WO1992016484A1 - Polyoxypropylene/polyoxyethylene copolymers with improved biological activity - Google Patents
Polyoxypropylene/polyoxyethylene copolymers with improved biological activity Download PDFInfo
- Publication number
- WO1992016484A1 WO1992016484A1 PCT/US1992/002254 US9202254W WO9216484A1 WO 1992016484 A1 WO1992016484 A1 WO 1992016484A1 US 9202254 W US9202254 W US 9202254W WO 9216484 A1 WO9216484 A1 WO 9216484A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- copolymer
- approximately
- polyoxypropylene
- molecular weight
- daltons
- Prior art date
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
Definitions
- a sickle cell crisis During a sickle cell crisis, sickled red blood cells aggregate because of the abnormal shape of the cells. In many cases, there are high concentrations of soluble fibrin due to disseminated intravascular coagulation. This results in pathological hydrophobic interactions between blood cells, cells lining the blood vessels and soluble fibrin and fibrinogen.
- the surface-active copolymer may be given prior to a sickle cell crisis to prevent onset of the crisis.
- the solution with the effective amount of surface-active copolymer may also contain an effective amount of anticoagulant.
- anti-inflammatories including, but not limited to, both steroids and nonsteroid antiinflammatory drugs;
- membrane stabilizers such as dilantin;
- the molecular weight of the hydrophobe portion of the octablock copolymer consisting of (C 3 H 6 O) is between approximately 5000 and 7000 daltons;
- the surface-active copolymers are effective in treating a viral infection in a human or animal including infections caused by the HIV virus or related strains.
- the present invention provides a composition that can be administered to patients who are infected with HIV viruses or similar viruses.
- the surface-active copolymer is effective in inhibiting or suppressing the replication of the HIV virus and related virus strains in cells.
- a is an integer such that the hydrophobe represented by (C3H6O) has a molecular weight of about 1200 to
- the present invention comprises novel preparations of polyoxypropylene/polyoxyethylene copolymers which retain the therapeutic activity of the commercial preparations, but are free from the undesirable effects which are inherent in the prior art preparations. Because the 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. In addition, the polyoxypropylene/polyoxyethylene copolymers which comprise the present invention are substantially free of unsaturation.
- the method of preparing a non-toxic surface-active copolymer includes first condensing propylene oxide with a base compound containing a plurality of reactive hydrogen atoms to produce polyoxypropylene polymer and then condensing ethylene oxide with the polyoxypropylene polymer to produce a polyoxypropylene/polyoxyethylene block copolymer with the following general formula:
- Fig. 3 is a chromatogram of fraction 1 of the poloxamer 188 collected from the chromatographic run described in Example I.
- Figs. 11A through 11C are gel permeation chromatograms of three fractions of poloxamer 188.
- Polydispersity measurements using different separation principles may give absolute polydispersity values which are different from those described herein.
- one of ordinary skill in the art can easily convert any polydispersity value that is obtained using a different separation method to the values described herein simply by running a single sample on both systems and then comparing the polydispersity values from each chromatogram.
- the surface-active copolymers of the present invention can be prepared in a number of ways.
- the polydispersity value can be reduced by subjecting the prior art compounds to gel permeation chromatography.
- the compounds can be subjected to molecular sieving techniques that are known to those of ordinary skill in the art.
- the present invention also includes a novel method of preparing a surface-active copolymer composition with the specifications described herein.
- the novel method involves the preparation of a uniform hydrophobic polyoxypropylene polymer and then proceed with the addition of the hydrophilic polyoxyethylene as is normally done. It is believed that the toxic copolymers that are the result of the standard commercial method of preparing poloxamer 188 are due to truncated polymer chains and to unsaturation in the polymer.
- Example IV The purified polyoxypropylene glycol from Example IV was placed in the same apparatus as described in Example III with an appropriate amount of anhydrous sodium hydroxide. An appropriate amount of ethylene oxide was added at an average temperature of 120°C using the same technique described in Example HI. The amount of added ethylene oxide corresponded to 20% of the total weight of the polyoxypropylene glycol base plus the weight of added ethylene oxide.
- y b As measured by gel permeation chromatography As shown in Table IV, the early eluting, the large molecular weight fraction had a high percentage of oxyethylene and corresponded to a poloxamer 258. The middle fraction had the smallest percentage of oxyethylene while the late eluting, small molecular weight fraction had the highest percentage of oxyethylene. The middle fraction had a calculated poloxamer number of 178 which corresponds closely to the desired number of 188. The late fraction had a calculated poloxamer number of 039. Thus, the commercially available poloxamer preparation has a significant population of polymers which may be harmful in a biological system.
Abstract
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU17730/92A AU662146B2 (en) | 1991-03-19 | 1992-03-18 | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
DE69230372T DE69230372T2 (en) | 1991-03-19 | 1992-03-18 | POLYOXYPROPYLEN / POLYOXYETHYLEN COPOLYMERE WITH IMPROVED BIOLOGICAL ACTIVITY |
CS931946A CZ194693A3 (en) | 1991-03-19 | 1992-03-18 | Copolymers polyoxypropylene/polyoxyethylene with enhanced biological activity |
SK1008-93A SK100893A3 (en) | 1991-03-19 | 1992-03-18 | Polyoxypropylene-polyoxyethylene copolymers with improved biological activity |
KR1019930702810A KR100224539B1 (en) | 1991-03-19 | 1992-03-18 | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
JP4509970A JP2647556B2 (en) | 1991-03-19 | 1992-03-18 | Polyoxypropylene / polyoxyethylene copolymers with improved biological activity |
CA002106474A CA2106474C (en) | 1991-03-19 | 1992-03-18 | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
EP92910791A EP0576612B1 (en) | 1991-03-19 | 1992-03-18 | Polyoxypropylene/polyoxyethylene copolymers with improved biological activity |
DK92910791T DK0576612T3 (en) | 1991-03-19 | 1992-03-18 | Polyoxypropylene / polyoxyethylene copolymers with improved activity |
NO933337A NO307890B1 (en) | 1991-03-19 | 1993-09-17 | Polyoxypropylene / polyoxyethylene copolymer blend, process for its preparation and medicament comprising a copolymer blend |
GR20000400425T GR3032726T3 (en) | 1991-03-19 | 2000-02-23 | Signal transmission and tag power consumption measurement circuit for an inductive reader. |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US67328991A | 1991-03-19 | 1991-03-19 | |
US673,289 | 1991-03-19 | ||
US84787492A | 1992-03-13 | 1992-03-13 | |
US847,874 | 1992-03-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1992016484A1 true WO1992016484A1 (en) | 1992-10-01 |
Family
ID=27100911
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1992/002254 WO1992016484A1 (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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EP0576192A2 (en) * | 1992-06-17 | 1993-12-29 | Amgen Inc. | Polyoxymethylene-oxyethylene copolymers in conjunction with biomolecules |
US5488034A (en) * | 1993-02-02 | 1996-01-30 | Xoma Corporation | Pharmaceutical composition comprising BPI proteins |
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US5932544A (en) * | 1994-05-31 | 1999-08-03 | Xoma Corporation | Bactericidal/permeability-increasing protein (BPI) compositions |
US6054492A (en) * | 1996-09-09 | 2000-04-25 | Supratek Pharma Inc. | Fluorinated copolymeric pharmaceutical adjuncts |
US6093391A (en) * | 1992-10-08 | 2000-07-25 | Supratek Pharma, Inc. | Peptide copolymer compositions |
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