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US5183660A
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Polyethylene glycol derivatives, their modified peptides, methods for producing them and use of the modified peptides
Assignee: Sumitomo Pharma Co Ltd
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Filing: 1991-08-15
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Granted: 1993-02-02
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Expires: 2011-08-15
Abstract
Abstract Polyethylene glycol derivatives of the formula ##STR1## wherein R 1 and R 2 are the same or different and each represents a lower alkyl, m and n are the same or different and each represents a positive integer and p is 0 or a positive integer, peptides modified by the polyethylene glycol derivatives, methods for producing them and use of the modified peptides. The peptides modified by the polyethylene glycol derivatives (I) of the invention, as compared with the corresponding non-modified peptides, show decreased antigenicity, are considerably delayed in biological clearance, and exhibit their physiological activities effectively over a long period, rendering them very effective as pharmaceuticals as well as drugs for animals.
Inventors
- 👤 Yoshiharu Ikeda
- 👤 Yoshiyuki Kai
- 👤 Keiichi Ono
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 09:09
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/02; C08G65/32; C08G65/329; C08G65/331; C08G65/332; C08G65/3324; C08G65/3326; A; A61; A61K; A61K47/00; A61K47/50; A61K47/51; A61K47/56; A61K47/59; A61K47/60; C08G65/3311; C08G65/3314; C08G65/3315; C08G65/3317
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
51 words
A polyethylene glycol derivative of the formula ##STR16## wherein R 1 and R 2 are the same or different and each represents a lower alkyl, m and n are the same or different and each represents a positive integer of 10 to 400, and p is 0 or a positive integer.
Claim 2
Dependent Claim
51 words
A polyethylene glycol derivative of the formula ##STR16## wherein R 1 and R 2 are the same or different and each represents a lower alkyl, m and n are the same or different and each represents a positive integer of 10 to 400, and p is 0 or a positive integer.
Claim 3
Dependent Claim
21 words
A polyethylene glycol derivative as claimed in claim 1 wherein p is 0 or a positive integer of 1 to 10.
Claim 4
Dependent Claim
21 words
A polyethylene glycol derivative as claimed in claim 1 which is selected from the group consisting of 3,5-bis-methoxypolyethylene glycol dihydrocinnamic acid.
Claim 5
Dependent Claim
21 words
A modified peptide wherein amino groups in the peptide are modified by a polyethylene glycol derivative as claimed in claim 1.
Claim 6
Dependent Claim
35 words
A modified peptide as claimed in claim 4 wherein the peptide has 2 or more amino acids bound by peptide bonds and at least one of the constituent amino acids has a free amino group.
Claim 7
Dependent Claim
35 words
A modified peptide as claimed in claim 4 wherein the peptide is selected from the group consisting of superoxide dismutase, insulin-like growth factor-I, insulin-like growth factor-II, calcitonin gene related peptide, elastase and growth hormone-releasing factor.
Claim 8
Dependent Claim
103 words
A modified peptide as claimed in claim 4 which is selected from the group consisting of superoxide dismutase modified by 3,5-bis-methoxypolyethylene glycol benzoic acid, insulin-like growth factor-I modified by 3,5-bis-methoxypolyethylene glycol benzoic acid, insulin-like growth factor-II modified by 3,5-bis-methoxypolyethylene glycol benzoic acid, calcitonin gene related peptide modified by 3,5-bis-methoxypolyethylene glycol benzoic acid, elastase modified by 3,5-bis-methoxypolyethylene glycol benzoic acid, superoxide dismutase modified by 3,4-bis-methoxypolyethylene glycol dihydrocinnamic acid, insulin-like growth factor-I modified by 3,4-bis-methoxypolyethylene glycol dihydrocinnamic acid, calcitonin gene related peptide modified by 3,4-bis-methoxypolyethylene glycol dihydrocinnamic acid, elastase modified by 3,4-bis-methoxypolyethylene glycol dihydrocinnamic acid and growth hormone-releasing factor modified by 3,4-bis-methoxypolyethylene glycol dihydrocinnamic acid.
Claim 9
Dependent Claim
78 words
A method for producing a polyethylene glycol derivative as claimed in claim 1 comprising reacting a compound of the formula (III) of (III') ##STR17## wherein X 1 and X 2 are the same or different and each represents an alkylsulfonyloxy, an aromatic sulfonyloxy or a halogen, and R 1 , R 2 , m and n are as defined in claim 1, with a compound of the formula (IV) ##STR18## wherein p is as defined in claim 1.
Claim 10
Dependent Claim
17 words
A pharmaceutical composition comprising a modified peptide as claimed in claim 4 and a pharmaceutically acceptable carrier.
Claim 11
Dependent Claim
17 words
A pharmaceutical composition comprising a modified peptide as claimed in claim 5 and a pharmaceutically acceptable carrier.
Claim 12
Dependent Claim
17 words
A pharmaceutical composition comprising a modified peptide as claimed in claim 6 and a pharmaceutically acceptable carrier.
Claim 13
Dependent Claim
17 words
A pharmaceutical composition comprising a modified peptide as claimed in claim 7 and a pharmaceutically acceptable carrier.
Claim 14
Independent Claim
71 words
A method for producing a modified peptide comprising reacting a carboxyl group-activated compound of a polyethylene glycol derivative of the formula ##STR19## wherein R 1 and R 2 are the same or different and each represents a lower alkyl, m and n are the same or different and each represents a positive integer and p is 0 or a positive integer, with a peptide having at least one free amino group.
Claim 15
Independent Claim
71 words
A method for producing a modified peptide comprising reacting a carboxyl group-activated compound of a polyethylene glycol derivative of the formula ##STR19## wherein R 1 and R 2 are the same or different and each represents a lower alkyl, m and n are the same or different and each represents a positive integer and p is 0 or a positive integer, with a peptide having at least one free amino group.
Claim 16
Dependent Claim
20 words
A method as claimed in claim 13 wherein m and n are respectively a positive integer of 10 to 400.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-02-02 | 1996-08-03 | 1997-02-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-02-02 | 2000-08-03 | 2001-02-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-02-02 | 2004-08-03 | 2005-02-02 | $7700.00 | Window Closed / Lapsed |