US4229537A
Expired / Lapsed
US
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Preparation of trichloro-s-triazine activated supports for coupling ligands
Assignee: New York University
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Filing: 1978-02-09
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Granted: 1980-10-21
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Expires: 1998-02-09
Abstract
Abstract Proteins and non-protein affinity ligands are covalently bonded to trichloro-s-triazine activated supports. The activated support is prepared by reacting a water-free insoluble solid support with trichloro-s-triazine in a non-aqueous medium and neutralizing HCl generated during the reaction with a tertiary amine which does not form an insoluble complex with the trichloro-s-triazine.
Inventors
- 👤 Leonard T. Hodgins
- 👤 Thomas H. Finlay
- 👤 Alan J. Johnson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 12:17
CPC Classifications
C; C12; C12N; C12N11/00; C12N11/02; C12N11/10; B; B01; B01J; B01J20/00; B01J20/30; B01J20/3071; B01J20/32; B01J20/3202; B01J20/3206; B01J20/3208; B01J20/3212; B01J20/3214; B01J20/3217; B01J20/3219; B01J20/3231; B01J20/3242; B01J20/3244; B01J20/3246; B01J20/3248; B01J20/3251; B01J20/3253; B01J20/3255; B01J20/3268; B01J20/3272; B01J20/3274; C08; C08B; C08B37/00; C08B37/0006; C08B37/0036; C08B37/0039; Y; Y10; Y10S; Y10S435/00; Y10S435/814; Y10S435/815
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
159 words
In a method for coupling substances selected from the group consisting of protein ligands and non-protein affinity ligands by covalent chemical bonds to insoluble solid supports for the preparation of solid phase catalysts and biospecific adsorbents comprising the steps of reacting the insoluble solid support material with trichloro-s-triazine to produce an activated support and thereafter, coupling the ligand to the activated support, the improvement wherein the production of the activated support is carried out by the steps comprising: (a) reacting a water-free insoluble solid support material with trichloro-s-triazine in a non-aqueous medium comprising an organic solvent which is compatible with the support material and is also a solvent for trichloro-s-triazine; (b) neutralizing the HCl generated during the reaction with a tertiary amine which is soluble in said organic solvent and which does not form an insoluble complex with trichloro-s-triazine in said organic solvent; and (c) washing the obtained dichloro-s-triazine activated support with an additional amount of said organic solvent.
Claim 2
Dependent Claim
159 words
In a method for coupling substances selected from the group consisting of protein ligands and non-protein affinity ligands by covalent chemical bonds to insoluble solid supports for the preparation of solid phase catalysts and biospecific adsorbents comprising the steps of reacting the insoluble solid support material with trichloro-s-triazine to produce an activated support and thereafter, coupling the ligand to the activated support, the improvement wherein the production of the activated support is carried out by the steps comprising: (a) reacting a water-free insoluble solid support material with trichloro-s-triazine in a non-aqueous medium comprising an organic solvent which is compatible with the support material and is also a solvent for trichloro-s-triazine; (b) neutralizing the HCl generated during the reaction with a tertiary amine which is soluble in said organic solvent and which does not form an insoluble complex with trichloro-s-triazine in said organic solvent; and (c) washing the obtained dichloro-s-triazine activated support with an additional amount of said organic solvent.
Claim 3
Dependent Claim
19 words
The method of claim 1 wherein the tertiary amine is selected from the group consisting of N,N-diisopropylethylamine and N,N-dimethylaniline.
Claim 4
Dependent Claim
22 words
The method of claim 1 wherein, in step (d) said organic solvent is selected from the group consisting of dioxane and acetonitrile.
Claim 5
Dependent Claim
47 words
The method of claim 1 including the further step of adding a nucleophile to the washed trichloro-s-triazine activated support in an organic solvent to replace one or both of chlorine atoms on the triazine ring, and when both chlorine atoms are replaced, the nucleophile is said ligand.
Claim 6
Dependent Claim
23 words
The method of claim 4 wherein said nucleophile is selected from the group consisting of aliphatic amines, aryl amines, phenols and alkoxyl amines.
Claim 7
Dependent Claim
46 words
The method of claim 1 including the further step of adding a weak nucleophile to the washed dichloro-s-triazine activated support in an organic solvent to replace a single chlorine atom on the triazine ring, leaving the remaining chlorine atom available for further replacement by said ligand.
Claim 8
Dependent Claim
11 words
The method of claim 6 wherein said weak nucleophile is aniline.
Claim 9
Dependent Claim
20 words
The method of claim 6 wherein the monochloro-s-triazine activated support is dried for storage and later coupling with said ligand.
Claim 10
Dependent Claim
24 words
The method of claim 1, wherein said support material initially contains water and is pretreated prior to step (a) to remove said water therefrom.
Claim 11
Dependent Claim
23 words
The method of claim 9 wherein said pretreatment of said support material is accomplished by washing the support material with an organic solvent.
Claim 12
Dependent Claim
21 words
The method of claim 9 wherein said pretreatment of said support material is accomplished by drying the support material under vacuum.
Claim 13
Dependent Claim
12 words
The method of claim 1 wherein said protein ligand is an enzyme.
Claim 14
Dependent Claim
23 words
A support coupled ligand obtained in accordance with the method of claim 1, wherein said non-aqueous medium consists essentially of dioxane or acetonitrile.
Claim 15
Dependent Claim
22 words
A support-coupled ligand obtained in accordance with the method of claim 8, wherein said non-aqueous medium consists essentially of dioxane or acetonitrile.
Claim 16
Dependent Claim
20 words
A support-coupled ligand produced by the method of claim 4, wherein said non-aqueous medium consists essentially of dioxane or acetonitrile.
Claim 17
Dependent Claim
20 words
A support-coupled ligand produced by the method of claim 6, wherein said non-aqueous medium consists essentially of dioxane or acetonitrile.
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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) | 1983-10-21 | 1984-04-21 | 1984-10-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-21 | 1988-04-21 | 1988-10-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-21 | 1992-04-21 | 1992-10-21 | $7700.00 | Window Closed / Lapsed |