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Triazolyl-coumarins

Assignee: Bayer AG
•
Filing: 1969-03-12
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Granted: 1977-01-25
•
Expires: 1989-03-12
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Abstract

Abstract Triazolyl-coumarins of the formula ##STR1## wherein R 1 to R 4 and X are as defined herein, or their quaternization products are useful as brightening agents.

Inventors

  • 👤 Alfons Dorlars
  • 👤 Carl-Wolfgang Schellhammer
  • 👤 Wolf-Dieter Wirth

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 04:18
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3472

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 328 words
A triazolyl coumarin of the formula ##STR35##wherein R 1 is a. hydrogen; b. C 1-12 -alkyl which may be substituted by halogen, hydroxy, C 1-4 alkoxy, C 1-4 alkyl carbonyl, COOH, C 1-4 alkoxycarbonyloxy, phenyl, halo-phenyl, lower alkyl phenyl, or lower alkoxy phenyl; c. cyclohexyl; or d. phenyl which may be substituted by fluoro, chloro, bromo, CN, C 1-4 -alkyl, C 1-4 -alkoxy, phenyl C 1-4 -alkyl, carboxy C 1-4 -alkyl, phenyl C 1-4 -alkoxy, carboxy C 1-4 -alkoxy, C 1-5 -alkoxy carbonyl, C 1-4 -alkyl sulfonyl, phenyl or phenoxy; R 2 is H or is a. R 1 ; b. CN; c. COOH; d. C 1-4 -alkoxy carbonyl; e. CONH 2 ; f. N-C 1-4 -alkyl carbonamide; g. N,N-di-C 1-4 -alkyl carbonamide; h. or acylamino wherein acyl is selected from the class consisting of alkoxycarbonyl with 1-4 carbon atoms in the alkoxy group; alkyl carbonyl with 1-10 carbon atoms in the alkyl radical; phenyl carbonyl; or substituted acyl as defined above but additionally containing a substituent selected from the class consisting of halogen, amino, phenyl, ethoxy, methoxy, propoxy, methyl, dimethylamino, diethylamino, or dipropylamino; R 1 and R 2 together with the two carbon atoms of the triazole ring may form a member selected from the group consisting of ##STR36##and R 3 and R 4 , independently of one another are selected from the group consisting of hydrogen, alkyl with 1-4 carbon atoms and phenyl; X is N or C-R 5 where R 5 is H or alkyl with 1-4 carbon atoms or their quaternization products of the formula ##STR37##where Y - is an anion, and R 6 is selected from the group consisting of alkyl with 1-12 carbon atoms, which is unsubstituted or substituted by a member of the class consisting of halogen; OH; alkoxy with 1-4 carbon atoms; alkyl carbonyloxy with 1-4 carbon atoms in the alkyl radical; COOH; alkoxy carbonyl with 1-4 carbon atoms in the alkyl group; phenyl; halophenyl; lower alkyl phenyl, and alkoxy-phenyl.
Claim 2
Dependent Claim 328 words
A triazolyl coumarin of the formula ##STR35##wherein R 1 is a. hydrogen; b. C 1-12 -alkyl which may be substituted by halogen, hydroxy, C 1-4 alkoxy, C 1-4 alkyl carbonyl, COOH, C 1-4 alkoxycarbonyloxy, phenyl, halo-phenyl, lower alkyl phenyl, or lower alkoxy phenyl; c. cyclohexyl; or d. phenyl which may be substituted by fluoro, chloro, bromo, CN, C 1-4 -alkyl, C 1-4 -alkoxy, phenyl C 1-4 -alkyl, carboxy C 1-4 -alkyl, phenyl C 1-4 -alkoxy, carboxy C 1-4 -alkoxy, C 1-5 -alkoxy carbonyl, C 1-4 -alkyl sulfonyl, phenyl or phenoxy; R 2 is H or is a. R 1 ; b. CN; c. COOH; d. C 1-4 -alkoxy carbonyl; e. CONH 2 ; f. N-C 1-4 -alkyl carbonamide; g. N,N-di-C 1-4 -alkyl carbonamide; h. or acylamino wherein acyl is selected from the class consisting of alkoxycarbonyl with 1-4 carbon atoms in the alkoxy group; alkyl carbonyl with 1-10 carbon atoms in the alkyl radical; phenyl carbonyl; or