US 4,788,285 AGranted

Indole-phthalide derivatives

OwnerWilliam M. Hung, Angelique M. Blackinventors

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Abstract

3-(1-R-2-R.sup.1 -5/6-Y-indol-3-yl)-3-(2-R.sup.2 -4-N-R.sup.3 -N-R.sup.4 -aminophenyl)-X-phthalides, 7-(1-R-2-R.sup.1 -5/6-Y-indol-3-yl)-7-(2-R.sup.2 -4-N-R.sup.3 -N-R.sup.4 -aminophenyl)furo[3,4b]-pyridine-5(7H)-ones and 5-(1-R-2-R.sup.1 -5/6-Y-indol-3-yl)-5-(2-R.sup.2 -4-N-R.sup.3 -N-R.sup.4 -aminophenyl)furo[3,4b]-pyridine-7(5H)-ones are useful as color formers in transfer imaging systems, pressure-sensitive carbonless duplicating systems and thermal-responsive marking systems. The phthalides are prepared by the interaction of the corresponding 2-(1-R-2-R.sup.1 -5/6-Y-indol-3-yl)carbonyl-X-benzoic acid with the corresponding 3-R.sup.2 -N-R.sup.3 -N-R.sup.4 -aniline or the interaction of the corresponding 2-(2-R.sup.2 -4-N-R.sup.3 -N-R.sup.4 -aminophenyl)carbonyl-X-benzoic acid with the corresponding 1-R-2-R.sup.1 -5/6-Y-indole. The furopyridines are prepared by the interaction of the corresponding 2/3-(1-R-2-R.sup.1 -5/6-Y-indol-3-yl)carbonylpyridine-3/2-carboxylic acid with the corresponding 3-R.sup.2 -N-R.sup.3 -N-R.sup.4 -aniline. The novel 1-R-2-R.sup.1 -5/6-Y-indol-3-yl)carbonyl-X-benzoic acids and 1-R-2-R.sup.1 -5/6-Y-indoles are useful as intermediates to the appropriate phthalides and furopyridinones.

Claims1

Dependent claims

A 3-(1-R-2-R.sup.1 -5/6-Y-indol-3-yl)-3-(2-R.sup.2 -4-N-R.sup.3 -N-R.sup.4 -aminophenyl) -X-phthalide having the formula ##STR17## wherein:

R represents alkylene-O-R.sup.5 in which alkylene represent --C.sub.2 H.sub.4 -- or --C.sub.3 H.sub.7 -- and R.sup.5 represent non-tertiary C.sub.1 to C.sub.6 alkyl;
R.sup.1 represents non-tertiary C.sub.1 to C.sub.4 alkyl or phenyl;
R.sup.2 represents hydrogen, ahlogen, non-tertiary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 to C.sub.8 alkoxy, dialkylamino in which alkyl is non-tertiary C.sub.1 to C.sub.4 alkyl, N-alkylamido in which alkyl is non-tertiary C.sub.1 to C.sub.4 alkyl, or trifluoromethyl
R.sup.3 and R.sup.4 independently represent non-tertiary C.sub.1 to C.sub.8 alkyl, alkylene-O-R.sup.5, alkylene-O-alkylene-O-R.sup.5 benzyl, or benzyl substituted in the phenyl ring by one or two non-tertiary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy, halo or nitro, or R.sup.3 and R.sup.4, taken together with the nirtogen represent piperidinyl, pyrrodidinyl or morpholinyl;
X represents ##STR18## in which Z represent OR.sup.6 wherein R.sup.6 represents hydrogen, a non-teriary C.sub.1 to C.sub.16 alkyl, benzyl or benzyl substituted in the phenyl ring by one or two of non-teritary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy, halo or nitro, or one to four halogen;
and
Y represents hydrogen or one or two non-tertiary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy, halo or nitro.

4 more elements

Dependencies are inferred from the claim text.

Facts

Application: 07/129,620Filed 7 Dec 1987 · division
Priority: 17 Jun 1985
Granted: 29 Nov 1988
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 491/04
In which the condensed system contains two hetero rings: ortho-condensed systems
B41M 5/145
Organic colour formers, e.g. leuco dyes: with a lactone or lactam ring
B41M 5/327
Organic colour formers, e.g. leuco dyes: with a lactone or lactam ring
C07D 405/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond

Family

Serial745,555Parent of this division · filed 17 Jun 1985
Serial937,782Parent of this division · filed 4 Dec 1986
US 4,736,027 AParent of this division
US 4,660,060 AParent of this division
US 4,788,285 AThis patent

From the US filing history. Foreign family members aren’t listed.