Preparation and uses of conjugated solid supports for boronic acids

• US 6,919,382 B2
• Filed: 08/31/2001
• Issued: 07/19/2005
• Est. Priority Date: 08/31/2000
• Status: Expired due to Fees

• Current Assignee: The Governors of the University of Alberta (University of Alberta)
• Original Assignee: The Governors of the University of Alberta (University of Alberta)
• Inventors: Hall, Dennis G.
• Primary Examiner(s): Lipman, Bernard
• Application Number:
  US09/943,465
• Publication Number:
  US 20030044840A1
• Time in Patent Office: 1,418 Days
• Field of Search: 525/332.2, 525/333.3, 525/333.4, 525/333.5, 525/333.6, 521/25, 521/26, 521/27, 521/28, 521/29, 521/30, 521/31, 521/32, 521/33, 521/34, 521/35, 521/36, 521/37, 521/38
• US Class Current: 521/25
• CPC Class Codes: C07B 2200/11 Compounds covalently bound to a solid support
• CPC Class Codes: C07F 5/025 Boronic and borinic acid compounds

Abstract

The invention provides novel solid supports comprising dihydroxyalkyl aminoalkyl and dihydroxyalkylaminobenzyl groups, and methods for making and using them. The supports are particularly useful for immobilizing and derivatizing functionalized boronic acids for use in solid phase synthesis, such as those used in combinatorial chemistries. The compositions and methods of the invention are also useful as scavenger solid supports, e.g., in solution-phase parallel synthesis of small molecule libraries, and for use in resin-to-resin transfer reactions via phase transfer of solid supported boronic acids under both aqueous and anhydrous conditions. The methods of the invention provide convergent solid-phase synthesis of symmetrically or unsymmetrically functionalized compounds, such as biphenyl compounds. Also provided are synthesizer devices, e.g., semiautomated parallel synthesizers.

Claims

1. A dihydroxyalkylaminoalkyl- or dihydroxyalkylaminobenzyl-conjugated solid support, wherein the dihydroxyalkylamino moiety comprises the formula HO(CH₂)₂N(CH₂)₂ OH, and wherein the solid support comprises a cross-linked polystyrene having about 1% to 2% cross-linking.

2. The solid support of claim 1, wherein the dihydroxyalkylaminoalkyl group or dihydroxyalkylaminobenzyl group is a diethanolaminoethyl, a diethanolaminoethyl, a diethanolaminopropyl, a diethanolaminobutyl group or a diethanolaminobenzyl group.

3. The solid support of claim 1, wherein the cross-linked polystyrene comprises a cross-linked poly(styrene-divinylbenzene) (PS-DVB) copolymer having about 1% to 2% cross-linking.

4. The solid support of claim 1, wherein tho solid support comprises a cross-linked poly(styrene-divinylbenzene) copolymer having about 1% cross-linking.

5. An N,N-diethanolaminomethyl-conjugated solid support, wherein the solid support comprises a cross-linked polystyrene having about 1% to 2% cross-linking.

6. The solid support of claim 5, wherein the solid support comprises a cross-linked poly(styrene-divinylbenzene) copolymer having about 1% to 2% cross-linking.

7. The solid support of claim 6, wherein the solid support comprises a cross-linked poly(styrene-divinylbenzene) copolymer having about 1% cross-linking.