US5053497A
Expired / Lapsed
US
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Phospholipid conjugates and their preparation
Assignee: Bayer Corp
•
Filing: 1988-07-21
•
Granted: 1991-10-01
•
Expires: 2008-07-21
Abstract
Abstract Phospholipid conjugate compounds derived from cardiac glycosides and steroids useful in liposome immunoassays are disclosed as well as their method of preparation.
Inventors
- 👤 Deng R. Hwang
- 👤 Mary E. Scott
- 👤 Eddie Hedaya
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 22:21
CPC Classifications
G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/74; G01N33/743; C; C07; C07J; C07J19/00; C07J19/005; C07J41/00; C07J41/0033; C07J41/0055; C07J51/00; G01N33/94; G01N33/9453; Y; Y10; Y10S; Y10S436/00; Y10S436/829
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
60 words
A phospholipid conjugate compound of the formulae: ##STR4## wherein R is derived from an organic compound containing 1,2-dihydroxy groups, which groups are subject to oxidative cleavage; X and X' are side chain moiesties connecting the carbon atoms resulting from oxidative cleavage of the 1,2-dihydroxy groups with the R moiety; P and P' are phospholipid ethanolamine moieties; and R' is hydrogen.
Claim 2
Dependent Claim
60 words
A phospholipid conjugate compound of the formulae: ##STR4## wherein R is derived from an organic compound containing 1,2-dihydroxy groups, which groups are subject to oxidative cleavage; X and X' are side chain moiesties connecting the carbon atoms resulting from oxidative cleavage of the 1,2-dihydroxy groups with the R moiety; P and P' are phospholipid ethanolamine moieties; and R' is hydrogen.
Claim 3
Dependent Claim
26 words
The compound of claim 1, having formula I, wherein R is derived from digoxin, X is ##STR5## X' is --CH 2 -- and R' is hydrogen.
Claim 4
Dependent Claim
15 words
The compound of claim 2, digoxin-mono-DPPE, wherein P is derived from dipalmitoyl phosphatidyl ethanolamine (DPPE).
Claim 5
Dependent Claim
13 words
The compound of claim 2 wherein P is derived from dimyristyl phosphatidyl ethanolamine.
Claim 6
Dependent Claim
24 words
The compound of claim 1 having formula II wherein R is derived from digoxin, and X is ##STR6## and X' is --CH 2 --.
Claim 7
Dependent Claim
18 words
The compound of claim 5, digoxin-di-DPPE, wherein P and P' are each derived from dipalmitoyl phosphatidyl ethanolamine (DPPE).
Claim 8
Dependent Claim
16 words
The compound of claim 5 wherein P and P' are each derived from dimyristyl phosphatidyl ethanolamine.
Claim 9
Dependent Claim
26 words
The compound of claim 1, having formula I, wherein R is derived from digitoxin, X is ##STR7## X' is --CH 2 -- and R' is hydrogen.
Claim 10
Dependent Claim
14 words
The compound of claim 8 wherein P is derived from dipalmitoyl phosphatidyl ethanolamine (DPPE).
Claim 11
Dependent Claim
26 words
The compound of claim 1, having formula II, wherein R is derived from digitoxin, X is CH 3 , ##STR8## and X' is --CH 2 --.
Claim 12
Dependent Claim
17 words
The compound of claim 10 wherein P and P' are each derived from dipalmitoyl phosphatidyl ethanolamine (DPPE).
Claim 13
Dependent Claim
26 words
The compound of claim 1, having formula I, wherein R is derived from gitoxin, X is ##STR9## X' is --CH 2 -- and R' is hydrogen.
Claim 14
Dependent Claim
14 words
The compound of claim 12 wherein P is derived from dipalmitoyl phosphatidyl ethanolamine (DPPE).
Claim 15
Dependent Claim
24 words
The compound of claim 1 having formula II wherein R is derived from gitoxin, and X is ##STR10## and X' is --CH 2 --.
Claim 16
Dependent Claim
17 words
The compound of claim 14 wherein P and P' are each derived from dipalmitoyl phosphatidyl ethanolamine (DPPE).
Claim 17
Dependent Claim
28 words
The compound of claim 1, having formula I, wherein R is derived from ouabain, X is ##STR11## ##STR12## or mixtures thereof, X' is ##STR13## and R' is hydrogen.
Claim 18
Dependent Claim
14 words
The compound of claim 16 wherein P is derived from dipalmitoyl phosphatidyl ethanolamine (DPPE).
Claim 19
Dependent Claim
29 words
The compound of claim 1 having formula II wherein R is derived from ouabain, X is ##STR14## or mixtures thereof, and X' is ##STR15## or zero or mixtures thereof.
Claim 20
Dependent Claim
17 words
The compound of claim 18 wherein P and P' are each derived from dipalmitoyl phosphatidyl ethanolamine (DPPE).
Claim 21
Dependent Claim
81 words
A method of preparing compounds of claim 1 having formula I or formula II, which comprises the steps of: (a) oxidatively cleaving the 1,2-dihydroxy group, (b) reacting the dialdehyde group resulting from step (a) with carboxy methoxylamine to form a corresponding dioxime intermediate, (c) reacting the dioxime intermediate of step (b) with N-hydroxysuccinimide in the presence of dicyclohexycarbodiimide to form a dioxime active ester, and (d) condensing the dioxime active ester with a phospholipid ethanolamine to form the phospholipid conjugate compound.
Claim 22
Dependent Claim
24 words
The method of claim 20, wherein the isolation of purified compounds of formula I in step (d) is performed by preparative thin layer chromatography.
Claim 23
Dependent Claim
24 words
The method of claim 20, wherein the isolation of purified compounds of formula II in step (d) is performed by preparative thin layer chromatography.
Claim 24
Dependent Claim
31 words
The method of claim 21 for isolating a phospholipid conjugate wherein R of the conjugate is derived from digoxin, R' is hydrogen, and P is derived from dipalmitoyl phosphatidyl ethanolamine (DPPE).
Claim 25
Dependent Claim
35 words
The method of claim 21 for isolating a phospholipid conjugate wherein R of the conjugate is derived from digitoxin, gitoxin, ouabain, or digitonin, R' is hydrogen, and P is derived from dipalmitoyl phosphatidyl ethanolamine (DPPE).
Claim 26
Dependent Claim
31 words
The method of claim 22 for isolating a phospholipid conjugate wherein R of the conjugate is derived from digoxin, and P and P' are each derived from dipalmitoyl phosphatidyl ethanolamine (DPPE).
Claim 27
Dependent Claim
34 words
The method of claim 22 for isolating a phospholipid conjugate wherein R of the conjugate is derived from digitoxin, gitoxin, ouabain, or digitonin, and P and P' are each derived from dipalmitoyl phosphatidyl ethanolamine.
Claim 28
Dependent Claim
21 words
The method of claim 20, wherein formation of reaction products of steps (a) through (d) is monitored by thin layer chromatography.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-09-30 | 1995-04-01 | 1995-10-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-09-30 | 1999-04-01 | 1999-10-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-09-30 | 2003-04-01 | 2003-10-01 | $7700.00 | Window Closed / Lapsed |