US4987237A
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Derivatives of monophosphoryl lipid A
Assignee: Ribi Immunochem Research Inc
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Filing: 1987-10-22
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Granted: 1991-01-22
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Expires: 2007-10-22
Abstract
Abstract Novel derivatives of monophosphoryl lipid A and a process for their preparation are provided. The derivatives contain one or more free groups, such as an amine, on a side chain attached to the primary hydroxyl groups of the monophosphoryl lipid A nucleus through an ester group. The derivatives provide a convenient method for coupling the lipid A through coupling agents to various biologically active materials, substrates, and the like, wherein the immunostimulant properties of lipid A are desired.
Inventors
- 👤 Kent R. Myers
- 👤 Edgar F. Ribi, deceased
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 13:28
CPC Classifications
C; C07; C07H; C07H13/00; C07H13/02; C07H13/04; C07H13/06; A; A61; A61K; A61K45/00; A61K45/05; C07K; C07K17/00; C07K17/02; C07K17/06; C07K9/00; C07K9/001
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
69 words
A derivative of monophosphoryl lipid A having the formula: ##STR16## wherein R 1 and R 2 are hydrogen, R 3 is a straight or branched hydrocarbon chain composed of carbon, hydrogen, and optionally oxygen, nitrogen and sulfur which if more than one atom may be the same or different, wherein the total number of carbon atoms does not exceed 60, and the circle represents a monophosphoryl lipid A nucleus.
Claim 2
Dependent Claim
69 words
A derivative of monophosphoryl lipid A having the formula: ##STR16## wherein R 1 and R 2 are hydrogen, R 3 is a straight or branched hydrocarbon chain composed of carbon, hydrogen, and optionally oxygen, nitrogen and sulfur which if more than one atom may be the same or different, wherein the total number of carbon atoms does not exceed 60, and the circle represents a monophosphoryl lipid A nucleus.
Claim 3
Dependent Claim
113 words
A derivative of monophosphoryl lipid A having the formula: ##STR17## wherein the segment of the derivative represented by: ##STR18## contains 2-60 carbon atoms and wherein R 3 is a straight or branched hydrocarbon chain composed of carbon, hydrogen, and optionally oxygen, nitrogen and sulfur which if more than one atom may be the same or different, and x is a minimum of 1 and can be any whole number such that the total number of carbon atoms of all x segments does not exceed 60, wherein the chemical structure of each R 3 may be the same or different in each such segment and wherein the circle represents a monophosphoryl lipid A nucleus.
Claim 4
Dependent Claim
113 words
A derivative of monophosphoryl lipid A having the formula: ##STR17## wherein the segment of the derivative represented by: ##STR18## contains 2-60 carbon atoms and wherein R 3 is a straight or branched hydrocarbon chain composed of carbon, hydrogen, and optionally oxygen, nitrogen and sulfur which if more than one atom may be the same or different, and x is a minimum of 1 and can be any whole number such that the total number of carbon atoms of all x segments does not exceed 60, wherein the chemical structure of each R 3 may be the same or different in each such segment and wherein the circle represents a monophosphoryl lipid A nucleus.
Claim 5
Dependent Claim
19 words
The derivative of claim 1, wherein the total number of carbon atoms in R 3 does not exceed 20.
Claim 6
Dependent Claim
74 words
The derivative of claim 2, wherein the segment of the derivative represented by: ##STR19## contains 2-20 carbon atoms and wherein R 3 is as indicated and wherein x is a minimum of 1 and can be any whole number such that the total number of carbon atoms of all x segments does not exceed 20, and wherein the chemical structure of each R 3 may be the same or different in each such segment.
Claim 7
Dependent Claim
45 words
The derivative of claim 2, wherein the segment of the derivative represented by: ##STR20## is an alpha-amino acid residue and wherein when the value of x is greater than 1, the alpha amino acid residue in each such segment may be the same or different.
Claim 8
Dependent Claim
44 words
The derivative of claim 4, wherein the segment of the derivative represented by: ##STR21## is an alpha-amino acid residue and wherein when the value of x is greater than 1, the alpha-amino acid residue in each such segment may be the same or different.
Claim 9
Dependent Claim
22 words
The derivative of claim 3, having the formula: ##STR22## wherein x is 5 and the circle represents a monophosphoryl lipid A nucleus.
Claim 10
Dependent Claim
27 words
The derivative of claim 5, wherein the alpha-amino acid residue is selected from the group consisting of glycine, alanine, methionine, valine, norvaline, leucine, isoleucine, phenylalanine and lysine.
Claim 11
Dependent Claim
27 words
The derivative of claim 6, wherein the alpha-amino acid residue is selected from the group consisting of glycine, alanine, methionine, valine, norvaline, leucine, isoleucine, phenylalanine and lysine.
Claim 12
Dependent Claim
12 words
The derivative of claim 9, wherein the alpha-amino acid residue is glycine.
Claim 13
Dependent Claim
12 words
The derivative of claim 9, wherein the alpha-amino acid residue is lysine.
References Cited (Backward Citations)
US4437728A
Cited
US4436727A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-01-21 | 1994-07-23 | 1995-01-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-01-21 | 1998-07-23 | 1999-01-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-01-21 | 2002-07-23 | 2003-01-22 | $7700.00 | Window Closed / Lapsed |