CA2106474A1 - Polyoxypropylene/polyoxyethylene copolymers with improved biological activity - Google Patents
Polyoxypropylene/polyoxyethylene copolymers with improved biological activityInfo
- Publication number
- CA2106474A1 CA2106474A1 CA002106474A CA2106474A CA2106474A1 CA 2106474 A1 CA2106474 A1 CA 2106474A1 CA 002106474 A CA002106474 A CA 002106474A CA 2106474 A CA2106474 A CA 2106474A CA 2106474 A1 CA2106474 A1 CA 2106474A1
- Authority
- CA
- Canada
- Prior art keywords
- polyoxypropylene
- preparations
- copolymers
- polyoxyethylene
- biological activity
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
- A61K31/77—Polymers containing oxygen of oxiranes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/60—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
- C08G65/2621—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups
- C08G65/2624—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups containing aliphatic amine groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/30—Post-polymerisation treatment, e.g. recovery, purification, drying
Abstract
The present invention comprises novel preparations of polyoxypropylene/polyoxyethylene copolymers which retain the therapeutic activity of the commercial preparations, but are substantially free from the undesirable effects which are inherent in the prior art preparations. The preparation entails first condensing propylene oxide to produce a polyoxypropylene polymer and then condensing ethylene oxide with the polyoxypropylene polymer to produce a polyoxypropylene/polyoxyethylene block copolymer of the general formula:
HO(C2H4O)b(C3H6O)a(C2H4O)b H
wherein a and b are integers. Because the preparations of polyoxypropylene/polyoxyethylene copolymers which comprise the present invention are a less polydisperse population of molecules than the prior art polyoxypropylene/polyoxyethylene copolymers, the biological activity of the copolymers is better defined and more predictable. The polydispersity of the copolymer is very low, average less than 1.07.
HO(C2H4O)b(C3H6O)a(C2H4O)b H
wherein a and b are integers. Because the preparations of polyoxypropylene/polyoxyethylene copolymers which comprise the present invention are a less polydisperse population of molecules than the prior art polyoxypropylene/polyoxyethylene copolymers, the biological activity of the copolymers is better defined and more predictable. The polydispersity of the copolymer is very low, average less than 1.07.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US847,874 | 1977-11-02 | ||
US67328991A | 1991-03-19 | 1991-03-19 | |
US673,289 | 1991-03-19 | ||
US84787492A | 1992-03-13 | 1992-03-13 | |
PCT/US1992/002254 WO1992016484A1 (en) | 1991-03-19 | 1992-03-18 | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2106474A1 true CA2106474A1 (en) | 1992-09-20 |
CA2106474C CA2106474C (en) | 2004-02-10 |
Family
ID=27100911
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002106474A Expired - Fee Related CA2106474C (en) | 1991-03-19 | 1992-03-18 | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
Country Status (19)
Country | Link |
---|---|
US (7) | US5523492A (en) |
EP (1) | EP0576612B1 (en) |
JP (1) | JP2647556B2 (en) |
KR (1) | KR100224539B1 (en) |
CN (1) | CN1069741A (en) |
AT (1) | ATE187154T1 (en) |
AU (1) | AU662146B2 (en) |
CA (1) | CA2106474C (en) |
CZ (1) | CZ194693A3 (en) |
DE (1) | DE69230372T2 (en) |
DK (1) | DK0576612T3 (en) |
ES (1) | ES2140408T3 (en) |
GR (1) | GR3032726T3 (en) |
HU (1) | HUT67762A (en) |
IE (1) | IE920860A1 (en) |
IL (1) | IL101305A (en) |
NO (1) | NO307890B1 (en) |
SK (1) | SK100893A3 (en) |
WO (1) | WO1992016484A1 (en) |
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-
1992
- 1992-03-18 HU HU9302628A patent/HUT67762A/en unknown
- 1992-03-18 ES ES92910791T patent/ES2140408T3/en not_active Expired - Lifetime
- 1992-03-18 AT AT92910791T patent/ATE187154T1/en not_active IP Right Cessation
- 1992-03-18 AU AU17730/92A patent/AU662146B2/en not_active Ceased
- 1992-03-18 KR KR1019930702810A patent/KR100224539B1/en not_active IP Right Cessation
- 1992-03-18 DK DK92910791T patent/DK0576612T3/en active
- 1992-03-18 JP JP4509970A patent/JP2647556B2/en not_active Expired - Fee Related
- 1992-03-18 EP EP92910791A patent/EP0576612B1/en not_active Expired - Lifetime
- 1992-03-18 IE IE086092A patent/IE920860A1/en not_active IP Right Cessation
- 1992-03-18 CZ CS931946A patent/CZ194693A3/en unknown
- 1992-03-18 CA CA002106474A patent/CA2106474C/en not_active Expired - Fee Related
- 1992-03-18 WO PCT/US1992/002254 patent/WO1992016484A1/en active IP Right Grant
- 1992-03-18 SK SK1008-93A patent/SK100893A3/en unknown
- 1992-03-18 DE DE69230372T patent/DE69230372T2/en not_active Expired - Fee Related
- 1992-03-18 CN CN92102964A patent/CN1069741A/en active Pending
- 1992-03-19 IL IL10130592A patent/IL101305A/en not_active IP Right Cessation
-
1993
- 1993-07-02 US US08/087,136 patent/US5523492A/en not_active Ceased
- 1993-09-17 NO NO933337A patent/NO307890B1/en unknown
-
1996
- 1996-06-03 US US08/657,161 patent/US5691387A/en not_active Ceased
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1997
- 1997-07-08 US US08/889,342 patent/US5990241A/en not_active Expired - Fee Related
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1998
- 1998-06-02 US US09/089,043 patent/USRE36665E/en not_active Expired - Lifetime
-
1999
- 1999-08-05 US US09/368,855 patent/US6359014B1/en not_active Expired - Fee Related
- 1999-11-19 US US09/444,417 patent/USRE37285E1/en not_active Expired - Fee Related
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2000
- 2000-02-23 GR GR20000400425T patent/GR3032726T3/en not_active IP Right Cessation
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2001
- 2001-12-14 US US10/017,223 patent/US6747064B2/en not_active Expired - Fee Related
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