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US5101028A Expired / Lapsed US ⏱️ 0.0 years remaining

(1,2,4)triazolo[2,3-a]pyridines

Assignee: Dystar Textilfarben GmbH and Co Deutschland KG
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Filing: 1990-08-10
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Granted: 1992-03-31
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Expires: 2010-08-10
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Abstract

Abstract Triazolopyridines of the formula <IMAGE> where R1 is C1-C20-alkyl which may be substituted, phenyl which may be substituted, or hydroxyl, R2 is hydrogen, formyl, nitroso, cyano or substituted methyl, R3 is hydrogen, cyano, carbamoyl, carboxyl or C1-C4-alkoxycarbonyl and R4 is hydroxyl, halogen, amino which may be substituted or the radical of a compound with an acidic CH, are prepared as described. The compounds are useful as intermediates in the preparation of dyes.

Inventors

  • 👤 Ernst Schefczik
  • 👤 Helmut Reichelt

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 10:21
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04

Claims Analysis

Total Claims: 3
Claim 1
Independent Claim 339 words
A triazolopyridine of the formula I ##STR20## where R 1 is C 1 -C 20 -alkyl optionally substituted with phenyl, phenoxy, carboxy or C 1 -C6hd 20-alkoxycarboxyl whose alkyl chain may be interrupted by 1 to 4 oxygens or substituted by phenyl or phenoxy, and may be interrupted by one or more oxygens, phenyl optionally substituted with C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen, nitro or carboxyl, or hydroxyl, R 2 is hydrogen, formyl, nitroso, cyano, C 1 -C 4 -alkoxymethyl or CH 2 --NL 1 L 2 where L 1 and L 2 are identical or different and each, independently of one another, is hydrogen or C 1 -C 4 -alkyl, or they form together with the nitrogen connecting them a 5- or 6-membered saturated heterocyclic radical, R 3 is cyano, carbamoyl, carboxyl or C 1 -C 4 -alkoxycarbonyl and R 4 is hydroxyl, halogen, --NL 1 L 2 where L 1 and L 2 each have the abovementioned meaning, or the radical of a compound with an acidic CH derived from the nitromethane, nitroethane or compounds of the formulae V to X ##STR21## where X 1 is cyano, nitro, C 1 -C 4 -alkanoyl, benzoyl optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen, C 1 -C 4 -alkylsulfonyl, phenylsulfonyl optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen, carboxyl, C 1 -C 4 -alkoxycarbonyl, phenoxycarbonyl, carbamoyl, momo- or di-C 1 -C 4 -alklcarbamoyl, phenylcarbamoyl optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen, phenyl optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or nitro, 2-benzothiazolyl, 2-benzimidazolyl, 5-phenyl-1,3,4-thiadiazol-2-yl or 2-hydroxy-3-quinoxalinyl, X 2 is C 1 -C 4 -alkoxy, X 3 is C 1 -C 4 -alkoxycarbonyl, phenylcarbamoyl or 2-benzimidazolyl, X 4 is hydrogen or C 1 -C 6 -alkyl, X 5 is hydrogen, C 1 -C 4 -alkyl or phenyl and X 6 is C 1 -C 4 -alkyl.
Claim 2
Dependent Claim 339 words
A triazolopyridine of the formula I ##STR20## where R 1 is C 1 -C 20 -alkyl optionally substituted with phenyl, phenoxy, carboxy or C 1 -C6hd 20-alkoxycarboxyl whose alkyl chain may be interrupted by 1 to 4 oxygens or substituted by phenyl or phenoxy, and may be interrupted by one or more oxygens, phenyl optionally substituted with C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen, nitro or carboxyl, or hydroxyl, R 2 is hydrogen, formyl, nitroso, cyano, C 1 -C 4 -alkoxymethyl or CH 2 --NL 1 L 2 where L 1 and L 2 are identical or different and each, independently of one another, is hydrogen or C 1 -C 4 -alkyl, or they form together with the nitrogen connecting them a 5- or 6-membered saturated heterocyclic radical, R 3 is cyano, carbamoyl, carboxyl or C 1 -C 4 -alkoxycarbonyl and R 4 is hydroxyl, halogen, --NL 1 L 2 where L 1 and L 2 each have the abovementioned meaning, or the radical of a compound with an acidic CH derived from the nitromethane, nitroethane or compounds of the formulae V to X ##STR21## where X 1 is cyano, nitro, C 1 -C 4 -alkanoyl, benzoyl optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen, C 1 -C 4 -alkylsulfonyl, phenylsulfonyl optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen, carboxyl, C 1 -C 4 -alkoxycarbonyl, phenoxycarbonyl, carbamoyl, momo- or di-C 1 -C 4 -alklcarbamoyl, phenylcarbamoyl optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen, phenyl optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or nitro, 2-benzothiazolyl, 2-benzimidazolyl, 5-phenyl-1,3,4-thiadiazol-2-yl or 2-hydroxy-3-quinoxalinyl, X 2 is C 1 -C 4 -alkoxy, X 3 is C 1 -C 4 -alkoxycarbonyl, phenylcarbamoyl or 2-benzimidazolyl, X 4 is hydrogen or C 1 -C 6 -alkyl, X 5 is hydrogen, C 1 -C 4 -alkyl or phenyl and X 6 is C 1 -C 4 -alkyl.
Claim 3
Dependent Claim 13 words
A triazolopyridine as claimed in claim 1, in which R 3 is cyano.

References Cited (Backward Citations)

FR2351978A1 Cited
US4288438A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1995-03-31 1995-09-30 1996-03-31 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1999-03-31 1999-09-30 2000-03-31 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2003-03-31 2003-09-30 2004-03-31 $7700.00 Window Closed / Lapsed

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