David M Knapp

US Patent:

8013203, Sep 6, 2011

Filed:

Nov 8, 2007

Appl. No.:

11/937338

Inventors:

Martin D. Burke - Champaign IL, US
Eric P. Gillis - Champaign IL, US
Suk Joong Lee - Urbana IL, US
David M. Knapp - Urbana IL, US
Kaitlyn C. Gray - Champaign IL, US

Assignee:

The Board of Trustees of the University of Illinois - Urbana IL

International Classification:

C07F 5/02
C07F 9/02

US Classification:

588 6, 560126

Abstract:

A protected organoboronic acid includes a boron having an sphybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. A method of performing a chemical reaction includes contacting a protected organoboronic acid with a reagent, the protected organoboronic acid including a boron having an sphybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. The organic group is chemically transformed, and the boron is not chemically transformed.

US Patent:

8338601, Dec 25, 2012

Filed:

Sep 25, 2009

Appl. No.:

12/567443

Inventors:

Martin D. Burke - Champaign IL, US
David M. Knapp - Urbana IL, US
Eric P Gillis - Champaign IL, US

Assignee:

Board of Trustees of the University of Illinois - Urbana IL

International Classification:

C07F 5/02
C07D 213/57

US Classification:

546 13, 546330, 546144, 544336

Abstract:

A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture:R—B-T  (I);where Rrepresents an organic group, T represents a conformationally rigid protecting group, and B represents boron having sphybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKof at least 1 and a palladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.

US Patent:

8557980, Oct 15, 2013

Filed:

Feb 18, 2011

Appl. No.:

13/030833

Inventors:

Martin D. Burke - Champaign IL, US
Graham R. Dick - Vancouver, CA
David M. Knapp - Boonville IN, US
Eric P. Gillis - Wallingford CT, US
Jenna A. Klubnick - Champaign IL, US

Assignee:

The Board of Trustees of the University of Illinois - Urbana IL

International Classification:

C07F 5/02

US Classification:

540467

Abstract:

Described are methods of forming protected boronic acids that provide in a manner that is straightforward, scalable, and cost-effective a wide variety of building blocks, such as building blocks containing complex and/or pharmaceutically important structures, and/or provide simple or complex protected organoboronic acid building blocks. A first method includes reacting an imino-di-carboxylic acid and an organoboronate salt. A second method includes reacting a N-substituted morpholine dione and an organoboronic acid.

US Patent:

20120059184, Mar 8, 2012

Filed:

Jul 25, 2011

Appl. No.:

13/190223

Inventors:

Martin D. Burke - Champaign IL, US
Eric P. Gillis - Wallingford CT, US
Suk Joong Lee - Urbana IL, US
David M. Knapp - Boonville IN, US
Kaitlyn C. Gray - Champaign IL, US

Assignee:

The Board of Trustees of the University of Illinois - Urbana IL

International Classification:

C07F 5/04

US Classification:

558289

Abstract:

A protected organoboronic acid includes a boron having an sphybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. A method of performing a chemical reaction includes contacting a protected organoboronic acid with a reagent, the protected organoboronic acid including a boron having an sphybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. The organic group is chemically transformed, and the boron is not chemically transformed.

US Patent:

20130296573, Nov 7, 2013

Filed:

Oct 18, 2012

Appl. No.:

13/654820

Inventors:

Eric P. Gillis - Willingford CT, US
Suk Joong Lee - Urbana IL, US
David M. Knapp - Boonville IN, US
Kaitlyn C. Gray - Champaign IL, US

Assignee:

The Board of Trustees of the University of Illinois - Urbana IL

International Classification:

C07F 5/04
C07F 5/02
C07D 213/55
C07C 51/353
C07C 67/343
C07C 45/68
C07D 307/81

US Classification:

546342, 558289, 568433, 562 7, 549 4, 549469, 568447, 554154, 560 59

Abstract:

A protected organoboronic acid includes a boron having an sphybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. A method of performing a chemical reaction includes contacting a protected organoboronic acid with a reagent, the protected organoboronic acid including a boron having an sphybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. The organic group is chemically transformed, and the boron is not chemically transformed.

US Patent:

20130317223, Nov 28, 2013

Filed:

Nov 6, 2012

Appl. No.:

13/669906

Inventors:

David M. Knapp - Boonville IN, US
Eric P. Gillis - Wallingford CT, US

Assignee:

The Board of Trustees of the University of Illinois - Urbana IL

International Classification:

C07B 61/00
C07D 307/80
C07D 333/16
C07D 409/04
C07D 401/04
C07D 209/12
C07C 41/30
C07D 307/36
C07D 413/04
C07D 405/04
C07D 307/42
C07D 207/333

US Classification:

544356, 549497, 549469, 549 78, 549 59, 548531, 548509, 568628, 549502, 549506, 548217, 544405, 544353

Abstract:

A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture:where Rrepresents an organic group, T represents a conformationally rigid protecting group, and B represents boron having sphybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKof at least 1 and a palladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.

US Patent:

20140073785, Mar 13, 2014

Filed:

Sep 24, 2013

Appl. No.:

14/035408

Inventors:

Martin D. Burke - Champaign IL, US
Graham R. Dick - Vancouver, CA
David M. Knapp - Boonville IN, US
Eric P. Gillis - Wallingford CT, US
Jenna A. Klubnick - Champaign IL, US

Assignee:

The Board of Trustees of the University of Illinois - Urbana IL

International Classification:

C07F 5/02

US Classification:

544229, 546 13, 548110, 558289

Abstract:

Described are methods of forming protected boronic acids that provide in a manner that is straightforward, scalable, and cost-effective a wide variety of building blocks, such as building blocks containing complex and/or pharmaceutically important structures, and/or provide simple or complex protected organoboronic acid building blocks. A first method includes reacting an imino-di-carboxylic acid and an organoboronate salt. A second method includes reacting a N-substituted morpholine dione and an organoboronic acid.

US Patent:

20200002368, Jan 2, 2020

Filed:

Aug 2, 2019

Appl. No.:

16/530109

Inventors:

- Urbana IL, US
Stephen Davis - Westfield IN, US
Brice E. Uno - Highland Park IL, US
Justin Struble - Ballwin MO, US
Ian Dailey - Maplewood MN, US
Kaitlyn C. Gray - Freeland MI, US
David M. Knapp - Arlington VA, US
Pulin Wang - Austin TX, US
Nagarjuna Palyam - Florence KY, US

International Classification:

C07H 17/08
A01N 43/90

Abstract:

Provided are certain derivatives of amphotericin B (AmB) characterized by reduced toxicity and retained anti-fungal activity. Certain of the derivatives are C16 urea derivatives of AmB. Certain of the derivatives are C3, C5, C8, C9, C11, C13, or C15 deoxy derivatives of AmB. Certain of the derivatives include C3′ or C4′ modifications of the mycosamine appendage of AmB. Also provided are methods of making AmB derivatives of the invention, pharmaceutical compositions comprising AmB derivatives of the invention, and methods of use of AmB derivatives of the invention.