US4519955A
Expired / Lapsed
US
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Method for optical resolution of DL-α-amino acid or (±)-α-phenylethanesulfonic acid
Assignee: Tanabe Pharma Corp
•
Filing: 1984-03-02
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Granted: 1985-05-28
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Expires: 2004-03-02
Abstract
Abstract alpha -(S)-amino acid. alpha -phenylethanesulfonate compounds and methods of optical resolution of alpha -amino acids and alpha -phenylethanesulfonic acids are described.
Inventors
- 👤 Ichiro Chibata
- 👤 Shigeki Yamada
- 👤 Chikara Hongo
- 👤 Ryuzo Yoshioka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 05:57
CPC Classifications
C; C07; C07B; C07B57/00
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
16 words
A compound comprising an α.(S)-amino acid and α-phenylethanesulfonic acid which is α-amino acid.α-phenylethanesulfonate, exclusive of p-hydroxyphenylglycine.α-phenylethanesulfonate.
Claim 2
Dependent Claim
16 words
A compound comprising an α.(S)-amino acid and α-phenylethanesulfonic acid which is α-amino acid.α-phenylethanesulfonate, exclusive of p-hydroxyphenylglycine.α-phenylethanesulfonate.
Claim 3
Dependent Claim
16 words
The compound of claim 1, wherein said α-amino acid and α-phenylethanesulfonic acid are optically active isomers.
Claim 4
Dependent Claim
40 words
The compound claimed in claim 1, in which the α-amino acid is selected from the group consisting of alanine, arginine, valine, leucine, isoleucine, phenylalanine, phenylglycine, tyrosine, trytophan, serine, threonine, proline, cysteine, glutamic acid, aspartic acid, histidine, ornithine, lysine and citrulline.
Claim 5
Dependent Claim
29 words
The compound claimed in claim 1, in which the α-amino acid is an optically active α-amino acid selected from the group consisting of arginine, valine, leucine, phenylglycine and lysine.
Claim 6
Dependent Claim
15 words
The compound claimed in claim 4, which is L-leucine. (+)-α-phenylethanesulfonate, L-valine.(-)-α-phenylethanesulfonate, L-arginine.(-)-α-phenylethanesulfonate, L-lysine.(-)-α-phenylethanesulfonate or D-phenylglycine.(+)-α-phenylethanesulfonate.
Claim 7
Independent Claim
48 words
A method for resolving DL-α-amino acid, exclusive of DL-p-hydroxyphenylglycine comprising a. reacting said DL-α-amino acid with optically active α-phenylethanesulfonic acid to yield the diastereoisomeric salt of DL-α-amino acid.optically active α-phenylethanesulfonate, b. collecting the less soluble diastereoisomeric salt, and c. converting said collected salt into optically active α-amino acid.
Claim 8
Independent Claim
48 words
A method for resolving DL-α-amino acid, exclusive of DL-p-hydroxyphenylglycine comprising a. reacting said DL-α-amino acid with optically active α-phenylethanesulfonic acid to yield the diastereoisomeric salt of DL-α-amino acid.optically active α-phenylethanesulfonate, b. collecting the less soluble diastereoisomeric salt, and c. converting said collected salt into optically active α-amino acid.
Claim 9
Dependent Claim
39 words
The method according to claim 6, wherein the DL-α-amino acid is selected from the group consisting of alanine, arginine, valine, leucine, isoleucine, phenylalanine, phenylglycine, tryptophan, tyrosine, serine, threonine, proline, cysteine, glutamic acid, aspartic acid, histidine, ornithine, lysine and citrulline.
Claim 10
Dependent Claim
23 words
The method according to claim 6, wherein the DL-α-amino acid is selected from the group consisting of arginine, valine, leucine, phenylglycine and lysine.
Claim 11
Dependent Claim
28 words
The method according to claim 6, wherein the optically active α-phenylethanesulfonic acid is used in an amount of 0.3 to 1.5 mole per mole of the DL-α-amino acid.
Claim 12
Dependent Claim
28 words
The method according to claim 9, wherein the optically active α-phenylethanesulfonic acid is used in an amount of 0.5 to 1.0 mole per mole of the DL-α-amino acid.
Claim 13
Dependent Claim
17 words
The method according to claim 9, wherein said reacting step is carried out in an aqueous solvent.
Claim 14
Dependent Claim
28 words
The method according to claim 7, wherein the optically active α-phenylethanesulfonic acid is used in an amount of 0.3 to 1.5 mole per mole of the DL-α-amino acid.
Claim 15
Dependent Claim
28 words
The method according to claim 8, wherein the optically active α-phenylethanesulfonic acid is used in an amount of 0.3 to 1.5 mole per mole of the DL-α-amino acid.
Claim 16
Dependent Claim
28 words
The method according to claim 12, wherein the optically active α-phenylethanesulfonic acid is used in an amount of 0.5 to 1.0 mole per mole of the DL-α-amino acid.
