US4033940A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Cyclization of peptides
Assignee: Aventis Pharmaceuticals Inc
•
Filing: 1975-11-12
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Granted: 1977-07-05
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Expires: 1995-11-12
Abstract
Abstract The synthesis of a disulfide cyclic peptide by preparing an intermediate peptide containing an amino terminal cystine residue and a cysteine residue located in a position within the amino acid sequence, to give a desired peptide, and placing such intermediate peptide in a solution substantially free of oxygen at a pH of from about 5 to 10 until rearrangement takes place to yield a cyclic disulfide peptide and to displace a molecule of cysteine from the amino terminal cysteine residue. 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
2026-10-30 17:29
CPC Classifications
C; C07; C07K; C07K1/00; C07K1/06; C07K1/061; C07K1/067; C07K14/00; C07K14/435; C07K14/575; C07K14/585; A; A61; A61K; A61K38/00; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/15
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
56 words
In a process for preparing a peptide having a disulfide ring structure, the step of holding a peptide which contains an amino terminal cystine residue and a cysteine residue located in a position within the amino acid sequence in a solution substantially free of oxygen until rearrangement has taken place to yield a cyclic disulfide peptide.
Claim 2
Dependent Claim
56 words
In a process for preparing a peptide having a disulfide ring structure, the step of holding a peptide which contains an amino terminal cystine residue and a cysteine residue located in a position within the amino acid sequence 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 inert 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
14 words
A process as set forth in clain 1 in which said peptide is: ##STR30##
Claim 10
Dependent Claim
14 words
A process as set forth in clain 1 in which said peptide is: ##STR30##
Claim 11
Dependent Claim
14 words
a process as set forth in claim 1 in which said peptide is: ##STR31##
Claim 12
Dependent Claim
14 words
A process as set forth in claim 1 in which said peptide is: ##STR32##
Claim 13
Dependent Claim
84 words
A process as set forth in claim 1 which includes the preparation of said peptide by coupling said cysteine residue into an amino acid chain while protecting the sulfhydryl function of said residue with a group selected from the class consisting of benzyl, 4-methoxybenzyl, 4-methylbenzyl, 3,4-dimethylbenzyl, 4-chlorobenzyl, 2,6-dichlorobenzyl, 4-nitrobenzyl, benzylhydryl, tertiary butylthio and isopropylthio, and coupling cystine residue into said chain at its amino terminal end, and treating the peptide so formed with anhydrous acid to cleave said selected group from said cysteine residue.
Claim 14
Dependent Claim
21 words
A process as set forth in claim 11 in which said chain includes the following sequence of amino acid moieties: ##STR33##
Claim 15
Dependent Claim
21 words
A process as set forth in claim 11 in which said chain includes the following sequence of amino acid moieties: ##STR34##
Claim 16
Dependent Claim
35 words
A peptide having an amino acid sequence the same as that of a natural calcitonin and which contains an amino terminal cystine moiety and a cysteine moiety within said sequence having a free sulfhydryl function.
Claim 17
Dependent Claim
35 words
A peptide having an amino acid sequence the same as that of a natural calcitonin and which contains an amino terminal cystine moiety and a cysteine moiety within said sequence having a free sulfhydryl function.
Claim 18
Dependent Claim
29 words
A peptide as set forth in claim 14 in which said amino acid sequence is the same as in salmon calcitonin except that the amino terminal moiety is cystine.
Claim 19
Dependent Claim
34 words
A peptide having an amino acid sequence which is the same as that of oxytocin and containing an amino terminal cystine moiety and a cysteine moiety within said sequence having a free sulfhydryl function.
Claim 20
Dependent Claim
34 words
A peptide having an amino acid sequence which is the same as that of oxytocin and containing an amino terminal cystine moiety and a cysteine moiety within said sequence having a free sulfhydryl function.
Claim 21
Dependent Claim
32 words
a peptide having an amino acid sequence the same as that of vasopressin and containing an amino terminal cystine moiety and a cysteine moiety within said sequence having a free sulfhydryl function.
Claim 22
Dependent Claim
32 words
a peptide having an amino acid sequence the same as that of vasopressin and containing an amino terminal cystine moiety and a cysteine moiety within said sequence having a free sulfhydryl function.
Claim 23
Dependent Claim
29 words
A peptide as set forth in claim 14 in which said amino acid sequence is the same as in human calcitonin except that the amino terminal moiety is cystine.
Claim 24
Dependent Claim
29 words
A peptide as set forth in claim 14 in which said amino acid sequence is the same as in procine calcitonin except that the amino terminal moiety is cystine.
Claim 25
Dependent Claim
29 words
A peptide as set forth in claim 14 in which said amino acid sequence is the same as in bovine calcitonin except that the amino terminal moiety is cystine.
Claim 26
Dependent Claim
54 words
A peptide having an amino acid sequence the same as that of a natural calcitonin and which contains an amino terminal cystine moiety and an intermediate cysteine moiety having its sulfhydryl function protected by a group selected from the class consisting of benzyl, 4-methoxybenzyl, 4-methylbenzyl, 3,4-dimethylbenzyl, 4-chlorobenzyl, 2,6-dichlorobenzyl, 4-nitrobenzyl, benzylhydryl, tertiary butylthio, and isopropylthio.
Claim 27
Dependent Claim
54 words
A peptide having an amino acid sequence the same as that of a natural calcitonin and which contains an amino terminal cystine moiety and an intermediate cysteine moiety having its sulfhydryl function protected by a group selected from the class consisting of benzyl, 4-methoxybenzyl, 4-methylbenzyl, 3,4-dimethylbenzyl, 4-chlorobenzyl, 2,6-dichlorobenzyl, 4-nitrobenzyl, benzylhydryl, tertiary butylthio, and isopropylthio.
References Cited (Backward Citations)
US3929758A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-04 | 1981-01-03 | 1981-07-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-04 | 1985-01-03 | 1985-07-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-04 | 1989-01-03 | 1989-07-05 | $7700.00 | Window Closed / Lapsed |