US4016146A
Expired / Lapsed
US
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Phenethylamine antigenic conjugates, their preparation, antibodies, and use
Assignee: Biological Developments Inc
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Filing: 1974-12-10
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Granted: 1977-04-05
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Expires: 1994-12-10
Abstract
Abstract Antigenic phenethylamine conjugates are produced by blocking the amine of the phenethylamine hapten with a group, coupling of the phenethylamine to a carrier, and removal of the blocking group. Specific phenethylamines useful in this invention are amphetamine, epinephrine, and norepinephrine. The antigens thus produced can be used to raise antibodies in animal bodies, the antibodies being specific to the phenethylamine compound employed. In particular, this disclosure is directed to blocked phenethylamines for production of antigens and to a process for preparing the antigens.
Inventors
- 👤 James R. Soares
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 22:16
CPC Classifications
G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/53; G01N33/531; Y; Y10; Y10S; Y10S436/00; Y10S436/803; Y10S436/804; Y10S436/815; Y10S436/816; Y10S436/822
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
145 words
A process for producing a synthetic antigen of formula ##STR10## where R' and R" are individually selected from the class consisting of --H, --OH, and --OCH 3 , where either R' or R" is --OCH 3 , the other is --OH; R"' is selected from the class consisting of --H and --OH; R"" is selected from the class consisting of --H, --OCH 3 , and --C 2 H 5 ; Q is selected from the class consisting of --H and --CH 3 ; Y is a linking group which is the residue of the reaction of a coupling agent with a reactive group derivatized into the phenyl ring and of the coupling agent with the carrier, and the carrier is a macromolecule conferring antigenicity; where said reactive group is and said Y group includes a -N = N- or a group having the formula ##STR11##
Claim 2
Dependent Claim
145 words
A process for producing a synthetic antigen of formula ##STR10## where R' and R" are individually selected from the class consisting of --H, --OH, and --OCH 3 , where either R' or R" is --OCH 3 , the other is --OH; R"' is selected from the class consisting of --H and --OH; R"" is selected from the class consisting of --H, --OCH 3 , and --C 2 H 5 ; Q is selected from the class consisting of --H and --CH 3 ; Y is a linking group which is the residue of the reaction of a coupling agent with a reactive group derivatized into the phenyl ring and of the coupling agent with the carrier, and the carrier is a macromolecule conferring antigenicity; where said reactive group is and said Y group includes a -N = N- or a group having the formula ##STR11##
Claim 3
Dependent Claim
34 words
where Q' is an alkylene chain having up to 20 carbon atoms; comprising 1. substituting a blocking group onto the amine of a phenylamine having the formula: ##STR12## to form an amine blocked phenethylamine;
Claim 4
Dependent Claim
34 words
where Q' is an alkylene chain having up to 20 carbon atoms; comprising 1. substituting a blocking group onto the amine of a phenylamine having the formula: ##STR12## to form an amine blocked phenethylamine;
Claim 5
Dependent Claim
31 words
forming a derivative on the phenyl ring of the amine-blocked phenethylamine; 3. coupling the derivative to a carrier; and 4. removing the blocking group and reforming the amine to yield the
Claim 6
Dependent Claim
31 words
forming a derivative on the phenyl ring of the amine-blocked phenethylamine; 3. coupling the derivative to a carrier; and 4. removing the blocking group and reforming the amine to yield the
Claim 7
Dependent Claim
28 words
phenethylamine conjugated to the carrier through the ring derivative. 2. The process according to claim 1 wherein the derivative formed on the phenyl ring is a nitro group.
Claim 8
Dependent Claim
27 words
The process according to claim 2 wherein the nitro group is subsequently reduced to the corresponding amino group and coupling to the carrier is effected by diazotization.
Claim 9
Dependent Claim
11 words
The process of claim 1 wherein the blocking group is trifluoroacetyl.
Claim 10
Dependent Claim
17 words
The process of claim 4 wherein the blocking group is removed by dialysis against an alkaline solution.
Claim 11
Dependent Claim
31 words
The process of claim 1 wherein the carrier is a protein having available aromatic groups with diazotiazable carbons and the coupling is effected by forming a diazonium group on the protein.
Claim 12
Dependent Claim
24 words
The process according to claim 6 wherein the phenyl ring is derivatized by acylation with a dicarboxylic acid anhydride in a Friedel Crafts reaction.
Claim 13
Dependent Claim
11 words
The process according to claim 7 wherein the anhydride is succinic.
Claim 14
Dependent Claim
38 words
The process according to claim 7 wherein the carrier is a protein having available amine groups and the blocked phenethylamine is coupled to the carrier through the acyl derivative by forming an amide bond using a protein-coupling agent.
Claim 15
Dependent Claim
20 words
A process according to claim 1 wherein the phenethylamine is a phenolethylamine and the derivatization of the phenol comprises diazotization.
Claim 16
Dependent Claim
16 words
The process of claim 10 wherein a primary aromatic amine group is diazotized into the phenol.
Claim 17
Dependent Claim
18 words
The process of claim 10 wherein the residue of a primary aromatic amine is coupled to the carrier.
Claim 18
Dependent Claim
22 words
The process of claim 1 wherein the phenethylamine is amphetamine, the blocking group is trifluoroacetic anhydride and the derivatization is a diazotization.
Claim 19
Dependent Claim
75 words
The process according to claim 1 wherein the phenethylamine is selected from the group consisting of epinephrine and norepinephrine and the process comprises blocking the amine with a trifluoroacetyl substituent, diazotizing the amine of a p-aminobenzoyl group into the phenyl of the phenethylamine, coupling the benzoyl group to a protein using a protein-coupling agent to form an amide bond, and removing the trifluoroacetyl block with reconstitution of the amine to form the corresponding protein-benzoylazo phenethylamine.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-04-04 | 1980-10-04 | 1981-04-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-04-04 | 1984-10-04 | 1985-04-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-04-04 | 1988-10-04 | 1989-04-05 | $7700.00 | Window Closed / Lapsed |