Claims
- 1. A chromogenic phthalide or azaphthalide of the formula ##STR119## in which V.sub.1 and V.sub.2 are each, independently of the other, hydrogen, halogen, lower alkyl, lower alkoxy, (lower alkoxy)carbonyl or --NR.sub.1 R.sub.2, at least one of the radicals V.sub.1 and V.sub.2 being lower alkoxy or --NR.sub.1 R.sub.2, A is an unsubstituted or halogen-, cyano-, nitro-, (lower alkyl)-, (lower alkoxy)-, (lower alkyl)thio-, (lower alkyl)-amino- or di(lower alkyl)amino-substituted benzene, naphthalene, pyridine, quinoline, pyrazine or quinoxaline ring, B is a substituted phenyl radical of the formula ##STR120## a 3-indolyl of the formula ##STR121## Q is --O--, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each, independently of the others, hydrogen, unsubstituted or halogen-, hydroxy-, cyanoor (lower alkoxy)-substituted alkyl having at most 12 carbon atoms, cycloalkyl having 5 to 10 carbon atoms or unsubstituted or halogen-, cyano-, (lower alkyl)- or (lower alkoxy)ringsubstituted phenalkyl or phenyl, or the substituent pairs (R.sub.1 and R.sub.2) and (R.sub.3 and R.sub.4) are each, independently of each other, together with the nitrogen atom joining them a five- or six-membered, heterocyclic radical, Y.sub.1 is hydrogen, lower alkyl, cycloalkyl, phenalkyl or phenyl, Y.sub.2 is hydrogen, lower alkyl or phenyl, Z.sub.1 and is hydrogen, unsubstituted or halogen-, hydroxyl-, cyano- or (lower alkoxy)-substituted alkyl having at most 12 carbon atoms, acyl having 1 to 12 carbon atoms or unsubstituted or halogen-, cyano-, (lower alkyl)- or (lower alkoxy)-substituted benzyl, X is hydrogen, halogen, lower alkyl, C.sub.1 -C.sub.12 -alkoxy, C.sub.1 -C.sub.12 -acyloxy, benzyl, phenyl, benzyloxy, phenyloxy, halogen-, cyano-, (lower alkyl)- or (lower alkoxy)-substituted benzyl or benzyloxy, or the group --NT.sub.1 T.sub.2, T.sub.1 and T.sub.2 are each, independently of the other, hydrogen, lower alkyl, cycloalkyl, unsubstituted or halogen-, cyano-, (lower alkyl)or (lower alkoxy)-substituted benzyl or acyl having 1 to 12 carbon atoms and T.sub.1 is also unsubstituted or halogen-, cyano-, (lower alkyl)- or (lower alkoxy)-substituted phenyl, and the benzene nucleus D is unsubstituted or substituted by halogen, cyano, lower alkyl, lower alkoxy, (lower alkoxy)carbonyl, amino, mono(lower alkyl)amino or di(lower alkyl)amino.
- 2. A phthalide or azaphthalide according to claim 1, wherein, in the formula (1), B is a 3-indolyl radical of the formula (1c).
- 3. A phthalide or azaphthalide according to claim 1, wherein, in the formula (1) V.sub.1 is --NR.sub.1 R.sub.2 or lower alkoxy and V.sub.2 is hydrogen, halogen or methyl.
- 4. A phthalide or azaphthalide according to claim 1, wherein, in the formula (1), Y.sub.1 is lower alkyl.
