US4212795A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Cyclization of peptides
Assignee: Aventis Pharmaceuticals Inc
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Filing: 1978-11-13
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Granted: 1980-07-15
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Expires: 1998-11-13
Abstract
Abstract The synthesis of a disulfide cyclic peptide by preparing an intermediate peptide containing two cysteine moieties, each of which is protected by an n-alkylthio group, or when one of such moieties is in an amino terminal position, this one moiety may be protected by a cysteine group while the other is protected by an n-alkylthio group, and placing such intermediate peptide in a solution substantially free of oxygen and preferably at a pH of from 5 to 10 until rearrangement has taken place, to yield a cyclic disulfide peptide. The disclosure also embraces said intermediate peptides as new compounds and the processes by which they are prepared.
Inventors
- 👤 John L. Hughes
- 👤 Jay K. Seyler
- 👤 Robert C. Liu
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 10:53
CPC Classifications
C; C07; C07K; C07K1/00; C07K1/06; C07K1/061; C07K1/067; C07K1/12; C07K14/00; C07K14/435; C07K14/575; C07K14/585; C07K14/655; A; A61; A61K; A61K38/00; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/15; Y10S930/16
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
79 words
In a process for preparing a peptide having a disulfide ring structure, the step of holding a peptide having in its amino acid chain two cysteine residues, one of which has an n-alkylthio group attached thereto, and the other of which has attached thereto an n-alkylthio group or, if said other residue is at the amino terminal position, a cysteine group, in a solution substantially free of oxygen until rearrangement has taken place, to yield a cyclic disulfide peptide.
Claim 2
Dependent Claim
79 words
In a process for preparing a peptide having a disulfide ring structure, the step of holding a peptide having in its amino acid chain two cysteine residues, one of which has an n-alkylthio group attached thereto, and the other of which has attached thereto an n-alkylthio group or, if said other residue is at the amino terminal position, a cysteine group, in a solution substantially free of oxygen until rearrangement has taken place, to yield a cyclic disulfide peptide.
Claim 3
Dependent Claim
16 words
A process as set forth in claim 1 in which said solution is an aqueous solution.
Claim 4
Dependent Claim
17 words
A process as set forth in claim 1 in which said solution is an aqueous alcoholic solution.
Claim 5
Dependent Claim
19 words
A process as set forth in claim 2 which includes the step of agitating said solution during said rearrangement.
Claim 6
Dependent Claim
18 words
A process as set forth in claim 1 including conducting said rearrangement under a stream of innert gas.
Claim 7
Dependent Claim
13 words
A process as set forth in claim 5 wherein said gas is nitrogen.
Claim 8
Dependent Claim
21 words
A process as set forth in claim 5 which includes continuing the process for a period of at least one hour.
Claim 9
Dependent Claim
25 words
A process as set forth in claim 1 in which said peptide is: ##STR37## in which Y is n-alkylthio and X is n-alkylthio or H-CYS.
Claim 10
Dependent Claim
14 words
A process as set forth in claim 1 in which said peptide is: ##STR38##
Claim 11
Dependent Claim
25 words
A process as set forth in claim 1 in which said peptide is: ##STR39## in which Y is n-alkylthio and X is n-alkylthio or H-CYS.
Claim 12
Dependent Claim
22 words
A process as set forth in claim 1 in which said peptide is: ##STR40## in which X is n-alkylthio Y is n-alkylthio.
Claim 13
Dependent Claim
25 words
A process as set forth in claim 1 in which said peptide is: ##STR41## in which X is n-alkylthio or H-CYS and Y is n-alkylthio.
Claim 14
Dependent Claim
54 words
A peptide having an amino acid sequence the same as that of a natural calcitonin and which has in said sequence a cysteine moiety protected by an n-alkylthio group and another cysteine moiety protected by an n-alkylthio group, or if said other moiety is in an amino terminal position, protected by another cysteine group.
Claim 15
Dependent Claim
54 words
A peptide having an amino acid sequence the same as that of a natural calcitonin and which has in said sequence a cysteine moiety protected by an n-alkylthio group and another cysteine moiety protected by an n-alkylthio group, or if said other moiety is in an amino terminal position, protected by another cysteine group.
Claim 16
Dependent Claim
18 words
A peptide as set forth in claim 13 in which each of said groups is an n-alkylthio group.
Claim 17
Dependent Claim
24 words
A peptide as set forth in claim 13 in which one of said cysteine moieties is in an amino terminal position and is cysteine.
Claim 18
Dependent Claim
23 words
A peptide as set forth in claim 13 in which said amino acid sequence is the same as that of a salmon calcitonin.
Claim 19
Dependent Claim
23 words
A peptide as set forth in claim 13 in which said amino acid sequence is the same as that of a porcine calcitonin.
Claim 20
Dependent Claim
21 words
A peptide as set forth in claim 13 in which said amino acid sequence is the same as that of somatostatin.
Claim 21
Dependent Claim
22 words
A peptide as set forth in claim 13 in which amino acid sequence is the same as that of an eel calcitonin.
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) | 1983-07-15 | 1984-01-14 | 1984-07-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-07-15 | 1988-01-14 | 1988-07-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-07-15 | 1992-01-14 | 1992-07-15 | $7700.00 | Window Closed / Lapsed |