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US4082736A Expired / Lapsed US ⏱️ 0.0 years remaining

Novel immunological adjuvant compounds and methods of preparation thereof

Assignee: Syntex USA LLC
•
Filing: 1976-04-26
•
Granted: 1978-04-04
•
Expires: 1996-04-26
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Abstract

Abstract This application relates to novel immunological adjuvant compounds of the formula: ##STR1## wherein each of R and R 1 are the same or different and are hydrogen or an acyl radical; R 2 is an unsubstituted or substituted alkyl radical, or an unsubstituted or substituted aryl radical; R 6 is an alkyl radical X is an aminoacyl moiety; and Y is D-isoasparagine or D-isoglutamine.

Inventors

  • 👤 Gordon H. Jones
  • 👤 John G. Moffatt
  • 👤 John J. Nestor, Jr.

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 01:12
CPC Classifications
C; C07; C07K; C07K9/00; C07K9/001; C07K9/005

Claims Analysis

Total Claims: 52
Claim 1
Independent Claim 173 words
A compound selected from those of the formula: ##STR6## wherein each of R and R 1 are the same or different and are selected from the group consisting of hydrogen or an acyl radical containing from 1 to 22 carbon atoms; R 2 is selected from the group consisting of an unsubstituted or substituted alkyl radical containing from 1 to 22 carbon atoms, or an unsubstituted or substituted aryl radical containing from 6 to 10 carbon atoms; R 6 is selected from the group consisting of an alkyl radical containing from 1 to 4 carbon atoms; X is an aminoacyl moiety selected from the group consisting of ______________________________________ L-valyl, L-phenylalanyl, L-leucyl, L-tyrosyl, L-isoleucyl, L-tryptophanyl, L-α-aminobutyryl, L-lysyl, L-threonyl, L-ornithyl, L-methionyl, L-arginyl, L-cysteinyl, L-histidyl, L-glutamyl, L-asparaginyl, L-glutaminyl, L-prolyl, or L-aspartyl, L-hydroxyprolyl; ______________________________________ Y is an amino acid moiety selected from the group consisting of D-isoasparagine and D-isoglutamine; and the wavy lines ( ) represent the α- or β-configuration or mixtures thereof, with the proviso that when one wavy line is α, the other is β.
Claim 2
Dependent Claim 173 words
A compound selected from those of the formula: ##STR6## wherein each of R and R 1 are the same or different and are selected from the group consisting of hydrogen or an acyl radical containing from 1 to 22 carbon atoms; R 2 is selected from the group consisting of an unsubstituted or substituted alkyl radical containing from 1 to 22 carbon atoms, or an unsubstituted or substituted aryl radical containing from 6 to 10 carbon atoms; R 6 is selected from the group consisting of an alkyl radical containing from 1 to 4 carbon atoms; X is an aminoacyl moiety selected from the group consisting of ______________________________________ L-valyl, L-phenylalanyl, L-leucyl, L-tyrosyl, L-isoleucyl, L-tryptophanyl, L-α-aminobutyryl, L-lysyl, L-threonyl, L-ornithyl, L-methionyl, L-arginyl, L-cysteinyl, L-histidyl, L-glutamyl, L-asparaginyl, L-glutaminyl, L-prolyl, or L-aspartyl, L-hydroxyprolyl; ______________________________________ Y is an amino acid moiety selected from the group consisting of D-isoasparagine and D-isoglutamine; and the wavy lines ( ) represent the α- or β-configuration or mixtures thereof, with the proviso that when one wavy line is α, the other is β.
Claim 3
Dependent Claim 11 words
A compound according to claim 1 wherein R 6 is methyl.
Claim 4
Dependent Claim 15 words
A compound according to claim 1 wherein each of R and R 1 are hydrogen.
Claim 5
Dependent Claim 21 words
A compound according to claim 1 wherein R 2 is an unsubstituted alkyl radical containing from 1 to 22 carbon atoms.
Claim 6
Dependent Claim 20 words
A compound according to claim 1 wherein X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 7
Dependent Claim 10 words
A compound according to claim 1 wherein Y is D-isoglutamine.
Claim 8
Dependent Claim 23 words
A compound according to claim 1 wherein R and R 1 are the same acyl radical containing from 1 to 22 carbon atoms.
Claim 9
Dependent Claim 24 words
A compound according to claim 1 wherein R is hydrogen and R 1 is an acyl radical containing from 1 to 22 carbon atoms.
Claim 10
Dependent Claim 24 words
A compound according to claim 1 wherein R is an acyl radical containing from 1 to 22 carbon atoms and R 1 is hydrogen.
Claim 11
Dependent Claim 22 words
A compound according to claim 1 wherein R and R 1 are different acyl radicals containing from 1 to 22 carbon atoms.
Claim 12
Dependent Claim 11 words
A compound according to claim 1 wherein R 2 is methyl.
Claim 13
Dependent Claim 11 words
A compound according to claim 1 wherein R 2 is hydroxymethyl.
Claim 14
Dependent Claim 39 words
A compound according to claim 1 wherein R and R 1 are both hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 15
Dependent Claim 39 words
A compound according to claim 1 wherein R and R 1 are both acetyl, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 16
Dependent Claim 39 words
A compound according to claim 1 wherein R and R 1 are both butyryl, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 17
Dependent Claim 39 words
A compound according to claim 1 wherein R and R 1 are both octanoyl, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 18
Dependent Claim 39 words
A compound according to claim 1 wherein R and R 1 are both lauroyl, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 19
Dependent Claim 39 words
A compound according to claim 1 wherein R and R 1 are both stearoyl, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 20
Dependent Claim 39 words
A compound according to claim 1 wherein R is acetyl, R 1 is hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 21
Dependent Claim 39 words
A compound according to claim 1 wherein R is butyryl, R 1 is hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 22
Dependent Claim 39 words
A compound according to claim 1 wherein R is octanoyl, R 1 is hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 23
Dependent Claim 39 words
A compound according to claim 1 wherein R is lauroyl, R 1 is hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 24
Dependent Claim 39 words
A compound according to claim 1 wherein R is stearoyl, R 1 is hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 25