- 5. A phthalide or azaphthalide according to claim 1, of the formula ##STR122## in which V.sub.3 is lower alkoxy or --NR.sub.5 R.sub.6,
- V.sub.4 is hydrogen, halogen or lower alkyl,
- A.sub.1 is an unsubstituted or halogen-, cyano-, (lower alkyl)-, (lower alkoxy)- or di(lower alkyl)amino-substituted benzene or pyridine ring,
- B is a substituted phenyl radical of the formula ##STR123## or a 3-indolyl radical of the formula ##STR124## Q.sub.1 is --O--, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each, independently of the others, unsubstituted or hydroxy-, cyano- or (lower alkoxy)substituted alkyl having at most 12 carbon atoms, C.sub.5 -C.sub.6 -cycloalkyl, benzyl, phenethyl or phenyl, or the substituent pairs (R.sub.5 and R.sub.6) and (R.sub.7 and R.sub.8) are each, independently of the other, together with the nitrogen atom joining them, pyrrolidino, piperidino or morpholino,
- Y.sub.3 is lower alkyl, C.sub.5 -C.sub.6 cycloalkyl, benzyl, phenethyl or phenyl,
- Y.sub.4 is hydrogen, methyl or phenyl,
- Z.sub.3 is hydrogen, unsubstituted or cyano- or (lower alkoxy)-substituted C.sub.1 -C.sub.8 -alkyl, acetyl, propionyl or benzyl,
- X.sub.1 is hydrogen, halogen, lower alkyl, C.sub.1 -C.sub.8 -alkoxy,
- benzyloxy or the group --NT.sub.3 T.sub.4,
- T.sub.3 and T.sub.4 are each, independently of the other, hydrogen, lower alkyl, (lower alkyl)carbonyl or unsubstituted or halogen-, methyl- or methoxy-substituted benzoyl and
- W is hydrogen or halogen.
- 6. A phthalide according to claim 5, wherein, in the formula (2), the ring A.sub.1 is unsubstituted or halogen -or di(lower alkyl)amino-substituted 1 2-benzo radical.
- 7. A phthalide according to claim 5, wherein in the formula (2), B.sub.1 is a substituted phenyl radical of the formula (2a) or (2b).
- 8. A phthalide according to claim 1, of the formula ##STR125## in which the benzene ring A.sub.2 is unsubstituted or substituted by a (lower alkyl)amino or halogen,
- B.sub.2 is a substituted phenyl radical of the formula ##STR126## or a 3-indolyl radical of the formula ##STR127## Q.sub.2 is --O--, V.sub.5 is hydrogen or halogen,
- V.sub.6 is --NR.sub.9 R.sub.10 or lower alkoxy,
- R.sub.9, R.sub.10, R.sub.11 and R.sub.12 are each, independently of the others, lower alkyl, cyclohexyl or benzyl, or the substituent groups --NR.sub.9 R.sub.10 and NR.sub.11 R.sub.12 are each, independently of the other, pyrrolidino, piperidino or morpholino,
- X.sub.2 is hydrogen, methyl, lower alkoxy, benzyloxy, acetylamino, propionylamino, benzoylamino or di(lower alkyl)amino,
- Y.sub.5 is lower alkyl,
- Y.sub.6 is methyl or phenyl, and
- Z.sub.5 is hydrogen, alkyl having 1 to 8 carbon atoms or benzyl.
- 9. A phalide according to claim 8, wherein, in the formula (3),
- A.sub.2 is an unsubstituted or dimethylamino-substituted 1,2-benzo radical,
- B.sub.2 is a substituted phenyl radical of the formula (3a) or the 3-indolyl radical of the formula (3c),
- Q.sub.2 is --O--,
- V.sub.5 is hydrogen or chlorine, V.sub.6 is --NR.sub.9 R.sub.10,
- R.sub.9 is methyl, ethyl or cyclohexyl,
- R.sub.10 is methyl or ethyl or --NR.sub.9 R.sub.10 is pyrrolidinyl,
- R.sub.11 and R.sub.12 are each methyl or ethyl or --NR.sub.11 R.sub.12 is pyrrolidinyl,
- X.sub.2 is hydrogen, methoxy or ethoxy,
- Y.sub.5 is methyl or ethyl,
- Y.sub.6 is methyl, and
- Z.sub.5 is methyl, ethyl, n-butyl, hexyl or n-octyl.
Priority Claims (2)
Number |
Date |
Country |
Kind |
4268/86 |
Oct 1986 |
CHX |
|
2148/87 |
Jun 1987 |
CHX |
|
Parent Case Info
This is a divisional of application Ser. No. 113,840 filed on Oct. 26, 1987, now U.S. Pat. No. 4,876,357.
US Referenced Citations (11)
Divisions (1)
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Number |
Date |
Country |
Parent |
113840 |
Oct 1987 |
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