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Details for Patent: 4,268,676

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Details for Patent: 4,268,676

Title: Mitomycin analogs
Abstract:Compounds of the formula, I, ##STR1## wherein: Y is hydrogen or lower alkyl; and X is a thiazolamino radical, a furfurylamino radical or a radical of the formula, ##STR2## in which R, R.sup.1, and R.sup.2 are the same or different and selected from the group consisting of hydrogen and lower alkyl, and R.sup.3 is selected from the group consisting of lower alkenyl, halo-lower alkenyl, lower alkynyl, lower akloxycarbonyl, thienyl, formamyl, tetrahydrofuryl and benzene sulfonamide. Also disclosed are novel methods for treatment of neoplastic disease states in animals, which methods comprise administering a therapeutically effective amount of a compound of the formula, Ia, ##STR3## wherein: Y is hydrogen or lower alkyl; and Z is a thiazolamino radical, a furfurylamino radical, a cyclpropylamino radical, a pyridylamino radical, or a radical of the formula, ##STR4## in which R.sup.4, R .sup.5, and R.sup.6 are the same or different and selected from the group consisting of hydrogen and lower alkyl, and R.sup.7 is selected from the group consisting of lower alkenyl, halo-lower alkenyl, lower alkynyl, lower alkoxycarbonyl, halo-lower alkyl, hydroxy-lower alkyl, pyridyl, thienyl, formamyl, tetrahydrofuryl, benzyl, and benzene sulfonamide.
Inventor(s): Remers; William A. (Tucson, AZ)
Assignee: University Patents, Inc. (Norwalk, CT)
Filing Date:Dec 05, 1979
Application Number:06/100,331
Claims:1. Compounds of the formula, ##STR11## wherein: Y is hydrogen or lower alkyl; and X is a thiazolamino radical, a furfurylamino radical or a radical of the formula, ##STR12## in which R, R.sup.1, and R.sup.2 are the same or different and selected from the group consisting of hydrogen and lower alkyl, and R.sup.3 is selected from the group consisting of lower alkenyl, halo-lower alkenyl, lower alkynyl, lower alkoxycarbonyl, thienyl, formamyl, tetrahydrofuryl and benzene sulfonamide.

2. The compounds according to claim 1 named:

1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(2-thiazol amino)azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate;

1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-furfurylam ino-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate;

1. 1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethyl-6-furfu rylamino-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate;

1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-allylamino -azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate;

1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethyl-6-allyla mino-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate;

1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(2-methyla llylamino)-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate;

1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethyl-6-(2-chl oroallylamino)-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate;

1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(N-methylp ropargylamino)-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate;

1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(1,1-dimet hylproparglyamino)-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate;

1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-proparglya mino-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate;

1,1a,8,8a,8b-hexahydro-8-(hydroxymethyl)-8-a-methoxy-1,5-dimethyl-6-proparg lyamino-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate;

1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(methoxyca rbonyl-methylamino)-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate;

1. 1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(2-thieny lmethylamino)-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate;

1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl-8a-methoxy-5-methyl-6-(aminocarbo nylmethylamino)-azirino[2',3':3,4]-pyrrolo-[1,2-a]indole-4,7-dione carbamate;

1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(2-tetrahy drofurfurylamino)-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate; and,

1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-[(4-sulpho namidophenyl)methylamino]-azirino[2',3':3,4]pyrrolo-[1,2a]indole-4,7-dione carbamate.
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