US4101721A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Solid phase synthesis of protected peptides
Assignee: Wisconsin Alumni Research Foundation
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Filing: 1976-12-09
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Granted: 1978-07-18
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Expires: 1996-12-09
Abstract
Abstract The invention is addressed to the preparation of 3-nitro-4-bromomethyl benzoic acid, as a new compound from which 3-nitro-4-bromomethyl benzoyl amide polystyrene resin can be prepared for solid synthesis of protected peptide acids and amides and separation thereof without cleavage of acid labile protecting groups or decomposition of aromatic acid groups and from which purified polypeptides can be formed.
Inventors
- 👤 Daniel H. Rich
- 👤 Sweet K. Gurwara
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 09:49
CPC Classifications
C; C07; C07K; C07K1/00; C07K1/04; C07K1/042; C08; C08F; C08F8/00; C08F8/30; C08F8/32; C08F2810/00; C08F2810/20; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/13
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
24 words
A supported 3-nitro-4-bromomethyl benzoyl amide having the general formula ##STR10## in which R is 0-8 carbon atoms in an alkyl or substituted alkyl group.
Claim 2
Dependent Claim
24 words
A supported 3-nitro-4-bromomethyl benzoyl amide having the general formula ##STR10## in which R is 0-8 carbon atoms in an alkyl or substituted alkyl group.
Claim 3
Dependent Claim
17 words
The supported 3-nitro-4-bromomethyl benzoyl amide as claimed in claim 1 in which the support is a resin.
Claim 4
Dependent Claim
18 words
The supported 3-nitro-4-bromomethyl benzoyl amide as claimed in claim 2 in which the resin is a polystyrene resin.
Claim 5
Dependent Claim
18 words
The supported 3-nitro-4-bromomethyl benzoyl amide as claimed in claim 1 in which the support is a polystyrene resin.
Claim 6
Independent Claim
18 words
The method for preparing 3-nitro-4-bromomethyl benzoyl amide polystyrene resin comprising reacting aminomethyl polystyrene resin with 3-nitro-4-bromomethyl benzoic acid.
Claim 7
Independent Claim
18 words
The method for preparing 3-nitro-4-bromomethyl benzoyl amide polystyrene resin comprising reacting aminomethyl polystyrene resin with 3-nitro-4-bromomethyl benzoic acid.
Claim 8
Dependent Claim
27 words
The method as claimed in claim 5 in which the aminomethyl polystyrene resin and the nitro benzoic acid are reacted in the presence of dicyclohexylcarbodiamide in dimethylformamide.
Claim 9
Dependent Claim
38 words
The method as claimed in claim 6 in which the product of the reaction of the amino methylated polystyrene resin and the nitro benzoic acid is treated with diisopropylamine while suspended in a solvent carrier and acetic anhydride.
Claim 10
Dependent Claim
32 words
A supported 3-nitro-4-aminomethyl benzoyl amide in which the amino group is protected, as represented by the formula ##STR11## in which R is 0-8 carbon atoms in an alkyl or substituted alkyl group.
Claim 11
Dependent Claim
32 words
A supported 3-nitro-4-aminomethyl benzoyl amide in which the amino group is protected, as represented by the formula ##STR11## in which R is 0-8 carbon atoms in an alkyl or substituted alkyl group.
Claim 12
Dependent Claim
18 words
A supported 3-nitro-4-aminomethyl benzoyl amide as claimed in claim 8 in which the support is a polystyrene resin.
Claim 13
Dependent Claim
18 words
A supported 3-nitro-4-aminomethyl benzoyl amide as claimed in claim 8 in which the support is a polystyrene resin.
Claim 14
Dependent Claim
21 words
A supported 3-nitro-4-aminomethyl benzoyl amide as claimed in claim 8 in which the protective group is a t-butoxy carbonyl (Boc) group.
Claim 15
Independent Claim
24 words
The method of preparing 3-nitro-4-t-butoxy carbonyl (Boc) aminomethyl benzoyl amide polystyrene resin comprising 3-nitro-4-t-butoxy carbonyl (Boc) aminomethyl benzoic acid with an aminomethyl polystyrene resin.
Claim 16
Independent Claim
24 words
The method of preparing 3-nitro-4-t-butoxy carbonyl (Boc) aminomethyl benzoyl amide polystyrene resin comprising 3-nitro-4-t-butoxy carbonyl (Boc) aminomethyl benzoic acid with an aminomethyl polystyrene resin.
Claim 17
Dependent Claim
21 words
The method as claimed in claim 12 in which the reaction is carried out in the presence of dimethylformamide and dicyclohexylcarbodiimide.
Claim 18
Dependent Claim
18 words
The supported 3-nitro-4-bromomethyl benzoyl amide as claimed in claim 1 in which the support is a polyamide resin.
Claim 19
Dependent Claim
18 words
A supported 3-nitro-4-aminomethyl benzoyl amide as claimed in claim 8 in which the support is a polymide resin.
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) | 1981-07-17 | 1982-01-16 | 1982-07-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-07-17 | 1986-01-16 | 1986-07-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-07-17 | 1990-01-16 | 1990-07-18 | $7700.00 | Window Closed / Lapsed |