Patent US3870694A successfully refreshed from Google Patents.
US3870694A
Expired / Lapsed
US
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Peptide synthesis with n-hydroxy-5-norbornene-2,3-dicarboximide
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1973-03-13
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Granted: 1975-03-11
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Expires: 1993-03-13
Abstract
Abstract The present invention relates to an improvement in a method for producing a peptide which comprises allowing an amino acid or peptide whose N-terminal amino or imino group has been protected to react with an N-hydroximide compound in the presence of a carbodiimide reagent to produce an N-hydroximide ester of an amino acid or peptide whose N-terminal group is protected and allowing thus produced N-hydroximide ester to react with an amino acid, peptide or derivative thereof whose N-terminal amino or imino group is free and optionally liberating the protected peptide into the free form, the improvement wherein the Nhydroximide compound is N-hydroxy-5-norbornene-2,3dicarboximide.
Inventors
- 👤 Masahiko Fujino
- 👤 Shigeru Kobayashi
- 👤 Mikihiko Obayashi
- 👤 Susumu Shinagawa
- 👤 Tsunehiko Fukuda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 20:17
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/08; C07K5/0821; C07K5/0825; C07D; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D207/24; C07D207/26; C07D207/273; C07D207/277; C07D207/28; C07K1/00; C07K1/06; C07K1/08; C07K1/084; C07K14/00; C07K14/435; C07K14/665; C07K14/695; C07K5/0802; C07K5/0804; C07K5/0806; A; A61; A61K; A61K38/00; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/13
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
91 words
IN A METHOD FOR PRODUCING A PEPTIDE WHICH COMPRISES ALLOWING AN AMINO ACID OR PEPTIDE WHOSE N-TERMINAL AMINO OR IMINO GROUP HAS BEEN PROTECTED TO REACT WITH AN NHYDROXIMIDE COMPOUND IN THE PRESENCE OF A CARBODIIMIDE REAGENT TO PRODUCE AN N-HYDROXYAMIDE ESTER OF AN AMINO ACID OR PEPTIDE WHOSE N-TERMINAL GROUP IS PROTECTED AND ALLOWING THUS PRODUCED N-HYDROXIMIDE ESTER TO REACT WITH AN AMINO ACID, PEPTIDE OR DERIVATIVE THEREOF WHOSE N-TERMINAL AMINO OR IMINO GROUP IS FREE AND OPTIONALLY LIBERATING THE PROTECTED PEPTIDE INTO THE FREE FORM, WITH THE PROVISO THAT:
Claim 2
Dependent Claim
91 words
IN A METHOD FOR PRODUCING A PEPTIDE WHICH COMPRISES ALLOWING AN AMINO ACID OR PEPTIDE WHOSE N-TERMINAL AMINO OR IMINO GROUP HAS BEEN PROTECTED TO REACT WITH AN NHYDROXIMIDE COMPOUND IN THE PRESENCE OF A CARBODIIMIDE REAGENT TO PRODUCE AN N-HYDROXYAMIDE ESTER OF AN AMINO ACID OR PEPTIDE WHOSE N-TERMINAL GROUP IS PROTECTED AND ALLOWING THUS PRODUCED N-HYDROXIMIDE ESTER TO REACT WITH AN AMINO ACID, PEPTIDE OR DERIVATIVE THEREOF WHOSE N-TERMINAL AMINO OR IMINO GROUP IS FREE AND OPTIONALLY LIBERATING THE PROTECTED PEPTIDE INTO THE FREE FORM, WITH THE PROVISO THAT:
Claim 3
Dependent Claim
37 words
IF THE AMINO ACID OR PEPTIDE WHOSE N-TERMINAL AMINO OR IMINO GROUP HAS BEEN PROTECTED HAS FREE FUNCTIONAL GROUP OR GROUPS IN SIDE CAIN, NONE, SOME OR ALL OF THESE FUNCTIONAL GROUP OR GROUPS ARE PROTECTED, AND
Claim 4
Dependent Claim
37 words
IF THE AMINO ACID OR PEPTIDE WHOSE N-TERMINAL AMINO OR IMINO GROUP HAS BEEN PROTECTED HAS FREE FUNCTIONAL GROUP OR GROUPS IN SIDE CAIN, NONE, SOME OR ALL OF THESE FUNCTIONAL GROUP OR GROUPS ARE PROTECTED, AND
Claim 5
Dependent Claim
37 words
if the amino acid or peptide whose N-terminal amino or imino group has been protected has free functional group or groups in side chain, none, some or all of these functional group or groups are protected, and
Claim 6
Dependent Claim
37 words
if the amino acid or peptide whose N-terminal amino or imino group has been protected has free functional group or groups in side chain, none, some or all of these functional group or groups are protected, and
Claim 7
Dependent Claim
91 words
In a method for producing a peptide which comprises allowing an amino acid or peptide whose N-terminal amino or imino group has been protected to react with an N-hydroximide compound in the presence of a carbodiimide reagent to produce an N-hydroximide ester of an amino acid or peptide whose N-terminal group is protected and allowing thus produced N-hydroximide ester to react with an amino acid, peptide or derivative thereof whose N-terminal amino or imino group is free and optionally liberating the protected peptide into the free form, with the proviso that:
Claim 8
Dependent Claim
91 words
In a method for producing a peptide which comprises allowing an amino acid or peptide whose N-terminal amino or imino group has been protected to react with an N-hydroximide compound in the presence of a carbodiimide reagent to produce an N-hydroximide ester of an amino acid or peptide whose N-terminal group is protected and allowing thus produced N-hydroximide ester to react with an amino acid, peptide or derivative thereof whose N-terminal amino or imino group is free and optionally liberating the protected peptide into the free form, with the proviso that:
Claim 9
Dependent Claim
14 words
A method as claimed in claim 1, wherein the objective peptide is L-pyroglutamyl-L-histidyl-L-proline amidE.