substituted acyl as defined above but additionally containing a substituent selected from the class consisting of halogen, amino, phenyl, ethoxy, methoxy, propoxy, methyl, dimethylamino, diethylamino, or dipropylamino; R 1 and R 2 together with the two carbon atoms of the triazole ring may form a member selected from the group consisting of ##STR36##and R 3 and R 4 , independently of one another are selected from the group consisting of hydrogen, alkyl with 1-4 carbon atoms and phenyl; X is N or C-R 5 where R 5 is H or alkyl with 1-4 carbon atoms or their quaternization products of the formula ##STR37##where Y - is an anion, and R 6 is selected from the group consisting of alkyl with 1-12 carbon atoms, which is unsubstituted or substituted by a member of the class consisting of halogen; OH; alkoxy with 1-4 carbon atoms; alkyl carbonyloxy with 1-4 carbon atoms in the alkyl radical; COOH; alkoxy carbonyl with 1-4 carbon atoms in the alkyl group; phenyl; halophenyl; lower alkyl phenyl, and alkoxy-phenyl.
Claim 3
Dependent Claim 97 words
Triazolyl-coumarins of the formula ##STR38##in which R 1 ' and R 2 ' stand for an alkyl radical with 1 - 4 carbon atoms, or in which R 1 ' stands for phenyl and R 2 ' stands for hydrogen or an alkyl radical with 1 - 4 carbon atoms, and their quaternisation products of the formula ##STR39##in which R 1 ' and R 2 ' stand for an alkyl radical with 1 - 4 carbon atoms; R 6 ' stands for an alkyl radical with 1 - 4 carbon atoms; and Y - means an anion.
Claim 4
Dependent Claim 97 words
Triazolyl-coumarins of the formula ##STR38##in which R 1 ' and R 2 ' stand for an alkyl radical with 1 - 4 carbon atoms, or in which R 1 ' stands for phenyl and R 2 ' stands for hydrogen or an alkyl radical with 1 - 4 carbon atoms, and their quaternisation products of the formula ##STR39##in which R 1 ' and R 2 ' stand for an alkyl radical with 1 - 4 carbon atoms; R 6 ' stands for an alkyl radical with 1 - 4 carbon atoms; and Y - means an anion.
Claim 5
Dependent Claim 6 words
The triazolyl-coumarin of the formula: ##STR40##
Claim 6
Dependent Claim 6 words
The triazolyl-coumarin of the formula: ##STR40##
Claim 7
Dependent Claim 5 words
The triazolyl-coumarin of the formula:
Claim 8
Dependent Claim 5 words
The triazolyl-coumarin of the formula:
Claim 9
Dependent Claim 5 words
The triazolyl-coumarin of the formula:
Claim 10
Dependent Claim 5 words
The triazolyl-coumarin of the formula:
Claim 11
Dependent Claim 5 words
The triazolyl-coumarin of the formula:
Claim 12
Dependent Claim 5 words
The triazolyl-coumarin of the formula:
Claim 13
Dependent Claim 6 words
The triazolyl-coumarin of the formula: ##STR41##
Claim 14
Dependent Claim 6 words
The triazolyl-coumarin of the formula: ##STR41##
Claim 15
Dependent Claim 57 words
A compound of claim 1 wherein R 1 and R 2 are selected from the group consisting of hydrogen, alkyl with 1-4 carbon atoms, benzyl, phenyl, chlorophenyl, fluorophenyl, bromophenyl, methylphenyl, methoxyphenyl, ethylphenyl, butylphenyl, phenylphenyl, benzylphenyl, benzyloxy or wherein R 1 and R 2 together form a cyclohexyl or cyclopentyl radical and wherein Y is a colorless anion.

References Cited (Backward Citations)

US3496188A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-01-25 1980-07-26 1981-01-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-01-25 1984-07-26 1985-01-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-01-25 1988-07-26 1989-01-25 $7700.00 Window Closed / Lapsed

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