherein Alk.sup.3 is a straight or branched chain lower alkylene having one to five carbon atoms and R.sup.5 and R.sup.6 are as defined herein.
2 more elements
A compound of formula IVb ##STR16## in which R.sup.1 is lower alkyl;
- R.sup.2 is hydrogen or lower alkyl;
- R.sup.3 and R.sup.4 are hydrogen;
- R.sup.5 is lower alkyl;
- R.sup.6 is hydrogen or lower alkyl;
- R.sup.7 is hydrogen or lower alkyl;
- and X is oxa or thia.
3 more elements
Dependencies are inferred from the claim text.