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Pyrenexulfonic acids useful in fluorescent lipid probes

Assignee: Individual
•
Filing: 1987-09-11
•
Granted: 1989-07-04
•
Expires: 2007-09-11
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Abstract

Abstract Compounds of formula ##STR1## wherein X is long-chain alkyloxy, long-chain alkylamino or long-chain dialkylamino, M is alkali metal, pyridinium or ammonium, Y is hydroxy or long-chain alkyloxy, which are especially useful in photometric and fluorimetric investigations of lipids and lipid-water interactions and of cationic biomolecules such as nicotine adenine dinucleotide.

Inventors

  • 👤 Ernst Koller
  • 👤 Otto S. Wolfbeis

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 16:06
CPC Classifications
C; C07; C07C; C07C309/00; C07C309/01; C07C309/28; C07C309/33; C07C309/38; C07C309/41; C07C2603/00; C07C2603/02; C07C2603/40; C07C2603/42; C07C2603/50

Claims Analysis

Total Claims: 25
Claim 1
Independent Claim 54 words
A compound having the formula ##STR6## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups; and M is chosen from the group consisting of alkali metal, pyridinum or ammonium.
Claim 2
Dependent Claim 54 words
A compound having the formula ##STR6## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups; and M is chosen from the group consisting of alkali metal, pyridinum or ammonium.
Claim 3
Dependent Claim 54 words
A compound having the formula ##STR7## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups; and M is chosen from the group consisting of alkali metal, pyridinum or ammonium.
Claim 4
Dependent Claim 54 words
A compound having the formula ##STR7## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups; and M is chosen from the group consisting of alkali metal, pyridinum or ammonium.
Claim 5
Dependent Claim 54 words
A compound having the formula ##STR8## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups; and M is chosen from the group consisting of alkali metal, pyridinum or ammonium.
Claim 6
Dependent Claim 54 words
A compound having the formula ##STR8## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups; and M is chosen from the group consisting of alkali metal, pyridinum or ammonium.
Claim 7
Dependent Claim 54 words
A compound having the formula ##STR9## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups; and M is chosen from the group consisting of alkali metal, pyridinum or ammonium.
Claim 8
Dependent Claim 54 words
A compound having the formula ##STR9## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups; and M is chosen from the group consisting of alkali metal, pyridinum or ammonium.
Claim 9
Dependent Claim 54 words
A compound having the formula ##STR10## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups; and M is chosen from the group consisting of alkali metal, pyridinum or ammonium.
Claim 10
Dependent Claim 54 words
A compound having the formula ##STR10## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups; and M is chosen from the group consisting of alkali metal, pyridinum or ammonium.
Claim 11
Dependent Claim 32 words
The compound of claim 1 wherein R is chosen from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 10-carboxy-decyl, 14-carboxy-tetradecyl, 10-ethoxycarbonyl-decyl, 14-methoxycarbonyl-tetradecyl, 10-chloro-decyl, 12-bromo-dodecyl, 12-hydroxy-dodecyl, 14-hydroxy-tetradecyl radical and M is sodium.
Claim 12
Dependent Claim 68 words
A compound have the formula ##STR11## wherein R 1 is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyloxy, alkenyloxy, arylalkyloxy, alkylamino, alkenyl-amino, dialkylamino, and dialkenylamino radical which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine, or sulfonato groups; R 2 is a hydroxy or sulfonato group; and M is chosen from the group consisting of alkali metal, pyridinium, and ammonium.
Claim 13
Dependent Claim 68 words
A compound have the formula ##STR11## wherein R 1 is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyloxy, alkenyloxy, arylalkyloxy, alkylamino, alkenyl-amino, dialkylamino, and dialkenylamino radical which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine, or sulfonato groups; R 2 is a hydroxy or sulfonato group; and M is chosen from the group consisting of alkali metal, pyridinium, and ammonium.
