IP Library Granted Patent US 8,993,767
Granted Patent B2
US 8,993,767 · App. 13/521,936 · Granted Mar 31, 2015

Multiphoton activable quinoline derivatives, their preparation and their uses

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Quick Facts
Patent No.
US 8,993,767
App. No.
13/521,936
Granted
Mar 31, 2015
Kind
B2
Abstract

The present invention relates to multiphoton activable organic compounds responding to the following formula (I). The present invention also relates to a method of synthesizing the compounds of the invention, to an aqueous solution comprising at least one compound of the invention, and to their specific uses. The present invention also concerns a method of liberating organic ligands, said method involving the step of irradiating a compound according to the invention.

Claims (22)

1. A compound of the following formula (I):

wherein:

n=0 or 1,

A is a nitrogen atom;

X is a direct single bond between A and the quinoline group, an alkyne group —C≡C—, or a

group;

R 1 , R′ 1 , R″ 1 , R 2 , R′ 2 , R″ 2 , R 3 , R′ 3 , R″ 3 , R 4 , R′ 4 and R″ 4 independently are hydrogen, halogen, amine, nitrile, nitro or optionally substituted linear or branched alkyl or alkoxy containing 1 to 30 carbon atoms; and

Y, Y′ and Y″ independently are OH, OC(O)CH 3 or OC(O)CH 2 CH 2 CH(NH 2 )COOH.

2. A compound according to claim 1 of the following formula:

3. A compound according to claim 1 of the following formula:

4. A compound according to claim 1 selected from the following compounds:

5. A method of synthesizing a compound according to claim 1 , comprising the following steps:

(i) a transformation step of an optionally substituted bromoaniline in a bromoquinaldine,

(ii) an amination step of the bromoquinaldine obtained in step (i), in the presence of copper and L-proline,

(iii) a reaction between the aminoquinaldine obtained in step (ii) and two equivalents of bromoquinaldine, and

(iv) an oxidation step, followed by a reduction step.

6. An aqueous solution comprising at least one compound according to claim 1 .

7. An aqueous solution according to claim 6 , wherein the compound is present at a concentration ranging from 10 −5 to 10 −1 mol·L −1 .

8. An aqueous solution according to claim 6 , having a pH of 6 to 8.

9. A method of liberating a Y—H, a Y′—H and/or a Y″—H compound, comprising the step of irradiating a compound according to claim 1 .

10. A method as defined according to claim 9 , wherein the irradiating step is carried out at a wavelength ranging from 600 to 1000 nm.

11. The method of claim 10 , wherein the wavelength ranges from 650 to 800 nm.

Assignments (5)
CORRECTIVE ASSIGNMENT TO CORRECT THE PROPERTY NUMBER 16930208 PREVIOUSLY RECORDED AT REEL: 060541 FRAME: 0336. ASSIGNOR(S) HEREBY CONFIRMS THE MERGER AND CHANGE OF NAME. Recorded Jan 11, 2023
From: UNIVERSITE PARIS DESCARTES; UNIVERSITE PARIS DIDEROT - PARIS 7
To: UNIVERSITE DE PARIS
Reel/Frame 062387/0346 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PROPERTY NUMBER 16930208 PREVIOUSLY RECORDED AT REEL: 060390 FRAME: 0122. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Jan 11, 2023
From: UNIVERSITE DE PARIS
To: UNIVERSITÉ PARIS CITÉ
Reel/Frame 062387/0489 →
CHANGE OF NAME Recorded Jun 20, 2022
From: UNIVERSITE DE PARIS
To: UNIVERSITÉ PARIS CITÉ
Reel/Frame 060390/0122 →
MERGER AND CHANGE OF NAME Recorded Jun 20, 2022
From: UNIVERSITE PARIS DESCARTES; UNIVERSITE PARIS DIDEROT - PARIS 7; UNIVERSITE DE PARIS
To: UNIVERSITE DE PARIS
Reel/Frame 060541/0336 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 29, 2012
From: DALKO, PETER; PETIT, MORGANE; OGDEN, DAVID; ACHER, FRANCINE
To: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
Reel/Frame 029377/0392 →