US4625016A
Expired / Lapsed
US
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Collagen inhibiting compositions and processes for manufacturing and using same
Assignee: Rutgers Health
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Filing: 1983-10-17
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Granted: 1986-11-25
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Expires: 2003-10-17
Abstract
Abstract There is disclosed the use of a collagen inhibiting composition including in polymeric form select analogs of proline and processes for the manufacture and use of such a collagen-inhibiting composition to reduce scar tissue formation.
Inventors
- 👤 Darwin J. Prockop
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 18:21
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/74; A61K31/785
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
78 words
A method for the synthesis of a polymer of cis-4-hydroxy-L-proline consisting essentially of: A. preparing an active diester comprising the reaction product of an N-Benzyloxycarbonyl-, t-butyl and O-pentachlorophenyl-substituted derivative of cis-4-hydroxy-L-proline, and N-benzyloxycarbonyl-cis-4-hydroxyproline-OH; B. reacting the product of Step A with ethyl acetate, tetrahydrofuran, pentachlorophenol and dicyclohexyldicarbodiimide; C. polymerizing the product of Step B by dissolving it in dimethylformamide, triethylamine and imidazole; and D. recovering the polymeric reaction product by catalytic hydrogenation of the product of Step C.
Claim 2
Independent Claim
78 words
A method for the synthesis of a polymer of cis-4-hydroxy-L-proline consisting essentially of: A. preparing an active diester comprising the reaction product of an N-Benzyloxycarbonyl-, t-butyl and O-pentachlorophenyl-substituted derivative of cis-4-hydroxy-L-proline, and N-benzyloxycarbonyl-cis-4-hydroxyproline-OH; B. reacting the product of Step A with ethyl acetate, tetrahydrofuran, pentachlorophenol and dicyclohexyldicarbodiimide; C. polymerizing the product of Step B by dissolving it in dimethylformamide, triethylamine and imidazole; and D. recovering the polymeric reaction product by catalytic hydrogenation of the product of Step C.
Claim 3
Independent Claim
51 words
A method for the synthesis of a polymer of cis-4-hydroxy-L-proline consisting essentially of: A. preparing an active ester of cis-4-hydroxy-L-proline comprising the N-benzyloxycarbonyl- and O-pentachlorophenyl-substituted derivative of cis-4-hydroxy-L-proline; B. reacting the ester of Step A in the presence of dimethylformamide and imidazole; and C. recovering the polymerized product of Step B.
Claim 4
Independent Claim
51 words
A method for the synthesis of a polymer of cis-4-hydroxy-L-proline consisting essentially of: A. preparing an active ester of cis-4-hydroxy-L-proline comprising the N-benzyloxycarbonyl- and O-pentachlorophenyl-substituted derivative of cis-4-hydroxy-L-proline; B. reacting the ester of Step A in the presence of dimethylformamide and imidazole; and C. recovering the polymerized product of Step B.
Claim 5
Independent Claim
132 words
A method for the synthesis of a polymer in which cis-4-hydroxy-L-proline is linked to a polypeptide chain formed from cis-4-hydroxy-L-proline, alanine and glycine, consisting essentially of: A. preparing a polymer of cis-4-hydroxy-L-proline, alanine and glycine from the reactants comprising N-benzyloxycarbonyl-substituted cis-4-hydroxy-L-proline, N-benzyloxycarbonyl-substituted L-alanine and O-benzyl-glycine; B. reacting reactant derivatives of glycine and cis-4-hydroxy-L-proline with each other; C. reacting the reaction product of Step B with the reactant derivative of alanine; D. reacting the reaction product of Step C with the N-benzyloxycarbonyl-, butyl and O-pentachlorophenyl derivative of cis-4-hydroxy-L-proline; E. polymerizing the product of Step D in dimethylformamide and triethylamine; and F. recovering the reaction product of Step E by catalytic hydrogenation, wherein said reaction product comprises comprising a polymer wherein cis-4-hydroxy-L-proline is associated with a polypeptide chain formed from cis-4-hydroxy-L-proline, alanine and glycine.
Claim 6
Independent Claim
132 words
A method for the synthesis of a polymer in which cis-4-hydroxy-L-proline is linked to a polypeptide chain formed from cis-4-hydroxy-L-proline, alanine and glycine, consisting essentially of: A. preparing a polymer of cis-4-hydroxy-L-proline, alanine and glycine from the reactants comprising N-benzyloxycarbonyl-substituted cis-4-hydroxy-L-proline, N-benzyloxycarbonyl-substituted L-alanine and O-benzyl-glycine; B. reacting reactant derivatives of glycine and cis-4-hydroxy-L-proline with each other; C. reacting the reaction product of Step B with the reactant derivative of alanine; D. reacting the reaction product of Step C with the N-benzyloxycarbonyl-, butyl and O-pentachlorophenyl derivative of cis-4-hydroxy-L-proline; E. polymerizing the product of Step D in dimethylformamide and triethylamine; and F. recovering the reaction product of Step E by catalytic hydrogenation, wherein said reaction product comprises comprising a polymer wherein cis-4-hydroxy-L-proline is associated with a polypeptide chain formed from cis-4-hydroxy-L-proline, alanine and glycine.
References Cited (Backward Citations)
US4428939A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1989-11-24 | 1990-05-26 | 1990-11-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-11-24 | 1994-05-26 | 1994-11-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-11-24 | 1998-05-26 | 1998-11-25 | $7700.00 | Window Closed / Lapsed |