US5169984A
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Synthesis and characterization of N-bromoacetyl-3,3'5-triiodo-L-thyronine using high speed countercurrent chromatography
Assignee: United States Department of Health and Human Services
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Filing: 1990-09-10
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Granted: 1992-12-08
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Expires: 2010-09-10
Abstract
Abstract A method for synthesizing N-bromoacetyl-3,3',5-triiodo-L-thyronine which involves subjecting 3,3', 5-triiodo-L-thyronine to a one-step bromacetylation reaction wherein 3,3', 5-triiodo-L-thyronine and bromoacetyl bromide are refluxed together in a solution of ethyl acetate. After formation the N-bromoacetyl-3,3'-triiodo-L-thyronine is purified by fractionation utilizing high speed countercurrent chromatography. Labeled N-bromoacetyl-3,3'-5-triiodo-L-thryonine may be made by a one-step bromacetylation reaction by reducing either [125I]T3 or [14C]T3 with bromoacetyl bromide.
Inventors
- 👤 Hans J. Cahnmann
- 👤 Yoichiro Ito
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 12:50
CPC Classifications
C; C07; C07C; C07C233/00; C07C233/01; C07C233/45; C07C233/46; C07C233/47; C07C231/00; C07C231/02; C07C231/22; C07C231/24
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
39 words
A method for synthesizing N-bromoacetyl3,3',5-triiodo-L-thyronine which comprises subjecting 3,3',5-triiodo-L-thyronine to a one-step bromoacetylation reaction with bromoacetyl bromide wherein after synthesis, said N-bromoacetyl-3,3',5-triiodo-L-thyronine is subjected to high speed countercurrent chromatography fractionation to obtain a product which consists essentially of N-bromoacetyl-3,3',5-triiodo-L-thyronine.
Claim 2
Independent Claim
39 words
A method for synthesizing N-bromoacetyl3,3',5-triiodo-L-thyronine which comprises subjecting 3,3',5-triiodo-L-thyronine to a one-step bromoacetylation reaction with bromoacetyl bromide wherein after synthesis, said N-bromoacetyl-3,3',5-triiodo-L-thyronine is subjected to high speed countercurrent chromatography fractionation to obtain a product which consists essentially of N-bromoacetyl-3,3',5-triiodo-L-thyronine.
Claim 3
Dependent Claim
31 words
A method for synthesizing N-bromoacetyl-3,3',5-triiodo-L-thyronine according to claim 1, wherein said high speed countercurrent chromatography utilizes a solvent system comprising hexane/ethyl acetate/methanol/15 mM ammonium acetate having a pH of about 4.0.
Claim 4
Dependent Claim
25 words
A method for synthesizing N-bromoacetyl-3,3',5-triiodo-L-thyronine according to claim 2, wherein said hexane/ethyl acetate/methanol/15 mM ammonium acetate are present in a ratio of 1:1:1:1 by volume.
Claim 5
Dependent Claim
25 words
A method for synthesizing N-bromoacetyl-3,3',5-triiodo-L-thyronine according to claim 2, wherein said hexane/ethyl acetate/methanol/15 mM ammonium acetate are present in a ratio of 4:5:4:5 by volume.
Claim 6
Dependent Claim
31 words
A method for synthesizing N-bromoacetyl-3,3',5-triiodo-L-thyronine according to claim 2, wherein said high speed countercurrent chromatography is conducted at a temperature in the range of from about 10° to about 30° C.
Claim 7
Dependent Claim
27 words
A method for synthesizing labeled N-bromoacetyl-3,3',5-triiodo-L-thyronine according to claim 1, further comprising labeling said N-bromoacetyl-3,3',5-triiodo-L-thyronine by conducting said bromoacetylation reaction in the presence of a labeled 3,3',5-triiodo-L-thyronine.
Claim 8
Dependent Claim
31 words
A method for synthesizing labeled N-bromoacetyl3,3',5-triiodo-L-thyronine according to claim 6, wherein said 3,3',5-triiodo-L-thyronine is labelled with an element selected from the group consisting of 125 I, 14 C, and mixtures thereof.
Claim 9
Independent Claim
25 words
A method of purifying crude N-bromoacetyl-3,3',5-triiodo-L-thyronine which comprises subjecting crude N-bromoacetyl-3,3',5-triiodo-L-thyronine to high speed countercurrent chromatography to obtain a product which consists essentially of N-bromoacetyl-3,3',5-triiodo-L-thyronine.
Claim 10
Independent Claim
25 words
A method of purifying crude N-bromoacetyl-3,3',5-triiodo-L-thyronine which comprises subjecting crude N-bromoacetyl-3,3',5-triiodo-L-thyronine to high speed countercurrent chromatography to obtain a product which consists essentially of N-bromoacetyl-3,3',5-triiodo-L-thyronine.
Claim 11
Dependent Claim
32 words
A method of purifying crude N-bromoacetyl-3,3',5-triiodo-L-thyronine according to claim 8, wherein said high speed countercurrent chromatography utilizes a solvent system comprising hexane/ethyl acetate/methanol/15 mM ammonium acetate having a pH of about 4.0.
Claim 12
Dependent Claim
26 words
A method of purifying crude N-bromoacetyl-3,3',5-triiodo-L-thyronine according to claim 9, wherein said hexane/ethyl acetate/methanol/15 mM ammonium acetate are present in a ratio of 1:1:1:1 by volume.
Claim 13
Dependent Claim
26 words
A method of purifying crude N-bromoacetyl-3,3',5-triiodo-L-thyronine according to claim 9, wherein said hexane/ethyl acetate/methanol/15 mM ammonium acetate are present in a ratio of 4:5:4:5 by volume.
Claim 14
Dependent Claim
32 words
A method of purifying crude N-bromoacetyl-3,3',5-triiodo-L-thyronine according to claim 9, wherein said high speed countercurrent chromatography is conducted at a temperature in the range of from about 10° to about 30° C.
References Cited (Backward Citations)
US4430216A
Cited
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