Claim 14
Dependent Claim 32 words
The compound of claim 7 wherein: R 1 is chosen from the group consisting of decyloxy, dodecyloxy, tetradecyloxy, hexadecyloxy, octadecyloxy, 10-carboxy-decyloxy, 14-carboxy-tetradecyloxy, 10-ethoxycarbonyldecyloxy, 14-methoxycarbonyl-tetradecyloxy, 12-bromododecyloxy, and 14-hydroxy-tetradecyloxy radical; and M is sodium.
Claim 15
Dependent Claim 32 words
The compound of claim 7 wherein: R 1 is chosen from the group consisting of a decylamino, didecylamino, dodecylamino, didodecylamino, tetradecylamino, ditetradecylamino, hexadecylamino, dihexadecylamino, bis(10-carboxydecyl)amino, and bis(12-carboxydodecyl)amino radical; and M is sodium.
Claim 16
Dependent Claim 54 words
A compound having the formula ##STR12## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, whch can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups; and M is chosen from the group consisting of alkali metal, pyridinum or ammonium.
Claim 17
Dependent Claim 54 words
A compound having the formula ##STR12## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, whch can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups; and M is chosen from the group consisting of alkali metal, pyridinum or ammonium.
Claim 18
Dependent Claim 54 words
A compound having the formula ##STR13## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups; and M is chosen from the group consisting of alkali metal, pyridinum or ammonium.
Claim 19
Dependent Claim 54 words
A compound having the formula ##STR13## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups; and M is chosen from the group consisting of alkali metal, pyridinum or ammonium.
Claim 20
Dependent Claim 32 words
The compound of claim 2 wherein R is chosen from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 10-carboxy-decyl, 14-carboxy-tetradecyl, 10-ethoxycarbonyl-decyl, 14-methoxycarbonyl-tetradecyl, 10-chlorodecyl, 12-bromo-dodecyl, 12-hydroxy-dodecyl, 14-hydroxy-tetradecyl radical; and M is sodium.
Claim 21
Dependent Claim 32 words
The compound of claim 3 wherein R is chosen from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 10-carboxy-decyl, 14-carboxy-tetradecyl, 10-ethoxycarbonyl-decyl, 14-methoxycarbonyl-tetradecyl, 10-chlorodecyl, 12-bromo-dodecyl, 12-hydroxy-dodecyl, 14-hydroxy-tetradecyl radical; and M is sodium.
Claim 22
Dependent Claim 32 words
The compound of claim 4 wherein R is chosen from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 10-carboxy-decyl, 14-carboxy-tetradecyl, 10-ethoxycarbonyl-decyl, 14-methoxycarbonyl-tetradecyl, 10-chlorodecyl, 12-bromo-dodecyl, 12-hydroxy-dodecyl, 14-hydroxy-tetradecyl radical; and M is sodium.
Claim 23
Dependent Claim 32 words
The compound of claim 5 wherein R is chosen from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 10-carboxy-decyl, 14-carboxy-tetradecyl, 10-ethoxycarbonyl-decyl, 14-methoxycarbonyl-tetradecyl, 10-chlorodecyl, 12-bromo-dodecyl, 12-hydroxy-dodecyl, 14-hydroxy-tetradecyl radical; and M is sodium.
Claim 24
Dependent Claim 32 words
The compound of claim 10 wherein R is chosen from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 10-carboxy-decyl, 14-carboxy-tetradecyl, 10-ethoxycarbonyl-decyl, 14-methoxycarbonyl-tetradecyl, 10-chlorodecyl, 12-bromo-dodecyl, 12-hydroxy-dodecyl, 14-hydroxy-tetradecyl radical; and M is sodium.
Claim 25
Dependent Claim 33 words
The compound of claim 11 wherein R is chosen from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 10-carboxy-decyl, 14-carboxy-tetradecyl, 10-ethoxycarbonyl-decyl, 14-methoxycarbonyl-tetradecyl, 10-chlorodecyl, 12-bromo-dodecyl, 12-hydroxy-dodecyl, 14hydroxy-tetradecyl radical; and M is a sodium.

References Cited (Backward Citations)

US2094224A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1992-07-03 1993-01-02 1993-07-04 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-07-03 1997-01-02 1997-07-04 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-07-03 2001-01-02 2001-07-04 $7700.00 Window Closed / Lapsed

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