Claim 17
Dependent Claim
28 words
The method according to claim 13, wherein the optically active α-phenylethanesulfonic acid is used in an amount of 0.5 to 1.0 mole per mole of the DL-α-amino acid.
Claim 18
Dependent Claim
17 words
The method according to claim 12, wherein said reacting step is carried out in an aqueous solvent.
Claim 19
Dependent Claim
17 words
The method according to claim 13, wherein said reacting step is carried out in an aqueous solvent.
Claim 20
Independent Claim
50 words
A method of resolving (±)-α-phenylethanesulfonic acid comprising a. reacting said (±)-α-phenylethanesulfonic acid with an optically active α-amino acid, exclusive of optically active p-hydroxyphenylglycine, to form to diastereoisomeric salts of α-amino acid.(±)-α-phenylethanesulfonate, b. collecting the less soluble diastereoisomeric salt therefrom, and c. converting said collected salt into optically active α-phenylethanesulfonic acid.
Claim 21
Independent Claim
50 words
A method of resolving (±)-α-phenylethanesulfonic acid comprising a. reacting said (±)-α-phenylethanesulfonic acid with an optically active α-amino acid, exclusive of optically active p-hydroxyphenylglycine, to form to diastereoisomeric salts of α-amino acid.(±)-α-phenylethanesulfonate, b. collecting the less soluble diastereoisomeric salt therefrom, and c. converting said collected salt into optically active α-phenylethanesulfonic acid.
Claim 22
Dependent Claim
41 words
The method according to claim 18, wherein the optically active α-amino acid is selected from the group consisting of alanine, arginine, valine, leucine, isoleucine, phenylalanine, phenylglycine, tryptophan, tyrosine, serine, threonine, proline, cysteine, glutamic acid, aspartic acid, histidine, ornithine, lysine and citrulline.
Claim 23
Dependent Claim
26 words
The method according to claim 19, wherein the optically active α-amino acid is used in an amount of 0.3 to 1.5 mole per mole (±)-α-phenylethanesulfonic acid.
Claim 24
Dependent Claim
25 words
The method according to claim 18, wherein the optically active α-amino acid is selected from the group consisting of arginine, valine, leucine, phenylglycine and lysine.
Claim 25
Dependent Claim
25 words
The method according to claim 21, wherein the optically active α-amino acid is used in an amount of 0.3 to 1.5 mole of (±)-α-phenylethanesulfonic acid.
Claim 26
Dependent Claim
27 words
The method according to claim 18, wherein the optically active α-amino acid is used in an amount of 0.3 to 1.5 mole per mole of (±)-α-phenylethanesulfonic acid.
Claim 27
Dependent Claim
28 words
The method according to claim 23, wherein the optically active α-amino acid is used in an amount of 0.5 to 1.0 mole per mole of the (±)-α-phenylethanesulfonic acid.
Claim 28
Dependent Claim
17 words
The method according to claim 23, wherein said reacting step is carried out in an aqueous solvent.
Claim 29
Dependent Claim
28 words
The method according to claim 20, wherein the optically active α-amino acid is used in an amount of 0.5 to 1.0 mole per mole of the (±)-α-phenylethanesulfonic acid.
Claim 30
Dependent Claim
28 words
The method according to claim 22, wherein the optically active α-amino acid is used in an amount of 0.5 to 1.0 mole per mole of the (±)-α-phenylethanesulfonic acid.
Claim 31
Dependent Claim
17 words
The method according to claim 20, wherein said reacting step is carried out in an aqueous solvent.
Claim 32
Dependent Claim
17 words
The method according to claim 22, wherein said reacting step is carried out in an aqueous solvent.
Claim 33
Dependent Claim
27 words
The method of claim 9 wherein said reacting step is carried out in a solvent selected from lower alkanol, lower alkanone, lower alkanoic acid and mixtures thereof.
Claim 34
Dependent Claim
27 words
The method of claim 33 wherein said reacting step is carried out in a solvent selected from lower alkanol, lower alkanone, lower alkanoic acid and mixtures thereof.
Claim 35
Dependent Claim
27 words
The method of claim 12 wherein said reacting step is carried out in a solvent selected from lower alkanol, lower alkanone, lower alkanoic acid and mixtures thereof.
Claim 36
Dependent Claim
27 words
The method of claim 13 wherein said reacting step is carried out in a solvent selected from lower alkanol, lower alkanone, lower alkanoic acid and mixtures thereof.
Claim 37
Dependent Claim
27 words
The method of claim 20 wherein said reacting step is carried out in a solvent selected from lower alkanol, lower alkanone, lower alkanoic acid and mixtures thereof.
Claim 38
Dependent Claim
27 words
The method of claim 22 wherein said reacting step is carried out in a solvent selected from lower alkanol, lower alkanone, lower alkanoic acid and mixtures thereof.
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| 7.5 Years (Year 8) | 1992-05-27 | 1992-11-26 | 1993-05-28 | $3760.00 | Window Closed / Lapsed |
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