IP Library Granted Patent US 6,863,782
Granted Patent B2
US 6,863,782 · App. 10/298,188 · Granted Mar 8, 2005

Method of preparing di(ketene acetals)

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 6,863,782
App. No.
10/298,188
Granted
Mar 8, 2005
Kind
B2
Abstract

Di(ketene acetals) are prepared by photoisomerizing the corresponding di(vinyl acetals).

Claims (23)

1. A method for preparing a di(ketene acetal) comprising photoisomerizing a di(vinyl acetal).

2. The method of claim 1 comprising photoisomerizing the di(vinyl acetal) in the presence of a transition metal organometallic compound.

3. The method of claim 2 where the transition metal organometallic compound is an iron organometallic compound.

4. The method of claim 3 where the iron organometallic compound is iron pentacarbonyl.

5. The method of claim 2 where the concentration of the transition metal organometallic compound is 0.001-10.0 mol % based on the di(vinyl acetal).

6. The method of claim 5 where the concentration of the transition metal organometallic compound is 0.01-1.0 mol % based on the di(vinyl acetal).

7. The method of claim 1 comprising photoisomerizing the di(vinyl acetal) in an inert solvent.

8. The method of claim 7 where the inert solvent comprises an alkane.

9. The method of claim 8 where the inert solvent consists essentially of an alkane.

10. The method of claim 8 where the alkane is a C 5 -C 7 alkane or a mixture of such alkanes.

11. The method of claim 1 where the di(vinyl acetal) is a compound of formula I:

where R 1 is hydrogen or a C 1 -C 2 alkyl.

12. The method of claim 11 where the di(vinyl acetal) is 3,9-divinyl-2,4,8,10-tetraoxaspiro[5,5]undecane.

13. The method of claim 1 where the di(vinyl acetal) is a compound of formula II:

where:

R is a bond, —(CH 2 ) a —, or —(CH 2 ) b —O—(CH 2 ) c —; where a is an integer of 1 to 10, and b and c are independently integers of 1 to 5;

R 1 is hydrogen or a C 1 -C 2 alkyl, and

R 2 is hydrogen or a C 1 -C 2 alkyl.

14. The method of claim 13 where the di(vinyl acetal) is di[(5-ethyl-2-vinyl-[1,3]dioxan-5-yl)methyl]ether.

15. The method of claim 1 where the di(vinyl acetal) is a compound of formula III:

where:

R is a bond, —(CH 2 ) a —, or —(CH 2 ) b —O—(CH 2 ) c —; where a is an integer of 1 to 10, and b and c are independently integers of 1 to 5; and

R 1 is hydrogen or a C 1 -C 2 alkyl.

Assignments (6)
RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT REEL 026177/FRAME 0874 Recorded Sep 27, 2023
From: TANG CAPITAL PARTNERS, LP
To: HERON THERAPEUTICS, INC. (F/K/A A.P. PHARMA, INC.)
Reel/Frame 065045/0730 →
RELEASE OF SECURITY INTEREST Recorded Mar 25, 2021
From: TANG CAPITAL PARTNERS, LP
To: HERON THERAPEUTICS, INC.
Reel/Frame 055725/0523 →
SECURITY INTEREST Recorded Aug 30, 2016
From: HERON THERAPEUTICS, INC.
To: TANG CAPITAL PARTNERS, LP
Reel/Frame 039590/0239 →
CHANGE OF NAME Recorded Feb 3, 2014
From: A.P. PHARMA, INC.
To: HERON THERAPEUTICS, INC.
Reel/Frame 032153/0273 →
SECURITY AGREEMENT Recorded Apr 25, 2011
From: A.P. PHARMA, INC.
To: TANG CAPITAL PARTNERS, LP, AS AGENT
Reel/Frame 026177/0874 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 27, 2003
From: NEWSOME, PETER W.; FRISBEE, A. ROGER; ITOV, ZINOVY; MORGAN, APRIL J.; NOE, ROBERT A.
To: AP PHARMA, INC.
Reel/Frame 013792/0775 →