Claim 10
Dependent Claim
47 words
if the amino acid or peptide derivative whose N-terminal amino or imino group is free has free functional group or groups in side chain or/and a C-terminal carboxyl group, none, some or all of these groups are protected, the improvement wherein the N-hydroximide compound is N-hydroxy-5-norbornene-2, 3-dicarboximide.
Claim 11
Dependent Claim
47 words
if the amino acid or peptide derivative whose N-terminal amino or imino group is free has free functional group or groups in side chain or/and a C-terminal carboxyl group, none, some or all of these groups are protected, the improvement wherein the N-hydroximide compound is N-hydroxy-5-norbornene-2, 3-dicarboximide.
Claim 12
Dependent Claim
45 words
IF THE AMINO ACID OR PEPTIDE DERIVATIVE WHOSE N-TERMINAL AMINO OR IMINO GROUP IS FREE HAS FREE FUNCTIONAL GROUP OR GROUPS IN SIDE CHAIN OR/AND A C-TERMINAL CARBOXYL GROUP, NONE, SOME OR ALL OF THESE GROUPS ARE PROTECTED, THE IMPROVEMENT WHEREIN 2,3N-HYDROXIMIDE COMPOUND IS NHYDROXY-5-NORBORNENE-A-DICARBOXIMIDE.
Claim 13
Dependent Claim
45 words
IF THE AMINO ACID OR PEPTIDE DERIVATIVE WHOSE N-TERMINAL AMINO OR IMINO GROUP IS FREE HAS FREE FUNCTIONAL GROUP OR GROUPS IN SIDE CHAIN OR/AND A C-TERMINAL CARBOXYL GROUP, NONE, SOME OR ALL OF THESE GROUPS ARE PROTECTED, THE IMPROVEMENT WHEREIN 2,3N-HYDROXIMIDE COMPOUND IS NHYDROXY-5-NORBORNENE-A-DICARBOXIMIDE.
Claim 14
Dependent Claim
15 words
A method as claimed in claim 1, wherein the objective peptide is L-pyroglutamyl-L-bistidyl-L-tryptophyl-L-seryl-L-tyrosyl-glycyl-L-leucyl-L -arginyl-L-prolyl-glycine amide.
Claim 15
Independent Claim
37 words
A method for producing L-pyroglutamyl-L-histidyl-L-proline amide, which comprises condensing a mixture containing N-carbobenzyloxy-L-pyroglutamyl-L-histidine, L-proline amide and N-hydroxy-5-norbornene-2,3-dicarboximide, by contacting said mixture with a carbodiimide reagent to produce N-carbobenzyloxy-L-pyroglutamyl-L-histidyl-L-proline amide and removing the carbobenzyloxycarbonyl group from the product.
Claim 16
Independent Claim
37 words
A method for producing L-pyroglutamyl-L-histidyl-L-proline amide, which comprises condensing a mixture containing N-carbobenzyloxy-L-pyroglutamyl-L-histidine, L-proline amide and N-hydroxy-5-norbornene-2,3-dicarboximide, by contacting said mixture with a carbodiimide reagent to produce N-carbobenzyloxy-L-pyroglutamyl-L-histidyl-L-proline amide and removing the carbobenzyloxycarbonyl group from the product.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-03-10 | 1978-09-09 | 1979-03-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-03-10 | 1982-09-09 | 1983-03-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-03-10 | 1986-09-09 | 1987-03-11 | $7700.00 | Window Closed / Lapsed |