Dependent Claim 39 words
A compound according to claim 1 wherein R 1 is acetyl, R is hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 26
Dependent Claim 39 words
A compound according to claim 1 wherein R 1 is butyryl, R is hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenyalanyl.
Claim 27
Dependent Claim 39 words
A compound according to claim 1 wherein R 1 is octanoyl, R is hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 28
Dependent Claim 39 words
A compound according to claim 1 wherein R 1 is lauroyl, R is hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 29
Dependent Claim 39 words
A compound according to claim 1 wherein R 1 is stearoyl, R is hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 30
Dependent Claim 39 words
A compound according to claim 1 wherein R is butyryl, R 1 is acetyl, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 31
Dependent Claim 39 words
A compound according to claim 1 wherein R is octanoyl, R 1 is acetyl, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 32
Dependent Claim 39 words
A compound according to claim 1 wherein R is lauroyl, R 1 is acetyl, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 33
Dependent Claim 39 words
A compound according to claim 1 wherein R 2 is trifluoromethyl, R 6 is methyl, R and R 1 are both hydrogen, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 34
Dependent Claim 39 words
A compound according to claim 1 wherein R 2 is n-undecyl, R 6 is methyl, R and R 1 are both hydrogen, Y is D-isoglutamine and X is selected from the group consisting of L-valyl, L-prolyl, L-leucyl or L-phenylalanyl.
Claim 35
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is L-valyl; 2-(2-acetamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-valyl-D-isoglutamine
Claim 36
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is L-prolyl; 2-(2-acetamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-prolyl-D-isoglutamine.
Claim 37
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is L-leucyl; 2-(2-acetamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-leucyl-D-isoglutamine.
Claim 38
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both hydrogen, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is L-phenylalanyl; 2-(2-acetamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-phenylalanyl-D-isoglutamine.
Claim 39
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both acetyl, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is L-valyl; 2-(4,6-di-O-acetyl-2-acetamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-valyl-D-isoglutamine.
Claim 40
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both butyryl, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is L-valyl; 2-(4,6-di-O-butyryl-2-acetamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-valyl-D-isoglutamine.
Claim 41
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both lauroyl, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is L-valyl; 2-(4,6-di-O-lauroyl-2-acetamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-valyl-D-isoglutamine.
Claim 42
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both acetyl, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is L-prolyl; 2-(4,6-di-O-acetyl-2-acetamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-prolyl-D-isoglutamine.
Claim 43
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both butryl, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is L-prolyl; 2-(4,6-di-O-butyryl-2-acetamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-prolyl-D-isoglutamine.
Claim 44
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both lauroyl, R 2 and R 6 are both methyl, Y is D-isoglutamine and X is L-prolyl; 2-(4,6-di-O-lauroyl-2-acetamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-prolyl-D-isoglutamine.
Claim 45
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both hydrogen, R 2 is hydroxymethyl, R 6 is methyl, Y is D-isoglutamine and X is L-valyl; 2-(2-glycolamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-valyl-D-isoglutamine.
Claim 46
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both hydrogen, R 2 is hydroxymethyl, R 6 is methyl, Y is D-isoglutamine and X is L-prolyl; 2-(2-gylcolamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-prolyl-D-isoglutamine.
Claim 47
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both hydrogen, R 2 is hydroxymethyl, R 6 is methyl, Y is D-isoglutamine and X is L-leucyl; 2-(2-glycolamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-leucyl-D-isoglutamine.
Claim 48
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both hydrogen, R 2 is hydroxymethyl, R 6 is methyl, Y is D-isoglutamine and X is L-phenylalanyl; 2-(2-glycolamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-phenylalanyl-D-isoglutamine.
Claim 49
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both acetyl, R 2 is hydroxymethyl, R 6 is methyl, Y is D-isoglutamine and X is L-valyl; 2-(4,6-di-O-acetyl-2-glycolamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-valyl-D-isoglutamine.
Claim 50
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both acetyl, R 2 is hydroxymethyl, R 6 is methyl, Y is D-isoglutamine and X is L-prolyl; 2-(4,6-di-O-acetyl-2-glycolamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-prolyl-D-isoglutamine.
Claim 51
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both acetyl, R 2 is hydroxymethyl, R 6 is methyl, Y is D-isoglutamine and X is L-leucyl; 2-(4,6-di-O-acetyl-2-glycolamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-leucyl-D-isoglutamine.
Claim 52
Dependent Claim 30 words
The compound according to claim 1 wherein R and R 1 are both acetyl, R 2 is hydroxymethyl, R 6 is methyl, Y is D-isoglutamine and X is L-phenylalanyl; 2-(4,6-di-O-acetyl-2-glycolamido-2-deoxy-D-glucos-3-O-yl)-D-propionyl-L-phenylalanyl-D-isoglutamine.

References Cited (Backward Citations)

US3960828A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-04-03 1981-10-03 1982-04-04 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-04-03 1985-10-03 1986-04-04 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-04-03 1989-10-03 1990-04-04 $7700.00 Window Closed / Lapsed

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