Dendritic core compounds

Patent metadata

Field	Value
Publication number	US-9828341-B2
Application number	US-201314646807-A
Country	US
Kind code	B2
Filing date	Nov 28, 2013
Priority date	Nov 28, 2012
Publication date	Nov 28, 2017
Grant date	Nov 28, 2017

Abstract

The invention relates to compounds that are useful for the preparation of dendrimer compounds, the use of these compounds for preparing dendrimers and processes for preparing the compounds.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein:
Y is O;
B is O;
R 1 and R 2 are absent; and
either A, E, D and X are all CH 2 ; or A, D and X are all CH 2 and E is (CH 2 CH 2 O) t # CH 2 ;
wherein # indicates a point of attachment of E to its adjacent carbonyl group;
t is an integer from 1 to 10;
or wherein:
Y is C;
R 1 and R 2 are both H; and
A, E, B and D are CH 2 and X is O;
or wherein:
Y is C;
X is O;
B is (CH 2 ) p ;
A, E and D are all CH 2 ; and
R 1 is H, NHZ or C 1-6 alkyl and R 2 is a radical of formula (i) or a radical of formula (ii)

Z is H, acyl, C(O)(CH 2 ) w N(H)G, *CH 3 *C(O)— where *C denotes 13 C or 14 C, 4-carboxytetramethylrhodamine, resorcinolphthalein, 7-amino-4-methyl-6-sulfocoumarin-3-acetic acid, 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene or 1-{3-{[4-(2-cyclooctyn-1-ylmethyl)benzoyl]amino}propyl}-4-{2-[4-(dimethylamino)phenyl]ethenyl}pyridinium hexafluorophosphate;
w is an integer from 1 to 11;
G is H, acyl, t-butoxycarbonyl, 2,2,2-trichloroethyloxycarbonyl, 9-fluorenylmethoxycarbonyl, benzyloxycarbonyl,*CH 3 *CO— where *C denotes 13 C or 14 C, 4-carboxytetramethylrhodamine, resorcinolphthalein, 7-amino-4-methyl-6-sulfocoumarin-3-acetic acid, 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene or 1-{3-{[4-(2-cyclooctyn-1-ylmethyl)benzoyl]amino}propyl}-4-{2-[4-(dimethylamino)phenyl]ethenyl}pyridinium hexafluorophosphate;
or wherein:
Y is C;
X is O;
B is (CH 2 ) p ;
A, E and D are all CH 2 ; and
R 1 and R 2 , both the same, are a radical of formula (i) or a radical of formula (ii)

R 3 is a radical of formula (iii) or a radical of formula (iv)

each T is independently selected from the group consisting of (CH 2 CH 2 O) x (CH 2 CH 2 and CH 2 ;
each x is independently an integer from 1 to 12;
m is an integer from 1 to 11, provided that when T is (CH 2 CH 2 O) x CH 2 CH 2 then m is 1;
n is an integer from 1 to 11, provided that when T is (CH 2 CH 2 O) x CH 2 CH 2 then n is 1;
p is an integer from 1 to 5;
R 5 is H,

and
M is sodium or ammonium.

2. The compound of claim 1 wherein each T is CH 2 .

3. The compound of claim 1 wherein at least one T is (CH 2 CH 2 O) x CH 2 CH 2 .

4. The compound of claim 1 , wherein Y is C.

5. The compound of claim 1 , wherein R 3 is a radical of formula (iii)

6. The compound of claim 1 , wherein R 3 is a radical of formula (iv)

7. The compound of claim 1 , wherein R 1 and R 2 are both a radical of formula (i)

or are both a radical of formula (ii)

8. The compound of claim 1 , herein R 5 is

9. The compound of claim 1 , wherein Y is C; R 1 and R 2 are both H; A, E, B and D are CH 2 and X is O.

10. The compound of claim 1 , wherein:
Y is C; X is O; A, E and D are all CH 2 ; B is (CH 2 ) p ;
R 1 is NHZ or C 1-6 alkyl;
R 2 is a radical of formula (i) or a radical of formula (ii)

Z is H, acyl, C(O)(CH 2 ) w NHG, *CH 3 *C(O)— where *C denotes 13 C or 14 C, 4-carboxytetramethylrhodamine; resorcinolphthalein, 7-amino-4-methyl-6-sulfocoumarin-3-acetic acid, 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene or 1-{3-{[4-(2-cyclooctyn-1-ylmethyl)benzoyl]amino}propyl}-4-{2-[4-(dimethylamino)phenyl]ethenyl}pyridinium hexafluorophosphate;
w is an integer from 1 to 11; and
G is H, acyl, t-butoxycarbony 2,2,2-trichloroethyloxycarbonyl, 9-fluorenylmethoxycarbonyl, benzyloxycarbonyl, *CH 3 *CO— where *C denotes 13 C or 14 C, 4-carboxytetramethylrhodamine, resorcinolphthalein; 7-amino-4-methyl-6-sulfocoumarin-3-acetic acid, 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene or 1-{3-{[4-(2-cyclooctyn-1-ylmethyl)benzoyl]amino}propyl}-4-{2-[4-(dimethylamino)phenyl]ethenyl}pyridinium hexafluorophosphate.

11. The compound of claim 1 , wherein Y is C; X is O; A, E and D are all CH 2 ; B is (CH 2 ) p ; R 1 and R 2 , both the same, are a radical of formula (i)

R 3 is a radical of formula (iii)

and p is 1.

12. The compound of claim 1 , wherein Y is C; Y is O; A, E and D are all CH 2 ; B is (CH 2 ) p ; R 1 and R 2 , both the same, are a radical of formula (ii)

and R 3 is a radical of formula (iv)

and p is 1.

13. The compound of claim 1 , wherein Y is C; R 1 and R 2 are both H; A, E, B and D are CH 2 ; X is O; and R 3 is a radical of formula (iii)

14. The compound of claim 1 , wherein Y is C; R 1 and R 2 are both H; A, E, B and D are CH 2 ; X is O; and R 3 is a radical of formula (iv)

15. The compound of claim 1 , wherein Y is C; Y is O; A, E and D are all CH 2 ; B is (CH 2 ) p ; R 1 is H; R 2 is a radical of formula (i)

R 3 is a radical of formula (iii)

and p is 1.

16. The compound of claim 1 , wherein Y is C; X is O; E and D are all CH 2 ; B is (CH 2 ) p ; R 1 is H; R 2 is a radical of formula (ii)

R 3 is a radical of formula (iv)

and p is 1.

17. The compound of claim 1 , wherein Y is C; X is O; A, E and D are all CH 2 ; B is (CH 2 ) p ; R 1 is H; R 2 is a radical of formula (ii)

R 3 is a radical of formula (iii)

Assignees

• Victoria Link Ltd

Inventors

• Tyler Peter Charles
• Zubkova Olga Vladimirovna

Classifications

• C07C237/22

  having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated (peptides C07K) · CPC title

• C07D207/46 Primary

  with hetero atoms directly attached to the ring nitrogen atom · CPC title

• C07C235/08

  having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms · CPC title

• C07C235/12

  having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups · CPC title