Macrocyclic compounds, polymers, and methods for making same

Patent metadata

Field	Value
Publication number	US-9783520-B2
Application number	US-201515311269-A
Country	US
Kind code	B2
Filing date	May 15, 2015
Priority date	May 16, 2014
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

The application relates to macrocyclic compounds and related polymers, as well as to processes for synthesizing them, e.g., using olefins as starting material.

First claim

What is claimed:

1. A compound according to Formula I or Formula II:

or a salt thereof, wherein,
R 1 is a bond, optionally substituted C 1 -C 12 alkyl, optionally substituted C 2 -C 12 alkenyl, or optionally substituted C 2 -C 12 alkynyl;
R 2 is optionally substituted C 1 -C 12 alkyl, optionally substituted C 2 -C 12 alkenyl, or optionally substituted C 2 -C 12 alkynyl;
X is O or NR x ;
R x is hydrogen or optionally substituted C 1 -C 12 alkyl;
Z is hydrogen or

one of the is a double bond and the other is a single bond;
m is an integer between 1 and 10; and
n is an integer between 1 and 100,000.

2. The compound of claim 1 , wherein, for the compound of Formula I, the number of atoms comprising the ring structure is between 13 and 19.

3. The compound of claim 1 , wherein X is O.

4. The compound of claim 1 , wherein X is NH.

5. The compound of claim 1 , wherein Z is hydrogen.

6. The compound of claim 1 , wherein Z is

7. The compound of claim 1 , wherein R 1 is optionally substituted linear C 1 -C 12 alkyl branched C 3 -C 12 alkyl, unsubstituted linear C 1 -C 12 alkyl, optionally substituted linear C 2 -C 12 alkenyl, unsubstituted linear C 2 -C 12 alkenyl or branched C 3 -C 12 alkenyl.

8. The compound of claim 1 , wherein R 2 is optionally substituted linear C 1 -C 12 alkyl, unsubstituted linear C 1 -C 12 alkyl or branched C 3 -C 12 alkyl.

9. The compound of claim 1 , wherein R 2 is linear C 1 -C 12 alkyl or branched C 3 -C 12 alkyl substituted with one or more hydroxyl groups.

10. The compound of claim 1 , wherein R 2 is optionally substituted linear C 2 -C 12 alkenyl, unsubstituted linear C 2 -C 12 alkenyl or branched C 3 -C 12 alkenyl.

11. The compound of claim 1 , wherein R 2 is optionally substituted linear C 2 -C 12 alkynyl, unsubstituted linear C 2 -C 12 alkynyl or branched C 4 -C 12 alkynyl.

12. The compound of claim 1 according to Formula II, selected from:

and salts thereof.

13. The compound of claim 1 according to Formula I, selected from:

and salts thereof.

14. A method of producing a compound of claim 1 , or a salt thereof, comprising reacting a compound of Formula III or Formula IV:

with a compound of Formula V:

to obtain a reaction mixture comprising a compound of Formula I or Formula II, a salt thereof, or a combination thereof:

wherein,
R 1 is a bond, optionally substituted C 1 -C 12 alkyl, optionally substituted C 2 -C 12 alkenyl, or optionally substituted C 2 -C 12 alkynyl;
R 2 is optionally substituted C 1 -C 12 alkyl, optionally substituted C 2 -C 12 alkenyl, or optionally substituted C 2 -C 12 alkynyl;
R 3 is hydrogen, optionally substituted C 1 -C 12 alkyl, optionally substituted C 2 -C 12 alkenyl, or optionally substituted C 2 -C 12 alkynyl;
R 4 is hydrogen, optionally substituted C 1 -C 12 alkyl, optionally substituted C 2 -C 12 alkenyl, or optionally substituted C 2 -C 12 alkynyl;
X is O or NR x ;
R x is hydrogen or optionally substituted C 1 -C 12 alkyl;
Z is hydrogen or

one of the is a double bond and the other is a single bond;
m is an integer between 1 and 10; and
n is an integer between 1 and 100,000;
wherein the ratio of the compound of Formula III or Formula IV to the compound of Formula V is 2 to 1 or greater; and
wherein the reaction of the compound of Formula III or Formula IV with the compound of Formula V comprises an esterification step, an etherification step, a first distillation step, and a second distillation step.

15. The method of claim 14 , further comprising an amidation step, wherein a compound of Formula I, wherein X is O, reacts with NH 3 under an elevated pressure to obtain a corresponding compound of Formula I, wherein X is NH.

16. The method of claim 14 , wherein the esterification step is performed at a first temperature that is greater than room temperature, and the etherification step is performed at a second temperature that is lower than the first temperature.

17. The method of claim 14 , wherein the etherification step is quenched with a base.

18. The method of claim 14 , wherein each of the first and second distillation steps is independently performed at a temperature that is between 25° C. and 260° C. and at a pressure between 0.1 and 1.6 mbar.

19. The method of claim 14 , wherein R 3 is hydrogen.

20. The method of claim 14 , wherein the compound of Formula III is selected from:

Assignees

• P2 Science Inc

Inventors

• Foley Patrick
• Yang Yonghua

Classifications

• C07D321/00 Primary

  Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00 · CPC title

• C07D267/00

  Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms · CPC title

• C07D323/00

  Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms · CPC title