IP Library Granted Patent US 9,669,098
Granted Patent B2
US 9,669,098 · App. 14/797,312 · Granted Jun 6, 2017

Metal-organic frameworks with exceptionally large pore aperatures

Inventors: Omar M. Yaghi (Berkeley, CA); Hiroyasu Furukawa (Berkeley, CA); Hexiang Deng (Albany, CA)
Assignee: The Regents of the University of California
A61K47/24A61K38/00B01D53/02B01J20/0225B01J20/226B01J20/28016B01J20/28066B01J20/28073B01J20/28076C02F1/285C07F3/02C07F3/06C07F5/025C07F7/2224C07K14/435B01D2253/204B01J2220/58
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Quick Facts
Patent No.
US 9,669,098
App. No.
14/797,312
Granted
Jun 6, 2017
Kind
B2
Abstract

The disclosure relates to metal organic frameworks or isoreticular metal organic frameworks, methods of production thereof, and methods of use thereof.

Claims (32)

1. A composition comprising a pharmaceutically active agent and a MOF or IRMOF comprising the general structure M-L-M, wherein M comprises a metal and L is a linking moiety of Formula I:

wherein,

A 1 -A 8 are independently either N or C;

X 1 and X 2 are functional groups (FG);

R 1 -R 12 are independently selected from the group comprising H, FG, (C 1 -C 12 )alkyl, substituted (C 1 -C 12 )alkyl, (C 1 -C 12 )alkenyl, substituted (C 1 -C 12 )alkenyl, (C 1 -C 12 )alkynyl, substituted (C 1 -C 12 )alkynyl, hetero-(C 1 -C 12 )alkyl, substituted hetero-(C 1 -C 12 )alkyl, hetero-(C 1 -C 12 )alkenyl, substituted hetero-(C 1 -C 12 )alkenyl, hetero-(C 1 -C 12 )alkynyl, substituted hetero-(C 1 -C 12 )alkynyl, (C 1 -C 12 )cycloalkyl, substituted (C 1 -C 12 )cycloalkyl, aryl, substituted aryl, heterocycle, substituted heterocycle, —C(R 13 ) 3 , —CH(R 13 ) 2 , —CH 2 R 13 , —C(R 13 ) 3 , —CH(R 14 ) 2 , —CH 2 R 14 , —OC(R 13 ) 3 , —OCH(R 13 ) 2 , —OCH 2 R 14 , —OC(R 14 ) 3 , —OCH(R 14 ) 2 , —OCH 2 (R 14 ),

wherein R 1 and R 2 are linked together to form a substituted or unsubstituted ring selected from the group comprising cycloalkyl, aryl and heterocycle, and wherein R 3 and R 4 are linked together to form a substituted or unsubstituted ring selected from the group comprising cycloalkyl, aryl and heterocycle;

R 13 is selected from the group comprising FG, (C 1 -C 12 )alkyl, (C 1 -C 12 )substituted alkyl, (C 1 -C 12 )alkenyl, substituted (C 1 -C 12 )alkenyl, (C 1 -C 12 )alkynyl, substituted (C 1 -C 12 )alkynyl, hetero-(C 1 -C 12 )alkyl, substituted hetero-(C 1 -C 12 )alkyl, hetero-(C 1 -C 12 )alkenyl, substituted hetero-(C 1 -C 12 )alkenyl, hetero-(C 1 -C 12 )alkynyl, substituted hetero-(C 1 -C 12 )alkynyl, hemiacetal, hemiketal, acetal, ketal, and orthoester;

R 14 is one or more substituted or unsubstituted rings selected from the group comprising cycloalkyl, aryl, and heterocycle;

y is a number from 0 to 3;

z is a number from 0 to 20; and

with the proviso that R is absent when bound to an A that is N; and

wherein the pharmaceutically active agent is located with pores of the MOF or IRMOF.

2. The composition of claim 1 , wherein M is either a transition metal or an alkaline earth metal.

3. The composition of claim 1 , wherein M is either Mg or Zn.

4. The composition of claim 3 , wherein X 1 and X 2 are carboxylic acids.

5. The composition of claim 4 , wherein A 1 -A 8 are C.

6. The composition of claim 5 , wherein

R 1 and R 10 are hydroxyls;

R 2 -R 5 , R 7 , R 9 , R 11 and R 12 are hydrogen; and

R 6 and R 8 are selected from the group consisting of (C 1 -C 12 )alkyl, (C 1 -C 12 )alkenyl, substituted (C 1 -C 12 )alkenyl, (C 1 -C 12 )alkynyl, substituted (C 1 -C 12 )alkynyl, hetero-(C 1 -C 12 )alkyl, substituted hetero-(C 1 -C 12 )alkyl, hetero-(C 1 -C 12 )alkenyl, substituted hetero-(C 1 -C 12 )alkenyl, hetero-(C 1 -C 12 )alkynyl, and substituted hetero-(C 1 -C 12 )alkynyl.

7. The composition of claim 6 , wherein

R 6 and R 8 are (C 1 -C 6 )alkyls.

8. The composition of claim 7 , wherein z is a number from 1 to 15.

9. The composition of claim 1 , wherein the MOF or IRMOF further comprises a post-framework reactant.

10. The composition of claim 9 , wherein the post-framework reactant decreases the hydrophobicity of the framework.

11. The composition of claim 1 , wherein at least one linking moiety comprises Formula I(a):

12. A composition comprising a pharmaceutically active agent and a MOF or IRMOF having the general structure M-L-M, wherein the pharmaceutically active agent is present in pores of the MOF or IRMOF, wherein M comprises a metal and L is a linking moiety, and wherein at least one linking moiety comprises Formula IV(a):

13. A composition comprising a pharmaceutically active agent and a MOF or IRMOF having the general structure M-L-M, wherein the pharmaceutically active agent is present in pores of the MOF or IRMOF, wherein M comprises a metal and L is a linking moiety, and wherein at least one linking moiety comprises Formula IV(b):

wherein, y is a number from 0 to 20.

14. The composition of claim 1 , wherein the pharmaceutically active agent is selected from the group consisting of a protein, a drug and a gas.

15. The composition of claim 12 , wherein the pharmaceutically active agent is selected from the group consisting of a protein, a drug and a gas.

16. The composition of claim 13 , wherein the pharmaceutically active agent is selected from the group consisting of a protein, a drug and a gas.

Assignments (2)
CONFIRMATORY LICENSE Recorded Mar 28, 2018
From: UNIVERSITY OF CALIFORNIA LOS ANGELES
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 045741/0117 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 21, 2017
From: YAGHI, OMAR M.; FURUKAWA, HIROYASU; DENG, HEXIANG
To: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
Reel/Frame 042118/0018 →
Continuity (3)
Continuation 13650232 · Oct 12, 2012
Provisional Application 61547031 · Oct 13, 2011
Related Publication 20160008472A1 · Jan 14, 2016