US4303786A
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Isonitrile derivatives of macromolecules containing hydroxyl groups
Assignee: Ramot at Tel Aviv University Ltd
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Filing: 1978-07-31
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Granted: 1981-12-01
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Expires: 1998-07-31
Abstract
Abstract The present invention relates to novel isocyano derivatives of linear or cross-linked, natural or synthetic macromolecules, the derivatives being of the general formula P-O-Q-NC, wherein P is the macromolecular backbone, the oxygen atom is part of the hydroxy group, Q is a group -(CH2)n-wherein n is an integer of at least 3 carbon atoms, and up to about 20 carbon atoms, or Q is an aralkyl group, to a process for preparing such derivatives and to a process of linking to same biologically active proteins and to the products thus obtained.
Inventors
- 👤 Leon Goldstein
- 👤 Amihay Freeman
- 👤 Mordechai Sokolovsky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 01:48
CPC Classifications
C; C08; C08B; C08B37/00; C08B15/00; C08B15/05; C08B15/06; C12; C12N; C12N11/00; C12N11/02; C12N11/08; C12N11/082; C12N11/084; C12N11/087; C12N11/10
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
97 words
An isocyano derivative of a linear or cross-linked polymer bearing a plurality of hydroxyl groups, said derivative having the general formula P--O--Q--N.tbd.C wherein P designates a polymeric backbone selected from the group consisting of cellulose, starch, linear dextran, cross-linked dextran, linear agarose, cross-linked agarose, polyvinyl alcohol and N-2-hydroxyethyl derivatives of a polyacrylamide, the oxygen atom is part of the hydroxy group, Q is a group --(CH 2 ) n -- wherein n is an integer of 3 to 20, said isocyano derivative containing from 9 to 100 micro-moles (μ-mole) isonitrile groups per gram of said isocyano derivative.
Claim 2
Dependent Claim
97 words
An isocyano derivative of a linear or cross-linked polymer bearing a plurality of hydroxyl groups, said derivative having the general formula P--O--Q--N.tbd.C wherein P designates a polymeric backbone selected from the group consisting of cellulose, starch, linear dextran, cross-linked dextran, linear agarose, cross-linked agarose, polyvinyl alcohol and N-2-hydroxyethyl derivatives of a polyacrylamide, the oxygen atom is part of the hydroxy group, Q is a group --(CH 2 ) n -- wherein n is an integer of 3 to 20, said isocyano derivative containing from 9 to 100 micro-moles (μ-mole) isonitrile groups per gram of said isocyano derivative.
Claim 3
Dependent Claim
26 words
An isocyano-substituted polymer according to claim 1, wherein Q designates a group --(CH 2 ) n -- wherein n is an integer from 3 to 12.
Claim 4
Dependent Claim
23 words
An isocyano substituted polysaccharide according to claim 1, wherein the polymer backbone is a cross-linked dextran, linear dextran, cross-linked agarose or linear agarose.
Claim 5
Dependent Claim
16 words
An isocyano substituted polymer according to claim 1, wherein the polymeric backbone is dextran or agarose.
Claim 6
Dependent Claim
14 words
An isocyano substituted polymer according to claim 4, wherein the polymeric backbone is dextran.
Claim 7
Dependent Claim
14 words
An isocyano substituted polymer according to claim 4, wherein the polymeric backbone is agarose.
Claim 8
Dependent Claim
114 words
A process for producing isocyano-substituted polyhydroxy linear or cross-linked polymer which comprises treating a polymer having hydroxy-groups with a strong base in a nonaqueous polar solvent so as to ionize the hydroxy-groups, reacting the ionized product with a compound of the formula X--Q--NC, wherein X is a good leaving group, Q is a --(CH 2 ) n -- group wherein n is an integer of 3 or more or an aralkyl moiety, resulting in a product of the formula P--O--Q--NC wherein P is the polymeric backbone, said polymeric backbone being selected from the group consisting of cellulose, starch, linear dextran, cross-linked dextran, linear agarose, cross-linked agarose, polyvinyl alcohol and N-2-hydroxyethyl derivatives of a polyacrylamide.
Claim 9
Dependent Claim
114 words
A process for producing isocyano-substituted polyhydroxy linear or cross-linked polymer which comprises treating a polymer having hydroxy-groups with a strong base in a nonaqueous polar solvent so as to ionize the hydroxy-groups, reacting the ionized product with a compound of the formula X--Q--NC, wherein X is a good leaving group, Q is a --(CH 2 ) n -- group wherein n is an integer of 3 or more or an aralkyl moiety, resulting in a product of the formula P--O--Q--NC wherein P is the polymeric backbone, said polymeric backbone being selected from the group consisting of cellulose, starch, linear dextran, cross-linked dextran, linear agarose, cross-linked agarose, polyvinyl alcohol and N-2-hydroxyethyl derivatives of a polyacrylamide.
Claim 10
Dependent Claim
14 words
A process according to claim 7, wherein the non-aqueous polar aprotic solvent is dimethylsulfoxide.
Claim 11
Dependent Claim
14 words
A process according to claim 7, wherein the base used for ionization is t-butoxide.
Claim 12
Dependent Claim
26 words
A process according to claim 7, wherein the isocyanide is first contacted with a solid alkali metal hydroxide and subsequently reacted with the ionized polymeric material.
Claim 13
Dependent Claim
39 words
A process according to claim 7, wherein the isocyanide is of the formula Z--(CH 2 ) n --NC wherein Z is a leaving group, n is an integer of 3 to 12, or wherein the isocyanide is 3-tosyl-1-isocyano propane.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1984-11-30 | 1985-06-01 | 1985-12-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-11-30 | 1989-06-01 | 1989-12-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-11-30 | 1993-06-01 | 1993-12-01 | $7700.00 | Window Closed / Lapsed |